My Crossdress up Darling Ch 5 : The Costume

Steve sat at his desk in the office, staring blankly at his computer screen. No matter how hard he tried to focus, the memory of his recent experience in the ladies' restroom kept flooding back—how awkward he felt standing there, how out of place he was, and the sheer embarrassment of almost being caught by Jenna. He could still feel the heat in his cheeks from the humiliation, the way he had hurried out of the café without so much as a word.

Just as he was trying to shake off the memory, a familiar voice came from behind him. “I can’t believe you left me in that café, Steve! What’s wrong with you?”

Steve jumped in his chair and spun around to see Lily standing there, her arms crossed and a playful smirk on her face. He felt his pulse quicken as he tried to come up with an excuse. “L-Lily... I-I’m sorry, I didn’t mean to... I just—”

“What’s wrong with you?” she interrupted, her tone teasing but with a hint of scolding. “Leaving a lady alone in a café is so rude!”

Steve opened his mouth, trying to explain himself, but all that came out was a nervous jumble. “I... It’s just... when we saw Jenna, I panicked. I didn’t want to get caught and make things awkward for you.”

Lily’s expression softened, though the playful glint in her eyes remained. She shook her head and sighed dramatically. “Steve, I told you before, I don’t care if people see us together. Why are you so worried about getting caught? And, by the way, why didn’t you answer my calls all weekend?”

Steve lowered his gaze, feeling the embarrassment creep back in. “Because I was so embarrassed, Lily. You pushed me too far that day... I went home wearing your dress, and the entire time, I was terrified that one of my neighbors would see me. As soon as I got into my apartment, I just... hid. I didn’t go out all day.”

Lily chuckled softly and sat on the edge of Steve’s desk, looking at him with a mix of sympathy and amusement. “Steve, your disguise was perfect! No one had a clue. Even Jenna didn’t realize who you were. After you left, she had no idea you were in the restroom.”

Steve blinked, taken aback. “R-really?” He still couldn’t believe it. The thought that he had successfully blended in without anyone noticing seemed impossible after how nervous he’d been.

Lily nodded confidently. “Yeah, really. You were so convincing. If you hadn’t bolted out of there, no one would’ve suspected a thing. Want me to call Jenna over right now and ask her if she remembers you?”

Steve’s eyes widened in panic. “No! Please, no!” He threw his hands up in surrender. “I believe you, okay? I just... it’s all been too fast. Too much, too soon.”

Lily laughed softly and patted his shoulder. “Alright, alright. I won’t push you... for now. But trust me, Steve—you’re doing better than you think. Next time, you’ll be more comfortable.”

Steve sighed in relief, feeling a weight lift off his chest. “Thanks, Lily. I’m sorry... I just need time to adjust.”

Lily smiled warmly. “You’ll get there, Steve. Besides, it’s kind of fun watching you squirm sometimes.”

Steve managed a small smile in return, knowing full well that with Lily around, things were never going to be completely comfortable—but somehow, that made it all the more interesting.

Just as Steve was starting to relax, the office phone rang sharply on his desk, snapping him back to reality. He picked it up, still feeling flustered. “Hello, Steve here.”



“Hey, Steve, it’s Chris from accounting. I’m going over some reports and need the data for last quarter’s expenses. You think you can send it over?”

“Uh, yeah, sure,” Steve replied, quickly pulling up his computer. “Give me a minute, I’ll get it over to you.”

“Thanks, man. Appreciate it,” Chris said before hanging up.

Steve turned back to Lily, who was still sitting on the edge of his desk, casually watching him. He gave her an awkward smile. “We’ll talk later, okay? After work.”

Lily flashed him a playful grin and gave him an exaggerated thumbs-up. “Sure thing, Steve,” she said, standing up and making her way back to her desk, leaving him to focus on his work.

Steve leaned back in his chair, trying to shake off the lingering embarrassment from their conversation. But as he opened up the spreadsheet to pull the data for Chris, his mind kept drifting back to the events of the past weekend. He couldn’t stop thinking about how soft Lily’s dress had felt, the smooth fabric brushing against his skin, and the sensation of wearing her underwear. It had been nerve-wracking at the time, but now that he was removed from the situation, he found himself replaying those moments in his head.

As he absentmindedly typed, Steve’s imagination started to wander even further. What if he showed up to the office in a dress? How would everyone react? The idea sent a rush of nervous excitement through him—walking through the office doors, dressed in a stylish women’s outfit, feeling the curious stares of his coworkers as they tried to figure out what was going on. It would be so embarrassing... but strangely thrilling at the same time.

His fingers paused on the keyboard as he pictured himself standing at the front of a meeting, his usual button-down shirt and tie replaced by a flowing skirt and soft blouse. Would anyone even recognize him at first? How would Chris react if he saw him dressed like that?

Steve shook his head quickly, snapping himself out of the daydream. What am I even thinking? he scolded himself silently, feeling a wave of embarrassment just from the thought. He focused back on his screen, trying to get the report done, but the image of him in a dress kept sneaking its way back into his mind.

The mixture of excitement and embarrassment was overwhelming. He knew it was ridiculous, but a part of him couldn’t help but wonder... what if?

Still lost in his strange mix of excitement and embarrassment, his phone buzzed on the table, pulling him from his thoughts. He glanced down and saw a notification from Lily. A message? He hesitated for a moment, unsure of what she had sent this time.

Curiosity got the better of him, and he opened the message. His eyes widened in shock as the image loaded. It was a photo of himself from the other day, wearing Lily’s dress. The angle was perfect—his makeup flawless, his figure convincingly feminine. He almost couldn’t recognize himself. He stared at the screen in horror. How did she even get this picture?



Steve’s eyes darted across the office, and sure enough, there was Lily at her desk, grinning mischievously and giggling to herself. She had an unmistakable look of triumph, clearly reveling in her little prank. Steve immediately felt a wave of panic.

He typed back quickly, "Lily, please don’t send that anywhere! It’ll be so embarrassing if someone sees it."

Lily’s reply came almost instantly, her playful tone coming through even in the text: "Okay, I won’t... but you have to promise me something first."

Steve sighed in frustration, already knowing that Lily had some kind of plan. "What do you want?" he typed, dreading the answer.

"You’re going to accompany me to Akiba Costume this Thursday after work. I have some items to pick up," Lily replied, her tone suggesting that she wasn’t going to take no for an answer.

Steve groaned. "Thursday? That’s a workday. Why not wait until the weekend?"

"Because I’m wearing it this weekend at the anime convention, and I need it ready," Lily responded almost instantly.

Steve leaned back in his chair, rubbing his temples. The last thing he wanted was to be seen at Akiba Costume during a busy workday. His imagination ran wild again, picturing someone from the office spotting him there. "What if someone from the office sees us?" he texted back, hoping for an excuse to get out of this situation.

"Don’t worry, Steve," Lily replied, "everyone is too tired after a long day at work to care. They just want to get home. Besides, no one from our office is going to be hanging around near Akiba Costume."

Steve hesitated for a moment, weighing his options. He didn’t want that picture of him circulating around the office, and Lily’s confidence in the plan was oddly reassuring, even if her methods were questionable. "Fine... okay. I’ll go with you on Thursday," he finally replied, feeling a mixture of resignation and relief.

Across the office, Lily gave him a thumbs-up, her grin wide with victory. "Great! See you then, Stephanie ;)" she texted back, clearly pleased with herself.

Steve sighed and slipped his phone into his pocket. This Thursday was going to be interesting, whether he liked it or not.

At Thursday afternoon, and Steve sat at his desk, feeling a mix of nervousness and anticipation. He knew he had agreed to accompany Lily to Akiba Costume after work, but the thought of being seen by any of their coworkers made him uneasy. He didn’t want to risk any awkward questions or assumptions from people at the office. 

With a sigh, he picked up his phone and sent Lily a message: "Hey, let’s meet up at the station after work so no one from the office sees us together."

A few moments later, Lily replied: "Okay, sure." The message was brief, but something about it felt off. It had a subtle tone of sadness, like Lily wasn’t entirely happy with the idea. 

Steve could feel it too, that lingering feeling of guilt. He knew that keeping their outings a secret from the office wasn’t fair to Lily, but he had convinced himself it was the only way to protect her reputation. He didn't want anyone thinking that she was dating someone like him—someone who had been caught up in embarrassing situations. She deserves better than that, he thought.

Still, the sadness in her reply weighed on him. Maybe it’s not fair to her, he mused. He could picture her, sitting at her desk across the office, disappointed that they had to keep their relationship hidden, like it was something to be ashamed of. But he was too worried about the potential gossip and rumors to consider doing anything else. His heart felt heavy with the decision.

As the clock ticked toward the end of the workday, Steve couldn’t help but wonder what Lily had planned. She had mentioned needing the costume for an anime convention that weekend, but she hadn’t told him what she was going to wear. He found himself thinking about it more than he expected. What kind of costume would she choose? Lily had always been bold and creative, so he knew whatever it was, it would be impressive. 

Maybe she’ll dress as an anime character, Steve thought, his mind wandering. Lily was a fan of vibrant and dynamic characters, so it wouldn’t be surprising if she picked a well-known anime figure. Or perhaps she’d opt for a video game character, with armor and intricate details. Either way, he could imagine her commanding attention at the convention, her confidence drawing people in like it always did.

Steve shook his head, trying to focus back on his work, but the curiosity lingered. Whatever she chooses, she’ll look amazing. She always does.

With a final glance at the clock, Steve began packing up his things, ready to meet Lily at the station and take the next step in their adventure together. Even if it was awkward or risky, part of him was looking forward to seeing what she had in store—and maybe, just maybe, he’d find a way to make it up to her for keeping things quiet at work.

Steve arrived at the train station, his heart pounding in his chest as he scanned the crowd. His eyes darted nervously across the platform, watching for anyone from the office. Every person walking by seemed like a potential coworker. What if I run into someone I know? What if someone sees us together? The thoughts raced through his mind as he waited, trying to calm his nerves.

And then he saw her.

Lily stood near the entrance of the station, her eyes immediately locking with his. A smile spread across her face, a bright, almost radiant expression that made Steve’s anxiety momentarily melt away. She was wearing a working outfit, but even in something simple, she still looked effortlessly stylish. Steve couldn’t help but notice how her smile made her look even more beautiful. 

She bounced over to him, her enthusiasm contagious. “Steve!” she exclaimed, her voice full of excitement. “At last! I finally get to go on a date with you!”

Her words sent a jolt of warmth through his chest, but at the same time, the awkwardness of the situation began to creep back in. Steve forced a small smile, though it was stiff. “Yeah, uh… finally.” His eyes flitted nervously around the station, checking for anyone who might recognize them. He kept imagining some coworker popping up and ruining everything.

Lily noticed immediately, her smile faltering just for a second. “Steve, relax,” she said gently, reaching out and placing a hand on his arm. “It’s just us. No one here knows us. We’re just two people going out for fun. You don’t have to be so nervous.”

But Steve still couldn’t shake the feeling. The idea of being seen with her, especially in public, felt foreign to him. The lines between their friendship and whatever this was they were doing had blurred so much in the past week, and he still wasn’t sure what to think. He glanced at the crowd again, his gaze darting from face to face. What if someone recognizes me in this outfit? He looked down at himself, suddenly self-conscious. 

Lily saw his hesitation and smiled softly, understanding his unease. “You’re still not used to it, huh?” she said, nudging him playfully with her shoulder. “It’s okay, Steve. You’ll get used to it. We’re just two people doing something fun together.”

“I know,” Steve muttered, trying to act casual. He was still unnerved, but he appreciated how calm and comfortable Lily seemed. She was so sure of herself, and her confidence made him feel like maybe he could ease up. 

Lily took a step closer, lowering her voice so only Steve could hear. “You know, this is the first time I get to spend some real time with you without hiding behind all the work stuff. It feels good.”

Steve nodded, still feeling the weight of his unease. "Yeah, it’s just... I don’t know. It feels so weird being out here, like we’re sneaking around."

Lily chuckled lightly. “Sneaking around? Oh, come on, Steve. You’re not the only one who gets nervous. But you’ll see, once we’re having fun, you won’t care about all the other stuff. I promise.”

Despite his reservations, Steve felt his tension ease a little. Lily’s words were reassuring, and the warmth in her eyes made him feel a little more at ease. Still, the nagging feeling of being watched lingered in the back of his mind.

He sighed, trying to push the thoughts away. “Alright, let’s just get this over with, then.”

Lily smiled, pulling him by the arm toward the platform. “Trust me, Steve. This is going to be fun. You won’t regret it.” 

As they walked toward the train, the bustling noise of the station around them, Steve couldn't help but glance at the faces of the people nearby. But despite his nerves, there was a spark of something new, something exciting. He was finally spending time with Lily, away from work, and maybe—just maybe—he could start to relax.

But he couldn’t stop looking over his shoulder.

At Akiba Costume, the bright lights and vibrant colors of the store overwhelmed Steve as they stepped inside. The shelves were lined with all sorts of costumes, wigs, and accessories. Maia, the store clerk, greeted them warmly with a big smile. "Hey there, Lily! And you must be Steve," she said, her eyes sparkling with enthusiasm.

Lily returned the smile, her excitement palpable as she eagerly started talking about the various costumes. “Look at this wig! And these accessories. Oh, and this one!" She pointed to a dazzling outfit on the rack, her hands flitting over the fabrics. "What do you think, Maia?"

Maia nodded approvingly. "That one would look amazing on you, Lily! But for Steve, we have a whole range of things that might be perfect."

Lily glanced at Steve, a mischievous gleam in her eyes. "C'mon, Steve, let’s dress you up! It'll be so much fun."

Steve blinked in confusion, a knot forming in his stomach. "Wait... Is the costume for you?" he asked, his voice laced with uncertainty.

Lily laughed softly, shaking her head. "No, silly. I have a lot of stuff already. This time, I want to make a costume for you. Think of it as a little fun before the anime con! Trust me, it’ll be amazing."

Steve’s mind raced as he tried to process what Lily was saying. A costume for me? he thought, feeling a mix of nervousness and curiosity. He had no idea what kind of costume she had in mind, and the idea of dressing up in something unfamiliar was both exciting and terrifying at the same time.

“Come on, it'll be fun!” Lily said, her voice bubbly with enthusiasm as she gently nudged him toward the dressing room. "You’ll see, it’ll be perfect for you."

With a deep breath, Steve nodded reluctantly. He could already feel his heart pounding in his chest as he made his way toward the dressing room, the excitement in the air making his nerves only worse. As he stepped inside and closed the door behind him, he could hear Lily and Maia chatting eagerly outside.

What kind of costume could it possibly be? Steve thought, the uncertainty settling into his mind. I just hope it’s not too... much.

His hands shook slightly as he looked at the costume laid out before him—a beautiful, detailed outfit that looked far too extravagant for his taste. His mind was spinning as he thought about how he’d look in it, how he’d feel, and what the reactions might be.

Steve stood in front of the mirror, still confused by the whole situation. He wasn't familiar with anime, or the characters, or the significance of the costume he was wearing. All he knew was that it felt strange. The dress was a Japanese school uniform—something out of a stereotypical anime scene—but all the details about it meant nothing to him. The skirt felt a bit short, the top a bit tight, and the entire ensemble was far from what Steve would normally wear.

With a sigh of resignation, Steve walked out of the dressing room and into the small area where Lily and Maia were waiting. He was trying his best to act casual, but his face was flushed with embarrassment. His steps were stiff, and his hands instinctively pulled at the skirt, trying to make himself as invisible as possible.

The moment Maia saw him, her eyes widened in delight. "Oh my god, I knew it! You totally fit as Sailor Uranus!" she exclaimed, a huge grin on her face.



Steve blinked, his expression still puzzled. "Sailor who?" he muttered under his breath, completely lost. 

Lily, however, was more focused on the bigger picture. She tilted her head and eyed Steve from top to bottom. "Yeah, she’s a bit of a tomboy, which works, but I want something a little cuter for you. This one’s okay, but let’s try a different look. C’mon, Steve, you’ve got to get the full experience," she said, her voice light and playful.

Steve tried to make sense of what they were saying but couldn’t wrap his mind around it. "I... I don’t really get what’s going on," he admitted, feeling increasingly awkward. But before he could even finish his sentence, Lily handed him another costume.

"This one will suit you even better!" she said excitedly. "Go change again, I want to see how cute you’ll look in it."

Steve stared at the dress in his hands. It was completely different—brighter, frillier, and more feminine. He had no idea what kind of character it was supposed to represent or why Lily wanted him to wear it. The pressure of the situation was starting to get to him, but he knew he didn’t have much of a choice. With a reluctant sigh, he went back into the dressing room and changed into the new outfit.

Steve took a deep breath and stepped out of the dressing room, the bright yellow dress feeling foreign against his skin. The fabric swayed slightly with his movements, and the big yellow bow in the center of his chest felt like a spotlight drawing attention to him. He could feel his cheeks heating up with embarrassment as he emerged into the brightly lit store.

Lily’s eyes widened in delight. “Look at him! He’s so cute!” she exclaimed, her voice filled with excitement. Steve could only manage a shy smile, feeling utterly self-conscious under her gaze.

Maia chimed in, nodding enthusiastically. “Yeah, you totally fit the role of Peace Pretty Cure!” she said, a wide grin on her face. “Let me help you with the hair ornament,” she added, stepping closer to Steve.



“What’s a Peace Pretty Cure?” Steve asked, confusion evident in his voice. He still had no clue what the character was about.

Lily, with a playful smirk, responded, “It’s a character from a magical girl anime. You look perfect for it!” She then glanced at Steve’s hair. “But wait, he needs hair extensions! Kise Yayoi has long hair, and we can’t have you looking short-haired in that dress!”

“Exactly! Don’t worry about it,” Maia assured him, rummaging through her bag. “I have some hair extensions right here. This will make the look complete!”

As Maia worked on clipping the extensions into his hair, Steve felt a mix of nervousness and curiosity. He tried to stay still, allowing them to fix him up, though part of him felt overwhelmed by the transformation.

Once Maia was done, she stepped back to admire her work. “Now it’s really done!” she said, beaming with pride. “You look amazing!”

Lily, however, wasn’t finished. She reached into her bag and pulled out another costume. “And here’s the last one, Steve!” she announced, holding it out for him to see.

Steve hesitated, staring at the new outfit. “What is this one?” he asked, feeling a sense of dread mixed with curiosity.

“Just go change into this one,” Lily urged, her eyes sparkling with excitement. “Trust me, it’ll be worth it!”

With a reluctant nod, Steve took the costume from Lily’s hands and headed back into the dressing room. As he changed, he couldn’t help but feel a swirl of emotions—nervousness, embarrassment, but also a strange thrill at the idea of stepping further into this new role. After a few moments, he took a deep breath and stepped out once more, ready to see what awaited him in the next costume.

As Steve stood in the dressing room, pulling on the new costume, he couldn’t help but think about the situation he found himself in. It felt surreal, like he was a Barbie doll being dressed up by two enthusiastic friends. Is this what it’s like to date a cosplayer? he pondered. 

Lily was not evil; she just wanted him to enter her world. He remembered the excitement in her voice as she spoke about the characters and the conventions. This was her passion, and for a moment, he thought maybe he could share in it too—if only he could shake off his nerves.

He glanced at the costume before him, a stunning red dress complete with a matching red hat and whimsical wing ornaments. An angel costume? he thought, feeling a mix of curiosity and apprehension.

He slipped the dress over his head and adjusted the fit, turning to face the mirror. As he looked at his reflection, he was taken aback. The cute costume transformed his appearance, giving him an entirely different persona. Who is that? he wondered, amazed at how the outfit changed his reflection into someone vibrant and full of life.

For a moment, he lost himself in the image. What would everyone think if he wore this out in public? Would they laugh at him, or would they tell him how pretty he looked? The thought sent a thrill through him. Maybe some girls would even say he was beautiful, and the idea excited him more than he cared to admit.

Suddenly, he became painfully aware of the physical reaction to his thoughts. His heart raced as he felt himself becoming aroused. Oh no, I can’t getting up in here! What if Maia sees? Panic surged through him. He quickly adjusted his dress, trying to hide his embarrassment.

“Are you almost done, Steve?” Maia called from outside the dressing room, her voice cheerful and oblivious to his turmoil.

“Y-Yeah, just a second!” he replied, attempting to sound casual while hoping she wouldn’t notice the tension in his voice. He took a few deep breaths, willing himself to calm down and regain control. 

Looking back at the mirror, he tried to focus on the costume and the character rather than his rising anxiety. This is just a costume, he reminded himself. It's about having fun with Lily and Maia, not about what anyone else thinks.

Taking a deep breath, Steve stepped out of the dressing room, ready to face whatever awaited him. As he emerged, Maia’s eyes widened in delight. “OMG, this is it! I knew it—Sakura was the perfect choice for you!” she exclaimed, practically bouncing on her feet.



Lily nodded enthusiastically. “Yeah! You look so cute, Steve!” 

But then, she paused, her brow furrowing slightly. “Wait, isn’t Sakura’s hair brown?” she asked, glancing at the wig they’d chosen.

Maia waved her hand dismissively. “Don’t worry about it! Clamp is inconsistent. Sometimes Sakura’s hair is brown, sometimes it’s blonde!”

“Yeah, as long as it fits with Steve,” Lily added with a wink.

Steve, still feeling a bit lost in all the character names and references, furrowed his brow. “Isn’t Sakura’s hair pink?” he asked, genuinely confused.

Lily chuckled, shaking her head. “The pink one is Haruno Sakura from Naruto, silly! The costume you’re wearing is Kinomoto Sakura from Cardcaptor Sakura.”

“Oh,” Steve said, finally understanding a bit better, though he still felt like he was missing some key details. 

“I’m going to cosplay as Li Shaoran, who is Sakura’s boyfriend,” Lily said, her excitement palpable. 

Steve blinked, processing what she was saying. “You mean you’re crossdressing too?” 

“Yeah, it’ll be fun!” Lily replied, her eyes sparkling with enthusiasm. “What do you say?”

Steve realized Lily just wanted him to join her in this colorful world, and it felt less like an obligation and more like an invitation. “Okay,” he said slowly, “but don’t push me too far this time.” 

Lily’s face lit up with joy. “Deal! We’ll take it one step at a time,” she promised, a grin spreading across her face. 

Feeling a bit more at ease, Steve smiled back, ready to embrace whatever adventures awaited him in this new role.