Many years ago, when I was in high school, I had a sleepover with my best friend. Late that night, he pulled out his collection of girlie mags and we ended up taking our cocks out. He asked if I had ever jacked off, and I said yes. Then he said "prove it", and we both started jacking. Not long after, we both had ejaculations. This became a routine for us, sometimes to see who could cum first or who could shoot farther and so on. After high school, we went to different colleges and we never did it again. Occasionally I think I might like to have a J/O buddy again, but I never have.

My high school buddy and I have been jerking off together for many years. Now in our 50's we still find time to keeping it up!

I was in college and had my best friend stay over while my Mom was away for the weekend. He was 4 years younger than me, I was a senior and he was a freshman. We spent the night watching tv, and came time to go to bed, and I asked him if he wanted to share my bed, or sleep in the guest room, and he immediately said he would share my bed. I had been sleeping naked, since my freshman year when I was in a dorm so I got naked and he did also, and we got into bed and turned on the tv to watch Saturday Night. About 15 minutes went by, we had huge boners, and he immediately got on top of me and started rubbing his dick against mine. We got on top of the covers and both of us never had had another guy jack us, so we decided to do it, and in a few minutes we both came with a huge load, we then showered together, and then during the night we both jacked each other 2 or 3 times.

After that we learned that we liked anal sex, and he used to stay over at my place frequently and we would do jacking and anal, as well as sucking and rimming. We never got tired of jacking each other.

He is straight married now, has 4 kids, and I am married to my husband (we are gay). He lives in Chicago and I live in Ft.Lauderdale. We see each other occasionally, and when we are alone we still have slept together and jacked each other off (as well as did sex), and decided it was not cheating, it was just reliving our younger times -- and getting each other off for feel good stuff. We both explode when we jack each other off.

I was in college and had my best friend stay over while my Mom was away for the weekend. He was 4 years younger than me, I was a senior and he was a freshman. We spent the night watching tv and having a couple of drinks, and came time to go to bed, and I asked him if he wanted to share my bed, or sleep in the guest room, and he immediately said he would share my bed. I had been sleeping naked, since my freshman year when I was in a dorm so I got naked and he did also, and we got into bed and turned on the tv to watch Saturday Night. About 15 minutes went by, we had huge boners, and he immediately got on top of me and started rubbing his dick against mine. We got on top of the covers and both of us never had had another guy jack us, so we decided to do it, and in a few minutes we both came with a huge load, we then showered together, and then during the night we both jacked each other 2 or 3 times.

After that we learned that we liked anal sex, and he used to stay over at my place frequently and we would do jacking and anal, as well as sucking and rimming. We never got tired of jacking each other.

He is straight married now, has 4 kids, and I am married to my husband (we are gay). He lives in Chicago and I live in Ft.Lauderdale. We see each other occasionally, and when we are alone we still have slept together and jacked each other off (as well as did sex), and decided it was not cheating, it was just reliving our younger times -- and getting each other off for feel good stuff. We both explode when we jack each other off.

Same with me. The first time we did it, I felt incredibly embarrassed and awkward. At the same time, I'd never felt anything like it. We did it at least a couple times every sleepover for years.

I live in Ireland and at the time my friend and I were about 13. I hadn't wanked myself before and was a late developer. I hadn't really got very much hair, I guess I still had a smallish cock at the time as I hadn't properly hit puberty. He was the opposite and had a neat bush above his cock which was proper teenage cock.

He was staying over and had brought a porn magazine. Our beds were beside each other, probably no more than a foot apart. We were looking at the porn magazine and both of us were getting really really hard. Then I suggested that we copy some of the poses that the girls in the magazine were doing. We were both in boxers so at first we kind made them into g-strings not actually showing anything. Then I took mine off and half covered my cock with the bed sheet in a pose and he did the same, we were kinda laughing as we went along. I will never forget that feeling of horniness and how hard I was at that moment in time but also the nervousness - I was totally shaking - but that feeling - wow!. I had a piece of ribbon beside my bed and decided to wrap it around my cock and do another pose. It didn't work and the ribbon just fell off. I was lying totally naked on my bed, I didn't cover up and then he tried the ribbon and he to was lying naked on his bed.

I knew he had started wanking from previous conversations and asked him did he want to try it now and he said sure. He began to wank himself off and then I asked him to show me. We sat on the sides our beds, opposite each other, knees touching. The atmosphere in the room was so charged, we were both so horny. He reached out and began to stroke my cock. I was covered in pre cum and he was just brining my foreskin up and down and massaging the head. It was ecstasy.

Then it was my go. He was covered in pre cum too and I remember the feel of his cock in my hand. It was smooth and soft yet throbbing hard. He was so turned on by my hand playing with his cock. I remember it didn't take long at all and he just came - not very much. Then he came back to me and finished me off - I didn't even have proper cum just sickly semen but it was intense.

We were both freaked out afterwards and went to sleep but for three or four years after that we fooled around at weekends or at sleepovers until we were 16 or 17. I am in happy hetro marriage now but I would love to have an experience with another guy like that again just to feel the sheer excitement, horniness and nervousness combined.

My first time jerking off and jerking with a bud was all at once, we were 13 at the time off from school on easter vacation. He was staying at my house for a couple days which was normal for us to have sleep overs at each others houses. One day we went roaming around the woods behind my house and after a while he just out of the blue asks me if I minded if he jerked off, I was like no go ahead...I really had no clue what he was talking about. The next thing I know is he pulls a much bigger dick out than I had and starts to stroke it, so he asks if I need to as well, I was hard just from watching so I pulled mine out and copied what he did.
It seemed to take a long time which I'm sure wasn't that long looking back now but when he shot his load I was shocked and just then we heard some noises and decided to split quick. I never did tell him that was my first time for anything like that but I practiced a lot after that day and was shooting in a couple weeks time. Then we progressed into doing it more often and helping eachother get off.
As for any advice on how to make it happen it's different with everyone you just have to get them horny enough to want to jerk it. Since my first time with him I tried to get a few friends to jerk with me and was successful too most of the time. Usually the method I used that worked the best was just get them talking about it and admitting they did it too. But I've also got them watching porn or skin mags too, or even having a few beers and some porn works too. A couple times I even pulled mine out and jerked in front of them which didn't always work but was still fun to be watched.

My first time I was 13, and it was with my friend who was a couple months younger. It kinda came out of nowhere, just watching American Pie. I mentioned I had a hard on, and he just said shall we have a wank. He had bunk beds, so I was on top bunk, him on bottom, both wanking. He came first and got it all over his legs so dashed to the toilet, leaving the door open and me on the top bunk shooting my load over the sheets. We regularly wanked together until about 19, he made big loads and I had good distance. Once did it in the woods behind my house, and in my conservatory with all the blinds open. We regularly used to sniff his sister's underwear and both cum in them.