Warden

A chilly winter breeze lapped at the windows of Warden Sloane Matthews’ office, breathing life into the silhouetted trees outside. She’d been the head of the Ravenmarsh correctional facility for over a decade and in that time she had overseen the successful rehabilitation of countless inmates. The key to her success was in a sacred, unspoken bond that she maintained with the prisoners, or at least the ones that took her fancy. Jason was one such inmate, a notorious gangster who had been convicted on three counts of armed robbery. He was precisely the kind of man that most people would cross the street to avoid. His tall, muscular body was decorated with a slew of elaborate tattoos to match his dangerous persona, and he sported a persistent angry grimace that could have frightened a ghost. He had caught Sloane’s eye the moment his first foot crossed the threshold into her domain. As was often the case, the sight of such a strong, powerful young man in shackles instantly had her salivating over the potential fun she could have with him. It was late in the evening and the various cell blocks had been cast into mandatory darkness, settling the prisoners like a brood of hens. She had called for Jason to be brought to her office and he arrived shortly after with a guard on each arm, dressed in a tangerine jumpsuit with his hands held out like a pauper. His wrists and ankles were cuffed and bound together by steel chains. They hauled him inside and placed him in the centre of her office before quickly making their exit and closing the door behind them. He gazed around at the finery of his surroundings, developing a conf
“Jason Carter…” Sloane addressed him, perching herself on the edge of her desk as she perused his file, “Armed robbery, grand theft auto, firearms offences… you’re a dangerous fellow to be around, aren’t you?”
“Unlock these cuffs and I’ll show you.” he grunted with a devious smirk. Sloane shot him a perplexed smile and shook her head in a disappointed, almost motherly manner. At 43, she was somewhat older and certainly more mature than the arrogant young buck that stood before her. She possessed an intimidating, authoritative persona that was emphasised by her striking blonde pixie cut hair and the black rimmed glasses balancing on the tip of her nose as she peered down towards him. She wore a tight, long black skirt that hugged her waist and clung to her thighs, highlighting the sublime curvature of her body from her bust to her knees. Her top to buttons flapped gently apart beneath the heating vent above her head, offering a tantalising glimpse of her cleavage to anyone who got close enough.
“Do you know why you’re here?” she asked, wondering if one of her other conquests had broken their vow of secrecy. Jason wasn’t the first man to be called to her office at such a late hour, and those who had been granted the privilege had been sworn to secrecy about what went on in that room.
“The shit you just mentioned…” he sneered. Sloane was most pleased. She had trained them well and the prospect of doing the same to Jason was making her itch with anticipation.
“Quite.” she responded bluntly. His brutish manner only made the knowledge of what was about to happen that much sweeter. He was completely oblivious to his impending fate and Sloane couldn’t help but chuckle as she placed his file down on the desk beside her. She moved closer and began to circle around him, draping the tips of her fingers over his shoulders to display her dominance over him.
“So…” he huffed, flinching slightly at the touch of her fingers, “Why am I here? I want to get some sleep.”
“Oh, don’t worry…” she grinned, coming to a stop directly in front of him, “You’ll be plenty tired by the time you leave here.”
She could see the mounting look of concern in his eyes and cherished it, feeding on his anxious frown.
“What’s that supposed to mean?” he replied, growing impatient with her games. Then, as she reached out and began to unbutton his jumpsuit, a knowing smile crept across his lips.
“Aahh…” he groaned with a sudden realisation, grabbing his crotch with his shackled hands, “You want some this…”
Sloane ignored his insolence for the time being, but made a note of every instance in her mind, ready for later.
“There’s something I’d really like you to do for me…” she explained in a sultry manner, quickly working her way down to the last button just below his waist. Seducing him was even easier than she’d expected, and she could hardly wait to introduce him to her very particular brand of discipline.
“Just say the word…” he answered, suggestively licking the air with his tongue. His eyes fell into the deep crevice of her breasts and lingered there while she fished a set of keys from her top blouse pocket and unlocked the shackles around his wrists and ankles. The metal clanged to the floor around his feet, completely liberating his arms and legs. They wouldn’t remain free for very long, though.
“Strip.” she commanded with a sharp nod. He gave her a cautious stare and proceeded to strip the simple orange fabric from his shoulders, allowing the whole thing to drop to his ankles. She flashed her eyebrows and nodded again towards his boxer briefs, compelling him to finish the job. He slowly pinched at the elastic and peeled them down, revealing his impressive, yet flaccid cock dangling between his muscular thighs. He bent down to remove his shoes and push the small mound of clothes aside, leaving him naked and far more vulnerable than he could have ever imagined.
“Your turn.” he winked, allowing his gaze to drop down over her incredible curvy hips. Sloane smiled and gave off an amused murmur, treasuring every second as her prey stumbled unknowingly into her trap.
“You’re going to do everything that I say.” Sloane explained, glancing up and down over the ripples and bulges of his impeccable stomach. She couldn’t deny that he was one of the fitter specimens she’d had in her office.
“Am I now?” Jason chuckled.
“Indeed.” she replied, collecting a stainless steel collar and chain leash from her top drawer. He watched with a mixture of burning curiosity and slight terror as she raised it up in to his neck, but didn’t resist even as she screwed it shut. It was a flat bar design, consisting of a single curved metal bar that only just fit around his tree-trunk neck. His every instinct told him to stop her, but there was something oddly hypnotic about her presence that kept him in check. The eyeful of her prominent cleavage had done much to quell his might, disarming him so that he was mere putty in her hands to meld however she wished. She had expertly planted the seed in his mind, convincing him that she wanted nothing more than a simple quickie with one of her strong, dangerous inmates. To him, the collar only added a kink factor and he couldn’t have known that her armoury of twisted devices went a lot deeper than a single metal hoop and chain. She tugged on the leash and guided him over to her grand oak desk, which she had cleared of all clutter in preparation.
“Sit back.” she said with a deceptive smile, “Let me take care of you…”
“This place isn’t as bad as I thought…” he laughed, sprawling himself back across the surface of her desk to rest on his elbows and he gazed down towards his stiffening cock. Sloane kept the leash in her left hand and reached out with the right, clasping his semi-erect shaft between her fingers. She began to stroke it up and down from the base to the tip, watching intently as he moaned his appreciation. A droplet of sticky pre-cum seeped out and smeared around the bulbous pink head as his foreskin rolled back and forth over it. His cock quickly firmed between her fingers and began to flex with every divine stroke that she gave him. The expert squeezing motion of her hand had massaged it to a full erection, and she couldn’t help but admire its beauty. She almost felt guilty for what she was about to do with it.
“Would you like me to put it in my mouth?” she teased, further seducing him and slowly bending him to her will. It was a small price to pay for the results it would achieve. His grin widened to a beaming white crescent and he nodded his approval, still glaring down beneath her top. Sloane moved around to the other side of the desk and placed her hand on his forehead, commanding him to lay even further back. Entranced by her beauty and the seductive peach blossom fragrance of her perfume, he lowered himself back onto the desk until his head dangled perilously over the edge. She rotated the collar around his throat and tightened the slack in the leash, leaning down to kiss him while she fastened the chain to a sturdy metal hoop that was bolted to the floor beneath her desk. Their lips stroked together upside down, distracting him just long enough for her to restrain his neck. She lifted herself away, leaving a few needles of warm saliva stretching between their lips. He tried to follow her for another taste, but the chain yanked on his throat and kept him securely in place.
“Heh…” he laughed nervously, moving his hand up to inspect the collar. Sloane immediately smacked his hand
“Good.” she said, easing another drawer open to reveal a set of four black leather cuffs. Each one was lined with soft black fur and featured a studded strap around the outside, with a D-ring to which she had attached small steel chains with triggers on the end. She took one out and began to wrap it around Jason’s left wrist, caressing his skin with the fur as she fastened it tightly and attached the trigger to a hoop at the far left edge of the desk. He was beginning to look restless, so she quickly repeated the procedure with his other wrist, shackling both of his arms to the desk with only an inch or so to move.
“What are you doing?” he grunted, alternating between states of confusion and aggression. Sloane shook her head with disapproval and fished out a black rubber bit gag and wedged it between his jaws. He tried to push it out with his tongue but his strength was no match for her determination. She fastened the strap around the back of his head, leaving the textured black spiral bar protruding from the sides of his lips and digging into his cheeks like a dog with a bone. She picked up the remaining two cuffs and waltzed around to stand in front of him. Noticing his temper, she reached out and took his cock in her hand again, jerking it and rubbing her thumb around the soft flesh just beneath the head to sedate him a little more. Predictably, his eyes wilted shut like she was injecting him with syrupy heroin, seemingly willing to sign away his life in exchange for a morsel of pleasure. She crouched in front of him and spread his thighs apart at the front of her desk. Then, she quickly fastened the two cuffs around his ankles and attached the connected triggers to a pair of metal hoops on the floor. Her desk was built for play as much as it was for work, and she could hardly wait to have her fun. He opened his eyes and watched as she collected a black leather zip-up case from her desk drawer and placed it on his chest. She began to peel the zip open, creating a bone-chilling hum that sent a shiver down his spine. He gazed down his chest out of the bottom of his eyes and winced as she pulled the case open, revealing a ruby red interior that housed a number of strange looking metallic devices. It was clearly a set of something, but he was clueless to their intended purpose. Each one consisted of a thin, wiry stem, with a bullet sized handle at one end and a series of increasingly large metal buds at the other, ranging from 1mm to 9mm in size. They were fashioned from surgical grade stainless steel and rested neatly inside the case in pairs of black fabric loops. Jason swallowed an anxious gulp and stared at Sloane, suddenly feeling overwhelmed and emasculated by her devilish laughter.
“Which one to pick…” she cackled as she ran the tips of her fingers over the steel buds. The stems jangled like piano strings, playing the song of his impending doom. He still didn’t understand what they were, but he suspected that whichever one she picked, he probably wouldn’t like it. Her fingers came to a rest on the third from the top, which held a bud measuring 3mm in width. It was only a tiny little thing, but to Jason it was about to seem a lot bigger. She slipped it out and set the case aside, allowing him gaze awkwardly down over his chest as she smeared the bud and the stem in a coating of lube. Then, she gripped his rigid cock in her hand and began to aim the tip of the device towards the bulging head. He immediately began to squirm in a vain attempt to evade it, but a sharp squeeze of her nails into the sides of his cock soon silenced his protests. She began to dab the tiny metal bud around the delicate opening of his urethra, gradually transferring some of the lube to make sure it was adequately coated. With the hole wet and glistening, she proceeded to slide the bud inside, splitting the sides gently apart as she pushed it deeper and deeper. Jason’s eyes bulged and his nostrils flared as he watched the spindly metal stem disappearing into his penis, but he was powerless to stop it – Sloane had made sure of it. She glanced up at him with a cruel smile and winked back at him. In that moment, he knew that submission was his only option.
At first it felt like the his cock was burning from the inside out, filling every blood vessel with a splintering pain that made him bite down hard on the gag. Every muscle in his body became tense as he heaved through wincing eyes, desperately trying to remain completely still so as not to rupture something. He couldn’t tell if his cock was turning numb or if he was simply acclimating to the strange prickling sensation, but as she inserted half of the stem into his throbbing penis, his muscles softened and his chest began to rise and fall once again. She maintained a gentle caressing motion with her other fingers, running them ever-so-softly up and down over the veiny bumps and ridges of his cock as she penetrated his cock over and over again. He was used to holding all of the power, so being restrained so severely and being subjected to whatever sex acts took Sloane’s fancy was anathema to him. It was the most uncomfortable, yet perversely arousing thing he’d ever felt and although his instinct was to resist, he found himself silently willing her to continue. Still, as she retracted the toy from his cock and selected the 5mm bud, the fear soon came rushing back.
She smothered it in another coating of slippery lube and aimed it towards his slightly gaping urethra. His cock remained as hard as ever, despite his best efforts to return it to its flaccid state. She nudged the new, slightly thicker bud into the hole, spreading it even further open so she could plunge it inside. Jason’s teeth began to form indentations in the bit gag as he chewed on it, groaning and squirming as much as he dared. He could feel the bud travelling deeper and deeper down the centre of his cock, spreading his urethral tract wide apart with vigorous force. Every firm flex of his cock caused it to press even harder against the tender tissue lining the walls, emphasising its size with every sadistic thrust. The fact that she seemed to delight in torturing him only added to the twisted thrill of it all. There was something oddly exciting about having the power stripped away. It was the most invigorating feeling he’d ever experienced, even though every surge of electrifying pleasure was matched by a sharp twinge deep in his groin. She pulled the toy clear of his cock and moved on to the 7mm option, repeating the same procedure while he lay helplessly on the desk. He howled as it burrowed into his penis and clenched his toes and fingers repeatedly as she mercilessly slid it in and out. His agony only compelled her to increase the force of her wrist, fucking his cock with the thick steel bud while she stroked the shaft up and down on the outside. Jason’s breath turned to an ecstatic quiver, inhaling tiny puffs of air in quick succession as she pushed him closer and closer to an orgasm.
Sloane could hear the sound of his anguished drone growing stronger and gave his left testicle a sharp, devastating flick with her finger to collapse the momentum before it could build any further. He yelped through the gag and tugged violently on the cuffs, but they kept him help down no matter how much he fought. She loved seeing such a powerful young man stripped of all his might, especially one that had shown such ill discipline. The act of bending a man to her will was the most exhilarating thrill she could imagine and it wasn’t the first time she’d done so. Jason was just one in a long line of now very obedient subjects for her to practice he deviant nature on. She grabbed the largest of the nine sounds and leaned over to tap the steel bud against his cheeks. He flinched sideways to avoid it, knowing that the worst was yet to come. She gave it a coating of lube and set it to work, splitting his pee-hole wide open to slide it inside just like the others. At almost a centimetre in diameter, it was a far more daunting prospect and the moment it entered his penis, Jason froze in place and didn’t move a muscle for almost a minute. She eased it down the middle, relentlessly pushing it deeper inside his aching cock until it had surely reached the base. Then, she left the stem protruding from the tip for a moment while she smeared her middle finger with some of the lube.
A startled jump snapped him out of his tense state as she pressed the cold, slippery finger between his parted buttocks. He felt it probing around the rim of his ass hole and baulked at the thought of it, squeezing his sphincter shut to block her passage. Sloane began to nudge the tip of her finger between the tight fleshy ripples of his ring, slowly but surely prising it open so she could slide it inside. He growled and kicked his heels against the front of the desk, but it was useless and he knew it. Her finger penetrated his rectum and began to stroke against the ceiling, quickly locating the walnut-sized bulge of his prostate. Jason’s disturbed frown soon transformed into a tormented yet oddly blissful smile as she massaged his g-spot with her expert touch. She knew precisely the right motion and pressure to apply to stimulate him and before long, any hint of resistance had dissipated from his body. He writhed on the desk and moaned softly as she continued to work the sound in and out of his cock while she fingered his ass. Every minute or so his cock would flex like he was about to cum, and each time she flicked his balls again, sending another searing pang shooting through his groin. She wondered just how much he could take and could have happily spent the entire evening keeping him balancing on the verge of an orgasm. However, there were far more ways for him to show his worth. From the moment she had inserted the first sounding bud, she had felt a slow trickle of moisture beginning to accumulate between her pussy lips. With him now fully restrained and responding like an instrument at her finger tips, her pussy was dripping wet and her clitoris throbbed so intensely that she could no longer simply ignore it.
The time had come for him to show his gratitude to her, so she retracted her finger from his ass and cleaned it off with a tissue. She left the sound sticking out of his cock and moved around to the other side of the desk to stand beside his head. His eyes were wet with delicious tears, though none had spilled over his cheeks yet. She leaned down above him, affording him a mouth-watering view of her heaving breasts tucked beneath her blouse as she unfastened the gag from around the back of his head.
“Show me that little tongue of yours…” she purred, leaning even closer with her fingers aimed like pincers above his lips. He cautiously extended his tongue just enough for her to get a grip between her sharp finger and thumb nails, and howled as they dug in to the soft, slippery appendage.
“This belongs to me now…” she said, squeezing it harder and harder until he shook his head to escape the pain, “Your cock belongs to me as well, and your cute little pink ass hole too.”
Jason simply nodded and pulled his tongue back into his mouth to suck the pain away. Sloane took a step back and allowed him to watch as she rolled the zip of her skirt down over the deep curve of her hip and along the side of her thigh. The fabric loosened from her waist and fell to the floor around her ankles, revealing her black lace-topped stockings and matching panties. She gripped the thin frills of lace at the edge of her knickers and peeled them down, allowing them to drop to her ankles so she could kick them away. Jason’s eyes immediately fixed on the thin strip of neatly trimmed pubic hair and the tight slit of her pussy descending between her thighs. She stepped closer and lifted her left foot off the floor, spreading her legs apart so she could straddle his dangling head. His cheeks bulged forward as her thighs clamped his head from both sides, keeping it locked in place as she lowered herself down on top of him. He knew his duty and obediently extended his tongue, still wincing at the prickly numbness left by her nails. Her labia split softly apart around the tip of his tongue as he licked between them, lapping up and tasting her sweet, sticky nectar. Sloane began to thrust against the pressure of his tongue, enjoying the slightly coarse texture of his taste buds slithering between her pussy lips and then lashing around her clitoris. A lustful smile spread across her lips as a satisfied moan drifted out from between them. The scent of her pussy was making his cock flex harder than ever, causing the protruding stem of the sound to swing back and forth above his crotch.
She leaned forward and lay atop his chest, still grinding her pussy on his tongue with her legs parted around his head. Her fingers could barely fit around the sides of his cock as she took it in her left hand and stroked it up and down, feeling it bulging with every gentle squeeze. She took the bullet-shaped handle of the sounding plug in her other hand and recommenced the deep, lubricated urethral insertions. The steel bud soared in and out of his penis with lightning force, but the initial discomfort had long since worn off and had been replaced by a strangely arousing tingle that continued to build in his groin. His hips rose softly off the desk as he clenched his ass cheeks, squeezing his prostate from deep within as she caressed his cock from the inside and out. The bulbous pink mushroom cap distended slightly around the bud as it plunged in and out, leaving a slow drizzle of excess lube spilling out over the top. She did it harder and faster, matching the relentless thrash of his tongue as he flicked her clitoris from side to side and lathered it in warm saliva. A chorus of hot, panting breath and elated moaning quickly filled the room as their bodies writhed together on the desk. The pressure of his crotch thrusting against his mouth left his head bending painfully down against the back of her desk, but she didn’t care. The only thing that mattered to her was the intense throbbing swell deep in her groin as she inched closer and closer to an orgasm. She could feel it rising with the steady, unstoppable pace of a juggernaut rushing towards her. It was the sudden groan from Jason’s gaping lips that finally tipped her over the edge, though not before she could whip the sound free of his cock and watch as his hot, milky load erupted from the tip.
Lashings of white, gooey cum spewed like magma over the sides of his cock, helped on its journey by the slippery coating of lube lining the walls of his urethra. Sloane could feel the sticky warmth of it drenching her hand and continued to jerk it until the last drop had spilled out. Her hips began to spasm in a fit of violent, uncontrollable orgasmic convulsions, brutally smashing her pussy against his face. All he could do was lay there and continue licking, diligently massaging her clit with his tongue until the very end. Her back arched up, causing her breasts to squeeze so hard against the inside of her blouse that a button popped off and shot across the carpet. Her cleavage wobbled chaotically beneath her bra as she wailed in ecstasy, feeling one overwhelming tingly rush of orgasmic bliss sweeping over her after another. Her legs trembled beside Jason’s face, gently smacking his cheeks from either side as he snacked on her pussy and licked up every drop the juices seeping from her engorged pink vulva. Then, with a frantic gasp, she collapsed on top of him and lay there twitching for a few minutes, slowly reclaiming control of her breath as his chest rose and fell gently beneath her. Eventually she managed to peel herself up from the glistening mountainous ridges of his body and mopped the sweat from her brow with a handkerchief. Then, she got dressed and fixed herself in the mirror hanging from the wall behind her desk.
Even with his balls completely emptied, Jason couldn’t help but gaze longingly at the curves of her ass beneath her tight skirt. He was completely spent, but he would have happily done anything to please her, no matter how much it hurt. Much like the other men that had entered her office at that hour, he had developed a sudden and inexplicable urge to satisfy her. However, as he watched her collecting another toy from her desk, he suspected that he would soon come to regret his newfound devotion. Sloane lifted out a stainless steel cock cage and moved around in front of him. It featured eight studs on the inside of the cage for heightened excitement and came with a chastity ring and padlock to keep it securely attached to her subject’s cock. With his arms and legs still bound in leather shackles, he was powerless to resist as she enclosed the steel ring around his balls and attached the cage around his limp penis. She slotted the metal pin between the two pieces and fastened them together with the padlock. Then, she released the shackles and removed the collar from his neck, allowing him to stand on his jellified legs for the first time in what seemed like an eternity. He glanced down at the cage and tested it with his fingers, feeling his heart plummeting to his stomach as he realised how secure it was.
“How long?” he whimpered, unable to raise his eyes to look at her.
“Until I next have use of you…” Sloane replied with a callous nod to his orange overalls. He collected them from the floor and quickly got dressed, pressing his wrists and ankles together ready to be shackled once more. She had trained him well and he clearly showed promise, but time would tell whether he had it in him to truly serve her. She had an entire menu of convicts to torture and claim for her sadistic pleasure, but she had to admit that he had quickly entered near the top of her list. He had certainly made an impression and as she watched him being escorted away to rejoin the prison populace, she couldn’t wait for their next encounter.