Where it happened: boarding school
Langauge: English
Sex: Male
Rating: 5
Category: Straight
I attended an all-boys school during adolescence. On Saturday nights we would have what were called sleep-overs, where you could sleep in a different dorm room. I had my friend “Billy” sleep in my room. He was about 18 months younger than me, 12 going on 13. There was a lot of sexual tension building up between us throughout the year, and though there were no spoken plans to mess around we both knew it was inevitable. When he carried his stuff into my room, he also brought a big bottle of hand lotion and said something to the effect of “I thought we’d use this.” Right before “lights out” staff would come around. Moments before a female staff member made her rounds, I sucked on his cock for 10-15 seconds and he returned the favor. He had a small dick at the time, and I was (am) exceptionally big and thick. We waited a couple of hours for everyone to go to sleep, then once the dorm was dead quiet we started fooling around. A lot of sexual tension had built up between us thoughout the year and things got pretty hot. We gave each other head for a while, and I sucked his nipples and licked his stomach with my whole lower lip. Then I sat on the lower bunk for a while while he gave me head. I gave him very specific directions which he acquiested to. At some point he asked me to “butt fuck” him. I was very nervous. So was he, he had tried it was another boy who had hurt him by going too fast. He said he was worried because I had such a large cock. We came up with a system where he would say “a little further” and I would go deeper. I lubed my cock up with lotion, and put on one of those weird mining lights on my head (he had also planned for this) so we wouldn’t have to turn the light on. When I turned it on, he was on his knees spreading his ass open for me. I was looking at his smooth, plump butt and perfect pink asshole and was REALLY turn on. I put the tip of my cock inside of his asshole, and slowly, we started fucking. When I was about halfway inside of him, I leaned forward and collapsed all of my wait on top of him, so that my naked body was blanketing his. It was hard for me to really get into it because I was going so slowly for fear of causing him discomfort. At one point I thought that I was completely in his ass, and he whispered again “a little further”. I told him it was in all the way. He got really bitchy and said kind of loudly “no it’s NOT!” and thrushed his ass into my cock, driving me deep inside him. So hot. That was the closest I came to cumming. Afterwords I took a shower and felt really ashamed. I turned out to be bi (which I am totally comfortable with today) and Billy is married with a kid. We have a facebook correspondence and none of this has ever been mentioned again.
Processing your request, Please wait....
