1 - 20 of 55 Works in Pennywise (IT) & Reader
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You have been living a weird, miserable life in Derry. Bullied by the self proclaimed "King of Derry" Henry Bowers, like any other kid in town. Every single day of your life you feel you are being pushed to your limit. You feel like a kettle on a low fire ready to boil anytime. So far you managed to keep yourself in check. Never stepping out of line and keeping up the appearances of what a good person is supposed to be. As Halloween settles into Derry. Your anger and rage leads you to release something horrifying upon the town. You need to fix your mistakes and set everything right again. Through these hardships you find that who you thought was your biggest enemy is just as scared as you are.
Basically a Bowers x reader, where you and Bowers and some of the losers team up and fight pennywise. You and Bowers trauma bond.
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Penny's Banana Puddin' Pie by Miscellaneous_Box
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
04 Jan 2026
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Though many may not have a name for the terror that plagued derry, most have a notion that something in derry is dying. The weaver of reality has fallen and a rift is now left behind. What's left of derry is a collection of memories and a supernatural air that seems built into the very foundations. Maybe it's time to stop and smell the roses and maybe even have a sweet slice of Puddin' Pie.
(Shyte writing: good typing practice for me and a time-waster for you!)
- Language:
- English
- Words:
- 1,616
- Chapters:
- 1/?
- Kudos:
- 1
- Hits:
- 35
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Sacrilege. by Glitter_shitter
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
01 Jan 2026
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Some’thing’ that shouldn't have wanted me.
And some’thing’ I shouldn't have wanted.
Moving back to your mother's childhood home isn't all that bad. Not the quiet streets, not the old trees that whisper in the evenings, not even the rumours people pretend not to believe, including you.
You've heard the folktales. The warnings.
How the town can never be left. Not really.How foolish.
You're logical. You don't believe in myths, in kids stories, or the lingering touch of something unseen. You don't believe in curses that breathe, or in eyes that linger in the dark.
Nothing will ever change your mind.
Until it does.
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End of all things by FaeryBlue
Fandoms: IT - Stephen King, IT (Movies - Muschietti), Horror - Fandom
31 Dec 2025
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This will be a collection of small stories (maybe a plot? if you squint?) of Bob Gray/Pennywise/IT, the "eater of worlds" finding a human (THAT'S YOU!) absolutely irresistible in the worst way (for Pennywise) possible. Please note this is a toxic relationship, forbidden love with smut and violence. Pennywise is an absolutely disgusting being who wants nothing more than to corrupt and possess you entirely.
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Pennywise: an eldritch horror beyond all human comprehension. Completely and irrevocably obsessed with you.
You: A deer , perfectly caught within the headlights. A moth to the flame.
“Float with me forever in this, the end of all things..”
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Warning!! Smut & other NSFW themes ahead. Reader x Pennywise You have experienced his love before. But this time, he is tougher than usual, and you make the mistake of saying. “No.” Therefore you suffer the consequences...
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Give Me Your Fire, Give Me Your Fear by xxdevildancingxx
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
22 Dec 2025
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Some people would call you crazy for going urban exploring at one of the scariest, most talked about places in town - Neibolt house. You weren't afraid, though. Not until you encountered...him. The man who referred to himself as Pennywise. This is your rememberance of that fateful night.
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Blow the Grounsils by Sinister_exaggerator
Fandoms: IT - Stephen King, It: Welcome to Derry (TV), IT (Movies - Muschietti)
21 Dec 2025
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Calliope music was carried over on the wind, and a dark sky reflected in the puddles at your feet. Uproarious laughter bounced off multifarious, peaked canopies—insubstantial as paint swirling in water—until the scene inexplicably changed: the only remaining object, a circus wagon with the visage of a clown painted on its side.
You had a thing about clowns.
As if by magic, the wagon would vanish into thin air, only to be replaced by a black, undefinable void.
It was as if time and space themselves were being manipulated, gravity breaking its own universal law. You stood motionless—or were you floating?
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La Danse Macabre by SleeplessRamblings
Fandoms: It: Welcome to Derry (TV), IT - Stephen King, IT (Movies - Muschietti)
20 Dec 2025
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Moving to Derry was supposed to be a fresh start. Slowly becoming studied by an ancient eldritch entity that roams the darkened streets was not part of the plan.
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so long, derry by theehorrorluvrr2
Fandoms: It: Welcome to Derry (TV), IT - Stephen King, IT (Movies - Muschietti)
13 Dec 2025
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1908. After you get stuck in Derry, you decide to check out a carnival. You meet Pennywise the Dancing Clown, but you'd rather get to know Bob Gray, the man under the makeup.
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To Keep a Fawner by Morgue_Friends
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
09 Dec 2025
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‘The game of manipulation was spelled out in broad daylight for you and yet still you turned a blind eye to it. “What a good pet to bring a gift with you as well.”
“But I didn’t bring a gift?”
“But you did!”’
Haunted and guilt-stricken, the entity that hollowed you out and remolded you into someone new has snuck it’s way back into your life.
Series
- Part 2 of Fawner Series
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Pennywise x reader smut by Tomura_Shigarakis_Cum_Dust
Fandoms: IT - Stephen King, It: Welcome to Derry (TV)
26 Nov 2025
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Pennywise comes to the reader at night.
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Clown Love by drclowndaddy
Fandoms: IT - Stephen King, IT (Movies - Muschietti), clowns - Fandom
26 Nov 2025
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One man versus all of society. One mans slow spiral into clown.
Clown vs the World, coming straight to your house and home.
You lived a life of prejudice, judging clowns without even knowing them, spitting on them as they passed and indulging in stomping on their big clowns shoes and making them go "AIIIIIIIEEEE!" -
Fawner by Morgue_Friends
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
18 Nov 2025
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“Fun night?” You looked in the direction of the voice and saw the clown leaning against the wall by his clothed elbow, mocking you for being tired and out of breath. The puffy white, gray, and red clown suit looked unchanged as if this monster had been in this form undisturbed the entire night. “Now you might just be the one I've kept down here the longest.”
Days happen to go far too slowly for you after the disappearance of your best friend. Guilt and regret plague you deeply. Your salvation is just a mere imaginary retreat that’s still far out of reach. And if that salvation is what you truly want, it will take a sinner to give it to you.
Series
- Part 1 of Fawner Series
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Writhe by lavenderbiscotti
Fandoms: IT (Movies - Muschietti), IT - Stephen King, It: Welcome to Derry (TV)
17 Nov 2025
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After having wet dreams of a peculiar alien entity in the form of a clown, you wander into the sewers. Pennywise fucks the daylights out of you.
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“Would you like to see…where you really are?” it murmurs, brushing close, as it stands before you, so tall your neck aches from looking up at it with wide eyes. Its voice curls inside your mind in an intimate purr.
“I d-don’t understand.”
It smiles. “You will.”
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A Tumblr Request that kept coming back is now an unofficial series.
Enjoy! -
Eating Pennywise Out by greenandsorrow
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
27 Oct 2025
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Penny usually has a cock during your intimate times, but the good thing about being a shapeshifter is that he can always try something new.
~Ginger Clussy~
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IF THE MONSTER UNDER YOUR BED NEVER HURT YOU, MAYBE IT WAS THERE TO PROTECT YOU. by greenandsorrow
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
28 Sep 2025
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"Derry is a strange place. The fog settles low in the mornings, making the town look ghostly, almost unreal. The playgrounds are empty and quiet, swings moving slowly without any breeze. On foggy days, the whole town feels like a memory, faded and worn at the edges."
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PENNYWISE HEADCANONS AND DRABBLES COLLECTION by greenandsorrow
Fandoms: IT (Movies - Muschietti), IT - Stephen King
06 Sep 2025
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A clown-ish collection of short one shots, headcanons, and drabbles I've written.