First of many. This happened when we were both 15
Brendon and I were best mates for about three years.
One night after we went ice skating he came back to my place to spend the night. We both had a shower and said goodnight to my folks, then headed off to my room. We did the usual chat about school, chatting up girls and assignments. Then we started talking about sex and masturbation. We both knew each other masturbated, and I asked him how he did it. He said he couldn't explain it.
He said jokingly he would have to show me. I said show me then, not thinking he actually would. He climbed on the top bunk and told me to move over. He asked me if I was naked, I said yes I was. So he took off his jockeys and got in. As soon as he got in his hands went straight for my cock and he started to massage it with both hands.
I started to rub his cock slowly at first but picked up the pace a bit. I was moaning the whole time. After about 15 mins I told him I was gonna cum and blasted onto his hand and my leg. He told me he was not far off coming, so I started to really jack him hard and he came soon after, spurting onto his stomach and chest.
We didn't get too much sleep that night. To this day Brendon and I are still the best of mates. We have shared my girlfriend many a time, but that's for another time.