1 - 20 of 507 Works in Pennywise (IT)/Reader
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stinky sewer boy and a fortunate soul by catboy_rookie
Fandoms: It: Welcome to Derry (TV), IT (Movies - Muschietti)
21 Dec 2025
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ive got nowhere else to post this, tumblr would be ideal but they’d probably nuke my whole account if i tried. so might as well put it here.
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The Lost Ones by DeadKopski
Fandoms: IT (Movies - Muschietti), IT - Stephen King, It: Welcome to Derry (TV)
21 Dec 2025
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After landing a job in Derry, you notice something is off… Children are going missing, and your health is getting worse by the minute.
Following a horrific encounter, you begin to experience things you can’t explain- as slowly, your life unravels into a waking nightmare…
One you’re not so sure you can escape…
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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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❝𝐘𝐎𝐔'𝐑𝐄 𝐃𝐈𝐒𝐆𝐔𝐒𝐓𝐈𝐍𝐆. 𝐀 𝐂𝐀𝐍𝐍𝐈𝐁𝐀𝐋. 𝐀 𝐂𝐎𝐍𝐒𝐔𝐌𝐄𝐑 𝐎𝐅 𝐇𝐔𝐌𝐀𝐍 𝐅𝐋𝐄𝐒𝐇. 𝐓𝐇𝐄𝐑𝐄 𝐖𝐀𝐒 𝐀 𝐓𝐈𝐌𝐄 𝐖𝐇𝐄𝐍 𝐈 𝐂𝐎𝐔𝐋𝐃𝐍'𝐓 𝐈𝐌𝐀𝐆𝐈𝐍𝐄 𝐀𝐍𝐘𝐎𝐍𝐄 𝐁𝐄𝐈𝐍𝐆 𝐖𝐇𝐀𝐓 𝐘𝐎𝐔 𝐀𝐑𝐄, 𝐀𝐍𝐃 𝐃𝐎𝐈𝐍𝐆 𝐖𝐇𝐀𝐓 𝐘𝐎𝐔 𝐃𝐎. 𝐁𝐔𝐓 𝐍𝐎𝐖 𝐈 𝐑𝐄𝐀𝐋𝐈𝐙𝐄 𝐈'𝐌 𝐉𝐔𝐒𝐓 𝐋𝐈𝐊𝐄 𝐘𝐎𝐔. 𝐈 𝐂𝐎𝐍𝐒𝐔𝐌𝐄 𝐄𝐕𝐄𝐑𝐘𝐎𝐍𝐄 𝐈 𝐋𝐎𝐕𝐄. ❞
⋅───⊱༺ 【 🎪 】༻⊰───⋅
𝐘𝐎𝐔 return to Derry to take custody of your younger second cousin, Richie Tozier, and try to build a quiet life as a teacher. That plan dies the moment you meet Bob Gray.
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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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Summary
You finally return to Derry, Maine, after many years after the death of your cousin's father. Through the naked eye, the town seems completely normal, but what happens when you find out what really lurks beneath, inside of the shadows?
This fanfiction takes place during Welcome To Derry.
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Squirm For The Clown by Decent_Arrow78
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
19 Dec 2025
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Summary
Pennywise has some fun with you.
- Language:
- English
- Words:
- 383
- Chapters:
- 1/1
- Kudos:
- 21
- Hits:
- 441
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Lacrymaria Olor by lemonade_tea
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
18 Dec 2025
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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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Down In The Sewers by Decent_Arrow78
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
18 Dec 2025
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You crave something fucked up. Pennywise has no issue giving you what you need.
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Sacrilege. by Glitter_shitter
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
18 Dec 2025
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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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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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Pennywise is especially pleased with you after you left him tasty gifts.
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Do You Want To Float? by Decent_Arrow78
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
16 Dec 2025
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You were always drawn to the dark and twisted, including Pennywise. When he finds you, your true desires are exposed.
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Welcome to Derry by Penitence
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
15 Dec 2025
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Candy and popcorn... And something else rotten. by Sweeneysshit
Fandoms: It: Welcome to Derry (TV), IT (Movies - Muschietti)
14 Dec 2025
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Historia tipo AU, basada en el episodio 7 de la primera temporada de It: Welcome to Derry.
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The Way He Knows How (Pennywise x Reader Drabble) by CinnamonTrashCrunch
Fandoms: IT - Stephen King
13 Dec 2025
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Just wanted to write a bit of fun cause I love Pennywise.
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Your Chemistry by LuciferaBlack
Fandoms: IT (Movies - Muschietti), It: Welcome to Derry (TV)
13 Dec 2025
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Temporarily moving to Derry has been stressful, lonely and boring, until you think you see a clown in a drain pipe. Deciding you need a break, you walk into town that evening and meet a charming and eccentric young man named Bob.
You quickly learn that the man and the clown are the same entity, and It is very curious about your feelings and the scents they produce.
The entity shifts back and forth between clown and man, trying to get you to feel love for It so It can experience the scent for the first time.
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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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Foolish Games by VelvetSkars
Fandoms: IT - Stephen King, IT (Movies - Muschietti), It: Welcome to Derry (TV)
12 Dec 2025
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Addicted to dangerous "games" with Pennywise, you are abruptly taken to his domain, where he reminds you of your place in his world.
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Begged To Be Bred by VelvetSkars
Fandoms: IT - Stephen King, It: Welcome to Derry (TV), IT (Movies - Muschietti)
10 Dec 2025
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You went looking for the monster in Derry’s sewers, half daring it to come take you. It did.