This happened about five years ago
I grew up in a house with four siblings. My two younger brothers and I shared a room and their was absolutely no time to masturbate there. Compound that with the fact that all five of us together (that includes me) had to share one (yes, only one) bathroom, which meant no more than 5 minutes in there, not enough time to masturbate properly. So, I was mainly left to let myself have wet dreams to take care of releasing my sexual tension, and that didn't make me very happy, but I had no other choice.
When I was 15, I had a friend (we'll call him John) who lived a block or so away from me. John was my main information source on all matters concerning sex, because his mother was very liberal with him and gave him sex education books and such when he was about 12. Whenever I had a question, John had the answer. One day when we were talking, the topic of masturbation came up, and it was revealed that I only did it once in a while, when no one was home (which was very rare). John was shocked, and revealed that he did it about once or twice a day, always at night. This was because he lived alone with his mom, who worked night shifts as a nurse and, since John was now 15, he didn't have a baby sitter. Because John was a really close friend of mine (in fact, we were best friends) he told me I could come over and do it at his house some time. I didn't take him too seriously and just kind of joked around and said something like 'That would be awesome', or something. Then John threw me a curve ball when he said 'We can go do it tonight if you want'. I was floored! I immediately told my mom I was sleeping over at John's house, and that evening I rode my bike over there.
I arrived just as his mom was leaving for work. She ordered a pizza for us and told John to call her if any emergencies came up. You know, standard mom stuff. Anyway, we joked around, talked, ate and just did things that guys do for about an hour or so. By about nine o'clock, John asked me if I wanted to watch something interesting. I asked him what it was and he said that he had found some porn tapes that his dad must have left behind before he divorced his mom. I was really excited, because I had never even seen porn before and immediately said yes.
John disappeared into his garage for a second and returned with a video cassette and popped it into the VCR. After some opening credits it showed a gorgeous woman having sex with a man. I immediately felt my dick spring to life and turned and realized John's had as well (either that, or his pants bulged a lot!). After about half an hour of watching the movie, John said 'I can't take it, I need to take it out', and with that he threw off his shirt, dropped his pants and removed his boxers revealing a six inch, uncircumcised penis. Being circumcised I stared at it wondering what all the extra skin was. After a while, John realized I was looking at his dick and laughed, saying, 'You can join in if you want'. At first I was shy but after another 5 minutes of the movie I had to let my cock out of my pants, and somewhat hesitantly removed my clothes and started jerking. I was surprised at how identical our cocks were, except mine was missing a foreskin. I remember being fascinated by John's penis because it was the first uncircumcised one I had ever seen (both my other brothers are circumcised). It was a nice shade of white, with low-hanging, pinkish balls. It wasn't arousing at all, but it was interesting to see what someone else's package looked like.
We kept watching the movie and after a while we were completely comfortable being naked around each other. A bit more into the movie there was one scene, which stood out vividly in my mind. There were two guys watching two lesbians go at it. The girls commanded the guys to masturbate each other while they watched. I must have said something like 'That looks good' because a minute later, my friend said, 'Do you want to try it?' Although I was a bit stunned at first, I agreed and John quickly slid right next to me. However, John made the obvious observation that we were both right handed. After a few minutes we agreed to do each other one at a time. John asked me if I'd mind doing him first. I said 'Yes' and he laid down in the middle of the room and I quickly joined him. I kneeled next to him and slowly wrapped my hand around his cock. I was surprised, and wasn't sure how to masturbate him. He told me to slide his foreskin back and forth, which I did. He gave me a few more tips and then told me it was feeling good. After about 5 minutes or so he told me to slow down, but that it was feeling amazing. Then, ten minutes or so into it, he said that he was going to cum. I jerked him harder and faster and he blew a huge load, hitting him as far up as his neck. After letting him recuperate for a few minutes, we switched places. John wiped some of the cum from his chest and used it to lube up my cock. He then slowly jerked me off. It was excruciatingly slow, but also very pleasurable. Every time I would get close to cumming, he would change his grip. After twenty or so minutes, I was begging him to let me cum. Finally, he decided I should blow my load and he jerked me really fast. I think I actually started screaming when I came, and I shot cum up and over my head! It was the best orgasm I've ever had (other than when I've had sex with a girl). I lay there in my after-orgasm relaxed state for a few minutes and observed that John had gotten a boner again. I reached over and gave him a quick jerk off. After a while we both just lay there naked and finished off watching the movie, jerking each other off at least once (though it might have been twice) more. Afterward, we cleaned up everything and went to sleep.
This was the beginning of my many masturbation experiences with John. Though neither of us are gay (we both now have steady girlfriends) we continued masturbating together as teenagers as a way to release our sexual tension. About a week after this happened, we got my younger brother (he's a year younger than me) involved as well, which I'll write about next time.