1 - 20 of 546 Works in Pennywise (IT)/Reader
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Welcome to Derry by Penitence
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
16 Feb 2026
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Lacrymaria Olor by lemonade_tea
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
16 Feb 2026
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Summary
And then, just as your eyelids begin to droop, you feel it.
A ghost of a touch drifting along your cheek—feather-light, teasing—raising goosebumps in its wake.
It stays there before trailing lower, tracing the curve of your jaw, the corner of your mouth. Every motion is filled with intent—like it’s memorizing you.
You sigh and lean into the touch before you can stop yourself.
Its name falls from your lips, soft and quiet, like a prayer.
Moving to Derry promised a fresh start, a new life. It was never meant to awaken a haunting, and yet it found you all the same.
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Bloodhound by Kahnitgoedeaper for Fungiandme
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
16 Feb 2026
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“Nothing is ever that easy. Remember?"
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This is a sequel to my previous book, "Blood Runs Cold." Twenty seven years later, you're lured back to Derry after a fresh start in a new city. You believe you've changed, you think that your time apart from Pennywise has given you a fresh state of mind, only to be completely confuddled the second you're met with his presence again.
You shouldn't want this again.
Yet, you do.
What will happen this time? Will the story remain the same? Will your end be full of heartbreak and the loss of yourself? Or will it be different?
This fanfiction takes place during IT 2017.
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crawling to thee by Anonymous
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
11 Feb 2026
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There's very little hope for someone like you—not human yet not as monstrous as the One you serve. What did you expect running into the backyard of a predator for protection?
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Ustulation - A burning Lust by vamp3h
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
10 Feb 2026
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Summary
It begins with infestation - slow, intimate, inescapable.
The ancient horror doesn’t just haunt you.
It seeps into you. Into your lungs, your veins, your thoughts. It plants visions that should never exist and turns every heartbeat into an offering.You are not prey. Not quite human. Not Its equal either.
It feeds on your fear - but craves your longing even more. And the worst part? You crave It back.
Because somewhere between devotion and decay, you stop knowing where you end… and where It begins.Was It the one who made you this way?
Or were you always meant to belong to It?
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This takes place in 2016, when Pennywise awakens again, following Its 1980s cycle. -
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Pennywise has fed on fear for centuries—until he meets a human who refuses to give him even the slightest trace of it.
She survives him. Studies him. Dares to challenge him. He studies, curious and possessive, as fascination replaces terror on both sides.
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Symbiosis by Graxy_weirdo
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
10 Feb 2026
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Summary
a town a clown.
Derry, a place where your worst nightmares come true, where people forget and which is forgotten by the rest of the world.
A life full of doubts and strange events, what will happen to you in the most curious place in the world?
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We meet again, but you don't remember me. by EdwardThee
Fandoms: IT (Movies - Muschietti)
09 Feb 2026
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Summary
First fic on AO3, tried to keep Pennywise as in character as possible.
Cis male!reader
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you got a call that your father has died in a horrible accident. so you move back to your home town, Derry. the place isnt the sunny cute town you remembered. not that you remember much anyways. things are eerie and off, you feel watched. soon enough you are face to face with a 7ft tall monster who has dreamt of you, missed you, craved you.
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Pennywise wakes up after 27 more years but this time with a need for revenge. he got interrupted when getting to his last victim of the season and he couldnt just let that go. when returning to that house, he finds the man that ruined his last attack and gets revenge, now he waits to finish off his meal. maybe he has a bit too much fun scaring her. maybe he doesnt want to eat her in the end. come find out;) -
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When Mary Poppins' granddaughter settles in 1960s Derry, she uses her magic umbrella and bottomless carpetbag to babysit, waitress... and quietly wage war against the thing in the drains.
But Pennywise takes one sniff of her storm-laced power and decides she's his new favorite obsession. Caught between protecting "her" kids and bargaining with the monster beneath the town, she's forced into a twisted game of rules, teeth, and a bond that feels far too much like being devoured.
!!!This fic is intended for 18+ readers only and may contain mature themes, explicit content, and adult situations. Please read at your own discretion!!!
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Familiar face [Pennywise x Reader] by PRXXIZ
Fandoms: IT - Stephen King, It: Welcome to Derry (TV)
30 Jan 2026
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Summary
Genderfluid reader.
In which,
Reader is a reincarnated being that's lived longer than IT, protecting the natives with their past encounter with IT. Seen as a gift sent by the Gods for the natives to help with the curse that laid upon them. Reader has been reincarnated many times, different people, different families, different genders. Yet they all remain with a familiar face. Always easily spotted by IT themselves, sometimes a little mixed up but never fail to find.Despite being a somewhat protector of derry, well, native land, IT or rather pennywise, one of IT's favorite forms can't help but mess with them, make them fear and become weak. Wanting to control them by messing with them mentally. Ending up having somewhat of a relationship between each other and the sudden need to make them a possible mate.
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A Fawner’s Rest by Morgue_Friends
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
28 Jan 2026
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Something’s gone awry with the entity that possesses and tends to abuse every aspect of your mind. He has you wrapped around his gloved finger like the toy you are. And yet, he’s become distant, behaving erratically and impulsively. It’s a test of wills and you need to be strong enough to endure it.
Series
- Part 3 of Fawner Series
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A year has passed with Pennywise back home safely. You’re doing your best to continue to grow as a person, and you’re thankful for your life every day, but having a family isn’t easy when you and your mate don’t always see eye to eye.
Series
- Part 2 of With Your Whole Heart
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A Curse For Eternity by Bee_Baddoo
Fandoms: IT - Stephen King, It: Welcome to Derry (TV)
25 Jan 2026
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Summary
This is pretty much a oc insert, with the reader as my oc, who is drawn to pennywise/derry. They find themselves constantly reborn and always ending up there with no memory of their past life. (In simple terms, at the end of each of IT’s cycles, IT kills the oc and the oc is reborn - there will be a depth explanation). Pennywise does NOT like the reader, finds them a nuisance and so on but gradually starts to grow fond of them and… we’ll see.
- Language:
- English
- Words:
- 5,265
- Chapters:
- 1/?
- Kudos:
- 4
- Hits:
- 72
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Sacrilege. by Glitter_shitter
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
24 Jan 2026
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Summary
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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Brat Taming by VelvetSkars
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
23 Jan 2026
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You've spent the day pushing Pennywise's buttons by flirting with every guy in sight, knowing it'll drive him insane. Now, in the sewers, he decides it's time to remind his little brat who she belongs to—with no mercy, no limits, and a whole lot of blood.
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Rose Water by VelvetSkars
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
23 Jan 2026
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Summary
Pennywise wakes up after his hibernation and is looking for you to give him a bath. [No gender specific terms used to describe reader insert]
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Epilogue: Mother and Bride by Sinister_exaggerator
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
22 Jan 2026
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Summary
“Tell me,” you cried, “tell me what I have to do to keep you, I love you so.”
The creature stiffened with a trill of Its embellishments, frozen as if by ice. It hovered over you with an arched back, eerily silent and completely motionless—then it smiled, unnatural and unnerving, Its grin a sharp knife bisecting Its face.
“What you have to do…” It languorously began, pushing Itself up off the ground to take a knee, “is wait here. Wait here like a goood girl, and no matter what you hear—no matter what you think you might hear, you will stay put.
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**Epilogue to "Blow and Grounsils" and "Rose Red." **
Series
- Part 3 of Down with the Clown
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Forgotten (Pennywise/Reader) by ZAULTIMATEBEARZ
Fandoms: IT (Movies - Muschietti), IT - Stephen King
19 Jan 2026
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The abandoned child of the Crimson King. The failure of creation, not what the King had wanted as a puppet. Discarded and trapped like trash, a 'lazy and slow' turtle came to the rescue. The turtle of enormous girth spoke onto the child "You are but not a mistake.. a world of possibilities.. you will watch over them.. but if you are to fall.. you will take time to heal.. coming back stronger than before.. my child of wonders.. eat.. sleep.. live amongst them.. but never forget.. who you are truly..". The child was sent onto earth, living amongst large animals well before humans, falling, healing.. forgetting.
As time passes and 1908 begins, a clown.. a friend.. a monster.. speaks onto the child who hold onto another's offspring "A friend you brought me? oh how fun! Now let's float! as high as the sun!"