Chapter 1: REQUESTS
Chapter Text
IT: WELCOME TO DERRY STORY REQUESTS
~RELATIONSHIPS~
LILLY BAINBRIDGE/VERONICA GROGAN
PHIL MALKIN/THEODORE "TEDDY" URIS
LILLY BAINBRIDGE/MARGE TRUMAN
LILLY BAINBRIDGE/PHIL MALKIN
LILLY BAINBRIDGE/ THEODORE "TEDDY" URIS
VERONICA GROGAN/WILL HANLON
WILL HANLON/RICH SANTOS
RICH SANTOS/MARGE TRUMAN
~STORY IDEAS~
ROMANCE
FLUFF
ANGST
HURT/COMFORT
SMUT
Chapter 2: The Walk Home (Lilly x Teddy)
Summary:
Paring: Lilly Bainbridge & Teddy Uris
Chapter Text
The final bell of Derry High School rang out sharp and metallic, echoing down the brick hallways as kids poured outside like a burst of wind. Lilly Bainbridge tugged her scarf tighter against the October chill and waited by the flagpole, rocking on her heels.
Teddy Uris emerged a moment later, his bookbag slung over one shoulder and his hair sticking up in the back like he’d fallen asleep on his math book again.
“You ready?” Lilly asked.
“Yeah,” Teddy said, falling into step beside her as they started toward Witcham Street. “Feels weird without Phil trailing behind us and coughing every two minutes.”
Lilly laughed, kicking at a pile of brittle orange leaves. “He’d probably say something dramatic like, ‘Go on without me. Tell my story.’”
“That’s because he likes attention,” Teddy said, but he was smiling. “Still, hope he’s okay. My mom said half the town’s got that stomach bug.”
“My mom says Phil probably just ate too many of those penny candies he’s always buying.” Lilly puffed warm breath into her cupped hands. “He was looking green yesterday.”
They crossed the intersection where the drugstore stood, its big front window full of Halloween masks—witches with warty noses, skeletons with crooked grins. Lilly slowed down.
“Phil would hate those,” she said. “You know how he gets with masks.”
“Yeah.” Teddy nudged her lightly with his elbow. “He makes us walk on the other side of the street just because Mr. Delacroix puts that clown dummy in his window.”
Lilly shuddered. “Okay, yeah, that thing’s creepy.”
They passed the park, nearly empty except for a few kids on the swings and the distant clang of someone’s bicycle chain slipping. The sky was turning that pale, early-evening gold that made Derry look softer, like a photograph.
“You think Phil’ll be back tomorrow?” Teddy asked, scraping his shoe along the sidewalk edge.
“Probably.” Lilly kicked another pile of leaves, sending them fluttering. “He’ll have a whole story about it, too. Like—” She dropped her voice an octave. “‘I battled the forces of sickness and emerged victorious.’”
Teddy chuckled. “And we’ll have to pretend it’s heroic.”
“Because it is heroic,” Lilly insisted, grinning. “Surviving being Phil.”
They walked a little more in comfortable silence. The trees rustled overhead, and somewhere a dog barked at nothing. Derry always had a way of feeling a little too quiet on days like this, but with Teddy beside her, Lilly didn’t mind.
“Hey,” he said suddenly, “maybe we should bring Phil his homework. And some comic books. You know, in case he’s too weak to go on.”
Lilly snorted. “He’d love that.”
They reached the corner where their paths split. Teddy adjusted his bag again.
“See you tomorrow, Lil.”
“See you, Teddy. And… let’s check on Phil after school, okay?”
“Yeah. Wouldn’t be the same without him.”
She waved as he headed down his street, then turned toward her own house, the cool air crisp against her cheeks. Behind her, leaves skittered across the pavement like tiny feet hurrying home.
Tomorrow, she thought, the three of them would be together again—walking, laughing, and arguing about ridiculous things the way they always did.
And Derry, for that small moment, would feel just right.
Notes:
Hope Everyone likes this chapter!
Please let me know in the comments how you liked this chapter
*IF YOU STILL WANT TO MAKE STORY REQUESTS, THE REQUESTS ARE STILL OPEN, JUST GO TO THE REQUESTS CHAPTER TO MAKE YOUR REQUEST :)
Chapter 3: The Bell Between Classes (Lilly Bainbridge)
Summary:
Character: Lilly Bainbridge
Lilly Bainbridge is at school and she gets her period and her friend Ronnie comes and helps her
Chapter Text
The hallway of Derry High School buzzed with the usual end-of-lunch energy—slamming locker doors, the squeak of saddle shoes on linoleum, the distant rattle of the gym teacher’s whistle. Lilly Bainbridge tried to keep pace with it all, hugging her books tightly to her chest as she made her way toward English class.
That was when it hit her—a warm, sinking feeling low in her stomach, followed by a different kind of sensation altogether. Her steps faltered.
No. Not today.
She swallowed hard and diverted to the wall, pretending to examine the class schedules posted there. Her hands trembled around her books.
It couldn’t be… she’d timed everything. She thought she had. But the calendar in her locker had been smudged, and she’d guessed, and—
“Lilly?” a voice whispered beside her.
Ronnie Grogan stood there, her black curls frizzing out from under hat. She wore her usual determined expression—softened only when she saw Lilly’s face.
“You look like you just saw Mr. Grady smile,” Ronnie joked lightly. When Lilly didn’t laugh, Ronnie’s expression sharpened with concern. “Hey. What’s wrong?”
Lilly lowered her voice to the faintest whisper. “I… Ronnie, I think I got my period.”
Ronnie blinked, then nodded once, a quick, decisive gesture. No teasing. No embarrassment. “Okay,” she said. “Do you need to go to the nurse?”
“I can’t move,” Lilly muttered. “If I walk, everyone’s gonna—”
“Hey.” Ronnie stepped in front of her, blocking the hall from seeing Lilly’s shaking hands. “It’s okay. We’ll handle it.”
The hallway suddenly felt twice as loud, students flowing past like a river Lilly couldn’t step into. Her cheeks burned; she wished she could disappear into the corkboard behind her.
Ronnie set her books down. “Here’s the plan,” she said quietly. “I’m going to walk right next to you, and you’ll hold your books behind you if you’re worried. Just until we get to the bathroom. Nobody will notice.”
Lilly hesitated. “Are you sure?”
“Lilly Bainbridge,” Ronnie said with a confidence she absolutely did not have in math class, “I’ve been your friend since third grade. I once pretended I had the chickenpox so you’d feel better about missing roller-skating night. Trust me.”
A tiny laugh slipped out of Lilly despite the panic sitting in her throat. Ronnie gave a triumphant smile at the sound.
“Ready?” Ronnie asked.
Lilly nodded, and together they stepped into the flow of students—Ronnie deliberately close, shoulder brushing Lilly’s like a shield. She chatted about nothing (how the cafeteria’s macaroni “looked like it was cooked in swamp water,” how Miss Alderidge’s new beehive hairdo was tall enough to get its own homeroom) because she knew talking made Lilly relax. And Lilly let her, grateful for the distraction.
By the time they reached the girls’ restroom, Lilly felt like she could breathe again.
Inside, the muffled noise of the school faded. The cool tiles, the faint smell of powder and cheap soap—everything felt calmer.
Ronnie reached into her bookbag and pulled out a small zipper pouch decorated with felt flowers. “Emergency kit,” she said proudly. “My mom made me carry it. I used to think it was dumb. Not today, though.”
Lilly’s eyes stung. “Ronnie… thank you.”
Ronnie waved her off. “Hey, it happens. It’s not your fault. And you’re gonna be okay. I promise.”
While Lilly got herself cleaned up, Ronnie leaned against the sink, humming some tune from the radio—something soft, something steady. When Lilly emerged, looking pale but composed, Ronnie straightened immediately.
“Feel better?” she asked.
“A little,” Lilly said. And then, after a moment: “A lot. Because of you.”
Ronnie slung an arm around her shoulders, warm and easy. “Good. Now let’s sneak into English class like nothing happened. We’ll blame the late bell. Or Nixon. Grownups blame everything on him.”
Lilly laughed again—really laughed this time—and together they stepped back into the hall, two girls walking shoulder to shoulder through the noisy world of 1964, one supporting the other without hesitation.
Because that was what friends did.
And Lilly knew, more certainly than ever, that she’d picked the best one.
Notes:
HAPPY THANKSGIVING EVERYONE!!!!!!
I hope you all like this chapter
*ALSO I WILL BE POSTING ANOTHER CHAPTER LATER ON TODAY SO BE ON THE LOOK OUT :)
Chapter 4: Quarry Confessions: Phil and Teddy's Summer Blaze
Summary:
Phil Malkin & Teddy Uris Romance
*SMUT WARNING!!!!!!!
Chapter Text
The summer of 1967 in Derry, Maine, wrapped the small town in a haze of heat and the faint scent of pine from the nearby woods. Phil Malkin, an 18-year-old with tousled brown, blue eyes that sparkled with quiet mischief, and a lean build from summers spent fishing the Kenduskeag Stream, wiped sweat from his forehead as he pedaled his beat-up Schwinn toward the old quarry on the outskirts. He wore faded jeans and a white t-shirt that clung to his chest, his heart pounding not just from the ride, but from the secret crush he'd harbored on his best friend, Teddy Uris, for what felt like forever.
Teddy, also 18, waited by the quarry's edge, his blonde curly hair cropped short under a newsboy cap, freckles dusting his nose and shoulders. He had a stocky frame, broad shoulders from helping at his dad's hardware store, and hazel eyes that held a fierce loyalty. Dressed in khaki shorts and a button-up shirt with sleeves rolled to his elbows, he tossed a pebble into the murky water below, the splash echoing in the still afternoon. Phil and Teddy had been inseparable since grade school—sharing comic books, sneaking smokes behind the Aladdin Theater, and lately, exchanging glances that lingered too long, charged with unspoken want.
'About time you showed,' Teddy grinned as Phil skidded to a stop, chaining his bike to a tree. 'Thought the heat might've melted you.' Phil laughed, rubbing the back of his neck, his cheeks warming under Teddy's gaze. They hiked down to a secluded spot by the water, spreading out an old blanket amid the rocks and wild grass. The quarry was their hideout, far from prying eyes in Derry, where whispers about 'queers' could ruin a guy's life. But here, with the sun filtering through the leaves and the distant call of birds, the world felt safer.
They talked for hours—about school ending, dreams of leaving Derry for Boston or maybe even California, the latest Beatles record spinning in Phil's mind. As the conversation lulled, their shoulders brushed, and neither moved away. Phil's hand found Teddy's on the blanket, fingers intertwining tentatively. 'Ted,' Phil murmured, voice low, 'I gotta say something. It's been killing me.' Teddy turned, eyes searching Phil's face, his thumb stroking the back of Phil's hand. 'Yeah? Me too, Phil. I... I like you. More than a buddy. Always have.' The admission hung between them, raw and real, before Teddy leaned in, pressing his lips to Phil's in a kiss that started soft but deepened with years of pent-up longing.
Phil responded eagerly, his free hand cupping Teddy's jaw, tongues meeting in a slow, exploratory dance. The kiss broke only when they needed air, foreheads resting together, breaths mingling. 'God, I've wanted this,' Teddy whispered, his voice husky. They shifted closer, bodies aligning on the blanket, hands roaming with newfound freedom. Phil's fingers traced Teddy's chest through his shirt, feeling the rapid beat of his heart, while Teddy tugged at Phil's t-shirt, pulling it over his head to expose smooth, sun-tanned skin.
Clothes came off in a rush—shirts discarded, jeans unbuttoned and shoved down with underwear, until they lay naked under the dappled sunlight. Phil's cock stood hard and flushed, curving slightly upward, while Teddy's was thicker, veins prominent along its length, both leaking pre-cum in anticipation. They stared, admiration turning to hunger. 'You're beautiful,' Phil breathed, reaching out to wrap his hand around Teddy's shaft. Teddy groaned, his own hand mirroring the action on Phil's cock, stroking slowly from base to tip.
They jerked each other off like that, side by side, fists pumping in unison. Phil's grip tightened on the upstroke, thumb swiping over Teddy's slit to spread the slickness, making Teddy's hips buck. 'Fuck, Phil... feels so good,' Teddy panted, his hand twisting gently around Phil's head, eliciting a moan that vibrated through them both. The rhythm built, skin slapping softly against skin, their free hands clutching shoulders or hair for leverage. Sweat beaded on their brows, mixing with the earthy scent of the quarry. Phil came first, his cock pulsing in Teddy's fist, ropes of cum splattering across his stomach as he cried out Teddy's name. The sight pushed Teddy over the edge seconds later, his release shooting hot across Phil's thigh, his body shuddering with the intensity.
But they weren't done. Panting, they cleaned up with the edge of the blanket, then Teddy pushed Phil onto his back, kissing down his neck, chest, and belly. He paused at Phil's softening cock, now twitching back to life, and took it into his mouth without hesitation. Phil gasped, fingers threading through Teddy's hair as Teddy sucked, lips sliding down the length, tongue swirling around the sensitive underside. He bobbed his head, taking Phil deeper with each pass, hollowing his cheeks for suction that made Phil's toes curl. 'Ted... oh shit,' Phil whimpered, hips lifting instinctively.
Teddy hummed around him, the vibration sending sparks up Phil's spine. He pulled off with a wet pop, grinning up at Phil's flushed face. 'Your turn.' They switched, Phil kneeling between Teddy's legs, admiring the way Teddy's cock hardened fully again under his gaze. Phil licked the tip first, tasting the salty remnants of cum, then engulfed him, sucking eagerly. Teddy's hands guided Phil's head, not forcing but encouraging, as Phil worked his mouth up and down, one hand stroking what he couldn't take. Teddy's moans filled the air, thighs tensing as Phil's tongue pressed flat against the vein running along the underside.
The blowjob turned mutual when they shifted to sixty-nine, bodies aligned on the blanket. Phil sucked Teddy's cock while Teddy did the same, mouths working in tandem, slurping and licking with desperate need. Fingers explored too—Phil teasing Teddy's balls, rolling them gently, while Teddy's hand dipped lower to circle Phil's tight hole, pressing just enough to make him clench and moan around the dick in his mouth. The dual sensations built fast, but they held back, savoring the intimacy.
Finally, need overtook them. Teddy grabbed the small bottle of lotion from his discarded shorts—meant for sunburn but perfect now—and slicked his fingers. He prepped Phil slowly, one finger breaching his ass, then two, scissoring and curling to find that spot that made Phil arch and beg. 'Please, Ted... I need you inside me.' Teddy nodded, positioning himself, cockhead nudging Phil's entrance. He pushed in inch by inch, both groaning at the stretch and fullness. Once seated, Teddy paused, kissing Phil deeply, whispering, 'I love you.'
Then he moved, thrusting slow at first, building to a steady rhythm. Phil wrapped his legs around Teddy's waist, pulling him deeper, their cocks rubbing together with each snap of hips. The quarry echoed with their grunts and the wet slide of skin. Teddy angled to hit Phil's prostate on every stroke, making stars burst behind Phil's eyes. 'Harder... fuck me harder,' Phil demanded, nails digging into Teddy's back. Teddy obliged, pounding faster, one hand jerking Phil's cock in time with his thrusts.
Phil came again, untouched now except for the friction, his ass clenching around Teddy, milking him until Teddy followed, burying deep and filling Phil with hot spurts of cum. They collapsed, Teddy still inside, arms wrapped tight, hearts racing in sync.
As the sun began to set, painting the quarry in golden hues, they dressed lazily, stealing kisses and promises. Derry's shadows loomed, but in each other, they'd found light—a romance forged in secrecy, but unbreakable.
Notes:
Another Chapter for Thanksgiving
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 5: The Clubhouse Afternoon (Lilly, Phil, Teddy & Susie)
Summary:
Just four friends hanging out at their clubhouse
Chapter Text
The sun hung low over Derry, laying warm stripes of gold across the clearing behind the Barrens. It was the kind of July afternoon that made everything feel slower, softer, as if the whole town were dozing off. But the old clubhouse—half-roofed, half-leaning, and entirely theirs—was buzzing with life.
Lilly Bainbridge was the first through the door, ducking under the low frame with a clatter of bracelets and a triumphant grin.
“I brought cream soda,” she announced, hoisting the clinking glass bottles like trophies. “Phil, you owe me two nickels for these.”
Phil Malkin lay sprawled on the floorboards with a comic book over his face. “Put it on my tab,” he said, voice muffled.
“You don’t have a tab,” Lilly said.
“Exactly,” Phil replied, lifting the comic just enough to wink.
Teddy Uris was perched on an overturned milk crate in the corner, carefully tightening one of the strings on an old, beat-up banjo he’d found at a yard sale. Nobody in the clubhouse really believed he could play it, but Teddy was stubbornly determined to prove otherwise.
“You tune that thing any more and it’s gonna explode,” Phil said.
“It won’t explode,” Teddy replied seriously, then paused. “Probably.”
Susie Malkin—Phil’s little sister—sat cross-legged near the doorway, drawing something in her notebook with total concentration. At nine years old, she had a habit of drifting in and out of the older kids’ adventures, usually without asking permission. No one ever said no to her, though; she was too earnest, too wide-eyed, and often too funny without meaning to be.
“What are you working on, Susie?” Lilly asked, cracking open her cream soda.
Susie turned the notebook around proudly. “A map.”
Phil squinted at it. “Of where?”
“Here,” she said. “The clubhouse. The trails. The Barrens. All the places monsters could hide.”
Teddy paused mid-tuning. “Monsters?”
Susie nodded with utter seriousness. “You never know.”
Lilly leaned over and tapped the corner of the page. “And what’s that supposed to be?”
“That’s where you keep losing your shoelaces,” Susie said matter-of-factly.
Lilly laughed, tossing her braid back. “Okay, that one’s accurate.”
A calm breeze drifted through the gaps in the boards, carrying the smell of warm pine and distant river water. The place creaked softly—the kind of sound that could be creepy at night, but in the afternoon felt almost comforting.
Teddy finally plucked a chord. It twanged with an alarming sharpness.
Phil sat up. “That sounded like a rubber band snapping off a mailbox.”
“It was art,” Teddy declared.
Lilly raised an eyebrow. “If that was art, my dad’s fishing line is a symphony.”
But Teddy just grinned and strummed again—this time a little more gently. The note came out surprisingly smooth, drifting around the small room like it belonged there.
They all went quiet for a moment, listening—not because the playing was good (it wasn’t), but because the clubhouse had a way of making even bad music feel like part of the day’s rhythm.
After a minute, Phil stretched and said, “We should do something. Explore, maybe.”
Susie looked up sharply. “Not the monster places, right?”
“We’ll stay on the safe paths,” Lilly assured her, ruffling her hair.
Susie narrowed her eyes. “Define ‘safe.’”
Phil laughed. “The ones that won’t eat us.”
“Oh.” She nodded. “Okay then.”
They stayed a little longer, finishing their sodas and letting the warm stillness settle around them. The clubhouse wasn’t perfect—its roof leaked, the floor slanted, and the walls whispered whenever the wind hit them just right—but to them, it was a fortress, a world apart. A place where nine-year-olds could draw monster maps, where banjos refused to stay in tune, and where summer felt endless.
By the time they finally spilled out into the clearing, the sun had started dipping toward the treeline, painting long shadows from their feet. They walked toward the trails together—four mismatched figures heading into the wide, green maze they knew like the back of their hands.
And behind them, the clubhouse stood watch, as it always did, over another small adventure in the summer of ’62.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 6: Ghosts in the Walls of Juniper (Lilly Bainbridge)
Summary:
Story of Lilly Bainbridge in Juniper Hill prior to IT: Welcome To Derry
Chapter Text
Even after a week, Lilly Bainbridge couldn’t remember the last words her father had said to her. The moments slid around inside her head, blurred and overlapping — his greased hands drawing sweat-dark smiles across her cheeks, the tick of the clock in their kitchen, the sour stink of old tobacco curling from his shirt as he said goodbye before another shift at the mill. She remembered thinking he’d come back. They always said he was lucky, that he could dodge the worst of what the machines threw at him. Funny how luck runs out.
She hadn’t seen his body. Her mother wouldn’t let her, and when she screamed herself hoarse trying, the neighbors arrived in brittle, crackling packs to help carry her away from the row house. Afterward, everything went gray. The world folded in on itself, edges sharp as glass.
Juniper Hill perched outside Derry like a scab, brick and iron, barred windows crusted with the salt of too many seasons. Her first night, she counted the cries in the walls and tried to work out which ones were real. They kept her in a women’s ward painted the color of weak milk, each bed chained in place. Her roommate was a girl with hair so white it looked blue in the moonlight. She spoke to someone Lilly couldn’t see, muttering nonsense or maybe spells, and the nurses didn’t bother correcting her. There were worse things, Lilly had noticed, than talking to phantoms.
Sleep came in fits — nightmares tucked under her sheets, cold and surgical. Her father’s face became the factory whistle, the sound a sick, mechanical scream. They told her he died fast, but what did they know? She suspected the truth was there among the slabs of meat, the teeth-marked machines, the way the foreman had looked everywhere but her eyes.
Days moved oddly at Juniper Hill. Breakfast that tasted like paste, group time that didn’t make a dent in the stale hush. They gave her little pills in paper cups and expected her to swallow them without asking why. No one at Juniper wanted troubles spoken aloud. You could hear it in the way the place exhaled at night: even the air seemed sick with secrets.
The doctor — Dr. Harper — had eyes like split stones and a handshake that bruised. He asked her about dreams. About the factory. About her mother (gone long before the rest of them). His notebook flickered in the sun, page after page, and Lilly realized early on that you could say whatever you wanted here — the words didn’t matter. They wanted her to be small, to shrink into a shape that made sense. Her father would have broken something at that thought, or at least tried.
Once, on a rain-heavy Thursday, Lilly watched lightning ripple above the trees. For half a second her skin flashed hot and raw, remembered her real self from the time before. Outside the fence, there were stories — she’d heard the whispered ones about Derry, about the old house on Neibolt, the dark under the canal, things with claws. Some of the other girls looked at her sideways, told their own lies about monsters, but most of them just shut their eyes and waited to be forgotten.
Lilly Bainbridge didn’t want to be forgotten, not even by the things that lived in shadow. As the sky split and the hallways filled with thunder, she thought of her father, luckless, falling, and wondered if ghosts could yell loud enough to break the world.
Inside Juniper Hill, everything rotted slow. But beneath the gray and the pills and the locked doors, something else moved. A seed of something restless, sharp. Maybe hate, maybe hope. Maybe a voice that refused to stay dead.
Soon Derry would remember her name. And sooner or later, the monsters would, too.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 7: The Boy on Neibolt Street (Phil Malkin & Teddy Uris)
Summary:
Phil & Teddy talk about Matty Clements and how they feel guilty for not being friends with him.
Chapter Text
Derry, Maine — Summer 1962
Teddy Uris liked to say that he didn’t believe in ghosts, but Derry had a way of making people liars. Even now, as he pedaled his beat-up Schwinn down Witcham Street, he couldn’t shake the prickling at the back of his neck. It wasn’t the town—that was familiar enough. It was the guilt.
Phil Malkin rode beside him, his handlebars rattling with every bump. Phil didn’t say much when he felt bad about something, but Teddy knew. They both knew. They just didn’t want to talk about it.
They’d been avoiding Matty Clements for weeks.
Matty, who always saved the best baseball card trades for them.
Matty, who could whistle any song he heard once.
Matty, who lived near the old Neibolt house, and therefore was, in the unwritten rules of Derry childhood, automatically “the weird kid.”
That was the real reason they’d drifted from him. Not that they’d ever speak it out loud.
“You think he’s mad?” Phil finally asked, eyes fixed on the pavement rushing under his tires.
Teddy shrugged, though his stomach twisted. “Maybe. I dunno.”
“Maybe we should go see him.”
Teddy let that hang between them. The heat was heavy; you could smell the tar softening on the road. “Yeah,” he said eventually. “Yeah, okay.”
They turned down the quieter streets—past the mill, past the corner store, until the houses grew older and the trees thicker. The closer they got to Neibolt, the quieter the cicadas became, which was strange. Teddy noticed it but didn’t say anything. Derry was full of strange things—missing posters, sudden silences, dogs that wouldn’t go near storm drains.
Matty’s house was a small, sagging place with gray clapboards and a porch that tilted like a shipwreck. But Matty was on the steps, flipping a baseball in one hand. When he spotted them, he froze.
Teddy felt something sharp in his chest. Guilt, maybe. Or shame.
Phil nudged Teddy forward. “Hey, Matty.”
Matty didn’t answer. He just squeezed the baseball like it was the last solid thing in the world.
Teddy cleared his throat. “We, uh… sorry we haven’t been around. There’s been… stuff.”
“Stuff,” Phil echoed weakly.
Matty’s eyes were red in a way that wasn’t from crying. More like from staying awake too long. “You guys hear about the boy who went missing?” he asked.
Teddy stiffened. “Which one?”
“The one near the tracks. Billy Harker.”
Teddy exchanged a look with Phil. They had heard. Everyone had. Derry whispered those stories like gossip, but with fear underneath.
“My mom won’t let me go out after dark anymore,” Matty said softly. “Says something’s wrong in this town.” He looked up at them, and Teddy saw it then—loneliness, yes, but also that same prickling fear he’d been carrying.
Teddy sat beside him. “Yeah,” he said. “There’s something wrong. But we shouldn’t’ve left you alone with it.”
Phil sat on Matty’s other side. “We’re really sorry.”
For the first time in weeks, Matty smiled. Just a little. “You wanna toss the ball around?”
They nodded. Something in the afternoon loosened, as if the cicadas finally remembered their song.
The three boys crossed the yard to the open lot. They tossed the baseball back and forth, letting the rhythm of it fill the space between them. And for a while, it felt normal—just kids in a small town in summer.
But every so often, one of them glanced toward the dark shape of the Neibolt house at the end of the street. And every time, each boy felt the same thing:
They weren’t alone.
Not in Derry. Not ever.
But at least now, they had each other again.
And somehow, that made the shadows seem just a little less close.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 8: Awakening Desires in Derry (Phil Malkin & Rich Santos)
Summary:
In the quiet summer haze of 1967 Derry, Maine, best friends Phil Malkin and Rich Santos share an ordinary afternoon flipping through comics in Phil's bedroom. As Phil drifts into a deep sleep, Rich's hidden cravings bubble over, leading him to tentatively explore Phil's body with trembling, calloused hands. What starts as a secretive stroke awakens Phil to waves of confusion and unexpected pleasure, pulling them into a raw, uncharted territory of mutual desire. Stripped bare and vulnerable, they surrender to urgent touches—fingers probing tight entrances, cocks hardening in rhythm—culminating in a frenzy of thrusts, moans, and shared release that shatters their innocent bond forever. Sweaty and spent, they linger in the afterglow, forever changed by the heat of their first forbidden union.
*SMUT WARNING!!!!!!!!!
Chapter Text
In the dim glow of a single bedside lamp, Phil Malkin's small bedroom in Derry, Maine, felt like a world apart from the crisp autumn chill outside. It was 1967 and the two eighteen-year-olds had spent the afternoon flipping through comic books and trading stories about school pranks, the air thick with the scent of cigarette smoke and teenage sweat. Phil, with his tousled brown hair and lanky frame, stretched out on his narrow bed, his flannel shirt unbuttoned at the collar. Rich Santos, shorter and wirier with dark curls and a mischievous glint in his eyes, sat cross-legged on the floor, leaning against the bedframe.
As the evening wore on, Phil's eyelids grew heavy. 'Man, I'm beat,' he mumbled, yawning wide. He kicked off his sneakers and rolled onto his side, facing the wall. Within minutes, his breathing deepened into the steady rhythm of sleep, his chest rising and falling under his shirt.
Rich watched him for a long moment, his heart pounding in his chest. They'd been friends since grade school, but lately, Rich's thoughts had twisted into something more urgent, more forbidden. The room was quiet except for the distant hum of a car on the street below. He glanced at the door—locked—and then back at Phil's still form. Biting his lip, Rich climbed onto the bed, the mattress dipping under his weight.
Phil didn't stir. Rich's fingers trembled as he reached for the zipper of Phil's jeans. The metal teeth parted with a soft rasp, and he tugged the fabric open, exposing the white cotton briefs underneath. Phil's bulge was soft but prominent, and Rich's breath hitched. He hooked his fingers into the waistband and pulled the briefs down just enough, freeing Phil's cock. It lay flaccid against his thigh, thick even in repose, with a nest of dark hair at its base.
Rich's small hands—calloused from summer jobs—wrapped around the shaft. His palms were warm, and he squeezed gently, feeling the velvety skin shift under his grip. Phil murmured something incoherent in his sleep but didn't wake. Emboldened, Rich began to stroke, slow at first, his thumb circling the circumcised head. The cock twitched in response, thickening as blood rushed in. Rich's own pants felt tight, his erection straining against the denim, but he focused on Phil, pumping steadily now, the length growing to a full seven inches in his fist.
Pre-cum beaded at the tip, slicking Rich's movements. He jerked faster, twisting his wrist on the upstroke, his other hand cupping Phil's balls, rolling them lightly. Phil's hips bucked once, unconsciously, and a low groan escaped his lips. Rich leaned closer, his breath hot against Phil's thigh, inhaling the musky scent. The room seemed to shrink around them, the world outside Derry fading away.
Phil's eyes fluttered open, bleary and confused. 'Rich? What the—' His voice was thick with sleep, but he didn't pull away. Instead, his cock throbbed harder in Rich's hand, betraying his arousal.
'Just relax,' Rich whispered, his voice husky. He didn't stop stroking, his small hands working the shaft with practiced rhythm, though this was his first time touching another guy like this. Phil's resistance melted, his head falling back against the pillow as pleasure overtook him.
Emboldened by Phil's moans, Rich shifted, pushing Phil's jeans and briefs lower, down to his ankles. He stripped off his own shirt, revealing his lean, smooth chest, then fumbled with his belt. Phil watched, dazed, his hand coming up to grip Rich's shoulder. 'This is crazy,' Phil breathed, but his hips lifted, urging Rich on.
Rich kicked off his pants, his own cock springing free—smaller, about five inches, but rock-hard and leaking. He climbed between Phil's legs, spitting into his palm and slicking his fingers. Phil tensed as Rich probed at his entrance, circling the tight ring of muscle before pushing one finger inside. Phil gasped, his body clenching, but Rich worked him open slowly, adding a second finger, scissoring them to stretch the virgin hole.
'Feels weird... good weird,' Phil panted, his cock leaking steadily now. Rich jerked him in time with his fingering, the dual sensations making Phil writhe.
When Rich deemed him ready, he withdrew his fingers and positioned himself, the head of his cock nudging Phil's ass. 'You want this?' Rich asked, voice rough with need.
Phil nodded, eyes locked on Rich's. 'Yeah. Do it.'
Rich pushed in, inch by inch, the tight heat enveloping him. Phil winced, gripping the sheets, but soon relaxed, pulling Rich deeper. Once fully seated, Rich paused, both of them breathing hard, sweat beading on their skin. Then he started thrusting—slow, deep rolls of his hips that made Phil's cock slap against his stomach.
Rich's small hands braced on Phil's chest, pinching his nipples as he fucked harder, the bed creaking under them. Phil wrapped his legs around Rich's waist, meeting each thrust, his own hand dropping to stroke his dick in frantic pumps. The room filled with the sounds of skin slapping skin, grunts and moans echoing off the walls.
Rich leaned down, capturing Phil's mouth in a messy kiss, tongues tangling as he pounded faster. Phil broke away to groan, 'I'm close—fuck, Rich—'
'Cum for me,' Rich urged, angling his hips to hit that spot inside Phil that made stars burst behind his eyes.
Phil arched, his cock erupting in thick ropes of cum that splattered across his chest and Rich's. The clench of Phil's ass around him pushed Rich over the edge; he buried himself deep and came, filling Phil with hot spurts.
They collapsed together, panting, Rich still inside as their bodies cooled. Phil's hand found Rich's hair, pulling him into another kiss. 'Didn't expect that,' Phil murmured, a lazy smile on his face.
Rich grinned, pulling out gently. 'Me neither. But damn, it was good.'
Outside, Derry slept on, oblivious to the shift in their friendship, but in that room, everything had changed.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 9: Summer Whispers in Derry (Phil Malkin & Teddy Uris)
Summary:
Phil Malkin & Teddy Uris hang out on a summer day and their hang out turns into something more.
*SMUT WARNING!!!!!!!!
Chapter Text
The summer sun hung low over Derry, Maine, casting a golden haze across the Kenduskeag Stream. It was 1967, and the town felt like it was holding its breath—kids splashing in the shallows, the distant hum of factories, and the faint echo of rock 'n' roll from a transistor radio somewhere down the block. Phil Malkin, eighteen and lanky with a mop of dark hair that never quite stayed combed, pedaled his Schwinn bike along the dirt path, his heart thumping harder than the chain's rattle.
Teddy Uris rode beside him, his glasses slightly fogged from the heat, freckles standing out on his pale cheeks. At eighteen, Teddy had that wiry build from years of dodging bullies and dreaming of escape, but today his blue eyes sparkled with something softer. They'd been dating for months now, stealing kisses behind the Aladdin Theater or holding hands under the bleachers at Memorial Park. In a town like Derry, where secrets festered like the mold in the old Barrens, their love was a quiet rebellion.
Phil glanced over, grinning. "Race you to the bend? Loser buys the sodas." Teddy laughed, a sound that always made Phil's stomach flip. "You're on, but you know I'll win." They kicked off, tires crunching gravel, wind whipping their shirts until they skidded to a stop at their spot—a hidden clearing by the stream, shielded by overhanging willows.
Dumping their bikes, Phil pulled Teddy close, their bodies pressing together in that familiar way. Teddy's hands slid up Phil's back, fingers tracing the sweat-damp fabric of his t-shirt. "Missed you," Teddy murmured, tilting his head for a kiss. Phil obliged, lips meeting soft and slow, tongues brushing in a lazy dance that tasted of spearmint gum and summer freedom. They sank onto the grass, the earth cool beneath them, and Phil's hand wandered to Teddy's thigh, squeezing gently.
"School's out for good soon," Phil said, breaking the kiss to nuzzle Teddy's neck. "We could hitch to Boston, get jobs, live like nobody's business." Teddy hummed in agreement, his breath hitching as Phil's fingers inched higher. Fluffing Teddy's hair, Phil added, "Or just stay here, build a life away from all the crap." Teddy smiled, eyes half-lidded. "As long as it's with you."
The affection built like the heat of the day, turning tender touches into something hungrier. Phil rolled on top, straddling Teddy's hips, grinding down just enough to feel the growing hardness between them. Teddy gasped, arching up, his hands fumbling with the buttons of Phil's shirt. "God, Phil..." They stripped slowly, shirts tossed aside, revealing sun-kissed skin and the faint scars from Derry's rougher days—Teddy's from a childhood scrap, Phil's from a bike crash.
Phil leaned down, capturing Teddy's mouth again, deeper this time, while his hand slipped into Teddy's jeans, palming the bulge there. Teddy moaned into the kiss, hips bucking as Phil freed his cock, stroking it with firm, deliberate pulls. The shaft was hot and thick in Phil's grip, pre-cum slicking his palm. "You feel so good," Phil whispered, thumb circling the head, drawing out another whimper.
Teddy's glasses fogged completely now, but he didn't care, pushing Phil's jeans down to return the favor. Phil's cock sprang free, hard and curving slightly, veins pulsing under Teddy's touch. They jerked each other off like that for a while, breaths mingling, bodies slick with sweat. The stream babbled nearby, a soothing backdrop to their gasps and the wet sounds of skin on skin.
"Want you inside me," Teddy breathed, voice rough with need. Phil nodded, heart pounding, and reached for the small tube of lubricant they'd stashed in Phil's backpack—contraband from a trip to Bangor. He slicked his fingers, kissing Teddy's collarbone as he prepped him, one digit then two sliding into Teddy's tight heat. Teddy writhed, legs spreading wider, his own hand still working Phil's cock to keep the edge sharp.
When Teddy was ready, panting and begging, Phil positioned himself, cock nudging against that puckered entrance. He pushed in slow, inch by inch, groaning at the vice-like grip. "Fuck, Teddy... so tight." Teddy's nails dug into Phil's shoulders, a mix of pain and pleasure twisting his face into something beautiful. Once fully seated, Phil paused, forehead to forehead, whispering, "Love you. Always."
They moved together then, rhythm building from gentle rocks to harder thrusts. Phil fucked into Teddy with steady drives, balls slapping against skin, while Teddy met him thrust for thrust, his cock trapped between their bellies, leaking steadily. The fluff lingered in their touches—Phil's hand cupping Teddy's jaw for a messy kiss, Teddy's fingers threading through Phil's hair, pulling him closer.
Teddy came first, crying out Phil's name as ropes of cum painted their stomachs, his ass clenching around Phil's pistoning cock. The sight and feel pushed Phil over, burying deep with a guttural moan, filling Teddy with hot spurts. They collapsed in a tangle, breaths ragged, bodies sticky and sated.
As the sun dipped lower, Phil pulled Teddy into his arms, tracing lazy patterns on his back. "That was... wow." Teddy chuckled, nuzzling Phil's chest. "Best date yet." They lay there, watching fireflies blink to life, the world feeling a little less cruel in Derry's shadow. In that moment, with cum drying on their skin and love in the air, nothing else mattered.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 10: Summer Heat in the Hideout (Phil Malkin & Teddy Uris)
Summary:
Phil Malkin & Teddy Uris hang out one summer day and they figure out what Masturbation is
*SMUT WARNING!!!!!!!!!!!
Chapter Text
The summer sun hung low over Derry, Maine, in 1967, casting long shadows across the cracked pavement of the neighborhood streets. Phil Malkin and Teddy Uris, both eighteen and thick as thieves since grade school, trudged through the overgrown lot behind the old textile mill. The air smelled of river mud and distant rain, the kind of sticky heat that made shirts cling to skin. They'd ditched their part-time jobs at the lumber yard early, claiming headaches, and now they were free for the afternoon—no parents nagging, no town busybodies watching.
Phil, with his tousled brown hair and lanky frame, kicked at a rusted can as they reached their spot: a rickety treehouse half-hidden in the willows by the Kenduskeag Stream. It was their hideout, built from scavenged boards years ago, now sagging but still standing. 'Hot as hell out here,' Phil grumbled, wiping sweat from his forehead as he climbed the rope ladder. Teddy followed, his blond curls matted, his broader shoulders straining against his faded t-shirt. 'Yeah, feels like my balls are sweatin' buckets,' Teddy laughed, the word slipping out easy between them, though neither had said much about that stuff before.
Inside the treehouse, the air was thicker, dust motes dancing in the slanted light filtering through the gaps in the walls. They flopped onto the old blankets spread across the floor, legs sprawled out. Phil pulled a crumpled pack of Lucky Strikes from his pocket and lit one, passing it to Teddy. They smoked in silence for a bit, staring at the knots in the wooden ceiling. Then Teddy shifted, his hand absently adjusting the front of his jeans. 'You ever... y'know, touch yourself down there?' he asked, voice low, like he was testing the waters of some forbidden river.
Phil's cheeks flushed under the tan, but he didn't look away. 'What, like jerking off? Yeah, sometimes. Feels good, right? But I don't tell nobody.' He took a drag, exhaling slow. Teddy nodded, eyes flicking to the bulge in his own pants. 'Me too. Started last year, I think. Woke up hard one morning and just... grabbed it. Shot all over my sheets.' They both chuckled, the tension easing into something electric, the shared secret hanging between them like the smoke.
Phil stubbed out the cigarette, his heart picking up pace. 'Wanna see? I mean, show each other how we do it?' The words tumbled out before he could stop them, bold in the dim light. Teddy's breath hitched, but he didn't back down. 'Hell yeah.' They both sat up, knees brushing, and unzipped their jeans with fumbling fingers. Phil shoved his down first, his cock springing free—half-hard already, veined and curving slightly upward, the head flushed pink. Teddy's followed, thicker, with a nest of blond hair at the base, already twitching as the air hit it.
'Like this,' Phil said, wrapping his hand around his shaft, giving it a slow pump. His skin was warm, the friction sending a jolt up his spine. Teddy watched, mesmerized, then mimicked him, stroking from base to tip, his thumb circling the slit where a bead of pre-cum glistened. 'Feels better watchin' you,' Teddy admitted, voice rough. They jerked in unison at first, eyes locked on each other's movements—the way Phil's fist twisted at the top, how Teddy's hips bucked slightly with each pull.
The rhythm built, breaths coming faster. Phil reached out, hesitant, his free hand hovering. 'Can I...?' Teddy nodded, scooting closer until their thighs pressed together. Phil's fingers replaced Teddy's on that thick cock, gripping firm and sliding down, feeling the heat pulse under his palm. Teddy groaned, low and guttural, his hand moving to Phil's in return. Now they were jerking each other off, hands slick with sweat and pre-cum, the treehouse filled with the wet sounds of skin on skin.
Phil's strokes quickened, thumbing the sensitive underside of Teddy's head, making him hiss. 'Fuck, that's good,' Teddy muttered, his grip tightening on Phil's cock, pumping faster, twisting just right. Their balls drew up tight, bodies leaning in, foreheads almost touching. Sweat trickled down Phil's back as the pressure coiled low in his gut. Teddy came first, a strangled curse escaping as his cock throbbed in Phil's hand, ropes of hot cum splattering across Phil's wrist and the blanket below. The sight and feel pushed Phil over, his own release hitting hard—cum shooting in thick spurts over Teddy's knuckles, some landing on his shirt.
They panted, hands slowing to a stop, sticky and spent. Teddy grinned first, wiping his hand on his jeans. 'That was... better than alone.' Phil nodded, zipping up with a lazy smile. The sun dipped lower outside, but in their hideout, the world felt a little less ordinary, a secret sealed in the summer heat of Derry.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 11: Summer Heat Confessions (Lilly Bainbridge & Veronica Grogan)
Summary:
*SMUT WARNING!!!!!!!!!!
Chapter Text
The summer heat draped over Derry, Maine, like a heavy blanket in 1967, the air humming with cicadas and the distant rumble of freight trains. Lilly Bainbridge, eighteen and brimming with unspoken fire, rode her rusty bike along the dusty back roads, her light dress fluttering against her thighs. She spotted Veronica Grogan, her closest companion, perched on a low stone wall near the edge of town, flipping through a dog-eared magazine. Veronica's dark hair cascaded in loose waves, her tank top clinging to her curves from the sweat, paired with cutoff shorts that rode high on her legs.
'Hey, Ronnie!' Lilly shouted, braking hard and hopping off. Her green eyes lit up as she approached. 'Been waiting long?'
Veronica looked up, smirking. 'Long enough to think this town's gonna melt us both. What's the move today, Lil?'
They roamed the outskirts, sharing a stolen apple from an orchard and whispering about school gossip under the sprawling branches of maples. By afternoon, they hit the local stream, dipping their feet in the cool water, splashing each other until their clothes stuck damp to their skin. As the sun dipped, painting the sky in oranges and pinks, Lilly wiped her brow. 'Sleepover at my place? Mom's away on that buisness trip, house to ourselves.'
Veronica's face brightened. 'Hell yeah. Beats listening to my folks argue all night.'
The Bainbridge home sat quiet on a quiet lane, its screens creaking in the breeze. Up in Lilly's room, posters of rock stars peeled at the edges, and the air smelled of vanilla from a flickering candle. They stripped down to underwear and tees, borrowing each other's clothes—Lilly in a loose tank that showed the outline of her bra, Veronica in shorts that hugged her ass. They piled onto the bed with a stack of records spinning on the player, Elvis crooning low as they passed a bottle of pilfered lemonade.
The night deepened, laughter flowing easy until a spark ignited. It flared over something trivial—Veronica teasing Lilly about dodging dances with the boys.
'You act like you're too good for 'em,' Veronica said, her tone sharpening. 'Always hanging back, watching me make a fool of myself.'
Lilly's jaw tightened. 'Maybe I don't like watching you throw yourself at idiots who don't deserve you. You're better than that, Ronnie.'
'Better? Says the girl who hides behind her books!' Veronica snapped, sitting up. 'What're you so afraid of, anyway?'
Words flew like daggers, accusations piling until Veronica bolted upright, snatching her scarf. 'Screw this. I'm out. Can't stand your holier-than-thou bullshit tonight.'
She yanked the door open, stepping into the hallway. Lilly's chest heaved, tears pricking her eyes. 'Ronnie, stop! I... I love you. Not just as friends. I love you like... like I want to kiss you, hold you, everything. Please don't go.'
Veronica halted, back turned, shoulders tense. The house fell silent, save for the faint tick of a clock downstairs. Then, slowly, she pivoted, her eyes locking on Lilly's—dark pools swirling with confusion and heat. Without a word, she closed the distance, grabbing Lilly's arms and crashing their mouths together.
The kiss was raw, desperate—lips bruising, tongues tangling in a slick dance. Veronica's hands fisted in Lilly's tank, pulling her flush, their breasts pressing through thin fabric. Lilly moaned into her mouth, tasting the tart lemonade on Veronica's tongue.
'Fuck, Lil,' Veronica gasped, breaking away just enough to speak, her breath hot against Lilly's neck. 'I've wanted to do this forever. You have no idea how bad I crave you.'
Lilly's fingers dug into Veronica's hips, yanking her closer. 'Then show me. Touch me, Ronnie. I need your hands on my pussy, making me wet.'
They stumbled back to the bed, Veronica shoving Lilly down onto the rumpled sheets. She straddled her, grinding down as she peeled off Lilly's tank, exposing her pale breasts, nipples stiffening under the cool air. Veronica's mouth latched onto one, sucking hard, teeth grazing the peak.
'Oh God, yes,' Lilly whimpered, arching up. 'Suck my tits harder. Bite them, make it hurt so good.'
Veronica obliged, nipping sharply before soothing with her tongue, her hand sliding under Lilly's waistband. Fingers found her soaked panties, rubbing the damp cotton over her clit. 'You're dripping already, you little slut. This pussy's begging for me.'
Lilly bucked against her palm. 'Rip them off. Finger my cunt, Ronnie. Fuck me deep.'
With a growl, Veronica tore the fabric aside, plunging two fingers into Lilly's tight heat. She thrust hard, curling them to stroke that inner spot, her thumb circling the swollen clit. Lilly's walls clenched, slick sounds filling the room as she rode the intrusion.
'Like that? My fingers stretching your wet hole?' Veronica panted, pumping faster. 'Gonna make you cum all over my hand.'
Lilly's head thrashed, moans turning to cries. 'Yes, fuck yes! Don't stop—I'm so close. Your fingers feel so fucking good inside me.'
Veronica leaned down, capturing Lilly's mouth in a sloppy kiss while her free hand pinched the neglected nipple. Lilly shattered, her pussy spasming, juices soaking Veronica's fingers as she screamed into the kiss.
Panting, Lilly flipped them, pinning Veronica beneath her. 'My turn to taste you. Spread your legs, let me eat that sweet pussy.'
Veronica kicked off her shorts and panties, thighs parting wide to reveal her glistening folds, clit peeking out swollen and red. Lilly dove in, tongue lapping flat from entrance to nub, savoring the musky flavor.
'Fuck, Lil, your tongue's magic,' Veronica groaned, hips lifting. 'Lick my clit, suck it like you mean it. Deeper—tongue-fuck my hole.'
Lilly obeyed, plunging her tongue inside the clenching warmth before sucking the clit between her lips, humming vibrations against it. Her fingers joined, three now sliding into Veronica's sopping cunt, stretching her wide.
'Oh shit, yes! Finger-bang me harder. Make my pussy squirt for you,' Veronica begged, hands clamping Lilly's head, grinding her face against her crotch.
Lilly's mouth worked relentlessly, tongue flicking, fingers scissoring until Veronica's body seized, a gush of wetness flooding Lilly's chin as she came with a guttural yell.
They weren't done. Veronica rolled them sideways, grabbing the lotion from the dresser. 'Want you in my ass now. Lube me up and fuck my tight hole.'
Lilly's eyes widened with lust, slicking her fingers generously. She teased Veronica's puckered entrance, pushing one in slow. 'So tight back here. Relax, baby—gonna fill your ass with my fingers.'
Veronica pushed back, moaning. 'Add another. Stretch my asshole wide. Fuck it like you own it.'
Two fingers breached, thrusting in rhythm with Lilly's other hand rubbing Veronica's clit. 'Your ass is gripping me so hard. Cum for me again, you dirty girl.'
Veronica shuddered through another orgasm, her hole pulsing around the digits. Then she returned the favor, prepping Lilly's rear with careful strokes. 'Bend over. I wanna rim you first—lick your pretty ass.'
Lilly knelt, ass up, as Veronica's tongue circled her rim, dipping in wetly. 'Tastes so good. Now fingers—fuck my ass deep while you play with my pussy.'
Veronica slid in, two fingers pumping the tight ring while her mouth devoured Lilly's dripping slit. 'Cum with my tongue in your cunt and fingers in your ass. Scream for me.'
Lilly did, her body quaking in release, waves crashing over her.
Finally, they locked legs, pussies grinding together in slick friction, clits bumping with each roll. 'Rub your wet cunt on mine,' Lilly urged. 'Make us both cum like this.'
'Fuck, yes—your pussy's so hot against me,' Veronica replied, hands squeezing breasts as they humped frantically. 'Gonna soak you with my cum.'
They peaked together, cries mingling, bodies slick and spent. As the first light filtered through the curtains, they tangled in each other's arms, the fight a distant memory, their bond forged in raw, explicit passion.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 12: The Evening Walk (Lilly Bainbridge & Marge Truman)
Summary:
Lilly and Marge take a walk and Marge confesses to Lilly that she loves her
Chapter Text
Derry, Maine had a way of swallowing sound at dusk. By the time the sun dipped behind the stand of pines past Witcham Street, the town seemed to exhale—quieting the mills, softening the clatter of shop doors, settling everything under a warm, amber hush.
Lilly Bainbridge and Marge Truman walked side-by-side down the cracked sidewalk of West Barrow, their sandals tapping lightly in unison. They’d spent the afternoon wandering the long aisles of Secondhand Stories, thumbing dog-eared paperbacks and giggling at the romance covers, then bought cherry sodas at King’s Diner before deciding to walk the long way home.
Lilly liked the long way home. It meant more time with Marge.
Marge had a way of walking like she was thinking her steps into existence—slow, careful, aware. Tonight, though, she was quiet in a different way. She kept fiddling with the ends of her cardigan sleeves and chewing her lip, like she had something folded up inside her that needed to be smoothed out.
“You’re awfully serious,” Lilly finally said, glancing over. “Did Mrs. Cardwell nag you again about the napkin folding at the diner?”
Marge let out a laugh, small and nervous. “No. It’s not that.”
They passed under one of the sputtering street lamps on Neibolt, the kind that always flickered like it couldn’t decide if it wanted to stay alive. The light caught Marge’s hair—dark auburn, tumbling out of its pins—and painted her face in soft gold.
Lilly felt her heart flutter, then immediately told it to be quiet.
“What is it, then?” Lilly asked.
Marge stopped walking. Just—stopped. Lilly took two steps before she realized and turned back, the summer wind pressing the hem of her dress against her legs.
“I need to tell you something,” Marge said. Her voice was steady, but her hands were trembling where they clutched one another. “And I figure… if I don’t say it now, I’ll lose my nerve forever.”
Lilly’s stomach tightened with a strange fear—one that felt a little like hope.
“Okay,” she said softly. “Tell me.”
Marge took a breath so deep it lifted her shoulders. “Lilly, I—” She pressed her eyes shut for a moment, gathering courage. “I’m in love with you.”
The words seemed to hang suspended in the warm air, like fireflies that refused to drift away.
Lilly blinked, stunned—not because she hadn’t imagined it, but because she finally heard it out loud, real and undeniable. A slow warmth spread through her chest, blooming like the lilacs behind her mother’s porch.
“Marge…” she whispered. “I—why were you so scared to tell me?”
“You’re my best friend,” Marge said, voice cracking. “And it’s 1965, and people talk, and I didn’t know if you—if you’d think I was wrong or strange or—”
Lilly closed the distance and took Marge’s hands, steadying them. “There’s nothing wrong about you. Not one thing.”
Marge’s eyes opened, glimmering with something fragile and astonished.
“And,” Lilly added, feeling her own courage rise, “I think I might be in love with you too.”
The flickering streetlamp finally held its light, steady and bright. Marge’s breath caught, then tumbled out in a relieved laugh that melted into a smile—wide, shy, beautiful.
Lilly squeezed her hands. “Come on,” she said gently. “Let’s keep walking.”
They resumed their path through the sleepy streets of Derry, shoulders brushing with every step, hearts lighter than the summer air. The town might have held its shadows and secrets, but for the first time, neither girl felt like they were walking alone.
And somewhere between the glow of the streetlamps and the soft chorus of crickets, the world seemed just a little kinder.
Notes:
SORRY THIS CHAPTER IS BEING POSTED IN THE EVENING TIME, BEEN REALLY BUSY, BUT THE NEW CHAPTER IS OUT NOW
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
NEXT CHAPTER WILL BE OUT TOMORROW AFTERNOON
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 13: Before the Streetlights Flickered (Lilly Bainbridge x Veronica Grogan)
Summary:
Lilly & Ronnie's first confessions
Chapter Text
Derry, Maine had a way of smelling like rain even when the sun was out—pine needles, old asphalt, and the faint sweetness of penny candy from O’Malley’s General Store. It was early June 1965, warm enough for short sleeves but cool enough that the wind still nipped at bare arms.
Lilly Bainbridge stood beside the rust-red bicycle she and her father had repainted, watching the pavement shimmer with late-afternoon light. She was waiting—pretending she wasn’t—outside the Derry Public Library. The front steps creaked, the same way they always did, and then Veronica Grogan appeared.
Veronica’s hair was tucked into a neat ribbon, pale yellow today, matching the buttons on her blouse. She held two books to her chest, but her smile—her smile was the brightest thing in town.
“You waited for me,” Veronica said, sounding shyly pleased.
“Maybe,” Lilly replied, kicking at a pebble.
They started down the sidewalk together, the way they always did, close enough that their elbows brushed. Derry bustled around them—a couple of boys tossing a football, Mrs. Mathers sweeping her porch, the far-off rattle of a passing truck—but the town felt like background noise whenever they were together.
“What’d you rent this time?” Lilly asked, nodding at the books.
Veronica laughed softly. “More poetry. My mother says I’ll rot my brain if I don’t read something ‘proper.’”
“You? Rot your brain? Impossible,” Lilly said. Then, because her courage was fickle: “You’re the smartest person I know.”
Veronica’s cheeks turned a lovely shade of pink. “You always say things like that.”
“Only when they’re true.”
Their steps slowed as they reached the small park beside the Kenduskeag Stream. Children shouted from the swings, but the big oak in the corner cast a shadow that felt almost private. They sat beneath it—Lilly with her knees pulled up, Veronica smoothing her skirt over her legs.
A slow, comfortable quiet settled in.
“Lilly?” Veronica’s voice was soft, but steady.
“Yeah?”
“I… I want to tell you something, but you mustn’t think it strange.”
Lilly’s heart thumped once, hard. “I won’t.”
Veronica looked down at her hands, fingers twisting in the fabric of her skirt. “When I’m with you, everything feels… lighter. Nicer. Like the day is brighter than it really is.” She swallowed. “I don’t feel that way around anyone else. Not ever.”
Lilly felt heat rush to her face. The world seemed to hold its breath—the breeze, the children, even the trees.
“Oh,” she said, breathlessly. “Well, that’s not strange at all.”
Veronica looked up, hopeful. “It’s not?”
“No,” Lilly said, shifting closer until their shoulders touched. “Because I feel the exact same way.”
Veronica blinked rapidly, the way someone does when they’re trying not to cry. “Really?”
“Really,” Lilly whispered. “I… think about you all the time. I hope that’s not strange.”
“It’s wonderful.”
The sun dipped lower, painting gold across Veronica’s cheeks. For the first time, she didn’t look away. And Lilly, shaking only a little, let her hand drift across the grass until her fingers brushed Veronica’s.
Veronica’s hand curled gently around hers.
“Is this okay?” Lilly asked.
“More than okay.”
They sat like that until the streetlights flickered on—warm fingers entwined, hearts too full and too new to hide. When they finally stood to leave, Veronica squeezed Lilly’s hand one last time.
“I’m glad I told you,” she murmured.
“Me too,” Lilly said, her smile soft, certain. “It feels like the start of something.”
And in the warm June dusk of Derry, Maine, 1965, it was.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 14: Window Of Desire (Lilly Bainbridge & Rich Santos)
Summary:
Rich goes over to his friend Lilly's house and catches her in a private moment........ What will Rich do?
*SMUT WARNING!!!!!
Chapter Text
It was a sweltering summer afternoon in Derry, Maine, 1967. The kind of heat that made the air thick and sticky, clinging to your skin like a second layer. Rich Santos, eighteen and full of that restless teenage fire, pedaled his beat-up Schwinn bike up the cracked driveway of the Bainbridge house on the edge of town. He'd been thinking about Lilly all day—her sharp green eyes, the way her sundresses hugged her curves, and that sly smile she flashed when no one else was looking. They were both seniors at Derry High, but lately, things between them had gotten charged, like static before a storm.
Rich propped his bike against the sagging porch and knocked on the screen door, the wood frame rattling under his fist. 'Lilly? You home?' he called out, his voice echoing off the quiet street lined with maple trees. No answer. He knocked again, harder this time. 'Come on, Lil, I know you're in there. Let's go down to the quarry, cool off.' Still nothing. The house looked empty, curtains drawn against the sun, but he swore he heard a faint sound from inside—a soft hum, maybe the radio.
Frustrated but not ready to leave, Rich circled around to the side of the house. The Bainbridges' place was old, with peeling white paint and a backyard that backed onto the woods. Lilly's bedroom window was on the first floor, half-hidden by overgrown bushes. He pushed through the leaves, heart picking up speed as he crouched low and peeked through the gap in the curtains. What he saw made his breath catch in his throat.
Lilly Bainbridge lay sprawled across her unmade bed, her lithe eighteen-year-old body bare from the waist down. Her sundress was hiked up around her hips, bunched fabric exposing her smooth thighs and the dark patch of curls between them. One hand gripped the sheets, knuckles white, while the other worked furiously between her legs. Her fingers plunged in and out of her pussy, slick with her own wetness, the motion rhythmic and urgent. She circled her clit with her thumb, pressing hard, her hips bucking up off the mattress.
'Oh fuck,' she moaned, her voice low and husky, carrying through the cracked window. 'Yeah, just like that... deeper, you bastard.' Her eyes were squeezed shut, head thrown back against the pillow, blonde hair fanned out like a halo. She was lost in it, whispering filthy encouragements to herself. 'God, my pussy's so wet... gonna make myself cum so hard.' Her fingers sped up, two digits now sliding deep inside her, stretching her open as she rubbed her swollen clit faster. Juices glistened on her thighs, the wet sounds of her fingering filling the room.
Rich's cock twitched in his jeans, hardening instantly. He couldn't tear his eyes away. Lilly's small tits heaved under her dress with each breath, nipples poking through the thin cotton. She arched her back, moaning louder. 'Fuck me, fill me up... I need that cock pounding my cunt.' Her body trembled, fingers pistoning in and out, clit throbbing under her touch. Rich's hand moved on instinct, fumbling with his zipper. He pulled out his throbbing cock, already leaking pre-cum from the tip. It was thick and veined, standing rigid in his fist as he wrapped his fingers around it and started stroking.
He matched her rhythm, pumping his shaft slow at first, watching her pussy clench around her fingers. 'Shit, Lilly,' he whispered to himself, breath ragged. Her moans grew desperate—'Yes, right there, rub my clit, make me squirt'—and it drove him wild. His hand flew faster, balls tightening as he jerked off to the sight of her writhing, her juices soaking the sheets. He imagined it was his cock buried in her, stretching that tight hole.
Lilly's eyes fluttered open suddenly, locking onto the window. She froze for a split second, then a wicked grin spread across her face. 'Rich? You dirty fucker,' she gasped, not stopping her fingers. Instead, she spread her legs wider, giving him a full view of her dripping pussy. 'Been watching me? Get in here.'
Rich's face burned, but he shoved his cock back into his pants, zipping up just as she lunged to the window. She yanked it open wide and grabbed his shirt, pulling him through with surprising strength. He tumbled inside, landing on the worn carpet of her room, the scent of her arousal thick in the air. Lilly shut the window behind him, her dress still askew, pussy glistening and exposed.
Before he could say a word, she dropped to her knees in front of him, eyes hungry. 'You think you can spy on me and just walk away?' she teased, her hands already at his belt. She unbuckled it swiftly, tugging his jeans down to his ankles. His cock sprang free again, hard and bobbing in front of her face. 'Look at this big dick. All stiff from watching me finger my pussy?'
'Lilly, I—' Rich started, but she cut him off by wrapping her soft hand around his shaft, stroking it firmly. Pre-cum smeared over her palm as she leaned in, her hot breath ghosting the head.
'Shut up and let me suck this cock,' she said, her voice dripping with lust. She parted her lips and took him in, tongue swirling around the tip before sliding down, engulfing half his length in one go. Rich groaned, his hands fisting in her hair as her mouth worked him over. She bobbed her head, sucking hard, her cheeks hollowing with each pull. Saliva dripped down his balls as she took him deeper, gagging slightly when he hit the back of her throat but not stopping.
'Fuck, your mouth feels so good,' Rich panted, thrusting gently into her warmth. Lilly hummed around him, the vibration shooting straight to his core. She pulled back, strings of spit connecting her lips to his cock, and looked up at him with those green eyes. 'You like that? My tongue on your fat cock?'
'Hell yes,' he growled, pushing her head back down. She obliged, sucking sloppily now, one hand pumping the base while the other cupped his balls, rolling them gently. Rich's knees weakened; it was the best blowjob of his life, her lips stretched wide around him, throat relaxing to take more. He reached down, slipping a hand under her dress to grope her tits. They were perky, nipples hard as pebbles under his fingers. He pinched one, twisting lightly, and she moaned around his cock, the sound muffled but intense.
'Your tits are perfect,' he said, squeezing both now, feeling their weight in his palms. Lilly popped off his dick with a wet smack, gasping for air. 'Play with them harder. Make my nipples ache.' She dove back in, deepthroating him fully, nose pressing against his pubes as she swallowed around him.
Rich couldn't hold back much longer. 'Shit, Lilly, I'm gonna cum if you keep that up.' But she didn't stop, sucking faster, her hand twisting on his slick shaft. He pinched her nipples roughly, eliciting a whimper from her. Finally, with a guttural moan, he exploded, hot spurts of cum flooding her mouth. She swallowed every drop, milking him dry with her lips and tongue until he was spent, legs shaking.
Lilly pulled away, licking her lips with a satisfied smirk. 'Tastes good. But I'm not done with you yet.' She stood, shoving him back toward the bed. Rich fell onto the mattress, still catching his breath, as she stripped off her dress completely. Her body was a vision—firm tits, flat stomach, and that soaked pussy begging for attention.
She climbed on top of him, straddling his hips. His cock, already stirring back to life, pressed against her wet folds. 'You watched me play with my pussy. Now fuck it,' she demanded, grinding down on him. Rich grabbed her ass, guiding her as she lifted and sank onto his hardening dick. Inch by inch, she took him in, her tight walls gripping him like a vice.
'Oh god, your cock's so thick,' Lilly cried out, bottoming out with a shudder. She started riding him, hips rolling in circles, pussy clenching around his length. Rich thrust up to meet her, hands roaming her body—squeezing her tits, slapping her ass lightly. 'Ride me harder, Lilly. Bounce on that dick.'
She did, slamming down repeatedly, the bed creaking under them. Wet slaps filled the room as his cock plunged deep into her sopping cunt. 'Fuck yes, pound my pussy! Deeper, Rich, stretch me out!' Her tits bounced with each drop, and he latched onto one nipple, sucking hard while pinching the other.
Rich flipped them over suddenly, pinning her beneath him. 'My turn,' he grunted, hooking her legs over his shoulders. He drove into her hard, balls slapping her ass with every thrust. Lilly's nails raked his back, her moans turning to screams. 'Yes! Fuck me like that! Your cock feels amazing in my wet hole.'
He pounded relentlessly, feeling her pussy flutter around him. Sweat slicked their bodies, the summer heat amplifying everything. 'You're so tight, Lilly. Gonna fill this pussy with cum.' She wrapped her legs around him, pulling him deeper. 'Do it. Cum inside me. Make me yours.'
Her words pushed him over the edge. With a final, brutal thrust, he buried himself to the hilt and unleashed, ropes of hot cum flooding her depths. Lilly came with him, her pussy spasming, milking every drop as she wailed, 'I'm cumming! Fuck, yes!'
They collapsed together, panting, bodies entwined on the rumpled sheets. The afternoon sun filtered through the curtains, casting a golden glow over their satisfied forms. In Derry, Maine, 1965, nothing had ever felt so right.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 15: Angsty Reunion In Derry (Lilly Bainbridge & Phil Malkin)
Summary:
In the shadowed streets of 1967 Derry, Maine, survivors Lilly Bainbridge and Phil Malkin, both 18, reunite after five years apart, haunted by the 1962 Theatre Massacre where a demonic entity claimed Phil's sister Susie and their friend Teddy. Believing Phil dead, Lilly grapples with her lingering trauma until their chance encounter sparks a raw reconnection at their childhood haunt, the standpipe. As polar opposites drawn together by shared grief, they confront their nightmares through tearful confessions and an intense, cathartic sexual awakening—fueled by desperation, desire, and the urgent need to reclaim life from the horrors that nearly destroyed them.
*SMUT WARNING!!!!!!!!!
Chapter Text
Lilly Bainbridge hurried down the cracked sidewalks of Derry, Maine, the summer heat of 1967 clinging to her skin like a bad memory. At eighteen, she was all sharp edges and restless energy—long dark curly hair tied back in a ponytail that swung with her quick steps, freckles dusting her nose from too many days under the gray skies. She clutched a grocery list from her mom, the paper damp in her palm, weaving through the familiar streets that still whispered horrors from five years ago. The Aladdin Theatre massacre in 1962 had scarred the town, but for Lilly, it had carved deeper. That night, she, her friend Teddy, Phil Malkin, and his little sister Susie had been caught in the chaos. A grotesque flying thing—a demon baby with leathery wings and razor teeth—had descended on them in the dark auditorium. It tore into Teddy first, ripping his throat out in a spray of blood that painted the seats. Susie, only ten, screamed as it latched onto her, shredding her tiny body before Phil could pull her away. Lilly had blacked out from the terror, waking up in the hospital with no sign of Phil. Everyone assumed he was dead, just like so many others.
She turned the corner near the old pharmacy, nearly colliding with a tall figure stepping out from the shadows of the alley. He was lean, almost gaunt, with messy dark hair falling over haunted blue eyes. A faded jacket hung off his shoulders, and his hands were shoved deep in his pockets, knuckles white.
'Watch it,' Lilly snapped instinctively, her voice carrying that fiery edge she used to keep the world at bay.
The man froze, his gaze locking onto hers. Recognition hit like a punch. 'Lilly?'
Her heart stuttered. 'Phil? Phil Malkin? Oh my God... you're... you're alive?'
He nodded slowly, a ghost of a smile tugging at his lips, but it didn't reach his eyes. 'Yeah. It's me.'
Lilly's bag of errands slipped from her fingers, apples rolling across the pavement. She didn't care. Five years of nightmares, and here he was, standing in front of her like he'd clawed his way out of hell. 'How? They said everyone in that row was gone. The papers, the cops—everyone thought you were...'
'Dead,' Phil finished, his voice low and rough, like gravel under boots. He bent to pick up her apples, handing them back with steady hands that betrayed a faint tremble. 'I almost was. That thing—the flying freak—got Susie right in front of me. I fought it off, grabbed a piece of broken seat and bashed its skull in. But the smoke, the screams... I got separated. Hid in the basement until it was over. Cops found me later, half-delirious. My folks... they didn't make it out either.'
Lilly's throat tightened. She could see it all again: Susie's small hand slipping from Phil's as the creature swooped down, its wings beating a foul wind. Teddy's gurgling last breath. 'I woke up in the hospital alone. Thought you were gone too. Jesus, Phil, why didn't you find me?'
He shrugged, looking away toward the distant canal. 'I was a mess. Bounced around foster homes after that. Derry felt like a graveyard. But I'm back now. For good, I guess.'
She studied him—the way he held himself apart, quiet and brooding, so different from the cocky kid he'd been at thirteen. Back then, Phil was the one cracking jokes, pulling pranks, while Lilly was the serious one, always planning their next adventure. Now, she was the spark, vibrant and unyielding, pushing through life with sheer will. He seemed dimmed, shadows clinging to him like the Derry fog. Opposites, yeah, but something pulled at her, a thread from that blood-soaked night.
'Come on,' she said, grabbing his arm without thinking. 'We can't talk here. Let's go to the standpipe. Like old times.'
Phil hesitated, then followed. The standpipe loomed on the hill overlooking the town, a rusted relic where kids used to hang out, sneaking smokes and sharing secrets. Now, at eighteen, it felt like a sanctuary from the ghosts.
They climbed in silence, the gravel crunching underfoot. At the top, Lilly leaned against the cold metal, catching her breath. Phil paced a few steps away, staring out at the sprawl of Derry below—the library, the barrens, the canal that swallowed secrets.
'Tell me everything,' Lilly demanded, her green eyes fierce. 'That night... I keep seeing it. The way it flew at us, eyes glowing like coals. Teddy tried to shove me out of the way, and it just... ripped him open. And Susie—God, she was so scared, clinging to you.'
Phil stopped pacing, his jaw clenching. 'I hear her screams every night. That thing latched onto her arm first, tearing flesh like paper. I swung at it, but it was fast. Susie looked at me, Lilly—right in the eyes—and said, "Phil, it hurts." Then it went for her throat. I killed it, but too late. Blood everywhere. I crawled out covered in it, thinking you'd all made it somehow. But you didn't see me in the panic.'
Tears stung Lilly's eyes, but she blinked them back. 'I searched for you. After the hospital, I went to your house, but it was empty. The town was in ruins, people whispering about some clown or worse. Derry's cursed, Phil. That thing wasn't natural.'
He moved closer, the space between them shrinking. 'No, it wasn't. But we survived. You and me. Out of all of us.' His voice cracked, and for the first time, she saw the raw pain beneath his stoic mask.
Lilly reached out, her fingers brushing his cheek. He was warm, real. 'I thought I was alone with this. The nightmares, the what-ifs. But you're here. How did we make it?'
Phil's hand covered hers, holding it there. 'I don't know. But seeing you... it makes it bearable. You're still fighting, Lilly. Always have been. Me? I just... exist.'
She laughed bitterly, a sound laced with old hurt. 'Fight? I'm running, same as you. But together? Maybe we don't have to.' Their eyes met, and something shifted—trauma twisting into connection, opposites drawing like magnets. She was fire, he was ice, but in Derry's chill, they needed each other.
Phil's gaze dropped to her lips, then back up. 'Lilly, I...'
She closed the gap, kissing him hard, pouring five years of unspoken grief into it. He stiffened for a second, then responded, his arms wrapping around her waist, pulling her flush against him. The kiss deepened, tongues tangling with desperate hunger, tasting salt from tears neither admitted to.
They broke apart, breathing ragged. 'This is crazy,' Phil murmured, his forehead against hers. 'But I need you. Need to feel alive.'
'Then feel me,' Lilly whispered, her hands sliding under his jacket, fingers tracing the hard lines of his chest. 'Fuck the past for once.'
He groaned, backing her against the standpipe's cool surface. His mouth claimed hers again, rougher now, teeth nipping her lower lip as his hands roamed up her skirt, bunching the fabric. Lilly arched into him, her body igniting despite the ache in her chest. She yanked at his belt, fumbling it open, her palm pressing against the growing bulge in his jeans.
'God, Lilly,' Phil rasped, his voice thick with anguish and want. 'You have no idea how many times I dreamed of this—of you—after that night. To forget the blood.'
She squeezed him through the denim, feeling his cock harden fully. 'Then fuck me, Phil. Make me forget too. Hard. Like we deserve to hurt a little less.'
He didn't need more urging. Phil shoved her skirt higher, his fingers hooking into her panties and yanking them down her thighs. She kicked them aside, spreading her legs as he freed his cock—thick and veined, already leaking at the tip. Lilly wrapped her hand around it, stroking firmly, guiding him to her entrance. She was wet, slick from the raw emotion surging between them.
With a guttural moan, Phil thrust in, burying himself deep in one sharp motion. Lilly gasped, her nails digging into his shoulders as he filled her completely, stretching her walls. 'Yes—fuck, just like that,' she panted, her hips bucking to meet him.
He pinned her harder against the metal, pounding into her with frantic rhythm, each slap of skin echoing their shared torment. 'You're so tight, Lilly—so fucking perfect,' he growled, his breath hot against her neck. 'This... this is us surviving.'
Tears slipped down her cheeks as pleasure coiled tight in her core, mingling with the grief. 'Harder, Phil. Don't stop—make it hurt good.' She clenched around him, drawing a curse from his lips.
His hand slid between them, thumb circling her clit roughly, sending sparks through her. Lilly's head fell back, a sob escaping as the tension built. 'I see them sometimes—Teddy, Susie—in my dreams. But you... you're real. Fuck me like you won't let go.'
Phil's thrusts grew erratic, his free hand gripping her ass, lifting her slightly to drive deeper. 'I won't. Never again. Cum for me, Lilly—let it out.'
She shattered then, her pussy spasming around his cock, waves of release crashing through her with a cry that mixed ecstasy and sorrow. Phil followed seconds later, groaning her name as he pumped hot cum deep inside her, hips jerking until he was spent.
They slumped together, still joined, breaths mingling in the afterglow. Phil kissed her temple softly. 'We're not alone anymore.'
Lilly nodded, holding him close. In Derry's shadows, they'd found a fragile light—in each other.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
ALSO IM SORRY FOR NOT POSTING ANYTHING YESTERDAY, I WAS NOT FEELING WELL SO I SKIPPED A DAY OF POSTING BUT IM BETTER NOW AND IM POSTING THE NEW CHAPTER, ALSO IM GOING BACK TO POSTING EVERYDAY
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 16: After Juniper Hill (Lilly Bainbridge & Veronica Grogan)
Summary:
After her release from Juniper Hill in 1962, Lilly Bainbridge returns to Derry, Maine, carrying the quiet scars of heartbreak and confinement. Waiting for her is Veronica Grogan—the woman who never stopped loving her. As Lilly learns to live outside locked doors and whispered judgments, Ronnie offers steady hands, gentle patience, and a love strong enough to hold what was broken. In a town that does not understand them, the two women find comfort, healing, and a second chance at a life built on trust, devotion, and the courage to choose one another.
Chapter Text
Juniper Hill had taken pieces of Lilly Bainbridge and returned her thinner, quieter, and frightened of her own thoughts.
The brick building loomed above her like a bad memory she could not quite shake, even as the taxi pulled away and the iron gates clanged shut behind her. June sunlight filtered through the tall elms along Kansas Street, but Lilly felt cold all the same. She stood with her small suitcase clutched in both hands, unsure where to look, unsure how to breathe without permission.
“Lilly.”
The voice came gently, as if afraid to startle her. She turned and there was Veronica Grogan, standing just beyond the shadow of the gates. Ronnie wore a pale blue dress, sensible shoes, her dark hair pinned neatly at the nape of her neck. She looked older than Lilly remembered—stronger somehow—but her eyes were the same: warm, steady, and full of concern she did not try to hide.
For a moment, Lilly forgot how to move. Then Ronnie crossed the distance between them and took the suitcase from her trembling hands.
“You don’t have to carry that,” she said softly. “You don’t have to do anything right now.”
Lilly swallowed. “I didn’t think you’d really come.”
Ronnie’s mouth curved into something sad and fond. “Of course I came.”
She reached for Lilly’s arm, not pulling, just offering. When Lilly leaned into her, Ronnie adjusted instantly, steadying her like it was the most natural thing in the world.
The drive back into town was quiet. Derry drifted past the window—storefronts, the canal, children on bicycles—but Lilly watched none of it. Her gaze stayed fixed on her hands, folded too tightly in her lap.
“They said I’m better,” Lilly murmured finally. “They always say that.”
Ronnie glanced at her but kept her eyes on the road. “You don’t have to believe them. We’ll decide together what better looks like.”
The word together settled warmly in Lilly’s chest, easing something that had been clenched for months.
Ronnie’s house sat at the edge of town, modest and clean, with white curtains fluttering in the open windows. Inside, everything smelled faintly of soap and fresh bread. Ronnie showed her the spare room—your room, she corrected gently—and set Lilly’s suitcase at the foot of the bed.
“I made soup,” Ronnie said. “If you’re hungry.”
“I might be,” Lilly said, surprised to find it was true.
They sat at the small kitchen table, knees almost touching. Ronnie watched Lilly carefully, like she was learning her all over again—how she held her spoon, how she flinched at sudden sounds, how she smiled apologetically when she spilled a drop on the tablecloth.
“It’s alright,” Ronnie said, wiping it away. “You’re safe here.”
The word safe brought tears to Lilly’s eyes before she could stop them. She pressed her lips together, embarrassed.
Ronnie stood, came around the table, and crouched beside her chair. She didn’t touch her at first.
“You don’t have to be brave with me,” she said quietly. “You never did.”
That was what broke her.
Lilly leaned forward, burying her face against Ronnie’s shoulder. She shook with sobs she had swallowed for months, for years. Ronnie wrapped her arms around her without hesitation, holding her firmly, anchoring her to the moment.
“I’ve got you,” Ronnie murmured. “I’ve got you.”
Days passed in small, careful increments.
Ronnie never rushed her. She left the door open when Lilly needed air and closed it when she needed quiet. She brewed tea at night when the nightmares came and sat beside her bed, humming softly until the tremors passed.
Sometimes Lilly talked—about the long corridors of Juniper Hill, the white walls, the way time lost meaning inside those rooms. Ronnie listened without interruption, her hand warm over Lilly’s, her thumb tracing slow, reassuring circles.
One evening, as they sat on the porch watching fireflies blink on and off in the dusk, Lilly finally asked the question that had haunted her.
“Why did you stay?” she whispered. “After everything.”
Ronnie inhaled slowly. “Because I loved you,” she said, simply. “And because loving you never stopped being the truest thing I knew.”
Lilly turned to her, heart pounding. In 1962, there were words you did not say aloud, feelings you folded carefully into yourself. But Ronnie had always been braver than her.
“I thought I’d lost you,” Lilly said. “In there.”
Ronnie reached out, brushing her knuckles along Lilly’s cheek. “You wandered. You didn’t disappear.”
Their eyes met. The space between them felt charged, fragile, full of everything they had not dared to name before.
Ronnie moved first, slow enough for Lilly to pull away if she needed. But Lilly didn’t. She leaned in, resting her forehead against Ronnie’s, breathing her in.
The kiss, when it came, was soft and reverent. Not desperate, not demanding—just a promise. Ronnie’s hand cradled the back of Lilly’s head, grounding her, reminding her she was here, she was real, she was cherished.
When they parted, Lilly laughed quietly through tears. “I’m still broken.”
Ronnie smiled, pressing another kiss to her temple. “Then we’ll be gentle with the pieces.”
That night, Lilly slept without fear for the first time in a year. And in the morning, sunlight filled the room, warm and unafraid, just like the life waiting for her—held steady by the woman who had never let go.
In Derry, Maine, in a quiet house near the edge of town, love did not fix everything.
But it made healing possible.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
Chapter 17: Quiet Places in Derry (Lilly Bainbridge & Veronica Grogan)
Summary:
In 1962 Derry, Maine, Lilly Bainbridge endures quiet bullying at school and retreats to hidden places to cope. Veronica “Ronnie” Grogan finds her there, offering comfort, reassurance, and understanding. As their secret relationship deepens, Lilly struggles with nervousness and uncertainty about her feelings, but Ronnie’s patience and kindness help her feel safe. A tender first kiss and a comforting hug affirm that Lilly is no longer alone, and that in the quiet corners of Derry, love can exist even when it must remain hidden.
Chapter Text
In 1962, Derry, Maine had a way of pretending nothing ever changed. The sidewalks still cracked the same way, the air still smelled like wet leaves and river water, and the town still expected its girls to walk straight lines and keep their heads down.
Lilly Bainbridge tried her best to do just that.
She kept her books pressed tight to her chest as she walked the halls of Derry High, eyes fixed on the floor. The whispers followed her anyway—snickers about her clothes, her quiet voice, the way she never quite fit. Some days the words stung more than others. On the worst days, she escaped to the bleachers behind the school, where the world felt far enough away to breathe again.
That’s where Veronica Grogan always seemed to find her.
Ronnie had a crooked grin and a confidence that felt reckless in a town like Derry. She wore her jacket slung over one shoulder and didn’t seem to care who was watching. When she sat beside Lilly, close enough that their arms brushed, Lilly’s heart always skipped.
“They didn’t get to you today, did they?” Ronnie asked one afternoon, her voice low but steady.
Lilly hesitated, then nodded. The words came tumbling out before she could stop them—what they’d said, how it made her feel small, how she wished she could disappear. Ronnie listened, jaw tightening, eyes dark with concern.
“They’re wrong,” Ronnie said firmly. “Every last one of them.”
Lilly looked at her then, really looked, and felt that familiar nervous flutter. Being near Ronnie made her hands shake and her cheeks burn, like she was standing too close to a fire. She didn’t know what to do with those feelings, only that they felt right and terrifying all at once.
Ronnie reached out, hesitating just a moment before taking Lilly’s hand. “You don’t have to face it alone,” she said.
The world seemed to hold its breath.
Lilly’s pulse thundered in her ears as Ronnie leaned closer. She barely had time to think before Ronnie’s lips brushed hers—soft, careful, like she was asking permission. Lilly froze for a heartbeat, then melted into it, the fear giving way to warmth.
When they pulled apart, Lilly laughed nervously, cheeks flushed. “I—I don’t really know what I’m doing,” she admitted, staring at her shoes.
Ronnie smiled, gentle and patient. “That’s okay,” she said. “We’ll figure it out together.”
She wrapped her arms around Lilly, pulling her into a hug that felt safe and solid. Lilly rested her head against Ronnie’s shoulder, breathing her in, letting the comfort sink deep into her bones.
For the first time in a long while, Derry felt quiet.
And in that quiet, Lilly realized she wasn’t alone at all.
Notes:
I hope you all like this story
If you guys like this story please feel free to let me know in the comments :)
*SINCE IT IS DECEMBER I'VE BEEN THINKING AND I AM GOING TO BE POSTING A CHAPTER A DAY FOR THE WHOLE MONTH OF DECEMBER SO Y'ALL WILL BE GETTING A CHAPTER EVERYDAY 🩷
*ALSO REQUESTS ARE STILL OPEN, IF YOU HAVE A STORY REQUEST, PLEASE FEEL FREE TO REQUEST YOUR STORY IN THE REQUEST SECTION!
ALSO THIS CHAPTER IS BEING POSTED ON DECEMBER 15TH, IT IS ALSO MY BIRTHDAY TODAY!!!!!