I've seen a couple of recent entries that have similarities to my situation, so I thought I would share my
I was 7 or 8 when I learned how comfortable it was to sleep in the raw. It happened when my older cousin visited for a week. He was about 12 or so, and he slept nude. I was surprised when he stripped down and slid into bed naked, but I looked up to him, and decided to do the same. Being in bed like that with him felt really neat. We wrestled around a little bit -- nothing sexual -- and that felt even better. Both of us got boners, but that was all. I slept well.
When he left, I decided I would sleep naked, too. I usually slept in boxers, and slipped them off after I got under the covers. For some reason I figured my mother wouldn't like me sleeping like that, so I was careful to not get naked before she said good night to me. I was right. She caught me once or twice, and wasn't happy with me. I don't remember what she said, but it was clear that nudity wasn't in her play book.
I soon found that it felt good to put a pillow between my legs and rub my little boner on it. I don't know how I discovered that, but I think it was an effort to replay the wrestling I had done with my cousin, where we rubbed our boners on each other.
I don't know how long it took me to discover masturbation that way, but I don't think it took that long. Rubbing my boner on the pillow felt good, so I kept doing it, and WHAM, my penis would twitch and I had a wonderful feeling in my crotch that left me breathless and tired. I started doing that almost every night.
The reaction of my friends was interesting. One got indignant when I got naked in bed during a sleepover. He called me a perv, nakey-boy, and things like that. He had no interest in getting naked, and obviously thought I was weird for doing so. So I put my shorts back on and never tried to sleep nude with him again.
But another friend had a very different reaction. I first got nude with him before I tried it with my other friend (otherwise I doubt I would have done it with him). As soon as he saw that I had taken my shorts off, he said 'neat,' and did the same. We wrestled around for a while, rubbed on each other, etc. It felt great and was fun. When he fell asleep, I put my pillow between my legs and rubbed on it, and got my good feeling.
That started the sex play between us that lasted into high school. We'd sleep nude, go into the woods to find places to get nude and run around and play that way, etc. At some point we both admitted that we liked to masturbate, and would do it together, but that is all we ever did.
One of our favorite activities was to sleep out in his tent in his back yard, and when everyone was asleep in the house, run around the neighborhood nude. It was risky, which made it great fun. We almost got caught in car headlights a couple of times, but always were able to hide.
We had a scare one day. We were in the woods playing in the nude when an older boy stumbled into us. He was 15 or 16. We started to run away, but he told us to stop or he would tell on us. So we did, and he came over to us and examined us. I felt really exposed as he looked us over. He felt our penises, and seemed really interested, but after a few minutes he got a thoughtful look on his face, and said for us to relax, he wouldn't do anything. He just left. I thought he was thinking of doing something nasty, but he didn't. We went back to our clothes, got dressed, and went home, relieved.
That didn't stop us, though. We found a place further into the woods, and kept up our naked play.
Those were fun times. By the way, I still sleep nude, and hump my pillow. That's the best.