masturbating in the bathroom while your roommates are out and are unsure of when they'll return; IE, maturbating while home alone.
Pun on the word "caulking" (pronounced "call-king"), the rubbery silicone sealant around tubs and sinks.
roommate: What the hell were you doing in the bathroom when I got home? You were in there for a while.
deviant: Oh just Macaulay Caulking the bathtub tiles... you didn't leave a note so I didn't know when you'd be home.
roomate: gross
by Donkeyfly July 12, 2013
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What comes out of a man's thingie when he has an orgasam.
After I pulled out, I shot my bitch caulk all over her face like a thug.
by DoctorThrottle April 29, 2004
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the effect on your insides,when you drink them raisin dry with lots of cheap whiskey (preferably The Great Macaulay Premium Scotch Whiskey 40 % Vol.)
A: Do you still have that horrible stomachache?!
B: It will be over soon, because tonight's gonna be macaulay caulking
by ChrisRiot December 18, 2012
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The act of pulling out during sexual intercourse (anal or vaginal) and ejaculating along the crack of the ass. Can be used alone or in combination with the Dirty Sanchez, the Tony Danza, the donkey punch, as a climax to the alligator fuckhouse, etc. depending on the level of frustration and/or kinkiness involved.
That bitch didn't want a creampie, so I caulked her wagon instead. Afterwards she floated in the bathtub. You would have thought she was on her way to Oregon. Caulk the wagon or ford it? I chose the former.
by Tyrone Biggums Brother January 26, 2009
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The adult film star shit his cock caulk all over his co-star’s back; it was considered a comeback film for both of them.
by Mr. H-A-R-T November 16, 2019
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After coming on a girl's asscrack, the guy uses his penis to smear the semen along the entire length of the ass crack.
The fat girl's ass stank so bad, I had to Caulk The Wagon to get to sleep.
by MrODoyle January 23, 2009
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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.
by Christian Suba September 8, 2007
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