When I was younger (15) my cousin Mike was sleeping over. He was two years younger than me, but just as mature. We were in the basement just fooling around as teens our age would, but we finally settled down and were sitting at my computer. We were looking for an online show to watch when a porno pop up came on. usually my first instinct is to close them, but this time I joked around with my cousin saying, "you like what you see?" He laughed and that got us into the conversation about girls and porn.
We started surfing the net for porn and realized we liked the same stuff. Something else about my cousin: he can be extremely shy, so I knew I'd be the one to have to start this. We were looking at this porn of this really hot brunette sucking off some guy and I started to drop hints that I wanted to masturbate, telling him how horny the video was getting me, etc. Finally I turned to him and asked, "Do you mind if I- you know... masturbate?" All he answered was, "yeah, I don't care," but I could tell he was a bit nervous.
So instead of just whipping it out and going at it right there in front of him, I began to masturbate through my pants. I could tell he was watching me, but pretending not to. After a while of the same porno I finally asked him if it was okay that I drop my pants. He told me it was okay so I dropped them and started masturbating in front of him. He still hadn't made a move to masturbate himself, so I turned to him and told him it was okay if he wanted to do it to, just so he knew that I was totally comfortable with it if he was. By the time I had came, he had just rubbed himself a bit through his pants. I could see that he was still a bit nervous, so we stopped for the night.
Before he left, i introduced him to one more site - Jackinworld.com, the site that taught me all I knew about masturbation and mutual masturbation. I wanted him to go through it and open his mind to all the joys of masturbating.
The next night he came over, we fell into the same routine as last time. We began to watch porn again, I asked him again if it was okay that I masturbate, and this time I wasted no time in doing it in front of him. What also changed, is that, after a while, he stuck his hand down his pants and began to masturbate also. I told him it was okay to drop his pants if he wanted to. And after a while he did! His penis was a lot smaller than mine, and he had less hair, but that was only because he hadn't fully matured yet. So there we were, two horny adolescent boys, going at it like no tomorrow.
Finally, I summed up the courage, turned to him and asked, "You need a hand?" in a joking sort of way. I knew he knew what I meant, because the site i showed him had billions of references to mutual masturbation. He laughed for a second, taking in the joke, but then I reached over and took his penis in my hand, and began slowly jacking him off. He was only surprised for a second, but then he began to enjoy it, as I could tell. I didn't pressure him to do it back ad if he wanted to stop me he could have, but he didn't. And after a while he turned to me, looked down at my penis and asked, "Do you want me to...?" I told him sure, of course, and he slowly wrapped his hand around my dick and began to stroke in rhythm with my strokes on his dick.
The sensation was amazing! I've never been so hard in my life and never felt so good masturbating! The feeling of his hand jacking me off while I did the same to him was the best I've ever had! I recommend every male to try mutual masturbating and some point in their lives. Because we're both guys we know what feels good and what we like. Girls that have masturbated me don't even do as good a job! We continue to do it to this day, and I can't wait for more!