First off I am a sixteen year old male, I swam on my school's swim team for two years, so I am somewhat fit, and not the thinnest or most built, but I have a decent amount of muscle. I have a small patch of pubic hair above my cock, and some hair on my ass and taint, and my cock is about six and a half inches long.
Now to the story. I recently stayed with my grandmother for a few days with my brother. We went to visit, and to see and help watch our younger cousins, a thing we did since we were young. I hadn't gotten to stay with my grandparents for a while, and at the time I was tiring of things at home (parents and my sister and such), so I took the opportunity to go. We had been at her house on the fourth of July, and my brother had stayed then, but I had come home for a few days first. When I left we went to her house, and my break started.
The third day we were there, we were told that neither grandparent would be home for a few hours, so we were on our own. My brother and I just lounged about for a bit, playing our PS2, and watching TV. While we were watching a comedy channel, a commercial for Girls Gone Wild came on, showing everything but their nipples and pussies, covering them up with their logo. It lasted for like three minutes, advertising different videos, and when it was over, I looked over to my brother.
'Aw, you'd better go get new boxers, you probably just came, huh?' I said jokingly. I honestly wondered at that point if my brother even did jack off. My brother is 13, which is when I first started to jack off, and he has had a 'friend with benefits' for about six months now, so I began to wonder just how sexually active he was. It's not that I was picturing my brother doing anything, I was just curious.
After about another half an hour, I told my brother we should go swimming in the pool out back. He told me he wanted to finish the last ten minutes or so of the show, so I got up, and went and changed into my swim trunks. (I don't wear boxers with them, that's just weird to me. Why not just swim in those?) I walked past my brother on the way out, and then closed the door behind me.
I was about to jump in the pool when I figured, hey, no one is home, and we're both guys. I have the old master bedroom at home, so there is an attached shower, so we've glanced at each other naked. I took off my trunks, and jumped in the water. A few minutes later my brother came out and saw me naked. At first he started protesting, saying that someone could come home, but it was true that no one would be home for a while. My grandma had gone out of town with her friends, and my grandpa had gone golfing. When he realized we were home free, he hesitantly pulled his suit down, and got naked.
I looked at his cock, which was smaller than mine, and he had a small amount of hair above his cock. He quickly jumped in, and then we started swimming around, until I just stopped, and kind of bummed around for a bit. Finally as he stopped too, I looked at him, and asked what I had been thinking.
'So do you jack off Brian?' I asked, catching his attention. He was quiet, and then nodded, saying that he had just started about two weeks ago. He told me that he could cum, but it didn't shoot, it just kind of ran down his dick. We got to talking about sex and girls and such, and after a while I was rock hard, even in the cold water. I started to rub my cock, and then I saw my brother do the same thing.
I starting to jack off, the water slowing down my hand, but increasing the sensation. My brother started to as well, and then stopped, asking if he could come over and see me. I stopped and shrugged, and then jumped out of the pool and sat on the edge. He came over and got close, looking at the head, size, and the way I was cut (we're both circumcised.). He then reached up and grabbed my dick, and started to jack it off. After a moment he too jumped out of the water, and I reached over and returned the favor.
There we were, naked in our grandparent's pool, jacking each other off. I took his hand off of my cock and told him I would show him a few things. I slowly jerked him while to took my other hand and rubbed his balls, pushed and rubbed the area right under them, rubbed the underside of his head. I showed him all the things that make me feel good, and then he finally came, dribbling cum all over my hand.
I jacked myself off to finish, my cum jetting into the pool. We sat there for a moment before heading inside, still naked, talking about sex and girls, and we jacked off together again later that night. We have only done it together once since we got home, but he's always wanting to now. I'm sure we will sometime soon.