Tootsie Pop

Used to describe a woman who is rather unattractive, except at her center, namely, her ass; an otherwise ugly woman with a good butt.

"Look at that tootsie-pop, man... if only the rest of her matched up with her ass."

by Pseudonym November 10, 2004

Tootsie Pop

The act of sneaking your finger into your buttcrack or butthole and having a girl unknowingly suck on that finger

"Yo dude, i gave that bitch a tootsie pop last night."

by kcchiefs07 October 13, 2007

Tootsie Pop

When someone falls asleep and gets a baguette shoved up their ass with a chocolate flavored donut put on the tip. The friends test how many licks it takes to get to the center.

Holy Cow look at that huge Tootsie Pop coming out of Vinny's ass, I cant wait to eat that shit up.

by the cotck August 20, 2009

towanda tootsie pop

Named after a small Northern Pennsylvania town known for incest. A Townada tootsie pop occurs after anal sex with a close relative when a penis is cleaned orally.

Sam gave Bill a towanda tootsie pop.

by Towanda Tootsie Pop March 8, 2016

Toronto tootsie pop

Where you insert a piece of candy into the pee hole of a man and have a partner suck it out while they are blowing you

"It hurt like a bitch, but that whore Megan Fogarty gave me a Toronto tootsie pop."

by SicNtwisted February 11, 2014

cherry tootsie pop

having anal sex with a girl on her period, followed by vaginal intercourse, followed by blowjob

Oh, Mackenzie, I just love cherry tootsie pops!

What's that?

When you let a guy fuck you in the ass while you're on your period, then let him put it in your pussy, then suck him off.

by Bull26 April 6, 2007

Cherry Tootsie Pop

An act involving a menstruating woman and a second subject, in which the menstruating woman takes a mustache ride and simultaneously releases her bowels, thereby covering the subject's face in the red and brown mixture.

"Last night that kinky bitch showed me how many licks it takes to get to the center of a Cherry Tootsie Pop."

by Shizzynat April 7, 2008