Jackinworld's question of the week this week was about if people had participated in same-sex masturbation, and if so, how it happened. I answered, but was frustrated because they limit your answer to 8 sentences, which isn't enough to describe more than one experience. He is the full answer.
I did it with a cousin and a couple of friends, and with all of them, it happened differently. I guess if I'd gotten involved the same way every time I would have to say I had a plan, but I didn't; it just happened, which to me indicates that, at least with these boys, both wanted to and were only looking for an opening. Let me start by saying that I am not gay, but I always enjoyed touching other boys, particularly if it involved masturbation, and the idea of another boy doing it was a huge turnon for me.
My favorite was with my cousin, when I was 13 and he was 11. We always used to give each other 'backrubs', which really were light tickling sessions where we'd run our fingers all over each others' bodies in turn, but always in our underwear. I enjoyed doing it to him more than having it done to me, since I could touch him almost anywhere. I never touched him in his crotch, but I did do his butt. I really liked to touch him around his neck and collarbone, which has always been a sensuous site for me.
I was doing him this night with him laying on his front, and he asked, 'Does it feel good when you rub on your bed,' and I immediately knew what he was talking about. I said yes, and asked if he wanted to turn over. He did, and his underwear were tented out with an obvious little boner. I kept tickling him, and finally got to his boner, and could tell he liked it, so I pulled his underwear down and ran my fingers up and down it, eventually stroking him to a dry orgasm. Then he did me. That was our little game for many years after that. I really looked forward to those sessions.
Another was a good friend who I'd played with for many years. We'd go skinny dipping and go naked in the woods together, and I always enjoyed the feeling of being naked with him. One night when he was sleeping over when we were about 12, he suggested we play strip poker, and I agreed. Somehow we agreed on the rule that whoever lost had to lay naked while the other did anything he wanted to get him to move, and if he did move, he had to do the same thing to the other.
I lost, and lay back naked, and felt my penis start to rise. He tickled me in all the normal places, and though I was very ticklish, I didn't move. Then he started to tickle my penis, which felt really good. He kept doing it, then began to stroke it, which felt even better. I think this is the first time anyone else had ever done anything with my penis other than quick exploratory feels. I could tell he was going to jerk me to a dry climax, and just lay there enjoying it. He seemed to be enjoying it, too. Of course when I came, my penis jerked, and he claimed that meant I had moved. I put up a token resistance, since I really did want to do it to him, but I didn't want it to be too obvious.
So he removed the rest of his clothes and lay back, and I did the same to him, first tickling all around and finally getting to his penis. I began to stroke him to climax, and he got really animated when he came, and I could feel his penis come alive in my hand. His was dry, too.
From then on, when we had a chance to be alone, one of us would suggest we play strip poker, and we'd eagerly go to one of our rooms. The funny part is that we never actually played poker after the first time; we'd just strip naked and take turns bringing each other off.
When I was much younger I had a friend who liked to pull down his pants and show me his privates, and I'd do the same. We were 7 and 8 years old then, and didn't know what to do, but we got hard and played with our own little penises for a while. Sometimes we'd get naked in the woods and run around chasing each other, and the fun part was that if we caught one another, we'd grab from behind and hold on, with the captor's little boner stuck in the captee's butt crack. It felt really good, but we never went further than that. I think we would have if we'd been sophisticated enough to think of it.
Another boy was a friend in junior high who stopped at my house after school fairly often. We'd mess around in my room, and one day he rummaged through my bedside table and found my hidden tub of Vaseline. Without asking, he went over to my reclining chair, pulled his pants to his knees, lubed up, and proceeded to stroke himself off. He was a little more developed than I was, and I was amazed how much semen he shot all over himself. I of course was turned on by watching him, but did it on the bed, and by then I was just starting to shoot, and laid a little pool of semen on my own stomach.
He started coming over a lot more after that, and the first thing he did when we went to my room was go for the Vaseline and have a good wank. It was fun, but I frankly got a little tired of him just doing that and not wanting to interact with me (meaning, do each other). He did that until we were in high school.
There were a few others, but the most memorable of them was at summer camp. We'd been there a couple of days and there was no sign of masturbatory activity, and I was getting to feeling the need to do it. Like in many situations, all you need is a catalyst, and we had one in the cabin. He wasn't shy about being seen naked, and he was the one who started things. One night he just announced that he had to jerk off, and pulled his shorts off and started doing it in front of us all, laying on his bunk. There was an uneasy pause, then another boy did the same, then another, and pretty soon all eight of us were masturbating like mad.
That broke the ice, and open masturbation was the norm every night, and pretty soon boys paired up to do it to each other, and by the end of the two weeks, we'd played all kinds of masturbation games, like the typical who could shoot furthest, who could do it the most times in a day, who shot the most (we'd catch it in a test tube that someone found somewhere), and other games that I can't even remember now. But I do remember that was the best part of summer camp. Any free time in our cabin was punctuated by heavy breathing and the slap of hands on penises. We were caught by a counselor one time, which scared us to death, but he just smiled and said, 'have fun, guys,' and walked off.