The name for a joint when it is being rolled by a Jamaican.
Jamaican 1: Look at Delroy ehhh!

Jamaican 2: What’s that the yardie’s lickin?
Jamaican 1: The Rasta man has a Jamaican Lollipop ehhh.
Jamaican2: D-Roy gettin’ irie.
Jamaican 1: Ahlieeee fam
by that22guy November 6, 2019
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When your having sex and the guy doesn't clean up his come and it hardens
by Pussy in my mouth February 9, 2017
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The other day in class I fell asleep while we were reading Hamlet, it is such a lollipop book
by Randomlifesaver April 20, 2011
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The action of pulling someone's foreskin and sucking all the dirt and body fluids out of it
by Carbiondioxideisha March 20, 2018
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When you remove earwax with a Q-Tip then feed it to your cat.

It's slightly disturbing, but to them, it's natural animal fats and oils. It's very common for people to report their cat eats earwax. Apparently, cats have the inability to taste the bitter flavor of it.
I fed my kitty a cat lollipop.
by unidenphone July 6, 2022
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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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When one girl on her period puts on a strap on with a whole in it an "cums" blood in the other girls vagina.
Last night when we were drunk Mary and I made a bloody lollipop.
by DEEZ NUTS ON THE BEAT April 5, 2018
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