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Tampon, A hidden meaning
{In frount of a large group of males aside to a friend}
Emo-weeker: Do you have errrm.....I could REALy use a lollipop right about now...
Friend:in the little pocket
by I'mInlovewithlipringBOY May 08, 2007
A one night stand.

A smash and dash sexual encounter.
shorty im just lookin for a lollipop.
by C.J. Duncan February 23, 2007
The true meaning of "lollipop" as referred to by Lil Wayne in his hit album makes an allusion to the two most prevalent methods of intoxication in the Dirty South. People actually make Lollipops out of the commonly used "Sizzurp".

These lollipops are a mixture of Promethazine VC with Codeine (sold by Atavis) which contain 10 mg of codeine phosphate, 6.25 mg of promethazine HCI, 5 mg of phenylephrene HCI and 7% alcohol. It has a red-orange color and strawberry flavor, and generally sells for $30 per pint

This mixed with some Xanax or Vicodein will have any girl licking you like a lollipop.
Hey you! Come over here so I can lick that lollipop and lean a bit.
by Haze Corps Theta Chi June 13, 2008
a man gential area
by SamanthaWeaver October 30, 2008
a heterosexual female who pretends to be bisexual or lesbian for attention
anne heche is such a fucking lollipop!
by Eris January 16, 2005
Tasty thing people like to suck
I like to lick a lollipop.
by Anna Maria July 17, 2006
A type of blowjob where she only licks the head of the dick, just as she would lick a lollipop. Can also be done after a guy finishes, to lick off the excess cum.
Yeah man she wouldn't actually give me head and put it in her mouth, she only gave me a lollipop.
After I finished, she gave me a lollipop so I wouldn't have to get a tissue to wipe off the cum dribble.
by Altamonte Alex April 21, 2008