When I was 16, I went on a three day backpack trip with a friend who I will call Rick (not his real name). He and I had been friends for 5 or 6 years, having been in Scouts and on the swim team together. This was the first time we'd been alone with each other for an extended time.
The first night, Rick and I lay on top of our sleeping bags in the tent (it was a warm night), in just our underwear. We talked for a fair while, and the conversation inevitably moved to sexual matters. We were both careful of what we said, feeling the natural nervousness of broaching such a subject the first time. It turns out neither of us had been with a girl, so our conversation on that topic didn't last long. There was a pregnant silence for a minute while we both struggled with how to bring up what turned out to be on both of our minds. I finally asked, "You ever do anything with anyone?" That didn't really come out and say "boys," but since neither of us had done anything with girls, the meaning was obvious.
"A couple of times, you?"
"Me too."
Again, a silent period. Then I said, "I've done things with my cousin and a couple of friends."
He again said, "Me, too."
I wanted to hear more, so I asked him how it had happened the first time. He told me, hesitantly at first, but then he got into it.
Turns out that when Robin, another friend who was in Scouts with us, turned 13, he had a sleepover with about 6 friends. I had been invited, but was out of town with my parents. I never knew what I'd missed since no one told what had happened at that sleepover. Robin had a long reputation for having no hang-ups about nudity and stuff. At summer camp he'd prance around the tent nude, shaking his thing at us, thinking it was enormously funny. He also jacked off in plain sight of the rest of us, though we were inhibited enough to do it quietly under the covers, trying to hide it from the others.
We all knew we were doing it, but we just didn't want others to see us.
Robin's birthday party turned out to be a lot of fun, I found out. I wished I'd been there. Robin, as usual, made up a game, and it basically consisted of chasing each other around, and if you were caught and the guy who caught you could pin you to the floor, you had to take off a piece of clothing. The end-point was if you lost every piece of clothing, you had to lay still and the winner got to do anything he wanted to you.
Rick was the first to lose, at the hands of Robin, so Rick lay quietly on the floor, awaiting his fate. He had no idea what was to come. Robin had put out a jar of Vaseline and a roll of paper towels earlier, and Rick had wondered what they were for. He was about to find out. Robin got them, and removed his underwear, revealing a hardon. He put the jar of Vaseline over his penis, and stuck it in, getting it all covered. Then he had Rick get on his hands and knees and got between Rick's legs and mounted him, pushing his boner into Rick's butt. It took a while to get centered on the hole, but when he did, he slid it slowly in. Rick said it hurt a little at first, but felt really good. He was totally taken by surprise, as was everyone else in the room. They all came over to watch in surprise. Robin told them he'd always wanted to try this, and this was the first chance he'd had. He told them it felt really good.
Rick meanwhile was really beginning to enjoy it, and Robin stroked in and out slowly at first, then got into a frenzy, until he stopped, and Rick could feel pulsing in his butt. Robin collapsed on top of him and just lay there, shaking.
After recovering, Robin asked Rick if he wanted to try it, and he did, so they reversed positions and Rick got greased up. He told me it felt so incredible as he slipped into Robin's butt, and he did Robin like Robin had done him. By that time the other boys had coupled up, and everyone was going at it, either on top or on bottom. Rick said they each had at least three, some four, gos at it, with a different boy each time. He said it was a pretty sloppy mess, but they had a great time.
So that was the first anal sex he or any of the others had ever experienced.
He said he and Robin got together several times after that to repeat the experience, and that he loved it.
By this time I was totally turned on, and my boner was tenting my underwear badly. And Rick was sporting a hardon, too. There was a little time of silence, then Rick asked me, in a whisper, "You want to give it a try?"
I didn't have to think long. Clearly I was going to have to relieve myself somehow, and that way sounded really great. So I answered in the affirmative, and Rick pulled a tube of Vaseline from under his pillow. Obviously he had planned this in advance. He said, "Here, you go first," and handed me the Vaseline. I hesitated a second, and he pulled his underwear off, revealing a nice long, slim penis. I was glad to see it wasn't too big; I was afraid it might hurt. Mine was slim, too, which was going to make it easy on both of us. I slid my underwear off and smeared a good amount of Vaseline on my penis.
Rick got on his hands and knees with his butt toward me, knees as far apart as he could get them. I scooted up behind him and pointed my penis at his hole, and slowly and gently pushed. It was kind of awkward at first, but I slid into him without any problem. And boy, did it feel good; tight and warm. The ring of anal muscles felt really good as I moved in and out. I started out slowly at first, then got into a rhythm. I didn't last long. The combination of being so turned on by hearing Rick tell the story of the birthday party and the intense stimulation his bottom was providing pushed me over the edge and I climaxed with a bang. I was holding onto Rick's hips, and pushed in as hard as I could, and I could feel my semen squirting into him. It felt like I came gallons, but of course it wasn't really that much. But it probably was the most I'd ever come. I collapsed onto Rick's back, breathing hard.
After a few minutes I got back up, and slid out of his bottom with a pop. My penis was really sensitive from all the action. "Your turn," I said, and dropped down on my hands and knees. Rick got behind me and greased up. He moved up and put the head of his penis at my hole and told me to relax. I did, and he pushed, and his head went in a little. It hurt at first, but Rick just held it there until I got used to the intrusion, then slowly slid all the way in. I felt really full, but there was no pain, and it actually felt good. I hadn't been sure ofwhat to expect.
Rick started stroking in and out, and really got into it. When he climaxed, he held still, as far into me as he could get, just like when I came in his bottom. He grunted at each throb that I felt in my butt, and I could feel a warm wetness spreading inside me. He also collapsed on top of me, and breathing hard, said, "That was sooooo good. Thanks."
When he pulled out, we both lay down next to each other, spent. I was amazed that we had done that, and glad of it.
We did it again before going to sleep, and again in the morning. When we stopped for lunch Rick asked if I wanted to do it again, and I sure did. We moved back away from the trail where we couldn't be seen if someone came. Rick got his sleeping bag out so we would have something to do it on, and we both stripped naked. I did him first, then he did me, and afterwards we lay together and took a short nap.
That was pretty much the pattern for the rest of the pack trip. I don't know how many times we did it, but it was a lot. While hiking we told each other about everything we had done with other boys, and that kept us well aroused, so that when we stopped, we'd have a go at each other. By the end of the hike my penis was so sore I was afraid it would drop off.
Rick and I got together many times after that. And guess what we did! We even had Robin join us once, and we spent an evening doing each other.
I don't think any of us was actually gay; we all married and had kids and happy families, but we get together for a camping trip at least once a year, and go at it like kids again.