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Dig Deep 

When you can't quite get deep enough into a man's anus and a little extra is required. The term digging infers excavating stool from the orifice in order to facilitate "digging deeper".
man 1 "oooh, can't you go in a bit further"
man 2 " ok, but i'm gonna have to dig deep"
Dig Deep by wit_tank August 25, 2013
Related Words

colombian deep fry 

To soak the male genitals in a fresh pot of Colombian brewed coffee usually to the point at which the genitals are ripe for the plucking
After that Colombian deep fry I hacked my sack off effortlessly and then went boating with Stacy.
colombian deep fry by MamaDuck April 24, 2009

Web- deep 

Referring to a method of insertion.

To insert a finger or several into one's body cavity (mouth, anus, vaginally etc.) all the way in until you reach the webbing of your hand.

Mostly this action is stated as a threat.
"I'm gonna stick both these fingers in that ass Web- deep!"
Web- deep by twiggy eksfaur February 21, 2009

baws deep 

when you're shagging a burd and you push your full boaby in, you're baws deep.
I was baws deep in that lassie from the dancing.
baws deep by Shug The Bug June 12, 2014

6 Feet Deep 

Similar to the casual use of RIP. Used when expressing mild frustration or defeat about a particular incident.
“I dropped my AirPods in the toilet”
“Damn, 6 feet deep”
6 Feet Deep by MegamindSex January 20, 2020

"twenty deep in the street"

when you're rollin with your crew in your pimped sittin on twenty inch daytons, 20 inch motherfucking daytons!
An example of this phrase used in modern language is: Holla at a playa when you see him "twenty deep in the street".