Kylie
Copyright© 2026 by J. Contorta
Chapter 4
Erotica Sex Story: Chapter 4 - 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 next morning, Kylie stared blankly at her locker door. Amid the usual clutter, a single folded slip of paper—identical to yesterday’s—waited. Her fingers brushed it, cold dread pooling in her gut. With trembling hands, she unfolded it. “Have fun at practice today,” it read, Harrington’s sterile font twisting the innocuous words into a venomous promise. She crumpled it instantly, shoving the paper deep into her pocket like a grenade pin.
In English class, Jameson’s smooth voice slithered through Shakespearean analysis. Kylie hunched over her notebook, sketching frantic spirals. Then Jameson paused, his gaze slicing toward her like a scalpel. “ ... Much like Lady Macbeth’s futile cleaning of imaginary stains,” he mused, eyes locked onto hers. His smirk widened faintly. “Some compulsion remains ... undeniable. Even amidst, he paused, letting the word hang, “convulsing guilt. Or perhaps,” he added softly, leaning on his desk, “a stolen climax buried deep.” Kylie flinched as if struck, her pen gouging the paper. The bell’s shriek was a mercy. She bolted from her seat, shoving past startled classmates, fleeing into the crowded hall.
Harrington materialized beside the gym doors like summoned smoke. Kylie froze mid-stride, her breath catching. “Going somewhere?” His voice cut through the locker chatter, low and intimate. She stammered, “I—I have to get to practice, Mr. Harrington.” He tutted softly, his hand closing around her bicep. “In here now,” he murmured, steering her toward a narrow janitorial closet. She stumbled as he shoved her inside, the door clicking shut behind them. Dank shadows swallowed them both, the sharp tang of bleach thick in the air. Harrington pinned her against cold metal shelves. “Are you wearing panties?” His breath warmed her ear. Defeated, she whispered, “Yes.” He chuckled, dark and soft. “Consequences require reminders.” His fingers dug into her waistband. “Drop your pants.”
Kylie obeyed mechanically, trembling fingers fumbling with her sweatpants’ drawstring. They pooled around her ankles. Harrington’s pocketknife flashed silver, its snick echoing sharply. He sliced through the delicate lace of her peach-colored panties, another favorite ruined, and tucked the damp fabric into his jacket. “Now, to help you recall...” He produced a small tube, unscrewing it to reveal icy-blue gel. Dipping two fingers deep, he coated them thickly. “Raise a leg.” She lifted her shaking leg, hooking her foot on a low shelf. His slick fingers dragged slowly over her mound, spreading chilling menthol. She gasped, muscles clenching—then cried out as he thrust one finger shallowly inside and pinched her clit hard, smearing it in gel. “Enjoy practice,” he purred, stepping back. The door opened, flooding the closet with hallway light before he vanished as Kylie scrambled to cover herself back up.
Inside the gym, Kylie limbered up desperately, stretching her hamstrings deeper than usual to distract from the icy burn searing her nethers. The menthol gel felt like frostbite layered over Harrington’s invasive touch, a cruel taunt masquerading as a “reminder.” Maya bounced over, adjusting her cobalt leotard straps. “Ugh, Coach Miller had us running sprints after beam drills!” she groaned, oblivious. “And guess what? Ezra finally asked me out! He wants to take me to that new pizza place Friday!” Maya beamed. Kylie forced a smile, relief flooding her at the mundane chatter—anything to drown out the phantom whispers and the frigid ache between her legs. “That’s ... great, Maya,” she managed, focusing on Maya’s excited blush instead of the lingering sting.
As Kylie took her starting pose for her floor routine—arms lifted, chin high—her gaze instinctively swept the near-empty bleachers. Harrington and Jameson sat side-by-side in the front row, Harrington’s arms crossed, Jameson leaning forward with predatory focus. Her breath hitched. The haunting Irish melody began, and Kylie launched into her sequence—a leap, a pirouette—but her landing faltered, legs wobbling. Coach Miller’s sharp bark sliced through the music: “Landing’s loose, Morgan! Tighter core!” Kylie stumbled into her next tumbling pass, the icy burn flaring violently with each impact. Her mind flashed to Jameson’s velvet voice praising her throat’s “cadence,” and she froze mid-cartwheel, crashing gracelessly onto the spring floor. Harrington’s smirk was a blade twisting deep.
When she looked up again, Harrington and Jameson were gone. Maybe I’m just imagining things, she thinks to herself. Coach Miller stormed over, her whistle bouncing against her chest. “Get up! Focus!” She jabbed a finger toward Kylie’s rear as she struggled to rise. “And tuck that butt tight—you’re flaring like a damn peacock!” Humiliation scorched Kylie’s cheeks hotter than the menthol’s bite. Jaw clenched, she shoved herself upright. She inhaled sharply, locking her trembling muscles. For the finale, she hurled herself into a double back tuck—landing hard, ankles jarring, but flawlessly vertical. The coach gave a curt nod. “Better.”
The locker room echoed with distant chatter. Kylie headed straight for the showers, locking herself in the farthest stall. Scalding water pelted her skin, steam billowing as she frantically scrubbed at her thighs. She rubbed viciously at the raw sting where Harrington’s gel still burned her skin, the menthol’s chill finally dissolving beneath the heat. Her fingers slid lower instinctively, brushing her pussy. A jolt of phantom sensation made her snatch her hand back like she’d touched fire. “No,” she hissed under the spray, squeezing her eyes shut. She rinsed faster, the water sluicing away suds and shame.
Wrapped in a towel, Kylie avoided the fogged mirror. She dressed quickly: sweatpants, hoodie, no underwear of course. At her locker, she grabbed her backpack, its familiar weight settling across her shoulders. As she slammed the metal door shut, her phone buzzed.
See you in 5 minutes
No sender name. No punctuation. Just those five words in sterile black font. Ice flooded her veins.
She knew exactly what it meant. Room 202. Oblivious students swirled around her, laughing, shouting, slamming lockers. Kylie moved like a sleepwalker through the current, feet dragging towards the science wing. The hallway grew quieter, emptier. The fluorescent hum intensified. Outside Room 202, she hesitated, hand hovering over the cold knob. Taking a shallow breath that tasted like chalk dust she pushed inside.
Harrington and Jameson leaned against opposite filing cabinets, bathed in the harsh overhead light. Harrington’s arms were crossed, Jameson cradled a mug of steaming coffee. Their conversation died instantly as she entered. Four eyes raked over her – Harrington’s sharp, assessing, Jameson’s hooded, lingering on the swell of her chest beneath the hoodie. “Ah, punctual,” Harrington stated, pushing off the cabinet. Jameson took a slow sip, his gaze never leaving her. “Remarkable recovery on that dismount,” Jameson murmured, his voice smooth as velvet. “Such resilience...” Harrington nodded curtly. “Competitive spirit, despite earlier ... distractions.” His gaze hardened. “take off your jacket.”
Kylie’s fingers trembled as they found the zipper of her hoodie. The metallic zzzzzip echoed sharply in the silent room. She shrugged the thick fabric off her shoulders, letting it slide down her arms and pool onto the floor beside the desk. Clad only in her leotard and sweatpants, the air prickled her exposed skin. She avoided their stares, focusing on the linoleum floor. Swallowing hard, she made her way to the desk. Her chest rose and fell in shallow, rapid breaths. Harrington’s shadow fell over her.
He caught her arm before she could lift herself onto the wood. “Not there today,” Harrington intoned. His voice was low, deliberate. He steered her away from the desk toward the center of the room. “Strength and stamina today,” he announced. “On your knees.” Confusion flickered across Kylie’s face as he pressed down firmly on her shoulder. Her gymnast’s muscles obeyed instinctively, folding her into a kneeling position. The cold floor bit into her knees through the thin leotard fabric. She knelt between them, head bowed, cheeks burning crimson. Her heart hammered against her ribs.
Shame scorched her neck and chest. She lifted her gaze slowly, cautiously. Harrington was unbuckling his belt with precise, unhurried movements. Beside him, Jameson mirrored the action, his fingers sliding smoothly over his expensive leather buckle. Kylie’s eyes widened slightly—a doe-like look of raw uncertainty. Harrington’s zipper rasped downward. Jameson’s button popped open. The sound seemed amplified, filling the room. Kylie flinched, dropping her gaze back to the floor. Her hands clenched into fists in her lap. Harrington cleared his throat. “Eyes up,” he commanded softly. “Pay attention.” She obeyed, forcing her chin up. Jameson’s smirk was faint, predatory. Harrington’s expression remained stern, detached. “The lesson,” Harrington murmured, his voice dropping to a gritty whisper, “is endurance.”
Kylie blinked rapidly as Harrington pushed his trousers and boxers down together in one fluid motion below his hips. Jameson followed suit, stepping out of his own pooled trousers. Twin erections sprang free—Harrington’s thick and flushed, rigidly pointing toward her face; Jameson’s longer, paler, pulsing faintly with each heartbeat. Kylie’s breath caught sharply in her chest. Panic flared, hot and blinding. She bit down hard on her lower lip to stifle a whimper. Tears welled instantly, blurring the obscene vision before her. She squeezed her eyes shut instinctively, unsure what to do.
Jameson snorted, a harsh, dismissive sound. “Get your hands up here, stupid girl,” he snapped down at her, the cultured eloquence entirely vanished, replaced by cold authority. “I know you can’t wait to get your slutty mouth around our cocks, but that’ll have to wait.” The sudden shift—the crude word slicing through his usual velvet tone—jarred Kylie. Her breath hitched, tears spilling over onto her cheeks. Tentatively, she opened her eyes as she raised her right hand, fingers visibly trembling. Her arm seemed impossibly heavy. She’d never willingly touched a penis before. Slowly, hesitantly, she reached toward Jameson’s erection—the closest one hovering inches from her face. Her fingertips brushed the hot, taut skin, flinching away instantly as if burned. “Slowly,” Harrington murmured, his own gaze fixed on her trembling hand. “Softly. Grip it.” Kylie obeyed, forcing herself forward again. Her slender fingers wrapped tentatively around Jameson’s shaft. The heat shocked her. The texture—soft skin over rigid hardness—felt alien, terrifying.
Kylie felt paralyzed, focused solely on the terrifying heat and pulse beneath her trembling right hand wrapped around Jameson. A soft, choked sob escaped her lips. “Put that other hand to use, Kylie,” Harrington’s stern voice cut through her haze. “Grab my cock.” Her left hand jerked upward instinctively. Her gaze flickered wildly between Harrington’s stern eyes and the thick, flushed shaft inches from her cheek. Her knuckles were white where she gripped Jameson. Slowly, achingly, her left hand lifted. Her fingers stretched out. The tip of Harrington’s cock bumped against her palm. She recoiled slightly. “Now, stroke us,” Harrington growled, the command uncompromising. Kylie gasped, squeezing her eyes shut again as she curled her fingers around the base of Harrington’s erection with bruising force, a reflexive clench born of fear, not control. Both men groaned softly, Jameson a low rumble, Harrington a sharp intake of breath, as her trembling hands held their rigid flesh, the gymnast’s grip strong and desperate.
She didn’t know what to do. Instinct screamed to pull away, but Harrington’s unspoken threat, the footage, her father’s rage, locked her bones. So she froze, fingers rigidly encircling them, trembling violently like a trapped bird straining against a cage. “Move,” Jameson hissed, his velvet voice replaced by icy impatience. “Jerk us off. Pretend you’re churning butter.” Panic clouded Kylie’s mind. She’d never done this before. Never touched a man like this. Her hands clenched tighter, knuckles pressing painfully against the shafts, and then she began to wiggle her wrists rapidly back and forth—a frantic, meaningless tremor transmitted through her stiffened fingers and palms. It felt like trying to shake off a spider clinging to skin. Harrington’s groan turned into an exasperated sigh. “Stop that,” he commanded sharply. “You’re not polishing a trophy.” Kylie froze again, breath catching. “Stroke it,” Harrington instructed, his tone shifting to unnerving calmness. “Up and down. Slowly. Use your whole hand.”
Tears tracked silently down Kylie’s cheeks as she forced her fingers to relax their death grip. She focused on Harrington first, sliding her left palm slowly up his shaft, the skin smooth and hot beneath her touch. She reached the swollen head, slick with pre-come, and shuddered violently. Then, she slid her hand slowly back down to the base, forcing her thumb to circle slightly where she’d gripped before. A low groan escaped Harrington. “Better,” he murmured, his gaze fixed intently on her face. She repeated the motion—up, down, tentative yet deliberate—on Harrington. Then, shifting her focus with agonizing slowness, she mirrored the motion on Jameson with her right hand: a slow upward glide, fingers brushing the sensitive ridge beneath his head, followed by a trembling descent back to the base. Jameson drew in a sharp breath, his hips pushing subtly against her fist. “Consistency,” Harrington urged softly. “Maintain the pace.” Kylie’s arms ached, her shoulders burning with tension, but she kept moving—slow, dragging strokes, her hands sliding up and down their lengths in a clumsy, terrified rhythm.
Jameson watched her glistening hands work, her knuckles white despite the gentler motion. “Spit,” he commanded abruptly, his cultured voice utterly devoid of warmth. Kylie flinched, her strokes faltering. “On them,” he clarified coolly, nodding toward his shaft held loosely in her palm. “It’s pretty dry.” Humiliation scorched Kylie anew. Harrington’s gaze remained fixed on her parted lips. Gathering saliva felt impossible; her mouth was desert-dry. She forced her tongue against the roof of her mouth, gathering what she could. Leaning forward slightly, she spat weakly onto Jameson’s cockhead—a small, glistening blob landing near the tip. “Again,” Jameson demanded, unmoved. “More.” Kylie did so, leaning closer, spitting more forcefully onto the shaft Harrington held. The saliva dripped down. “Now keep stroking,” Harrington ordered, his voice thick. “Use it.” Kylie obeyed, squeezing her eyes shut against the shame as she resumed the jerking motion on both of them, her wet palms now sliding more easily—and sickeningly—over their hardened cocks, the slick sounds filling the silent room. Kneeling between them, she jacked them off, her slender gymnast’s arms moving mechanically, tears dripping silently onto the cold linoleum floor beneath her knees.
Harrington’s voice cut through the rhythmic sounds. “Kylie,” he murmured, “Have you ever given a handjob before?” Kylie’s heart slammed against her ribs. She shook her head frantically back and forth, her cheeks flushing crimson. “No, sir,” she choked out, her voice barely audible. Harrington’s lip curled in a dismissive smirk. “It shows,” he stated flatly, his gaze hardening. “Clumsy grip. No rhythm. Embarrassing.” The words landed like blows. Jameson chuckled darkly beside her, shifting his weight slightly, his cock pulsing hotly against her slick fingers. “Fix it,” Harrington demanded coldly. Before Kylie could react, his hands descended. He grabbed the high collar of her leotard and yanked violently downward. The sturdy fabric tore audibly, peeling away from her shoulders and chest until it bunched around her waist. Kylie gasped, her bare breasts suddenly hanging free, taut and vulnerable in the harsh light, her nipples hardening instantly against the chill air drifting through the room. She instinctively tried to hunch forward, but Jameson’s sharp “Keep stroking!” froze her movement.
Kylie’s arms burned as she kept moving—up, down—on both shafts, her exposed breasts trembling slightly with each jerky movement. Harrington studied her flushed face intently. “Focus,” he snapped suddenly. Kylie flinched, her rhythm stuttering briefly. Instantly, Harrington’s rough thumb and forefinger flicked sharply against her left nipple—a sharp, stinging snap that made her cry out softly. “Don’t stop,” Harrington growled. Kylie gasped, fighting back a sob, forcing her hands back into motion. The slick slide continued—Harrington’s thick shaft in her left hand, Jameson’s longer one in her right. She tried to steady her trembling arms, tried to find the monotonous rhythm Harrington demanded. But fear and uncertainty blurred her focus. Her pace slowed slightly. “Pathetic,” Jameson muttered. Kylie flinched again. This time, Jameson’s knuckle flicked out—a swift, hard tap against her right nipple that sent a jolt of sharp pain radiating through her breast. Kylie whimpered, tears streaming freely now. She clenched her jaw, her hands moving faster, harder, a desperate bid to avoid the next flick. “Consistency,” Harrington reminded her coolly, his voice thick with satisfaction. “Maintain it.” He watched her frantic motions, the flicker of pain in her eyes each time she faltered and earned another sharp sting on her hypersensitive skin. The cruel rhythm settled—strokes punctuated by stinging flicks—as Kylie knelt exposed, her hands working and her bare chest offering silent targets for their torment.
She squeezed her eyes shut tighter, blotting out the terrifying sight of them looming over her. All her concentration narrowed to the screaming ache in her shoulders, the trembling fatigue in her wrists, and the relentless, slippery glide in her palms. If she kept moving ... if she kept the pace fast and steady ... the sharp snaps against her nipples would pause. Her mouth hung slackly open, breaths shallow and ragged, tasting the stale air thick with cologne and exertion. Every tiny dip in her rhythm, every hesitation, brought another sharp flick—Harrington’s thumb or Jameson’s knuckle landing with precise cruelty on her tender buds. Pain bloomed fresh each time, hot and sharp, pulling choked whimpers from her throat. She poured everything into her arms—disciplined gymnast’s muscles recalling vaults and leaps—pushing through the fire in her shoulders. Faster. Harder. Keep the strokes smooth. Avoid the sting. Avoid the sting. Her world shrank to the motion of her hands and the fragile hope that compliance might end the torment sooner. Sweat beaded along her hairline, mingling with tears, running down her cheeks.
Suddenly, Harrington’s hand stopped flicking. Instead, his palm engulfed her entire left breast—rough and possessive—squeezing the firm flesh brutally tight as she stroked him. Simultaneously, Jameson’s fingers tangled sharply in her hair, holding her bun tight in his grip.
A thick, unfamiliar warmth pressed firmly against her bottom lip, nudging upward past her teeth. Kylie recoiled violently, her eyes flying open. Her hands froze mid-stroke on both cocks, fingers instinctively curling inward as she stared wildly down. Two. Only two shafts pulsed wetly in her palms. Yet, something hot and rigid pushed against her mouth. Confusion tore through her terror—a jagged bolt of disbelief as dhe dropped both hands instantly, jerking her head back sharply, her eyes flying open. Her gaze flew upward past Harrington’s sneering face.
Standing directly before her, where moments ago only empty air had been, was a naked stranger. His thick erection bobbed obscenely inches from her face, slick with her own spit. Kylie gasped, but unable to scramble anywhere as Jameson maintained his grip on her bun, the torn leotard bunching painfully around her waist. Her knees scraped harshly against the cold linoleum. “Ah,” Harrington chuckled darkly, releasing her breast to gesture lazily at the newcomer. “I see you’ve met Ben.” The stranger grinned, stepping closer, slapping his cock wetly against Kylie’s flushed cheekbone as she flinched away. “Our resident IT specialist,” Jameson added smoothly, his hand still twisted in her hair, preventing escape. “You can thank Ben for the clarity of your little video,” Harrington taunted, his voice dripping malice. “And for ensuring it reaches every admissions office, and your father ... should you disappoint us.”
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