Let's share our creepiest, most horribly inappropriate rpg stories!
Well, three players in my old Pathfinder group were starting new characters on the same day, due to half our party being wiped (in an incredibly stupid fashion) during the last session. So there's me with my half-orc rogue (I spoke in this annoying growly voice, it was a miracle I didn't get hoarse from it), a tiefling ranger (played by a more experienced DnD player, probably the most competent of the trio) and a halfling. I don't even remember what class the halfling wa- actually, that's right, he was a druid who later learned to ride around on a velociraptor.
Anyway, the three of us were in a tavern, having met recently on the road to whatever city we were in now.
It was a very ambiguous opening, but oh well. As all good adventurers do, we started drinking heavily. (It was at this point my character gained the nickname 'Shitdrinker', which followed him around for the rest of his life, due to saying the booze "tastes like shit".)
There was some various stupidity with the rough-looking occupants of the seedy place we were in, we moved on to stronger drinks, and then we ended up failing a whole bunch of CON rolls and blacking out. We came two under a wagon somewhere in the city, naked (almost? I think we still had underwear, or some sort of loincloths, but I can't remember) and incredibly hungover, and the halfling had some lewd phrase written around his mouth.
So, we'd lost all our gear, money, dignity (pfft), everything.
Once the tiefling and I had managed to beg some rubbishy clothing off a sympathetic shopkeeper, we had to think up a way to make some cash. We ended up hanging a sign around the halfing's neck (he was still wearing his loincloth) advertising a price for a sweet piece of halfling ass. He then wandered through the seedy dock area we were in, flirting with likely customers whilst the rest of us followed at a discreet distance.
Once he finally found an unscrupulous, scummy-looking sailor who was actually interested, we waited until his purse was in his hands and they were standing in some sort of alleyway, then the tiefling and I jumped out, bashed him over the head and grabbed the money before running off.
Unfortunately for us, the city we'd decided to commit this crime in turned out to be Waterdeep, which apparently has a pretty hardcore system of law enforcement. (I didn't even know about this OOCly) It wasn't long before we were being pursued. The tiefling surrendered peacefully, I tried to fight and was swiftly knocked out, and the halfling used some feat-or-other to run a ridiculous distance in a short space of time.
That was when they called in some sort of Wizard-Cops to catch him, which they did quite quickly.
So, we ended up thrown into some dungeon or other, having nowhere near enough money to bribe our way out of it.
Tl;Dr: We whored out our halfling on the docks of Waterdeep and robbed his customers to make quick cash, were promptly caught and jailed.
(This is just one of many creepy, inappropriate stories from that group, haha. Man, I miss playing with them.)