Chapter 15: Cheryl's second cliché
Lisa had dinner at a sandwich shop on the first floor of her
building. The shop was fairly crowded around 6, mostly with
businessmen in large groups who would come into the shop, see Lisa
in her short skirt and high heeled shoes, her nipples poking
through her blouse. They would comment to each other as if she
weren't there, eating her sandwich, trying to keep her legs closed
even though she knew everyone could see her panties. Lisa tried
to ignore them, but found that their audible comments and their
laughter only served to heighten the arousal that had already
reached record highs in anticipation of Cheryl's unknown plan.
When she comes back to the office, it is indeed empty. One or two
workers are still there, but from countless nights working after
hours Lisa knows the place would be deserted in a few minutes.
She finds Cheryl in her cubicle. She is reading her email.
"Hi," says Lisa. Cheryl looks over at her.
"C'mon," says Cheryl, "let's go over to your cubicle." Cheryl
grabs a black bag from under her desk before they go.
At Lisa's cubicle, Lisa sits in her usual chair and Cheryl pulls
up a chair from the next cubicle over.
"Okay," says Cheryl, "It's time we had a talk."
Lisa is worried. This is all so much easier if she doesn't have
to talk about it, she thinks.
"Did you enjoy yourself last night?" asks Cheryl.
"Well, yes, I guess I did. I don't really remember."
"Do you remember the shoe store?"
Lisa tugs at her skirt. Her legs are still naked. "Yes."
"Did you enjoy showing off?"
Lisa remembers how aroused she was. It felt so very good, but . .
. but how could she have enjoyed such humiliation? "Of course not.
That was . . . obscene. I would never do that again."
"Really? You seemed awfully . . . turned on . . . at the time."
Lisa crosses her arms across her chest. "Well . . . " she
admits, "I was turned on, because I didn't know what would
happen. But that's all. I would never do it again. Never."
Cheryl smiles and reaches into her bag. She pulls out a long,
plastic object with a power cord dangling from one end.
"Lisa, I want you to put your hands behind your head, and leave
them there. It's a skirt day, and this is a direct order." Lisa
gives a worried look but puts her hands behind her head. Her body
seems to be presented to Cheryl.
"Are you turned on right now, Lisa?" asks Cheryl, touching Lisa's
bare knee. "You don't know what's going to happen now, do you?"
Cheryl traced her finger up Lisa's thigh, sending shivers
throughout Lisa's body.
"I am very turned on," says Lisa. "You said I could have
permission."
Cheryl plugs the plastic object into an outlet by Lisa's desk.
"Do you know what this is?"
Lisa looks closely at it. White, plastic, smooth, wand-shaped.
"It looks like . . . a vibrator?"
"Have you played with one of these before?"
Lisa had heard of them, but had always been too shy to go to any
kind of store where she could buy one. "No."
"Well, then, I can't wait to see what you think." Cheryl pushes
Lisa's legs apart and rests the tip of the plastic wand against
Lisa's panties. The feel of the hard object against her makes her
shudder with pleasure. "Are you ready?"
Lisa can feel her pussy gushing. She couldn't believe she was
letting Cheryl do this, but she knew she wanted it. "Yes," she
says. And suddenly, a flick of Cheryl's fingers starts what felt
the injection of pure pleasure straight into Lisa's engorged
clitoris. Lisa had no idea how good it would feel. The
vibrations on her barely-covered sex cause her to moan and push
herself against the wand. She can feel her orgasm coming
quickly, very quickly!
But Cheryl flicks off the switch. "How was that?"
"Oh my god, I need more. I need more NOW," says Lisa. "Please."
Cheryl pulls the vibrator away. "Then be honest with me. Did
you enjoy what we did in the shoe store?"
Lisa still has her hands behind her head, but the arousal in her
crotch left behind by the vibrator seems to scream for one of her
fingers. She looks at the vibrator. "Please, Cheryl. Please!"
"Did you enjoy yourself? Just be honest!"
"I already said I did!"
"Would you do it again if I asked?"
"Well, if you asked, I guess I would."
"But you said you'd never do it again."
Lisa feels like she is on trial, but she could feel the juices
from her pussy starting to leak from her silk panties. This would
all be so much easier if I could just have that orgasm, she
thinks.
"I really would do it again if you asked."
Cheryl smiles. "I'm not so sure. We'll come back to the vibrator
in a few minutes; I want to show you something first."
Cheryl reaches over to Lisa's computer keyboard. She opens a web
browser and types in a URL. "This is what I want to show you." A
web page loads with a window for streaming video. Cheryl clicks
the play button. The video shows an office Lisa has never seen
before. Nothing happens for a few seconds.
As Lisa watches the movie, Cheryl lightly touches Lisa's thighs,
occasionally brushing her fingers against Lisa's panties, just
inches from the hem of Lisa's skirt. "There's no sound," says
Cheryl to Lisa, "so I'll have to tell you what's going on."
A blonde woman in a beige, knee-length skirt, white hose, and
white blouse enters the office. The camera's field of view
includes one edge of a large desk; the blonde sits at a chair a
few feet away from that edge of the desk. Cheryl says "This
woman's boss is on the other side of the desk. He is asking her a
few questions, and reminding her of an agreement they had made the
previous day."
Lisa sees the woman start to look worried. She looks down at the
buttons of her blouse.
"See," says Cheryl, "this woman is a lot like you, except she got
herself in some trouble. Her boss caught her making fraudulent
purchase orders in order to embezzle over $14,000 of company
money. She should have been fired and sent to prison, but she was
saved by her good looks. Watch this."
The woman starts to unbutton her blouse. When it is completely
unbuttoned, she pulls it off and hands it to the man on the other
side of the desk, off-camera. Her white bra is extremely low-cut,
and Lisa thinks she can see the woman's nipples, except the
resolution of the video leaves her unsure.
"Like you," says Cheryl, "this woman agreed to do everything she
was told. That's why she's undressing. See, she has no choice."
Lisa watches as the woman unhooks her bra and removes it. Then
she stands up and pulls her beige skirt up to her waist, revealing
a white garter belt holding up her white stockings. Lisa sees
that she is not wearing any panties.
Meanwhile, Cheryl's hand is tickling Lisa's inner thigh, reminding
her of her own arousal. Cheryl whispers "That woman is so aroused
right now, she can barely stand it. She is just like you. Well,
almost." Lisa's hands are still behind her head, and she wishes
Cheryl would touch her panties again. She has never before been
touched by a woman but the vibrator left her in dire need.
The woman in the video sits back down in the chair and, looking
ahead across the desk, hesitantly reaches between her legs and
begins stroking herself.
"He has ordered her to pleasure herself," says Cheryl. "She says
no at first; she says she can't possibly do that in front of
someone else, but then he threatens to go to the police, and she
tells him she'll try. What do you think? Is she going to go all
the way?"
Lisa sees the woman close her eyes as her rubbing speeds up. Lisa
has never seen another woman masturbate, and it desperately makes
her want to touch her own pussy. "Yes," said Lisa, "I think she
really wants to go all the way."
"Wait. Watch this." Lisa watches. It looks as though the woman
in the video is now looking at her, Lisa, right in the eye! She
must be looking at the camera, Lisa thinks! "He told her she's on
film and pointed out the camera." Lisa notices that the woman has
not stopped touching herself. Now the woman is looking at the
camera as she strokes her clit.
Lisa is transfixed by the woman. "See," says Cheryl as she pulls
away from Lisa and gets another item from her black handbag, "she
is just like you, but unlike you, she has no choice. She needs to
do this or go to jail."
The woman's eyes have closed again, and she is clearly writhing in
pleasure. Both hands are at her pussy now, and their motions are
nicely framed by her white garters and stockings.
"You can touch yourself now, Lisa, but you may not come," says
Cheryl. Lisa takes her hands from behind her head and starts to
rub her panties as she watches the woman. Cheryl is doing
something in her bag, but she looks up and says, "Take off your
panties, Lisa. Don't worry, no one is here." Lisa pulls the red
silk panties off and pulls them down her legs, leaving them
puddled at her ankles. They really do match her shoes. She
immediately starts rubbing her clit again. It feels so delicious
to finally touch myself, she thinks, as her fingers fill her with
her familiar warmth.
"Now," says Cheryl, "don't come yet. Just listen. You are not
like that woman, because you have a choice. You don't have to do
this."
Lisa is confused. "Yes, I have to do this. It's a skirt day.
I'm wearing a skirt. So I have to do what you say."
"What will happen if you don't?"
"Well, nothing, but . . ."
"Who enforces your skirt day rules?"
"Just me, I guess, but . . . "
"But nothing," says Cheryl. "You have a choice. You could stop
touching yourself right now, pull up your underwear, and go home,
couldn't you?"
"I guess."
"Wouldn't it be nice to not have a choice? Wouldn't it be better
if you knew that, like the woman in the video, you were doing what
I and everyone else said because something awful would happen if
you didn't?"
Lisa is furiously rubbing her clit now, as is the woman in the
video. Lisa can see that the woman in the video is close to her
release, but Cheryl had told Lisa she could not yet come. Why
/did/ she have to listen to Cheryl? She knows she could disobey
and have the orgasm she craves right now. Not having a choice
seems easier. It seems . . . better.
"Be honest, Lisa," says Cheryl, "this is all your choice, but you
would rather it were mine, don't you? If you're honest with me,
then you may use the vibrator."
The thought of the pleasure that the wand brought her drives Lisa
to the edge. She has to stop rubbing to keep from coming. "Yes,"
she says, "yes! It would be better!"
Cheryl finishes her work in the bag and pulls out a digital
camcorder. She points it at Lisa. "Okay, Lisa. Like the woman,
you are on film." Lisa pulls her attention from the video and
scrambles to hide her wet, nude pussy from the camera. She
looks at the camera lens which seems to stare at her, unblinking.
"If you want to," says Cheryl, "you can take that vibrator and
give yourself all the pleasure you want. But if you do, I will
capture it on film."
Lisa looks at the vibrator and remembers how good it felt. "You
can get up and leave right now if you want," says Cheryl, "but
then you and I will always know that your skirt days are your
choice. We will both know that you are the sort of woman who
simply enjoys shoving her wet, naked cunt in the faces of
unsuspecting shoe salesmen. But if you're really doing it because
it's not your choice, then it shouldn't matter if I've caught you
on film."
Lisa looks at the camera, confused. She looks at the woman on the
video who is now clearly moaning her pleasure as she orgasms on
film. The woman's nipples are hard, her back is arched, her head
is back, her eyes are closed, and her fingers are deep inside her
dripping pussy, and although there is no sound Lisa can almost
hear her screaming in pleasure. Lisa's own sex can still remember
the pleasure of the vibrator, and Lisa is dying to feel it again,
but the camera continues its steady gaze.
This is it, thinks Lisa. She thinks about what has led her to
this point. She knows that if she pulls on her panties and
leaves, her life will go back to normal. But if she gives herself
the orgasm she craves, then she knows that she is embarking on a
new, sexual adventure that could lead her to unthinkable
pleasures. She reaches for the vibrator on her desk. She knows
the camera can see up her tiny skirt; she knows it can see that
she is wet, that her clit is giant and red, and she knows that it
can see her touch the vibrator to herself. "Good," says Cheryl.
"Go ahead, turn it on."
When Lisa flicks the switch, the pleasure is overwhelming. With
the vibrator in her hands, Lisa realizes that nothing, not Cheryl,
not even a pair of panties, stands between her and the orgasm.
The vibrations on her clit are almost too much; they make her
scream out loud. She moves the vibrator between her lips with one
hand and touches her clit with the other. She gently pushes the
vibrator inside her, feeling the vibrations emanate pleasure all
through her body. The pleasure is so intense she forgets the
camera, but only for a moment.
"If you disobey me," Cheryl says as she films, "then this video
will end up on the internet, just like that woman's." Lisa looks
over at the video and sees that there is now a large black man in
the shot, his pants around his ankles, his cock in the mouth of
the blonde woman. "She disobeyed, and now everyone knows. Think
about that, Lisa. Do you want to end up like her?" The
vibrations are sending Lisa over the edge. She looks at the
camera. She knows what this means. This means she is committed.
This means that she will have no choice. She is now thrusting the
vibrator in and out of herself as she furiously rubs her clit.
This means that skirt days are for real. The thought that Cheryl
can now ruin her if she backs down sends the final jolt of
pleasure through her body, sending every muscle in a violent,
pleasurable convulsion. "OOOOH GOOOOOODDDDD!!!!" she screams as
the orgasm rips through her, stimulating every nerve from head to
toe.
The orgasm seems to last for hours, coming back in little spurts
as Lisa returns the vibrator to her clit, as she opens her eyes
and sees the camera's unblinking lens, as she recalls what she has
gotten herself into.
When it is over, she feels completely exhausted. The video is
still playing; she sees that the woman is now being fucked from
behind by the large black man, whose uniform suggests a custodial
position. She realizes what Cheryl's video has captured. It has
captured Lisa, in her cubicle, at work, furiously masturbating
with a vibrator as footage of a woman giving a blowjob to a large
black man is showing on her computer screen. The video shows no
struggle, no circumstance, no context. Lisa realizes that if her
coworkers saw this video, she could not work here again. She
probably could not work anywhere. And yet, she thinks, she did
this to herself. She wanted this.
"Please," says Lisa, "Don't show that video to anyone. Please."
Cheryl smiles as she packs the camera and the vibrator in her bag.
"Don't worry," she says. "It will be for my eyes only, as long as
you stick to your promises. When you're wearing a skirt, you do
what anyone says. Just like you promised. If I find you've
disobeyed me or anyone else, then I know just how to get that
promotion." Cheryl patted the camera. "But as long as you stick
to the deal, you'll probably get the promotion. Heck, you deserve
it more than me. You work much harder."
Lisa pulls her panties up her legs. The wet silk makes contact
with her even wetter pussy.
"And don't forget," says Cheryl, "to meet me before you go golfing
on Friday. And no more pantyhose, ever. And no masturbating
without my permission."
Lisa nods, realizing that she will really have to obey, now. "Oh,
and I almost forgot. You and I are going to a party on Saturday.
My friend Martin - you'll like Martin - he gave me lots of advice
about you and really wants to meet you, so he's throwing a small
party. I'll pick you up at your place. Wear one of your skirts,
of course. We'll go shopping and buy an appropriate cocktail
dress before we go."
Lisa's nervousness grows. But now she has no choice. "Okay," she
says.
"I have one last thing for you to do this evening," she says. She
takes a notepad from Lisa's desk and scrawls down an address. "Go
to this address now. You can get there by taking the red-line.
Don't worry, it's a safe neighborhood. The apartment is just a
couple blocks from the subway stop. Knock on the door, and don't
leave until someone answers. Then you are to do everything that
person says. Understood?"
Lisa again nods.
"Good night," says Cheryl. "See you tomorrow morning!"
Cheryl leaves with her black bag. With the vibrator that gave
Lisa so much pleasure. With the camera with the footage. With
Lisa's future.
Meanwhile, the blonde in the video is still being fucked from
behind, this time by the janitor's mop handle. The woman is still
screaming in ecstasy. "Is this really real?" asks Lisa, as she
looks at the footage more carefully. It starts looking more and
more like a low-production-value porn movie. "It doesn't matter
now," she thinks, as she closes the window and shuts down her
computer.
