Now I have a lot of masturbation adventures to share but we might as well start with my first with another guy.
The background story: I was 16 and jacking off at least four to five times a day, but really wanted to stroke my cock with another guy.
Sadly I'm from a small redneck town, so if it didn't go to plan then word would spread and I would be in a whole heap of trouble if others at my school found out.
I was very popular at my school (no jock, just got on with everyone quite well) and there was one guy aged 14 (let's call him Jamie), who I was friendly with but we weren't best friends (we soon would be!).
One night I was on ICQ chatting with friends and Jamie came online. We chatted a bit about different friends, movies, sport and the topic among two teenage boys of course turned to sex and porn.
Somehow the topic turned to jacking off and I did the typical teenage 'wanking is gay' speech even though every teenager does it.
But Jamie then wrote: 'Why? Theres nothing wrong with it'
Lets just say that broke the first layer of ice and from there we openly admit we masturbated, how we liked to do it, our first time and than I took a big leap and confessed to him that I wanted to mutually masturbate with someone. To my relief he said he wanted to do the same.
So after some planning at 4am in the morning (we spent the whole night chatting) we decided he would bring some Buttman porn around to my place on Tuesday, since I lived by myself during the weekdays (My parents had to always go out of town on business).
Tuesday night came, and lets just say I was nervous as hell. Jamie turned up and we watched the porno, making remarks whenever one of us had to go to the bathroom like 'what were you up to in there?'.
The porno ended so we looked at some on the internet, still both a little nervous with neither wishing to make the first move.
I made the comment I wanted to whack off but he still was a little hesitant. About three hours had gone by since Jamie turned up and no one had made a move. It was turning out to be the cold war of mutual masturbation.
I put one of my porn videos in the vcr and we sat back down and watched it.
About ten minutes into it, I decided to be shameless and go for it. I said I felt super horny and with that took off my shirt and pulled down my shorts and boxers to my ankles, sat back down and began to stroke my large boner. Jamie smiled and watched me. I knew he was still a little timid for some reason so I joked that if he didn't pull down his pants I would cum all over him.
Jamie then unzipped his jeans and pulled them down revealing his cute 5 inch boner. Compared to mine (remember I was nearly two years older) his cock looked tiny and he kind of felt shamed by this (ego boost for me, but I didn't think his cock was anything to be ashamed of).
We began stroking to the lesbian orgy on the tv and Jamie got comfortable by stripping nude like me. I than confidently reached over and grabbed his cock, stroking it and he returned the favor, jerking mine up and down. Heavy breathing all around.
I than decided for us to get in a better position (by now we had forgotten about the lesbian orgy!), so we lay on the floor in a sideways 69 position. We jerked each other off and Jamie didn't last long, squirting layers of cum all over the place including on my face and body. He than sat and watched with his now shrinking penis as I blasted stream after stream of cum from my beautiful 16 yr old cock.
It's safe to say we became jacking buddies after that, and to this day, still meet up for a stroke.