Crossdressing Stories - Turned Into A Personal Doll

Published on Mar 14, 2024 by Tohka Crow

In the icy embrace of the night, the small city pulsed with an uneasy tranquility, its narrow alleys echoing with the remnants of merriment from nearby pubs. Shaun, a figure misplaced amidst the late-night revellers, wove his way through the ancient cobblestone streets. He wore the weight of failed exams and a shattered relationship like a leaden cloak, his mind awash with regret and self-reproach.

His shoes, once shining with the sheen of university pride, now sloshed through puddles left by a passing rainstorm. The lingering burn of cheap alcohol on his tongue provided a fleeting fortress of courage, an unsteady bulwark against the tide of his distress.

Under the harsh lights of a round-the-clock coffee shop, a girl was haloed, seeming to exist in a world apart from the surrounding chaos. As fragile and beautiful as a porcelain doll, she cradled a cup of steaming coffee, her eyes glinting with reflected neon. Shaun, surrounded by an aura of sour liquor, stumbled toward her. His clumsiness sent her drink tumbling, creating a dark stain on the stone.

"Hey, doll," he mumbled, an unsteady arm reaching for her waist, his words slurring into one another. "Let me...let me get you another one," he offered, a lopsided grin distorting his face as the world spun in dizzying circles.

Before she could respond, a heavy hand landed on Shaun's arm. His blurry gaze met the stern face of a man, an imposing figure dressed in a tailored black suit. Sunglasses concealed his eyes, creating an aura of mystery and danger. Shaun's smile wilted as he recognized the imminent threat. The next thing he knew, a punch sent him spiralling into a whirlpool of darkness, his momentary bravado knocked out cold.

Shaun's eyes fluttered open to unfamiliar surroundings, the harshness of the room's fluorescent light stinging his already throbbing head. He was sitting on a cold steel chair, the rigidity of which reminded him of his grim situation. Across the room stood the mountain of a man who had sent him spiraling into darkness.

"You assaulted the daughter of the city's most influential man," the man stated, his voice cutting through Shaun's foggy consciousness like a knife. "You've landed yourself in some serious trouble, lad."

Before Shaun could muster a response, the door creaked open. The porcelain doll from last night entered, her eyes carrying a softness that sharply contrasted the grim situation. "We're not mobsters or anything like that, so you can relax," she reassured him, her words a soothing balm on his fraying nerves. "We're not going to keep you here against your will."

She paused, then laid out an unexpected proposition. "Here's my offer. You stay here for a month, working as my personal assistant, or we call the police. They'll have you booked for assault."

Shaun felt as if the room was spinning again, but this time, not from intoxication. The prospect of a criminal record chilled him to the bone, stinging more than the failed exams or the breakup with his girlfriend. He was young, his life just beginning, and he could not afford to have his future tarnished by a reckless mistake.

In his heart, he knew he had only one choice. With a lump in his throat and a reluctant nod, Shaun agreed to her terms. "I accept," he mumbled, not quite knowing what he was getting himself into.

"What's your name?" she asked, a smirk playing on her lips.

"Shaun," he replied, trying to adjust to the sudden turn of events.

"No, wrong answer. From today, you're Sandy," she declared with a gleam in her eye. "I didn't quite like how you referred to women as dolls. So, you'll be my personal doll now. Let's see how you like it."

Shaun was taken aback, disbelief rippling across his face. But before he could react, she was guiding him through a door and into his new room. The room was an explosion of pink and floral patterns, overly feminine and surreal.

"How do you like your new room, Sandy?" she asked, her voice laced with amusement. Shaun, now Sandy, found himself at a loss for words.

Before he could respond, the door opened again and three women walked in. "Sandy, meet your transformation team," the girl, who Shaun now understood to be Megan, introduced them with a flourish. "I'll leave you with them, and I'll see you once you've fully transformed into Sandy."

With those final words, Megan exited the room, leaving Sandy with the three women and a new reality that was as unpredictable as the city's night.

The three women were patient yet insistent. "First, you need to take a bath and shave entirely," one of them ordered, her tone kind but firm.

Sandy felt a hot blush creeping up her neck, embarrassment and unease swirling within her. She'd never done anything like this before. As she moved towards the bathroom, a pair of soft, pink lace panties was handed to her. She held them gingerly in her hands, the fabric foreign and the implications startling. A whirl of confusion twined with a strange intrigue coursed through her.

The warmth of the bath was a small comfort amidst the tumult. The sensation of the razor sliding over her skin, removing the coarse stubble was unnerving, yet there was an odd sense of liberation accompanying it. Each stroke seemed symbolic, as though she was shedding parts of her old self, leaving her bare and vulnerable yet strangely invigorated.

Emerging from the bath, she hesitated before the mirror, the pink panties a stark contrast to her damp, freshly shaven skin. She took a deep breath, then stepped into them, the lace fabric feeling unusually soft against her smooth skin. The snug fit felt oddly comforting, though it served as a continuous reminder of her unusual predicament.

This journey of transformation, every second of it, was a constant tug-of-war between her old self and the person she was being asked to become. No longer Shaun, she was morphing into Sandy, and in an unexpected twist, the dread was slowly being overtaken by a peculiar sense of intrigue.

As Sandy emerged from the bathroom, one of the ladies efficiently fitted her with a silicone breastplate, the foreign weight settling against her chest. A bra was slipped on to hold the prosthetic in place, contouring a new shape on her body. Hip pads followed, slipped into a pair of tights that sculpted a more feminine form.

But it was the corset that brought the real transformation. Tightened around her midsection, it cinched her waist into an hourglass figure, the laces digging into her skin as they redefined her silhouette. She felt a peculiar mix of discomfort and fascination, the unfamiliar curves of her body igniting a strange curiosity within her.

She found herself standing in front of the mirror, her reflection a stranger. The woman staring back at her was not Shaun, but Sandy, a person she was just beginning to understand. Her new figure, shapely and feminine, was a stark contrast to the reflection she was accustomed to.

An unexpected wave of curiosity swept over her. She studied her new silhouette, traced the curves that the corset and pads had crafted. There was a sense of uncanniness, of course, but also a sense of intrigue, as if she was looking at a different version of herself through a looking glass.

This wasn't just a physical transformation; it was a journey of self-discovery that was stirring a dormant curiosity within her. Sandy was not just a facade she wore to avoid punishment; she was becoming a mirror into a side of herself that Shaun had never explored.

Next came the makeup, an intricate process that seemed like a dance between art and deception. A subtle layer of foundation smoothed over her skin, followed by a blush of color on her cheeks. Mascara brushed against her eyelashes, lengthening and darkening them. Eyeliner framed her eyes, giving them a defined and distinct look, and a shade of red graced her lips, turning them into a bold statement.

The process was mesmerizing, each brush stroke bringing forth a new facet of her face. Sandy found herself becoming more intrigued by the transformation, her initial apprehension fading into the background. She saw how makeup could sculpt and highlight, could camouflage and reveal, all at once.

When the wig was placed onto her head, the long, wavy tresses framing her made-up face, she hardly recognized herself. The person in the mirror was Sandy, through and through - a woman with sparkling eyes, defined curves, and a radiant smile. It was surreal, and she found herself smiling back at her reflection, a strange but not unpleasant warmth spreading through her.

Finally, they brought in a tight pencil skirt and a secretary-style white shirt, both hugging her new figure closely. As she slipped into them, Sandy realized she was no longer just enduring this transformation, she was actually starting to enjoy it.

Her new persona, Sandy, was as real as Shaun ever was, a persona she was beginning to embrace with curiosity and amusement. Sandy was no longer just a character she had to play, but a part of herself she was beginning to explore, and surprisingly, to enjoy.

Sandy, the woman Shaun had become, entered the room where Megan awaited, each click of her heels echoing a new facet of her emerging personality. Megan scrutinized her transformation, her smile revealing a sense of satisfaction.

"And how does it feel, Sandy, to be the doll now?" Megan asked, an edge of playful mockery in her tone.

Her expression softened as she continued, "I've reconsidered the situation. You can leave right now if you want to, we won't press any charges." A momentary silence fell between them as she offered an alternative, "Or, you can stay and I can teach you more about being a 'doll'."

A surge of confusion washed over Sandy. She was caught in a tumultuous storm of thoughts and emotions. She thought of her failed exam, her recent heartbreak, and the icy silence that had descended between her parents and her since their fight last year. There was no one expecting her return, no one who would miss Shaun.

In that moment, amidst the whirl of uncertainty, clarity emerged. Looking into Megan's expectant eyes, her cheeks tinged with a blush of embarrassment and perhaps a hint of excitement, she finally spoke. "I...I want to stay," she admitted softly, her decision solidifying her commitment to this unusual path.

Megan smiled, her gaze soft yet holding a hint of playful mischief. "Good decision, Sandy. Now, let's get started."

As the days passed, Sandy found herself adjusting to her new environment. She began to understand the nuances of her role as Megan's "personal assistant". Each day brought new challenges, and each night, a sense of accomplishment. Tasks that initially felt awkward and uncomfortable, like choosing outfits and applying makeup, gradually became second nature.

The three girls, initially strangers, slowly became friends. They helped Sandy navigate her new life with kindness and patience. From styling her hair to teaching her how to walk in heels, their support became invaluable.

After a few days of intense training, Megan dropped the bombshell. "There will be a party at the house," she announced one morning, her tone casual. "It's a business meeting. All important figures of the city will be there, and you, Sandy, will join the ladies in serving them." She added, stressing the last part, "You cannot fail."

A wave of panic swept over Sandy. She had no prior experience in such a setting, let alone as a waitress. The days leading up to the event were a blur of practice and preparation.

The day of the party finally arrived. Sandy was dressed in a short black pencil skirt that hugged her figure, a crisp white blouse with a neat bow tie and elegant black heeled shoes. She looked at her reflection, a cocktail of excitement and nervousness churning inside her.

The party was a grand affair. The house was filled with men in sharp suits and ties. Sandy, along with the other girls, swirled around the room, serving canapes and refilling glasses of expensive wine. The air was filled with a mix of cigar smoke and men's cologne.

She could feel the eyes of the men following her every move. Some even went as far as to catcall her, their lewd comments sending waves of embarrassment through her. But Sandy held her head high, remembering Megan's stern warning. She couldn't afford to fail.

She was no longer Shaun, the university student with a failed exam and a broken heart. She was Sandy now, Megan's assistant, standing tall amidst a room full of powerful men, serving them with a grace she never knew she possessed. This was her new reality, one that she was still learning to navigate.

After the successful party, Sandy felt a sense of accomplishment, and Megan's subtle nod of appreciation further bolstered her confidence. Over the next few days, they found themselves spending more time together, the bond between them gradually deepening.

One evening, they sat together on the balcony, the city sprawling before them under a palette of breathtaking sunset hues. In the quietness of the moment, Megan opened up about her innermost feelings. "Behind this facade of a strong, confident woman, I'm just... lonely," she admitted, her voice barely more than a whisper. "I'm the daughter of a powerful man, and it isolates me. No one wants to be friends with someone they see as intimidating or unreachable."

Sandy listened quietly, her heart aching for Megan. She realized then that they were both victims of circumstance in their own ways, struggling to navigate the challenges life had thrown at them.

Encouraged by Sandy's understanding and empathy, Megan began to trust her more. Over time, Sandy found herself entrusted with more important responsibilities. She was no longer just a personal assistant but a valued part of Megan's business. She was involved in decision-making processes and even managed certain aspects of the business.

Every day brought new challenges and experiences, but Sandy was ready to face them all. Her journey was not merely a transformation from Shaun to Sandy anymore; it was a journey of growth and self-discovery, of finding her place in an unexpected world.

As the thirty-day mark approached, Sandy could feel a tension brewing. Then, on that fateful day, Megan summoned Sandy to her office. As Sandy walked into the room, she found Megan sitting behind her desk, her eyes staring down at the polished mahogany surface, a sense of sadness etched on her face.

"Megan?" Sandy queried, her heart pounding. The room felt unnervingly silent.

"It's been a month, Sandy," Megan said, her voice barely above a whisper.

Sandy felt her heart sink, but she said nothing. She didn't want to leave. She'd grown fond of this place, of Megan, and of herself - Sandy. She yearned to tell Megan, but the words seemed to stick in her throat.

Seeing that Megan had nothing more to add, Sandy nodded, her heart heavy. She turned towards the door, her hand resting on the doorknob. She was about to leave when she heard Megan's voice.

"Sandy, wait."

Sandy turned around. Her eyes met Megan's, and in that moment, both women understood the unsaid. They didn't want to part ways. Megan broke the silence, her voice trembling slightly, "Do you really want to leave, Sandy?"

For a moment, Sandy was silent. She thought back to the whole month she'd spent here, her failed exam, her breakup, and her transformation. These experiences, albeit chaotic, had allowed her to truly express herself, to find happiness in an unexpected manner. She found her voice and said, "No, I don't want to leave. I want to stay, and...I want to keep being Sandy."

Megan's eyes welled up, she swiftly crossed the room to give Sandy a warm, genuine hug. It was a moment of understanding and acceptance. It marked a new beginning for Sandy, who was offered an official role as Megan's assistant, and for Megan, who found in Sandy a companion she'd been longing for.