I had been friends with Bill since I moved to his school. We had sleepovers occasionally in primary school, and also during high school. We went to different high schools and lived quite far away from each other, but we still managed to keep in touch. One night when we were about 16, he was sleeping at my house. I had found a website about masturbation and showed it to him that night. We looked at it for a while reading about the different techniques each saying what we had or hadn't tried. After a while we decided we should go to bed.
We went to my room and stripped to our underwear and got into our beds. He was on a mattress on the floor of my room, and I was in my double bed. We talked for a while more about sex and masturbation, and then he told me that he was pretty sure he was gay. I confessed to him that I liked guys also and I asked him how he knew he was gay. He said because he had tried sex with guys and girls, and preferred it with guys. I was a virgin at the time, but had jerked off with two friends before. I asked him about his experiences and he told me about the things he had done. Both of us were getting hornier and hornier as the stories went on. I told him about the times I had jerked off with my friends and asked him if he had ever done anything similar. He said he had also jerked off with two other guys. I asked him if he wanted to make it 'three all' that night and he agreed.
I took off my boxers, he took off his briefs and we threw off the covers and started masturbating ourselves. We had read about mutual masturbation on the website earlier. I was incredibly nervous about asking him to try it, but after a while I asked if he wanted to jerk each other. He agreed and climbed up onto my bed. We sat crosslegged facing each other, and took hold of each other's dicks. It felt awesome to have someone else touching my cock. I grabbed his and instantly realised how much bigger than mine it was; thicker as well as longer. We were both uncut and he was leaking quite a bit of precum. I knew what it was, but didn't realise people could produce so much of it, as I, nor the two friends I had jerked off with before never had as much. We jerked each other off for a while, and were massaging each others balls, until he decided we should go back to jerking ourselves. In hindsight, I think I may have been too rough with them.
He stayed on my bed and we both lay back and continued jacking for a while. Eventually he asked me to pass him some tissues. He lay them on his stomach and shot into them. I shot into some tissues the same way shortly after. We both put our underwear back on and went to sleep. We fooled around a few times in the couple of years after that until he moved overseas and we lost contact. I still think about him sometimes and wonder what it would be like to meet up again and if he would be interested in a relationship.