Crossdressing Stories - Sister Feminized Me and then HE Appeared?! 🙈

Published on Dec 25, 2023 by Tohka Crow

As the golden dusk gently fell upon the city, Victor navigated through the bustling city streets. He had always preferred solitude over the constant chatter and hustle of urban life, yet today, it was different. The crowd seemed overwhelming, just like the task he was about to undertake.

"Are you sure, Skylar?" He recollected his words from the previous day's phone call, "I mean, makeup?" There was a certain uncertainty in his voice, a slight tremor indicating the uncharted territory he was about to venture into.

"Yes, Vic! Trust me, you'll be doing me a huge favor!" Skylar had retorted, her jovial tone contrasting starkly with his.

Walking along the sidewalks, he noticed the laughter of a couple nearby, a child throwing a tantrum over an ice cream, a lady hurriedly applying lipstick in her car's mirror. Everything around him seemed to pulsate with life, an intoxicating mixture of sounds, colors, and emotions. Yet, all he could think of was that daunting prospect of being a canvas for his sister's aspirations.

"It's just makeup, not a big deal." He tried to console himself, even though his stomach was in knots. He wasn't worried about the actual makeup but about the perception it might cast. He had always been conscious of his masculinity, almost to the point of paranoia. Would this make him less of a man in the eyes of others? Or worse, in his own eyes?

But as he continued to navigate the crowded streets, his thoughts turned towards his sister, Skylar. She had always been there for him, her exuberant spirit somewhat filling the void of his own social awkwardness. She had her dreams, and she was on her journey to fulfill them. If this was a way he could contribute, then perhaps, he was willing to set aside his apprehensions.

Victor reached the towering apartment building where Skylar resided, her abode amidst the urban sprawl. The vibrant graffiti on the brick walls, the occasional flickering neon lights, they all seemed too loud, too boisterous, like his sister's personality. He took a deep breath, trying to quell the nervous flutters in his stomach, and stepped inside.

"Okay Victor, it's just for practice, you're helping her. You're not less of a man," he muttered to himself in the elevator, his reflection in the polished steel walls echoing back his apprehensive expression. His heartbeat echoed in his ears, as the elevator ascended, floor by floor, towards his sister's apartment.

The moment he knocked on her door, it flew open revealing Skylar, beaming with a vibrancy that put the city lights outside to shame. "Vic! I knew you wouldn't chicken out. Come in!" Her cheerfulness eased his tension a bit, making the knot in his stomach loosen.

Inside, her living room was a colorful chaos of makeup palettes, brushes, sponges, and mirrors. A feeling of foreignness washed over him as he looked around, the world of colors and brushes so alien to him.

"You ready, bro?" Skylar's question pulled him back from his thoughts. He managed a weak nod, before uttering, "Yeah, I guess."

Skylar's eyes gleamed with excitement as she led him to a chair facing a large mirror. He saw himself seated, a man about to step out of his comfort zone, all for his sister. "I guess some things are worth the discomfort," he thought, forcing a smile on his face.

As Skylar began applying a gentle layer of foundation, Victor couldn't help but watch his transformation in the mirror. He felt the soft brush strokes against his skin, the cool, damp sponge dabbing, blending the alien substance into his pores. It felt strange but not entirely unpleasant. He could understand why Skylar was so fascinated by this art.

"Vic, you need to relax," Skylar's voice cut through his introspection. He looked up to see her smiling at him, a genuine, affectionate smile. He gave a slight nod and tried to unclench his fists, releasing a tension he hadn't realized he was holding.

Victor lost track of time as his sister worked her magic, applying eyeshadow, mascara, and even some lipstick. He had to admit, the precision and skill with which she worked was admirable. It was clear that this wasn't merely a hobby for her; it was a passion, a dream she wanted to chase.

"Alright, done!" Skylar finally announced, stepping back to admire her work. Victor glanced in the mirror, his heart pounding. The face that stared back wasn't the same old Victor he knew. It was different, softer, and more colorful.

Despite the shock, Victor couldn't ignore the spark in Skylar's eyes as she looked at her masterpiece. The apprehension, the discomfort, the nervousness, they all seemed trivial compared to the joy he could see in his sister's eyes. Victor realized that this wasn't about him at all. It was about supporting someone he cared about, irrespective of societal norms and expectations.

"It's... different," he managed to say, "but I'm glad I could help, Skylar." His voice was shaky, but the sincerity in it was unmistakable.

Skylar beamed at him, her eyes welled up with happiness and gratitude. That sight, that single moment of pure, unadulterated joy in his sister's eyes, made all of Victor's worries fade away. After all, wasn't that what family was all about?

"You look cute, Vic! But we're not done yet," Skylar suddenly chirped, her eyes gleaming with a playful mischief. She disappeared into her room for a moment, returning with an armful of items that made Victor's face turn several shades redder.

In her hands were some girly clothes, lingerie, and a short curly blonde wig. Victor gulped, his eyes widening. He knew he was in for more than just makeup, but this was something he hadn't quite expected. However, he swallowed his hesitation, seeing the glint of excitement in Skylar's eyes.

"Just...just don't laugh, okay?" he implored, accepting the clothes from her. Skylar's grin was a reassuring one, her hand giving his a comforting squeeze. "You're doing great, bro. And I promise, no laughing."

He hesitated, then disappeared into the small bathroom to change. The lingerie was a soft pink, lacy and delicate to the touch. The clothes were similar - a short, floral sundress. It was a stark contrast to the casual, loose clothes he was accustomed to. Once dressed, he gingerly placed the blonde wig on his head, adjusting the curls until they framed his face naturally.

Coming out, he met Skylar's gaze, her wide-eyed look of surprise melting into a beaming smile. "Victor, you look...amazing," she said, circling him. It was not mockery or ridicule in her voice, but sincere admiration, making him feel somewhat at ease.

Despite the initial awkwardness, Victor couldn't help but feel a certain warmth spreading in his chest. It was strange, even comical to an extent. But in that moment, he realized the lengths to which he was willing to go to support his sister. He wasn't just Victor anymore. He was Skylar's muse, her guinea pig, her supportive brother. "Just this once, Skylar. Only for you," he murmured, meeting her happy gaze with a soft, tentative smile of his own.

Standing in front of the mirror, Victor, or the person who looked back at him, was unrecognizable. He found himself oddly fascinated by the stranger he had become, the smooth complexion, the way the dress accentuated his slim physique, the golden curls that framed his face. He felt an unanticipated pang of... what? Admiration? Satisfaction? He wasn't sure.

"I'm a man," he murmured to his reflection, trying to reconcile the image with his own sense of self. Yet there was a strange allure to this new identity, a curiosity that tugged at the edges of his comfort zone. The thought made his heart pound. Was he supposed to enjoy this? Was it okay to find himself... attractive?

"Victoria," a voice broke through his internal turmoil, and he turned to find Skylar watching him, her eyes twinkling. Victor blinked, a new jolt of surprise washing over him. Victoria? He looked back at the mirror, the name echoing in his mind. Victoria. It felt oddly right. "I think I like that," he confessed, his voice barely above a whisper.

Skylar beamed, wrapping her arm around him. "You're more than just my brother, Victor. You're my best friend, my confidante. Whether you're Victor or Victoria, that won't change. I'm proud of you."

Victor felt a warmth spreading through him, a sense of acceptance that eased his internal conflict. Maybe it didn't matter what he wore or how he looked. Maybe what mattered was that he felt comfortable in his own skin, and he was willing to explore new aspects of himself. "Thank you, Skylar," he said softly, meeting her gaze in the mirror. "For showing me a different side of myself. I think I needed that."

Victor, or Victoria as Skylar had so affectionately named him, found himself lost in a cascade of memories. His past seemed to unfurl in front of him, a tapestry of moments woven with threads of self-doubt, introversion, and the endless struggle of fitting into a box he was never quite comfortable in.

His mind harked back to his childhood, the time when his short stature and slight build would often lead people to mistake him for a girl. He remembered the confused glances, the awkward laughter, and the attempts to correct people without losing his composure. Those memories had once been sources of embarrassment, but now they appeared in a new light, less bitter, more enlightening.

His thoughts wandered to the countless times he'd shrunk back in social situations, preferring the quiet comfort of his own company over the anxiety-inducing crowd. The inability to muster the courage to talk to women, to express his feelings, to initiate a relationship. It had always seemed like a personal failing, a gaping void in his life that he was incapable of filling.

But staring at his reflection, this beautiful, feminine version of himself, he wondered. Had he been seeking the wrong thing all along?

He'd been so engrossed in the conventional ideas of relationships, of masculinity and femininity, that he'd never considered there might be another way.

Victoria. The name echoed in his mind again. It had a pleasant ring to it, a comforting cadence that seemed to resonate with a part of him he'd been unaware of. Could it be that he wasn't meant to seek a girlfriend, but rather embrace this new side of himself? Was it possible that his happiness lay not in conforming to societal norms, but in understanding and accepting his own uniqueness?

The revelation was simultaneously overwhelming and liberating. But for the first time, Victor felt a sense of relief. As if a weight he'd been carrying around had been lifted. A smile crept onto his face as he stared at his reflection. "Victoria," he murmured, and this time, it sounded just right.

An unexpected knock rattled the door, startling both Skylar and Victor from their shared celebration. With a look of surprise, Skylar moved to open the door, revealing a tall figure bathed in the warm glow of the hallway light.

Mark was undeniably handsome. Dark hair, chiseled jawline, and a muscular build that hinted at a regular workout regimen. He was clad in a well-fitted shirt that accentuated his broad shoulders, and his cologne - a rich, woody scent - filled the room as he stepped inside, cradling a six-pack of beer.

"I thought we should celebrate," he declared, a grin dancing on his lips. He began to explain his recent victory at work - a pay rise he'd earned with Skylar's help. His joy was infectious as he embraced Skylar in a grateful hug. Then, as he pulled away, his gaze wandered and landed on Victor.

The unexpected guest had left both Skylar and Victor momentarily flustered. They shared a glance, a silent conversation passing between them. Then, Skylar broke the silence, her voice calm despite the surprising circumstances.

"Mark, meet Victoria," Skylar began, her eyes flicking to Victor's dolled-up figure. "An old childhood friend of mine."

Mark looked taken aback for a moment, but then his expression softened into a warm smile. "Nice to meet you, Victoria," he said, his eyes flickering over Victor's transformation with a hint of intrigue. For Victor, the moment was a blend of fear and thrill, a potent cocktail that left his heart racing. The night, it seemed, had taken an unexpected turn.

"You too, Mark," Victor responded, his voice coming out softer and higher-pitched than he'd expected. He met Mark's outstretched hand, noticing the firmness of his grip and the warmth radiating from his skin. He could still smell that tantalizing cologne, and it made his heart pound harder in his chest. Was it possible he was feeling attracted to Mark? The thought was as scary as it was exciting.

"Come in, Mark," Skylar beckoned, leading him towards the couch. She handed Mark a beer and took one for herself, leaving Victor to fetch his own. As Victor moved around the apartment, he couldn't help but feel Mark's eyes on him. His face heated up under the man's gaze, but a part of him also enjoyed the attention.

As they settled down, Mark began regaling them with tales of his work, his jokes making them laugh. Victor found himself stealing glances at Mark, the light from the lamp highlighting the contours of his face, making him even more attractive. Each laugh, each smile from Mark sent a shiver down Victor's spine, making him acutely aware of his lingerie-clad body underneath the feminine outfit.

Later, as they started playing a round of card games, Victor felt a sense of ease settling in. Despite the initial shock, it seemed as if the evening was going to be an enjoyable one. He shared glances with Skylar, her reassuring smiles making him feel less out of place. In the soft light of the apartment, with the city noises forming a distant hum, Victor felt a strange sense of contentment. Could it be that Victoria was more than just a disguise? Perhaps it was a part of him he had yet to fully understand. The night was still young, and Victor found himself eager to see where it would lead.

As the evening wore on, Skylar suddenly jumped to her feet, breaking the ongoing conversation with an apology. "We're out of snacks," she announced, frowning at the empty bowls on the coffee table. "I'll just run to the store. Won't be long."

With a wink at Victor, she grabbed her purse and headed out, leaving him alone with Mark. Suddenly, the apartment felt too quiet, the silence punctuated only by the ticking of the wall clock. Victor's heart pounded in his chest like a wild drum, his hands slightly shaky.

Time seemed to stretch on endlessly, until finally, Mark broke the silence. His voice was steady, the conversation trivial - something about a funny incident at work - but it was enough to cut through Victor's nervous tension. Gradually, his heart rate slowed, his breathing returned to normal, and he found himself able to meet Mark's gaze without flinching.

As the minutes passed and the small talk ebbed and flowed, Victor's apprehension began to melt away. He found himself more comfortable, more present in the situation. Emboldened by this newfound confidence, Victor's hand drifted, almost unconsciously, to rest lightly on Mark's thigh. The contact was electric, a jolt of sensation that had Victor's breath hitching in his throat. The boundaries between Victor and Victoria were blurring more than ever, and the anticipation of what might happen next was nothing short of intoxicating.

Mark paused mid-sentence, his gaze shifting down to where Victor's hand rested. An unreadable expression crossed his face, and for a moment, Victor feared he had crossed a line. But then, Mark turned back to him, his eyes softening as he studied Victor's face.

"You okay, Victoria?" he asked, his voice low and surprisingly gentle. Victor nodded, unable to find the words. He made no move to withdraw his hand, and Mark didn't push him away. Instead, Mark placed his hand over Victor's, an acknowledgment, a silent acceptance that made Victor's heart skip a beat.

The room felt heavy with unsaid words and lingering looks. Victor felt a warm blush creeping up his cheeks. His mind was a whirlpool of emotions; confusion, excitement, and a strange sense of liberation. He was living in a moment he'd never imagined himself in. He was Victor, but he was also Victoria, caught between identities yet oddly at peace with the uncertainty.

The silence stretched on, but it wasn't uncomfortable. Victor felt a magnetic pull towards Mark, a connection he couldn't deny. As they sat there, waiting for Skylar's return, the boundaries between them seemed to dissolve, replaced by a growing understanding. This was a night of discovery, a turning point in Victor's life. Where it would lead, he didn't know. But for the first time in a long time, he felt excited about the journey.

The tension between them was electric, their faces drawing closer together. Victor could see every detail of Mark's face, the light stubble on his jaw, the faint scar on his cheek. His heart pounded in his chest, his breath hitching as their lips moved dangerously close.

Just as their lips were about to meet, the rattling of keys in the lock broke the spell. They pulled away from each other abruptly, Victor's hand slipping from Mark's thigh. Skylar walked in, her arms full of shopping bags, completely oblivious to the charged atmosphere she'd just walked into.

The rest of the evening was a blur, filled with light-hearted conversation and laughter. The air was thick with unspoken words, but both Victor and Mark played their parts well. As the night came to a close, Mark left with a smile and a casual peck on Victoria's cheek that sent shivers down Victor's spine.

Not wanting to break the illusion, Victor left Skylar's apartment still dressed as Victoria, the city lights reflecting off his makeup. When he reached his own apartment, he slowly removed the wig, the makeup, the clothes, shedding Victoria and returning to Victor.

As he lay in bed, Victor found himself replaying the night's events over and over. His mind spun with thoughts and emotions, a confusing mess that he was unable to untangle. He was Victor, but he had also been Victoria, and that realization had unearthed feelings he had never before acknowledged. He knew he had a lot to think about, a lot to understand, but for the first time in his life, he felt a spark of excitement for the journey ahead.