I never saw it coming
This story takes place about a year ago.
It was summer time and school was out. During the day I didn't really do much. I sat at home, watched T.V., and of course jerked off. I was pretty horny for my age, 14, but then again, which 14-year-old isn't? After a couple of weaks of waking up, masturbating, eating breakfast, masturbating, watching T.V., masturbating, I was getting pretty bored. I had some friends in the neighborhood that I would play video games with and do other things with, but I wanted to do more. I had seen some of my other friends naked and we would sometimes talk about sex, girls, and eventually jerking-off but nothing more. I would sometimes fantasise about some of the other boys, not in a homosexual way, but more in a experimental way. There was one boy in particular, Taylor.
He was a little younger than me, 13 around the time. He was a little shorter than me with long, shoulder-length, dirty blonde hair. He was on the heavy side, with a round gut and small little man boobs starting to appear. He only lived a few houses down from me and he had a swimming pool too. I would sometimes call him to go swimming if it was hot and we would go for a swim. One time we did a little more than just swim.
I had just called him and was walking down the street. It was really hot that day and I was relieved to see his Mom at the front door to let me in. By the way, Taylor's mom is quite a MILF. She said that Taylor was up in his room and she told me to meet him up there. So I went up the stairs and into his room. I opened the door and walked in to find him completly naked. Startled he said, 'Oh... Hey. I was just putting my suit on.' He was walking around, naked I might add, looking for his swim suit. Seeing him in such a state started to get me aroused and he was showing some signs of excitement too. His small little cock was starting to poke out from under his round stomach and flop around when he walked. He finally got his swimming trunks on (I put mine on before I came) and we headed out to the pool.
We splashed around for a while and started to wrestle in the water. He came at me and jumped into me. His big tummy pinned me under the water for a bit. When I came back to the surface, I leapt at him, pushing him under. Underwater, I felt around, running my hand over his big belly and his man tits, feeling them jiggle and move. He leapt back at me pushing be under. Again I started to grope him, and Taylor started to feel me back, touching my own belly. We were splashing around at the surface, but under the cover of water we were secretly indulging ourselves. The contact made was getting me very aroused. We slowly went from feeling each other's nipples to feeling each other's boners. I grabbed him and squeezed lightly. He grabbed me back, leaving his hand on my hard member for a few seconds. We finally both surfaced and I suggested to end the game and go get dried off in his room. He looked at me and I looked back at him and he knew what I was thinking.
He quickly agreed and we hopped out of the pool. Dripping wet with huge erections, we passed Taylor's mom and went up the stairs. I went behind him up the stairs and got a good view of how big he actually was. He had large love handles that overflowed over his tight swim suit and a round ass. We got up to his room and we both stopped. He looked at me and I looked at him. At the same time we both pulled off our swim suits, exposing our cocks. He was uncut at around five and a half inches and I was cut at six inches. I walked over to him and grabbed his dick. It was wet with pre-cum and his balls were slowly dropping after the cold pool. He grabbed mine and it sent electric shockwaves through my body. He slowly started stroking me, from the bottom of the shaft to the top, caressing the head before moving back down. Although he was younger, he was somewhat well developed and knew pretty well how to work his hand. I stroked him, rubbing up and down his cock, rubbing his round gut and small man boobs. We fell back onto his bed, entangled in each other. We grinded our bodies together. Taylor's warm, smooth stomach rubbed against my dick. His hands were all over me, stroking my cock and playing with my balls. I wrapped my arms around him actually grasping how big of a kid he is, an arm's full. I slid my hands down his back and grabbed his ass. He whispered, 'play with my asshole...' I reached around his flapping cheek and found his warm hole and just played with it, running my finger around it, but not actually going in. He started pumping me faster and faster. I started finger and stroking him faster too. I heard Taylors breath quicken, I focused on his cock. He stiffened and he shot 6 ropes of cum all over me and his belly. He pumped out the last bit of his cum and lubed me with it. He stroked me hard going faster and faster. My hands felt his cum-covered chest and tits. He pulled on last time on my cock and I shot my load. I spilled all over him. He looked at me and smiled. He started licking some of it and finally cleaned it up. It was quite an experience, having Taylor, such a big kid, jerk me off. Needless to say we spent many more afternoons 'swinging' together.