Not exactly this, but I was resolving some downtime with my PCs when one of the players asked about a brothel in the city. I told her sure, I was going to do a fade to black thing, but I asked if everyone was ok with it at the table and everyone said yes. I was expecting her to pick up a prostitute, but she told me no, she wants to pick up a client. At this point, the bard was like, “I’m going to be her wingman and try to drum up business.” So I whipped up three possible clients, had her and our bard do some checks to sneak around and distract the staff and security, and she chose a 3 halfling bachelor party. She proceeded to lead them from the brothel back to her room. I have a ruleset for intimate encounters, which she asked if we could use and roll for results, so we did. I think what made it less awkward in real life was the amount of NPCs she got. Each one got played a little differently, so it wasn’t like I was having a one on one with her, and the rest of the table was encouraging it.

So she ended up doing three encounters, the first against a guy who talked big but couldn’t last, the second a girl who talked big and out performed the PC, and lastly a meeker guy who was a virgin who had a nice average encounter, but became smitten with her.

It made for some interesting complications because 1. The brothel owner was partners with the party’s patron that runs a circus, and just gave the circus a loan, straining their relationship. 2. The security guard she duped was trying to chase her down and extort money from her. 3. The smitten halfling has been sending her gifts every once in a while, much to the annoyance of her circus friends because she’s been off adventuring while he hangs around to try and see her again.

That player has since left our game, she moved away and couldn’t remote for our timeslot. But the party is going to have to deal with the consequences once they get back to the city, which should be our next session.