A boy and his sister’s best friend… in love

Ok, first let me start off with a little background information. My name is Chris and this story takes place in the summer between my senior year in high school and my freshman year in college. I was 17 at the time. I have a sister, Jill, who is 3 years younger than I am, which makes her 14 at this time. Her best friend since kindergarden, Allison, or Allie as we all call her, is also 14 at this time. Jill and I do not get along at all. We might as well be from different planets. We are always butting heads and are always getting on each other’s nerves. I could not wait until the day I moved away to college, 1000 miles away to college… Things didn’t always used to be that way though. Back when we were younger, say elementary school aged, we got along just fine. We often rough housed with each other, slept in the same bed together (we called them our little sleepovers, even though it was just that, sleeping, nothing sexual at all), and even bathed together. That all changed as soon as she hit puberty around 10 years old. At that time, I was in puberty full force and couldn’t help but noticing my kid sister deveolping into a woman. I knew it was wrong to fantasize about her, but I did anyway, and she knew it. She would always flash me her cute little panties, clinging to that sweet petite butt of hers, and during the summer when we went swimming in our pool , she would often let her bikini ride up into her butt crack and flaunt it around me, and she even flashed me her cute little AA titties every once in a while. That all changed when she turned 12 and starting having her period. No more showing off and I was getting sick of not having any new images to jack off to. I knew it was wrong, she being my sister and all, but I didn’t care. I figured as long as our parents never found out, it would all be good.

Anyway, enough useless information… onto the story.

It all started a couple days before my grad party. Allison was spending the weekend here with Jill (as they often did) which kept Jill out of my hair so I had no complaints about all of the extra noise. Allie is a very interesting person. I’ve always had a little crush on her, but I could never act on it because of the 3 year age difference. She’s just the cutest person in the world. Long, breast-length blonde hair, sky-blue eyes, her face covered in freckles, and a rack and a tight bum that made you know she was a woman and not just a cute little kid. She’s normally a very bubbly and happy person, but this week was different. She had just gone through a nasty breakup with her boyfriend, and wasn’t talking much about it. She would occasionally lock herself up in my sister’s room and I’d find out that she would just be lying there on the bed crying for an hour or more.

Now before I go any further, I should probably give some information about myself. I’m 6 feet 2 inches tall, and weigh anbout 210 pounds. I’m by no means fat, but I could afford to drop a few pounds. But I’m built pretty well and I have a lot of muscle, but it’s not toned very well. I have been told by numerous, unbiased people, that I am a very attractive person, but I don’t think so. You see, I’ve had self-esteem issues since middle school. I had (and sometimes still get) very bad acne and even though my wide football-player build gives the impression of a well-toned body, it’s not. I don’t play any sports and I spend my free time either playing computer games or trying to pick up extra hours at work. I’ve only had one girlfriend, and that only lasted 3 weeks before we broke up and we didn’t get any further than kissing. Obviously, I’m still a virgin (at this point in the story, anyway) at 17 years old and with the way my life was going, I was not going to get laid anytime soon.

Well, the day before my grad party, that all changed. Jill and Allie had decided to go for a bikeride that lovely Friday morning around 11:00, or so that’s what I was told in my sister’s text message (I was working 6am to 1:30pm that day).