jamaican tootsie pop

When you take your friends toe and shove it in your ass and then take it back out and cut it off. Then wrap it up in paper and let chill. When you proceed to eat it it will be like a tootsie pop.

Bro I had the best damn Jamaican tootsie pop ever last night with Humey.

jamaican tootsie pop by ItsDonnyP July 11, 2016

Urban Tootsie

Man with female assets (tits and ass) who live in urban neighborhoods dresses and lives as a woman.

Damn! That urban tootsie was from the hood?! Man, that gurl got a big booty!

Urban Tootsie by jrqix August 19, 2017

toledo tootsie roll 

To take a shit in ones hand, and proceed to stick just the head of the shit inside ones partner, then take the unprotruded end of the shit in both hands and proceed to roll it like Martha Stewart would roll dough.

Lee - "Dang Mark, I heard you gave her a Toledo Tootsie Roll."
Mark - " yeah I know man it was awesome but now my hands are covered in shit so I just wiped it on her."
Lee - "that sounds awesome I would have definitely rubbed it all over."

toledo tootsie roll by Steve scuba September 22, 2017

Brazilian tootsie pop

Sticking a toe inside a male or females rectum and making a pop noise

Yo last night nick gave that girl a Brazilian tootsie pop and it was so loud

Brazilian tootsie pop by Rusty cheese steak November 22, 2018

360 tootsie roll 

A sexual maneuver in where the participants assume the 69 position and then proceed to rotate on the Y axis 360 degrees.

Man: I 360 tootsie rolled my girl last night
Other Man: I've heard that drives the girls wild.

360 tootsie roll by keifchief November 28, 2018

Mississippi Tootsie Tickler

The act of spitting chewing tobacco juices upon a females toes in order to lubricate them to stick your penis in between them repeatedly.

My sister was horny so I gave her the ol’ Mississippi tootsie tickler.

Mississippi Tootsie Tickler by Distorted toast November 16, 2019

Lennie Tootsie Roll 

When you make out with a girl in a sleeping bag and she shits on you.

Jenny gave me a Lennie Tootsie Roll lastnight.

Jenny has a case of the Lennie Tootsie Rolls.

Lennie Tootsie Roll by Hotel Whiskey November 27, 2019