Chapter 4: The New Wardrobe
The black mini-skirt was a second skin, a sleek, constricting hug that ended high on her thighs. The sheer white blouse felt like a whisper against her skin, the delicate fabric doing nothing to conceal the dark circles of her nipples or the heavy swell of her breasts. She stood in front of the full-length mirror, a stranger reflected in the glass. The heels—strappy, black, with a thin, punishing stem—added four inches she didn’t need and a wobble in her stance that felt like vulnerability itself.
She looked expensive. She looked cheap. She looked like a theory she was testing.
Her hands, palms damp, smoothed over the skirt, feeling the way it stretched taut across the rounded fullness of her ass. She turned sideways, watching the fabric pull. A flush crept up her neck. Three days away from the forum had been a silence filled with grinding teeth and textbook paragraphs that swam before her eyes. The digital noise had become a phantom itch. Now, dressed in the armor she’d bought online with the stranger’s money, the itch had a name.
She picked up her phone. The camera app was a familiar window. She angled the mirror, capturing the full length of this new creature—the long black hair falling over one shoulder, the blouse falling open, the skirt that promised everything, the shaky legs in their netted stockings. She posted it.
LeahChen21: New look. Who wants to see more?
She placed the phone face-down on her desk. The silence was absolute. She stared at her reflection, at the high color in her cheeks, the dilated pupils. She looked feverish.
The first ping was a gunshot in the quiet. Then another. A cascade. A deluge. She let them pile up for a full minute, a lifetime measured in frantic vibrations against the wood. She turned the phone over.
(87) notifications.
The first comment loaded. Fuck, that ass in that skirt. Bend over and show me what's underneath.
Her breath left her in a soft, shuddering exhale. The command was a direct current to her core. She didn’t hesitate. The authority she’d ceded was now her compass. She turned her back to the mirror, looked over her shoulder at her own wide, dark eyes. She bent forward from the waist, slow, letting the skirt ride up her thighs, up over the curve of her ass. The cool air hit the backs of her legs, the tops of her thighs. She reached back, hooked her thumbs in the waistband of the black lace thong—the same one from the first photo—and tugged it down just enough, exposing the lower halves of her cheeks, the deep cleft between them, the faint, shadowed hint of something darker at its apex. The lace dug into the plump flesh. She held the pose, her heart hammering, and snapped the picture.
The image was a masterpiece of implication. The expensive shoes, the ruined stockings, the expensive skirt shoved up, the lace and the yielding flesh. She posted it without a caption.
The forum erupted.
Comments scrolled faster than she could read. JESUS. I would ruin you. That ass needs handprints on it. Red ones. Pull that thong to the side, you teasing bitch.
Leah read the comment, the words ‘teasing bitch’ sending a jolt through her that wasn’t offense. It was recognition. He was right. A dizzying, electric warmth flooded her pelvis, a total-body flush that made the sheer blouse feel stifling. She was so wanted they were begging, their virtual hands reaching through the screen to take what she dangled.
“Okay,” she whispered to the empty room, her voice rough. She tapped the video recorder, propping the phone against her biochemistry textbook. The screen showed her from behind, bent over, the black skirt a ruffled halo around her waist. She watched her own reflection execute the command. Her fingers, trembling slightly, hooked into the lace at her hip. She pulled the flimsy fabric to the side, revealing the swollen, pink lips of her pussy, already glistening with a clear, slick sheen in the dorm light.
“See?” she breathed to the camera, her voice a husky thing she didn’t recognize. “Not teasing.”
But it wasn’t enough. A reckless, giddy power surged through her veins, hotter than the shame. She felt incredibly sexy and just so wanted. Her right hand, the one not holding the thong aside, lifted high. She brought it down hard on the exposed curve of her right ass cheek.
The crack was startlingly loud in the quiet room. A sharp, stinging heat bloomed instantly on her skin. She gasped, the pain a bright, clean line that cut through the fog of arousal. She did it again, on the other side, harder. Her flesh jiggled from the impact, the red imprint of her own hand flashing into existence, vivid against her skin.
A low moan escaped her as she spanked herself a third time, watching in the phone’s screen as the mark deepened. The sting reverberated deep into her core, clenching her empty cunt. She was so wet she could feel it dripping down her inner thigh, a hot, shameful trickle. She held the pose, panting, the thong strained to the side, her reddened ass on display, her slickness visible.
She stopped the recording. She uploaded the video without watching it. The notifications began to scream.
HOLY FUCKING SHIT.
SHE’S DRIPPING!
LOOK AT THAT RED MARK I WANT TO MAKE MORE.
Private messages bloomed like bruises. Payment alerts chimed. One hundred. Fifty. Another two hundred. The money was a numbing stream, a quantifier of her decay. But one name cut through the noise.
LordSinister: The red on your skin is pretty. The wetness on your thigh is prettier. You’re finally being honest. Now stop playing with yourself. Go to the drugstore. Buy a toy. A realistic one. Seven inches. Thick. You know what to do.
Leah’s eyes locked on the words. Her throbbing ass, her aching, empty cunt, her trembling hands—all of it coalesced into a single, obedient tremor. The transaction was already complete. He hadn't sent money. He’d sent a purpose.
He’d sent a purpose. Leah straightened up, wincing at the pleasant throb in her cheeks. The sharp heat had subsided into a deep, radiating ache that pulsed in time with her heartbeat.
She didn’t clean herself up. She let the wetness cool on her thighs, a sticky, shameful proof. She glanced once more at the mirror, at the woman with the reddening handprints and the skirt around her waist. The blush on her face wasn’t from spanking. It was from the undeniable, humiliating thrill.
Her heels clicked a frantic, uneven rhythm on the linoleum as she grabbed her keys and a long winter coat. She shoved her arms into it, the coarse material a stark contrast to the sheer blouse, and belted it tight. It covered the skirt, the stains, everything. She was just a student in a coat.
The drive to the local sex shop was ten minutes of surreal silence. Every slight pressure of the car seat against her sore ass was a reminder. The dried, tacky feeling on her inner thighs itched. At a red light, she caught her own eyes in the rearview mirror. They looked hollow, glittering. She flipped the visor down and saw the faint, angry red welts peeking above the lace. A shudder ran through her.
“The Lion’s Den” was a nondescript storefront in a strip mall between a pawn shop and a laundromat. The neon sign in the window buzzed. Her hand hovered on the handle. For a full minute, she just stood there, breathing, feeling the cool air seep through her coat. She pushed inside.
A bell jingled. The air was thick with the cloying scent of synthetic strawberries and disinfectant. Racks of glossy costumes and packaged fantasies lined the walls. A bored-looking woman with magenta hair glanced up from behind a glass counter filled with vibrators. “Hey,” she said, her voice flat.
“Hi,” Leah managed, her own voice small. She wandered the aisles, her eyes skimming over packages labeled “GIGANTIC” and “TIGHT VIRGIN.” Her heart pounded. She felt monstrously out of place, a good girl trespassing. She stopped in front of a wall of dildos, silicone and latex versions in absurd colors and inhuman sizes. She felt a panic rising. None looked like the one in LordSinister’s command. Realistic. Seven inches. Thick.
“You look lost.” The clerk was suddenly nearer, leaning against the end of the aisle.
“I… just need a… a toy,” Leah stammered.
“First time?” The woman’s smile wasn’t unkind, just weathered.
Leah nodded, unable to speak. The clerk pushed off the wall and walked to a different section. She pulled a box from a shelf. “This is a good starter. Silicone, body-safe, decent girth without being intimidating. Realistic feel.” She handed it to Leah.
The box was heavy. The photo showed a flesh-toned cock, veined and curved, lying on black satin. It looked like it belonged to someone. The dimensions were listed: 7” x 1.8”. Exactly. Leah’s throat closed. He’d known. He’d known what she would find.
“That’s… perfect.” Her voice was a whisper. She clutched the box.
“Need lube?” the clerk asked, already moving. “You’ll want it. Water-based, silicone hybrid if you’re using it for…” She trailed off, eyeing Leah’s frozen expression. “For anything. Here.” She handed her a bottle. “Anything else? Nipple clamps? A butt plug?”
The words hung in the chemically-scented air. A butt plug. The untouched place. The virgin asshole. Her own photo flashed in her mind’s eye, the lace cutting into the cleft. Her heartbeat thudded in her ears. LordSinister’s voice echoed. Prep that sweet pussy for me.
The clerk’s eyebrow lifted just a fraction. She followed Leah’s pointed finger to a small display of anal trainers, shiny silicone in pinks and purples. The one with the delicate heart-shaped jewel glittered under the store lights, a childish, pretty little thing that promised gentle intrusion.
“Sure thing,” the clerk said, plucking it from the rack. “This is a petite. Good for beginners.” She placed it on the counter next to the dildo and lube, a trio of commitments.
Leah paid in cash, the bills from her forum transactions crisp and anonymous. The plastic bag felt impossibly heavy, swinging from her hand like a pendulum counting down her walk of shame back to the car. She drove home in a daze, the ghostly sting from her own palm whispering to her from the driver’s seat.
Back in her sterile dorm, she locked the door. The bag sat on her pilates mat, a dark blotch on the purple foam. She poured a glass of wine, needing the chemical courage. Her laptop sat closed, a sleeping beast. She knew he was waiting. LordSinister. The name made her clench inside.
She opened the bag, setting the items in a row on her bed. The flesh-toned dildo, veined and serious. The small bottle of lube. The petite, glittering plug. It looked like a ridiculous piece of costume jewelry. She drained the glass, the warm buzz starting to blur the sharp edges of her shame. She quickly poured another. Her phone buzzed. A direct message.
LordSinister: Show me what you bought.
Leah took a shaky picture of the three items lined up on her pale blue duvet. She sent it.
His reply was immediate.
LordSinister: Good. Now set up the camera. I want to see you use the big one first. Get that cunt nice and ready.
Leah stared at the command on her screen. Her hands felt cold. The wine spun a lazy, careless warmth in her head, but beneath it sat a cold, hard ball of fear. The dildo looked monstrously large laid out on her bed, a pale, veined imitation that promised to split her open.
She typed, her fingers unsteady.
LeahChen21: It’s really big. I don’t think it will fit.
The reply was instantaneous, a slap.
LordSinister: Yes you will. Your tight pussy is begging for it. You’re dripping just looking at it. Now set up the camera. Show the forum what a good little slut you are when you’re given proper instructions.
The words ‘good little slut’ coiled in her stomach, warm and dreadful. He was right. A fresh pulse of wetness seeped from her, a humiliating confirmation. She fumbled with her phone, setting it to record on a stack of textbooks, angling it to capture the bed. She peeled off the skirt and the ruined stockings, leaving only the unbuttoned blouse. The red handprints on her ass were fading to a tender pink.
She unscrewed the lube, the sound obscenely loud. She squeezed a cold, clear glob onto her fingers and smeared it over the head of the silicone cock, watching it gleam. She hesitated, then poured more directly onto her own sex, gassing at the chill. She spread her lips with one hand, her breathing shallow.
“See?” she whispered to the unblinking eye of the camera, her voice thin. “I’m… preparing.”
Her other hand, slick and trembling, guided the broad, rounded tip to her entrance. It felt huge, an implacable pressure against her most tender flesh. She pushed, gently. Her body resisted, a tight, burning ring of denial. A whimper escaped her lips. She pushed harder, the blunt head starting to stretch her, to invade. The burn was immediate, a bright, whitening sensation that made her eyes water.
“Fuck,” she choked out, her hips twisting automatically away from the intrusion.
But she didn’t stop. She thought of the wine bottle, that first brutal stretch. This was more. This was precise. She bore down, swallowing a cry as the thickest part of the head suddenly popped past her tight entrance. The feeling of being forcibly opened was breathtaking. She stopped, panting, impaled just an inch, feeling her inner muscles flutter wildly around the foreign object.
LordSinister’s words were in her head. Your tight pussy is begging for it.
She pushed again, a slow, excruciating slide that forced a guttural moan from her throat. There was pleasure woven into the pain, a deep, shocking fullness that rubbed against something primal inside her. She watched in the phone’s screen as her hand worked, forcing more of the thick, pale shaft into her glistening, stretched cunt.
She watched in the phone’s screen as her hand worked, forcing more of the thick, pale shaft into her glistening, stretched cunt. Each inch was a burning conquest, a brutal remodeling of her insides. Her breaths came in ragged pants, her knuckles white around the silicone base.
It burned, a deep, internal ache that vibrated through her pelvis, but layered beneath the hurt was an intense, shocking sensation of fullness. Her body, traitorously, began to adjust, the sharp protest fading into a throbbing, profound stretch that touched places she’d never felt. She had it about halfway in and she already felt impossibly full, stuffed, her vision swimming with the effort.
“Oh god,” she whimpered, her hips making a shallow, involuntary rock. The movement sent a jolt through her, a spike of something that wasn’t quite pleasure but was devastatingly close. She swallowed hard, tasting wine and panic. She summons the strength and buries the dildo to its hilt and gasps. A raw, punched-out sound tore from her throat as the molded balls pressed against her, the entire thick, veined length now imprisoned inside her. She says, “Fuck I did it!”
Her voice was a shocked, triumphant whisper. She lay there for a moment, impaled, feeling her heartbeat in her cunt, around the invading object. The initial burn was softening, transforming into a dense, all-consuming pressure. She experimentally flexed her inner muscles and gasped again, a spark of pure, electric pleasure shooting up her spine.
“Fuck,” she breathed, this time with awe. She began to move, a slow, tentative withdrawal that made the textured veins drag exquisitely against her sensitized walls. The slick, wet sound was obscenely loud in the quiet room. She pushed it back in, less gingerly now, a moan escaping her parted lips.
She fucked herself with it, gaining a ragged rhythm, her blouse sticking to her sweaty skin. The camera captured it all: the desperate focus on her face, the obscene glide of the artificial cock, the way her entire body jerked with each thrust. She was chasing something, a release that felt different, somehow deeper and more punishing than anything her fingers could provide.
A notification chimed from her laptop, a discordant sound beneath her moans. Her eyes flicked to the screen. A private message preview glowed.
LordSinister: You take it so well. Such a good, hungry cunt. Now make yourself come on it. I want to see you lose control. Then clean it.
The command cut through the physical haze. She obeyed, her movements becoming frenzied, her free hand flying to her clit, rubbing frantic circles. The dual stimulation—the deep, bruising fullness and the sharp, focused friction—coiled the tension in her belly into a unbearable knot. “I’m… I’m gonna…” she chanted, her voice breaking.
The climax wasn’t a wave; it was a detonation. It ripped through her with a violence that arched her spine off the bed, a silent scream tightening her throat as her cunt convulsed in fierce, gripping pulses around the thick silicone. Tears leaked from the corners of her eyes. The sensations were too much, overwhelming, a seismic shift inside her.
Slowly, the tremors subsided. A profound emptiness followed, not just physical but cellular. She pulled the dildo out with a soft, wet pop, feeling suddenly and terribly vacant. She stared at it, glistening with her own spend, her mind blank. The camera’s red light still blinked.
Mechanically, she brought the toy to her mouth. She hesitated for only a second, smelling the sterile silicone and her own salt, before closing her lips over the head. She tasted herself—musky, bittersweet—as she cleaned it, her eyes closed, performing the debasement precisely as instructed.
She set the dildo aside, a spent thing. Her body felt used, gloriously and terribly ruined. She reached for her phone, stopping the recording. She uploaded the file directly to him, a raw document of her obedience.
His response was swift.
LordSinister: Good girl. I’m going to upload this to the forum and tag you
LEAH LOOKED AT THE MESSAGE. MORE WOULD SEE WHAT SHE DID. GRANTED, HER FULL FACE WASN’T PRESENT IN THE VIDEO BUT SHE SHOWED A RAUNCHY CARNAL SIDE OF HERSELF THAT WENT BEYOND SIMPLE PICS AND VIDEOS OF HER PUSSY AND ASS. THIS WAS HER FUCKING HERSELF—the raw, unedited mechanics of it, the sounds of her struggle and her choked-off moans, the precise moment her body surrendered to the artificial cock. It was a documentation of breakdown. A cold wave of nausea washed over the lingering heat in her belly.
Her laptop chimed, a soft, poisonous sound. A notification appeared in the forum thread, tagged for her: @LeahChen21. He’d done it. The title he gave it was just two words: Obedience Training.
She clicked.
The video loaded, her own naked body filling the screen, the pale dildo slick and urgent. The comments unfolded below in real time, a ticking counter of her exposure.
FUCK ME SHE TOOK THE WHOLE THING.
listen to those slutty little cries.
I just came watching her clean it off. $50 sent you whore.
Her face burned. Her hands trembled. Another payment alert chimed on her phone. Then another. The money was a cold, numerical applause for her performance. She could see the view count climbing, three digits, then four. Strangers were watching her come apart. They were watching, and paying, and wanting more.
LordSinister DM’d her again.
LordSinister: They love you. Now they’re hungry. The little plug is for your ass. Use the leftover lube. Get it ready for me.
Her eyes darted to the glittering heart-shaped jewel on the nightstand. It looked absurd, innocuous. The wine-fueled courage had curdled into a thick, metallic fear in her mouth. That place was not a place. It was a boundary. She thought of her own photo, the lace cutting into the cleft, the untouched hole beneath.
LeahChen21: I can’t.
LordSinister: You said that about the dildo. You can. You will. Film it. Or I take the video down and keep all the money they’re sending. You’ll be just another forgotten tease.
Her breath hitched. The money was proof. The video was proof. If it vanished, had any of it even happened? Would she just be Leah again, the girl her ex left for someone sleeker? The hollow ache answered for her. It was a void that demanded proof of existence, no matter how degrading.
“Okay,” she whispered to the empty room. The word tasted like ash.
She retrieved the bottle of lube, the plastic cold in her hand. She repositioned the phone, her movements sluggish, drained. She lay on her side, knees drawn up, a clinical posture. Her fingers were clumsy as she squeezed more lube, the clear gel shockingly cold against the tight, nervous pucker of her asshole. She flinched at the touch.
“It’s… really tight,” she said to the camera, her voice hollow. Her fingertip pressed, just a tentative circle. The muscle resisted, a tight, defiant ring. She pushed, a sharp, insistent pressure. A gasp was torn from her as the very tip of her finger breached the outer ring, a burning, alien fullness that made her stomach clench. “Oh… fuck.”
She worked her finger, a shallow, brutal in-and-out that made tears spring to her eyes. It wasn’t pleasure. It was a violation she was orchestrating, a slow-motion puncture. She added a second finger alongside the first, the stretch a white-hot bite that forced a ragged sob from her throat. Her other hand flew between her legs, her fingers seeking her clit, pawing at it roughly, needing a distraction from the sharp, claiming pain in her ass.
“Does it hurt?” she panted to the camera, her face contorted. “It hurts. It’s so small. It doesn’t want it.”
But she continued, fucking herself with her own two fingers, stretching the virgin orifice until the burning subsided into a throbbing, full ache. She pulled her fingers out, shiny with lube. She grabbed the plug, the silicone heart cool against her palm. She pressed the narrow, tapered tip against her loosened entrance.
“Wait,” she breathed, her whole body tensing.
She pushed. The tip popped past the clenched resistance with a sickening, internal slide. She cried out, her back arching, as the widest part of the bulbous middle stretched her open with a relentless, burning pressure. It felt like being split. She shoved it harder, desperate to be done, until the heart-shaped base sealed itself against her, a full, intrusive presence lodged deep inside her. She collapsed onto the bed, panting, feeling stuffed in two places, profoundly and unnaturally occupied.
She stopped the recording, uploaded it to him directly, a document of her own defilement. She didn’t wait for his response. She crawled to the edge of the bed and vomited a thin, acidic stream of wine into her small metal trash can. Her body shook, the plug a constant, brutal reminder inside her.
Her laptop chimed endlessly. The forum was in a frenzy.
WHERE IS THE ASS VIDEO? DID SHE DO IT?
SHE'S A NATURAL SLUT.
$100 FOR A PIC OF THE PLUG IN PLACE.