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jack boot day 

'Tis a day dedicated to booting people up the jacksie i.e kicking them up the arse. Popular with school children. Also you should note that it can be any day the kicker chooses and they can kick you in the shin if they so wish.
Kid: *runs up and kicks you in the shin*
Kid: Jack boot day. HA HA!
Kid *runs off*
You: WTF?? *hobble home*
jack boot day by Tenna May 13, 2005

Boot Jack 

It's where you stick your dick in a boot and jack off then wait until the unsuspecting character sticks their foot in the pile of semen.
I went to the boot store and did a Boot Jack in all the boots.
Boot Jack by Jack N. Dick December 10, 2006

bootysex Jack month 

Jack Kennedy should be bootysexed for a month because it deserves it. And the month should be June because its gay.
“Its June! You know what that means!”
Pride month..?”
“BOOTYSEX JACK MONTH.”

Boot Jack 

A person who needs to clean up their act. They are typically lazy, but a know it all at the same time.
Did you see that drunken boot jack trying to explain how to parallel park my car?

That boot jack over there has spilled more food on himself then has went into his mouth.
Boot Jack by JonnyTsunami2 May 1, 2023

jack sparrow`s boot 

The appearance of a highly sexually active older woman`s vagina. A hanging and leathery labia, resembling the flappy bits at the top a pirate`s boot.
"Steve, I saw you getting off with that blonde MILF last night. What was she like, then?"
"Bud, she went like a fucking steam train. Her twat was a bit worn out though; pissflaps looked like the top of Jack Sparrow`s boot".
jack sparrow`s boot by Clothears January 11, 2014
1. A thick military boot.
2. A common epithet, used to conflate someone with Nazism.
"I am still without any clear information as to what a jackboot is. It is a kind of boot that you put on when you want to behave tyrannically: that is as much as anyone seems to know."

-George Orwell
jackboot by nedlum February 15, 2006