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The act of picking your nose and/or not choosing to eat it, while others have witnessed you actually do it & are secretly betting money on whether or not you actually are going to eat the booger you just freshly picked or do the right thing and just wipe it on your pants or blow your nose...
Oh my fucking God Jesse, LOOK, Bettyann's Caddyshacking AGAIN! She just picked her nose and she even didn't notice us watch her do it. I'll make you a bet, if she eats the booger or not & remember just yesterday we just were laughing at that particular scene in the movie Caddyshack: "Say, $50 bucks- the Smails' kid picks his nose. $50 bucks more, says he eats it!..."
by green eyed lady 13 July 09, 2014
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When you dress up like a golfer and have "golf themed" anal sex while watching golf on television.
If your lover, mistress, partner, or friend is an avid fan of the sport of golf it is suggested that you incorporate Caddy Shacking into the act of watching golf on television. Caddy Shacking is an anal sex party game, where you must announce the events that are occurring on TV while having anal sex.

Recipient: I need to pull the pin (butt-plug) out before you try to sink the putt.
Giver: I need to line up this putt so I can get a good, long, and a solid stroke.
by Cocktavious Vagsquirten October 16, 2011
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The act of ejaculating in ones hand, then promptly slapping your woman with the jizz filled palm.
Woah dude, did you hear how hard Ron has been caddyshacking his girl lately?
by Ronaldo Stevens November 02, 2017
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The act of lining a golf ball up to your sexual partners vagina or anus, then smashing it in with a gold club, usually a 9-iron.
Hey bro, can I borrow your 9-iron, me and my girl are gonna try caddy shacking
by giggles mglongdong November 21, 2011
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