Sissy Corner - Sissy Caption Story TG TF Comic - Businessman to a Secretary!

Published on Nov 14, 2024 by Tohka Crow

In the high-stakes corporate world, power games can take unexpected turns. Michael, a once-confident businessman, had climbed the corporate ladder with ambition and drive. However, beneath the polished exterior of the executive suite lay a different game altogether—a world where dominance is wielded with a velvet glove and submission becomes the ultimate transformation.

This is the sissy caption story of Michael’s journey from a determined businessman to something far more delicate—a sissy secretary molded under the commanding gaze of his powerful boss, Ms. Veronica Steele. With every sharp word and calculated demand, she intends to strip away his old identity and unveil a more suitable role at her side.

Sissy Caption Story - New Beginning

Ms. Veronica Steele, a commanding figure with her blonde hair styled elegantly in a tight updo, sat with a poised confidence behind her desk. The fitted blue dress she wore emphasized her striking silhouette, exuding both power and allure. Her deep blue eyes, cold yet piercing, fixed on Michael, who stood uncertainly before her. With one leg elegantly crossed over the other, she rested her chin lightly on her manicured hand, giving the faintest hint of a smirk. The office was impeccably organized, with warm light streaming in through large windows, casting a soft glow on her flawless skin.

"We've reviewed your sales performance," she said, her voice both smooth and unyielding. "I'm afraid we'll have to let you go."

Michael’s face flushed with confusion and a hint of fear, his lips trembling as he managed to stammer, “L-let me go…where?” His voice was soft, almost childlike, betraying the uncertainty churning inside him.

His tailored suit, which once seemed a perfect fit for the ambitious businessman, now hung awkwardly on his frame, as if it no longer belonged. The bright sunlight filtering through the window cast a warm glow around him, emphasizing the blush creeping across his cheeks and the tension in his posture. Hands clasped nervously behind his back, he stood exposed, waiting anxiously for his powerful boss’s response.

Ms. Veronica’s lips curled into a small, knowing smile as she tilted her head slightly, her blonde hair catching the light. Her blue eyes gleamed with a mix of amusement and command. "Let you go…" she said slowly, savoring each word, "as in, release you from this job, darling."

The word "darling" rolled off her tongue with a mix of patronizing sweetness and unmistakable dominance, leaving no room for doubt about who controlled the room. She leaned back in her chair, crossing her legs with deliberate elegance, the fabric of her blue dress shifting slightly to accentuate her poised, confident posture. It was clear—she was not just ending his current position; she had plans that went far beyond what Michael could yet comprehend.

Panic washed over Michael’s face as he took a shaky step forward, his hands clutching nervously at the front of his shirt. "W-wait!" he blurted, his voice cracking under the weight of desperation. "I-I can do better...I promise!"

His wide eyes, glistening with worry, darted toward his boss, searching for any hint of mercy or reconsideration. The sunlight streaming in through the office windows cast a harsh light on his flushed cheeks, making his vulnerable state all the more apparent. His once-confident composure had crumbled entirely, leaving only a pleading man on the verge of losing everything—or perhaps on the brink of a different kind of fate entirely.

Ms. Veronica's smile widened slightly, a glimmer of satisfaction dancing in her blue eyes as she leaned forward, resting her chin on her hand. "Honestly, you don't make a good salesman," she said, her voice deceptively soft yet edged with authority. "But...if you're interested, we do have a vacancy for a secretary."

The words hung in the air, a mix of challenge and invitation, as her gaze pierced him. She knew exactly what she was offering, and the weight of her expectations was clear. Sunlight bathed the room in a warm glow, highlighting the smooth curves of her blue dress and her unshakeable poise. This was a turning point, and she was determined to savor every moment of his reaction.

Michael's eyes widened, and a deep blush spread across his cheeks as the reality of Ms. Veronica's words sank in. "S-secretary? Me...?" he whispered, barely able to form the words. His voice trembled with disbelief and a hint of dread, the idea sounding completely foreign and unfathomable.

He shifted uncomfortably, his fingers fidgeting with the edges of his belt. The crisp lines of his business suit suddenly felt constrictive and ill-suited to the conversation unraveling before him. The sunlight streaming through the window framed his tense posture, highlighting his vulnerability in stark contrast to the strength and composure exuded by the woman before him. This moment would change everything, and deep down, he felt it.

Ms. Veronica leaned back slightly, an amused smile playing on her lips as she regarded Michael with an almost playful glint in her blue eyes. "Only thing is... due to our diversity rules," she said, her voice smooth and unwavering, "it’s a position for a female. So, you’d need a change of style." She paused for emphasis, letting the weight of her words sink in. "And you could start right away."

Her gaze never wavered, watching him closely, measuring every flicker of emotion on his face. The casualness of her tone made it clear she was serious—and that she held all the power in the room.

Michael's cheeks burned a deeper shade of red, and he shifted awkwardly, his hands fidgeting with the hem of his jacket. His eyes darted to the side, unable to meet Ms. Veronica’s piercing gaze for too long. "I-I mean...if it helps the team," he mumbled, his voice barely above a whisper, "I...I could give it a go."

The words stumbled out hesitantly, each syllable laced with both reluctance and a desperate need to please. His posture, once confident and assured, now sagged under the weight of uncertainty and the implications of her offer. In the soft afternoon light, his vulnerability was laid bare, as though he already sensed he was stepping into a role he had never imagined for himself.

Ms. Veronica’s touch was surprisingly gentle, but her words carried a teasing edge that left Michael squirming. She leaned in closer, her perfume intoxicating, as she carefully applied blush to his cheeks. "Let’s see... a little blush here," she cooed, her voice dripping with playful condescension. "And some color there... Oh, you’re going to look simply adorable."

She pulled back for a moment, a wicked smile playing on her lips as she studied his flushed face. "Who knew underneath that dull suit was someone just begging for a bit of color?" she teased, her eyes dancing with amusement. Her fingers trailed down his jawline, making him shiver. "You’re going to be the prettiest little secretary this office has ever seen."

Her words hung in the air, equal parts teasing and humiliating, and Michael could feel his face growing even hotter under her relentless gaze.

Ms. Veronica stepped back slightly, tilting her head as she admired her work so far. A satisfied smirk spread across her lips. "Oh, look at you!" she exclaimed, her voice rich with mocking praise. "You're almost too pretty to be my secretary..." She let the words hang for a moment, savoring his flushed, uncertain expression.

Her eyes narrowed with playful intent. "Now, let's do something about that hair," she added, a glint of mischief sparking in her gaze. She reached out, her fingers brushing through his locks with an almost tender touch that only served to heighten the humiliation. Every moment seemed to underline her control—and his surrender to her whims.

Ms. Veronica stepped back, taking in the transformation with a satisfied nod. "Much better!" she declared, a wicked smile curling her lips. "Now you’re starting to look the part."

Her eyes gleamed with a mix of mischief and dominance as she circled him slowly, the weight of her gaze lingering on every detail. "Oh, but we’re not done," she said, her tone as sweet as it was condescending. "This calls for a complete wardrobe change."

With a flourish of her hand, she motioned toward the next step in his transformation. The playfulness in her voice was unmistakable, but it carried an undercurrent of authority that left no room for resistance.

Ms. Veronica crossed her arms, a pleased but teasing glint in her eyes as she took in the full transformation. "Well, well... you’re almost unrecognizable," she purred, a playful smirk tugging at the corners of her lips. "I never thought you’d clean up this nicely!"

She tilted her head, her gaze lingering for a moment longer, as if savoring every ounce of his discomfort. "You know," she continued, her voice dripping with feigned surprise, "I think you might even enjoy this new role more than you’d like to admit."

Each word was laced with both mocking praise and subtle dominance, reminding him of how deeply under her control he had fallen.

Ms. Veronica stood confidently, hands on her hips, exuding a mix of authority and satisfaction. Her smile was equal parts charming and commanding as she addressed him. "Alright, here’s the deal," she said, her voice firm yet teasingly smooth. "Your probation as a secretary is three months."

She paused for effect, her eyes never leaving his. "I’ll be consulting with our top salesman, Brad, on your performance," she added, letting the implication sink in. The way she said it left no doubt—this was more than just a trial period; it was a test of how well he would submit and adapt to his new role. The stakes had been set, and she clearly relished every second of his reaction.

Ms. Veronica's smile widened, her eyes gleaming with a hint of mischief. "And be nice to Brad, too," she added, her voice low and teasing, dripping with suggestion. "He can be... very persuasive."

The playful lilt in her tone left no doubt that she was enjoying every second of this exchange. She leaned in just slightly, as if sharing a secret, making the implications of her words even more unsettling. The atmosphere thickened with the weight of her authority and the unspoken expectations that now hung over him.

He quickly adjusted to his new duties... sorting files, delivering coffee, and taking detailed notes at every meeting. Each task, no matter how small, was a stark reminder of his new place in the office hierarchy. With each passing day, the suit and tie that once symbolized authority were replaced by polished nails, a crisp blouse, and the expectation of perfect poise. The clip-clop of his heels echoed in the hallway as he carried out his tasks, under the watchful eyes of his colleagues, each step both humiliating and strangely... inevitable.

...and assisting Brad, the top salesman, whenever needed. Each task came with a subtle reminder of his new position, every glance from Brad a mix of scrutiny and barely concealed amusement. The weight of expectation pressed on him as he navigated this unfamiliar role, striving to meet every demand—no matter how trivial or pointed.

Brad's presence was always commanding, making each moment of assistance feel like an unspoken test. Michael couldn’t help but feel the power dynamic shift with every request, every clipboard handed over, and every report carefully organized to perfection.

Three months later… The office hummed with the usual rhythm of daily tasks, but for Michael, everything had changed. The probation period had passed in a blur of adjustments, subtle humiliations, and the relentless demands of his new role. He had learned to navigate every expectation with precision, from managing schedules to fetching coffee—always with perfect poise and an ever-present smile.

Colleagues who once regarded him with professional respect now saw him through a different lens, one of curiosity or quiet judgment. He had grown accustomed to the sidelong glances, the whispers, and the pointed remarks. Yet, beneath it all, he had survived—and perhaps even started to thrive, molded by the dominant hand that had reshaped his sissy side.

"Hey," Brad's voice cut through the office's usual hum, low and confident as he leaned in just a little too close. "Heard there’s a board meeting tomorrow. I’m supposed to give my thoughts on your performance..." He paused, letting the tension hang thick in the air between them. "But honestly, I’m not sure I’m convinced yet."

His gaze was piercing, a mix of challenge and playful dominance that left no room for misinterpretation. Michael could feel the weight of Brad's scrutiny, every word a reminder that his future here was anything but guaranteed.

"Not convinced?!" The thought raced through his mind, panic surging with every heartbeat. "I’ve been working my ass off for three months, and he’s still not convinced! I... I can’t lose this job!"

The weight of his effort, his sacrifices, and the humiliations endured over the past months came crashing down. Fear mixed with desperation in his wide eyes. Every fiber of his being ached at the possibility of failure—and the cost of starting over again.

"M-maybe... there's something I can do to... convince you?"

His voice carried a teasing lilt, the faintest hint of a playful smile tugging at his lips. He leaned in slightly, his eyes sparkling with a mix of flirtation and mischief. Beneath the teasing exterior, there was still that undercurrent of nerves, but he hid it well—letting his words linger, inviting the reaction he hoped for. It was a bold move, one that danced the line between daring and desperation...