My freshman college roommate was voted "hottest guy in the freshman dorms." High school running back, cute face, fun to be around. He had no inhibitions changing in front of me, so I knew he was average-endowed and had a nice set of balls. Still, I never got more than a brief look.
Until that night.
He always stayed out later than I did. Usually I'd sleep through him coming back. One night, late in the year, I didn't.
I was sleeping on my side, facing his bed. I opened my eyes just as he was pushing the sheet down on his body. He wore bikini briefs, and those went down next, about mid-thigh. It was the dark of night but there was a lighted parking lot outside our dorm room, so I could see shadows but no specifics.
He was soft at the time. I watched him play with his balls till he worked up what seemed to be a half-hard-on. He masturbated more slowly than I did, at first at least, and his technique was different. He used his thumb and first two fingers to focus more on the tip. Every dozen strokes or so he'd then stroke the whole shaft. There was enough light for me to see his full erection. That night I got my wish to know what his erection looked like and how big it was. It was probably just under 6 inches, but thicker than mine.
As he got harder his pace increased. His other (left) hand/arm stayed at his side.
Our beds were positioned so that there was a nightstand between us. You could not see the other guy's head when it was on the pillow, but when he lifted his head I could see the side of his face.
As he jacked off he lifted his head about three times to watch him manipulate his erect penis. Then he'd drop his head back onto the pillow and keep jacking.
My heart skipped a beat when he raised his head and looked right at me. I closed my eyes tight but stayed put. To this day I'm not sure whether he saw me.
Either way, he returned to what he was doing. The jacking got faster and faster. He never used his palm ... only his thumb and first two fingers. He was going at a very good clip when suddenly he stopped, held the middle of his shaft tight, and ejaculated. It was too dark for me to see his semen, but after what must've been a few spurts he jacked himself a little more, stopped, shot more cum, and repeated this a few times.
He took his hand away and put it at his side. For a little while he just laid there, his softening penis in what must've been a little pool of semen.
Eventually, he wiped cum from just above his belly button into his pubes. Then he pulled up his briefs, then the covers, and rolled over, and went to sleep.
The next morning I barely slept because I wanted to get my hands on his briefs. Sadly, I never did (I think he wore them to the shower), and strangely there was not much evidence in the dorm room of his ejaculate that time or anytime.
It was late in the year when this happened, but as luck would have it we were roommates again the next year. This happened again a couple times. One night, he brought a girl back and she wouldn't have sex with him but she did jack him off. Yes that was hot, but nothing was hotter than that first time catching the hottest guy in the dorms masturbating, and seeing his erection in the shadows.