Memories of these times have given me some very erotic and powerful orgasms over the years. I still regret not giving him the pleasure of satisfying me completely.
By the time I was 14, I had never actually taught another person how to masturbate. I had enjoyed masturbation experiences with several other guys but they had usually taught me things as they were usually more experienced than I was. One warm summer morning, I was sleeping late as I liked to do and a playmate of my younger brother was over. He came into my room and interrupted my sleep as he sat on the bed talking. As was the norm at that age, my cock was erect, expecting the usual jacking off it got every morning. By then I was jerking off every night before going to sleep and every morning after waking up and at least one other time during the day. During summer school breaks, I probably beat it off several times during the day! Anyway, I lay there underneath a sheet, not noticing that my cock was erect but Larry did. I guess he was curious. He was about 10 at the time and was likely just becoming aware of his sexuality. Before I was aware of what was happening, I felt him grasp my cock with his hand. I was startled but didn't resist. He proceeded to play with it, slapping it back and forth and feeling its size. I made no attempt to touch him, just let him explore mine. Of course the sheet covered me and he couldn't see it. After a short time, he was called away to play with my brother. Nothing else happened for several weeks until he was over again one afternoon. I was upstairs in my room working on a model and he joined me there. We worked on the model for a while but soon the conversation got around to our cocks. I asked him if he played with his and made it tickle. No, he didn't know about that but wanted to know more. We ended up with his zipper fly open and his erect, immature 10-year-old cock protruding through for me to play with. It was so small that I couldn't really grasp it for a full stroke but just held it with my thumb and forefinger and moved his circumcised skin back and forth. Of course he had nothing close to an orgasm but it was pleasant enough and exciting enough that he enjoyed it. Several weeks passed and there were a few occasions when he wanted me to play with his cock and of course I was quite willing to do. He never experienced the tickling sensation that I had described to him that jerking off would produce but apparently it was pleasant enough that he would frequently come to my home early in the morning before I had gotten out of bed and crawl into bed with me. I never actually taught him how to masturbate my cock but he would play with it and get me quite close to orgasm. Somehow, I felt uncomfortable in encouraging him to bring me to orgasm. One morning, he came in quite excited and confessed to me that he had played with his cock and had made it tickle and feel good just like I told him it would. After that, I would always be able to give him a good tickle. As a 10 year old then an 11 year old he wasn't mature enough to ejaculate but he sure enjoyed the pleasure of his dry orgasms. He didn't like the idea of lubricating his cock with spit and preferred me to beat him off dry. Of course while he was playing with my cock, it was dripping precum which he would always wipe off with the sheet. I tried to convince him that using lubrication would feel much better but he just didn't like it. Soon, he wanted me to change my technique of jerking his little cock with my thumb, fore and middle fingers and wanted me to wrap my hand around it. It was too small to really hold it well but I would do it the way he liked it. I preferred to be able to watch his cock as he began to tickle and see how red it would become. Hidden inside my hand, I couldn't observe that. Our masturbation sessions occurred weekly for about 2 1/2 years. We had a number of favorite places where we could go and have our masturbation sessions. Still, he rarely brought me to orgasm. I was embarrassed for him to see my cock shoot off as he was so turned off by the cock juice that flowed so freely and I felt that if he saw my cock explode with cum, he wouldn't like that at all. Usually, after I had made his cock tickle and he had begged me to stop beating him, I would turn away, give my cock a few quick strokes and shoot my load out of his view. As he got older, his cock grew quite a bit and it now filled up my hand when I would stroke him and he began to produce a few drops of clear, slick cock juice while I was playing with him. Now, he understood and enjoyed the feeling of my masturbating his cock all wet and slick. The last time I brought him to orgasm occurred when he was about 13 and I was 17. We were with a group of guys who were camping in a group camp. We each had military style cots to sleep on and that night he pulled his cot over close to mine and shortly after lights were out, I felt his hand under my blankets. I felt for him and found he was naked below the waist with his cock fully hard. We spent a long time that night playing with each other's cock and I felt that his was well lubricated from cock juice and several times, I added a copious amount of my own and gave him at least two good orgasms before we went to sleep. The next year, I was away at college and had decided that it wasn't a good idea to continue this relationship so when I came back home for summer break didn't pursue any occasions to masturbate with him. One afternoon when we were alone at my house, he asked if I remembered how much fun we used to have. I told him I sure did and he wanted us to do it again but I resisted. He said that his cock had really grown a lot in the past year and wanted to show me. I acted like I wasn't interested but he, at 14 was as horny as I used to be when we first began so he proceeded to drop his pants and show me his erect cock with his big, hair-covered balls and the thick bush of hair growing around his cock. He then wanted to show me how he could shoot cum and proceeded to jerk himself off as I watched, uncomfortably. He stroked himself and in just a short time, shot several jets of thick, white cum that splattered on the floor in front of him. He tucked his softening cock back into his pants with out having the opportunity to give me the same relief that I so desperately wanted and needed. Again, as I had done so many times before, when he had gone, I grabbed my cock and stroked it into a cum-spewing orgasm with my cum splattering with his on the floor. Never again did we mention the exciting times we had experienced during those almost 4 years.