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Lollipopping is the act of inserting one's big toe into someone's anus for sexual pleasure. The feeling when it is first inserted is likened to a 'pop'
He has a foot fetish and likes butt stuff, so one of our favorite activities is lollipopping.
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.
When you get a piece of shit stuck in your ass hairs and another person sucks on it like a lollipop
Nathaniel had his lollipop surprise taken care of by Cameron as Sean, Jonathan, Ethan and Simon watch.
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.
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
Helps at crossings outside school and makes me lick his lollipop
I like licking lollipop man's lollipop
Peanut butter on a spoon.
Her hank can you grab me a polish lollipop ?