My first college roommate was a boring nerd, except that he liked to stroke with me!
At the last moment my Freshman year of college, I didn't have a roommate for my apartment, and I registered with a service that placed a guy with me. I knew it would be temporary. He was really boring, an engineering student who spent all his time building a train set in his basement with his father. But it turned out he didn't spend ALL his time doing that.
I was a pretty secret in high school I had masturbated with one friend, a couple of times, and we both were embarrassed and felt dirty. Well, to be honest I felt something else, too. I felt it was really hot and had the urge to do it again. But my friend didn't want to, and I was afraid to ask anyone else.
As David (the roommate) and I got to know each other, I was surprised that such a nerd as him was kind of open talking about masturbation. It came up a couple of times. And a couple of times I saw him walking to the bathroom naked and half hard, and figured out it was to 'clean up.' He was really nerdy and boring, and it wasn't clicking that we could jack off together....until one night.
We were kind of bored and it was a warm night, so we walked down and got some ice cream and brought it back to eat. David had gone home to his small town the weekend before, and so just to make conversation, I asked what he did (so far, all I'd heard was work on his train). He said he got together with a couple of friends. I asked something about what they did (figuring they might work on the train, too). He kinda stumbled and had a hard time saying anything. I jumped in and said, well, what do you guys do there for fun, anyway?
'We jack off!' he said, and laughed. I really wasn't sure if it was a joke or not. I couldn't believe that if it was the truth, I was hearing that!
But I said, 'Really??'
'Yeah. Been jacking together since we met in high school.'
I was pretty speechless...and excited. And all the way home, and through our ice cream, I nervously asked him questions. They were pretty hot. Three of them got together regularly and weren't shy about who's cock they were stroking. And another two guys sometimes joined in. One of them lived close to David, and he said that all through high school they probably jacked off together 2-3 times a week.
I was shaking with excitement. And so nervous I couldn't ask. But David did. He asked if I wanted to stroke together. I'm sure I said yes, but I hardly remember anything, except feeling his cock in my hand. It was limp and soft and rubbery when I first touched it, but it got hard pretty quickly. David had spread a towel on the sofa, and we both had stripped naked. His hand was stroking me, and he was really, really good at it. I came in a couple of minutes.
It took longer for him to cum, I was really nervous I guess and he'd felt better hands on his cock...but he did cum, seven inches of hard cock shooting cum onto his belly! Wow!
The next morning, I wanted to jack off again, but he was into his engineering books. But that night, after dinner, he got out the towel again and we sat together on the couch, cocks in each hand. It was early, and David said, 'Let's see how long we can last.' God, it felt so good, but I think I lasted about an hour before I couldn't resist. David could have gone longer, but let go his wad right after.
I figured, hell, I masturbate in bed every night, and David does too, so let's just do it together. Most of the time, he was totally into it, but sometimes he either didn't feel like it, or wanted to jack alone. Maybe you can tell that I was ALWAYS up for it! We roomed together for two years before I transferred. My cool friends couldn't figure out why I kept him as a roommate!