Road to Ruin
Jamie's Road to Ruin Part
I am about to tell a story that is true. It was my first experience but
it shaped my life forever, not necessarily for the better. As a c***d,
I used to fantasize about being a woman, but never acted on it.
Anything "gay" freaked me out. In any event, I was very closeted and
repressed. And very awkward around women I was attracted to, but seemed
to be able to make a lot of female "friends."
Years ago when I was in my twenties, a female friend of mine, Karen,
tripped and fell and cut her chin open. One of her girlfriends, Kathy,
loaned me her car to give Karen a ride to the hospital. After taking my
friend Karen to the hospital and getting her stitched up I drove her
home and then drove the car to a bar that had bands that play jazz where
Kathy was, so I can return the car. I had expected Kathy to have the
courtesy to drive me home but she didn't want to do that so I was kind
of stuck.
I decided to hitchhike home. After a brief period of time, a fairly
conservative looking guy picked me up and asked me where I was going. I
gave him directions and off we started. I suppose I should describe
myself. In those days I have very long hair which reached down to the
middle of my back. I was tall and very slender. Jerks used to shout at
me from their car windows "are you a boy or a girl?' In any event, my
rescuer was a fairly large and burly looking guy, but seemed friendly
and we had a pleasant time talking. In those days, I lived in a college
town and hitchhiking was a viable means of transportation and a good way
to meet interesting people. He asked me if I needed to get home right
away and I told him not necessarily. We stopped at another bar he was
familiar with and listened to a live band this guy knew about. It was a
country and western band, which wasn't really my thing, but they sounded
pretty good. It didn't seem like a shitkicker bar so after my initial
anxiety, I was reasonably comfortable. I remember my benefactor kept
saying of the guitar player "he plays a mean guitar doesn't he?" He
said that many times and I think he was pretty drunk by then. We got
back into his car and he then asked if I wanted to stop at his house for
more drinks (he said it was close by and that he would drive me home
after that). I was pretty blasted at that point, having been drinking
all night. I said ok, and we talked some more, then, after a few minutes
as we were driving, he asked me if I had ever sucked a cock. Out of the
blue, as we had not talked about anything sexual all night. I was very
nervous, and felt butterflies in my stomach like never before, but at
the same time, I became pretty excited (and as I said, I was really
drunk).
It had been something but I had fantasized about for a long time but
never had acted on. I have always had fantasies of being a woman, or at
least playing that role with a man. When I looked at porn, it was
always straight porn, but I loved watching cocks and cumshots more than
anything. In any event, I said no I had never sucked a cock. He looked
disappointed, but then I told him that I had fantasized about it for
some time. I then asked him why he asked me that question. He reached
over and took my hand and put it on his crotch. I could feel him getting
hard and I remember thinking that he was pretty big too. I was filled
with anxiety but I got hard too. I was way too anxious to say anything.
With his hand over mine and, therefore, making me do it, I fondled his
cock on the way to his house, but only through his pants.
When we got to his house and went inside, he told me to strip. His
attitude changed quite a bit all of a sudden. He wasn't exactly mean
but suddenly he seemed very demanding. He told me he was divorced, but
had some of his wife's stuff still. I had long hair back in those days.
He left for a minute, came back with a skirt and some lipstick. He
again told me to strip and I was worried for a while that something
really bad was going to happen to me. However, I have always been a
little submissive and I felt like I should obey. I said "Yes Sir" and I
peeled off my clothes and was standing there in front of him naked with
my dick as hard as it has ever been in my life. He told me to put on
the skirt and then he applied the lipstick to me. My heart was
pounding.
At that point he kissed me and stuck his tongue in my mouth. He put his
hands on my shoulders and pushed me down to my knees and told me to suck
his cock. I unzipped his pants, he was partially hard and in order to
please him I licked the shaft of his cock and his balls and then
proceeded to start to suck his cock while my hand cradled his balls.
While I was doing that, he started calling me names, telling me that I
was a whore and a cocksucker. I pulled back a bit, startled that he
was treating me like this, but at the same time was incredibly turned
on. He told me to keep sucking and pushed my head on his shaft. I
started gagging a bit and that seemed to turn him on more. He really
was pretty big and my jaw was getting very tired and I wasn't sure how
much longer I could keep it up, but when I squeezed his balls a bit, he
came in my mouth and all over my face. I was freaked out and spit out
the cum, which dribbled down my chin, but he wouldn't let me get up for
a while and there I was, on my knees with cum dripping down my chin and
lipstick smeared on my face.
He did not do anything to get me off and I asked if he minded if I
jerked off. He told me I could if I ate my own cum, but then didn't
make me do it when I came. I never came so hard in my life and it only
took a few seconds as I was so turned on.
He told me to clean myself off in the bathroom. I went and wiped
everything off of me and came back to the living room topless and still
wearing the skirt. He pulled out the lipstick again and painted my lips
for the second time. He started kissing me again, really hard and then
made me lie down on the floor. He got some Vaseline (which is not a
very good lubricant as I was about to find our the hard way) and smeared
a handful on my ass. He then mounted me missionary style and I wrapped
my legs around him as he entered me. You read all of these stories that
say that anal sex hurts at first and then the fuckee loosens up and it
feels ever so good? I am sorry to say that it hurt a lot at first and
just got worse. I had a drunken guy fucking the hell out of me and he
would not stop until he came. I think that it took a very long time
both because he was drunk and it was his second shot of the evening. I
wasn't sure what to do, and I was in pain, so I reached around and put
my finger in his ass and at the same time, started sucking on his
nipples. That seemed to do the trick as he started grunting and I could
feel him shaking all over as he bred me.
After that, we both kind of passed out. I woke up a few hours later. He
was still lights out. I had sobered up a bit and the reality of what I
was doing hit me and I was in a panic. I tip toed to the bathroom,
wiped off the rest of the lipstick, put on my clothes and left. As I
sobered up, I was pretty freaked out. It had been my first experience
with a man and as a k** growing up, the worst insult anybody could throw
at you was fag. And here I was, completely emasculated, but really
turned on by it. I was not sure of what that meant, or the consequences
of my actions.
I had blood in the toilet the next day when I went to the bathroom, but
I was scared to go to the hospital. It took about four days for my butt
to stop hurting. I masturbated a couple of times every night reliving
the memory of that evening. I did not know my new friend's phone number
and wasn't sure if I wanted to, or should, ever try to contact him
again. I was not sure what my reception would be. At the same time, I
was fascinated with the role I had played.
I went back and forth about the experience, but what it did for me was
to start me on the road to my slow transformation. I shaved all my body
hair off, including my armpits and legs. I mail ordered some panties
and got some nail polish from the store and started wearing panties
under my regular clothing and also started painting my toenails. It
turned me on to think about having that secret as I went about my
regular business. I also bought a bra and some breast forms and would
put them on when I was alone. But I was scared to venture out with
those on.
Since the time of my first experience, I spent a bit of time troubled by
what happened. On the one hand, it turned me on like I had never
expected. On the other hand, I was experiencing a lot of conflict with
my sexuality. I will say in those days, that I would have more than a
bit of anxiety thinking that I was gay. I was more than a bit ignorant
of the transgender scene, which was non-existent in my home town as far
as I knew, and the internet was not as sophisticated as it is now. It
may sound odd, or contradictory, but I guess I convinced myself that if
I was a woman, it would not be so wrong, but I was a man. In any event,
I was pretty sure that I had taken my walk on the wild side and spent
some time overcompensating for it. A nice fantasy to use, but not
something I would repeat. I would walk down the street desperately
trying to make sure that I was attracted to every woman that went by.
Unfortunately, my period of real chastity didn't last all that long.
After a few weeks of trying to be very macho, I reverted back to being
more feminine, at least in private. In short order, I became addicted
to my closet dressing and wore panties underneath my regular clothes
almost every day. I also painted my toenails and went about my business
with my covered up toes screaming alternative lifestyle. In addition
to the feminine clothes that I had purchased, I went to the local
"marital aids" shop and purchased a number of toys. I bought a butt
plug and a couple of dildos. My fantasy life for masturbating mainly
consisted of me dressing up fully, putting on makeup and getting one of
my dildos and putting it in my mouth and pretending that I was sucking
cock, while at the same time, stretching my ass with a fairly good sixed
butt plug. I really liked wearing bright red lipstick for some reason.
I would also practice sucking cock on the dildo and got my jaw muscles
in better shape than they were before.
I fantasized about men cumming in my mouth. I liked to watch bukakke
videos. I would tell myself that I would swallow my own cum to practice
doing it for the next man I might pleasure. Of course, as soon as I had
an orgasm, I would be disgusted with myself and take off my clothes,
wipe the cum off my hand and not swallow anything. Fantasy and reality
do not always mix. I did have a few times where I would lay on my back
and bring my legs over my head so that my cock was in front of my face.
If I really forced it, I could just get the head of my cock in my mouth.
I started getting some neck pain from that and stopped that practice
pretty quick.
In any event, as was my practice, I had driven to school for class and
was driving home to the West side of town. From the outside, I looked
like a typical college student with boots, bluejeans and a flannel
shirt. However underneath I had painted my toenails red, had red thigh
highs on and red panties on underneath everything. I picked up a hitch-
hiker who was going about half way down Main Street. He said his name
was Frank. Frank was a tall very built, black man in his early 20's.
We started talking about music and found we had a lot in common. We
both liked the same kind of music and he said that he invited me back to
his place. He seemed like a nice guy and I had nothing to do, so I
agreed to take him home.
It was snowy out, so I took my boots off when we got to his place. We
spent what seemed like a few hours talking and we were drinking a fair
amount and I was pretty buzzed. He was playing a bunch of records by
artists that I was not familiar with and I think he enjoyed turning me
on to new music. At some point, his phone rang and he picked it up.
The conversation sounded like he was talking to a friend. All of a
sudden, he had a odd, kind of puzzled look on his face and it looked
like he was staring at my feet. I looked down and to my dismay, saw
that there was a hole at my big toe in my right sock. My bright red
toenail and the red stockings were poking out, and apparently, giving
away my secret. I could tell from the conversation that his friend
wanted to come over right away, but Frank was telling him to come by in
a few hours. I could make out what sounded like the question being
asked on the other side of the line: "What, do you have a girl over?"
and definitely heard Frank say "you might say something like that."
Frank hung up and gave me a funny look. I kind of raised my arms and
shrugged. Frank said "is there something you want to tell me?" He took
a step towards me, but still was about 3 feet away from the couch I was
sitting on. I wasn't sure what to say, and maybe Frank wasn't either,
but I said "I have a bit of a secret - here let me show you. " I stood
up and pulled off my jeans, which exposed my thigh highs, panties and
toenails. He kind of stared at me for short while, and I wasn't sure
how he would react, but in a few seconds, it was clear what he was going
to do. He simply unbuckled his belt and zipped his fly down and let
his pants drop to his ankles and then looked at me with an Ok, what are
you going to do now look? I could have said something, or jumped up and
left, but instead, l found myself looking at the most perfect cock I had
ever seen in my life. I was immobilized for a few seconds. Flaccid, his
dick was bigger than mine when it was fully erect. In any event, I
found myself kneeling in front of him with my mouth open. I put my lips
on the head of his cock and started sucking, feeling him getting bigger
and bigger. Frank's cock was a "shower" because while it did get bigger
when he was erect, it didn't increase in size proportionately the way
mine does. That was a good thing, otherwise, I could not have taken it
in my mouth. In any event, Frank had to be a good 8 or 9 inches when
hard. I licked his shaft and sucked on his balls for a while and then
got to work on the head of his shaft. I had one hand on his balls and
another on his shaft and was sucking on the head of his cock for all I
was worth. I could feel him start to shake and in a few seconds after
that, felt his cum hitting my mouth. I swallowed and swallowed until he
was done and then sat back up on the couch. The whole event couldn't
have taken more than 5 minutes. I wasn't sure what was going to happen
next. Frank told me that I was the first man he had been with and I
told him he was the second. He said that his friends were coming over
soon and I should leave, but he said I should call him later in the
week. He gave me his phone number and I left his apartment with the
taste of cum in my mouth and thought to myself that I was pretty sure I
was about to begin another bout of anxiety and self doubt. And indeed I
did. While I went home and masturbated to the memory of what I had just
done, I am sad to say that I never called Frank and never got together
with him again. Looking back on it I got the sense that might've been
the most normal relationship I might've had in all this. But at the
same time, what was a pleasant afternoon ended with a blow and go (and
with no though of my pleasure at the time). In any event, this second
step pretty much made it impossible to pretend that my feminization was
something I could stop at any time. Also, it worried me that my
immediate reaction to seeing another man's cock was to drop to my knees
and start sucking. And why was I only concerned about pleasing him and
not myself at the time? As future episodes will reveal, that reaction
would dictate the path my life was about to take.
After a few weeks had passed since my encounter with Frank, I felt like
maybe I should try to make contact with the man that had started my path
to ruin. Since it was still winter, I could do a lot of things without
people noticing. I continued to shave my legs, chest and underarms and
paint my toenails. In preparation to meet John (I really wanted to make
a good impression) I got a pair of red panties and red thigh high
stockings and put those on. I put on a bra with my breast forms and
topped it off with a red form fitting dress. I put jeans on over this
and put on my down coat and boots. The coat covered the breast forms
nicely and I looked pretty normal and nobody would know I was femmed up
underneath. I also got some KY jelly as I had learned my lesson about
Vaseline.
It was a Saturday night and I went to John's house. The lights were on
and my heart was pounding as I rang the door bell. He answered the door
and looked very surprised to see me. I said hello and told him that if
this was a bad time or if he didn't ever want to see me again I would not
bother him. He had a funny look on his face and then smiled and told me
to come in. When I stepped into the hallway, I heard him close and lock
the door behind me and then I heard voices in another room. He took my
hand and pulled me into his living room. There, to my shock and horror,
were two other men. They were both drinking beer and there was a porn
video playing on the television. One of the men was in a chair, with his
pants around his ankles jerking off.
"This is the sissy I was telling you about" he said. It turned out that
since my encounter with John, he had discovered social media and was
getting his needs fulfilled by putting ads in for guys to get together
and jerk off to porn. I had stepped into one of those times. In any
event, he then turned to me and told me to take off my jacket. Seeing my
dress, panties and the stockings, all three men started laughing and
calling me names and asked me what I was going to do for them. John went
to the bathroom and got out the lipstick. On it went and next thing I
knew, I was on my knees with three men in front of me. I had a cock in
my mouth and one in each hand, while on the television a naked female
slut was doing the same thing, only with five men.
The first man came in my mouth pretty quickly and all three of the men
told me to swallow his come like a whore would. (I am not sure that real
whores do that, but swallow I did). It tasted bad. So many times the
fantasy never lives up to the reality. The first comer (I never did get
his name) then went to the kitchen to get beers for the others and I
moved on to sucking the other stranger's cock. My jaw started to get
tired again and I was not sure how long I could keep sucking. John was
looking at me and I tried squeezing the stranger's balls to see if that
would hurry things up. Fortunately it did, and I was swallowing my
second load of the evening.
The two strangers sat down on the couch to watch me suck off John's cock.
His was the biggest one, and I was trembling to keep my jaw from locking
up. Oddly, a minute after I started, he turned his back to me. I was
afraid I had displeased him, but at the same time, needed a moment to
rest my jaw. My relief turned to grief when he told me to lick his
asshole. I had never done that before and was grossed out. He said it
again and told me he did not want to have to tell me a third time. I got
nervous and did what I was told. I could smell excrement and was
gagging, but stuck my tongue in his butt hole like he demanded. He told
the others "looks like this sissy is will do anything I tell her to." I
guess I would, or so it appeared at the moment. My fault for going back
I guess. After I had licked his ass clean, he told me to stand up and
stay in place. He went to another room and came back with an old looking
dog collar and a leash. I was collared and he pulled the leash and made
me follow him to the bedroom. I was made to take off my dress and
panties. He lay down on the bed on his back and told me to get on all
fours and suck him off. A minute later, his friends came into the
bedroom and one of them started playing with my ass. I felt some lube go
on and then I felt a cock pushing to get into me. Pretty soon, I was
being spit roasted. I found it hard to concentrate on sucking cock with
another one slamming into me, but fortunately, the stranger came quickly.
Then it was the other's turn. He too was relatively quick, something for
which I was grateful, as I was still not used to anal sex. My jaw was
giving out when John moved around, pushed my face into the pillow and
rammed his big cock into my butt. He pumped for all he was worth. I
was glad the other two smaller men had opened me up, because I think I
would have really had a bad time otherwise. He came and then it seemed
like the guys were done with me. "Get dressed slut" I was told. As soon
as I was dressed, John told me it was time to leave. As he closed the
door, he told me that I should return in two weeks and that I would have
a night I would never forget.
I had already had a night I would never forget. I never returned as I
was afraid of what lay in store for me. I think that, originally, I
thought that by going back, I might be able to develop a regular kind of
relationship with John and perhaps have regular outlet for my submissive
urges, but I wasn't ready to be passed around like some prison bitch. I
was also a bit disturbed and scared by my acquiescence at being ordered
to do kinky things. Of course, like so many New Year's resolutions, it
seemed like I was destined to forget this lesson all too soon.
This chapter is a bit creepy, but it is part of my story. I had a very
weird relationship with my mother. She was an alcoholic and very
flighty. In many ways, I feel that she unmanned me growing up. In any
event, I had not seen her for a while, and she called me up and told me
that she wanted to come by and take me to the movies. When she got to
my apartment she then said that she had been dating some guy for a while
and wanted him to come along as well and asked if I would mind. I said
no, I wouldn't mind (like I had a choice).
On the way over to the fellow's place, (his name was Bob) mom was
complaining that she wondered if the guy was gay. She said usually when
she went out with a man, he would be all over her but this guy had never
made a move on her or had even tried to kiss her. (Mom had a habit of
sharing her sex life with me-never mind that I had told her that such
talk makes me very uncomfortable). She said Bob was a photographer and
indeed when we go to his house he did have a very elaborate photo studio
in one of his rooms with a backdrop and lights.
We made some small talk and then went to the movies. Mom and Bob talked
through the entire film, with people in the seats around us telling them
to be quiet. Mom always did things that embarrassed me and never seemed
to care. After the movie, we went back to Bob's house to have some
drinks. Bob made us all martinis and the conversation livened up quite
a bit. It was the first time I had ever had a martini (or three) and I
was pretty buzzed.
We spent a little time talking and Bob seem to be a bit taken with me,
or so I thought. He spent most of the time talking to me and ignoring
my mother. He asked a lot of questions about my long hair and asked if
men confused me for a girl. My mom did not like that line of
questioning and it made me a little uncomfortable too, since she was
there. I am not sure how I would have felt about it if she wasn't with
me.
At one point, as Bob was showing us around the house, we were standing
in Bob's living room. My mom asked to use the bathroom, which was down
a long hall. As she was walking down the hall, Bob stood to my side and
sort of caressed my ass with the palm of his hand and told me that I was
welcome to come by anytime. Oddly, I did not pull away at this touch.
I started getting hard and took my hand to adjust my cock to be more
comfortable in my jeans. Bob noticed immediately and ran his hand up
underneath my ass and cupped my balls. I heard the toilet flush and
found a couch to sit on so that mom would not come out of the bathroom
and see me with a hard-on. Bob was grinning like the cat that ate the
canary and I knew I was in trouble, again.
When it was time to leave, Bob told me in front of my mother that I was
welcome to come by anytime. He said if I want to use his place to study
I could do that. When mom went to use the bathroom again before we
left, the conversation changed a bit. Bob said that he would be
interested in photographing me with some other young men he knew. He
mentioned the word "masculine" when describing them. The whole time he
was talking, he caressed my ass. I felt like he knew my secret. I was
a bit nervous since I expected my mother to come out of the bathroom at
every second. What a weird situation to be in. He slipped a business
card into my hand and said, "Call me." Moments later, mom got out of
the bathroom and off we went
I have to confess that I was pretty curious about all this, although at
the same time, to be hanging out at this guys house would be bad news if
it got back to my mother. Also, Bob was considerably older than I was,
by at least 25 years. Despite any misgivings, I waited a couple of days
and gave him a call. He seemed very happy to hear from me and asked me
to come over that afternoon. As usual, I had my red panties and
stockings on underneath my clothes. I went to his house and he greeted
me very warmly with a big smile and invited me in. We talked for what
seemed a long time and after a number of drinks and after swearing him
to secrecy I told him my life story. He acted like he was very
interested in hearing my story and kept urging me to continue telling it
to him, though I was not sure at the time what his goal was.
At some point he put his hand on my thigh and I was pretty sure where
his hand was going to go next. Next thing, I knew he had his hand on my
cock and he was kneeling in front of me. He unzipped my pants, pushed
my panties aside and pulled my cock out and started sucking my cock. I
came in seconds. Moments later, I stood up and took my outer clothes
off. Exposing my panties and stockings. I undid his belt, unbuttoned
his pants, unzipped his fly and attacked his cock for all I was worth.
He too came in just a very short while and I swallowed his cum. This
act was getting easier and easier for me.
Since I had already told him my story about how I like to dress in girls
clothing and he seemed kind of turned on by it, I didn't feel too much
anxiety at the time. He asked me if I wanted to come over another time
and have him take pictures of me dressed but that made me very nervous
because I didn't want pictures like that of me circulating. After all,
it was possible that my mother would come by and see them and that would
really be a problem for me.
Bob asked me if I would come by on the weekend. He told me that he had a
couple of other young "masculine" male friends that were coming over and
he would like us all to get together. I told him I would come by. He
asked if I would come by and get dressed and I said that I would think
about it. He said that I could come by dressed normally and get dressed
as a girl at his place. He also said that if I was a girl, that I might
have a very nice time with his two other young friends.
I did go to his house that Saturday afternoon and spent a fair amount of
time in his bathroom getting ready. As I have told you, I had really
long hair in those days. I had a bra and breast forms, panties, thigh
highs, short miniskirt, spike heels and a nice blouse that I put on. I
spent a lot of time on my makeup. I put on false eyelashes and
foundation and eyeliner and bright red lipstick. When I came out of the
bathroom, I felt I look pretty hot. Bob's two friends came over and
they looked like they were about 18 or 19 years old thin and built.
They had apparently been over to Bob's before and were quite familiar
with the place. In any event, they quickly took off their clothes and
were standing naked in front of me. Bob took charge and told me that
these two boys were my dates for the day and that I should take care of
them.
Somehow I felt like I had no will of my own and I took a few steps
towards these two guys I had never seen before in my life. Next thing I
knew I was on my knees sucking the cock of the first of the two to get a
hard on. There was a mattress on the floor and he pulled me onto it. So
he was lying on his back and I was sucking his cock. The other boy got
behind me and pulled my panties down and I could feel his cock probing
my ass. Next thing I knew I had one cock in my mouth and one in my ass
and both boys were pumping me for all they were worth. Neither of the
two was very well endowed so I had an easy time on both fronts.
Apparently, while all this was going on Bob had a video camera going.
So I was being recorded for posterity without my knowing. The two boys
took turns with me and I was their receptacle for what seemed like a
couple of hours. When they were done, we all got dressed and the two
boys left and I got ready to say goodbye to Bob. He told me about the
video and I got pretty upset since I told him I didn't want him to take
pictures. He showed me the video and said that he was only going to use
it to jerk off, but then he said that he wanted me to come to his
"parties" again. He told me that if I didn't cooperate that he would
show the video to my mother.
I didn't know if you would or not but I felt like he was blackmailing me
into being a sex slave for his videos. Also, I wanted to know what he
was doing with the videos. I was worried that he might be putting them
on the Internet. However he had me in the worst possible position and I
felt like I was stuck doing whatever he wanted. Bob told me to show up
the next Saturday and to come fully dressed.
I did show up the next week and when I got there, five naked college
boys were standing around in Bob's house. I went into the bathroom to
put on my make up and when I got out Bob said to all of us, "Well, you
know what to do." One of the older boys walked up to me and kissed me.
I kind of liked that as it made me feel little less used than what had
happened the week before. But that was short lived.
Next thing I knew I was on my knees with cocks surrounding me. I went
from cock to cock keep it all five hard for a while. I then started to
concentrate on the boy with the biggest cock, sucking and squeezing his
balls. Pretty soon I could feel him tense up. He puled pulled his cock
out of my mouth and squirted his cum on my face and in my hair. With
his cum dripping down my face and onto my blouse, I then turned to the
next hard cock I could see and concentrated on it. In about two
minutes, this boy blasted my face with his cum as well. A that instant
a third guy who had been jerking off said "look at me" and sprayed me
down with his cum.
The fourth boy told me to lie down on the mattress and spread my legs
and pulled off my panties. He lubed me up and entered my ass and I
wrapped my legs around him. As soon as he came in my ass, the fifth
boy took his place and pumped me for all he was worth. Bob seem very
happy with all this and I noticed that he had a camera in his hands.
After all the sex was done, the boys got dressed and left. I was pretty
spent and in the need of a little time to recover. However while I was
lying on the mattress, Bob came over and unzipped his pants and motioned
me over to his cock. I had cum dripping off my face and my hair and all
my clothes and also dripping out of my ass. My jaw was tired but I
opened my mouth and started sucking on the head of his cock. I guess
the show had really turned him on because it only took him about half a
minute to ejaculate. When it was done I got up and went to the bathroom
and cleaned up a bit. As I was leaving he told me to be sure to come by
the next weekend for "more fun." I left his house wondering what I had
gotten myself into.
Unfortunately a few days after all this, I started to get a sore throat.
I had trouble swallowing and there were white spots on my throat. When
I went to the doctor I was diagnosed with oral gonorrhea. I was pretty
freaked out. I called Bob yelling. I told him I didn't care what he did
but I wasn't coming back. Oddly enough he did not give me a hard time.
I never did see any pictures of me having sex on the internet, but I am
not sure that I would know where too look. One comforting thought that
I had was that if the boys gave me VD, I probably transmitted it to Bob
at the end of the day. I took my tetracycline and put away my clothes
for a while. I later was told that my *** test was negative, so I had a
bit of relief, but this was a real wake up call about safe sex and what
I was doing. But the memory of the group sex really turned me on and I
think that I was hooked on the adrenaline rush of it all. Talk about
conflicted. But no death wish here, so I vowed to be more careful in
the future.
At this point my life I was pretty much torn between my desires, almost
compulsion, to cross dress and have sex with men and clinging to whatever
semblance of what was left of my former normal life. I am a bit of a
hypochondriac, and was worried about disease. I had already learned my
lesson regarding that the hard way. In any event I was hanging out at my
apartment with my roommates and one of them came in with the campus
newspaper and was laughing about an ad in the personal section. The ad
said "free lodging and a Mustang convertible to use during the week in
exchange for pleasurable weekends." It went on to say that the person
that placed the ad lived in New York City but traveled to my town
frequently for business. While my roommates were making fun of this, it
sounded like a pretty interesting idea for me.
In any event I called the number that was in the ad and spoke to a
pleasant sounding man. He said his name was Malcolm and he was a doctor,
and that he managed emergency rooms and hospitals and as part of his
business, he came to my town pretty much every weekend. We arranged a
time for him to "interview" me and I thought about how I would prepare.
I did not ask him over the phone if he was looking for a masculine
boyfriend but figured there would be plenty of those but I might stand
out if I should come fully dressed.
In any event, I want the whole 9 yards. I put on panties, thigh highs,
stiletto heels, very short miniskirt, and my biggest breast forms, very
tight top and with the full make up including eyeshadow, false eyelashes
and deep red lipstick. To top it off, I put on a beautiful blond wig. I
really looked pretty hot. The big question of course was whether or not
the good doctor wanted a submissive girl or a masculine boy.
I snuck out of my apartment and drove over to the meeting place. I rang
the doorbell and my heart was pounding. The man that opened the door
looked to be in his early 40s, he was tall maybe 6'3" and had very
chiseled good looks. He was clearly surprised to see me dressed up as I
was, but after the first look of surprise, he got a really big smile on
his face and invited me in.
He asked me if I wanted anything to drink and I told him that a glass of
wine would be very nice. He brought me glass of Cabernet and we chatted
for a few minutes about his business and his marital status, which was
single and how his interviewing process was going. He said he talked to
three other men but certainly nobody like me, and the way he said it he
seemed very impressed with me. I finished my wine and he asked me if I
wanted another glass and I said not at the moment. He took my glass back
to the kitchen and came back out to his living room. He sat down in a
chair and told me to sit wherever I like. I thought about it for a few
seconds and then decided to play this up for all I was worth. Instead of
sitting in a chair I walked over to where he was a knelt down at his
feet. If he was looking for a submissive slut, I was the girl for him.
If he wasn't, it would not have worked out anyway.
So I asked him, "Sir what do you expect from a person you wish to share
house with?" Unfortunately, he answered with a question. "What are you
willing to give up?" I told him everything. He stood up from a chair
and I reached up and unzipped his pants. I pulled his rather large cock
out, and kissed it with my red lipsticked lips. He got hard immediately
and I toyed with his penis for a long time. I sucked on his balls and he
seemed to enjoy that as well. I then started sucking his cock in
earnest, and it did not take very long until I realized he was about to
come. I kept going and felt his cum hit the back of my throat. I just
swallowed all of it and kept sucking until he pushed my head away.
He seemed very pleased. He pulled me up to a standing position and kissed
me very hard. He then took my hand and lead me into the bedroom. He had
me remove my panties and skirt and lie facedown on the bed. I felt him
lube my ass up and then moments later I felt him enter me. This second
time around it took quite a bit longer and since I was facedown, I
couldn't use any of my usual tricks to get him to come quicker. But I
was pretty happy and I was pretty turned on by how things were going.
It may have been a casting couch kind of interview, but I got the job.
We made arrangements for me to move in and in a week I had my very own
sugar daddy. I was to keep the house clean while he was gone and when he
showed up on Friday afternoons I was to greet him at the door on my
knees. I was falling in love but it did seem pretty clear to me that, to
him, it was just an arrangement.
One night, after we had been doing this for about a month, we were
talking for a bit. Malcolm asked me how much I wanted to be a woman. I
told him as much as possible. He asked if I would be interested in
taking hormones and perhaps getting breast implants. I told him I was
very much interested, especially in getting breast implants. All through
this I dreamed about having large breasts. He said that since he was a
doctor, prescribing the hormones would be easy and he would do it right
away. He said he just wanted to read up to see what the doses would be
correct. He told me that he had a friend that was a plastic surgeon that
we might talk to about getting implants.
Needless to say, I started on the hormone regimen right away. I felt
kind of odd physically at first and I didn't see much difference other
than my nipple seem to be very sensitive. However, after about three
months I could detect changes in my physique. All this time my
benefactor was buying me new dresses and shoes to wear. He also bought a
variety of restraints and toys for me to use. He bought a stainless
steel collar for me that looked kind of like jewelry, but it was pretty
obvious that it was a slave collar. When he was home, I would frequently
have to wear handcuffs and a ball gag in my mouth. I would make him
dinner and kneel at his feet waiting for him to finish. Clearly he
wanted me to be a serving wench.
After a while, he took more and more control. He liked to control my
bathroom habits too. He would lock my penis in a chastity cage and also
make me wear a butt plug that was locked in place. In theory, I was only
supposed to go to the bathroom when he said it was allowable. Of course,
the bathroom control was only when he was around, however the chastity
cage was locked in place constantly. There were times when I couldn't
control myself and ended up soiling myself. When that happened he would
make me sit on my own filth and suck his cock first before I could go to
the bathroom and clean up.
One day he told me to get in the car and said that we're going to go meet
his friend the plastic surgeon. When we got there, it was clearly not
the surgeon's regular office hours. Malcolm told me to wait in the
waiting room and he went to talk to his friend. In a few minutes, he
came out and motioned for me to come in. I said hello to the other
doctor and then Malcolm told me to take off my clothes. I was little
surprised with this but at this point I was pretty used to doing what I
was told and it was a doctor's office after all. I got a pretty thorough
examination and there was a lot of discussion about what medical
procedures could be done. I didn't really participate very much in the
discussion. The one thing I did say was when there was some talk about
size of implants and I said I wanted very big ones. However as soon as I
said that, it was made clear to me that I was to speak only when spoken
to. Malcomb and his friend discussed breast implants, butt implants,
laser hair removal, liposuction, and lip injections.
To my great surprise, at one point Malcolm told me it was time to take
care of his friend. I started to ask what he meant, but in a few seconds
it became pretty clear as his friend opened his zipper and pulled his
cock out. Malcomb told me to start sucking. I was just stunned by this
because up till now, it had appeared as if Malcolm only wanted me all to
himself. He got a little cross at my delay, and said just do it. So,
dutiful slut that I am, I took care of the new doctor.
After we left the doctors office, Malcolm explained to me that the
various surgeries that he was talking about performing were very
expensive. Instead of Malcolm paying the surgeon, the surgeon was going
to take it out in trade with me. Malcolm would have me for the weekends,
and the surgeon would have me the rest of the week. This made me more
than a little nervous, as I was not crazy about being whored out for
medical procedures, but at the same time I had bought into my
transformation at this point. In any event, I could see that Malcolm was
conflicted by this and I leaned over and sucked his cock on the way home
to console him.
The first operation I got were the breast implants. They were not quite
as big as I would've liked but I was told anything bigger would've looked
like cantaloupes glued to my chest since I didn't have much breast tissue
to begin with. Still, I ended up with a nice large C cup. I spent quite
a bit of time with laser hair removal. Then came the lip injections
which I thought really altered my features quite a bit. The two doctors
kept remarking about my cock sucker lips, but it was the one thing they
did to me I thought made me look a little odd and that looked like I had
had plastic surgery. At some point, I realized I could never go home to
my parents again..
The one real mistake I made one was when I signed a release form for an
orchiectomy. I was signing release forms right and left and at one point
we were talking about shaving my Adam's apple and that's what I thought
it was for. Imagine my surprise when I woke up with no testicles. I was
somewhat upset but at the same time realize that this whole process has
been going on without a whole lot of input from me and that I was going
along with everything so why not this too? Malcolm said that they did it
so the hormones would work better. That did indeed seem to be the case.
I never got the butt implants, however they did do liposuction on my
stomach and injected the fat into my butt, which rounded it out nicely.
I got to a point where, if I went out, I couldn't walk down the street
without men whistling or making comments. Except for my limp penis and
the fact I had no vagina I was pretty much a girl at this point.
My life was divided between the two doctors, although they each treated
me quite a bit differently. Malcolm was becoming a little meaner and a
little rougher. I suspected that he was taking out his anger at having
to share me with the other doctor on me. He started taking to slapping
my face during sex which I didn't like all. I was completely on board
with getting spanked but slapping in the face was bad.
The other doctor like to have parties. He would invite friends over and
have me serve them. At first I was mostly window dressing. The one night
when I asked one of his guests what he wanted, he responded with beer and
a blowjob. I gave him a beer and walked away and the doctor accosted me
and said why aren't you giving him the blowjob he asked for? I started
to protest but he said just go and do it. Next thing I know, I'm giving
blowjobs to everybody in the room and then a short time after that I'm
face down on the bed pulling a train.
The doctor said I was to not to tell Malcomb any of this. And this
started a period of my life where for a few months, at least once a week,
my doctor friend would have a party with anywhere from 5 to 10 people
where I was expected to service anyone that wanted it.
Unfortunately between the hormones and the castration, my own sex drive
had very much diminished to nothing. Where in the early stages of this
transformation, this sort of thing would have turned me on like nobody's
business, it just didn't do anything for me at all. I could not get an
erection anymore and no amount of tugging would give me an orgasm. I had
had some girlfriends in the past that told me they were frigid and I
guess I could sense what they must have been going through.
It had now been almost two years. I could sense that things were going
wrong in many ways. Malcomb was getting meaner and more distant and the
good doctor was getting more and more perverted. Maybe I just needed a
rest, I don't know. I had no money, and had dropped out of school. I
hadn't seen my parents in all this time and figured they would probably
have a heart attack if they saw me. I needed a plan.
Malcomb was only coming to town two weekends a month at this point. So I
had a couple of weekends to myself. I started placing ads in the local
classifieds whoring myself out. I found that the going rate was $200 per
hour. I advertised a girlfriend experience, though business was not too
brisk. It seems that most men looking for a walk on the wild side want
the transsexual to top them, or at least be "fully functional." That
wasn't me. But for those generous men that wanted a submissive
girlfriend that would do almost anything, I fit the bill nicely and I
found I could make anywhere from $600 to $1200 on a weekend. At one
point, I found a fellow that wanted me to spend the night and was willing
to pay nicely for that. I managed to squirrel away some get out of town
money pretty quickly.
I bided my time. I figured the best time to leave was on one of those
weekends when Malcolm was not in town. I figured I could get a head
start and get out of town before anyone noticed. I am not sure why I was
acting like I was in prison. I pretty much had free reign when either of
the doctors were working. But I just didn't know how they would take it
and didn't want the confrontation. I had long ago found the key to the
chastity cage and at that point it was more self imposed than anything.
In any event, the surgeon dropped me off at the house and I wrote a note
to Malcolm saying thanks and that I was heading to Florida (I was really
going to California) and goodbye. I paid ******** a bus ticket to Los
Angeles and got on the bus. And off I went on my next adventure.
I am about to tell a story that is true. It was my first experience but
it shaped my life forever, not necessarily for the better. As a c***d,
I used to fantasize about being a woman, but never acted on it.
Anything "gay" freaked me out. In any event, I was very closeted and
repressed. And very awkward around women I was attracted to, but seemed
to be able to make a lot of female "friends."
Years ago when I was in my twenties, a female friend of mine, Karen,
tripped and fell and cut her chin open. One of her girlfriends, Kathy,
loaned me her car to give Karen a ride to the hospital. After taking my
friend Karen to the hospital and getting her stitched up I drove her
home and then drove the car to a bar that had bands that play jazz where
Kathy was, so I can return the car. I had expected Kathy to have the
courtesy to drive me home but she didn't want to do that so I was kind
of stuck.
I decided to hitchhike home. After a brief period of time, a fairly
conservative looking guy picked me up and asked me where I was going. I
gave him directions and off we started. I suppose I should describe
myself. In those days I have very long hair which reached down to the
middle of my back. I was tall and very slender. Jerks used to shout at
me from their car windows "are you a boy or a girl?' In any event, my
rescuer was a fairly large and burly looking guy, but seemed friendly
and we had a pleasant time talking. In those days, I lived in a college
town and hitchhiking was a viable means of transportation and a good way
to meet interesting people. He asked me if I needed to get home right
away and I told him not necessarily. We stopped at another bar he was
familiar with and listened to a live band this guy knew about. It was a
country and western band, which wasn't really my thing, but they sounded
pretty good. It didn't seem like a shitkicker bar so after my initial
anxiety, I was reasonably comfortable. I remember my benefactor kept
saying of the guitar player "he plays a mean guitar doesn't he?" He
said that many times and I think he was pretty drunk by then. We got
back into his car and he then asked if I wanted to stop at his house for
more drinks (he said it was close by and that he would drive me home
after that). I was pretty blasted at that point, having been drinking
all night. I said ok, and we talked some more, then, after a few minutes
as we were driving, he asked me if I had ever sucked a cock. Out of the
blue, as we had not talked about anything sexual all night. I was very
nervous, and felt butterflies in my stomach like never before, but at
the same time, I became pretty excited (and as I said, I was really
drunk).
It had been something but I had fantasized about for a long time but
never had acted on. I have always had fantasies of being a woman, or at
least playing that role with a man. When I looked at porn, it was
always straight porn, but I loved watching cocks and cumshots more than
anything. In any event, I said no I had never sucked a cock. He looked
disappointed, but then I told him that I had fantasized about it for
some time. I then asked him why he asked me that question. He reached
over and took my hand and put it on his crotch. I could feel him getting
hard and I remember thinking that he was pretty big too. I was filled
with anxiety but I got hard too. I was way too anxious to say anything.
With his hand over mine and, therefore, making me do it, I fondled his
cock on the way to his house, but only through his pants.
When we got to his house and went inside, he told me to strip. His
attitude changed quite a bit all of a sudden. He wasn't exactly mean
but suddenly he seemed very demanding. He told me he was divorced, but
had some of his wife's stuff still. I had long hair back in those days.
He left for a minute, came back with a skirt and some lipstick. He
again told me to strip and I was worried for a while that something
really bad was going to happen to me. However, I have always been a
little submissive and I felt like I should obey. I said "Yes Sir" and I
peeled off my clothes and was standing there in front of him naked with
my dick as hard as it has ever been in my life. He told me to put on
the skirt and then he applied the lipstick to me. My heart was
pounding.
At that point he kissed me and stuck his tongue in my mouth. He put his
hands on my shoulders and pushed me down to my knees and told me to suck
his cock. I unzipped his pants, he was partially hard and in order to
please him I licked the shaft of his cock and his balls and then
proceeded to start to suck his cock while my hand cradled his balls.
While I was doing that, he started calling me names, telling me that I
was a whore and a cocksucker. I pulled back a bit, startled that he
was treating me like this, but at the same time was incredibly turned
on. He told me to keep sucking and pushed my head on his shaft. I
started gagging a bit and that seemed to turn him on more. He really
was pretty big and my jaw was getting very tired and I wasn't sure how
much longer I could keep it up, but when I squeezed his balls a bit, he
came in my mouth and all over my face. I was freaked out and spit out
the cum, which dribbled down my chin, but he wouldn't let me get up for
a while and there I was, on my knees with cum dripping down my chin and
lipstick smeared on my face.
He did not do anything to get me off and I asked if he minded if I
jerked off. He told me I could if I ate my own cum, but then didn't
make me do it when I came. I never came so hard in my life and it only
took a few seconds as I was so turned on.
He told me to clean myself off in the bathroom. I went and wiped
everything off of me and came back to the living room topless and still
wearing the skirt. He pulled out the lipstick again and painted my lips
for the second time. He started kissing me again, really hard and then
made me lie down on the floor. He got some Vaseline (which is not a
very good lubricant as I was about to find our the hard way) and smeared
a handful on my ass. He then mounted me missionary style and I wrapped
my legs around him as he entered me. You read all of these stories that
say that anal sex hurts at first and then the fuckee loosens up and it
feels ever so good? I am sorry to say that it hurt a lot at first and
just got worse. I had a drunken guy fucking the hell out of me and he
would not stop until he came. I think that it took a very long time
both because he was drunk and it was his second shot of the evening. I
wasn't sure what to do, and I was in pain, so I reached around and put
my finger in his ass and at the same time, started sucking on his
nipples. That seemed to do the trick as he started grunting and I could
feel him shaking all over as he bred me.
After that, we both kind of passed out. I woke up a few hours later. He
was still lights out. I had sobered up a bit and the reality of what I
was doing hit me and I was in a panic. I tip toed to the bathroom,
wiped off the rest of the lipstick, put on my clothes and left. As I
sobered up, I was pretty freaked out. It had been my first experience
with a man and as a k** growing up, the worst insult anybody could throw
at you was fag. And here I was, completely emasculated, but really
turned on by it. I was not sure of what that meant, or the consequences
of my actions.
I had blood in the toilet the next day when I went to the bathroom, but
I was scared to go to the hospital. It took about four days for my butt
to stop hurting. I masturbated a couple of times every night reliving
the memory of that evening. I did not know my new friend's phone number
and wasn't sure if I wanted to, or should, ever try to contact him
again. I was not sure what my reception would be. At the same time, I
was fascinated with the role I had played.
I went back and forth about the experience, but what it did for me was
to start me on the road to my slow transformation. I shaved all my body
hair off, including my armpits and legs. I mail ordered some panties
and got some nail polish from the store and started wearing panties
under my regular clothing and also started painting my toenails. It
turned me on to think about having that secret as I went about my
regular business. I also bought a bra and some breast forms and would
put them on when I was alone. But I was scared to venture out with
those on.
Since the time of my first experience, I spent a bit of time troubled by
what happened. On the one hand, it turned me on like I had never
expected. On the other hand, I was experiencing a lot of conflict with
my sexuality. I will say in those days, that I would have more than a
bit of anxiety thinking that I was gay. I was more than a bit ignorant
of the transgender scene, which was non-existent in my home town as far
as I knew, and the internet was not as sophisticated as it is now. It
may sound odd, or contradictory, but I guess I convinced myself that if
I was a woman, it would not be so wrong, but I was a man. In any event,
I was pretty sure that I had taken my walk on the wild side and spent
some time overcompensating for it. A nice fantasy to use, but not
something I would repeat. I would walk down the street desperately
trying to make sure that I was attracted to every woman that went by.
Unfortunately, my period of real chastity didn't last all that long.
After a few weeks of trying to be very macho, I reverted back to being
more feminine, at least in private. In short order, I became addicted
to my closet dressing and wore panties underneath my regular clothes
almost every day. I also painted my toenails and went about my business
with my covered up toes screaming alternative lifestyle. In addition
to the feminine clothes that I had purchased, I went to the local
"marital aids" shop and purchased a number of toys. I bought a butt
plug and a couple of dildos. My fantasy life for masturbating mainly
consisted of me dressing up fully, putting on makeup and getting one of
my dildos and putting it in my mouth and pretending that I was sucking
cock, while at the same time, stretching my ass with a fairly good sixed
butt plug. I really liked wearing bright red lipstick for some reason.
I would also practice sucking cock on the dildo and got my jaw muscles
in better shape than they were before.
I fantasized about men cumming in my mouth. I liked to watch bukakke
videos. I would tell myself that I would swallow my own cum to practice
doing it for the next man I might pleasure. Of course, as soon as I had
an orgasm, I would be disgusted with myself and take off my clothes,
wipe the cum off my hand and not swallow anything. Fantasy and reality
do not always mix. I did have a few times where I would lay on my back
and bring my legs over my head so that my cock was in front of my face.
If I really forced it, I could just get the head of my cock in my mouth.
I started getting some neck pain from that and stopped that practice
pretty quick.
In any event, as was my practice, I had driven to school for class and
was driving home to the West side of town. From the outside, I looked
like a typical college student with boots, bluejeans and a flannel
shirt. However underneath I had painted my toenails red, had red thigh
highs on and red panties on underneath everything. I picked up a hitch-
hiker who was going about half way down Main Street. He said his name
was Frank. Frank was a tall very built, black man in his early 20's.
We started talking about music and found we had a lot in common. We
both liked the same kind of music and he said that he invited me back to
his place. He seemed like a nice guy and I had nothing to do, so I
agreed to take him home.
It was snowy out, so I took my boots off when we got to his place. We
spent what seemed like a few hours talking and we were drinking a fair
amount and I was pretty buzzed. He was playing a bunch of records by
artists that I was not familiar with and I think he enjoyed turning me
on to new music. At some point, his phone rang and he picked it up.
The conversation sounded like he was talking to a friend. All of a
sudden, he had a odd, kind of puzzled look on his face and it looked
like he was staring at my feet. I looked down and to my dismay, saw
that there was a hole at my big toe in my right sock. My bright red
toenail and the red stockings were poking out, and apparently, giving
away my secret. I could tell from the conversation that his friend
wanted to come over right away, but Frank was telling him to come by in
a few hours. I could make out what sounded like the question being
asked on the other side of the line: "What, do you have a girl over?"
and definitely heard Frank say "you might say something like that."
Frank hung up and gave me a funny look. I kind of raised my arms and
shrugged. Frank said "is there something you want to tell me?" He took
a step towards me, but still was about 3 feet away from the couch I was
sitting on. I wasn't sure what to say, and maybe Frank wasn't either,
but I said "I have a bit of a secret - here let me show you. " I stood
up and pulled off my jeans, which exposed my thigh highs, panties and
toenails. He kind of stared at me for short while, and I wasn't sure
how he would react, but in a few seconds, it was clear what he was going
to do. He simply unbuckled his belt and zipped his fly down and let
his pants drop to his ankles and then looked at me with an Ok, what are
you going to do now look? I could have said something, or jumped up and
left, but instead, l found myself looking at the most perfect cock I had
ever seen in my life. I was immobilized for a few seconds. Flaccid, his
dick was bigger than mine when it was fully erect. In any event, I
found myself kneeling in front of him with my mouth open. I put my lips
on the head of his cock and started sucking, feeling him getting bigger
and bigger. Frank's cock was a "shower" because while it did get bigger
when he was erect, it didn't increase in size proportionately the way
mine does. That was a good thing, otherwise, I could not have taken it
in my mouth. In any event, Frank had to be a good 8 or 9 inches when
hard. I licked his shaft and sucked on his balls for a while and then
got to work on the head of his shaft. I had one hand on his balls and
another on his shaft and was sucking on the head of his cock for all I
was worth. I could feel him start to shake and in a few seconds after
that, felt his cum hitting my mouth. I swallowed and swallowed until he
was done and then sat back up on the couch. The whole event couldn't
have taken more than 5 minutes. I wasn't sure what was going to happen
next. Frank told me that I was the first man he had been with and I
told him he was the second. He said that his friends were coming over
soon and I should leave, but he said I should call him later in the
week. He gave me his phone number and I left his apartment with the
taste of cum in my mouth and thought to myself that I was pretty sure I
was about to begin another bout of anxiety and self doubt. And indeed I
did. While I went home and masturbated to the memory of what I had just
done, I am sad to say that I never called Frank and never got together
with him again. Looking back on it I got the sense that might've been
the most normal relationship I might've had in all this. But at the
same time, what was a pleasant afternoon ended with a blow and go (and
with no though of my pleasure at the time). In any event, this second
step pretty much made it impossible to pretend that my feminization was
something I could stop at any time. Also, it worried me that my
immediate reaction to seeing another man's cock was to drop to my knees
and start sucking. And why was I only concerned about pleasing him and
not myself at the time? As future episodes will reveal, that reaction
would dictate the path my life was about to take.
After a few weeks had passed since my encounter with Frank, I felt like
maybe I should try to make contact with the man that had started my path
to ruin. Since it was still winter, I could do a lot of things without
people noticing. I continued to shave my legs, chest and underarms and
paint my toenails. In preparation to meet John (I really wanted to make
a good impression) I got a pair of red panties and red thigh high
stockings and put those on. I put on a bra with my breast forms and
topped it off with a red form fitting dress. I put jeans on over this
and put on my down coat and boots. The coat covered the breast forms
nicely and I looked pretty normal and nobody would know I was femmed up
underneath. I also got some KY jelly as I had learned my lesson about
Vaseline.
It was a Saturday night and I went to John's house. The lights were on
and my heart was pounding as I rang the door bell. He answered the door
and looked very surprised to see me. I said hello and told him that if
this was a bad time or if he didn't ever want to see me again I would not
bother him. He had a funny look on his face and then smiled and told me
to come in. When I stepped into the hallway, I heard him close and lock
the door behind me and then I heard voices in another room. He took my
hand and pulled me into his living room. There, to my shock and horror,
were two other men. They were both drinking beer and there was a porn
video playing on the television. One of the men was in a chair, with his
pants around his ankles jerking off.
"This is the sissy I was telling you about" he said. It turned out that
since my encounter with John, he had discovered social media and was
getting his needs fulfilled by putting ads in for guys to get together
and jerk off to porn. I had stepped into one of those times. In any
event, he then turned to me and told me to take off my jacket. Seeing my
dress, panties and the stockings, all three men started laughing and
calling me names and asked me what I was going to do for them. John went
to the bathroom and got out the lipstick. On it went and next thing I
knew, I was on my knees with three men in front of me. I had a cock in
my mouth and one in each hand, while on the television a naked female
slut was doing the same thing, only with five men.
The first man came in my mouth pretty quickly and all three of the men
told me to swallow his come like a whore would. (I am not sure that real
whores do that, but swallow I did). It tasted bad. So many times the
fantasy never lives up to the reality. The first comer (I never did get
his name) then went to the kitchen to get beers for the others and I
moved on to sucking the other stranger's cock. My jaw started to get
tired again and I was not sure how long I could keep sucking. John was
looking at me and I tried squeezing the stranger's balls to see if that
would hurry things up. Fortunately it did, and I was swallowing my
second load of the evening.
The two strangers sat down on the couch to watch me suck off John's cock.
His was the biggest one, and I was trembling to keep my jaw from locking
up. Oddly, a minute after I started, he turned his back to me. I was
afraid I had displeased him, but at the same time, needed a moment to
rest my jaw. My relief turned to grief when he told me to lick his
asshole. I had never done that before and was grossed out. He said it
again and told me he did not want to have to tell me a third time. I got
nervous and did what I was told. I could smell excrement and was
gagging, but stuck my tongue in his butt hole like he demanded. He told
the others "looks like this sissy is will do anything I tell her to." I
guess I would, or so it appeared at the moment. My fault for going back
I guess. After I had licked his ass clean, he told me to stand up and
stay in place. He went to another room and came back with an old looking
dog collar and a leash. I was collared and he pulled the leash and made
me follow him to the bedroom. I was made to take off my dress and
panties. He lay down on the bed on his back and told me to get on all
fours and suck him off. A minute later, his friends came into the
bedroom and one of them started playing with my ass. I felt some lube go
on and then I felt a cock pushing to get into me. Pretty soon, I was
being spit roasted. I found it hard to concentrate on sucking cock with
another one slamming into me, but fortunately, the stranger came quickly.
Then it was the other's turn. He too was relatively quick, something for
which I was grateful, as I was still not used to anal sex. My jaw was
giving out when John moved around, pushed my face into the pillow and
rammed his big cock into my butt. He pumped for all he was worth. I
was glad the other two smaller men had opened me up, because I think I
would have really had a bad time otherwise. He came and then it seemed
like the guys were done with me. "Get dressed slut" I was told. As soon
as I was dressed, John told me it was time to leave. As he closed the
door, he told me that I should return in two weeks and that I would have
a night I would never forget.
I had already had a night I would never forget. I never returned as I
was afraid of what lay in store for me. I think that, originally, I
thought that by going back, I might be able to develop a regular kind of
relationship with John and perhaps have regular outlet for my submissive
urges, but I wasn't ready to be passed around like some prison bitch. I
was also a bit disturbed and scared by my acquiescence at being ordered
to do kinky things. Of course, like so many New Year's resolutions, it
seemed like I was destined to forget this lesson all too soon.
This chapter is a bit creepy, but it is part of my story. I had a very
weird relationship with my mother. She was an alcoholic and very
flighty. In many ways, I feel that she unmanned me growing up. In any
event, I had not seen her for a while, and she called me up and told me
that she wanted to come by and take me to the movies. When she got to
my apartment she then said that she had been dating some guy for a while
and wanted him to come along as well and asked if I would mind. I said
no, I wouldn't mind (like I had a choice).
On the way over to the fellow's place, (his name was Bob) mom was
complaining that she wondered if the guy was gay. She said usually when
she went out with a man, he would be all over her but this guy had never
made a move on her or had even tried to kiss her. (Mom had a habit of
sharing her sex life with me-never mind that I had told her that such
talk makes me very uncomfortable). She said Bob was a photographer and
indeed when we go to his house he did have a very elaborate photo studio
in one of his rooms with a backdrop and lights.
We made some small talk and then went to the movies. Mom and Bob talked
through the entire film, with people in the seats around us telling them
to be quiet. Mom always did things that embarrassed me and never seemed
to care. After the movie, we went back to Bob's house to have some
drinks. Bob made us all martinis and the conversation livened up quite
a bit. It was the first time I had ever had a martini (or three) and I
was pretty buzzed.
We spent a little time talking and Bob seem to be a bit taken with me,
or so I thought. He spent most of the time talking to me and ignoring
my mother. He asked a lot of questions about my long hair and asked if
men confused me for a girl. My mom did not like that line of
questioning and it made me a little uncomfortable too, since she was
there. I am not sure how I would have felt about it if she wasn't with
me.
At one point, as Bob was showing us around the house, we were standing
in Bob's living room. My mom asked to use the bathroom, which was down
a long hall. As she was walking down the hall, Bob stood to my side and
sort of caressed my ass with the palm of his hand and told me that I was
welcome to come by anytime. Oddly, I did not pull away at this touch.
I started getting hard and took my hand to adjust my cock to be more
comfortable in my jeans. Bob noticed immediately and ran his hand up
underneath my ass and cupped my balls. I heard the toilet flush and
found a couch to sit on so that mom would not come out of the bathroom
and see me with a hard-on. Bob was grinning like the cat that ate the
canary and I knew I was in trouble, again.
When it was time to leave, Bob told me in front of my mother that I was
welcome to come by anytime. He said if I want to use his place to study
I could do that. When mom went to use the bathroom again before we
left, the conversation changed a bit. Bob said that he would be
interested in photographing me with some other young men he knew. He
mentioned the word "masculine" when describing them. The whole time he
was talking, he caressed my ass. I felt like he knew my secret. I was
a bit nervous since I expected my mother to come out of the bathroom at
every second. What a weird situation to be in. He slipped a business
card into my hand and said, "Call me." Moments later, mom got out of
the bathroom and off we went
I have to confess that I was pretty curious about all this, although at
the same time, to be hanging out at this guys house would be bad news if
it got back to my mother. Also, Bob was considerably older than I was,
by at least 25 years. Despite any misgivings, I waited a couple of days
and gave him a call. He seemed very happy to hear from me and asked me
to come over that afternoon. As usual, I had my red panties and
stockings on underneath my clothes. I went to his house and he greeted
me very warmly with a big smile and invited me in. We talked for what
seemed a long time and after a number of drinks and after swearing him
to secrecy I told him my life story. He acted like he was very
interested in hearing my story and kept urging me to continue telling it
to him, though I was not sure at the time what his goal was.
At some point he put his hand on my thigh and I was pretty sure where
his hand was going to go next. Next thing, I knew he had his hand on my
cock and he was kneeling in front of me. He unzipped my pants, pushed
my panties aside and pulled my cock out and started sucking my cock. I
came in seconds. Moments later, I stood up and took my outer clothes
off. Exposing my panties and stockings. I undid his belt, unbuttoned
his pants, unzipped his fly and attacked his cock for all I was worth.
He too came in just a very short while and I swallowed his cum. This
act was getting easier and easier for me.
Since I had already told him my story about how I like to dress in girls
clothing and he seemed kind of turned on by it, I didn't feel too much
anxiety at the time. He asked me if I wanted to come over another time
and have him take pictures of me dressed but that made me very nervous
because I didn't want pictures like that of me circulating. After all,
it was possible that my mother would come by and see them and that would
really be a problem for me.
Bob asked me if I would come by on the weekend. He told me that he had a
couple of other young "masculine" male friends that were coming over and
he would like us all to get together. I told him I would come by. He
asked if I would come by and get dressed and I said that I would think
about it. He said that I could come by dressed normally and get dressed
as a girl at his place. He also said that if I was a girl, that I might
have a very nice time with his two other young friends.
I did go to his house that Saturday afternoon and spent a fair amount of
time in his bathroom getting ready. As I have told you, I had really
long hair in those days. I had a bra and breast forms, panties, thigh
highs, short miniskirt, spike heels and a nice blouse that I put on. I
spent a lot of time on my makeup. I put on false eyelashes and
foundation and eyeliner and bright red lipstick. When I came out of the
bathroom, I felt I look pretty hot. Bob's two friends came over and
they looked like they were about 18 or 19 years old thin and built.
They had apparently been over to Bob's before and were quite familiar
with the place. In any event, they quickly took off their clothes and
were standing naked in front of me. Bob took charge and told me that
these two boys were my dates for the day and that I should take care of
them.
Somehow I felt like I had no will of my own and I took a few steps
towards these two guys I had never seen before in my life. Next thing I
knew I was on my knees sucking the cock of the first of the two to get a
hard on. There was a mattress on the floor and he pulled me onto it. So
he was lying on his back and I was sucking his cock. The other boy got
behind me and pulled my panties down and I could feel his cock probing
my ass. Next thing I knew I had one cock in my mouth and one in my ass
and both boys were pumping me for all they were worth. Neither of the
two was very well endowed so I had an easy time on both fronts.
Apparently, while all this was going on Bob had a video camera going.
So I was being recorded for posterity without my knowing. The two boys
took turns with me and I was their receptacle for what seemed like a
couple of hours. When they were done, we all got dressed and the two
boys left and I got ready to say goodbye to Bob. He told me about the
video and I got pretty upset since I told him I didn't want him to take
pictures. He showed me the video and said that he was only going to use
it to jerk off, but then he said that he wanted me to come to his
"parties" again. He told me that if I didn't cooperate that he would
show the video to my mother.
I didn't know if you would or not but I felt like he was blackmailing me
into being a sex slave for his videos. Also, I wanted to know what he
was doing with the videos. I was worried that he might be putting them
on the Internet. However he had me in the worst possible position and I
felt like I was stuck doing whatever he wanted. Bob told me to show up
the next Saturday and to come fully dressed.
I did show up the next week and when I got there, five naked college
boys were standing around in Bob's house. I went into the bathroom to
put on my make up and when I got out Bob said to all of us, "Well, you
know what to do." One of the older boys walked up to me and kissed me.
I kind of liked that as it made me feel little less used than what had
happened the week before. But that was short lived.
Next thing I knew I was on my knees with cocks surrounding me. I went
from cock to cock keep it all five hard for a while. I then started to
concentrate on the boy with the biggest cock, sucking and squeezing his
balls. Pretty soon I could feel him tense up. He puled pulled his cock
out of my mouth and squirted his cum on my face and in my hair. With
his cum dripping down my face and onto my blouse, I then turned to the
next hard cock I could see and concentrated on it. In about two
minutes, this boy blasted my face with his cum as well. A that instant
a third guy who had been jerking off said "look at me" and sprayed me
down with his cum.
The fourth boy told me to lie down on the mattress and spread my legs
and pulled off my panties. He lubed me up and entered my ass and I
wrapped my legs around him. As soon as he came in my ass, the fifth
boy took his place and pumped me for all he was worth. Bob seem very
happy with all this and I noticed that he had a camera in his hands.
After all the sex was done, the boys got dressed and left. I was pretty
spent and in the need of a little time to recover. However while I was
lying on the mattress, Bob came over and unzipped his pants and motioned
me over to his cock. I had cum dripping off my face and my hair and all
my clothes and also dripping out of my ass. My jaw was tired but I
opened my mouth and started sucking on the head of his cock. I guess
the show had really turned him on because it only took him about half a
minute to ejaculate. When it was done I got up and went to the bathroom
and cleaned up a bit. As I was leaving he told me to be sure to come by
the next weekend for "more fun." I left his house wondering what I had
gotten myself into.
Unfortunately a few days after all this, I started to get a sore throat.
I had trouble swallowing and there were white spots on my throat. When
I went to the doctor I was diagnosed with oral gonorrhea. I was pretty
freaked out. I called Bob yelling. I told him I didn't care what he did
but I wasn't coming back. Oddly enough he did not give me a hard time.
I never did see any pictures of me having sex on the internet, but I am
not sure that I would know where too look. One comforting thought that
I had was that if the boys gave me VD, I probably transmitted it to Bob
at the end of the day. I took my tetracycline and put away my clothes
for a while. I later was told that my *** test was negative, so I had a
bit of relief, but this was a real wake up call about safe sex and what
I was doing. But the memory of the group sex really turned me on and I
think that I was hooked on the adrenaline rush of it all. Talk about
conflicted. But no death wish here, so I vowed to be more careful in
the future.
At this point my life I was pretty much torn between my desires, almost
compulsion, to cross dress and have sex with men and clinging to whatever
semblance of what was left of my former normal life. I am a bit of a
hypochondriac, and was worried about disease. I had already learned my
lesson regarding that the hard way. In any event I was hanging out at my
apartment with my roommates and one of them came in with the campus
newspaper and was laughing about an ad in the personal section. The ad
said "free lodging and a Mustang convertible to use during the week in
exchange for pleasurable weekends." It went on to say that the person
that placed the ad lived in New York City but traveled to my town
frequently for business. While my roommates were making fun of this, it
sounded like a pretty interesting idea for me.
In any event I called the number that was in the ad and spoke to a
pleasant sounding man. He said his name was Malcolm and he was a doctor,
and that he managed emergency rooms and hospitals and as part of his
business, he came to my town pretty much every weekend. We arranged a
time for him to "interview" me and I thought about how I would prepare.
I did not ask him over the phone if he was looking for a masculine
boyfriend but figured there would be plenty of those but I might stand
out if I should come fully dressed.
In any event, I want the whole 9 yards. I put on panties, thigh highs,
stiletto heels, very short miniskirt, and my biggest breast forms, very
tight top and with the full make up including eyeshadow, false eyelashes
and deep red lipstick. To top it off, I put on a beautiful blond wig. I
really looked pretty hot. The big question of course was whether or not
the good doctor wanted a submissive girl or a masculine boy.
I snuck out of my apartment and drove over to the meeting place. I rang
the doorbell and my heart was pounding. The man that opened the door
looked to be in his early 40s, he was tall maybe 6'3" and had very
chiseled good looks. He was clearly surprised to see me dressed up as I
was, but after the first look of surprise, he got a really big smile on
his face and invited me in.
He asked me if I wanted anything to drink and I told him that a glass of
wine would be very nice. He brought me glass of Cabernet and we chatted
for a few minutes about his business and his marital status, which was
single and how his interviewing process was going. He said he talked to
three other men but certainly nobody like me, and the way he said it he
seemed very impressed with me. I finished my wine and he asked me if I
wanted another glass and I said not at the moment. He took my glass back
to the kitchen and came back out to his living room. He sat down in a
chair and told me to sit wherever I like. I thought about it for a few
seconds and then decided to play this up for all I was worth. Instead of
sitting in a chair I walked over to where he was a knelt down at his
feet. If he was looking for a submissive slut, I was the girl for him.
If he wasn't, it would not have worked out anyway.
So I asked him, "Sir what do you expect from a person you wish to share
house with?" Unfortunately, he answered with a question. "What are you
willing to give up?" I told him everything. He stood up from a chair
and I reached up and unzipped his pants. I pulled his rather large cock
out, and kissed it with my red lipsticked lips. He got hard immediately
and I toyed with his penis for a long time. I sucked on his balls and he
seemed to enjoy that as well. I then started sucking his cock in
earnest, and it did not take very long until I realized he was about to
come. I kept going and felt his cum hit the back of my throat. I just
swallowed all of it and kept sucking until he pushed my head away.
He seemed very pleased. He pulled me up to a standing position and kissed
me very hard. He then took my hand and lead me into the bedroom. He had
me remove my panties and skirt and lie facedown on the bed. I felt him
lube my ass up and then moments later I felt him enter me. This second
time around it took quite a bit longer and since I was facedown, I
couldn't use any of my usual tricks to get him to come quicker. But I
was pretty happy and I was pretty turned on by how things were going.
It may have been a casting couch kind of interview, but I got the job.
We made arrangements for me to move in and in a week I had my very own
sugar daddy. I was to keep the house clean while he was gone and when he
showed up on Friday afternoons I was to greet him at the door on my
knees. I was falling in love but it did seem pretty clear to me that, to
him, it was just an arrangement.
One night, after we had been doing this for about a month, we were
talking for a bit. Malcolm asked me how much I wanted to be a woman. I
told him as much as possible. He asked if I would be interested in
taking hormones and perhaps getting breast implants. I told him I was
very much interested, especially in getting breast implants. All through
this I dreamed about having large breasts. He said that since he was a
doctor, prescribing the hormones would be easy and he would do it right
away. He said he just wanted to read up to see what the doses would be
correct. He told me that he had a friend that was a plastic surgeon that
we might talk to about getting implants.
Needless to say, I started on the hormone regimen right away. I felt
kind of odd physically at first and I didn't see much difference other
than my nipple seem to be very sensitive. However, after about three
months I could detect changes in my physique. All this time my
benefactor was buying me new dresses and shoes to wear. He also bought a
variety of restraints and toys for me to use. He bought a stainless
steel collar for me that looked kind of like jewelry, but it was pretty
obvious that it was a slave collar. When he was home, I would frequently
have to wear handcuffs and a ball gag in my mouth. I would make him
dinner and kneel at his feet waiting for him to finish. Clearly he
wanted me to be a serving wench.
After a while, he took more and more control. He liked to control my
bathroom habits too. He would lock my penis in a chastity cage and also
make me wear a butt plug that was locked in place. In theory, I was only
supposed to go to the bathroom when he said it was allowable. Of course,
the bathroom control was only when he was around, however the chastity
cage was locked in place constantly. There were times when I couldn't
control myself and ended up soiling myself. When that happened he would
make me sit on my own filth and suck his cock first before I could go to
the bathroom and clean up.
One day he told me to get in the car and said that we're going to go meet
his friend the plastic surgeon. When we got there, it was clearly not
the surgeon's regular office hours. Malcolm told me to wait in the
waiting room and he went to talk to his friend. In a few minutes, he
came out and motioned for me to come in. I said hello to the other
doctor and then Malcolm told me to take off my clothes. I was little
surprised with this but at this point I was pretty used to doing what I
was told and it was a doctor's office after all. I got a pretty thorough
examination and there was a lot of discussion about what medical
procedures could be done. I didn't really participate very much in the
discussion. The one thing I did say was when there was some talk about
size of implants and I said I wanted very big ones. However as soon as I
said that, it was made clear to me that I was to speak only when spoken
to. Malcomb and his friend discussed breast implants, butt implants,
laser hair removal, liposuction, and lip injections.
To my great surprise, at one point Malcolm told me it was time to take
care of his friend. I started to ask what he meant, but in a few seconds
it became pretty clear as his friend opened his zipper and pulled his
cock out. Malcomb told me to start sucking. I was just stunned by this
because up till now, it had appeared as if Malcolm only wanted me all to
himself. He got a little cross at my delay, and said just do it. So,
dutiful slut that I am, I took care of the new doctor.
After we left the doctors office, Malcolm explained to me that the
various surgeries that he was talking about performing were very
expensive. Instead of Malcolm paying the surgeon, the surgeon was going
to take it out in trade with me. Malcolm would have me for the weekends,
and the surgeon would have me the rest of the week. This made me more
than a little nervous, as I was not crazy about being whored out for
medical procedures, but at the same time I had bought into my
transformation at this point. In any event, I could see that Malcolm was
conflicted by this and I leaned over and sucked his cock on the way home
to console him.
The first operation I got were the breast implants. They were not quite
as big as I would've liked but I was told anything bigger would've looked
like cantaloupes glued to my chest since I didn't have much breast tissue
to begin with. Still, I ended up with a nice large C cup. I spent quite
a bit of time with laser hair removal. Then came the lip injections
which I thought really altered my features quite a bit. The two doctors
kept remarking about my cock sucker lips, but it was the one thing they
did to me I thought made me look a little odd and that looked like I had
had plastic surgery. At some point, I realized I could never go home to
my parents again..
The one real mistake I made one was when I signed a release form for an
orchiectomy. I was signing release forms right and left and at one point
we were talking about shaving my Adam's apple and that's what I thought
it was for. Imagine my surprise when I woke up with no testicles. I was
somewhat upset but at the same time realize that this whole process has
been going on without a whole lot of input from me and that I was going
along with everything so why not this too? Malcolm said that they did it
so the hormones would work better. That did indeed seem to be the case.
I never got the butt implants, however they did do liposuction on my
stomach and injected the fat into my butt, which rounded it out nicely.
I got to a point where, if I went out, I couldn't walk down the street
without men whistling or making comments. Except for my limp penis and
the fact I had no vagina I was pretty much a girl at this point.
My life was divided between the two doctors, although they each treated
me quite a bit differently. Malcolm was becoming a little meaner and a
little rougher. I suspected that he was taking out his anger at having
to share me with the other doctor on me. He started taking to slapping
my face during sex which I didn't like all. I was completely on board
with getting spanked but slapping in the face was bad.
The other doctor like to have parties. He would invite friends over and
have me serve them. At first I was mostly window dressing. The one night
when I asked one of his guests what he wanted, he responded with beer and
a blowjob. I gave him a beer and walked away and the doctor accosted me
and said why aren't you giving him the blowjob he asked for? I started
to protest but he said just go and do it. Next thing I know, I'm giving
blowjobs to everybody in the room and then a short time after that I'm
face down on the bed pulling a train.
The doctor said I was to not to tell Malcomb any of this. And this
started a period of my life where for a few months, at least once a week,
my doctor friend would have a party with anywhere from 5 to 10 people
where I was expected to service anyone that wanted it.
Unfortunately between the hormones and the castration, my own sex drive
had very much diminished to nothing. Where in the early stages of this
transformation, this sort of thing would have turned me on like nobody's
business, it just didn't do anything for me at all. I could not get an
erection anymore and no amount of tugging would give me an orgasm. I had
had some girlfriends in the past that told me they were frigid and I
guess I could sense what they must have been going through.
It had now been almost two years. I could sense that things were going
wrong in many ways. Malcomb was getting meaner and more distant and the
good doctor was getting more and more perverted. Maybe I just needed a
rest, I don't know. I had no money, and had dropped out of school. I
hadn't seen my parents in all this time and figured they would probably
have a heart attack if they saw me. I needed a plan.
Malcomb was only coming to town two weekends a month at this point. So I
had a couple of weekends to myself. I started placing ads in the local
classifieds whoring myself out. I found that the going rate was $200 per
hour. I advertised a girlfriend experience, though business was not too
brisk. It seems that most men looking for a walk on the wild side want
the transsexual to top them, or at least be "fully functional." That
wasn't me. But for those generous men that wanted a submissive
girlfriend that would do almost anything, I fit the bill nicely and I
found I could make anywhere from $600 to $1200 on a weekend. At one
point, I found a fellow that wanted me to spend the night and was willing
to pay nicely for that. I managed to squirrel away some get out of town
money pretty quickly.
I bided my time. I figured the best time to leave was on one of those
weekends when Malcolm was not in town. I figured I could get a head
start and get out of town before anyone noticed. I am not sure why I was
acting like I was in prison. I pretty much had free reign when either of
the doctors were working. But I just didn't know how they would take it
and didn't want the confrontation. I had long ago found the key to the
chastity cage and at that point it was more self imposed than anything.
In any event, the surgeon dropped me off at the house and I wrote a note
to Malcolm saying thanks and that I was heading to Florida (I was really
going to California) and goodbye. I paid ******** a bus ticket to Los
Angeles and got on the bus. And off I went on my next adventure.
10年前
