Going Too Far With My 13-Year-Old Neighbor

As soon as Tim moved in, I knew I wanted to get into his pants. He was skinny and smooth, like me. He smelled nice - something about the laundry soap his mom used. It wasn't easy getting sexual with him. Even at 14, I knew I had to tread carefully, so as not to get tagged as a weirdo - or so I thought at the time. So, over the course of a month or two, as he and I became better and better friends, I'd try to bring up sexual matters in conversation, but he wasn't buying it. Then, one day, out of the blue, while fiddling around with the metal spring clamp on the luggage carrier on the back of his bike, he said, "I wonder what it would feel like to get your dick caught in this thing?" That was the opening I needed! We talked about getting one's penis and testicles caught in various situations, and finally, we worked it out that we'd go in the bushes behind my house, and I'd try putting my dick under the luggage carrier spring clamp. I insisted that he had to pull his shorts down, too, even though it was only I who was going to try out the clamp. We both reluctantly pulled our shorts and underwear down at the same time. We were both hard. I can't even describe what a delight it was to see his cock and balls, after hoping, and waiting for more than a month. I was a bit surprised at how skinny and small his penis was, but so happy to see it. It was all I could do to not reach out and touch it, maybe put it in my mouth. But I restrained myself. I was still concerned about seeming to be a "weirdo." So, I gingerly walked up to the bicycle, lifted the clamp, and placed my dick under it. I let it down slowly, and was disappointed. It didn't feel like much of anything. I told Tim, and he tried it, with the same result - not much of anything. We pulled our pants up, and that was that. Fast forward a month, and we had become jerk-off buddies. While my mom was glued to the TV and her soap operas downstairs, we'd lock my bedroom door, and we'd trade places on my bed, one guy jerking the other guy off, and visa versa. At first, he didn't ejaculate. He'd have an orgasm like an adult, and as far as I could tell, it felt the same to him as it did to me, but nothing came out. Then, after a while, he could spit out a few drops of mostly clear cum. We experimented with hollow chess pieces. I could fill a knight or rook with creamy white cum, whereas he couldn't fill a pawn. He actually felt bad about that, like a competitor that can't win. I reassured him over and over that eventually he'd cum as much as me, or more. In time, we discovered a new technique. I don't remember how or why, but we figured out glans rubbing. If you've never had that done, you're in for a treat - if you can stand it. When someone rubs the palm of their hand over your glans, the tip of your penis, it is a horrible tickle-like feeling. You want to get away. You have to be held down, or you'll squirm away. But then, after a minute or so, it transmutes into something remarkable. It feels like you have to cum and pee, at the same time. But usually, neither happens. Later, I was with a guy in whom glans rubbing triggered an involuntary release of urine, which intrigued us both. Sometimes, a guy will ejaculate. But usually, it just feels great, and you can keep going for quite a while. So, Tim and I were doing that. His dad had given him a stop watch, and one day we decided that the effect might transmute again. From squirming, to wonderful, and back to squirming, or something else, or maybe we'd finally ejaculate. We didn't know. We decided that we'd challenge each other to go seven whole minutes by the stopwatch, no matter what, and see what happens. I went first. We were both totally naked. I laid down on the bed, while he sat next to the bed in my rolling chair. He started the watch, grabbed my dick, and started rubbing. As usual, it was too much, and I squirmed away. So, he climbed on the bed, on top of me, so that his knees were pressed against the palms of my hands, and his delicious little round butt was practically in my face, just below my chin. I had a clear view of his smooth, hairless, pink asshole, which I could look at for hours. It hadn't yet occurred to us to lightly touch around each others' assholes or stick fingers in. That pleasure was to come later. And later, it did. We learned to press against each others' prostates, to try fisting (unsuccessfully, only making it to four fingers), and other things. Anyway, there I was with him kneeling on top of me. Theoretically, I couldn't squirm away, although I'm sure with a grand effort, I could have shaken him off. But I didn't want to. I wanted the 'torture' as we called it. He restarted the stopwatch and started rubbing me, and I squirmed and squirmed, but at the same time delighting in the very strong sensation. In time, it did change, as expected. It became less intense, and much more delightful. This was before we learned edging, so it was a way to enjoy that semi-orgasmic feeling while holding off orgasm. I lasted the whole seven minutes without peeing or cumming. Toward the end, my glans started to sting a bit. When we hit seven minutes, Tim quit rubbing, and started jerking me off. I came almost instantly. After I came down from the ejaculatory high, and wiped up the cum, I noticed my glans was quite red. Oh well, no big deal. Now, it was Tim's turn, and we did the same thing. I kneeled on his hands, and gave him seven minutes of treatment. Of course I couldn't see my own anus, but remember thinking how cool it was that he had a clear view of my ass, since it was right in his face. In that kneeling position, I felt the cool air right on my anus, and it was nice. Very nice. My penis became hard again as I hovered over my neighbor-friend. And I rubbed and rubbed. At first he squirmed considerably, and then he settled down, enjoying the sensations as much as I had. Finally, the time was up, and I stroked him to a quick ejaculation. He released his usual few clear drops, which excited me all over again. I grabbed a paper towel and tried to clean up those drops off his stomach and the tip of his dick. When I touched the paper towel to his glans, he jumped more than usual. Of course one's glans is sensitive after cumming, but his was red, like mine, and he jumped more from a stab of pain than just a post-orgasm sensitivity. Fast forward a day. After school we got together again in my room. We were both horny, but neither of us wanted to masturbate in any way. We showed each other our dicks, both soft, and each had a small crescent-moon shaped scab across the top. My scab was more prominent than his, but we both had obviously gone too far with the rubbing. Fortunately, neither of us was freaked out. We had scraped our knees and other parts countless times, and so had no fear that this was anything serious. And it wasn't. After a few days, we healed up just fine. Being the horny little devils we were, we went right back at it, trying for nine minutes the next time. But, we learned to use some oil to prevent subsequent injuries. We found, to our joy and amazement, that the oil made the terrible initial sensation even more intense. A few years and hundreds of mutual masturbation sessions later, after we had both grown full hair on our genitals, both became around six inches long when hard, and even had facial hair, we ended up going to different schools and losing track of each other for a while. Several years after that, we met up, and compared lives. Both were married and had families. He had three kids, I had two. Although he had a degree in mechanical engineering, he was running his own car repair shop. I went into business and computer technology. We discussed 'playing' again for old-time's sake, but never did, or at least, we haven't yet.