The first time I ever fucked a guy up the man beaver was in my Senior year of high school. We had been grinding cocks and fucking each other's mouths for a while before then. Anyway, one night we were making out when I told him we should try something new. He agreed with a look of wonder on his face. I went into the bathroom and got myself all lubed up. When I returned (lube in hand) I told him to get on all fours. He did as directed and I moved in from behind. A quick squirt of lube on his boy hole was all it took to get his attention. When I put my cock-head on his asshole he made an uneasy groan. I slowly popped it in and got the whole shaft in. When I started pumping he made moans of pain. I asked him if he wanted to stop, but he said "No, I have to get over the pain". After a few minutes of getting his rectum used to being full, the cries of pain turned into moans of pleasure. He beat his dick as I ass-fucked him for about 15 minutes. We both had huge orgasms. For another good 6 months , I'd do him up the shit pincher almost every other day. I can still remember how his little red hole looked with my cock ripping it at the seams.