i was about 23 (bi) at the time and just starting to experience with guys. was chatting to a guy in his "late 30's" who seemed really chill and awesome. He was on the large/heavy side, about 6ft 280lb. mostly fat. but i had only tried some oral and j/o stuff before and he was the only guy around who wasnt looking for more. we agreed that he would come over while my parents were away inthe afternoon, to watch some porn and have a quick mutual jo session.

Guy comes over stumbling like he had been drinking. he looked about 10 or 20 years older than his picture. pulls out a big bottle of long island ice tea and pours me and himself a big cup. we start drinking and chatting and watching porn and jerking off in my bedroom. By the time i was nice and buzzed he said he wanted to try anal with me. just the tip, nothing else. I said no way but he insisted and he was getting pretty drunk and loud so i said fine just the tip.

long story short, a j/o session turned into my first time trying anal and my first creampie. He came inside after I asked him not to and then he got up, said i had a cute ass, and left.

I was face down on my bed, my ass hurting like crazy, my back covered in his fat man-sweat, and cum all over the clean bedsheets. worst hookup ever.