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 waiting - 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...just as she rubs her ass on me. She goes, did you just cum???I said no it’s just precum. I was rock hard still from how hot it all was and kept going.

I have a pretty small dick and was pleasantly surprised I was able to fuck her prone bone on the bed. I was thinking ..."no way i can make it through these ass cheeks into her pussy"...but it was ecstasy when i felt her pussy suck me in. I was biting her neck and resting my weight on her hips while i pumped into her, thinking "i can't believe this is happening". She didn’t want me to eat her out - my go to to last longer and compensate for my small cock. She eventually straddles me, and swallows my little dick in her surprisingly tight pussy. . Moving her hips slowly but forcefully. I loved being able to see that thigh/ass crease. I grabbed her ass so firmly, pulling downwards, making sure she got every bit of this little dick (make sure you work on your glutes/legs so you thrust up my friends)

It was so fun looking up at her freckled, older skin. Her short dark hair with these white pearls contrasting her brown skin. Her hands in her hair, eyes closed. It made me feel so good she was loving my small dick (i'm so self conscious about it obviously - despite being a good looking guy). She still had her bra on at this point. Her tits were spilling out as her bra fell off slowly. Ending with a titty fuck where I cum on her freckled tits squeezed together, getting cum on her pearl necklace. 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 work 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 STOMACH DROPSSS. "How do they know what happened???...do they???"

Apparently she came back to the hotel. Banging on random doors trying to find my room again (she didn't know my name though). 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 wouldn’t leave the hotel lobby and got arrested…

The executive mentions she saw me chatting her up at the bar. I smoothly 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 my exec and my team for looking out for her (how gentlemanly ;) ). I said that’s all I knew. They def bought it but wow, was not expecting any of that.

That was the 1 of 2 hotel bar milf encounters.