Tokyo Tootsie Roll

A competition between two people when they have their legs interlocked. Their anuses firm pressed together. Then one person begins to push a large length of firm excrement completely into the other persons anus. The goal of the person receiving is to push the excrement back into the originating person's body as if it were a normal bowel movement.
I tried to give bro that Tokyo Tootsie Roll but he pushed it back.

On our date we stayed up all night playing Tokyo Tootsie Roll.
by July 19, 2024
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Dark chocolate tootsie roll

When a black man is getting jerked off and he is about to ejaculate.
by Digger faggot September 14, 2016
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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 01, 2012
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Creamsicle Tootsie Roll

A sexual act, in which a man of standard height or stature, grabs a hold of a midget, or vertically challenged female, and holds her upside down. He may bear hug her lower body, or use both hands to hold her by the ankles if he has the hand strength to do so. But while she is being held upside down, she is performing oral sex on him, and simultaneously he is licking and sucking on all ten of her toes. This must continue until the man ejaculates into the dwarf's mouth
Little Gina from the strip club, she's asleep in the other room right now, she blacked out while I creamsicle tootsie rolled her... I had to finish bro, her toes tasted like pig asshole
by Kramardi September 16, 2022
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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
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toledo tootsie roll

To take a shit in ones hand, and proceed to stick just the head of the shit inside ones partner, then take the unprotruded end of the shit in both hands and proceed to roll it like Martha Stewart would roll dough.
Lee - "Dang Mark, I heard you gave her a Toledo Tootsie Roll."
Mark - " yeah I know man it was awesome but now my hands are covered in shit so I just wiped it on her."
Lee - "that sounds awesome I would have definitely rubbed it all over."
by Steve scuba September 19, 2017
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