The context here is that when the lich is too busy to handle captured adventurers and such, he lets the monsters in the dungeon screw with them. There's a sign up sheet to get to be the one to do it. And very strict rules for what you can do of course.

In this case, there's an elaborate betting system for whether or not Derek and Antonio can guilt this guy into eating a pair of panties and drinking a glass of mayonnaise, with payouts depending on how much you bet he eats, if he pukes etc.

Half the dungeon has bets riding on this.

(art life hack: you just draw shitty if you're feeling lazy like I did with this!)