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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!
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!
A girl that has such a beautiful asshole that you would stick a lollipop in it and then take it out and suck on it.
That girl in the thong has a lollipop asshole.
When someone is giving a blowjob and the receiver goes limp in their mouth.
Man, this bitch was giving me head last night and I lollipop flopped!
One that licks sausages at the local grocery market and then proceeds to kill every man next to themselves. Usually a female Human being.
Jasmine: Is it alright if i go to the supermarket to buy sausages for our hot dog party tonight?
Chammy: It depends what kinds of sausages if you know what I mean.
Jasmine: Actually, I always like the sausages that were skinned so you couldn't see the burn marks of your enemies anymore.
Passerby: You fucking lollipop murderer, go jump off a bridge and die.
Either lollipops with leggings on or leggings with lollipops on.
See also Lollies.
Oooh I love those Lollipop Leggings!!
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.”