My Crossdress up Darling Ch 2 : Secret Relationship

The next morning, Steve woke up earlier than usual. The sunlight streamed in through the curtains, casting a soft glow over Lily, who was still asleep beside him, her brown hair sprawled across the pillow. Steve watched her for a moment, feeling a mix of warmth and nervousness as memories of the night before flooded back. His heart raced slightly at the thought of what had transpired, but he quickly shook it off. He needed to focus. He had work today.

Carefully, he slipped out of bed, trying not to wake her. He dressed quickly, his mind still buzzing from the intensity of the previous night. After glancing back at Lily, still peacefully asleep, Steve quietly left her apartment and headed to the office.

At his desk, Steve tried to concentrate, but his mind kept drifting back to Lily—specifically, the way she looked in her cosplay costumes. He could still feel the softness of the fabric against his skin and the way her hands had guided him through the night. The memory of her teasing smile, the way she had whispered in his ear, kept replaying in his mind.

He adjusted his glasses and sighed, trying to refocus on the spreadsheet in front of him, but the numbers blurred. Instead, flashes of the night before kept intruding—Lily’s laughter, her warmth, the way she’d called him "Stephanie" in that teasing tone. 

Steve leaned back in his chair, running a hand through his short blonde hair. Focus, Steve. This is work. You can't—

"Why did you leave me this morning?"

Steve’s head snapped up, startled. Lily stood beside his desk, smiling, but there was a playful glint in her eyes. She was dressed in her usual office attire, looking professional, though her presence alone was enough to make his heart race again.

"L-Lily," he stammered, quickly adjusting his glasses. "I, uh, didn’t want to wake you. And... I thought it’d be better if I came in earlier."

Lily tilted her head, her smile never fading as she raised an eyebrow. “Better, huh? Or were you trying to avoid me?” Her voice was light, teasing, but there was a curious edge to it.

Steve shifted in his chair, avoiding her gaze. "No, it’s just... I didn’t want the others to... you know, see us together. I don’t want people to know we’re, um, going out."

Lily frowned slightly, crossing her arms. "And why’s that? You think it’s bad if people know we’re together?"

Steve sighed, rubbing the back of his neck nervously. “It’s not that, Lily... it’s just... I don’t want to ruin your reputation. You’re new here, and you're, well, you. Everyone likes you, and if people find out you’re going out with someone like me...”

Lily’s expression softened. “Someone like you? Steve, what are you talking about?”

Steve looked away, feeling the heat rise in his cheeks. “You’re a pretty new employee... and I’m just, you know, me. People are going to talk, and it might be bad for you. You might have a hard time getting promoted, and... I don’t want to make things harder for you.”

Lily let out a soft chuckle and leaned closer, resting her hand on his desk. “Steve, I don’t care what people think. If they know we’re together, that’s fine by me. You’re worried about my reputation, but you shouldn’t be. I’m not.”

Steve shook his head, still unconvinced. “It’s just not good for a new employee like you to be seen dating a coworker. You’ll get bullied, or people might think you’re just—”

“Using you to get ahead?” Lily interrupted, her tone slightly sharper now. “You really think that’s going to happen?”

Steve hesitated, then nodded slowly. "It could. People can be mean. And... it’s just better if we keep things between us for now. I don’t want to make things harder for you, Lily. I really don’t."

Lily sighed and leaned in closer, her lips dangerously close to his ear. “Well, Steve,” she whispered, her voice soft but teasing, “I guess we can keep it a secret if that’s what you want. But...” She paused, her breath warm against his skin. “I can’t guarantee that what happened last night will stay a secret forever.”

Steve’s eyes widened, his face turning a deep shade of red as her words sank in. His heart pounded in his chest as he fumbled for a response. “L-Lily... don’t... don’t say that here...”

Lily leaned back, grinning at his embarrassment. “You’re too cute when you blush, you know that?” she teased, giving him a quick wink before straightening up.



Before Steve could respond, she turned and walked away, leaving him sitting at his desk, completely flustered. He glanced around, making sure no one else had heard their conversation, but his mind was spinning. He couldn't shake the thought of what Lily had just said, and his focus was now completely shot for the rest of the day.

Steve trying his best to focus on the endless tasks piling up for the day. The office buzzed with activity, coworkers discussing projects and the soft hum of ringing phones filling the air. He rubbed his eyes and glanced at the clock—just a few more hours until lunch.

His phone buzzed on the desk. Not looking at it yet, he muttered, “Focus, Steve... you’ve got work to do.”

With a sigh, he dove back into the latest email from his boss.

"Steve, could you prepare the report for the quarterly meeting this afternoon?" his coworker, Jenna, called over from her desk.

“Yeah, I’m on it,” Steve replied, trying to sound more focused than he felt. His fingers flew over the keyboard as he started compiling the necessary data for the meeting. Every few minutes, his mind would wander back to Lily, their morning exchange, and how she teased him. “Why did she have to say those things at work?” he thought, shaking his head with a small grin.

“Steve, can you double-check the numbers in this?” Another voice—Chris, from accounting—leaned over his cubicle wall and handed him a printout.

Steve glanced at it quickly, nodding. “Sure thing, just give me a sec.”

He looked over the spreadsheet Chris had handed him. His eyes scanned the rows of numbers, but the memory of Lily whispering in his ear kept creeping in. He shook his head again, trying to concentrate.

“Uh, Steve? You okay?” Chris asked, raising an eyebrow.

“Yeah, yeah. Just... distracted. You know how it is,” Steve mumbled, glancing briefly at Lily’s desk across the office, before focusing back on the sheet.

"Big project? Or something else?" Chris teased, smirking.

Steve forced a chuckle, waving him off. "Just... trying to keep up with everything."

Chris nodded, still looking amused. "Well, don't let me slow you down."

As Chris walked away, Steve breathed a sigh of relief, trying to clear his head. He looked back at his computer and muttered to himself, “Okay, focus. Get through the numbers, finish the report, and then you can take a break.”

For the next half hour, Steve powered through the report, keeping his head down and working through the requests from his team. Jenna passed by again, this time placing a stack of documents on his desk. “Can you review these before lunch?” she asked, giving him an apologetic smile.

“Yeah, sure,” Steve replied, adding them to the growing pile. “I’ll get them done.”

Jenna chuckled. “You’re always so calm, Steve. How do you handle all this?”

Steve smiled slightly. “Just... used to the pressure, I guess.”

The conversation quickly ended as his phone buzzed again. This time, he glanced at the screen out of curiosity, expecting another work-related notification. Instead, he froze when he saw the message:

"Surprise... I hacked your phone and got your number last night. Could you accompany me to downtown tomorrow? I have a few things to buy ;)"

Steve blinked, reading the message again to make sure he wasn’t imagining things. Hacked my phone? His heart raced. The sender was an unknown number, but there was no doubt in his mind—this was Lily. He glanced across the room to where she sat, looking completely focused on her computer screen.

How did she even— Steve thought, but then Lily looked up, her eyes meeting his for a brief second. She flashed him a playful smile, clearly amused by his reaction.

His heart pounded as he quickly typed out a response:

"You hacked my phone? Really? Fine, I’ll come to your apartment at 9 a.m. tomorrow."

He stared at the message for a moment, his fingers trembling slightly before pressing send. Just as he placed the phone back down, it buzzed again:

"Then it’s a date. XOXO"

Steve’s face went red. A date? He glanced around to make sure no one saw his sudden reaction, then discreetly looked back at Lily. She was still smiling, her eyes meeting his briefly before she went back to typing, as if nothing had happened.

“Hey, Steve,” Jenna called from her desk again. “You okay? You seem... distracted.”

Steve cleared his throat, his voice slightly shaky. “Yeah, just... a lot on my mind.”

Jenna tilted her head. “You sure? You’re turning a little red.”

“N-no, I’m fine. Just work stuff,” Steve replied quickly, turning back to his computer to hide his embarrassment.

As the lunch break neared, Steve tried to focus on his work, but the thought of tomorrow’s “date” with Lily kept creeping into his mind. He took a deep breath, trying to shake off the nerves. Tomorrow was going to be... interesting.

At Saturday morning, Steve stood nervously outside Lily’s apartment door, bundled up in a long jacket, a hat pulled low over his head, a flu mask covering most of his face, and large shades hiding his eyes. He felt ridiculous, but in his mind, it was the only way to keep their outing a secret. His heart pounded as he knocked, glancing around the hallway to make sure no one was around.

Moments later, the door swung open, and Lily stood there, beaming with excitement. But as soon as she saw Steve, her expression shifted to one of amused surprise. She blinked, looking him up and down with wide eyes.

“Steve... what on earth are you wearing?” she asked, crossing her arms with a half-smile.

Steve adjusted his shades nervously. “Like I said before,” he mumbled through the mask, “it’s dangerous for you if someone from the office sees us going downtown together. I don’t want to cause any trouble for you. This way, no one will recognize me.”

Lily let out a soft laugh, shaking her head. “Steve, if anyone saw you like this, they’d think I’m walking around with a criminal or something.” She gave him a playful nudge, her eyes gleaming with amusement. “You look like you’re about to rob a bank.”

Steve hesitated for a moment, then let out a small, awkward laugh, realizing she was right. The jacket, hat, mask—he really did look suspicious. “Yeah... maybe I overdid it a little,” he admitted, scratching the back of his head. “But still... I just don’t want anyone talking.”

Lily tilted her head, tapping her chin thoughtfully. “Hmm, well... if you’re that worried about being recognized, I think I have a better idea.” Her eyes lit up with mischief as she grabbed Steve’s hand and started pulling him inside.

“W-wait, what are you doing?” Steve asked, confused, as Lily led him down the hallway to her bedroom.

She didn’t answer until they were standing in front of her closet. With a wide grin, she opened the door and began rummaging through her collection of clothes. “If you don’t want to look suspicious,” she said, glancing over her shoulder at him, “then how about you use another disguise?”

Steve’s eyes widened in alarm as Lily pulled out a cute sundress—a soft blue fabric with a floral pattern and delicate lace details. He froze, immediately realizing what she was suggesting. “N-no... please, no,” he stammered, holding up his hands in protest. “I’ll look like a sissy!”

Lily turned to face him, holding the dress up with a playful smile. “Come on, Steve. No one will even recognize you like this. You’ll look like a completely different person—like a girl.” She winked. “Trust me, no one will give us a second glance.”

Steve took a step back, his mind racing. “But... I mean... I can’t...”

Lily stepped closer, her smile softening as she reached out to gently take his hands. “Don’t worry, Steve,” she said reassuringly, her voice soothing. “You won’t look silly. I’ll do your makeup and everything. No one will ever know it’s you.”

Steve stared at the dress in her hands, his pulse quickening. The thought of going out in public dressed like that made his stomach twist with anxiety. But at the same time, he could see the excitement in Lily’s eyes, and part of him couldn’t deny how much he wanted to make her happy.

He swallowed hard, glancing down at the dress again. “You really think this will work?” he asked quietly, his voice barely above a whisper.

Lily’s smile widened as she gave his hands a reassuring squeeze. “I know it will. Just trust me, Steve. You’ll look great.”

Steve hesitated for a moment longer, then let out a sigh, resigning himself to the idea. “Okay,” he muttered, “but this better be convincing.”

Lily’s eyes sparkled with excitement as she pulled him toward the vanity. “Oh, don’t worry! By the time I’m done with you, no one will ever guess who you really are.”

Steve sat in front of Lily's vanity, feeling the gentle brush of makeup on his skin as she worked meticulously. He couldn’t see much of what she was doing, just the occasional glimpse of her focused expression in the mirror as she dabbed, blended, and perfected his look. Part of him still couldn’t believe he’d agreed to this—going out in public, dressed in a sundress, of all things. But there was something about the way Lily handled everything with such confidence that made it hard to refuse.

After what felt like an eternity, Lily finally stepped back with a satisfied smile. “All done!” she announced, clapping her hands together in excitement. “Take a look.”



Steve hesitated before turning toward the mirror, nervous about what he’d see. But when his eyes finally landed on his reflection, his breath caught in his throat. The person staring back at him was... someone else entirely.

His short blonde hair had been styled with soft, feminine waves, and his blue eyes—usually hidden behind his glasses—were now accentuated with subtle, expertly applied makeup that made them seem larger and brighter. His lips were painted a delicate shade of pink, and his face had been contoured just enough to give him a more delicate, feminine look.

He blinked, leaning in closer to the mirror, almost unable to believe that the reflection was actually him. "Is... is that really me?" he murmured, his voice barely above a whisper.

Lily beamed with pride, stepping beside him and admiring her handiwork. “Yep! Told you I’d make it work. You look amazing, Steve... or should I say, Stephanie?”

Steve couldn’t help but stare, still trying to process the transformation. The sundress fit him perfectly, the soft fabric flowing gently around his body, making him look completely different. His usual awkwardness seemed to disappear beneath the layers of makeup and the outfit, and for the first time, he felt like he could actually pull this off.

“I... I can’t believe it,” he admitted, touching his cheek lightly as if to make sure the reflection was real.

Lily grinned, clearly enjoying his reaction. “See? I told you no one will recognize you.”

But then, as she looked him up and down, she frowned slightly. “There’s just one thing,” she said, tapping her chin thoughtfully. “If I had a bigger bra, we could really complete the look. You’d need a little more up top to make it convincing.”

Steve hesitated, biting his lip. The last thing he wanted was to draw more attention to himself, especially after all the effort they’d gone through to make him unrecognizable. “Are you sure this is a good idea?” he asked, uncertainty clear in his voice.

Lily clapped her hands again, practically bouncing with excitement. “Yeah its not bad. Now let’s go out and prove it. You’re going to be the cutest girl in town, Stephanie.”

Steve swallowed hard, looking at his reflection one last time. “Let’s hope no one from the office sees us...” he mumbled, before following Lily out of the room, nerves buzzing in his stomach as they prepared to step out into the world.

The sun was shining brightly as Steve and Lily walked down the sidewalk, the soft breeze ruffling the hem of Steve's sundress. He couldn’t help but feel a strange mix of nervousness and self-consciousness with every step, his legs slightly trembling beneath him. The dress swayed with his movements, and he could still feel the light tug of the bra straps underneath, making him hyper-aware of every glance that passed by.

Lily, on the other hand, seemed completely at ease, walking confidently beside him as if it were the most natural thing in the world. Her hand was firmly clasped around his, her fingers intertwined with his in a casual, affectionate grip.

“L-Lily,” Steve muttered, glancing nervously at the passersby, “I... I think maybe we shouldn’t hold hands so tight. People might... you know... notice.”

Lily turned to him, smiling softly. “Oh, come on, Steve. It’s completely normal for girls to hold hands with each other. No one’s going to think anything of it. Trust me, no one’s going to see us as... you know, gay.”

Steve swallowed hard, still feeling awkward. He could feel the eyes of people passing them on the sidewalk, though he wasn’t sure if it was just his imagination. “I guess,” he said hesitantly, “but it still feels... strange. Like... maybe people are staring.”

Lily laughed gently, squeezing his hand. “Of course they’re staring,” she teased, leaning in slightly. “You’re cute! It’s normal for people to watch a cute girl like you walk by. Don’t worry about it. You’ll get used to it, and eventually, you’ll enjoy the attention.”

Steve blinked, feeling his face heat up. Cute? He glanced down at himself again, the sundress swirling around his knees, his makeup flawlessly applied, but still—this wasn’t him. The idea of being seen as a "cute girl" made his stomach churn, and he couldn’t shake the feeling that every person who looked their way could somehow see through the disguise. They must know... They have to know...

But Lily walked beside him with such confidence, her fingers still tightly wrapped around his hand. Steve stole a glance at her, trying to draw strength from her relaxed demeanor. She didn’t seem worried in the slightest, smiling as they continued walking down the busy street.

Still, Steve couldn’t shake the unease that clung to him. Every time someone passed, he felt a spike of anxiety. His gaze darted around nervously, searching for signs that someone had noticed—someone giving him a weird look, or whispering to their companion. The sounds of the city buzzed in his ears, making him feel more and more out of place.

Lily seemed to sense his tension and gave him a reassuring smile. “You’re worrying for nothing, Steve. I promise. You look great—no one’s thinking anything weird. It’s just a bunch of people walking down the street. We’re just two girls enjoying the day.”

Steve nodded slowly, trying to relax, though the awkwardness still clung to him. “I guess you’re right... it’s just... new. I’m not used to it.”

Lily giggled. “Well, get used to it. You’re doing fine, Stephanie.”

They walked for a little longer, Steve’s hand still tightly held by Lily’s. Despite her reassurances, he couldn’t shake the feeling of being out of place. But as they neared the metro station, Steve’s attention shifted. The station was bustling with people—crowds moving in and out, commuters brushing past one another as they hurried to catch their trains.

When they arrived at the entrance to the metro, Steve’s anxiety spiked again. The crowds looked dense, the constant flow of people intimidating. “It’s... pretty crowded,” he mumbled, eyeing the throng of people moving through the turnstiles.

Lily gave him a quick squeeze on the arm. “Relax. Just follow me. No one’s going to give you a second thought.”

Steve hesitated, glancing at the mass of people again. They all seemed so absorbed in their own lives—no one was stopping to notice him. Maybe Lily’s right, he thought. Maybe no one’s paying attention to me after all.

They boarded the train heading downtown, and after just one stop, the train began to fill up rapidly. It was rush hour, and the space around them quickly became cramped. Steve leaned against the wall, trying to find a comfortable position, while Lily stood in front of him, her body uncomfortably close.

As the train moved along, the crowd grew denser, pushing their bodies together until they were pressed tightly. Steve could feel every shift of the crowd, every nudge and bump, but nothing prepared him for what happened next. Without warning, Lily’s hand slipped down to his crotch, her fingers brushing against the fabric of his dress.

Steve’s eyes widened in shock, his breath catching in his throat. He glanced around nervously, hoping no one would notice. Lily leaned in close, her voice a low, teasing whisper, “How do you feel, Steve? Enjoying being a girl? How about experiencing what it’s like in a crowded metro?”

Steve’s mind raced. He’d thought the day would involve a simple ride through the city, but now it felt like he was trapped in a twisted scenario designed to push his boundaries. His heart pounded as he realized Lily’s intention—to simulate the fear and vulnerability of being a girl subjected to unwanted attention in public. Panic surged through him, and he managed to whisper urgently, “Please… not here…”

Lily’s smirk grew as she continued to stroke his bulge through the fabric of his dress. “Is it soft in there?” she murmured, her fingers expertly tracing the outline of his cock. “Can you feel how soft my panties are?”

Steve’s face flushed with embarrassment. His body was betraying him, reacting to her touch despite his best efforts to stay calm. The sensation of her panties against him was almost overwhelming, and he could feel himself growing harder with every movement. He tried to suppress his moans, but the pleasure was too intense.

Inside, Steve was a whirlwind of panic and shame. “This can’t be happening. Why is this happening?” His thoughts raced as he squeezed his eyes shut, desperately wishing that the train would clear out, that everyone would forget what was happening, that he could disappear. “Someone must see us. Please, no one look.”

Lily’s voice was a teasing whisper, full of mock sympathy. “You’re so cute, Stephanie… like a naive, young virgin girl. You know, most girls are too scared to fight back against someone like this, just like you are now.”



Steve’s breathing grew erratic. “Please… don’t… not here…” he managed to gasp, his voice trembling. The tension was unbearable, and he could feel his control slipping. He tried to focus on anything other than the growing need inside him, but it was futile.

“Lily.. plea…ssee… ahh… aahhnn…” A moan escaped his lips, soft and involuntary, his body reacting to Lily’s touch. He felt a wave of shame wash over him as he heard a few murmurs and felt eyes turning in their direction. The sound of his moan seemed to echo in the small space, drawing unwanted attention.

Lily finally pulled her hand away, leaving Steve trembling and humiliated. The train continued to jostle with every stop, but Steve was acutely aware of the lingering stares. His face burned with a deep crimson as he met the curious gazes of nearby passengers, his heart pounding in his chest.

“I can’t believe this is happening. Everyone is watching me.” He tried to regain his composure, his mind spinning with embarrassment. He wished he could vanish, sink into the floor, or just disappear from the train entirely.

Lily’s expression was one of amused satisfaction, and Steve knew there was no escaping the aftermath of this moment. He stood there, trying to steady his breathing, feeling every eye on him as the train continued its journey.