Cool kid: I slept with your sister.
Me: Never knew my brother was a girl.
Everyone else: :O
Cool kid: I slept with your sister.
Me: Never knew my brother was a girl.
Everyone else: :O
Listen up, numbskull! The joke is that the dude is implying he slept with the other dude's sister, but the dude flips it by saying his 'brother' is the one who's actually a girl. It's unexpected because people usually assume it's a sister, not a brother. As for you, I bet you still use training wheels.