When you’re excessively going far back into someone’s social media past, and cannot afford to be caught out (e.g- accidentally liking a photo)
Omg I’m 85 weeks back into Jonathan’s Instagram...I’m so deep in the creep right now! I better not like anything!!
by Tilly Jay April 4, 2018

When a man has no testicles he can then proceed to go Leg Deep, as there is no balls to get in the way.
by perpetualpunks May 28, 2011

by unclekrackalacka October 17, 2010

During penetration a man is so deep inside his partner, both his penis and balls are inside the hole.
by Something-more-original December 4, 2016

When a male transitions to a female then has sex with a male. A male putting his penis inside a transitioned males penis now vagina.
by JohnnyJackHammer June 10, 2023

One has an itchy asshole in public and does not want to be seen scratching, so he proceeds to drill his hips downward and slightly side to side thereby discarding of the itchy asshole.
Bro, I was on a date with this chick when I got the most itchy asshole you could imagine! Yeah, I didn't want her to know so when I sat down I did the deep grind, and she had no idea I just took care of the most itchy bunghole in the whole building!
by ch@gmail.com cosmiksuckerpumcb January 29, 2018

by SlyFox08 November 28, 2016
