There once was a time, pre-Grindr and such, when CL was practically the only online hookup option. At the time I was still dating and fucking women while exploring fun with guys. Well, with all the flakes, fakes and pic collectors on CL, it could be painful finding any fun, especially with work and regular dates with women and hanging out with my straight guy friends. I could easily go months without gay sex even though I was looking weekly if not daily. For those that remember CL had its fair share of escorts looking for biz which usually annoyed me.
This one escort in particular, who in addition to being hot, was persistent and charming. He was one of the few escorts I conversed with and I was a rare potential client he’d spend time trying to lure into his regular book of business. After one particularly long dry-spell, I finally made his persistence pay off and we started negotiating. The first session came and went and was good, not great. First a little mutual sucking then I fucked him - with a condom since this was before PrEP and him being a hooker and all, he couldn’t really let his clients play raw - we chatted and he left. This continued for 18-24 months but I was starting to get bored. The condom thing I could manage initially but they seemed to increasingly deaden my sensation with pussy and ass. The other factor was I was getting more interested in trying to bottom more (I had bottomed maybe 4 times with 4 guys in my life, all wrapped up with an orgasm-killing piece of latex on my cock). During one session I was trying to fuck him but was somewhere between soft and limp and my escort buddy was getting annoyed and I think he had another client coming and saw how long this would take if he let me keep going. So, instead, he just took control, telling me to stop trying, take off the condom and lay down. At first I thought he was going to let me in him raw but instead, he told me to lay on my stomach and I saw him reach for the lube which he applied to his cock and my hole. My initial thought was one of confusion followed by concern, then fear and ultimately, arousal. He didn’t waste any time mounting me bareback which I noticed but remained silent about and eagerly spread my bubble butt cheeks apart, spread my legs a little and lifted my butt and arched for his best access. Shortly he managed to get all 7” in and he was harder than I’ve ever seen him, and began pounding my hole relentlessly, slapping my ass and talking really nasty to me. I want partially scared I was taking raw dick from an escort but mostly I was turned on beyond belief. I soon was moaning until he finally finished dropping his seed deep inside. It was my first load and all I could do was ask him if he came in me. He said yes and we dressed in silence and I left. After that I paid him to breed me, I never tried to fuck him and he never offered it. I started having a harder and harder time staying hard to fuck pussy and eventually gave up on vaginas altogether. I’m out and I’m a cumdump now, thanks to my escort buddy who recognized what I really needed.
