My Crossdress up Darling Ch 8 : The Meet Up

Steve found himself in the middle of the crowded convention hall, still dressed in his bright pink Cardcaptor Sakura costume. He clutched his magical wand nervously, scanning the crowd. Everything around him seemed larger and more chaotic than before. People passed by in a blur, their faces indistinct, the noise of the crowd growing louder. He felt small, vulnerable, and alone.

Then, out of nowhere, a man in a hoodie approached, his face shadowed. Steve instinctively backed away, but before he could react, the man grabbed his arm, pulling him toward a dark corner of the hall. Fear shot through him. His heart pounded in his chest as he struggled to pull free, but the man’s grip tightened.

“Let me go!” Steve shouted, his voice coming out high-pitched, more like Sakura than his real self. The noise of the crowd seemed to fade away, and suddenly, he felt completely isolated. No one around him noticed, no one came to help.

Just as Steve thought there was no way out, a deep, commanding voice boomed behind him.

"Yare yare daze."

Steve whipped his head around, and there he was—Mitch, in his full Jotaro cosplay, looking more like the anime character than ever. His presence was overwhelming, towering over the man in the hoodie. Mitch’s face was stern, his jaw clenched in determination, and his sharp gaze zeroed in on the hooded man who had dared to lay a hand on Steve.

“You picked the wrong girl to mess with,” Mitch growled, stepping forward, his coat billowing behind him like a cape. “Time to teach you a lesson.”

The man tried to pull Steve away, but Mitch was already in action. “Star Platinum!” he shouted, and in an instant, the air seemed to ripple with energy. Steve blinked, and suddenly, Star Platinum, the powerful Stand from JoJo’s Bizarre Adventure, appeared behind Mitch—massive and intimidating, its fists clenched and ready for action.

"ORA ORA ORA ORA ORA!" Mitch roared, commanding Star Platinum into a rapid flurry of punches. The Stand’s fists flew at blinding speed, each hit landing with incredible force, the blows echoing through the air as they collided with the hooded man. The man’s grip on Steve loosened immediately as he stumbled back, completely overwhelmed by the onslaught of attacks.

Steve watched in awe, his fear giving way to amazement as Mitch’s Star Platinum pummeled the man with lightning-fast strikes. The power of the punches sent the hooded man flying backward, crashing into the ground with a thud. He didn’t stand a chance against Mitch’s sheer force.

“Yare yare daze,” Mitch muttered again, walking over to Steve, extending his hand with a soft but confident smile.

“You alright, Stephanie?” Mitch asked, his voice a low rumble that was both reassuring and protective.

Steve’s heart raced, but this time not from fear. The way Mitch had saved him—his strength, his control over the situation—it left Steve feeling both grateful and strangely flustered. “I-I’m okay,” Steve stammered, still in awe. “You... you saved me.”

Mitch’s expression softened, and before Steve could react, Mitch pulled him into a close embrace. His arms wrapped securely around Steve, making him feel safe in a way he hadn’t expected. “I’ll always protect you,” Mitch said, his voice soft now, full of warmth.

Steve could feel his own heartbeat quicken. He rested his head against Mitch’s chest, breathing in the scent of his cologne mixed with the faint smell of leather from his costume.

The world around them seemed to blur, the convention fading away. All that was left was Mitch, standing tall and strong, his arms wrapped protectively around Steve. It felt... safe. Safe in a way that Steve had never experienced before.

Then, something shifted. Mitch tilted his head down, his eyes meeting Steve’s in a way that sent a shiver down Steve’s spine. Mitch’s hand slid to the back of Steve’s neck, his touch gentle yet firm. For a brief moment, it felt like time had stopped. Mitch leaned in closer, his face just inches away from Steve’s, his breath warm against Steve’s cheek.



Steve’s heart pounded in his chest, his mind racing. Was this really happening? Did he want this to happen? His thoughts tangled together in confusion, but his body remained still, frozen in the moment.

Then, just as Mitch’s lips were about to meet his, Steve jolted awake.

Steve sat up suddenly, heart pounding, as the lingering feelings from his dream faded away. The dream had been so vivid—Mitch, dressed as Jotaro, coming to his rescue like some kind of superhero. The way Mitch had hugged him afterward, that intense moment where it felt like something more might happen. And then... he had woken up.

Rubbing his eyes, Steve tried to shake the strange feeling that lingered. Why did I dream about that? he wondered. The dream was unsettling, not because Mitch had saved him, but because of how real it had felt—the hug, the closeness, and the way his heart had fluttered in that moment. It left him feeling confused.

Am I... gay? The question hung heavy in his mind, and he wasn’t sure how to answer it. He had never thought of himself that way before, and yet here he was, in a Cardcaptor Sakura costume, dreaming about being saved by a guy like Mitch. Was it admiration for Mitch’s strength and confidence, or was it something deeper? Something he hadn’t fully realized yet?

Steve sat on the edge of the bed, staring at his reflection in the mirror. The costume, the makeup—it was all part of the day’s events, just cosplay, a fun way to step into a different character. But now, after everything, he couldn’t help but wonder if it had stirred something in him that he hadn’t considered before. Maybe it wasn’t just about the costume or the convention. Maybe it was about discovering a part of himself he hadn’t been ready to face.

“Why did I dream about that?” Steve asked aloud, his voice barely above a whisper. He was still trying to process the mix of emotions. Is it because Mitch saved me earlier? Was I just grateful and that turned into something else in my dream? Or... am I starting to feel things I didn’t expect?

He thought back to the moment Mitch had stepped in at the convention. The guy had been so cool, so composed, and undeniably heroic. Steve had felt small and vulnerable, but Mitch had made him feel safe, like he could relax because someone else was in control. Maybe it was just admiration. Maybe Steve was simply in awe of Mitch’s confidence and strength.

But then again, why did his heart race whenever Mitch looked at him or gave him a reassuring pat on the back? And why did the dream feel so... intense?

Steve sighed, frustrated with his own thoughts. “I’m just overthinking it,” he muttered, but he knew it wasn’t that simple. The dream had left him with questions he wasn’t ready to answer.

Maybe he was still figuring things out about himself. Maybe the lines between admiration, friendship, and something more were blurrier than he thought. All Steve knew was that today had been more than just a day at a convention. It had opened a door to something he hadn’t expected—something he wasn’t sure he was ready to confront just yet.

With a heavy sigh, Steve laid back down, staring at the ceiling. He didn’t have all the answers right now, and maybe that was okay. For now, he could take it one day at a time, figuring out what all of this meant for him.

……

It was a typical busy Monday morning at the office. The buzz of keyboards clacking, phones ringing, and coworkers chatting filled the air as Steve sat at his desk, organizing his paperwork and preparing for the tasks ahead. He tried to focus, but after the weekend at the convention, his mind kept wandering back to everything that had happened—the cosplays, the photos, and the strange but vivid dream he’d had about Mitch. He shook his head, trying to push the thoughts away. Focus, Steve, he told himself. It’s work time now.



As he settled into his routine, suddenly, he felt a presence behind him. Before he could turn around, a soft whisper brushed past his ear. “Morning, Sakura.”

Steve jumped, his heart skipping a beat. He spun around to see Lily standing there, grinning mischievously, clearly enjoying his reaction. “Oh my god, Lily!” he whispered back, his face flushing slightly. “You could’ve given me a heart attack!”

Lily laughed softly, her eyes twinkling with mischief. “Relax, Steve. It’s just me,” she teased, leaning against his desk. “What? You don’t like being called Sakura anymore?”

Steve glanced around nervously, his pulse still racing. “Please, Lily... don’t talk about that here. Not in the office. I don’t want anyone to know about... you know, the convention and everything. I’d rather keep it private.”

Lily smirked, clearly not concerned. “Oh, come on. What’s the big deal? If people found out, they’d just know that you make a very cute Sakura.”

Steve’s face turned red as he tried to hush her, glancing over his shoulder to make sure no one was listening. “Lily, please... seriously. I don’t want anyone in the office knowing about us, or our... activities.”

Lily grinned, unfazed by his worry. She leaned in closer, her voice still playful but quieter this time. “It’s okay, Steve. No one’s going to judge you. Besides, if they knew, they’d just think it was cool. And they’d all know how cute you were in that dress.”

She winked at him with a playful, naughty glint in her eye, clearly enjoying making him squirm. Steve sighed, trying to keep his cool, but her teasing was hard to brush off.

Just as Steve was settling back into his work, Lily leaned over again, her voice dropping to a casual whisper. “Oh, by the way, Angela wants us to meet up later. She’s organizing a post-mortem about our cosplay from the convention—you know, to talk about how it went and what we’ll do for the next event.”

Steve paused, feeling a flicker of nervousness rise up. The thought of another cosplay gathering made him uneasy, especially after the strange dream he’d had about Mitch the previous night. He tried to act casual but couldn’t stop himself from asking, “Wait, is Mitch coming too?”

Lily shot him a curious glance, a slight smirk forming on her lips. “Yeah, he’s coming. Why? Why are you asking about him?”

Steve’s pulse quickened as he scrambled for an answer. “I... I just wanted to make sure we had another guy in the conversation. You know, for balance.”

Lily raised an eyebrow, clearly not buying the excuse. She grinned and leaned in closer. “Uh-huh, sure. Just making sure there’s another guy, huh?” She poked his arm playfully. “You’re acting a little jumpy. Something on your mind, Stephie?”

Steve flushed, his thoughts flashing back to the dream, but he quickly shook it off, trying to regain his composure. “No, no, nothing. Just curious, that’s all.”

Lily’s smirk widened, but she decided to let it slide—for now. “Well, don’t worry. Mitch will be there, and maybe a few others too. I want to introduce you to the rest of our cosplay community.”

Steve blinked, a little taken aback. “Wait... there’s more?”

“Of course!” Lily said, her excitement showing. “We’ve got a whole group—people you’ll love. We get together all the time to talk about events, plan new cosplays, and just hang out. You’re one of us now, so it’s time to meet the rest of the crew.”

Steve was silent for a moment, processing what that meant. On the one hand, he enjoyed the time he’d spent with Lily, Angela, and Mitch at the convention. But now, joining a whole community? It felt like a big step—one he wasn’t sure he was ready for, especially with the confusing feelings he was trying to sort through after his dream.

“I don’t know, Lily...” Steve started, his voice hesitant. “I’m not sure if I’m ready for all that.”

Lily gave him a reassuring smile. “Trust me, Steve. You’ll fit right in. Everyone’s super friendly, and they’ll love having you in the group. Plus, you’ve already impressed everyone with your Sakura cosplay. You’ve got nothing to worry about.”

Steve still wasn’t sure, but Lily’s confidence helped ease his nerves. He nodded slowly. “Alright, I guess I’ll give it a shot. Just... no surprises, okay?”

Lily grinned mischievously. “No promises, Stephie. But I’ll make sure it’s fun.”

Steve sighed, his nerves still bubbling under the surface. It looked like he was about to dive even deeper into this cosplay world—and with Mitch and others in the mix, it was bound to be an interesting experience.

It was Wednesday evening, and Lily stood at the metro station, casually checking her phone while she waited for Steve. The day had been long, and she was looking forward to the meet-up with Angela and the rest of their cosplay crew. As she glanced up from her phone, she saw a woman with short blonde hair approaching her, dressed in a neatly tailored office suit.



At first, Lily didn't recognize her, but as the woman got closer, something clicked. The way she moved, the way her glasses sat just right on her face—it wasn’t just any woman from the office. It was Steve, in full disguise.

Lily couldn’t help but giggle, her hand covering her mouth in amusement. “Oh my god, Steve, is that you?” she asked, her voice filled with surprise.

Steve, clearly nervous but trying to maintain his composure, gave a small smile. “Yeah... it’s me. I, uh, thought it would be better to meet your friends like this.” He adjusted the collar of his suit, still getting used to the feel of the fabric. “I ordered this online. Figured it’d help keep everything... discreet.”

Lily laughed softly, shaking her head in disbelief. “You’re full of surprises, you know that?” She stepped closer and gave his hand a light squeeze. “You look pretty convincing, I’ve got to say. A little too good, actually.”

Steve blushed slightly, still feeling self-conscious. “Thanks, I guess,” he muttered. “I didn’t want to make things awkward with your friends. I just thought it’d be easier this way.”

Lily, still amused, looped her arm around his, pulling him close. “Well, it’s cute that you went through all this effort just to meet them like this. But you know you didn’t have to, right? They’ll love you either way.”

Steve smiled shyly, feeling a little better with her support. “Yeah, but... I figured this would be easier.”

With Lily still holding his arm, they began walking toward the café where they were meeting Angela. The evening air was cool, and the streets were alive with the sounds of people wrapping up their day. As they strolled, Steve felt a strange mix of anxiety and excitement. He wasn’t sure what to expect from this meeting, especially given his recent experiences, but with Lily by his side, he felt a little more confident.

As they approached the café, Steve glanced at Lily. “So, what’s the plan? Just talking about cosplay stuff?”

Lily grinned, her usual playful glint in her eyes. “Yep, just a casual hangout. We’ll talk about what went well at the last convention, brainstorm ideas for the next one, and probably get distracted by a million other things. But don’t worry, we’ll ease you in.”

Steve chuckled nervously, but nodded. “Okay. I’ll follow your lead.”

As Steve and Lily entered the cozy café, they immediately spotted Angela seated at a table near the window. She wasn’t alone; sitting beside her was a girl with wavy brown hair and a warm smile, whom neither Steve nor Lily recognized.

Angela waved them over enthusiastically. “Lily! Over here!”

Steve felt the usual flutter of nerves as they walked toward the table, but he took a deep breath, reminding himself that this was just a friendly meet-up. As they reached the table, Angela stood up to greet them. However, her eyes widened the moment she took a proper look at Steve, who was still dressed in his carefully tailored office suit, his hair styled, makeup done subtly but convincingly.

“Oh my god, Steve?” Angela blurted out in surprise, her jaw dropping. “Wait, are you crossdressing daily now?”

Lily couldn’t help but giggle at Angela’s reaction, her eyes twinkling with amusement. “It’s a long story,” she said, sliding into the chair next to Angela. “In short, Steve didn’t want any of our office mates seeing us walk together, so... this was his solution.” She laughed softly. “He takes things seriously.”

Steve’s face flushed slightly at all the attention, but he managed a shy smile, adjusting his glasses. “Yeah, uh... just trying to avoid any awkward situations,” he muttered, still feeling a little self-conscious.

The girl sitting next to Angela giggled softly, her brown eyes twinkling with curiosity. “It’s okay, Stephanie,” she said warmly, clearly getting into the spirit of things. “You’re really cute! I’m Evelyn, by the way,” she added, extending her hand.

Steve shook her hand, still adjusting to being called “Stephanie” so casually. “Nice to meet you, Evelyn,” he replied in the soft, girlish voice he had been practicing. It felt strange, but the way everyone was treating him put him more at ease.

Angela was still grinning, clearly entertained by the whole situation. “I’m shocked! But hey, if this is what keeps you from getting spotted by your coworkers, more power to you. Honestly, I didn’t think you’d actually go through with it.”

Lily laughed, leaning back in her chair. “Oh, you should’ve seen his face when I first saw him in this outfit. He really nailed the look.”

Evelyn chuckled and leaned forward, resting her chin on her hand. “You know, Stephie, you’re fitting in pretty well already. If you’re this convincing, no one’s going to suspect a thing.”

Steve blushed at the compliment but felt a little more relaxed as the conversation flowed. “Thanks... I just didn’t want anyone from the office to see us and start asking questions.”

Angela nodded understandingly. “Makes sense. But still, I have to say—you’re doing great. If I didn’t already know you, I’d think you were just another girl here to hang out.”

Steve smiled, feeling his nerves ease with every passing moment. The playful energy between his friends made everything feel a lot less intimidating. It wasn’t long before he found himself laughing along with their jokes, forgetting that he was even in disguise.

The café door swung open, and a small bell above it jingled softly. Steve’s heart skipped a beat as he glanced toward the entrance. There, standing in the doorway, was Mitch. His broad shoulders filled the frame as he stepped inside, followed by another man Steve hadn’t seen before. Mitch’s familiar presence immediately stirred something in Steve, especially after the vivid dream he had the other night.



Why now? Steve thought, his pulse quickening as Mitch casually scanned the room. Mitch looked even more manly than Steve remembered—his strong, confident stride made it hard for Steve to look away. He couldn’t help but notice how his heart seemed to beat faster the closer Mitch came.

“Hey, everyone!” Mitch called out as he approached their table, flashing a grin. “Sorry we’re late. Traffic was a nightmare.”

Lily waved them over with a wide smile, and Mitch quickly introduced the man next to him. “This is my buddy William,” Mitch said, gesturing to the well-dressed man beside him. William had an easygoing smile and a relaxed demeanor that instantly made him seem approachable. “We work out at the same gym.”

William nodded and gave everyone a polite wave before sitting down. His eyes settled on Steve, who was still in his crossdressed disguise as Stephanie. “And you must be Stephanie, right? Mitch told me about you.”

Steve felt a lump form in his throat, but he forced a smile. “Yeah, that’s me. Nice to meet you.”

Mitch’s eyes lingered on Steve for a moment longer, and then, with a playful grin, he added, “I didn’t realize you were crossdressing every day now.”

Steve’s face turned beet red, his mind flashing back to the dream, and he quickly shook his head. “N-not every day,” he stammered, nervously adjusting his glasses. “Just... you know... when it’s needed.”

Mitch chuckled softly and leaned against the table, his relaxed, confident energy making Steve feel even more self-conscious. “Hey, it’s all good. As long as you’re cute, Stephie,” he said with a teasing wink.

The playful comment sent a wave of heat rushing to Steve’s cheeks, and he blushed deeply. He opened his mouth to respond, but the words caught in his throat. His heart was racing, and he could barely manage a small, shy smile in return. “Th-thanks,” Steve finally muttered, feeling more flustered than ever.

Lily, sitting beside him, noticed his reaction and smirked, clearly entertained by the situation. She nudged Steve’s arm gently. “See? Told you no one would care. You’re killing it.”

Steve shot her a quick glance, feeling both embarrassed and relieved that everyone was being so accepting. But the way Mitch had spoken to him, so casual and confident, lingered in his mind. He couldn’t help but feel a bit awkward and, strangely, flattered.

Angela and Evelyn had already started chatting with William, leaving Steve to stew in his own thoughts. Mitch settled into his seat across from Steve, giving him a friendly smile every now and then, which only made Steve’s heart race even more. Why do I keep getting so flustered around him? Steve thought, trying to calm his nerves.

The evening continued, but Steve’s mind kept drifting back to Mitch’s words, his teasing smile, and the way his presence made Steve feel—something he was still trying to figure out.

As the conversation settled, Angela clapped her hands lightly, gathering everyone’s attention. “Alright, everyone, let’s officially welcome our newest member—Steve, or should I say, Stephanie?” she said with a teasing grin, giggling as she glanced over at Steve.

Steve, still feeling a bit flustered from earlier, smiled shyly but nodded, accepting the playful new identity he was slowly getting used to. The entire group had been so welcoming that it was hard not to feel a part of things.

Angela continued, “Our last project at the convention wasn’t bad at all, though we did have some incidents.” Her eyes flicked toward Steve briefly, a small, knowing smile crossing her lips. “But it only means we need to stick together even more next time.”

Steve felt a bit of heat rise to his cheeks at her mention of the “incident,” remembering how he’d felt when he was briefly cornered by the perverts. But before he could dwell on it too long, Angela moved on, leaning forward with excitement. “For our next project, we’ve been invited to participate in the launch event for the mobile game Shining Kiky. It’s this super cute fashion girly game, and they want us to help liven up the event!”

Lily perked up, her eyes lighting up. “Ooh, that sounds like fun! What kind of cosplays do we need for this?”

Angela grinned. “We need four girls and three guys for the event. It’s going to be a big showcase, and the more in-character we are, the better. They want us fully immersed in the fashion world of Shining Kiky.”

Steve blinked, doing the math quickly in his head. “Wait... so how many people do we have in the group right now?”

Lily gave him a playful smile. “Well, including you... it’s just Six of us.”

Steve furrowed his brow. “So we just need to find another girl, right?”

Evelyn chimed in, shaking her head slightly. “It’s not that easy. Finding another girl cosplayer who fits in with the group is harder than you think. There’s a lot of drama sometimes, and it’s tricky when the personalities don’t mesh.”

Angela nodded in agreement. “Exactly. Plus, Stephie, you’re a great crossplayer. You already showed us how well you can pull off being Sakura. So...”

Steve’s heart skipped a beat, catching onto what she was implying. “Wait... you mean...?”

Before he could finish, Mitch spoke up, casually leaning back in his chair. “I can handle the extra guy slot. I know a few other cosplayers who’d be up for it. But yeah, we still need one more girl... unless, of course, Stephie’s willing to fill that spot again.” Mitch’s gaze turned toward Steve, his teasing tone sending a ripple of nerves through Steve’s body.

Steve blinked, trying to process what was happening. “So you’re saying... I’m crossdressing again?”

Lily, ever the playful one, leaned closer to him with a grin. “Yeah, come on, Steve! You did amazing last time, and it’ll be fun—just like before!”

Steve hesitated, memories of the previous convention flooding back. Sure, it had been a blast... but he also remembered the awkward moment when he’d been approached by those perverts. “I don’t know... last time was fun, but remember what happened with those creeps?”

Before Lily could respond, Mitch’s voice cut in, firm yet reassuring. “Don’t worry about that, Stephie,” he said, his tone calm but protective. “This time, we’ll all keep an eye out for each other. No one’s going to mess with you again.”

For some reason, hearing Mitch say that made Steve feel... safer. His heart fluttered a little, though he wasn’t sure why. The way Mitch said it, like he’d personally make sure nothing went wrong, made Steve blush slightly, despite himself.

Angela, sensing the decision was made, clapped her hands together. “So it’s settled! We’ve got our fourth girl for the event.” She winked at Steve, her smile wide. “Welcome to the Shining Kiky team, Stephie!”

Steve let out a soft sigh, feeling a strange mix of nervousness and excitement. He knew what he was getting into now, and despite his reservations, he couldn’t help but feel a bit of excitement bubbling up inside him. Maybe this wouldn’t be so bad after all.