Kylie
Copyright© 2026 by J. Contorta
Chapter 9
Erotica Sex Story: Chapter 9 - 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. This is more of a work of tribute to Dr. Wu than anything else as it was one of the first stories I loved a long time ago. If you don't like AI generated content, then don't read it.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft ft Mult Blackmail Coercion NonConsensual Rape Reluctant Heterosexual Fiction School MaleDom Humiliation Rough Spanking Gang Bang Group Sex Anal Sex Analingus First Facial Masturbation Oral Sex Petting Sex Toys Tit-Fucking Big Breasts Teacher/Student AI Generated
The blinds in Harrington’s office were blinds pulled tight against the afternoon sun. Kylie stood rigidly beside his desk, her feet planted on the cold linoleum. “Gymnastics season’s over,” he stated, flipping through a manila folder. “We can’t have our star getting soft.” He snapped the folder shut and tossed a plastic-wrapped bundle onto the desk. “Here get into these.” The crinkling plastic revealed a pair of black leggings—thin, seamless—and a cropped tee the size of a dishrag, the words “Girl Boss” emblazoned across the chest. Kylie’s cheeks burned. “Mr. Harrington, I can’t—” His hand cracked across her ass before she finished, silencing her with a sharp sting. “Did I ask?” Harrington spun his chair lazily, watching as she peeled off her uniform with shaking hands. The leggings clung to her like tape, the fabric digging into her freshly shaved mound. The shirt barely grazed her ribs, leaving her tits in danger of showing. She crossed her arms instinctively, her nipples hardening against her forearms. Harrington smirked, circling her slowly. “That’s great,” he murmured, dragging a fingertip up her exposed spine. “You’ll turn heads.”
Before they headed out, Harrington rummaged through his desk drawer with a rustle of papers. Kylie’s pulse jackhammered in her throat. His hand emerged gripping a sleek black remote, kind that looked like those used for presentations. He clicked a button experimentally; the motion made her flinch. “Bend over,” he ordered, his voice serious, indicating zero patience. “Hands on your ankles.” The position was familiar for Kylie—a gymnast’s stretch. She swallowed hard, then folded forward, her slender fingers wrapping easily around her ankles. The stretch pulled the leggings taut across her ass, the fabric straining against her cheeks. Harrington exhaled sharply. “Jesus,” he muttered, tracing the curve of her ass with a finger. The waistband pulled away from her skin as he peeled the leggings down, exposing her bare ass to the office air. Kylie’s breath quickened—her thighs trembled as she panicked—but she held position. “Easy, Princess,” he soothed, stroking a fingertip along her plush cheeks. The clinical touch sent an involuntary shiver up her spine. “I’m not going to fuck you.” Yet. The unspoken word hung between them.
Kylie’s knuckles whitened around her ankles as Harrington’s finger circled her asshole lazily—once, twice—the dry glide making her clench instinctively. He chuckled at her reaction, knowing this was a new sensation for her. She heard the crinkle of plastic as a package was opened, then a cool, smooth shape nudged against her bare pussy lips—smaller than she expected, tapered—as she gasped. Harrington ran it up and down her entrance, then pushed it in with a single practiced thrust, the intrusion burning despite its small size. Kylie whimpered, her thighs shaking, but the stretch faded quickly. The vibrator settled snugly inside her, inert for now. “Now we’re ready,” Harrington declared, patting her ass lightly before tugging her leggings back into place.
Kylie straightened slowly, her legs unsteady. The vibrator shifted inside her with every step towards the door—a constant, taunting presence. Harrington held the door open, his gaze dropping pointedly to her crotch. “After you, Princess,” he purred. Kylie ambled after him, the foreign presence making her strides awkward. Every movement tugged at her inner walls, reminding her of its presence as Harrington’s fingers brushed the remote in his pocket. The hallway stretched endlessly under flickering fluorescent lights. Kylie clenched subtly around the vibrator, testing its shape—sleek, egg-like, barely noticeable unless she moved wrong.
The gym’s automatic doors hissed open, releasing a wave of stale sweat and disinfectant. Kylie had never been here, as it was far away from where she lived, and she usually worked out at the school’s gym. Kylie hesitated before Harrington’s palm pressed firmly between her shoulder blades, propelling her forward. Eyes followed her instantly—men’s gazes lingered on her exposed midriff and the leggings that clung obscenely to her butt; women’s stares flickered between judgment and envy. A blonde in Lululemon whispered something sharp to her workout partner, who smirked. Kylie’s ears burned. Harrington guided her to an open mat near the squat racks. “Stretch,” he commanded, rolling his shoulders with ease. Kylie knelt then folded into a butterfly stretch—hips protesting as the vibrator pressed deeper. Her thighs trembled visibly. Harrington crouched behind her, his hands sliding up her back. “Deeper,” he murmured, fingers digging into her hips until she winced. Behind them, someone dropped a weight with a clang.
“Leg day,” Harrington announced as he rose fluidly. He selected two dumbbells, muscles flexing effortlessly as he performed lunges—his form impeccable, controlled. Kylie mimicked him with smaller weights, her first lunge ending in a choked gasp as the vibrator jostled against her pussy. Harrington’s lips twitched. “Again,” he ordered, adjusting her hips with possessive hands. She lunged forward—right leg bending, left extending—just as Harrington’s thumb grazed the remote in his pocket. A soft buzz ignited between her thighs mid-motion. Kylie’s knee buckled as she whimpered, but she caught herself on the rack, knuckles white after dropping the weights. The vibration intensified—not enough to overwhelm, just enough to make her thighs quiver with each rep. Sweat beaded along her hairline. Across the gym, a man in a tank top paused his set, staring openly.
Harrington leaned close, his breath hot on her ear. “Keep going, we’ve just started,” he murmured, clicking the remote higher. The vibrator pulsed sharply—once, twice—matching her lunges rhythmically. Kylie’s breaths turned shallow. Every downstroke sent pleasure skittering up her spine; every rise left her clenching the vibrator. Harrington watched her pupils dilate, her cheeks flush. “Atta girl,” he praised, palming the remote like a conductor. Nearby, a woman in yoga pants elbowed her friend, nodding pointedly at Kylie’s trembling form. Harrington smirked, increasing the speed subtly. “Almost there,” he lied, knowing full well he’d just begun.
By the time he mercifully clicked it off, Kylie’s shirt clung translucently to her chest, sweat-darkened fabric outlining every curve of her breasts. Her ponytail sagged, damp tendrils sticking to her neck. Harrington admired his handiwork—the way her nipples stood taut against the wet fabric, the shaky inhale she took when the vibrations ceased. “Cardio,” he announced cheerfully, steering her toward the treadmills by the small of her back. His fingers brushed the remote again. “Don’t worry,” he murmured, guiding her onto the nearest machine. “We’ll take it nice and slow.”
He programmed the treadmill deliberately—a deceptively gentle incline, a pace just shy of comfortable. Kylie gripped the rails, her thighs still quivering from earlier. Behind them, a cluster of men lingered near the water fountain, staring in her direction, their laughter carrying. Harrington leaned against the adjacent treadmill, arms crossed. “Hands off the rails,” he instructed. Kylie obeyed reluctantly, releasing her white-knuckled grip. The moment her palms left the plastic, Harrington’s thumb found the remote again. The vibrator whirred to life—low, persistent, like a mosquito’s buzz beneath her skin. Kylie’s breath quickened; her steps faltered. The treadmill belt slid beneath her sneakers. “Eyes forward,” Harrington commanded. “Posture perfect. You’re being watched.”
A bead of sweat traced the dip of her collarbone, vanishing beneath the damp fabric. Harrington tracked its path hungrily with his eyes. On the treadmill, Puppy’s tail flashed in Kylie’s memory—white, fluffy, bobbing obediently with every hard thrust. Harrington’s fingers twitched toward the remote’s intensity dial. Not yet. Let her wonder. Let her dread. The real game hadn’t even begun.
Kylie’s breath came in ragged bursts, her thighs trembling with each forced stride. The vibrator pulsed rhythmically—just enough to tease, not enough to push her over. Harrington matched her pace effortlessly beside her, his jogging form impeccable. His gaze slid sideways, drinking in the way her ponytail stuck to her flushed neck, the way her leggings clung to the dampness between her thighs. “Eyes forward,” he murmured, clicking the dial up a single notch. Kylie gasped, her knees buckling momentarily before she caught herself. The vibrator’s hum deepened, vibrating her clit now—relentless, clinical. Her arms flailed briefly for balance. Harrington chuckled. “Posture, Princess. You’re an athlete.”
The dial turned again—another incremental click, barely audible over the gym’s thumping bass. Kylie’s moan tore free unbidden, high and desperate. Her hands scrabbled at the treadmill’s console, knuckles white. The vibration intensified—sharp, focused, exactly where she couldn’t escape it. Her hips stuttered mid-stride, her body quivering. Across the room, the blonde in Lululemon whispered something to her friend, both sets of eyes locked on Kylie’s writhing form. Harrington watched her pupils dilate, her lips part around silent pleas. “Almost there,” he said, his thumb hovering over the dial. One more notch. Just one.
Her orgasm hit like a sucker punch—wave after wave of involuntary pleasure wracking her frame. Kylie’s knees gave out completely; she collapsed against the treadmill’s rails, her thighs clamping together instinctively as she came with a broken whimper. The machine’s belt sent her stumbling backward, her sneakers squeaking against the rubber, her tits bouncing wildly, but Harrington was there. He caught her effortlessly, pulling her upright and pulled her against himself. His lips brushed her ear, his voice dripping with mocking praise: “It’s ok, Princess.” Behind them, someone wolf-whistled. Harrington didn’t turn. He simply clicked the vibrator off, leaving Kylie shuddering against him. “Went too hard,” he said to no one in particular. Sweat plastered her hair to her temples; her leggings were soaked through—a dark, spreading stain impossible to miss. He guided her stumbling steps to the gym’s juice bar.
Harrington pressed a protein shake into her trembling hand—chilled condensation beading on the plastic. Kylie, face beet-red, choked down the chalky vanilla liquid, her throat working convulsively. He leaned against the counter beside her, surveying the room with detached amusement. “See that guy?” he murmured, nodding toward the water fountain where a red-faced teenager refilled his bottle. “He filmed the whole thing on his phone.” Kylie froze mid-sip, dread iced her veins as she tried to hide her face. Harrington chuckled, low and dark. “Drink up, Princess. What’s one more set of eyes?” His finger traced the remote’s dial meaningfully. Kylie gulped the shake, shuddering as the cool liquid hit her stomach trying to ignore the still lingering sensation between her thighs.
Outside the gym, afternoon shadows had deepened into dusk. Harrington tossed the car keys at Kylie. “You drive,” he commanded, sliding into the passenger seat. She stared blankly at the keys in her palm. Kylie timidly got behind the wheel, fingers trembling on the ignition. As the engine roared to life, Harrington leaned back, one hand casually clenching the remote nestled in his pocket. The dashboard lights cast hollows under his eyes. “Home, Princess,” he murmured. “Nice and slow.” His thumb brushed the dial. “Keep vibing.” The buzz reignited low and deep inside her. Kylie’s knuckles whitened on the steering wheel. “I can’t drive with that ... Thing ... It’s not s-safe,” she stammers. Harrington smiled darkly. “Then I suggest you focus.”
Her thighs trembled as the vibrator pulsed rhythmically—low at first, then sharper. Every stop sign, every red light stretched into eternity as she fought to keep her legs from jerking. Harrington lounged beside her, one finger tapping the window absently. “Left here,” he directed, just as he turned the dial up another notch. Kylie gasped, her foot slipping off the accelerator momentarily. The car jerked, tires screeching. Harrington tutted disapprovingly. “Careful,” he murmured. “Wouldn’t want an accident.” His thumb circled the dial lazily, intensifying the vibration subtly—just enough to make her grip the wheel tighter. Streetlights blurred past; her vision swam.
A sharp turn sent Kylie’s hip grinding into the seatbelt buckle, the pressure sending an unexpected jolt through her core. Harrington smirked, noticing instantly. “Almost home,” he said, his fingers tightening around the remote. Kylie’s stomach twisted—part terror, part unwanted anticipation. The vibrator buzzed faster now, mimicking the ragged pace of her pulse. Her fingers slipped on the wheel, damp with sweat. She felt it—the familiar coil tightening low in her belly, the pressure building relentlessly despite her silent pleas. Harrington watched her from the periphery, his breath evening out in quiet satisfaction.
The car rolled to a stop on the street down from her house just as the vibrator hit its peak—sharp, unrelenting waves wracking her frame. Kylie slumped forward, forehead pressing against the steering wheel, a choked sob escaping her lips. Harrington turned the keys in the ignition, the sudden silence deafening. He leaned in, his lips brushing her ear as she trembled. “Good job,” he whispered, fingers stroking the damp hair at her nape. Then, cold and clinical, he added, “Next time, maybe I won’t stop it.” Kylie shuddered, her body still thrumming with aftershocks.
“Pop it out,” Harrington commanded. His fingers tapped the glove compartment impatiently. Kylie hesitated—legs still sticky where the leggings clung—before reaching beneath the waistband with trembling fingers. The vibrator slid free with a wet sound, dangling from her grip like evidence. Harrington snatched it, tossing it carelessly into the compartment where it landed among pens and loose receipts. “Fix yourself up.” He jerked his chin toward the rearview mirror where Kylie’s reflection shows flushed cheeks and chapped lips. She swiped hastily at the sweat beading along her hairline just as the porch light flickers on.
The passenger door clicked open as Harrington stepped out into the cool night air. Harrington pulled Kylie upright out of the car and smoothed her clothes, palming her breasts. Kylie wrenched free as she stumbled toward the house with legs that barely supported her. Harrington’s low chuckle follows her up the steps. “Sweet dreams, Princess.”
The foyer rug scratched against Kylie’s feet as she toes off her sneakers, her mother’s chatter about reheated lasagna washed over her like static. She focused on the mundane—the chip in the baseboard, the loose thread on her sleeve—anything to keep from screaming. Her father glanced up from his newspaper, frowning. “You alright, kiddo? You’re shaking.” Kylie fisted her hands behind her back, forcing a laugh. “Just cold! Lots a sweet from the workout,” she muttered as she fled up the stairs. Upstairs, the shower ran hot—but no amount of scrubbing erased the phantom vibrations still thrummed beneath her skin.
Downstairs, her father laughed at something on TV. The sound is warm and normal, utterly detached from the reality that clawed at her ribs. Kylie turned the shower knob to cold, stepping under the spray with a gasp. The icy water shocked her skin into numbness, but her mind kept replaying the remote’s soft beep, the way Harrington’s thumb had circled the dial like he was adjusting a thermostat.
She emerged trembling and toweled off with mechanical motions. The leggings—still damp with sweat and other fluids—lay crumpled in the hamper and Kylie pulled on a set of oversized pajamas. She stared at the razor again before she tucked it carefully into her makeup case beneath tampons. A hiding place no one would check. The bed creaked as she collapsed onto it, every muscle aching. She counted the glow-in-the-dark stars on her ceiling—childhood remnants she’d never taken down. Thirty-seven. The house settled around her, quiet and oblivious. Somewhere across town, Puppy whimpered into a pillow. Kylie pressed her own face into the fabric and drifted off to sleep.