sexstories.com

Introduction:

Yes, the name is a terrible play on a TV show name, forgive me. I plan on this story arc being a slow build up, bear with me.

“Oh my god, what are you two doing?!” my mother shrieked.

I looked up, dumb with shock. Unfortunately I was precariously perched above my sister, her legs on my shoulders. Even more damning, my cock was quite visibly sticking halfway inside of her, though at sound of the door flying open and the shriek that followed, all the blood in that particular extremity was doing its utmost to return to more pertinent areas of my body, such as my heart which had decided to get a head start on the marathon it’d evidently decided I was about to run.

But let’s back up a bit, a lot of things happened before this point. They say that when you’re about to die your life flashes before your eyes, let’s call this that.

Let us begin at a time when all was still right in my world, say eight or nine months prior to what shall henceforth be referred to as “the incident.” We can start with the basics. My name is Jason. My sister, whom I introduced earlier as an anonymous pair of legs, is named Kimmy. My room does not have a lock. My mother has a habit of not knocking. Those things will come to haunt me later, but for now, they are just random facts in the tapestry of my life. In the less hectic timeframe we are revisiting I am sixteen.

I’d just gotten my license a few months back, roughly two weeks after my birthday. This was, unfortunately, cooler in theory than in practice. There was no car I could drive, I couldn’t buy my own, and I couldn’t afford insurance even if some distant relative keeled over and left me a 1957 Mustang. I mention this only because it explains a bit about what happened next. And because I continue to wish, with no ill will toward anonymous hypothetical relatives, that someone in the family would die and leave me the aforementioned car.

It was lunch time at school. The cafeteria was cordoned off into groups of cliques. To sit at a table with whom you did not click was to invite ridicule and shame. But these are not things that a bold young man fears. The homecoming dance was taking place in three weeks. Despite my best efforts, I still didn’t have a date. Ridicule and shame was one thing, but imagine the consequences of going dateless?

With as much courage as I could muster I walked across the cafeteria towards an exclusively female table. Sitting in the middle of this gathering was an angel with blond hair. Her name was Lisa. In my eyes she represented everything that was perfection. Her butt looked perfect in her jeans and her lipstick was colored on inside the lines. She was a sophomore. I was a junior. That meant I was the cool one, right? That was my mindset as I approached her anyway.

“Lisa? Can I have a word?” I asked in a voice that was, perhaps, a shade lower than was naturally honest.

“Do I know you?” she asked. The girls around her giggled in a coordinated attack on my cool.

“No,” I answered, “but I hope that won’t stop you from going with me to the homecoming dance.” The surrounding giggles reached an entirely new pitch.

“No way, Lisa, he doesn’t even have a car,” said a voice. I looked over to identify my antagonist. I was expecting horns and a pitchfork, but instead I saw barrettes and lip gloss. Kimmy. The barrettes held waves of curly red hair in check. She had a pouty mouth which was twisted in a smirk. The twinkle in her blue eyes might have been attractive in other circumstances, but certainly not then. I stared daggers at her, but they were easily deflected by the impenetrable layer of smug that surrounded her.

“Uh… sorry, I, um, already have a date,” Lisa lied awkwardly.

“Oh, yeah, don’t worry about it,” I replied a little too quickly. I gave Kimmy one last glare and stalked off to an empty table. There I sat and brooded.

“Aw, did you get shot down?” Kimmy asked in simpering voice as she sat beside me. She was only a year younger than me. Unfortunately for my love life, she also had the same lunch schedule.

“You know, you really can be a bitch sometimes,” I said.

“Hey! I’m a lady, watch your mouth, you remember what dad always says,” she warned with a passable impression of dignity. My dad was very much in the women-can-do-no-wrong camp. But I was no such knight in shining armor. I couldn’t have afforded the horse insurance anyway.

“A lady? Don’t they usually have…,” I leaned forward and made a show of unzipping Kimmy’s hoody, “breasts?” She smacked my hand away.

“For your information, I have perfect breasts. And anyway if it weren’t for the internet you probably wouldn’t even know what breasts looked like. You definitely won’t be seeing boobs anytime soon if that back there was the best you can do.”

“I’ve seen plenty of boobs,” I muttered. “And what was wrong with my pickup line? I just asked Lisa to the dance. I think what really bombed me back there was your insult dropping.”

“Please, with Lisa? You had no chance, I just saved you from getting really awkward. You need to stay in your own league.”

“Whatever,” I said. “We’ll see how you handle it next year when you can’t find a date to homecoming.”

“I’m sure I’ll cry myself to sleep. But at least I’ll have memories of this year’s dance to help me through it,” she replied.

“What?!” I nearly yelled. “Who are you going with?”

“Brad Inman,” she said with a smirk.

“That loser?” I said with contempt. Brad was junior like me, but he wasn’t one of the cool kids. Not that I was exactly cool either, but I didn’t spend my free periods battling other nerds with playing cards.

“Hey! He’s got a car. That’s pretty cool in these circles. And he’s got a date. Between the two of you I think he’s winning,” she said.

“Well sure, I could get a date too, let me go ask the next flat girl who’s willing to put out for a ticket to the dance, I’ll let you know how it goes.” Even as I said it I knew it was a step too far. I was mad about Lisa, but Kimmy had been right, it was a long shot that I’d have gotten a yes either way.

“Asshole,” Kimmy said, in a voice that actually sounded hurt. She got up and left the table in a hurry.

“Kimmy!” I called after her, I wanted to try and apologize, but she was having none of it. A passing group of students masked her exit and I lost sight of her. The odds were very good that I’d pay for that one later.

I don’t know if it was the guilt, or some heretofore unknown feeling of fraternal protection, but my mind suddenly drifted to Brad, who also happened to have the same lunch schedule as me. My eye wandered to a table in one of the corners of the cafeteria. It had an assortment of odd students, those who sought haven together as they didn’t belong to any of the more established cliques. Cards were haphazardly spread across the tabletop, food having long since given way to the real priorities at hand. Sitting behind one of the large assortments of cards was Brad. He had glasses and medium length blond hair. Truth be told he didn’t look the part of a stereotypical nerd, really he looked downright average. It seemed to be his love of nerdy pursuits that so firmly entrenched him in this role.

I wandered aimlessly for a little bit, exchanging greetings with some passing friends, but eventually I found myself drawn toward the card strewn table. Brad was in the middle of some kind of intense battle as I approached. There was a rapid back and forth between him and his opponent. They seemed to know their cards well, I’d give them that. Whenever one would throw down a card the other would know exactly where to look in his deck to find some counteracting stratagem. Nerds.

I poked Brad’s shoulder to get his attention. He nearly flung his deck across the table.

“What?!” he asked angrily.

“Can I have a word? Out in the hall?” I asked.

“Can’t this wait? This is a ranking match. And he’s a cheater!” Brad hissed, pointing at his opponent.

“That was never proven!” his opponent shot back.

“Look, I don’t care about your stupid match, we need to talk, now,” I said.

“Fine,” Brad said in exasperation, “but I’m taking my cards with me. You hear that? You can’t peek at them, cheater.” Brad and the nerd across from him traded a few more heated comments before he followed me out into the hall.

Exiting the cafeteria cut the ambient noise down appreciably, the hall was almost deserted.

“Well, what do you want?” Brad asked.

“I heard you were going to the dance with my sister. I just wanted to tell you not to try anything, and you better be nice to her,” I said with a stern accompanying gesture.

“Whoa, you’re Kimmy’s brother? Listen, I… uh, actually I’m not going with her. Could you tell her that?”

“What?!” I shouted.

“Well, I’m going with Mort’s sister instead,” he explained.

“Mort? Isn’t his sister the one with the pig-nose and buck teeth,” I asked incredulously.

“Yes, that’d be her,” Brad confirmed.

“My sister is way hotter than her! Ok… that sounded weird, but come on, man.”

“Yes, that’s true, but Mort is trading me a very rare—“

“Wait…,” I cut him off and placed a hand over my face, “you’re dumping my sister for a pig-girl and some playing cards?”

“Limited-edition playing cards,” he corrected. My anger got the better of me -- I pushed him back against some lockers.

“Get off me!” he shouted. His face had grown red and splotchy and he shook with a nervous sort of rage. “You stay the hell away from me, you and your skanky sister!” He hurried back into the cafeteria before I could get my hands on him again. I was certainly no saint, but Brad had some seriously bad karma coming his way. And if karma didn’t get around to balancing things out maybe I’d help it along if I got the chance.

But that was the least of my worries. How was I supposed to tell Kimmy that her date had dumped her? She was already pissed at me.

***

Kimmy managed to avoid me the rest of the day at school. I hung around her locker during passing periods, I even tried texting her. Nothing. I didn’t even catch her on the bus, she must have gotten a ride home with someone.

It wasn’t until that evening that I heard her door close. I’d been sitting in my room, ruminating over the same math problem for at least twenty minutes. Every time I forced myself to focus I’d get halfway through it and then my mind would wander back to my inevitable confrontation with Kimmy. How would I say it? How would she take it? And before I knew it I’d be starting the problem all over again. It was almost a relief when I heard her come in. I set the notebook and pencil down. I’d have to finish it in the morning -- something told me I’d be in no mood for homework after this.

I knocked on her door.

“Just a second,” came her muffled reply. That was probably the nicest thing she was going to say to me all night. She opened the door. The barrettes were gone from her hair and a thick lock of it hung down, covering half of her face. As soon as she saw me her eyes narrowed and her lips compressed. “What do you want?”

“I… uhm… well, first, I’m sorry… for today,” I half mumbled. I readily admit that I was in the wrong, at least intellectually, but emotionally, well, it was galling to give such of show of submissiveness.

“Go to hell, I don’t need your apologies. Seeing your face when my date picks me up, knowing you’re sitting at home alone during the dance, that’ll be enough for me,” she spat.

Deep breaths, I told myself. Remember to be kind, she had bad news coming. I think some small part of me was happy to deliver the news given the epic levels of bitchiness Kimmy was striving to achieve. That small part of me was, however, vastly outweighed by the rest of me which feared getting my butt kicked by a hundred pound redheaded girl.

“Yeah… about that. I, uh, talked to Brad. He told me to tell you that… something came up, he can’t take you,” I finished lamely.

“Hah, is that the best you’ve got? Is the president on the phone too? And speaking of Brad, I should call him,” she replied and then slammed the door in my face.

Well… this would be awkward. I heard a brief and muffled conversation through the thin bedroom door. The volume seemed to grow proportionately louder the longer the conversation went on until it reached a climax that I was pretty sure was Fuck you. This was followed by silence.

The door opened once again and Kimmy stood there looking at me. At first I thought she was going to yell at or slap me, anything except what she actually did. She started crying. Aside from injuries I don’t think I’d ever seen my sister cry, once she was out of diapers anyway.

“You… you were telling the truth,” she said between sobs.

“Yeah, look, Brad’s a jerk. You’re better off.” I awkwardly put my arms around her and she returned the embrace with far more certainty than I had initiated it.

“All my friends have dates. I’m such a loser. I’ll be the only one who doesn’t go,” she sobbed.

“Hey, it doesn’t look like I’ll be going either, and I’m a junior,” I said reassuringly.

“Oh like hell, you’ll get a date, you’ve got half the sophomore girls in the school to pick from, idiot,” she said without any real menace.

“And you’ve got half the upperclassmen in the school. And I seem to recall somebody saying something about perfect breasts, those are pretty useful when looking for dates, you know.”

“Shut up!” she said. But then she kissed me. It was an entirely ambiguous kiss, too long to be a chaste peck and too short to draw conclusions. As I stood there dumbfounded the door closed and she was gone again. I went back to my room and sat down at my desk once more. I tried returning to the math problem but found myself distracted for entirely new reasons.

***

The next morning Kimmy acted like nothing had happened. And maybe that was the truth, maybe nothing had happened. I was probably just reading too much into the kiss. What did that say about me? It said I really needed to find a date, I think. Unfortunately it was Friday, which meant that another week had passed and I was no closer to finding my ticket out of loserville.

Later on at school I was standing at my locker. It was a passing period and I needed to drop off a few books.

“Jason?” I turned around. Standing behind me was a girl I’d never seen before. She had blonde hair that was drawn back into a pony tail. When she spoke I could see that she had braces as well, though a more subtle kind than some and frankly they looked cute on her. She was a good bit shorter than I was, my best guess was about five foot two, maybe three with shoes.

“Yes?” I finally replied.

“Your sister told me you didn’t have a date to the dance… and well…” she lowered her amber eyes to the floor.

“Ah, listen, I’m sure you’ll find a guy that wants to take you to the dance, I was kind of looking for someone that it would actually be a, well, date with, not just someone to go with,” I said, mentally kicking myself even as I said the words. I might regret this another week or two down the line when desperation took hold.

“No! It’s not like that,” she exclaimed. “I think you’re cute. In fact, I was wondering if we could do something tonight… you know, like a date,” she looked up at me shyly.

“Sorry, I just kind of assumed, and well… Alright, sure, let’s do something. I, uh, well my sister probably told you, I don’t have a car, so my options are kind of limited… What did you have in mind?”

“I was going to see Kimmy today anyway, and I just got a new movie, you want to watch it with me at your house?”

“Sure,” I said, hoping my relief didn’t show on my face. On the bright side I was pretty sure I’d set a new record in awkward, maybe I could call the world record people and get my face plastered beneath a headline that read World’s Most Awkward Guy. That would make the ladies swoon, I’m sure.

“Great! My name is Sam, by the way, see you tonight!”

We could go on through the rest of my rather boring day but instead let’s just go over the highlights. I had a pop quiz, I found five dollars in an old pair of pants when I went through my closet, and my mom made cookies.

***

Sam showed up at my house around six that evening. I wasn’t sure exactly how much Kimmy had to do with all this. Had she tried to set me up with a friend? Maybe she had merely mentioned my desperate dating situation in passing and her friend saw an opportunity. How awkward this evening could turn out seemed to hinge on the answer to that question. But seeing as Sam was willing to show up here where Kimmy was almost guaranteed to be suggested that it was more of a fix up.

It was a little weird to think about my sister setting me up with someone, I’ll admit, but it was better than getting shot down day after day. There’s only so much a guy’s ego can take until sweatpants and a basement start to sound like a good retreat from the cruel outside world.

The question of Kimmy’s involvement went unanswered for the moment, she hadn’t come home yet, which left me and Sam alone. My father was out of town for work and my mother was out running some last minute errands. I raced down the stairs from my room to answer the doorbell.

“Hi” I said, opening the front door.

“Hi,” Sam replied.

“Oh, um, come in, please.”

I awkwardly stepped out of the way and she stepped in, slipping her shoes off by the door.

“I brought the movie,” she declared, holding up a case. It had pictures of giant robots on it.

“Great, we’ve got a player down stairs, and I’ve got one up in my room,” I offered and then blushed a bit as I realized the implications of the latter. I might as well have invited her up to my room for a cup of coffee while I was at it. That’s me, as smooth an operator as has ever prowled the dating scene.

“Oh, you’ve got a TV in your room? Nice. I always love to see people’s bedrooms, it can say a lot about a person. Sorry, that sounds weird doesn’t it?”

“No, not at all. My room’s right up stairs, follow me,” I said, relieved she hadn’t taken my offer the wrong way.

I led her up the stairs and into my room. It was the first door on the left, just before Kimmy’s door. I flipped on the light switched and grimaced at the state of things. There were a few dishes stacked on my desk and dirty laundry was strewn about the floor. Why hadn’t I cleaned up? Well probably because I hadn’t expected my first date with Sam to be in my bedroom, of course. Maybe it was a sign I needed to start being more optimistic about these types of things. I hurriedly picked up a few pairs of jeans and tossed them in a hamper.

“Sorry about the mess… I, um…” I trailed off. There really wasn’t a good excuse.

“My room is way worse, don’t worry about it,” Sam said graciously.

She hopped onto my bed which was the only real piece of comfortable sitting furniture in the room, aside from my desk chair. Across from my bed was a thirty-two inch television, my pride and joy. Well, it was my pride and joy until I could manage to get a car, anyway. My parents had given it to me for my last birthday, that and the bluray player that sat under it.

“Nice setup,” Sam said admiringly. “My parent’s won’t let me get a TV in my room, they say it’ll interfere with my studies or something, it’s lame.”

“Yeah, I got a stern warning that it’d be the first thing to go if my grades slipped. I mean, come on, will watching a movie in here really keep me from doing my homework?”

“Exactly!” Sam agreed.

I took the movie from her and slipped the disc into the player. I flicked off the light and grabbed the remote. A few button presses later and giant robots and monsters were fighting an epic battle in earnest in thirty-two inches of high definition goodness.

“Sorry if you’re not into this kind of thing, I just thought it looked like a fun movie,” Sam said.

“Hey, anything with giant robots has to be good,” I said reassuringly.

“Right?” Sam smiled at me.

At some point during the first half of the movie Sam had leaned over against me. I was almost scared to breath, as if that slight movement might be enough to make her realize what she was doing and send her scurrying off to the farthest end of the bed.

“Oohh, check that out,” Sam said, pointing at the TV as a robot whacked a particularly nasty monster around with a cargo ship.

“I know, poor monster,” I said, deliberately misinterpreting her comment.

“No way, they deserve it!” Sam countered.

“Why, just because they are ugly? Because they eat people? Monsters have to eat too, you know!”

“Then they should work for it like everyone else, I strongly believe in smacking monsters around,” she said with a tone of finality.

“Then I’m afraid we’ve reached an impasse. I just don’t know if I can take a girl to the dance who feels no sympathy for the plight of giant monsters and their robot oppressors.”

Sam’s response to this was to whack me upside the head with my own pillow.

“Rawr!” I replied, moving my hands in what I thought was an appropriate monster fashion.

“Ah, you leave me no choice, Jason-zilla, I have to save the town.”

She leapt at me, pillow in hand. I fell back and she landed on top of me. Things seemed to slow down for a moment. How had I ended up here? Laying there with a beautiful girl sitting on top of me, and in my own bed. And then time abruptly sped back up and the pillow in her hand came down with a whap, hitting me in the face.

“Oh my god! I’m sorry! I thought you’d catch it,” Sam said, yanking the pillow away.

“Sam? Is that you? I can’t see,” I said, waving my arms blindly, my eyes closed.

“Hold on, I can fix this!” she said and leaned down over me, and I felt her lips touch each eyelid in a gentle kiss. “All better?” she asked.

I opened my eyes to find her face very close to my own.

“All better,” I repeated.

I don’t know who moved first, but suddenly the movie was forgotten and there was nothing but my mouth and hers. Our tongues twined, my hands found her body and my awareness seemed to leave my mouth and travel to my fingertips.

In our mock tussle her shirt had ridden up a little, and the pads of my fingers found the warm, smooth skin beneath. I ran my hands under her shirt and up her back and her hands laced through my hair, pulling me closer. I felt my erection pressing almost painfully against her leg as we kissed, fortunately she didn’t seem to mind.

What she did next showed me that not only did she not mind, she approved. One of her hands had detached from my hair and wrapped around my jeans-cloaked member. She squeezed gently. I could feel a spot spreading on my jeans where precum oozed from my cock.

Sam fumbled with my zipper and suddenly my cock was in her bare hand. I kissed her with redoubled passion as she gently rubbed. Her lips traveled across my jaw and to my neck. Each press of her warm lips made my cock spasm in her grasp. I could feel the warmth of her breath on my skin.

And then I felt her teeth nibble on my earlobe. It was too much. Though I would have given much to stretch the encounter out, this sent me over the edge as she must have guessed it would. My cock jerked in her grasp and cum shot up to a crazy height above us. In the uncertain light of the television I guessed it went some four feet in the air before spattering back down. Just as another spurt of cum jetted forth my door opened.

Now I know what you’re thinking – if this guy is always getting walked in on, why the hell doesn’t he get a lock? Or a motel room? Well, first, my parents wouldn’t let me. As for the second, I didn’t have the money. And lastly, it was not my mother who walked in, it was Kimmy.

“Hey Jason I heard you got a—Oh, um, I…” she seemed entranced for a moment as an arc of cum shot out and landed on Sam’s hand. Then she turned and walked back out of the room, shutting the door again behind her.

“Oh, wow, that was awkward,” Sam said, though bless her she kept rubbing until my cock had finished its business.

“You didn’t tell her you were coming over?” I asked, as soon as I’d recovered.

I knew I should really feel embarrassed by my sister seeing my cock, and what’s more seeing it in the act, but at the moment, I was still relishing the pleasant feeling that seemed to permeate my being. I’d leave feeling embarrassed for later when I had to look Kimmy in the eye. And besides, she’s the one that walked into my room without knocking, it almost served her right.

“Well… no, I told her I was going to see if you wanted to go to the dance, but… she didn’t know I had a crush on you,” Sam confessed.

“Ah well, maybe next time she’ll knock,” I said and kissed her.

I had a date to the dance and now it looked like I had a girlfriend. Life was good. Well, for the moment. Obviously things didn’t go as planned, as my introduction made obvious. How things went so weird so fast with Kimmy… well, we’ll get there in due course.

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