Sheryl's Experience at the Edgewater

Sheryl's Experience at the Edge


I first met Sheryl several years ago when I was trolling the
AOL chat groups as, Spanksalot. Ever since my divorce I had been
talking advantage of my business travel schedule to meet with
couples as a third. Lately, I had been introduced to some mild
bondage and Dom/sub games with an older couple I had been partying
with. I found that I liked to spank and sometimes Dom a wife while
the husband watched. And I found many other couples who liked to
play this fantasy. Hence the name Spanksalot.
Sheryl Im'd me one night and told me that she liked to be
spanked. Suspicious as I am, I quickly arranged to call her, and
to my surprise she was real. She was married at the time, although
I could tell she was having problems. She told me that she wanted
her husband to be more Dom but that he wasn't interested. The more
we talked, the more I found that she grew silent and breathless
when I told her of some of my experiences with dominating other
wives. She finally told me that some of my stories matched many
of her fantasies.
I knew at this same time that Sheryl was seeing other Doms,
was very active in the Le Chateau chat room and had started
attending some lifestyle meetings and parties. Although I had
friends that were heavily into the Dom/sub lifestyle, I was still
on the peripheral of the whole scene. My interests were strictly
focused on meeting fun couples that need some help fulfilling
certain creative fantasies, as well as my personal sexual
titillation. So sometimes I thought the serious Le Chateau crowd
was a bit over the edge for me; and they probably thought I was not
a serious player.
Although I've met some great folks in the group, I've also endured
a lot of psychobabble, jealousy and ego.
It was my pleasure to finally meet Sheryl several weeks ago.
She had finally left a miserable situation with her husband and
moved to the Bay area. Since I travel to the Bay area on a regular
basis, I arranged to meet her for dinner one night.
I told her to meet me at a Mexican Restaurant down from the
SF Airport. She told me what she would be driving, so I waited in
the parking lot to see if she was real. When her car drove into
the parking lot, I waited to see her before I introduced myself.
She was a BBW (I knew that) and was wearing a black dress that came
down to just above her knees, black stockings, heels and white
pearls. Since it was rather windy in the parking lot, I watched
her walk into the restaurant hoping the wind would blow her skirt
up (always the optimistic voyeur).
When I met her we laughed about the fact that we both wore
black. We ordered drinks, ate our meal and got to know each other.
I mentioned that I was going to spend the weekend at the
Edgewater, an Oakland "swingers" hotel and invited her to join me
the next night for some fun. She was up for it, so the plans were
set. Since I had to get ready for more meetings in the morning, I
paid the bill and e*****ed Sheryl to her car. I mentioned how
windy it was and how I would've loved to see her skirt fly up. She
replied that she was ready for that, since she was wearing
something that I would like.
While she was sitting in her car, I took the hint and ran my
hand up her thigh, discovering that she was wearing stockings and
garter belt....that she was not wearing panties...and that she was
freshly shaven. I looked at her and then inserted two fingers into
her moist cunt. I kissed her and kept my fingers in her pussy, all
the while checking to see if we were being watched. I finally
decided to start testing her submissive inclinations. I pulled out
my hand from under her dress and ordered her to clean her cunt
secretions from my fingers. Sheryl eagerly complied, sucking my
fingers with her eyes closed.
The next day I had lost a client (and a substantial fee) and
was in a foul mood when I escaped to the Edgewater. I settled into
my room, fixed a drink, clipped a Partagas and perched my self on
the second floor balcony. I had just gotten comfortable when I
saw a classy looking couple stroll into the middle of the courtyard
and sat near the Jacuzzi. He was older and she was a gorgeous
brunette with a page boy cut. They both looked like lawyers. She
took off her business dress, underneath was a one piece chamois and
pantyhose. I watched as she took those off and slipped into some
thong bikini bottoms. Her lover, who was in swimming trunks,
started to caress her breasts and kiss her. All of this was in
front of me and several other guys who were waiting for some
action. As we all watched he would stroke her pussy through her
bikini and she would go into a convulsive shudder that signaled her
orgasm. This went on for 45 minutes before she finally bent her
head down and sucked his cock. I don't think he ever came. Since
it seemed they were there for the lunch hour, after an hour, they
both dressed and left in separate cars.
That scenario certainly made me forget my lousy morning and
start planning for Sheryl to arrive. I had put together a bag a
presents for her and couldn't wait to start testing her submission.
When she arrived in the lobby, the clerk called me to e*****
her into the private entrance. I couldn't believe what she was
wearing. A short tight red skirt, a black satin clinging top,
stockings and high heels. Unlike the rather classy black dress she
wore the night before, tonight she looked like a dirty slut. The
clerk looked at me like I had paid less than ten bucks for the
nastiest whore in Oakland. Sheryl needed to be punished for this.
I walked her back to my room through the courtyard, past
leering, horny old men as well as several young well hung studs. I
could see from their faces that they knew they were going to see
more of the cum slut in the red skirt later in the night.
When I got Sheryl to my room, I turned on all the lights and
open curtains to the glass sliding door leading to the balcony
Then I handed her a bag with her presents and a wine cooler.
"Here, some presents for you, and you might want to have a
drink before we start," I said. "Just remember, that we will be
exploring some fantasies tonight and we might push some to the
edge. You just tell me if you are uncomfortable with anything and
I will stop." She acknowledged that she understood.
She opened the gift bag and extracted a chain leash, a dog
collar and a paddle. I fitted the collar around her neck and
attached the leash. Then I ordered her to kneel. I unzipped my
fly, pulled my cock out and ordered her to suck.
"Yes Sir," she replied and lowered her head to engulf my
cock. I could tell Sheryl had been well trained as a submissive
and that she was eager to please. I looked down at her as she
bobbed her head up and down on my cock. I positioned her with her
back to the window. When I looked up, I could see at least two
guys situating themselves out side for a better view. Sheryl, who
was kneeling fully dressed in her slut outfit was starting to
attract the attention of the Edgewater voyeurs.
"Stand up", I ordered, while I sat in a chair in the middle
of the room. Sheryl stood with her back to the window. Strip for
inspection. Top first.
"Yes Sir," she answered, as she took off her blouse, a
chamois and then her black bra.
I stopped her before she bared her breasts. "Take off your
skirt."
She struggled to get out of the red skirt and then stood in
front of me in a black bra, red garter belt, black stockings and
medium heeled black shoes. "Show me your tits," I ordered.
She unclasped her bra and showed me her huge 40DD breasts.
They were full and white, lightly veined, with silver dollar sized
aerioles and nipples that need to be stimulated. She had attached
a set of nipple clamps on a gold chain to her breasts. I thought
that was a nice touch for a second meeting. "Turn around slowly,
show me your ass."
Sheryl was a big woman. Her huge breasts were full, and she
was thick around the middle. Her ass was nice and round and her
thighs accentuated her bare pussy. I ordered her to bend over and
spread her ass cheeks. As she exposed her asshole to me I admired
how her tits hung down. And as I looked past her outside, I could
tell that three guys were also enjoying the show. (Especially
since the mirrored walls gave them views from different angles.)
"OK, Sheryl, very nice," I said. "Now go over to the bed,
bend over and put your hands on the end"
As she complied I ran my hands over her ass to access the
texture and elasticity of her skin. Then I got my paddle, a large
sized "paddleball" paddle that I use on beginners. I could tell
that Sheryl's behind was not virgin to some heavy spanking, so I
wouldn't have to go easy. I brought paddle down medium hard on
her ass. The crack echoed off the walls and even escaped outside,
so that people in the hot tub below could hear. It was about the
fourth whack that I finally heard the first whimper from Sheryl.
By this time, I was giving her full strokes and her ass had just
started to blush. I reached down and spread her cheeks, dipped my
fingers into her cunt to gauge her excitement. That's when I
noticed the size of her outer pussy lips.
Sheryl s pussy lips were huge. I could stretch them out to
about two inches or more! And her bare pussy even accentuated
them. After several more swats, I moved to her nipples, pulling
them to assess their elasticity and sensitivity. Sheryl had a high
pain threshold. I could pull and pinch her nipples pretty hard.
Of course, I know from talking to her that she has had pretty
extensive nipple training before.
"Ready for a walk?", I asked Sheryl.
I don't think she was ready for her first public exhibition.
I attached the leash, and had her put her black camisole over her
naked body. With only her heels, camisole and dog collar/leash, I
led her out the door and down stairs to the hot tub. I purposely
went the long way, leading her around the Edgewater courtyard
hoping that I could expose her as much as possible. When we got to
the hot tub, an older couple and two other guys were already
soaking. Their eyes followed us as I had Sheryl stop and I
unhooked her leash. I then told her to strip. As those in the hot
tub looked on, Sheryl stripped and we joined the others in the hot
tub.
The other woman was also a BBW, with long brown hair, nice
large breasts and ruebenesque ass. We had a nice conversation with
them, as the other two guys in the hot tub leered at Sheryl and the
other woman s tits. Sheryl's especially looked nice floating in
the bubbles of the hot tub.
After a nice soak, I led Sheryl to her car to get her bag of
toys.

I e*****ed Sheryl out of the hotel and into her car for her
bag of toys. Since the Edgewater was on a busy street to the
airport, there was plenty of time for folks to glance at her and
wonder what the hell was going on.
When she gathered her bag from her car, I e*****ed her back
through the gate and made her walk through the court yard. Her
bag of toys was pretty revealing, since at least a couple of crops
and whips were protruding from the top. Once we got to my room, I
sat her down and I inspected her toy bag. It contained several
crops, paddles, clothes pins, rope, nipple clamps, and
other implements of punishment. It also included two sizes of butt
plugs, a thick black battery powered dildo, several anal dildoes,
anal ease lubricant and other goodies. Again, I was finding out
that Sheryl is an experienced submissive.
I was like a k** in a toy store. I couldn t decide what toy
use on her first, until I found a black leather riding crop that
hand a small leather flap in the shape of a hand. On the hand was
silk-screened bad girl . That was it. I picked it up, made
Sheryl stand in front of the open window, lifting her black slip
up, then I tested the crop on her revealed ass. I whipped her ass
with increasing intensity, watching what speed and power it took to
make a slight mark or welt. I got to the point where it created
enough sting to make Sheryl whimper.
I then made her strip naked and stand facing me, with her
freshly whipped ass toward the window. I traced her breasts and
abdomen with the crop, before I raised the crop and delivered some
blows to her tits, making sure to catch her nipples with the
leather hand .
After a while I had Sheryl sit in a chair, directly in front
of the open window. I attempted to tie her with her legs spread so
she was totally exposed to the folks in the courtyard below. Since
I was in a hurry, excited and not much of a Boy Scout, my ****s
were pretty lame, and Sheryl and I laughed at my inept rope-based
bondage skills. Next time I will bring my cuffs, straps and maybe
even borrow my friend s stocks. While she was tied to the chair, I
blindfolded her and whipped her tits. She flushed when I attached
the clothespins to her nipples and then continued bring the crop
down on her nipples.
I then moved to whipping the front of her thighs, before I
ordered her to lie on her back on the bed.
Sheryl laid on her back, blindfolded and spread her legs. I
leered at her willingly spreading her legs to me, showing me her
bald spread pussy lips. I savored the sight for awhile before I
stood between her legs then brought the crop down directly on her
bald mound. Her whimpers got more intense. I continued to aim
the end of the crop so it would land a stinging blow to her clit
and pussy lips.
I reached back into the bag and pulled out her black dildo.
The batteries were not staying in and the thing didn t work. I
brought it to her mouth and told her to wet it. It looked lovely
going in and out of her mouth, and she willingly open her mouth to
except it. I wondered then if I could find I huge black cock for
her to suck. (I saw some in the courtyard, but things didn t
work out that night).
Sheryl s pussy was so wet, that the dildo popped right in and
I vigorously worked it up and around her pussy. She whimpered and
sighed as I roughly pushed it in and out.
Also, in her bag was a smaller anal dildo. I told Sheryl to
turn over, and while the black dildo was still in her pussy, I
spread her ass cheeks and inserted the small dildo. It slid in
just as easily, and I pushed it in and out. Then I stuffed them
both in as far as they would go and I stood back to admire my
creativeness and her private parts (that were so lewdly on display
to me).
Let s see how good your muscle control is Sheryl, I said,
as I picked up the crop. I want you to keep both in place while
you are whipped.
Crack. I forcefully whipped her thighs right under her
buttocks. The anal dildo feel right out as her asshole tightened
up in response to the blow.
Sheryl, you are not doing too well, I snickered, as I
pushed the anal dildo into her asshole.
Crack. This time the dildo stayed in, although her
constricted sphincter pushed it out half way.
CRACK!. The dildo almost shot out this time, and Sheryl was
whimpering and shivering like she was on the verge of another
orgasm.
This went on for a while. I would shove the dildo back into
her ass, forcefully whip her ass, and the dildo would pop right
out. I told her she would need to work on this and I went on to
another diversion. I turned her over and whipped her breasts while
she laid with her legs spread like she wanted me to whip her pussy.

So Sheryl, tell me about the first guy who you sucked off,
I said, while still delivering a blow to her pussy and tits every
few seconds. When she hesitated, I beat her with more power. I
found that this was one thing she was reluctant to do-- so I
pursued it more. I started asking her more personal questions,
about her husband, ex lovers, etc.
Who shot a load of sperm in your mouth first?
Crack.
Who fucked your asshole first? Tell me about it.
Crack.
This went on for a while. It was particularly interesting
because I had opened the sliding glass door and I knew that
everybody in the courtyard below could hear the cracks of the whip
on Sheryl. And most of them could look up and see her receiving
her punishment.
I finally crawled up to straddle, sitting on her tits and
feeding my cock into her mouth. At the same time I was continuing
the assault on her pussy. Soon, her whimpers and the contractions
of her pussy told me she was actually having an orgasm from being
whipped. I continued to feed my cock into her mouth, sometimes
actually fucking her mouth and other times making her lick my balls
and watching her gobble up and down the sides of my cock. The slut
was truly a first class cock sucker and cum junkie.
About this time I remembered one of my favorite kinks. And I
thought Sheryl was ready to be tested. I turned around so that my
ass was to her face.
Sheryl, I love to have a woman s tongue on my asshole, I
teased her. Then I lowered my ass closer to her face, so she could
stretch her tongue and start to rim me. It felt wonderful, and I
remembered why this was so great. I took the crop and whipped her
pussy and inside thighs to encourage her performance.
C mon, you know what to do...
Crack.
Stick your tongue up my ass more.
Crack.
Well, she certainly did a great job, I thought that I was
going to cum right there and shoot a wad on her stomach.
Her tongue was feverishly exploring my asshole. Again, I
knew that several old guys were watching us from below, and they
probably were not believing what they were seeing. I held her head
by her hair and forced her face and tongue into my ass, and kept
whipping her inner thighs. I finally had to stop, because I
thought I was going to erupt, and I had a lot more that I wanted to
do. I felt then that I had taken Sheryl to new heights of
humiliation and submission. But I had more plans for her.
After a short few minutes of catching her breath and taking a
drink of water, I told Sheryl to get ready for another walk. This
time, I told her to put on her black slip, heels and nothing else.
I attached her leash on the dog collar and led her out the door.
(At the Edge, if you are upstairs, you have to leave the back way,
which faces the highway and a major road leading to the airport.
It must have been quite a site for someone seeing me lead Sheryl on
a leash out of my motel room!).
I led Sheryl downstairs to the courtyard and again, thought I
would take her for a walk. Leading her round by the leash, I
passed an older guy who had obviously been watching our recent show
.
I purposely led Sheryl past him slowly and watched as he
leered at her and enjoyed the humiliating exposure of this woman s
submission.
Now, that s the way to treat a lady, he muttered under his
breath.
Do you like what you see? I asked. I think he was
surprised that I heard him.
Sure do, he smiled.
I then nodded at him and told him see ya later, man.
I led Sheryl to the hot tub, where there were two males with
a woman. They were all nude, and seemed to be having a nice
philosophical discussion. When we appeared, I made Sheryl stand at
attention, head bowed, hands behind her back, while I unleashed
her and took her collar off. I then told her to strip, while the
two guys and the woman watched. Either the woman didn t want
competition, or they might have thought we were too intense, since
they quickly got out and retired to a room nearby for some mutual
massage (as the woman s older husband watched).
I told Sheryl to sit while I took a walk around the
courtyard.
I found the older guy who I talked to and gave him a
proposition he couldn t turn down.
Hey, I noticed you admiring my slave. She s got a great
mouth if you want to try it out.
The look on his face was priceless. He wasted no time
joining us in the hot tub. I noticed then that he wore a cock ring,
and I wondered if I had picked the best guy. I wanted to watch
Sheryl try her best to get a stranger to shoot a load of sperm down
her throat. This guy was already making some excuses about not
being able to cum.
The guy sat on the edge of the hot tub. I looked around to
see if we could be discreet (no sexual activity is allowed in the
hot tub or pool). And then I revealed Sheryl s directions.
Sheryl, I want you to suck this man s cock and swallow his
cum. I will watch, and if you don't please him, you will receive a
severe whipping, I said. Since Sheryl was sitting in the tub, she
turned to her right, positioned her self between the stranger s
legs and took his flaccid cock into her mouth and started sucking
for all she was worth.
I sat and watched for a while, making lewd comments and
suggestions as she sucked.
Go ahead and cum in her mouth, I nonchalantly told the guy.
She ll swallow. I continued to watch and casually have a
conversation with this guy about Sheryl s cocksucking prowess.
I ve been watching you whip her upstairs, he said, as we
both watched Sheryl s head bob up and down his cock. She looks
like she can really take some punishment.
Yeah, she surprises me at her pain threshold. I said,
looking at her laboring to get the guy s cock hard. Lick his
balls, you d better please him, I threatened. She went right to
work. The guy glanced at me with an amazed look and I smirked.
Grab her tits, and pinch her nipples if you need to spur her on
some, I winked. I ll be back, I m going to get a beer.
I walked away and went upstairs. I went to the balcony so I
could view the scene. It was beautiful. I could see Sheryl,
exposed to whoever walked by, frantically bobbing her head up and
down trying to get this stranger off. She went at it for what
seemed like fifteen minutes. When I returned, she was dripping
with sweat and the guy apologized and said he didn t think he could
cum.
I realized that Sheryl was in danger of a heat stroke,
working hard, and sitting in the rather hot water.
OK Sheryl, get up. I will decide how to punish you. I know
you put in the effort.
Yeah, she s really something, he said.
After that, we were both pretty exhausted. Since I didn t
bring condoms, I wasn t going to fuck Sheryl this night. We
returned to the room and fell into bed. After about an hour of
more playfulness, we finally fell asleep.
I woke up several hours later after dreaming/thinking of the
night with Sheryl, I woke her up too. Sheryl had to go to work
early.
OK Sheryl, time for your breakfast protein. I joked.
She obediently positioned her self between my legs, as I sat
up in the bed. I felt her tongue licking my balls and up my shaft.
I thought about her sucking on the stranger in the hot tub last
night. I remembered the feeling of her tongue embedded in my
asshole. I thought of how the dildo kept popping out of her ass
when I whipped her, I dreamed about the look on the old guy s face
when I ordered her to strip for him, and I especially though about
how she would orgasm when she experienced certain types of pain and
humiliation.
Grabbing the sides of her head, I started to fuck her mouth
to an intense rhythm looked down and saw my slut/slave, with my
cock in her mouth, willingly submitting to a wanton lewd mouth
fucking. I had saved my jism just for this moment, and I held her
face and fucked it hard. I soon could feel my sperm churn and
soon it was spurting into Sheryl s mouth and throat. She seemed
to relish the taste of cum and I saw her swallow hard. It was one
of the greatest feelings in the world. I only wish I had a video
of the experience.

Sheryl made quite a conversation topic the nest morning in
the Edgewater courtyard. I met several guys who had watched almost
the entire night as I tested Sheryl s limits. They saw a lot of
details and they recalled some of what they witnessed for me. It
was incredibly stimulating and I couldn t wait to take Sheryl back
to the Edge. There is so much more to explore.

The END