Strip Poker can be Painful
I am a manager with many people reporting to me. I do not believe
in mixing office with work. So what happened to me 4 years
ago was a real shock. One of the professionals in my department
was Rendy. That's the name she went by, although her real
name was Susan Rendlemen. Anyway, Rendy and I had a major
corporate project that required that we spend a lot of long
days and a number of evenings getting to the final presentation.
During all the time spent on the project and the three previous
years she was in my department, nothing had ever transpired
between us that would hint at a sexual attraction. So it
was no big deal to work long hours together. I saw Rendy as
a professional colleague and nothing more.
It was a Wednesday afternoon that we made our presentation
to the company's management. We were trying to spin off
a $35 million operation into a separate Business Unit.
We made an outstanding presentation and our proposal was
approved. Life was good!! After the presentation, we decided
to go out to the local Bennigan?s to celebrate. We were both
really high because a separate business unit would give
us the opportunity to expand the operation beyond the scope
currently limited by our corporate management. So we had
a lot of drinks as the euphoria of "victory" made us high.
The conversation turned to "risk". Rendy said that I was
only a "marginal" risk taker. I only took risks that I understood
where I could gauge the odds of success. Naturally, I disagreed.
I think of myself as one who will throw caution to the wind
for the right results. Well Rendy had found my "hot button."
I was not about to let her think that I couldn't handle risk - it's
a macho thing. So she had me all set up and I never suspected.
So Rendy laid down a challenge. It was not done in an asking
manner but rather as a dare. A session of strip poker with
the winner collecting the prize agreed to at the beginning.
Keep in mind that both of us are pretty high and a little more
adventuresome than normal. I'm more interested in how
the game will by played, so Rendy gives me a choice of games
as follows: "Luck Draw - you lay all the cards out on the table
and you draw for best card. Whoever draws the best card removes
the other person's article of clothing. When the last piece
is removed, the winner collects the agreed to "prize."
The twist in this approach is if the lady draw the Queen of
Hearts, then she automatically wins, and if the man draws
the King of Spades, he wins. It adds an element of potential,
that even if you are behind, you can win with one draw. "Skill Poker
- This is traditional draw poker with a change. Instead of 5-card
draw, you do 7-card draw. This expands the strength of the potential
hand and makes it harder to know if you have a winner. This approach
requires that you know some fundamentals of poker odds and hand value.
As a decent poker player, I naturally chose the skill-based
approach. It was now time to decide what we were playing
for. I went first and said that if I won, I could shave Rendy's
pussy. Rendy's stakes seemed milder. All she asked is that
I wear her Kali Bracelet, which was something that made
her feel close to the person wearing it. She didn't describe
it and I didn't ask. Was I ever stupid? It seemed so "female"
and "feel good" that I never saw the risk coming. I agreed
in a heartbeat. Now remember, we are in a bar, so we decided
to go back to Rendy's place. On my drive to her house, I only
thought about how silly/stupid she was to propose this
arrangement. First, I was a good poker player and the game
favored a good player. Second, I had a real sexy objective
as my win, versus her bracelet wearing. I got really pumped about the
outcome. I followed Rendy to her house and entered her living room.
We had to agree on the number of clothing items and we decided
on five(5). I'm going to bore you with the details of the
competition, because we agreed that the winner of each
hand would have free rein over the clothing removal. So
we each got ourselves a drink and let the competition begin.
I won the first hand. Rendy stood up and I went around behind
her. I got up close behind her and slowly slid my hands down
the back of her skirt until I could grip her ass cheeks, which
were still guarded by her panty hose. After a little feel,
the hands moved around to the front, across the pussy and
then exiting the skirt with the blouse in hand. A fulfilling
venture to prepare the blouse for removal. I then started
with the lowest button and undid each while maintaining
maximum physical contact with her breasts. As the last
button was undone, my hand brushed firmly across the erect
nipple that protruded through her thin bra. I turned Rendy
around and removed the blouse from her shoulders and arms.
She seemed unconcerned. "Never thought you'd see this, did you?" I
won the second hand. This was easy! I got up close to Rendy and
reached around her to unfasten the bra. I allowed it to dangle as I
circled to the rear. My hands slowly slide under the bra, around to
the front until I held the breasts firmly in my hands. Rendy has small
breasts (a small 34B), but they are very firm with nipples that are
large and achieve a magnificent erection. I spent a short time slowly
nuzzling her neck and fondling those beautiful nipples. By the time
I finished removing the bra, she had an erection as hard
as mine. Rendy won the next hand and quickly removed my belt. I was
surprised by the lack of foreplay or exploration. She also
won the next hand and had me stand up. Like I had done to her,
she approached from the back with her hands going down my
pants to the ass except she was all the way inside. She slowly
made her way to the front and found my hard and very sensitive
cock. I mentioned that this didn't seem to have anything
to do with removing my tie and she told me that it was my pants
she was taking. I didn't think this was fair because everyone
knows that you start at the top and work down. As she massaged
my balls, we discussed the merits of the move and what had
been agreed to. But she had my balls in her hand and I was in
no position to enforce a protest. So off came my pants.
At this point, I was hot, and not nearly as confident as I
started out. Especially when Rendy won the next hand. She
had me stand up facing her. She positioned herself on her
knees in front of me with her face at my cock's front door.
She started massaging my balls through my underwear and
mouthing the tip of my cock through the cloth. At this point
the poker game had lost most of it's meaning. Rendy continued
her attack by pulling my cock from my pants and taking it
totally in her mouth. She got less than 10 slurry strokes
in before my knees buckled and I lost it all in a super cumm
shot. The feeling of this orgasm was the best of my entire
life. My underwear was now off and I was left with trying to not lose
totally. I also lost the next two hands. Rendy did nothing more than
remove my tie and then my shirt. I could not believe I had
lost 5 hands in a row, but it happened. I found out that Rendy
knows poker and I lost!! It was not what I had expected, but
not a big deal. What was I to care about wearing a friendship
bracelet?? But here I was in an alcoholic high, naked and
obligated, with a lady that worked for me with whom I had
only had a professional association. Rendy then went to
her closet and brought out Velcro hand and ankle restraints.
She took me into the bedroom and had me lie on the bed. I thought
this step a little unnecessary, since I had agreed to accept
the terms of the oral agreement. But once strapped down
to the bed, Rendy brought out her Kali's bracelet. It was
then that I fully understood that I was on the short end of
the deal. I had traded short.
The Kali bracelet is a 1" metal ring that is 1 inches around
and 1 " long. It has internal "teeth" that are 38" deep
with sharp points on the end. What you do is attach this to
a male's relaxed cock. The inside dimension is 1" which
is small enough to get the spikes into the sensitive flesh
without creating a problem with normal functions. Did
I tell you that this device has a locking (real locks) hasp
that allows a real lock to "chastise" the male such that
you cannot get to the lock to "cut" it off. When locked on
your cock, it is there until the owner of the key unlocks
you. Until you have used it, you have no appreciation of
how much psychologically this small device renders a woman
control over a man. This is control, not submission. Because
I had just cum, my cock had somewhat gone back to a relaxed
state. But Rendy still had to wait 15 minutes before she
was ready.
Rendy installed the bracelet on my cock. I still remember
the clicking sound of the lock as it secured the bracelet
into place. Rendy released me from the restraints and told
me to go home and she would see me tomorrow. Here I was, ready
to get sexually active, and the woman who just "won" the
poker match is sending me home. On the way home I got to thinking
about the evening and developed a big hard. NOT GOING TO
WORK!!! As my dick swelled, the sharp teeth on the Kali bracelet
dug into my sensitive cock and caused extreme pain. With
the Kali bracelet, you cannot afford an erection. Now Rendy
had only installed the normal bracelet. I understand that
there is a bracelet with slightly smaller inside dimensions
that really gets the "point" across. As I drove home, I tried
to minimize my sexual thoughts because an erection was
very painful.
Now there is one "guy thing" that needs to be understood.
I went home and figured to ride out the discomfort. But guys
get "hards" at the strangest times. And each "hard" is now
extremely painful. Being controlled by the woman with the key now is
at the front of the mind. This is a very psychological
thing. If you control my dick, you control my body. If you
understand that statement then all of this may appeal to
you. No matter how much you freely participate in alternative
behaviors, I would challenge the guy who wouldn?t be turned on by a
situation where a woman has real sexual and psychological control over
you. Once I examined the bracelet and realized that I could not get
it off, that?s when it became both a turn-on and an apprehension. What
would Rendy do with me? That night was a little rough. I woke up
twice with erections and a lot of cock pain. This was both my most
sexual experience and my most painful. When I arrived at work, my
colleagues congratulated me on the success of the presentation. Rendy
was back to her usual self as if nothing had happened. At
8:30, I dropped by her office and told her that she had had
her fun and when could I get the "damn bracelet off." She
smiled and only said, "you lost" and returned to her work.
At 9:30, Rendy dropped by my office and said that she would
like a large cup of ice water with lemon and a bagel. She then left. I
was in shock. This is not what I do. I am not her administrative
assistant; I'm her supervisor. I had a good mind to go in
and tell her to get her own water, when I realized my dilemma.
She had the key and I had no good bargaining position. Corporate
hierarchy had little relevance when your cock is locked
in a bracelet of sharp spikes. I did what she asked and I could
tell she was loving it. The day was busy, so I didn't notice
the discomfort of the bracelet most of the day. At 5 p.m.,
Rendy came by my door and said that I was to be at her house
at 7 p.m. the next night. She then walked out. I was beginning
to see her in a different light and my cock suddenly got hard
and the pain came with it and I couldn't decide whether this
was sexual or torture. But what I could tell was that mentally, I was
so emotionally tied to this situation and my fate in the hands of
Rendy, that little else mattered. The second night was more difficult
than the first. I was so sexually charged that it was almost
impossible to prevent an erection. And every time I moved, I could
feel the subtle presence of the bracelet and the potential pain from
an erection, and this makes the erection come. Or as I look
at it and realize that this is for real and Rendy does control
my cock. I'm not exaggerating when I say that getting the bracelet off
requires either a locksmith or ripping your penis to shreds, neither
of which is acceptable. That is why it is such a psychological device.
At work on Friday, not much was said. By this time my penis
was tender and sudden movements made me all too aware of
the fact that I was chastised. After work, I went to a local
bar, had a couple of drinks to prepare for the evening and
waited. I arrived at Rendy's place at 7 p.m. and went into
the family room. There were two ladies besides Rendy, sitting
on the couch, having a drink and talking. We greeted each other. I was
introduced as Rendy's boss in a gloating manner. I then sat down.
I probably need to put this situation in context. For many
people who are experienced "swingers", what I describe may seem mild.
But the situation with Rendy was my first "sexual" encounter outside
my marriage, except for overseas adventures during my travels. Now
arriving to a room with Rendy and 2 strangers was almost too much.
Rendy solved the comfort problem by telling me to get the ladies
drinks. I complied immediately, because this part I had figured out.
They then got out a XXX videotape and put it in the VCR. As it
started, I hung back behind the couch, trying not to be too visible.
But no such luck! The tape was not more than 5 minutes old when
Rendy turned down the volume and began to talk about men's duty to
please women. And if they didn't get the message then they needed to
be trained. So here we have a tape of men going down on women on the
TV, and Rendy calls me over. She makes a point of letting them
again that I'm her boss before she tells me to take off my
clothes. The shock on the ladies faces told me that they
were not in on what was going on. And I was not sure of complying.
But I had little choice, so I decided to make it a presentation
to remember. The ladies just ate it up, all the while being
somewhat embarrassed. But when the underwear came off
and the Kali bracelet was revealed, the look of wonderment
on each lady?s eyes told me they were impressed. I was their
subject and they grasped my balls and examined this magnificent
chastity that adorned my shaft. My cock was trying to swell
and the pain was sending the signal to get away from the examination.
But these women were truly enjoying having a man at their
bidding. Rendy then came with a half hood that covered the eyes but
not the mouth. It fit snugly over the head with a lace tie
in the back and a small lock at the bottom. I could see nothing.
Again, like the bracelet, the hood would not come off until
Rendy decided it would. I was led into the bedroom and told
to lie on the bed. I lay there for about 15 min. Here I was,
naked on the bed, with a cock chastity on my shaft and a hood
locked to my head, and 3 horny women in the next room plotting
my fate. I heard the door to the bedroom open and someone entered.
She didn't speak but came over and lay on the bed. She grabbed
my balls in a vise like grip, and directed my mouth to her
pussy. It was very clear to me what this lady wanted. As my
cock swelled, my manhood ached, both from the grip as well
as the Kali bracelet. It was very hard to concentrate on
achieving good results. But there is nothing sweeter than
a woman's pussy. To take a set of lips and gently caress them
with your tongue until they swell with emotion is a remarkable
feeling. And to be able to apply the proper rhythm to a good
tongue fucking and to bring a woman to climax is a beautiful
achievement. So forget that I'm under chastity. The unknown
lady before me has serious expectations and I do not want
to fail. I gently caress her breasts. They are smallish
but not as firm as Rendy, so it is not her. But I?m unsure who.
As I fondly the breasts, and slowly suck on the clitoris,
an emotional sound comes from ?my lady.? I increase the
stroke of the tongue and concentrate on the breast nipple
and this lady gives it up in a very short time. The XXX movies
had her well prepared. Her orgasm was unlike anything I
had heard or seen before and it puts my cock on maximum swell.
And it hurt like hell. I wish I were not chastised because
this was a lady that would be great to fuck to climax. The
sounds, the tension in the pussy and the hunger for the tongue
probe that was entering her made her special. I wanted to fuck her and
I paid with pain. The second lady in was also not Rendy. I knew this
because she was larger breasted. She was also very unsure about
this situation. She allowed me to massage her breasts, but when I
dropped my attention to her clit, I could feel the body stiffen. For
a period I tried to do a gentle, non-sexual massage to relax her
apprehensions, but obviously this was not for her. After an
appropriate length of time she left. I'm sure her stories do not match
reality. The third lady was Rendy. I know that because of the
distinctive nature of her breasts. To Rendy, I know that she thinks
they are too small. But, to me they are a real turn-on. When she
gets the least bit excited or sexual, her nipples swell
and protrude through her blouse. She may not even know that
her tendency to have erect nipples sends the guys in the
office to the cold showers. And when I embraced her breasts
the other night, a second fact became known to me, and that
is that Rendy's breasts are very firm. From most guys? perspective,
a firm 34B with responsive, erect large nipples wins everyday
over sloppy 38DD. As Rendy lay beside me, I could feel the
connection. She kissed me on the mouth and her tongue penetrated
until it found mine. She massaged my shoulders and neck,
and I was unsure what was going on. Gently, Rendy took my
hand and placed it on her pussy. The touch was enough to cause
her to react with a pleasure stiffening that was really
stimulating. I began the slow methodical massage of her
pleasure box. Rendy went inward with her emotions, like
a cat enraptured by petting. I you have ever seen a cat that
is really enjoying being petted, they will have the outer
eye open and the inner eye closed. The body will arch and
move toward the stimulation that is most pleasurable.
Well this was Rendy. Hardly a sound, eyes closed and the
body swaying with each stroke. Each time I tried to speed
up she moaned a no. So for what seen like a half-hour, I gently
caressed her clitoris and held her in my arms. By this time
the bracelet on my cock was under some serious pressure.
So I increase the pace and this time Rendy came out of her
shell and actively arched toward each rapidly increasing
stroke. I knew that this was my chance at "freedom", so I
whispered in her ear that I wanted to fuck her and now. "Fuck
me" was the reply. But I had a small problem with I led her
hand to. Rendy got up quickly, went to the nightstand to
retrieve the key, unlocked the bracelet in very short order.
She used some lotion from the nightstand to sooth my tender
cock. It only took a few strokes until my sexually charged
body all resided in the stiffest member I could remember.
Rendy had a condom and placed it over my tender shaft. It
really helped because a flesh to flesh encounter after
the bracelet could have been painful. I then pulled Rendy
toward me. As I returned to massaging her pussy, she grabbed
my balls. That was all it took. I mounted that hungry, wet
organ with an organ that was free and on fire. Rendy arched,
attacking my body with every increasing stroke. Because
I am not well endowed, I have learned to mount high in order
to increase the stimulation on the clitoris, and it was
working. In a final burst, Rendy said "Fuck me harder" and
then went into a full arch, body stiffening, nails in my
back climax. Not much noise, but her body sent me over the
edge. Her pussy tightened and her legs closed and she just
sucked the juices out of me like I had never experienced.
We lay on the bed for about 5 min. recovering and unsure what
to say. Rendy then reached over and removed the condom and
applied more lotion to my "damaged" member. She asked if
it was all right after its ordeal. I said, "Yes", although
I had my doubts. We joked about how this had come to pass and
said that we must do this again. I was in a dream when I left
her place. The next Monday, all was normal at work, and nothing was
ever mentioned except for the ordering form for a Kali bracelet
with a note that said, "I enjoyed winning. And next time
- bet smarter". About 6 months late Rendy took a job in Atlanta.
But when she left she gave me a present - the equipment from
our encounter. I still have it and it goes unused.
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