My Crossdress up Darling Ch 6 : Preparing for the Con

The next day at the office, Steve sat at his desk, but his mind was miles away. All he could think about was the costume he had tried on at Akiba Costume—a full Cardcaptor Sakura outfit, complete with the signature red dress, wand, and accessories. It had been a surreal experience, and now, the thought of actually wearing it at the upcoming anime convention filled him with a mix of excitement and nervousness.



He couldn't stop thinking about the character, so during his lunch break, he found himself flipping through a borrowed volume of Cardcaptor Sakura that Lily had lent him. Steve hunched over the comic, trying to absorb every detail. He was completely engrossed in the story, wanting to understand the character better, especially since he’d soon be cosplaying her. Sakura and Shaoran... but what about Yukito? he thought to himself, puzzled by the dynamics between the characters.

Just as he was deep into his reading, Lily appeared at his desk, leaning over to peek at the comic in his hands. “Wow, Steve, you’re really getting into the role, huh? Doing some research for your big debut?”

Steve looked up, startled but smiling awkwardly. “Uh, yeah... I want to understand it better, you know? Like... why did Sakura end up with Shaoran when it seemed like she was in love with Yukito?” He was genuinely confused, flipping back through the pages for clarity.

Lily grinned mischievously and sat on the edge of his desk. “Ah, that’s a fun part of the story! But here’s the thing—Yukito wasn’t into Sakura like that. He actually likes Sakura’s older brother, Touya.”

Steve blinked, surprised. “Wait, Yukito’s gay? And he likes Touya? Isn’t this a kid’s comic?”

Lily laughed, nodding. “Yep! That’s Clamp for you—mixing all kinds of relationships into their stories. It’s kind of surprising when you think about it, especially in a series like Cardcaptor Sakura. They added all sorts of complex romances.”

Steve looked back at the comic, trying to process the idea. “But... this is supposed to be a comic for kids, right? Isn’t that kind of... heavy?”

Lily smirked. “Oh, it gets more interesting. Have you reached book 9 yet? Rika, the girl from Sakura’s class? She has a relationship with one of the teachers.” 

Steve’s eyes widened, shocked. “Wait—what? She’s a kid! And with a teacher? That’s... whoa, that’s a bit much. Stop... stop, that’s way too vulgar for a children’s story.”

Lily burst out laughing at his reaction. “I know, right? Clamp has a way of sneaking in some seriously unexpected stuff. But that’s why it’s so fascinating. They don’t shy away from... well, unconventional romances.”

Steve shook his head, still processing. “I just wanted to get a better understanding of the character, and now I’m learning about all these complicated love stories! No wonder you like this series—it’s more intense than I thought.”

Lily grinned. “Welcome to the world of anime and manga. It’s full of surprises. Don’t worry, Steve. By the time you’re in costume at the con, you’ll have a deep appreciation for Sakura’s journey.”

Steve sighed but couldn’t help smiling back. “Well, at least I’ll know my character inside and out... even if the romance stuff gets a little out of hand.”

Lily patted his shoulder. “That’s the spirit. And who knows? Maybe you’ll surprise yourself with how much you enjoy the con.”

Steve chuckled nervously. “I guess we’ll see.”

Lily turned to Steve with a thoughtful look. “You know, if you’re going to cosplay Sakura, you’ve got to do it right. She has some iconic poses that you have to master.”

Steve blinked, caught off guard. “Poses? Like... how she stands and stuff?”

Lily grinned, nodding enthusiastically. “Exactly! She’s such a bright, energetic character, so you need to get her spirit right. Plus, you’re going to be posing with people who cosplay Shaoran at the convention. There’s no way you’re getting out of that.”

Steve’s nervousness grew at the thought of posing in costume at the anime convention. “Wait, wait—posing ? Like... like couples poses?”

Lily chuckled at his awkwardness. “Well, kind of! You don’t have to worry, though. It’s all in good fun. But if you’re going to do Sakura justice, you need to be ready for anything.” She flip the comic book page and showing to steve. “Here, this is one of her most iconic poses—just like when she’s holding her magical staff. You should practice this one.”

Steve shifted nervously. “I don’t know if I can pull that off, Lily. I’m going to look ridiculous.”

“Don’t worry!” Lily reassured him. “It’s mostly cute stuff. Sakura’s all about energy, confidence, and those iconic poses that everyone loves. But we’ll need to work on the smile—it needs to say ‘I’m a magical girl, and I’m about to save the day!. Plus,” she added with a mischievous smile, “I’m cosplaying as Shaoran, so we’ll need to practice our duo poses.”

Steve looked a little hesitant, shifting nervously. “Posing together? Like from the comic?”

Lily nodded enthusiastically. “Exactly! Think about that scene from the comic where Shaoran and Sakura stand side by side after capturing a card. You know, that heroic moment? We’ll be doing things like that. It’s all part of the experience at conventions.”

Steve tried to recall the scene she was talking about, flipping through the mental images of the comic she had lent him. “But I’m not sure I’ll get it right. Shouldn’t we practice?”

Lily waved a hand dismissively, though she still smiled warmly. “We don’t have time to practice much right now, but don’t worry about it. You’ll get it. Just take it easy—this is your first convention, so no one expects you to be perfect.”

Steve sighed, feeling a bit overwhelmed. “I don’t know, Lily. What if I mess up? I don’t want to look ridiculous next to you.”

Lily stepped closer, resting a hand on his arm in reassurance. “Hey, the key to this is just having fun. It’s not about being perfect. It’s your first time cosplaying, so it’s all about enjoying yourself. The poses will come naturally if you’re relaxed and in the moment. Besides,” she added with a wink, “you’ve done your research. You know Sakura’s spirit, right?”

Steve nodded slowly, remembering how he had spent hours reading the manga and getting to know the character. “Yeah, I guess I do.”

Lily grinned. “Exactly. And if you’re worried about us posing together, don’t be. Just remember that scene when Shaoran is all flustered next to Sakura—if you end up looking awkward, it’ll just make the whole thing even more in character.”

Steve couldn’t help but laugh a little at that. “So, if I look awkward, it’ll actually work?”

Lily giggled. “Pretty much! We’ll be adorable together. But really, just take it easy. Have fun—that’s the most important part. You’ll see how much everyone enjoys themselves, and you’ll forget all about being nervous.”

Steve took a deep breath, feeling a little more confident. “Okay, I’ll try to relax. As long as no one from the office shows up.”

Lily gave him a playful nudge. “Stop worrying about that! No one’s going to know it’s you anyway—you’ll be completely in character. By the end of the convention, you’ll be posing like a pro. Just enjoy yourself.”

Steve nodded, the nervousness starting to fade as Lily’s confidence and encouragement began to settle in. “Alright, I’ll do my best. Let’s just hope I don’t trip over my costume.”

Lily grinned. “Don’t worry, I’ll be there to catch you. Now, let’s go show them how it’s done!”

Then at Saturday, the day of the convention, and Steve was already feeling the weight of nerves as he made his way to Lily’s apartment. It was still early—4:00 AM to be exact—and the sun hadn’t even risen. The city streets were quiet, empty, and cold, but the excitement of the day kept Steve moving. Lily had insisted on meeting early to prepare for the event, and although Steve still wasn’t sure why they had to start this early, he didn’t want to question her plans.

When he knocked on the door to her apartment, it swung open almost immediately, and Lily greeted him with a wide grin, her eyes sparkling with energy despite the early hour. “Steve! You made it. Come in, come in!” she exclaimed, clearly excited.

Steve stepped inside, still trying to shake off the last bit of sleepiness. “Why did I need to come so early?” he asked with a yawn. “It’s not even light outside.”

Lily was practically bouncing as she led him inside. “Because the convention opens at 9:00, and we need plenty of time to get ready! We’ve got makeup to do, costumes to get into, and then we’re taking the train. We need to be fully prepared, and trust me, it takes longer than you think.”

Steve blinked, still processing the plan. “Wait... we’re going to take the train in costume?”

Lily nodded enthusiastically. “Of course! It’s normal for cosplayers, Steve. Trust me, you’re not going to be the only one dressed up on the metro. Besides, it’s part of the fun. Now, come on, sit at the vanity—I need to start your makeup.”

Before Steve could protest, Lily guided him to her vanity table and gestured for him to sit down. He hesitated but eventually complied, settling into the chair with a mix of anxiety and curiosity. He wasn’t used to this—being pampered and made up—but Lily’s excitement made it hard to say no.

Lily got to work immediately, starting with the basics. “First things first,” she said, grabbing a makeup wipe, “we’ve got to clean your face.” She carefully wiped his skin, making sure to cleanse and prep it for the makeup.

Steve shifted awkwardly in the chair. “I feel weird about this. Are you sure we need to do the whole makeup thing?”

Lily grinned as she applied the foundation next, smoothing it over his face. “Absolutely! You want to be the best Sakura you can be, right? Plus, makeup is a big part of the look. Trust me, by the end of this, you’ll look amazing.”

Steve wasn’t entirely convinced, but he let Lily continue. As she worked, she talked him through the process, explaining each step as she applied the foundation, eyeliner, eyeshadow, and blush. Despite his initial awkwardness, Steve found himself relaxing as Lily’s expert hands transformed his face.

Finally, after what felt like an eternity of brushes and powders, Lily stepped back to admire her work. “Perfect!” she declared proudly. “Now it’s time for the costume.”

Steve stood up nervously as Lily handed him the Cardcaptor Sakura costume. The fabric was soft, smooth, and felt luxurious in his hands, just as he remembered from when he tried it on at the shop. But there was one thing that was still bothering him. “Wait... are we seriously going to wear these costumes on the metro?” he asked, feeling the anxiety return.

Lily rolled her eyes playfully. “Steve, it’s totally normal for cosplayers to wear their costumes to conventions. It’s half the fun! You’ll see tons of people dressed up on the way. Now hurry up—we don’t have time to waste. I still need to get ready as Shaoran!”

Reluctantly, Steve nodded and began putting on the costume. He slipped on the bra and panties first, feeling the smooth fabric against his skin. Then came the iconic red Cardcaptor Sakura dress, followed by the hat, the wings, and the magical rod. With each layer, his heart pounded faster—not just from nerves, but from a strange excitement building inside him. The softness of the fabric, the way it hugged his body, and the fact that he was transforming into someone else entirely—it all made his pulse race.

Once the costume was fully on, Steve glanced at the mirror in front of him, and what he saw made him stop in his tracks. Staring back at him was not the awkward, nervous Steve he had seen every morning—it was Sakura. The cute, magical girl from the manga he’d been reading, complete with the bright eyes, flowing dress, and confident smile. He blinked, unable to believe what he was seeing.



“That... that’s me?” he whispered, stepping closer to the mirror. He barely recognized himself. The makeup, the costume—it had transformed him into someone completely different. He looked like a character straight out of an anime.

Lily stood beside him, grinning with pride. “Yep! You’re Cardcaptor Sakura now, Steve. What do you think?”

Steve’s heart was still racing. “I... I can’t believe it. I look... I don’t even look like me.”

“That’s the point!” Lily said, laughing. “You’re supposed to look like Sakura. And trust me, you look perfect. Now come on—we need to finish getting ready. I’ve got to become Shaoran, and then we’ll be off to the convention.”

Steve tore his gaze from the mirror, still feeling the excitement coursing through him. “Okay... let’s do this.”

After some time, Lily finally finished getting ready, emerging from her bedroom dressed as Shaoran. The costume was striking—green with intricate gold detailing, resembling a traditional Chinese priest’s robe. A bold yin-yang symbol was emblazoned on her chest, capturing the essence of Shaoran’s character perfectly. The costume fit her well, and she had even added the final touch: a fake sword strapped to her side as a cosplay prop. 

Lily grinned, holding the sword up dramatically as she struck a heroic pose. “What do you think?” she asked, spinning around to show off the full costume.

Steve, still dressed as Sakura, stared in awe. The costume was impressive, no doubt about it, and Lily carried herself with an air of confidence that made it even more believable. To tell the truth, she looked fantastic, even if the subtle femininity in her features came through. It didn’t matter—she was still every bit the Shaoran character she was supposed to be, and she pulled it off effortlessly.

“That looks amazing, Lily,” Steve admitted, unable to hide his admiration. “You really nailed it. The costume, the pose—it’s like you stepped right out of the manga.”

Lily grinned wider, clearly pleased with his reaction. “Thanks, Steve! I was worried about pulling off Shaoran, but it’s coming together. Plus, I’ve got you as Sakura by my side, so we’ll totally rock this at the convention.”

Steve laughed nervously, still feeling a bit self-conscious in his own costume. “Yeah, I just hope I don’t trip over this dress on the way there.”

Lily chuckled and gave him a reassuring pat on the shoulder. “You’ll be fine! Just relax and enjoy it. We’re going to have so much fun.” She glanced at the clock on the wall, her eyes widening. “Oh, it’s already 7:30! We need to catch the metro by 8:00 if we want to get to the convention on time.”

Steve felt a surge of nervous energy at the thought of stepping onto a crowded metro dressed as Cardcaptor Sakura. “Are you sure we’re going to be okay walking around in full costume?” he asked, glancing down at his elaborate outfit.

Lily nodded confidently, grabbing her sword and adjusting her costume. “Steve, this is totally normal for conventions. You’ll see—there will be other cosplayers on the metro. It’s part of the experience! Trust me, no one’s going to bat an eye.”

Steve took a deep breath, trying to calm the nerves that had returned. “Alright... I guess I’ll just have to trust you.”

Lily gave him a playful wink. “You’ll be fine. Now, grab your wand and let’s go. Cardcaptor Sakura and Shaoran have a convention to get to!”

Steve nodded, taking up the wand that completed his look, and together they headed out the door, ready for their cosplay adventure.

At the metro station, Steve felt like every single person there was staring at him. The bright red Cardcaptor Sakura costume, the wand in his hand, and the wings on his back made him stick out like a sore thumb. His face flushed red with embarrassment as he tried to avoid eye contact with anyone around them. Every glance, every whispered comment made his heart pound faster, and his awkward smile felt even more forced.



Lily, dressed confidently as Shaoran, was walking beside him, completely at ease. In fact, she was giggling at how flustered Steve was. “You’re turning as red as your dress,” she teased, watching his face grow redder with every step.

Steve shot her a nervous look, then looked around the station again, hoping that no one would pay him too much attention. But it didn’t help. A group of men passed by them, and one of them smiled and said, “Nice dress, sweetheart.” Another let out a whistle, and a third gave a thumbs-up, saying, “Great costume, sis!”

Steve’s cheeks burned even hotter as he pulled his hat lower, trying to hide. He couldn’t believe it—Lily’s makeup work had been so good that everyone thought he was a girl. They have no idea I’m a guy, he thought, torn between relief and embarrassment.

Lily leaned in closer, still laughing softly. “Just like I said before,” she whispered, “my work was perfect. No one can tell you’re male. You’re completely in character.”

Steve bit his lip, glancing around nervously. “Ssshh!” he hissed, his eyes wide. “Please, don’t say that so loud. I’m already dying of embarrassment here, and you’re going to blow my cover.”

Lily’s laughter turned into a soft chuckle as she patted his arm. “Relax, Steve. No one’s going to figure it out. You’re the perfect Sakura, and everyone’s loving it. Just enjoy the attention—you’ve got nothing to worry about.”

But Steve wasn’t so sure. Every step toward the train felt like a lifetime, and every comment made him want to disappear. His heart pounded in his chest, and his mind raced with the constant thought that someone might realize he wasn’t actually a girl. “I don’t know how you do this,” he muttered, trying to keep his voice low. “I’ve never felt so... exposed.”

Lily smiled warmly, trying to reassure him. “It’s part of the fun, Steve. Cosplaying is about stepping into a new identity, right? You’re not Steve right now—you’re Sakura. So just go with it.”

Steve sighed, glancing around again as they waited for the train to arrive. “I guess... but it’s so much harder when people actually think I’m a girl.”

Lily winked at him. “That just means I did my job well.” She gave him a playful nudge. “By the time we get to the convention, you’ll be used to it. Trust me.”

As the train pulled into the station, Steve took a deep breath, trying to calm his nerves. He wasn’t sure how the rest of the day would go, but with Lily’s support, maybe—just maybe—he could survive it without dying of embarrassment.

The train arrived with a soft hiss, and Steve and Lily stepped inside. It was still early in the morning, so the train wasn’t packed yet, with just a few scattered passengers seated throughout. Steve immediately felt a wave of nerves wash over him, his heart pounding in his chest. He was hyper-aware of the Cardcaptor Sakura costume he was wearing—the bright red dress, the wings, and the magical wand in his hand.

“I need to keep my distance,” Steve muttered, his eyes darting around. He was terrified that if anyone came too close, they’d figure out his secret—that he wasn’t really a girl but a guy crossdressing for the convention. He moved to a quieter corner of the train, trying to stay as far from the other passengers as possible.

Lily followed him, her Shaoran costume giving her a confident, almost regal look. She was clearly enjoying the cosplay experience, but she could see the tension in Steve’s body. “Relax, Steve,” she whispered, holding his hand gently. “Don’t worry. Just enjoy it. Everything will be fine as long as you stay in character and play it as Sakura.”

Steve gripped the magical wand in his hand tightly, his knuckles turning white. “I hope you’re right,” he said nervously. He tried to smile, but it came out as more of a grimace. 

Lily gave him a reassuring squeeze on the hand. “You’re doing great. Just breathe.”

As the train continued to the next stop, more passengers began to enter, filling the train car bit by bit. Steve’s anxiety spiked as the space around him shrank. A few people stood closer than he would’ve liked, and he was terrified that someone would notice something off. His grip on the rod tightened, and he silently wished he could be invisible.



Suddenly, a man walking by paused, his eyes lighting up as he looked at Steve and Lily. “Hey! I know these costumes!” he exclaimed, a friendly smile spreading across his face. “You’re Cardcaptor Sakura and Li Shaoran, right? Man, that’s awesome!”

Steve felt his heart stop. He froze, avoiding eye contact, praying the conversation would end quickly. But then the man tilted his head, his smile curious. “Wait... are you crossdressing?”

Steve’s stomach dropped. His worst fear had come true. He stayed silent, too scared to respond, his eyes glued to the floor.

Before Steve could spiral further, Lily stepped in, unfazed. “Yep!” she said with a playful grin. “I’m crossdressing as Shaoran. What do you think?”

The man laughed, nodding approvingly. “Well, it suits you. You make a cute Shaoran! And Sakura over there—super cute too. You two are going to the con, right?”

Lily smiled, sensing Steve’s rising panic. She squeezed his hand gently again and said, “Yeah, we’re headed there now. It’s actually Stephanie’s first time joining the convention.” She motioned to Steve, her voice soft but encouraging. “She’s a little shy.”

The man gave a warm smile, turning to Steve. “Don’t worry, Stephie! Everything’s going to be fine. First cons are always nerve-wracking, but you both look awesome. Good luck at the con!” He gave a friendly wave. “I’m John, by the way. Hope I see you both there.”

Steve’s pulse was racing, but with Lily’s hand still holding his, he felt a tiny bit more grounded. He had no choice but to play along. Summoning every ounce of courage, he forced a shy smile and replied, in the most girly voice he could muster, “I-I’m Sakura.. I mean Stephanie. Nice to meet you.”

John grinned and gave them both a thumbs-up before heading to the other end of the train. “Have fun, you two!” he called out.

As soon as he was out of earshot, Steve let out a shaky breath, his nerves still rattled. “I thought I was done for...”

Lily giggled beside him, clearly proud of how he handled the situation. “You did great, Stephanie!” she teased, giving him a playful nudge. “See? No one’s going to know. We’ve got this.”

Steve smiled weakly, the tension slowly leaving his body. “I just hope I survive the rest of the day.”

Lily winked at him. “You will. And by the end of it, you’ll be having more fun than you thought possible.”