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Whatever Caulks Your Wagon 

"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.

Caulyn Gross 

The most amazing, sexy, beautiful, awesome, and intelligent male being in the entirety of reality in any plane of existence. He also has the thiccest booty.
I pray to my lord and savior Caulyn Gross every night in hopes he will grace me with his divine and all powerful presence.
Caulyn Gross by The Dankster #87 September 23, 2019
Often confused with the word "cock." Here's to clear up any misconceptions.
Caulk - A gun that spews white stuff.
Cock - A gun that spews white stuff.
caulk by TenInchPlaya October 9, 2006

Caulk the wagon and float it

To take your time and be cautious when crossing rivers, but also not so cautious that you will only cross a river if there is a ferry present.

Originally a mindset used in the classic computer game The Oregon Trail, but can also be a way of life.
Don't be foolhardy and just try to ford the river. Take your time, be cautious, caulk the wagon and float it.

silicone caulking 

A titty fuck finishing on fake boobs.
Candy doesn't like me playing with her boobs since she got a boob job. But, she always enjoys a good silicone caulking.
silicone caulking by L&AW March 31, 2009
A white, viscous liquid adhesive which is waterproof when dry. The most common use is in buildings, to seal spaces (i.e., around windows) that would ordinarily reduce the efficiency of insulation.
Frylock: He - man - what the - you've been eating all my caulk!

Meatwad: Caulk? Nah, this is cheese!

Frylock: No, it's highly toxic industrial adhesive, used to connect electronic circuitry to steel. It's caulk!

Meatwad: And it's good, too!

Frylock: Listen to this, OK? Avoid human contact. May cause dizziness, nausea, and an ability to THINK you can see the future, but you can't!

Meatwad: Well, what does it say about finding oil?

Frylock: Nothing!

Meatwad: Uh oh.