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 28, 2021

latina lollipop

Watching an over weight Mexican man or woman at a laundry mat, while awaiting clothes to dry

Kirk and I enjoyed a Latina Lollipopoing at the local laundry mat.

by HurtRussLE9300 November 12, 2015

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 8, 2022

crack lollipops

Crack lollipops are lollipops that obtain crack inside of them. They make you bleed eternally.

Crack lollipops from Nathan kakaka

by Cracklollipops November 8, 2019

Fish Lollipop

A term used for a man with an affinity for cheap hookers and prefers to be finished off orally

“My buddy got real drunk last night and gave someone the ol’ fish lollipop”

by Mini!!! April 12, 2024

Lollipop(in)

To try and sucker someone to think you're a good person. To seem innocent or without knowledge so other people can help or baby you when a person does not want to help themselves. Created by: Zaneeta Davis

Ex. Stop trying to lollipop me okay.

He be lollipop(in) all day but I can see through him.

by Neeta Dee August 28, 2024

lollipopping

When someone is being overly sweet, cheesy, or lovey-dovey with their partner on the phone—especially in front of their friends—causing secondhand embarrassment.

“Oi, stop lollipopping and help me carry this sofa!”
“She was full-on lollipopping with her boyfriend while we were trying to eat.”

by Benjamin Dawn June 10, 2025