Crossdressing Stories - Caught Crossdressing By Sales Assistants!

Published on Jan 20, 2024 by Tohka Crow

Chapter 1

Robert, a 24-year-old successful businessman known for his disciplined and conservative lifestyle, always adhered to society's expectations. However, beneath the layers of his professional demeanor was a fascination that few could guess. He was captivated by the world of femininity, especially the elegance and variety of women's clothing.

"I wonder how these clothes feel on the skin, how they transform a person," he'd think in the silence of his mind, only to dismiss such thoughts due to societal norms.

On a business trip out of town, in the anonymity of a foreign city, he found himself drawn to a bustling shopping mall. Drawn towards the women's section like a moth to a flame, he couldn't help but imagine himself in each piece.

"Let's try this," he murmured to himself, holding up a skimpy short dress. "I'll just see how it looks on me." Hidden behind the safety of the changing room door, he tried on the dress, experiencing a rush of excitement and a sense of identity that he'd longed for. In the midst of his exploration, he lost track of time.

Suddenly, the door to the changing room opened. Three young female store assistants stood at the threshold, their eyes wide with surprise. "Oh, we're so sorry!" one of them exclaimed, "We didn't realize anyone was still here. The store's closing."

Their apologies trailed off, replaced by an awkward silence that was soon broken by a knock on the door. Sophie, one of the store assistants, said, "Since it’s Friday, the shop is closed, the manager is gone. You seem to enjoy women's clothing, why don't we have some fun helping you embrace your femininity?" In the background, Robert could hear the other girls giggling. His journey of self-exploration had just taken an unexpected turn.

A wave of emotions cascaded through Robert. Embarrassment, fear, but also a strange kind of relief. They had caught him in the midst of his secret exploration, yet instead of judgment, he found understanding in Sophie's voice.

Sophie, her eyes twinkling with friendly mischief, opened the door fully. "Come on out, Robert," she urged. "No one's going to bite."

Stepping out of the changing room, Robert felt oddly vulnerable. He tugged at the hem of the skimpy dress, his face flushed. The other girls looked at him with surprised amusement, their giggles resonating in the empty store.

"I'm Grace, and that's Chloe," said one of the girls, pointing at herself and then her friend. "We can help you, if you'd like. Give you some advice, help you get comfortable."

Robert hesitated, then gave a slight nod. "Alright," he said, his voice barely above a whisper. He could feel his heart pounding in his chest, but there was a sense of excitement too, a thrill of anticipation at what was to come. For the first time, he was openly acknowledging his fascination with femininity, and he was ready to delve deeper into this hidden part of his identity.

Chloe returned with a handful of wigs, each with a unique style and color, while Sophie presented her personal makeup kit with an excited smile. "We're going full makeover mode, Robert," she declared, her eyes gleaming with enthusiasm.

As Robert tried on different wigs, he felt the strands brushing against his skin, a new and intriguing sensation. "It's odd, isn't it?" he mused. "To think something as simple as hair could change one's appearance so dramatically."

When Sophie began applying makeup, Robert closed his eyes, feeling the soft brushes on his skin, the delicate scent of the powders and creams filling his nostrils. He felt a strange thrill at this new exploration of his identity. "It's like painting a picture," Sophie explained. "You're creating a new identity with each stroke."

Then came the heels. Grace provided some guidance, helping Robert find his balance. He winced at the discomfort, yet he couldn't help but admire the elegance that came with the height. "They're tough to walk in," he confessed. "But I think I'm getting the hang of it."

Amidst all the transformation and laughter, Grace's phone buzzed. "It's an invitation," she announced, after a brief glance at her screen. "A friend's throwing a party. What do you say, girls? Robert, would you like to join us?"

Chapter 2

Robert's heart pounded in his chest at the idea. It was daunting, yes, but it was also an opportunity. An opportunity to present this newfound part of his identity to the world, albeit a small part of it. With a deep breath, he responded. "I'd love to." His journey had just taken another unexpected, exhilarating turn.

The prospect of going to a party in his new attire set Robert's mind abuzz with nerves and excitement. For the first time, he was about to step out in the world, dressed in a way that reflected his secret desires. The very thought of it sent shivers down his spine.

As he stepped into the flowing sea-green dress, Robert felt a rush of emotions. The dress felt soft and comforting against his skin, the heels added an extra few inches to his height, and the wig made him feel bold and beautiful. It was as if he was seeing a new side of himself reflected in the mirror, a side that he'd only ever fantasized about before. The sight stirred feelings of joy and trepidation within him.

The girls noticed his nervousness and rallied around him. "You look stunning, Robert," Sophie reassured him, her words warming him from the inside. "Remember, you're not alone. We're here with you."

With the encouragement of his newfound friends, Robert found the strength to step out of the store, his heart pounding with excitement. The city streets seemed to gleam brighter that night, and each step felt like a stride into a new world, a world where he could be true to his desires.

The journey to the party was a blur, yet Robert could feel every heartbeat, every breath. This was his moment, his step towards acceptance and self-love. As he walked into the party, with Sophie, Grace, and Chloe by his side, Robert knew his life would never be the same again. His journey into the world of femininity, which had started with a secret fascination, had led him to this moment of self-acceptance and courage. It was a new beginning, one he had never anticipated, but one he was ready to embrace.

The party was a lively blend of music and laughter, a whirlwind of conversations. Robert, now introduced as "Roberta" to the guests by Sophie, Grace, and Chloe, felt a surge of nervous excitement. Stepping into this new role felt like exploring uncharted territory, yet he was buoyed by the unwavering support of his newfound friends.

"Roberta, I'd like you to meet Alex," Grace said, gesturing towards a tall, handsome man near the bar. Alex's eyes, filled with friendly curiosity, lit up as he extended a warm hand. "It's a pleasure to meet you, Roberta. You're looking stunning tonight."

Alex's compliment sent a blush spreading across Robert's cheeks. "Thank you, Alex," he replied, his voice betraying a mix of gratitude and surprise. This was a new, but thrilling experience for him.

Throughout the evening, Robert found himself drawn to Alex. They shared stories, drinks, and laughter. There was a spark between them, undeniable and exhilarating. Alex's attentiveness made Robert feel seen in a way he had never experienced before.

As the music softened, Alex extended a hand towards Robert. "May I have this dance, Roberta?" he asked, his voice warm and inviting. Taking a deep breath, Robert accepted, allowing Alex to guide him onto the dance floor.

The intimate dance marked a profound moment for Robert. Alex's hands rested on his waist as they swayed to the rhythm. Robert could feel the steady beat of Alex's heart against his, their bodies moving in sync. The heat radiating from Alex, his familiar scent – it all stirred a whirlwind of emotions within Robert.

The night was far from over, and with every passing moment, Robert was embracing his authentic self more and more. The connection he was building with Alex felt like a testament to his courage and an affirmation of his journey of self-exploration.

As the dance with Alex ended, Robert felt a pang of disappointment, but it quickly dissipated when Alex leaned in, his voice soft as he suggested, "Let's go grab a drink?"

A shy nod was all Robert could manage. The evening was turning out to be more than he had imagined. In the hustle and bustle of the party, he found a sanctuary with Alex, where he could explore his identity and feelings more openly.

The hum of the party faded into a pleasant background noise as Alex led Robert to a more secluded corner of the room. They sat on a plush couch, their bodies close, sipping on chilled champagne. The conversation flowed naturally - they discussed everything from favorite books to childhood memories.

Alex had a way of making him feel comfortable, accepted. He laughed at Robert's jokes, listened intently when he spoke, and shared his own stories with an openness that was inviting. It was this feeling of acceptance, this sense of belonging, that made Robert's heart flutter in his chest.

The intimacy of the situation didn't go unnoticed by Robert. Alex's arm resting on the back of the couch, occasionally brushing against his shoulder, his warm smile, the intensity in his gaze - everything was making Robert feel things he hadn't allowed himself to feel before.

As the party continued around them, Robert and Alex remained in their own little bubble. Their conversation deepened, their smiles grew wider, and the spark between them burned brighter. This night was turning into a milestone in Robert's journey, a night where he was not only embracing his identity but also exploring new emotions. It was far from over, and Robert looked forward to every minute of it.

Chapter 3

Throughout the evening, Robert and Alex's connection had deepened with every shared laughter and whispered secret. Alex's allure lay not just in his charisma, but in his unreserved acceptance and understanding of Robert's exploration into his femininity.

As the party buzzed with energy around them, a quiet moment presented itself. The lull in their conversation was filled with an electric tension, and Robert found himself unable to ignore the pull he felt towards Alex.

He looked into Alex's eyes, seeing his own reflection amidst a myriad of emotions. The thought of a kiss lingered at the forefront of his mind, a thrilling possibility that sent his heart racing. "Alex," he started, his voice a touch quieter than before, "May I..."

Alex's gaze softened, understanding dawning in his eyes. "Yes, Roberta," he murmured, a gentle nod affirming his consent.

The distance between them diminished rapidly as Robert leaned in, his heart hammering in his chest. Their lips met in a slow, soft kiss, a moment of exploration that seemed to stretch into eternity. It was a dance of a different sort, one played out in the intimacy of their shared breath and the quiet hum of their connection.

When they finally pulled away, a shared smile spread across their faces, the energy between them crackling with a new intensity. The world around them seemed to fade into a muted backdrop, their shared moment a vibrant splash of color in the midst of the ongoing party.

In the sea of dancing bodies and flashing lights, this quiet moment of shared affection was an unforgettable milestone in Robert's journey of self-discovery. The rest of the evening passed in a blissful blur, but the memory of their shared kiss remained, a beacon of acceptance and exploration that illuminated Robert's path forward.

As the party's final notes dissipated into the late-night air, it was time for the attendees to part ways. Alex, offering to escort Robert back to his hotel, led the way through the quiet city streets. Their path was lit only by the soft glow of the streetlights and the faint radiance of the moon overhead.

The journey back was filled with a quiet yet warm camaraderie, their laughter and whispered exchanges echoing through the otherwise tranquil night. As they neared Robert's hotel, a question hung in the air, unspoken yet insistent.

"Do we meet again, Roberta?" Alex finally broke the silence, his voice filled with a hope that mirrored Robert's own feelings.

Caught in the whirlwind of emotions, Robert could only offer a shaky nod, quickly retrieving a business card from his pocket and handing it to Alex. "I... I'd really like that, Alex."

Accepting the card, Alex studied the neat print on it. His gaze lingered on the name 'Robert', understanding flashing in his eyes. Instead of addressing the name, he simply looked back at Robert, a warm smile tugging at his lips. His silence was a tacit acknowledgment, a pledge of understanding without words.

Their farewell was marked with a tender kiss, a promise of potential future meetings, leaving Robert standing at the hotel entrance, his heart pounding in his chest. Alex's understanding and acceptance echoed in his mind, providing a sense of comfort he hadn't realized he'd needed.

Returning to his hotel room, Robert was enveloped in a storm of emotions. He sat in silence, pondering over the events of the day, his mind spinning with thoughts and feelings. As sleep finally claimed him, the memory of the day, the night, and Alex's kiss remained, vivid and palpable.

The next morning, Robert rose from his bed, feeling a sense of certainty he hadn't expected. Choosing to don the same outfit he'd worn to the party, he decided to attend his business meeting as Roberta. The earlier apprehension was replaced with a newfound sense of resolve as he walked out of his room. His journey of self-discovery was just beginning, and he was ready to embrace it.