My college roommate and I were very good friends, even before we went to college. We masturbated together for years, but we never touched each other. Let's call him 'Jon.'
One night, when our girlfriends were out of town for the weekend, Jon and I went to rent a porno DVD. Like always, we began arguing over which movie to rent, since I am a boob freak and he is an ass freak. After much discussion, he jokingly said, 'We'll rent the one you want if you jerk me off.'
I said, 'OK,' thinking he was serious. I have masturbated other friends, and other friends have also masturbated for me.
Jon then said: 'Are you serious?!'
I just said 'Yes.'
So we rented the movie I wanted and went home.
We both sat on the couch like we usually do when watching a porn movie. Our pants were down already. About five minutes into the movie, he asked me if I was going to jerk him off. I then moved closer to him and grabbed his cock with my right hand and my own cock with my left hand, pumping both at around the same speed. After awhile, he said: 'You have too much on your hands, let me help,' and he held my cock firmly, stroking it. After about half an hour, we both came together.
We cleaned up, and continued watching the movie. We came two more times afterwards. After the last time we came, we talked about masturbating for each other. I said I had done it many many times before, and that it is really great. He then said it was great indeed. As we continued talking, Jon said he wondered how it would feel to have his penis rub against someone else's. I said I had imagined that too, but I'd never tried it.
We both then stood up, and began to move our penises against each other, eventually making contact. We were both rock hard again. It felt awesome! We then began to hit our penises on each other's, which was even better. After playing like this for a long time, we jerked each other off again and came.
From then on, we've jerked each other off quite frequently, despite the fact that we have girlfriends.