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10.
1. Refering to someone as a sucker.

2. Being sweet (not in a good way)
You must be a lollipop if your gunna let her treat you like that!

that dude is a lollipop
by The highest of the high February 21, 2010
 
1.
A frigid bitchy cunt.
Sue is such a Lollipop. She won't talk to anybody that isn't loaded.
by AHGiz1337 March 10, 2009
 
2.
Frigid Bitchy Cunt
Well aren't you a fucking lollipop?
by AHG Fan March 18, 2009
 
3.
An innocent children's treat that implies penis.
Lil' Wayne: "I'll let you lick a lollipop."
Small child: "REALLY?!?!"
by Candicks August 21, 2009
 
4.
1. a form of candy on a stick.

2. a penis.

3. a wack ass song made by some pussy ass wannabe gangster named lil wayne who single handedly killed hip hop. He also stole the title from Snoop Dogg like most of the time he does. Dont like to hate on people but I mean, EVERY WHERE I GO somebody is riding his dick, if he has a dick.
1. WOW this lollipop tastes so good!

2. *sex sounds* oh yeah baby, now lick the lollipop *cums*

3. *Lil Wayne in Concert*

Lil Wayne: She l-l-l-l-licked me like a lollipop

Real Hip Hop fan: Shut the fuck up, the only pussy ur gonna get is birdman's, go suck a dick. You cant rap, a 5 year old could spit better lyrics then you ever will. You know why everyone is riding your dick? Because you sell records to a bunch of spoiled rich kids and a bunch of teenage girls who think your hot even though you look like my dog's ass. I actually should apologize to my dog's ass.

Lil Wayne: *cries and runs off the stage*

Concert host: Ok, Lil Wayne got off stage so now lets welcome, the renegades, JAY-Z AND EMINEM! MAKE SOME NOISE!

*Jay-Z and Eminem start to perform Renegade.*

Real Hip Hop fan: Ok this is more like it.
by The Man3455 August 01, 2009
 
5.
A phrase used in an awkward situation.
Person 1: "I'm not going to school tomorrow."
Person 2: "LUCKY!!!"
Person 1: "...I'm going to a funeral..."
Person 2: "Lollipop?!"
by Beckster09 June 19, 2009
 
6.
A sweet that is sucked. The interesting thing about this word is that originally meant a toffee apple. It is a fairground word from the Romany 'loli phaba', meaning red apple.
Telly Savalas sucks lollipops

loli phaba maishinava khal, khal,
yek pash tutir, yek pash mandir, hop, hop, hop. (Romany song)
by klidenengro November 06, 2011
 
7.
The vital force, heart, and tremendous power that permanently rests within only a diminutive handful of individuals with exceptional courage, drive, and strength, who have limitless potential in life that can never be taken away from them.
"They may be able to steal your candy, but they can never take away your lolli pop"
by Jolly Rancher May 02, 2005