Lollipopping

Lollipopping is the act of inserting one's big toe into someone's anus for sexual pleasure. The feeling when it is first inserted is likened to a 'pop'
He has a foot fetish and likes butt stuff, so one of our favorite activities is lollipopping.
by HasAndWas May 20, 2024
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Covid lollipop

To solve covid by having the world infect themselves with covid via licking hypothetical lollipop contaminated with covid
We licked the covid lollipop, with the hope of going out without a mask or social distancing .

I'd rather lick the covid lollipop, then take the vaccine.
by Gocian March 07, 2021
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Lollipop Surprise

When you get a piece of shit stuck in your ass hairs and another person sucks on it like a lollipop
Nathaniel had his lollipop surprise taken care of by Cameron as Sean, Jonathan, Ethan and Simon watch.
by PrayerHub May 29, 2021
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Red Toed Lollipop

When a girl is on her period and you insert your foot into her vagina and forcefully rip it out make a loud popping sound, and leaving your toes red.
Yo dude, last night I performed the Red Toed Lollipop on my GF.
by Mr. Horror November 16, 2016
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Satans lollipop

When you fuck a girl on their period then you put it in their mouth.

This term is also applicable for any other circumstance where a bloody cock is devoured.
I took her home to give her a taste of Satans Lollipop.
by SacredScrotum January 30, 2024
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Ruby Lollipops

Somewhat similar to the game 'Soggy Biscuit', but for women. Starting at a predetermined time, a group of women will menstruate as soon as possible. When a woman has finished her period, she places the used, bloody tampon into a bucket or other storage system. The last woman in the group to have her period must then eat all the used tampons of the other women in the group.
Woman: I have terrible stomach cramps due to my period. On the plus side, at least I won't lose THIS game of ruby lollipops, last time I had to eat 7 of the fuckers.
by Barry Stevington January 01, 2011
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lollipop sandwich

Suck a lollipop right out you’re bitches sandwich (pussy)
by Dr.ASAP23 August 20, 2019
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