It was a Tootsie roll, but now it ain't.

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

tootsie roll critical number

the number at which the tootsie roll effect, therein goes into effect.

I met and surpassed the tootise roll critical number, as i am now here suffering the consequences on the shitter.

by rudog September 8, 2005

tootsie roll critical number

the number at which the tootsie roll effect, therein goes into effect.

You have surpassed the tootsie roll critical number, suffer the consequences.

by rudog September 26, 2005

Eastern Washington Frosting Covered Tootsie-Roll

A variation on the cleveland steamer where you are pokin your bitch in the ass, but she didnt take a poop before-hand, and you climax inside her rectum, and she takes a dump on your chest, and it resembles a frosting covered tootsie roll.

"I heard Reed got some of dat Eastern Washington Frosting Covered Tootsie-Roll from his skank last night. Truf."

by jram October 15, 2006

how many licks does it take to get to the center of a tootsie roll pop

One...two...three...*CRUNCH*

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

by Sparkle355 June 9, 2017

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

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