I enjoyed the recent post about how two brothers used a treehouse as their private masturbation place. I had a private place of my own, but not a tree house.
When I was growing up we had a detached garage that was pretty far from the house. It had a rickety stair up to the second floor, which though not finished out, had a floor and windows on each end, and it was where my parents stored extra stuff they no longer used but never got around to throwing away. When I was very young I discovered it was a great place to make little forts to hide and play in, and I'd take my friends up there and we'd play for hours. At 7 or 8 we of course did a lot of 'you show me yours and I'll show you mine,' and other innocent little naked games. Often it was just pulling down our pants for a few seconds to look at each other, other times it was more involved. One of my friends liked to wrestle naked, and it was more a rubbing session, where we'd rub our hard little penises on each other, than real wrestling. He was pretty adventurous, and even at an early age he liked to create dares like running down the stairs naked to the garage, putting our penises in each others mouths, and things like that. None of it was serious sex play, just fun. One time he spent the night and he dared us to go outside naked and run around the yard. I don't know what my parents were doing, but we spent an hour or so naked in the back yard, having a great time rubbing on each other and stuff, scared to death someone would see us.
At about 9 or 10 I discovered masturbation by rubbing on an old foam pillow I found up there. I found if I lay on top of it and humped it, I'd get this great feeling, which I began doing frequently when no one else was around. It was my little secret.
By the time I started to ejaculate when I was 12, I had thought of making a little hole in the end of the pillow and inserting my penis into it, and pretending to have sex with it. That felt really great, and I'd shoot into the pillow and lay there panting, thinking of how great that felt. I could use the same hole many times before it got too crusty inside, then I'd just make a new hole to use.
One day I was up there with a friend, and got the urge to do that, but had never broached anything like that with a friend. Somehow he asked if I masturbated (I don't know what he called it, but it wasn't the formal word for it). I admitted I did, and he asked how. I told him I used a pillow. He seemed puzzled by that, since I found he used his hand, and he asked if I would show him what I meant. So I got my pillow out of its hiding place and showed him the hole. He asked how I did it, so I pulled my pants down and mounted my pillow for a demonstration. I was pretty excited by this by that time, and I went to completion, orgasming into my pillow. He seemed impressed and asked if he could try, and I said yes. He pulled his pants down and lay down on my pillow, sticking his penis into the same hole I had just used. With a smile, he said he could feel my spunk, and said it felt good. He proceeded to hump my pillow, and soon went stiff and jerked in his own orgasm.
We were both a little embarrassed at what we had just done, but we both just sat there with our pants around our ankles idly playing with our penises, with the dregs still dripping out of our pee holes, and we agreed that was fun.
The next time he was over, he said he'd show me how he did it, and proceeded to pull down his pants and lay back, gripping his penis. He stroked himself for about five minutes by hand, then stiffened, and shot all over his stomach. I was really interested, since I had never tried that technique, but was willing to give it a shot. I followed his lead and jacked off. It was a little different, but felt just as good.
From then on we would sneak up there whenever we could and have masturbation sessions, alternating between using my pillow and using our hands. We graduated to doing it in each others butt cracks, but never tried penetration. I don't know why we didn't, but it did feel good the way we did it. Of course since we didn't always use my pillow, which meant we didn't need to clean up, I snuck an old towel up there, and we soon had a very crusty cum rag that we used for years. It would have been really gross if my mother had found that, or my pillow, but she never did (as far as I know).
The same friend introduced me to hand lotion up in the upstairs of my garage, and I was hooked. I loved the slick feeling of my hand on my penis while lubricated -- it felt much better than a dry hand, and from then on that's the way we did it. We also found that lubricating our butt cracks made that technique feel better, too. We experimented with various lotions, and found our favorite was Vaseline Intensive Care Lotion.
We kept that up until we started high school, then the frequency dropped off. We still did it occassionally all through high school, but it was very occasional.
I did it with four or five other friends, and my cousin, as well, but never as much with any of them as with that one friend. I can still remember him coming over to my house and us doing things in my room or out in the yard, and he'd whisper, 'Lets go to the fort.' That's all he needed to say. We both knew it was to masturbate together, and we'd circle around the back door so no one would see us go in the front, dash up the steps, crawl into the fort and get naked together.
The closest we ever got to being caught was once when we were naked in my fort doing each others' butt cracks, when we heard someone coming up the stairs. It was my mother, bringing something up for storage. I didn't even dare to get off my friend, and just lay there on top of him with both of us breathing as softly as we could. My mother didn't see us, but the thought of her finding us in that situation (laying naked one on top of the other) scared the you-know-what out of us, and we found we couldn't get aroused again that day after that incident. But the next day we were at it again!