#Pennywise The Clown | Explore Tumblr posts and blogs

greenandsorrow · 3 days ago

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IF THE MONSTER UNDER YOUR BED NEVER HURT YOU, MAYBE IT WAS THERE TO PROTECT YOU. 🎈

Pennywise bonding with a teen!reader/ platonic

-> For technical reasons (for the plot to continue plotting), this chap focuses mostly on the past! Another thing... I appreciate your feedback and comments more than you realise, so don't hesitate to interact with my fics 🥺❣️

-> It's giving Stockholm Syndrome, I'm aware, but that's why it's called fanFICTION.

-> I think it's funny how each chapter turns longer than the last. I'm getting hooked to my own writing I guess.

-> Pennywise the Dancing Clown: A trans-dimensional entity that shapeshifts and feeds on the fear -and sometimes the flesh- of kids and animals. IT hibernates for 25 to 27 years, then wakes up for 12 to 16 months, manipulating reality and slipping past the notice of adults.

Listen to: Ilomilo by Billie Eilish

~ 3 ~

Pennywise's POV 🎈

For five long years he has stayed awake, stalking the streets of Derry... waiting. Pennywise's usual cycle -hibernating after a killing and terrorizing spree- has been disrupted. This time, something -someone- kept him from descending to the deep slumber he usually craves.

He can't fully understand it, but it's because of you -the spark, the tug of connection he isn't familiar with. He's hunted countless children without a second thought. But with you... When he had expected you to cower and break, instead, you had resisted, you had played his twisted games and stared back at him without losing your soul. You had made him so curious. And that curiosity has gnawed at him enough to eat away at his rest, putting him in a sort of restless trance.

Every time he tries to slip beneath the Earth and to return to the darkness he came from, he feels a pull, a shudder that makes him cling to the surface for just a little more, for just another silly, little, stupid, meek year.

But as the years have been slipping by, something else has shifted in him as well -a subtle thing that feels almost like restraint. He still lurks in the shadows, his instincts are still telling him to frighten and to feed… but each time he sees you, that impulse falters. Instead of scaring you, he finds himself watching, almost guarding you from afar.

It feels a twinge of protectiveness -an urge that should definitely not exist in a creature made to hunt and devour. It doesn't get it, doesn't know why It lingers to ensure no danger befalls you, before It vanishes for the usual twenty-seven years. Almost as though, Pennywise the Clown is bound to you by something unexplainable, something that's kept him from retreating to sleep.

And It hates it.

The longer Pennywise watches, the more he wishes he didn't feel this way. But when he does try to stir up the familiar darkness within his core, it's dulled and quieted. All he knows is that his hunger has been overpowered by something else, something… protective.

And this fact is as unnatural as it is inappropriate, for no other than The Eater of Worlds.

1979 Derry, Maine

"Let's play another game..! I... There is... There's one we haven't played!"

The door creaked open and the clown stepped inside with a look you had never seen before on him. He wasn't smiling, wasn't performing... he was serious, unsettlingly so. A reminder that Pennywise wasn't -and isn't- a real clown, not in the way he pretends to be. Drool slipped from his red lips, glistening in the early morning light filtering through a crooked and badly shut window. He had probably just interrupted his breakfast -maybe to see you- and the hunger in his eyes was unmistakable.

"What kind of game?" his voice rumbled low, sending a chill across your skin. Your stomach tightened and you swallowed down the bile that rose. His piercing, yellow gaze left you feeling exposed.

You struggled to think of something, anything that could buy you more time. You had to say something, or else he would just get pissed and maybe have you for breakfast, instead of the one he was -so rudely- interrupted from.

"The first one to… If I can name one friend before you do, I get to leave. If you win… You get to do whatever you want with me." You knew you were cornered, but the words had come out anyway.

A strange look flickered across his face.

"What's your name?"

You frowned at what sounded like an absurd thing to ask out of the blue. "Y/n."

He giggled.

"Oh really?! And I'm Pennywise the Dancing Clown! Now we've both properly introduced ourselves... We can be friends!!!"

The point of the game was for you to win... but he just had to be a smartass.

"WE CAN'T- CAN'T BE FRIENDS!"

Pennywise pouted, almost like a child who's just been told no. You could see the contradiction in him as he considered your words -a clown who loves games, whose eyes practically gleam with excitement... and yet a predator who's always calculating, always one step ahead, keeping his prey exactly where he wants it. He knew you had just tried to outsmart him, yet he stepped closer, drawn in by the idea of another game. Your captor knew way more about you than you had realized -he had been watching you long before he had decided to 'kidnap' you.

Actually, your desperate answer made him leave his spot by the doorframe and advance toward you, crouching down to your eye level. You were paralyzed in fear he could probably smell. Even while holding your breath, you could feel his own on your face... It smelled like a butcher's shop.

"Don't. Shout. At. Me."

You nodded.

His drool was still glistening.

"You're not leaving either."

Another nod.

Then, he left the room.

Later, you'd realize he had let you have your way with that idiotic game purely out of boredom -a way to break up the ancient routine It'd followed since the beginning of time. But in that moment, you were just trying to survive.

What happened next is clouded in fragments, your memory blurred by fear -or maybe it's nostalgia. Somehow, over time, you became something to him. Indeed... a friend... of sorts.

As more days passed, you dared to start speaking more freely, filling the silence between you. You'd mention that you were cold, or hungry and he would tilt his head in that curious way of his. The next day, a bag of chips might appear on the bed. Once, you coughed, your throat parched. Fortunately, you managed to murmur "water". A few hours later, there it was -water in a bowl.

You found your book -Alice in Wonderland- left in a corner of the room. You read to him, each word trembling from your lips but never letting your voice falter fully. Pennywise would sit at the edge of the bed, sometimes even curling up like a cat -making you question if he had any bones-, his gaze fixed on you with an unnerving intensity. You were scared that when you finished reading the book, your life would end along with Alice's story.

But it didn't.

Still, sometimes you made desperate attempts to escape, bolting to the door. But he'd catch you with a taunting grin.

"Tag, you're it!" he'd chuckle, pinning you effortlessly. "Winner gets a prize!" he'd mock, as if the only reward he needed was to see your defeated face. But despite the mocking, the punishing appearances of the enormous cockroach stopped.

Even his gaze softened over time, slipping from the predator's yellow stare to an electric blue. The games also shifted -grew less cruel- and with them, so did he. He no longer seemed intent on hurting you and instead, observed you with a cautious neutrality.

Each day It brought you random bowls of food and water -most likely stolen from unsuspecting housewives... And sometimes, It would linger just outside the door, listening to your voice as you read to yourself.

One evening, you found yourself in the backyard, gazing up at a lilac sky. He had taken you there -unbeknownst to you- because he had brought a little snack inside and didn't want that to scare you.

You missed your old life with a pang that made your throat burn, a feeling so deep you didn't even notice him approaching. Without thinking, you pressed yourself into the clown's chest, burying your face against his ruffled collar. His strange scent -a mix of damp earth and something much older- washed over you and for the first time, you felt… safe with him.

He didn't hug you back, didn't mimic the gesture, but his voice murmured strange words about humans, their fragile nature and then the usual pet name he would call you: "little one".

It was then that you realized -he wouldn't hurt you. Not now. Not after all this time. But the realization broke something in you, a dam holding back all the emotions that had been bubbling under the surface.

"Y- You won. You won!" you stammered, choking back tears. "I'm your friend! Kill me now!"

You collapsed to your knees and he watched -bewildered- as tears streamed down your face. For a moment, he just stood there and watched you cry. Then, tentatively, he reached out in an almost inquisitive manner, to catch a tear with a long, white finger and taste it. He seemed to pause, reflecting on something only he could understand.

And then on another day, another attempt to escape. You had found a tiny window in the basement and tried to squeeze through it. But he noticed, his monstrous form scraping against the window's frame, shattering the glass in a frenzy to reach you.

When you saw the shards cutting into his skin... You froze, guilt flooding over you. You returned to his side while murmuring apologies, your hands trembling as you pulled the glass from his wounds, piece by piece.

He didn't attack you -just stared at you with a seriousness that sent chills down your spine. You knew in that moment, that you had crossed a line, that there was something between you that shouldn't have been there -because you could've left but didn't and because he could've killed you but didn't either.

When you finished pulling out the glass pieces, he was pouting at you. "Meanie..." he said and stuck his tongue out.

In the days that followed, Pennywise grew quieter. He watched you differently, as if seeing you with new eyes -ones that held a warmth you'd never expected. And in a way, it made you feel… comfortable. Comfortable enough that one day, you dared to reach out, brushing a hand along his white cheek.

He froze under your touch, as if unsure how to react -his usually fierce, yellow eyes softening to that strange blue. A low sound rumbled from him -somewhere between a purr and a growl- and he tilted his head, pressing into your hand like a cat, seeming almost… content.

But that wasn't right. He wasn't human and he definitely wasn't a pet. It was something ancient and boundless... and yet here It was, in its favorite form, accepting your touch and even starting to crave it. You pulled your hand away and his eyes opened, watching you in a way that felt unexpectedly intimate.

Time continued to flow onward.

You were now given strange meals in even stranger containers -a cracked bowl, a chipped mug, even a metal dish that you could have sworn was meant for a dog! He didn't seem to understand the details of human routines, didn't quite grasp what you needed beyond food and water. Yet he tried, even if it were in ways that felt utterly alien.

One evening, just as the sun began to dip, you asked if you could go outside again. You hadn't meant it as a real question, but in the morning, you found the door to the backyard unlocked.

You didn't dare leave the property, but you enjoyed how the air was fresh and the grass was soft and the sky a little cloudy. You stayed out until evening came.

Pennywise watched you from a distance, the colors of the twilight reflecting in his eyes, giving him an almost haunting beauty. He joined you, sitting in the overgrown grass... murmuring things in a language that sounded both ancient and musical, like whispers from an old spell.

In the quiet, you leaned against him, letting the stillness speak for you both. And though he didn't return the gesture, just like last time, he didn't pull away either. You looked up at the stars, feeling that deep ache for home... He patted your head in a comforting manner... and in that moment you could almost believe he was a friend.

You were just a kid, but even with your naivety, deep down you knew the truth -he was a monster that had killed before and would kill again. Yet for now, he seemed content with your presence, more curious than threatening. He tilted his head, watching you with softness in his gaze, as if pondering the mystery of your existence.

Somewhere in your heart, you felt the shift. Pennywise, the monster, had grown attached to you. And you… well, you couldn't deny the attachment had become mutual.

The days blurred together even more after that, filled with silly games, with quiet moments and fragments of a bond you could neither define nor understand.

And yet, even as you tried to push away the thought, you feared that someday he might wake up and no longer see you as friend, or even as a curiosity, but as something he was hungry for once more. Still, in the quiet of the night it felt like a small, tragic eternity -two beings from worlds apart, drawn together and held by something both tender and terrifying.

The last days in the house at Neibolt St were the strangest. Pennywise grew quiet, almost pensive, as if some hidden clock was winding down inside him. You noticed how his smiles and giggles were fading, as if the game he'd once delighted in was losing its thrill. Sometimes, he would simply watch you with an unreadable expression, his eyes that odd, bright blue that almost felt... sad.

You felt a pang of sympathy for him. For all his power and for all his malevolence, he was still somehow... alone. You had felt it in those strange moments when -almost wistfully- he'd listen to you talk and read.

The last night felt different, filled with an air of finality.

As you laid on your creaky bed, you noticed him standing in the corner of the room, like some sort of sleep paralysis demon. He was staring at you with an intensity that used to scare you three months ago. You felt the impulse to speak, but you knew he wouldn't respond. Instead, you held his gaze, feeling a strange sense of sorrow settle over you.

When he finally spoke, his voice was almost too soft to hear.

"Little one, when you leave…will you forget about me?"

The question caught you off guard and you didn't know how to answer. You wanted to tell him that you wouldn't, that everything you'd been through would be impossible to forget. But Pennywise knew that memories could fade, that as you grew older, the edges of this nightmare would blur.

You just stared at him, searching for the right words.

His eyes held a strange depth, a rawness you hadn't seen before. But he didn't wait for your answer. He simply turned, drifting back into the shadows as he whispered...

"The game isn't over."

And as he vanished, you were left in the cold darkness, with the silence pressing down around you like a final embrace. You clutched your knees to your chest, feeling the weight of those words settle heavily in your heart. You knew that even if you did forget him one day, some part of him would linger -an echo in the back of your mind, a memory that would never truly die.

That night, as sleep began to take you, you imagined him in the backyard... looking up at the stars and wondering if you'd remember.

It really felt like something precious had been taken away from you too early.

The next morning, you woke up in your own bed, in your home in Witchham Street.

For a moment you thought you'd died... Εveryone around you acted as though you'd never disappeared, as if those harrowing months at Neibolt hadn't happened at all. But there was one particular detail that hinted otherwise... A red balloon, floating silently at the edge of your bed.

That morning, you also got your period for the first time.

Stepping outside, the daylight was so bright and so warm, a stark contrast to the darkness you'd lived in for weeks. You squinted at the light, feeling almost as though you'd stepped into another world. It was hard to believe that just the night before, you had been in his arms -you had been seeking comfort from the monster who had held you captive.

Part of you seriously considered whether it had all been just a dream. Still, for days, you felt his absence like a missing heartbeat.

The world around you seemed much louder and the colors almost too vivid. Sometimes, you'd catch yourself looking for him in the shadows, half expecting to see his shape looming in the corners of your room.

At night you'd lie awake, thinking of his strange question...

"When you leave… will you forget me?"

You didn't know how to answer, even to yourself.

As much as you wanted to return to your old life and to move on from that nightmare, you felt a small part of you ache with the loss. You had lived through something impossible, something that had left you changed.

There was no going back to who you were before.

Over time though, the memory of him faded into something almost surreal. You didn't speak of it to anyone -the words felt fragile and sacred, as if telling the story might diminish it.

But the craziest thing that happened? You continued living as if everything was perfectly normal.

You only thought of Pennywise again that Christmas, in 1979...

The holidays had come to Derry and your family decorated the house with lights and garlands, the scents of pine and cinnamon clinging to every corner. There were gifts under the tree and snow falling outside the windows. Everything was festive and happy.

But when you woke up in your cozy little bedroom -on the 24th-, near the foot of your bed laid a single, crumpled sunflower. It must've been from the patch in the backyard where you'd sometimes sit with him, where the wildflowers had managed to grow despite the gloom. You held it gently, careful not to disturb its fragile petals. It felt like a memento of your time together -a reminder that what you had shared was real, however bizarre and terrifying.

On some nights, when the world was silent, you'd find yourself reaching for that sunflower, feeling the dried petals crumble beneath your fingertips. You'd lie awake, wondering where he was -if he still remembered, if he still waited. And though you'd never say it out loud, a small part of you hoped he did. Because no matter how much time passed, no matter how much you grew or changed, there was one truth you could never deny... He had left his mark on you, a scar that you'd carry forever.

And somewhere out there, you felt certain, Pennywise was waiting.

In the years that followed, you held onto those fleeting memories. They had a strange, magnetic pull -a mix of terror and fascination. You couldn't help but feel that if you let them slip, if you completely forgot, you'd be leaving behind a piece of yourself.

The Losers helped ground you.

They were your anchors to the present, pulling you back to laughter, to familiar faces and to the warmth of friends who shared their own scars and secrets. They never asked about the nightmares that sometimes made you stir, the shadows you occasionally saw out of the corner of your eye. And you never told them.

But there were also moments -quiet and lonely moments- when the weight of it all crept back, haunting you with unspoken questions. You'd wonder if he thought of you, if he missed you in his own twisted way. Did he ever feel the same hollow ache?

And deep down, you even wondered what might happen if he came back. Would he be nice and protecting? Or would he be just as monstrous and alien as before?

On some other nights, when the wind picked up, you swore you could feel his gaze -a distant yet familiar watchfulness that was both comforting and unnerving. It was as though he was still guarding you.

And so you moved forward, feeling the tug of those memories lessen but never fully vanish.

Would he stay away? Or would there come a day when that half-remembered monster with the childlike heart would find his way back to you?

1984 Derry, Maine

You tell yourself you hate Pennywise.

You tell yourself that, because you have to believe it is true, because that's the only way to move on. But deep inside your mind you can still feel him -his question echoing faintly in you, lesser and lesser each year, like a bond stretching thinner and thinner.

Currently, you're pondering over a glass of Cherry Coke. Yesterday, Bill had asked you about your dreams. He wanted to know if the clown that took away his little brother haunted you as well. You had simply shaken your head 'no', but the truth was the complete opposite.

Until you turned fifteen, Pennywise was still in your dreams. You remember those dreams even more vividly than your days in the house on Neibolt St...

You always had a strong imagination, which came with vivid dreams and equally vivid nightmares. In those dreams, Pennywise would come to you whenever you were scared. He'd pull you close in that tender way he never did in reality, fighting off every dark shape in your mind and then wrapping you in a kind of warmth you can't explain with words.

Sometimes, you'd apologize to him in those dreams -feeling an unnamed guilt- and he'd boop your nose with a soft and soothing "It's okie-dokie, Y/n."

Sometimes there'd be a red balloon waiting by your bed when you woke up, or maybe floating outside your school window. And on one specific evening, when the sadness felt like too much to bear, he appeared at the edge of your bed instead of the balloon. He hugged you and stayed with you until morning came, his glowing eyes softly illuminating the darkness. For once, they didn't scare you.

But as you grew up, you began to dream of him differently. In the nightmares, he'd chase you with a crooked smile and eyes that were dark with hunger, until you couldn't run anymore. Then you'd turn, tears streaming down your face, pleading with him and saying you were sorry over and over. You could never remember why you were sorry, but you knew that somewhere deep inside... you had hurt him. And somehow, you couldn't shake the feeling that it was you who'd let him down.

You tried to explain this to him, even though it was only in dreams -your Penny, who had watched over you. But he still seemed sad. So the dreams began to fade and he stopped showing himself altogether. Even then, you could still feel his presence, as if he was looking over you but choosing to stay hidden.

The few glimpses you have left are rather strange. Once, you had a dream with an uncanny intensity. It was the first different kind of dream -a dream where Pennywise was there as well, but puzzled, as you began to see him through a different lens. It left you feeling unsettled. Not sure what it meant, only that it somehow changed everything.

And still, each time you're scared, you call out for him in your dreams. You search, even while knowing he won't appear like he used to. Maybe it's because you had once blurted out that he was a killer, that he took innocent people like Georgie. It's all so blurry now, all these things you can't quite remember but can't entirely forget either.

You miss him.

You know Georgie's disappearance and so many others are somehow linked to that clown. But if his pattern is to stay on Earth for a year and hibernate for two decades (like Ben figured out), why then, hasn't he gone to sleep in five? It's almost as though he can't bring himself to leave.

Maybe you are asking too many questions. Or maybe you are starting to find the answers...

You're just a girl. And he… he's a boy in a strange, unfathomable way.

There are times when you think he's gone for good. But then there are other times -like when Oscar, the thick orange cat you've taken to caring for, curls up by you in a way that feels just a little too familiar. His stare, intense and watchful, feels more like an any ordinary cat.

You call him Oscar, but maybe -just maybe- you know it's him.

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alcinaslittlemaid · 9 months ago

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Naughty Little Lamb~

Pennywise 2017xFem!reader

•Warnings: Smutty smut, degradation, spanking (a lot), angry sex.. and much much more, Mild DD/LG (tiny bit) uses of pet names

(I’m not great at writing buts it’s the red hour 😳🌶️)

Come join the clown~

🎪🎈🤡

——————————

The hour was very late, you had struggled to get to sleep and Pennywise had gone out hunting. You felt a familiar throbbing in your underwear, by god you were missing him so much, your hand slipped down between your silky thighs and coating your fingers were your own sinuous juices.

You smirked and began pleasuring yourself, grabbing your vibrator imagining penny’s long slippery tongue slurping your insides out, your toes began to curl as you bucked your hips in submission, your mind travelling further, now imagining how smaller tentacles would slither out, gripping your thighs to keep you in place, long slimy tentacles restricting your movement, as his long, hard alien-like tentacle is forcible pushed into your tight hole, the ridges of his length hitting your clit as he completely ruins you.

Trying to get his entire length inside your tight, little cunt, you were getting close, finally going to be rid of your need for him (until tomorrow that is) you were almost riding your vibrator with pleasure

“Dooonnnt youuuu Dareeee~” that taunting voice in your head rang out like a bell you had recognised all too well

“Fuck…” you whined “Watch your mouth little slut” the voice growled, it’s raspy voice grunted in your ear as you slowly peeked up at the darkened side of your room, there…two golden orbs stared back at you, dark red circles rimmed it’s golden stare

“Oh my~ look at the filthy mess you’ve made, you dirty little slut” pennywise barked, stepping towards you “my! Dirty little sewer slut” he grinned before sitting down

“Come” he snapped patting his lap “But you said I couldn’t-“ you attempted a joke, but the state he gave you was stern, cold and deadly

“I said…COME!” He snapped, before dragging you roughly over his knee, your ass now presented to him like his next meal on a silver platter “Ah! Ow your hurting me! Penny what the fu-“ you were soon cut off by his to clawed fingers “Good little girls should be seen and not heard” his fingers were almost in your throat, you hadn’t a clue what was happening.

“You’ve been such a naughty, filthy little lamb Y/N” he teased before hiking your skirt up higher, his tentacles keeping you tightly in place as his hand slowly lifted behind your rear

“Now, we’re gonna play a little game~” he began, you shook your head at his silly games, but he was having none of it

“your gonna count every time I spank that little ass” he continued “and if you mess up or miss a number, they’re gonna restart and be even harsher…got it?” He hissed, you squealed and tried to squirm out of his grasp

“Ohhhh you wanna play hide and seek? Okay! If hide and I don’t find you in under 2 minutes I won’t punish you! We can doooo whatever you want~” he had crossed his fingers behind his back while saying that. You nodded and took off running, trying to find a hiding place he hasn’t seen yet, meanwhile the clown began to the countdown to your demise

“1…..2……3”

“Shit” you winced

“4…..5….6”

“Fuck fuck fuck!”

“7……8….9…”

You finally found a spot, sliding into it and shutting the door behind you ever so silently, you sunk beneath the piles of sheets and bedding

“10! Ready or not little bunny! Mr wolf is coming to find you hahahah” He cackled maniacally and began searching for you, his boots thudding against the ground in desperation. This was horrifying, he could do anything to you…you could hear doors opening and the disappointed sigh when you weren’t there “Oh my little lamb you are clever..” He then opened the door to your linen cupboard “but not clever enough- oh! Oh fuck where on earth is that little girl?” He slammed the door shut and began walking away…or so you thought

As soon as you heard a door downstairs creak open, you poked your head out and began sneaking back to your bedroom thinking you had won.

You were suddenly pinned to the ground by his clawed glove “You! You are so gullible…you think I couldn’t smell that throbbing, aching slit? Hahaha oh little one, you fell for the oldest trick in the book! You are a fly in my spider web” he giggled maniacally in pure pleasure, before dragging you back to the bedroom, a thread of drool trailing behind and a sinful, sadistic look in his eye.

@sootrootdoot

@pennywise-fucker

End of part 1🎈

Lemme know what y’all think and I’ll write the next part!!