Chapter 16 Who's the Boss?
The city is dark and uncrowded as Lisa takes the subway to an
unfamiliar stop. She feels vulnerable in her tiny skirt and high
heels, but indeed she is able to find the address Cheryl gave her
without any difficulty.
It is a small apartment complex. The apartments make a U-shape
around a shared parking lot. She looks at door number 3, where
she is supposed to knock according to Cheryl's instructions.
She tries to imagine what---and who---lies behind the door. Her
imagination tends toward the large black janitor, forcing himself
into the blonde woman who had no choice. What if she was going to
have to have sex with this person? What if this person beats her?
She feels very frightened. Her trust for Cheryl is uncertain, but
not completely absent. The danger awakens her pussy again. She
has no choice, she thinks, as she feels the warmth return to her
pussy.
She knocks on the door three times. After a brief pause, she
knocks again. "Hold on," shouts a male voice. She waits.
Finally, the door opens. She looks down and sees that the man is
wearing simple gray sweat pants and a plain white undershirt. She
looks at his face, which is unshaven and looks confused.
Then she recognizes him. It is Steve.
"Lisa!" he says, "Wha---what are you doing here?"
Lisa is as surprised as he. "I. . . didn't you talk to Cheryl?"
"Cheryl? Cheryl from the office? Why would I talk to Cheryl?"
There is a pause, and Lisa can see Steve's eyes wander down her
body, past her red lacy camisole beneath her mostly unbuttoned
blouse, to her black skirt, barely hiding her sex, and onwards
down the full expanse of her bare legs to the high red heels. Lisa
feels exposed, standing outside Steve's door.
"Can I come in?" asks Lisa, and Steve nods, watching her ass as
she walks past him into his small living room.
"I, um," stutters Steve, "I've been sick, but I'm okay now, and
was going to return to work tomorrow morning."
Lisa lets out a little laugh. "Oh, don't worry about it. I
understand. May I sit?"
"Of course," says Steve, as he clears some newspaper from a small
black couch. The couch is quite low, and as Lisa sits she
suspects that she cannot help but show Steve her bright red silk
panties.
Steve sits on an armchair across from the couch. Then Lisa
notices: Steve's loose grey sweatpants reveal a rather large lump
at his crotch. He's clearly hard. Very hard.
She realizes that she is staring, and Steve seems to notice. He
uncomfortably crosses his legs. Lisa wonders---does this
embarrass him? Is it humiliating for him to have his arousal on
display in that way? She crosses her own legs, knowing that this
exposes more of her ass than she feels comfortable with. She
smiles at him. He smiles at her. An awkward silence ensues.
Lisa waits for Steve to speak, but he seems nervous. He seems so
different from the confident, almost cocky man who ordered her to
wear stockings, to unbutton her blouse, to do all those things.
She finally loses her patience with his hesitant silence.
"Steve," she begins, not quite knowing what to say, but trying to
imagine instead what Joan, her therapist, would say, "maybe we
should talk about why you \emph{really} have not been at work. You
haven't actually been sick, have you?"
Steve blushes and uncrosses his legs. His erection is still
visible through the thin sweatpants, and Lisa catches herself
staring again, but then forces herself to look at Steve's face. He
crosses his legs the other way. "Well?" she prods.
Steve stammers, "Well, I guess, when you wore that skirt, like I
asked, I thought maybe you wanted to play a game with me, where I
was the boss. You know, with the stockings, and the water bottle,
and all that. You really seemed to be into it. But then you got
really upset, and you yelled at me and gave me a huge pile of
work, and I got really worried. I didn't know what to do or what
would happen on Monday so I took a sick day. This morning I still
didn't know. . . "
Lisa remembers that she had meant to apologize, and that she never
got around to it. But Steve's reluctance this evening, and the
sight of his large erection beneath his pants, somehow makes her
feel less apologetic. Perhaps even a little annoyed with him. He
was supposed to be calling the shots, right? Why does she have to
direct this awkward conversation?
"Well, Steve," says Lisa, feeling herself for the first time
today, "that was a pretty wimpy response. Apparently, if you
don't know what to do, you just don't show up."
"I thought maybe. . . "
Lisa finds herself on familiar ground. She is the boss. "I don't
think you thought at all, Steve. I expect my employees to confront
their problems. If you need to ask for help, ask for help. But
don't just run away."
"I thought you needed time."
Lisa raises her voice. "And how can you possibly know what I
need? The fact is I needed you at work. And if you want to keep
your job, you had better return tomorrow morning, since it is very
clear that you are not at all sick!"
Steve's erection only seems to grow as he silently listens to Lisa
berate him.
When she seems to be done, he raises his hand, as though he were
again a young student in the schoolroom. "Yes?" says Lisa, still
wearing a scowl.
"Are you going to wear a skirt tomorrow, again, like last
Wednesday?"
Lisa is stunned. Usually her stern voice and harsh words resulted
in only hushed compliance. Perhaps it is her naked legs and her
visible red underwear that undermined her authority, she thinks.
Unable to take her eyes off Steve's crotch, she feels her pussy
moisten again. How would that cock feel inside her?
"I am," she says, with waning confidence.
"And does that mean you're doing what I say, like last week?"
Lisa again does not know what to say. Cheryl had told her to obey
Steve, hadn't she? And she promised to obey while wearing a
skirt. The answer is clearly yes. Yes, Steve, I will do what you
say. She thinks it but does not say it. She again looks at the
shape of his cock beneath his sweatpants; his erection had not
shrunk in the least. Yes. Yes. Fuck me, yes. Yes!
"Maybe," she says.
"Maybe?"
Lisa starts to feel uneasy. Does she want him? She begins to
feel threatened. He looks. . . big. Ever bigger. Will it hurt?
It has been so long since she's been with a man, and that one time
was. . . small.
"What is it that \emph{you} want, Lisa?" Steve raises his
eyebrows, expectant. Lisa feels she has lost her ground, but
somehow, after everything that happened with Cheryl, wants to
regain it.
"I want you at work tomorrow. I have a lot of work for you to
catch up on." She tries to exert her authority, but her voice is
now uneasy. I want you to fuck me, she thinks.
"Okay," says Steve, "I'll go to work. Is there anything else?"
How would it feel? she thinks. Maybe I could just touch it. . .
"If not, I guess you should be getting home. It's getting late."
Steve stands up, and his erection is even more obvious when
standing. He walks to the door and opens it.
"But. . ." Lisa stands up, spreading her legs and flashing her
red panties as she does so. "Wait, Steve, I. . ."
"Yes?" Steve holds the door open, waiting for Lisa to speak.
"I. . . " Lisa still does not know what to say. She cannot ask
him for what she wants, can she? If he knows. . .
"The answer is yes. Yes, I will do what you say, when wearing a
skirt."
Steve smiles. While still holding the door, he pushes Lisa by her
tightly-skirted ass through the door. The feeling of his hand on
her rear is electrifying, but very brief.
"Excellent. Then this is what I want you to do. Tomorrow, I want
you to wear the world's shortest skirt."
Lisa is again standing on the doorstep, conscious of her
visibility. She sees a couple walking down the sidewalk; surely
they can see how much she wants him, in her tiny skirt, high
heels, and unbuttoned blouse, desperately trying not to leave.
They must think me lusty, horny. . . and why doesn't Steve want
me to stay? And what did he just say?
"What?" asks Lisa, "what do you mean, world's shortest skirt?"
"Here's the rule," says Steve, "and this goes for every
Wednesday. I want you to wear the shortest skirt in the world.
The one you're wearing would probably do, it's barely there; but
you really shouldn't wear the same thing twice in a row. So
whatever skirt you are wearing, make sure that no one is wearing a
shorter one."
"But how will I know if someone is wearing a shorter one?"
"Well, how about we work it this way. If I see someone wearing a
shorter skirt than you, I will point her out, and then you'll be
in trouble. Then you'll be punished."
"Um, punished how?" Lisa feels her arousal build. Why won't he
just fuck me?
"When we find someone with a shorter skirt, you will be required
to give me your underwear. All of it. That's the rule. Now, I
had better get to sleep. I have to go to work tomorrow." And he
shuts the door.
Lisa stood on the doorstep, perplexed, for a few minutes, before
walking back to the subway, barely balancing on her heels. Why
must he play these games? She thought of his hard cock, straining
his sweatpants, and wondered why it was not inside her, right now.
Oh well, she thought, I'll just have to get myself off when I get
home---but then she remembered Cheryl, and her skirt, and knew
that she could not.
