My Crossdress up Darling Ch 4 : Cafe Date

As they left the shop, the air outside felt thick with tension, at least for Steve. His mind was still reeling from the experience in the dressing room, and his nerves were on edge. Every step felt heavier than the last, and he couldn’t help but fidget with the edges of his dress, trying to distract himself from the anxiety gnawing at him.

Lily, on the other hand, seemed completely at ease. “How about we stop at that café up ahead and have a little chat?” she suggested, her voice light and casual as if everything that had happened was perfectly normal. Steve hesitated but eventually nodded. His heart pounded in his chest as he followed her lead.

The café was bustling with life when they walked in. The hum of conversation filled the space, mingling with the clinking of coffee cups and the hiss of the espresso machine. Steve could feel every pair of eyes on him, or at least, it felt that way. His mind raced with the irrational fear that someone would notice—that they’d see through his disguise, his awkward steps, his too-tight dress, and realize that "Stephanie" wasn’t who she appeared to be.

As they moved further into the café, Lily placed her hand lightly on Steve’s back, her touch both comforting and commanding. She leaned in close, her breath tickling his ear as she whispered, “Relax, Stephanie. You’re doing fine.” 

Steve tried to take comfort in her words, but his heart wouldn’t stop hammering. He kept his eyes down, avoiding glances from the other customers, his hands trembling slightly as they reached the counter.

Then, in a mischievous tone, Lily nudged him forward. “You’re ordering for us,” she said with a smirk, her eyes twinkling with amusement. 

Steve’s breath caught in his throat. “Me? Ordering?” The thought alone was enough to send his anxiety spiraling. “I… I can’t do that, Lily,” he whispered, his voice shaky. “What if someone notices?”

Lily arched an eyebrow, her smirk growing wider. “You’re already dressed, and you look gorgeous. No one will notice. Unless…” She paused for effect, her eyes gleaming with playful challenge. “Unless you make it obvious.” She winked at him, as if daring him to rise to the occasion.

Steve swallowed hard, trying to muster up some courage. His heart raced as he stepped up to the counter, the bright smile of the barista only making his nerves worse. The moment felt like it stretched on forever. 

The barista’s voice was kind and casual. “What can I get for you today?”



Steve opened his mouth, praying that his voice wouldn’t betray him. “Two lattes, please…” he said, his voice cracking slightly despite his best effort to make it sound softer like a girl. He felt like the words were barely coherent, and he braced himself for the barista to raise an eyebrow, to ask some question that would expose him.

But instead, the barista simply smiled and nodded. “Coming right up,” she said, moving on without a second thought.

Relief washed over Steve, but it was mixed with paranoia. “She didn’t notice… right?” He couldn’t shake the feeling that his nervousness was giving him away, even though no one seemed to be paying him any special attention. 

Lily stood beside him, her grin wide and amused. “See?” she whispered teasingly. “That wasn’t so hard, was it?”

Steve shot her a nervous glance, his face flushed with a mix of relief and embarrassment. “I can’t believe I did that,” he muttered under his breath, his hands still trembling.

Lily chuckled softly. “You’re doing great, Stephanie,” she said, her voice low and sweet. “But this is just the beginning…”

After getting their drinks, Steve hoped they would find a quiet, secluded corner of the café where he could hide away from prying eyes. But, of course, Lily had other plans. With a confident smile, she led him to a table right in the middle of the café—where they were surrounded on all sides by other patrons. Steve’s heart sank. 

His hands trembled slightly as he adjusted his skirt, trying to sit down as inconspicuously as possible. Every movement felt awkward. He nervously tucked his legs beneath the chair, suddenly hyper-aware of how his body was positioned and how his dress fit. It felt like everyone was watching, even though no one seemed to care.

Lily sat across from him, entirely at ease. She sipped her latte with a knowing smile, her eyes sparkling with amusement at Steve’s discomfort. “How are you feeling, Stephanie?” she asked, her voice dripping with playful curiosity.

Steve squirmed in his seat, casting a quick glance around the room. His pulse pounded in his ears, drowning out the sounds of the café. “This is crazy,” he muttered, his voice barely above a whisper. “Someone’s going to notice… they have to.”

Lily chuckled softly, leaning in close as if sharing a secret. “No one’s paying attention, sweetie,” she said, her voice calm and soothing. “You’re just another girl enjoying her coffee. Trust me, you look perfect. If you keep acting nervous, that’s when people will start to notice.”

Steve bit his lip, glancing at the other patrons. Some were busy typing away on laptops, others chatting with friends, but no one seemed to be looking in his direction. Lily’s words were reassuring, but the tightness in his chest refused to let up.

“I don’t know how you do this so easily,” Steve said, taking a hesitant sip of his latte. The warmth of the drink helped calm him slightly, but his nerves were still buzzing beneath the surface.

Lily smiled wider, her eyes twinkling with a hint of mischief. “It’s all about confidence, darling. If you believe you belong here, everyone else will too. Besides…” She paused, her gaze traveling over Steve’s body. “You look so cute in that dress. How could anyone think otherwise?”

Steve blushed, shifting uncomfortably in his seat. The compliments from Lily only made him feel more self-conscious, but there was also a strange thrill in hearing her say it. “I don’t know about cute…”

“Oh, trust me,” Lily said, leaning back in her chair with a satisfied smile. “You’re more than cute, Stephanie. You’re adorable. And if you keep practicing, maybe you’ll even start to believe it yourself.”

Steve glanced around once more, trying to find reassurance in the way people ignored him. Maybe Lily was right—maybe he was just another face in the crowd. But the constant knot in his stomach wouldn’t go away. He was still terrified someone might come up and call him out, even though that fear seemed more irrational with every passing minute.

Lily took another sip of her drink, her gaze never leaving Steve’s face. “You’re doing great,” she said softly. “Just keep playing the part, and soon it’ll feel natural.” Then, with a playful glint in her eye, she added, “And if you get through this little outing without freaking out, maybe we’ll do something a bit more daring next time.”

Steve’s anxiety started to ease ever so slightly—until he felt something unexpected. Underneath the table, Lily’s foot gently brushed against his leg. At first, it seemed like an innocent movement, but then her foot slowly began to slide higher, teasing him in a way that sent a jolt of panic and excitement through his body.

“You’re doing so well,” Lily whispered, her voice soft but laced with mischief. “But let’s see how long you can keep calm.”

Steve’s breath hitched, his heart racing as Lily’s foot reached his crotch. He squirmed in his seat, trying to focus on anything else—the murmur of café conversations, the warm latte in his hand—but the growing pressure from Lily’s teasing touch was impossible to ignore. A rush of heat flooded his face as his body began to respond, and the bulge beneath his dress became harder to hide.

“Not here…” his mind screamed. “What if someone sees?”

He forced himself to look around, scanning the café in a panic. Other customers were going about their business, seemingly unaware of what was happening at the table in the middle of the room. But that didn’t stop the fear from gnawing at him. “What if someone looks over? What if they notice?”

Lily’s foot pressed more firmly against him, her movements slow and deliberate. Steve bit his lip, trying to suppress a gasp, his fingers gripping the edge of the table in an effort to maintain his composure.

“You like being out here, don’t you, Stephanie?” Lily’s voice was low, teasing, and full of wicked amusement. “You love being seen, even if you’re terrified.”

Steve’s body tensed, torn between the thrill of her words and the intense embarrassment that threatened to overwhelm him. His mind was a whirl of conflicting emotions—fear, arousal, shame—all blending together as Lily continued to push him further.

“L-Lily…” he stammered, his voice barely above a whisper. “Please… someone might notice…”

Lily only smirked, her eyes sparkling with delight as she leaned in closer. “They won’t. Not unless you let them. And I think part of you wants them to.” Her foot kept its steady, teasing pressure, sending waves of pleasure through Steve’s body. 

Steve’s breathing became shallow, his heart hammering in his chest. He wanted to protest, to beg her to stop, but there was another part of him—one he barely wanted to admit—that was excited by the danger. By the possibility of being caught. 

Lily leaned back in her chair, casually sipping her latte as if nothing was happening. “You’re doing such a good job, Stephanie,” she murmured, her foot never leaving its spot. “But I wonder how much longer you can hold out before you completely lose it…”

Steve’s face was flushed, his body betraying him as he struggled to keep himself under control. The café felt like it was closing in around him, every clink of a cup, every murmur of conversation, only amplifying the tension inside him.

“Lily, please…” he whispered, his voice shaky with both desperation and desire.

But Lily wasn’t about to let up. Not now. “Just a little longer,” she purred, her foot sliding with agonizing slowness. “I know you can handle it, Stephanie. After all, you love this, don’t you? The thrill of it all…”

Steve’s head spun as he fought to keep his composure. He could only hope that no one would glance over and see the turmoil he was in.

Steve sat stiffly, doing his best to appear calm while the pressure of Lily’s foot at his crotch was making it increasingly difficult. He struggled to focus, his mind a haze of nervous excitement and fear. Every subtle movement of Lily's teasing touch sent jolts through his body, but he tried desperately to act normal.

Then, as if things couldn’t get worse, the café door swung open, and a group of girls walked in, their cheerful chatter filling the air. They passed by their table, one of them glancing in their direction before giggling with her friends. Steve’s heart plummeted, his face turning bright red in an instant. “Did they notice?” Panic gripped him. “Are they laughing at me?"

His mind raced, trying to figure out what to do, but Lily noticed his anxiety and leaned in with a calm, reassuring smile. “Relax, they’re just girls talking,” she whispered, her voice soothing yet playful. “They don’t know anything.”

Steve tried to believe her, but before he could settle his nerves, one of the girls waved at them, flashing a bright smile. “Hey, cute dress!” she said warmly, clearly unaware of Steve’s true identity.

Steve’s heart pounded in his chest, and his breath caught. He tried to act natural, forcing a smile that felt far too shaky. “T-Thank you…” he managed to stammer, his voice weak and a little higher-pitched than usual as he tried to sound like a girl. The girl smiled again and turned back to her friends.

Just as Steve exhaled in relief, the sudden sensation of Lily’s foot pressing firmly into his crotch caught him completely off guard. His eyes widened, and his body tensed as a wave of arousal hit him, causing his already fragile composure to waver.

Lily's foot stroked him again, teasingly, and this time, Steve couldn’t stop himself. A soft, barely audible moan slipped from his lips. “Aahh… Aaahhnn…” The sound was quiet, but to Steve, it felt like the entire café could hear it.



Some of the girls lingered nearby, still chatting, and Steve’s heart raced even faster. He quickly covered his mouth with his hand, his eyes darting around, hoping no one had noticed. His face flushed deeply, embarrassment and arousal mixing into a whirlwind of emotions.

Lily, meanwhile, smirked, clearly pleased with herself. She glanced at Steve, her eyes sparkling with amusement as she watched him struggle to maintain control. “You’re so cute, Stephanie,” she whispered, her voice filled with mischievous delight.

Steve watched her, feeling a mix of admiration and irritation. “Lily, I can’t believe you did that back there,” he said, his voice low. “You made a scene in the middle of the cafe!”

Lily set her cup down, her smirk never fading. “Oh, come on, Steve. It wasn’t that bad. You looked adorable, and everyone had a good laugh. No harm done.”

Steve crossed his arms, still blushing from the memory. “It’s not just that. You keep pushing things... in public. People were staring.”

Lily leaned back, her smile growing even more mischievous. “And what’s wrong with that? A little attention never hurt anyone. You’ve got to loosen up, Steve. Besides, it’s fun watching you get all flustered.”

Steve sighed, knowing that arguing with her was pointless. Lily loved teasing him, especially when it meant stepping outside his comfort zone. “Yeah, well... not everyone likes being the center of attention,” he muttered, glancing around the café as if to make sure no one was watching.

Lily shrugged, still grinning. “You’ll get used to it. And hey, if I didn’t push you, you’d never have tried half the things you’ve done today.” She took another sip of her coffee, then set the cup down decisively. “Come on, I’ve got something fun to show you.”

Steve raised an eyebrow, wary of whatever idea Lily had brewing. “What now?” he asked, his tone half-annoyed, half-curious.

“Follow me,” Lily said with a playful wink, standing up from the table. She nodded toward the back of the café, where a sign pointed to the ladies restrooms.

Steve blinked, suddenly nervous. “Lily, you’re not serious... we’re not going to—”

But Lily was already walking, her confidence unwavering. Steve hesitated, glancing around to make sure no one was paying attention before reluctantly following her. When they reached the restroom, Lily turned back to Steve, her eyes dancing with mischief.

“Come on, Steve. It’ll be fun,” she said, holding the door open.

Steve’s heart pounded in his chest, his face flushing red. “Lily, no way. This is... it’s too much,” he whispered, panicking at the thought of being caught. “We could get in serious trouble!”

Lily stepped closer, her expression softening but still playful. “Relax, Steve. No one’s going to know. It’s just us, and I promise it’ll be fun.” She grabbed his hand, pulling him gently but firmly toward the door.

Steve hesitated, his mind racing with a mix of fear and curiosity. “I... I don’t know...” he stammered, feeling every ounce of his nerves screaming at him to stop.

But Lily wasn’t taking no for an answer. “Trust me,” she whispered, her voice filled with a mix of teasing and genuine encouragement. “You’ve come this far, haven’t you? What’s one more little adventure?”

Steve followed Lily into the ladies' bathroom, his heart pounding as he stepped inside. It was his first time in a place like this, and everything felt strangely foreign. He walked closely behind Lily, trying to stay as inconspicuous as possible, but the unfamiliar setting only made him more nervous.

“Why do girls always go to the bathroom together?” Steve asked, his voice a whisper as they walked in. 

Lily glanced back at him with a cheeky grin. “Oh, it’s fun! You get all the good gossip, share secrets, and sometimes help each other out. It’s like our little hidden world—our secret room.”

Steve nodded slowly, taking it all in. The bathroom was brighter and cleaner than any men’s room he’d ever seen, and as they walked past a row of sinks, he noticed a large mirror stretching across the wall. Two girls stood in front of it, chatting as they reapplied their lipstick, fixing their makeup with the kind of practiced ease Steve had only seen in movies.

The girls were deep in conversation, giggling and talking about their recent dates. “He was so boring,” one of them said, rolling her eyes. “I don’t know why I even bothered to come out.”

The other girl sighed, capping her lipstick. “Tell me about it. Mine was so stingy. It’s like, come on, I’m not asking for much.”

Steve awkwardly glanced away, feeling like an intruder in a world he wasn’t supposed to see. Meanwhile, Lily confidently entered one of the stalls, leaving Steve to stand by the sinks, unsure of what to do. He hesitated, looking for somewhere to hide, and quickly ducked into an empty stall nearby, closing the door behind him.

Inside, Steve leaned against the wall, trying to keep his breathing steady. He could hear snippets of the girls’ conversation outside, feeling more and more out of place. His disguise was holding up, but this was pushing his nerves to the limit.

After a few moments, he heard the sound of a toilet flushing, followed by Lily’s footsteps as she exited her stall. Steve peeked out cautiously, watching as she walked over to the sinks to wash her hands. Relieved to see her, Steve quickly stepped out of his hiding place and joined her, hoping to get out of there as quickly as possible.

Steve tried to keep his composure as he joined Lily at the sinks, but his mind was still spinning from the awkwardness of being in a place that felt so off-limits. As he washed his hands, his thoughts were interrupted by the sound of the bathroom door swinging open again. Steve’s stomach dropped as Jenna, his coworker from the office, walked in.

Jenna’s eyes lit up when she spotted Lily. “Hey, Lily! What a surprise running into you here!” she exclaimed, pulling her hair back into a ponytail as she approached the sinks.

Lily turned to her with an easy smile. “Jenna! I know, right? Small world!” she said, her tone cheerful as if they’d just bumped into each other at the break room.

Jenna rolled her eyes playfully. “Ugh, tell me about it. I’m just taking a break; the guy I’m supposed to meet up with was a total no-show. Men are the worst sometimes, right?”

Lily giggled, nodding sympathetically. “Oh, I hear you. Some guys just don’t get it. So, what else is going on?”

Jenna leaned against the counter, her expression shifting into the familiar look of office gossip mode. “You know, the usual. The work drama never stops. But enough about that—what about you? Are you here alone?”

Lily shook her head, shooting a quick glance at Steve, who was desperately trying to act like he wasn’t eavesdropping. “Actually, I’m not alone,” she said with a coy smile. “I came with my friend Stephanie.”

Steve’s eyes widened, and he tensed up, hearing his alias being casually dropped into the conversation. He dared not look up, fearing that Jenna might piece together who he really was.

Jenna’s curiosity piqued. “Oh? Stephanie, huh? Is she a new friend? I’d love to meet her,” Jenna said, craning her neck as if to look around.

Steve felt his panic spike—his heart pounding louder with each passing second. He knew he couldn’t stay any longer. Before Lily could elaborate further, Steve turned off the faucet hastily and mumbled a barely coherent excuse. 



Steve darted toward the door, pushing it open and slipping out as fast as he could.

As the door swung shut behind him, Steve could still hear the faint sounds of Jenna and Lily talking, but he couldn’t make out the rest of their conversation. He hurried back to the café, his face flushed and his mind racing, relieved to be out of that situation but worried about what Lily might be saying next.