I love this site, reading all the great stories.
Many years ago I had a friend who had a pool in his back yard. Every summer he and his family would go away on vacation for a week. Usually when they went away, they asked me to take care of their dog and the pool. Of course this meant that I could use the pool when I was there.
Usually, in the morning, I would go over by myself to feed the dog and hang out for a while. When I was there I would usually go upstairs to his sister's (younger) room and look through her dresser for bra's and panties and such. Unfortunately because they were on vacation, most of the good stuff was with them. But I found a bra and panties to play with. This of course would make me hard. I'd have to strip down to nothing and stroke my cock until I was shooting cum in her bedroom, all over my hand and stomach. I then cleaned myself up, put away the bra and panties and left.
Usually in the afternoon, I would go back with one of my other friends to go swimming. Of course we didn't just swim. We would get into the pool in our bathing suits, because we had to walk across the back yard to get to the pool. Once in the water though, they came right off. Kevin and I would then play around, swimming in the pool naked. Kevin was two years younger than me. He had about a four to five cock, not very thick and no hair yet. We would wrestle and screw around in the pool naked, stroking each other when ever we had the chance. We'd take turns putting on goggles and going under water to check out each other's cocks. Playing with it as we checked it out. The entire time we were in the pool we would be hard as could be.
After an hour or so of this we'd put on our suits and go into the house to dry off and change. Usually once inside though, changing our clothes was the furthest thing from our minds. We'd go upstairs to my other friends bedroom and start wrestling, grabbing and playing with the other's hard cock as we played. We would take turns getting on top of each other and rubbing our cocks against the others, humping like we were fucking each other. Then we would finally jerk each other off to orgasm, clean up and be on our way. Coming back the next day to play again, or going into Kevin's pool to play, but it wasn't as much fun in his pool, he had a lot of brothers around all the time.