Torturous Turnabout (Patreon)

Winifred Doe was as ruthless as her name was contrived. A nasty female guard that the prisoners of the facility knew not to draw the ire of. A sadist by nature, she enjoyed her power over the male inmates and wielded it as a weapon.

No prisoner grew to know that better than Isaac Walker, an embezzler kept here by slighted higher ups. His incarceration seemingly a better idea for retribution than a simple pink slip would provide. Other guards were never clear if Winnie was payed to make Isaac’s life a living hell, but she approached the subject with enthusiasm.

Learning of his ticklish nature early on, Winnie was sure to take advantage at every opportunity. She’d attack his sides during feeding hours, often dragging him off later for ‘causing a scene’. She’d drive her fingers into his pits as he was trying to work in the yard. And at night, the other prisoners could barely sleep with the deranged sounds she would have him making.

Winnie herself never let on to any reason to why she treated him so harshly, but seemingly to pleasure in the unfairness of it all. As the days went in the ticklish attacks got longer, and much to Isaac’s dismay no one would say or do anything to stop it.

The worst of it though was that one evening in the cafeteria where Isaac was not allowed to be released from his cuffs. Unable to defend himself, Winnie and several other guards spent the time dragging him to a corner of the room and tickled him past his limits.

Held fast by male and female guards alike, the marked inmate spewed laughter like never before as he was mocked. Stripped naked so no part was safe, even some of the inmates found fun in his suffering as all of his sensitive spots were assaulted.

Hours passed, until the poor man was dragged off to his cell. That would be the last anyone would see of Isaac. Rumors of his death circulated after the ordeal, but anyone who seemed to know anything remained tight lipped. Some talked about his release, some talked of his escape, but at the end of the day one fact remained true-

Isaac Walker had vanished, like a ghost.

Life went on as normal inside of the prison walls. That was until months later, Winnie found herself carted off by several of her own coworkers while in handcuffs. Barking like a mad dog, the blood haired woman demanded answers to why she would be taken away and treated like any lowly inmate.

Blissfully unaware at just how true that statement was to become….~

——

“NOAHAHA! NO PLEHAHAHAH! WHAHAAHAHAH ARHEAHAH DAHAOAOHOOHING!”

The feathers danced wildly as the captured woman roared in her chair. With effortless flicks of their tools her tormentors had effectively taken all control from her. All she could do now was laugh and struggle as the fuzzy fiends stroke lovingly along the sensitive bottoms of her soles.

The two officers had been at it for hours now. Using the sensual sensations of their feathers to further ‘loosen the lips’ of their helpless ‘coworker-gone rogue’. As her hysteria grew, so did their smug smiles. Under these conditions, it wouldn’t be long now until she blabbed.

“Come now Winnie, don’t be a tease. Why not share what you know and I’m sure I can convince them to give you a break.” The warden’s condescending lie boomed through the intercom. No doubt Copper was enjoying every minute of his underling’s ordeal.

All the while the poor redhead could respond with nothing but helpless guffaws. Oh how she wanted to curse out her boss. To wring the necks of her coworkers and stick those feathers up their asses, but it was impossible. Instead she shrieked and begged for them to not saw their dreaded implements between her toes. Her request obviously falling on def ears.

Repeatedly her tormentors would demand she confess to what they wanted to know, but the prison guard turned prisoner had no idea what they where talking about. Only able to cry out her confusion through a garbled messed of laughter and swears.

“HAHAHAHA! AHAHAA PLEHEHAHAHASE! FUAHAHACYHAHA FAHAHAHA!” Winnie babbled, her intimidating demeanor crumbling to dust in front of her coworkers eyes.

Suddenly ‘Winifred Doe’ wasn’t as big as she had always made herself look. In fact, she looked rather small. Where once was a sadistic woman ready to abuse her power on a moments notice, now sat a ticklish girl begging for the mercy she’d never sho anyone. It only drove the guards to swish their feather’s faster.~

“Don’t you dare give her an inch you two.” Warden Copper’s voice sounded off again from the intercoms. “I don’t care if you have to strap vibrators to her feet, do your jobs!”

“Yes sir!” The two guards said, smiles beaming on their faces as they looked at the tray of implements they were provided for such a seemingly special interrogation. An assortment of brushes and pokers were organized by size and practically begging the two of them to experiment.

Winnie’s eyes went wide as one reached for the itching powder and the other the back scratches. What could she have possibly done to warrant any of this? Why was she being treated in such a cruel way? All those questions and more filled her head while the first slathering of powder was applied to her arches.

——

As the frantic laughter blared from the screen in the wardens office, the two well dress men continued to drink their expensive liquor. Copper, visibly delighted by the results of his deal turned to his benefactor with a wheezily smile.

“And you can keep the bitch like that for as long as the donations keep coming. The minute they stop, I set her free and let her loose on you, Capeesh?” The portly man threatened, ending it with a gargled laugh of his own.

The other man just gripped his drink tightly. His expressionless face now twisted into a look of disgust and contempt.

“It is a lot of money isn’t it? So much so that I don’t understand as to why you think you can mouth off to me. You fat, filthy urchin.” His voice was soft, but clearly filled with rage.

Warden Copper smug smile quickly fell as the other man then leaned over him, whispering into his ear.

“Now get out…. Before I pay enough money to have you thrown down there with her.” The man said bluntly. His firm hand pressing down into the soft shoulder of the head of the prison, until he quickly got up and ran out.

Finally alone, the man sat in Copper’s seat, putting his feet up on the desk of the man who once sentenced him to life in this hell hole. It was a delicious kind of irony that Isaac thought he’d never be privy to-

Until today.

Breaking out was hard. And getting revenge on the people who incarcerated him was harder, but it was worth it in the end, all for this. All for her. The woman who haunted his dreams and brightened his nightmares for all these months.

In those months of Isaac’s disappearance he had thought of nothing else but to see his cruel security guard once more. And how she was everything he could have ever wanted. He looked affectionately at the screen as the one guard forced a ball gag tight into her mouth.

His beloved Winnie, there was no way she would have fallen for him before, as weak and helpless as he was. Now he can prove himself to her. Show her how cruel he could be in return. Then he would earn her respect. Then they would live happily ever after.

But there was no time to rush. Isaac finished the rest of his drink as he watched the display on the screen in full bliss. When he felt she was ready, he’d reveal himself to her. But for now, now it was time for him to take in the sights.

He had missed her for so long, and God… she was beautiful…

---

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