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

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

Tootsie Rolled

The act of defecating inside of a condom and then inserting the condom into a woman's vagina.

Friend: "Hey bro, how did your date with that girl go last night?
Me: "It got a little weird, we Tootsie Rolled on the top of an old Indian burial ground by midnight."

by Gunner25 January 1, 2012

tootsie

a feminine gay man. calling someone a tootsie can be both derogatory or playful, it really depends on the context in which it is used.

derogatory: "stupid fucking tootsie... i bet he can't even tie his own shoes!"

playful: "i see you staring at him. you must really like him, huh, tootsie?"

by delaanii July 30, 2020

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

Dark chocolate tootsie roll

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

Stacy had herself a real dark chocolate tootsie roll.

by Digger faggot September 14, 2016

Wisconsin Tootsie Roll

Where an Asian man puts his penis in cheese

Chen got drunk and did a Wisconsin Tootsie Roll.

by PunchMunch August 13, 2024