Inside Out Tootsie Pop

Stick the lollipop in her ass and take a nice big suck.

Dude I dipped a big inside out tootsie pop from my girl’s butthole last night.

by jnullz September 3, 2023

Tootsie-Roll-Smear

by Heartmonger June 19, 2019

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

To cum from either a blowjob or getting eaten out. It plays on the phrase "How many licks does it take to get to the center of a tootsie pop?"

Person 1: How was it last night with Veronica?
Person 2: Awesome, She Tootsie popped me.

by BeePosting September 26, 2021

a joking slur to describe a gay person

"shut up tootsie pop"

by meek-hai-ell July 13, 2021

How many licks would it take to make it to the center of a tootsie pop? The world may never know!

by Canadian Keyboard October 23, 2019

by GoofyGoober2004 January 1, 2021