WITCH
W.I.T.C.H.
A story about a group of men duped by their wives into attending the W.I.T.C.H. Institute in order to learn more appropriate behavior. They are forced to do many humiliating things to "earn" tokens acknowledging their accomplishments.
W.I.T.C.H.
Women's Institute for Training ......... Husbands
Some of them were caught cheating on their wives. Some were caught in
various ways while wearing women's clothing. Others were miscreants who
had in some way so displeased their wives that their actions had driven
their wives to take drastic action.
All the men had in common the fact that their unexpected behavior
infuriated their wives enough to want to punish their husbands in some
unique way. The wives had in common that they had each found the same
way. It had not been easy to find this way either. But they had all
navigated through a series of websites, each directing any new members
to join the next website where they were instructed on how to pursue a
slightly more devious way of exacting revenge on a misbehaving spouse.
The last one directed any women having come this far to a small
newspaper ad which in turn gave them a phone number to call for further
instructions if they used the proper code from the website,. It had all
been part of a grand plan to capture the interest of a very small,
select, and curious group of women intent on seeking revenge on a man
that had wronged them.
The inventor of this grand scheme, Lady L. was herself a fabulously
wealthy woman who had been nearly cheated out of her vast inherited
fortune by a conniving husband. Her experience was so bitter and her
personality so vengeful that she had not only "taken care of" her own
problem but she decided she was going to help other dedicated women with
solutions to their problems.
And so it was. One by one each of the dozen ladies had made the phone
call. Actually others had called but they backed out after hearing the
direction that their revenge would take.
It was a truly thorough screening process. One that resulted in only
those fully dedicated to making their victims pay for their
transgressions following through on the plan. Immediately after the
women agreed to join, the websites were closed, newspaper ad cancelled
and phone number disconnected. The trail would be untraceable.
One by one each of the parties received the same letter telling them
that they had won a fortune ($20,000,000) in the contest that their
wives had entered. In addition to the money they had also won a
fractional interest in a private Caribbean island. The only condition
was that they move there for a period of time to consider permanent
possession. It was not difficult to get the men to go along with this
life changing experience when they saw the $20,000,000 credited to their
bank accounts. (None of which they could spend, of course, until they
arrived on the island as agreed.) That is not to say that some were not
skeptical about their fantastic good luck--one even had his lawyer look
into the legitimacy of this contest--but Lady L. had left nothing chance.
The contest had been private and there was only a limited number of
things anyone could check, but with all that money in the joint account
belonging to themselves and their wives, the attempts to disprove their
good fortune were limited indeed. It was not long before all the men had
quit their jobs (some at the insistence of their wives) and said goodbye
to their old lives. The timing so that each would arrive at the island
within a few days of each other was the most difficult to arrange, but
in the end, Lady L. had also cleverly managed to slow down the most
anxious ones with legal issues and papers to sign and speed up the
hesitant ones with time limitations so that all couples were in place
and ready to participate within days of each other.
At last, all of the couples were assembled in a small meeting room of
the one hotel on the island. Each of the men thought that the other
couples were the other winners that would share their fractional
interest in island ownership. The women knew differently.
The one named Andrew had always had strong sexual urges and many sexual
fantasies. He was at a point in his marriage that he simply wanted to
satisfy these fantasies but knew his wife would not understand, much
less approve of them. So, in secret, he sought out the services of a
professional dominatrix. This actually worked well for him for a while
until he wanted still more than the domme was willing to provide.
Dissatisfied, but still insisting on having it his way, he made the
mistake of not paying his domme for services she had already rendered.
His domme repaid his ignorance of this aspect of her business in spades
by affirming to his wife what she was already beginning to suspect. When
she confronted him about his indiscretions he arrogantly brushed her
aside thinking that he could get away with anything. His substantial
income, coupled with the fact that his wife, therefore, did not need to
work, insulated him from reprisals by his wife, or so he thought.
Bradley had led a relatively normal life until after he got married. He
had always been somewhat submissive and his wife actually found that to
be one of his endearing qualities as she thought that he was just sweet.
Then she too began to wonder why his sexual interest seemed to decline
so suddenly. She discovered, quite by accident, that he was seeing
someone. That someone happened to be another man! Her shock at the
discovery of his bisexuality, led her to begin her search for answers on
the internet. That search ultimately led her here.
Charlie had been cross-dressing since he was 15. He discovered his
attraction to wearing women's clothing when he saw his sister's panties
hanging on a clothes line to dry and could not resist the urge to try
them on. His immediate reaction, a rock-hard erection. He remained a
cross-dresser ever since. The problem was, he always did it in secret
and never even hinted to his wife, that he enjoyed it so much. His lack
of interest in sex led his wife to believe that he was cheating on her,
but she eventually found his stash of women's clothing and pornography
and when she confronted him with her discovery, very embarrassed and
trying to search for a reasonable explanation, he insisted that this was
"normal" male behavior and, therefore he was unwilling to change.
Daniel was slight of build, submissive by nature and seemed to be a
perfect match for his somewhat shy wife. It was surprising that they had
met at all, given that both had reclusive personalities. But their
friends recognized this and set them up on a blind date. With more than
a little pressure from their friends, eventually they agreed to marry.
No one doubted that they belonged together until his wife found him
cross-dressing in secret. He had the physique that allowed him to pass
easily as a female when dressed as such. What surprised her is that he
did this on a regular basis without her knowledge. She found out only
when their neighbor let it slip that she had seen him in women's
clothes. His wife was mortified. The neighbors knew and she did not and
this ate at her core. His refusal to talk with her about it, coupled
with his insistence that he continue cross-dressing without her approval
set her on a course she was determined to pursue. That is how they ended
up at the W.I.T.C.H. institute.
Edward was the handsome, dynamic world beater that no one would have
guessed had a feminine side to his personality. In every way he
appeared normal but his deep dark secret, which was ultimately, perhaps
inevitably revealed to his wife was that he often wore lingerie under
his male clothing. Usually very outgoing by nature, he became very
sheepish and embarrassed when his wife found his hidden "stash" of
unmentionables in the garage. He had hoped his loving wife would have
been more understanding. She was not. She saw this fetish as a great
threat to her social standing should it ever leak out. She was
determined to nip it in the bud. A series of covert inquiries had led
her to the institute.
Frank and his wife were members of the local BDSM club. Both were into
alternate lifestyle fantasies until he went over the top and demanded
that his wife do things she was not comfortable with. He continued to
press her already liberal limitations until she finally said enough. She
decided to take him to a totally new level beyond even his dreams.
George was a happy-go-lucky sole, never married and with no current
girlfriend. He was somewhat overweight but this did not stop him from
pursuing his desire to get in touch with his feminine side. Having no
significant other made it easier and perhaps more necessary for him to
surround himself with feminine things. He enjoyed cross-dressing when
he could and made only half-hearted efforts to hide his somewhat unusual
pursuits, which he felt were perfectly natural. He was a member of
several femdom internet groups in which he had a picture of his femme
self proudly on display in his profile. His naturally trusting nature
eventually resulted in him believing a prank that one of his internet
"friends" decided to play on poor George. Purely at random some college
student somewhere had chosen George to be the guinea pig when he had
discovered purely by chance the phone number Lady L. had planted.
George's case was only different from the others in that he was set up
by someone whom he didn't even know. The result was the same. George
took the bait and arrived at the island with the others expecting
something far different than he was going to get.
Harry began with an almost idyllic relationship with his beautiful wife.
Successful in business, he and his wife frequented some of the worlds
nicest beaches, most popular casinos and trendy hot spots. So enamored
with himself was Harry, that he felt one woman was not enough for him
and eventually he succumbed to his desires, and was immediately caught
by his wife who just as quickly decided what his fate would be.
Irv and his outgoing spouse had been married a long time and his wife
began to tire of the relationship. When she wanted to join a local wife
swapping club he acquiesced. His wife met another member she apparently
just could not live without. Irv was OK with this and even found it
erotic to see his wife with other men. She became tired of having such a
"wimp" of a husband and decided she needed a way to change their
relationship.
Larry is my name, or at least was my name. I had had a normal
relationship with my wife too, until we had grown apart as many couples
do over time. As the years went by our interest in each other grew less
and less until sex was nonexistent. By that time I had begun to revert
to an old habit I had begun many years ago. Whenever I had found myself
between girlfriends, I seemed to find comfort in cross dressing. It was
as though I was providing myself with my own female companionship. It
worked because there was no one around to keep me from satisfying myself
in this private, harmless way. That is, until I was married and began
doing it again in "private". I had been wearing a bra and panties from
my well hidden stash when my wife came home unexpectedly early one
evening. I though I had it covered when I quickly removed and hid my
feminine things dove into bed and pretended to be asleep before she
walked in. I didn't realize that the very snug bra had left
unmistakable impressions on my back. My wife noticed this, of course
and most unfortunately for me without my knowledge. She then was able
to set traps for me in the form of hidden video cameras. In short order
she literally had the "goods" on me without me knowing. For my wife
this was the last straw and set her on her vengeful ways. It did not
take her long to find the "Institute".
There were a few others and their stories are remarkably similar to the
stories of the readers of this tale.
When all of the participants were finally settled in their hotel rooms
we each received a note that their would be an introductory meeting that
evening in the hotels small conference room. Everyone was anxious to
attend. Especially the ladies.
It was Lady L. herself who got up at the podium in front of the room and
welcomed us all to the island, her island. The shocking news was broken
to all the men at once. After her initial welcome, she got right down to
business.
"You men think that all of your worries are over. Well, I'm afraid that
you have been intentionally misled about your stay here. You see, while
most of your needs will be taken care of while you're here, I'm afraid
that you will be trading in one thing during you're stay here. That
thing is your freedom. You see, all of you have been captured on video
doing things that you should not have been doing."
Each of the men suddenly became silent... and worried.
Lady L. went on, "I am going to show all of you a brief video of what I
am talking about." The lights slowly dimmed and a screen lowered
silently from the ceiling. For a brief moment there was absolute
silence in the room. When the video began to play the men remained
silent. Among the ladies could be heard an occasional giggle, snicker or
an "Oooh" or "Ahhh".
One by one, the men's actions were displayed on the screen for all to
see. They were all clearly from the angles of **********eras but each
displayed some of the most humiliating scenes that the men could
remember. The insertion of a butt plug, the wet spot appearing on the
front of a pair of panties, the delight showing on one's face as he
slipped on a pair of pantyhose. A visit to a Dominatrix. It was all
there.
As their own peculiar behavior eventually appeared on the screen for all
to see, the look on each of the men's faces went from shock to utter
red-faced humiliation. In contrast, by the end of the video the women,
all good friends by now, were laughing hysterically.
The screen went blank and rose into it's place in the ceiling. Lady L.
again stood at the podium but did not speak until the laughter of the
ladies had subsided several moments later.
"Well gentlemen, and I use the term very loosely, do you have anything
to say for yourselves?" Andrew mumble something unintelligible under his
breath but the room was otherwise silent. "Don't be afraid. The reason
we are here is to give you a chance to redeem yourselves in front of the
one who sent you here!" She glanced at George. "You will have one
chance to recover your dignity and again become worthy in the eyes of
your spouse. Otherwise these videos will make their way on to the
internet, into the places you used to work and into the mailboxes of
many of your relatives. In short, your life as you knew it would be
over."
"You see, we ladies have come to the realization that there are many men
out there who enjoy being feminine or have unusual fantasies. The
problem is that they also want regular relationships with women but
don't consider the affect your fetish has on that woman.
"So, we are giving you the opportunity to have your cake and eat it too.
The only thing we require of you is your complete and unquestioning
obedience! You must do what is required of you or you will fail and
suffer the consequences. But don't worry, it's not all bad news. You
will be permitted a transition phase in which you will be able to wear
clothing that more closely fits your temperament. Yes, women's clothes.
But before you get too excited, let me explain that you must agree to
this course of behavior modification, in writing, otherwise you're
screwed as previously mentioned."
Their minds racing, the men could each be seen mentally weighing their
choices. None was their silent and unanimous conclusion.
"Any questions?" Lady L. asked.
After a brief pause, Edward raised his hand.
"How long will this take?"
"As long as necessary, until your significant other says you are ready."
"Will we be allowed to contact anyone from back home?" Again Edward
spoke.
"No. There are no phones on the island and no cell phone service."
"You know this is k**napping." Andrew interjected forcefully.
"Not after you sign the agreement which, among other things, states that
you voluntarily accept these requirements for your own betterment."
"I won't sign it!" Andrew barked abruptly.
"You're choice. The previously stated consequences would still apply.
Gentlemen, (cough) so that you don't miss the point of this rather
extravagant operation, our sincere hope that you will come to see that
we are doing this for your own good. We truly believe that once you
have been immersed in our programs for each of you, that you too will
come to appreciate your lifestyle choices. We know that you will be
happier and more content than you have ever been. This is as much for
your benefit as for that of your spouse...or significant other."
Cathy, a very attractive young lady appeared at the door of the
conference room with papers and pens. She passed them out to the men
while the ladies watched smiling. There were several pages of fine print
which several of the men began to read in earnest, fearing the worst.
Lacking much detail about specifics, nothing appeared unusual for a
contract except the phrase "Total Obedience." There was little else to
do but sign. All of the men did as each lady gave a "thank you dear"
smile to their new charge.
We were then each given a pamphlet containing a lot of material which
proved to be pretty convincing. The first information was on the Fem Dom
lifestyle and why it made sense and how it made life better for all
parties involved. It told why women were superior in the marriage and
why women should be in control providing many examples of marriages made
successful by Fem Dom rule. It explained why males were meant to serve
their female "owners" and why it was natural for that to happen. It also
explained some of the fears and concerns males would have and why they
were nothing to worry about. Males in these 'advanced lifestyle'
marriages would learn to accept that the only thing that truly brought
them happiness was serving and pleasing their wives.
As males, except for Harold, we had all expressed varying degrees of
femininity or acceptance of female dominance somewhere along the line in
our lives. And in varying degrees we all anticipated anxiously what was
going to happen to us next. But none of us was ready for what the
ladies had in store.
We then took a short break to eat lunch and each receive a pep talk from
our respective lady. This was to set the tone of our training which
would be all praise and rewards for obedience and both mental and
physical punishments for disobedience.
Upon restarting our meeting Cathy gave us another pamphlet which we were
given ample time to quietly read.
This information was on sissy training and how much more pleasure a male
would get from being dressed and trained to be a sissy. Most of the
emphasis was on sissy maid training and how such tremendous feelings of
worth and value would be felt by the well trained sissy maid. It posed
questions to ask ourselves about our own feelings of becoming such an
important part in the life of a woman.
A highlighted section noted in detail how much a woman needed powerful
sexual experiences and how few men could actually provide them. It
strongly supported cuckoldry as the best way for the woman to be happy
and satisfied and to improve her attitude. It even had testimonies from
cuckold husbands who said they found it to be true.
There was a great deal of information on how the greatest feeling a
sissy maid cuckold husband could have was serving his wife in front of
her lover and friends and seeing the expression of pride and joy on her
face. Husband after husband related how wonderful it made them feel to
perform in this manner. Toward the end it went on to explain about
serving and taking care of madam and her lover(s). It all seemed to be
hinting that our wives were intent on taking on lovers while we suffered
extreme embarrassment of some sort. The range of reactions from our
group were from an occasional gasp or muffled "WHAT? NO WAY!" to
squirming in a poorly hidden attempt to hide an erection. It had a
profound effect on my mind and feelings. I began to consider my wife's
needs, the wrongs I had committed and my place in our relationship.
"Wonderful! You have all agreed in writing to take steps to improve
yourselves." Lady L. stated enthusiastically. "In your cases this may
take quite a while. In order to measure your progress we have to have a
base line to start from. That means we are going to start each of you
out in feminine mode and make progress from there. We will soon see how
each of you handles it."
The ladies in the room were all wearing ear to ear grins. The men were
all deathly silent.
"Each of you will begin at an appropriate starting point for your own
level of feminization and you will progress toward the goal that your
spouse or significant other has established for you. I will warn you
that our expectations for you are high. If you do not immediately get
with and stay with the program you will be made to regret your
decision." Lady L's tone as the ultimate authority was unmistakable.
It seemed the ladies could barely contain themselves. The men remained
silent and wide-eyed as to what might be required of them. Only Andrew
remained expressionless and looked as though he was prepared to be
openly defiant.
"From now on you address any woman as 'Mistress' or 'Madam', whatever
their preference. You will be referred to in the feminine tense, as
'she' or 'her'. Each of your sponsors, that is your spouse or
significant other, has suggested a feminine name for you.
And since each of you has, in some form or another, expressed some
feminine behavior, this will be your new name. Any objections?"
Andrew spoke in an almost sarcastic tone. "What if we don't like the
name?"
Lady L. remained silent. She looked us over with an expression of utter
disdain.
"You will now pair up in two's. You will shower and then you will shave
every hair off of your body from your sideburns down. That is every
hair, neck, chest, back, armpits, forearms, pubic area, legs, toes, etc.
You will be paired in twos and each will inspect the other for any
flaws. If upon our inspection a single hair is found anywhere below your
sideburns you will both be punished severely. Since there are an odd
number, Andrew will be shaved by his sponsor. You have one hour."
Now in near panic mode the males looked around the room in confusion
while the ladies directed each pairing to the bathroom of one of the
hotels suites. I was paired with Charlie. The circumstances resulted
in us forming an immediate friendship. Both of us had a moderate level
of self-acceptance of our feminine sides and were more than willing to
go with the "program," given the unknown but certain consequences. We,
in fact, were the first ones done in showering and shaving, leaving us
enough time to carefully inspect each other to make sure not a hair was
missed. It was a most unusual experience, however, washing, lathering
and then shaving my entire body, and then having Charlie closely look me
over and I him. Oddly, or perhaps not, the sensation of slowly being
made totally hairless and then closely examined by another man resulted
in first Charlie, then myself, becoming sexually aroused. We each
laughed at the other's involuntary acceptance of this humiliation and
this ended up helping us bond together even further. For both of us,
our situation seemed very erotic in a way. Having no control and being
forced to do something so against our basic nature.
After the hour was up we all assembled again in the meeting room. The
males were all nude and very embarrassed. The ladies were all giggling
and whispering to each other.
Each of the males, including me, tried to ignore the new "look" each of
us was sporting, but could not help but notice that Andrew alone still
had his pubic hair.
Again, Lady L. took charge of the meeting. "Andrew, henceforth to be
known as Andrea, has been a little slower than the others in accepting
her fate. And as you will see, being unacceptably slow to fulfill our
wishes for you has consequences."
Andrew (now Andrea) displayed a worried look of defiance as a wooden
table with straps was wheeled into the room by his wife and one other
lady. Suddenly Andrea began to head for the door muttering "screw this"
as she tried to leave. Just as suddenly, two large black men who had
been standing silently close by, grabbed his arms and held him while one
of Lady L.'s assistants stuck a syringe in Andrea's arm and caused her
to fall limply to the floor almost immediately. When she awoke, she was
bound helplessly spread-eagle to the table. Finally, when she was fully
aware of what was going on, her wife placed two wooden matchsticks in
Andrea's pubic hair with the flammable end pointing upward. Her wife
then lit another match and held it to the tips of those nestled in
Andrea's bush. They ignited and slowly burned down until the crackle of
burning hair could be both heard and smelled. Andrea shouted, "Damn you!
Stop it. Let me out of here!" Then her pubic hair began to burn more
quickly as individual hairs lit up and burned like filaments of a light
bulb. "Aaaaahhh! Stop it," she screamed. As the rest of us watched,
Lady L. put a damp cloth over Andrea's groin to stop the spectacle.
"Are you going to shave yourself now?" Lady L. insisted. No reply. Lady
L. then placed three more matches in the stubble that remained of
Andrea's pubic hair.
"No! I'll shave," Andrea squeaked.
"No, you won't" said Lady L. "The other 'males' will do it for you."
Lady L. signaled Daniel (now Daniella) to go get some shave cream and a
razor from the bathroom she had used herself. She hurried obediently and
was back within seconds. At Lady L.'s instruction, each of us carefully
shaved a small patch of the remaining hair until Andrea was as smooth as
the rest of us. At this point, each of us was too afraid to not follow
Lady L.'s next command: "I want each of you to file by Andrea and tell
her how pretty her penis looks now." Reluctantly, each in turn did
exactly as told. Andrea, infuriated and clearly wanting to curse at all
of us, remained silent.
With that Lady L. snapped her fingers and the two black men placed a
cock-gag in Andrea's mouth, completely muffling any potential
objections.
"Let this be a lesson to each of you as to what will happen if you do
not willingly follow directions." Lady L. insisted. "This is just a
taste. And as a consequence for each of you for your friend's behavior,
you will each spend tonight in a cage. You may thank Andrea later."
The males stood aghast. The ladies were also silently with stern looks
on their faces.
That night, each of the males spent naked, confined in a locked dog cage
approximately 2' x 3' x 4'. We were thus given the incentive to keep
each other in line or suffer as a group for the indiscretions of any
member.
<<<<<<<<<<< >>>>>>>>>>>>>
Early the next morning we were each released from our confinement with a
series of moans and groans because of our stiff joints. As we stood
naked as a group before the ladies, Lady L. presented each of us with a
plaque honoring our acceptance of much deserved punishment for
"CHEATING" on our wives. Each was customized to show our own particular
method of "cheating". Then Lady L. began to explain more about what was
going to happen to us.
"If you perform satisfactorily what is required of you today you will
avoid having to sleep in the kennel cage tonight. I think the
alternative sleeping arrangements will be much more to your liking."
In unison all of the males let out a sigh of relief. The cage was very
unpleasant.
"You will sleep in a comfortable bed. Since there is only a limited
number of beds you will double up with your assigned partner." We looked
at each other, somewhat perplexed. "Oh, and by the way, going forward
each of you will refer to your partner as your "boyfriend". You will
either refer to her by her feminine name or as "my boyfriend. Is that
understood?... IS THAT UNDERSTOOD?"
"Yes, Madam" was mumbled by all except Andrea, who earned another icy
stare from Lady L.
"Also, as you walk between buildings on campus with your boyfriend, you
will hold her hand at all times, again, no exceptions." After a short
pause, "UNDERSTOOD?"
"Yes Madam," a little louder this time.
"I know this may seem difficult for you now but it is an integral part
of your training on this campus. I call it a campus because this is
where you will be taught what you need to know. You have each expressed
your feminine side in some way and this is where that side of you will
be cultivated and nurtured. In essence you will receive feminization
training and learn to cast aside the undesirable characteristics of any
masculinity you may possess."
Each of the males mumbled her own unique but subdued response, still
somewhat in disbelief of what was happening.
"Each of you will pair up with your boyfriend and Monday through Friday
will attend the following classes together:
One; Domestic Sciences, Two; Feminine Dress and Behavior, Three; Dance,
Four; Women's Studies and Five, Anatomy. Other classes will be
organized for each of you on an individual basis as needed. You will
have homework... QUIET!!" Grumblings were growing louder among the
males but Lady L.'s quick rebuke silenced us instantly. "You will have
homework and you will be tested on what you learn. Anyone receiving
failing grades will be punished accordingly. Classes start next Monday
and you will be given more details by that time. That is all." Lady L.
turned and began walking away.
Again a murmur arose between the males when Andrea spoke just loudly
enough to assure that Lady L. could hear, "This is bullshit!" At this
comment, Lady L. slowly turned back to face Andrea with another cold
stare. She then gave a slight nod to one of the black men standing
nearby who then quickly raised a dart gun and shot Andrea in her
buttock. "Aaahhh, owww. Dammit. F*** you!" Andrea only gave these
brief remarks before falling flat on her face, u*********s. The black
man with the dart gun as well as two others promptly grabbed Andrea and
carried her into one of the small dwellings near our meeting place.
This event left the other males in stunned silence, fearing the same
might happen to them if even the slightest objection were made. We were
then led back in our "boyfriend" pairs to our rooms to try to absorb all
that had just happened that morning.
It wasn't until several days later that Andrea was released from her
confines and allowed to rejoin the group. It was not difficult to see
that something was very different about her. She was walking slowly,
with head down. When she approached close enough to us we could see
what had happened. Her penis had been given what is called a Prince
Albert piercing, a large thick metal ring had been inserted through the
tip and it was locked to another ring through her perineum. This made
it impossible for her to achieve an erection. This was a shock to the
rest of us. We had been exposed to our first real example of how far
the ladies were willing to go.
Monday finally arrived and the males all were full of a combination of
fear and anticipation. Despite the fact that Charlie and I got along
well, I had difficulty accepting that I would have to walk hand in hand
with him, both wearing knee socks, matching plaid skirts and ruffled
blouses, across an open courtyard to a class that was to teach us how to
dance. When we arrived we were instructed to put on pink leotards and
tights, which, by some coincidence fit each of us perfectly. It was one
thing to dress in feminine things in private but quite another to be
humiliated in front of three women. It helped to have Charlie there as
it cut my embarrassment exactly in half.
We were also presented with another plaque honoring our acceptance and
desire for full time CROSS-DRESSING as a means of enhancing our
preferred feminine characteristics.
My realization of just how humiliating this was going to be hit home
when the first lesson, first through fifth positions began. Ballet! We
were going to learn ballet! Demi plies, first, second and third
arabesques, it was all so confusing, and embarrassing at first. But we
would be made to repeat the moves over and over again until we got it
right. When I mocked the pirouette during training, the penalty was an
ice cold shower after class, followed by a painful whipping with the a
cane. It was clear from the start, in every class that Charlie and I
attended that there would be no nonsense. We were there to learn and
learn we did. Obedience was indeed the rule. Deliberate errors were
met with severe punishment. I received a heart tattoo on my ankle for
one offense, a pink butterfly on my shoulder blade for another and a
rainbow tattoo just above my buttocks for a third. Errors during honest
attempts were met with encouraging remarks and additional repetitions.
At first to avoid punishments, and later to earn praise, Charlie and I
began to put forth our best efforts to learn ballet. As unnatural as it
seemed to us, our overwhelming desire eventually became to please the
ladies and avoid pain. Progress was rewarded. Lack of progress was
punished with increasing severity. It was a classical case of
conditioning.
Charlie and I eventually became modestly proficient at ballet positions
and moves. We could not perform lifts or joint moves with lady
ballerinas but they began to call us novice danseurs (male ballerinas).
Privately, the ladies were overjoyed if even somewhat surprised to see
the program was off to such a good start. Here it was, a group of
contrite males that were going to accept much deserved humiliation by
learning to be feminine.
As further encouragement to our transformation into sissies, Lady L.
provided each of us with a locking chastity cage to which our mistress
held the key. We were told that this would assist us in our desire to
please the ladies by enhancing our submission. And given that we each
stayed locked up for one month before being released she was 100%
correct.
At the end of that month each of us received a plaque honoring our
acceptance of long-term CHASTITY as a way to reform ourselves.
When I awoke the next morning it was as if I had awakened from a bad
dream. I was lying next to Charlie (now "Charlene") our backs turned to
each other. We were both wearing matching black nighties and despite the
fact that we had become friends, it was very embarrassing having to share
the same bed with him and have to refer to him as "she, her or my
boyfriend" from now on.
The next thing I noticed were my three plaques hanging over the bed. The
lettering made them look like diplomas signed by Lady L.
In bold script the first read:
CHEATING,
For allowing my wife to believe I was a man while I dressed as a woman
The second:
CROSS DRESSING
For wearing women's clothing while pretending to be masculine
And finally:
CHASTITY
For transferring all rights to my sexual activity to my wife
I felt that they were foolish but did not dare try to take them down for
fear of the consequences. I glanced at the alarm clock and realized I
would have to hurry to dress for our Domestic Sciences class. I awakened
Charlene and we raced to dress in our matching plaid skirts and ruffled
blouses. We both misjudged how long it would take to dress and get to
class because we could not move very fast in our high heels while holding
hands. We were five minutes late to class and earned two extra weeks in
chastity as a result.
Domestic Sciences class began with each of us being given two types of
maid uniforms. One was a classic professional style in powder blue
complete with knee length skirt, apron, flat shoes and name badge,
engraved with our feminine names of course. The other was a short French
maid outfit in black, with garter, black stockings and 4" high heel pumps
which happened to fit each of us perfectly.
I tried not to show it but I was actually very pleased to be able to wear
such feminine things which seemed to be made especially for me. I
guessed the other regular cross dressers in the group must be happy too
as these were quality clothes. I reveled in this small pleasure even
though it was the reason I was here in the first place.
Immediately after receiving the maid's outfits we were informed that this
would be a learn-by-doing class. (Note: The instructors in these classes
were strangers to us but generally were very pretty and very
knowledgeable about their subject. Our wives often sat in on some of the
classes to watch our progress, and witness our humiliation at being
exposed as sissies in front of our instructors.)
In this class we would learn all of the responsibilities of maintaining
the island's hotel rooms, including making the beds, washing the laundry,
ironing, dusting, cleaning the bathrooms and all of the other mundane
tasks associated with a maid's work. After being shown just once exactly
how to fold and tuck the sheets on the bed, for example, we were then
expected to do them ourselves. And we did. Over and over and over again
until we got it right. It was mind-numbing work and caused the discontent
with our group's situation begin to grow....silently.
Despite the fact that there were few visitors to the island, a small boat
would appear occasionally and it's crew and guests would stay for a week
or so. Keeping the hotel rooms in perfect condition soon became our
responsibility. We would each work in teams a couple of days a week and
were closely supervised by our instructor. A good job was praised and a
bad job... well, you know the story.
Some of us, myself included, began to worry when we were told that the
French maid's uniforms would be worn when we served at a party. As fun
as it was to wear the outfit, it was terrifying to think that we would
have to display ourselves in front of strangers while wearing it. The
more people that knew of my fetish the less I liked it. We were even
taught how to curtsey. This was getting out of hand.
<<<<<<<<<<<<>>>>>>>>>>>
Women's Studies, our next class, began with the various articles of
makeup, their applicators and what colors and tones looked best together.
Cathy, the same pretty girl who had handed out the agreements for us to
sign at our first meeting, was our instructor. I noticed she smiled my
way a few times and I began to daydream of striking up a friendship (or
more?) with her.
The first time we practiced applying makeup it was a comedy of errors.
Bradley ("Beth"), Daniela, Charlene and I had all experimented at some
point in the past and therefore, did a passable job. Cathy actually
complimented me. The others ended up looking more like clowns than women.
I was happy that for once I did not have to do countless repetitions.
Andrew did and you could tell he was not happy about it.
Early the next morning, each of us was lead individually to a small hut
at the edge of our compound. Each left the hut a short time later and
was lead out of sight of the others, directly back to our rooms. When my
turn came I was lead by the arm by my wife to the hut. Lady L. and a
smiling black man and woman were there. A case was placed before me and I
was told to choose one pair among it's contents. It was then opened to
reveal a wide selection of silver hoop earrings. They were not clip-on
earrings. It was held in front of me until I selected a set of large but
otherwise plain ones.
Lady L. spoke first. "Do you willingly accept this precious gift as a
reward for your high marks in Women's Studies?"
I naturally hesitated allowing time for my wife to interject, "You looked
so pretty with that make-up on! I was so proud of you!"
All three of them gazed into my eyes expecting a quick answer. What
choice did I have?
"Y-Yes, I do".
"Now please sit up in your chair and remain still" said the black lady.
My heart sank.
I closed my eyes and braced myself, my mind racing. Lots of men have
pierced ears, I thought, I'll just have to pretend I'm liberal minded.
"Ouch" I said as the first piercing was done. Half in shock, I just sat
there motionless as an identical piercing was done on my other ear. I
was given studs to place in each of the new holes to keep them from
healing shut.
"They look so good on you!" my wife chimed in. "I can't believe how nice
you look! I'm so proud of the progress you've made!" She lead me back to
my room where I had all evening to enjoy listening to Daniela rave about
how good she thought we would both look with our new earrings. The
compliments did help me accept my situation but in the back of my mind I
feared that this took me yet one step closer to femininity. Was there any
way out?
Women's Studies would eventually give all of us difficulty as it included
reading and memorizing some of the articles in women's magazines.
Cosmopolitan, Glamour and Elle became our standard reading material. In
fact we read nothing else. We were being totally immersed in the feminine
way of life.
On one important test in this class I had failed to read the assignment
because I had maid duty the day before. I failed it miserably. Even worse
than Andrea, whom I had suspected of cheating. I then learned why
finishing last in anything was to be avoided.
Even though Cathy tried to talk her out of it, later that afternoon as I
stood bound naked with my legs spread apart, a large dollop of Ben Gay
was smeared on my scrotum by one of Lady L.'s assistants. In a matter
of moments my balls seemed as though they were on fire and the pain kept
getting worse and worse until I begged her to wipe it off which she, of
course, did not. I was in tears by the time the affects of the ointment
wore off. I obediently thanked my tormentor for teaching me right from
wrong and promised that I would do better in the future.
A funny thing about trying not to be last. You never know how good or bad
any one else will be so you are forced to really try to do your best and
not rely on someone else being worse than you.
Such behavior and punishment (I was not alone in receiving this) had an
effect on the entire class. We then made a special effort to learn how to
apply lipstick, mascara, blush, eye liner, nail polish and the like.
Failure was punished, success was rewarded with lavish praise about how
good the makeup made us look. It was not difficult to see that we were
being conditioned to accept our new femininity but despite the entire
group of us trying to think of something, there was simply nothing we
could do about it. At the end of the first 'semester', as our final test
we each had to apply our own makeup as though we were going on a formal
date. After our pictures were taken, (for 'judging' purposes of course)
we were assembled as a group and given lavish praise for a job well done.
Whether we had indeed done a good job or not I really didn't care, just
to hear it from Lady L. herself was relief.
<<<<<<<<<<<<<<>>>>>>>>>>>>>>
In our first class in Feminine Dress and Behavior our instructor told us
that no matter what (if anything) we were wearing at the moment, when we
were around the ladies, we must be wearing a smile. This sounded
innocuous enough but at first was very difficult to do. When you are
naked, ashamed and humiliated, it is difficult to smile. But when you
must as a condition of total obedience, you learn to suppress those
feelings and put on a façade of happiness. This had the odd effect of
making me feel more comfortable around the ladies even when I was naked
and holding my boyfriend's hand. After all, how are you supposed to feel
ashamed while you are smiling? And, of course, it had to be a 'genuine'
smile.
Imagine dressed completely en femme, holding hands with your "boyfriend"
who is also wearing a skirt, smiling at a group of ladies. You naturally
tend to reassess who you are.
In subsequent Feminine Dress and Behavior classes, we learned about
fabrics, what blouses looked best with what skirts, the difference
between mules and espadrilles, shirred versus bias cut, what a "Dolman"
sleeve is and on and on. It was difficult and boring but it was drilled
into each of us with the same rewards for learning and punishments for
failing to learn. Each of us in our own way could still be found to be
rebelling against this forced education. It was unnatural and at times,
even though many of us loved cross-dressing, it seemed that it was too
much against our nature, too feminine, even for a sissy. There was no
respite from the constant bombardment of feminine things. The required
reading of women's magazines. Videos of 'Oprah', 'The Shopping Channel'
and "chick flick" movies. Never even a hint of anything remotely
masculine. No sports on television, no getting together to do "guy"
things. Everything was 100% feminine all of the time.
As pleasant as some of the feminine things we were exposed to seemed, the
complete lack of anything masculine eventually led Andrea to crack. She
went as far as to openly suggest to our sissy group that we all rebel,
steal a boat and take off. Her arguments included the apparent
permanence of our situation and were convincing. Her private plans had
begun to find sympathetic ears the longer we went without any break from
the classes in femininity.
<<<<<<<<<<<>>>>>>>>>>>
A new "term" has just started and as part of our "socialization" training
as the ladies call it, we each were assigned a new boyfriend. I got
Daniela, the one among us that perhaps looked most feminine even without
all of our training. This time I am actually kind of glad about it. He
(sorry, 'she') is very friendly when you get to know him (sorry, 'her')
and we seem to share a lot in common. In addition, our new classes have
started and, as usual, we will attend them together, sometimes naked,
holding hands as we walk between classes. This is particularly fortunate
for me because one of our classes this term is called "Gay By Choice" and
if I have to attend a class like that I would rather be doing it with
Daniela, who is probably the best looking of us sissies. (Yes, I have
finally broken down and accepted the fact that we must always refer to
each other, and indeed accept ourselves, as sissies.)
In Gay By Choice class we first learned about the history of
homosexuality dating back from earliest recorded times until the present,
with a heavy emphasis on how common it once was and how it is now, each
day, again becoming more acceptable. Our instructor gave us heavy
indoctrination in the fact that gays are among the few groups that hold a
parade to express their pride in their beliefs. We learned that
homosexuality is a noble goal that we in particular should strive for.
This was scary. It did not matter how averse any of us were (if at all)
to this orientation. We were given more homework than in any other
class. The daily homework generally was to watch two hours of videos of
attractive males of all ages making love in every way imaginable. I say
love and not just sex because the gays in the videos did seem to be
genuinely fond of each other. There was plenty of romance leading up to
the sexual acts, which were always portrayed as a wonderful and logical
happy ending.
We all seemed to tolerate these classes until our homework assignments
changed. Our period of chastity was increased to almost two months. We
were told that we would see this actually wind up as a reward and not a
punishment. Then, one evening at the end of this period, Jane, who was
Daniela's wife, and my wife Laura, came to our room for a visit. In eager
anticipation we both thought that this might be the end of our chastity
period as they were both wearing the keys to our chastity cages on
necklaces.
"Gurls, it's bedtime!" Laura announced. "But before we release your
members from their confinement, we have to be sure that you are not going
to jump our bones right on the spot!"
Daniela and I were practically drooling.
"So we're going to cuff you before we release you. Now put your hands
behind each others back" Jane said. Daniela put her hands behind her
back causing Jane to roll her eyes and say "No. Behind each others back!"
We eagerly complied, my right arm over his left shoulder and his over
mine. Then each of the women placed padded pink bracelets over their
husbands wrists and locked them into place so that we were hugging each
other and could not jump and grab the ladies.
Then Laura spoke, "To further control the two horniest men alive we are
going to put these collars on you so that we can attach leashes if
necessary."
It sounded wonderfully erotic to me.
Then Jane placed pink dog collars snugly around our necks and connecting
them together as Laura tightly secured a large belt around our waists.
Daniela and I became confused at all of this bondage but there was little
we could do now with our movement so restricted.
Laura again, "And for good measure lets strap your ankles together,"
Which she proceeded to do.
"And now gurls, your release!" Jane then unlocked Daniela's chastity
device and Laura mine.
So there we were. Two nude sissies with the full length of our bodies
pressed together in an unbreakable hug. Two sissies that had not had so
much as an erection in two months.
Laughing with looks of delight on their faces, Laura spoke. "By the way,
we are also here to grade you on your 'How to kiss a man' quiz. So let's
see those red lips pressed together! And if you fail Lady L. will be
informed immediately."
Under these circumstances, Daniela and I both became erect immediately.
Our hairless, naked bodies pressed together and our cocks free at last.
The feeling was just too much. I took one look into Daniela's eyes with
her perfect mascara and eye shadow and kissed her passionately. She
kissed me back and thoughts of a quiz grade evaporated as we opened our
mouths and began to twirl our tongues together. I cared only about how it
felt and not how it looked. I was in heaven.
And so were the ladies. Laughing and snapping pictures as fast as she
could, Jane said, "Well, I guess it is each other that they prefer. There
is no room for a real woman in this scene. I guess we'll just have to go
find us some real men!"
The ladies continued to stand there watching in amazement as Daniela and
I began to hump each others cocks. There was no stopping us now. We
wanted relief. Was it only sex or was it more? Neither of us cared.
Within a couple of minutes we both ejaculated at the same time and
squirted our cum on each other's stomach and cock. It was such a good
feeling. I then gave Daniela a long slow kiss as though to thank her.
As I did that, Laura leaned over me and whispered in my ear, "Thank you
sweetie. I have given you what you really wanted. And you have given me
what I really want. My freedom to find a real man!" With that and an ear
to ear grin both ladies left the room with arms around each other's
waist.
<<<<<<<<<<<<>>>>>>>>>>>
Our bodies were still locked together when we awoke the next morning. I
kissed Daniela and both of our erections returned. This time is was
slower and more passionate as we made love again. For a while I didn't
want our bodies to be separated but it was our day to do maid service.
Eventually two of the large black men from the island came into our room
with keys to both the handcuffs and our chastity devices. They released
us and then stood by and made Daniela lock my cage and I hers, then
giving the keys back to the black gentlemen. We had only enough time to
shower together, dress and head off to the hotel to go clean bathrooms.
On the way, again holding hands, we passed my wife talking to the black
man and getting my key back from him. I smiled at them as required.
The next day I felt ashamed, not even knowing how I could do such a
thing. I was depressed at my situation. I had committed a homosexual
act, was wearing women's clothing exclusively, had several extremely
effeminate tattoos, worked as a maid and was at risk of losing my wife to
another man. Outside of that things were going pretty well. And I still
had to sleep in the same bed with my boyfriend Daniela. There we were
expressing our regrets for being attracted to each other. There seemed to
be no good way to handle this new situation.
I ran into Cathy, our Women's Studies instructor, on the beach the
following afternoon and we got to talking about my feelings. She was
genuinely sympathetic and hinted to me that my situation was not a
permanent one. She left me feeling better about myself. I sensed that if
I ever needed a friend among our tormentors she would be the one.
<<<<<<<<<<<<<<>>>>>>>>>>>>>>
A couple of days later Daniela and I were making the bed in one of the
hotel rooms when our wives walked in. They directed us to move some of
the furniture and to place scented candles around the room. As we stood
at attention at the foot of the bed they inspected every square inch of
the room. They found several 'violations' of their cleanliness rules
which we had to correct immediately. I vacuumed again, dusted again,
cleaned the mirror again and polished the furniture. When they were
finally satisfied, Laura spoke.
"It would be a shame if Lady L. were to find out about all of the
problems we found," My heart sank. Here was my lovely wife threatening
that I would be severely punished.
"We can go two ways on this" Laura said. "I can either turn you over to
Lady L. for punishment, I would probably recommend a Prince Albert
piercing, or you can be here tonight to do exactly as I say, in which
case I would praise you greatly right in front of her. And that would
probably mean less work, more free time, better rations... " She looked
me directly in the eyes. Again, what choice did I have? I opted for the
latter.
At the appointed time that evening I arrived at the room. Laura was there
alone and dressed to kill. She directed me to take off my blouse and
skirt while leaving my bra and panties on. She had me sit in one of the
chairs I had moved earlier to the foot of the bed. Then she cuffed my
wrists and ankles to the chair using the same pink cuffs she had used on
Daniela and I the other evening. I knew that whatever was going to happen
I probably would not like it. She unlocked my chastity device and sat on
the foot of the bed looking directly at me.
"Let me remind you of our little agreement. You obey, you win. You
disobey, you lose. Is that clear?"
"Yes mam."
Moments later there was a gentle knock at the door. I think I knew what
to expect. Laura let in the same black gentleman that had taken the key
from my chastity cage the other evening. "Lynn, meet... well you can just
call him 'Sir'. Sir, meet my 'husband' Lynn.
Lynn is anxious to have me enjoy sex with a real man, aren't you Lynn?"
"Yes, mam."
"You want to compare his cock with your little dick don't you?" Laura
asked me.
"Yes, mam," I replied. The humiliation was almost too much to bear. Laura
then slowly, very slowly removed 'Sir's' shirt, jeans and underwear. She
then took his arm and had him stand directly in front of me, completely
naked. He was truly a physical specimen. Broad chest, ripped abs,
powerful thighs, and, of course a thick, 9", perfectly shaped cock that
would be the envy of any man.
Laura then pulled down the front of my panties to expose my 'manhood'.
She pretended to carefully analyze both members, looking back and forth
from one to the other. "Hmmmm. There seems to be a bit of a difference!"
she said sarcastically. "Now Lynn, do you see why I would rather have sex
with this man than with you? Do you see how masculine he is and how
feminine you are"
"Yes, mam," I choked out the words.
"Are you happy for me and do you want this real man to screw my brains
out all night long?"
"Yes, mam," I whispered.
"I can't hear you and have you forgotten to smile? Remember our
agreement."
"Yes, mam," I said quite audibly this time and with a forced smile on my
face.
"Good," Laura then kissed the gentleman right in front of me and asked
him to help her undress, which he eagerly did. I watched as they sat on
the end of the bed not three feet in front of me making out. After about
ten minutes of this she pushed him back on the bed, got up, took my half-
aroused dick in her hand and whispered in my ear, "I want you to enjoy
this as much as I'm going to. I want you to be happy and supportive. Can
you do that for me?"
"Yes, mam," I said, now with a raging erection.
She then returned to her lover and proceeded to practically jump on his
now erect penis. I watched as he slid his beautiful member in and out of
my wife, first slowly and then more quickly. The sounds were incredible.
Her moaning, his balls slapping against her ass, the wet sounds of her
now moist pussy being penetrated by her lover.
I was erect but could do nothing about it save for dripping a lot of pre-
cum. I was incredibly aroused.
Laura gasped, "Oh Lynn, talk to me. Tell me how much you are enjoying
this. Tell me how happy you are for me."
I did all of those things and with a growing sincerity as I spoke. I was
beginning to realize that she truly needed to be penetrated to places I
had never been able to reach. Eventually they fell asleep in each others
arms while I remained awake for a time to contemplate the fact that I
truly was a submissive feminized sissy.
Thinking about it, there are an enormous number of differences between
men and women; all types of clothing from hats to shoes, makeup, hair,
jewelry, the walk, the curves, the voice, the mannerisms, likes and
dislikes of things like shopping and sports.
I had enjoyed the clothing for many years but that was pretty much the
extent of it. Now I had been “introduced” (more correctly forced) to
accept most of the other things. I now wore women’s clothes exclusively.
I always wore makeup and a wig. I had many articles of feminine jewelry,
including dangling hoop earrings. I had been taught to walk so that my
hips swayed back and forth. With the help of a strict diet, corset and
breast forms I also had developed a passable woman’s physique. I had no
hair of my own below my sideburns. The only books, magazines and
television I had been exposed to for the last 15 months were intended
for the fairer sex. I had several feminine tattoos. I had even been
heavily pressured to accept the gay lifestyle and sex with my fellow
sissies had become the only way I could obtain a release from total
chastity. There was all of this and still the threat of exposure as a
sissy to everyone I knew back home via emails sent by my wife or Lady L.
if I did not cooperate.
Yet despite all of this, thoughts of escaping and starting over still
plagued me. After all, my hair would grow back, tattoos can be removed
and nothing else of a permanent nature except for pierced ears had been
done to me... yet!.
Several in the group were intent on planning an escape by stealing a
boat and taking it somewhere. But where? And how could we steal a boat
when they were constantly under guard by the ladies and the men who Lady
L. had hired to protect her island domain? There was one small airstrip
and plane which was used infrequently by Lady L. or some of her guests
but none of us knew how to fly. Any escape attempt would certainly take
careful planning.
This never had a chance to happen however. Seeing that the group was
divided about an escape plan and refusing to wait any longer, Andrew
(her new name “Andrea”), Harry (“Vanessa”) and Frank (“Susan”) hatched a
plan on their own to escape. They had waited until Vanessa and Susan
were assigned as roommates so no one else would see them leave their
rooms. Andrea had always been in a smaller room by herself as there
were an odd number of us and Andrea certainly was the odd “man” out with
her previous disruptive behavior.
Ignoring the rest of our group, the three left their rooms just before
dawn one morning. They met at a predetermined place and raced down to
the beach near the dock. While Vanessa and Susan hid behind a beached
lifeboat, Andrea began to engage the black male guard in conversation.
Something about not being able to sleep and needing fresh air. With his
back turned, the guard did not see Vanessa and Susan approach him
silently from behind. Vanessa grabbed him around the neck and began
choking him while Andrea punched him in the stomach. He soon passed
out. Then while Susan began making certain that one of the faster boats
was fully fueled, Andrea and Vanessa prepared to cast off the lines
holding the boat against the dock.
They were not aware that there were always two guards watching the docks
overnight. Cathy, our Women’s Studies instructor and my only friend
within Lady L.’s band, who had been down the beach a short distance was
returning to the docks when she heard the noise. She immediately ran
toward the docks and upon realizing what was happening, began blowing a
whistle. When she got there the three were still fueling the boat and
trying to figure out why the key to start the engine was not where they
thought it would be. Andrea jumped off of the boat and ran at Cathy
while she was still blowing the whistle. He punched her right in the
face and she went down.
By now several other of Lady L.’s guards were racing to the docks. As
inept as their plan had been, Andrea, Vanessa and Susan were soon
grabbed by a small angry mob of island men before they even had a chance
to start the boat. They were swiftly taken back to the hotel.
Later that same day, Andrea, who was bound and gagged, was loaded on the
very same boat she tried to hijack. We watched as they took her out
toward the only other nearby island which was barely visible and much
smaller than our own. It was too far away for us to see. When the boat
returned, Andrea was not on it.
The next morning Lady L. gathered the rest of the sissies together in
the hotel meeting room. She seemed calm but the tone of her voice left
no doubt that she was furious.
“As you may know by now there was an attempt to escape the island by
some of your friends early yesterday. During this little escapade,
Cathy, one of your instructors suffered a broken jaw and had to be taken
off of the island. In addition, one of my male assistants was injured
but he will be alright, thankfully. As a result of this you will not be
seeing the leader of these three criminals again. I will not discuss her
punishment with you. Let me assure you she has been ‘dealt with’. The
other two are receiving their punishments as I speak. If any of you have
similar ideas I would highly recommend that you reconsider. For now
guards will be placed outside your rooms and a curfew will be strictly
enforced. If I should EVER even suspect something like this happening
again you will all be dealt with accordingly.” There was no mistaking
the sincerity in her words.
She continued to speak. “As these two will be under the weather for a
while, I want the rest of you to go into their room and do all of the
cleaning required. Are there any questions?”
Instinct told each of us to remain quiet. None of us wanted to be
noticed over the others by asking a question. Lady L. left the room
without saying another word.
While we were being led back to our rooms to change into our regular
maids outfits I thought of Cathy. She and I had become good friends and
I thought that if I ever needed someone inside the clan of our
Mistresses to help me in any way, including an escape attempt, she would
be the one. Now even that slim hope was gone.
We arrived in pairs outside the room of Vanessa and Susan. The first
ones to arrive whispered their guesses to each other as to what their
punishment might have been. Finally, the entire group was there. We
knew that we would make quick work of the room as they were small and
there were ten of us. We were all scared of what we might see when the
door was opened. So we were generally relieved to find that they were
not there, some expecting to see bruised and battered individuals. We
set out to do our work when Lisa was the first to see the newest plaque
above the bed:
CASTRATED,
Chose to lose my balls forever and to be feminine rather than masculine
After sharing a brief moment of shock, then sympathy, then even a little
anger toward them for wrecking any plans that the rest of us might have
had, we started again cleaning the room. I am sure I was not alone in
wondering what had happened to Andrea if Vanessa and Susan had suffered
such a fate. An unspoken feeling passed through the remainder of our
group that there could be no other path than complete acceptance of the
ladies wishes for us.
I was profoundly affected. It was one thing to be feminized and
sissified but I shuddered at the thought of having some of my more
prized parts removed. Somehow a line had been crossed.
The next several days were hard on us. In the classes we shared with
Vanessa and Susan each of us could not help but to try and grab glimpses
of their wounds. As horrible as they were we seemed to need to verify to
ourselves that this did indeed happen. There was no mistaking the stitch
marks and the dejected looks on the faces of the two.
There was a new low point here for our group of sissies as we pondered
our fates.
Then, as if in an attempt to lift our spirits, Lady L. announced that
the island would have some of it’s first visitors and that it would be
our responsibility to prepare for them.
Our hours and our ‘homework’ in Gay By Choice and several of the other
classes were increased. Emphasis on performing gay acts was the
unmistakable message. I could see where this was going. At the same time
our work as maids increased. Even more attention had to be paid to
detail. We basically learned to ‘get it right’ the first time or else.
And the threat implied by ‘Or Else’ had taken on a whole new meaning.
Soon the big day had arrived. Three boats had tied up at the dock all
together. As we had been instructed, and practiced, we each ran down to
the dock from the hotel while wearing only a bikini to welcome our new
guests. With my elbows near my waist and my arms out to my sides I did
an exaggerated feminine trot. If not for the fact that the ten of us
were all doing it (while smiling!) I would have died from the
humiliation. (Vanessa and Susan had been reassigned to kitchen duties.)
Coincidentally, there happened to be ten men all together on the boats.
We took the arms of the men and walked them back to their hotel rooms
while Lady L.’s island men brought their suitcases. After we helped them
settle in, our group of ten sissies was directed to the conference room
once again. There Lady L. explained to us that these were executives who
just happened to have unusual fantasies and fetishes and that it was
going to be our job to fulfill them. Failure in this was not an option.
Later, while the gentlemen were resting from their long journey, we
sissies changed into our French maid’s outfits. This was a time I had
been dreading even though I was well practiced for it and loved cross-
dressing in general. We were to serve the gentlemen appetizers, drinks
and dinner and do it flawlessly. Back and forth to the kitchen while
wearing our outfits, including aprons, garters, black hose, 4” high
heel pumps and, of course, the ever present smile. Soon the gentlemen
came down to the dining room and we sissies sprang into action.
I had gotten through the dinner without error but while serving desert,
I carelessly dropped a fork on the floor. Fortunately, I remembered to
keep my knees together shifting them slightly to one side when I stooped
to pick it up. I prayed that this small infraction would not bring
consequences.
We served our guests their after dinner drinks and thought we were
nearly done when Lady L. gathered us in the kitchen and said, “OK gurls,
so far so good. Now the gentlemen are gathering in a circle in the
lounge for a little review of each of you.”
A look of surprise shown on all of our faces. She continued, “You will
each walk out one at a time with your sexiest walk, stand in the center
of the circle, do a little spin for them, pausing if they want you to,
and walk back here. Does everyone understand?” It didn’t matter if we
did or not. We were on our way without ever having rehearsed this part.
One by one we each did exactly as instructed. First Lisa, then Charlene
then George (Gail) who, due to her weight drew a little good natured
laughter. By chance I would go last and Daniela was right before me.
Daniela was naturally attractive with a petite build and a pretty face.
She got several Ooohs and Ahhhhs. I knew I couldn’t match her but that I
had better try. With ten men gawking at me wearing a pretty French
maid’s outfit, I was as humiliated as I have ever been in my life, I
knew every inch of me and every movement was being scrutinized by a
group of gentlemen strangers. I was careful to take small mincing steps,
sway my hips without overdoing it, smile the brightest smile I could
muster, and as if to enhance my humiliation, I made eye contact with
each man. This required me to spin twice instead of once but I could
tell that I was attractive to several of the men. This made me proud of
myself (and glad that I was wearing my chastity cage!) As I walked back
I kept my smile but it was no longer a forced smile. And as I got to the
edge of the circle, I turned and bowed in a deep curtsey without even
knowing why. At this the men applauded. I had nailed it!
We were to learn that the men had used our display to rank us as prizes
in a poker game they were about to start. Winner got first choice,
second got second and so on.
I was changing. forced together under unbearable conditions and
unbreakable rules, we were all learning to handle it in our own way.
There seemed to be no other course than to cave in to the ladies desires
for us, desires that seemed much more clear now. This fact did not go
unnoticed by Lady L. While the men played poker, she praised us and told
us to think of ourselves as the “third” gender. Not women and certainly
not men but we were attractive to these gentlemen. As such, she
instructed, we should accept any sexual offering that they make and do
our absolute best to please them. “Pleasing a woman is beyond you” she
said, “but pleasing these men is what you have been trained to do!”
They had indeed been training and conditioning us to accept and actually
prefer same-sex relationships. Acceptance of this ‘behavior
modification’ was easier for some than for others as most of us had some
gender issue to begin with. I think I fell somewhere in the middle. It
was not going to be easy to make the transition. The ladies had
treated us as a team and set before us a team objective of becoming
feminine males. Defeat was unacceptable and victory required complete
obedience to our “coaches”.
It seemed our next competition would be to win at being the best at
pleasing the man who picked us to spend the week with.
.
I HAD changed. But subconscious doubt still lingered.
It was very late when the poker game ended. By then we had done all of
the dishes and cleaned up the hotel’s dining room. Next, and while being
pretty much exhausted, we were instructed to stand at attention in a
neat row still in our French maid’s outfits. This time it was our wives
who were telling us what to do. Lady L. was relaxing and taking it all
in from her easy chair.
As we stood, the gentlemen sat in comfortable chairs facing us. Lady
L., with some fanfare, then announced the winner of the poker game. Bob,
of course, chose Daniela who stepped forward, but was then ordered by
her wife to sit in Bob’s lap. The whole room (sissies excepted) thought
that this was a great idea, and each of us would end up doing the same
when our name was chosen. Lisa went next. I wasn’t as concerned when I
would be picked as who would pick me. There were some less than
attractive men in this group.
I was fortunate enough to be picked third and by a relatively decent
looking guy, Steve. He was taller and larger than me, I was 5’11” and
(with my dieting) 150 lbs. while Steve was around 6’2” and looked to be
slightly over 200 lbs. I went to sit on his lap and he immediately put
his hand on my thigh and began rubbing it up and down. We both smiled at
each other. He had gotten what he wanted and I had gotten what I learned
that I had wanted. My wife was very pleased. She came over to Steve and
I and gave me a kiss on the cheek. And then she gave Steve a kiss on his
cheek. “Now you’ll take good care of my little sissy this week won’t
you?” she asked. As embarrassed as I was I kept smiling.
“Oh I’ll take the best of care of her little sissy ass! Ha, Ha, Ha! You
can bet on it!” he replied.
My wife simply beamed as she then went back to stand with her
boyfriend., the same one she had had sex with while I had watched.
Mentally, I think the only way to survive a situation like this is to go
with the program. You would go crazy if you tried to fight it to say
nothing of the consequences if you did not please your new gentleman
friend and Lady L. were to find out.
Steve kept rubbing my thighs as the men’s other choices were made.
Honestly, it felt wonderful.
And last, Gail ended up with Tim who seemed just odd enough to have
thrown the poker game deliberately just to get last pick.
At that point we all stood to return to our rooms. Or that is the
gentlemen’s rooms. Already well tanned, Steve let his arm slip from my
shoulder to my waist as we walked down the hall to his hotel room.
“Thank you for picking me,” I said, thinking that this would have to be
the right thing to say.
“Oh, my pleasure, believe me it WILL be my pleasure, Ha, Ha, Ha!” was
his reply. A little tasteless, I thought, but I smiled back at him for
saying it anyway.
When we got inside his room we both sat on the bed and I nervously began
to make small talk.
“Where are you from?”
“Texas. Lynn...that is you name isn’t it?”
“Uh Huh,” I answered affirmatively.
“Just how does a pretty boy like you end up being a chick with a dick if
you don’t mind me asking?”
I did mind but pretended not to. “Well, I always had a strong urge to
get in touch with my feminine side, I guess.”
“Well in your case your feminine side seems to be about 99% of you, Ha,
Ha, Ha!”
I was getting angry at this line of questioning but could not show it.
“Lady L. and my wife have helped me along in realizing how much fun it
can be to dress up.” I thought this was the safe answer.
“Oh you’re doin’ more than dressing up my little lady! Lady L. says
you’re a little firecracker!”
I was getting even more nervous. “Well I do hope to please you, Sir.” I
was terrified of what would happen if he did not approve of me. I tried
to focus my thoughts on doing the best I could to please him.
“Well thank you mam I’m sure you will. Ha, Ha, Ha. Now why don’t you hop
out of that pretty little dress?”
I smiled at him as I took off my French maid’s outfit, including the
corset which was killing me by now. I was honestly hoping he would
prefer to nod off to sleep given the late hour, but no such luck.
As I lay on my back, wearing only makeup, a wig and my chastity cage,
Steve climbed on top of me, raised my head in his big, strong hands and
gave me a deep kiss. Our mouths opened in unison and our tongues met. My
chastity cage was becoming painful as my penis tried without success to
grow. We kissed for a long time before Steve spread my legs apart with
his.
I hadn’t thought about it this before but I was about to be “bitched,”
getting screwed in the ass for the first time. The idea frightened me in
that it would be yet one more step in my feminization which I could
never again deny happening, at least to myself.
I applied lube to my boy pussy in expectation of this moment. I felt
Steve gently place his manhood at my opening and slowly begin to enter
me. He was big but went slowly enough that I felt only pressure and not
pain. Ever so slowly... deeper... deeper... deeper inside of me as my
boy pussy slowly expanded to accommodate his erection. My own penis
hurt from the cage but I knew I was there only to please Steve. “I want
you in me,” I whispered. He held his entire 7” inside of me for what
seemed like an eternity before he started slowly rocking, out.. in...
out... in. He gradually began to pick up the pace until he was pumping
me hard and fast. I began to moan softly with pleasure until I could
tell that he was about to cum. Then my moaning became much louder.
”...Oh...Oh... Ohhhhhhhhhhh!” Squeezed inside its tiny cage, my penis,
straining to become erect, oozed out a dollop of cum at the same time
that Steve released his load.
He gave me one more lingering kiss before falling asleep still on top of
me.
The next morning Steve had gone fishing before I got up. I was thankful
for that as I was exhausted from the day, and night before.
The next couple of days we spent some time together, sunning on the
beach or going for walks. The rest of the time Steve talked to the
friends he had arrived with about their boats or other ‘manly’ things
while us sissies chatted about our new ‘boyfriends’. So this is what
being a woman is really like, I thought.
Then, each night, it was back to bed with Steve, and I didn’t get much
sleep.
By Wednesday it was time for our mid week review by Lady L.
I was shaking as Lady L. read Steve’s comments:
Lynn was a delight except for two little things, she did not anticipate
my needs (like a Scotch the way I like it after noon) as well as she
might have, and she seemed a little too nervous in bed, insisting that I
wear a rubber. If she can get over these things I would love to see her
again next time.
Lady L. summarized the review for me, “Well, you definitely have some
work to do. You should know what he wants even before HE does. Be
constantly thinking one step ahead of him. And then, you insisted he
wear a rubber!?. How could you? You should have known that our guests
are clean. If bareback is what he wants then bareback is damn well what
he better get! This is highly embarrassing for me! My friends are very
clean and don’t need to wear condoms if they don’t want to.”
I nearly broke down in tears at the tone of Lady L.’s voice knowing that
this almost certainly meant severe punishment.
“Still...” Lady L. continued, “he did say that he definitely wanted to
spent the rest of the week with you and that is a big plus. That IS
important. At least you don’t scare him away.”
Hearing this stopped a potential flood of tears on my part.
“Oh, by the way, did you curtsey for him each time you left the room?
He likes that.”
Pause. “Uhh... no,” I said meekly.
“Well next time remember that.” Then Lady L. paused. “Good and bad. I
think that indicates both a reward and punishment are due!” she
s****ered. “I think a second piercing in each ear is called for. Steve
likes lots of jewelry on his gurls. You’ll have the prettiest ears on
the island!”
My heart sank as I felt that this act of discipline would remove even
more of what little masculinity I had left. Then Lady L. surprised me
again.
“And as for your PUNISHMENT, how about a little fairy tattoo just above
your ‘cock’.”
“Oh god not another tattoo,” I thought.
I was relieved but still haunted by deeper thoughts. I had all but
given up trying to escape the island. Now I had multiple feminine
tattoos, wore only women’s clothing, was about to receive a second ear
piercing on each ear, and had made love only to men in the last 18
months. No real man could say this I thought. In addition, Steve would
be coming back before long. Mmmm...Steve. I was beginning to believe
that I could never be a man again. Could I accept this? The canings
and Ben-Gay that made my scrotum burn would be painful but temporary.
The tattoos and piercing were of a more permanent nature and would make
any hope of some day returning to manhood seem even more distant.
Still, I had to soldier on because there were punishments that were even
worse. In the back of my mind lurked the horror of castration or even
worse, if there was anything worse than that.
We had come to the island as a motley, diverse group of transgendered
males. Those of us remaining were now totally obedient, submissive,
feminized sissies, willing to do absolutely anything we were told to do.
We were physically still males but any vestige of masculinity was gone.
Each of us began to fully accept our true roll as servants to a superior
gender.
It was Saturday and Steve would be leaving the next day. I had
pleasured him in one way or another each night of his stay so far and as
a result, he asked my wife if he could have the key to my chastity cage
for one day. She agreed on the condition that any release that I have
be done in a way that would humiliate me. She explained how that helps
me maintain my submissiveness. She agreed to his offer knowing that I
had indeed pleasured him each night as she had the videos taken by the
**********era in Steve’s room as proof. Any images of Steve that were
identifiable were destroyed by agreement with Lady L. Any videos where I
was identifiable were copied, cataloged and saved in a secure place.
As a surprise, Steve asked me if I wanted to go up in the plane with
him. I was overjoyed. This meant that he must have approved of me. I
quickly agreed.
He knew how to fly too! There was so much he could do that I could not.
I even asked him about the controls, perhaps subconsciously thinking
that I could fly off of the island. He pointed to this dial and that
switch while rattling off some technical jargon and I quickly gave up
that idea.
He took me high enough to see a couple of other small islands.
“I’m not sure but I don’t think this looks like the Caribbean,” I said.
“Ha, Ha, Ha,” Steve laughed. “Who told you that? We’re a little north
of Madagascar!”
I was shocked. The sissies had been lied to since the beginning.
Andrea never had a chance to escape from here.
The next day he offered to take me out on his boat. The only condition
was that I wear the bikini he saw me in the first day he arrived and,
again, I readily agreed. He took us out several miles before shutting
off the engine.
Suddenly a thought came over me. A terrifying thought. This might be
the only chance I would ever have to leave the island. While Steve was
concentrating on steering the boat out to sea, I had noticed a boat hook
attached to the side of the boat by clips. It was simply a rod about
six feet long with a hook at the end for grabbing things out of the
water. I quietly removed it from its fasteners. Gripping it like a
long baseball bat I would be able to swing it freely and certainly be
able to at least disable Steve. I hesitated just a moment. I couldn’t
do it! I held the boat hook poised to swing but I could not do it! I
quickly lowered it when Steve began to turn around. I held the end of
the pole in my hands and began sliding one hand up and down the last
foot of its length, stroking it gently.
I smiled at Steve as I did this and a moment later he caught my idea and
smiled back at me. He then stopped the engine, took me by the hand and
led me to the stern of the boat where he sat on the cushioned seats
there. He then took a life preserver and set it on the deck between his
knees. I understood what he wanted. Kneeling on the life preserver I
began to slide his bathing suit down his legs then lifting them so I
could remove it completely. I noticed for the first time the amount of
hair on his legs... and his arms. It was thick yet curly and soft. I
ran my hands through it as he had run his hands over my hairless thighs
as I sat in his lap after the poker game. I could not help noticing the
contrast between his arms and legs and mine. His were the arms and legs
of a real man. I had only perfectly smooth skin, feminine skin,
highlighted by the fact that I was in a bikini. No REAL man would EVER
be in the position I was in wearing what I was wearing, doing what I was
about to do. At no other time in my life was I as aware of who I was
than at that moment.
I began gently caressing his penis. My mind began to wander. When he
had reached his full erect length I began kissing it. I wanted to make
love to it. I gently cupped his balls in one hand while I lightly
grasped his shaft in the other. I kissed the entire length. I sucked
on his balls until he started to groan. I licked around his penis. I
licked under it. I ran my tongue slowly up its length, then down, then
up again pausing to put my lips around his corona. Sliding his
beautiful penis slowly into my mouth inch by delicious inch until my
nose was nestled in his light brown pubic hair. His penis was touching
the back of my throat but I was able to suppress the gag reflex because
I had been trained to do so. I let my mouth linger there as Steve began
to groan louder. I wanted to please him. I wanted his penis to feel
the warmth of my moist throat. I wanted to use every lesson I had
learned about performing the perfect blowjob. Excruciatingly slowly I
brought my lips up the length of his shaft. I paused with my lips again
caressing his glans and my tongue flicking the underside of its head.
Steve grabbed my head and began to hump my face. All that mattered to
me was that I pleasure him as he has never been pleasured before.
Nothing else mattered to me. I was going to make him experience ecstasy.
From the volume of cum I swallowed I think he came pretty close.
A minute or so later Steve finally caught his breath and then reached
down into the pocket of his bathing suit and produced the key to my
chastity cage. My eyes widened as he unlocked the wretched device and
my cock sprung free. That felt wonderful but it got even better as
Steve put his large hand around my shaft and gently squeezed. I began
to raise my hips to gain some friction but Steve told me to stop and
remain motionless. It was a heavenly torture. I wanted desperately to
reach an orgasm but could not. One minute. Two minutes! Then Steve
told me to repeat what he was going to tell me to say.
I think it went something like this:
“Mr. Steve Sir, for you I promise that I will be YOUR gurl whenever you
come back to the island.
For myself I promise that I will work to become more feminine every day.
For my Mistress wife Laura, I promise to let her have sex with whoever
she pleases.
For Lady L. I promise to work as hard as I can to please her in every
way possible.
For all other ladies everywhere I promise that I will never think of
women in a sexual way again.
“Ha, Ha, Ha!” Steve laughed at that last one.
He then stroked my penis and I quickly ejaculated with my cum running
down on his hand. He held that hand up to my mouth and I licked it
clean. Then he locked me up once again in my chastity cage.
In his final comment, Steve said, “I am going to tell Lady L. exactly
what you just said. After all, this will give everybody just what they
want!”
“Yes, Sir,” I replied with my mind gone blank.
Steve let me steer the boat back to the island and over the drone of the
engines he said, “Hey, let’s get that down in writing! And you’ll
agree to sign it or this only key to your cock cage goes overboard. And
there is no locksmith on the island. Ha, Ha, Ha, Ha!”
Why he had chosen to be so cruel after what I had done for him I didn’t
know. I didn’t care.
And with that my fate was sealed.
Shortly after the gentlemen had left the island and I had indeed signed
a letter acknowledging what I had stated on the boat, Lady L. gave us
our final reviews. They were generally excellent with mine ranking among
the best and she was beaming with pride. She then happily announced, “We
are going to hold a graduation ceremony for you gurls! Instead of a cap
and gown you will get to wear an EVENING gown and be recognized in front
of all of the ladies and men on the island!”
The actual ceremony turned out to be similar to our parade in front of
the gentlemen in our French maid’s uniforms, except we were now decked
out in beautiful evening gowns in front of perhaps fifty ladies and men.
This time it was easier for me as I dreamed how good I must look in the
silky fabric, beautiful jewelry and perfect make-up.
Following the ceremony I saw my wife, Laura, leave TWO men to come over
to congratulate me. “I’m so proud of you for following this through!”
Laura exclaimed. As if I had a choice.
“I hadn’t realized by your cross-dressing you were screaming out to me
that you really wanted to be a woman! You wanted to be the person that
is caring, devoted, submissive, obedient and pretty to look at all at
the same time! When I realized that I had missed all of the signals I
knew I had to help you to become what you really were all the time!
You’ve really earned this!” With that, she kissed me on the cheek and
went back to her boyfriends. I couldn’t tell whether she was mocking me
or being genuinely honest.
It didn’t matter.
This IS who I am now. If I ever was a man I’m not now so I had better
learn to make the best of it. I really DO want to please the ladies on
the island and I know that if I try hard enough I will be able to.
Above all of the promises I had made to others, I decided to promise to
MYSELF that I would do the best job I knew how to as maid, servant,
danseur or anything else Lady L. or Mistress Laura wanted of me.
Manhood had slipped far away. Over the last two years in which I had
experienced only feminine things I had forgotten who was on which
professional sports team and even the names of some of the teams. Such a
lack of knowledge would have been more embarrassing if I had anyone to
carry on a masculine conversation with but I did not. The occasional
visits by men to the island did not help me relate to the outside world
as they never talked "guy" stuff with us sissies. We were left to chat
amongst ourselves about the latest fashions, fabrics, and famous
females.
Could I ever be a man again? I tried to put this question out of my
mind as it wouldn't matter under the current circumstances. And it
didn't look like the current circumstances were going to change. All of
us sissies were kept in chastity for long periods and the only release
we were allowed was with men visiting the island or with each other.
Before I had arrived on the island being forced into this type of
behavior would have seemed impossible but sex is a powerful motivator
and the ladies knew it. They had provided the physical and mental
punishment and scaled it up as high as necessary to get each of us to do
what they desired. Eventually, each of us succumbed to their superior
power and accepted a gay lifestyle. What had seemed so unnatural at
first now seemed erotic. Ahh the power of an "education" at the
W.I.T.C.H. Institute.
Over the next two months a few men visited the island. There were never
enough to go around for each of the twelve of us sissies remaining here.
But this was a good thing for the visiting men as they then got to
choose between us. Daniela was chosen most frequently, every time in
fact. We all knew that she was the most attractive and passed as being a
real female quite easily. I was afraid to admit it to myself but this
was making me jealous of her. I was often left to my maid duties while
Daniela was being wined and dined by one of the male visitors. It was
particularly frustrating to have to make the bed that she and her male
friend would soon sleep in or had just slept in. But I did it just the
same and I did it with a smile on my face as was required of me.
Perhaps this is why I was so happy when, one day three men arrived at
the island and I was chosen by the one named John. After all, the
competition was tough. Each of us sissies greeted them in the usual
way, by running down to the beach in our bikinis and begging to be
chosen as their consort for the week.
I was hoping that John chose me because he liked the way I looked. By
dieting I had lost even more weight and had gotten a nearly perfect tan
by making sure that the strings to my bikini were in exactly the same
place each of the times I was allowed to lie on the beach in the sun. I
had been paying much more attention to such things recently because my
wife encouraged it and these were important to a "gurl" trying to
attract men. After all, this was the only way any of us would be
granted a sexual release.
I felt rewarded for all my hard work that night when I saw John naked
for the first time. When erect, his cock was a full 10" long! It was as
long as any of the hundreds of cocks I had seen in photographs during my
classes. I could finally understand why women were so attracted to such
a display of manhood. After having seen so many naked males up close,
VERY close, I was beginning to appreciate certain qualities in a cock.
Length was definitely one of them and John's was, simply beautiful on
that score. A cock had become my main source of physical pleasure and I
had learned to appreciate the opportunity to please them with my lips
and tongue. This is why John was such a special treat for me.
On John's first night, while I was on my knees pleasing him with my
mouth, I looked up into his eyes and found him looking down into mine.
No words were spoken and none were needed. At that moment the dramatic
difference in our status was crystal clear, and seemed so right. This
wonderful specimen of manhood also reinforced my acceptance of what the
ladies had taught me, that some of us were just meant to be "real men"
and some of us sissies. It made perfect sense that he is what he is and
I am what I am.
I later learned that John was not only talented in the bedroom, but had
made a considerable sum developing a popular app for smart phones. It
made me doubly proud that he had chosen ME to be submissive to him. He
had proven himself to be a real man in the business world as well.
Something I had never quite been able to accomplish.
And it is a good thing John had a lot of money. You seemed to need a
considerable amount to visit this island because you needed a boat or
plane to get there, to say nothing of the fee that Lady L. must be
charging for the accommodations and the services of us sissies.
Naturally, we never saw a penny of those fees and there was no place to
spend them if we did.
My week with John seemed to fly by and my only regret was that he did
not want to kiss me. I had learned that not wanting to kiss a feminine
male is just a peculiarity that some men have.
That wonderful week was followed by a less auspicious one. My wife Laura
had decided to make a change.
"Lynn, I was so happy that you really got to hit if off with John. It
makes me feel so good that you have found yourself, that you now know
who you really are. There is no shame in being a complete sissy. It's
wonderful that you are able to make love to only men now and that you
accept that you are a total submissive to both women and men."
The way she had just blurted these thoughts out shocked me.
"But," she continued, "it is now time for me to find MYSELF. I have had
divorce papers drawn up so that we can each follow our own destinies.
Our paths have always been separate ones, you an effeminate submissive
sissy wanting to be completely dominated, and me, an attractive,
dominant woman desiring to make her mark on the world!"
I was blown away. "B-b-but you're dominant and I'm submissive. You said
so. So why can't you just dominate me while we stay married?"
"Lynn, I HAVE dominated you, TOTALLY. And now it's time for me to move
on. Look at you in you're pretty little skirt and blouse. This is your
future. But there is no room for that in my future. I am going to want
REAL men. In fact, Marc and Darius are going back to the States with
me."
I knew, even if I never admitted it to myself, that she had fallen in
love with one or both of these other men, but, despite this, I could
still never envision her leaving me. "B-b-but Laura, I thought you still
loved me," I said, starting to cry.
"Oh, but I do! That's exactly why I am doing this. I hope you appreciate
ALL I have done for you... letting you wear women's clothes, encouraging
you to become more and more feminine, helping you become gay, just like
you wanted!"
Did I want that? Or was it forced on me? I could not deny that I now
enjoyed having sex with other men and that I loved women's clothes. I
couldn't seem to find a hole in her argument. "But I don't want you to
leave!" was all I could think to say.
"Lynn, dear Lynn, you'll always have the memories of me and I will leave
you with pictures of me and I will keep pictures of you, recent
pictures." She stifled a laugh. "Don't you want me to be happy? As happy
as I've made you?"
Thinking as quickly as I could, "Of course, but I won't be happy without
you!"
"Now Lynn, you must be realistic. I would only be in the way of you and
your lovers. You have a wonderful job here and what about your many
friends, all of your 'boyfriends'? It IS the way it has to be Lynn."
I was out of arguments. What could a submissive male say to change the
mind of a dominant woman? Nothing I could think of.
"Here Lynn, sign this, here and here" she said as she pointed to the
divorce decree.
I tried to hold back a flood of tears unsuccessfully. "B-b-but what
about our house back home? The one we bought together?" As though
anything back home would do me any good now.
"I'll keep the house and whatever else we owned. You won't be needing
anything you don't already have here. So it only makes sense that I have
it. In fact I think I'll put a big picture of you as you are now over
the fireplace. It will help me remember you as the sweet generous little
sissy you are."
"Won't I ever see you again!?" my desperation growing..
"Well, as happy as you are here, you have no reason to leave the island.
Besides, I threw out all of your male clothing back home. I knew
you'd never need them again and they won't fit Marc or Darius, you're
smaller than they are." Again she stifled a chuckle. "Now sign unless
you want to go discuss this further with Lady L.".
I could not refute anything she had said. I could not go back to my old
life and I was not about to lose all of the goodwill I had built up with
Lady L. over an argument I could not win. With tears flowing freely, I
signed.
One week later, at the 'urging' of Lady L., I reluctantly said my
farewells to Laura, Marc and Darius as they left on the nicest boat
still at the dock. "Goodbye, Mistress Laura, I love you and thank you
for everything you have done for me." I had to say this even though I
knew that this could be my final admission that I would never leave this
island.
As the boat slowly pulled away from the dock the image of Laura's face,
as happy as I had ever seen her, was burned in my mind.
It had hit me like a ton of bricks as I knew deep down that there was no
way I could ever go back to living anywhere but here with anyone but
those that already lived here or came to the island. I loved Laura and
hated her at the same time for leaving me.
<<<<<<<<<<<>>>>>>>>>>
Several days later, while Lisa (Edward) and I were cleaning one of the
hotel rooms, the subject of Andrea had come up. "What do you think ever
happened to her?"
"I don't know but I hate to think about it."
Just then Lady L. and Cathy entered the room. Lady L. spoke, "Oh hello
gurls. I just wanted you to know that Cathy was back. She's fully
recovered from that beating she took when Andrea tried to escape. I
overheard you and funny that you should be asking about Andrea. Do you
want to see her? I think she might enjoy it actually."
Lisa and I looked at each other, speechless.
"Well I'll arrange something for all you gurls. That will satisfy your
curiosity. In the mean time, how about a welcome back for Cathy?" asked
Lady L.
Both Lisa and I gave her an enthusiastic welcome at the same time. She
was indeed welcome as she was not only the most friendly of Lady L.'s
assistants but she was also the most beautiful.
The following Sunday, when all of the work and class schedules of the
sissies allowed it, we gathered together at the dock. (I say Sunday
because that's what day I thought it was. Actually, each day, each week
and each month blended into the next so I really didn't know when it
was.) The sissies were tied to each other with soft but sturdy pink
handcuffs and helped onto the largest of the boats by three of Lady L.'s
male assistants.. By this time thoughts of escape were gone but Lady L.
was never again going to risk it.
As this was one of the slowest boats it took us quite a while to reach
the smaller island where we had indeed guessed Andrea had been taken.
All of us sissies were sharing a nervous curiosity as we were helped
from the boat by the three male assistants.
"Follow me gurls." Lady L. said as she walked from the beach to a narrow
trail in the underbrush. About 100 meters in, we came to a clearing
with a small hut in the center.
Lady L. went into the hut and soon emerged at the doorway to announce
"Gurls, the Queen of the island!" Holding the woman's hand in the air,
Lady L. led Andrea in to a spot in front of us.
Her face, although made up in an exaggerated fashion with eye shadow,
mascara and lip stick, left no doubt that this was indeed Andrea. From
the neck down, however, she was unrecognizable as Andrea. She had a
beaded necklace hanging over small uncovered breasts, a very narrow
waist supporting a grass skirt, and bracelets all up and down her arms.
Her own long, uncombed hair was topped off with a gaudy tiara.
None of us sissies could speak as our mouths just hung open is
disbelief. Lady L. broke the silence, "Sissies, curtsey to your Queen!"
The authority of Lady L. was all that was needed for us to obey. We all
did as directed although in a very unorganized manner.
"I am your Queen and you are my subjects" 'Queen' Andrea had spoken.
With the sight before us we didn't know whether to laugh or just try to
remain silent. Between us there was a little of each.
Lady L. again spoke, "Your Majesty, why don't you show your subjects the
changes that have made you even more beautiful now?"
With that, Andrea removed her grass skirt and revealed a surprisingly
attractive hourglass figure. Except for her jewelry she was completely
naked as she did a slow turn before us.
The sissies still had trouble speaking as we each took in this image. We
began murmuring amongst ourselves. "She must have been put on a large
dose of female hormones to develop her breasts and expand her hips like
that" said one. "There has definitely been some serious corset training
too" said another. With her private area smoothly shaved it was obvious
too, that her Prince Albert piercing was still in place. She clearly
would not, could not use her male parts for sex of any kind.
Annoyed with the whispering of the sissies, Andrea declared "Silence! I
am your Queen and you are my subjects!"
Lady L. turned to us, "Gurls...?" hinting for us to do something.
Gail caught what Lady L. had implied and quickly curtsied with the rest
of us following. Lady L. then led 'Queen' Andrea back to her hut. "I am
your Queen...."
"Susan and Vanessa" Lady L. said in a matter-of-fact way, "I want you to
stay with your Queen. She will appreciate the company and I think you
will too." Susan and Vanessa had been gelded as punishment for their
roles in Andrea's failed escape plot. With hopes that this might provide
at least a bit of the freedom from the W.I.T.C.H. institute that they
had learned to hate, they willingly agreed. They had never been great
fans of having to meet and entertain any men that visited our island to
say nothing of losing their manhood there.
On the boat headed back to that island we were still somewhat in
disbelief. Relieved that nothing worse had happened to Andrea and yet
surprised at what HAD happened. Clearly some type of 'medication' had
been part of her punishment.
"You know," said Charlene jokingly and perhaps with a hint of jealousy,
"she's smokin' hot!"
"She's smokin' something!" I chimed in.
We all laughed, including Lady L.
<<<<<<<<<>>>>>>>>>>
The next week was relatively uneventful and we all did our maid duties
and attended our classes as usual. There was one change, however. Susan
and Vanessa had been our main chefs and were responsible for preparing
most of the meals. Without them the rest of us had to take on a class
in cooking. Mistress Noreen, herself an accomplished cook, took on the
task of teaching us. The class was pleasant enough except for the
Mistress's habit of continually reminding all of us to keep our knees
together We each wore the standard short, pleated plaid skirt for class
and often one or more of us would fall into the old male habit of
letting our knees drift apart a few inches.
"Knees together gurls!" she would say whenever she noticed. Over time
this began to bring a smile to my face as I dutifully obeyed. I found
this class a pleasant change from some of the other more mundane tasks
us sissies were required to perform. It meant that I was learning yet
one more traditionally feminine skill. Complete feminization is a big
job but I was well on my way.
Life on the island was beginning to get more interesting. One day Beth
and Irene (formerly Bradley and Irv) made a surprise announcement that
they were going to get married. Lady L. had granted them permission to
become 'husband' and wife. Which would be which no one seemed to care
but we were all genuinely happy for them.
Reflecting, I guess it was only natural as they had been through so much
together and had been taught to accept a same-sex lifestyle as we all
had.
Perhaps most surprising was the fact that Lady L. was going to allow
them to return to the States to live as domestic partners. Since this
turn of events had fulfilled all of the goals the spouses of these two
had set for them, Lady L. was very confident that her work on them was
now complete.
Was this a course I too should pursue? What had been my wife's goals for
ME? She had left the island telling me that I had already achieved
them.
The remaining island sissies, including myself, were truly happy for the
lucky couple. A ceremony and celebration were in order. To make it
legal, their wives had also made them sign divorce papers and Lady L.
had arranged that they would be married by the 'captain' of the next
vessel that would visit the island. We were told that such a ship would
be arriving in exactly one week. That did not give us much time to plan
the ceremony or make wedding gowns for them. They would, however, be
wearing beautiful matching white dresses. The variety of women's
clothing that Lady L. had made available to the sissies never ceased to
amaze me. I was never sure where it had come from. Perhaps delivered
by one of her visiting gentlemen friends in payment for a week of
pleasure?
With such a short time frame there wasn't a moment to lose, what with
our routine maid's work and classes. (Although Lady L. did suspend
classes except for Cooking in which we quickly learned how to make a
beautiful wedding cake.) Many of our experiences in feminization were
paying off for the first time. Collecting and arranging flowers, sewing
dresses, planning and cooking the reception dinner, helping each other
get our nails and hair done. It is amazing what the feminine work ethic
can accomplish when tasked with such an enjoyable event.
When the big day arrived I was tired but happy that we had been able to
bring it all together. There was not a large crowd sitting in
attendance as all of us sissies were standing up as bridesmaids for the
happy couple. We had argued about what our dresses should look like but
finally decided on a light blue satin dress with a sweetheart neckline
and cap sleeves. It was gathered on one side at the waist and had a
back zipper and small slit at the bottom in back. I loved it. As long
as I could remember I enjoyed cross-dressing but this was a most
wonderful feeling looking as feminine as I did.
It was a beautiful ceremony and the reception was lovely. I got to
dance with the 'captain' and several of the other sissies. All in all I
had an amazing time. It made me reassess how nice it felt to be
feminine instead of masculine. The day that Beth and Irene left for
home and a honeymoon, I actually became jealous of them. Having just
finished the now requisite two months in chastity I begged Charlene to
make love to me. She was just as anxious as I and we ended up spending
an entire night kissing, caressing and having oral and anal sex.
After having spent over two years without so much as touching a woman it
was much easier now to accept that I would probably never have a
heterosexual experience again. In all of this time women physically
would have nothing to do with us sissies and yet us sissies (when not in
chastity) were always available to each other. We looked feminine. We
acted feminine. The transition to homosexuality had become fairly easy.
<<<<<<<<>>>>>>>>
There was even more news the following week. Lady L. had informed us
that we were going to have some unusual guests that weekend. These
guests were going to be ladies. Real ladies. Not only that, they were
the spouses of other unsuspecting males like us island sissies. They
were going to be shown the facilities of the island and the curriculum
of the training classes. It was an important step in convincing the
ladies that this was indeed what their spouses needed to adjust
whichever of their behaviors that was inappropriate or not to their
wife's liking.
As one would expect, Lady L. gave us a stern warning about being on our
absolute best behavior while the guests were here. She strongly hinted
at the fact that 'Queen" Andrea might need a couple of 'princesses' on
her island. The implication was crystal clear. Any error on the part of
a sissy could result in a fate like that of Vanessa and Susan. We, in
fact, were going to be instrumental in convincing the ladies that their
husbands NEEDED to be sissies.
The big day soon arrived. We island sissies were already at the dock
waving when the boat pulled up. I heard one of the ladies say to
another "Why are there girls here to meet us? I thought we were going to
see some sissified men!" The lady she had spoken to turned and whispered
something in her ear and she froze, mouth open, staring at us.
"Wonderful!" she said as she began to laugh.
The ladies were all types, young, middle-aged, thin and fashionable,
somewhat over- weight. For some reason the heaviest one instantly took
a liking to me. Perhaps I looked like her husband. In any event, she
was also the jolliest and most talkative one.
"Oh sweetie, we're going to get along just fine! I'm pickin' you! I
hope none of you other ladies mind!"
The other ladies seemed to be so delighted with the whole scene at the
dock that they had no trouble picking one of the other sissies for
themselves and leaving Mistress Marge to me. ('Large Marge' I silently
thought but would never say out loud.)
The sissies took the lady's luggage to their rooms and began to explain
where everything was, much the same as we had done when men visited the
island. When they were settled in Lady L. had the group convene in the
hotel's conference room to go over their stay in more detail, and to
insist that there be no sex with any of the sissies. None of the women
saw any problem with that. Two of the sissies, including Lisa, were
somewhat disappointed, as they had been chosen by a couple of foxes.
Most of the time during the week the ladies spent in meetings with Lady
L. and her assistants, going over the fine points of what would happen
to their spouses and what specific training they would need. Us sissies
were not allowed in those meetings.
Each day the sissies would e***** their respective woman to breakfast,
lunch and dinner. Between meals were their meetings and tours of the
island's limited facilities. Over the several days that they were
there, the ladies got to know their personal sissy fairly well.
Marge could not seem to stop talking about my heart, rose and butterfly
tattoos, pierced ears and feminine mannerisms. She seemed delighted with
me. Of course, the rule that I had to constantly smile did not give away
my true feelings. It didn't matter. The potential consequences from
Lady L. prevented me from showing Marge anything but the best of times.
A special dinner was arranged for the ladies final night on the island.
I had to work double duty that night as both chef before dinner and
waitress after.
During desert, Lady L. stood up and made an announcement.
"I am proud to let you know that each of you lovely ladies has chosen to
allow us to train your spouse in the ways of a true sissy. You have
seen the results of our previous work and you have all told me how
magnificent it would be if all insubordinate males could be like this. I
promise you we will do our best to make your spouses the feminized,
obedient, submissive sissies that they secretly have always wanted or
deserved to be!
"And now, after you finish dessert, as a special treat we will have our
current sissies dress however you would like them to dress and do
whatever you would like them to do! They are yours to command. Use your
imaginations ladies! "
Charlene (formerly Charlie) and I glanced at each other with the 'what
just happened here' look on each of our faces. But all of the time
smiling.
Much to my chagrin, Marge had me dress in a corset, garter, panties,
stockings and 5" high heels, all black. She also insisted on the blonde
wig and bright red lipstick, which were very unusual for me. The rest of
my make-up, well you can probably guess.
The sissies adjourned to dress and waited until the last of us was ready
before we all rejoined the ladies. We had to assist Daniela and rush her
along as her owner for the week had insisted she wear a full length
dress and be made up immaculately, which, of course, she was when we
were done with her. (Note: I think I can speak for all of us sissies
when I confess that there is no better feeling than when applying eye
shadow, mascara, eyeliner, blush and lipstick properly.)
The ladies were so taken by the sight of us when we entered the room
that they all stood up in unison, applauding and shouting cat calls as
Lady L. introduced us individually.
I, wearing less than any of the others, was particularly embarrassed at
the volume of the cheers. We joined the lady who had chosen us and began
to mingle in pairs around the room.
We ran into Daniela and her beautiful Mistress first. Obviously trying
to learn more about the nature of Lady L.'s plan, Daniela's Mistress
asked me, "Do you enjoy being feminine?"
"Oh yes!"
"Could you ever imagine yourself as a man again?"
"No, not really."
"Are you gay? Were you gay when you started here?"
"I was straight, but, well, I only sleep with men now, but... "
"Then you are GAY, little one, don't be ashamed of it. I'm hoping to
convert my husband. Maybe you two could get together some day. I think
you would like him and I KNOW he would like you!" she giggled and I was
becoming more and more humiliated.
"Well I must go talk to some of the others. This is such a fascinating
group. I simply love the work they do here. Bye for now."
"Bye." I curtsied out of habit as she left and she smiled a broad smile.
Marge then looked down at my waist. "Take your panties off."
"But, no one else...uh.. of course Mistress Margaret!" I did as she
directed.
"Well son of a gun! I THOUGHT you were wearing a chastity cage. Don't
want that little mouse escaping now, do we? I was wondering why she
called you 'little one'. Now I know!" She laughed loudly at my obvious
embarrassment and since my predicament called for it, I laughed with
her.
"Hey! I have an idea. I be back in a second," said Marge. I had no
idea what she was up to but for a minute I stood there alone wearing
even less than I had entered the room with. I noticed that a couple of
the ladies were involved in other conversations but were also eyeing me
up and down. How humiliating.
Marge returned with a length of string and, surprisingly, the key to my
chastity cage which she promptly unlocked and put in her purse. Saying
nothing, she then tied the string firmly around my 'manhood'.
"There!" she remarked. "Now let's go mingle some more."
With that she wrapped the string several times around her pudgy hand,
grabbed my penis and began to walk over to the largest group of guests
she saw. With my 5" heels and being tugged by my penis I was forced to
take small, quick, mincing steps to keep up.
Marge interrupted the conversation of the other group, "Hey gang, look
what I've got!"
She pulled me into the center of the group again by my cock. "I think I
want my husband to look like this. Hah hah hah!"
I kept smiling but was trying to get Lady L.'s attention hoping she
would make this humiliation stop. Lady L. narrowed her eyes and gave me
an evil smile. After all, we were there to please the guests.
Letting the string unwind from her hand, Mistress Margaret (as she now
insisted that I call her) tugged me again to another pair of ladies with
their sissies. "Hello ladies, and sissies" she said, less imposingly
this time. Mistress Lena, one of the ones who had been staring at me
earlier, began to look at me closely again. She looked first at the
rose tattoo on my hairless chest, stroking it gently. Then at the
butterfly tattoo in the center of my back just below my neck. Also
touching it softly as though she wanted to make it come alive. Finally
she perused the small rainbow very low on my back. "The colors will
probably fade over time" she said, "but the idea behind this one will
last forever".
"Fine work" she said. Could you lift your leg with the heart tattoo on
it?" asked Mistress Lena. I instantly obliged, bracing myself on Lisa's
shoulder so as not to fall. She bent slightly to look closely at it.
"Umm." She uttered. Then Mistress Lena knelt down to look at the last
tattoo I had received, that of a fairy just above my penis.
"Such fine hair... A beautiful face... and delicate wings. Kudos to
Lady L. for having the nasty hair removed so that we can see your pretty
fairy" Mistress Lena spent what seemed like an eternity analyzing my
fairy. She cupped my balls and moved so close to my tattoo that I could
feel her breath on my now erect penis. "You are a fine example of what
males can become with the proper education." She seemed to be intent on
perfecting my humiliation and she was certainly succeeding.
Mistress Lena was beautiful, gentle, a real woman's woman, and yet she
terrified me.
Then her round of questioning began:
"Were you happy with yourself as a man?"
"Not really, Mistress, I used to cross-dr..." She interrupted before I
could finish.
"Are you glad your spouse brought you here?"
"Oh yes Mistress."
"Do you enjoy being so feminine?"
"Yes, Mistress."
She took one of my hands and placed it on her breast much to the chagrin
of Mistress Margaret who began to pull on the string around my cock as
if to pull me away from Mistress Lena. Then Mistress Lena leaned over to
whisper in my ear.
"Do you prefer women or effeminate males?" Under these circumstances
this was one tough question!
"Ahhh..." I knew how I had to answer even though she was almost offering
herself to me. "ah... males" I said under my breath.
"I want you to show me? Undress this nice sissy here and suck his..
excuse me, HER cock!"
At my hesitation she became insistent, "NOW!"
Lisa mockingly reminded me to smile.
I knelt down and reached around Lisa's waist to unzip her pencil skirt
which zipped in the back. It fell to her ankles. Then I slowly slipped
her pantyhose down. Then her lace panties. Darn the luck! She also was
wearing a chastity cage! Not a problem as Lisa's wife had rushed over
with a key. And she was followed by the entire group of ladies. Before
you could say Jack Robinson, her cage was also in Lady Margaret's purse.
I had just been intoxicatingly close to an absolutely beautiful woman.
Despite what I had said out loud, I could not help to wonder what it
would have been like to be with a woman like this. Everyone on the
island knew there would never be a chance of that happening. Instead, I
now had a golden opportunity to please another male with my mouth. And
to the oohs and aahs of the ladies surrounding us, I kissed her penis
and placed my moist lips around it as I had done many times with many
males. I put no less effort into pleasing Lisa than anyone I had gone
down on. I was trained how to do it. It had been burned into my mind
that I must try to make this the best experience possible for my lover.
The only difference this time was that there were approximately a dozen
beautiful women up close watching me. I had been conditioned to enjoy
what I was doing despite the fact that this was possibly the most
degrading thing I had ever done. The ladies saw that I was not forced
to do this, that I was not only doing it willingly, but that I was
showing an extraordinary amount of enthusiasm for it. Lady L. would be
proud of me for providing such a convincing display for her potential
clients. The heightened sense of awareness. The TOTAL humiliation. I
DID enjoy it. I could not see which one of the ladies said it, but she
dubbed me 'Best Cock Sucker of the Week' and I heard the other ladies
chuckling in agreement.
I think it was Mistress Lena that told me to swallow it all when Lisa
ejaculated but that was what I had already been trained to do. My mind
started to wander with lust as I tasted the slippery cum. I so wanted to
enjoy this perfect total humiliation that I let the sperm and semen rest
for a time on my tongue in order to savor it's taste and give the ladies
a further visual treat.
Refusing to continue to share me with the entire group, Mistress
Margaret gave one tug on the string tied to my dick which I could not
ignore. She seemed jealous that she had not taken me to this level of
embarrassment first.
"Take off the rest of your things, except the high heels" she ordered.
"Huh?" I wasn't sure of her intent.
"You heard me. Get naked right now! I want to show off the best cock
sucker ever!" she said. Then whispering in my ear so only I could hear,
"Don't you ever embarrass me by letting some other woman tell you what
to do! I am in charge of you now!" With that, she slapped me hard in
the face. It hurt a lot. The other ladies were watching anxiously to
see what my reaction to the slap would be. I knew Lady L. would be
watching closely as well. They all laughed and seemed delighted when
all I did was let out a meek "Thank you Mistress Margaret".
Nude except for the high heels, I had to try to keep up with Mistress
Margaret using tiny delicate steps as she began to stride around the
room pulling the string tied to my penis. It was almost too much even
for me. Somehow, but I did not know how, I had turned out to be the
center of attention that evening. First, as the most scantily clad one
in the room I had been questioned about my lack of virility. Then me and
my tattoos were studied closely by one woman followed by my performance
of a homosexual act witnessed by all of these beautiful women. And now
all eyes seemed to remain on me as I scurried around the room naked
being pulled on a leash by the least attractive woman there. Regardless
of the fact that I thought she was the ugliest of our lady visitors, I
knew I was her submissive for as long as she wanted me to be and I would
have to act accordingly or risk severe punishment.
With all of this going on I began to drift into sub-space, that place
where all of your fears of embarrassment disappear. My mind, no longer
able to accept such abject humiliation, had begun to welcome it as the
only defense left. My smile returned and I began to wriggle my hips in
an exaggerated feminine movement to provide the maximum entertainment
value for the ladies. Sub-space. A level of submission where you begin
to feel a serenity with the fact that you have no control and that you
are actually intoxicated with the humiliation surrounding you. A rapture
of sorts. Finding pride in being SO degraded that your status as the
lowliest, obedient submissive ever is etched in your mind. A happiness
of pleasing others by having them see you squirm in embarrassment. I
wanted to let Lady L. know that I had joined her in trying to show just
how far you could go with a submissive male.
Our little party went on for another two hours before the ladies finally
began to run out of ideas on how me and the other sissies could serve
and perform for them. At last Lady L. got everyone's attention.
"Ladies, ladies. Grab a glass. I want to propose a toast!" When all
of the Mistress's glasses had been filled by their respective feminized
servant, she continued. "To SISSIES! May they continue to grow in
numbers and serve their Mistresses as our pretty slaves have done here
tonight!"
A loud cheer rose from all of the ladies as each took a swig of their
beverage. Looking around the room I noticed that each and every one of
the sissies was also sporting a smile. Was it that we had pleased Lady
L. and, thus avoided punishment or were we glad to have served and
committed ourselves to join an important cause?
<<<>>>
Days later, as the husbands of the Mistresses we had entertained that
night began to arrive, I smiled. I knew what they were in for.
As she had done with my group, Lady L. gathered the men in the hotel's
conference room and shocked them with the REAL reason they were there.
Not to retire wealthy to this island, but to become totally feminized
and learn how to serve women. Each of the remaining eight of us current
sissies were waiting outside the conference room wearing our French
Maid's outfits and at just the right moment, Lady L. signaled to us to
enter the room. The look on their faces was priceless.
"Boys, this is what you will become after you have received your
training at the Institute" Lady L. announced.
The men looked shocked as though they considered this a threat certainly
impossible to fulfill but a threat to their manhood nonetheless. As a
group they seemed more timid than we had been at first. Perhaps it was
the sight of we sissies who had been transformed that made the threat of
total feminization more real.
There were eight of them all together. Just the right number to have
each of them assigned to one of us, which was Lady L.'s plan.
After a short discussion, the ladies had chosen which of the new males
would be paired with each of the experienced sissies. It seemed a
natural match when I was put in charge of Mistress Margaret's husband,
an awkward individual named Wayne. He started with the usual whining
that there was no way he would ever succumb to this training. He
obviously did not know who he was dealing with. My group had
experienced the training and conditioning. We had learned our place in
the grand scheme developed by Lady L. and our spouses. Our behavior had
been corrected and now we were the individuals we were supposed to be.
We knew that our purpose was to serve the Ladies and the real men that
would visit here. And now we would assist in the transformation of
another group.
What fun!
Tied naked spread-eagle over his bed, Wayne received the first lesson it
was my privilege to give him...
Thwack! "Oww!" The paddle landed squarely on his ass.
Thwack! "Owww!"
Thwack! "Owwww!"
This continued until his buttocks were beet red. "Alright, alright I'll
shave!" he finally agreed.
The process had begun again. He was totally shaved of his body hair by
his 'boyfriend' and then he did the same to this new 'boyfriend'. It
was genuinely fun to perform the inspection on my 'student'. I enjoyed
causing him fear and humiliation as I closely reviewed his body looking
for shaving "errors". Of course I found an errant strand of hair here
and there for which he paid a price. Thwack! Thwack! Thwack!
And when the redness had finally gone away several days later, he
received his first tattoo, a large cock design on his right ass cheek.
I actually got to watch one of Lady L.'s male assistants perform the
work, my first class in being able to do body art myself.
Initially when Wayne was unwilling to wear a bra, I placed nipple clips
on him for one-half hour at a time. It was certainly painful, but not
as painful as when the clips were removed. On one-half hour, off for
one-half hour. Ouch!
His building anger with me finally got the best of him and he took a
swing at me. He missed and was quickly subdued by all eight of us
graduate sissies. We were there to assist each other in just such an
event.
It was the only time Wayne (now Wendy) would try such a thing, as the
punishments for violent behavior were more severe. Wanda was much more
docile after having her nipples pierced and studs placed in them.
Transgression followed by punishment. Obedience followed by reward.
The lessons that had worked so well on the first batch of sissies were
just as effective on the second. It was nice sharing the maid
responsibilities with the new group. More time for lying on the beach
in my bikini. Ahh. Life is good.
It was not perfect however, as Mistress Margaret was always there to
make sure I did my job in properly training Wayne to her specifications.
If Wendy did not advance in her feminization as rapidly as Mistress
Margaret desired, I would receive another slap on the face which was
followed by my now routine "Thank you Mistress Margaret" and a deep
curtsey.
In about a year, half as long as it had taken us, the second group of
feminized males were very close to completion of their training. Lady
L. was so proud of all of us. I even received a reward. Wendy's wife
(now ex-wife) got to watch as Wendy licked and sucked on my cock for
nearly half an hour. It was a wonderful experience. Sexual release of
any kind was a real rarity for a sissy. The sensation of another male's
lips pressing on my penis was extraordinary. The warmth of her tongue
was exquisite. I was moaning audibly as I held her head and slid my
member in and out with increasing speed. After my orgasm I looked down
to see the red lipstick smeared on my cock and felt a sense of pride in
knowing how good I must be making the real men and other sissies feel
when I serviced them in this same way.
We were all accepting of who we were and what we had become. Long ago
it seemed impossible to conceive of me being subservient to women and
having sex with males, Now it was inconceivable that it be any other
way. I now had fifteen potential 'boyfriend' sissies sharing the island
with me in addition to the real men who occasionally visited.
Immediately after the graduation of the second class of sissies from
W.I.T.C.H., Lady L. announced that she was again starting a campaign to
find even more women dissatisfied with their spouses. Perhaps sixteen
this time to match the new number of 'mentors'.
I was becoming as enthusiastic as Lady L. in my desire to help transform
submissive males with dominant wives into the proper feminized sissies
that they were surely meant to be all along. I went to Lady L. herself
and with a broad smile and a proper curtsey, I said to her, "I think
we're going to need a bigger island!"
"I'm so glad you think so Lynn," Lady L. said in a way to convince me
of her sincerety. "I am as pleased as your ex-wife was with your
progress. So pleased in fact that I have been talking it over with
Mistress Margaret and we would both like to see you move to the next
step."
"Next step?" I said. My tone had shifted quickly from happy to fearful.
"Yes. It's a big one but we now know you're ready. It would involve
HRT, hormone replacement therapy."
I was speechless.
"If you're not already familiar with the process, let me explain. It is
called therapy because it is actually a course of treatment. In your
case it would be treatment for those remaining undesirable male
characteristics. You will begin taking certain medications. The
'replacement' would be substituting estrogen and progestin for androgens
such as testosterone. But I don't want to confuse you with a bunch of
medical terminology..."
"But what if I don't want to do it?" I interrupted.
"Hear me out." Lady L. spoke in a stern voice.
"We are looking at the long term benefits of this. You will have a
softer more curvey body. You won't have to shave as often and
eventually you won't need that chastity cage anymore. Wouldn't that be
wonderful?"
"That's because I won't be able to get it up anymore, isn't that what
you're saying?" I said, now terrified.
"Oh, you're sex drive may be diminished a little but that will be
replaced by a whole new set of wonderful feminine feelings. You will
finally be able to enjoy the extraordinary intimacy that a woman feels
when a man makes love to her. Our clients would appreciate that
improvement and, after all, aren't we here to please them?"
Starting to cry, I tried to protest, "You're going to castrate me too!
No...no... I don't want that!"
"Silly gurl! No one is going to do any such thing. My clients actually
tend to prefer feminine males. I don't question their motives but they
basically want women with that one male part. We all know how strange
men's desires become when sex is involved but you would be in the best
of all possible worlds. You could have the best female parts and the
best male part all at the same time! The real men who visit here would
all want you!
You could be dating them instead of doing chores as a maid! How
wonderful is that?!"
I was truly relieved that no surgery was involved but I still had my
doubts. "Can I have some time to think it over?"
"Of course, little one. And let me say that you will be getting the
best medical attention available. Don't forget Mistress Margaret is a
former nurse. These things must be monitored for side affects and we
will want our favorite *********** to be in the best shape possible for
our clients. I promise you that you will not be sorry!"
I was going to have a lot to think about.
Or perhaps not. Lady L. then left to see Mistress Margaret. A short
conversation followed.
"Have the tests come back?" Lady L. asked.
"Yes. They were all fine", replied Mistress Margaret.
"Great. Then I think it's time to up the dose. What do you think?"
"I agree. 50 micrograms of the synthetic estrogen twice daily but I
think I'll leave the progesterone and Propecia, that's that anti-
androgen d**g, where they are for now. I never thought this would be so
much fun. I can't wait to try it on my ex-husband."
I had no idea that Lady L. had been ******* my meals for several weeks
already. I had been pushed down the road less traveled at breakneck
speed and U-turns were i*****l!
<<<<<<<<>>>>>>>>>
In the end several of the wives, including Daniela's wife, chose to take
their 'husbands' back to the States. They would become the docile,
submissive slaves to their wives that they had been trained to be.
Andrea, Susan and Vanessa would continue to live on their own tiny
island as the 'Queen' and her 'Princesses'. There certainly would be
very little sex on that island but no one, including those three
inhabitants would probably care. The best I could hope for was to avoid
joining them as Andrea's third 'Princess".
Only Charlene, Lisa, Gail and I, Lynn of the original group would remain
on the island.
It was amazing what the training and conditioning of W.I.T.C.H. had
done. Was this what any of us sissies either wanted or deserved? Were
we proud of what we had become? Were our wives right? Were we any
happier? It didn't matter for this is the way it was and the way it
would be from now on. You could either choose to be miserable with
yourself or accept who you were and make the best of it. Ultimately I
was never told that I had been on hormone replacement therapy from much
earlier on but when I looked in the mirror and began to notice the
changes in my body, I could only smile.
As roughly as my ex-wife had treated me I still love her and am happy
for her. She had left me behind but I somehow knew that it was the
right thing to do. She lived with both of her own boyfriends now and
she did indeed end up putting a very large picture of me in my
bridesmaids dress over the fireplace. It was actually quite flattering
in displaying my femininity and would prove to be a real conversation
piece with our friends back home. Lady L. continued to send her
progress reports on my new appearance.
With the arrival of yet a third group of submissive males it was clear
that this was truly going to be a growth business. My fellow
'boyfriends' and myself had been promoted to instructors to help
accommodate this new class of trainees.
There was also a rumor that Steve and John would both be returning to
the island at the same time soon. Ummmm... I couldn't wait!
A story about a group of men duped by their wives into attending the W.I.T.C.H. Institute in order to learn more appropriate behavior. They are forced to do many humiliating things to "earn" tokens acknowledging their accomplishments.
W.I.T.C.H.
Women's Institute for Training ......... Husbands
Some of them were caught cheating on their wives. Some were caught in
various ways while wearing women's clothing. Others were miscreants who
had in some way so displeased their wives that their actions had driven
their wives to take drastic action.
All the men had in common the fact that their unexpected behavior
infuriated their wives enough to want to punish their husbands in some
unique way. The wives had in common that they had each found the same
way. It had not been easy to find this way either. But they had all
navigated through a series of websites, each directing any new members
to join the next website where they were instructed on how to pursue a
slightly more devious way of exacting revenge on a misbehaving spouse.
The last one directed any women having come this far to a small
newspaper ad which in turn gave them a phone number to call for further
instructions if they used the proper code from the website,. It had all
been part of a grand plan to capture the interest of a very small,
select, and curious group of women intent on seeking revenge on a man
that had wronged them.
The inventor of this grand scheme, Lady L. was herself a fabulously
wealthy woman who had been nearly cheated out of her vast inherited
fortune by a conniving husband. Her experience was so bitter and her
personality so vengeful that she had not only "taken care of" her own
problem but she decided she was going to help other dedicated women with
solutions to their problems.
And so it was. One by one each of the dozen ladies had made the phone
call. Actually others had called but they backed out after hearing the
direction that their revenge would take.
It was a truly thorough screening process. One that resulted in only
those fully dedicated to making their victims pay for their
transgressions following through on the plan. Immediately after the
women agreed to join, the websites were closed, newspaper ad cancelled
and phone number disconnected. The trail would be untraceable.
One by one each of the parties received the same letter telling them
that they had won a fortune ($20,000,000) in the contest that their
wives had entered. In addition to the money they had also won a
fractional interest in a private Caribbean island. The only condition
was that they move there for a period of time to consider permanent
possession. It was not difficult to get the men to go along with this
life changing experience when they saw the $20,000,000 credited to their
bank accounts. (None of which they could spend, of course, until they
arrived on the island as agreed.) That is not to say that some were not
skeptical about their fantastic good luck--one even had his lawyer look
into the legitimacy of this contest--but Lady L. had left nothing chance.
The contest had been private and there was only a limited number of
things anyone could check, but with all that money in the joint account
belonging to themselves and their wives, the attempts to disprove their
good fortune were limited indeed. It was not long before all the men had
quit their jobs (some at the insistence of their wives) and said goodbye
to their old lives. The timing so that each would arrive at the island
within a few days of each other was the most difficult to arrange, but
in the end, Lady L. had also cleverly managed to slow down the most
anxious ones with legal issues and papers to sign and speed up the
hesitant ones with time limitations so that all couples were in place
and ready to participate within days of each other.
At last, all of the couples were assembled in a small meeting room of
the one hotel on the island. Each of the men thought that the other
couples were the other winners that would share their fractional
interest in island ownership. The women knew differently.
The one named Andrew had always had strong sexual urges and many sexual
fantasies. He was at a point in his marriage that he simply wanted to
satisfy these fantasies but knew his wife would not understand, much
less approve of them. So, in secret, he sought out the services of a
professional dominatrix. This actually worked well for him for a while
until he wanted still more than the domme was willing to provide.
Dissatisfied, but still insisting on having it his way, he made the
mistake of not paying his domme for services she had already rendered.
His domme repaid his ignorance of this aspect of her business in spades
by affirming to his wife what she was already beginning to suspect. When
she confronted him about his indiscretions he arrogantly brushed her
aside thinking that he could get away with anything. His substantial
income, coupled with the fact that his wife, therefore, did not need to
work, insulated him from reprisals by his wife, or so he thought.
Bradley had led a relatively normal life until after he got married. He
had always been somewhat submissive and his wife actually found that to
be one of his endearing qualities as she thought that he was just sweet.
Then she too began to wonder why his sexual interest seemed to decline
so suddenly. She discovered, quite by accident, that he was seeing
someone. That someone happened to be another man! Her shock at the
discovery of his bisexuality, led her to begin her search for answers on
the internet. That search ultimately led her here.
Charlie had been cross-dressing since he was 15. He discovered his
attraction to wearing women's clothing when he saw his sister's panties
hanging on a clothes line to dry and could not resist the urge to try
them on. His immediate reaction, a rock-hard erection. He remained a
cross-dresser ever since. The problem was, he always did it in secret
and never even hinted to his wife, that he enjoyed it so much. His lack
of interest in sex led his wife to believe that he was cheating on her,
but she eventually found his stash of women's clothing and pornography
and when she confronted him with her discovery, very embarrassed and
trying to search for a reasonable explanation, he insisted that this was
"normal" male behavior and, therefore he was unwilling to change.
Daniel was slight of build, submissive by nature and seemed to be a
perfect match for his somewhat shy wife. It was surprising that they had
met at all, given that both had reclusive personalities. But their
friends recognized this and set them up on a blind date. With more than
a little pressure from their friends, eventually they agreed to marry.
No one doubted that they belonged together until his wife found him
cross-dressing in secret. He had the physique that allowed him to pass
easily as a female when dressed as such. What surprised her is that he
did this on a regular basis without her knowledge. She found out only
when their neighbor let it slip that she had seen him in women's
clothes. His wife was mortified. The neighbors knew and she did not and
this ate at her core. His refusal to talk with her about it, coupled
with his insistence that he continue cross-dressing without her approval
set her on a course she was determined to pursue. That is how they ended
up at the W.I.T.C.H. institute.
Edward was the handsome, dynamic world beater that no one would have
guessed had a feminine side to his personality. In every way he
appeared normal but his deep dark secret, which was ultimately, perhaps
inevitably revealed to his wife was that he often wore lingerie under
his male clothing. Usually very outgoing by nature, he became very
sheepish and embarrassed when his wife found his hidden "stash" of
unmentionables in the garage. He had hoped his loving wife would have
been more understanding. She was not. She saw this fetish as a great
threat to her social standing should it ever leak out. She was
determined to nip it in the bud. A series of covert inquiries had led
her to the institute.
Frank and his wife were members of the local BDSM club. Both were into
alternate lifestyle fantasies until he went over the top and demanded
that his wife do things she was not comfortable with. He continued to
press her already liberal limitations until she finally said enough. She
decided to take him to a totally new level beyond even his dreams.
George was a happy-go-lucky sole, never married and with no current
girlfriend. He was somewhat overweight but this did not stop him from
pursuing his desire to get in touch with his feminine side. Having no
significant other made it easier and perhaps more necessary for him to
surround himself with feminine things. He enjoyed cross-dressing when
he could and made only half-hearted efforts to hide his somewhat unusual
pursuits, which he felt were perfectly natural. He was a member of
several femdom internet groups in which he had a picture of his femme
self proudly on display in his profile. His naturally trusting nature
eventually resulted in him believing a prank that one of his internet
"friends" decided to play on poor George. Purely at random some college
student somewhere had chosen George to be the guinea pig when he had
discovered purely by chance the phone number Lady L. had planted.
George's case was only different from the others in that he was set up
by someone whom he didn't even know. The result was the same. George
took the bait and arrived at the island with the others expecting
something far different than he was going to get.
Harry began with an almost idyllic relationship with his beautiful wife.
Successful in business, he and his wife frequented some of the worlds
nicest beaches, most popular casinos and trendy hot spots. So enamored
with himself was Harry, that he felt one woman was not enough for him
and eventually he succumbed to his desires, and was immediately caught
by his wife who just as quickly decided what his fate would be.
Irv and his outgoing spouse had been married a long time and his wife
began to tire of the relationship. When she wanted to join a local wife
swapping club he acquiesced. His wife met another member she apparently
just could not live without. Irv was OK with this and even found it
erotic to see his wife with other men. She became tired of having such a
"wimp" of a husband and decided she needed a way to change their
relationship.
Larry is my name, or at least was my name. I had had a normal
relationship with my wife too, until we had grown apart as many couples
do over time. As the years went by our interest in each other grew less
and less until sex was nonexistent. By that time I had begun to revert
to an old habit I had begun many years ago. Whenever I had found myself
between girlfriends, I seemed to find comfort in cross dressing. It was
as though I was providing myself with my own female companionship. It
worked because there was no one around to keep me from satisfying myself
in this private, harmless way. That is, until I was married and began
doing it again in "private". I had been wearing a bra and panties from
my well hidden stash when my wife came home unexpectedly early one
evening. I though I had it covered when I quickly removed and hid my
feminine things dove into bed and pretended to be asleep before she
walked in. I didn't realize that the very snug bra had left
unmistakable impressions on my back. My wife noticed this, of course
and most unfortunately for me without my knowledge. She then was able
to set traps for me in the form of hidden video cameras. In short order
she literally had the "goods" on me without me knowing. For my wife
this was the last straw and set her on her vengeful ways. It did not
take her long to find the "Institute".
There were a few others and their stories are remarkably similar to the
stories of the readers of this tale.
When all of the participants were finally settled in their hotel rooms
we each received a note that their would be an introductory meeting that
evening in the hotels small conference room. Everyone was anxious to
attend. Especially the ladies.
It was Lady L. herself who got up at the podium in front of the room and
welcomed us all to the island, her island. The shocking news was broken
to all the men at once. After her initial welcome, she got right down to
business.
"You men think that all of your worries are over. Well, I'm afraid that
you have been intentionally misled about your stay here. You see, while
most of your needs will be taken care of while you're here, I'm afraid
that you will be trading in one thing during you're stay here. That
thing is your freedom. You see, all of you have been captured on video
doing things that you should not have been doing."
Each of the men suddenly became silent... and worried.
Lady L. went on, "I am going to show all of you a brief video of what I
am talking about." The lights slowly dimmed and a screen lowered
silently from the ceiling. For a brief moment there was absolute
silence in the room. When the video began to play the men remained
silent. Among the ladies could be heard an occasional giggle, snicker or
an "Oooh" or "Ahhh".
One by one, the men's actions were displayed on the screen for all to
see. They were all clearly from the angles of **********eras but each
displayed some of the most humiliating scenes that the men could
remember. The insertion of a butt plug, the wet spot appearing on the
front of a pair of panties, the delight showing on one's face as he
slipped on a pair of pantyhose. A visit to a Dominatrix. It was all
there.
As their own peculiar behavior eventually appeared on the screen for all
to see, the look on each of the men's faces went from shock to utter
red-faced humiliation. In contrast, by the end of the video the women,
all good friends by now, were laughing hysterically.
The screen went blank and rose into it's place in the ceiling. Lady L.
again stood at the podium but did not speak until the laughter of the
ladies had subsided several moments later.
"Well gentlemen, and I use the term very loosely, do you have anything
to say for yourselves?" Andrew mumble something unintelligible under his
breath but the room was otherwise silent. "Don't be afraid. The reason
we are here is to give you a chance to redeem yourselves in front of the
one who sent you here!" She glanced at George. "You will have one
chance to recover your dignity and again become worthy in the eyes of
your spouse. Otherwise these videos will make their way on to the
internet, into the places you used to work and into the mailboxes of
many of your relatives. In short, your life as you knew it would be
over."
"You see, we ladies have come to the realization that there are many men
out there who enjoy being feminine or have unusual fantasies. The
problem is that they also want regular relationships with women but
don't consider the affect your fetish has on that woman.
"So, we are giving you the opportunity to have your cake and eat it too.
The only thing we require of you is your complete and unquestioning
obedience! You must do what is required of you or you will fail and
suffer the consequences. But don't worry, it's not all bad news. You
will be permitted a transition phase in which you will be able to wear
clothing that more closely fits your temperament. Yes, women's clothes.
But before you get too excited, let me explain that you must agree to
this course of behavior modification, in writing, otherwise you're
screwed as previously mentioned."
Their minds racing, the men could each be seen mentally weighing their
choices. None was their silent and unanimous conclusion.
"Any questions?" Lady L. asked.
After a brief pause, Edward raised his hand.
"How long will this take?"
"As long as necessary, until your significant other says you are ready."
"Will we be allowed to contact anyone from back home?" Again Edward
spoke.
"No. There are no phones on the island and no cell phone service."
"You know this is k**napping." Andrew interjected forcefully.
"Not after you sign the agreement which, among other things, states that
you voluntarily accept these requirements for your own betterment."
"I won't sign it!" Andrew barked abruptly.
"You're choice. The previously stated consequences would still apply.
Gentlemen, (cough) so that you don't miss the point of this rather
extravagant operation, our sincere hope that you will come to see that
we are doing this for your own good. We truly believe that once you
have been immersed in our programs for each of you, that you too will
come to appreciate your lifestyle choices. We know that you will be
happier and more content than you have ever been. This is as much for
your benefit as for that of your spouse...or significant other."
Cathy, a very attractive young lady appeared at the door of the
conference room with papers and pens. She passed them out to the men
while the ladies watched smiling. There were several pages of fine print
which several of the men began to read in earnest, fearing the worst.
Lacking much detail about specifics, nothing appeared unusual for a
contract except the phrase "Total Obedience." There was little else to
do but sign. All of the men did as each lady gave a "thank you dear"
smile to their new charge.
We were then each given a pamphlet containing a lot of material which
proved to be pretty convincing. The first information was on the Fem Dom
lifestyle and why it made sense and how it made life better for all
parties involved. It told why women were superior in the marriage and
why women should be in control providing many examples of marriages made
successful by Fem Dom rule. It explained why males were meant to serve
their female "owners" and why it was natural for that to happen. It also
explained some of the fears and concerns males would have and why they
were nothing to worry about. Males in these 'advanced lifestyle'
marriages would learn to accept that the only thing that truly brought
them happiness was serving and pleasing their wives.
As males, except for Harold, we had all expressed varying degrees of
femininity or acceptance of female dominance somewhere along the line in
our lives. And in varying degrees we all anticipated anxiously what was
going to happen to us next. But none of us was ready for what the
ladies had in store.
We then took a short break to eat lunch and each receive a pep talk from
our respective lady. This was to set the tone of our training which
would be all praise and rewards for obedience and both mental and
physical punishments for disobedience.
Upon restarting our meeting Cathy gave us another pamphlet which we were
given ample time to quietly read.
This information was on sissy training and how much more pleasure a male
would get from being dressed and trained to be a sissy. Most of the
emphasis was on sissy maid training and how such tremendous feelings of
worth and value would be felt by the well trained sissy maid. It posed
questions to ask ourselves about our own feelings of becoming such an
important part in the life of a woman.
A highlighted section noted in detail how much a woman needed powerful
sexual experiences and how few men could actually provide them. It
strongly supported cuckoldry as the best way for the woman to be happy
and satisfied and to improve her attitude. It even had testimonies from
cuckold husbands who said they found it to be true.
There was a great deal of information on how the greatest feeling a
sissy maid cuckold husband could have was serving his wife in front of
her lover and friends and seeing the expression of pride and joy on her
face. Husband after husband related how wonderful it made them feel to
perform in this manner. Toward the end it went on to explain about
serving and taking care of madam and her lover(s). It all seemed to be
hinting that our wives were intent on taking on lovers while we suffered
extreme embarrassment of some sort. The range of reactions from our
group were from an occasional gasp or muffled "WHAT? NO WAY!" to
squirming in a poorly hidden attempt to hide an erection. It had a
profound effect on my mind and feelings. I began to consider my wife's
needs, the wrongs I had committed and my place in our relationship.
"Wonderful! You have all agreed in writing to take steps to improve
yourselves." Lady L. stated enthusiastically. "In your cases this may
take quite a while. In order to measure your progress we have to have a
base line to start from. That means we are going to start each of you
out in feminine mode and make progress from there. We will soon see how
each of you handles it."
The ladies in the room were all wearing ear to ear grins. The men were
all deathly silent.
"Each of you will begin at an appropriate starting point for your own
level of feminization and you will progress toward the goal that your
spouse or significant other has established for you. I will warn you
that our expectations for you are high. If you do not immediately get
with and stay with the program you will be made to regret your
decision." Lady L's tone as the ultimate authority was unmistakable.
It seemed the ladies could barely contain themselves. The men remained
silent and wide-eyed as to what might be required of them. Only Andrew
remained expressionless and looked as though he was prepared to be
openly defiant.
"From now on you address any woman as 'Mistress' or 'Madam', whatever
their preference. You will be referred to in the feminine tense, as
'she' or 'her'. Each of your sponsors, that is your spouse or
significant other, has suggested a feminine name for you.
And since each of you has, in some form or another, expressed some
feminine behavior, this will be your new name. Any objections?"
Andrew spoke in an almost sarcastic tone. "What if we don't like the
name?"
Lady L. remained silent. She looked us over with an expression of utter
disdain.
"You will now pair up in two's. You will shower and then you will shave
every hair off of your body from your sideburns down. That is every
hair, neck, chest, back, armpits, forearms, pubic area, legs, toes, etc.
You will be paired in twos and each will inspect the other for any
flaws. If upon our inspection a single hair is found anywhere below your
sideburns you will both be punished severely. Since there are an odd
number, Andrew will be shaved by his sponsor. You have one hour."
Now in near panic mode the males looked around the room in confusion
while the ladies directed each pairing to the bathroom of one of the
hotels suites. I was paired with Charlie. The circumstances resulted
in us forming an immediate friendship. Both of us had a moderate level
of self-acceptance of our feminine sides and were more than willing to
go with the "program," given the unknown but certain consequences. We,
in fact, were the first ones done in showering and shaving, leaving us
enough time to carefully inspect each other to make sure not a hair was
missed. It was a most unusual experience, however, washing, lathering
and then shaving my entire body, and then having Charlie closely look me
over and I him. Oddly, or perhaps not, the sensation of slowly being
made totally hairless and then closely examined by another man resulted
in first Charlie, then myself, becoming sexually aroused. We each
laughed at the other's involuntary acceptance of this humiliation and
this ended up helping us bond together even further. For both of us,
our situation seemed very erotic in a way. Having no control and being
forced to do something so against our basic nature.
After the hour was up we all assembled again in the meeting room. The
males were all nude and very embarrassed. The ladies were all giggling
and whispering to each other.
Each of the males, including me, tried to ignore the new "look" each of
us was sporting, but could not help but notice that Andrew alone still
had his pubic hair.
Again, Lady L. took charge of the meeting. "Andrew, henceforth to be
known as Andrea, has been a little slower than the others in accepting
her fate. And as you will see, being unacceptably slow to fulfill our
wishes for you has consequences."
Andrew (now Andrea) displayed a worried look of defiance as a wooden
table with straps was wheeled into the room by his wife and one other
lady. Suddenly Andrea began to head for the door muttering "screw this"
as she tried to leave. Just as suddenly, two large black men who had
been standing silently close by, grabbed his arms and held him while one
of Lady L.'s assistants stuck a syringe in Andrea's arm and caused her
to fall limply to the floor almost immediately. When she awoke, she was
bound helplessly spread-eagle to the table. Finally, when she was fully
aware of what was going on, her wife placed two wooden matchsticks in
Andrea's pubic hair with the flammable end pointing upward. Her wife
then lit another match and held it to the tips of those nestled in
Andrea's bush. They ignited and slowly burned down until the crackle of
burning hair could be both heard and smelled. Andrea shouted, "Damn you!
Stop it. Let me out of here!" Then her pubic hair began to burn more
quickly as individual hairs lit up and burned like filaments of a light
bulb. "Aaaaahhh! Stop it," she screamed. As the rest of us watched,
Lady L. put a damp cloth over Andrea's groin to stop the spectacle.
"Are you going to shave yourself now?" Lady L. insisted. No reply. Lady
L. then placed three more matches in the stubble that remained of
Andrea's pubic hair.
"No! I'll shave," Andrea squeaked.
"No, you won't" said Lady L. "The other 'males' will do it for you."
Lady L. signaled Daniel (now Daniella) to go get some shave cream and a
razor from the bathroom she had used herself. She hurried obediently and
was back within seconds. At Lady L.'s instruction, each of us carefully
shaved a small patch of the remaining hair until Andrea was as smooth as
the rest of us. At this point, each of us was too afraid to not follow
Lady L.'s next command: "I want each of you to file by Andrea and tell
her how pretty her penis looks now." Reluctantly, each in turn did
exactly as told. Andrea, infuriated and clearly wanting to curse at all
of us, remained silent.
With that Lady L. snapped her fingers and the two black men placed a
cock-gag in Andrea's mouth, completely muffling any potential
objections.
"Let this be a lesson to each of you as to what will happen if you do
not willingly follow directions." Lady L. insisted. "This is just a
taste. And as a consequence for each of you for your friend's behavior,
you will each spend tonight in a cage. You may thank Andrea later."
The males stood aghast. The ladies were also silently with stern looks
on their faces.
That night, each of the males spent naked, confined in a locked dog cage
approximately 2' x 3' x 4'. We were thus given the incentive to keep
each other in line or suffer as a group for the indiscretions of any
member.
<<<<<<<<<<< >>>>>>>>>>>>>
Early the next morning we were each released from our confinement with a
series of moans and groans because of our stiff joints. As we stood
naked as a group before the ladies, Lady L. presented each of us with a
plaque honoring our acceptance of much deserved punishment for
"CHEATING" on our wives. Each was customized to show our own particular
method of "cheating". Then Lady L. began to explain more about what was
going to happen to us.
"If you perform satisfactorily what is required of you today you will
avoid having to sleep in the kennel cage tonight. I think the
alternative sleeping arrangements will be much more to your liking."
In unison all of the males let out a sigh of relief. The cage was very
unpleasant.
"You will sleep in a comfortable bed. Since there is only a limited
number of beds you will double up with your assigned partner." We looked
at each other, somewhat perplexed. "Oh, and by the way, going forward
each of you will refer to your partner as your "boyfriend". You will
either refer to her by her feminine name or as "my boyfriend. Is that
understood?... IS THAT UNDERSTOOD?"
"Yes, Madam" was mumbled by all except Andrea, who earned another icy
stare from Lady L.
"Also, as you walk between buildings on campus with your boyfriend, you
will hold her hand at all times, again, no exceptions." After a short
pause, "UNDERSTOOD?"
"Yes Madam," a little louder this time.
"I know this may seem difficult for you now but it is an integral part
of your training on this campus. I call it a campus because this is
where you will be taught what you need to know. You have each expressed
your feminine side in some way and this is where that side of you will
be cultivated and nurtured. In essence you will receive feminization
training and learn to cast aside the undesirable characteristics of any
masculinity you may possess."
Each of the males mumbled her own unique but subdued response, still
somewhat in disbelief of what was happening.
"Each of you will pair up with your boyfriend and Monday through Friday
will attend the following classes together:
One; Domestic Sciences, Two; Feminine Dress and Behavior, Three; Dance,
Four; Women's Studies and Five, Anatomy. Other classes will be
organized for each of you on an individual basis as needed. You will
have homework... QUIET!!" Grumblings were growing louder among the
males but Lady L.'s quick rebuke silenced us instantly. "You will have
homework and you will be tested on what you learn. Anyone receiving
failing grades will be punished accordingly. Classes start next Monday
and you will be given more details by that time. That is all." Lady L.
turned and began walking away.
Again a murmur arose between the males when Andrea spoke just loudly
enough to assure that Lady L. could hear, "This is bullshit!" At this
comment, Lady L. slowly turned back to face Andrea with another cold
stare. She then gave a slight nod to one of the black men standing
nearby who then quickly raised a dart gun and shot Andrea in her
buttock. "Aaahhh, owww. Dammit. F*** you!" Andrea only gave these
brief remarks before falling flat on her face, u*********s. The black
man with the dart gun as well as two others promptly grabbed Andrea and
carried her into one of the small dwellings near our meeting place.
This event left the other males in stunned silence, fearing the same
might happen to them if even the slightest objection were made. We were
then led back in our "boyfriend" pairs to our rooms to try to absorb all
that had just happened that morning.
It wasn't until several days later that Andrea was released from her
confines and allowed to rejoin the group. It was not difficult to see
that something was very different about her. She was walking slowly,
with head down. When she approached close enough to us we could see
what had happened. Her penis had been given what is called a Prince
Albert piercing, a large thick metal ring had been inserted through the
tip and it was locked to another ring through her perineum. This made
it impossible for her to achieve an erection. This was a shock to the
rest of us. We had been exposed to our first real example of how far
the ladies were willing to go.
Monday finally arrived and the males all were full of a combination of
fear and anticipation. Despite the fact that Charlie and I got along
well, I had difficulty accepting that I would have to walk hand in hand
with him, both wearing knee socks, matching plaid skirts and ruffled
blouses, across an open courtyard to a class that was to teach us how to
dance. When we arrived we were instructed to put on pink leotards and
tights, which, by some coincidence fit each of us perfectly. It was one
thing to dress in feminine things in private but quite another to be
humiliated in front of three women. It helped to have Charlie there as
it cut my embarrassment exactly in half.
We were also presented with another plaque honoring our acceptance and
desire for full time CROSS-DRESSING as a means of enhancing our
preferred feminine characteristics.
My realization of just how humiliating this was going to be hit home
when the first lesson, first through fifth positions began. Ballet! We
were going to learn ballet! Demi plies, first, second and third
arabesques, it was all so confusing, and embarrassing at first. But we
would be made to repeat the moves over and over again until we got it
right. When I mocked the pirouette during training, the penalty was an
ice cold shower after class, followed by a painful whipping with the a
cane. It was clear from the start, in every class that Charlie and I
attended that there would be no nonsense. We were there to learn and
learn we did. Obedience was indeed the rule. Deliberate errors were
met with severe punishment. I received a heart tattoo on my ankle for
one offense, a pink butterfly on my shoulder blade for another and a
rainbow tattoo just above my buttocks for a third. Errors during honest
attempts were met with encouraging remarks and additional repetitions.
At first to avoid punishments, and later to earn praise, Charlie and I
began to put forth our best efforts to learn ballet. As unnatural as it
seemed to us, our overwhelming desire eventually became to please the
ladies and avoid pain. Progress was rewarded. Lack of progress was
punished with increasing severity. It was a classical case of
conditioning.
Charlie and I eventually became modestly proficient at ballet positions
and moves. We could not perform lifts or joint moves with lady
ballerinas but they began to call us novice danseurs (male ballerinas).
Privately, the ladies were overjoyed if even somewhat surprised to see
the program was off to such a good start. Here it was, a group of
contrite males that were going to accept much deserved humiliation by
learning to be feminine.
As further encouragement to our transformation into sissies, Lady L.
provided each of us with a locking chastity cage to which our mistress
held the key. We were told that this would assist us in our desire to
please the ladies by enhancing our submission. And given that we each
stayed locked up for one month before being released she was 100%
correct.
At the end of that month each of us received a plaque honoring our
acceptance of long-term CHASTITY as a way to reform ourselves.
When I awoke the next morning it was as if I had awakened from a bad
dream. I was lying next to Charlie (now "Charlene") our backs turned to
each other. We were both wearing matching black nighties and despite the
fact that we had become friends, it was very embarrassing having to share
the same bed with him and have to refer to him as "she, her or my
boyfriend" from now on.
The next thing I noticed were my three plaques hanging over the bed. The
lettering made them look like diplomas signed by Lady L.
In bold script the first read:
CHEATING,
For allowing my wife to believe I was a man while I dressed as a woman
The second:
CROSS DRESSING
For wearing women's clothing while pretending to be masculine
And finally:
CHASTITY
For transferring all rights to my sexual activity to my wife
I felt that they were foolish but did not dare try to take them down for
fear of the consequences. I glanced at the alarm clock and realized I
would have to hurry to dress for our Domestic Sciences class. I awakened
Charlene and we raced to dress in our matching plaid skirts and ruffled
blouses. We both misjudged how long it would take to dress and get to
class because we could not move very fast in our high heels while holding
hands. We were five minutes late to class and earned two extra weeks in
chastity as a result.
Domestic Sciences class began with each of us being given two types of
maid uniforms. One was a classic professional style in powder blue
complete with knee length skirt, apron, flat shoes and name badge,
engraved with our feminine names of course. The other was a short French
maid outfit in black, with garter, black stockings and 4" high heel pumps
which happened to fit each of us perfectly.
I tried not to show it but I was actually very pleased to be able to wear
such feminine things which seemed to be made especially for me. I
guessed the other regular cross dressers in the group must be happy too
as these were quality clothes. I reveled in this small pleasure even
though it was the reason I was here in the first place.
Immediately after receiving the maid's outfits we were informed that this
would be a learn-by-doing class. (Note: The instructors in these classes
were strangers to us but generally were very pretty and very
knowledgeable about their subject. Our wives often sat in on some of the
classes to watch our progress, and witness our humiliation at being
exposed as sissies in front of our instructors.)
In this class we would learn all of the responsibilities of maintaining
the island's hotel rooms, including making the beds, washing the laundry,
ironing, dusting, cleaning the bathrooms and all of the other mundane
tasks associated with a maid's work. After being shown just once exactly
how to fold and tuck the sheets on the bed, for example, we were then
expected to do them ourselves. And we did. Over and over and over again
until we got it right. It was mind-numbing work and caused the discontent
with our group's situation begin to grow....silently.
Despite the fact that there were few visitors to the island, a small boat
would appear occasionally and it's crew and guests would stay for a week
or so. Keeping the hotel rooms in perfect condition soon became our
responsibility. We would each work in teams a couple of days a week and
were closely supervised by our instructor. A good job was praised and a
bad job... well, you know the story.
Some of us, myself included, began to worry when we were told that the
French maid's uniforms would be worn when we served at a party. As fun
as it was to wear the outfit, it was terrifying to think that we would
have to display ourselves in front of strangers while wearing it. The
more people that knew of my fetish the less I liked it. We were even
taught how to curtsey. This was getting out of hand.
<<<<<<<<<<<<>>>>>>>>>>>
Women's Studies, our next class, began with the various articles of
makeup, their applicators and what colors and tones looked best together.
Cathy, the same pretty girl who had handed out the agreements for us to
sign at our first meeting, was our instructor. I noticed she smiled my
way a few times and I began to daydream of striking up a friendship (or
more?) with her.
The first time we practiced applying makeup it was a comedy of errors.
Bradley ("Beth"), Daniela, Charlene and I had all experimented at some
point in the past and therefore, did a passable job. Cathy actually
complimented me. The others ended up looking more like clowns than women.
I was happy that for once I did not have to do countless repetitions.
Andrew did and you could tell he was not happy about it.
Early the next morning, each of us was lead individually to a small hut
at the edge of our compound. Each left the hut a short time later and
was lead out of sight of the others, directly back to our rooms. When my
turn came I was lead by the arm by my wife to the hut. Lady L. and a
smiling black man and woman were there. A case was placed before me and I
was told to choose one pair among it's contents. It was then opened to
reveal a wide selection of silver hoop earrings. They were not clip-on
earrings. It was held in front of me until I selected a set of large but
otherwise plain ones.
Lady L. spoke first. "Do you willingly accept this precious gift as a
reward for your high marks in Women's Studies?"
I naturally hesitated allowing time for my wife to interject, "You looked
so pretty with that make-up on! I was so proud of you!"
All three of them gazed into my eyes expecting a quick answer. What
choice did I have?
"Y-Yes, I do".
"Now please sit up in your chair and remain still" said the black lady.
My heart sank.
I closed my eyes and braced myself, my mind racing. Lots of men have
pierced ears, I thought, I'll just have to pretend I'm liberal minded.
"Ouch" I said as the first piercing was done. Half in shock, I just sat
there motionless as an identical piercing was done on my other ear. I
was given studs to place in each of the new holes to keep them from
healing shut.
"They look so good on you!" my wife chimed in. "I can't believe how nice
you look! I'm so proud of the progress you've made!" She lead me back to
my room where I had all evening to enjoy listening to Daniela rave about
how good she thought we would both look with our new earrings. The
compliments did help me accept my situation but in the back of my mind I
feared that this took me yet one step closer to femininity. Was there any
way out?
Women's Studies would eventually give all of us difficulty as it included
reading and memorizing some of the articles in women's magazines.
Cosmopolitan, Glamour and Elle became our standard reading material. In
fact we read nothing else. We were being totally immersed in the feminine
way of life.
On one important test in this class I had failed to read the assignment
because I had maid duty the day before. I failed it miserably. Even worse
than Andrea, whom I had suspected of cheating. I then learned why
finishing last in anything was to be avoided.
Even though Cathy tried to talk her out of it, later that afternoon as I
stood bound naked with my legs spread apart, a large dollop of Ben Gay
was smeared on my scrotum by one of Lady L.'s assistants. In a matter
of moments my balls seemed as though they were on fire and the pain kept
getting worse and worse until I begged her to wipe it off which she, of
course, did not. I was in tears by the time the affects of the ointment
wore off. I obediently thanked my tormentor for teaching me right from
wrong and promised that I would do better in the future.
A funny thing about trying not to be last. You never know how good or bad
any one else will be so you are forced to really try to do your best and
not rely on someone else being worse than you.
Such behavior and punishment (I was not alone in receiving this) had an
effect on the entire class. We then made a special effort to learn how to
apply lipstick, mascara, blush, eye liner, nail polish and the like.
Failure was punished, success was rewarded with lavish praise about how
good the makeup made us look. It was not difficult to see that we were
being conditioned to accept our new femininity but despite the entire
group of us trying to think of something, there was simply nothing we
could do about it. At the end of the first 'semester', as our final test
we each had to apply our own makeup as though we were going on a formal
date. After our pictures were taken, (for 'judging' purposes of course)
we were assembled as a group and given lavish praise for a job well done.
Whether we had indeed done a good job or not I really didn't care, just
to hear it from Lady L. herself was relief.
<<<<<<<<<<<<<<>>>>>>>>>>>>>>
In our first class in Feminine Dress and Behavior our instructor told us
that no matter what (if anything) we were wearing at the moment, when we
were around the ladies, we must be wearing a smile. This sounded
innocuous enough but at first was very difficult to do. When you are
naked, ashamed and humiliated, it is difficult to smile. But when you
must as a condition of total obedience, you learn to suppress those
feelings and put on a façade of happiness. This had the odd effect of
making me feel more comfortable around the ladies even when I was naked
and holding my boyfriend's hand. After all, how are you supposed to feel
ashamed while you are smiling? And, of course, it had to be a 'genuine'
smile.
Imagine dressed completely en femme, holding hands with your "boyfriend"
who is also wearing a skirt, smiling at a group of ladies. You naturally
tend to reassess who you are.
In subsequent Feminine Dress and Behavior classes, we learned about
fabrics, what blouses looked best with what skirts, the difference
between mules and espadrilles, shirred versus bias cut, what a "Dolman"
sleeve is and on and on. It was difficult and boring but it was drilled
into each of us with the same rewards for learning and punishments for
failing to learn. Each of us in our own way could still be found to be
rebelling against this forced education. It was unnatural and at times,
even though many of us loved cross-dressing, it seemed that it was too
much against our nature, too feminine, even for a sissy. There was no
respite from the constant bombardment of feminine things. The required
reading of women's magazines. Videos of 'Oprah', 'The Shopping Channel'
and "chick flick" movies. Never even a hint of anything remotely
masculine. No sports on television, no getting together to do "guy"
things. Everything was 100% feminine all of the time.
As pleasant as some of the feminine things we were exposed to seemed, the
complete lack of anything masculine eventually led Andrea to crack. She
went as far as to openly suggest to our sissy group that we all rebel,
steal a boat and take off. Her arguments included the apparent
permanence of our situation and were convincing. Her private plans had
begun to find sympathetic ears the longer we went without any break from
the classes in femininity.
<<<<<<<<<<<>>>>>>>>>>>
A new "term" has just started and as part of our "socialization" training
as the ladies call it, we each were assigned a new boyfriend. I got
Daniela, the one among us that perhaps looked most feminine even without
all of our training. This time I am actually kind of glad about it. He
(sorry, 'she') is very friendly when you get to know him (sorry, 'her')
and we seem to share a lot in common. In addition, our new classes have
started and, as usual, we will attend them together, sometimes naked,
holding hands as we walk between classes. This is particularly fortunate
for me because one of our classes this term is called "Gay By Choice" and
if I have to attend a class like that I would rather be doing it with
Daniela, who is probably the best looking of us sissies. (Yes, I have
finally broken down and accepted the fact that we must always refer to
each other, and indeed accept ourselves, as sissies.)
In Gay By Choice class we first learned about the history of
homosexuality dating back from earliest recorded times until the present,
with a heavy emphasis on how common it once was and how it is now, each
day, again becoming more acceptable. Our instructor gave us heavy
indoctrination in the fact that gays are among the few groups that hold a
parade to express their pride in their beliefs. We learned that
homosexuality is a noble goal that we in particular should strive for.
This was scary. It did not matter how averse any of us were (if at all)
to this orientation. We were given more homework than in any other
class. The daily homework generally was to watch two hours of videos of
attractive males of all ages making love in every way imaginable. I say
love and not just sex because the gays in the videos did seem to be
genuinely fond of each other. There was plenty of romance leading up to
the sexual acts, which were always portrayed as a wonderful and logical
happy ending.
We all seemed to tolerate these classes until our homework assignments
changed. Our period of chastity was increased to almost two months. We
were told that we would see this actually wind up as a reward and not a
punishment. Then, one evening at the end of this period, Jane, who was
Daniela's wife, and my wife Laura, came to our room for a visit. In eager
anticipation we both thought that this might be the end of our chastity
period as they were both wearing the keys to our chastity cages on
necklaces.
"Gurls, it's bedtime!" Laura announced. "But before we release your
members from their confinement, we have to be sure that you are not going
to jump our bones right on the spot!"
Daniela and I were practically drooling.
"So we're going to cuff you before we release you. Now put your hands
behind each others back" Jane said. Daniela put her hands behind her
back causing Jane to roll her eyes and say "No. Behind each others back!"
We eagerly complied, my right arm over his left shoulder and his over
mine. Then each of the women placed padded pink bracelets over their
husbands wrists and locked them into place so that we were hugging each
other and could not jump and grab the ladies.
Then Laura spoke, "To further control the two horniest men alive we are
going to put these collars on you so that we can attach leashes if
necessary."
It sounded wonderfully erotic to me.
Then Jane placed pink dog collars snugly around our necks and connecting
them together as Laura tightly secured a large belt around our waists.
Daniela and I became confused at all of this bondage but there was little
we could do now with our movement so restricted.
Laura again, "And for good measure lets strap your ankles together,"
Which she proceeded to do.
"And now gurls, your release!" Jane then unlocked Daniela's chastity
device and Laura mine.
So there we were. Two nude sissies with the full length of our bodies
pressed together in an unbreakable hug. Two sissies that had not had so
much as an erection in two months.
Laughing with looks of delight on their faces, Laura spoke. "By the way,
we are also here to grade you on your 'How to kiss a man' quiz. So let's
see those red lips pressed together! And if you fail Lady L. will be
informed immediately."
Under these circumstances, Daniela and I both became erect immediately.
Our hairless, naked bodies pressed together and our cocks free at last.
The feeling was just too much. I took one look into Daniela's eyes with
her perfect mascara and eye shadow and kissed her passionately. She
kissed me back and thoughts of a quiz grade evaporated as we opened our
mouths and began to twirl our tongues together. I cared only about how it
felt and not how it looked. I was in heaven.
And so were the ladies. Laughing and snapping pictures as fast as she
could, Jane said, "Well, I guess it is each other that they prefer. There
is no room for a real woman in this scene. I guess we'll just have to go
find us some real men!"
The ladies continued to stand there watching in amazement as Daniela and
I began to hump each others cocks. There was no stopping us now. We
wanted relief. Was it only sex or was it more? Neither of us cared.
Within a couple of minutes we both ejaculated at the same time and
squirted our cum on each other's stomach and cock. It was such a good
feeling. I then gave Daniela a long slow kiss as though to thank her.
As I did that, Laura leaned over me and whispered in my ear, "Thank you
sweetie. I have given you what you really wanted. And you have given me
what I really want. My freedom to find a real man!" With that and an ear
to ear grin both ladies left the room with arms around each other's
waist.
<<<<<<<<<<<<>>>>>>>>>>>
Our bodies were still locked together when we awoke the next morning. I
kissed Daniela and both of our erections returned. This time is was
slower and more passionate as we made love again. For a while I didn't
want our bodies to be separated but it was our day to do maid service.
Eventually two of the large black men from the island came into our room
with keys to both the handcuffs and our chastity devices. They released
us and then stood by and made Daniela lock my cage and I hers, then
giving the keys back to the black gentlemen. We had only enough time to
shower together, dress and head off to the hotel to go clean bathrooms.
On the way, again holding hands, we passed my wife talking to the black
man and getting my key back from him. I smiled at them as required.
The next day I felt ashamed, not even knowing how I could do such a
thing. I was depressed at my situation. I had committed a homosexual
act, was wearing women's clothing exclusively, had several extremely
effeminate tattoos, worked as a maid and was at risk of losing my wife to
another man. Outside of that things were going pretty well. And I still
had to sleep in the same bed with my boyfriend Daniela. There we were
expressing our regrets for being attracted to each other. There seemed to
be no good way to handle this new situation.
I ran into Cathy, our Women's Studies instructor, on the beach the
following afternoon and we got to talking about my feelings. She was
genuinely sympathetic and hinted to me that my situation was not a
permanent one. She left me feeling better about myself. I sensed that if
I ever needed a friend among our tormentors she would be the one.
<<<<<<<<<<<<<<>>>>>>>>>>>>>>
A couple of days later Daniela and I were making the bed in one of the
hotel rooms when our wives walked in. They directed us to move some of
the furniture and to place scented candles around the room. As we stood
at attention at the foot of the bed they inspected every square inch of
the room. They found several 'violations' of their cleanliness rules
which we had to correct immediately. I vacuumed again, dusted again,
cleaned the mirror again and polished the furniture. When they were
finally satisfied, Laura spoke.
"It would be a shame if Lady L. were to find out about all of the
problems we found," My heart sank. Here was my lovely wife threatening
that I would be severely punished.
"We can go two ways on this" Laura said. "I can either turn you over to
Lady L. for punishment, I would probably recommend a Prince Albert
piercing, or you can be here tonight to do exactly as I say, in which
case I would praise you greatly right in front of her. And that would
probably mean less work, more free time, better rations... " She looked
me directly in the eyes. Again, what choice did I have? I opted for the
latter.
At the appointed time that evening I arrived at the room. Laura was there
alone and dressed to kill. She directed me to take off my blouse and
skirt while leaving my bra and panties on. She had me sit in one of the
chairs I had moved earlier to the foot of the bed. Then she cuffed my
wrists and ankles to the chair using the same pink cuffs she had used on
Daniela and I the other evening. I knew that whatever was going to happen
I probably would not like it. She unlocked my chastity device and sat on
the foot of the bed looking directly at me.
"Let me remind you of our little agreement. You obey, you win. You
disobey, you lose. Is that clear?"
"Yes mam."
Moments later there was a gentle knock at the door. I think I knew what
to expect. Laura let in the same black gentleman that had taken the key
from my chastity cage the other evening. "Lynn, meet... well you can just
call him 'Sir'. Sir, meet my 'husband' Lynn.
Lynn is anxious to have me enjoy sex with a real man, aren't you Lynn?"
"Yes, mam."
"You want to compare his cock with your little dick don't you?" Laura
asked me.
"Yes, mam," I replied. The humiliation was almost too much to bear. Laura
then slowly, very slowly removed 'Sir's' shirt, jeans and underwear. She
then took his arm and had him stand directly in front of me, completely
naked. He was truly a physical specimen. Broad chest, ripped abs,
powerful thighs, and, of course a thick, 9", perfectly shaped cock that
would be the envy of any man.
Laura then pulled down the front of my panties to expose my 'manhood'.
She pretended to carefully analyze both members, looking back and forth
from one to the other. "Hmmmm. There seems to be a bit of a difference!"
she said sarcastically. "Now Lynn, do you see why I would rather have sex
with this man than with you? Do you see how masculine he is and how
feminine you are"
"Yes, mam," I choked out the words.
"Are you happy for me and do you want this real man to screw my brains
out all night long?"
"Yes, mam," I whispered.
"I can't hear you and have you forgotten to smile? Remember our
agreement."
"Yes, mam," I said quite audibly this time and with a forced smile on my
face.
"Good," Laura then kissed the gentleman right in front of me and asked
him to help her undress, which he eagerly did. I watched as they sat on
the end of the bed not three feet in front of me making out. After about
ten minutes of this she pushed him back on the bed, got up, took my half-
aroused dick in her hand and whispered in my ear, "I want you to enjoy
this as much as I'm going to. I want you to be happy and supportive. Can
you do that for me?"
"Yes, mam," I said, now with a raging erection.
She then returned to her lover and proceeded to practically jump on his
now erect penis. I watched as he slid his beautiful member in and out of
my wife, first slowly and then more quickly. The sounds were incredible.
Her moaning, his balls slapping against her ass, the wet sounds of her
now moist pussy being penetrated by her lover.
I was erect but could do nothing about it save for dripping a lot of pre-
cum. I was incredibly aroused.
Laura gasped, "Oh Lynn, talk to me. Tell me how much you are enjoying
this. Tell me how happy you are for me."
I did all of those things and with a growing sincerity as I spoke. I was
beginning to realize that she truly needed to be penetrated to places I
had never been able to reach. Eventually they fell asleep in each others
arms while I remained awake for a time to contemplate the fact that I
truly was a submissive feminized sissy.
Thinking about it, there are an enormous number of differences between
men and women; all types of clothing from hats to shoes, makeup, hair,
jewelry, the walk, the curves, the voice, the mannerisms, likes and
dislikes of things like shopping and sports.
I had enjoyed the clothing for many years but that was pretty much the
extent of it. Now I had been “introduced” (more correctly forced) to
accept most of the other things. I now wore women’s clothes exclusively.
I always wore makeup and a wig. I had many articles of feminine jewelry,
including dangling hoop earrings. I had been taught to walk so that my
hips swayed back and forth. With the help of a strict diet, corset and
breast forms I also had developed a passable woman’s physique. I had no
hair of my own below my sideburns. The only books, magazines and
television I had been exposed to for the last 15 months were intended
for the fairer sex. I had several feminine tattoos. I had even been
heavily pressured to accept the gay lifestyle and sex with my fellow
sissies had become the only way I could obtain a release from total
chastity. There was all of this and still the threat of exposure as a
sissy to everyone I knew back home via emails sent by my wife or Lady L.
if I did not cooperate.
Yet despite all of this, thoughts of escaping and starting over still
plagued me. After all, my hair would grow back, tattoos can be removed
and nothing else of a permanent nature except for pierced ears had been
done to me... yet!.
Several in the group were intent on planning an escape by stealing a
boat and taking it somewhere. But where? And how could we steal a boat
when they were constantly under guard by the ladies and the men who Lady
L. had hired to protect her island domain? There was one small airstrip
and plane which was used infrequently by Lady L. or some of her guests
but none of us knew how to fly. Any escape attempt would certainly take
careful planning.
This never had a chance to happen however. Seeing that the group was
divided about an escape plan and refusing to wait any longer, Andrew
(her new name “Andrea”), Harry (“Vanessa”) and Frank (“Susan”) hatched a
plan on their own to escape. They had waited until Vanessa and Susan
were assigned as roommates so no one else would see them leave their
rooms. Andrea had always been in a smaller room by herself as there
were an odd number of us and Andrea certainly was the odd “man” out with
her previous disruptive behavior.
Ignoring the rest of our group, the three left their rooms just before
dawn one morning. They met at a predetermined place and raced down to
the beach near the dock. While Vanessa and Susan hid behind a beached
lifeboat, Andrea began to engage the black male guard in conversation.
Something about not being able to sleep and needing fresh air. With his
back turned, the guard did not see Vanessa and Susan approach him
silently from behind. Vanessa grabbed him around the neck and began
choking him while Andrea punched him in the stomach. He soon passed
out. Then while Susan began making certain that one of the faster boats
was fully fueled, Andrea and Vanessa prepared to cast off the lines
holding the boat against the dock.
They were not aware that there were always two guards watching the docks
overnight. Cathy, our Women’s Studies instructor and my only friend
within Lady L.’s band, who had been down the beach a short distance was
returning to the docks when she heard the noise. She immediately ran
toward the docks and upon realizing what was happening, began blowing a
whistle. When she got there the three were still fueling the boat and
trying to figure out why the key to start the engine was not where they
thought it would be. Andrea jumped off of the boat and ran at Cathy
while she was still blowing the whistle. He punched her right in the
face and she went down.
By now several other of Lady L.’s guards were racing to the docks. As
inept as their plan had been, Andrea, Vanessa and Susan were soon
grabbed by a small angry mob of island men before they even had a chance
to start the boat. They were swiftly taken back to the hotel.
Later that same day, Andrea, who was bound and gagged, was loaded on the
very same boat she tried to hijack. We watched as they took her out
toward the only other nearby island which was barely visible and much
smaller than our own. It was too far away for us to see. When the boat
returned, Andrea was not on it.
The next morning Lady L. gathered the rest of the sissies together in
the hotel meeting room. She seemed calm but the tone of her voice left
no doubt that she was furious.
“As you may know by now there was an attempt to escape the island by
some of your friends early yesterday. During this little escapade,
Cathy, one of your instructors suffered a broken jaw and had to be taken
off of the island. In addition, one of my male assistants was injured
but he will be alright, thankfully. As a result of this you will not be
seeing the leader of these three criminals again. I will not discuss her
punishment with you. Let me assure you she has been ‘dealt with’. The
other two are receiving their punishments as I speak. If any of you have
similar ideas I would highly recommend that you reconsider. For now
guards will be placed outside your rooms and a curfew will be strictly
enforced. If I should EVER even suspect something like this happening
again you will all be dealt with accordingly.” There was no mistaking
the sincerity in her words.
She continued to speak. “As these two will be under the weather for a
while, I want the rest of you to go into their room and do all of the
cleaning required. Are there any questions?”
Instinct told each of us to remain quiet. None of us wanted to be
noticed over the others by asking a question. Lady L. left the room
without saying another word.
While we were being led back to our rooms to change into our regular
maids outfits I thought of Cathy. She and I had become good friends and
I thought that if I ever needed someone inside the clan of our
Mistresses to help me in any way, including an escape attempt, she would
be the one. Now even that slim hope was gone.
We arrived in pairs outside the room of Vanessa and Susan. The first
ones to arrive whispered their guesses to each other as to what their
punishment might have been. Finally, the entire group was there. We
knew that we would make quick work of the room as they were small and
there were ten of us. We were all scared of what we might see when the
door was opened. So we were generally relieved to find that they were
not there, some expecting to see bruised and battered individuals. We
set out to do our work when Lisa was the first to see the newest plaque
above the bed:
CASTRATED,
Chose to lose my balls forever and to be feminine rather than masculine
After sharing a brief moment of shock, then sympathy, then even a little
anger toward them for wrecking any plans that the rest of us might have
had, we started again cleaning the room. I am sure I was not alone in
wondering what had happened to Andrea if Vanessa and Susan had suffered
such a fate. An unspoken feeling passed through the remainder of our
group that there could be no other path than complete acceptance of the
ladies wishes for us.
I was profoundly affected. It was one thing to be feminized and
sissified but I shuddered at the thought of having some of my more
prized parts removed. Somehow a line had been crossed.
The next several days were hard on us. In the classes we shared with
Vanessa and Susan each of us could not help but to try and grab glimpses
of their wounds. As horrible as they were we seemed to need to verify to
ourselves that this did indeed happen. There was no mistaking the stitch
marks and the dejected looks on the faces of the two.
There was a new low point here for our group of sissies as we pondered
our fates.
Then, as if in an attempt to lift our spirits, Lady L. announced that
the island would have some of it’s first visitors and that it would be
our responsibility to prepare for them.
Our hours and our ‘homework’ in Gay By Choice and several of the other
classes were increased. Emphasis on performing gay acts was the
unmistakable message. I could see where this was going. At the same time
our work as maids increased. Even more attention had to be paid to
detail. We basically learned to ‘get it right’ the first time or else.
And the threat implied by ‘Or Else’ had taken on a whole new meaning.
Soon the big day had arrived. Three boats had tied up at the dock all
together. As we had been instructed, and practiced, we each ran down to
the dock from the hotel while wearing only a bikini to welcome our new
guests. With my elbows near my waist and my arms out to my sides I did
an exaggerated feminine trot. If not for the fact that the ten of us
were all doing it (while smiling!) I would have died from the
humiliation. (Vanessa and Susan had been reassigned to kitchen duties.)
Coincidentally, there happened to be ten men all together on the boats.
We took the arms of the men and walked them back to their hotel rooms
while Lady L.’s island men brought their suitcases. After we helped them
settle in, our group of ten sissies was directed to the conference room
once again. There Lady L. explained to us that these were executives who
just happened to have unusual fantasies and fetishes and that it was
going to be our job to fulfill them. Failure in this was not an option.
Later, while the gentlemen were resting from their long journey, we
sissies changed into our French maid’s outfits. This was a time I had
been dreading even though I was well practiced for it and loved cross-
dressing in general. We were to serve the gentlemen appetizers, drinks
and dinner and do it flawlessly. Back and forth to the kitchen while
wearing our outfits, including aprons, garters, black hose, 4” high
heel pumps and, of course, the ever present smile. Soon the gentlemen
came down to the dining room and we sissies sprang into action.
I had gotten through the dinner without error but while serving desert,
I carelessly dropped a fork on the floor. Fortunately, I remembered to
keep my knees together shifting them slightly to one side when I stooped
to pick it up. I prayed that this small infraction would not bring
consequences.
We served our guests their after dinner drinks and thought we were
nearly done when Lady L. gathered us in the kitchen and said, “OK gurls,
so far so good. Now the gentlemen are gathering in a circle in the
lounge for a little review of each of you.”
A look of surprise shown on all of our faces. She continued, “You will
each walk out one at a time with your sexiest walk, stand in the center
of the circle, do a little spin for them, pausing if they want you to,
and walk back here. Does everyone understand?” It didn’t matter if we
did or not. We were on our way without ever having rehearsed this part.
One by one we each did exactly as instructed. First Lisa, then Charlene
then George (Gail) who, due to her weight drew a little good natured
laughter. By chance I would go last and Daniela was right before me.
Daniela was naturally attractive with a petite build and a pretty face.
She got several Ooohs and Ahhhhs. I knew I couldn’t match her but that I
had better try. With ten men gawking at me wearing a pretty French
maid’s outfit, I was as humiliated as I have ever been in my life, I
knew every inch of me and every movement was being scrutinized by a
group of gentlemen strangers. I was careful to take small mincing steps,
sway my hips without overdoing it, smile the brightest smile I could
muster, and as if to enhance my humiliation, I made eye contact with
each man. This required me to spin twice instead of once but I could
tell that I was attractive to several of the men. This made me proud of
myself (and glad that I was wearing my chastity cage!) As I walked back
I kept my smile but it was no longer a forced smile. And as I got to the
edge of the circle, I turned and bowed in a deep curtsey without even
knowing why. At this the men applauded. I had nailed it!
We were to learn that the men had used our display to rank us as prizes
in a poker game they were about to start. Winner got first choice,
second got second and so on.
I was changing. forced together under unbearable conditions and
unbreakable rules, we were all learning to handle it in our own way.
There seemed to be no other course than to cave in to the ladies desires
for us, desires that seemed much more clear now. This fact did not go
unnoticed by Lady L. While the men played poker, she praised us and told
us to think of ourselves as the “third” gender. Not women and certainly
not men but we were attractive to these gentlemen. As such, she
instructed, we should accept any sexual offering that they make and do
our absolute best to please them. “Pleasing a woman is beyond you” she
said, “but pleasing these men is what you have been trained to do!”
They had indeed been training and conditioning us to accept and actually
prefer same-sex relationships. Acceptance of this ‘behavior
modification’ was easier for some than for others as most of us had some
gender issue to begin with. I think I fell somewhere in the middle. It
was not going to be easy to make the transition. The ladies had
treated us as a team and set before us a team objective of becoming
feminine males. Defeat was unacceptable and victory required complete
obedience to our “coaches”.
It seemed our next competition would be to win at being the best at
pleasing the man who picked us to spend the week with.
.
I HAD changed. But subconscious doubt still lingered.
It was very late when the poker game ended. By then we had done all of
the dishes and cleaned up the hotel’s dining room. Next, and while being
pretty much exhausted, we were instructed to stand at attention in a
neat row still in our French maid’s outfits. This time it was our wives
who were telling us what to do. Lady L. was relaxing and taking it all
in from her easy chair.
As we stood, the gentlemen sat in comfortable chairs facing us. Lady
L., with some fanfare, then announced the winner of the poker game. Bob,
of course, chose Daniela who stepped forward, but was then ordered by
her wife to sit in Bob’s lap. The whole room (sissies excepted) thought
that this was a great idea, and each of us would end up doing the same
when our name was chosen. Lisa went next. I wasn’t as concerned when I
would be picked as who would pick me. There were some less than
attractive men in this group.
I was fortunate enough to be picked third and by a relatively decent
looking guy, Steve. He was taller and larger than me, I was 5’11” and
(with my dieting) 150 lbs. while Steve was around 6’2” and looked to be
slightly over 200 lbs. I went to sit on his lap and he immediately put
his hand on my thigh and began rubbing it up and down. We both smiled at
each other. He had gotten what he wanted and I had gotten what I learned
that I had wanted. My wife was very pleased. She came over to Steve and
I and gave me a kiss on the cheek. And then she gave Steve a kiss on his
cheek. “Now you’ll take good care of my little sissy this week won’t
you?” she asked. As embarrassed as I was I kept smiling.
“Oh I’ll take the best of care of her little sissy ass! Ha, Ha, Ha! You
can bet on it!” he replied.
My wife simply beamed as she then went back to stand with her
boyfriend., the same one she had had sex with while I had watched.
Mentally, I think the only way to survive a situation like this is to go
with the program. You would go crazy if you tried to fight it to say
nothing of the consequences if you did not please your new gentleman
friend and Lady L. were to find out.
Steve kept rubbing my thighs as the men’s other choices were made.
Honestly, it felt wonderful.
And last, Gail ended up with Tim who seemed just odd enough to have
thrown the poker game deliberately just to get last pick.
At that point we all stood to return to our rooms. Or that is the
gentlemen’s rooms. Already well tanned, Steve let his arm slip from my
shoulder to my waist as we walked down the hall to his hotel room.
“Thank you for picking me,” I said, thinking that this would have to be
the right thing to say.
“Oh, my pleasure, believe me it WILL be my pleasure, Ha, Ha, Ha!” was
his reply. A little tasteless, I thought, but I smiled back at him for
saying it anyway.
When we got inside his room we both sat on the bed and I nervously began
to make small talk.
“Where are you from?”
“Texas. Lynn...that is you name isn’t it?”
“Uh Huh,” I answered affirmatively.
“Just how does a pretty boy like you end up being a chick with a dick if
you don’t mind me asking?”
I did mind but pretended not to. “Well, I always had a strong urge to
get in touch with my feminine side, I guess.”
“Well in your case your feminine side seems to be about 99% of you, Ha,
Ha, Ha!”
I was getting angry at this line of questioning but could not show it.
“Lady L. and my wife have helped me along in realizing how much fun it
can be to dress up.” I thought this was the safe answer.
“Oh you’re doin’ more than dressing up my little lady! Lady L. says
you’re a little firecracker!”
I was getting even more nervous. “Well I do hope to please you, Sir.” I
was terrified of what would happen if he did not approve of me. I tried
to focus my thoughts on doing the best I could to please him.
“Well thank you mam I’m sure you will. Ha, Ha, Ha. Now why don’t you hop
out of that pretty little dress?”
I smiled at him as I took off my French maid’s outfit, including the
corset which was killing me by now. I was honestly hoping he would
prefer to nod off to sleep given the late hour, but no such luck.
As I lay on my back, wearing only makeup, a wig and my chastity cage,
Steve climbed on top of me, raised my head in his big, strong hands and
gave me a deep kiss. Our mouths opened in unison and our tongues met. My
chastity cage was becoming painful as my penis tried without success to
grow. We kissed for a long time before Steve spread my legs apart with
his.
I hadn’t thought about it this before but I was about to be “bitched,”
getting screwed in the ass for the first time. The idea frightened me in
that it would be yet one more step in my feminization which I could
never again deny happening, at least to myself.
I applied lube to my boy pussy in expectation of this moment. I felt
Steve gently place his manhood at my opening and slowly begin to enter
me. He was big but went slowly enough that I felt only pressure and not
pain. Ever so slowly... deeper... deeper... deeper inside of me as my
boy pussy slowly expanded to accommodate his erection. My own penis
hurt from the cage but I knew I was there only to please Steve. “I want
you in me,” I whispered. He held his entire 7” inside of me for what
seemed like an eternity before he started slowly rocking, out.. in...
out... in. He gradually began to pick up the pace until he was pumping
me hard and fast. I began to moan softly with pleasure until I could
tell that he was about to cum. Then my moaning became much louder.
”...Oh...Oh... Ohhhhhhhhhhh!” Squeezed inside its tiny cage, my penis,
straining to become erect, oozed out a dollop of cum at the same time
that Steve released his load.
He gave me one more lingering kiss before falling asleep still on top of
me.
The next morning Steve had gone fishing before I got up. I was thankful
for that as I was exhausted from the day, and night before.
The next couple of days we spent some time together, sunning on the
beach or going for walks. The rest of the time Steve talked to the
friends he had arrived with about their boats or other ‘manly’ things
while us sissies chatted about our new ‘boyfriends’. So this is what
being a woman is really like, I thought.
Then, each night, it was back to bed with Steve, and I didn’t get much
sleep.
By Wednesday it was time for our mid week review by Lady L.
I was shaking as Lady L. read Steve’s comments:
Lynn was a delight except for two little things, she did not anticipate
my needs (like a Scotch the way I like it after noon) as well as she
might have, and she seemed a little too nervous in bed, insisting that I
wear a rubber. If she can get over these things I would love to see her
again next time.
Lady L. summarized the review for me, “Well, you definitely have some
work to do. You should know what he wants even before HE does. Be
constantly thinking one step ahead of him. And then, you insisted he
wear a rubber!?. How could you? You should have known that our guests
are clean. If bareback is what he wants then bareback is damn well what
he better get! This is highly embarrassing for me! My friends are very
clean and don’t need to wear condoms if they don’t want to.”
I nearly broke down in tears at the tone of Lady L.’s voice knowing that
this almost certainly meant severe punishment.
“Still...” Lady L. continued, “he did say that he definitely wanted to
spent the rest of the week with you and that is a big plus. That IS
important. At least you don’t scare him away.”
Hearing this stopped a potential flood of tears on my part.
“Oh, by the way, did you curtsey for him each time you left the room?
He likes that.”
Pause. “Uhh... no,” I said meekly.
“Well next time remember that.” Then Lady L. paused. “Good and bad. I
think that indicates both a reward and punishment are due!” she
s****ered. “I think a second piercing in each ear is called for. Steve
likes lots of jewelry on his gurls. You’ll have the prettiest ears on
the island!”
My heart sank as I felt that this act of discipline would remove even
more of what little masculinity I had left. Then Lady L. surprised me
again.
“And as for your PUNISHMENT, how about a little fairy tattoo just above
your ‘cock’.”
“Oh god not another tattoo,” I thought.
I was relieved but still haunted by deeper thoughts. I had all but
given up trying to escape the island. Now I had multiple feminine
tattoos, wore only women’s clothing, was about to receive a second ear
piercing on each ear, and had made love only to men in the last 18
months. No real man could say this I thought. In addition, Steve would
be coming back before long. Mmmm...Steve. I was beginning to believe
that I could never be a man again. Could I accept this? The canings
and Ben-Gay that made my scrotum burn would be painful but temporary.
The tattoos and piercing were of a more permanent nature and would make
any hope of some day returning to manhood seem even more distant.
Still, I had to soldier on because there were punishments that were even
worse. In the back of my mind lurked the horror of castration or even
worse, if there was anything worse than that.
We had come to the island as a motley, diverse group of transgendered
males. Those of us remaining were now totally obedient, submissive,
feminized sissies, willing to do absolutely anything we were told to do.
We were physically still males but any vestige of masculinity was gone.
Each of us began to fully accept our true roll as servants to a superior
gender.
It was Saturday and Steve would be leaving the next day. I had
pleasured him in one way or another each night of his stay so far and as
a result, he asked my wife if he could have the key to my chastity cage
for one day. She agreed on the condition that any release that I have
be done in a way that would humiliate me. She explained how that helps
me maintain my submissiveness. She agreed to his offer knowing that I
had indeed pleasured him each night as she had the videos taken by the
**********era in Steve’s room as proof. Any images of Steve that were
identifiable were destroyed by agreement with Lady L. Any videos where I
was identifiable were copied, cataloged and saved in a secure place.
As a surprise, Steve asked me if I wanted to go up in the plane with
him. I was overjoyed. This meant that he must have approved of me. I
quickly agreed.
He knew how to fly too! There was so much he could do that I could not.
I even asked him about the controls, perhaps subconsciously thinking
that I could fly off of the island. He pointed to this dial and that
switch while rattling off some technical jargon and I quickly gave up
that idea.
He took me high enough to see a couple of other small islands.
“I’m not sure but I don’t think this looks like the Caribbean,” I said.
“Ha, Ha, Ha,” Steve laughed. “Who told you that? We’re a little north
of Madagascar!”
I was shocked. The sissies had been lied to since the beginning.
Andrea never had a chance to escape from here.
The next day he offered to take me out on his boat. The only condition
was that I wear the bikini he saw me in the first day he arrived and,
again, I readily agreed. He took us out several miles before shutting
off the engine.
Suddenly a thought came over me. A terrifying thought. This might be
the only chance I would ever have to leave the island. While Steve was
concentrating on steering the boat out to sea, I had noticed a boat hook
attached to the side of the boat by clips. It was simply a rod about
six feet long with a hook at the end for grabbing things out of the
water. I quietly removed it from its fasteners. Gripping it like a
long baseball bat I would be able to swing it freely and certainly be
able to at least disable Steve. I hesitated just a moment. I couldn’t
do it! I held the boat hook poised to swing but I could not do it! I
quickly lowered it when Steve began to turn around. I held the end of
the pole in my hands and began sliding one hand up and down the last
foot of its length, stroking it gently.
I smiled at Steve as I did this and a moment later he caught my idea and
smiled back at me. He then stopped the engine, took me by the hand and
led me to the stern of the boat where he sat on the cushioned seats
there. He then took a life preserver and set it on the deck between his
knees. I understood what he wanted. Kneeling on the life preserver I
began to slide his bathing suit down his legs then lifting them so I
could remove it completely. I noticed for the first time the amount of
hair on his legs... and his arms. It was thick yet curly and soft. I
ran my hands through it as he had run his hands over my hairless thighs
as I sat in his lap after the poker game. I could not help noticing the
contrast between his arms and legs and mine. His were the arms and legs
of a real man. I had only perfectly smooth skin, feminine skin,
highlighted by the fact that I was in a bikini. No REAL man would EVER
be in the position I was in wearing what I was wearing, doing what I was
about to do. At no other time in my life was I as aware of who I was
than at that moment.
I began gently caressing his penis. My mind began to wander. When he
had reached his full erect length I began kissing it. I wanted to make
love to it. I gently cupped his balls in one hand while I lightly
grasped his shaft in the other. I kissed the entire length. I sucked
on his balls until he started to groan. I licked around his penis. I
licked under it. I ran my tongue slowly up its length, then down, then
up again pausing to put my lips around his corona. Sliding his
beautiful penis slowly into my mouth inch by delicious inch until my
nose was nestled in his light brown pubic hair. His penis was touching
the back of my throat but I was able to suppress the gag reflex because
I had been trained to do so. I let my mouth linger there as Steve began
to groan louder. I wanted to please him. I wanted his penis to feel
the warmth of my moist throat. I wanted to use every lesson I had
learned about performing the perfect blowjob. Excruciatingly slowly I
brought my lips up the length of his shaft. I paused with my lips again
caressing his glans and my tongue flicking the underside of its head.
Steve grabbed my head and began to hump my face. All that mattered to
me was that I pleasure him as he has never been pleasured before.
Nothing else mattered to me. I was going to make him experience ecstasy.
From the volume of cum I swallowed I think he came pretty close.
A minute or so later Steve finally caught his breath and then reached
down into the pocket of his bathing suit and produced the key to my
chastity cage. My eyes widened as he unlocked the wretched device and
my cock sprung free. That felt wonderful but it got even better as
Steve put his large hand around my shaft and gently squeezed. I began
to raise my hips to gain some friction but Steve told me to stop and
remain motionless. It was a heavenly torture. I wanted desperately to
reach an orgasm but could not. One minute. Two minutes! Then Steve
told me to repeat what he was going to tell me to say.
I think it went something like this:
“Mr. Steve Sir, for you I promise that I will be YOUR gurl whenever you
come back to the island.
For myself I promise that I will work to become more feminine every day.
For my Mistress wife Laura, I promise to let her have sex with whoever
she pleases.
For Lady L. I promise to work as hard as I can to please her in every
way possible.
For all other ladies everywhere I promise that I will never think of
women in a sexual way again.
“Ha, Ha, Ha!” Steve laughed at that last one.
He then stroked my penis and I quickly ejaculated with my cum running
down on his hand. He held that hand up to my mouth and I licked it
clean. Then he locked me up once again in my chastity cage.
In his final comment, Steve said, “I am going to tell Lady L. exactly
what you just said. After all, this will give everybody just what they
want!”
“Yes, Sir,” I replied with my mind gone blank.
Steve let me steer the boat back to the island and over the drone of the
engines he said, “Hey, let’s get that down in writing! And you’ll
agree to sign it or this only key to your cock cage goes overboard. And
there is no locksmith on the island. Ha, Ha, Ha, Ha!”
Why he had chosen to be so cruel after what I had done for him I didn’t
know. I didn’t care.
And with that my fate was sealed.
Shortly after the gentlemen had left the island and I had indeed signed
a letter acknowledging what I had stated on the boat, Lady L. gave us
our final reviews. They were generally excellent with mine ranking among
the best and she was beaming with pride. She then happily announced, “We
are going to hold a graduation ceremony for you gurls! Instead of a cap
and gown you will get to wear an EVENING gown and be recognized in front
of all of the ladies and men on the island!”
The actual ceremony turned out to be similar to our parade in front of
the gentlemen in our French maid’s uniforms, except we were now decked
out in beautiful evening gowns in front of perhaps fifty ladies and men.
This time it was easier for me as I dreamed how good I must look in the
silky fabric, beautiful jewelry and perfect make-up.
Following the ceremony I saw my wife, Laura, leave TWO men to come over
to congratulate me. “I’m so proud of you for following this through!”
Laura exclaimed. As if I had a choice.
“I hadn’t realized by your cross-dressing you were screaming out to me
that you really wanted to be a woman! You wanted to be the person that
is caring, devoted, submissive, obedient and pretty to look at all at
the same time! When I realized that I had missed all of the signals I
knew I had to help you to become what you really were all the time!
You’ve really earned this!” With that, she kissed me on the cheek and
went back to her boyfriends. I couldn’t tell whether she was mocking me
or being genuinely honest.
It didn’t matter.
This IS who I am now. If I ever was a man I’m not now so I had better
learn to make the best of it. I really DO want to please the ladies on
the island and I know that if I try hard enough I will be able to.
Above all of the promises I had made to others, I decided to promise to
MYSELF that I would do the best job I knew how to as maid, servant,
danseur or anything else Lady L. or Mistress Laura wanted of me.
Manhood had slipped far away. Over the last two years in which I had
experienced only feminine things I had forgotten who was on which
professional sports team and even the names of some of the teams. Such a
lack of knowledge would have been more embarrassing if I had anyone to
carry on a masculine conversation with but I did not. The occasional
visits by men to the island did not help me relate to the outside world
as they never talked "guy" stuff with us sissies. We were left to chat
amongst ourselves about the latest fashions, fabrics, and famous
females.
Could I ever be a man again? I tried to put this question out of my
mind as it wouldn't matter under the current circumstances. And it
didn't look like the current circumstances were going to change. All of
us sissies were kept in chastity for long periods and the only release
we were allowed was with men visiting the island or with each other.
Before I had arrived on the island being forced into this type of
behavior would have seemed impossible but sex is a powerful motivator
and the ladies knew it. They had provided the physical and mental
punishment and scaled it up as high as necessary to get each of us to do
what they desired. Eventually, each of us succumbed to their superior
power and accepted a gay lifestyle. What had seemed so unnatural at
first now seemed erotic. Ahh the power of an "education" at the
W.I.T.C.H. Institute.
Over the next two months a few men visited the island. There were never
enough to go around for each of the twelve of us sissies remaining here.
But this was a good thing for the visiting men as they then got to
choose between us. Daniela was chosen most frequently, every time in
fact. We all knew that she was the most attractive and passed as being a
real female quite easily. I was afraid to admit it to myself but this
was making me jealous of her. I was often left to my maid duties while
Daniela was being wined and dined by one of the male visitors. It was
particularly frustrating to have to make the bed that she and her male
friend would soon sleep in or had just slept in. But I did it just the
same and I did it with a smile on my face as was required of me.
Perhaps this is why I was so happy when, one day three men arrived at
the island and I was chosen by the one named John. After all, the
competition was tough. Each of us sissies greeted them in the usual
way, by running down to the beach in our bikinis and begging to be
chosen as their consort for the week.
I was hoping that John chose me because he liked the way I looked. By
dieting I had lost even more weight and had gotten a nearly perfect tan
by making sure that the strings to my bikini were in exactly the same
place each of the times I was allowed to lie on the beach in the sun. I
had been paying much more attention to such things recently because my
wife encouraged it and these were important to a "gurl" trying to
attract men. After all, this was the only way any of us would be
granted a sexual release.
I felt rewarded for all my hard work that night when I saw John naked
for the first time. When erect, his cock was a full 10" long! It was as
long as any of the hundreds of cocks I had seen in photographs during my
classes. I could finally understand why women were so attracted to such
a display of manhood. After having seen so many naked males up close,
VERY close, I was beginning to appreciate certain qualities in a cock.
Length was definitely one of them and John's was, simply beautiful on
that score. A cock had become my main source of physical pleasure and I
had learned to appreciate the opportunity to please them with my lips
and tongue. This is why John was such a special treat for me.
On John's first night, while I was on my knees pleasing him with my
mouth, I looked up into his eyes and found him looking down into mine.
No words were spoken and none were needed. At that moment the dramatic
difference in our status was crystal clear, and seemed so right. This
wonderful specimen of manhood also reinforced my acceptance of what the
ladies had taught me, that some of us were just meant to be "real men"
and some of us sissies. It made perfect sense that he is what he is and
I am what I am.
I later learned that John was not only talented in the bedroom, but had
made a considerable sum developing a popular app for smart phones. It
made me doubly proud that he had chosen ME to be submissive to him. He
had proven himself to be a real man in the business world as well.
Something I had never quite been able to accomplish.
And it is a good thing John had a lot of money. You seemed to need a
considerable amount to visit this island because you needed a boat or
plane to get there, to say nothing of the fee that Lady L. must be
charging for the accommodations and the services of us sissies.
Naturally, we never saw a penny of those fees and there was no place to
spend them if we did.
My week with John seemed to fly by and my only regret was that he did
not want to kiss me. I had learned that not wanting to kiss a feminine
male is just a peculiarity that some men have.
That wonderful week was followed by a less auspicious one. My wife Laura
had decided to make a change.
"Lynn, I was so happy that you really got to hit if off with John. It
makes me feel so good that you have found yourself, that you now know
who you really are. There is no shame in being a complete sissy. It's
wonderful that you are able to make love to only men now and that you
accept that you are a total submissive to both women and men."
The way she had just blurted these thoughts out shocked me.
"But," she continued, "it is now time for me to find MYSELF. I have had
divorce papers drawn up so that we can each follow our own destinies.
Our paths have always been separate ones, you an effeminate submissive
sissy wanting to be completely dominated, and me, an attractive,
dominant woman desiring to make her mark on the world!"
I was blown away. "B-b-but you're dominant and I'm submissive. You said
so. So why can't you just dominate me while we stay married?"
"Lynn, I HAVE dominated you, TOTALLY. And now it's time for me to move
on. Look at you in you're pretty little skirt and blouse. This is your
future. But there is no room for that in my future. I am going to want
REAL men. In fact, Marc and Darius are going back to the States with
me."
I knew, even if I never admitted it to myself, that she had fallen in
love with one or both of these other men, but, despite this, I could
still never envision her leaving me. "B-b-but Laura, I thought you still
loved me," I said, starting to cry.
"Oh, but I do! That's exactly why I am doing this. I hope you appreciate
ALL I have done for you... letting you wear women's clothes, encouraging
you to become more and more feminine, helping you become gay, just like
you wanted!"
Did I want that? Or was it forced on me? I could not deny that I now
enjoyed having sex with other men and that I loved women's clothes. I
couldn't seem to find a hole in her argument. "But I don't want you to
leave!" was all I could think to say.
"Lynn, dear Lynn, you'll always have the memories of me and I will leave
you with pictures of me and I will keep pictures of you, recent
pictures." She stifled a laugh. "Don't you want me to be happy? As happy
as I've made you?"
Thinking as quickly as I could, "Of course, but I won't be happy without
you!"
"Now Lynn, you must be realistic. I would only be in the way of you and
your lovers. You have a wonderful job here and what about your many
friends, all of your 'boyfriends'? It IS the way it has to be Lynn."
I was out of arguments. What could a submissive male say to change the
mind of a dominant woman? Nothing I could think of.
"Here Lynn, sign this, here and here" she said as she pointed to the
divorce decree.
I tried to hold back a flood of tears unsuccessfully. "B-b-but what
about our house back home? The one we bought together?" As though
anything back home would do me any good now.
"I'll keep the house and whatever else we owned. You won't be needing
anything you don't already have here. So it only makes sense that I have
it. In fact I think I'll put a big picture of you as you are now over
the fireplace. It will help me remember you as the sweet generous little
sissy you are."
"Won't I ever see you again!?" my desperation growing..
"Well, as happy as you are here, you have no reason to leave the island.
Besides, I threw out all of your male clothing back home. I knew
you'd never need them again and they won't fit Marc or Darius, you're
smaller than they are." Again she stifled a chuckle. "Now sign unless
you want to go discuss this further with Lady L.".
I could not refute anything she had said. I could not go back to my old
life and I was not about to lose all of the goodwill I had built up with
Lady L. over an argument I could not win. With tears flowing freely, I
signed.
One week later, at the 'urging' of Lady L., I reluctantly said my
farewells to Laura, Marc and Darius as they left on the nicest boat
still at the dock. "Goodbye, Mistress Laura, I love you and thank you
for everything you have done for me." I had to say this even though I
knew that this could be my final admission that I would never leave this
island.
As the boat slowly pulled away from the dock the image of Laura's face,
as happy as I had ever seen her, was burned in my mind.
It had hit me like a ton of bricks as I knew deep down that there was no
way I could ever go back to living anywhere but here with anyone but
those that already lived here or came to the island. I loved Laura and
hated her at the same time for leaving me.
<<<<<<<<<<<>>>>>>>>>>
Several days later, while Lisa (Edward) and I were cleaning one of the
hotel rooms, the subject of Andrea had come up. "What do you think ever
happened to her?"
"I don't know but I hate to think about it."
Just then Lady L. and Cathy entered the room. Lady L. spoke, "Oh hello
gurls. I just wanted you to know that Cathy was back. She's fully
recovered from that beating she took when Andrea tried to escape. I
overheard you and funny that you should be asking about Andrea. Do you
want to see her? I think she might enjoy it actually."
Lisa and I looked at each other, speechless.
"Well I'll arrange something for all you gurls. That will satisfy your
curiosity. In the mean time, how about a welcome back for Cathy?" asked
Lady L.
Both Lisa and I gave her an enthusiastic welcome at the same time. She
was indeed welcome as she was not only the most friendly of Lady L.'s
assistants but she was also the most beautiful.
The following Sunday, when all of the work and class schedules of the
sissies allowed it, we gathered together at the dock. (I say Sunday
because that's what day I thought it was. Actually, each day, each week
and each month blended into the next so I really didn't know when it
was.) The sissies were tied to each other with soft but sturdy pink
handcuffs and helped onto the largest of the boats by three of Lady L.'s
male assistants.. By this time thoughts of escape were gone but Lady L.
was never again going to risk it.
As this was one of the slowest boats it took us quite a while to reach
the smaller island where we had indeed guessed Andrea had been taken.
All of us sissies were sharing a nervous curiosity as we were helped
from the boat by the three male assistants.
"Follow me gurls." Lady L. said as she walked from the beach to a narrow
trail in the underbrush. About 100 meters in, we came to a clearing
with a small hut in the center.
Lady L. went into the hut and soon emerged at the doorway to announce
"Gurls, the Queen of the island!" Holding the woman's hand in the air,
Lady L. led Andrea in to a spot in front of us.
Her face, although made up in an exaggerated fashion with eye shadow,
mascara and lip stick, left no doubt that this was indeed Andrea. From
the neck down, however, she was unrecognizable as Andrea. She had a
beaded necklace hanging over small uncovered breasts, a very narrow
waist supporting a grass skirt, and bracelets all up and down her arms.
Her own long, uncombed hair was topped off with a gaudy tiara.
None of us sissies could speak as our mouths just hung open is
disbelief. Lady L. broke the silence, "Sissies, curtsey to your Queen!"
The authority of Lady L. was all that was needed for us to obey. We all
did as directed although in a very unorganized manner.
"I am your Queen and you are my subjects" 'Queen' Andrea had spoken.
With the sight before us we didn't know whether to laugh or just try to
remain silent. Between us there was a little of each.
Lady L. again spoke, "Your Majesty, why don't you show your subjects the
changes that have made you even more beautiful now?"
With that, Andrea removed her grass skirt and revealed a surprisingly
attractive hourglass figure. Except for her jewelry she was completely
naked as she did a slow turn before us.
The sissies still had trouble speaking as we each took in this image. We
began murmuring amongst ourselves. "She must have been put on a large
dose of female hormones to develop her breasts and expand her hips like
that" said one. "There has definitely been some serious corset training
too" said another. With her private area smoothly shaved it was obvious
too, that her Prince Albert piercing was still in place. She clearly
would not, could not use her male parts for sex of any kind.
Annoyed with the whispering of the sissies, Andrea declared "Silence! I
am your Queen and you are my subjects!"
Lady L. turned to us, "Gurls...?" hinting for us to do something.
Gail caught what Lady L. had implied and quickly curtsied with the rest
of us following. Lady L. then led 'Queen' Andrea back to her hut. "I am
your Queen...."
"Susan and Vanessa" Lady L. said in a matter-of-fact way, "I want you to
stay with your Queen. She will appreciate the company and I think you
will too." Susan and Vanessa had been gelded as punishment for their
roles in Andrea's failed escape plot. With hopes that this might provide
at least a bit of the freedom from the W.I.T.C.H. institute that they
had learned to hate, they willingly agreed. They had never been great
fans of having to meet and entertain any men that visited our island to
say nothing of losing their manhood there.
On the boat headed back to that island we were still somewhat in
disbelief. Relieved that nothing worse had happened to Andrea and yet
surprised at what HAD happened. Clearly some type of 'medication' had
been part of her punishment.
"You know," said Charlene jokingly and perhaps with a hint of jealousy,
"she's smokin' hot!"
"She's smokin' something!" I chimed in.
We all laughed, including Lady L.
<<<<<<<<<>>>>>>>>>>
The next week was relatively uneventful and we all did our maid duties
and attended our classes as usual. There was one change, however. Susan
and Vanessa had been our main chefs and were responsible for preparing
most of the meals. Without them the rest of us had to take on a class
in cooking. Mistress Noreen, herself an accomplished cook, took on the
task of teaching us. The class was pleasant enough except for the
Mistress's habit of continually reminding all of us to keep our knees
together We each wore the standard short, pleated plaid skirt for class
and often one or more of us would fall into the old male habit of
letting our knees drift apart a few inches.
"Knees together gurls!" she would say whenever she noticed. Over time
this began to bring a smile to my face as I dutifully obeyed. I found
this class a pleasant change from some of the other more mundane tasks
us sissies were required to perform. It meant that I was learning yet
one more traditionally feminine skill. Complete feminization is a big
job but I was well on my way.
Life on the island was beginning to get more interesting. One day Beth
and Irene (formerly Bradley and Irv) made a surprise announcement that
they were going to get married. Lady L. had granted them permission to
become 'husband' and wife. Which would be which no one seemed to care
but we were all genuinely happy for them.
Reflecting, I guess it was only natural as they had been through so much
together and had been taught to accept a same-sex lifestyle as we all
had.
Perhaps most surprising was the fact that Lady L. was going to allow
them to return to the States to live as domestic partners. Since this
turn of events had fulfilled all of the goals the spouses of these two
had set for them, Lady L. was very confident that her work on them was
now complete.
Was this a course I too should pursue? What had been my wife's goals for
ME? She had left the island telling me that I had already achieved
them.
The remaining island sissies, including myself, were truly happy for the
lucky couple. A ceremony and celebration were in order. To make it
legal, their wives had also made them sign divorce papers and Lady L.
had arranged that they would be married by the 'captain' of the next
vessel that would visit the island. We were told that such a ship would
be arriving in exactly one week. That did not give us much time to plan
the ceremony or make wedding gowns for them. They would, however, be
wearing beautiful matching white dresses. The variety of women's
clothing that Lady L. had made available to the sissies never ceased to
amaze me. I was never sure where it had come from. Perhaps delivered
by one of her visiting gentlemen friends in payment for a week of
pleasure?
With such a short time frame there wasn't a moment to lose, what with
our routine maid's work and classes. (Although Lady L. did suspend
classes except for Cooking in which we quickly learned how to make a
beautiful wedding cake.) Many of our experiences in feminization were
paying off for the first time. Collecting and arranging flowers, sewing
dresses, planning and cooking the reception dinner, helping each other
get our nails and hair done. It is amazing what the feminine work ethic
can accomplish when tasked with such an enjoyable event.
When the big day arrived I was tired but happy that we had been able to
bring it all together. There was not a large crowd sitting in
attendance as all of us sissies were standing up as bridesmaids for the
happy couple. We had argued about what our dresses should look like but
finally decided on a light blue satin dress with a sweetheart neckline
and cap sleeves. It was gathered on one side at the waist and had a
back zipper and small slit at the bottom in back. I loved it. As long
as I could remember I enjoyed cross-dressing but this was a most
wonderful feeling looking as feminine as I did.
It was a beautiful ceremony and the reception was lovely. I got to
dance with the 'captain' and several of the other sissies. All in all I
had an amazing time. It made me reassess how nice it felt to be
feminine instead of masculine. The day that Beth and Irene left for
home and a honeymoon, I actually became jealous of them. Having just
finished the now requisite two months in chastity I begged Charlene to
make love to me. She was just as anxious as I and we ended up spending
an entire night kissing, caressing and having oral and anal sex.
After having spent over two years without so much as touching a woman it
was much easier now to accept that I would probably never have a
heterosexual experience again. In all of this time women physically
would have nothing to do with us sissies and yet us sissies (when not in
chastity) were always available to each other. We looked feminine. We
acted feminine. The transition to homosexuality had become fairly easy.
<<<<<<<<>>>>>>>>
There was even more news the following week. Lady L. had informed us
that we were going to have some unusual guests that weekend. These
guests were going to be ladies. Real ladies. Not only that, they were
the spouses of other unsuspecting males like us island sissies. They
were going to be shown the facilities of the island and the curriculum
of the training classes. It was an important step in convincing the
ladies that this was indeed what their spouses needed to adjust
whichever of their behaviors that was inappropriate or not to their
wife's liking.
As one would expect, Lady L. gave us a stern warning about being on our
absolute best behavior while the guests were here. She strongly hinted
at the fact that 'Queen" Andrea might need a couple of 'princesses' on
her island. The implication was crystal clear. Any error on the part of
a sissy could result in a fate like that of Vanessa and Susan. We, in
fact, were going to be instrumental in convincing the ladies that their
husbands NEEDED to be sissies.
The big day soon arrived. We island sissies were already at the dock
waving when the boat pulled up. I heard one of the ladies say to
another "Why are there girls here to meet us? I thought we were going to
see some sissified men!" The lady she had spoken to turned and whispered
something in her ear and she froze, mouth open, staring at us.
"Wonderful!" she said as she began to laugh.
The ladies were all types, young, middle-aged, thin and fashionable,
somewhat over- weight. For some reason the heaviest one instantly took
a liking to me. Perhaps I looked like her husband. In any event, she
was also the jolliest and most talkative one.
"Oh sweetie, we're going to get along just fine! I'm pickin' you! I
hope none of you other ladies mind!"
The other ladies seemed to be so delighted with the whole scene at the
dock that they had no trouble picking one of the other sissies for
themselves and leaving Mistress Marge to me. ('Large Marge' I silently
thought but would never say out loud.)
The sissies took the lady's luggage to their rooms and began to explain
where everything was, much the same as we had done when men visited the
island. When they were settled in Lady L. had the group convene in the
hotel's conference room to go over their stay in more detail, and to
insist that there be no sex with any of the sissies. None of the women
saw any problem with that. Two of the sissies, including Lisa, were
somewhat disappointed, as they had been chosen by a couple of foxes.
Most of the time during the week the ladies spent in meetings with Lady
L. and her assistants, going over the fine points of what would happen
to their spouses and what specific training they would need. Us sissies
were not allowed in those meetings.
Each day the sissies would e***** their respective woman to breakfast,
lunch and dinner. Between meals were their meetings and tours of the
island's limited facilities. Over the several days that they were
there, the ladies got to know their personal sissy fairly well.
Marge could not seem to stop talking about my heart, rose and butterfly
tattoos, pierced ears and feminine mannerisms. She seemed delighted with
me. Of course, the rule that I had to constantly smile did not give away
my true feelings. It didn't matter. The potential consequences from
Lady L. prevented me from showing Marge anything but the best of times.
A special dinner was arranged for the ladies final night on the island.
I had to work double duty that night as both chef before dinner and
waitress after.
During desert, Lady L. stood up and made an announcement.
"I am proud to let you know that each of you lovely ladies has chosen to
allow us to train your spouse in the ways of a true sissy. You have
seen the results of our previous work and you have all told me how
magnificent it would be if all insubordinate males could be like this. I
promise you we will do our best to make your spouses the feminized,
obedient, submissive sissies that they secretly have always wanted or
deserved to be!
"And now, after you finish dessert, as a special treat we will have our
current sissies dress however you would like them to dress and do
whatever you would like them to do! They are yours to command. Use your
imaginations ladies! "
Charlene (formerly Charlie) and I glanced at each other with the 'what
just happened here' look on each of our faces. But all of the time
smiling.
Much to my chagrin, Marge had me dress in a corset, garter, panties,
stockings and 5" high heels, all black. She also insisted on the blonde
wig and bright red lipstick, which were very unusual for me. The rest of
my make-up, well you can probably guess.
The sissies adjourned to dress and waited until the last of us was ready
before we all rejoined the ladies. We had to assist Daniela and rush her
along as her owner for the week had insisted she wear a full length
dress and be made up immaculately, which, of course, she was when we
were done with her. (Note: I think I can speak for all of us sissies
when I confess that there is no better feeling than when applying eye
shadow, mascara, eyeliner, blush and lipstick properly.)
The ladies were so taken by the sight of us when we entered the room
that they all stood up in unison, applauding and shouting cat calls as
Lady L. introduced us individually.
I, wearing less than any of the others, was particularly embarrassed at
the volume of the cheers. We joined the lady who had chosen us and began
to mingle in pairs around the room.
We ran into Daniela and her beautiful Mistress first. Obviously trying
to learn more about the nature of Lady L.'s plan, Daniela's Mistress
asked me, "Do you enjoy being feminine?"
"Oh yes!"
"Could you ever imagine yourself as a man again?"
"No, not really."
"Are you gay? Were you gay when you started here?"
"I was straight, but, well, I only sleep with men now, but... "
"Then you are GAY, little one, don't be ashamed of it. I'm hoping to
convert my husband. Maybe you two could get together some day. I think
you would like him and I KNOW he would like you!" she giggled and I was
becoming more and more humiliated.
"Well I must go talk to some of the others. This is such a fascinating
group. I simply love the work they do here. Bye for now."
"Bye." I curtsied out of habit as she left and she smiled a broad smile.
Marge then looked down at my waist. "Take your panties off."
"But, no one else...uh.. of course Mistress Margaret!" I did as she
directed.
"Well son of a gun! I THOUGHT you were wearing a chastity cage. Don't
want that little mouse escaping now, do we? I was wondering why she
called you 'little one'. Now I know!" She laughed loudly at my obvious
embarrassment and since my predicament called for it, I laughed with
her.
"Hey! I have an idea. I be back in a second," said Marge. I had no
idea what she was up to but for a minute I stood there alone wearing
even less than I had entered the room with. I noticed that a couple of
the ladies were involved in other conversations but were also eyeing me
up and down. How humiliating.
Marge returned with a length of string and, surprisingly, the key to my
chastity cage which she promptly unlocked and put in her purse. Saying
nothing, she then tied the string firmly around my 'manhood'.
"There!" she remarked. "Now let's go mingle some more."
With that she wrapped the string several times around her pudgy hand,
grabbed my penis and began to walk over to the largest group of guests
she saw. With my 5" heels and being tugged by my penis I was forced to
take small, quick, mincing steps to keep up.
Marge interrupted the conversation of the other group, "Hey gang, look
what I've got!"
She pulled me into the center of the group again by my cock. "I think I
want my husband to look like this. Hah hah hah!"
I kept smiling but was trying to get Lady L.'s attention hoping she
would make this humiliation stop. Lady L. narrowed her eyes and gave me
an evil smile. After all, we were there to please the guests.
Letting the string unwind from her hand, Mistress Margaret (as she now
insisted that I call her) tugged me again to another pair of ladies with
their sissies. "Hello ladies, and sissies" she said, less imposingly
this time. Mistress Lena, one of the ones who had been staring at me
earlier, began to look at me closely again. She looked first at the
rose tattoo on my hairless chest, stroking it gently. Then at the
butterfly tattoo in the center of my back just below my neck. Also
touching it softly as though she wanted to make it come alive. Finally
she perused the small rainbow very low on my back. "The colors will
probably fade over time" she said, "but the idea behind this one will
last forever".
"Fine work" she said. Could you lift your leg with the heart tattoo on
it?" asked Mistress Lena. I instantly obliged, bracing myself on Lisa's
shoulder so as not to fall. She bent slightly to look closely at it.
"Umm." She uttered. Then Mistress Lena knelt down to look at the last
tattoo I had received, that of a fairy just above my penis.
"Such fine hair... A beautiful face... and delicate wings. Kudos to
Lady L. for having the nasty hair removed so that we can see your pretty
fairy" Mistress Lena spent what seemed like an eternity analyzing my
fairy. She cupped my balls and moved so close to my tattoo that I could
feel her breath on my now erect penis. "You are a fine example of what
males can become with the proper education." She seemed to be intent on
perfecting my humiliation and she was certainly succeeding.
Mistress Lena was beautiful, gentle, a real woman's woman, and yet she
terrified me.
Then her round of questioning began:
"Were you happy with yourself as a man?"
"Not really, Mistress, I used to cross-dr..." She interrupted before I
could finish.
"Are you glad your spouse brought you here?"
"Oh yes Mistress."
"Do you enjoy being so feminine?"
"Yes, Mistress."
She took one of my hands and placed it on her breast much to the chagrin
of Mistress Margaret who began to pull on the string around my cock as
if to pull me away from Mistress Lena. Then Mistress Lena leaned over to
whisper in my ear.
"Do you prefer women or effeminate males?" Under these circumstances
this was one tough question!
"Ahhh..." I knew how I had to answer even though she was almost offering
herself to me. "ah... males" I said under my breath.
"I want you to show me? Undress this nice sissy here and suck his..
excuse me, HER cock!"
At my hesitation she became insistent, "NOW!"
Lisa mockingly reminded me to smile.
I knelt down and reached around Lisa's waist to unzip her pencil skirt
which zipped in the back. It fell to her ankles. Then I slowly slipped
her pantyhose down. Then her lace panties. Darn the luck! She also was
wearing a chastity cage! Not a problem as Lisa's wife had rushed over
with a key. And she was followed by the entire group of ladies. Before
you could say Jack Robinson, her cage was also in Lady Margaret's purse.
I had just been intoxicatingly close to an absolutely beautiful woman.
Despite what I had said out loud, I could not help to wonder what it
would have been like to be with a woman like this. Everyone on the
island knew there would never be a chance of that happening. Instead, I
now had a golden opportunity to please another male with my mouth. And
to the oohs and aahs of the ladies surrounding us, I kissed her penis
and placed my moist lips around it as I had done many times with many
males. I put no less effort into pleasing Lisa than anyone I had gone
down on. I was trained how to do it. It had been burned into my mind
that I must try to make this the best experience possible for my lover.
The only difference this time was that there were approximately a dozen
beautiful women up close watching me. I had been conditioned to enjoy
what I was doing despite the fact that this was possibly the most
degrading thing I had ever done. The ladies saw that I was not forced
to do this, that I was not only doing it willingly, but that I was
showing an extraordinary amount of enthusiasm for it. Lady L. would be
proud of me for providing such a convincing display for her potential
clients. The heightened sense of awareness. The TOTAL humiliation. I
DID enjoy it. I could not see which one of the ladies said it, but she
dubbed me 'Best Cock Sucker of the Week' and I heard the other ladies
chuckling in agreement.
I think it was Mistress Lena that told me to swallow it all when Lisa
ejaculated but that was what I had already been trained to do. My mind
started to wander with lust as I tasted the slippery cum. I so wanted to
enjoy this perfect total humiliation that I let the sperm and semen rest
for a time on my tongue in order to savor it's taste and give the ladies
a further visual treat.
Refusing to continue to share me with the entire group, Mistress
Margaret gave one tug on the string tied to my dick which I could not
ignore. She seemed jealous that she had not taken me to this level of
embarrassment first.
"Take off the rest of your things, except the high heels" she ordered.
"Huh?" I wasn't sure of her intent.
"You heard me. Get naked right now! I want to show off the best cock
sucker ever!" she said. Then whispering in my ear so only I could hear,
"Don't you ever embarrass me by letting some other woman tell you what
to do! I am in charge of you now!" With that, she slapped me hard in
the face. It hurt a lot. The other ladies were watching anxiously to
see what my reaction to the slap would be. I knew Lady L. would be
watching closely as well. They all laughed and seemed delighted when
all I did was let out a meek "Thank you Mistress Margaret".
Nude except for the high heels, I had to try to keep up with Mistress
Margaret using tiny delicate steps as she began to stride around the
room pulling the string tied to my penis. It was almost too much even
for me. Somehow, but I did not know how, I had turned out to be the
center of attention that evening. First, as the most scantily clad one
in the room I had been questioned about my lack of virility. Then me and
my tattoos were studied closely by one woman followed by my performance
of a homosexual act witnessed by all of these beautiful women. And now
all eyes seemed to remain on me as I scurried around the room naked
being pulled on a leash by the least attractive woman there. Regardless
of the fact that I thought she was the ugliest of our lady visitors, I
knew I was her submissive for as long as she wanted me to be and I would
have to act accordingly or risk severe punishment.
With all of this going on I began to drift into sub-space, that place
where all of your fears of embarrassment disappear. My mind, no longer
able to accept such abject humiliation, had begun to welcome it as the
only defense left. My smile returned and I began to wriggle my hips in
an exaggerated feminine movement to provide the maximum entertainment
value for the ladies. Sub-space. A level of submission where you begin
to feel a serenity with the fact that you have no control and that you
are actually intoxicated with the humiliation surrounding you. A rapture
of sorts. Finding pride in being SO degraded that your status as the
lowliest, obedient submissive ever is etched in your mind. A happiness
of pleasing others by having them see you squirm in embarrassment. I
wanted to let Lady L. know that I had joined her in trying to show just
how far you could go with a submissive male.
Our little party went on for another two hours before the ladies finally
began to run out of ideas on how me and the other sissies could serve
and perform for them. At last Lady L. got everyone's attention.
"Ladies, ladies. Grab a glass. I want to propose a toast!" When all
of the Mistress's glasses had been filled by their respective feminized
servant, she continued. "To SISSIES! May they continue to grow in
numbers and serve their Mistresses as our pretty slaves have done here
tonight!"
A loud cheer rose from all of the ladies as each took a swig of their
beverage. Looking around the room I noticed that each and every one of
the sissies was also sporting a smile. Was it that we had pleased Lady
L. and, thus avoided punishment or were we glad to have served and
committed ourselves to join an important cause?
<<<>>>
Days later, as the husbands of the Mistresses we had entertained that
night began to arrive, I smiled. I knew what they were in for.
As she had done with my group, Lady L. gathered the men in the hotel's
conference room and shocked them with the REAL reason they were there.
Not to retire wealthy to this island, but to become totally feminized
and learn how to serve women. Each of the remaining eight of us current
sissies were waiting outside the conference room wearing our French
Maid's outfits and at just the right moment, Lady L. signaled to us to
enter the room. The look on their faces was priceless.
"Boys, this is what you will become after you have received your
training at the Institute" Lady L. announced.
The men looked shocked as though they considered this a threat certainly
impossible to fulfill but a threat to their manhood nonetheless. As a
group they seemed more timid than we had been at first. Perhaps it was
the sight of we sissies who had been transformed that made the threat of
total feminization more real.
There were eight of them all together. Just the right number to have
each of them assigned to one of us, which was Lady L.'s plan.
After a short discussion, the ladies had chosen which of the new males
would be paired with each of the experienced sissies. It seemed a
natural match when I was put in charge of Mistress Margaret's husband,
an awkward individual named Wayne. He started with the usual whining
that there was no way he would ever succumb to this training. He
obviously did not know who he was dealing with. My group had
experienced the training and conditioning. We had learned our place in
the grand scheme developed by Lady L. and our spouses. Our behavior had
been corrected and now we were the individuals we were supposed to be.
We knew that our purpose was to serve the Ladies and the real men that
would visit here. And now we would assist in the transformation of
another group.
What fun!
Tied naked spread-eagle over his bed, Wayne received the first lesson it
was my privilege to give him...
Thwack! "Oww!" The paddle landed squarely on his ass.
Thwack! "Owww!"
Thwack! "Owwww!"
This continued until his buttocks were beet red. "Alright, alright I'll
shave!" he finally agreed.
The process had begun again. He was totally shaved of his body hair by
his 'boyfriend' and then he did the same to this new 'boyfriend'. It
was genuinely fun to perform the inspection on my 'student'. I enjoyed
causing him fear and humiliation as I closely reviewed his body looking
for shaving "errors". Of course I found an errant strand of hair here
and there for which he paid a price. Thwack! Thwack! Thwack!
And when the redness had finally gone away several days later, he
received his first tattoo, a large cock design on his right ass cheek.
I actually got to watch one of Lady L.'s male assistants perform the
work, my first class in being able to do body art myself.
Initially when Wayne was unwilling to wear a bra, I placed nipple clips
on him for one-half hour at a time. It was certainly painful, but not
as painful as when the clips were removed. On one-half hour, off for
one-half hour. Ouch!
His building anger with me finally got the best of him and he took a
swing at me. He missed and was quickly subdued by all eight of us
graduate sissies. We were there to assist each other in just such an
event.
It was the only time Wayne (now Wendy) would try such a thing, as the
punishments for violent behavior were more severe. Wanda was much more
docile after having her nipples pierced and studs placed in them.
Transgression followed by punishment. Obedience followed by reward.
The lessons that had worked so well on the first batch of sissies were
just as effective on the second. It was nice sharing the maid
responsibilities with the new group. More time for lying on the beach
in my bikini. Ahh. Life is good.
It was not perfect however, as Mistress Margaret was always there to
make sure I did my job in properly training Wayne to her specifications.
If Wendy did not advance in her feminization as rapidly as Mistress
Margaret desired, I would receive another slap on the face which was
followed by my now routine "Thank you Mistress Margaret" and a deep
curtsey.
In about a year, half as long as it had taken us, the second group of
feminized males were very close to completion of their training. Lady
L. was so proud of all of us. I even received a reward. Wendy's wife
(now ex-wife) got to watch as Wendy licked and sucked on my cock for
nearly half an hour. It was a wonderful experience. Sexual release of
any kind was a real rarity for a sissy. The sensation of another male's
lips pressing on my penis was extraordinary. The warmth of her tongue
was exquisite. I was moaning audibly as I held her head and slid my
member in and out with increasing speed. After my orgasm I looked down
to see the red lipstick smeared on my cock and felt a sense of pride in
knowing how good I must be making the real men and other sissies feel
when I serviced them in this same way.
We were all accepting of who we were and what we had become. Long ago
it seemed impossible to conceive of me being subservient to women and
having sex with males, Now it was inconceivable that it be any other
way. I now had fifteen potential 'boyfriend' sissies sharing the island
with me in addition to the real men who occasionally visited.
Immediately after the graduation of the second class of sissies from
W.I.T.C.H., Lady L. announced that she was again starting a campaign to
find even more women dissatisfied with their spouses. Perhaps sixteen
this time to match the new number of 'mentors'.
I was becoming as enthusiastic as Lady L. in my desire to help transform
submissive males with dominant wives into the proper feminized sissies
that they were surely meant to be all along. I went to Lady L. herself
and with a broad smile and a proper curtsey, I said to her, "I think
we're going to need a bigger island!"
"I'm so glad you think so Lynn," Lady L. said in a way to convince me
of her sincerety. "I am as pleased as your ex-wife was with your
progress. So pleased in fact that I have been talking it over with
Mistress Margaret and we would both like to see you move to the next
step."
"Next step?" I said. My tone had shifted quickly from happy to fearful.
"Yes. It's a big one but we now know you're ready. It would involve
HRT, hormone replacement therapy."
I was speechless.
"If you're not already familiar with the process, let me explain. It is
called therapy because it is actually a course of treatment. In your
case it would be treatment for those remaining undesirable male
characteristics. You will begin taking certain medications. The
'replacement' would be substituting estrogen and progestin for androgens
such as testosterone. But I don't want to confuse you with a bunch of
medical terminology..."
"But what if I don't want to do it?" I interrupted.
"Hear me out." Lady L. spoke in a stern voice.
"We are looking at the long term benefits of this. You will have a
softer more curvey body. You won't have to shave as often and
eventually you won't need that chastity cage anymore. Wouldn't that be
wonderful?"
"That's because I won't be able to get it up anymore, isn't that what
you're saying?" I said, now terrified.
"Oh, you're sex drive may be diminished a little but that will be
replaced by a whole new set of wonderful feminine feelings. You will
finally be able to enjoy the extraordinary intimacy that a woman feels
when a man makes love to her. Our clients would appreciate that
improvement and, after all, aren't we here to please them?"
Starting to cry, I tried to protest, "You're going to castrate me too!
No...no... I don't want that!"
"Silly gurl! No one is going to do any such thing. My clients actually
tend to prefer feminine males. I don't question their motives but they
basically want women with that one male part. We all know how strange
men's desires become when sex is involved but you would be in the best
of all possible worlds. You could have the best female parts and the
best male part all at the same time! The real men who visit here would
all want you!
You could be dating them instead of doing chores as a maid! How
wonderful is that?!"
I was truly relieved that no surgery was involved but I still had my
doubts. "Can I have some time to think it over?"
"Of course, little one. And let me say that you will be getting the
best medical attention available. Don't forget Mistress Margaret is a
former nurse. These things must be monitored for side affects and we
will want our favorite *********** to be in the best shape possible for
our clients. I promise you that you will not be sorry!"
I was going to have a lot to think about.
Or perhaps not. Lady L. then left to see Mistress Margaret. A short
conversation followed.
"Have the tests come back?" Lady L. asked.
"Yes. They were all fine", replied Mistress Margaret.
"Great. Then I think it's time to up the dose. What do you think?"
"I agree. 50 micrograms of the synthetic estrogen twice daily but I
think I'll leave the progesterone and Propecia, that's that anti-
androgen d**g, where they are for now. I never thought this would be so
much fun. I can't wait to try it on my ex-husband."
I had no idea that Lady L. had been ******* my meals for several weeks
already. I had been pushed down the road less traveled at breakneck
speed and U-turns were i*****l!
<<<<<<<<>>>>>>>>>
In the end several of the wives, including Daniela's wife, chose to take
their 'husbands' back to the States. They would become the docile,
submissive slaves to their wives that they had been trained to be.
Andrea, Susan and Vanessa would continue to live on their own tiny
island as the 'Queen' and her 'Princesses'. There certainly would be
very little sex on that island but no one, including those three
inhabitants would probably care. The best I could hope for was to avoid
joining them as Andrea's third 'Princess".
Only Charlene, Lisa, Gail and I, Lynn of the original group would remain
on the island.
It was amazing what the training and conditioning of W.I.T.C.H. had
done. Was this what any of us sissies either wanted or deserved? Were
we proud of what we had become? Were our wives right? Were we any
happier? It didn't matter for this is the way it was and the way it
would be from now on. You could either choose to be miserable with
yourself or accept who you were and make the best of it. Ultimately I
was never told that I had been on hormone replacement therapy from much
earlier on but when I looked in the mirror and began to notice the
changes in my body, I could only smile.
As roughly as my ex-wife had treated me I still love her and am happy
for her. She had left me behind but I somehow knew that it was the
right thing to do. She lived with both of her own boyfriends now and
she did indeed end up putting a very large picture of me in my
bridesmaids dress over the fireplace. It was actually quite flattering
in displaying my femininity and would prove to be a real conversation
piece with our friends back home. Lady L. continued to send her
progress reports on my new appearance.
With the arrival of yet a third group of submissive males it was clear
that this was truly going to be a growth business. My fellow
'boyfriends' and myself had been promoted to instructors to help
accommodate this new class of trainees.
There was also a rumor that Steve and John would both be returning to
the island at the same time soon. Ummmm... I couldn't wait!
10年前
