Poor Kaity

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 highschool.

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 Aspergers 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 highschool 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 highschool 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.

"Noone 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 too 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-sequiter, 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 epipen 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 breasts 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 buttocks, 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 facepalm.

"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, its 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 dick, 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 breast 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 breast 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 sweetspot 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 breast 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 wetness begin to soak through her bikini bottom as the swelling of her pussy started to engulf the fabric. I decided to speed up the process by tugging her bottoms up so they slipped inside her, pressing down on her clitoris while giving me more flesh to lick and suck. Her hips started to buck roughly against my face, so I pulled the fabric aside and pressed my mouth into her cunt, eager for the flood I was sure would come next.

Kaitlyn didn't disappoint me, wrapping her legs around my head and cumming convulsively, letting wave after wave of delicious nectar find my tongue. I sucked it up greedily, admiring her taste and the musky smell of her pleasure. When she finally released her death grip on my head, I rolled off the bed, dragging her ass down with me. Still somewhat limp from the power of her orgasm, she rolled with it, putting her ass in the air invitingly.

My cock twitching in anticipation, I slid her bikini down off her legs, letting my fingers find and play with her cunt as I balled up the soaking garment and tossed it on the bed. My fingers slipped in and out of her easily, her slick pussy coating them generously, prompting Kaity to moan into the mattress. As I withdrew my fingers reluctantly, she looked over her shoulder dreamily, "Are you going to put it in?"

I grinned at her, my dick in my hand, and started rubbing my head between her pussy lips. "Am I going to put what in?" I asked innocently as I could given the circumstances.

She bit her lip before asking, "Are you going to put your penis in-"

"My what?" I feigned confusion as I pushed my cock between her legs and let it drag back across her pussy. Her cunt was practically twitching, dripping down her leg as she finally grew brazen enough to demand, "Put your cock in me!"

"There's the slut I've been trying to bring out!" I said cheerfully and pushed my shaft slowly into her. She moaned and grabbed handfuls of bedding as I eased in, mindful of her virginity. To my surprise, I didn't meet the resistance I was expecting. There was no sensation of tearing hymen, and she certainly didn't seem to be in pain. Well, I did remember reading somewhere that not all girls lose their hymen during sex. I pushed the distraction aside as I focused on the pure sensation of pushing into her. I started a rhythmic pumping and reached up to drag her bikini down off her breasts, grabbing and fondling them as I pressed into her. She started to push back against every thrust, eager for my cock, seeming to forget her earlier shyness.