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

Lollipop Top

One having skinny legs, accentuated by wearing "skinny jeans or jeagings" with a large round booty on top resembling that of a Lollypop.

Man that girls fine, did you see that booty? Yeah she got a Lollipop Top bro!

by Grafix Guy September 21, 2014

Pizza Lollipop

When one licks a disc-style pizza cutter after dividing a pizza fresh from the oven.

Shit! I just burnt my tongue on this god damned pizza lollipop!

by IGSDann April 26, 2014

furry lollipop

After completing no shave and no nut November, when the penis is super hairy and the balls are full of cum, and a blow job is given.

Tim: It’s finally destroy your dick December.
Hailey: Ugh FINALLY. I’m so horny I’d even suck your furry lollipop.

by Lordticklemaster November 4, 2021

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

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