My First Time

Poor Kaity

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Poor Kaity
The world's most awkward school girl.

Based on

a post by NiceDayReboot. Listen to the Podcast at Steamy Stories.



Kaitlyn was

a charity case, and I knew it. Of course, I always held a sense of guilt about
that knowledge because I had to keep her from figuring it out. Oddly, for how
often I'd acted as a surrogate older brother to her, she was a year older than
me at nineteen. She'd been held back at least once to my knowledge, making her
a junior when I was enrolling in college full time. Kaity was a bit distraught
at the thought of me moving on and leaving her to fend for herself in her
remaining two (given her track record, possibly more) years of high school.

I should

probably point out that this wasn't her fault. She had some kind of condition
that left her both a little slow on the uptake, and bafflingly naive when it
came to social situations. I would have assumed Asperger’s or something,
but she wasn't actively antisocial. Far from it, she actively threw herself at
people with a witless enthusiasm that generally drove anyone with a sense of
self-preservation away. Add to that a conservative, very religious upbringing
and a complete inability to detect sarcasm, and it became quite clear how she'd
made it this far without friends to speak of, to say nothing of a boyfriend.
The few friends she did have were the type of socially unconscious girlfriends
you'd pick up through Sunday school, with the Christian charity to befriend the
poor dear and self-righteous enough to be persona non grata in any of the
popular social circles. For all the effort she had put into acquiring a
boyfriend, she couldn't seem to think of a use for one aside from holding hands
and filling in the required space on a well-adjusted high school student's
checklist. The few boys new and ignorant enough to accept her attentions
generally called it off after an awkward day or so, going on to insist that it
had never happened should anyone bring it up in the future.

Which left

me. When I came to high school as a sophomore, transferring in from another
school, I'd also been met with her amorous attentions within a week of my
arrival. Unlike most of her usual victims, I had the foresight to turn her
down. However, I'd used the "Let's just be friends" approach I'd
found effective at warding off unwanted advances in the past, citing that I
didn't know her well enough to date her. Kaitlyn took that literally, to the
point where I was abruptly transferred from potential token boyfriend to Best
Friend Ever without much say in the matter on my part.

Now I might

be genuinely antisocial. I don't hate people, per se. I just often find better
things to do with my time. So it was no small amount of trepidation that I
faced her daily enthusiastic greetings, surprise hugs and torrential reports on
anything that might have happened to her in the space of her attention span,
which was mercifully brief. I have to admit it was a bit embarrassing to be
greeted every day by my name squealed at the top of her lungs, usually
accompanied by a cheerfully spastic wave and an intense hug whenever she got
within range. But I wasn't trying to impress anybody, so I endured it with as
much friendliness as I could muster. Besides, she did squish pleasantly against
my chest whenever she hugged me, a pleasure somewhat mitigated by a habit of
forgetting to wear deodorant at least twice a week. Still, I often had to
dispense chaste "side-hugs" lest certain anatomical reactions betray
exactly how I enjoyed them.

My own

peculiar scholastic situation meant I only saw her at most twice a week,
spending the rest of the time in advanced or college level courses, to which I
was consigned despite my relative antipathy to studying. I may be a smartass,
but I never put much work into it. I owed most of my advancement to parents who
were constantly jockeying to have their "genius son" skip grades,
take advanced courses and whatever legal or illegal means would put me further
ahead of my peers. Despite that, it became pretty clear to me that I was
probably Kaity's only real friend. She never seemed to notice, but most people
went out of her way to avoid her. I couldn't really blame them either, I just
happened to be more susceptible to guilt than most, and letting her putter away
in all the wrong directions was easier than possibly hurting her feelings by
telling her how to fix herself. In hindsight, she may have been aware of the
situation to some degree, but I don't think her position really dawned on her
until her nineteenth birthday.

She invited

me, of course. She must have ended up inviting half the damn school. I was
wondering how she was going to cram all of these people into her house, let
alone feed them. It was supposed to be a pizza and pool party in her backyard
and she was expecting twenty or thirty people. So, when I rattled up her
driveway in my battered Mazda, I was a bit confused by the utter lack of
people. The confusion slowly turned to horror as I figured out what was going
on. It became pretty obvious as I let myself in that I wasn't just the first to
arrive: I was the only one to arrive. Kaity perched forlornly on a bar stool in
front of a counter laden with full pizza boxes, cake and assorted party snacks,
none of which had been touched. Her mother busied herself non-nonchalantly
about the kitchen, apparently unwilling to risk disturbing her daughter more
when she was obviously upset. I caught sight of her younger brother gazing
longingly at the food, wondering if it was ok to begin eating with no party
guests in sight. At the risk of embroiling myself in what was obviously an
awkward situation, I spoke up.

"Hey

Kaity! Sorry I'm late. Where's the party?" She perked up a bit as I
announced myself, and I caught a grateful glance from her mother as I tried to
salvage the occasion.

"No one

is coming." She let a bit of her melancholy show through her happiness at
seeing me, "My friends all had more important things to do than come to my
birthday,"

My eyebrows

rose involuntarily at hearing Kaity of all people resort to sarcasm.
"Well," I retorted, "To hell with them then. I know I'm worth
ten or twenty of them on a good day, so why not have a party of our own?"
I punctuated my declaration by leaning down and lifting her unruly dark hair
out of her eyes, giving her my best devil-may-care grin.

She

responded about at well as I could have hoped, giving me a hopeful smile
through tear-reddened eyes. "Okay."

Her mother

took advantage of the distraction immediately, shooting me another thankful
glance as she took charge, "Let's just have dinner then, we can go out
back later, maybe break out a movie or something once it gets dark out."

Despite the

poor turnout, I felt like I'd managed to bring enough life back into her for
the family to pick things up. We gathered round the pizza for her mom to say
grace. We talked more than ate, for once I felt like an actual friend, and a
bit more human than I'd felt in a while, struggling to help my naïve little
friend through the realization that most people didn't really want to be around
her when it really came down to it. Still, I made sure she had a good enough
time. Even her mother seemed to be in a rare good mood as she snagged some
pizza for herself. He little brother was in hog heaven, going to town on the
overabundant food like a starving man, which should have been a warning sign
that the disasters weren't over.

Not content

with going into a food coma like any sensible child, the little bastard decided
he wasn't feeling well and promptly threw up down my back. I was disgusted and
a bit outraged, feeling hot bile soaking into my clothes and listening to the
middle-schooler hacking up a storm. I might have felt a little sorry for him
had I noticed how red he was getting while I politely excused myself to change
into the swimming trunks I'd brought with me.

While I was

skinning out of my slimed clothes and tossing them into the family washing
machine, I caught some frantic raised voices and the slamming of the front
door. A few minutes later, a soft tapping at the laundry-room door prompted me
to finish pulling on my trunks and call out, "I'm decent."

I had my

back to the door, bent over the washer when Kaity walked in talking quickly,
"Mom's taking Kyle to the emergency room. She said it's ok if we used the
pool while she's gone."

Running over

that little non-sequitur, I choked out a surprised, "Wait, the Emergency
Room, why..." before I turned around and abruptly lost all will to
continue. Kaity was standing framed in the door, somewhat dopey smile still
showing on her face, in what had to be the smallest bikini in the county. In
her habitually loose clothing, I'd always assumed she was a little pudgy, but
her current attire was busy banishing such notions, as well as most rational
thought, from my mind. Strips of white fabric with black polka dots did a rather
poor job of covering curvy pale flesh, and I swore I could hear the strings of
her top humming with tension as they tried to restrain the snow-white balcony
which dominated the landscape, and certainly made a fair bid for my attention.
The sudden ringing in my ears drowned out whatever she had to say, forcing me
to stammer out, "I'm sorry, what was that?"

"Oh, I

said he had an allergic reaction to the tomatoes. We got him a special pizza
without them, but he ate the wrong one." She answered, oblivious to the
effect she was having on me.

"Right."

I responded curtly, more like he'd eaten that one and then kept going. "Is
he going to be ok?"

"Mom

got him his epi-pen in time, but he's probably going to have to spend the night
in the hospital again. It's happened before, so he'll probably be fine."
She sounded like she was reassuring me for some reason. "So, you want to
go swim?"

For some

reason cold water sounded like a great idea just then. "Sure." I
responded, regaining some clarity. As long as I just kept looking at her eyes; she
turned around and I lost lock, my eyes dropping lower. I could see the presence
of some baby fat clinging to her belly, but those honestly impressive tits and
rolling hips served to even her out into an hourglass anyway. She was by no
means supermodel thin, but the figure she cut in that bikini was favorable
regardless. A fact that my mind only confirmed as I watched her stride dragging
her bikini bottom between her ass cheeks, revealing more beautifully rounded
pale ass cheek with every step. I barely made it halfway down the hall when the
evacuation of blood from my brain was answered by a swelling elsewhere. My
rising cock twitched, tenting the fabric of my swim trunks too obviously for me
to play off. I fought off a little irrational panic as I tried to free it by
tugging at my waistband. No such luck. Please don't turn around I, thought
futilely in Kaitlyn's direction.

Telepathy

not being the most reliable of methods, she chose just that moment to look back
at me with that silly fucking grin. She stopped walking when she saw my
mortified expression, then saw the reason why I looked so embarrassed, her
hands flying up to cover her mouth as she gasped and turned the rest of the way
around.

We both

stood at a loss for words as the awkward pause grew and my face only got more
red. Then again, so did hers.

"Chris;

" She broke the silence hesitantly, "Is that your; your; penis?"
She almost whispered that last word fearfully, and I felt the irrational urge
to face palm.

"Yes."

I said dumbly. "Look, can we sit down for a moment? This is really
awkward."

"Uh,

sure." She very distractedly led me into the closest room, which happened
to be her bedroom, a fact which only heightened my discomfort, although I
didn't want to explain to her why. She sat down on the bed, and I couldn't find
any other place to sit, so I sat on the bed a few feet from her.

By this

time, my erection had decided to tangle itself in the netting of my trunks and,
despite the embarrassment it was causing, showed no signs of backing down.
Especially with Kaitlyn sitting so close and staring at it so fixedly. I tried
to fix it as subtly as I could, given the circumstances, but the stupid netting
only conspired to pinch the head, making me wince involuntarily.

"Does

it hurt?" she asked, and I abruptly wondered if she was doing this on
purpose. I managed to mutter an apology.

"Sorry,

it's like this being a guy. Sometimes you see someone; something and it's kinda
got a mind of its own."

"So; I

did that?" She asked with some amazement, once again leading me to believe
she was fucking with me.

"Yeah,

I mean, sorry. I don't think of you like that or anything, it’s just
you're very attractive and..."

She cut me

off, this time she was blushing, "I'm attractive?" She seemed genuinely
surprised that I'd admitted it.

Taking a

refuge in audacity, I responded, "Well yeah, when you come around wearing
that, and with the way it shows your body and stuff." Honestly this couldn't
get any more awkward if;

"Can, I

see it?" she whispered, bringing my train of thought to a screeching halt.
I stared at her mutely for a long moment, before some impulse in my brain
pushed me over the edge. I slid my shorts down around my ankles, freeing my
cock and letting it stand free and in plain sight. I looked at Kaity to see her
go furiously red, bite her lower lip and unconsciously cross her legs.

"Kaity?"

I asked, worried I'd gone too far, reaching over to touch her shoulder. She
twitched in reaction before tearing her eyes away from my erection.

"Looking

at me gave you that?" She said in a tone of disbelief. I was about three
seconds from calling bullshit. There was no way she was that naïve.

"Kaitlyn;

you're a virgin?" She nodded slowly, looking me in the eye. "But you
at least had sex ed, right? Right?"

"No.

Mom called the school when she heard it was happening and got me excused."

Oh. My.

Fucking. God. "Oh, Kaity. So you've never seen a; man naked before?"
Her face answered the question for me, and I noticed her hands clutched
white-knuckled behind her back. "Would you like to touch it?" She
looked at me like a dear in the headlights, a mixture of shock and guilt in her
eyes before she looked back down and extended a hand gingerly towards my groin.
Cool knuckles grazed the curve of my shaft before she pulled her hand back as
if it had been burned.

I gave her

my best patient smile, becoming less embarrassed for me and more for her by the
second. "Here." I took her hand and guided it back to my cock,
wrapping her fingers around my girth and feeling myself shiver at the soft
touch. I looked back at her, "Have you never masturbated before?"

She seemed

too distracted by the feel of my warmth in the palm of her hand to be taken
aback by the question. "No, I; it doesn't feel right!"

Once again I

felt something like pity for the poor repressed girl. I edged closer until our
thighs were together, forcing her to straighten up to keep her hand on my cock,
which she did without thinking.

Fair's fair,

I wrapped an arm around her to cup a tit through the bikini. "Here, let me
show you."

It was her

turn to shiver as I stroked her through the soft fabric, when she didn't
protest, I made sure my other hand found a tit and softly squeezed.
"Stroke my cock a little, Kaity."

She blushed

at the profanity, but her hand started to gently rub my shaft and she
stammered, "Like, this?"

In answer, I

leaned in and kissed her, my lips leaving hers after only a moment to trail
down her jawline before finding the sweet spot behind her ear. A nibble here, a
lick there, and I was rewarded by feeling her breathing increase. Her arousal
manifested in other ways too, as my hands found her nipples beginning to show
through her bikini. I caught one and rolled it between my fingers, and her
breath caught in her throat.

I let my

other hand fall to her lap, only to find myself denied access by her
reflexively crossed legs. "Kaity." I prompted into her ear as my hand
wormed itself between her thighs to stroke her through the fabric. I could
instantly feel the profile of her swelling clit through the cloth, and I
massaged it gently.

Kaitlyn was

still somewhat hesitant in her attentions towards my cock, although it hadn't
stopped swelling the entire time. By now I was almost painfully erect, and
there was no way her hesitant fingers were going to ease that, no matter how
welcome they were.

I disengaged

myself from Kaitlyn smoothly, and she opened her pleasure numbed eyes in
chagrin as I stopped stroking her. I just smiled mischievously, "Lie back
and open your legs." I commanded. She inhaled sharply, looking a little
worried.

"But,"

I cut her off before she could say another word, "Don't worry, just lie
back." I eased her gently down, letting my mouth trail down her body as
she went, latching onto one of her nipples and sucking on it through the
fabric, enjoying the way her arching back drove her down faster.

I

reluctantly released her tit and turned my attentions towards the joining of
her legs, where her tightly closed thighs still denied me access. What was the
old saying? Persuasion is better than force? I kissed her belly button before
driving my mouth eagerly towards her locked thighs, forcing my tongue between
them to feel the swelling of her pussy lips through the polyester. When my lips
found the soft protrusion of her clitoris and latched on like a suckling baby,
Kaity let out an explosive gasp and her legs parted involuntarily. I lifted up
her ass to position myself better, getting my head between her legs before I
began to feast on her slit in earnest. Even through the fabric I could feel
both my saliva and her w

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