My first time masturbating with someone else was in the eighth grade. There was a kid in my grade who lived down the street named Derek. Derek was kind of a family friend and came over a lot, but he and I were not what you would call friends.
One day we got a phone call from his mom asking if one of us would help him to get on and off the bus because he had broken his leg. I was chosen for the job and so before school I had to get ready earlier than usual and head down to his house to carry his books for him as he got on the bus and the same thing when he got off in the afternoon.
One afternoon I helped him off and we went into his house and started to just hang out. We watched a little TV and bullshitted and then I left. We started doing that every day after school and we soon became friends.
Eventually, we were good enough friends that we started talking about our crotches. I don't remember exactly how it happened, but one day we got in a conversation about who had more pubes. We finally decided that the only way to know for sure was to check. We pulled our pants down to show just our bushes and it turned out I had more pubes, a fact of which I frequently reminded him.
More time passed with nothing happening until we inevitably began talking about our dicks. Both claimed to have the larger dick and we again decided that the only way to know for sure was to measure. We found a ruler and went into the closet to get a boner and measure. I came out and told him I was 5' and he said the same thing.
Again, long periods of nothing happening between this and what happened next. One day I was over his house (his leg long since healed) when he asked me if I had ever seen porn before.
'I haven't,' I lied to him. (I had actually seen lots of porn, but I wanted to see what he was planning.)
He took me upstairs to his room and pulled out a magazine. 'My grandpa left that here the last time he stayed,' Derek told me, indicating the Playboy laying on the bed. We giddily looked through it and commented on the magnitude of hotness of each of the girls. When we got to the section where one girl was having sex with a guy, we laughed and closed it because we didn't want to seem gay to each other.
Once again, nothing else happened for a while after that. Then one day, I was over his house after school. His sister had not come home and his mom wasn't supposed to be back from work until 5:00. We were sitting around and got to wrestling, which turned into us pretending to have sex and trying to hide the boners it gave us.
'Let's go on the computer,' he suggested. I consented and we sat at his desk, checking out our myspaces and then just surfing the internet. I was surprised when he typed the word 'porn' into Google. He searched through the images and we looked at the pictures, loving the pictures of girls and gagging at the pictures of guys. Eventually, we both started to rub our semis through our shorts. He got up and grabbed a bottle of lotion.
'Have you ever done it with lube before?' he asked me.
'I haven't,' I lied. (Again, I wanted to see where this was going.)
'You haven't?' he almost shouted. 'You're missing out.' He squirted some lotion into his hand and some into mine and then slid his hands into his pants again, slowly moving his hand up and down. I did the same. I was so hard and horny, masturbating in front of another person.
We did that for a little bit until, gathering my courage, I said, 'Do you mind if I take off my pants?'
'Go ahead,' he said. 'I'm gonna too.' With that we dropped our shorts and underwear to the floor and continued viewing the pictures. We were both careful not to look at the other's dick, in case we were accused of being gay. But I couldn't help to sneak glances. I saw that he had been lying when he told me that he was 5', he was smaller. I later found out that he was only about 4' long.
Somehow, (I forget how it happened) we ended up sitting side by side and openly jerking. It was very freeing to be able to just stroke in front of another person. Tentatively, he asked what I thought about maybe touching his dick.
'Only if you touch mine,' I told him. He agreed and we flipped a coin to see who would touch first. I lost and grabbed his penis. It was so weird feeling in comparison to mine. It was a lot smaller but a lot stiffer than mine. I moved my hand up and down. He leaned his head back and told me to hold it tighter. I tightened my grip and jacked him again. After about 30 seconds I told him that it was my turn. He nodded and reluctantly leaned over to grab my dick.
He hesitated for a second, and then wrapped his hand around my shaft. It was absolutely incredible. I think he stroked me about three times before I blew my load all over my shirt. He started cracking up when he saw that I did that and, after regaining my breath, I joined him. I left to get a rag to clean my shirt and in my abscence he gave himself an orgasm.
I left before his mom got home with empty balls and a stain on my shirt. That wasn't the last time we did anything, but it was the one with the best orgasm.