The summer after my senior year of high school, I worked at a small business from midnight to 6 am. I was going to college in the fall, and I was rather enjoying my the time I had with nothing related to school. I usually went right home and to bed after work, but midway through the summer, I decided I needed to get in shape before the fall. So, I started going from work to my best friend's house. He had a swimming pool, and they never minded when I used it. His mom is a teacher, so she was usually there, since school was out. (Oh, and by the way, don't get the idea that this is about me and my best friend Jeff, because I have never had an encounter with him. He is very straight, and we have done nothing. However, something really interesting did happen.)
Another guy who Jeff had introduced me to (Brandon) started calling me at work almost every night. It was slow, so I didn't care. We didn't talk about much of anything. One night, I mentioned that I was swimming at Jeff's every morning. He thought that was cool and asked me if he could join me. I said he could whenever he wanted. I had no idea he was into cock. I had been screwing around with guys since I was 11.
The next morning when I got to Jeff's, Brandon was waiting there for me. He had his swim trunks on, and did he ever look hot. I was 17 and he was 15. We headed to the pool and started to swim. After about 15 minutes, Jeff's mom came out and said that the whole family had stuff to do out of town, so there would be no one around. I secretly was very glad. She said to stay as long as we wanted, and she would leave the house unlocked if we would lock it before we left. I told her it was no problem.
After the last vehicle pulled out of the drive, Brandon changed a little. I couldn't swim past him that he didn't grab at me or want to wrestle. Well, I was up to it, so we started grabbing each other and dunking. He would grab me around the waist, quickly brush my crotch, then take me under. Then I would do the same to him. It was becoming obvious that we were aroused. Everytime we picked the other up, someone got a hard cock in his ass cheek. We tired of dunking and began to just swim around again. I would go under and swim between his legs, making sure to brush my cock across him somewhere as I passed. He picked up on it and did the same. After we tired of that we went to dunking again. There was one alteration though. When I went to pick him up, I would grab him, then take my hard cock and position it so it was right on his ass crack, then I would squeeze his huge basket, and dunk him. He liked that and started to do the same to me.
At that point, I thought it was obvious that we were hot to fuck. So, I went to the shallow end, went under, and came up with my trunks in my hand. After I threw them on the deck, I asked him if he wanted to skinneydip since no one was home. Even though we had been groping, he was a bit shy. Finally, I gave up and said, "OK, if you aren't gonna swim naked, neither am I." I reached for my trunks, and he dipped underwater (wearing goggles). He popped up, after having seen my hard-on, and said "OK!" So, off came his trunks.
We started to swim around again. It was no time until we started wrestling and groping again, too. I would swim up behind him, wrap one arm arounf his hard body, and position my cock with my other hand just so it would hit him in the right places. He did the same to me. As we continued, we got bolder. Soon we were grabbing each others' cocks and squeezing balls. It was fucking great. Then I went on the offensive.
I started getting rougher with him. We worked our way to the shallow end. I reached around and grabbed his cock in my left hand, while holding mine in my right hand. I pushed him against the railing, and all of a sudden he says, "Fuck my ass!"
I tried to fuck his tight, hard ass right there, but it was difficult in the water. So, I went under and wrapped my hot lips around his huge 9-incher. It was fat too. I began to suck, then I deepthroated him. He was going crazy fucking my face. Then he went under and sucked my prick.
We decided to get out of the water to make insertion easier. We dried off and headed inside the house. We went to my best friend's room to hang out. Brandon went to get a snack. He didn't seem interested anymore. When he came back, I said "Don't you wanna fuck?" He said he sure did and asked if I wanted his ass. I asked him who he had been fucking around with, but he wouldn't tell me. But, I had to be good to him, so I told him I'd plow his ass (my cock got big early and was about 10 inches). He got on his hands and knees and wiped some lotion all over his cornhole. I licked it for a minute, then I put the head of my one-eyed monster right on his flower and pushed. It was obvious he'd been getting rammed for quite a while because I slid right in. He was still very tight though, and he really got into being fucked. He was moaning and panting and gasping. All of a sudden, he jerked, and I realized he'd just emptied a major load all over the floor. That was too much for me, and I asked him where he wanrted it. He said he had to have it in his mouth, so I pulled out and he was on it in a second. My cum shot out harded than I ever remember before. He couldn't swallow it all, so I shot some on his face, too. I licked it off. We just laid there for about ten minutes, then I felt his pecker poking me in the leg. He wanted to 69, so we did, then he fucked me up the ass until he shot a gallon inside. He took my second load down his throat too. It was fucking great.
We hooked up a few times after that, but Brandon and I never had another encounter that was as awesome as that first.