I have read a lot of the other stories on this site, and I think mine will be pretty good.
2 years ago I lived with my mom right after my parents' divorce. It was a pretty boring place were I lived, I spent most of my time hanging out with my friend Eric. I am straight and have a girlfriend of a over a year now, but I always thought Eric was kinda good looking. He had a tan and a very muscular look with the six pack and everything, but he wasnt bulky or tall. I was about 2 inches taller than him and we would play basketball or football at his house. Some nights I would stay over at his house. When I visited my dad he would give me money and I would by condoms and lube and other things with it. I would bring those things down to his house when I spent the night and he would get excited over the condoms. Since he didn't feel comfortable with jacking off in front of me, we would take turns going into his bathroom. But I could hear him jacking off with the condom from his room and I would get a huge hardon from it. I had just been circumcised a month earlier. That's how we actually started to get onto the subject of our 'members'. He had been circumcised a year earlier than me and we talked about stuff like the differences in feeling after the surgery. After a couple of weeks of me coming down to his house with condoms and stuff, I decided to ask him to spend the night at my house. He said sure.
When he came down, we watched some movies after my mom and her husband went to bed. Then I asked Eric if he wanted to play truth or dare (like most people do to break the ice). After a couple of minutes of some lame dares and truths I asked him to show me his dick, and like most other guys , he told me he would only if I showed him mine, so I said sure. And we both showed our dicks. Then I dared him for us to just stay there naked. He said he would again only if I was naked too. So I of course said yeah. And I could tell after a couple more turns of the game that he was hard (DUH!), so I suggested we jack-off. We hadn't jacked off in front of each other before so I wasn't sure of his reaction, but he didn't even answer. He just started stroking his cock. His cock was about 5 1/2 inches long, mine being 6 1/2 at the time (I was 8 months older than him). I noticed that he wasn't using any lube so I asked him if he wanted any. He said that he never had used any, I thought that was strange that he never had tried it with some. But I got some out and told him it was messier but much better with some. I put some on his hand and noticed that even with the lube he was just beating away like there was no tomorrow. I told him to slow down and he said it didn't feel good that way. So I suggested that we jack each other off, that way he would understand how good lube and a slow pace feel if done right. He was a little hesitant about this, but I guess he was so horny he said sure. So, I re-lubed us both up and started to jack him off while he jacked me off. It kinda backfired on me. He was in heaven from the way I was slowly going over his head and massaging his balls while doing it, but he was so into what I was doing that he was jacking me off at lightning speed with small stops. It felt really good, but I wasn't use to it, so I exploded only about 5 minutes into it. He didn't realize I had cum on his hand and he just kept on jacking me of , which was really good feeling. About 2 minutes afterwards I realized that there was warmth all over my hands and that he came all over my hand and his stomach. All he could say was , oops....and then we laughed. We talked some afterwards and we jacked off some more that night and the next night. I eventually moved back in with my dad and am really into my girlfriend right now. We have had some excellent masturbation sessions too, but there's something forbidden about doing it with another guy that makes it feel a little better. I guess it's because when a guy thinks of sex they think of there dick, so some guys see another guy's dick and they suddenly think of sex, which gives them a chubby in return. So jacking off another guy and visa versa would be sexy for that reason. Eric was my only person - I don't think I'll do it again. But I'm glad I experimented to see what's out there.