I would have never guessed this would happen that night
Senior year of high school. I was a 17 year old senior, straight (still am) . I loved going on choir trips because it was so much fun to be with friends and have freedom to mess around for a whole weekend. This year, I had to room with 3 other guys. One was a junior, the other two were freshman. lets call the junior, Max. Max and I were ok friends before we went on this trip. I actually thought he was gay for a while but never said anything. the first night in the hotel as everyone was getting ready for bed I started to get really horny, as always before I go to bed. I have jacked off many times with my close friends and it never seems weird to me. But I knew it was not going to happen so I was waiting for everyone to fall asleep. I foolishly started messing around with max, I texted his phone, even tho he was lying in his bed 5 feet from me. I texted him 'are you gay?' Only to mess around with him. and he texted back 'no why are you?' I laughed and looked at him and said 'NOO!!' after a few awkward moments he said 'ok I have another question' he texted me and asked 'how much do you jerk off?' it was at that point at which I realized, maybe well jerk it together tonight. I said 'i dont know, maybe 2 or 3 times a week'
This baffled him! he was very surprised! He thought that it was weird to jack off and he felt guilty about doing it. I had alot of things to clear up with him that night. He was a bit sheltered. About an hour of talking went by and at this point he was sitting on my bed and the other 2 boys in the room were in deep sleep, so we were free to talk and do anything. He said 'ok I have to ask you a question, it is very embarrassing but I want to ask you anyway.' he was very shy about this but I convinced him to tell me anyway after about 10 minutes. he said 'i just got circumcised.' 'thast it?' I said. I laughed for about 5 minutes. 'what??? what??' he said. 'MAX!!! you are too funny, just about everyone is circumcised' 'really?' he said in awe. he was VERY sheltered thought you would not have guessed it. He was a 16 year old junior who was very smart and played off his sheltered thoughts well. after more talking he said 'ok, I get that alot of people are circumcised but I think mine looks weird' in my mind I thought, 'hmm maybe his got messed up during the surgery or something' so I said to him 'uhh ok ill tell you what I think, whip it out and show me' then as if he had been planning to do it the whole time he pulls out his cock, which was hard as hell, and shows it to me. I was very shocked, not really expecting him to do that, but I went along with it. It looked fine to me, infact it looked very similar to my cock. I said 'Naw bud, it looks fine not weird at all' then after he put his away he said 'ok now its your turn, you show me yours' Even though I really wanted to show him I pretended as if I was hesitant. but after about 5 minutes I just pulled it out and he pulled his out again and we established that both of our dicks were about the same size ( 6.5-7 inches and very similar shape). He started to play with his dick a little, I could tell that he was horny beyond belief. he looked at me and said 'dude.. im so hard.' that was basically code for 'ok I need to rub one out right now' With my cock throbbing in my hand I said 'ok lets do it' we were both sitting on a huge bed in a hotel room with 2 other sleeping boys, beating our cocks at about 3 in the morning. We were both so horny that we came within just a few minutes. He then went back to his bed, and we both quickly fell asleep. Even though I had blown a load, I was still hard as a rock and ready to do it again.
We didn't talk much about it ever again, besides small hints that he gave me to let me know that he wanted to do it again, but it is still possible. well see! maybe ill have another story soon
So buddy, if you are reading this then you know who you are and I bet you want to do it again. Just so you know, IM GAME!!!