Oh god, I’ve got loads… but the one that springs to mind is letting 7 black guys fuck me in the middle of a room in a sex club

3 guys over one weekend. I was 19 and hot so no ragrets

(Long story I may post in full if people are interested)

Short version: Years ago I, 21M was on a break with GF at the time, was out clubbing, picked up an attractive 45F milf. Went back to hers, thankfully had a condom, fucked like crazy for a couple hours. For someone who claimed she hadn’t had sex in a few years she took it like a champ, folded her up with her legs behind her head etc. Gave her a rough drunken pounding and she loved it. She came a couple of times while whisky dick got the better of me and I didn’t cum and we passed out

Next morning we started where we left off, didn’t have another condom but she told me to hit it raw and she’d take a morning after pill. (Had a few kids and didn’t want anymore) Some more fun ensued, graduating from gentle sex to some pretty rough stuff, enjoying all of her holes. While eating her out and fingering her I found where the condom went the night before 😂 After plowing her hard in doggy for what felt like 45 mins she told me to cum as she was getting sore. Told me to finish anywhere I wanted, I figured as we’d already fucked twice without protection and she’d take the pill I might as well blow inside her. I filled her up, made out briefly and left.

I get home and just minutes later my ex arrives to talk about us. I hadn’t even had time to change let alone shower… After some talking she’s on top of me, giving me head. Sucking the dick that had been sucked on and blown in a woman double my age less than an hour ago. She then rides me until I cum I’m inside her.

I felt extremely guilty but it was so hot at the same time.

I think it’s best to announce! It keeps things open and fun. What about you?