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The Hanging of the Lady Pirate

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arrakur

Assistant executioner
A short story based on a roleplay i did some time ago. My partner´s inspiration for the Lady Pirate´s look was a certain playboy model. Hence her name. This story is a sequel of sorts but there is no need to know of the roleplay´s content to understand what is going on.
English is not my native language so bear with me.

The Hanging

Of

The Lady-Pirate


Jamaica. In the year of our Lord 1690



Karen McDougal, late captain of the pirate vessel “Marauder” now sunken into the depths of the Caribbean Sea lay on the cold floor of her dungeon cell naked and groaning. Her arms and joints ached horribly from her ordeal on the rack and every muscle in her body was in pain.

She faintly heard the screams of her crew, her men being tortured in the vast chambers of pain and torment which occupied more space in the dungeon of Port Royal then the cells that held its captives. Obviously the Governor intended to make the crew and captain of the “Marauder” suffer to the fullest before having them hung in groups and no doubt there already where plenty of her crew wishing for being among the lucky first to do their last dance in suffocation at the end of a rope.

Being the captain Karen knew that she would hang last and thus suffer the longest under the cruelty of the Governor and captain Diego whose vile seed´s sticky remains still clung to her sex.

She heard steps approaching outside her cell and her stomach clenched at the sound of keys rattling in the lock of her cell-door. It could only mean that someone was coming to take her back to one of the torture-chambers. How long could she hold out without demeaning herself? Without begging? Without giving these vile creatures what they crave the most beside her pain?

The door opened and the fat Governor entered with three guards. He looked down at the naked woman on the floor and smiled.

“You hear your men, don´t you?” he smiled.

“I have all my torturers busy themselves with them and there seems to be not much courage in them to begin with. Already the first are begging for mercy. Soon I´ll have them begging for death and suck each other´s cock for the briefest time of grace. My guards always find that quite amusing, I might add.”

Karen stared up at him in hatred, lips trembling. She wanted to kill him or even attack him so that the guards may strike her dead in that endeavor. But weak with pain and lying on the floor she could do nothing.

“You are scared that we come to take you one of the torture chambers below now, aren´t you?” he says with a thin smile.

“No need to act brave. We are not. In fact, you will leave this dungeon.”

Karen could not prevent a spark of hope glimmering in her. Leaving the dungeon could not mean salvation. But it might, just might provide the tiniest chance of escape.

“Lady McDougal, now you shall hang!” the Governor said with stern voice.

She felt the spark of hope flicker and fade out. So this was the end. At least she got to die more quickly than poor Jasmine and her men and the thought felt her with shame and despair. Dead she could do even less for her crew then being imprisoned and tortured with them.

“Take her!” the Governor barked and the guards bent down to pick the doomed woman up.



Karen groaned, fighting to stifle a sob of pain and misery.

She had been taken from the dungeon garbed in a few rags. Her hands had been cuffed behind her back and her feet shackled so she could only walk with tiny steps. But instead of being taken to the gallows she had been taken to a chariot, driven to the Governors palace and, still in cuffs, had been washed and then taken downstairs to learn that the Governor had lied to her. At least in part.

“I told you, you would hang, didn´t I?” the Governor said with cruel amusement.

Karen was completely naked. Her hands were shackled together behind her back. Both her legs were spread wide apart. Cuffs were closed around her ankles and connected by a long iron bar which held her legs spread. From her ankle-cuffs two additional chains were bolted into the floor to her left and right.

And she wore another pair of iron cuffs, larger than those around her wrists and ankles but woefully not by far. Those cuffs were closed around the very bases of her breasts, cruelly separating her breast-globes from her chest and forcing them into two reddened, tight-skinned mushroom-shaped balls of pain. Even worse than that pain was the fact that the cuffs around her breasts were hanging from the ceiling by two thick chains and thus poor Karen was hanging by her breasts. The toes of her feet were mere inches above the floor but those may as well have been miles. She couldn´t touch the floor, couldn´t reach anything with hands or feet to give her any leverage and relief.

She was hanging from the ceiling by her breasts in mid-air, completely helpless, the weight of the cuffs and the long iron bar even adding to her weight and she could do nothing else but feel the pain in her tits grow from horrible to unbearable and then get worse. It felt like her breasts would tear off her chest or explode at any second. But neither happened and so the insufferable pain announcing those horrifying events went on and on.

She clenched her teeth trying not weep and cry out in pain but neither could be subdued for much longer. She had known rape and she had known torture. But what was being done to her now filled her with shock, outrage and fear. That someone who had her in his power was as depraved as this, to torture a woman in such a way pointed out to her that her captivity would be far, far more excruciating as she could ever have imagined.

She tried to keep her head up since that was less painful for her breasts by the tiniest fraction of whatever measure with which one might quantify pain. This room below the palace was clearly a torture-chamber. Other than the chambers of pain at the city dungeon this one was neat and clean. The stonewalls were carefully crafted and there were comfortable chairs and a sofa. There were, of course, also a huge collection of chains, ropes, whips, a rack, a pillory and at least a dozen devices so bizarre that Karen could only determine that they were for giving pain but lacked the depraved cruelty and lust to cause suffering to fathom how they worked.

Clearly, the Governor had the pain of his captives as clear in mind as his own comfort when he had this torture-chamber equipped.

A fireplace and torches at the walls illuminated the room and highlighted the sweat-glistening curves of Karen´s hanging body. The cracking of the firewood mingling with her ongoing groans and small sobs.

The Governor sat at a table, picking up a grape and savoring it as he watched her agony.

“So,” he said “do you like being here? Not as dull as the city dungeon, yes?”

Karen said nothing but groaned and sniffed. The pain was so horrible she was at the verge of screaming at the top of her lungs.

“You will have to go back, of course.” He continued with the tone of apology in his voice.

“It´s for morale. The guards deserve to see the great Lady-Pirate McDougal being tortured and begging for mercy. And the opportunity to amuse themselves with your body. But don´t worry, my sweet.”

He took a sip of his wine and continued with a leering, evil grin.

“I will take my time torturing your men within an inch of their life’s before I have them hung by their necks a mere two a three at a time. And you will be the very last one to hang. So, plenty of time for you to visit me here from time to time to escape the dullness of the rack and the whip and the branding iron. My equipment here is so much more interesting for a woman, don´t you think?”

He got up and walked up towards her. She watched him with dagger in her eyes and a face wrecked with pain.

“Getting a mere taste of my creativity it would be meet for you to agree.”

She groaned and sobbed, then gave out a short, sharp cry of pain as he yanked her head back by her full, black hair. As horrible as the pain in her breasts was, it got worse by the strain it put on her chest to have her head pulled back.

“You don´t agree?” he smiles mock benevolence. His other hand went to her bloated, pain-filled breasts and cupped them on after the other. Then he squeezed, or tried to squeeze, the tight tit-globe making Karen scream and sob with pain.

As he let go of her breast and hair, her head went up and a surge of fury and outrage caused her to finally speak as he went in front of her.

“Bastard!” she cursed. “Somehow! Somehow I will get free and I will KILL YOU, YOU…. ANIMAL!”

“You will never be free. Except after your death. And until then, my insolent little slut…” he said with a vicious smile, positioning himself in front of her.

“… you will learn that when it comes to pain no woman can take what I can give.” With a smile becoming even crueler he put his boot on the iron bar, stepping down on it.

Karen screamed into his leering face in blinding pain as he added a good part of his weight to hers and worse agony than ever before exploded in her breasts.

“AAAAAAAAAAAAAAAAAAAAAAAAAAAAAaaaaaahhhhhyouuuu….bastard!”

Her chest heaved and gave out shuddering sobs as he stepped of the iron bar.

Tears born out of pain and outrage ran from her eyes now and she muttered and sobbed under her breath, softly uttering words like `bastard`, `lowest of pigs` and `sick animal` as she wept.

“Such language.” He said with pursed lips.

“Such coarseness. Makes one wonder what you would do to me now if our positions where reversed, eh? Probably something as crude and unimaginative as this?” He smiled and with sudden, vicious brutality rammed his knee up against her sex.

WUMPH!

Karen eyes bulged out and she cried out in pain again. The brief pain in the most vulnerable, sensitive part of her body briefly overshadowing the agony in her breasts.

He kneed her pussy again. And again. He brought the bony point of his knee with frightening brutality and horrible precision directly against her slit and pussy-lips, aided by her defenseless immovability. A fourth time. A fifth time.

“That´s what you would like to do to me,eh?” He barked as she screamed.

“You boorish pirate cunt! You are among your civilized betters now! You don´t get to do things like that ever again!” He crushed her pussy at the tip of his knee again. And yet again.

He repeatedly, relentlessly rammed his knee into her defenseless sex with all his strength until Karen was at the verge of passing out from the pain.

Then he stopped and walked up to his collection of whips at the wall as Karen heaved and sobbed and cried. She did not know how much more of this she could take. It wasn´t just the ungodly pain that started to crush her but also the might of her tormentor. Not his might as a man, but the power of his complete and utter cruelty.

He came back at her side, smiling, holding a wooden paddle in his hand. It was thick and heavy, eight inches in breadth and twenty inches in length. As he went to get it he had opened his breeches and his cock stuck out and pointed up, angry red in full erection. She looked at him and his two weapons, fearfully, sobbing from the horrible pain in her breasts and her pussy.

“For a captain, a leader of men, you don´t seem to have the balls for it. At least not down there as far as I could feel.” He said with a vicious smile.

“Let´s test your mettle by seeing what your other balls can take, then.”

He lifted the paddle high behind him, took aim and brought it in a high arc down on her breasts. The wood struck across both her breasts, flattening them against the cuffs around them which denied them the slightest retreat and at the same time increased their tenderness and capacity to feel pain, immeasurably. White-hot agony exploded in her breasts and Karen shrieked in pain. She shook her head madly, whipping her black hair to and fro. Her hands worked madly against the cuffs around her wrists and her legs trembled and shivered. Her body, her entire being concentrated on the demented effort to escape, to ESCAPE the pain. In her agony she was blind to the fact that her struggle against the bondage increased the pain in her breasts even more.

The Governor watched her pain and anguish play out and slowly subsiding. She sobbed and panted madly, desperately trying to get control of her voice so she could beg him to stop. Before she could utter a word he smacked her breasts again with terrifying, devastating brutality.

Again she yelled out in pain, trashing madly and bulge-eyed against her chains as the Governor watched with enjoyment. He was standing there, watching a woman in the kind of pain that only a woman can feel and the kind of which no man can imagine how horrifically immense it truly is. But if he could, if some magical or divine interfering would make him actually feel her pain for a little while instead of just watching it in glee, it would only increase his pleasure and deepen his arousal. Truly knowing how much he was hurting her.

He stepped in front of her as she howled and sobbed and wept. Her breasts were dark-red and pulsating in a kind of pain Karen could never have imagined possible. She saw him in front of her, raising the paddle high and desperately tried to beg for mercy.

“Oh, pl….” she sobbed, and then howled in pain as the paddle flattened her left breast against the cuff imprisoning it. The paddle went up and the tit bounced back into its eternally painful tightness. Still Karen screamed at the top of her lungs. Then screamed again as the paddle crushed her right tit. Then her left again. Her right, her left.

The Governor kept beating her tits with the heavy paddle as she screamed and howled and sobbed, pitifully, at the verge of madness from the pain.

He was in a state of bliss. His cock was hard and pointing up, eager for ravagement. His belly was knotting and churning with pleasure. To say that torturing a woman was as pleasurable to him as taking her was a false assessment. For the Governor, torturing a woman was even better than fucking them. The prime pleasure.

He felt his balls tightening as he beat her breasts with the paddle, punishing her tits like a madman from hell. He felt his orgasm building up and it was too late to be inside of her in time. But he felt the almost desperate urge at the verge of cumming to do something to her to coincide with it. Something exquisite.

He put threw the paddle down on the floor and quickly got something else from his collection of whips. He almost ran back in front of her and steadied himself with effort on the cusp of release, his breathing deep and heavy. In his hand he had a thin rod. Not a wooden one but a very thin rod made especially of steel. He raised it high above the sobbing, broken woman and brought it down on her right breast.

For a moment it seemed to have cut her breast in half, right across the middle as the thin steel rod divided the bulging tit cone into two halves, each twice in pain as just before. For a second Karen was suddenly quite, in shock of a pain to great to express. Then the Governor pulled the rod back and her tit bulged out again like before, but with a horrible, long, dark line over her nipple. She took a deep breath, and then gave out a roaring, animalistic cry of mindless, female torment that made him cum.

He did not even touch himself, just stood there with his back arched and his cock poised at the trashing, howling, sobbing woman as he shot the strands of his white semen against her twitching belly.

He stood there for a while, letting his pleasure subside as Karen’s screams and sobbing slowly became less hysterical. By the time she calmed herself into crying in broken hopelessness his cock was soft again and he sighed in contentment and went to his chair to sit down.

He drank his wine as he watched her hanging, sobbing. She babbled something that sounded like `no more` and `please`. He smiled thinly.

The evening had just started and he was not the kind of man to be satisfied by mere one climax. He would have her pussy around his cock at least once before the night was over. But before that his cock needed hardening so he stood up and went in front of her again. He looked at her poor breasts, smiling cruelly, and with his soft cock twitching he raised the steel rod again.

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I am afraid not. I wrote it on a whim and it should be regarded as more of a vignette as a story.
I seldom find the time and the discipline to write these days so I stay away from posting long stories and then disappointing the readers by not finishing it.
Too bad
 
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