Coital positioning that allows for maximum penile depth.
I was digging deeper last night when that Ho hooked her legs around my neck. Next thing she’s yelling you are pounding my cervix.

He was a power bottom and shower no end to his gut rearrangement when I was digging deeper.
by Dick Onchin November 8, 2020
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Dig Deeper Watson is a smart reply to the popular exclamation "No Shit Sherlock!" Watson was sort of Sherlock's side-kick.
Scenario: *Yoon & Meg walk up to THE COFFEE BEANERY in a mall*

Yoon: Hey, the Coffee Beanery sells coffee!
Meg: No shit, shirlock!
Yoon: Dig deeper Watson... >.<;
by Dr3amingnDigital March 11, 2006
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