Pennywise Stories

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1.2K Stories

  • Baby Doll (Pennywise X Male! Reader) by 6Tim_Wright9
    6Tim_Wright9
    • WpView
      Reads 97,623
    • WpPart
      Parts 14
    (Y/n)'s different then other kids. He doesn't know his mother. He's mocked over the clothes he wears and his father's 'fey' appearance. He doesn't even seem to have fear. Everyone in town wonders how 'the little dandy' hasn't been taken some how. That kind of thing happens in Derry. It happens all the time. It's a normal occurrence, one that he's used to seeing. Until he became an infuriating puzzle to something lurking beneath the city. I feel some regret for the idea that's plaguing me right now, but eh... I hope it's enjoyable. ~So come and read it if you want to see it ~ No art belongs to me. Pennywise doesn't belong to me, nether does anyone else mentioned from IT. Reader belongs to themselves. all I own is the story line presented here.
  • Stranger things x IT x reader  by megaapandaa
    megaapandaa
    • WpView
      Reads 6,753
    • WpPart
      Parts 23
    Meet y/n l/n a misfit, a "Loser", she had never had...a great life but she's had her best friends the losers until the terrifying summer of 84 when she runs away from everyone and everything and finds herself in Hawkins Indiana...changed. What will happen? Read to find out...if you dare. First time writer be warned SLOW UPDATES IT chapter 1: ✓ ST Season 2: in progress... ◌ ST Season 3: 𝕏 ST Season 4: 𝕏
  • Pennywise Loves Me?》It (2017) by lovethebreeze
    lovethebreeze
    • WpView
      Reads 103,351
    • WpPart
      Parts 14
    In the quiet town of Derry, Main, join Jenny Denbrough help the Losers Club fight the evil clown known as Pennywise. But along the way, she realizes that the clown is doing more than terrorizing her brother and friends...It's growing fond of her. And if you think this story will have a happy ending...you're wrong. [Book 1.] [Very slow updates.] [Disclaimer: I only own Jenny and her plot.]
  • scared, love? || eddie kaspbrak x oc {1} (COMPLETED!!) ~under editing :)~ by canadiantiredalways
    canadiantiredalways
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      Reads 293,515
    • WpPart
      Parts 50
    "What are you smiling about?" Stanley stared at him. "She called you a dumbass." Eddie's smile only grew bigger. "I know. Ali Sumner called me a dumbass." *** in which ali sumner befriends a group of outcasts and finds herself harassed by ronald mcdonalds fucked up crackhead cousin :) *** just a btw, the y/n character is technically an oc but i j didnt wanna write a story using "y/n" the entire time so j pretend "ali" actually says "y/n" for any xreader readers loll
  • Deal with God// It 2019 by irishsnowflakeluv
    irishsnowflakeluv
    • WpView
      Reads 558
    • WpPart
      Parts 15
    Book 2 ___________ Its been 27 years... It's back.... Will Sarah survive? ________________ I do not own IT 2019, this is just afun silly hobby. All rights reserved. ------------------------- Idea from 2019 Written '24/'25 Posted 2025 Completed 2025
  • The Daughter of Pennywise the Clown by b0nerfart
    b0nerfart
    • WpView
      Reads 59,811
    • WpPart
      Parts 13
    Carissa Thompson was totally normal. Ish. She never really looked normal, or acted normal. Because she wasn't. Recently she moved to Derry Maine. She meets the losers club along with someone she thought she would never meet. Sorry. This is my first story. I use profanity. But uhh just read the book and enjoy!
  • Not Afraid {completed} by codyfernswaifu
    codyfernswaifu
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      Reads 63,287
    • WpPart
      Parts 19
    Hardened by New York streets, fearless Y/N moves into Neibolt house, grateful she got the house for such a low price. After months and months of renovating, finally she got the old house renovated and all to her liking, not knowing something very old lived right under her.
  • Ezra's Purple Eyes by jebby78
    jebby78
    • WpView
      Reads 7,600
    • WpPart
      Parts 10
    Sequel to Daughter of Pennywise It's been 27 years since Pennywise and his daughter, Ezra, we're killed by the losers club. Or so it seemed. Now the losers have been called back by Mike Hanlon for IT has started killing again, but when Ezra waltzes in its just like it was 27 years ago. Which side is Ezra on this time?
  • Taken (a Pennywise fanfic) by sotrueactually
    sotrueactually
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      Reads 15,778
    • WpPart
      Parts 12
    warning: i started writing this when i was 13 so please dont expect anything mindblowing... anyway its a very cliche wattpad story. girl gets taken (by pennywise) and tries to escape.
  • Love is pain, pain is mine. (Pennywise X Reader) by PennywisePens
    PennywisePens
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      Reads 83
    • WpPart
      Parts 5
    A pennywise X reader story.
  • When the Road Leads to You || Reddie + Stenbrough by rachelswrites
    rachelswrites
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      Reads 24
    • WpPart
      Parts 7
    "What if we did date? What if it actually worked? He's everything I'd want. But what would my mom think? What would the others think?" After graduation, the Losers Club head out on a month-long trip to the Rangeley Lakes Region. Just a chance to relax and goof off before life gets serious. But between campfire jokes, late-night swims, and teasing that turns a little too warm. Stan and Bill become open about their relationship and Richie and Eddie began to realize their connection wasn't just a joke anymore... and maybe it never was.
  • LOLLIPOPS || STANLEY URIS by Roxy_r0cks
    Roxy_r0cks
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      Reads 19
    • WpPart
      Parts 5
    If I had a Flower every time I thought of you,I could walk in my garden forever. -Alfred Lord Tennyson
  • 𝐀𝐋𝐋 𝐅𝐎𝐑 𝐘𝐎𝐔 | 𝙇𝙄𝙇𝙇𝙔 𝘽𝘼𝙄𝙉𝘽𝙍𝙄𝘿𝙂𝙀 by pattycak3s
    pattycak3s
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      Reads 52
    • WpPart
      Parts 4
    ┃𝐖𝐄𝐋𝐂𝐎𝐌𝐄 𝐓𝐎 𝐃𝐄𝐑𝐑𝐘 1960, 𝘿𝙚𝙧𝙧𝙮, 𝙈𝙖𝙞𝙣𝙚. In 1960, the city of Derry is engulfed in strange disappearances, noises echoing through the sewers, and smiles that last a second longer than they should. It is in this setting that Clara Marsh, 13 years old, emerges-the girl everyone knows but no one really sees. The younger sister of Alvin Marsh, Clara has always been treated like a ghost within her own home: invisible to her family, stifled by her brother's harsh words and the suffocating atmosphere that dominates the Marsh residence. When Clara begins to suffer strange fainting spells and nightmares with laughter that doesn't belong to anyone alive, she tries to distance herself from the world... until she meets Lilly Bainbridge, a reserved redhead from school, marked by the tragedy that took her father and left her with a fear that never fades. Between the two, a silent connection is born-a complicity made of glances, escapes to the woods, and secrets whispered in each other's ears. But what could have been a forbidden and fragile love ends up becoming something bigger: Clara realizes that Lilly hears things that no one else hears, and that Derry seems to react strangely every time Clara gets close to her. As the town plunges into paranoia and children begin to disappear, Clara discovers disturbing clues about the dark history of the Marsh family, about the true weight of the blood she carries... and about the hungry creature that awakens in the depths of Derry every 27 years. Now, Clara and Lilly must decide: how far will they go to protect each other, when the town itself tries to swallow them alive? ꗃ ༘ ⋆ ⌗ ɪᴛ ғᴀɴғɪᴄᴛɪᴏɴ ⭑.ᐟ ٠࣪⭑» cover made by © - newtm4as ٠࣪⭑» written by © - newtm4as ٠࣪⭑» translation made by © - pattycak3s ٠࣪⭑» aesthetics made by © - newtm4as 𝄃𝄃𝄂𝄂𝄀𝄁𝄃𝄂𝄂𝄃 © » newtm4as
  • lies || stanley uris x reader by izzysimaginationn
    izzysimaginationn
    • WpView
      Reads 163,552
    • WpPart
      Parts 23
    "i love you." "what if you're lying?" "i will lie forever, then."
  • Pennywise is in love by i_hate_life2006
    i_hate_life2006
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      Reads 11,802
    • WpPart
      Parts 8
    There is a new girl in Derry and her name is Alexa Peirce she encounters Pennywise but somethng happens there just something about her that he likes...
  • Surprise, bitch! [pennywise x reader] by Therizin
    Therizin
    • WpView
      Reads 219,334
    • WpPart
      Parts 16
    DISCONTINUED He's been watching you for months now, never had the chance to get his clawed hands on you. Now he does. "Surprise, bitch!" Discord - https://discord.gg/wFHS6hB [2017 new IT based fanfiction. Pennywise x reader. Not much romance, Pennywise is depicted as the demon, evil spirit he is. Long, detailed story - easing into the relationship. If you want a story that doesn't rush, around 2k+ words each chapter I suggest this story! Contains curse words, mentions of depression/suicide, rape]
  • Kiss Me or Don't by DarlingBeanz
    DarlingBeanz
    • WpView
      Reads 56,887
    • WpPart
      Parts 21
    Reddie One-Shots Trigger Warning for those afraid of Pennywise Please be sure to vote and comment I love those😊 Enjoy!
  • Don't leave by h0e4owen
    h0e4owen
    • WpView
      Reads 1,865
    • WpPart
      Parts 10
    Patrick Hockstetter x hallucination reader!!! 'She looked like an angel wearing her night gown.'
  • 𝐒𝐓𝐎𝐋𝐄𝐍 𝐅𝐑𝐄𝐄𝐃𝐎𝐌 by basinmarvel
    basinmarvel
    • WpView
      Reads 176
    • WpPart
      Parts 5
    Will I ever get the chance to be free?
  • tag, you're it.           r.tozier. act l. by sydlikestea
    sydlikestea
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      Reads 300,057
    • WpPart
      Parts 29
    ❝ gosh, I'd do anything to be the bra you're wearing. ❞ ❝ beep beep, richie. ❞ - richietozierxoc teenromance highest ranks : #1 in It2017 (out of 4.23k stories) #1 in richietozier (out of 4.58k stories) Written by @sydlikestea Enjoy!!