Old Man Billy
Copyright© 2025 by Ayra Atkinson
Chapter 2
Western Sex Story: Chapter 2 - In the dusty town of Dreadworth, sixty-five-year-old Bill—known only as Old Man Billy—walks a fine line between survival and ruin. Haunted by a lifetime of violence and regrets, he finds himself lured into a world of brutal underground fights, crooked bets, and dangerous liaisons. Every gamble carries the weight of his last chance at redemption—or his final descent into despair. With his Colt at his side and nothing left to lose, Billy wagers his soul against the darkness of a town that devours
Caution: This Western Sex Story contains strong sexual content, including Ma/Fa Slavery Fiction Crime Western Anal Sex Cat-Fighting Violence Illustrated AI Generated
The lamp lights of the Booty Bo Brothel beckoned from down the street, casting a garish glow on the dusty sidewalks. The building was a stark contrast to the rest of the town, its vibrant colors and garish decor a stark reminder that there was more to life than the daily grind. The sound of laughter and music spilled out from the open windows, a siren’s song to those looking for a brief reprieve from the harsh realities of the Old West.
With a mix of excitement and trepidation, Bill pushed open the swinging doors and stepped into a world of velvet and lace. The air was thick with the scent of perfume and sweat, a heady mix that seemed to cling to the walls and the very fabric of the place. The madam, a plump woman with a smile that didn’t quite reach her eyes, greeted him with a nod. “Looking for a good time, old-timer?” she asked, her voice a purr that seemed to stroke the very air around her.
Bill swallowed hard, his heart hammering in his chest. “I’m looking for someone,” he said, trying to keep his voice steady. “A lady with a ... generous figure, you know?” He cleared his throat, feeling a blush creep up his neck. “Someone with ... big ... assets.” He couldn’t quite bring himself to say the words.
The madam’s smile grew wider, a knowing glint in her eye. “Ah, I see,” she said, her voice a seductive whisper. “You’re looking for Mrs Kelly.”
Mrs. Kelly was a legend in Dreadworth, a woman whose beauty and figure had inspired sonnets and bar fights in equal measure. Her reputation was as vast as the desert that surrounded the town, and her talents were said to be unparalleled. The madam nodded to a young girl with a tray of drinks, who scurried away to fetch the woman in question.
Moments later, Mrs. Kelly appeared, her voluptuous form squeezed into a dress that was more suggestion than actual fabric. Her breasts, like two overripe melons, threatened to spill over the corset that barely contained them. Her hair was a cascade of dark curls that framed a face that could have graced the cover of a dime novel. She had the kind of curves that could make a man forget his name, his past, and even his future.
“Bill,” the madam said with a knowing wink, “meet Mrs. Kelly.”
Bill’s eyes widened as he took in the woman standing before him. She was indeed as bountiful as the rumors had painted her, with a figure that could make a saint reconsider his vows. He licked his lips nervously, feeling the weight of his decision pressing down on him. “Ma’am,” he mumbled, tipping his hat. “Could I ... uh ... see your ... assets?” He felt his cheeks burn with embarrassment.
The madam chuckled, a knowing look in her eye. “Mrs. Kelly is a woman of discretion, but for a man with such fine taste, I’m sure she’ll make an exception.”
With surprising agility for a woman of her size, Mrs. Kelly stepped closer to Bill, the fabric of her dress whispering against her skin. The madam’s eyes never left his as she began to untie the strings of Mrs. Kelly’s corset, revealing the bountiful treasure beneath. Inch by inch, the garment loosened, the tension in the room tightening like a coiled spring. When it finally fell away, Bill’s breath caught in his throat. Her breasts were indeed as magnificent as the stories had told, full and firm, the large areolae puckered with anticipation.
Mrs. Kelly’s hands slid down her body, tracing the curve of her waist and the swell of her hips. She stepped closer to Bill, her ample cleavage nearly spilling into his face. He could feel the heat radiating from her body, a stark contrast to the cool evening outside. The madam stepped back, her smile a knowing smirk as she watched the exchange. “As you can see,” she said, her voice a silky purr, “Mrs. Kelly is everything we’ve promised and more.”
Bill’s gaze was drawn to the woman’s backside, a monument to fertility and temptation. The madam, sensing his interest, stepped in again. “Now, let’s make sure we avoid any misunderstandings,” she said, her hand sliding around Mrs. Kelly’s waist. “You’re looking for the full experience, aren’t you?”
With a dramatic flair, the madam guided Mrs. Kelly to turn around, revealing an ass that was as round and firm as a pair of freshly baked bread loaves. The woman’s cheeks were pale and unblemished, a stark contrast to the rest of her tanned body. Bill felt his mouth go dry as he took in the sight, his thoughts racing with a mix of lust and anxiety. The madam leaned in, her breath hot in his ear. “You see, old-timer, Mrs. Kelly’s got more than just a pretty face. She’s got the kind of assets that’ll make you forget all about your troubles.”
With a deft hand, she reached up and grabbed the fabric of Mrs. Kelly’s dress, pulling it up to expose her nether regions. The woman’s pussy was a thing of beauty, shaved smooth and glistening with the sheen of arousal. The sight of it made Bill’s cock stir in his pants, a feeling he hadn’t felt in a long, long time. “This,” the madam said, her voice a seductive purr, “is what you’re really after, isn’t it?”
Mrs. Kelly giggled, a sound that was both innocent and knowing. She turned around to face Bill, her breasts bouncing slightly with the movement. “You want to see more, darling?” she asked, her voice a siren’s call. She bent over the bar, her ample ass in the air, and spread her cheeks wide. The madam leaned in, her finger tracing the line of Mrs. Kelly’s anus, a small, puckered hole that seemed to wink at Bill in the dim light.
He couldn’t take his eyes off of it. The thought of being with a woman like Mrs. Kelly, feeling her warm, wet flesh against his own, was almost too much to bear.
“What’s the price?” he croaked, his voice sounding foreign even to his own ears.
The madam’s smile grew wider, revealing a set of teeth that had seen better days but were still surprisingly white. “For a man with your ... particular tastes, I’d say fifty gold pieces for the night,” she said, her eyes gleaming with greed. Bill felt his heart drop into his stomach. That was more than he’d won from the fight, more than he’d had in years.
But before he could protest, she leaned in closer, her breath smelling faintly of mint and something else, something darker. “Or,” she whispered, “you could win her for free.”
The madam’s proposal was simple, yet ludicrous. “If you can make Mrs. Kelly scream so loud she won’t be able to walk out of here by dawn,” she said, her eyes gleaming with a mix of challenge and amusement, “your night is on the house. But,” she added with a dramatic pause, “if you can’t, you’ll have to pay double.”
Billy’s mind raced. The thought of being with Mrs. Kelly was tempting beyond measure, but his gold was all he had, all he’d won from the night’s thrilling spectacle. The madam watched him, her expression unreadable, as the room fell into a hush. The weight of the decision pressed down on him like a boulder, his heart thumping in his chest. He swallowed hard, his throat dry as dust. “Is there a time limit?” he finally managed to ask, his voice a hoarse whisper.
The madam leaned back, a glint of amusement in her eye. “Oh, I’m feeling generous tonight,” she said with a laugh that held a hint of malice. “You can have her from now until tomorrow midday. Twelve whole hours to show her what you’re made of.” She paused, letting the words hang in the air like a noose waiting to be tightened. “But remember, if you can’t make her scream in pain, and if she can walk you’ll owe me double.”
Bill’s heart hammered in his chest as he weighed his options. The sum was exorbitant, but the prize ... Mrs. Kelly’s curves, her soft skin, and the promise of a night filled with passionate ecstasy ... it was almost too tempting to resist. He knew the madam was watching him, her gaze sharp as a knife, waiting for him to either fold or rise to the challenge. With a deep breath, he nodded. “Alright,” he said, his voice steady despite the storm raging within him. “I’ll do it.”
The madam’s smile grew even wider, and she clapped her hands together. “Excellent!” she exclaimed. “Follow me.” She led Bill and Mrs. Kelly through a set of velvet curtains and down a dimly lit hallway, the air thick with the scent of musk and desire. The walls were lined with doors, each one a gateway to another man’s secret desires. They stopped in front of one with a small, brass number 7. The madam opened the door with a dramatic flourish, revealing a room that was surprisingly clean and well-appointed. A large four-poster bed dominated the space, its red satin sheets a stark contrast to the wooden floorboards.
Mrs. Kelly stepped inside, her naked body casting shadows that danced across the walls. She climbed onto the bed with the grace of a gazelle, her breasts bouncing slightly with the motion. She lay back, her arms stretched out to either side, and beckoned Bill with a crooked finger. “Come on, darling,” she purred. “Let’s get started.”
Bill’s heart was racing as he followed her into the room, the madam’s words echoing in his ears. He tried to ignore the knot in his stomach as he approached the bed, his eyes locked on Mrs. Kelly’s voluptuous figure. The madam closed the door with a finality that made him jump, leaving him alone with the woman whose screams would determine his fate.
The room was lit by a single candle, casting a soft, flickering light that danced across Mrs. Kelly’s skin. She looked up at him, her eyes dark and hungry. “Take your clothes off,” she ordered, her voice a command that brooked no argument. Bill fumbled with his shirt, his trembling hands making the simple task seem Herculean. He felt ridiculous, a withered old man standing before a goddess of the flesh.
Finally, he was naked, his cock standing at half-mast, a sad testament to his excitement and his fear. Mrs. Kelly looked him over, a hint of disappointment in her eyes that made him wilt even further. But she said nothing, instead reaching out to stroke his chest with a gentle hand that seemed to whisper promises of pleasure. Her touch was like a brand, searing him with desire, and suddenly, his cock was as hard as a length of iron.
The madam’s challenge loomed over him like a specter, a constant reminder of the high stakes of this game. But as Mrs. Kelly began to kiss her way down his body, her lips leaving a trail of fire in their wake, Bill couldn’t help but push those thoughts aside. Her mouth found his cock, and she took him in with a greed that was both terrifying and exhilarating. He groaned, his hand tangling in her hair as she worked her magic. The room was filled with the wet sounds of her mouth, the slap of her breasts against his thighs, and the harsh rasp of his own breath.
The hours ticked by like seconds, the candle burning low as Bill threw himself into the challenge. He explored every inch of Mrs. Kelly’s body, his hands and mouth worshipping her curves with a fervor that surprised even him. He’d forgotten what it was like to be with a woman, to feel the warmth of flesh against flesh, the slide of skin on skin. And Mrs. Kelly, for all her professionalism, seemed to be enjoying herself as well, her moans and sighs growing more genuine with each passing moment.
But as the night wore on, the doubt began to creep back in. Could he really make her scream so loud she wouldn’t be able to walk out of here come dawn? He’d heard stories of men who’d tried and failed, their pride bruised and their wallets lighter. The room grew hot, the air thick with the scent of their mingled sweat and the smell of their passion.
In a final, desperate bid, Bill reached for the jar of lard that sat on the bedside table. It was a common enough request in a place like the Brothel, used to ease the way when the client was particularly ... enthusiastic. He coated his cock with the greasy substance, watching as Mrs. Kelly’s eyes grew wide with surprise.
With a grim determination, he slid back inside her, his movements rough and urgent. Mrs. Kelly’s eyes rolled back in her head, and she let out a low moan that grew louder and louder, until it was a scream that seemed to shake the very walls of the room. The sound was like music to Bill’s ears, a sweet symphony of pain and pleasure that drowned out the doubt and fear that had plagued him all night.
He felt himself nearing climax, his balls tightening with the promise of release. With a final, powerful thrust, he emptied himself into her, his own shout of triumph mingling with her cries. The room was silent for a moment, the only sound the harsh, ragged breaths of the two spent lovers.
And then, with a final, guttural moan, Mrs. Kelly collapsed onto the bed, her legs trembling uncontrollably. Bill watched in amazement as she rolled over, her face a mask of agony and ecstasy.
But the madam’s voice cut through the silence like a knife. “I didn’t hear a scream, old-timer,” she said, her tone cold and unyielding. “Looks like you’ve got some more work to do.”
Bill’s heart sank, his body already aching from the exertion of the night. He looked down at Mrs. Kelly, her breasts heaving with each breath, her pussy red and swollen from his relentless pounding. He knew he couldn’t go on much longer, but the thought of losing his gold, of failing in front of this woman who had come to mean so much to him in such a short time, was unbearable.
With a grim determination, he began again, his cock slick with lard and sweat. He took her from behind this time, her plump ass jiggling with each thrust. Mrs. Kelly’s cries grew louder, her body tightening around him like a vice. But still, the madam’s voice echoed in his ears, a taunting reminder of the challenge that lay before him.
The candle had burned down to a nub, casting the room in a flickering, hellish glow that painted Mrs. Kelly’s skin in shades of red and black. Bill felt the pressure building, his cock swelling until it was painful. He reached around, his hand finding her clit, and began to rub it in time with his thrusts. She screamed again, the sound a mix of pain and pleasure that seemed to resonate through the very fabric of the room.
But it wasn’t enough. The madam’s footsteps grew louder in the hallway, and he knew she was waiting, her greedy eyes eager for the moment when she could claim his gold. He had to push himself further, to find a way to make Mrs. Kelly scream so loud she’d be heard in the very bowels of the earth.
With a snarl, he increased his pace, his cock slamming into her with a ferocity that seemed to shake the bed. Mrs. Kelly’s nails dug into the wood, leaving little half-moons in the finish. Her eyes were squeezed shut, her teeth bared in a grimace of pain. And then, with a final, desperate lunge, he found it, that sweet spot that made her entire body spasm.
Her scream was like nothing he’d ever heard before, a sound that seemed to come from the very depths of her soul. It was a sound that could have woken the dead, a sound that made the hairs on the back of his neck stand on end. And as the last echoes of her cry faded into the night, he knew he’d won. The madam’s footsteps retreated down the hallway, her challenge met and bested.
Bill collapsed onto the bed beside Mrs. Kelly, his chest heaving. He looked into her eyes, the pain and pleasure mingling there in a way that was almost beautiful. “Thank you,” he murmured, his voice hoarse from his own shouts. She looked back at him, a knowing smile playing on her lips.
“You’re welcome, darling,” she whispered, her voice a mere breath of sound. “But don’t think you’re off the hook just yet. You’ve still got four more hours to go.”
The room grew quiet once more, the candle casting shadows across their exhausted forms. But in that silence, a new challenge was born. Bill knew that he had to give Mrs. Kelly everything he had, to push her to the very limits of what she could endure. And as he leaned in to kiss her bruised and swollen lips, he felt a spark of excitement flare in his chest.
The night was far from over, and the stakes had just gotten higher. But with each passing moment, the fear and doubt began to recede, replaced by a fierce, burning desire to conquer this woman, to claim her as his own. He knew it was a fool’s errand, that no man could ever truly own a creature so wild and fierce. But in the dim light of the Brothel’s room number 7, with the scent of lard and sweat heavy in the air, he felt invincible.
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