A few months ago I had gone to my aunt and uncle's house for a family party, as well as to stay over for a few days. It's sort of a family tradition, usually held at their house since they have the largest pool out of anyone in the family. I knew that several of my cousins would be there, but I usually ever hung out with one, Jack, who I had known since his birth, and the cousin I saw the most. Jack was 13, and while I was four years older, we still held a pretty close bond, and he usually came to me for help when he could.
So I packed a bag full of clothes and video games and stuff, and my parents and I headed a town over to my cousin's house for the party. It was the usual, parents leaving the kids with the kids. Since I was one of the oldest (there were two who were seventeen, and one who was eighteen, though he was off with the adults), I was kind of entrusted with watching all the kids, so my time with Jack and the others was spent watching everyone in the pool.
As me and Jack finished wrestling around in the pool, two boys that were family friends began whispering about jacking off. They thought no one could hear them, and with my back to them, I could listen and not be caught. They were both talking about the 'school hoe' and how hot she was, and how they both got off to her. They turned to Jack, swimming over, and quietly asked if he ever got off to her. They didn't wait for an answer, since their mom called them over, but I could tell Jack was confused.
One thing Jack and I never really talked about was sex, but I let it be since he didn't immediately ask me anything. We all swam for a while later until we decided to head inside since the food was almost done, and the guys wanted to watch a basketball game. I walked down the hall into the bedroom I was staying in, and began digging through my bag for the clothes I would be wearing. I heard people yelling in the hall, and walked out to find Jack trying to open his door. Someone had gotten to his room to change first, and the bathroom was closed too. I told him to just come change in the room I was in, and that was the end of that.
Once he was inside I locked the door, and then pulled my trunks off. I didn't mind that Jack and I would be naked in the same room for a few seconds, since we had seen each other naked on occasion, but as I pulled my boxers on and adjusted, I caught Jack looking away from my crotch. I ignored it, he was a kid, and just got finished dressing.
Later that night, after everyone had left, including my parents, Jack and I were in their den, watching t.v. He looked over after a while, and said he would be right back, and left the room. After a second he came back, an excited look on his face, and told me his parents were asleep. He sat on the couch next to me, rather than on the recliner where he had been, and then looked up at me. He asked if he could see my penis, and the hair around it. I was caught off guard at first, and wasn't sure if I should be doing this in front of my 13 year old cousin, but after he assured me that his parents were asleep, I nodded, and slowly removed my gym shorts and boxers, letting my cock slide out and rest on my thigh.
Jack looked at it closely, and at the hair around it. He told me that last time he had seen it, it had been small. Now it was 'huge and hairy', and my balls were big too. I laughed, and told him that it would happen to him soon, that he would start to grow around his age and then get hair shortly after. He glanced at his crotch, and I knew he was picturing it. He then shifted a little, and I knew he was hard. I started to get hard too, and he watched as my cock stood up, hard and thick. I asked if that happened to him a lot, and he said he started getting boners a lot lately, but he just let them go away on their own.
I looked around, making sure his parents weren't up, and then told him to come into my room. I pulled up my shorts, walked to my room, and waited for him to enter. I locked the door, and then told him to sit on the bed. I explained that there was an easier way to get rid of boners, and that it felt good too. I asked if he knew what 'getting off' was, and he asked what the two boys in the pool had said. I said yes, and that this might get weird, but I promised him he would like it.
I pulled my shorts down again, and let my hard on spring up, and then told him to do the same. Once he was naked from the waist down, I told him to do what I did, and then I sat next to him, and started to jack off. He watched for a minute, and then loosely grabbed his penis and started to tug at it. I continued, and then as I got closer to my orgasm, I told him that if he did it long enough, that he could shoot cum out of it, but that would probably happen in the next year. He wanted to see, so I increased my pace, grunting quietly, and then I shot a few ropes of cum up to my chest.
He was determined to do the same, and a few minutes later a single drop of cum came out of the top of his penis, and he sighed with relief. He agreed that it felt good, and that he wouldn't tell anyone we did this. I just told him to make sure and do it when he wouldn't get caught, and he said he would. Over the next few days, he wanted to jack off together again, so when I knew it was safe, we would.
Jack just emailed me shortly, saying that he could make more cum, and that he jacked off every chance he got. Guess I helped again