Jim and I were long time friends. Met each other working at summer camp in high school and went to the same local college. Jim was a preppy kind of guy while I was a lot more casual. We had both had long time girl friends and always did our best to flirt with whoever we could. In the past at summer camp and the Friday trips we would play a game similar to the one in Top Gun where you had to meet a girl and get name and hometown. Whoever got the most information would win. This was a fun game to play and even the kids got into it, verifying the winner.
We knew everything about each other and often strange subjects would come up while drinking and playing SNES. One particular conversation that came up that led to a more open relationship between us was about the size of our dicks. Jim would ask what I thought was a normal size. I didn't really know because the internet wasn't really around so all I knew was the size I had seen in a porno and what I had read. After a while, the conversation wasn't really going anywhere because he wouldn't drop the subject I stated that I thought it was the length of his hand. A few minutes passed and he disagreed stating that he was sure that his hand was bigger. Not knowing and trying to just move on I stated that I really don't know. I just felt like I was average compared to what I had seen in pornos.
"How big is yours?" was his next question. Me stating average wasn't a frame of reference for him. Then he asked me to measure. Taking aback, I just laughed it off. He pressed on wanting me to measure so he could feel either good or bad about himself. He had never had any issue with any girl he was with so I didn't know why he was that concerned. We were drunk. He was very concerned about this and I really didn't give a shit. He wore me down so I had to figure out how to measure. He handed me a ruler. I went into the next room to check. I unzipped and realized that measuring soft wouldn't work. So I stroked myself some, thought of the girl that I helped out the other day and the blowjob I got in return and got hard pretty quick. I put the held my dick straight out and laid the ruler on the top and measured the top from the base too the tip. Granted my head wasn't engorged but it was just shy of 6 inches.