Chapter 18: Office Politics
The offer of more money was awfully tempting. But after the experience as Santa’s helper in that humiliating costume, Tommy wasn’t eager to repeat it. Deciding to avoid the risk of an even more embarrassing situation, he took the secretarial position instead.
On Wednesday morning, Tommy clicked through the doors of a private law firm in a head-turning pair of platform pumps. The journey had been a long one, requiring two trains and a bus to get th...
2024-10-11 17:38:30 +0000 UTC
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Chapter 14: The Hand That Leads
At seven-thirty, as the city lights shimmered against the evening sky, a taxi pulled up to the curb outside a towering glass building. On the thirteenth-floor an overpriced cocktail bar awaited, promising a night of business chat and casual flirting. In the cab's backseat, two feminine figures sat in tense silence, the weight of unspoken words hanging heavy between them.
Mr Wright shifted uncomfortably in his seat, rearranging his legs and hearing...
2024-10-10 18:28:19 +0000 UTC
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Chapter 17: Edgy Resolutions
“Erm... hey Henry. Maybe we can talk somewhere a little more private?” Tommy said nervously, glancing around at a group of girls he used to go to school with, all eagerly listening in.
“Er… yeah... sure,” Henry replied, looking shell-shocked at the sight of his oldest friend looking more feminine than most of the girls in the room.
Spotting the open door to the kitchen, Tommy led the way, mincing across the living room, his painful he...
2024-10-04 13:40:48 +0000 UTC
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Chapter 1: NINA
In a room devoid of personality, three agents, whose names would never appear on any official records, began their secret meeting. The space was as bland as it was functional - no windows, no decorations, just neutral walls and a dim overhead light. A large round table dominated the room, its smooth surface holding only a jug of water and three glasses. The only feature breaking the monotony was a crisp, clear screen mounted on the far wall, where profiles scrolled by in...
2024-10-01 13:10:00 +0000 UTC
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Chapter 16: Familiar Faces, Unfamiliar Truths
After overindulging on Christmas Day, Tommy’s stomach had churned with discomfort, making the idea of a detox seem almost appealing. However, after a few days on a strict liquid diet, those thoughts had vanished. He felt perpetually hungry, and although there was no limit on how much juice he could drink, it never truly satisfied him. By Tuesday, he was beginning to doubt how much longer he could endure the emptiness gnawing at him.
<...
2024-09-13 09:13:01 +0000 UTC
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Chapter 13: Polished and Powerless
Mr Wright shifted uncomfortably on the hard plastic stool in the cramped bathroom of his overly feminine apartment. His lower back ached, and his pantied backside had gone numb as he fidgeted under the salon cape draped over his altered body. A clear plastic sheet wrapped around his shoulders, adding to the claustrophobic feeling that seemed to suffocate him. The air was thick with the sharp scent of hair dye, mixing unpleasantly with the aroma of th...
2024-09-10 14:23:00 +0000 UTC
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Chapter 15: Time to Face the Music
"Maddison, I don’t think going out tonight is such a good idea," Tommy said, his tone giving away the anxiety churning inside him.
Maddison rolled her eyes and scoffed. "Come on, Tammy. It’s the Saturday before Christmas. Why wouldn’t you want to go out and have fun?"
"I... I just don’t think I’m ready," Tommy muttered, gritting his teeth.
"Ready for what? To have fun? Nonsense. You took the bus over here, right? And when ...
2024-09-06 09:35:00 +0000 UTC
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Comments welcome
2024-09-03 18:39:15 +0000 UTC
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Chapter 14: Maddison
Shaking atop a pair of Sarah's stiletto-heeled boots, Tommy waited nervously after ringing the doorbell. His trembling wasn’t just from the cold, though the December wind bit through his sheer tights as if they weren’t even there. The main reason was that he was waiting outside his long-term crush’s house, dressed like a woman. He glanced down at what he was wearing - a playsuit, as Monica had called it - and let out a long, drawn-out sigh. Though comfortabl...
2024-08-30 22:47:11 +0000 UTC
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Epilogue
With little choice in the matter, Scott was forced to fully step into Amy's life, taking over her apartment, her extensive wardrobe of designer clothes and shoes, and even working the occasional day at the family business. To Amy’s friends and family, Scott was - and always had been - Amy. As days turned into weeks, and weeks into years, the distinctions between Scott and Amy blurred until they were nearly non-existent. Scott found himself forgetting what it was like to be ...
2024-08-28 14:45:53 +0000 UTC
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Chapter 13: A New BFF
Stretching out his aching body in a rare moment of quiet, Tommy cursed his luck for landing what felt like the worst job imaginable. Standing in a bustling shopping centre with a forced smile plastered across his painted red lips, he had been tasked with greeting parents and their children before escorting them to visit Santa.
He glanced down at the glossy red claws protruding from the tips of his fingers - acrylic extensions he was still struggling to get ...
2024-08-23 09:35:00 +0000 UTC
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Chapter 22: Home Sweet Home
With his towering high-heeled pump pressed firmly on the accelerator, Scott raced back to Epsford. His entire body ached, every muscle sore from the feminine attire he had endured for what felt like an eternity. Yet, despite the physical discomfort, a strange sense of calm began to wash over him. The future was uncertain and filled with unanswered questions, but one thing was clear - whatever challenges lay ahead, he would face them as Scott, as a man.
<...
2024-08-21 10:46:37 +0000 UTC
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Chapter 12: The Pouting Princess
The room fell silent after the possible forfeits were pulled from the hat. Everyone seemed to realize these choices were perhaps the most extreme yet. Breaking the tension, Sarah finally spoke. "So, what will it be, Tammy? New lips or a new man?"
Monica suppressed a giggle as Tommy turned to glare at Sarah. “You can’t be serious?” he whined, his voice filled with frustration. “Why would you even put those choices in there? Do you really h...
2024-08-16 08:45:00 +0000 UTC
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Chapter 12: The Daily Grind
Mr Wright took a deep breath and cautiously stepped out of the coffee shop, the sharp click of his stiletto heels on the concrete echoing in his ears. The door snapped shut behind him, and he flinched, the sound jolting him like a slap on the back. He felt exposed and vulnerable as if the world were watching his every move. He scanned his surroundings, his head pivoting with the wariness of a meerkat on high alert. It was his first solo excursion in public ...
2024-08-14 16:42:27 +0000 UTC
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Chapter 11: Work It Girl
“I hate my sisters,” Tommy thought to himself as he stood in a high end boutique watching the clock tick down towards the end of another long and boring shift. His feet throbbed having been on his high-heeled feet all day, clomping around the shop floor folding and re-folding items of clothing, tidying racks, and worse of all engaging with customers while pretending to know what he talking about.
It was his third and final day and he couldn’t wait ...
2024-08-09 10:12:01 +0000 UTC
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Chapter 21: Breaking Free
'How on Earth has it come to this?' Scott wondered as he sat down, causing the hem of his short dress to ride perilously high up his pantyhosed thighs. Attempting to maintain some semblance of modesty, he crossed his legs, which only increased the tightness and discomfort inside his silky black panties. Exhausted from the emotional toll of the funeral the previous day and the ensuing reception where drinks flowed more freely than tears, his gaze shifted nervo...
2024-08-07 15:24:34 +0000 UTC
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Chapter 10: Rapunzel
On Monday morning, Tommy was jolted awake by the shrill sound of his alarm, feeling utterly exhausted. It was a strange experience to be up so early, meticulously applying makeup to ensure it was perfect for his interview. Despite the sleepiness weighing on his eyelids as he carefully blended his eyeshadow and lined his waterlines, he tried to stay positive as he prepared for the day ahead.
As Tommy stepped out of the house into the freezing morning air to c...
2024-08-02 16:57:06 +0000 UTC
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Chapter 11: Steps of Change
Mia strode confidently out of the hotel, warmly greeting the doorman with a "Good morning." It was a typical late autumn day - the last leaves clinging stubbornly to the trees and a crisp chill hanging in the air, though not uncomfortably cold. Dressed in jeans, a cashmere sweater, and ankle boots with a low heel, Mia was the epitome of smart casual. Glancing back towards the hotel, she caught sight of her former boss, Morgan Wright, looking decidedly less ...
2024-07-31 16:35:28 +0000 UTC
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Chapter 9: The Social Butterfly
Tommy looked up slowly, his eyes meeting those of his sisters, who loomed above him with amused smiles. "You can't be serious! These choices are awful," he exclaimed, his voice cracking.
"Come on, Tammy! Are you sure you're not secretly loving this?" Sarah teased, a mischievous glint in her eyes as she playfully rolled them. "You've plenty of chances to find a job.”
"Of course, I'm not loving this!" Tommy responded sharply. "I've been look...
2024-07-26 16:26:28 +0000 UTC
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Chapter 20: Echoes of Past Life
Scott sat shaking in the chilly embrace of an ancient stone church, his shivers partly from the cold and partly from the crippling fear of the eulogy he was about to deliver. The surreal experience deepened as the priest began the funeral ceremony for a person Scott had never known.
As the priest's voice echoed throughout the space, Scott's gaze wandered around the interior of the old church. Stone walls, buttressed and solid, framed the large sta...
2024-07-24 23:47:28 +0000 UTC
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Chapter 8: As Hope Flutters Away
With Monday's interview at the forefront of his mind, Tommy faced a critical decision. He had never had long nails or work false eyelashes before, meaning he wasn't sure how easy either would be to remove. However, his decision was ultimately influenced by a memory of Ruby O'Shay, an old classmate who was never seen without her long, colourful nails. He remembered how she had once broken one, the pain evident as she nursed her finger while cursing. Not...
2024-07-19 08:34:00 +0000 UTC
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Chapter 10: Signed, Sealed, and Delivered
Glancing to her right, Mia couldn't help but smirk. The sight of Mr Wright perched on a high stool was nectar to her soul. With his curvaceous thighs pressed tightly together and his nylon-covered ankles crossed neatly, he stared blankly at the far wall of the room, his expression one of utter mortification. When she had first concocted her plan to embarrass her boss - to teach the arrogant, entitled man a lesson, she never imagined it would e...
2024-07-17 17:08:18 +0000 UTC
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Chapter 7: Mr Smarty ‘No’ Pants
"I can't pick one of these!" Tommy exclaimed in despair, throwing his arms in the air. "It's too much! Please, can I pick again?"
"Sorry, Tom," Monica replied sternly, her tone brooking no argument. "You know the rules."
Shaking his head, Tommy let out a heavy sigh as he weighed the consequences of his choices. Whichever choice he made, he was going to look even more feminine; it just boiled down to which option he could stomach more. To...
2024-07-12 09:54:01 +0000 UTC
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Chapter 19: A Family Affair
Scott gazed at his reflection in the hotel bathroom mirror as a wave of anxiety washed over him. It was the eve of the funeral, and he would be spending the next few hours at the Brooks family estate for a meet and greet that promised to be both emotionally charged and socially challenging. He had driven to Bakerton with Jessica earlier that day - a journey that felt much longer than two hours - and was already mentally drained. The radio had filled the voi...
2024-07-09 21:14:43 +0000 UTC
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Chapter 6 – Extended Punishment
"Oh, goody!" Monica exclaimed, clapping her hands together excitedly as she saw the two options Tommy had pulled out. "Time for a trip out. You’ve been cooped up inside for weeks."
"What?! No way! I can't go out!" Tommy protested, a hint of fear creeping into his voice. "I don't have anything to wear!"
"Don't worry about that," Sarah reassured him, "You can borrow something from us."
"But why do we have to go out?" Tommy whined.
2024-07-05 09:24:01 +0000 UTC
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Chapter 9: Third Time is a Charm
Later that evening, Mia and Mr Wright sat side by side in the hotel lobby, awaiting their taxi to Giovanni’s Italian restaurant. The restaurant was a mere ten-minute stroll away, but given the height of Mr Wright's new shiny leather pumps, navigating the distance on foot would have been quite the journey. Mia had briefly entertained the idea of making up some excuse just to watch the pompous man awkwardly stagger through the streets. However, delight...
2024-07-02 21:14:56 +0000 UTC
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Chapter 5: Reflections
Tommy gazed down at his legs, encased in thick, stretchy material and peeking out from beneath a pair of Monica's shorts. Over the shorts, he wore her hoodie and a T-shirt beneath it. Looking up to see Russell the bear smiling at him, Tommy let out a deep, growl-like groan. "Don't say it, Russell," he said firmly. "I know what I look like, but what choice did I have?”
Terrified that the few remaining items of his own clothing would disappear like every o...
2024-06-28 09:36:00 +0000 UTC
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Chapter 18: Tinted Reflections
Emily's salon was a serene oasis of calmness, punctuated only by the soft hum of hairdryers and fragments of conversations drifting from nearby chairs. In this tranquil atmosphere, Scott sat, his hair divided into neat sections and wrapped in foils, while his mind was anything but calm. As the dye worked its magic, adjusting the colour of his natural hair to match the newly added extensions, his thoughts weighed heavily on him. Catching his distant expre...
2024-06-25 18:56:35 +0000 UTC
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Chapter 4: Russell
Tommy gritted his teeth, staring in horror at his reflection. His brows, once thick and bushy, had been plucked into almost non-existence. He had agonized over his decision, flip-flopping between daunting forfeits, before finally settling on this one. Monica, visibly surprised by her brother’s choice, had eagerly set to work, while Sarah captured the entire process on camera, her giggles filling the room. Running his fingers over his now nearly pencil-thin arches,...
2024-06-20 10:12:00 +0000 UTC
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Chapter 8: Round Two
After thanking Madame Maria for her exceptional work and for coming on such short notice, Mia escorted the large woman out of the door of her luxurious penthouse suite. Turning to face Mr Wright, she found it hard to believe the pouting, feminized figure before her was the same imposing boss she had endured for so long. Dressed in the outfit Mia had bought while out shopping that morning - a perfect mix of preppy and provocative - he epitomized the stereotypical b...
2024-06-16 09:24:00 +0000 UTC
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