A modern retelling of a classic story from a time long past. Following in the footsteps of Tiffany Daniels, Kylie Morgan stars in her own story. In the end, it's a classic blackmail story within a modern setting. AI-assisted story telling. All characters are over the age of 18.

Chapter 11

The calculus textbook lay open on Kylie’s bed, its pristine pages mocking her as she doodled spirals in the margin, the same looping motion as a well-executed pirouette. Her phone buzzed against her thigh, Maya’s latest meme lighting up the screen: a cartoon kitten captioned, "When you realize it’s only Tuesday." Kylie’s thumbs flew across the keyboard, three laughing emojis and a "SO TRUE" sent before she could register the dull ache in her ass from Friday's "celebration."

Liam’s text bubble popped up next, "Movie this weekend?" and she bit her lip, imagining his lopsided grin. Her reply came effortlessly cheerfully: "Only if we see that new superhero one!! :D" Perfect punctuation, perfect excitement. No hint that she’d spent Friday night being anally gang banged. The phone slipped onto the comforter as she stretched, her thighs brushing together. No panties and hairless every day, their rule, and the fabric of her jeans rubbed just enough to remind her.

Maya FaceTimed unexpectedly, her smile glinting as she launched into a rant about their physics teacher’s pop quiz. Kylie giggled on cue, tossing her hair over one shoulder like always, but her fingers strayed to the hem of her shirt that riding up to reveal a fading bruise below her ribcage. She yanked it down fast, veering the conversation toward Sadie Hawkins dresses. "I’m thinking blue!" she chirped.

Her mom called from downstairs: "Dinner!" Kylie bounded off the bed with practiced pep, her ponytail swinging. Just a normal girl. Just a happy Tuesday. At the table, her little brother mashed peas into his forehead while Dad rattled off golf scores. Her mom slid a plate her way, extra greens, protein for the gymnast, and Kylie stabbed a carrot with gusto. "Coach says off-season prep starts next week, " she announced, voice bright. Her mom beamed across the table. Her dad nodded approvingly. Complete ignorance.

— --

At 3:15 Wednesday, Kylie hovered by the janitor’s entrance. Ben's SUV purred up, passenger window already down. "Hop in, Cinderella, " Harrington said. Ben's fingers drummed the gearshift as he idled. Jameson was already in the other seat when Kylie opened the back passenger door and slid into the back seat. "We’re going somewhere special, " Harrington murmured. The GPS showed 23 minutes to their destination. Jamesons' left hand settled on her knee, thumb stroking the inner seam of her jeans.

Once on the highway, Harrington twisted in his seat and tossed a crumpled Forever 21 bag to Jameson. "Upgrade time, " he said. Tiny shorts and tight tank top of course. Kylie took off her baggy shirt and Jameson ordered, "Arms up!" reaching back to unhook her bra one-handed while Ben navigated traffic. Cool air prickled her bare nipples instantly, goosebumps prickling her arms. "Why don't you show them your pretty tits?" Jameson told Kylie, indicating the car cruising next to them. Before she realized it, the window rolled down. Kylie tried to cover herself, but Jameson slid over and held her arms at her sides and pushes her against the door, forcing her to thrust her tits out. The man in the next car looked over, eyes wide, and pumped his brakes, disappearing from view.

Free from Jameson's hands, Kylie collapsed back into the seat, crimson spreading across her chest. Jameson tugged a tight spaghetti strap top over her head and shoulders. "Better, " he approved. Ben smirked at the rear-view camera. The shorts were worse; they barely covered her cheeks; the denim frayed at the edges to showcase more thigh. Every bump caused the shorts to ride up further, the frayed edges tickling her labia.

Kylie’s fingers dug into the vinyl seat as she attempted to discreetly tug the shorts downward. Ben caught the movement in the mirror. "Uh-uh, " he chided, reaching back to slap her wrist away. Harrington leaned over to tap the climate controls, goosebumps rising on Kylie’s skin as chilled air blasted her exposed crotch. The SUV’s leather creaked as Jameson shifted, his bulge straining against khakis while tracing her body with his eyes.

The off-ramp appeared abruptly, Ben taking the curve fast enough to make Kylie slide across the seat, jean shorts rasping against vinyl, tank top riding up to expose her navel. Jameson exhaled sharply through his nose, his fist tightening around the oh-shit handle above the door. Kylie stared at the passing shop signs. The GPS chimed cheerfully: You have arrived.

Harrington unbuckled first, his polished oxfords hitting the pavement with the same crisp efficiency as his classroom strides. He didn’t wait for her. Kylie scrambled out behind Jameson, the mall’s afternoon glare making her squint. The shorts, barely legal when standing, threatened to vanish entirely with each step. A cool breeze wicked through the flimsy top, hardening her nipples against the fabric like twin accusations. They didn't give her a jacket in the crisp autumn air. "I can't go in there, " she stammers haltingly, "Everyone will see me."

"That’s cute, " Ben remarked, nodding toward her chest. Harrington chuckled, gripping Kylie’s elbow to steer her toward a service entrance. "You do realize, " Jameson murmured against her ear, his breath hot, "That’s the whole fucking point." The metal door screeched open and Kylie’s bare thighs eased at the sudden temperature increase. Fluorescent lights hummed overhead, bleaching the empty corridor in antiseptic white.

Their footsteps echoed eerily in the vacant food court. A janitor buffing the tiles didn’t glance up as the group passed, their mop handles squeaking. Kylie’s pulse throbbed in her throat when a teenage employee pushing a rack of denim jackets finally noticed her, his Adam’s apple bobbing before he hurried away. Harrington palmed the small of her back, fingers dipping below the shorts’ waistband. "Relax, " he said.

They lingered at a sunglass kiosk, Ben testing mirrored aviators while Jameson traced the rim of Kylie’s ass with his pinky. The cashier, a woman with chipped nail polish, studied her inventory log extra hard. Harrington steered them next toward Victoria’s Secret, its pink neon buzzing audibly. Kylie’s flush deepened as mannequins in peekaboo lace bras loomed in the display. Her nipples tightened further against the cotton, visibly tenting the fabric.

Jameson hooked two fingers through her belt loop, tugging her inside with the ease of someone retrieving prepaid merchandise. Overhead speakers cooed a breathy pop song as Harrington ran his thumb along a satin garter belt hanging from a display. "What do you think, Kylie?" Ben asked, holding up a corset that wouldn’t cover half her ass. The salesgirl approaching them froze mid-step, backpedaling toward the register. Kylie’s thighs pressed together involuntarily, she could feel her own sweat smearing the denim.

"Look at that, " Jameson marveled, plucking at her taut nipple through the fabric. "She’s ready for the occasion, " as he pulled her toward the back of the store.

Harrington guided them toward the dressing rooms with a hand at the small of her back, too low, fingers pressing into the cleft of her ass through the shorts. "Our little mannequin, " he murmured in the dressing room with her. They had her try on a dark blue lace teddy. It clung to her frame like it was painted on, the lace detailing puckering around her breasts. Inside the cramped dressing room, Harrington exhaled sharply through his nose as he watched her wiggle into the matching thong, one hand braced against the mirror, the other gripping her hip to steady her. The leggings went on last, sheer enough to highlight every contour of her tones legs. "Breathe, " he reminded her, thumb tracing the waistband as it settled just below her navel. Kylie’s pulse hammered against his palm where it lingered.

"Out, " Ben ordered, rapping his knuckles against the frame. Kylie hesitated, just long enough for Jameson to yank the curtain aside. The cold air hit her bare thighs first, then the fluorescent glare of the spotlights. A sales associate dropped her clipboard. Harrington’s chuckle curled around her ear as he nudged her forward. "Five steps, then pivot, " he instructed, like coaching a runway model.

Kylie’s first step faltered, the leggings whispering against her inner thighs, the thong riding up with each movement. Ben’s low whistle cut through the music. "Arch your back, " Jameson commanded. She obeyed, feeling the teddy’s lace dig into her ribs as her breasts lifted. Two teenage girls froze by the panty display, mouths agape. Jameson’s hand settled between her shoulder blades, guiding her turn.

Ben seized her wrist before she got to the dressing room. "Upgrade time, " he said, dragging her into the dressing room behind him. In no time, he stripped her out of the teddy. The corset’s boning jabbed her ribs as he tightened the laces, each tug stealing breath. "Better, " he approved, thumbing her protruding nipple through the satin. The micro mini dress barely covered her ass, the hem fluttering when she breathed. Kylie stared at her reflection—barely recognizing herself.

The second catwalk began with Ben’s gentle push between her shoulder blades. Kylie stumbled forward, the corset forcing her posture into a pornstar’s exaggerated arch, tits bulging from the cups. She pivoted on cue, the mini dress flaring to reveal the garters clipped to thigh-highs. Harrington murmured something to Jameson, she only caught the word "ass." Her next step faltered when she saw the crowd forming by the entrance: mall employees, shoppers, a security guard with his arms crossed, all male. The dressing room’s curtain fluttered behind her, Ben’s shadow stretching long across the tiles as he followed with the discarded teddy dangling from his fist.

"Again, " Ben ordered. Kylie’s second pass drew whistles from a group of college boys lurking by the perfume counter. One filmed sideways on his phone until Harrington stepped into frame, to a chorus of awws. The corset’s lace dug deeper with each breath, she counted ceiling tiles to avoid meeting anyone’s gaze, flushing red again. A toddler pointed from his stroller before his mother jerked him away. Jamesons' fingers trailed up her spine as she neared the dressing room. The curtain’s metallic screech drowned out her whimper. Outside, someone dropped a coin into the fountain, a wish obviously.

Kylie braced against the mirror, watching Jameson lay out her next outfit. Black bustier with matching thong and another set of sheer stockings. He also held a pair of sharp stiletto heels in his other hand.

Kylie grimaced as she changed. "Do I really have to wear those?" she asked, nodding toward the heels. Jameson smirked and tossed them onto the bench beside her. "We want to see how you walk in them, " he replied. "So put them on."

With a reluctant sigh, Kylie bent down and strapped the heels onto her feet. They were high, taller than anything she'd ever worn before. Standing up, she wobbled slightly, gripping the wall for balance. The bustier squeezed her chest, pushing her breasts up and together in a way that made her feel even more exposed. The thong was practically nonexistent, just a thin strip of lace between her thighs.

"Ready?" Jameson asked, his tone mocking. He pulled the curtain aside without waiting for an answer, and she stepped out, her heels clicking against the tile floor. Every step was a struggle, her ankles straining, her thighs trembling as she tried to maintain her balance. The stockings hugged her legs tightly; the fabric sheer enough to see her strong muscles from years of gymnastics.

Harrington and Ben stood near the entrance of the dressing area, watching her with hungry eyes. Ben whistled low as she approached, his gaze locked onto her chest. "Damn, " he murmured. "Those heels make your ass look even better."

Kylie forced herself to keep moving, her face burning with humiliation. The bustier dug into her ribs, making it hard to breathe, and the heels forced her to arch her back in a way that thrust her hips forward. She could feel every eye in the store on her; sales associates, shoppers, even passing janitors slowing down to stare.

She completed the walk, pivoting unsteadily at the end before making her way back toward the dressing room. Her legs ached, her feet already sore from the unfamiliar posture. Just a few more steps. Just get back inside. Jameson leaned in, his breath hot against her ear. "Keep the heels on, " as she changes back into her shorts and tank.

The cashier's fingers trembled as she scanned the tags, three outfits, all lingerie, and heels, all purchased by the trembling girl in six-inch stilettos. Harrington pressed against Kylie's back, his hand guiding hers to enter the PIN. The receipt printer whirred. "What do you say to the nice clerk?" he asked Kylie while looking at the wide-eyed girl at the counter. Kylie's tongue darted out to wet her lips. "Th-thank you, " she whispered.

Ben scooped up the bags with a laugh, handing them to Kylie. The weight made her wobble, one heel skidding on polished tile. Jameson caught her elbow just before she fell, his grip tightening until her knuckles whitened around the bag handles. The mall's air circulation raised goosebumps as they neared the exit, every step echoing in the sudden silence. A group of construction workers by the fountain stopped mid-conversation, their coffee cups frozen halfway to their mouths.

Ben flung the door open with a theatrical bow. "After you, Princess." Kylie's next step faltered, the automatic doors' sensors beeping as she teetered on the threshold. Harrington's palm between her shoulder blades propelled her forward into the mall’s concourse. The bags swung against her bare thighs with each uneven step.

"Look left, " Jameson murmured. A minivan's worth full of soccer moms slowed to a crawl, one woman's manicured fingers tightening around her Starbucks cup. Kylie's heel caught a crack in the floor, Harrington's and Jamesons' hands the only thing preventing a face-first spill as they headed to another shop.

The boutique's LED lights threw kaleidoscope shadows across the dressing room's velvet curtains as Harrington selected the first outfit: a backless emerald wrap dress that would've made her mother faint. "Arms up, " Ben ordered, watching the fabric slither over her torso like oil. Kylie's fingers trembled at the waist tie, Harrington slapped them away to knot it himself, the bow resting directly over her crotch. The mirror showed too much thigh, too much collarbone, the slit climbing higher with every breath.

"Strut, " Harrington commanded, flinging the curtain wide. Kylie's stilettos sank into plush carpet as she stepped into the walkway, every head swiveling toward the sudden flash of bronzed leg. A middle-aged couple froze mid-argument over tie colors, the wife's mouth forming a perfect O. Kylie's pivot sent the dress flaring open to reveal her skin beneath, Ben's chuckle vibrated against her spine as he nudged her forward again.

“Green suits you, " Ben mused, thumbing the emerald fabric in his hands. He turned her toward the three-way mirror. "Tell us what you really think." Her reflection showed flushed cleavage, pupils blown wide with adrenaline. "It's... nice?" The words tasted like bile. "The color—" She swallowed hard, watching Harrington's smirk bloom in the glass. The dress did make her look regal, if royalty were bred for public consumption, every curve on display.

Jameson's chuckle ruffled the hairs at her nape. "She likes it, " he announced to the boutique at large. A sales associate pretended not to hear, folding tissue paper. Harrington steered Kylie into a spin, the slit parting to reveal her stockings. "Emerald's her color, " he agreed, fingers lingering where the neckline plunged. She wondered if they could feel her heart trying to escape her ribs.

The second dress came with instructions: "You’ll never need a bra with this one, " Harrington said, holding up a blush-pink bandage dress that looked two sizes too small. Kylie's breasts ached as Jameson yanked the zipper up her back, the spandex compressing her ribs until her nipples strained visibly against the fabric. She stumbled during her first pass, nearly kneeling a mannequin. Harrington caught her wrist, "Again, properly this time", his thumb pressing as he forced her posture straighter. The store manager adjusted his glasses, tracking her progress between racks of cocktail dresses.

By the third outfit, a sheer black mesh number with strategic sequin patches, Kylie's thighs burned from the heels' unnatural angle. Ben made her pause mid-walk, turning in slow circles for a trio of college boys lurking by the formalwear. One mouthed holy shit. Harrington peeled a damp strand of hair from her neck. "You're dripping, Princess, " he observed. The dressing room's velvet line walkway swallowed her whimper whole when she got back to it.

The salesgirl's clipboard hit the floor when Harrington demanded a fourth fitting, "Something white. Bridal adjacent." Kylie's knees actually buckled this time. Jameson caught her with a hand splayed across her back, fingers dipping beneath the mesh to trace her spine. "Almost done, " he said, as Harrington pulled a pearl-encrusted veil from the rack. Outside, a child asked her mother why that lady was crying.

The bridal consultant arrived clutching a garment bag like a shield. Kylie's vision tunneled on the zipper's teeth as it descended, revealing frothy white lace with corset ties. Ben made a show of checking his watch. "Places to be, things to do, " he reminded nobody, rattling car keys in his pocket, while staring at Kylie’s ass. Kylie reached for the dress with shaky hands. Harrington intercepted, unfolding the gown himself with ceremonial slowness.

"Last one, " Jameson promised, nudging her toward the curtain. His knuckles brushed the back of her thigh. Kylie stepped into the gown without being told, the satin whispering against her skin. The zipper's ascent was its own violation, each millimeter stealing what little free will she thought she had.

The mirror showed a stranger, pearls glinting at her collarbones, waist cinched to nothing. Jameson whistled through his teeth. "Wouldn't kick that out of bed, " he said, palming the train after her cat walk. Harrington adjusted a strap with mock reverence. "Almost too pretty to fuck." Ben's phone camera clicked, bright white burst against her pupils.

Kylie turned and fled into the dressing room, breathing hard. The white gown brought unbidden thoughts of her future. She struggled not to tear up as she shrugged out of the gown and back into her "street" clothes.

Kylie's heel caught in tile as they pushed her toward the register. The consultant's pen hesitated over the receipt. "Will that be cash or..." Harrington slid a black Amex across the counter. "Gift for my girlfriend, " he said, squeezing Kylie's hip. She stared at the security camera's red eye above the door, willing it to see her, really see, as the cashier bagged the emerald dress. The only one who saw the security footage was the store manager, who promptly deleted it from the computer after saving a copy to a flash drive.

— --

Of course, they all railed her ass when they got back to the school, spread her wide in the faculty lounge taking their turns. It was after hours, no chance of disturbance. Kylie grunted when the first cock entered her, her tight hole stretching to accommodate the girth. "That's it, take it like a good little slut, " Harrington murmured, gripping her hips as he drove in deeper. She arched her back, her breasts free for the others to see, the emerald dress they had had her change back into bunched up around her waist. The others watched, stroking themselves, waiting for their turn, as Harrington grunted and came inside her.

Jameson went next, flipping her onto her back and spreading her legs wide. He didn't bother with foreplay, just shoved in hard, making her gasp. Her heels, still strapped on, dangled over his back as he fucked her, the stilettos scratching his back each time her body rocked. Ben filmed it all, zooming in on her face, on the way her lips parted with each thrust. "Say you love it, " he ordered, and when she hesitated, Jameson pinched her nipple. "I—I love it, " she squeaked out, the lie tasting bitter on her tongue. She whimpered when his hands gripped her breasts roughly.

The final stretch came when Ben had her on her hands and knees, fucking her ass with long, slow strokes. Kylie was panting, head hung low, as he thrust deep into her core. In front of her, Harrington pulled her head up and lined up his cock, slick with her juice and still trailing semen, into her open mouth. "Open wide, " he commanded, tapping her head with his finger. She obeyed, her mouth stretching further open around him as he pushed in deep, her tears finally streaming down her face. Ben adjusted his angle and sped up. "God, you're perfect, " Harrington groaned, as he pistoned in her throat. For the first time, Kylie had two cocks inside her at the same time as she was spit roasted. Ben and Harrington timed their thrusts, both driving deep at the same moments, making her gag and clench rhythmically.

Jameson watched, stroking himself lazily. "You're a fucking work of art, " he muttered as she whimpered around Harrington's cock. Ben suddenly gripped her hips tighter, his thrusts gaining momentum. "Fuck, I'm gonna—" He didn't finish, just buried himself deep in her hole and came inside her rectum, his groan loud in the quiet room. Harrington followed shortly after, pulling out to paint her face with thick spurts. Kylie panted, saliva coating her chin as her body trembled from exertion and overload.

The men tidied up quickly, adjusting their clothes with casual indifference. Harrington smoothed his tie, glancing at his watch. "Dry cleaner closes at seven, " he reminded Kylie, indicating the dress still around her waist. Jameson clapped Ben on the shoulder, already laughing about some football game as they headed for the door. The latch clicked shut behind them, leaving Kylie kneeling in the afterglow of their violation, her body still thrumming from the forced penetration.

Slowly, she pushed herself up, wincing as semen trickled down her inner thighs. The faculty lounge mirror showed her reflection, mascara smudged beneath her eyes, semen smeared in her hair, white streaks glistening on her face. She reached for a box of tissues, dabbing at the mess with mechanical precision. The dress clung to her hips as she held it up in one hand as she tried to keep it out of the mess.

Why? The question circled in her mind as she wiped herself clean, the tissues sticking to her damp skin. She had done everything they asked, wore what they wanted, walked where they told her, even thanked the cashier like a trained doll. And still, they treated her like something disposable, a toy they could shove into any position before tossing aside. Her fingers trembled as she wiped a tear away, not just from humiliation, but from the ache pulsing between her legs.

The roughness was the worst part. Ben never eased in, always slammed deep on the first thrust, like he enjoyed hearing her grunt. Jameson pinched and twisted her nipples hard, grinning when she winced. She swallowed, pressing a fresh tissue against her sore entrance. They didn't even try to make me come. If they’d just been... gentler, maybe she could’ve pretended it wasn’t so bad and gotten off. Maybe she could’ve dissociated completely.

Semen leaked onto her thigh, still warm. She shuddered, grabbing another tissue. The clock above the door read 6:42 PM. Dry cleaner closed at seven. She scrambled into her shorts, wincing as the fabric brushed against her sensitive skin. The tank top stuck to her back, sweat or something worse. She grabbed the emerald dress after throwing on her hoodie, hoping the mess hadn’t smeared onto her clothes.

Outside, the parking lot lights hummed to life, orange pools flooding the asphalt. She dashed through the parking lot then stumbled. Fuck. A car honked, some asshole revving his engine as she crossed the lot. She flipped them the bird as he clutched the dress tighter, the plastic bag crinkling.

The dry cleaner’s bell jingled at 6:58 PM. The clerk didn’t look up from his crossword. “Next day pick-up, ” he droned, pointing to a clipboard. Kylie hesitated, the dress reeked of them, of her, of everything trapped in the fibers. The man finally glanced at her. His nose wrinkled. “You okay, miss?” She smiled, handed over the dress, and lied through her teeth: “Just spilled something on it.”