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I'm a Cross-dresser and the President Wants Me as His Girlfriend

Jacy_Vikey
14
chs / week
The average realized release rate over the past 30 days is 14 chs / week.
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Synopsis
Alex Chen is a quiet, shy and timid student, transferring to the prestigious Matires Academy after years of being bullied for his delicate, almost feminine features. With no friends and a history of being ridiculed, he has learned to keep to the shadows, carefully crafting a new identity: a stunning girl who blends effortlessly into the school. Though he avoids attention, jealous classmates can’t help but resent his beauty, and Alex treads carefully to remain unnoticed. His fragile peace shatters when an iPhone belonging to Dave Henry, the cold and enigmatic student council president, is found in his bag. Expecting harsh punishment, Alex braces himself—but instead, Dave delivers a shocking ultimatum: Alex must pretend to be his girlfriend while serving as his personal assistant. Confused and wary, Alex struggles to maintain the charade, all while wondering how long he can keep his secret—and what Dave will do if he discovers he is not actually a girl. As punishment, Dave, a class ahead and known for his authoritative demeanor, must confront the situation directly. But as he administers the consequences, Alex begins to sense something unusual: does Dave actually enjoy controlling him? The punishments escalate in their peculiarity, leading Alex to question Dave’s motives, especially when they take a bizarre turn—forcing him to maintain the persona of a girl. Caught in a whirlwind of confusion and unexpected emotions, both find themselves grappling with their feelings. Alex wonders why Dave seems to derive a strange satisfaction from their encounters, while Dave is increasingly drawn to Alex’s vulnerability and resilience. As the lines between authority, deception, and attraction blur, they must navigate their complex relationship and uncover the secrets lurking beneath their circumstances. Can two seemingly opposite personalities forge a connection amidst misunderstanding and societal expectations? In this story of self-discovery and unexpected romance, Alex and Dave must confront their true selves and each other, ultimately leading to a surprising twist in their lives.
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Chapter 1 - The Unofficial Punishment: Be My Girlfriend

The air in the grand corridor of Matires Academy turned cold and stagnant, as if the very oxygen had been sucked out of the hallway.

Alex stood frozen, his heart hammering against his ribs like a trapped bird. At his feet, the contents of his worn canvas bag lay scattered across the polished marble—a humiliating mosaic of thrift-store notebooks, a cracked pencil case, and a cheap bottle of floral-scented lotion he used to maintain the "feminine" softness of his skin.

But it was the object resting right in the center that held the crowd spellbound: an iPhone 17 Pro, its titanium frame gleaming under the recessed lighting with a predatory sheen. It was a piece of technology that cost more than Alex's entire wardrobe, and it certainly didn't belong to a scholarship student who spent his lunch breaks hiding in the library.

"Is that mine, Alex?"

The voice was like silk stretched over a blade. It didn't ripple with anger; it was terrifyingly level.

The circle of onlookers parted instantly, a silent wave of students retreating to make way for the apex predator of Matires Academy. Dave Henry stepped forward. He was the embodiment of the school's "old money" prestige—uniform pressed to a razor's edge, his posture radiating a chilling, effortless authority. As the Student Council President, he was the law. As a Henry, he was the royalty.

Dave came to a halt just inches from the mess on the floor. His dark, enigmatic eyes were fixed entirely on Alex's pale, trembling face. Alex felt the weight of every gaze in the corridor pressing against him like a physical bruise. He wanted to melt into the shadows, to become the invisible boy he had spent a year trying to be, but today, the shadows had betrayed him.

Slowly, Dave leaned down. The movement was graceful, almost hypnotic. As he reached for the phone, his fingers brushed against Alex's shaking hand.

The contact sent a jolt through Alex—a strange, heavy heat. For a split second, the President's gaze didn't feel like a judgment. It felt like a claim.

Dave straightened up, the phone balanced in his palm. He looked at the device, then back at Alex, a faint, unreadable twitch at the corner of his mouth. "See me in the student council office. Immediately."

Without waiting for a response, Dave turned on his heel. The crowd remained silent until the click of his expensive loafers faded down the hall. Only then did the whispers erupt—vicious, jagged sparks of "thief," "liar," and "crazy." Alex scrambled to shove his belongings back into his bag, his vision blurring with hot, stinging tears. He didn't belong here. He never should have come to this school.

The trek to the Student Council office felt like a walk to the gallows. The hallway grew quieter the closer he got to the administrative wing, the walls lined with oil paintings of former deans who seemed to sneer at him as he passed.

When Alex reached the heavy oak door, he hesitated, his hand hovering over the brass handle. He took a shaky breath, adjusted the wig that felt like a lead weight on his head, and pushed.

The door clicked shut behind him, the sound muffled by the thick, sound-dampening insulation of the room. The office smelled of expensive cedarwood, old paper, and something uniquely Dave—a crisp, cold scent of winter air.

Alex kept his head down, staring at the scuffs on his shoes. He braced himself for the lecture, the immediate call to the police, or the expulsion papers he was certain were already sitting on the desk. The silence stretched, long and agonizing, punctuated only by the rhythmic ticking of a grandfather clock in the corner.

"Look at me, Alex," Dave commanded.

It wasn't a request. It was an executive order.

Alex forced his chin up. He expected to see the "Perfect President" mask—the one Dave wore for assemblies and faculty meetings. Instead, Dave was leaning casually against his massive mahogany desk, his legs crossed at the ankles. The iPhone was dangling from his fingertip, swinging back and forth like a lure.

There was a flicker in Dave's eyes—a dark, playful spark that Alex had never seen in any of the school's promotional materials.

"A thief deserves a punishment," Dave whispered, pushing off the desk and stepping into Alex's personal space. The height difference was staggering. Alex felt small, fragile, and utterly exposed. "But I think the school's rules are far too... unimaginative for someone as quiet as you."

"I... I didn't take it," Alex whispered, his voice cracking, the pitch higher than his natural register as he struggled to maintain his female persona. "I don't know how it got there. Someone must have put it in my bag."

Dave tilted his head, his eyes roaming over Alex's face with a clinical, terrifying intensity. He reached out, using a single finger to lift Alex's chin, forcing their eyes to meet and stay met.

"The disciplinary committee wants you gone, Alex," Dave said, his voice dropping to a low, melodic hum that vibrated in Alex's chest. "Theft of a luxury item is a stain on the school's prestige. And on my reputation, since I'm the one who 'lost' it. Normally, I'd have the security footage reviewed, the police called, and you'd be back in whatever gutter you crawled out of by sunset."

Alex's breath hitched. "Please..."

"But," Dave interrupted, his thumb slowly brushing against Alex's lower lip. It was a gesture far too lingering, far too intimate for a disciplinary hearing. "I believe you."

Alex blinked, stunned. The air in the room felt thick, like honey. "You... you do?"

"Yes. You're too timid to be a thief. You're the type who hides in the back of the class and hopes the world forgets you exist." Dave's thumb pressed a little harder against the soft flesh of Alex's lip. "But the school needs a 'consequence.' The rumors are already flying. If I let you go with a pat on the head, I look weak. And I don't like looking weak."

Dave leaned in closer, his lips inches from Alex's ear. "I've decided I don't want to lose you to a suspension. I'd rather keep you where I can see you. Where I can use you."

Alex's heart hammered a frantic rhythm. "Use me? How?"

Dave pulled back just enough to look Alex in the eye, a predatory smirk finally breaking across his face. "You're going to be my personal assistant. You'll carry my books, you'll organize my schedule, and you'll be at my beck and call every hour of the school day. But that's just the official version."

Dave's hand moved from Alex's chin to his shoulder, gripping the fabric of his blazer. "The unofficial version? You're going to be my girlfriend. You will play the part of the devoted, beautiful girl who managed to melt the ice around the President's heart. You will sit with me at lunch. You will walk with me through the halls. And you will do exactly as I say, when I say it."

"I... I can't," Alex gasped, his mind racing. If he was that close to Dave every day, the secret would come out. The wig, the padding, the voice—it would all crumble. "Why me? Why would you want me?"

"Because," Dave murmured, his eyes darkening with a strange, possessive satisfaction, "I find your vulnerability... addictive. And I want to see how long it takes for you to break."

Dave stepped back, returning to his desk as if the intense encounter had never happened. He sat down and gestured to a stack of papers. "Start by filing these."

As Alex reached for the papers with trembling hands, he couldn't shake the feeling that Dave wasn't just punishing a thief—he was playing with his prey. And the most terrifying part wasn't the threat of being caught; it was the way his heart hadn't stopped racing since Dave first touched him.