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when a bullet fired from a gun strikes its target at a funny angle, the resulting asymmetrical hole looks like a keyhole, hence the name. usually caused by a worn or damaged barrel, or poor quality/incorrect caliber ammunition.
that ancient pistol i inherited from my grandfather is so worn out, half the time the bullets will keyhole and the other half of the time i can't even hit the target.
keyhole by facefault November 13, 2011
Pounding the pussy so hard with such a massive member that it thins or demolishes the taint leaving only a keyhole shaped chasm.
DAMN! I gave that ho a keyhole last night!
Keyhole by Dudeman Rokk August 15, 2011
You friggin' keyhole, shut up!
keyhole by RedRabbit October 1, 2004
Town drunk of Sauk Prairie. Do not headbutt or you will be injured. Has been known to "keyhole" a beer in .85 seconds and did a keg stand of 4 minutes and 20 seconds. Has retarded people assist him rolling joints. He had to wear a 40 lb. vest in jail.
Keyhole can keyhole a beer in .85 seconds.
Keyhole by Billy Tomcat January 5, 2005
He's such a keyhole! He never stops insulting me. He's quite annoying!
keyhole by Junglejim1 January 19, 2009

Keyhole squish 

A key is inserted into the mans cock hole and twisted as if unlocking a door. The inner penile tissue should tear and can be sucked out using a woman’s lips.
That guys dick is fucked, I heard Sandra gave him a keyhole squish
Keyhole squish by Swaggy longbottom September 21, 2017