Crossdressing Stories - Caught Wearing Pantyhose and Thong at Work!

Published on Dec 27, 2023 by Tohka Crow

In the bustling heart of the city, nestled between high-rise buildings and the constant hum of urban life, stood a modest, aging apartment. It was here, in a cramped but cozy living room, that Arthur found solace. At 19, his life was a blend of routine and hidden complexities. He lived with his mother, a gentle woman worn by years of hard work, and his younger sister, Lily, who was blissfully unaware of the world beyond her high school dramas.

Arthur had recently embarked on a new journey, an internship at a prestigious company. It was a basic administrative role, but to him, it felt like a step towards something bigger. His days were filled with filing, organizing documents, and the occasional coffee run. The job was mundane, but it provided a sense of purpose that Arthur craved.

In the privacy of his room, Arthur harbored a secret. When the world outside became too overwhelming, he found comfort in crossdressing. It was his escape, a way to express a part of himself he kept hidden. He would often borrow clothes from Lily's wardrobe, careful to choose items she seldom wore. It was a risky endeavor, but the thrill of it added to the allure.

On a particular day, a day like any other, Arthur's routine took an unexpected turn. Dressed in his usual work attire, he concealed beneath it his sister's delicate thong and pantyhose. It was a daring choice, even for him, but it made him feel exhilaratingly bold.

As the day neared its end, Arthur was tasked with delivering documents to the director's office. It was a simple task, yet he felt a surge of anxiety. The director's office was on the top floor, a place Arthur had never been. The elevator ride seemed to last an eternity, his heart pounding in his chest with each passing floor.

Upon arriving, he was greeted by the director's vast, immaculately organized office. Sunlight streamed through the large windows, casting a warm glow on the polished wooden desk. The director, a figure of authority and elegance, acknowledged Arthur with a nod, his attention momentarily diverted from the pile of paperwork before him.

As Arthur handed over the documents, his clumsy fingers betrayed him. Papers slipped from his grasp, scattering across the floor. Flustered, he bent down to retrieve them, his shirt sliding up ever so slightly. In that moment, he realized his mistake. The fabric of the thong, a stark contrast to his otherwise mundane attire, and the pantyhose were now exposed. His heart raced, fear and embarrassment flooding his senses.

The director, a man known for his stern demeanor and meticulous nature, caught the brief glimpse of the unexpected attire. His sharp eyes narrowed slightly, a flicker of surprise evident in his normally impassive expression. Arthur, mortified, hurried to collect the papers, his mind racing with the potential consequences of his secret being revealed. The air in the room felt heavy, filled with unspoken questions and Arthur's palpable anxiety.

The director, observing Arthur's panic-stricken and embarrassed demeanor, remarked dryly, "That's a bold attire to wear to work, but it's against the dress code." Arthur's heart pounded in his chest, his apologies tumbling out in a rush of words, each one laden with panic and mortification.

Seizing the moment of awkwardness, the director leaned back in his chair and said, "If that's your thing, you know, we're currently recruiting for a personal assistant internally. Our diversity guidelines restrict this position to females or under-represented minorities, so you could be a perfect fit if you're willing to continue crossdressing."

Arthur's face, already flushed with embarrassment, contorted with uncertainty. The idea of crossdressing in a professional setting was worlds apart from the secrecy of his private life.

Sensing Arthur's hesitation, the director added, "This role is significantly better compensated than your internship."

Arthur, grappling with the proposition, voiced his concern, "It would be awkward. I live with my mom and sister, and they don't know about this."

The director's response came with an unexpected chuckle, "That's perfect. Your mother and sister can lend you clothes, help with makeup. You could start as early as tomorrow."

Arthur stood frozen, the offer hanging in the air like a surreal dream. The possibility of turning his secret indulgence into a professional reality was both terrifying and exhilarating. The director's proposal, while offering a path to greater acceptance and financial stability, also meant stepping into the light with a part of himself he had always kept hidden.

The director, sensing the whirlwind of emotions coursing through Arthur, reached for a piece of paper and quickly printed out a job offer. He slid it across the desk towards Arthur with a decisive movement. "Show this to your family," he suggested, his voice carrying a tone of practicality. "It might help them understand where this is coming from. Take some time to think about it."

But then, his expression turned serious again, the familiar sternness creeping back. "Don't take too long, though. This position won't be open for long. Opportunities like this are rare, and I need someone committed."

Arthur held the paper, feeling its weight as if it was much more than just ink on parchment. It symbolized a crossroads, a potential shift in the very fabric of his life. The director's offer was not just a job proposal; it was an invitation to a new world, one where his secret could be a part of his identity, not just a hidden aspect of it.

As he left the office, job offer in hand, Arthur felt a mixture of dread and excitement. The thought of discussing this with his family was daunting, yet there was a glimmer of hope. Maybe, just maybe, this could be the start of a journey where he no longer had to hide a part of who he was.

Arthur stepped out of the director's office, the job offer clenched in his hand, feeling as though he had just stepped off a roller coaster. His mind was a tumult of thoughts and emotions as he made his way back to his desk. The office around him buzzed with the usual activity, but to Arthur, everything seemed distant, muffled by the intensity of his own inner turmoil.

The journey home that evening felt longer than usual. The crowded bus, the familiar streets, everything appeared surreal, as if he was viewing his life through a different lens. The job offer burned a hole in his pocket, a symbol of a life that could be – vastly different from the one he had known.

When he finally reached his apartment, he found his mother in the kitchen, cooking dinner, and Lily sprawled on the couch, engrossed in her phone. The normalcy of the scene was both comforting and jarring. How could he bring up the job offer, the secret life he had been living, in such an ordinary setting?

Gathering his courage, he joined his mother in the kitchen. "Mom, I need to talk to you about something important," he began, his voice unsteady. His mother turned to him, sensing the seriousness in his tone. He handed her the job offer, watching as a frown creased her brow while she read.

Arthur explained everything – the internship, the director's offer, and his secret of crossdressing. His words tumbled out in a rush, a mix of confession and plea. His mother listened quietly, her expression unreadable. When he finished, there was a heavy silence.

Finally, she spoke, her voice tinged with a mix of surprise and concern. "Arthur, this is a lot to take in. But I want you to know, whatever you choose, I'm here for you. We'll figure this out together."

Lily, having overheard the conversation, joined them. Her initial shock quickly gave way to a mischievous grin. "Well, looks like I'm going to have to keep a closer eye on my wardrobe from now on," she joked, trying to lighten the mood.

That night, Arthur lay in bed, the weight of his family's acceptance both a relief and a new kind of burden. The path ahead was uncertain and daunting, but for the first time, he felt a sense of hope. The possibility of not only embracing but also living his truth, even in the most unexpected of ways, seemed within reach. The decision lay before him, a road less traveled, but perhaps one that led to a place where he could truly be himself.

The following morning, Arthur awoke with a sense of purpose he had never felt before. The conversation with his mother and sister had lifted a weight off his shoulders, their acceptance providing him with newfound courage. He realized that no matter the decision he made regarding the job offer, he had crossed a significant threshold in his life.

During breakfast, the atmosphere was a mix of awkwardness and support. His mother, still processing the revelations from the night before, poured extra care into making his favorite breakfast, while Lily chattered about fashion and makeup, a topic that was previously uncharted territory between them.

After breakfast, Arthur retreated to his room with the job offer in hand. The words of the director echoed in his mind: "Don't take too long." He sat at his desk, staring at the paper, the words blurring as he contemplated his next steps. The role of the personal assistant was not just a job; it was a gateway to living openly in a way he had never considered possible. Yet, the fear of the unknown, of how his colleagues might react, held him back.

Finally, with a deep breath, Arthur made his decision.

Arthur's fingers trembled slightly as he dialed the director's number. The phone rang twice before it was answered, the director's voice brisk but welcoming on the other end. "I've decided to accept the offer," Arthur said, his voice carrying a mix of resolve and underlying anxiety.

"That's excellent news, Arthur," the director responded with a note of genuine enthusiasm. "If you're up for it, you can start today. I understand you might need some time to prepare, so let's make it a half-day. Come in when you're ready, and we'll get you acquainted with everything."

Ending the call, Arthur felt a rush of mixed emotions. His decision, now vocalized and real, seemed both daunting and liberating. He walked back into the kitchen, where his mother and Lily were waiting, their faces etched with anticipation.

"I accepted the offer," he announced, trying to sound more confident than he felt.

His mother's eyes softened, a mixture of pride and concern in her gaze. "Arthur, this is a big step. We're here for you, through all of this," she said, her voice warm and reassuring.

She turned to Lily. "And I have faith that you'll help your brother look his best," she added, a hint of amusement in her tone. Lily's face lit up with excitement. "This is going to be so much fun!" she exclaimed, a spark of inspiration glinting in her eyes. Without missing a beat, she began bombarding him with ideas and suggestions on everything from outfits to makeup, her energy infectious and welcoming.