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.
Make all of the prostitutes in the brothel female goblins that sound like Danny Devito after 30 years of chain smoking. If you have to suffer, they can suffer too
Exactly this. I had a character go to a brothel in a campaign I ran. I just said okay, you go to the brothel and have whatever you consider a good time. No further detail or RP was requested or required.
Yup. No matter how hard the PC tries, just pan over to the fireplace and fade to black:
https://youtu.be/v7eJEsf11WM
(had to include the obligatory Top Secret! clip)
I did this to my brother in law. He critically failed every single roll I've never seen that many 1's. He woke up married to an "elf" named Ralph and a mysterious -1 to CON that went away next time he drank a healing potion.
The rogue I DM always asks where the brothel is. I just make up names and charge him gold for the stay.
While on the road the party stopped at a tavern in a small town. It was run by two sisters that were very friendly with the rogue and the paladin. The sisters led them downstairs and into their respective rooms. When their backs were turned the doppelgangers attacked!
The paladin's steed sensed he was in trouble and burst in the tavern and hoofed it to the cellar. The monk and wizard realized what was happening and begrudgingly put down their drinks to go help.