Urban Dictionary: Tootsie Roll

It is a sentence...........but OK. how many licks does it take to get to the center of a tootsie roll pop

by Sparkle355 March 13, 2017

When a male inserts his big toe into a woman’s anus, pulls it out and let’s her lick his big toe.

“I heard Jennifer’s into Brazilian Tootsie Rolls; must be a freak”

by DeepFriedAss October 07, 2020

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.

by keifchief November 28, 2018

When a black man is getting jerked off and he is about to ejaculate.

by Digger faggot September 14, 2016

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.

by Hotel Whiskey November 27, 2019

When something starts out good and then goes to shit, sometimes literally.

I went to the party Saturday. At first it was a Tootsie roll, but now it ain't.

by P3R53RT August 18, 2020

Sarah took off her edible panties prematurely because she accidentally made me a, “Tootsie Roll”.

by St@rdu$t January 24, 2021