In consulting, often travel with a big group of young professionals who like to drink. Everyone was closing up their tabs. It was just me, our executive, and some randos at the hotel bar. A milf, 50 started chatting me up. Executive closes her tab and heads out. Keep chatting up this milf. She said I was cute. She says she’s here to meet up with a friend. Never imagined I’d say this, but I ask if she wants to wait in my room until her friend gets here.

For context, I only had a few sexual encounters in college. I never go out to pull women, just have fun. My senior year my laid back, no strings attached, fun but respectful attitude attracted a lot of girls. But still only had sex a few times.

We go up to my room. I lost my keycard lol. I tell her to just wait here, outside my room (lol). I sprint (lol) to the elevator and to the front desk to get a replacement. I wonder if anyone saw this play out on security cameras. I hustle back to my room. She’s sitting on the ground - I’m thinking, is she drunk? Side note, I’ve learned a lot about consent since then and idk if I would’ve done it again, but she was the one that initiated ya know?

We go in and start kissing, she takes off my pants and sucks me bit from the edge of the bed. As she’s crawling onto the bed wanting to stick her ass up to fuck her (had only done missionary thus far). Dude, I came already. She goes, did you cum? I said no it’s just precum. I was rock hard still and plaid it off.

I have a pretty small dick and was pleasantly surprised I was able to fuck her prone bone on the bed. She didn’t want me to eat her out, obvi my go to to last longer. She eventually straddles me, and swallows my whole little dick. Ending with a titty fuck where I cum on her freckled tits squeezed together, getting cum on her pearl necklace (so cliche but amazing lol). She gets dressed. I offer to walk her to a nearby bar where her friend is. Drop her off.

Fast forward. I wake up so so so late to the working session I need to be at. I change but don’t have time to shower. I feel like I just smell like sex. My team members say “maybe sidd knows what happened with her last night” my heart sinks.

Apparently she came back to the hotel. Banging on random doors trying to find my room again. Because I mentioned my company, she mentions it to the front desk. THEY GIVE HER MY PROJECT MANAGERS ROOM NUMBER. They are obviously like wtf. Apparently she like wouldn’t leave the hotel lobby and got arrested…

The executive mentions she saw me chatting her up at the bar. I cooly mentioned that she was meeting a friend nearby so I offered to walk her over there cuz it was so late and we’re downtown after all. Ironically got kudos from her and my team for looking out for her. I said that’s all I knew. They def bought it but wow, was not expecting any of that.