This happened when I was 15.
John and I had been best friends since the seventh grade. We went to movies together, played sports, and generally do what other friends do at that age. When we became freshmen it was totally awesome and John and I became jack-off buddies. It started when he was going to stay over for the first time at my house. I was so excited.
After watching our share of movies and eating pizza we decided to go to bed about 1:00 am. As we were laying there we started talking about girls who were hot and that we wanted to do it with. Then I asked John if he had a lot hair around his dick. He said that he had some and asked me the same question and I said, 'Yeah, I have some too.' John then asked me how big my dick was and I told him I did not know. He asked if I would want to measure it and I said sure. So John got up out of bed and went to my desk to get a ruler. When he got up I saw the bulge sticking straight up in his shorts and the thought of seeing John's dick got me so hard.
John got the ruler and then dropped down his shorts and revealed his boner. He measured it to be 5.5 inches and had dark pubes around it. It looked so hot. He then asked me to measure mine. So I threw the covers off and then took down my boxers and there it was. I measured mine to be 5 inches and I have dark pubes too. John did not put his shorts back on and climbed into bed. He asked me if I had ever jacked off and I said of course. He then asked me if another guy ever jerked me off and I said no. I told him he could if he wanted and he said he would if only I would twist and play with his nipples. I played with them, and even sucked and licked them while he jerked me off. I then reached down and started playing with his dick and then jerked him off. It was so hot. I then told John I had an idea to pretend we were doing girls in our school in the same bed. We both laid there and started talking about screwing these girls and even switching off. John then said he wanted to cum and let's cum on each other's dick. I said sure and then we jerked hard and fast to eventually we shot on each other's dick and into our pubes. It was so awesome.
John and I had many sessions like that in high school. It was a time I would not forget.