Philly Boot Brush

Requires a two headed woman, the man must stand overtop of the heads, and gyrate back and forth allowing the mouths to “brush” his asshole and penis.

I went on a date with lacy and Lucy last night and we did the Philly boot brush! It was the best when lacy chewed on my hemorrhoid like a gob stopper.

by Greenknuckles September 5, 2025

Proctologist boot

Proctologist boot, where you take a hookers stiletto and strap it on your foot and you banger in the ass with it.

Man, that chick guy I met last night had the most baddest stilettos. I had to give her a proctologist boot.

(David): man that chick last night had some expenses stilettos
(Benny): yeah that’s why I had to take her home last night and give her the proctologist boot.
(David): I get it now that’s why she’s walking so funny man you must’ve done that for hours

by 0069RIGID December 10, 2025

Shoot and Boot

Shoot your load and boot them out.

I'd shoot and boot that chick.

by torminator October 16, 2012

Tuscaloosa Tooter Boot

In the middle of making tender love to a diabetic girl, your blood sugar levels start to spike. She, in a fit of passion, injects her insulin shot into your dick. You scream but realize that it feels good, so you ask for more. You're swollen with insulin, which reincorporates into your bloodstream and causes a coma. While in the coma the diabetic girl tap dances on your chest, which expels all the extra gas in your colon, the "tooter". After long enough the last meal you ate will be expelled as feces - all natural - and she collects in a pair of red cowboy boots, which she places on your feet. Then you wake up from the coma and realize the diabetic girl was your sister. You scream and shot but she just seems pleased with herself, and after you take off the red cowboy boots in disgust, she licks your feet clean. It feels good, but you're confused.

"Hey Dave! How'd it go with the girl from the bar last night?"

"Not so good, Brian. She Tuscaloosa Tooter Booted me."

"Damn, we both must have been drunk. That was Shelly?"

"'Fraid so."

by Dave TTB September 6, 2013

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".

by Clothears January 11, 2014

mississippi mud boot

Foot in Anus.

I can't sick down because I got Mississippi mud boot last night at the Trump rally.

by poopNow July 11, 2016

as a boot

Can be applied to anything, anytime, best used in groups of people from Delaware

"Dude I'm hungry as a boot" or "that shit was hard as a boot" or "let's get high as a boot"

by deadlikeu82 June 21, 2016