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.

by keifchief November 28, 2018

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!

by jrqix August 19, 2017

Tootsie pouch

slang for butthole i.e. place you poop from.

Yesterday I had to go to the bathroom so bad my Tootsie pouch was ready to explode.

by King Ross 207 February 25, 2025

Tootsie Roll

A pair of edible panties with a human shit inside.

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

by St@rdu$t January 24, 2021

Tootsie roll

Calling someone (usually a man) queer for liking feminine stuff or kissing boys. It is basically the same as calling a feminine man a twinkie or using "gay" to shame a homosexual, but in a funny way.

*watching Winx Club* Woo yeah! Boyyyyyyyyyyy!
Guy stalking on him: HOLY SHIT OUR BOSS IS A MASSIVE TOOTSIE ROLL!

by Pickle_ur_Tickle April 30, 2024

California Tootsie Roll

When he/she pisses you off so much that you take a dump on the person in your sleep

Just wait… If she pisses me off again i’m going to giver her a California Tootsie Roll

by ManiacMonsterMalcom July 14, 2025

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.

by Hotel Whiskey November 27, 2019