Crossdressing Stories - Business Negotiations in Heels!
Published on Jan 17, 2024 by Tohka Crow
"This has got to be a joke, Mia?" The words tumbled from Ryan's lips, bouncing around the expansive office as his bewildered eyes met his boss's stern gaze. The faint aroma of old leather and pine filled his nostrils, a sharp contrast to the bitter taste of his predicament.
"Ryan, I'm not joking." Mia's voice remained firm, her steely resolve glaring in the stark office lights. A sprawling cityscape sat behind her, a silent spectator to their predicament, its skyline a testament to countless battles won and lost.
His thoughts swirled like a tornado, the reality of her words pulling him into its tumultuous core. "I'm the best... but this?" He was the golden boy of the sales department, yet he found himself cornered by a paradox he couldn't talk his way out of.
"Our client has a weakness for women," Mia explained, her hazel eyes holding his gaze, "and we have no women in sales. It's an advantage we cannot ignore in our current state, Ryan." The intensity of her stare was a mirror to the gravity of their situation.
"And if I refuse?" Ryan choked out, already knowing the answer. His gaze drifted to the glowing metropolis outside the window, the city's pulse a cruel reminder of the life he might lose.
"We can't afford your salary if we don't make this deal. I'm sorry, Ryan, but it's either this or... we let you go," Mia confessed, her voice holding a trace of regret. A heavy silence filled the room as the reality of her ultimatum sank in.
"Think it over, Ryan," she implored, her tone softer now, yet equally determined. "Come back tomorrow with your decision." Her words, filled with painful truths and harsh realities, hung in the air long after she had finished speaking.
Throughout the night, Ryan's mind whirred with thoughts and scenarios. His bed, usually a haven of rest, now felt like a platform of torment. He glanced at the clock, its red digits glaring against the room's darkness. The new mortgage hung over his head like an unwelcome specter, a reminder of the crushing responsibilities he had to fulfill. With a weary sigh, he made up his mind.
The morning sun had barely washed over the city when he pushed open the door to Mia's office. His heart pounded in his chest, the looming decision echoing in every beat. To his surprise, three women were already there, their gazes turned curiously towards him as he entered.
"It's okay, Ryan," Mia reassured, gesturing him inside. His apprehension must have been as evident as the morning light streaming through the office windows.
"I... I agree," he finally managed to utter, his voice barely audible over the hum of the air conditioning. His decision felt like a stone sinking into the pit of his stomach, yet he knew it was his only viable option.
A slow smile spread across Mia's face. "I knew you'd be reasonable, Ryan. That's why I've called these three ladies for help." Mia's words rang clear and confident, an anchor in the swirling sea of his uncertainty.
The women, introduced as a makeup artist, voice trainer, and personal trainer, all nodded at him, their eyes assessing yet encouraging. His world, once filled with sales targets and boardroom presentations, was about to take a drastic turn.
"From now on," Mia continued, her gaze steady, "you'll be working closely with us. Your regular job takes a backseat until we close this deal." Her words marked the beginning of a new journey for him, a journey he never anticipated, but one he had to undertake nonetheless.
"We can't waste any time, Ryan," Mia said, her voice brimming with determination. The clock was ticking, and the office was a whirl of activity. Piles of clothing, shoes, wigs - all potential keys to their success - littered the room.
Hours stretched on as the ladies meticulously worked on him, each outfit change taking him further away from his familiar self. The initial embarrassment of trying on feminine clothes in front of the women was a visceral punch, yet he couldn't deny a strange sense of enjoyment that fluttered in the pit of his stomach. Each piece, with its soft fabrics and delicate designs, awakened a new aspect of him.
As the day wore on, the transformation became more startling. Makeup made his features softer, the chosen wig completely altered his appearance, and the sight in the mirror was a woman, an entity far removed from the man he knew. The reflection stirred a cauldron of emotions within him, leaving him unsure of his feelings.
With the setting sun casting long shadows in the office, Ryan was ready to call it a day, his mind and body exhausted. But Mia had different plans. "Not so fast, Ryan," she chided, a glint in her eyes. "Natasha is waiting to get you started at the gym."
He started to protest, to argue about the impracticality of gymming in a dress and makeup. But Mia was relentless. "You need to immerse yourself in the role, Ryan," she said firmly.
Handed a pair of yoga pants and a sports bra by Natasha, he sighed, tied his wig into a ponytail and changed. As he followed Natasha out of the office, the city lights greeted him, the gym looming ahead like a new battlefield to conquer.
Chapter 2
The city was bathed in the soft hues of the evening as Ryan walked into the gym, a place he had been to several times before. Only, this time was drastically different. The heavy thrum of anxiety pounded in his ears, the sight of the crowded gym triggering a wave of apprehension.
Automatically, he made his way to the men's changing room, an action ingrained by habit. A sudden collision with a muscular figure brought him back to reality. "Did you get lost, babygirl?" the man asked, laughing. His cheeks flushed with embarrassment, Ryan stuttered out an apology before making a swift exit, drawing some surprised glances.
Entering the ladies' changing room felt no less surreal. He quickly stowed his bag in a locker, the muffled chatter and perfume-infused air creating an atmosphere starkly different from what he was accustomed to. He met up with Natasha, who was waiting with a determined look on her face.
The next hour was a series of humiliating and challenging exercises, focusing primarily on his glutes. His form-fitting leggings accentuated his movements, drawing occasional glances from onlookers. Although embarrassed, he couldn't help but feel a small thrill at the attention he was receiving.
The following weeks followed a similar routine: intensive training with Natasha, voice coaching sessions, and strategy discussions with Mia. Each day brought him closer to his feminine persona, and the deal he had to close.
And then, finally, the day of the business talks arrived. Ryan, now fully embraced his new persona, was as ready as he could be. It was time to put his weeks of preparation to the test.
Chapter 3
The day of the business dinner arrived with a flutter of nervous anticipation. The chosen setting was an elegant Japanese restaurant, and it was here that Ryan had to introduce himself as "Vivienne" to the businessman. The ensemble chosen for him by the image consultant and makeup artist was nothing short of striking. They selected a high neck asymmetric dress, its fiery red fabric embellished with intricate embroidered trim. It hugged Ryan's body in all the right places, with a daring slit that ran up the side, revealing a swath of his leg.
Accompanying the dress were a pair of matching red heels, their high arch and delicate straps serving to lengthen the line of his leg. His hair, or rather the wig he had grown accustomed to over the past week, was styled into an elegant updo that utilised chopsticks, a nod to the setting of their dinner. The finishing touch was a pair of sophisticated, dangling earrings that captured the light each time he moved his head.
Dressing up, Ryan watched his reflection morph from the familiar to the feminine. Each element of his appearance, from the sweep of eyeliner to the contouring of his cheekbones, was meticulously crafted to enhance his transformation. The result was beyond anything he could have imagined - he was attractive, alluring, even. For a moment, he allowed himself to revel in the novelty of his own reflection.
There was an odd sense of satisfaction to be found in his new persona. Looking back at the week spent cross-dressing, he realized he had actually begun to enjoy the change. The nervousness he had initially felt had all but dissipated by the time he reached the restaurant.
Upon meeting, the businessman complimented Ryan's look with an approving glance, and proceeded to greet him with a gentlemanly kiss on the hand. Ryan responded by introducing himself as Vivienne, his voice steady and sure. The businessman, ever the gentleman, pulled out the chair for Ryan, offering assistance as he navigated the precarious task of sitting down in a dress and heels. It was a delicate dance, one that Ryan was quickly learning to master.
Throughout dinner, their conversation ebbed and flowed between personal anecdotes and business talk. The businessman's demeanor grew bolder as the evening wore on, fortified by the steady flow of wine. He was a tough negotiator, shrewd and unyielding, but Ryan could tell the man was becoming increasingly attracted to him, his gaze often straying from Ryan's face to the rest of his figure.
Ryan maintained his composure, holding his own in the conversation while limiting his alcohol intake. He encouraged the businessman to have another glass, and another, weaving his charm into the fabric of their negotiation.
As the evening wore on, the businessman's actions grew more forward. Emboldened by the wine, he moved closer to Ryan, his hand creeping up to rest on his thigh, fingers tracing the bare skin revealed by the dress's daring slit. Ryan suppressed a shudder, feeling a mix of discomfort and a strange thrill at the touch.
Using the businessman's growing interest to his advantage, Ryan grew more assertive in his negotiation. He knew the deal hinged on his performance tonight. He was firm in his stance, insistent on the terms that would favor his company. The businessman frowned, unhappy with the proposed terms but seemingly unable to refuse Ryan.
At one point, the businessman leaned in closer, his intentions clear as he moved as if to kiss him. Ryan mirrored his movements, leaning in so their lips were a breath apart. He paused, holding the man's gaze with a teasing smile before leaning closer, his lips brushing against the shell of the man's ear as he whispered, "Are you willing to accept my terms?"
He could see the goosebumps rise on the man's neck, a sign of his vulnerability. After a moment of silence, the man nodded, a curt agreement that was music to Ryan's ears. They toasted to the prosperous future of their companies, glasses clinking in the quiet restaurant. Ryan allowed himself a moment of triumph - he had done it, he had sealed the deal.
Upon arriving home, Ryan was greeted by a familiar yet unfamiliar sense of relief. He had successfully closed the deal, ensuring his continued employment. He was free to shed Vivienne's persona and return to being Ryan again. But as he stared at the assortment of suits, ties, and button-up shirts hanging in his wardrobe, a sense of emptiness crept over him. They looked drab, colorless, almost lifeless compared to the vibrant and feminine clothing he had grown accustomed to over the past weeks.
He turned to the mirror, Vivienne's reflection staring back at him. He studied her image - the elegant hairstyle, the meticulously applied makeup, the red dress that clung to his new, more feminine physique. He was no longer looking at a man dressed as a woman, but a confident, beautiful woman. Ryan, trapped within his masculine shell, had never felt so at ease, so liberated, as he did when he was Vivienne.
His feelings were a whirlwind. He felt confusion, happiness, fear, and a hint of sadness. He realized he was mourning the imminent loss of Vivienne, a character he had created and inhabited. He had not merely been pretending to be a woman - he had become one, and he had liked it. He had enjoyed the attention, the freedom to express himself in ways he had never dreamed of before. He was beginning to question his identity, his place in the world, and the path he wanted to take.
With the sunrise of the next day, Ryan knocked on Mia's office door. "Come in, Ryan," she began, before correcting herself. "I mean, good morning, Vivienne."
Despite the quiver in her voice, her smile was warm and welcoming. Ryan took a deep breath, pushing open the door. He knew, in that moment, he didn't want to let go of Vivienne. She was no longer just a disguise, but a part of him - a part that had brought him joy and freedom. Vivienne was here to stay, and Ryan was more than ready to embrace her.
