This story happened in the summer of 2004, on the last week of June, only a few days after my fifteenth birthday. My youth group and several other youth groups were doing a retreat together that would involve mission work in the local community. We stayed in dorms at a local state university during the week. It just so happened that a longtime acquaintance was assigned as my roommate that week. He has been my neighbor since we were in kindergarten. We have not really been good friends since about second grade, but we have always at least been friendly to one another.
After we got to our dorm and got our beds set up and everything, I was getting bored. I then asked him how often he jacked off. He said he had actually jacked off only two hours before. I told him that I needed to jack off really bad and asked him if he minded. He said I needed to cover myself, but eventually, I complained about having to cover myself up, so he let it go.
He started to glance over at me and he made a comment that I had a big dick. The strange thing about this was that my cock was actually quite under-developed for my age, as I hadn't started puberty until the previous October, at age fourteen. My dick was probably about four and a half inches at the time, though, now it is a little over five inches. I was stunned that he thought my dick was big, but I knew that he was quite a bit overweight, meaning that his dick was probably smaller.
My suspicion proved to be correct after I finally convinced him to jack off with me the next day. His dick was only about two inches hard. I had an endless boner the entire time we were at this retreat, which was five days. I jacked off non-stop in our room every chance that I got at which time I wasn't supposed to be anywhere else. I actually touched and squeezed his little dick once, just like I would squeeze my own when jacking off, and he said that it hurt. My dick, although it is not very long, is about five and a half inches round. I tried to get him to jack me off and I tried to get his permission for me to jack him off, but neither worked. Eventually, I just gave up on us jacking each other off. Oh well, it was a very fun week, filled with lots of excitement and lots of cum, too!