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Red Toed Lollipop

When a girl is on her period and you insert your foot into her vagina and forcefully rip it out make a loud popping sound, and leaving your toes red.

Yo dude, last night I performed the Red Toed Lollipop on my GF.

by Mr. Horror November 16, 2016


Ruby Lollipops

Somewhat similar to the game 'Soggy Biscuit', but for women. Starting at a predetermined time, a group of women will menstruate as soon as possible. When a woman has finished her period, she places the used, bloody tampon into a bucket or other storage system. The last woman in the group to have her period must then eat all the used tampons of the other women in the group.

Woman: I have terrible stomach cramps due to my period. On the plus side, at least I won't lose THIS game of ruby lollipops, last time I had to eat 7 of the fuckers.

by Barry Stevington January 1, 2011


turn you into a lollipop

When you go elbow deep in your missus arse and pick her up with one arm walk down the street eating her pussy

Im going to turn you into a lollipop

by BL110 May 15, 2021


lollipop pole

a pole with a disc marked "Stop! Children crossing" that is used by lollipop men or women to help children to cross roads safely.

The lollipop pole has broken.

by uttam maharjan December 29, 2011


Triple Lollipop

A very intense wedgie in which the victim is given an atomic wedgie. But instead of stopping at the face, it goes down through the legs and back up into an atomic again. Now do that last part 2 more times. Viola, a triple lollipop.

Dude did you see that guy get a triple lollipop yesterday? Shit was gnarly.

by Wedgie_expert101 August 22, 2022


plumbers lollipop

A plumbers lollipop is when a male sticks his penis in a woman’s ass, then proceeds to maker her suck his penis

Jimmy “hey Deloris, want a PLUMBERS LOLLIPOP?” Deloris “ew no your so weird, why would anyone want a PLUMBERS LILLIPOP?”.

by ChanDaMan05 June 16, 2024


Give Him a Lollipop

A nice but useless person who you don’t want to involve but also you don’t want to be excluded.

Give him a lollipop and let him sit & listen to the discussion.

by Prometheusofwestsussex March 11, 2020