When I started to develop I began getting orgasms in my sleep to very sexy dreams and would have this happen more than once every night especially in the early mornings. Sometimes a few times in a row. It would wake me up and I would mop up as best I could and go back to sleep hoping for another dream.
I talked to my friend about this (we were pretty open with each other, but never did much that could be called sexual, just fooling around like when we would get boners we would compare and even feel each other to see whose was hardest). I talked about my sexual dreams and how good it felt and he said he never had that happen in his sleep and wanted to know what it was like.
He, like me, had masturbated before but not to getting an orgasm yet, just rubbing ourselves to get a hard on. He sometimes slept over, and he wanted me to play with his dick when he fell asleep to see if he would have a dream. I have two twin beds. He went to bed completely naked and had just a sheet over him for "easy access". I stayed up and played some games for about another half hour. When I was sure he was asleep, I did like he wanted and went over and pulled down the sheet. He was deep asleep and I just slowly laid my hand on top of his dick just barely touching it and held it there for a while. It took a while till my hand warmed him up but I could feel his dick getting plumped up a little and that made it easier for me to move my hand to actually take a gentle hold of it.
I was kneeling alongside the bed and was in an uncomfortable position but had to remain still. Sometimes I could see he was coming out of sleep a little and I would stay very motionless until he fell back asleep. After what seemed like a long time, all of a sudden and very quickly his dick shot up hard in my hand which I kept firm around it. It took only a few seconds then until it started to pulse and then ooze out a short band of thick stuff like toothpaste. He woke up with a startle and was in a sitting position in about a second. It was his first orgasm and he was confused for a few more seconds about what all happened until his mind could put it all in place. We both were pretty amazed by it all and I will never forget it. The most amazing thing is how quick he went from being almost totally soft, to coming. Just seconds. This also made us closer and feel better about trusting each other and we experimented in other ways over the next year or two after this.