So, I went to boarding school my last year in high-school. I am gay and by that time I was out of the closet. Almost immediately, I became best-friends with this straight guy there. We bonded and quickly became room-mates. We were very open about our sexuality and masturbating habits and even made out once (he just wanted to try it out)-one of our favourite things to do was take showers together (it sounds very sexual, but it was really just a way of feeling close as friends). I of course would always get hard (he is ripped and it turns me on to this day) which didn't bother him. He would sometimes get turned on too (proximity and all that), but never worried about being gay.
Anyway, one time I asked him if he wanted to jerk off in the shower (I had recently broken up with my boyfriend and really needed release)-he looked at me for a moment then said sure, I was already hard so I grabbed some conditioner and started to stroke. He did the same-at first he didn't look at me, then he asked if I wanted him to finish me off (he knew I'd like that). I asked him if he was sure, and he said yeah, still stroking his dick. I let go and he grabbed on, between heavy breaths, I asked him if he wanted a hand. This one he really had to think about, but he finally said yes.
As soon as I had his dick in my hand, I started to lose it. I told him and he said he was close too. I held off as long as possible and he started to moan and closed his eyes. I stared at his dick as he erupted and I let myself go. Both of our hips were swinging with the orgasmic force. We came all over the shower walls. We cleaned off and went on with our days no problem. We jacked off in front of each other a few more times that year. It will probably happen again, but right now I'm in college and he's still at boarding school (he's a year younger). Once in a while, I think about him when I masturbate.