This is absolutely true. Name has been changed, of course.
While I was a teenager I had occasion to masturbate with two different guys. This story will deal with the second, because it's a little more brief and I'd like to get to it first. The other will come later, so keep your eyes peeled.
I knew my friend (we'll call him Charlie) from back in junior high school. We were in music together and a few other classes... didn't hang out outside of school much but were well aquainted. At 16 and a junior in high school, he was one year younger than me. He seemed fairly sheltered and was one of the 'good kids'... very studious, well mannered, good grades and such (although, so was I, for that matter). Our group of friends had gotten into some racy discussions lately, and we'd admitted to each other that we both enjoyed porn. I told him about a particular video I was borrowing from a friend and he suggested that we watch it.
We exchanged several emails about a day and time, it would be after school when my parents were away. We also made kind of indirect hints at not being uncomfortable with masturbating in front of someone. So I was on edge about this when the day came, since I was really more interested in seeing him jack off than seeing the movie I'd already seen 15 times. Charlie wasn't wildly attractive to me, just OK, but I was totally into watching someone else masturbate. For... various reasons... at previous discussions with other friends, Charlie had also mentioned that he typically ejaculated what I considered to be a huge amount... about 6 to 10 shots is what his estimate was. This had me totally pysched... porn was OK, but I wanted to see the real thing.
When he came over we sat in couches opposite each other, him looking to the left at the television and me to the right... although I sat further away and had a great view of him. We actually got through about 15 minutes of the movie before either of us did anything... there was a lot of tension. I could tell he was uncomfortable and had a bulge going in his jeans. I made a comment about needing to 'relieve some tension' that he didn't quite understand (or chose to avoid) but he really seemed simply a bit shy... we'd discussed this over email where he'd already said he was into it.... He said I could go ahead if I wanted, but I told him I'd feel silly doing it alone. 'It's up to you,' he said. 'OK.' ... 'OK.' There was a moment where we looked at each other, motionless... and it became apparent that he wanted to see me too... neither of us was going to pretend that we were watching the film at that point.
We both unbuttoned our pants at the same time, and started to sort of mirror each other. I had switched to boxers at this point-there was a time in the late 90s when this was necessary to be 'cool'... and a previous girlfriend had started buying them for me.) I had seen Charlie change previously so I knew he wore briefs, and as he unzipped and folded down the sides of his fly, I could see the patch of soft white fabric below a blue striped waistline, the bulge from his hardon pressing slightly up, slightly out and to the left. I could see him also staring at my crotch as I did the same, my own dick sticking straight up with the flimsly boxer material draped from it. I raised the waistband with my left thumb and grabbed my dick, sort of keeping a little shield up with my boxers for a moment. He did the same, giving a couple of slow tugs to his own dick behind his briefs. I knew he'd mirror me, so I pushed my boxers down flat so he could see my dick, and he did the same. I got a view of a few dark pubes around the base of his dick, his hand wrapped around it, and then a pinkish head that was almost fully engorged. He was circumcised, and the shaped of his dick head was really cool to look at as he stroked it really slowly. I had about a 4.5' cock (which is only slightly larger now) but his was easily 6', which fascinated me. He could stroke his entire fist up and down a good distance.
So we watched the film and made pretty obvious extended glances at each other's equipment for about 30 minutes. We went through a couple scenes and talked about what was going on, which was very very hot. I had to really slow down to avoid cumming, I was right on the edge after about a minute of this! I couldn't get over how electric it felt to stroke myself while watching him... I was so incredibly horny from this I could barely jack off at all without blowing it. He said that he normally took a long time... which was fine with me.
He sped up and slowed down quite a bit, and watching the technique was really educational. He'd stop to simply rub it a bit, and stroke his balls... and I tried the same. At several points he stopped momentarily, using his thumb to rub his precum all over his cock head. He was also breathing heavily...both of us were. 'How close are you?' I asked him. 'I'm pretty close now'... He was jacking really fast now, his hips were bucking a little bit, thrusting his cock up into the air. I couldn't take it... my cock felt hard enough to explode, the head was almost purple, and I felt the cum collect at the base. It traveled up my dick just before I let loose... I let out a couple little gasps as I blew my load on my stomach. Two really small squirts and then a long dribble...this was still a lot for me. It was a breathtaking release, the feeling of my penis lurching and pumping the jizz out of me, and seeing that Charlie's penis was doing the same.
Somehow during my orgasm, I missed his. Either that, or he dribbled... but I never quite saw exactly when he came. Very disappointing, but I could hear the sloshing wet sound suddenly as he continued jerking, so I knew his hand was covered in cum. It was a very wet sound, so I'm sure it was quite a big load. I just wish I could have seen the ejaculation. This was his first time seeing hardcore stuff on a real television (not grainy low-res videos that were on the Internet at the time), so I figured he'd go off like a cannon. He definitely seemed to be mellowed out, slouching now, stroking his wet and sticky dick. It was strange to see Charlie that way... he wasn't a big guy, and his cock just looked huge and manly on him from my angle.
That's about it. There was no cleanup, he just pulled up his underwear...and so did I. So we talked a bit and left the house... both knowing that we still had semi-hardons and wet, sticky underwear full of cum. We never really got a change to do it again, although he said he liked doing it with someone else. To this day, I wish I had 'offered him a hand'... I'm pretty sure now he would have accepted, because we were trying to be very liberal and free and rebellious at the time. We talked about porn several times after that, commenting on a great jackoff session we'd had and how much cum we shot, stuff like that. I've masturbated to this memory countless times since the experience (including this very moment!).