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

Lollipop Leggings

Either lollipops with leggings on or leggings with lollipops on.

See also Lollies.

Oooh I love those Lollipop Leggings!!

by Emerald Star November 27, 2020

Covid lollipop

A hypothetical lollipop containing covid that the whole world licks

Stop wearing your mask now,and lick the covid lollipop today.

by Gocian March 8, 2021

Strawberry Lollipop

When a girl's period starts during intercourse and leaves your dick covered in blood.

I was all up in that girl and pulled out a strawberry lollipop. I kickstarted her period for her.

by eh-game May 16, 2016

Ohio Lollipop

The act of triggering the prolapse of one's partner's anus, either through applying enough pressure on his/her buttcheeks or by simply reaching out to the depths of his/her anus with one's hand and pulling the rectum out while twisting it, in order to lick it and suck it with progressively intense tongue and lip motions, as when performing oral sex. It is important to bear in mind that, after the act is performed, it is conventionally considered a lack of courtesy for the active partner not to return the receiving partner's anus to its original state, usually done by administering an Alabama Whack-a-Mole.

Man, I can still feel my asshole burning from the Ohio Lollipop Sally gave me last week!

by The Molester 69 March 17, 2018

Cobain lollipop

A shotgun

Jackweed 1: bruv did you hear what happened to austin
Jackass 1: nah bruv
Jackweed 1: he got a cobain lollipop from me

by XxpussySlayerxx9000000 January 7, 2019

Canadian Lollipop

The true canadian sexual act!

When a canadian had a new partner, it is traditional for the man to dip his dick into a bowl of maple syrup in order to have his partner lick it off.

Dude, you wouldn't believe it last night! Meredith gave me a Canadian Lollipop. It was great!

by HostelKris July 13, 2019