hole-in-two

The act of cumming any two of the following: a woman's ass, pussy, or her mouth all in one orgasm (or a man's ass AND mouth). It takes both good control and, with the ass or pussy to mouth, a longer orgasm with a large load.

Patrick fucked her ass hard until he started to cum. Then he used his kegel muscles to hold himself mid-cum while he quickly slipped his cock from her ass to her pussy and completed the hole-in-two.

hole-in-two by Kate Charlton February 9, 2008

Hole in two

When a male performing anal sex to a girl, proceeds to pop both of his testicles into the girl's anus with his genitalia. Proceeding this the male often will say "whole in two"

*pop pop*
Guy: HOLE IN TWO!!!!!
Girl: Take em out...

Hole in two by TheBigGH September 25, 2011

Hole in Two

A sexual act of the "German Miner Surpise" category, in which the male has the female positioned 'doggy style' (P-1469) and prepares for insertion, but surprises the female by instead inserting himself into 'door no. 2' (Hole-2).

"Oh yeah, stick it in"
"It's going in"
"John.....?......OH MY GOD! YOU DID NOT JUST GIVE ME A HOLE IN TWO!"

Hole in Two by German Sexual Deviant April 11, 2005

San Francisco Hole in Two 

When one sticks his own or a partners testicles inside the anus of a person.

They were having such rough sex that he gave her a San Francisco Hole in Two.

San Francisco Hole in Two by SanFranbuttsecks October 25, 2007

i'd throw it in the two hole 

An expression used to indicate that one finds a female reasonably attractive. Literally means that given the chance, you would like to engage in anal intercourse with her.

Britney: "Dad, I'd like you to meet my boyfriend, Kevin."
Dad: "Nice to meet you, Kevin. Now I want you to take good care of my daughter. She's a beautiful young lady and you should treat her with the respect she deserves."
Kevin: "You got that right, Pops. I'd throw it in the two hole. Can't wait to chuck my junk in that."
Dad: "Excuse me?"
Kevin: "Hey old man, you got a shitter around here? I got fuckin' plastered last night at the strip club and I've got some wicked beer shits."

i'd throw it in the two hole by Nick D August 28, 2005

Two in the Glory Hole 

when a man sticks his testicles into a woman's agape asshole repeatedly until he then sticks his penis into her asshole and ejaculates.

Depending on the radius of the asshole one's testicles may be sore after repeated penetration

Friend 1: Dude how wild was that chick last night?

Friend 2: Crazy man, she made me do two in the glory hole until i nutted right up in her ass, my balls hurt like hell though

Two in the Glory Hole by Barcelona Supporter April 25, 2011