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Old 15-May-18, 23:46
MikeyG MikeyG is offline
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Default The Jailer Becomes the Jailed

Longtime lurker, first time poster. I’ve enjoyed how many excellent authors there are on this forum, and was inspired to write this based on a scenario I came up with. Hope you enjoy!

Midnight approached at the Clarksdale Women’s Correctional Facility. For Correctional Officer Jack Bennett, it was the best time to be on duty.

Jack had been an officer at the maximum security prison for ten years now (he corrected anyone who referred to him as a “guard” by saying guards worked at museums or banks). The facility was more than just a prison - it was the biggest employer in the remote desert town where he was born and raised. As jobs went, it wasn’t half bad for a guy like Jack: the prisoners could be a pain in the ass sometimes, but he never had anything to fear from them.

And there were certain perks to the job besides the health benefits and pension he was counting down to. While the pay wasn’t great, he made a lot of extra money selling contraband to the inmates. A single cigarette fetched $1 a piece. A plastic water bottle filled with discount vodka could earn him $40 if a prisoner had smuggled in a few twenty-dollar billls.

Of course, the prisoners had other currency to buy with too. There were a lot of former prostitutes, and women who had done sex for cash at some point in their life. In Jack’s experience, even those who were initially hesitant to exchange their services for a valuable piece of contraband could usually be persuaded without too much effort. It didn’t hurt that he was still a handsome guy not far removed from his varsity glory in high school. He had a confidence and swagger about him that elicited glances and banter from the women in the facility. There were plenty of prisoners who offered themselves to him freely, without even asking for a cigarette, drugs, or alcohol in exchange.

Jack was smarter than to engage in any relationship with an inmate that wasn’t transactional. Every sexual act was done using protection, and he was always sure to properly dispose of condoms himself so that the inmates never had any evidence of their transgression. Any sex act with an inmate was a fireable offense, and Jack had seen enough former co-workers get blackmailed by an inmate who kept the physical evidence of their time together.

He whistled to himself as he did his night rounds. Tonight he had pulled his favorite duty for the night shift: Administration Segregation, also known as Ad Seg. This was a modern equivalent to being sent to “the hole”, or solitary confinement. An inmate who refused to obey orders, who fought with other inmates or staff, or who was a danger to others was sent here. For Jack, though, this meant the Inmates in his unit were all kept in their own cells so there was no bickering to deal with, and since their cell doors were protected by thick steel and plexiglass he didn’t have to listen to any of them snore. All he had to do was perform a check once an hour, mark in his logbook that all prisoners were accounted for, and then he was free to do crossword puzzles, Sudoku, or read a book.

He peeked into the plexiglass window of each cell door window as he passed. At this time of night, all of them were asleep on their cots. The Inmates all knew the drill at this point, leaving their blankets down enough for him to see their face and confirm their identity (and that they were breathing) so he didn’t have to wake them up and force them to do this.

Jack smiled as he approached the next cell - this was the new home of Inmate Rhodes, his latest guest in Ad Seg.

Inmate Rhodes (Cecily was her first name, which Jack discovered after a little investigation into her file) was an anomaly at Clarksdale Correctional Facility. She was very well-spoken, although she kept to herself. She was tall, athletic, and most of all she was beautiful. It made her a target for the other women in the facility. While one might think that a woman like her would be victimized by the gangs, it was quite the opposite - Cecily Rhodes hadn’t just stood up for herself, but she’d hospitalized the last two Inmates who tried to make an example of her. No one knew where this skill came from - nothing in her file suggested she could possibly be a threat to others.

Jack was curious how a woman like Cecily ended up in a place like Clarksdale - she wasn’t a local, and had been sent from another maximum security facility from upstate where she’d been in similar trouble with the inmates. After researching her name on the internet Clark found information about her case, and learned of her history as a Black Widow who’d been prosecuted after her husband died under a mysterious illness that a coroner discovered was poisoning.

Jack slowed down as he got to the door, shining his flashlight through the window. The beam cut through the heavy darkness within the cell, illuminating Cecily seated, naked, in a lotus position on her bunk.

He was taken aback - the flashlight trembled in his hands. He gaped at the sight. Cecily’s thick, raven hair was down, spilling over her creamy white shoulders. The hair framed a heart-shaped face within which her blue eyes sparkled in the flashlight’s glow. Her heavy breasts seemed to defy gravity, hanging like orbs. Her nipples were hidden behind her black locks, and Jack suddenly felt the need to see what they looked like.

Cecily stared, unblinking, into the light. She smiled without making any move to unfold her legs. Her slender fingers remained curled over her pale knees.

Habit forced Jack to continue down the hall. He finished checking the other cells, confirmed all Inmates present, accounted for, and asleep. He logged his patrol into the logbook, his hand shaking just a bit as his mind raced with the wonder he’d just seen.

It wasn’t an accident, he decided - she would have heard his footsteps in the concrete hallway approaching her door. What’s more, she would have seen him pass the other way, first, before he made his way down the hall.

He had one hour until his next patrol to find out…

He carefully made his way back down the hall. This time he was quiet, sliding his feet carefully so as not to alert her or any other Inmate in his wing.

When he got to Cecily’s door he slowly peeked into the window. In the dim red glow of the cell’s prison-controlled night light he could see Cecily was still on her cot. Still in the lotus position. Still naked. Jack studied the soft outline of her features. Licked his lips - he didn’t even realize how dry they’d gotten.

“Can I help you, Officer Bennett?” She asked quietly. He could barely hear her through the heavy door. He hadn’t known she was looking back at him in the window.

His cover blown, he shined his flashlight into the window. She barely blinked, staring back at him.

“Inmate Rhodes, put your clothes back on,” he said, as forcefully as he could. As much as he enjoyed the sight, something about how cavalier she was being about her nudity bothered him - as if she was doing it to taunt him rather than to offer herself to him. If there was one thing he hated, it was games - especially from Inmates.

Cecily smiled wickedly. She still hadn’t moved from her lotus position. “Make me.”

Jack knew the smart thing to do would be to write up an infraction report detailing her refusal to put her clothes back on in the presence of a male officer, but a part of him wanted to teach her a lesson himself and remind her this was his wing tonight. She was supposed to listen to his orders, not the other way around.

“Are you scared?” she asked. “You don’t think I have a weapon hidden on me, do you?”

That was it - he grabbed the keyring. Unlocked the door. Slid it open as quietly as he could.

Her cell was immaculate, a light smell of disinfectant and soap lingered in the air. He quickly shined the light over the small area - confirmed everything was in order. Saw her state-issued uniform neatly folded beneath the steel cot.

Cecily was relaxed. She casually stretched her legs out. Flexed her toes. Jack gazed at the mound of black hair over her pussy.

“You want me to write you up? Looking at a loss of privileges for that,” he said, his flashlight tracing across her long, lean legs. Her skin glistened like porcelain in the light.

“It’s something about a Saturday night,” she said as she stretched. Her back arched - her breasts moved from under her hair - Jack saw the most perfect pink nipples standing erect over the luscious mounds.

“What are you talking about?” he asked.

“I never spent a Saturday night alone - not since high school. Not until I got here, anyway. You’re not gonna make me spend the night by myself, are you?”

Now she looked at him. Her lips were pursed, pouting. Yet her eyes weren’t playing along with the act. Jack could see they were like ice, staring coldly through him.

She traced a hand down her chest. Cupped one breast, lifting it slightly. Her fingers gently squeezed, tracing over her nipple. She moaned sweetly.

Jack forgot about her eyes. Forgot about the way she stared passively. His eyes were focused on her breasts. He was already erect inside his uniform pants.

He fumbled in his pocket. Pulled a wrapped condom from his wallet.

Cecily saw the foil wrapper in his hands. She shook her head, “Put that away. I won’t let you use it.”

Jack smirked. “What do you mean, let me?”

She laughed - he almost didn’t recognize the sound. He realized he was hearing what she really sounded like for the first time. “You don’t really think you’re still in control, do you?”

Her words stopped Jack. She was within reach, but he no longer wanted to touch her. He was no longer focused on her alluring breasts, or those shapely legs; for some reason he wondered now at what point her dead husband had realized he’d been poisoned.

Jack shook his head, trying to shake whatever spell she’d had on him. “Fuck you.” He turned for the door.

He barely heard her leap off the cot - she was on him before he could turn around.

She caught his right wrist and pulled his arm behind him as she drove him face-first into the wall beside the open cell door. For a moment he was too shocked to react - was this crazy bitch really trying to assault him!? He knew she was tall - nearly his height - but he outweighed her by at least fifty pounds, and he was a trained correctional officer on top of that.

He pushed back into her - she yanked his right wrist up, bending his arm behind his back at an unnatural angle. “Hold still. Don’t make me break your arm,” she said calmly.

He gasped in pain. She shoved him back into the wall. His face was pressed against the cold concrete. “Are you fucking crazy, bitch?” he growled. He reached behind him with his left hand, grabbing for a handful of hair to force her off him.

While still pinning his right wrist she jammed his thumb back. He howled in pain, spasming at the pressure point.

She kept him pinned to the wall. He felt her hot breath in his ear as she whispered, “Ssh, darling - what will the neighbors think?”

He couldn’t believe what was happening. His mind raced with a way to escape, but the pain pulsing up his forearm and elbow was overwhelming. He couldn’t help but obey her as she kept him still against the wall.

He felt her left hand fumble with his weapon belt. “Don’t move,” she commanded as she yanked the clasp. He felt the belt, along with his pepper spray, handcuffs, and two-way radio fall to the ground in a heap. If only he could get his hands on any of them, he could show his Inmate who was boss.

She suddenly released him - it was the moment he’d been waiting for! He knew he’d get the upper hand again after she got in her cheap shot. Now he wanted to show her what a mistake she’d made.

Knowing she was as tall as him he spun towards her, swinging his left fist out to catch her on the jaw. He knew it was uncouth to hit a woman, but he wanted to see the look on her face when she was put in her place.

She had anticipated this move, though, and was already ducked in a crouch. His fist sailed over her head. He cocked his right arm to punch down.

From her prone stance she shot her right fist out into his solar plexus. He felt the breath leave his chest. His knees shook, unsteady. His right hand dropped, clutching his belly as pain shot through his entire body.

Cecily lunged forward, driving her right shoulder into him. She drove him back into the wall. His head snapped back onto the concrete. His vision gave out for a split moment. As he pitched forward he was dizzy. His ears were ringing. He wobbly knees gave out completely.

She caught him over her shoulder, wrapping her arms around his legs. Jack had a shameful sense of helplessness as she somehow stood up with him draped over her shoulder. She didn’t even seem to have to exert herself to carry him. “I told you I was in control,” she said with a laugh.

His vision slowly coalesced. His arms hung uselessly, swaying above him as she carried him across the cell. His vantage point gave him a close up view on her perfect ass - her muscles pumped with each step she took. A split second of arousal gave way to fear as he realized his precarious situation. What was she going to do to him? He had the humiliated realization that she could do anything she wanted to him, given how helpless he was slung over her shoulder like this. “Let me go,” he moaned.

Cecily laughed again. “You’re mine, now.”

He willed his tingling arms to move. He grasped her slim waist, hooking his fingers into her smooth skin. He could feel the hard muscle just beneath the deceptively soft flesh. He pushed himself up with a groan, ready to twist off of her - she clenched her arms over his legs, locking them tight against her. Jack could lift his torso, but he was trapped in her grasp.

She suddenly pitched forward, yanking his knees. He was flung backwards off of her, his body slamming into the corner of her metal cot and the concrete wall beside it. The flimsy mattress did little to cushion the blow - pain shot through his neck and shoulders.

She stood before him with her hands on her hips, sneering wickedly down at him. The thinnest layer of sweat glistened on her naked body.

“You call yourself a man?” she snarled. “You’re pathetic!”

He kicked at her knee, hoping to knock her down. She easily dodged the blow, sidestepping it.

Jack had a feeling this would be his last shot at freedom - he lunged forward through the space she just cleared, hoping he could reach his radio before she caught him. He would deal with the humiliation of her ambush later - right now all he could think about was escaping her.

Cecily hooked her left arm around his throat, and with a fluid motion she used his momentum to spin him down onto the concrete floor. Jack could hear her mocking laughter, but he had expected her to do this. He caught himself before hitting the ground, and summoned every ounce of energy to get to his feet even as she held onto his neck. He knew with his weight advantage he could carry her the last few feet to the door where his radio was - and then all it would take would be one quick press of the panic button there…

She leaped on his back as he stumbled to the door. Her arms locked in a chokehold around his neck - he knew he had one last chance before she squeezed.

If he’d slapped her legs away when he felt her wrap them around his waist, he may have escaped. Instead she hooked her ankles together. And as she flung herself backwards she pushed her legs down, forcing his head backwards. His outstretched hands forgot all about the safety of the radio - still just out of his reach - and clawed at her arms as he struggled for breath.

At the same time Cecily leaned further back, bending him off-balance. He stumbled backwards - she steered him back to the cot, and pulled him on top of her.

He was flailing, panicked. All of his training was forgotten as he was strangled. He bucked wildly, trying desperately - and in vain - to loosen her chokehold. She had wrapped her legs around him again, squeezing him between her thighs and keeping her leverage on his writhing body. He felt nothing but taut muscles constricting his ribs and throat. Pain shot through his entire body. His rapid heartbeat pulsed in his ears.

“Ssh” she cooed to him quietly. He felt her lips against his ear as she softly kissed him. “This will all be over soon.”

As he faded from consciousness, he hoped she was right.


Jack awoke with a ragged gasp of breath. His head throbbed, his ribs ached. His vision slowly came into focus - he recognized Cecily’s cell and was immediately overwhelmed with panic.

He sat up, and Cecily rose from beside the bunk. She was still naked, her breasts swaying as she pushed him back down on the cot.

“Don’t move,” she commanded. He lay there as she had ordered, sick to his stomach at the realization he was obeying her out of fear. His throat was still sore.

He realized his chest was bare - his uniform shirt and cotton white undershirt laying heaps in the middle of the floor beside his discarded boots and socks. Cecily stood at the foot of the cot - she jerked his pants off in one quick motion, dropping them down at her bare feet.

“What are you doing?” Jack asked. His voice, once strong and defiant, was nothing but a whimper now. He tried to scramble backwards - there was nowhere to go on the small cot.

Cecily grabbed his ankles and pulled him back so he was lying flat on the cot. “I said don’t move!” she hissed. Jack raised his hands defensively before him, immediately ashamed at his cowardice. He glanced at the open cell door - the hallway was still dark. He had a realization that he must have been unconscious only for a few minutes. That meant he was due for his next patrol in under an hour. If central control didn’t hear from him, they’d send backup.

He felt her pull his boxer shorts off - he was now as naked as she was. He shivered as she stared over him, like a huntress sizing up her kill. He was afraid of her - yes, he was willing to accept that now, as sad as it was to be afraid of a woman. He was more afraid, though, of how he would have to explain this when backup finally did arrive. How could he possibly explain his current position? No one would believe a woman had beaten him up and disrobed him. He’d be fired - and worse, he’d be mocked by everyone he worked with. People would talk about this for decades after he was gone!

Cecily seemed to read his mind. As if knowing he was about to try and escape her yet again, her hand shot out, grabbing his balls. She gently squeezed them, threatening.

“Don’t even think about it,” she said. Jack tensed, but she didn’t squeeze any harder. Her grip was like steel - he felt her wrist twist just enough to let him know she would rip them off if she were so inclined.

With one hand still clutching his balls she knelt on the cot next to him, facing his feet. She swung her right knee past his face - he flinched, twisting his head away. She dropped her left knee on the other side of his head, and he was staring up at the black mass of hair over her pussy. A hint of fragrant aroma from her wafted down at him.

Then she leaned forward. Jack felt her nipples brush across his stomach. She slid her knees back, and her soft thighs slid over his ears, pressing into either side of his head.

Cecily reached back and grabbed a handful of Jack’s hair. She yanked his head forward, off the cot. In the next instant her thighs crushed his neck, and when she released Jack’s hair his neck was trapped between her legs. She flexed her muscles, and immediately the soft flesh went rigid. Jack couldn’t breathe. He clasped her thighs, but was unable to pull them apart.

“If you do anything stupid, I’ll break your neck,” she said matter-of-factly.

She relaxed, and he sucked in a ragged breath. At the same time she grabbed his wrists, pulling his arms down to his side. She held them there, propping herself up on them.

“Now be still,” she whispered. He wanted to ask what she was going to do to him, but then he felt her breath on his crotch. Her wet tongue licked the length of his limp penis. He shuddered, his hips bucking involuntarily. Cecily’s thighs pulsed. She giggled.

Jack felt her run the tip of her tongue along the head of his dick. Pleasure swam the tip of his penis up through his stomach. He moaned, momentarily forgetting he was pinned down with his head trapped in a reverse head scissor from a deadly female inmate.

His penis twitched. Cecily took it in her mouth, gently sucking from the base to the tip. Jack felt himself stiffen inside her warm mouth.

He wondered what she wanted from him. If she meant to give him a blowjob then she could have done so without kicking his ass first. He knew this had to be a trap of some kind - she couldn’t possibly be doing this unless she meant to arouse him before inflicting more pain.

His fears were lost in another wave of pleasure as she slowly moved her head up, and down. Up, and down. Her lips and tongue worked around the head. Despite what she had done to him, despite his fear, he wanted to pull her to him. She slammed his hands back down the moment he tried to lift them.

He was fully erect, now. She’d make him cum, and there’d be nothing he could do about it. Once he came she’d have all the physical evidence she needed to prove their liaison, and have him fired.

“Stop. Please,” he whispered. She didn’t respond. Her warm, wet, mouth continued moving slowly over his dick. Up, and down. Up, and down.

He tried to think of anything unsexy but it was no use. The pure physical pleasure overrode any negative thoughts he tried to convey.

She raised her mouth off of him. His erect member flopped against him, wet with her saliva. He felt her legs open. She rose off of him.

Before he could react she had spun around, dropping her hips onto his. She leaned onto him, pinning his shoulders beneath hers. Her heavy breasts smashed onto him. She pressed her cool cheek against his, and he realized her neck was so strong he couldn’t even move his head side-to-side. He felt her hands grope for his as her legs intertwined with his own. She wiggled her hips, finding his cock beneath the warm mound of her pussy.

Jack realized she meant to mount him. The thought of being forced inside her, without protection, subject to whatever STDs she was carrying, was enough to make him try to escape again.

It was no use. With her legs wrapped around his, and her feet hooked inside his calves, she spread her feet, forcing his legs apart. He couldn’t get the traction needed to buck her off of him, and at the same time her hands found his wrists and locked over them in a vice grip. She slammed his hands down above his head.

She lifted her face over his, smiling down at him. Their noses almost touched. He tried to move, but she had him held tight. She had him held captive.

“Stop squirming - you can’t get away,” she said, a wicked glint in her eye. He was too ashamed to look at her. With his eyes closed he felt her slowly grind her hips in a circle. The heat from her pussy found his cock, still wet with her saliva. She teased his tip with the moist lips of her pussy. She moved slowly, gently pushing herself onto him an inch at a time, then withdrawing. Then pushing him in her just a little deeper, and pulling out again.

“Oh, God, no!” he pleaded, pulling from her. He was able to push her arms up - he thought for a moment he might be able to twist away from her onto the floor.

Then she adjusted her leverage and slowly pushed his arms back down above his head. She laughed. “Where do you think you’re going? I’m stronger than you, remember?”

Jack collapsed back against the cot. He felt Cecily’s hips find his dick again. Her pussy was wet now. She slid him into her like a bullet being chambered.

He gasped, pleasure coursing through every inch of his body now. She moaned, wiggling her hips side to side. He felt her pussy lips completely envelop him. She began to thrust her hips forward and back. Her legs released his as she curled them up beside him, using her knees brace herself as she pumped her hips.

She pulled Jack’s wrists so his hands were pinned beside his head as she leaned over him. Her breasts swayed above him, the nipples brushing against his chest. She ground her hips faster now.

Jack didn’t move his hips with hers, hoping in vain to keep himself from climax - but he knew within a moment she’d triumph over his efforts. She moved on him with the skill of a pro. Even without his help she was taking what she wanted from him. He had never been premature with his orgasms before, but she was riding him so good that he felt the telltale tingling sensation spread from his dick - he was about to come. He tried to pull out from beneath her, but it was no use - she had his hips pinned beneath hers, and as soon as she felt him try to wriggle out of her she fell onto him, wrapping her legs back into the grapevine and spreading his feet apart so he couldn’t get any leverage to escape. All the while she kept him inside of her, pinning his hands above his head as she kept pumping her hips down onto him.

The sensation grew stronger - Jack tried to squeeze his urethra like he’d been told they do in tantric sex to prohibit ejaculation. It was no use. She seemed to sense how close she’d gotten him and ground into him with new fervor. He couldn’t take it anymore - he exploded inside of her with a gasp.

Cecily didn’t slow down or change her rhythm - if anything, she was riding him faster now. As he came inside her she switched positions back so her legs were bent on either side of him, leveraging her to sit up on top of him. She pulled his wrists forward, holding his hands to her breasts.

Jack’s pleasure gave way to intense pain as the sensitive head of his dick seemed to burn with every thrust of her hips. Still, she didn’t stop. She kept riding him, moving his hands in circles over her breasts. She brushed his fingers over her nipples. Jack gasped in pain. “Stop!”

“Oh, yes!” she moaned. Her hips bucked wildly - she jammed his hands into her breasts and squealed with delight.

And then she froze over him, shuddering. She exhaled deeply, a smile on her lips. A sheen of sweat glistened over her body. She slowly moved her hips once more. Twice more, seeming to soak up every drop of him she could as her own juices flowed onto him. Pain shot through Jack’s sore dick. He gasped with each thrust of her hips. He couldn’t wriggle out from under her.

She released his wrists. His hands fell onto her moist thighs - she brushed them away as if his touch disgusted her.

She sneered down at him, her hands on her hips again. Her breasts heaved as she caught her breath. Jack couldn’t look her in the eye - he stared up at the ceiling instead, his mind slowly processing everything that had just happened to him. He rubbed his aching neck. Covered his face in shame. His eyes burned - he felt like he might weep beneath her mocking glare.

“Do you want me to release you?” she asked. Jack could hear the disdain in her voice. Gone were the playful taunts from earlier.

“Yes,” he pleaded. She didn’t move. He knew he couldn’t move her - he had to wait. She sneered down at him another moment, her hands still on her hips. She jutted her chin at him.

“Yes, what?” she demanded.

“Yes, please.”

“Very well. I’ll let you leave.” Cecily leaned over him, lifting her hips off of him. He gasped with pain again as his sensitive penis flopped out. She grabbed his shoulder and rolled him off the cot - he fell in a heap on the cold concrete floor.

He scrambled to his feet, ready for her to attack him again. He was relieved to see her lying on her back on the metal cot, her knees pulled to her chest.

“Get dressed. Your next patrol is in about ten minutes,” she said. Her voice was ice.

Jack did as he was commanded without thinking about it. He pulled on his boxers first, robotically, acting purely off muscle memory. His mind was still racing. His fingers trembled. He felt like he might throw up.

Cecily remained on her back with her knees to her chest. She caught Jack looking at her. Saw the confusion on his face. “This helps ensure I get pregnant.”

Jack’s face went white. Even in the low light Cecily could see his terror. She laughed mockingly. “I’m ovulating. Why else do you think I took you tonight?”

He didn’t reply. He couldn’t reply. He buckled his pants. Fumbled with his shirt buttons. Cecily continued, speaking as she would to a child: “Once I’m pregnant they’ll need to move me to medical for examination. Medical is minimum security - that’s where I’ll escape.”

She pointed to the open door - she was commanding him to leave. Jack shuffled out in his untied boots, too afraid to turn his back to her. He scooped up his weapon belt and slammed the door shut behind him. Even with the steel door between them, he didn’t feel safe. He raced down the hallway to the small office at the end of the cell block. Once inside he shut and locked that door, too. He checked the small clock there - he had nine minutes until his next rounds were due. He’d have to look back in on her - the thought of facing her brought him to tears.

Jack sat at the desk, his face in his hands. He wept in humiliation and shame, the realization of what had just happened to him setting in. Inmate Cecily Rhodes may have been an inmate, but Jack knew he was now her prisoner.
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Old 16-May-18, 07:25
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Default Re: The Jailer Becomes the Jailed

Thread approved.
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Old 16-May-18, 16:58
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Default Re: The Jailer Becomes the Jailed

Great story, really love this one.
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Old 18-May-18, 09:12
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Default Re: The Jailer Becomes the Jailed

Great idea and well written. Loved it.

Thank you, and more please.
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