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1.
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.
by Kate Charlton February 09, 2008
 
2.
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...
by TheBigGH May 24, 2011
 
3.
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!"
by German Sexual Deviant April 11, 2005