Cindy Inc. – Pilot

This was the very first Cindy Inc. story I wrote for
my story club (posted in four parts as “Recruitment,”
and presented here intact and unchanged – apart from
the title – for better or worse); think of it as the
pilot for the series. Which explains a few
differences, and why this doesn’t begin with the
ending of the previous one.

This isn’t meant for under-18s; praise or complaint to

* * * * * * * * * *

Cindy Crawford’s new job as a madame was working
beyond her wildest dreams; though not all of the women
she had under contract were available all the time
of other commitments (filming, tours, etc),
you could always arrive at Cindy, Inc. and guarantee of
having someone famous tending to your needs –
prostitutes maybe, but you wouldn’t find better paid
(or better done) ones anywhere. Not even at Anna
Nicole Smith’s rival establishment.

However, Cindy was never one to keep still. She was
always on the lookout for new blood; she believed in
giving the best service she could – “We charge a lot,
we have to give them a lot,” she told her shareholders
at one meeting. As a result, it was hard to find one
attractive celeb who WASN’T under contract to either
Cindy or Anna. For instance, when Cindy signed up
Britney Spears, Anna retaliated by getting Christina
Aguilera. Cindy had snapped up Destiny’s Child, Anna
had acquired Li’l Kim and Pink. Cindy had talked Sarah
Michelle Gellar and Jessica Alba into signing on the
dotted line, Anna had gotten her mitts on Charisma
Carpenter and Lucy Lawless. The feuding and fussing
went on and on. And now, as Anna Nicole Smith’s limo
ferried her over to get Carmen Electra, Cindy was en
route to finalise negotiations with Jennifer Love

Cindy sat back, an exhausted and newly-signed Jessica
Simpson next to her. “Does it have to be a tattoo,
Miss C?” Jessica asked.

“Only a tiny one,” Cindy told her. “That way
everyone’ll know you work for me.” Indeed, all Cindy’s
ladies had a small C somewhere on their person. “I
wish I didn’t have to do this today though…”

“You do want JLH, don’t you?” the singer asked. “And I
hear Anna Nicole is after her as well.”

“Only because I was asking,” Cindy replied. “But if I
don’t make it, you’ll be great to have anyway. That
audition you did was something.”

Indeed, Jessica Simpson’s confession that she was
pretty eager to have sex had been more than just

* * * * * * * * * *

In the hotel suite that Jennifer Love Hewitt had
booked while she was in the city, she paced back and
forth, wondering whether this was such a good idea. It
wasn’t like the two celebrity brothels were such a
secret, but no one knew for sure who belonged to who.
And there were still a few holdouts – Jennifer didn’t
mind a few dents to her good-girl image, but it might
still be better to hold out a bit…

“Howdy, heartbreaker!” Jessica said happily, entering
the room.

“Hey, Jess!” Jennifer replied in kind, embracing the
arrival (was she NAKED under her dress?). “What are
you doing here?”

“It’s the boss’s idea,” the Texan explained. “Cindy
always likes the new girls to meet the most recent
arrival. Helps put them at ease.”

“Now before we get started,” Cindy added as she
entered, “I need to tell you that we don’t have paper
contracts here – we’re going to put you through your
paces before we talk a deal.”

“My paces?” Jennifer repeated. “What, I’m going to
fuck in front of you? I’m going to fuck…” and she
looked at Jessica.

“No,” Cindy told her. “Not unless you want to. I was
thinking more of you joining me and Jessica on a pilot
job. (Like TV series, each potential new member went
on a preliminary test, a “pilot,” to see how she
worked out.) One of my clients thinks you’d be great
waiting tables…”

* * * * * * * * * *

That evening, Cindy, Jennifer and Jessica were working
undercover at a club (not one of Rande’s clubs,
although he knew what his wife was doing). For one
night only, the three would be serving as waitresses.
And the three had had their shapely behinds pinched so
often that they had been tenderized.

“Man, dinner is served and we haven’t even ordered
yet!” one customer drooled as Jennifer bent before
him, giving him a clear view of her chest. “What a
rack… and some great buns for dessert!” he added,
patting Jennifer’s seat.

“You know, you don’t get the full effect with this
covering them,” Jennifer cooed, taking his hand and
slowly pushing it under the fabric. (“Unless he or she
wants to hurt you and you haven’t asked,” Cindy had
told her, “the customer is always right.”) The man
beamed; she was right. Her ass did feel better without
the fabric.

“Meet me later and you can do more than squeeze,” she
told him with a wink. “I get off in an hour…”

An hour and five minutes later, the customer made his
way to the private area of the club – the back room,
where you could have any special sessions you desired.
He had set himself up for a bit of disappointment –
just in case he wasn’t about to put his cock inside
Jennifer Love Hewitt.

His fears were unfounded. There were two other men
there already, one with his head buried between Cindy
Crawford’s legs, the other gasping as Jessica Simpson
swallowed his equipment. Jennifer was sitting on the
face of the latter, grinning away. “You’re late,” she

Within seconds he was making up for lost time, his own
prick journeying down her throat. Jennifer had never
been the giver and recipient of oral sex before, and
she was enjoying it. But no more so than Cindy, who
was thrashing around for something to hold on to as
her own customer squeezed her firm rump; or Jessica,
who scrambled around to suck Cindy’s man off as her
own customer took Miss Simpson’s first-class bosom in
his hands and started to rub the nipples.

Jennifer soon felt the man’s cock start to produce its
come – she pulled back and took it in her hand,
thrusting three times before she felt the cream
moisturise her face. She then dragged down her
customer – “Don’t worry, we’re not through yet” – and
thrust her tongue down his throat. It was a weird
sensation being kissed by a woman covered with his own
jism. But at least the woman was tasty little Jennifer
Love Hewitt. If only Cindy or Jessica could be
persuaded to taste her snatch (but the word had it
that Cindy was a one-woman woman, and Jessica wasn’t
prepared to do that just yet).

Jessica and Cindy were double-teaming the second man
now, Cindy working on his front while Jessica did his
back, and the third man was happily rimming Cindy’s
perfect puckery asshole, loving her groans as he did
so. He had never eaten a woman’s ass before, and he
was over the moon to be starting on this particular
one. With visions of his jacking off to Jessica
Simpson’s buns, he promised that the sweet young Texan
would be next. He gently pinched Cindy’s buttocks as
he went further up.

“Wanna watch me fist-fuck?” Jennifer asked her

“Who?” the man asked, already happy at Jennifer’s
and lips.

“Jessica and the guy Cindy’s blowing.”

Jessica and the guy Cindy was blowing nearly came on
the spot. Jennifer started to slather her arms up to
the elbow with the Vaseline, while Cindy began to
apply the jelly to her man’s ass, and Jessica’s guy
started to do the same to Miss Simpson. “Pile it up on
there,” Cindy told him.

“Aren’t you afraid there’ll be more Vaseline than
butt?” laughed Jessica.

“We did something like this once at the London branch
with Martine McCutcheon and Cat Deeley,” Cindy
explained. “Martine’s buns weren’t oiled enough,
and…” She left it unfinished, but everyone knew that
that was the real reason Martine had kept missing
performances of “My Fair Lady.”

“You heard the boss,” Jessica nodded. “Pile it on.”

Jennifer’s customer, in case you’re wondering, was
keeping Miss Hewitt occupied by feasting on her tight
little snatch. He continued doing this even as the two
recipients, all oiled up, spread themselves and felt
Jennifer’s squeezed fists prodding against their back
doors. Cindy’s man was a bit nervous – he had been
butt-fucked before, but not with a fist.

“Here,” said Cindy softly. “Suck on this – it’ll ease
your mind.”

She was right – having one of Cindy Crawford’s hard,
freckled, erect nipples in his mouth did help relax
him. He just managed to keep from biting into it as he
felt Jennifer Love Hewitt’s right hand slowly bore
into him.

Jessica Simpson, being as she was with someone a bit
more nervous, had to settle for fondling the man’s
prick – which was just as well. As Jennifer’s left
hand began to widen her beautiful chute, she clamped
her teeth down hard.

Jennifer started to push one arm up as she slipped the
other down, slowly working her two partners as if she
was driving a car. She watched as Jessica and the man
found themselves accommodating more and more of her
arms – heavens above, how was she getting so much
inside? There were six loads of sexual happiness
boiling over in the room that night, as they wondered
who would come first. As Jessica felt herself
approaching the heights from Jennifer’s fist, and as
Cindy enjoyed the best suckling of her life from a
grown man, and as Jennifer felt her lover’s tongue
finishing her off, it was anybody’s guess…

The customers took turns kissing Jennifer’s left arm
afterwards (“Better Jessica Simpson’s asshole than a
cow’s”), as she gazed at a satisfied Cindy.

“So, did I make the grade?” she asked.

“Let me put it this way – when are you available
next?” Cindy queried.

“How much do we owe you?” one guy asked.

“Field tests are always on the house. And so’s the
first time at Cindy Inc. If you’d like to make the
appointment now for a rematch…”

“But this time I want to cornhole Jenny,” Jessica
interrupted, looking at Jennifer’s ass. “The view
looks great from here.”

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