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

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

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.

by Distorted toast November 16, 2019

tootsie-wootsie

used to refer someone who you in love or you lile, in a childish way.

she's like my tootsie-wootsie.
hello, Carin, what's up tootsie?

by beax April 17, 2018

trump tootsie roll

A steaming dog turd wrapped in a candy wrapper with trumps face on it

those morons ate their trump tootsie roll and said, "please sir, may i have some more"

by The Phrogg May 07, 2025