My best friend’s daughter irl decided to charm the bugbear guard. I made puppy dog eyes at her while her parents giggled their asses off. She was thirteen at the time.
Bam! Succubus questline
Or: engagement in prostitution is punished by death, while prostitution is legal. They need to kill the major. Then, they find out that an underground organization is behind the ban on prostitution and is picking up speed and converting other parts of the continent. And after weeks of following the breadcrumbs of information next to their real story, they find out that this organization is ….
Nope sorry, you found the one city with no brothels.
Please remember that your DM is a person. They are also playing the game and deserve to have fun, and for their boundaries to be respected. They are not just a physics engine for your shenanigans.
That being said, some DMs in specific groups might be totally fine with this. Just don’t spring it on someone without prior discussion and consent. That is (among other things) what session zero is for.
One of my DMs is my gf. So I think that if I were to cause such a situation, it might play out something like:
ME: I go look for a brothel.
DM/GF: Sure, you do that. Now, what’s everyone else up to?
ME: that’s fine, we can play it out later 😏
