A few nights later, I was pacing nervously in my office as I waited
for my guest to arrive. I’d pimped girls out before of course, but it
was especially important tonight that nothing was fucked up. The
client was a very powerful and very dangerous mobster, and the girl
that he wanted was Michelle, who was quickly making a name for herself
in the business, but who still had a veneer of respectability and
innocence about her.
This was, of course, why Vinnie wanted to fuck her.
I’d been over what the whole procedure would be with Michelle a few
times now. I’d rigged up a camera and panic button in one of the VIP
rooms towards the back of the club, and showed Michelle how she could
call for help if things got a bit too rough. To my surprise, Vinnie
had agreed to these conditions if it meant that he got to fuck
Michelle bareback, which had really been my biggest worry. It had
also been impressed upon Michelle that the financial rewards if she
did well here would be significant.
Still, it was hard not to be nervous. Moreso for her than for me, I suspected.
An hour or so before the appointed time, Michelle had arrived at the
club, done up in heavy black eyeliner and cherry red lipstick like
she’d been told to. Previously she hadn’t gone heavy with the makeup,
but the extra black shading around her eyes made her look especially
hot, like she’d been doing this for years. I could feel myself
getting hard as I watched her undress in my office, but even I wasn’t
brave enough to fuck her and give Vinnie sloppy seconds.
Vinnie had made some quite specific requests for Michelle’s attire, so
I had done by best to oblige. Michelle was okay with the thigh-high
fishnet stockings, having worn them a couple of times before, but the
shiny black platform boots presented a little bit more of a challenge.
Try as I might, I couldn’t convince Michelle to start wearing heels
when she wasn’t working, even though it would have made getting around
the club a lot easier for her. Not that her unsteady, dizzy gait
while wearing the stripper heels I’d been making her wear wasn’t
unattractive, but there would be definite advantages for her once
she’d gotten used to getting around in them.
Once she had the boots on and she’d gotten used to standing in them, I
gave her the final item, a short little black cocktail dress.
Michelle looked as it quizically for a moment before pulling it on
over her head, the expensive black fabric just covering her arse, but
not much more. I’d decided that underwear wouldn’t be necessary for
her, as Vinnie was probably going to make her strip anyway, and it was
probably a good idea to have her in and out as soon as possible.
I had to admit, even though the cocktail dress wasn’t really my thing,
she looked absolutely stunning. She even smiled sweetly for the
camera when I took a couple of non-nude shots of her in the outfit,
after I declared that she looked stunning. You could see the
nervousness in her eyes, but she was doing a fairly good job of hiding
it.
I got a call from one of the bouncers to let me know that Vinnie had
arrived, and that he was waiting for Michelle in the room that had
been set up for them. “Now,” I said. “You remember what we talked
about? Talk dirty, ride on top of him, and remember that the panic
button is just underneath the sideboard. If he starts getting violent
or you’re in trouble, we’ll be watching and the bouncer will be in
there to get you out. Okay?”
She nodded. I wasn’t sure that I was brave enough to send security in
to drag a girl off Vinnie mid-coitus, but she didn’t have to know
that. I took her gently by the arm and guided her to the room where
he was waiting, concealing my annoyance at how slow she was walking in
the eight inch heels. Now wasn’t the time to make her nervous.
As we both entered the room, Vinnie, who had been sitting waiting on
the bed, stood up. “Ahh, Richard,” he said. “She looks perfect, as I
knew she would be. I knew that I could count on you.”
I nodded in response. “Thanks Vinnie. Michelle, say hello to Mr Hunt.”
“Hello… Mr Hunt,” she said, somewhat nervously. “I’ve… been
looking forward to meeting you.”
Vinnie laughed. “Oh, I’m sure you have! I’ve been looking forward to
meeting you as well. Richard here seemed to think that you’d be a bit
skittish about spending some time alone with me.”
Michelle looked at me, as if seeking support, but I just smiled back
at her. “I… um… well I haven’t done this before…” she
eventually managed to stammer.
Vinnie seemed to find this amusing. “Well, I’m sure that a knockout
like you will get lots of experience soon enough,” he laughed.
Sensing that I was overstaying my welcome, I backed off towards the
door. “Well, I guess I’ll leave you two to it,” I said. “Once you’re
done Vinnie, just let security know, and they’ll help you out with all
the usual stuff.”
“Sure thing, Richard,” said Vinnie as he turned his attention to
Michelle, running his hands over her tits through the thin black
material of her cocktail dress. I shot him a grin before leaving the
room, closing the door behind me.
I walked back up to my office, sat down behind my desk, and flicked on
the monitor that was monitoring what was going on in the room
downstairs. Vinnie was still fondling Michelle’s tits with one hand,
but the other was stroking up and down her thighs and grabbing her
bare arse underneath the dress. The picture quality was quite good,
and there was a sound hookup as well, which I also took the time to
flick on.
Vinnie was murmuring various things into Michelle’s ear that I
couldn’t hear, but from the expression on her face, she didn’t
particularly like what he was saying. Not that Vinnie appeared to
give a shit at all, as he pulled down the front of her dress enough
for her tits to spill out into his eagerly awaiting hand.
I had to admit, watching Michelle turning her first trick for a total
stranger like this was having an effect on me; it felt like my cock
was going to burst out of my pants at any moment. One of the perks of
owning and running your own strip joint though is that you never have
to jerk off. Turning my attention away from the monitor for a moment,
I picked up the phone and called the bar. “Yeah, send Courtney up
here for me now,” I instructed the night manager, as I began sliding
my trousers off.
A couple of minutes later, Courtney bounded up the stairs and into my
office. She was clad only in a tiny black bikini set and a pair of
obscenely high stiletto heels. I couldn’t actually remember ever
seeing her fully dressed inside the club, which was fine.
“You wanted me?” she asked.
“Yeah,” I said. Pushing back in my chair and letting her see that I
was pantless and that my cock was sticking up into the air. “Come and
sit over here.”
Giggling, she obliged, coming and perching her soft slut arse onto my
lap. I’d lost count of the number of times that I’d had my dick
inside Courtney, but I never seemed to tire of it. In many ways, she
was the exact opposite of Michelle, and while there’s always a lot of
fun to be had having to gently cajole a good girl into doing things
that she doesn’t want to do, it’s equally as fun sometimes to have
access to a slut who will do whatever you tell her to do, whenever you
tell her to do it.
My hands went to her body, rubbing up and down her smooth stripper
skin as I turned back to the monitor. “Oooh, what are we watching?”
Courtney asked excitedly.
“Michelle with Vinnie,” I responded curtly, parting her legs and then
pulling her panties aside. She gasped slightly as my cock easily
slipped into her banged open slut hole, and I began slowly pumping it
in and out.
“I don’t see what you see in her anyway,” Courtney said as she began
rocking her hips instinctively back and forth onto my cock. “I mean,
what does the frigid bitch do for you that I won’t do?”
“That’s the fucking point, Courtney,” I said, less after a
conversation than something tight and wet to park my cock in while I
watched Michelle fuck. Vinnie had kept pulling her dress down, and it
was now all bunched up around her waist as he fondled her tits and
fingered her now naked clit. He said something to her, and she began
fumbling with his belt, obviously trying to get his trousers off.
After what seemed like an age, she managed to undo his belt and
unbutton his pants, running her hands around to his behind and tugging
them downwards. Vinnie’s cock sprung free, almost hitting Michelle on
her face as she squatted down to pull his trousers and underwear down
around his knees.
Once his pants were off, he said something else to her, and she closed
her eyes and leaned forward, taking his cock in her mouth. She
started sucking it and rubbing up and down along his shaft with her
lips, just as I’d taught her to, and I felt a flash of pride that I
had managed to teach her to suck cock so well.
“I mean, look,” said Courtney, interrupting my train of thought.
“She’s not even deepthroating him. I mean, I always do that for him!
Can’t see why he’d want her and not me.”
“Courtney, do you think I called you up here so that I could hear your
thoughts on Michelle’s style at turning tricks?”
“Well, I’m just saying, that’s all,” Courtney protested, before
quietening down again. My cock was pumping harder into her now, and
she was grinding her hips up and down on me like a fucking pro. On
the screen, Vinnie had evidently gotten tired of Michelle slobbering
over his cock, and he was getting up on the bed that had been
prepared. Michelle lifted the crumpled black dress up over her head,
and began straddling him, throwing her head back as he penetrated her
tight little cunt.
She began riding him, making little moans of pleasure every time she
pushed herself down and impaled herself on Vinnie’s cock. Vinnie
seemed to be content just to lie there, stroke her thighs, and let
Michelle do all of the work for him. Michelle, for her part, had her
eyes closed and was covered in a thin layer of shiny sweat as she
worked his cock as hard as she could with her cunt.
“Oh, you’re so big,” she eventually cooed, just as I’d taught her.
Courtney managed to snort out a laugh at that. “Oh, christ, where’d
she learn to do that? How fucking cheesy?”
Despite the fact that I was enjoying having my cock in her, I was
really beginning to tire of Courtney’s attitude. Grabbing her by the
hips and lifting her up off my cock, I set her down onto the ground,
and thrust my cock at her face. She knew better than to ask
questions, and took my meat into her mouth and started expertly
sucking it, rubbing her lips and tongue hard up against it.
With her mouth full, she wouldn’t be able to make any more unhelpful comments.
I turned my attention back, again, to the monitor, to see that now
Michelle was sitting on the side of the bed, while Vinnie stood in
front of her, his cock in her mouth again. He was a bit more lively
now, gently rocking his hips back and forward, lightly fucking her
mouth and her cherry red lips. Michelle had one of her hands guiding
his hips in and out of her mouth, while she used her other arm to hold
herself up on the bed.
Vinnie said something to her that I couldn’t make out, but Michelle
looked up at him, her mouth full of cock, a look of disgust and fear
on her face. After a second, and without taking the meat out of her
mouth, she nodded up at him.
Vinnie slid his lipstick-stained cock out of Michelle’s mouth, and
started frantically jerking it right in front of her face. Michelle
closed her eyes instinctively at the sight of a cock being jerked off
mere inches away from her face, her expression of apprehension clear
to see, even over the monitor.
His grunt of ecstacy and pleasure was also clear to hear over the
speakers as he orgasmed, spurting a sticky string of cum into her
hair. Michelle grimaced as the warm, sticky ooze hit her face, but
stayed still for the next lot, which shot in a big diagonal line
across her face from her left eye down to her mouth. The next spurt
just congealed in a sticky white globule on her cheek, before the rest
of his shots fell short, splattering against her breasts, stomach, and
down onto the bed.
Vinnie looked very pleased with himself, and Michelle looked
absolutely horrified. She sat there silently as he pulled his pants
on and left a small pile of bills on the dresser beside the bed, his
seed dripping and oozing down her face and her body. The look of
humiliation and shame on her face was enough to tip me over the edge,
so I grabbed Courtney’s head and pulled her as far forward as I could,
my cock shooting cum deep into her tight wet little throat.
Courtney spluttered and choked as she swallowed down my cum and as I
watched Vinnie leave the room, leaving Michelle sitting distraught on
the side of the bed. Rolling backwards in my chair, I stood up and
did up my pants, satisfied now that I’d gotten off. “Get back to
work,” I hissed at Courtney as I grabbed a towel and left the office
and headed back to the VIP room where Michelle was.
When I arrived, Vinnie was long gone, and Michelle had started looking
around for something to clean the semen off of her face and her body.
She jumped a little and turned around as I entered, but relaxed when
she saw that it was only me.
She was a site for sore eyes, at least if you like seeing freshly
fucked redhead strippers. The makeup around her eyes had run in
irregular black streaks down her face where the semen had been shot
into her eyes, and her lipstick was smeared and messy where she’d been
working Vinnie’s cock with her lips. Her body was still covered in
gobs of rapidly drying white semen, and her stockings were ripped and
torn at the top where Vinnie had been pawing and grabbing at her legs.
I took a moment to enjoy the site, then tossed her the towel. “Why
don’t you clean yourself up, have a shower, then come up to my
office.” I said to her. She caught the towel, nodding, and began
wiping the sticky goo off her body and her face, her expression one of
quiet resignation more than anything else. Savouring for a moment the
sight of her humiliation, I lingered for a second before returning to
my office.
About twenty minutes later a freshly showered Michelle came back
through the door of my office, wearing the short black cocktail dress
again, but with the boots and her fishnets under her arm. The streaks
of black makeup that had been running down her cheeks were gone, but
her eyes were still smeared with messy black shadow.
“See, that wasn’t so hard, was it?” I asked her.
“It was… awful,” she whispered back. “He kept calling me a slut,
and a whore, and…” she trailled off.
“Well, you’ll have to get used to that,” I said. “Some of the punters
get off on that sort of shit. It’s part of the job that you’ll just
have to get used to.”
“I don’t know that I can get used to…” she began, before trailling
off again, as she watched me start counting money out onto the desk.
Even Michelle’s cut of the money that I was not going to have to pay
Vinnie was a sizable amount of cash, which looked even more impressive
when counted out onto the table in banknotes. “How, how much is
that?”
I told her. Her eyes seemed to bulge at the figure.
“That much?” she asked.
“I told you before, if you were willing to do some extra things, that
there would be a monetary incentive in it for you.”
“Yes, but… that much?”
I nodded. Suddenly the shame and embarassment of taking a stranger’s
cock in her cunt and his jizz on her face took a back seat to her
delight at the money that she had just made. She eagerly crossed my
office to count the money that she had just earned, as if she could
scarcely believe what she’d just gotten. I gazed at her, a satisfied
smile on my face, at just how easily at had been in the end to twist
her.
She looked up at me, the expression on my face obviously giving away
what I was thinking, and she quickly moderated her own expression to
something more neutral.
“You know, there’s a lot more where that came from. The payoff
probably won’t be as lucrative every time, but if you start doing it
regularly, the money will build up…” I said.
She looked at me, the doubt that I’d gotten used to still in her eyes,
but pushed down further than usual. “How regularly?”
I smiled. “I think that we could probably arrange something for you
as often as you’re willing. Perhaps… between your first and second
dances every night?”
“Every night?”
“Every night.”
“Well… I don’t know”, she said. “I’ll have to think about it.”
“You do that,” I said. “And let me know. Remember, the sooner you
start earning some serious money, the sooner that debt of yours will
be paid off.”
She looked down at the ground again, doubt flickering over her face.
“Well…” she began. “Alright. When do I start?”
I smiled. “How about tomorrow night? I’ll make a few calls, I’m sure
I can find someone for you.”
She nodded sadly.
“Look, at least you’re making more than you would tending the bar, or
making café latte at some bistro, right?”
She nodded again, obviously unhappy, but resigned to her fate.
“Good girl,” I said, patting her butt through her little black
cocktail dress as I showed her to the door. I was as pleased as
punch, because not only had I managed to keep Vinnie happy, I’d also
gotten myself a new, slightly reluctant, but still willing whore.