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Horse Jockey's Boot 

1)Dilapidated, engorged membranous tissue forming the external covering or integument of a vagina.

2)Reflects a pliable pelt-like substance adhering to a womans loins.
1)Rumor had spread that Maria's horse jockey's boot was the largest external appendage in the Benton County Area on a female whore.

2) In the jungle, the mighty jungle, the horse jockey's boot sleeps tonight...
Horse Jockey's Boot by Toosh March 21, 2008
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Grandpa's Boot Camp

When the elderly is admitted to a rehab center for physical or occupational therapy.
Grandpa's Boot Camp is for new admittance, with strict discipline regime

lil' wayne's boot purse 

apperently its what lil' wayne keeps his pistol in when he walks around. its a very fashonable accessory which you can obtain by killing lil' wayne and prying it from his cold dead hands....good luck
"i got my gun in my boot purse"
lil' wayne's boot purse
from the song right above it by lil' wayne

Complain on one hand, take a dump in someone's boot on the other hand and see which is more interesting to talk about 

A twist on the saying ,"shit in in one hand and ask with the other and see which one gets filled 1st", targeted at complainers and whiners.
Whiney person: Everything sucks as usual.
Me: Complain on one hand, take a dump in someone's boot on the other hand and see which is more interesting to talk about.
Whiney person: That's the last time I complain to you about my life and also why are my boots in the bathroom?

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

Pilgrim’s Boot 

Taking “Das Boot” to the face post-Thanksgiving feast and proceeding to puke all over the family dining table.
Ever since Normandy, Grandpa Wallace has done the pilgrim’s boot at every Thanksgiving dinner.. I think he took i t too far this year after he puked in Grandma Lenora’s ashes.”

that's a boot

An activity that would take a considerable effort.
Nah dude, you're friend's house is to far to walk to--that's a boot.
that's a boot by Luisscarchi September 7, 2016