Cheeky drilla 

One who is very cheeky in his drilling. One who drills on his own usually in his own time and under the bed sheets in the dark at courageous times of the day.

Freddy is a cheeky drilla. You never know what to expect but sometimes his drilling is cheeky and done at very clever moments.

Cheeky drilla by UBBI GIUM June 22, 2022

drill cheeks 

The act of penetrating ones buttcheeks with a phallic object i.e. sexual intercourse

Damn son Tonya say she feelin me im bouta drill cheeks

drill cheeks by REALOBT September 15, 2016

drill them cheeks 

to roughly thrust your dick into a female from behind.

"Aye Larrice what you doing tonight bruh ? "
"Ole girl coming over tonight I'm finna drill them cheeks my dude!"

drill them cheeks by KingK2 March 22, 2016

drill yo cheeks 

Drill yo cheeks meaning you want to fuck the shit out of a gurll really hard because she either A. Has a fat ass or B. looks really good

Person A: Yea I Wanna drill yo cheeks

Person B : What that mean

Person A: Basically it means I wanna fuck the shit out of you bc you ass look fat and you look good

drill yo cheeks by Robert Mims April 19, 2018

drill them cheeks 

Another word for eatin ass like groceries

"Yo lemme come over your house and drill them cheeks"

drill them cheeks by KIng.seth12 August 1, 2016