The Duchess and the Highwaymen Pt. 02

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Duchess and her highwayman are reunited in jail.
6.6k words
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Part 2 of the 3 part series

Updated 06/08/2023
Created 11/04/2017
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The Dowager Duchess of Hereford dragged in a shaky breath as she made her way through the crowded streets of Leeds. Fighting the fear that threatened to bubble to the surface, Willamina lifter her black silk gown out of the muck, straitened her spine and walked steadfastly onward. Though she couldn't resist casting occasional anxious glances behind her at the smiling nine-year-old boy and the grim-faced nanny clutching his hand.

Nanny Jones didn't approve of Willamina's mission. She had made that very clear when she described it with words such as 'foolish', 'reckless' and 'bloody daft'. The old woman was probably right, she usually was, but Willamina still had to try. She couldn't miss her last chance to see him again.

It was only by sheer chance that she had seen a poster advertising the execution of the notorious criminal Black Jack Turner in the market the day before.

Nearly ten years had passed since that day when she had met him, yet in all that time he had never been far from her thoughts. She could practically see it now- lost in the forest she had stumbled on Jack and his band of highwaymen. Every detail of her woodland ravishment was emblazoned in her memory; the power of their groping hands, the punishing pleasure of their cocks and finally the sweet sense of surrender that lifted her to the gates of paradise.

Her husband had not exactly been pleased when she had returned that night covered in sweat and other men's come. But once it was determined that she was with child, all was quickly forgiven. Nine months later she had given the Duke the one thing he wanted from a wife- a son. As the only child of a long line of unfruitful descendants Giles knew securing a legal heir was paramount. Even if that heir was a dark-eyed, raven-headed, little stranger.

With the Worthington legacy assured, in name at least, she and the Duke enjoyed a happy marriage due largely to the fact that they lived entirely separate lives. She had her beloved son John and he had his mistresses. That agreeable arrangement had ended nearly a year ago when Giles suddenly died of the pox leaving Willamina a wealthy widow of only thirty.

But there was no more time to contemplate the past as the present suddenly intruded. For she had reached her ultimate destination- the imposing stone archway of Bentlow Prison. Nothing about the location was inviting; from the severe architecture, to the grated windows, to the rank odor that hung about the place like an abattoir on a hot summer day.

After a few rapid knocks, the rusty wrought-iron gate creaked open. The fact that the gate bore an unfortunate resemblance to the yawning mouth of hell did nothing to quell her jangled nerves. Still, in she stepped clutching her basket close to her side.

Once inside it was surprisingly easy to gain an appointment with Warden Stokes. A few smiling words and a couple of coins was all it took to persuade the guards. In a matter of minutes she found herself waiting in his office. Outwardly she tried to appear calm but on the inside her stomach was turning summersaults.

Mr. Stoke entered proceeded by the sound of heavy boots and rattling keys. He was a large, imposing man with an air of command about him. He was slightly past middle age, judging by the grey shading at the temples of his chestnut hair, but still quite handsome with strong but regular features.

He was richly dressed in a suit of vibrant blue with shiny golden buttons down the front. A warden's income is reliant on the 'donations' of his inmates. Stokes showy garb was a calculated message to prisoners and their families that within his walls basic necessities and moderately humane treatment would not come cheaply.

He settled in the chair behind his desk, eyeing her shrewdly. Despite the outward appearance of gentility, he gave off a rather hard, menacing aura. Willamina couldn't decide if that frightened or excited her. Perhaps a little of both.

"I was told there was a lovely lady awaiting my presence and I see now that I have not been deceived." The warden said with a broad smile. His voice was low and as rough as burlap. "How might I be of service to you, my lady?"

"Well, Mr. Stokes, I-"

"Warden." He interrupted.

"Yes, warden." She fidgeted nervously in her seat, "I wish to be granted an audience with the prisoner John Turner."

He smiled at that though it didn't reach his eyes. "There are many ladies who would like to see that particular prisoner to offer him relief in his final hours."

"You mistake me sir." She replied sharply, bristling at his crass accusation and condescending tone. "The man is a distant relation and my kindly and quite wealthy grandmother would never forgive me if he were to end his days without a friendly face and a few creature comforts."

As she spin her yarn he snatched her basket from the desk and began riffling through it. He plucked a pastry from the linen-lined interior and sniffed it dubiously.

"A wealthy relation, you say. I didn't think such a notorious outlaw would have his roots in such exulted ground." Digging deeper, he took a bite of an apple he found there and then tossed it carelessly to the floor.

She watched the crimson orb roll across the ground before turning her gaze back to the smug warden. "This particular apple has fallen very far indeed from his ancestral tree. But even the rottenest fruit is a creation of god and therefore deserving of a little Christian charity."

Finally, he reached the bottom of the basket and the sizable bag of coins that she had put there. This time the smile made it to his eyes. In fact, they practically lit up like pound signs. The bag quickly disappeared into the pocket of his fine silk waistcoat.

"I see you are serious about performing your Christian duty." He regarded her from across his desk with obvious interest like a wolf eyeing a tasty hare. It was clear from that ravenous look that he wanted more than just a pecuniary payoff from her.

Willamina had hoped that a heavy purse would be sufficient to pay her way into Jack's cell but she had walked into that office willing to do anything necessary to achieve that goal. She knew that she was a beautiful woman with the kind of fine features and womanly curves that men seemed to find endlessly appealing. If her beauty was the only bargaining chip left to her then she would play it to full advantage.

"Entirely serious." She dropped her voice to a seductive purr.

"I'm not sure if my conscience would allow a lady of delicate breeding to meet with a notorious criminal alone."

"Be assured that despite my breeding I am not as delicate as I look." She leaned in so that he could get a good look of the two lush mounds of flesh as they spilled forward.

Taking in the view, he tipped back in his chair, thoughtfully stroking his chin. Before long a rapacious smile spread across his face as if he was the first cat to ever consider eating the canary. "Perhaps if we might find a way to test your fortitude."

"And if I satisfied your... conscience in the matter of my fortitude then you would allow me to see the prisoner?" She ventured.

"You have my word."

With that he rose from his chair and stalked towards her. Something about the predatory flash in his eyes momentarily shook her resolve. Before she knew what she was about, Willamina had leapt up and shuffled backwards until she was pressed flat against the wall.

Still, he advanced. She tried to hold back a shudder of apprehension but didn't quite succeed. While the gentleman was admittedly attractive, Willamina was disgusted by his apathy and avarice. So she was surprised to feel the tell-tale tingle of desire rise in her as he sandwiched her between the hard wall and his equally hard chest.

He leaned in to whisper in her ear. "So do we have a deal?"

She shuddered at the feeling of hot breath against her neck. "Yes."

"Good, now remove your dress." He announced matter-of-factly.

Willamina jumped to obey though her hands trembled. He didn't offer aid as she struggled to unfasten the elaborate mourning dress. Fearing she would lose her nerve, she tried to keep her gaze cast downward and away from the warden's tight breeches. Particularly the prominent bulge therein.

One by one she stripped off her gown and petticoats. As the cool air hit each part of her body it caused her delicate white flesh to rise in goosebumps, enhancing the sensation of vulnerability.

Only once she stood before him in nothing but a corset and stockings did she dare to raise her eyes from the floor. She watched his gaze upon her, roaming keenly over her body. It was rather obvious that he approved of what he saw.

Abruptly he grabbed her by the nape of the neck and forced her to bend at the waist so that her cheek was pressed against the cool desk. His hand caressed her raised buttocks before delivering a brutal slap. She bite back a whimper as fear and arousal warred within her.

"Lovely," he breathed. "A pearl of great price."

Her heart raced as she sensed him unbuckling his belt directly behind her. Her arms were then efficiently pinned together at the small of her back and the rough leather belt was being wound around her slender wrists.

She gulped, wondering just what she had gotten herself into. But it was too late for second thoughts. Her heart beat even faster when she felt his fingers prying open the lips of her sex. First one then two digits slipped into the snug passage. The slick, wet sound of his fingers entering her quim proved that despite her reluctance, she was not entirely unmoved by his actions.

He laughed mockingly. "Not such a proper Christian lady after all."

She blushed at his humiliating words, grateful that her scarlet face was hidden from his view.

Once inserted his fingers curled and spread inside her, stretching her to his liking. Suddenly he removed his hand and something much larger replaced the fingers. She did not have to see to know what that something was.

The warden's impossibly large member forced its way into her soaking pussy. She shrieked at the abrupt penetration. Even with his preparations and her copious wetness it hurt. To be violated so suddenly and brutally was a shock to the system. But as he slammed into her she quickly got over it as she felt her body begin to adjust to his girth and her mind began to submit to his control.

The rough handling rekindled a long dormant spark of excitement. The shock was replaced by a fierce need. A need to be dominated. A need to be mastered. She moaned deep in her throat. The tension in her limbs dissolved as she reveled in the delicious sense of helplessness that took hold.

Indifferent to her own pleasure, the warden rammed into her. He grabbed her hips, fingertips digging firmly into her flesh, and delivered several punishing thrusts from behind. The motion rocked her whole body, causing her to slide up and down along the surface of the desk. The coarse wood abraded her bare breasts while books and papers tumbled off the edge and onto the floor.

As the warden continued to fuck her wet cunt, his rigid cock seemed to swell further inside her. She could hear the evidence of his excitement from his harsh breathing, punctuated by masculine grunts. The primal sound thrilled her. It called to her, filling her with a violent desire to be used by him even more thoroughly.

To be reduced to a sexual object by a commanding male made her feel more alive than she had in years. Not since the day she met Jack had she experienced the exquisite thrill of submission.

That pleasure was swiftly mounting. Her release was so very close, she could practically taste it. Yet before it could come to fruition he was pulling out of her and dowsing her raised backside with warm seed. Willamina heaved a sigh of frustration at being denied that final satisfaction.

The warden didn't seem bothered by her frustration. He removed himself from her and staggered away, leaving her to awkwardly push herself from off his desk.

"If you would be so kind." She turned so he could unbind her wrists.

"Who said I was done with you yet?" Suddenly he grabbed her arm with bruising strength and then shoved her forward. "Guards!"

Two men rushed into the room. Both were wearing uniforms of a bright red coat and tightly fitted buff breaches. The first man was young, no more than twenty, with light blond hair and vibrant blue eyes. He held his tall, lean frame in a rigid stance which gave the impression that he was once a soldier.

Willamina's breath caught momentarily when she took in the appearance of the second turnkey. With his jet-black hair, sharp brown eyes and swaggering good looks he bore a rather strong semblance to Jack. Only this fellow had a cold glint to those dark eyes that his counterpart did not possess.

They caught sight of her at once, hair disheveled, tits exposed and heaved forward by the way her hands were secured behind her back. Judging by their hungry stares she must have looked like a well trussed piece of meat ready for the feast.

"Here you are boys." The warden gestured toward her. "Don't say I never share my payoffs."

The blond guard stood unmoving, as if frozen by indecision or maybe just shock. The darker guard seemed to share none of his colleague's misgivings. He rushed towards her.

As he came at her, fear tore through her. Willamina's eyes widened in panic as he seized her roughly by the shoulders. But with her hands tied behind her back she could do very little to defend herself.

"Grab her, Mr. Hale. That's an order." Stokes barked.

At that, the one called Hale snapped out of his trance. He grasped her legs so that she was lifted off the ground and suspended between the two men.

"This was not part of our bargain sir." She shot the warden an accusing look.

"Does not your Christian love apply to all god's creatures? After all, the bible says to love thy neighbor." Stokes laughed at his own profanity. "Put her on the desk." He directed the men as he settled into a nearby chair.

They placed her on the desktop on her back so that her nether parts were aligned with one edge of the desk and her head dangled over the other. With her arms secured behind her she felt the bite of discomfort as her weight pressed down on her wrists.

She struggled to sit up but the guard situated between her parted legs nudged her back down. The two pinned her down as they fumbled to remove their pricks from their breeches. Once free she could see that the substantial instruments were already standing at full attention.

"Get on with it, Mr. Marlow." Stokes commanded to the dark-haired guard.

She gazed up to find Marlow smiling down on her. It was not a kind smile. Before she had a chance to react he grabbed a fistful of her coppery hair so that she couldn't escape the swollen tip of his flesh-hot cock that was being insistently pressed between her lips. The pressure on her scalp increased until her neck was strained backwards and she was obliged to open wide.

He wasted no time in ramming his salty length into her mouth and back out repeatedly. The angle of her head allowed him to hit the back of her throat with every thrust while his grip on her hair held her in place. Tears sprang up in her eyes but he carried on, unbothered by her gasping sobs. If anything, the tears seemed to excite him further.

She squealed in pain as Jack's double reached down to squeeze her nipple in a vice-like grip. "Take that you filthy little slut." He hissed.

At the same time she felt her thighs being nudged wider. Hale entered her roughly. The slick flesh of her sex parted as he filled her in one decisive thrust. Slowly he withdrew to the tip and then lunged forward hard, letting her feel his power. His previous reservations had clearly faded, replaced by a driving need to conquer. All the while his calloused hands held her firmly against the desk, reminding her of the vulnerability of her position, both literally and figuratively.

To make matters worse, Willamina could feel tendrils of arousal creeping back in. Beneath the fear and humiliation, unsatisfied desire had been simmering just under the surface. As the two cocks moved inside her that desire bubbled to the top.

"Suck my cock bitch." As he fucked her mouth Marlow rained demeaning insults on her.

To her surprise she found her body responding to the harsh language and the even harsher handling. It sent a rush of moisture to wet the folds of her sex. She could not name it or explain it but some dark secret part deep inside of her found all this degrading treatment wildly exciting.

Through the haze of pain laced pleasure Willamina was unceasingly aware of the warden's eyes on her. She turned her head to confirm Stokes was watching her intently, holding a mug of ale in one hand and idly stroking his cock with the other.

"Harder!" He commanded. "Give the lady the fucking she deserves."

The men happily complied. In alternating tempos, they pistoned into her with all their might. Every thrust in her quim drove her forward so that she was compelled to take the cock in her mouth deeper. The duel assault kept her teetering on the edge of agony and ecstasy.

"I think the whore likes it." Marlow sneered.

She moaned in agreement though the sound was largely muffled by the cock that was lodged in her throat.

Careless of her feelings, the guards took their pleasure from her body as though she was a lifeless ragdoll. Willamina could do nothing but lie perfectly still, helpless against their rough usage of her body. The one between her legs was clamping onto her thighs, leaving fingertip shaped bruises on her pale skin. The other was pulling her hair and roughly fucking her face until fresh tears ran down her cheeks.

It hurt but Willamina accepted it, enjoyed it even. She was learning to master the pain, to convert it into something pleasurable. She would find her own pleasure, despite their best efforts to the contrary. Turning the tables on her tormentors gave her a surge of power that only intensified the pleasure.

Seized by a sudden impulse to be an active participant in her own degradation, Willamina sucked harder on the meaty shaft between her lips. She rocked her hips to take the man between her thighs further into her battered cunt.

All the while she was becoming more and more aware of the steadily mounting tension between her legs. The tension became increasingly urgent as Mr. Hale reached to frig her clit. At that her whole existence shrunk down to nothing but the sweet friction of his fingers on her aching bud. As he sped up his circular stroking her whole body grew taut like a tightly wound spring ready to unravel.

And unravel she did when the sensation suddenly peaked and erupted in pulses of bliss that wracked her body and filled her consciousness. She could feel her channels contracting and convulsing around the cocks filling them. Moments later, Mr. Hale followed, fetching his warm seed on her stomach. Marlow found his release next. He drove into her mouth a few more times before pumping it with hot spurts of briny liquid which she had no choice but to gulp down.

They both withdrew from her at the same time, leaving her feeling strangely cold and empty. She was still trembling when they untied her brusquely and threw her back her clothes. Using a torn piece of her petticoat, she wiped the men's fluids from her body and dressed in silence.

"I am quite satisfied by your fortitude my dear." Mr. Stokes pronounced before turning to Marlow. "Mr. Marlow, if you would escort the lady to Turner's cell."

Once suitably put together Willamina grabbed her basket and headed for the door. She breezed past them, chin up, head high, to remind them that though they could use her body they could not truly touch her.

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