“I can’t believe I’ve never done this” [MF] Anal

My buddy invited me to a pool hall with a clubby vibe downtown, a few years after college. Lots of pool tables, foozeball, and other games, in a black light setting with a lot of music and a bar. It was a fun scene. I don’t know if I had realized when he invited me, but it was the birthday party of a friend of his. This friend had gone to school with us but I had never met her.

His friend was an Asian woman named Jessica. Maybe 5’4” or 5’5” with B cup tits and a cute little butt. She could’ve stood to lose ~5 lbs, but can’t we all? She wouldn’t drop any jaws, but she looked nice. She was also really friendly and bubbly. We all had a good time, playing pool, drinking, occasionally breaking to dance. The kind of chill night you look forward to.

Anal on the roof with hotel hostess [MF]

Long story with some background before the night in question. It culminates in an admittedly far fetched story, though I can assure you it’s true.

In my first job, I traveled a lot, to the same hotel for about a year and a half. When I joined the team, many had already been staying at the same hotel for months, so they knew the hotel staff quite well. They quickly introduced me to the front desk staff, including a girl named Jen. Jen was super helpful and got me hooked up with hotel status earlier than I would have otherwise.

Jen was hot and had done some amateur runway modeling. She was about 5’8″, brunette hair partway down her back, thin, perky ass, and large B / small C tits. (Also later found out she’d tan a lot and often had the outline of a little sticker she’d put on her hip before she’d go in the tanning bed.) I was a young guy, so I was interested. I learned that Jen had messed around with a colleague of mine several months prior. Now, I’m not the type to really hold people’s past experience against them as long as they’re clean, so I wasn’t put off. In fact, I was actually more interested – it meant she was down to play with hotel guests.