To get as deep as you can inside someones vagina and make a digging motion with your penis...

When you bum fuck a virgin so hard that it leaves a huge hole in place of her asshole

A tracked machine with a arm attachment used to dig below the surface. Used often in construction and industry.

the action of excavating something, especially an archaeological site.

When a man puts his penis into a woman's mouth and pulls it out on her cheek, sometimes causing a popping sound.

A drill used to impale zombies and flip them around like a merry go round striking surrounding zombies with its body.

Verb -- Any sexual situation in which you "have to dig." i.e., if she is a virgin (and you have to "hollow that shit out"), or if you are engaging in anal intercourse and the girl has a tight ass.