Leo is a friend who will always try things out no matter how wild they may sound. He has a great imagination. I am more careful and usually am the one who says, 'no, that's stupid!' when he suggests some crazy stunt. But we like each other anyway and hang out together a lot.
One Saturday afternoon we got finished from playing some basketball and we went to his house to watch a movie. I was so tired I fell asleep on the couch and I woke up having a wet dream. He was watching me and saw what was happening and laughed at me and joked saying I must have been dreaming about him and other stuff. We talked about wet dreams and jerking off, and he wanted us to jerk each other or at least in front of each other but I wouldn't because I was afraid of it.
Then he said ok but we should sleep over without anything on except a t shirt and when I fell asleep he'd rub my dick to see if he could give me a wet dream. I said no but he talked me into it saying it was ok since I would not be awake or responsible for it myself.
So six days later, on Friday night, he calls and says I promised to sleep over. I never exactly promised but I went over anyway and when it was bed time I went to his bed with my underpants on like I always sleep, and he told me I said I would take them off. So I did roll them off. I was so anxious I did not go to sleep for a long time.
I woke up in the middle of the night and he was asleep and nothing had happened so I thought it was all just going to be a joke and went back to sleep. Right about at sunrise though, I woke up in the middle of this huge wet dream that felt SO good, much better than ever, and I was still shooting all over when I woke up. I came aware of things pretty slow because I was so relaxed and felt so good I didn't want it to ever stop. Then I realized that there was a warmth around my dick and I looked and he had his hand still on it, moving up and down very slow and easy. I didn't move till I was finally so drained and lying soaked all over in my cum.
He rolled on his back. He had a real huge hard on himself and started to wank it. I was too relaxed and felt too good to move or say anything. He still had one hand on my dick. He came a really good one. I didn't want to talk about it but it was all he wanted to talk about. I admitted it was really nice. He is a good talker and convinced me since we did it and liked it we wouldn't need to wait for sleep. He said I owed him one, and just wanted me to cup my hand over his balls while he jerked off a second time. I admit I liked to watch him cum too. And I got hard almost right away again.
Since then I have thought it was ok for us to jerk each other off when we really needed it and it has worked out ok. I am going away to college next year and I think I will really miss this.