Happy Gilmore is known for the way he takes 6-7 steps up to his golf ball before driving it further than humanly possible. Happy Gilmoring/Happy Gilmored piggy backs off this idea in that you take your fully erect penis and sprint right towards the bent over ass of the person you are trying to have sex with. The intent is to have your dick go further up the vagina/asshole than any other cock that has been in there in the past.
Dude: Yo man my chick drank so much and passed out leaning on the bed last night.
Friend: Did you do anything weird to her?
Dude: Weird? No. But I happy Gilmored the shit outta that ass. Got like 3 inches deep!
Friend: Did you do anything weird to her?
Dude: Weird? No. But I happy Gilmored the shit outta that ass. Got like 3 inches deep!
by Uncle Gary's Potato Farm May 18, 2017