This is a story based on actual events. The names have been changed to protect the innocent.
*
My junior year of college was an interesting year socially. I found myself a part of a large and weird group of friends. They were a crazy and diverse group of dorm misfits. More than anything, we were a study in unrequited love.
I would say there were love triangles, but a love triangle didn't really explain it properly. If you mapped it out it would look more like a straight line. For instance, I liked a girl. Her name was Christine. She was attractive and blonde with a great personality and a big smile. She only wanted to be friends with me. A girl liked me that I wasn't interested in. One of the guys liked her but she couldn't care less. One of the girls liked him but he didn't even notice. And so on. Anyway, our story centers on me and the girl I wasn't interested in.
Her name was Janet. She was a mousy girl, with short black hair. She was an attractive enough girl physically. Her problem was she had an awful personality. She was spoiled, obnoxious, and whiny. Lord knows why we put up with her. But she was one of the gang, so she was there night after night when we got together, pining over me while I pined over Christine, who was best friends with Janet.
The trouble began when I agreed to sleep with Janet. I know what you're thinking... what were you thinking? The truth is I don't remember why the heck I agreed to it. I think we were talking one night about how much better sleep is when you're not alone. Janet saw her opportunity to get closer to me and offered to share her bed with me. I must have been really hard up for human contact by that point. The school year was almost over and it had passed for me without any kind of relationship at all. Christine had recently made her disinterest in me abundantly clear, and I was depressed and frustrated. Of course, I made it clear that Janet and I were only sleeping together as "friends". We would share a bed but nothing else was going to happen.
Janet had her room to herself most nights because her roommate and another one of my friends were the only pair of our group of friends to actually hook up during that year. So, we picked a Saturday night and I shuffled off down the hall to spend my night with Janet, dressed in a t-shirt and boxers. She was also dressed in a t-shirt and shorts. We curled up back-to-back in her tiny dorm bed and went to sleep.
Nothing happened. I had such a good night's sleep that I agreed to do it again the following week. Again, it was just a good night's sleep. Sharing a bed with Janet was actually a pleasant experience. For starters, she was quiet because she was asleep. But, she did have a nice body. She was a swimmer and had a soft, firm body which included a nice pair of breasts. I couldn't say I minded sleeping butt to butt with her.
It was the third time around that something happened. At least, I should say that it was the first time that I knew that something happened. I woke up in the darkness and noticed that the bed was shaking rhythmically. Next, I noticed that Janet was making whimpering noises. I was about to say something, or at least turn around to see what was going on, when I realized that Janet was masturbating. Her butt cheeks were brushing against mine. Part of me was mortified. I had no romantic interest in Janet, and "hooking up" would probably be an awful idea on so many levels. Still, my proximity to sexual activity of any kind was starting to turn me on. I could feel my penis starting to stiffen despite the awkwardness of the situation.
Janet seemed to be unaware of the fact that I was awake. She was still rocking back and forth and whimpering. I could only imagine that she had one or both of her hands between her legs, rubbing her clitoris and/or finger-fucking her pussy. I must have slept through a good deal of masturbating already because only moments after I woke up the bed shook harder and her whimpering grow into little shrieks, climaxing in a number of spastic jolts, and then Janet was still.
I felt her moving around behind me. I felt her turn around to look at me, to see if her performance had disturbed me in any way. I decided to pretend I was still asleep. She gave a little sigh and settled back down. My mind was racing. Do I pretend to wake up now? Maybe pretend like I suddenly had an urge to leave that had nothing to do with what just happened? I hardly even cared what she thought. Why would I even make such a big deal about it? Despite all of the trepidation, I must have been more tired than I thought I was, because after a few minutes I simply drifted back off to sleep.
I woke up sometime later and was immediately aware that Janet was pressed up against my back. Her hand was reaching around me and fumbling around my boxers, feeling for my penis. I don't know what she was thinking. I was usually a very light sleeper, and although apparently I slept through her masturbating at least once, there was no way I was going to sleep through her actually touching me.
What was I supposed to do? The prudent thing to do would be to jump out of the bed, run back down the hall to my own room, and never speak to Janet again. However, her hand found my penis through my boxers, and her small, warm hand felt good. I was starting to grow hard despite myself. My mind was racing. Part of me was mortified, but the other part of me was 20 and horny, and grateful for just about any kind of human contact. Against my better judgment, I stayed silent and still, waiting to see what Janet was going to do.
I felt Janet snuggle up against me, her breasts pressed against my back, and her thighs against my butt. Her hand continued to touch and stroke my hardening cock through my boxers. I wondered if she thought I was still asleep. I felt her pick her head up to look at me. I kept my eyes closed. I guess she figured I was actually still sleeping, because she lay back down and ever-so-slowly began working her hand underneath the waistband of my boxers. I could feel her other hand sliding between our bodies and down between her own legs.
