My Crossdress up Darling Ch 3 : Shopping Date

The train screeched to a stop at the downtown station, and as the doors slid open, the crowd surged forward, spilling out onto the platform. Steve and Lily followed, weaving their way through the throngs of people. Steve’s heart was still pounding from the crowded train ride, and his cheeks were burning red—not from the rush of people, but from the way Lily had teased him the entire time. As they stepped onto the platform, he took a deep breath, trying to calm himself.

Once they were a little farther from the crowd, Steve turned to Lily, his face still flushed. “L-Lily, that was too much,” he mumbled, his voice filled with a mix of embarrassment and frustration. “You didn’t have to do that...”

Lily, ever the playful spirit, simply smiled at him, her eyes twinkling with mischief. “Oh, come on, Steve,” she said with a teasing lilt. “Don’t be mad. You enjoyed it, didn’t you?”

Steve’s blush deepened, and he avoided her gaze, his hands fumbling nervously with the hem of his dress. He opened his mouth to argue, but the words wouldn’t come out. The truth was, part of him had enjoyed the attention, even if it made him nervous and embarrassed. But admitting that? No way.

Lily leaned in closer, her smile widening as she saw his reaction. “Your face says it all,” she teased, poking his cheek gently. “You liked it very much, didn’t you?”

Steve’s heart raced, and he felt a wave of embarrassment wash over him. He looked down, biting his lip. “I... I didn’t,” he muttered, though his voice was weak and unconvincing.

Lily chuckled softly, stepping even closer until they were side by side. “Mmm-hmm,” she said with a knowing smirk. “You can say you didn’t like it, but that blush says otherwise. Maybe we should make this a regular thing, hmm? Imagine how fun it would be.”

Steve’s eyes widened in surprise, and he shook his head quickly, his blush only deepening. “N-no! Please don’t...” he stammered, his voice trailing off as he tried to compose himself. “I-I don’t like it...”

Lily laughed, her amusement clear as she leaned in closer, her voice dropping to a playful whisper. “Oh, Steve, you’re adorable when you pout like that. But don’t worry, I won’t push you too much.” She winked. “But I have a feeling you’ll come around.”

Steve crossed his arms and pouted, trying to hide his embarrassment, but it was no use. His face was burning, and he knew he couldn’t hide how flustered he was. “Just... don’t do it in public again, okay?” he mumbled, his voice barely audible.

Lily grinned, clearly enjoying his reaction. “Alright, alright,” she said, raising her hands in mock surrender. “I’ll behave... for now.”

They continued walking toward the station exit, the playful tension still lingering between them. Steve’s heart was still racing, but despite his embarrassment, he couldn’t help but feel a strange thrill from Lily’s teasing. Maybe she was right—maybe he had enjoyed it, even if he’d never admit it out loud.

As they stepped out of the crowded station and onto the busy downtown sidewalk, Steve adjusted the strap of his dress, still feeling a little out of place as the city buzzed around them. He was grateful for the fresh air and open space after the cramped train ride, though his nerves hadn’t completely settled.

“So... where are we going?” Steve asked, glancing over at Lily, who was walking confidently beside him.

Lily’s eyes lit up with excitement. “I need to pick up a few things for my next cosplay,” she said casually, as though this were the most normal errand in the world.

Steve blinked, still wrapping his head around the fact that his coworker—someone he saw in meetings and office gatherings—was also an avid cosplayer. “I’m still having trouble believing you’re into cosplaying,” he admitted with a small smile. “I mean, I don’t think I’ve ever met anyone from work who’s into it.”

Lily giggled, nudging him playfully with her elbow. “That’s because we cosplayers tend to keep it hidden from the normies. You know, some people think it’s childish or weird, so we don’t always share it in professional settings.”

Steve tilted his head, thoughtful. “Really? I don’t see why. I mean, you’re really passionate about it, and I think it’s pretty cool. It’s definitely not childish.”

Lily beamed at him, her smile widening. “Thanks, Steve. That means a lot. Some people don’t get it, but it’s nice to know you do.” She paused for a moment, then glanced at him with a soft expression. “And you know... that’s one of the reasons I love you.”

Steve froze for a moment, feeling the words sink in. His face flushed, and he glanced away, flustered by how effortlessly Lily could say things like that. “W-well, I mean... it’s just true. You’re... um... cute when you wear your cosplay,” he mumbled, his voice barely above a whisper.

Lily’s laughter rang out, light and cheerful as she reached for his hand. “See? You’re sweet too. That’s why we’re such a good pair, Steve.”

Steve’s heart fluttered at her words, though he still couldn’t meet her eyes. He let her hold his hand as they walked, feeling a little more at ease now, despite the earlier tension. Her confidence always had a way of rubbing off on him, and somehow, with Lily by his side, things felt a little less awkward.

They walked hand-in-hand down the bustling sidewalk, and before long, Lily led Steve to a small storefront nestled between a café and a bookstore. The sign above the door read Akiba Costume in bright, colorful letters. From the outside, it looked like a simple shop—nothing too flashy, and easy to miss if you weren’t looking for it.

“This is the place,” Lily said, giving Steve a little tug as they approached the door.

Steve followed her inside, his curiosity piqued. But as soon as they stepped through the entrance, his eyes widened in awe. The store was nothing like he expected. The walls were lined with racks of vibrant wigs in every imaginable color—long flowing ones, short pixie cuts, rainbow streaks, and even fantastical styles that looked straight out of a cartoon. There were costumes everywhere—dresses, suits, armor sets, and even elaborate gowns that looked like they belonged in another world.

Steve took a few steps inside, his gaze wandering over the endless aisles of costumes. “Whoa...” he breathed, his eyes wide as he took it all in. “This... this is amazing.”



It felt like he had stepped into a completely different world, one filled with fantasy and color. There was even an aisle that looked like a mini-weapon shop, with prop swords, shields, staffs, and other accessories carefully displayed on racks.

Lily noticed his amazement and smiled. “Pretty cool, right? It’s like walking into an anime convention all year round.”

Steve nodded, still trying to wrap his head around everything he was seeing. “Yeah, I’ve never seen anything like this. I had no idea stores like this even existed.”

Lily laughed softly, clearly pleased with his reaction. “That’s because it’s more than just a store. The owner’s a cosplayer like me. But she dedicated herself to helping the community and opened this place to provide for other cosplayers.”

Steve turned to her, still in awe. “Wow... that’s incredible. It must be a dream come true for anyone into cosplay.”

Lily nodded. “It is. And she doesn’t just sell stuff—she’ll help you make custom costumes, too. She’s helped me with a few of mine. She’s a genius with fabric and design.”

Steve took another look around, now with a deeper appreciation for the place. “I didn’t realize there was so much creativity behind all of this. It’s... kind of inspiring.”

Lily squeezed his hand, her smile warm. “That’s one of the things I love about cosplay. It’s not just about dressing up—it’s about bringing characters to life, creating something unique. It’s an art form.”

Steve nodded slowly, feeling a newfound respect for the passion Lily and others had for this world. “I can see why you love it so much. It’s like stepping into a different reality.”

“Exactly,” Lily said, her eyes sparkling with enthusiasm. “And today, I’m here to pick up a few things for my next project. Wanna help me find what I need?”

Steve smiled, still a little out of his depth, but excited to explore this new world with her. “Yeah, I’d love to.”

As Steve and Lily wandered deeper into the store, admiring the rows of colorful costumes and wigs, a woman approached them, her footsteps light. She had dark hair tied into a stylish bun, wearing a vibrant outfit that looked custom-made, fitting right into the creative atmosphere of the store.

“Lily! Long time no see!” the woman called out, her smile bright and genuine.

Lily’s face lit up immediately. “Maia!” she exclaimed, rushing to give the woman a quick hug. They both laughed, exchanging a few giggles as though they’d known each other for years.

Steve, still trying to take in the overwhelming array of costumes around him, watched the two women, feeling a bit like an outsider in this world of creativity and cosplay. But before he could get too lost in thought, Maia’s attention shifted to him.

“And who’s this pretty boy?” Maia asked with a teasing grin, her eyes scanning Steve from head to toe.

Steve’s heart skipped a beat, his face flushing bright red. He opened his mouth, unsure of what to say. “Uh...”

“Oh, Maia, this is Steve,” Lily said, leaning into Steve playfully. “He’s... trying something new today.”

Maia raised an eyebrow, amused. “Ah, I see. And Steve, does this ‘something new’ include crossdressing, or is this more of an undercover mission?” Her grin widened as she spoke, clearly having fun.

Steve’s eyes widened, and he felt his cheeks burn hotter. “Y-you knew I’m a guy?” he stammered, embarrassed.

Maia laughed softly, waving a hand dismissively. “Of course, silly. You’re not the first man I’ve seen crossdressing here. Trust me, I’ve seen all kinds of people in all kinds of outfits. Lily did a great job on your look, though.” She paused, studying Steve closely. “Although... there are a few small things that could be improved.”

Steve’s blush deepened, and he felt the need to explain himself. “I-I’m not a crossdresser,” he muttered quickly. “I’m just... um... disguising.” He fumbled for words, unsure how to explain his situation without sounding ridiculous.

Lily giggled beside him, clearly enjoying his awkwardness. “Maia, be nice! Steve’s new to this whole thing. I had to drag him out of his shell a bit today.”

Maia chuckled and nodded. “Don’t worry, Steve. I’m just teasing you.” She winked at him. “And trust me, you wouldn’t be the first guy to say, ‘I’m not a crossdresser, I’m just disguising.’” She gave him a lighthearted nudge. “It’s pretty much everyone’s first excuse.”

Lily laughed at that. “It’s true! You wouldn’t believe how many guys come in here with the same line.” She turned to Steve, her expression softening. “But honestly, you’re pulling it off better than most.”

Steve could only manage a sheepish smile, still feeling a bit out of place. “I... guess so,” he muttered.

“Don’t worry,” Maia said, her tone growing more encouraging. “You’re doing great for someone new to all of this. And if you ever feel like going all-in, just let me know. I can help with the finer details.”

Lily turned to Maia with a grin. “Maia’s helped me with some of my best cosplays. She’s practically a wizard when it comes to costumes. Remember that one time you helped me sew those wings for the Valkyrie outfit?”

Maia laughed, her eyes lighting up at the memory. “Oh, that was a challenge! We worked through the night on those wings, and I thought we’d never finish. But when you wore it to the convention, it was all worth it.”

Lily nodded eagerly. “It was perfect! People kept stopping me to take pictures. I wouldn’t have pulled it off without you.”

Steve, listening to their conversation, felt a bit more at ease now. There was something comforting about how naturally Lily and Maia talked about their shared passion, like it was a world he could start to understand.

“So,” Maia said, turning back to Steve, “what do you think of all this? Overwhelmed yet?”

Steve chuckled nervously. “Honestly? A little bit. It’s... a lot to take in.”

Lily smiled, nudging him gently. “You’re doing fine, Steve. And who knows? Maybe by the end of the day, you’ll feel like a natural.”

Maia grinned at that. “Lily’s right. Cosplay is all about fun and creativity. There’s no right or wrong way to do it, as long as you’re enjoying yourself.”

Steve nodded, starting to relax a little. “Yeah... I can see that. It’s a whole different world, but it’s kind of inspiring.”

Lily squeezed his hand. “That’s the spirit! Now let’s get what we need for my next project. You’ll be my assistant today.”

Lily pulled out her notebook and excitedly flipped through her costume designs. "Look at this one, Maia," she said with a bright smile, turning the pages to show off her intricate sketches. Maia leaned in, her eyes lighting up as she admired the details.

"Oh, I love this!" Maia giggled, pointing to one of the designs. "It's so playful but still so elegant. You really outdid yourself this time, Lily."

They both laughed, their voices blending with the quiet atmosphere of the shop as they talked about colors and fabrics. Their animated conversation filled the space, and Steve, standing nearby, felt a bit out of place.

Then, without any hesitation, Lily began to undress herself, slipping off her top and stepping out of her skirt until she was standing in nothing but her panties and bra. Steve's eyes widened, and he shifted awkwardly. “What is happening right now?” he thought, feeling heat rise to his cheeks.

Maia, seemingly unbothered, took out her measuring tape and moved to Lily’s side, beginning to take her measurements with practiced ease. Lily stood confidently, arms stretched out as Maia wrapped the tape around her waist, bust, and hips, noting down the numbers.

Steve, on the other hand, couldn’t look away, feeling incredibly out of place. He wasn’t sure where to focus his attention—anywhere but on Lily’s half-naked body. “I shouldn’t be watching this. This feels wrong…” He shifted on his feet, staring down at the floor, wishing he could disappear.

Lily, noticing Steve’s discomfort, turned to him with a teasing smile. “What’s wrong, Steve?” she asked, a playful lilt in her voice. “You look a little... distracted.”

Steve cleared his throat, his face flushed. “Nothing... I’m just, uh, getting used to it,” he muttered, hoping she wouldn’t press further. “Please don’t make a big deal out of this. I’m fine. Just act normal, Steve.”

Lily chuckled, not about to let him off that easily. “Well, since you’re getting used to it, how about we take your measurements, Steve?” she suggested, her eyes gleaming with mischief. “It’ll be fun!”

Steve felt a wave of panic surge through him. “No thanks,” he replied quickly, his voice a little too sharp. He tried to laugh it off, but he could already feel the knot tightening in his stomach. “No way. Not happening. Not here.”

But Lily wasn’t one to take no for an answer. She stepped closer, her grin widening. “Oh, come on, Steve. I insist. It’ll be a good time, I promise.”

Before Steve could protest, Lily moved swiftly, her fingers already undoing the buttons on his dress. He froze, utterly embarrassed as she undressed him, leaving him standing there in just his underwear. His body tensed, and his face flushed with humiliation. How did this happen? he thought, his mind racing. This is so embarrassing…

Lily stood back, satisfied with her work, while Maia approached with the measuring tape in hand, the same bright smile on her face as she began to take his measurements. Steve stood stiffly, trying to stay calm, but the sheer awkwardness of the situation made it nearly impossible.



As Maia worked, her eyes trailed down to his panties, and she couldn’t help but notice the small bulge of penis. A playful smirk crossed her lips. “Well, no wonder you like crossdressing,” she teased. “With a tiny bulge of penis like that, you won’t be caught by anyone.”

Steve’s face went bright red, the words hitting him like a wave of embarrassment. He wanted to disappear, to sink into the floor and never be seen again. “Why does this keep happening to me?” he thought, his hands nervously fidgeting at his sides. His heart pounded in his chest, and he could barely bring himself to look at either of them.

Lily laughed softly, clearly enjoying the moment, while Maia continued taking his measurements, as though this were the most normal thing in the world. “See, it’s not so bad,” Lily teased, giving Steve a playful wink. “You’re fitting right in.”

Maia finished taking Steve’s measurements, stepping back with a satisfied smile. As she tucked the measuring tape away, she glanced at Steve, her eyes sparkling with an idea. “You know, Steve, I’ve got something perfect for you,” she said, her voice filled with excitement.

Steve, still standing awkwardly in just his underwear, raised an eyebrow. “Something for me?”

Maia rummaged through a drawer behind the counter, her movements swift. After a moment, she turned back, holding up a bra with built-in silicone breast forms. The realistic feel of the silicone and the soft lace design made the bra look almost indistinguishable from the real thing. Maia grinned as she held it out to him. “This will make your crossdressing absolutely perfect, Steve. Trust me, you’ll look incredible.”

Steve stared at the bra, feeling his stomach drop. “I-I don’t think that’s necessary,” he stammered, taking a small step back. His face flushed as he glanced at Lily, hoping she’d back him up. “I’m fine as I am…”

But Lily, always quick with her teasing remarks, stepped closer, her eyes gleaming with amusement. “Oh no, you definitely need them, Steve,” she said, her voice soft but insistent. “Think about it—what if one of your coworkers happens to see you while we’re out? Wouldn’t you want to blend in completely? With these,” she gestured to the bra, “you’ll look just like a cute girl. No one will ever suspect a thing.”

Steve hesitated, his mind spinning. “What if someone from work really did see us?” The thought made his heart race. The last thing he wanted was to be recognized by anyone, especially when he was dressed like this. He could feel Lily’s and Maia’s eyes on him, waiting for him to respond.

Reluctantly, Steve sighed. “Okay... I guess I can try it,” he mumbled, knowing he had little choice but to go along with it.

Lily beamed at his agreement, and Maia handed him the bra with a smile. “Great! You can change in the dressing room over there,” she said, pointing toward the back of the boutique.

Steve took the bra, feeling the weight of the silicone breast forms in his hands. His fingers trembled slightly as he made his way to the changing room. The small, private space felt like a temporary refuge from the overwhelming embarrassment that seemed to follow him everywhere today. “This is insane. I can’t believe I’m actually doing this…”

He slipped into the dressing room and quickly pulled the curtain shut behind him. Standing in front of the mirror, he stared at his reflection. The sight of himself in just his panties was strange enough, but now, with the bra in his hands, he felt like he was crossing a new line.

Steve took a deep breath and gingerly slipped the bra over his shoulders. The silicone breast forms settled into place, filling out the cups of the bra and giving him the appearance of a much fuller chest. He adjusted the straps, feeling the unfamiliar weight of the fake breasts pressing against his skin. “This feels so weird… but they do look realistic.”

His moment of quiet was interrupted when the door to the dressing room swung open. Startled, Steve turned to see Lily standing there, a playful smile on her lips. “What’s wrong, Steve?” she teased, closing the door behind her. “Don’t be so shy. I’m your girlfriend, remember? I’m here to help you.”

Steve blinked, still trying to process her sudden presence. “L-Lily, I wasn’t expecting you to come in here…”

Lily laughed softly, stepping closer. “Oh, come on. You know you need help with this,” she said, taking the breast forms from his hands. “Let me show you.”

Without waiting for a response, Lily began to position the breast forms inside the bra Steve was wearing. She adjusted the straps, making sure everything was secure before stepping back to admire her work. “There we go,” she said, grinning. “See? It fits you like a glove.”

Steve hesitated for a moment, then gingerly reached up to touch the forms. His fingers pressed into the soft silicone, and he couldn’t help but squeeze them slightly. The sensation was surreal—heavy yet soft, just like real breasts. His cheeks flushed as he continued to grope the forms, feeling both curious and embarrassed.

Lily watched him with a knowing smile. “Do you like it?” she asked, her tone teasing but gentle.

Steve’s face turned even redder. “Yeah… I think so,” he admitted, still exploring the feel of the breast forms.

As Steve continued to touch the forms, he suddenly felt a hand brush against his crotch. His eyes widened in shock as he realized Lily was gently groping his bulge. “L-Lily… please… we’re in public,” he whispered urgently, glancing toward the door as if expecting someone to barge in.

Lily, unfazed, leaned closer and whispered in his ear, “It’s okay, Steve. No one’s going to come in. As long as you don’t scream, we’ll be fine.” Her hand continued to stroke him through his underwear, her touch deliberate and slow.

Steve’s body tensed, his breathing growing shallow as he tried to suppress the growing arousal. “Lily, we shouldn’t… not here…” he murmured, his voice strained.

But Lily’s hand only moved more purposefully, her fingers tracing the outline of his erection. “Do you like it, Steve?” she asked, her voice soft and seductive. “Do you like your pretty body?”

Steve closed his eyes, struggling to maintain control. His mind was racing, torn between the pleasure building in his body and the sheer embarrassment of the situation. “Lily… please… someone might hear…”

Lily chuckled softly, her hand sliding beneath the waistband of his panties to free his now-erect penis. She began to stroke him slowly, her movements calculated and teasing. “You say you don’t want this, but your body says otherwise,” she whispered, her lips brushing against his ear.



Steve’s breath hitched as he felt her lips press against his, the kiss deep and hungry. His body responded instinctively, his hips pushing forward into her hand despite the voice in his head screaming at him to stop. “Oh god, Lily… please, not here…”

Lily broke the kiss just long enough to smile at him. “It’s okay, Steve. Just let go. I know you want to.”

Steve’s body trembled as the pressure inside him built to an unbearable level. “I… I’m going to… Lily, please… not here…”

But Lily didn’t stop. She stroked him faster, her lips capturing his in another kiss. “It’s okay. Just let it happen,” she whispered against his lips.

With a low moan, Steve’s body tensed as he climaxed, his release spilling into her hand. His knees went weak, and he slumped back against the wall, his breath coming in ragged gasps. The intensity of the moment left him feeling lightheaded, his body trembling with the aftermath of his orgasm.

Lily stepped back slightly, her eyes glinting with satisfaction as she wiped her hand on a nearby towel. “See?” she said with a smirk. “Told you it’d be fine.”

Steve, still trying to recover, glanced at her with a mixture of exhaustion and embarrassment. His face was flushed, and his body felt like it had turned to jelly. “I can’t believe we just did that…”

Lily leaned in and kissed his forehead, her touch unexpectedly tender. “You’re cute when you’re embarrassed, Steve. Don’t worry, no one will ever know.”

Steve’s heart raced as he stared at his reflection in the mirror, still wearing the bra and breast forms. “What am I even doing?” he thought, feeling a confusing mix of shame and excitement. The experience had left him shaken, yet something deep inside him had enjoyed it more than he wanted to admit.

Lily gave him a playful wink before heading toward the door. “Get dressed, Steve. I’ll waiting outside”

He stood there for a moment, looking at himself in the mirror. The bra, combined with his panties, made him look almost convincingly feminine. I guess they were right… it does make the look more complete.

From outside, Lily’s voice called teasingly, “Come on, Stephanie! Let’s see how you look!”

Steve hesitated, his heart pounding. He didn’t want to step out, didn’t want to face their teasing smiles and comments. But he knew there was no avoiding it now. Might as well get it over with…

Slowly, he opened the curtain and stepped out of the changing room, his face flushed with embarrassment. Lily and Maia turned toward him, and immediately, their eyes lit up with approval.

“Oh my god, Steve! You look perfect!” Lily said, clapping her hands together in delight. “Doesn’t he look adorable, Maia?”

Maia grinned and nodded. “Definitely. The bra makes all the difference. You really do look like a cute girl now, Steve.”

Steve’s face burned with a mixture of shame and reluctant acceptance. He glanced down at himself, seeing how the bra gave him a feminine silhouette. It was strange, almost surreal, to see himself like this. I don’t know if I’m ever going to get used to this...

“See?” Lily said, stepping closer and giving him a playful nudge. “Told you it would be fun.”

Steve forced a small smile, trying to laugh it off. “Yeah… fun,” he muttered, though he still couldn’t shake the feeling of unease. The idea of someone he knew seeing him like this sent a fresh wave of anxiety through him.

“Well, now that you’re all dressed up,” Maia said with a wink, “let’s go show you off!”

Steve’s eyes widened in horror. “Wait, what? No, I didn’t agree to that!”

But Lily and Maia were already giggling, clearly enjoying the game far too much to stop now.