Crossdressing Stories - Caught Crossdressing When Babysitting
Published on Mar 2, 2024 by Tohka Crow
Bryan hesitated for a moment as he stood outside the towering glass building. Taking a deep breath, he pushed the buzzer. From his time at Uni, he had learned to be independent, but nothing could prepare him for the opulence that awaited him. The door swung open to reveal Anna, her hourglass figure prominent in a sharp suit that screamed authority. Her piercing eyes scanned him for a moment, a sly smile playing on her lips.
"You must be Bryan," she said, her voice dripping with charm. "Come in, let's get you acquainted with the place." As he stepped inside, he couldn't help but take in the expansive penthouse apartment, with its panoramic view of the city. It was clear that this was a world far removed from his humble dormitory.
John emerged from the home office, a contrast to Anna, with a demeanor that spoke of quiet strength. "Glad you could make it, Bryan. We hope this arrangement works for both of us. Our son mostly sleeps through the day. You shouldn't have much trouble."
Anna, leaning against a marble countertop with a glass of wine, chimed in, "This isn't your regular babysitting job. We travel a lot for work, sometimes together. We need someone flexible, someone who can adapt. We're glad you're on a break from Uni." Her gaze lingered on Bryan, flirtatious and assessing.
Handing Bryan the keys, John said, "We'll be off this evening. Flight's in a few hours. Your official duties start tomorrow. Just ensure our boy is alright." As Bryan nodded, taking the keys, he felt the weight of the responsibility they were bestowing upon him, intertwined with the magnetic pull of Anna's presence.
As morning rays permeated the penthouse, Bryan found himself navigating the vast space with a mix of awe and diligence. The serenity of the child, the distant hum of the city below, and the luxury surrounding him made his initial hours quite seamless.
It was during one of his routine checks on the child that he stumbled upon Anna's room, the door slightly ajar. Laid out on the plush bed was a black dress, the fabric appearing like liquid shadow against the stark white sheets. Its elegance was undeniable, but it was the lingering scent of Anna's perfume in the air that truly captured his attention, a seductive blend of jasmine and something more elusive, almost forbidden. The aroma seemed to hang in the room, tantalizing and intimate, like a whispered secret.
His heart raced as he approached the bed. The dress felt cool and soft under his fingertips, the fabric whispering tales of evenings out, of power, of Anna. The thought of trying it on was as unexpected as it was overwhelming. A swirling tempest of emotions bubbled up inside him: curiosity, excitement, fear of the forbidden, and a deep, compelling desire to experience, if only for a moment, the world from Anna's perspective. He questioned his own sanity; why was he so tempted? Was it the allure of the forbidden, the mystique of Anna herself, or some hidden desire within him yearning to be free? The room, with its haunting perfume and the beckoning dress, felt like a siren's call, pulling him deeper into a realm of possibilities he had never dared to explore.
With every heartbeat pounding loudly in his ears, Bryan carefully lifted the dress from the bed. The fabric felt even more luxurious in his grasp, the cool silkiness of it sending shivers down his spine. There was a heady rush of adrenaline coupled with a sensation he couldn't quite place, something akin to standing on the edge of a cliff, ready to jump into the unknown.
Hesitantly, he slipped the dress over his head. The fabric whispered against his skin as it cascaded down, fitting him surprisingly well. Every movement brought forth a new sensation; the way the fabric hugged his form, the gentle caress of lace on his thighs, the cool zephyr-like brush of the hem against his legs. Each feeling was a revelation, introducing him to facets of himself he hadn't known existed.
With bated breath, he approached the ornate full-length mirror in the corner of the room. The reflection that greeted him was both familiar and foreign. The dress, molded to his body, transformed him into an enigmatic figure. He looked different, vulnerable yet empowered, a beautiful blend of masculinity and femininity. There was a certain allure in the juxtaposition; his angular features softened by the flow of the dress, his eyes wide with a mix of surprise, elation, and trepidation.
For a moment, he allowed himself to truly see the person in the mirror, unburdened by society's expectations or his own preconceptions. It was liberating, this dance with the forbidden, allowing him to see a world of possibilities and self-expression he had never previously considered. The reflection staring back at him was a testament to the complexity of the human soul, proving that identity was never just skin deep.
As the weight of the dress slipped away, a new weight settled onto Bryan's shoulders. The apartment suddenly felt too small, the walls inching closer, making his heart race. He packed his belongings swiftly, desperate to escape the scene of his personal revelation.
On the bus ride home, the world outside blurred as his mind raced. The dress, the mirror, the feelings, they merged into a whirlwind of confusion and clarity. He pondered on the boundaries of masculinity and femininity he had grown up knowing, feeling both constrained and curious. There was an unmistakable allure in the softness he had briefly experienced, a sense of freedom in embracing what was traditionally termed as 'feminine'. Was it wrong to desire such softness, such vulnerability?
The more he delved into these thoughts, the more he realized that his attraction to the dress wasn't just about the garment; it was a deeper exploration of his own identity. When he reached home, a sudden urge overtook him. Without hesitation, he began shaving his body, each stroke of the razor removing a layer of societal expectation, revealing smooth, unblemished skin beneath. The process was cathartic, but also a tad painful. Every swipe was both an unshackling and a confrontation with years of suppressed feelings.
Lying in bed that night, the soft sheets against his newly smooth skin felt foreign yet intimate. The events of the day replayed in his mind like a dream, their gravity slowly sinking in. It wasn't just about the dress or the shaving; it was about the freedom to discover oneself, to blur the lines, and to redefine what felt right. Bryan tossed and turned, grappling with his newfound awareness, conflicted yet strangely elated. Sleep seemed a distant luxury, but in its stead came a deeper understanding of the layers that constituted his self.
The morning sun filtering through the penthouse painted everything in a golden hue. But for Bryan, the lure wasn't the sprawling city outside; it was the allure of Anna's room. The memory of the dress danced in his mind, a siren's call that beckoned him closer. The battle inside him raged between curiosity and the constraints of societal judgment. Yet, the very thought of how the fabric felt against his skin, of how the mirror had shown him a different side of himself, made his heart race.
Drawn like a moth to a flame, he soon found himself standing before Anna's wardrobe. As he pushed the door open, the soft light revealed a myriad of colors and fabrics. Among them, he spotted the sultry black lingerie. The very idea of wearing it felt forbidden, sending shivers down his spine. With trembling fingers, he picked it up, feeling the delicate lace and soft silk. The act of wearing it was about more than just clothing; it was about exploring a hidden part of his soul, embracing vulnerability, and testing the bounds of self-expression.
As he slipped into the lingerie, the fabric hugged his form, creating a sensation of intimacy and revelation. The gentle embrace of lace against his smooth skin created a blend of comfort and exhilaration. The undergarments, so different from anything he'd ever worn, transformed not just his physical appearance but also his perception of himself. They became symbols of defiance against norms, a secret shared only between him and the mirror.
With the foundation set, he reached out for the black dress. Its familiar weight settled on him, molding him, guiding him further into this dance with the forbidden. The addition of heels was the final touch, a challenge to his balance both physically and emotionally. Each step in those heels felt like a step into uncharted territory, a bold stride into a realm of fluidity and self-exploration.
Gazing at his reflection once more, the transformation was astounding. The man from yesterday had evolved, revealing a complex blend of strength and vulnerability, masculinity and femininity. His heart raced at the daring persona staring back, the striking vision of himself draped in shadows of black. The inner turmoil of right and wrong, guilt and curiosity, continued to churn, but in this moment, the reflection spoke of freedom, of breaking chains, and of discovering realms within that he never knew existed.
On Anna's dresser lay a makeup kit, its contents spread out in an array of colors and brushes. Each piece seemed to beckon Bryan closer, offering another layer of transformation. He remembered snippets from the makeup tutorials he had watched earlier, the beauty influencers with their seamless strokes and dazzling transformations. Taking a deep breath, Bryan decided to dive in.
He began with the foundation, feeling the cool liquid texture against his fingertips. As he spread it across his face, he marveled at the even tone it provided, masking imperfections and creating a smooth canvas. With each application, from the subtle blush on his cheeks to the eyeshadow that brought out the depth in his eyes, Bryan felt like an artist painting on a fresh canvas. The eyeliner was tricky, demanding precision, but he managed a neat line, enhancing the shape of his eyes. Finally, he chose a bold lipstick that mirrored the audacity of his actions. The transformation was almost spiritual; with each brushstroke, he was not just altering his appearance, but also embracing a side of himself he had only just begun to understand.
The makeup made him feel empowered, but there was still one piece missing. Spotting Anna's wig, a cascade of raven-black waves, he felt an irresistible pull. Carefully, he placed it on his head, adjusting until it sat perfectly. The sensation was startlingly new, the weight of the hair, the way it framed his face, how it fell over his shoulders. It felt like the final piece of a puzzle, solidifying his metamorphosis.
Stepping back to view his reflection, Bryan was met with a visage that was both foreign and intimately familiar. The person in the mirror was no longer just Bryan; he was an exquisite blend of Bryan and this newfound persona. The makeup accentuated his features, and the wig added a softness that contrasted and complemented his natural features. The whirlwind of emotions continued, exhilaration, trepidation, and a deep sense of realization. He had ventured into uncharted territories of his soul, confronting and embracing complexities of identity, gender, and self-expression. The reflection told a story of courage, curiosity, and the boundless horizons of self-discovery.
The world around Bryan seemed to slow down to an agonizing pace. The rhythmic jingle of the keys, each echo amplifying his dread, was like the grim beat of a heart about to shatter. The gravity of his situation finally dawned on him: he was trapped in the midst of a transformation that he couldn't reverse in mere seconds.
His mind raced, trying to process his next move. Every rational instinct told him to hide, to run, to find an escape. But there was no escaping this. The weight of the dress, the makeup, the wig; it was all too palpable, too present.
Taking a steadying breath, he opted for the only viable choice he had: to face the music. With each step towards the front door, he felt a mix of vulnerability and a surprising surge of defiant pride. This was him, in this moment, raw, exposed, and unapologetically authentic.
The door creaked open, revealing John's familiar face. But the expression was anything but familiar. Shock, confusion, and a hint of disbelief clouded his eyes as they traveled from Bryan's heeled feet, up the length of the dress, past the meticulously done makeup, and to the wig that crowned him.
For a moment, the silence was deafening, stretching the seconds into what felt like hours. Bryan's heart pounded so loudly he was sure John could hear it. Words failed him, and all he could do was stand there, waiting for the impending storm of judgment, regret, or anger.
John blinked rapidly, his face draining of color, processing the unexpected tableau before him. The stillness was eventually broken by the soft rustling of Bryan shifting his weight from one foot to the other, unsure of what to say or do.
Finally, John cleared his throat, "Bryan... I wasn't expecting to come back so soon. The meeting got canceled."
Bryan swallowed hard, the weight of his choices pressing down on him. "John, I can explain," he began, voice trembling. "It's not what it looks like, or maybe it is... I don't know. I just... I felt something when I saw Anna's dress and I wanted to... explore."
John looked at him, the surprise in his eyes now mingling with a softer emotion, maybe understanding or sympathy. He let out a deep sigh. "You know, life has a way of making us confront parts of ourselves we never knew existed. Sometimes it's through others, sometimes through situations, or even objects." He paused, rubbing the bridge of his nose, seemingly searching for the right words. "But Bryan, you should have respected our privacy."
"I know," Bryan whispered, eyes glistening. "And I'm so sorry. It was wrong."
John's initial shock was replaced quickly with an amused smirk. Taking a few steps closer, he tilted his head to the side, evaluating Bryan with a teasing glint in his eye. "You know, Bryan," he began, voice dripping with playful mischief, "you make quite the cute girl."
Bryan's cheeks flushed, a rush of embarrassment and unexpected pleasure at the compliment hitting him simultaneously. The tension in the air seemed to lighten as John continued, "Should we alter the job contract? Maybe to... Beth?"
The name hung in the air between them. Bryan felt it wrap around him just as comfortably as Anna's dress had. "Beth," he whispered, letting the new name roll off his tongue, a shy smile breaking on his face. It felt oddly fitting, a sweet reprieve in the midst of the day's chaos.
John chuckled, "Well, Beth, welcome to our home. Just remember, next time, ask before you borrow." He winked, turning the potentially awkward situation into a moment of camaraderie and unexpected bonding.
John, leaning against the door frame with a thoughtful look, began, "Anna's trip's been extended, and I've got a series of meetings coming up. This place," he gestured around the vast, modern apartment, "can be oppressively lonely. We could still use some help around here."
Bryan, or Beth, as it felt increasingly natural to think took a moment to consider. The weight of what had transpired hung in the air, but the initial fear had dissipated, replaced with a growing camaraderie.
Seeing the hesitance, John continued, "And if you're up for it, maybe... Beth could continue to help out? At least until Anna returns." He raised an eyebrow playfully, "Our little secret?"
A whirlwind of emotions swept over Beth: uncertainty, excitement, fear. But also an undeniable allure at the idea of exploring this newfound side of himself more freely. With a deep breath, he finally nodded, "Alright, but only until Anna returns. And," he added with a smirk, "only if you promise not to tease too much."
John laughed, "No promises there. Welcome aboard, Beth."
