I've enjoyed the first time and early experiences stories here. I have fond memories of my early years, so I thought I'd share them.
I was about four when I first started masturbating. I didn't have a clue about what I was doing; I just knew it felt good and did it a lot.
I always liked the feel of thick terry cloth. I can remember sucking my thumb while rubbing a thick towel between my fingers. For some reason I would get an erection while doing that. I can remember it feeling tingly and good, and one time I rubbed the towel on it, and it really felt good. Liking that, I pulled my pillow down to my crotch, pulled my pjs down, put the towel over the pillow, and gently rubbed my penis on the towel while I rubbed the other end between my fingers. It was a delicious feeling. At this early age I didn't mount the pillow; I lay on my side pressing my crotch into the pillow.
I don't remember how long I did this before I had my first orgasm, but I do clearly remember the surprise and awe I felt the first time it happened. I felt a slow build up to some sort of climax, then all of a sudden I felt pulsing all through my crotch and the most incredible pleasure, and afterwards, I felt really warm, relaxed, and tired. I'd usually fall asleep quickly after that, and often woke up in the morning with my pjs still pulled down and tangled around my legs. I finally got the idea to take them off completely, and that was more comfortable.
One time when I was about 6 I had a friend for a sleepover. I thought he was asleep, so started my nightly ritual. But he wasn't asleep, and asked me what I was doing. I told him I was rubbing on my pillow. He asked why, and I told him because it felt good. He had me pull the sheet away so he could see what I was doing, then said he wanted to try. He pulled his pjs down, moved the pillow so the other end of it was at his crotch, and started rubbing like I was doing. So there we were, the two of us humping opposite ends of the same pillow. I tried to hold off the climax to give him time, and sure enough, after a while I could see a look of concentration on his face and he humped harder, then he stopped and I could see his butt tensing. Then I let loose, and we were both having the good feeling at the same time.
He said he really liked that, and wanted to do it again as soon as we woke up. That, I think, was the first time I'd done it at any time other than at night, and was the beginning of my long term habit of doing it whenever I could.
My friend and I had plenty of sleepovers after that, and of course always used my pillow. This went on until we reached puberty and started to make a mess when we did it. We learned we could get the same feelings using our hands, so switched to that mode. I still occassionally hump my pillow, but now I mount it and do it from above.
I'm still friends with him, and we sometimes reminisce aobut the fun we had as kids. As adults we have masturbated together a couple times for old times sakes, and it is always fun.