I was 13 years old and had been best friends with Luke (not his real name) since we were babies. We used to sleep over at each other's houses all the time. We occasionally played truth or dare over the years and had seen each other naked lots of times before, either from just being kids and showering together, or playing truth or dare. He is circumcised and I am not. After primary school, we went to seperate high schools and we hadn't played truth or dare for sometime, so I had not seen him naked for several months. He was an early bloomer and I was a late bloomer.
One day he had told me about a guy from school's birthday party he had been to, where a group of about 6 other guys had camped out in the backyard for the night, in a tent. He said they had all played truth or dare and that one person had been dared to wank and then ended up sleeping in the wet spot afterwards. I had heard about jerking off and wanking from other friends and TV, but didn't really know what it was.
A couple of days later it was the weekend and I was to sleep at Luke's house. Earlier in the year he had moved out of his bedroom in the house to what used to be his older sister's room, in a small building in the back yard, seperate from the main house.
We had dinner and went to his room to settle for the night. We got changed and lay on his double bed in our boxers to watch TV. I can't remember who initiated it, but we decided to play truth or dare. Late night ads on TV for sex phone lines probably made us horny. We both usually chose dare for our turns in the game and after a few lame dares each, Luke dared me to strip and run around the room naked. The only light we had was from the TV, but I was very self-concious, as I had no pubic hair at all. I had become fascinated by his underarm hair he had developed that summer, but also very jealous of it. I did the dare and stayed naked, but got under the covers. I dared him to do the same, and I got my first view of his 'new' teenage body. His dick and balls were massive compared to mine, and what I remembered his to look like. He had pubic hair also, which I found fascinating. He seemed to enjoy flaunting what he now had and did the dare slowly and without trying to cover up at all. He finished his saunter around the room and got back on the bed, but stayed on top of the covers. He then dared me to have a wank. I said I didn't know how, so he reminded me of a 'Hale and Pace' (English comedy duo) song lyric about masturbating that went 'one finger one thumb keep moving...'. I said I would try, but only if he did it too. He agreed and we both lay next to each other with the TV dimly lighting the room.
I masturbated just as the song said, with just a finger and thumb wrapped around my penis, as my dick was too small at the time to jerk with a full fist.
I remember the feeling being unlike anything I had felt before and being hornier than I ever had before. I kept looking at Luke's comparatively huge balls as he jerked his cock. I wasn't sure what I was supposed to do other than tug my dick for a while. I didn't know there was supposed to be a fantastic ending. I couldn't cum anything other than air at the time either, so the real fantastic ending wouldn't come for a few months later.
We must have jerked off for about 20 minutes before he stopped and decided he was going to go to sleep. I'm guessing now that he must have cum, but I didn't notice anything to that effect at the time. I carried on for a while longer until I got a strong pain in my lower back and had to stop. I found out with further experimentation later that this pain would come back if I continued to masturbate after cumming, so I must have passed this point that night, but with my inexperience and inability to ejaculate, had not noticed.
The next morning we had the house to ourselves. We got up and decided to stay in our boxers. We went into the house and had breakfast. He had a shower and came out of the bathroom wearing only a towel. I had a shower after him and followed suit. We went into the living room to watch TV and sat on seperate chairs that were facing each other. He had one leg draped over the arm of the chair and I could see his balls again which I found just as fascinating as the night before and kept taking glances at them. Again I can't remember who initiated it, but we decided to masturbate again like the night before. We took off our towels and stayed in the chairs we were in and masturbated ourselves again. I think he must have gone to the bathroom to cum, but as I didn't realise anything like that was supposed to happen, I took no notice of his lack of cum. We stayed naked for most of the rest of that day and masturbated together a few more times that day and from time to time over the next year to come, after wich he lost interest in doing it together.
I moved away shortly after and the friendship sort of petered out. He moved to a town 600km away after high school. I've seen him once since then and I was secretley remembering the times we used to have together and wishing something like that would happen again. I've always wanted to thank him for teaching me how to jerk off.