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Intern Affair
Feeling the last of the pulsations flow through
his cock, the last bit of cum draining deep into
Tonnie and the inevitable shrinking of his
manhood he couldn't help but think, "I've failed
her again." As he caught his breath, his cock
slipped out of her wet, unsatisfied cunt and he
groans, "I'm sorry Tonnie."
Sliding off him, she quickly straddles his thigh
whispering, "It's okay, I'll just finish here."
She begins pushing her pussy against his thigh,
lubricated by his cum as it oozed from her.
"Fuck," he thought to himself, "I fail her and
she doesn't even realize it." Not sure if that
was a good or bad thing, he reached up and
cupped her tiny breasts, one in each hand. Using
his thumbs to tease her nipples, he tried to
speed her orgasm, since her grinding was now
beginning to make his leg ache.
Finally, she cried out, "Oh yes, yes... ahh,"
ending with a feral growl and collapsing down
onto him. Remaining still while she recovered,
he could feel the cum running down his thigh and
undoubtedly onto the bed sheets. They started on
a towel, but her move onto his thigh moved the
mess onto the bed.
"I just love lying in your arms like this," she
said. "Let's just spend the whole afternoon
here."
Wondering if she had left a bruise on his thigh,
he merely groaned in response, hoping the
feeling would come back to his foot so he could
get up. Letting his young lover relax on him he
pondered his situation. When he first started
seeing her, she was fresh out of college,
working at the company as an intern. As his
business lunches with the group of interns
slowly migrated to lunch with just her, he
promoted her to be his personal assistant.
That soon progressed as lunches became small
outings as he took her to some of the art
galleries in the area, all in the interest in
her professional development. Although he never
tried to seduce her or anything during this
time, they did get closer on a personal basis,
discussing increasingly personal details of
their lives.
In the course of her development, she learned of
his disastrous sexless marriage. Granted his
extra-marital dalliances in the past basically
created the situation, but he was cautious about
the real dirty details, letting Tonnie think the
problem was all because of his wife.
While divulging a one-sided look into his
private life, he was rewarded with some
interesting details about his young associate.
The one that interested him the most was that
she was still a virgin. Remembering his younger
years, he had never had a chance to deflower any
of the girls he slept with; most of them had
been more experienced than he had. Even his
wife, he learned years after he married her, had
much more experience than he did, even then.
The thought of introducing sex to a young woman,
guiding her on a journey of sexual enlightenment
intrigued him. Here was a chance to be the
teacher, the one to introduce her to all the
possibilities her young body held inside. He
began putting together a plan to initiate sexual
contact with her.
It was only a short time later that an
opportunity presented itself. A convention in
Atlanta would give him the perfect set of
circumstances to seduce his protégé. It was not
unusual for assistants to travel with their
bosses on sales trips and conventions, so he
scheduled Tonnie to make the trip with him.
This trip was her first business trip, so he got
a real kick out of her exuberance during their
ride to the airport and the wait at the
terminal. She was a non-stop blur of energy, as
she checked their email, made a few business
calls, chased down some coffee for the both of
them and then generally just barraging him with
non-stop questions about the convention.
He just took it all in, hoping that this
excitement would carry over into the bedroom.
When they arrived at the hotel, she didn't have
any problems when they suddenly discovered her
reservation was strangely "lost" and she'd have
to stay in his suite in an adjoining bedroom
instead of having a room to herself.
"This will work out well, if you need anything
I'll be right there," she said, "Much more
convenient than if I was in another room."
From that point onward the seduction was on, as
he took her to a romantic dinner at the posh
roof level restaurant in the hotel, making sure
she had plenty of wine. Afterwards, they visited
the jazz club downstairs where he danced with
her a bit, and basically treated her like a
princess all night long.
They returned to the room a bit before midnight,
but before she could head to her room he held
her hand and pulled her closer to him. Gently
brushing her brunette hair back from her eyes,
he slowly tilted his head and softly kissed her
lips, pausing there long enough so it was clear
what the kiss was about.
Pulling back from her, he gazed into her eyes
and seeing she was receptive, he leaned in and
kissed her again, this time slipping his tongue
in between her lips and toying with her tongue.
He drew her against him and continued to kiss
her, letting her feel his erection grow against
her.
After a few moments he reached up under her
hair, unhooked her dress and began moving the
zipper downward. She was motionless, letting him
carefully remove her dress and arrange it over
the chair. He quickly pulled off his clothes,
while she stood silently, watching his every
move, her eyes locking on his hard cock as he
pulled off his underwear.
As he moved toward her, she continued staring at
his cock and said, "I've never..."
Touching two fingers to her lips he whispered,
"Shhh... I know. I'll be gentle."
He stepped into the restroom and came back with
a towel and condom. Placing the towel on the
bed, he then tore open the wrapper so the condom
was readily available and placed it on the edge
of the towel.
She had already reached behind herself, removed
her bra and then slipped out of her panty hose,
finally standing before him in only a lace
panty. He guided her backwards to the edge of
the bed, where he kneeled on the floor and
daintily removed her panties, watching her sit
on the towel as she stepped out of them.
He paused a moment to look over this young
woman. She was not the most attractive of his
recent conquests, but her innocence more than
made up for the minor deficiencies. Her breasts
were not large, and the nipples and areola were
just a faint pink, almost indistinguishable from
the color of the rest of her breasts. The
nipples did stiffen up nicely, looking almost
something that could poke out an eye.
Noticing her shivering a bit, he leaned forward,
opening her knees and sliding between them, so
he could reach around her waist and hold her.
"It's okay, we'll go slowly," he assured her,
kissing her belly and then descending through
her curly triangle of hair to her pussy. Just
the thought of slipping his tongue inside her
and tasting her fresh cunt had him feeling a bit
dizzy, but he continued pushing his tongue deep
inside her.
He could hear her breathing hard as he reached
his hands up to her breasts and pushed her back,
so she could lie on the bed. Sliding his tongue
up the length of her slit he found her clit and
slowly ran his tongue in tiny circles over it
while moving his hand back down between her
legs. Carefully working a finger inside her, he
moved it up against the top of her cunt trying
to stretch her hymen a bit.
Wanting to open her up as much as he could
before penetrating her with his cock, he
continued working two fingers in and out of her
as he kept his tongue working on her clit. It
wasn't evident if his fingers were causing any
pain and in a few moments more, he could feel
her lift her hips in unison with her fingers.
She came quickly and noisily, crying out
something he couldn't decipher. Leaving his
fingers inside her, he felt her pulsate around
them, moaning the entire time.
"Oh God," she groaned, "I've never felt like
that."
"Is that the first time..."
"Oh no, I've come before, once even with a
boyfriend, but it was nothing like that."
"Did he use his mouth on you?" he asked.
"No, he just fingered me. It was nothing like
this."
Sensing it was time to go a step further he
climbed up on the bed, kneeling between her
widespread legs and asking, "Are you ready to
try a little more."
"Okay," she replied tentatively.
He reached and pulled the condom out of the
wrapper and rolled it down over his cock. "If it
hurts too much tell me and I'll stop," he
whispered in her ear as he moved his cock
against her pussy. "Pull your lips open a bit
and guide it in," he continued.
Feeling her fingers take him, he leaned closer,
slowly easing himself into her opening. He
pushed a bit and then felt a tightness inside
her cunt. Pausing a moment, he took a breath and
pushed harder, feeling resistance and then a
sudden release as he entered her to the hilt.
"Ohhh...," she whimpered.
He paused, looking into her face. A tear had
collected at the corner of an eye and he moved
his mouth to her and kissed it, tasting the
salty liquid. Slowly withdrawing, he noticed her
wince just as the head passed what remained of
the hymen. He then moved forward, thrusting back
into her. He continued, slowly increasing his
pace, noticing her begin to feel something more
than the pain. Soon she moved beneath him,
seeming to enjoy what they were doing.
Though he wanted to make her come that way, he
knew she probably wouldn't this time, so he let
himself go, feeling the sensations of her pussy
on him and just thinking of how he was the first
man inside her inspired him. Even wearing the
condom, with a few more thrusts he felt the
intense pleasure roll down his shaft and he
spurted his cum into the condom, his cock buried
deep inside her.
Recovering from it all he looked back at her
face and noticed she was silently crying. He
immediately held her head between his hands and
said, "Oh no, does it hurt that much?"
"No, no. It hurt a little, it's just, it's
just... well, what we... my first...."
"Shhh... it was so beautiful," he said kissing
her lightly on the lips and then kissing her
face all over, collecting the tears as he went.
Withdrawing from her, he carefully removed the
condom and laid it on the towel. There was some
blood, but not a lot, all caught in the towel.
Looking back on it all, it was a beautiful
thing, he thought, trying to wiggle out from the
now sleeping woman. He was finally getting some
feeling back in his foot after her humping his
thigh and he wanted to limp off the pain.
"Hmmm, you awake?" she asked.
"Yeah, go back to sleep," he whispered, still
trying to wrestle from beneath her.
"You didn't even fall asleep did you?"
"No, I was just thinking," he answered.
"About what?"
"I was thinking about that first time, our first
time... your first time."
"Oh yes," she said, kissing him passionately on
the lips, coming up for air she continued, "You
know how much that turns me on: you thinking
about that?"
Her hand grabbed his cock, but seeing it still
wouldn't be ready for a while, she changed her
plan, getting up on her hands and knees and
tossing one leg over his head and lowering her
pussy onto his face. "Damn," he thought, "this
girl's gonna kill me." He turned his head and
took a deep breath before moving back and
plunging his tongue into her recently fucked
pussy, thinking about the virgin taste of her
just a few months before.
Fighting her for each breath as she ground
herself on his mouth, he wondered what it might
be like with a more mature woman, where you
could just have sex once and then go to sleep.
He thought to himself, "Somehow I've got to
figure a way to get out before she kills me.
I've got to figure a way to leave..."
She ground her pussy onto his face, her juices
wetting him thoroughly. Trying to concentrate on
her clit, her movements took over and soon she
was basically grinding over his face much like
she did to his leg. All he could do was fight to
catch a breath here and there between her
thrusts. Thankfully in just a few more moments
her heard her loudly exclaim, "I'm coming, I'm
coming."
Climbing off of him, she noticed him panting,
trying to catch his breath. Kissing his face she
exclaimed, "I love it that this turns you on so,
look at how you're breathing."
"Yeah, it's so exciting," was all he could say,
wondering how much longer he could take all
this.
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