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Teenagers (typically females) from mid to high income families with little to no disposable income due to high mortgages, car payments, etc have been know to engage in prostitution. These teenagers can typically be found in large malls standing or walking around sucking on a lollipop. The teenagers will perform sexual acts in exchange for money to purchase designer clothing and/or clothing that fits the latest trends.

A typical "lollipop girl" would be wearing pajama pants or sweatpants and a tank top or similar casual top. The dead give away, as stated before, is the lollipop in their mouth. One would not be surprised to see them enjoying the lollipop in a seductive way.

If you find one of these girls in your local mall you should probably avoid them as they are most likely jailbait.
"All I could find in the mall yesterday was lollipop girls."

"Damn, there are so many lollipop girls today they are a dime a dozen!"
by iburnmycd August 01, 2006
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2
Main Entry: lol-li-pop girl
Pronunciation: \ˈlä-li-ˌpäp ˈgər(-ə)l\
Function: noun
Etymology: Modern English, American slang associating the cheerfully bright, playful aspects of a colorful candy lollipop with a woman who recalls those same qualities
Date: May, 2010

1 a: a fun, carefree female who is widely considered delightful
1 b: a woman with an upbeat, colorful disposition : a perky, usually young, woman with a winning personality and sunshiny outlook
1 c: a lively, lighthearted female who often easily attracts amorous admirers
Being the consummate lollipop girl, Natasha endeared herself to all when she casually joked the spilled punch on her dress would bring back the tie-dye look.
by Pseudolus3 May 03, 2010
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-1.A girl whom is a virgin or so called a virgin and does only oral pleasures with her mates
-2.One who believes oral is not as bad as sex so is more willing to give oral sex over other things to please sexual desires
A girl is in the room with you and says she doesn't do sexual things but is willing to do oral therefore wether she has had sex or not nor does it matter if she is lying about past experience she is a "lollipop girl" by standards.
Usually will allow cumming on face but not in mouth

Note: some will allow cumming on face
via giphy
by Truth bout Girls July 26, 2017
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4
A person (usually a teenaged girl) who dances onstage with the popstar, Mika, during his song, "Lollipop,"which Mika wrote to his younger sister as a warning about the dangers of having sex too early. These people wear either a pink or blue dress (depending on gender) and a blonde bob wig w/a matching bow, and skip around stage with lollipops at the end of Mika's show. They are modeled after the character in the music video and CD booklet. The lucky ones interact with Mika himself. They also might be seen dancing with big girls.
Mika fan girl #1: I was Mika's lollipop girl.

Mika fan girl #2: OMG! Did you touch his curls?

Mika fan girl #1: No, he's too tall, but I touched his Gloomy Bear necklace!

Mika fan boy: I was a lollipop girl too, and I DID touch his curls!

Mika fan girls: SHOCK SHOCK us!
by Britney-the-lollipop-grl July 02, 2009
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