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A Burglar's Regression — Chapter One & Two


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Chapter One

The Job

 

Jake crouched in the shadows of the sprawling estate, the weight of his duffel bag pulling slightly on his shoulder. He adjusted his gloves, the cool leather stretching snug over his knuckles, and scanned the mansion for signs of life. It was massive, the kind of house people dream about when they imagine making it big. Jake smirked. For him, it wasn’t about dreams. It was about opportunity.

The place looked dead—no cars in the driveway, no lights on in the windows. Exactly as his research had suggested. He’d spent weeks watching this house, noting the schedules of anyone who came and went. No one was supposed to be home tonight.

His breath fogged in the crisp night air as he moved to the side of the house. The lock on the basement window was a joke. A couple of minutes with a thin blade, and it popped open. He slid inside quietly, landing on carpeted floors. The faint scent of lavender hit him as he straightened, but he ignored it. Focus was everything now.

Jake pulled a small flashlight from his pocket, the beam barely cutting through the darkness. His goal was simple: quick in, quick out. Jewelry, cash, maybe electronics if he had time. Nothing too bulky—stuff he could flip fast without raising eyebrows.

The mansion was even more ridiculous on the inside. Everything was oversized, polished, and pristine. It screamed wealth, from the marble flooring to the ornate chandeliers. Jake’s chest tightened slightly as he moved through the rooms, his footsteps silent on the rugs. This kind of place was out of reach for guys like him—always had been. But tonight, a small piece of it would be his.

The first haul was easy. A couple of expensive watches from the bedroom dresser, a sleek tablet, and a gold bracelet from a jewelry box on the vanity. Jake worked efficiently, his movements automatic. He didn’t stop to admire the decor or question how someone could afford all this. It didn’t matter. What mattered was getting out before anyone noticed anything was gone.

Then he found that room.

Jake paused, his hand hovering over the doorknob. Something about this one felt different. The rest of the house was all open spaces and luxury; this door was plain, almost out of place. It was locked, but the lock itself was basic—a cheap tumbler mechanism. Jake didn’t think twice. A quick twist with his pick, and the door clicked open.

His flashlight beam swept across the room, and he froze.

It wasn’t a storage room. It wasn’t an office. It was something... bizarre. The walls were painted pastel pink, and shelves lined with stuffed animals and other childish knick-knacks hugged the perimeter. But the furniture was what hit him the hardest—an oversized crib, a highchair clearly made for an adult, and a wardrobe partially open to reveal rows of frilly dresses that could only be described as costumes.

“What the hell...” Jake muttered under his breath, taking a step inside. The smell here was different—sweet, powdery. Something about it turned his stomach.

Curiosity outweighed caution. He walked further in, his gloved hand brushing over the smooth wood of the crib. He didn’t understand it. What kind of person owned a room like this? A joke? A kink thing? His brain scrambled for an explanation that made sense. Rich people were weird—he’d seen enough during his jobs—but this was on another level.

Jake moved to the wardrobe, reaching for one of the dresses. He wasn’t sure why. Something about it felt unreal, like he needed to confirm it wasn’t some elaborate prank. The fabric was soft and frilly under his fingers, and he quickly dropped it back into place, disgust curling in his gut.

A sound behind him made his blood run cold.

The lights clicked on, and Jake spun around, his heart slamming into his ribs. Standing in the doorway was a woman. Tall, elegant, and composed, she had sharp features framed by dark, perfectly styled hair. She wore a sleek black dress that hugged her figure, and her heels clicked against the floor as she stepped inside.

Jake’s instincts kicked in, and he dropped the flashlight, reaching for the knife in his pocket. Before he could pull it, the woman raised her hand.

“Don’t bother,” she said, her voice smooth but commanding. “You’re not going to use that.”

Jake hesitated. Her eyes pinned him in place. She didn’t look scared. She didn’t even look angry. She looked... amused.

“Listen, lady, I don’t want any trouble. I’m leaving.” His voice sounded shaky to his own ears, and he hated it. He didn’t wait for her to respond. He moved toward the door, but she blocked his path.

“I’m afraid you’re not going anywhere, Jake.”

The sound of his name stopped him cold. His chest tightened as panic bubbled up. “How the hell do you know my name?”

The woman smiled, and it sent a chill down his spine. “Oh, I know everything about you. Your name, your little ‘side hustle,’ even the last three houses you broke into. You’ve been sloppy.”

Jake’s grip tightened on the knife. He could push past her. He could run. But something about the way she looked at him made him hesitate.

“I could call the police,” she continued, tilting her head. “Show them the security footage of you breaking in. But that’s not nearly as interesting as what I have in mind.”

Jake’s mouth went dry. “What are you talking about?”

Her smile widened, and she stepped closer. “I’m offering you a choice, Jake. Prison... or me. Stay, and I’ll teach you some lessons you clearly never learned.” Her eyes flicked to the room around them, and Jake’s stomach turned. “Lessons in discipline. Obedience. Manners.”

His mind raced. Prison would mean years behind bars—he’d never survive that. But staying here, with her, in this... nightmare of a house? Every instinct screamed at him to run, to fight, to do something.

And yet, all he could do was stand there, frozen, as her words echoed in his ears.

“You’re going to thank me for this one day.”

The last thing Jake felt was the door shutting behind him.

 

 

Chapter Two

Jake’s Nightmare

 

Jake’s wrists burned where the zip ties dug into his skin. He sat slumped on the floor of the strange room, his back pressed against the oversized crib. The polished wooden bars felt cold and unyielding, a sharp contrast to the warmth of his rising panic. His legs were stretched out in front of him, useless with his ankles bound the same way as his wrists.

“What... what are you doing?” His voice came out shaky, more desperate than he wanted.

Madame Evelyn didn’t respond immediately. She was at the wardrobe, methodically pulling out items and laying them on the changing table—a stack of diapers, bottles of powder, and frilly clothes he couldn’t even bring himself to look at directly. Her calm, deliberate movements made his skin crawl. It was like she had all the time in the world, and that scared him more than if she’d been angry or frantic.

“Hey! I’m talking to you!” Jake twisted his arms against the restraints, wincing as the ties bit deeper. “This isn’t funny, lady. Let me go!”

Evelyn finally turned to face him, holding something in her hands that made his stomach drop—a large, white diaper, absurdly oversized. She raised an eyebrow, clearly unimpressed with his struggling. “You agreed to my terms, Jake. This is part of your rehabilitation.”

His throat tightened. “No, no, no. This isn’t happening.” He kicked his bound legs, scooting away from her as much as he could, which wasn’t far. His shoulders banged against the crib bars. “You can’t—this is insane! You’re insane!”

Evelyn didn’t flinch. “Insane, perhaps,” she said with a faint smile, “but effective.” She crouched in front of him, her dark eyes locking onto his. “You’re not in control here, Jake. That’s the point. The sooner you accept it, the easier this will be.”

Jake’s breathing quickened. His heart pounded so loudly in his chest that it drowned out the rest of the room. “You can’t do this. I’ll—I’ll report you. You think you’re untouchable?” He tried to sound threatening, but his voice cracked. It wasn’t convincing, even to him.

“You’ll report me?” Evelyn’s voice dripped with amusement. “And tell them what? That you broke into my home and now you’re upset about the consequences? Be my guest.”

Jake opened his mouth but found no words. She was right. He had no leverage, no way out. The realization hit him like a punch to the gut, and he slumped back against the crib.

She stood and crossed the room again, grabbing a pair of scissors from a nearby shelf. Jake’s stomach twisted as she approached. “What are you doing with those?” He tensed, instinctively trying to scoot away again, but she reached for his zip-tied wrists.

“Relax,” she said sharply. “I’m not going to hurt you. Not physically, anyway.”

The plastic ties snapped under the blade, and his arms fell limply to his sides. He rubbed at the raw skin on his wrists, glaring up at her. His anger flared for a moment, but it fizzled as she gestured toward the changing table.

“Up,” she commanded.

Jake blinked. “What?”

“Up. On the table. Now.” Her voice had an edge that left no room for argument.

He shook his head, his lips curling into a bitter smile. “You’re out of your damn mind if you think I’m—”

Evelyn didn’t wait for him to finish. In one swift motion, she grabbed his arm and hauled him to his feet with surprising strength. Jake stumbled, caught off guard, and before he could regain his balance, she shoved him toward the table.

“Get up, or I’ll make this worse for you,” she said, her tone ice-cold. “You’ll learn soon enough that defiance doesn’t get you anywhere.”

Jake hesitated, his muscles locking as he glanced at the open door. Could he make a run for it? The thought vanished almost as quickly as it came. Even if he got past her, his legs were still tied. He wouldn’t make it five steps.

Grinding his teeth, he climbed onto the table, the padded surface creaking under his weight. Every fiber of his body screamed at him to fight, to resist, but fear kept him rooted.

Evelyn wasted no time. She secured his ankles to the table’s built-in straps, immobilizing him completely. Jake struggled instinctively, but the restraints held firm.

“This isn’t happening,” he muttered under his breath, his voice barely audible. His fists clenched at his sides. “This isn’t real.”

“Oh, it’s very real,” Evelyn said, her voice maddeningly calm. She pulled a fresh diaper from the stack and unfolded it with a practiced ease. Jake turned his head away, his cheeks burning with humiliation. He felt her grip his ankle and heard the sound of the Velcro straps tightening further.

“Don’t you dare—”

His protest was cut off by the cold air hitting his skin as she unceremoniously tugged his pants and boxers down. The fabric bunched around his restrained ankles, leaving him exposed. Jake’s face burned hotter. “Stop! What the hell is wrong with you?”

Evelyn didn’t respond. She simply lifted his legs by the ankles with one hand—like he weighed nothing—and slid the diaper beneath him with the other. Jake squirmed, but it was useless. She had complete control.

“You need to stop fighting, Jake,” she said as she sprinkled powder over him. The scent was cloyingly sweet, and he gagged slightly, turning his head further away. “It’ll only make this harder for you.”

“This is sick,” he spat. His voice cracked with frustration, and he hated himself for how small he sounded. “You’re sick.”

“Perhaps,” she said, pulling the diaper snugly between his legs and taping it into place. The sound of the adhesive tabs fastening made Jake’s stomach churn. “But I’m not the one who thought breaking into a stranger’s house was a good idea.”

When she stepped back, Jake refused to look at her. He stared at the ceiling instead, his jaw clenched so tightly it ached. The diaper felt bulky and foreign against his skin, a constant, humiliating reminder of his helplessness.

Evelyn walked to the side of the table and leaned down, her face close to his. “That wasn’t so bad, was it?”

Jake finally snapped, his voice rising. “You’re insane! You think you can just—”

Her hand clamped over his mouth, silencing him. Her eyes bore into his, calm but deadly serious. “I can, and I will,” she said softly. “You have no idea what’s in store for you, Jake. But you’ll learn.”

When she let go, Jake stayed silent. For the first time, the reality of his situation began to sink in. He wasn’t just trapped in her house. He was trapped in her world.

And there was no way out.

 

----------------------------------------------------------------------------------------------------------------------------------------------------------

 

Hi guys, here's one of my latest stories. You can read it now on Amazon Kindle here: https://www.amazon.com/dp/B0DQYQQ2D1

You can also read Daisy's Perfect Summerhttps://www.amazon.com/dp/B0DLVJYHH5

Here's a link to The Diary of a Diapered Cuckoldhttps://www.amazon.com/dp/B0DPFLGMNJ

  • Like 10
  • 2 weeks later...
Posted
On 12/19/2024 at 10:50 PM, TheLittleWriter said:

Chapter One

The Job

 

Jake crouched in the shadows of the sprawling estate, the weight of his duffel bag pulling slightly on his shoulder. He adjusted his gloves, the cool leather stretching snug over his knuckles, and scanned the mansion for signs of life. It was massive, the kind of house people dream about when they imagine making it big. Jake smirked. For him, it wasn’t about dreams. It was about opportunity.

The place looked dead—no cars in the driveway, no lights on in the windows. Exactly as his research had suggested. He’d spent weeks watching this house, noting the schedules of anyone who came and went. No one was supposed to be home tonight.

His breath fogged in the crisp night air as he moved to the side of the house. The lock on the basement window was a joke. A couple of minutes with a thin blade, and it popped open. He slid inside quietly, landing on carpeted floors. The faint scent of lavender hit him as he straightened, but he ignored it. Focus was everything now.

Jake pulled a small flashlight from his pocket, the beam barely cutting through the darkness. His goal was simple: quick in, quick out. Jewelry, cash, maybe electronics if he had time. Nothing too bulky—stuff he could flip fast without raising eyebrows.

The mansion was even more ridiculous on the inside. Everything was oversized, polished, and pristine. It screamed wealth, from the marble flooring to the ornate chandeliers. Jake’s chest tightened slightly as he moved through the rooms, his footsteps silent on the rugs. This kind of place was out of reach for guys like him—always had been. But tonight, a small piece of it would be his.

The first haul was easy. A couple of expensive watches from the bedroom dresser, a sleek tablet, and a gold bracelet from a jewelry box on the vanity. Jake worked efficiently, his movements automatic. He didn’t stop to admire the decor or question how someone could afford all this. It didn’t matter. What mattered was getting out before anyone noticed anything was gone.

Then he found that room.

Jake paused, his hand hovering over the doorknob. Something about this one felt different. The rest of the house was all open spaces and luxury; this door was plain, almost out of place. It was locked, but the lock itself was basic—a cheap tumbler mechanism. Jake didn’t think twice. A quick twist with his pick, and the door clicked open.

His flashlight beam swept across the room, and he froze.

It wasn’t a storage room. It wasn’t an office. It was something... bizarre. The walls were painted pastel pink, and shelves lined with stuffed animals and other childish knick-knacks hugged the perimeter. But the furniture was what hit him the hardest—an oversized crib, a highchair clearly made for an adult, and a wardrobe partially open to reveal rows of frilly dresses that could only be described as costumes.

“What the hell...” Jake muttered under his breath, taking a step inside. The smell here was different—sweet, powdery. Something about it turned his stomach.

Curiosity outweighed caution. He walked further in, his gloved hand brushing over the smooth wood of the crib. He didn’t understand it. What kind of person owned a room like this? A joke? A kink thing? His brain scrambled for an explanation that made sense. Rich people were weird—he’d seen enough during his jobs—but this was on another level.

Jake moved to the wardrobe, reaching for one of the dresses. He wasn’t sure why. Something about it felt unreal, like he needed to confirm it wasn’t some elaborate prank. The fabric was soft and frilly under his fingers, and he quickly dropped it back into place, disgust curling in his gut.

A sound behind him made his blood run cold.

The lights clicked on, and Jake spun around, his heart slamming into his ribs. Standing in the doorway was a woman. Tall, elegant, and composed, she had sharp features framed by dark, perfectly styled hair. She wore a sleek black dress that hugged her figure, and her heels clicked against the floor as she stepped inside.

Jake’s instincts kicked in, and he dropped the flashlight, reaching for the knife in his pocket. Before he could pull it, the woman raised her hand.

“Don’t bother,” she said, her voice smooth but commanding. “You’re not going to use that.”

Jake hesitated. Her eyes pinned him in place. She didn’t look scared. She didn’t even look angry. She looked... amused.

“Listen, lady, I don’t want any trouble. I’m leaving.” His voice sounded shaky to his own ears, and he hated it. He didn’t wait for her to respond. He moved toward the door, but she blocked his path.

“I’m afraid you’re not going anywhere, Jake.”

The sound of his name stopped him cold. His chest tightened as panic bubbled up. “How the hell do you know my name?”

The woman smiled, and it sent a chill down his spine. “Oh, I know everything about you. Your name, your little ‘side hustle,’ even the last three houses you broke into. You’ve been sloppy.”

Jake’s grip tightened on the knife. He could push past her. He could run. But something about the way she looked at him made him hesitate.

“I could call the police,” she continued, tilting her head. “Show them the security footage of you breaking in. But that’s not nearly as interesting as what I have in mind.”

Jake’s mouth went dry. “What are you talking about?”

Her smile widened, and she stepped closer. “I’m offering you a choice, Jake. Prison... or me. Stay, and I’ll teach you some lessons you clearly never learned.” Her eyes flicked to the room around them, and Jake’s stomach turned. “Lessons in discipline. Obedience. Manners.”

His mind raced. Prison would mean years behind bars—he’d never survive that. But staying here, with her, in this... nightmare of a house? Every instinct screamed at him to run, to fight, to do something.

And yet, all he could do was stand there, frozen, as her words echoed in his ears.

“You’re going to thank me for this one day.”

The last thing Jake felt was the door shutting behind him.

 

 

Chapter Two

Jake’s Nightmare

 

Jake’s wrists burned where the zip ties dug into his skin. He sat slumped on the floor of the strange room, his back pressed against the oversized crib. The polished wooden bars felt cold and unyielding, a sharp contrast to the warmth of his rising panic. His legs were stretched out in front of him, useless with his ankles bound the same way as his wrists.

“What... what are you doing?” His voice came out shaky, more desperate than he wanted.

Madame Evelyn didn’t respond immediately. She was at the wardrobe, methodically pulling out items and laying them on the changing table—a stack of diapers, bottles of powder, and frilly clothes he couldn’t even bring himself to look at directly. Her calm, deliberate movements made his skin crawl. It was like she had all the time in the world, and that scared him more than if she’d been angry or frantic.

“Hey! I’m talking to you!” Jake twisted his arms against the restraints, wincing as the ties bit deeper. “This isn’t funny, lady. Let me go!”

Evelyn finally turned to face him, holding something in her hands that made his stomach drop—a large, white diaper, absurdly oversized. She raised an eyebrow, clearly unimpressed with his struggling. “You agreed to my terms, Jake. This is part of your rehabilitation.”

His throat tightened. “No, no, no. This isn’t happening.” He kicked his bound legs, scooting away from her as much as he could, which wasn’t far. His shoulders banged against the crib bars. “You can’t—this is insane! You’re insane!”

Evelyn didn’t flinch. “Insane, perhaps,” she said with a faint smile, “but effective.” She crouched in front of him, her dark eyes locking onto his. “You’re not in control here, Jake. That’s the point. The sooner you accept it, the easier this will be.”

Jake’s breathing quickened. His heart pounded so loudly in his chest that it drowned out the rest of the room. “You can’t do this. I’ll—I’ll report you. You think you’re untouchable?” He tried to sound threatening, but his voice cracked. It wasn’t convincing, even to him.

“You’ll report me?” Evelyn’s voice dripped with amusement. “And tell them what? That you broke into my home and now you’re upset about the consequences? Be my guest.”

Jake opened his mouth but found no words. She was right. He had no leverage, no way out. The realization hit him like a punch to the gut, and he slumped back against the crib.

She stood and crossed the room again, grabbing a pair of scissors from a nearby shelf. Jake’s stomach twisted as she approached. “What are you doing with those?” He tensed, instinctively trying to scoot away again, but she reached for his zip-tied wrists.

“Relax,” she said sharply. “I’m not going to hurt you. Not physically, anyway.”

The plastic ties snapped under the blade, and his arms fell limply to his sides. He rubbed at the raw skin on his wrists, glaring up at her. His anger flared for a moment, but it fizzled as she gestured toward the changing table.

“Up,” she commanded.

Jake blinked. “What?”

“Up. On the table. Now.” Her voice had an edge that left no room for argument.

He shook his head, his lips curling into a bitter smile. “You’re out of your damn mind if you think I’m—”

Evelyn didn’t wait for him to finish. In one swift motion, she grabbed his arm and hauled him to his feet with surprising strength. Jake stumbled, caught off guard, and before he could regain his balance, she shoved him toward the table.

“Get up, or I’ll make this worse for you,” she said, her tone ice-cold. “You’ll learn soon enough that defiance doesn’t get you anywhere.”

Jake hesitated, his muscles locking as he glanced at the open door. Could he make a run for it? The thought vanished almost as quickly as it came. Even if he got past her, his legs were still tied. He wouldn’t make it five steps.

Grinding his teeth, he climbed onto the table, the padded surface creaking under his weight. Every fiber of his body screamed at him to fight, to resist, but fear kept him rooted.

Evelyn wasted no time. She secured his ankles to the table’s built-in straps, immobilizing him completely. Jake struggled instinctively, but the restraints held firm.

“This isn’t happening,” he muttered under his breath, his voice barely audible. His fists clenched at his sides. “This isn’t real.”

“Oh, it’s very real,” Evelyn said, her voice maddeningly calm. She pulled a fresh diaper from the stack and unfolded it with a practiced ease. Jake turned his head away, his cheeks burning with humiliation. He felt her grip his ankle and heard the sound of the Velcro straps tightening further.

“Don’t you dare—”

His protest was cut off by the cold air hitting his skin as she unceremoniously tugged his pants and boxers down. The fabric bunched around his restrained ankles, leaving him exposed. Jake’s face burned hotter. “Stop! What the hell is wrong with you?”

Evelyn didn’t respond. She simply lifted his legs by the ankles with one hand—like he weighed nothing—and slid the diaper beneath him with the other. Jake squirmed, but it was useless. She had complete control.

“You need to stop fighting, Jake,” she said as she sprinkled powder over him. The scent was cloyingly sweet, and he gagged slightly, turning his head further away. “It’ll only make this harder for you.”

“This is sick,” he spat. His voice cracked with frustration, and he hated himself for how small he sounded. “You’re sick.”

“Perhaps,” she said, pulling the diaper snugly between his legs and taping it into place. The sound of the adhesive tabs fastening made Jake’s stomach churn. “But I’m not the one who thought breaking into a stranger’s house was a good idea.”

When she stepped back, Jake refused to look at her. He stared at the ceiling instead, his jaw clenched so tightly it ached. The diaper felt bulky and foreign against his skin, a constant, humiliating reminder of his helplessness.

Evelyn walked to the side of the table and leaned down, her face close to his. “That wasn’t so bad, was it?”

Jake finally snapped, his voice rising. “You’re insane! You think you can just—”

Her hand clamped over his mouth, silencing him. Her eyes bore into his, calm but deadly serious. “I can, and I will,” she said softly. “You have no idea what’s in store for you, Jake. But you’ll learn.”

When she let go, Jake stayed silent. For the first time, the reality of his situation began to sink in. He wasn’t just trapped in her house. He was trapped in her world.

And there was no way out.

 

----------------------------------------------------------------------------------------------------------------------------------------------------------

 

Hi guys, here's one of my latest stories. You can read it now on Amazon Kindle here: https://www.amazon.com/dp/B0DQYQQ2D1

You can also read Daisy's Perfect Summerhttps://www.amazon.com/dp/B0DLVJYHH5

Here's a link to The Diary of a Diapered Cuckoldhttps://www.amazon.com/dp/B0DPFLGMNJ

Hi, I'm following you on amazon and quite enjoy your stories .Have you done a sissy baby cuckold story  husband dressed as a baby girl rather than baby boy ?

  • Like 1
Posted

I like how this is starting.  I've enjoyed your stories on Amazon

Posted
11 hours ago, sissysusie1 said:

Hi, I'm following you on amazon and quite enjoy your stories .Have you done a sissy baby cuckold story  husband dressed as a baby girl rather than baby boy ?

I'm working on a long sissy baby story. It's about this married man who wants to be cuckolded by his wife. She finally gives him what he wants, but it takes him down a rabbit hole. Diapers, breastfeeding, forced bisexuality, feminization, exposure, and more! 

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