13-14 then---we're both straight
Towards the end of grade school, everyone was going through puberty, or at least starting to. I was maybe half way through at the time, with plenty of pubes and what I thought was a big dick. My best friend, Ray, was clearly further into puberty than I was. He had plenty of hair on his legs and even had some facial hair that was starting to grow. The both of us were about average size, Ray being a little bit skinnier than me. He had black hair and brown eyes, and I have brown hair and brown eyes.
Ray and I would have sleepovers all the time, mostly at his house in his finished basement. We played games like truth or dare, or just scare the crap out of each other in the dark. However, now that we were getting a little older, the dares began to change and the game got a little more intense. We had both agreed to a rule in the beginning that if you didn’t do one of the dares, you had to take off an article of clothing and stay like that until the next morning.
My first turn, I chose dare. Ray dared me to go upstairs and walk around with no shirt on. Now it was late, so none of his family would be awake. I agreed to do this, quickly. When I came back down, it was Ray’s turn. He chose dare. I dared him to go walk around upstairs with no pants on. He stood up and took off his sweatpants. I saw his hairy legs and his light blue boxers. When he came back down, I chose truth. He asked me if I ever jacked off, to which I said yes, and we moved on. He chose truth and I asked him the same question, to which he answered, “Yes, all the time.” Next, I chose dare. Ray dared me to go upstairs and walk around naked. But I thought it was too risky, so I chickened out and took off my shirt. Ray chose truth next. I asked him if he ever got caught jacking off. He said that he got caught by is younger brother when he was lying on his bed doing it naked. “Wow,” I thought to myself. All I could say was, “That SUCKS.”
It was now getting late, and by this time, we were both sitting there in our boxers from chickening out on other dares and having to take off articles of clothing. Ray was wearing nothing but his light blue boxers. I could see his hairy legs and the hair under his armpits. I was wearing a pair of red boxers, and didn’t have nearly as much hair on my legs or in my armpits.
It was Ray’s turn for a dare again. I told him to go outside and do a naked lap around the house. (It was about 28 degrees outside). He said, “No way! I’m chickening out for this one.” That’s when I think he realized that the only thing he had left to take off was his boxers. So, he would have to stay naked until the next morning. I reminded him of this and it seemed like he wasn’t sure what to do. He eventually said, “Yeah I know, because I am not going outside right now.” He hesitated, but I watched him slowly pull down his light blue boxers, revealing a nice bush of pubes and what I thought was the biggest dick I have ever seen. It was about 4 inches, SOFT, with pretty big balls, and really hairy. Mine was maybe 2 inches soft and 5 inches hard, so this was amazing to me. He sat back down on the floor, crisscrossing his legs and letting his dick hang out in front. I knew that one way or another, Ray was going to get me to take my boxers off too. I chose truth for the next couple of turns, obviously trying to avoid having to be naked, and so did Ray. However, Ray eventually said, “You can’t choose truth for every single turn!” I finally chose dare. Ray dared me to jack off. I responded “Where?!” and he said, “Right here!” I told him that there was no way I was going to do that right here. Ray then said, “OK then, chicken out! Take off your boxers!” There was no other option for me, we agreed to this rule at the beginning, so I just did it. One quick motion, I slipped them off and sat back down in front of the couch on the floor across from Ray, kind of embarrassed about my size in comparison to Ray’s. Little did I know his was huge for our age.
His next dare I told him to measure his dick. He said, “Hard or soft?” I said hard. He grabbed his dick and began rubbing it to get it hard. His four inch dick quickly turned into a massive rod. I was amazed. He ran upstairs with his boner bobbing back and forth to get a ruler. He came back down and stood in front of me and measured. “8 inches,” he said, “Wow.” Naturally, it was my turn to measure next. It was 5 inches hard and I told Ray that his dick was humongous. Ray picked dare again next. I told him to jack off right there, thinking that he wouldn’t do it either. However, against my expectation, he leaned back against the couch and began stroking. I didn’t say anything, but once again watched his dick get bigger and harder. He had been jacking off for about ten minutes now, when he started to pump his dick harder and faster and let out a few moans. All of a sudden he let out a long moan and gasped. He spewed multiple ropes of cum all over his chest. I don’t know why, but this made me so horny. When he dared me to jack off too, I had no problem with it. It only took me about five minutes, and as Ray watched, I dribbled cum all over my lap.
We both fell asleep next to each other, naked. We were lucky that no one came downstairs the next morning, because when I woke up, I saw that we both had big hard-ons and the blankets had slipped off, so you could see everything.
We had many more sleepovers and truth or dare sessions like this after that. Now that we are in high school, we don’t really talk about stuff like this anymore. We are still best friends and still see each other naked from time to time when we are getting changed or when we’re in the showers in the locker room. Ray still has a bigger dick than me, even though mine has definitely grown since then.