What was the hottest inappropriate sex you ever had?
07.06.2025 21:23

I'll try and keep the backstory short. My mom does housekeeping and some other stuff for this pretty well off older guy, like, late 50s older. He's divorced and has a couple kids that don't live with him anymore. He was going to take them to Manhattan, I guess some sort of bring everyone back together family trip, but something happened and they didn't want to go, or his ex-wife vetoed the trip or whatever, so he was stuck with three extra bookings and no people. He ended up offering them to my mom to take my sister and I if we wanted (obviously we did). The plan was just we all fly there together, he does his thing, we do ours. After all we're not like, friends friends or anything. But we all felt really bad and didn't want him just solo vacationing, so we ended up doing a lot of stuff together. Anyway, the spicy bit is this guy's cock is HUGE, really really fucking huge. Like, you can tell even when he's wearing jeans and stuff. There's a print. I couldn't help but constantly stare, the guy was easily twice, maybe even three times as long as my boyfriend, thicker too. One night towards the end of the trip my mom and sister went to bed early and me and him were just chilling on the hotel balcony. He'd had a few beers and I could see him constantly checking out my tits. He had been all trip, but was respectful enough about it. This was just staring. At some point he asked if I wanted a beer and I decided to flirt a bit and said sure, but I'd rather have something else, looking right at the imprint of his cock, which, was pretty obvious and a bit hard. Maybe ten minutes later I was on my knees for him. I couldn't fit the whole thing, but he didn't mind and kept playing with and using my tits instead. He finished in my mouth that time. We ended up doing it every night for the rest of the trip, rode him, took him in doggy... all of it was so hot.