My Crossdress up Darling Ch 10 : Gown Fitting

Steve found himself standing at the grand doors of a beautiful church, sunlight streaming through the stained glass, casting colorful patterns across the polished floor. He looked down and froze, realizing he was wearing a white gown—layers of satin and lace flowing around him, delicate embroidery glistening in the light. His hands were holding a bouquet of soft pink and white roses, the petals so perfect they seemed almost unreal.

“What… what’s happening?” he murmured, his voice barely a whisper. He glanced around, still dazed.

“Stephanie!” a voice called out. He looked up to see Lily standing nearby, dressed in a soft pastel dress, her face lit up with a smile. Beside her was Angela, waving with equal enthusiasm, both of them looking at him like he was exactly where he was meant to be.

“You look stunning, Stephie!” Angela laughed, her eyes twinkling.

Lily gave him a little thumbs-up. “I can’t believe you’re finally doing this! Go get your happily ever after!”

Steve lifted a hand to wave back, his mind still swimming with confusion. “Wait… doing what?” he mumbled, more to himself than to anyone else.

Just then, the gentle strains of a piano filled the air—the unmistakable melody of the wedding march. The sound echoed through the church, and Steve’s heart raced. He glanced around, trying to make sense of everything, but the music was all-consuming, the gentle notes wrapping around him, urging him forward.

“I… what am I supposed to…?” he muttered, feeling his nerves spike. He took a shaky breath, the weight of the gown making him feel both graceful and strangely vulnerable. His gaze darted around, searching for some kind of answer.

And then he felt it—a warm hand slipping into his. He looked up and saw Mitch standing beside him, dressed in a crisp white suit, his face relaxed, eyes shining with a warmth that made Steve’s heart skip a beat.

“Hey,” Mitch said softly, his smile gentle. “Ready?”

Steve stared at him, utterly entranced. “I… I think so?”

Mitch’s smile widened, and he gave Steve’s hand a reassuring squeeze. “Good. I’m right here with you.”



Mitch’s words settled over him like a balm, calming his racing heart. With Mitch at his side, he felt a strange sense of peace, like this was exactly where he was supposed to be. Together, they began to walk down the aisle, Mitch guiding him gently, his hand firm and steady.

Steve took in the faces around him—Angela and Lily were beaming, their smiles filled with pride. Scattered among the guests, he recognized coworkers from the office, each of them clapping and smiling, as if they’d been waiting for this moment as long as he had.

As they approached the altar, Steve’s heart was pounding, the reality of the moment sinking in. Mitch turned to face him, his gaze so soft, so filled with something that looked a lot like… love.

Mitch took a step closer, his hand still holding Steve’s. “You look amazing, Stephie,” he murmured, his voice just loud enough for Steve to hear.

Steve felt his cheeks warm, a shy smile breaking through. “You… really think so?”

“Absolutely,” Mitch replied, his eyes never leaving Steve’s. “I’m the luckiest guy here.”

Steve’s heart fluttered, and he felt an overwhelming urge to say something, but his voice seemed to fail him. Instead, he found himself gazing back, caught in the quiet strength of Mitch’s smile.

The pastor’s voice seemed distant as he spoke, saying something about love, commitment, promises. Steve couldn’t focus on the words; all he could think about was Mitch’s hand in his, the way it grounded him, the way it made everything feel so beautifully, perfectly real.

Then came the moment he’d been waiting for, even if he hadn’t known it. Mitch reached up and lifted the veil from Steve’s face, his touch gentle and reverent. They were close now, so close that Steve could feel Mitch’s breath, could see the warmth in his eyes as he took in every detail.

“Are you ready?” Mitch whispered, his voice filled with affection.

Steve’s voice was barely a whisper. “I… I think so.”

With a soft smile, Mitch leaned in, closing the distance between them. Steve’s heart was racing, his breath catching as Mitch’s lips came closer and closer, until—

Steve’s eyes snapped open, and he found himself staring at the familiar shadows on his bedroom ceiling. He sat up, his heart pounding, his face flushed as the remnants of the dream lingered, vivid and disorienting.

He ran a hand over his face, trying to shake off the fog of sleep. “It… it was a dream?” he whispered to himself, still caught between reality and the surreal images that felt so real just moments ago.

The details of the dream came rushing back—the way Mitch had looked at him, the warmth in his eyes, the feeling of his hand holding Steve’s so gently yet so firmly. And that final moment, the kiss that had almost happened. Steve pressed a hand to his chest, trying to calm his racing heart.

What was that all about? he wondered, a mix of embarrassment and something he couldn’t quite name flooding through him. He thought back to the way he’d felt in the dream—the excitement, the certainty, the feeling that being beside Mitch was exactly where he was supposed to be.

He glanced at the clock, still blinking in the darkness. It was just a dream… right? But as he lay back down, trying to find sleep again, he couldn’t help but wonder if his feelings for Mitch went deeper than he’d ever realized.

At the office, Steve found it nearly impossible to focus. With each passing day, the pressure of the upcoming event felt heavier, and no amount of training seemed to ease his nerves. Twice a week, he and Mitch would go over every step, every spin, and every dip. Mitch would guide him with that calm confidence, his hand steady on Steve’s back, his voice patient. But the closer they got to the big day, the more Steve’s feelings complicated everything.

He wasn’t sure when it had happened, but he knew now that it was more than friendship he felt for Mitch. This wasn’t like his close bond with Lily, who was fun and encouraging. What he felt for Mitch was different. It felt intense, almost overwhelming—something that made him feel like he could be someone entirely different, someone… softer, someone who belonged by Mitch’s side.

He was so lost in thought, staring blankly at his computer screen, that he didn’t notice Jenna standing beside him.

“Steve?” Jenna’s voice snapped him out of his daze. “Earth to Steve.”

He blinked, turning to her, trying to gather his thoughts. “Oh! Hey, Jenna. Sorry, I was just… somewhere else.”

She smiled, watching him with amused curiosity. “Yeah, I noticed. You’ve been daydreaming a lot lately. Got something on your mind?”

His face grew warm, and he struggled to find the right words. “Uh… yeah, you could say that. Just… personal stuff.”

Jenna tilted her head, her expression turning playful. “Mmm, personal stuff, huh? That sounds a little suspicious. Romance?”

Steve’s face went even redder, and he laughed awkwardly. “No, no, nothing like that,” he said quickly, though his heart betrayed him with a quick flutter. “It’s just… complicated.”

She gave him a knowing smile. “Well, if you ever need a sounding board, I’m here. Sometimes a fresh perspective can make all the difference.”

“Thanks, Jenna,” he replied, feeling both relieved and flustered. He didn’t need her knowing the real reason for his distraction. The truth was, every time he practiced with Mitch, he felt his heart grow a little fonder, his admiration turning into something he couldn’t quite control. 

Mitch made him feel… different, almost like he could let go of everything he thought he was supposed to be. Mitch made him feel as if, in his presence, he could be as vulnerable, as soft, as openly affectionate as he wanted. It was almost like being someone else—someone who didn’t have to pretend.

Jenna gave his shoulder a friendly pat. “Whatever it is, I’m sure you’ll work it out. You’ve got that look, you know?”

Steve’s brows furrowed. “What look?”

“That look people get when they’ve found something special.” She winked, then walked away, leaving Steve even more confused.

He managed to nod, watching her go, but his mind had already wandered back to Mitch. Something special, he thought. He hadn’t thought of it like that, but maybe Jenna was right. Whatever he had with Mitch felt unique, different from anything he’d felt before.



Just then, Lily appeared beside him, breaking through his thoughts. “Hey, Stephie! Are you ready for the big event this weekend, honey?” Her tone was light and teasing, but that word—honey—made him jump.

“Lily!” he hissed, his face flushing. “Please don’t call me that. Especially not here!”

Lily laughed, clearly unfazed. “Relax, no one’s listening,” she said, giving a quick glance around the office. She lowered her voice, though her grin stayed playful. “Besides, it’s cute.”

“Maybe to you,” Steve muttered, trying to ignore the heat rising in his cheeks. “But I don’t know, Lily… I really don’t think I can go through with this.”

Lily raised an eyebrow, pulling over a chair and sitting down beside him. “What are you talking about? You’ve been practicing, right?”

“Yeah, but…” he trailed off, sighing. “Practicing is one thing, but being in front of an actual audience? That’s different. I keep thinking I’ll mess it up and ruin everything.”

Lily shook her head, her expression softening. “You’re not going to mess up, Steve. You’ve been doing great in every practice. You just have to trust yourself.”

Steve looked down, fiddling with his pen. “It’s just… what if I freeze up? Or forget the steps? Everyone’s counting on me to do this right.”

Lily placed a hand on his shoulder, giving it a reassuring squeeze. “You’re not alone up there. You’ll have your friends beside you, and we’ll all be in it together. No one’s expecting perfection, Stephie. Just go out there and have fun, like we always do.”

He looked at her, his anxiety easing just a little. “You really think it’ll be okay?”

Lily grinned, her confidence infectious. “I know it will. And honestly, once you’re in costume, under the lights, you’ll feel like a different person. Just let yourself enjoy it, and the rest will fall into place.”

A small smile crept onto Steve’s face, a hint of relief finally breaking through his nerves. “Thanks, Lily. I… I needed to hear that.”

“Good,” she said, standing up and giving him an encouraging nod. “Now, try to stop worrying so much. Save the overthinking for the performance.” She shot him a wink as she walked away, leaving him with a little more confidence than before.

As Lily took a seat beside him, her face lit up with a mischievous grin. “By the way I’ve got news. Your gown is finally ready!” she whispered, as if sharing a secret.

Steve’s eyes widened. “Wait… really? It’s done already?”

“Yep! Maia just finished it. We’ll be doing the gown fitting on Thursday,” she replied, her eyes sparkling with excitement. “Just in time for the big event this weekend.”

He took a deep breath, trying to process it. The nerves that had been simmering all week suddenly felt much closer to the surface. “I can’t believe it’s happening so soon,” he murmured. “It felt like we had all the time in the world, and now…” He trailed off, running a hand through his hair with a faint smile. “How about you? Are you all set?”

Lily shrugged, waving a hand. “Oh, don’t worry about us. Evelyn, William, and I are just wearing simple gowns, nothing too elaborate. I’ll be dancing with William, but we’re just there as background.”

Steve raised an eyebrow, a little incredulous. “Background? You’re calling yourself ‘background’ now?” he teased, half-relieved to focus on something other than his own nerves.

Lily gave a light laugh, nudging him with her elbow. “Hey, we all know who the real stars of the night are. It’s you and Mitch,” she said, lowering her voice with a wink. “The spotlight’s yours, Stephie.”

Steve swallowed, feeling his heart pick up. “So… no pressure, then?” he joked, but the tremor in his voice gave away just how nervous he really was.

“None at all,” Lily replied with a grin, but her tone softened as she continued, “Seriously, Steve, you’ve got this. I’ve heard you practice, and you’re going to be incredible. Just trust yourself and enjoy it.”

Steve let out a shaky laugh, rubbing his neck. “It’s hard not to think about all the ways it could go wrong, you know?”

“Hey,” Lily said, placing a reassuring hand on his shoulder. “You’ve worked so hard for this, and you have all of us rooting for you. The only thing you need to do is show up and let yourself have a little fun.” She gave his shoulder a squeeze, her confidence in him somehow making his own nerves settle a bit.

As she stood to head back to her own desk, she threw him one last smile. “Remember—Thursday, gown fitting. And then on Saturday… you’re stepping into that spotlight.” 

He watched her go, her words sinking in. The event was right around the corner, and the thought of stepping into that gown, standing in the spotlight, and performing for the crowd was both terrifying and thrilling. He didn’t know if he was truly ready, but with a little help from his friends, maybe—just maybe—he could pull this off.

On Thursday afternoon, Steve waited nervously at the train station, adjusting his bag and glancing around to see if Lily and Evelyn were on their way. His heart thumped with anticipation. Today was the gown fitting, and while he’d tried to act casual about it all week, he couldn’t deny he felt both nervous and excited.

“Steve!” Lily’s cheerful voice called from behind him, snapping him out of his thoughts. He turned to see her hurrying over with Evelyn right behind her, both of them practically bouncing with excitement.

“Hey, Stephie!” Lily said with a grin, using her favorite nickname for him. “Ready to see yourself in the gown?”

Steve laughed, feeling his face flush a bit. “I… I guess so? It still doesn’t feel real.”

“Oh, trust us,” Evelyn chimed in, giving him a playful nudge. “It’s going to feel real when you see yourself in that mirror.”

The three of them headed to Akiba Costume together, their laughter and chatter filling the air. As they approached the shop, Steve’s nerves returned, but seeing Lily and Evelyn’s excitement helped keep him steady. The whole thing felt surreal—just last month, he would’ve never imagined himself doing a gown fitting.

When they entered the shop, Maia, the owner, greeted them with her usual warm smile. “Welcome back, everyone! I’ve been waiting for you. All the gowns are ready, and I think you’re going to love them.”

Lily practically clapped her hands in excitement. “I can’t wait! Let’s see them, Maia.”

Maia gestured to a rack near the dressing rooms, where several beautiful gowns hung, each one delicate and carefully crafted. Lily and Evelyn gasped, and Steve’s eyes widened as he took in the details—the soft fabrics, the intricate embroidery, the rich colors. It was like stepping into a dream.

“Lily, Evelyn,” Maia said, handing them each a gown, “you’re in changing rooms one and two. And, Steve,” she continued, carefully handing him a dress wrapped in protective fabric, “you’re in room three.”

Steve took the gown, feeling its surprising weight and softness. He glanced at Lily and Evelyn, who were already beaming with excitement as they headed for their changing rooms.

“Good luck, Stephie!” Lily whispered with a wink before disappearing behind her curtain.

“Can’t wait to see you all dressed up,” Evelyn added with a grin, then closed her own dressing room door.

Steve took a deep breath, then stepped inside the changing room, closing the door behind him and carefully setting the gown down, feeling its weight in his hands. He slowly unzipped the protective bag, peeling it open to reveal the dress inside. His breath caught as he saw it fully for the first time. The fabric was a soft, ethereal blue, with delicate silver embroidery that shimmered under the light, catching every small movement. Intricate swirls and patterns danced along the bodice and skirt, like starlight woven into silk.

For a long moment, he just stared at it, almost afraid to touch it. This gown… it’s beautiful, he thought, feeling a mixture of excitement and nervousness. The craftsmanship, the detail—everything about it was stunning.

Taking a deep breath, he reached for the gown and carefully began slipping it on. He managed to get it over his shoulders, but the back zipper seemed just out of reach, and the gown was heavier than he’d expected, the layers of fabric slightly cumbersome.

Suddenly, the door swung open, and Maia stepped in, smiling brightly. Startled, Steve let out a small yelp, almost a squeal, sounding far more like a little girl than he intended. His face flushed red instantly.

“Maia!” he stammered. “I… I didn’t realize you’d—”

Maia chuckled, completely unfazed. “Don’t worry, sweetheart. I knew you’d need a hand with this gown,” she said, moving forward with practiced ease. “Here, let me help you with that zipper.”

He turned, letting Maia adjust the gown, gently fastening the zipper and adjusting the shoulders. Her hands moved expertly, smoothing out any creases and arranging the fabric so that it flowed perfectly. She stepped back, admiring her work with a satisfied smile.

“There,” she said, nodding approvingly. “You’re all set.”

Steve took a deep breath and turned to face the mirror. When he finally looked up, he froze, barely recognizing himself. The gown fit him perfectly, the bodice snug but comfortable, the skirt flowing out in soft, shimmering waves that reminded him of the classic ballgown from the Cinderella movie. The way the fabric moved, the sparkle of the embroidery, the shape of the skirt—it was like stepping into a fairytale.

He felt like he was looking at a completely different person in the mirror. He wasn’t Steve, a nervous guy waiting to perform. In that moment, he truly felt like a princess.

“I… I can’t believe it,” he murmured, his voice barely a whisper as he touched the fabric, feeling the cool, smooth material under his fingers.

Maia beamed, watching his reaction. “You look stunning, Steve. Or should I say… Stephanie?”

He blushed, a shy smile tugging at the corners of his mouth. “Thank you, Maia. It’s… it’s perfect. It’s everything I imagined and more.”

“You’re going to take everyone’s breath away at the event,” she said with a proud smile. “Now, come on—let’s show Lily and Evelyn. I think they’ll agree you’re ready for the spotlight.” 

Steve took a deep breath, bracing himself as he stepped out of the changing room. The soft rustle of his gown echoed around him, and when he finally looked up, he saw Lily and Evelyn standing there, both already transformed into their own fairytale versions. 

Lily wore a yellow gown, the color rich and deep, flowing around her like Princess Belle straight out of Beauty and the Beast. She was practically glowing, the dress fitting her with an effortless elegance. Beside her, Evelyn was dressed in a soft pink gown that looked just like Princess Aurora from Sleeping Beauty, complete with delicate details that gave her a timeless, storybook grace.

The moment they saw him, their eyes widened, and then they erupted into delighted squeals.



“Oh my god, Steve!” Lily’s voice was a mix of excitement and awe as she clapped her hands. “You look adorable! Like, I mean it—you could be straight out of a Disney movie!”

Evelyn nodded enthusiastically, her own face lit up with a wide grin. “I knew the dress would be stunning, but wow… you look like an actual prince—no, a princess.”

Steve’s face flushed at their reactions, a bit overwhelmed by their enthusiasm. “Thanks… it’s a little surreal,” he admitted, smoothing the skirt self-consciously. The dress truly did feel magical, and seeing Lily and Evelyn’s reactions only made it feel more real.

Maia, watching the scene with a warm smile, stepped forward. “Oh, we’re not quite finished yet,” she said, holding up a wig that Steve hadn’t even noticed before. “This will complete the look.”

She guided him to a seat and gently placed the wig on his head, adjusting it with practiced hands. The hair was a rich, golden blonde, styled with soft curls that framed his face and fell gracefully over his shoulders. The transformation felt almost instant—he barely recognized himself, feeling like a different person entirely.

When he stood up and faced Lily and Evelyn again, their jaws dropped.

“Oh my god, Steve,” Lily breathed, her hands flying to her mouth. “You… you look exactly like Lily James in Cinderella! It’s unreal.”

Evelyn’s eyes sparkled with excitement. “Seriously, I don’t even know what to say. You’re like a living fairytale princess. I can’t wait to see you in action!”

Steve’s cheeks turned a bright shade of pink as he took in their reactions, but deep down, he couldn’t help but feel a surge of excitement. For the first time, he felt like he was truly stepping into a role, ready for the magic of the upcoming event.

Lily grinned, practically bouncing with excitement. “This is going to be amazing. I can’t wait to see you dance at the event! You’re going to steal the show.” 

Steve stood in front of the mirror, entranced by the way the gown shimmered and flowed around him. The soft blue fabric caught the light beautifully, the delicate embroidery adding an almost magical glow to the whole dress. He couldn’t resist—it was like he was seeing a completely different person in the reflection, someone who actually looked like a character from a fairytale. He reached down to lightly touch the skirt, feeling the smoothness under his fingertips, and gave a gentle swirl.

The skirt flared out, catching the light even more, and for a moment he felt like he was lost in a story. A smile crept onto his face, and without even thinking, he did a little spin, watching as the gown twirled around him. The feeling was… thrilling, really, something he’d never felt before. He gave another spin, letting the fabric sweep gracefully around his legs, feeling free, elegant, and almost… radiant.

Lily raised an eyebrow, barely holding back a laugh as she watched him. “Calm down, Stephie,” she teased, grinning. “Don’t wear yourself out twirling before the big event.”

Steve stopped mid-spin, his face instantly heating up. He looked back at her, suddenly self-conscious. “Oh, right, sorry,” he said, rubbing the back of his neck with a shy laugh. “Guess I got a little carried away.”

Lily laughed, giving him a playful nudge on the shoulder. “Don’t apologize! You look amazing, and it’s obvious you’re loving it. Just save a little of that energy for when you actually have an audience, okay?”

He nodded, still feeling his cheeks warm as he stole another glance in the mirror. An audience, he thought, the word sending a nervous thrill through him. But it wasn’t just any audience he was thinking about. His mind drifted to Mitch—what would he think when he saw him like this? Steve imagined Mitch’s face as he walked into the room, eyes widening just a bit, his usual calm expression giving way to surprise and, maybe, admiration. Mitch would probably smile, maybe even say something kind.

Steve’s breath hitched slightly as his thoughts took a turn he hadn’t expected. He imagined Mitch stepping closer, leaning down, and, as if enchanted by the sight, brushing a gentle kiss on his lips. The image was so vivid that his heart sped up, and he felt a sudden rush of warmth that he couldn’t quite explain.

Wait… what am I thinking? He blinked, surprised at his own thoughts, and a wave of confusion flooded over him. Why am I… wanting that? He turned away from the mirror, fidgeting with the gown as if to distract himself, but the question lingered.

Am I turning into gay now? The thought trailed off, leaving him both flustered and strangely exhilarated. He’d never felt this way before—never like this. But now, with the upcoming performance and everything about it, he couldn’t shake the feeling that something was changing. And for the first time, he wasn’t sure if he wanted it to stop.