This is the true story of me and my best friend.
It was my brother who taught me how to masturbate, using my hand. He was 12 and I was 10. Later he told me he taught me for two reasons. First, he didn't want me to miss out on all the fun until I discovered it on my own. Second, since we shared a room, he didn't want to have to hide his own nocturnal activities. So he showed me, and we jacked off next to each other almost every night before going to sleep. Sometimes we did it to each other.
Once I learned, I longed to do it with my best friend, Will. He was my age, and we were together almost all the time. I greatly admired his looks. He was blond, had high cheekbones, a cute button nose, slightly slanted eyes, and was slim but not skinny. I always thought of him as cute, but never said so to his face.
Despite many hints on my part, I was never able to engage him in any kind of masturbation. The only thing of a semi-sexual nature we did together was our routine of 'wrestling' before going to sleep when we had our frequent sleepovers. We had been doing this since we were about 7 or so, and it was always the same. Will slept in just shortie PJ bottoms, and I slept in boxers (funny, I didn't like wearing boxers during the day, but I liked them for sleeping). What we did wasn't really boxing; it was more just rolling around with each other in bed, rubbing against each other and feeling around. For me it was terribly arousing - the skin on skin touch, full body contact, feeling him. I loved to feel his legs, his butt, his stomach, his neck, and the contours of his collarbones. We would each always do fleeting feels of each others' crotch, but not as long as I'd like. I would always get a raging boner, which Will obviously noticed, but he always stayed soft. We would wrestle for about a half hour, then stop, and Will would fall asleep almost immediately. He was a heavy sleeper, so, after my brother taught me how to jack off, I'd do it laying next to Will, with our bodies touching. It was always a good orgasm (dry), but I longed to do it with Will.
One night when we were almost 13 was a turning point. We were sleeping out in my tent in the backyard. It was a warm night, so we were on top of our sleeping bags doing our wrestling routine. There was a full moon, so we could see pretty well. In the course of our wrestling this night, Will put his hand in my crotch, and instead of immediately moving on like usual, he kept it there. I stopped moving, encouraging him to keep his hand there. He felt around a little, holding my boner between two fingers, cupping my balls, that sort of thing. He did a little up and down motion, then quit, laying over on his back. I took that as a hint (I hoped that was what it was!), and put my hand on his crotch and held it there. For the first time, he wasn't totally soft. He was at least half hard. I played around with his penis (both of us were about 4 inches hard, and hairless at this point) and balls for a few minutes, and he got totally hard.
Will was laying there quietly with his eyes closed, and I could tell he was enjoying what I was doing to him. I decided to take a risk and go a little farther, so I put my fingers into the fly of his pjs and gripped his penis skin-on-skin. This was the first time I'd touched another person's penis other than my older brothers, and it was really exciting. It felt hard and soft at the same time, about as big around as my thumb, and warm. After doing that for a bit, I took the next step, and unsnapped his pjs, letting the flaps open, and his penis stood right up, almost perpendicular to his body, unlike mine which slanted upwards a lot.
I slid Will's pjs down his hips to get better access, and proceeded to play with his hard little penis in earnest, working up to a full-blown masturbation movement up and down using my forefinger and thumb in a grip like I used when I jacked off. Will put his arms behind his head and relaxed, and I could tell he was enjoying my ministrations. It didn't take long before I could feel him tense and hold his breath. He arched his back, and I could feel his penis begin to throb. I just held my hand still, gripping tightly just below the head, as his penis lurched like it had a life of its own. At about the third pulse, I felt a warm wetness engulf my fingers, and realized he was coming, which surprised me. I had seen my brother come many times, but I had never had a wet orgasm, and here was Will dribbling all over my hand and his stomach.
After Will calmed down, he looked down at my hand still holding his penis, and asked, 'What did you do, spit on me?'
'No, you had a wet come.'
'That's never happened before.'
I was amazed that I had given Will his first wet orgasm.
I got up and grabbed an undershirt and wiped Will and I up, and, as always, Will fell asleep almost immediately. He didn't even pull his pjs back up. So I lay next to him and jacked off desperately, but this time holding his penis and feeling the warm softness of it and his ballsack. Oh, it felt so good, and I had a great climax, though still dry.
A day or so later, I was on my computer in a chat room chatting with another kid that also knew Will. We three often chatted back and forth. He asked me what Will and I had done the other night. I asked why, and he said Will had said he'd had a lot of fun while sleeping over, but refused to tell him what we'd done. I was tempted to tell him, but decided against it because I knew Will would be upset if he found out. So I just told him it was between Will and I. He probably guessed, but he dropped the subject. What was neat was that I now knew for sure that Will really liked what I had done, so I could do it again.
The next time we had a sleepover was the next weekend, at his house. There we always slept on a mattress that they stored under a couch in the family room. Before going to sleep, we started our normal wrestling session, but this time Will pulled off his pjs so he was naked, so I pulled off my boxers. He pulled a sheet over us in case anyone came in they would see we were naked, and we went to it. The body to body contact this time was even better than ever before, and we rubbed our crotches against each other like really dirty little boys! When Will started feeling me in my crotch, I again lay still and enjoyed it, then he stopped and I played with him like I'd done last week. I again brought him to a wet orgasm, cleaned him up, and jacked off holding him while he slept.
The next night I lay in bed slowly stroking my hardon under the sheet, thinking about what Will and I had been doing. It was a great turn-on for me. I didn't notice my brother walking in, so all of a sudden I saw him standing above me, smiling. 'So what has you all boned up tonight?' he asked.
I hesitated a minute, then decided to tell him. 'I finally did it with Will.'
'Tell me about it.'
So I did. I told my brother all about it, and he got turned on, as well. As I was telling him, he got naked and got in my bed with me, and we played with each other while I told the story. We both got really turned on, and came in each others' hands after I finished telling my story.
Will and I kept doing that for several years, following the same scenario. I never pushed him to do it to me, but hinted several times. He never did, but I didn't care. I enjoyed our wrestling and playing with him and jacking off afterwards while I played with his genitals. And my brother and I kept up our mutual activities until he went off to college.
These are some of my finest memories.