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 03, 2023
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tootsie pop

a joking slur to describe a gay person
"shut up tootsie pop"
by meek-hai-ell July 13, 2021
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Tootsie pop

The OG commercial that everyone saw
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
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Tootsie Pop

Man that guy is such a Tootsie Pop
by GoofyGoober2004 January 01, 2021
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Milwaukee Tootsie Pop

When one has a Pink Sock and takes a shit in the pink mass that is their own prolapsed anus.
"Ah man, I should not have eaten all that Mexican Food before I got anally plundered. I'm not going to be able to hold my shit in much longer and my Pink Sock is going to become a Milwaukee Tootsie Pop."
by Jay Shepherd May 26, 2023
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Chocolate Tootsie Pop

Is defined as the sexual act of giving anal following the male or female licking fecal matter off of the penis and or testicles
Person 1: How was your date with Jane
Person 2: It was great! I tired anal for the first time and slipped her the old Chocolate Tootsie Pop
by Pizzaeater69 December 04, 2019
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jamaican tootsie pop

When you take your friends toe and shove it in your ass and then take it back out and cut it off. Then wrap it up in paper and let chill. When you proceed to eat it it will be like a tootsie pop.
Bro I had the best damn Jamaican tootsie pop ever last night with Humey.
by ItsDonnyP March 24, 2016
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