(DISCLAIMER: This story is set in a high school. However, everyone involved in this story is at least 18 years of age. Some of the ages are not explicitly given in the text. Let it be explicitly given right now that all characters are at least 18.)
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Senior year of high school is tough for a nerd. You get your fair share of teasing, you're not good at sports, and no one wants to have sex with you. By the time I reached senior year, the extent of my sexual experience was the one time I got a hand job from the only girl trombone player, and she had moved away a year ago.
I was a senior and the closest I had come to having actual sex with a girl was jacking off to Facebook pictures. I'd be ashamed of that, but, I mean, can you blame me? Some of the pictures that girls put up on the internet are practically porn.
In fact, I think I preferred it to regular porn. None of my sexual fantasies were ever about porn stars. They were about the girls that I knew. Fantasizing about a girl I had known for years always got me more turned on than some fake-tit-pornstar that I didn't even know.
There were a few girls that regularly turned up in my fantasies. There was Ashley, a girl in my physics class. She was a ridiculously smart girl; class A nerd like me. She had always been shy and never went to parties or anything. But, during our sophomore year, she started to... fill out. By senior year, her tits were like two full melons bulging against her shirts.
She had never really been a popular girl growing up, but damn did she ever grow up. The appeal of Ashley was that sex with her would be like exploring untreaded territory. She had never even had a boyfriend. I often got caught-up staring at her chest during physics labs, imagining burying my face in her cleavage and titty-fucking her until I came on her glasses.
Another girl I fantasized about was Mallory. This one is harder to explain because I don't even find Mallory all that hot. Mallory belongs to a group of friends that I hang out with regularly. We've all been friends since the fifth grade. I never found Mallory attractive until junior year of school. The reason is beyond me.
Have you ever had a friend that you don't find attractive, but then, maybe just because you've known them for so long, you suddenly want to fuck the shit out of them? That's as best as I can describe it. Mallory and I would usually sit next to each other during study hall. I never got any work done because I was always thinking what it would be like to bend her over the desk and fuck her up the ass right there in the library.
As you can imagine, I spent a lot of my time at school concealing the fact that I had a raging erection. However, at no other time during the school day was this harder to do than during math class. Math was my last class of the day, and I both looked forward to and dreaded it. I dreaded the class because I hate math. I was in the advanced classes for every other subject, but I was in a lower math class.
However, this created a unique opportunity for me. My class consisted of the typical jocks, pretty girls and all around more popular people than I usually had class with. And, one girl stood out in my mind more than all the rest - Kayleigh Spencer. Kayleigh was a blonde bombshell that sat directly to my right.
Kayleigh was popular, athletic, and gorgeous. She wasn't like all the anorexic, sickly-looking girls that most people thought were hot. Kayleigh had curves. Not chubby, mind you. She had curves in the exact right places. She would often wear shorts, and I would lose myself following her long legs up past her thick thighs until I was staring at her ass. Holy shit, her ass. It was a beautiful, full, round ass. Any guy who tells you he's looking for a girl with a small, flat ass is either lying to your face or has never met Kayleigh Spencer.
I wanted desperately to smack it every time she got up out of her desk. I spent hours and hours fantasizing about Kayleigh. During class, I would make excuses to stand up, just so I could try and get a look down her shirt at her shapely breasts. Or, I would "accidentally" drop a pencil so I could bend down and get a view up her skirt on the days she would wear them.
One day when she was wearing a skirt, I glanced over, not actually intending to look at her this time, and happened to see that her skirt had fallen down a little ways in the back. The top of a bright orange thong was exposed, and I actually got a good view of the top of her ass crack. I couldn't believe she was wearing a thong under her skirt. Wasn't she scared someone would see? I sneakily used my cell phone to take a picture.
That night, I must have jacked off three times to it. It seems sort of stalker-ish talking about this now, but it's not like I was dangerous. I was just a horny guy that needed to jack off. I knew I would never be able to actually sleep with Kayleigh. She didn't even know my name. So, I did the next best thing. Our "relationship" consisted of her looking hot and me imagining her sucking my cock.
One day, I decided to look her up on Facebook. Kayleigh's profile wasn't private, so I decided to take a look at her pictures, and damn were they sexy. Some of the best ones were from Halloween. There were all sorts of pictures of her and several of the other popular girls from my high school dressed up in tight outfits that exposed more than enough skin to get me hard. Many of these pictures made their way into my spank bank.
Being a popular girl, there were always rumors floating around about Kayleigh. Most popular girls have rumors about them. Usually, it's a rumor some guy started, saying she gave him a blowjob or slept with him. Kayleigh had these same rumors about her, but some of the rumors people heard about Kayleigh were more hardcore than the average popular girl got.
A football player named Eric said that she was into bondage. An outspoken lesbian had claimed that Kayleigh loved to eat pussy. There was even a rumor that Mr. Boyd, the guidance counselor, had fingered her in his office. Most people were dismissive of these rumors. I didn't believe most of what I heard about anyone at my school. One rumor stuck out in my mind though.
Kayleigh was dating a guy named Patrick Larson. After they broke up, Pat went around telling everyone that he had buttfucked Kayleigh. Not only that, Pat said that she had begged him to do it. When I heard about this, my brain shorted out. I thought the rumor was probably just Pat getting revenge for being dumped.
But, the image of Kayleigh begging for a cock in her asshole was suddenly imprinted in my mind. It was all I thought about. I mean, that's the sort of thing you see in a porno. That's not real life. Hell, Kayleigh was 18 years old. What teenager is so sexually experienced that they actually request anal sex? Nevertheless, the thought of her taking it up the butt got me off countless times.
If I had a love of Kayleigh's ass before, it had become an obsession. All of my fantasies were tuned into that big ass that sat next to me during math class. I found myself staring more often. Every day, I checked to see if her ass crack was showing. On a few occasions, I was pretty sure I got caught staring. She never said anything though, so she must not have taken much notice.
One day, in the fall, I stayed late at school to work on a research paper. Around five o'clock, I decided I should probably go home. As I was passing the gym, I noticed a large commotion coming from inside. My history teacher was at a desk by the entrance, taking tickets.