Kylie
Copyright© 2026 by J. Contorta
Chapter 6
Erotica Sex Story: Chapter 6 - 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
Room 104 wasn’t tucked away; it sunk into the hallway near the rear of the school. Its sole window faced a brick wall inches away. Kylie traced her fingers as she entered along cold plywood panels—recently installed, judging by the raw sawdust scent. A few desktop workstations lined the far wall and the incessant buzz of electronics permeated the room. Piles of computer components lined the floor near the walls, as was always the case with IT. Kylie’s eyes moved around the room, noticing Ben spinning in a luxurious office chair in front of one of the workstations. “Ah, there she is,” he says as Kylie closes the door behind her.
A futon sat in the middle of the room, Kylie wondered why it wasn’t against the wall absently, as Ben stood up and moved toward her. He grinned, tapping his thigh. “Heard you’re my study partner today. Lose the uniform.” Room 104’s air tasted of damp concrete and ozone from humming servers. Kylie’s fingers trembled as she peeled her clothes downward, skirt catching briefly on her hips before pooling at her ankles. “We’re gonna try something new today ... Well, at least new for you, I’m sure,” Ben smirks as Kylie hugged herself. Goosebumps erupted across her skin, as she wondered what he planned to do. Before she could step free, Ben grabbed and pulled her onto the futon. She landed half-straddling him with a yelp, her heartrate thumping in her chest. Ben seized her hips, flipped her bodily upward until her knees bracketed his shoulders, her head hung low near his pelvis. “Perfect,” he breathed, guiding her thighs apart until her exposed pussy hovered inches above his mouth. “Show me how well you learned male anatomy.” He thrust his erection upward, nudging her lip, rubbing his cock on her cheek. “Suck.”
Kylie obeyed mechanically, opening her mouth just as Ben’s tongue plunged deep into her pussy. The dual sensations slammed into her: the hot, wet intrusion below warring with the thick intrusion filling her mouth above. Salty bitterness coated her tongue while his tongue flicked hard against her clit, relentless as a metronome. She moaned around his shaft. Below, Ben groaned against her flesh, the vibration humming through her pelvis. “Fuck yes, keep sucking,” he mumbled, breath hot against her inner thighs. Kylie hollowed her cheeks, bobbing her head clumsily, mimicking Harrington’s rhythm. Her jaw hurt from the new angle as Ben’s cock thrust up and down into her moist mouth. Every ragged inhale through her nose carried Ben’s musk mingling with a different scent, one which she realized was her own arousal—a reminder of her body’s involuntary betrayal.
Ben’s grip tightened on her hips, fingers digging into soft flesh as he pulled her pussy harder against his mouth. He devoured her cunt, sucking fiercely on her clit while driving his tongue deep inside. Above, Kylie whimpered around his cock, tears stinging her eyes. Pleasure coiled low in her belly—tight, terrifying, unstoppable. Her thighs began to shake uncontrollably against his shoulders. Each rough thrust of Ben’s hips drove his cock deeper, scraping her throat. “Guh—uh!” she choked, saliva dripping down her chin. Ben only growled, “Don’t stop, slut!” The command fused with the electric jolts radiating from her clit. Resistance dissolved. Her hips bucked, grinding against his face, seeking friction Ben eagerly gave. The orgasm tore through her, violent and shuddering. Her back arched violently; her scream muffled by his shaft as she convulsed, flopping like a ragdoll against his relentless mouth. Every spasm drove his cock impossibly deeper, triggering gagging sobs she couldn’t contain, but they were sobs of pleasure this time. The squirming girl above him drove Ben over the edge and he latched his fingers into her hair, driving upward south one final thrust. “Fuck yes, swallow it all,” he snarled. Hot spurts flooded her mouth and throat—salty, thick. She gulped frantically, choking down every drop while aftershocks trembled through her limbs. “Amazing,” Ben says as Kylie swallows.
Ben pushed her off him and rose from the futon, sighing contentedly. “Room 217, tomorrow” he murmured, as Kylie wiped her lips with the back of her hand. Jameson’s classroom, she thought. Ben was oblivious, sitting down and turning toward his monitor, as Kylie stood and pulled her clothes back on with shaky hands. Without a word, she stepped quietly toward the door. Once through, she sped down the hallway.
Jameson’s knuckles were white against the dark leather belt buckled around Kylie’s waist. The coarse leather dug into her hip bones, anchoring her trembling form on hands and knees on the floor of Jameson’s office. Of course, she was naked, except for the belt. Jameson knelt before her, one hand gripping her ponytailed hair vice-like and the other on the belt, holding it like reins. He shoved his cock deep into her mouth without preamble—a thick, brutal thrust that scraped her palate and triggered an immediate gag reflex. Tears blurred Kylie’s vision instantly. Above the frantic wheezing through her nose, Jameson’s voice rasped like gravel, “Yeah ... fuck my cock with your mouth.” The eloquent well-spoken man Kylie once knew was gone, replaced by a rough brute. He pumped shallowly at first, grinding against her lips, a smirk audible in his tone. Kylie’s jaw screamed under the relentless stretch, her saliva pooling thick and slick around the intrusion. Each retreat and slam forward dragged her hair painfully against her scalp. She tried to focus on the posters on the wall—Hamlet, Ray Bradbury, Herman Melville—anything to escape the bitter tang flooding her senses. Jameson releases the hand in her hair slaps her ass. She flinched—braced harder on her palms. “Tighter,” Jameson ordered sharply, grabbing her hair again as he pulled her bodily toward his groin. “Suck harder.”
He leaned forward, shifting his weight onto her skull. The angle forced her chin lower, her throat opening wider to accommodate him. Jameson’s thrusts grew frantic—short, jerking movements that scraped her throat raw. “Here it comes ... take it, bitch!” he choked out. Kylie recognized the tremor in his thighs pressing against her shoulders, the tightening grip on her belt. She hollowed her cheeks instinctively, creating suction, swirling her tongue over the swollen vein pulsing beneath the slick skin. She squeezed her eyes shut against the tears streaming freely now. The rhythm was brutal, unforgiving—the wet slap of skin against skin, Jameson’s ragged grunts, the muffled choking sounds escaping her own throat. She could smell his sweat mixed with stale coffee clinging to his shirt. His hips pistoned faster, driving deeper with each slam. Kylie swallowed convulsively around him, her throat muscles spasming in protest, trying to clear space for air. The first stream hits the back of her throat—hot, thick, and sudden. The coppery tang explodes across her taste buds, sharp and unmistakable. Jameson lets out a guttural roar, locking her head in place as his hips buck violently against her face. The thick flood pours into her throat, coating her tongue, filling her mouth with its viscous warmth. She gagged, her body convulsing, but his hand on the belt and her hair held her firm, grinding her face against him. “Swallow it ALL!” he snarled, punctuating the command with another brutal thrust. She gulped obediently, frantically, her throat working against the sheer volume and texture, tears and snot mixing with the salty mess dripping from her chin.
The hot water scalded Kylie’s skin as she slumped against the cold tiles later, the shower spray drumming rhythmically against her hunched shoulders. She hadn’t planned it; her trembling fingers just slid down her slick belly and pressed hard against her clit. Her touch was frantic, rough, devoid of finesse, driven by a desperate need to come, which Jameson had denied her. The water plastered her hair to her face, mixing with tears as she bucked her hips against her own hand, seeking friction on the slick porcelain floor. Each gasp echoed in the small space, drowned out by the roar of the shower. She mumbles “perfect” under her breath. She couldn’t stop—wouldn’t stop—until she felt that release she was denied. Her thighs trembled violently; her breath hitched in ragged sobs. The orgasm built like a tightening coil low in her belly, urgent. She pressed harder, circling faster. She wanted to scream Harrington’s name. She choked out “yes” instead. Her climax ripped through her—a searing, shuddering wave that arched her back off the tiles. It was sharp, brutal, and utterly devastating. She arched her back, hips thrusting wildly as she rode the waves of pleasure. Her thighs trembled violently, knees buckling inward as her hips rolled against her own palm. Gasping sobs escaped her lips, muffled by the spray. It left her gasping, shaking, curled fetal on the wet floor, water pooling around her.
That Friday, the fluorescent lights of Pinecrest High’s gymnasium buzzed like angry hornets overhead, casting harsh rectangles onto the polished floor where Maya bounced on the balls of her feet, her sequined leotard catching the glare. “Can you believe it? Regionals!” she hissed, adjusting the strap digging into Kylie’s shoulder, the green mesh fabric Harrington demanded feeling like barbed wire against her skin. Kylie forced a smile, her fingers trembling as she re-tied her hair bun—too tight, like a vise holding her fractured thoughts together. The scent of chalk dust and sweat thickened the air, punctuated by the rhythmic thuds of vaults and the tinny blare of warm-up music. Maya’s chatter blurred into static; Kylie’s gaze snagged on Jameson leaning against the far bleachers, arms crossed, his stare a cold anchor dragging her under while Maya chirped about Ezra cheering them on.
Maya scanned the crowded bleachers, her brow furrowed slightly as she rose onto her toes. “Where is he?” she muttered, chewing her bottom lip. “He promised he’d be front row for my vault.” Kylie tore her gaze away from Jameson’s predatory smirk across the gymnasium, forcing her attention back to Maya’s anxious fidgeting. She plastered on her brightest smile—the one that crinkled her eyes and hid the tremor in her voice. “Probably stuck buying overpriced nachos,” Kylie offered, her tone light as she adjusted Maya’s sparkly hair clip. “You know how concession lines get. He’ll be here.” Maya nodded, visibly relaxing, and turned so Kylie could smooth the shimmering powder across her friend’s shoulders. Their reflections shimmered side-by-side in the practice mirror: Maya radiant in purple sequins, Kylie rigid in forest-green mesh, both bodies honed for flight but anchored by vastly different weights.
Kylie began pacing instinctively—short, sharp strides that mirrored the frantic drumming of her heart. Her bare feet slapped against the cool vinyl floor, each step echoing the countdown in her head. An hour before it starts. Maya kept pace beside her, chattering about her beau’s favorite illusion flip, but Kylie’s focus frayed. Without conscious thought, her steps carried her further from Maya, edging toward the dimly lit corridor leading to the locker rooms, a sliver of shadow in the glittering chaos. Curiosity got the best of her, as she drifted toward the light, the harsh gym sounds fading into muffles. The corridor’s cold draft raised goosebumps on her exposed shoulders, a stark contrast to the overheated arena. Then, a low whistle sliced through the noise—a familiar, predatory sound. She froze. Harrington leaned against the lockers. “Come with me. Now.” His voice was a blade wrapped in velvet.
Further into the locker room, he handed her a blind fold and instructed her to put it on. She followed his orders and Harrington makes sure it’s snug and tight, double knotting it. He takes her by the hand and leads her through the school, down stairs, through corridors she didn’t know existed. The air grew colder and smelled of damp concrete and mildew. “Turn,” he commanded, guiding her into a space that echoed with dripping water.
They stood in a forgotten boiler room, illuminated by a single bulb. Steam pipes hissed like angry serpents coiled in the shadows. Harrington reached down and wrapped knee pads around her and lowered her to her knees with a hand on her shoulder, leaving Kylie kneeling in confusion. He mounted the stairs to a catwalk above, his footsteps echoing hollowly. “Stay put.” His command slices through the humid air. Kylie obeyed, trembling on the cold concrete, blind. She heard a door open and close nearby.
“I’m sure you remember our star?” Harrington says, his voice close again. Kylie sweeps her head back and forth, is he talking to me? Who else is there?! She thinks, panic rising urgently in her chest. “You expected Jameson? Ben?” Harrington chuckled somewhere above her as the footsteps stopped nearby. Kylie flinched as cold, familiar fingers brush her shoulder. Kylie’s breath hitched. She didn’t recognize the touch and tried to pull away. “Gentlemen, meet starts soon, so don’t take too long,” she heard Harrington murmur, “Remember, no hands, and keep it clean and quiet, our star still has to perform. Have fun” Gentlemen!?, screams Kylie in her mind, Oh no, this is it, they’re going to rape me.
Kylie had no idea who is in the room with her as three unknown men circled around her, the blind fold tightly obscuring her vision. They never said a word. Her hands reached out in front of her, trying to fend off any advances, as she yelped at imaginary movement. The damp air chilled her skin beneath the thin leotard, and the echo of dripping water amplified her shallow breaths straining the fabric. She flinched violently when a boot scuffs concrete beside her thigh, jerking her head away as if struck. Her fingers clawed uselessly at nothing, trembling so hard the knee pads rasp against the floor. Footsteps encircled her again, deliberate and slow, pressing closer until she felt body heat radiating against her shoulders. The silence stretched, thick with menace. Her imagination conjured Harrington’s smirk hanging in the darkness above.
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