After a long break because of shyness, I again stroked another guy.
When I was younger, my friend Randy and I used to masturbate each other (and a few other boys), but as the throes of puberty put demands on Randy's manhood, he decided that masturbating other boys was a queer thing to do, and he dropped me as a friend. All the way through high school I was afraid to bring up masturbation with other boys, even though, in gym class and at the beach, I used to see their dangling cocks and imagine how it would feel to be stroking them.
When I got to college in the big city, I realized that, unlike home in our small town, I could fulfill my desires without the risk of exposure and embarrassment. For several months I tried to drop subtle and safe hints with friends, but none of them took the bait. Just by chance I met a guy a couple of years older than me, on a dormitory swimming trip to a lake. At one point, a bunch of us broke away to go skinny dipping (in flagrant violation of the rules of the lake!) in a cove. Rob was tall, red-headed, and with a light tuft of hair circling an ample dick and handsome balls, and I noticed him right away.
After the initial splashing and dunking, Rob and I ended up in shallow water just chillin' and talking a little. I noticed his eyes kept going to my crotch, and his hand hovered around his dick most of the time, as if to touch it, and without realizing it, my dick began to get puffy, and his too. Quickly, though, we were caught up in the party going on and, though the moment itself passed, the memory of his penis swelling stayed in my mind for the afternoon.
On the way back, Rob came up to me and asked if I wanted to go out for pizza later, and, of course, I agreed. We went out, and had a great time talking. He asked me a lot about how I liked my first months of college, and I must have said something about enjoying the freedom to do things I couldn't in my small town, because he asked me what I meant. The day of partying must have loosened my tongue, because I said something about being able to masturbate whenever I wanted to, or something like it.
I don't remember much about what happened next, except that Rob invited me back to his dorm room to jack off together. I don't remember, but Rob told me later that on the way I talked a lot about how beautiful his cock was and that I was dying to stroke it. Within seconds of locking his door, his pants were down and his cock in my hand; and in a couple of minutes big gobs of Rob's cum were splattered onto my face.
Rob and I masturbated each other two or three times a week for two years, until he went off to graduate school.