My friend and I have been best friends since middle school. we're over each others houses virtually every weekend. We do everything together and talk about everything. We had been pretty open in talking about masturbation for a very long time, but were not very comfortable around each other when it came to actually doing it until last summer.
The summer began and we had been hanging out almost every day and night. We eventually started watching some porn videos on my computer and had to get some relief. At first we went into the bathroom and eventually we got more and more comfortable doing it in the same room but generally under the covers. I have always wanted to try jacking off/getting jacked by my friend. I know i'm not gay or anything, but just wanted to do something different. I've read a bunch of stories about how brothers do it all the time and since i'm an only child and my friend and I were practically brothers I decided it's only natural. One night we were talking about masturbation, and somehow it got onto the subject of mutual masturbation. My friend said that the farthest he would go with a guy would be mutual..kind of hinting. After working up the nerve, I asked him if he wanted to try it and after thinking for a few seconds he said sure.
He got out of his bed completely naked and I turned on the light. He sat on the floor looking down at his rock hard erection. His was a bit smaller in length than mine, but it was much thicker. I reached over and started pumping his cock. I rhythmically stroked and only a minute or so later he came to an orgasm. My friend had not masturbated in almost two weeks so he came all over. He shot load after load and I kept stroking through his orgasm. His cum was all over my hand...so we wiped up and I leaned back. He started stroking my dick and it took me a little longer than him to cum. I didn't cum as much as him being that I had already done it that day. We cleaned up and got into bed. My friend confessed that he too had wanted to try this, but was a little weird and didn't wanna do it again. I didn't want him to feel weird or anything so I didn't really push it, but a few months later it happened again...but that's another story.