First, there was balls deep. Then, came hips deep. Now we have (drum roll) cheeks deep!
1. (noun) anything or person beyond that of hips deep, the farthest possible to man; 2. (noun) to shove one's lower abdomen into a cunt, until the gluteus maximus is at least one fifth obscured by the outer labial tissue of the cunt.
1. "You are way out there man. Fucking cheeks deep out there!"
2. Phillip DeFranco wishes he was cheeks deep in Katy Perry. He must wait for Russel Brand, to revert back into little British boys, to get a whack at it.
Reference to eating pussy. Like "balls deep" is to fucking.
Guy1: I heard he got balls deep in her last night.
Guy2: No. he's a pussy. he only got cheeks deep and then she left.