Lollipopping

When an older man aggressively sucks a twink’s penis.
Oh my god, I just caught Greg lollipopping the new guy!
by MagruffTheCrimeDog April 08, 2022
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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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Louisiana Lollipop

A sex act typically down way south, where you do your sister in the ass. When you pull out your mom licks your Dick clean.
We had family fun night last night. We performed sex act on my sister called the Louisiana lollipop. Dad said my brother was next.
by The professor 827 December 28, 2021
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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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Midwest Lollipop

An alternative to I-70 or I-80 road head. The name for the act of getting suddenly blindfolded and tied up by your girlfriend in a two-star midwestern hotel off the highway; so she can whack you with a potholder, then fellate and ride your lollipop, while you lie there unable to thwart her fast food and White Claw-fueled demands.
“It was a long drive back to Colorado, but I gave him the Midwest Lollipop to break up the monotony.”

“Driving through the Midwest is tediously boring, but the GF gave me the Midwest Lollipop when we overnighted in Omaha.”

“Welcome to Iowa. Home of the Midwest Lollipop.”
by MammaCitaMeowMeow March 18, 2022
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