I love all the descriptions of first time experiences. Here's mine. I hope you enjoy it. I'm going to enjoy writing it, since thinking about it is a very pleasant memory.
I don't know how old I was when I first started masturbating, but it was very, very young. I can remember reaching into my pants to play with myself at least as far back as kindergarten, and I think it was earlier than that. Sometime around then my memory started to stick, so I remember some things about my life at that age.
One of the best memories was my nightly exercise after my mother tucked me in. She always had me wear just shortie pjs, with no underwear. After being cooped up in tight undies all day, it always felt good to dangle free. For some reason it always excited me, and I got little boners while enjoying the feeling. To this day I like that feeling.
Like many kids, I had a favorite blanket that I slept with. Mine was a very soft terrycloth one that resembled a towel. My mother still has it as a memento of my childhood, since I used it for so many years. But she didn't know what I used it for after she put me to bed.
I can remember sucking my thumb while holding the blanket to the side of my face and rubbing the nubs of the terrycloth under my fingernails. For some reason that was comforting to me. Even more comforting was what I was doing with my other hand. I would grab the blanket in my other hand and shove it down into my underwear, and rub my penis with it. It would soon get hard in an immature little erection. I would roll on my side, almost onto my stomach but not quite, and suck my thumb and rub my penis. It always felt so good that I never argued with my mother about going to bed early. I always looked forward to my little private time.
I would suck and rub for a while, probably about 5 or 10 minutes, and then the warm throbbing would start. I'd press myself hard into the blanket and the waves of pleasure would roll over me. I'd lay there panting for a few minutes, then just drift off to a blissful sleep.
I did that until I started to ejaculate at age 12, and the mess became too obvious. Instead of my blanket I'd use a hand towel that I could shoot into and then hide under my mattress. When it got too crusty I'd slip it into the laundry basket and get another one. By that time I'd stopped sucking my thumb, so I didn't need the large blanket any more.
I can remember when I was 7 or 8 a friend slept over for the weekend. I think his family went out of town. On the first night I felt like doing my thing, and I debated with myself, but decided to go ahead. So I did. He saw me, and about halfway through, he asked me what I was doing. I didn't know what to call it, so I just said I was 'making myself feel good.' He watched closely, and when I had my orgasm he could tell I was enjoying it. The next night he asked me to show him how to do it, so I did, and there were the two of us going at it side by side. I was surprised that he came before I did since, according to what he said he'd never done anything like that before. I was excited to see the look on his face when he had his orgasm. It was a mixture of surprise and pleasure. He loved it. We started having sleepovers nearly every week from then on, and he always wanted to do that with me. It was a lot of fun. He said he was doing it every night, just like me.