I was a freshman in high school when my best friends family was going to Ixtapa for winter break. Frank's brother was a senior on the basketball team, and when they unexpectedly made the playoffs, he couldnt go. so his parents asked Frank if I he wanted me to go, and off we went. As soon as we arrived, Frank and I went to our room to change and go to the pool. I had never seen Frank naked before, just shirtless. When he dropped his boxers, it looked huge. My jaw dropped, and he just stared at me and said 'What?'
I kinda laughed and said shit man that thing is like an elephant truck... you feed it peanuts?. He laughed pulled on his board shorts and off we went to the pool. We had a great time that day, barely ever saw his parents, and ended up hitting the sack about one or two in the morning. The room had one king sized bed, and while it was a little weird to share a bed at 15, at least it was the size of two twins, so we wouldn't be bumping into each other. We both slept in our boxers, and we both fell asleep quickly. I woke up about seven needing to pee. I could feel Frank had spooned up behind me, and I could feel his dick against my back. I was already sporting my morning wood, but the thought that that monster dick was touching my back was making me kinda hot.
I turned my head over my shoulder, and I could see that Frank was asleep, I said... dude that better be your flashlight pushing against my back, not what I think it is. He woke up in a start and rolled over quickly. I got up to travel to the bathroom, and he saw my boxers tenting out, and laughed and said well looks like someone liked my flashlight, and rolled back over to go back to sleep. I managed to piss through my wood, and headed back to bed. He had rolled over and his back was to me. I got in bed, slowly moved up behind him, and rubbed my dick against his back, and said so how do you like that queerball? He didnt say a word, so I did it again. He flipped over and pinned me down before I could even react, and suddenly our dicks were pressed against each other, and our bare chests touching.
He looked in my eyes and said.. you know I kinda liked it. Then he started rubbing his dick against mine. We dry humped each other for a little bit, and he rolled over, and tugged his boxers down. I watched as he started to slowly jerk off. I pulled my boxers down and matched him stroke for stroke. I looked at him and said I can't believe how big you are, and he said do you want to feel it. I reached over and started to jerk him off, and he reached down and did the same to me. Soon we both came, him first then me. We laid there covered in cum, just breathing hard. Frank and I messed around a lot that week, one day alone we had five orgasms together. By the end of the week, we had progressed to dry humping each other We both agreed we loved getting it, hated giving it, so that stopped.
We got back home, we decided that we should stop, and we did mostly. Over the next three years we stayed great friends, both of us got girlfriends and laid within a week of each other, and talked about sex constantly. I have no desire to have sex with any other guy, but would in a heartbeat again with my best friend.