I love stories about how guys first learned to masturbate. There are so many different experiences that lead to one of the most universal forms of recreation. Here is my story.
I first discovered masturbation when I was about 6 years old. I was an occasional bed wetter, and thankfully had a mother who made me feel OK about it. She just told me that when it happened, I should get out of my wet pjs and lay on a towel, and she'd wash up the next day. One of my few strong memories from that age was the night I wet the bed just a little, and stripped down and lay on a nice, fluffy towel. I lay on my stomach, and the feeling of the terry cloth against my penis was very nice, so I rubbed around on top of the towel. I got a little boner, and it felt even better. I just kind of squirmed around on top of that towel until I fell asleep. I think it relaxed me. In the morning when I woke up I remembered how good it felt, and did it some more before getting up. That was my first recollection of getting a boner, and I liked it.
The next night I thought again about how good it felt, so as soon as I got into bed I pulled my pjs off and lay on the towel again, rubbing around on it until I got a boner again. This time I stayed awake longer, and as I rubbed around, I could feel a strange urgency as the feeling got better and better. It got really intense, and suddenly I felt a warm, tickling pulsing in my crotch, and my penis became very senstive. So I stopped moving it, but held it firmly against the bed on top of the towel as this indescribably great feeling engulfed me. My first orgasm. I had no idea what it was, but I knew immediately that I would want to do that again. I put my pjs back on and fell into a heavy sleep.
Of course that became a nightly habit, and I slept nude and made love to my towel almost every night. On those rare occasions when my mother went to the store and left me home alone I'd slip into bed and do it during the day, and those were very special times.
I had a friend who slept over fairly often. The next time he was there we lay in bed talking for a while, and when he was ready to go to sleep, I matter-of-factly slipped my pjs off and rolled over onto my towel and began my nightly routine. After I did it for a while, he asked me what I was doing. I had no sense that there was anything wrong with what I was doing, though I was careful not to let my mother see me, so I just told him I was getting a 'good feeling.' He asked me to show him, so I pulled the covers down and showed him how I rubbed on my towel. He said, 'Oh, I do that too, but on my pillow.' I asked him to show me, and he agreed. He pulled his underwear down and pulled his pillow down and lay on top of it, and began rubbing on it, much like I did to my towel. I was somehow surprised to see that someone else did the same kind of thing I did, and then I went back to rubbing on my towel. I could tell when he got his 'good feeling,' because he got real tense and his butt dimpled when he thrust hard into the pillow as he had his orgasm. That excited me, and I came too. That was a lot of fun, and of course this became a staple of our sleepovers for years.
The next night I remembered what he did with his pillow, so I lay my towel on top of my pillow and rubbed on that. That was even better than using just the towel, since I could make a groove in my pillow and my penis was enveloped in a nice tight grip. That became my method from that night on. I'd climb into bed, arrange my towel on top of my pillow, and hump it to a great orgasm every night.
I stopped using the towel in favor of my hand (my friend showed me that trick, too) when things started to get messy when I was 13. But even today, many years later, I get turned on at the thought of me humping my pillow and towel when I was a little boy.