I've always thought it odd how hard it is to describe how it feels to masturbate and orgasm. Words just don't do it justice.
I started masturbating when I was around seven years old. I'm not sure how I discovered it, other than finding that it felt good to rub my penis, and one day I got this fantastic feeling that was so good that I kept wanting to do it anytime I was alone. I tried it a lot of different ways, like rubbing on my mattress, on my pillow, and using my hand. I did it laying down, sitting in a chair, standing up. I did it in my room, outside in the yard, in the family room while watching TV, and even in the back seat of the car when my mother drove me places. I didn't know if other boys did it, but I didn't care. I loved the feeling.
When I was 8 or 9, my best friend was sleeping over, as usual. He did on most weekends. On Saturday morning we were watching TV on the couch in the family room in our PJs. I had my hand in my lap, and my little penis got hard, and it felt good to lightly stroke it through the soft cloth, as I never wore underwear under my PJs. My friend did, though, which I could never understand.
It was feeling better and better, and I decided I wanted to get my good feeling, even though my friend was right there. So I lifted my butt off the couch and pulled my PJs down to my knees. My little penis was sticking straight out, and I gripped it between my finger and thumb and began stroking it. My friend was staring at me wide-eyed, as though he had no idea what I was doing, and I'm sure he didn't. I didn't care, because it felt good to me. I rubbed it until I got my good feeling, then pulled my PJs back up. At that point I felt funny about having done it in front of my friend.
He was still looking kind of surprised, and asked me why I did that. I said I did it because it felt really good. He said 'Oh,' and dropped it.
After that incident, I never hesitated to do it in front of him if I wanted to get my good feeling. I noticed that it was fun to have him watch me, and I was surprised that he never showed any sign of interest in doing it to himself. He just watched me.
A couple of years later, when we were 11 or 12, he finally asked me what it felt like. I thought about it, and found it hard to explain. I'd done it hundreds of times, but I couldn't describe the feeling. I told him it kind of felt like a tickle that felt better and better until I got close to the end, then my penis would twitch and feel really good. I told him it would twitch like that for five or six times, then I'd feel tired and really relaxed.
'That all?' he asked. I said no, but it was hard to explain, and that maybe if I did it I could describe the feelings as I did it. He said OK, so we went up to my room and I dropped my pants, lay on the bed, and started in, giving him a running commentary as I did it. It was still hard to describe, but I did my best, and when I had my orgasm I couldn't talk at all until the throbbing was over, and then I was panting and all I could say was, 'Boy, that feels good.'
I asked if he wanted to try, and he said he might, but he made no move to do it, so I pulled up my pants and we went about our business.
A couple of days later he was over and mentioned that he had tried it, but didn't feel anything good. I asked if he wanted me to do it to him, since I knew what to do, and he agreed. So for the first time he pulled down his pants in front of me and lay on the bed. I reached for his limp little penis and rubbed it to get it hard. I asked if he had gotten it hard when he tried to get the good feeling, and he said 'no,' so I knew what his problem was.
After playing with it for a minute or so, it got hard, and I started to rub it like I did mine. He said he was starting to feel good, and sounded surprised. I kept going, and after about five minutes I sped up and gripped harder, then suddenly he stiffened. I felt one throb in his penis, a pause, then four or five throbs in close succession. He had his head thrown back and his mouth open, and was moaning in pleasure. I just held onto his penis as it calmed down and began to get soft. He looked at me and said, 'Now I know what you mean. That feels great!'
From that day on he joined me in getting our good feelings whenever we were together. We found a great hiding place in the woods where we could do it naked in the sun, and that was the most fun. He finally admitted to me that he had been a little grossed out at first when I started doing it in front of him, but that now he wished he had joined me much earlier. He felt he had missed out on some good times.