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.
When a girl is performing oral sex and inserts the penis into her mouth side ways pushing the head of the penis into the side of her cheek until his whole package is fully imerged into her mouth.
If a girl is capable of fitting your entire fist into her mouth she is a perfect candidate for deep cheeking.