Context: So into one of our longer campaigns we encountered a deadly threat in the form of what I think was a succubus/siren type thing. She had this special power over men that would cause them to fall asleep while she preyed upon the women. I was the only female in the party and all of the dudes failed their checks miserably (ALL OF THEM), so it was just me an the elf wizard, Ekmetiel (or “Ekky”), who was male but looked quite feminine. This is what ensued.
Me: (halfway into a fight we are losing horribly) Okay, look, lady, we’re women just like you!
Ekky: Excuse me?
Me: Ignore her. Can’t we just have girl talk?
Monster: Very well. (Proceeds to explain how she captures the men by hypnotizing them and smiles creepily rather than explain what happens to the females.)
Me: Um, okay… so are you going to kill us? ‘Cause I’m almost out of arrows.
Me (OOC): DM, how high would I have to roll to convince her that we’re actually male?
Ekky (OOC): I am male!
DM: Pretty high. Even you’d have to roll a twenty at least.
Me (OOC): M'kay (rolls Nat 20) AH YES!
Me: Miss Monster… Lady… Thing, please, have mercy, for we are cursed like you! We are but humble elves.
(A lie. I was a half-elf. But I just happened to be one suave BAMF half-elf.)
Me: Thus, from birth we were cursed to look female. In actuality we are male!
Monster: …I’m listening.
DM: Okay, if you want to actually convince her, you’re going to have to roll almost that high again.
Me (OOC): Screw that, how high do I have to roll to pull down Ekky’s pants?
Not very high, it turned out. But when I tried to convince her I was male as well I rolled another Nat 20. She left in a huff (because she couldn’t put us to sleep) and in sheer embarrassment.
I saved my entire team by pantsing our wizard.