The recent post about 'My Early Times' was so similar to my childhood that I thought it was almost me.
I also masturbated from an early age, around 5 or 6, maybe younger, in a way similar to the recent post. I'd lay on my side and pull my pillow down to my crotch, put my leg over the pillow, and kind of roll into the pillow so my penis was nestled into it, and gently hump it, eventually speeding up and humping harder until I had my dry orgasm.
I did this a lot. Unless I was unusually tired, I'd do it every night before I went to sleep. It was a great way to relax and end the day. On nights when I was really tired I'd think it over, and it was a conscious decision not to, and I promised myself I'd do it in the morning. On mornings that I didn't have to get up early, like on weekends, I loved to luxuriate in my warm bed for a while, rubbing my penis on my pillow and eventually going to it for a relaxing and pleasant orgasm. Often I'd fall back asleep for a few minutes because I was so relaxed.
I had one really embarrassing moment, though, when I was, I think, 8 years old. My mother's college friend came to visit for about a week, and she had a son a couple of years older than me. I think he was 12, but might have been 13. I liked him, since he paid attention to me and was nice to me. Since I had a large bed, he slept with me. I liked that, since we lay there talking until late, but I missed my opportunity to use my pillow.
The second morning he was there, I completely forgot about him being in my bed. I woke up already on my side, facing away from him and with my pillow between my legs. I pulled my pjs down and started my gentle humping, and after about 5 or 10 minutes of that had a wonderful dry orgasm. I lay there holding the pillow to my penis for a while, enjoying the throbbing, then rolled onto my back. To my horror, I rolled right up against my bedmate, and for the first time I remembered I wasn't alone. I looked at him, and he was awake, looking at me with a big smile on my face.
He asked me, 'That feel good?'
I didn't know what to say, so said nothing, but pulled my pjs back up to hide my little boner. He could tell I was embarrassed, and being the nice guy that he was, tried to put me at ease by saying, 'Don't worry, I do that all the time.' After a pause, he said, 'But I do it a different way. Want to see?'
I just nodded my head, and he pulled down the sheet and I saw he also had pulled his pjs down, and was holding his boner in his hand. It looked huge to me, but it wasn't really all that big. Maybe 4 1/2 inches, and he had just a few wisps of hair at the base. He then started jacking off, which was new to me. I watched carefully as he rubbed his hand up and down, and when he began to stiffen, he shot a couple of small jets of white stuff onto his stomach. I knew he was having the same feeling I had when I did my pillow thing, but the white stuff was news to me.
After he cleaned up, he explained what the white stuff was, and we went about our business for the day as though nothing had happened, though of course nothing really had. But I couldn't get it out of my mind, and was looking forward to doing it in bed that night.
When we went to bed I didn't know what to do to initiate it. I didn't feel like I could just start masturbating, but he took charge and pulled his pjs down and started in, so I pulled my pillow down and went to it.
We did that side by side both morning and night the rest of the time he was there, and even did it one afternoon when the grownups were out shopping and we had some time at the house alone. I liked to watch him as he did it, and I noticed that he was watching me, too. It was a fun thing to share.
Over the next several years his mother and he visited several times, and we'd always do that together. It was very special.