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Stimulating
Stories About First Time Sex
A Compilation of Literate
Erotica
Emma in the
Afternoon
by Harry Merkin
These
short stories are
works of fiction.
Names, characters,
places and incidents
either are the
product of the
author’s vivid
imagination or are
used fictitiously.
Any resemblance to
actual human beings,
living or dead,
business
enterprises, events
or locales is
entirely
coincidental.
My dorm door is ajar so I can hear when
the guy across the hall is back so we
can shoot some baskets.
I hear a soft knock.
“Come in.”
Emma comes in. She’s wearing a pretty
dress!
I smile, stand and take her hand.
“I liked what we did last night.”
“Me too. You are a good kisser.”
“And you are beautiful today. Did you
want to go somewhere?
“The dress?”
“Yeah.”
“It’s my interview dress.”
“You want to interview me?”
“No, silly. I went for an interview for
my summer grant request.”
“How did that go?”
“Probably very well. The man from the
foundation couldn’t keep his eyes from
my breasts.”
“So that’s why it’s your interview
dress.”
Emma grins while blushing.
“I doubt you came to watch me study, did
you want to do something?”
“What do you want to do?”
I start pulling down the zipper on her
dress. Her eyes go wide.
“May I continue pulling down the
zipper?”
“Part of me wants you to undress me. I’m
also a bit nervous, even scared. I’m not
sure I’m as pretty as some of the girls
I’ve seen you with.”
“Emma, we spent more than two hours
making out last night. We left a big
dent on the sofa in the TV room. Would I
have done all that if I wasn’t more than
fond of you”
“Insecurity is my middle name.”
We kiss, lightly at first, then
passionately.
“Would you be less nervous if I asked
you to undress me first?
She nods yes.
“Have you ever seen a naked boy?
She nods yes.
“Was it one my age or was it while you
were babysitting a baby or toddler?”
“The oldest one was about 3 or 4.”
“My wee wee is bigger. Much bigger.”
She giggles while pulling down the
zipper on my cargo shorts.
”Take your time. I trust you so much
that I’m giving you full access to my
body. You may touch me anywhere.”
Emma touches my crotch, first gingerly,
then probes the contours of my bulge.
“What should I take off first?”
“You’re in charge.”
She takes my T-shirt and pulls it over
my head then off. She gives me her best
smile then unbuckles my belt and
unbuttons my pants. She sees my
sneakers, looks at me, then asks me to
take them off.
”I couldn’t think of a graceful way to
take off your shoes while wearing this
dress.”
“You could sit on my bed, slide my chair
close to you and have me put one foot on
it, then the other.
“I’ll do that next time.”
She pulls down my shorts and stares at
my briefs.
“Remember, you may touch me. … You know,
it might be better if you didn’t debrief
me just yet. I wouldn’t want to get
anything sticky on your dress.”
We then kiss for several more minutes,
during which I pull down her dress
zipper all the way and fumble to undo
her bra.
“Do you want your dress taken off over
your head or pulled down?”
She shrugs, slumps her shoulders,
allowing the dress to slide down to her
ankles. She steps over the puddled
dress and takes off her patent leather
heels.
“You are beautiful. Absolutely
beautiful.“
We embrace. We kiss some more.
“Since you are wearing a half slip, may
I first reach underneath to pull down
your panties?”
“It’s a thong. Watch where you put your
fingers.”
“I’ll pull it down from the waistband.”
“You’re such a gentleman.”
“Will you still say that after we
eventually unlock my door and go out?”
“It all depends on how you react when I
tell you I’m a virgin.”
“I would tell you that you could remain
a virgin even after we spend a while
writhing on my bed. We could still enjoy
intense pleasure. I would still be just
as fond of you. I would still want to
get to know you better in the weeks and
months ahead.”
“You are a perfect gentleman.”
I reach under her slip, caress her butt
cheeks. Pinch them gently and slide down
her thong.
She pulls down my briefs. She then
raises her half slip up to her armpits,
revealing a neatly trimmed bush and
glistening labia.
“You are even more beautiful.”
I take the beach towel from the foot of
the bed, toss my swim trunks to the
dresser and spread the towel on the bed.
“Is that towel for me?”
“Yes, once I help you with the slip.”
Emma, now gloriously naked, sits on my
bed, lays back, brings her feet up, then
spreads her legs. She places her right
hand on her mound.
“Do you want to touch me here?”
“Yes, though I don’t know how you like
it done.”
“I’m going to be so embarrassed doing
this.”
“You’re naked, on my bed, with your legs
spread and you’re not already
embarrassed?”
“Well, no. That sort of snuck up on me.
I was so excited undressing you, then
you undressing me aroused me so much
that I didn’t fully process that I was
naked with a boy for the first time.”
“Would you prefer that we just kiss for
awhile?”
“Where will you put that?”
“It will be least in the way between
your legs, but not in you.”
“Are you sure it’s not going sneak in
and fuck me?”
“Not today.”
I mount her, place my erection between
her legs, and ask her to move her legs
together.
After a few minutes of intense kissing:
“Your dick between my legs feels almost
as good as when I touch myself there.”
“My dick between your legs feels so much
better than when I touch it myself.”
We continue kissing.
“Are you ready to show me how you touch
yourself?”
“Yeah, I won’t be embarrassed now.”
Emma places her left index finger one
knuckle deep in her vagina and rubs her
nub with her other hand. She starts
slowly, increases the tempo then
suddenly whimpers, then groans and
finally yelps.
After a minute or two:
“Do you have a condom?”
“Yes.”
“PUT IT ON.”
“Emma, let me put a finger inside you to
check the size of the opening.”
“That’s okay, I do that all the time.”
One finger, then two fingers, then I try
three fingers, gently stretching her so
I don’t hurt her when entering
“You’re barely a virgin. This won’t be
difficult.”
I kneel between her legs, bring the tip
of my erection to her opening, and
plunge in.
Emma looks startled, then laughs.
“Why did I dread this for so long?”
“You had been misled. Are you ready for
more?”
”Oh, yes.”
“Tell me if this hurts.”
I start going in and out slowly with
short strokes.
“Rub your clit.”
“Now?”
“Yes.”
I send her over the edge when I fill my
condom.
After I slip out of her, she grins,
looks at me:
“How soon before we can do this again?”
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