Pennywiser

When you don't know what to call a transgender person because you don't really care, so you call them "it" which is a reference to the monster Pennywise from the movie "It". He's a clown, just like people who claim to be a different gender than what they were born as.
Dude 1: "Bro! I seen Mr. Petersen getting head from a Pennywiser in a porta-potty!"
Dude 2: "Who was the Pennywiser?"
Dude 1: "It was Mr. Sparks. He was telling Mr. Petersen to call him Ms. Sparkles while dressed in drags!"
by Fearsomes March 29, 2018
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pennywise

when you’re engaged in anal sex and you begin to whisper “take it, take it” to your sex partner.
Ryan: I just gave my hoe a pennywise last week!
Will: Awesome!
by Slhapp Thatahse October 27, 2017
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Pennywise surprise

When you are banging a chick you pull out nut on a cherry pie , then hand her a balloon to distract her , you say " hello Georgie " to get her attention and smash the pie in her face to resemble being bloody . You say you'll float too and take off.
Did you hear about Joe he gave that stripper a pennywise surprise last night
by Turtle9376 September 19, 2017
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pennywise smut

pERSON 1: PeNnYWiSe sMuT1!!!1!!!!!!11!!!!1!!
Person 2: wtf man ur going 2 hell
by TumblrTrashHelpMe February 21, 2018
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dirty pennywise

A dirty pennywise is when someone is sucking dick and overstimulating the person until 'their soul leaves their body' or until they simply cant take it anymore.

the name comes from the soul-eating demon clown, pennywise, from the popular movie 'IT' by stephen king, hence the name, dirty pennywise.
bro i nearly died last night when my wife gave me a dirty pennywise!
by bloody octagon September 17, 2021
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