What are your experiences with roommates and masturbation? Here's my best story:
My college roommate was voted "hottest guy in the freshman dorms," and for good reason. High school running back of a body, deep brown eyes, great smile. I'd catch good glimpses of his genitals, which were a bit bigger than mine. I yearned to see him erect and/or to find evidence of his masturbation, but never did.
One night, I heard him come in from a party but stayed sleeping on my side, with my face to the wall. Something made me turn over. When I did, I saw that he had pushed his covers down past his knees. There was a streetlight outside our dorm room, so it was dimly lit. A nightstand was between our beds. I could barely see his chin.
He heard me turn over and lifted his head to see if I was awake. I shut my eyes tight. I opened them a few seconds later as he pushed his underwear down his thighs. I held my breath. I could not believe what I was seeing!
I watched him play with his flaccid penis, and then his balls. He had lovely testicles, and I remember him pushing them up around the base of his penis and generally paying a lot of attention to his scrotum.
Only when his penis was getting erect did he touch the shaft. He moved it very slowly, with just his first two fingers and thumb, and took his time turning it into a full erection.
I was a bit surprised to see he was about my same size when he was erect -- less than 6 inches. He was to the right of me, and was using just those few fingers of his right hand, so I had a very good view of his erect penis. The light was coming into the room in a way that let me clearly see the shaft, head, and testicles.
He masturbated more slowly than I did, with just those two fingers and thumb. But he picked up speed as the session went on. Then he started lifting his head from the pillow to watch himself masturbate. Then he'd put his head back down, lift it up, put it down, etc. He never put his palm around his cock. He just used those two fingers and thumb, and seemed to be holding the skin tight and being aroused by the feel of the skin sliding up and down over the erectile tissue. I had a good view.
He started doing this really fast. He put his head back and although it was not quite light enough for me to actually see him ejaculate, I knew he was doing so because he held the mid-part of his shaft very tightly and sort of stopped furious jacking motions to let his penis expel the semen. After the ejaculation was over, I watched him lift his head as he pushed his semen down into his pubic bush.
Then he turned and looked at me. I had my eyes open and closed them as fast as I could, but to this day I think he saw me watching him push his semen into his pubic hair.
I rolled over onto my side and played with my raging hard-on, emulating what I had seen -- the way that he masturbated with just his first two fingers and thumb. Then I waited for sounds of him sleeping, and then masturbated until I had an amazing orgasm -- one of the most-intense ever.
It was in March. I saw him masturbate two other times. He might've known I was watching; I'm not sure.
But the first instance was one of the hottest things I've ever seen. And to this day, I occasionally masturbate like he did -- with just the first two fingers and thumb.