Cindy Inc.: The First Time

The continuing adventures of Cindy Crawford –
supermodel, mother, and celebrity bordello owner.
These tales are fictional, not meant to represent
actual conduct, and not for readers under 18. And a
special note: This one is concerned with an unusual
aspect of celebrity sex – bad celebrity sex. (Face it;
celebs are people too.) Normal service will resume
next time.

Incidentally, if you have any requests for celebrities
you’d like to see guesting in any future stories (and
specify if you want them working for Cindy Crawford or
Jennifer Lopez) or any kind of feedback on this or any
other of my tales, write to me at

* * * * * * * * * *

When Cindy stood in for Kathie Lee Gifford on “Live
with Regis and Kathie Lee,” Regis Philbin told her
that she’s always attached to really good-looking men
(thereby providing a clue to why Cindy has never been
with Mr. Is That Your Final Answer?) – Gere, Kilmer,
and now her present hubby. He forgot to mention that
they all tended to look pretty pleased with
themselves. Not that Rande could be blamed, especially
at this time.

Cindy sometimes wasn’t in the mood for sex at home,
particularly if it had been a rough day at work.
Happily, tonight she was up for it; they were
thiscloseto signing Britney Spears, her kids had been
as good as gold lately, and she was picking up some
new fans from her new Pepsi ad. She always loved
swallowing her husband’s equipment, and as she enjoyed
Rande’s gurgles of delight while consuming his
tingling rod, she felt things couldn’t get any better
than this. Granted, Cindy Crawford blowjobs were
always a pleasure to give and to recieve, but the
better her life was, the better the O levels were.

Her gusto-packed fellatio and his panting as his
wife’s soft, warm mouth did its work didn’t quite
drown out the phone ringing, or the answering machine
taking the message: “Cindy? It’s Jennifer Love
Hewitt… I quit.”

“OhmyGOD!!!!!!” Rande shouted to the ceiling as he
felt his cock starting to boil, vocalising Cindy’s
state of mind at that moment. Unlike him, she had
heard and paid attention to the message…

* * * * * * * * * *

It was quite the day for cursing in the world
according to Cindy Crawford; first that bombshell, and
now the set that Jennifer was making her current movie
on was of the closed variety, meaning she’d have to
wait until shooting was over for the day to find out
what the hell the bosomy, bubbly actress – one of
Cindy’s most frequently requested employees – was up

Cindy finally left a message requesting the lovely
Love’s presence at Cindy Inc. and returned home,
fretting. Maybe it was a family thing (the parents of
Serena Williams and Anna Kournikova, for instance, had
no idea that Venus’s sister and little Hornykova were
regularly handling balls of another kind at J-Lo’s –
not that Cindy Inc. was free of such subterfuge, as
Martina Hingis and, er, Venus Williams could testify).
Perhaps she was tired of the rush, if not the money.
Whatever it was, it had to be serious.

* * * * * * * * * *

“I don’t think you’re going to want me back after what
I have to say,” Jennifer Love Hewitt said shyly as she
joined Cindy in her office.

“Why? What happened? Did you say yes to ‘I Know What
You Did Three Summers Ago’? Did you get a better offer
from J-Lo?” That had been known to happen, which was
why Cindy tended to spit on the ground and cross
herself at the briefest sight of one of the Trio of
Treachery – Kirsten Dunst, Tara Reid and Julia Stiles.
(At J-Lo’s, meanwhile, it was a sackable offence to
even mention Katie Holmes, Alicia Keys or Faith Hill.)

“What, are you kidding? Of course I’ve received them –
I’ve just said no to them. It’s just… this guy
called Lewis went with me the other night and… I
tried EVERYTHING, Cindy! I did everything I could to
make him happy; I even let him slap me around a bit –
anything to get him to come…” JLH finally broke down
in her chair.

“He said he’d had better sex by himself!” she sobbed.
“He was so cruel, and I tried so hard… I don’t know
what was wrong… was it me? It was me, wasn’t it?”

Cindy shook her head as she got up. “Have you seen the
waiting list, Jen?” she asked, holding the weeping
actress in her arms to comfort her. “The feedback
people left about you? Some of them are coming back
for seconds, thirds, you name it. You’re a
perfectionist – you just had a bad night. It happens
to all of us.”

“It never happened to me before,” Jennifer sniffled.
“Not ever.”

“Well, it happened to me,” Cindy told her. “C’mon –
school is in session…”

* * * * * * * * * *

“Thanks Inger – you’re a gem. Okay ladies,” Cindy said
briskly as Inger deposited their cups and coffee pots
on the table, “I know you’re all on duty this evening,
but I’ve called you in early because Jen here is
suffering from a crisis of confidence.”

“Maybe she’s heard the Stallion is coming in tonight?”
Rebecca Romijn-Stamos suggested. “Trust me, you WILL
get back to normal once he’s put his-”

“She had her first time the other night,” Cindy
explained. Rebecca and the others – Halle Berry, Kate
Winslet and Eliza Dushku – looked at JLH with complete

“First time since you joined us?” Eliza asked through
her cigarette.

“First time EVER,” Jennifer corrected, and told them
what she’d told Cindy, but without the breakdown.

“Well, it couldn’t be any worse than mine,” Kate
chipped in, squeezing Jennifer’s hand in solidarity.
“This was back in ’95, BC – Before Cameron.”

“You and Cammie Diaz? Fuck you! When the hell did that
happen?” asked Halle.

“In your imagination. And I meant James Cameron,” Kate
continued. “Anyway, I’d made friends with a crewman on
‘Sense and Sensibility’…”


and Kate had had a couple of drinks with him. Chatting
aimlessly about nothing in particular, they had
stumbled into his flat. From that point, it hadn’t
been long before they had fallen into bed.

They were hardly long-time friends, but Kate was
hardly bashful about baring her body, especially since
she had nothing to be modest about. “That would liven
up this costume drama… wish this wasn’t going to be
a U film,” the crewman slurred apprroving as Kate
shrugged out of her clothes. “You just lie back and
enjoy it.”

“I don’t just lie back,” she assured him as he
enfolded her beautiful, full body in his arms. She was
such a yummy lady – no Dame Judi thank God. They
started to explore each, loving their respective
odours and contours. “Eat me,” Kate murmured.

“Um… do I have to?” the crewman asked. “I’ve never
really tried it…”

“Come on,” Kate begged between kisses. “I’ll blow you

He really expected each lady he slept with to go down
on him, but if you had to munch someone it might as
well be Kate Winslet. She felt a deep sense of
satisfaction as he journeyed down her soft and pink
frame; he enjoyed the trip to her shaven slot. It did
feel nice in his fingers, he had to admit. Then he
started to poke his tongue inside.

Suddenly Kate felt a lot damper down there.

“You’re kidding!” Cindy spluttered through her coffee.
“The guy actually threw up?!? All over your…”

Kate nodded, wrinkling her nose at the memory.
“Drenched me like a flood – some of it went inside me
as well. He told me he never liked how it tasted but
he thought he might as well see what a Star tasted
like… it was years before I let another fellow do
that to me.”

“Okay, that was gross, but that wasn’t your fault!”
Jennifer protested.

“So Katie,” Eliza laughed, ignoring Miss Hewitt, “when
you say that, do you mean letting a guy EAT your pussy
or PUKE on it?”

“Just for that you’re next, Miss My Hands Are Clean
But My Mind’s Dirty,” Rebecca retorted.

“Like I ever have bad sex,” Eliza parried, to
disbelieving glares from the others (except a still
preoccupied Jennifer. How long did Kate’s snatch
smell, she wondered?). “Okay,” she relented, taking
another long drag from her cig, “there was this one
time I went to a party…”


and she was dancing with the only man there who had
been at her very high energy level. Eliza was a
maniac, MANIAC on the floor, and she was dancing like
she – like she usually danced, frankly. Horny and
enticing, she was the envy of the other ladies there,
and she knew it. This was her third night with this
man; she felt tonight would be the night for sure.

“Let’s get out of here, El,” he breathed.

“You read minds too?” she laughed as they gyrated off
the dance floor towards the door. Watching his tight
butt twitching, Eliza laid mental odds she was in for
a treat when they hit the sheets in half an hour.

30 minutes later, she was indeed naked on his bed and
waiting. “Come on, loverman,” she purred. “Don’t leave
me hanging all night…”

There he was – he was on top of her, he was sticking
himself inside her… and then he was out. Not even a
slight wet spot as an afterthought. If this had been a
Steven Bochco show, it would have been “Public
Morals.” Well okay, it lasted a bit longer than that –
the sex, not the show; he did take the time to kiss
and hold her first as his idea of foreplay before
poking her, and he did say “Thanks, Eliza” before
beddybyes, but as he snored beside her (“Jeez, he
snores?” she thought. “Bad in bed and he SNORES?”} she
wondered how best to let him know that his bed
technique left something to be desired.

Even then she might have used some tact, but then he
started to talk in his sleep. Eliza Dushku’s mouth
dropped open as he muttered approvingly in his sleep
and even made little kissy faces. But even that in
itself wasn’t what finally drove her to get up, get
dressed, leave a note telling him to go fuck himself
in future, and call a cab. It was WHAT he said…


“The guy was dreaming about Rosie O’Donnell!” a still
enraged Eliza confessed. “Can you imagine that? Rosie

“Maybe you misheard him? Could’ve been mentally
jerking to Rose McGowan?” Halle asked.

“Edited highlights of what he said – ‘Mmmm Rosie, I’ll
make you forget Tom Cruise,’ ‘You don’t want women
when you can have me, baby,’ ‘Yeah Rosie, stick that
fat ass up in the air.’ Is Rose McGowan hot for
Cruise? Does she go for girls? Does she have a big fat
ass? No, no, and no.”

“OK OK, turn down the heat Dushku,” Rebecca urged.
“You’re scaring Jen.”

“Yeah, right,” Jennifer snickered as she finished her
drink. “Pass the pot, Cin – refill? This is helping a

“There you go,” Cindy said passing the coffee pot.
“But maybe if you talked about it it would help.”

“Maybe if one of you told a tale where it wasn’t the
man’s fault it would help even more,” Jennifer pointed

“You win,” Rebecca sighed, setting down her own cup.
“Just before I did my last ‘House of Style,’ John had
to go out of town for the evening.”


Rebecca had been pining for some company, but all her
friends were out, and she didn’t want to spend the
night by herself. Flipping through channels, she
remembered a model friend boasting about an escort
service that only employed the most polite, best
looking male prostitutes. “In the business they’re
called the Pinocchio Boys,” her friend had explained.

“How come?”

“Because they have long legs and short noses; didn’t
you read the book? Lies come with short legs and long
noses – they never lie and they don’t shrink or get
Streisand honkers. Plus, they’re ALWAYS hard,” she
added with a laugh. Rebecca had jotted down the
number, and on finding it she was on the phone making
arrangements, but carefully not giving her real name –
you could never tell with these people.

Right on time the doorbell buzzed; Rebecca had kept a
small bit of caution in her heart to make sure she
wouldn’t be disappointed. Opening it to a handsome,
perfectly groomed man in his late 20s, she wasn’t.

“You must be Christopher,” she said.

“I am indeed,” the gentleman answered. “And who would
I have the honour of addressing?”

“Just call me Rebecca,” she urged, letting him in and
wondering how long the pleasantries would take. As it
turned out, they lasted a while – Christopher was not
one for rushing things.

Miss Romijn-Stamos soon found out, to her delight,
that this also applied in bed. Feeling him nibbling
her nipples gently, she was dying to come. She was
wondering why she hadn’t called these people before
(OOOOH YES!!!) before. She closed her eyes as she
stroked Christopher, waiting for him to slide into

She could feel his lips on her slot, gently teasing
her. Rebecca was all charged up, and all he had to do
was take her…and there it was, her cunt was suddenly
stuffed full with a wonderful, wonderful logjam,
leaving her feeling…

Nothing. What should have been a fabulous experience
was all buildup, no climax. Christopher withdrew from
Rebecca, a look of disappointment in his eyes. “You’re
a very beautiful and friendly woman, Miss
Romijn-Stamos,” he told her calmly as he dressed. “I’m
sure you’ll improve with time.”

Rebecca somehow managed to retain enough composure to
bid him goodnight; when he was gone she spent the next
half-hour railing against her own reflection. The
worst of it was, it wouldn’t have been so bad if he
had told her blankly that she was bad in bed; then she
could have berated him and be done with it… but it
would have been bad for her in future if she had.

No, that wasn’t the worst. What was the worst was –
did that mean she was letting John down as well? Was
she really only coasting on her looks?


“So the next time I tried a lot harder in bed. And the
time after that even harder. And I’m still not sure
I’m over that time yet,” Rebecca finished. “I’m not
sure I ever will be.”

“Did you ever call the guy again?” Eliza asked.

“Hell, no! That was for MY benefit, not his!”

Halle had looked lost in thought throughout. “Did you
say his name was Christopher? The guy I was with last
night said he was Christopher…”



“Then it wasn’t him,” Rebecca sighed in relief as
Halle turned to Jennifer.

“Guess we should all stay away from guys called


Halle gagged at the man’s pale, blubbery backside. She
had forsaken any kind of belt or whatever, and looking
at the expanse before her she regretted it – ANYTHING
to avoid direct contact. “Do it!” he begged. “I’ve
been a bad boy (“Not since Reagan was in office you
haven’t,” Halle thought)… I need to take my

Halle winced and gave him a tentative slap.
Uuuugghhh!!! On top of all that he had a sweaty ass!
Disinfectant for sure when she got home – thank heaven
he wasn’t flatulent. “Harder!” he cried. “I need this!

She paddled him again, with more force this time.
“Hurt me, Miss Berry! Harder! HARDER!!!”

And Halle slapped his jiggling rump rapidly,
channeling her disgust at what was happening into her
spanking. “Yes!!! That’s it!!! Punish me, Halle baby!

Halle felt as if she was the one being punished as she
whacked him, feeling the flesh starting to sting. She
could actually feel herself starting to get into it…
not as the slave, uh-uh. She was the MISTRESS, baby!

“Stop,” he said suddenly in a different tone of voice.
Not weeping or feigning sorrow, but noncommital. Her
hand stopped an inch or two above the glutes.

“You’re not into this, are you?” he said. “And I
thought you big Hollywood stars were up for

“Hey, I can do it!” Halle said a little too eagerly.
“I can even get out the cat-o’-nine-tails if you like,
or do you want to try something else next time?”

“There’ll be a next time,” he replied. “Just not with


“I told him I’d go through it with him for free, and
he said forget it I didn’t have my heart in it!” Halle

“Well, you didn’t did you?” JLH pointed out, and Halle
shook her head.

“You’re fired,” Cindy said laughing, as she looked at
the clock. They’d been sitting there for about an hour
or so, and the ice had been broken – Jennifer had even
stopped complaining about Eliza’s cigarettes.

“Well, what about the boss lady?” Jennifer asked.

“We’ve all told.”

“Fair enough,” Cindy sighed. She was feeling that this
had been a better idea in theory than in practice, but
she had no choice but to put her pretty head on the
block. “I’ve had a couple,” she began. “But the worst
one was with someone I knew before…”


This person had been a good friend of hers, and he had
invited her to a private party thrown by a mutual
friend. He wasn’t the best looking guy she’d ever
seen, but at the time she was totally wet – mainly
because at the time she and he were in a swimming
pool. It was after midnight, but the party showed no
signs of ending any time soon; with so much noise and
merry-making, it was hardly as if anyone was noticing
Cindy and her date/friend getting very comfortable in
the deep end.

Up above the two were merrily laughing and kissing,
but under the surface they were naked, limbs floating
and chests touching. Until now they had just been
friends, but now… this could be the start of
something else. This was going to be a quickie,
nothing more; but it wasn’t like sex had an inflexible
time limit.

Cindy leaned in closer and thrust her tongue into his
mouth. He was just as keen on Frenchies as she was,
and he wasn’t smashed into the bargain. In the water,
she felt the lapping around her pussy be blocked up;
his prick was hot and hard against her opening. She
spread her legs apart to make it easier. “Don’t wait
up for me,” she begged, and felt the bone start to go

“OW!” she tried to bite back as it went inside.

“Sorry…” he groaned, as he started to thrust again.
This time Cindy told herself she was ready as he
clutched her, the two bobbing in the chlorine as he
entered. Cindy started to rotate with him, and this
time it seemed as if…

“OW! Dammit…” It still hurt, and by now he could
tell something was wrong. He was doing everything
right, so was she; they liked each other…


“I think that might have been it,” Cindy finished. “We
liked each other, we just didn’t fit.” She finished
her second coffee, fingering the cup. “I guess friends
just shouldn’t fuck.”

“Why did you try then?” asked Kate.

“Don’t you know why? It was a party, a spur of the
moment thing,” Eliza explained with the air of someone
who knew whereof she spoke.

“So, you still wanna quit, Jen?” asked Halle. “We’ve
all been there, none of us became nuns…”

“Well… maybe one more chance,” Jennifer smiled
weakly. “But if it ever happens again, I’m-”

“-taking the next day off,” Cindy interrupted. “I’m
not letting you go that easily. Now come on, let’s get
all this caffeine off our breaths.”

“I don’t know…” Kate mused as they got up. “When I
was down in Baja shooting ‘Titanic’ I once nearly
drank a Starbucks out of existence and then had an
allnighter with some Mexican crew members. I didn’t
hear them complain about the cappucino on my breath.
Mind you, they were all drunk…”

* * * * * * * * * *

Jennifer Love Hewitt and her customer were fast asleep
in the Plaza Suite (the staff’s name for the plushest
room in the building – every lady took turns using it
and tonight it was Jennifer’s). Her last thought
before falling asleep in his arms was that she had
tried her hardest this time, and hopefully that had
been good enough.

His last thought before falling asleep was that his
friend had been wrong – not all celebs were crap in

* * * * * * * * * * *

“That’s the third tape she’s filled up,” Cindy laughed
to herself, ejecting the answering machine tape Pink
(one of J-Lo’s ladies) had used to leave abusive
messages about Cindy Inc. for, and dumping it in the
incinerator. By pure coincidence, tonight was the
night that Britney Jean Spears would be holding court
at Cindy Inc. for one night only, having rejected the
Boeing jet-loads of money that Lopez et al had

Not only had they been inundated with demands to be
among the lucky few who’d get to bone Britney, but all
Cindy’s other ladies had benefitted from the overspill
– Cindy Inc.’s roster was booked for the rest of the
year and well into the next one. And best of all,
Britney was already on the premises (all had agreed
that a repeat of the London fiasco was best avoided).

“You’ve got mail,” said Cindy’s computer as she was
about to go and get ready for tonight. She considered
leaving it for later, but felt a quick check couldn’t
hurt, and soon found she only had one letter in the
box. It was a link to another site.

“Hm,” Cindy thought as she clicked it out of
curiosity. “Probably another stupid spam site, but you
never know…”

Then she sat down in shock. It had opened onto a
webcam picture of the Plaza Suite; no one was inside
as yet. Above the picture was a clock counting down to
8pm Pacific time. Below was the line “See Britney
Spears Lose Her Virginity LIVE From Cindy Inc. Tonight
From 8pm PT.”

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