When I was 8, my best friend and I used to walk to and from the community swimming pool in the summer. There was a shortcut of about a quarter mile through the woods, and we never saw anyone else on that path. The normal way we went to the pool was by putting our suits on under our shorts and walking there, so that after we were done and took off our wet suits, we were naked under our shorts for the walk home. I always liked the feeling of being loose and free like that, and it felt good for my penis head to rub in the inside of my shorts as I walked. I'd get little boners almost every time. I knew it would have made mores sense to just carry my suit to the pool, but then I wouldn't have an excuse to go naked under my shorts and would miss the nice sensations it gave me.
This one day we were walking along and it was feeling really good, so I put my right hand in my pocket and reached around to play with my penis a little. My friend noticed and started to do the same. So there we were walking along, both playing pocket pool and sneaking looks at each other. It was exciting to be doing something naughty like that out in the open.
The next day we did the same thing, and I was just as excited. Halfway through the woods, my friend stopped and said, 'Want to see something neat?' Of course I said yes, and he had me follow him into the woods until he found a small tree, which he stood up to. He pushed his crotch into the tree, and grabbed around it with his arms and his legs, so he was essentially hanging there, pressing himself into the tree. He rubbed up and down on it for a few minutes and got really intense. Then he stopped and held tight and still, breathing hard. After a minute he let go and slumped down looking exhausted, but he had a smile on his face.
'That feels really good,' he said. 'You try it.'
I could tell he had something good there, so I walked up to the same tree and did what he had done. Being hard and stimulated already, it immediately felt good and nature took over. It wasn't long before my first orgasm shook me from head to toe. Boy, that felt good.
That became a daily ritual. Every day on the way home we'd stop in the woods and hump a tree, and I loved it. It felt better every time. I eventually found a tree that had kind of a double trunk, so that when I pressed my penis against it, there was a groove for it to fit in. That felt even better. Once we got into the habit of doing that, we innovated. I found that if I pulled my shorts down and put my towel up against the tree and rubbed into that crack, it felt really, really, good. When we did it we would both watch each other, and I really enjoyed seeing his bare butt flex as he thrust against his tree and towel.
That was great entertainment for the summer, but then labor day came and the pool closed so we had no excuse for a walk home from the pool. That's when my friend told me he did the same thing using his pillow on his bed, and we rushed to his room so I could try it. I wasted no time pulling my pants down and mounting the pillow he handed me, and watched as he did the same. It was great!
His mother came home from work about an hour after we got home from school every day, so we got into the habit of rushing home, stripping naked, and humping the pillows every afternoon right after school. Sometimes we did it in his bedroom, but other times we did it in the family room, which was fun because there was a big sliding glass door so that if anyone walked up they would see us. The risk made it seem more exciting. That was loads of fun, and we did that for several years.