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"whatever floats your boat" - whatever makes you happy. Caulk wagon is taken from the classic Apple II game Oregon Trail. A phrase meant to sound dirty when its really not.
ME: I'm gonna fuck MAD BITCHES
Hunter: Hey man, whatever caulks your wagon.
to stick your dick in a girl doggy and then pick her ass up and bounce it on you
dont bend your hips, dont ask her to do it; just caulk the wagon and float it.
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When a females vaginal area starts to leave a stench
I can smell your pussy juice caulking from over here
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An individual who is long dicked but is usually lacking in girth. One who cannot stand for a girthy bastard.
Ole boy Hires-caulk was hitting it dirty on that hooker last night.
A macho asshole who thinks his shit don't stink
Check out this buff caulk, stealing candy from children and blankets from homeless men
Pushing a female's face and mouth away from your cock while she is kneeling in front of you attempting to suck your dick
The foreman gave the secretary a caulk turndown and she was distracted and in need of some for the remainder of the day.
Hey didn’t you hear? Andrews mom is a caulk gobbler and she’s the best