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Cross Dressing Villainess Cecilia Sylvie

Volume One: Part 1

Volume One: Part 1

Jun 23, 2026

Prologue

Dearest Mama and Papa,

Please forgive me for not being your ideal daughter.

In order to live a peaceful and carefree life from now on, I, Cecilia Sylvie…


…have decided to become a boy!


Cecilia Sylvie, daughter of a duke, was only five years old when she realized something that could rock the very foundations of this world, something that revealed it for what it really was.

So earth-shattering was this revelation that she didn’t dare say a peep about it, even at the age of five, fearing that it would cause her anxious mother and maid to turn pale and call for doctors if she let it slip. Still, she couldn’t just pretend like all was well in the face of the twisted shape of her world and her own bleak future. Subsequently, she came down with a fever and was laid up in bed for a week.

Namely, the truth Cecilia realized was that she had transmigrated into the world of the girl’s dating sim Holy Maiden of Vleugel Academy 3.

And Cecilia Sylvie was the main character’s love rival. In other words, she was the villainess of the story.

Even before this realization, she’d always felt that something had been off.

She would sometimes get the distinct sensation that she had someone else’s memories mixed in with hers; she would meet someone for the first time and already know them somehow or would envision unimaginable foods she’d never eaten before, such as “instant ramen.” That last one almost tasted so real it made her mouth water.

Thanks to all this, her parents thought of her as a little bit special, but they loved her all the same. In fact, they spoiled their one and only daughter rotten. They bought her anything she wanted, instructed the servants and maids to prioritize her above all else, and anticipated her every whim.

In short, they were overly indulgent parents who had raised a spoiled, irresponsible, and selfish daughter.

And in fairness, up until that moment, Cecilia had indeed been an incredibly selfish girl.

Happily thinking of herself as the center of the universe, she spent money with such flagrancy that it was clear she didn’t understand the concept of wastefulness. She believed she could get absolutely anything she wanted if she only cried hard enough, and she was entirely convinced that she had a bright future in store.


But upon meeting him, her entire personality changed.

Gilbert Coulson, presently known as Gilbert Sylvie.

The Coulsons were distant relatives, and he was adopted into Cecilia’s family as her brother, one year younger than her.

The instant she laid eyes on him, she froze as though she’d been struck with a powerful bolt of lightning.

That was because she knew him.

Gilbert Sylvie was a love interest in Holy Maiden of Vleugel Academy 3.

There, he had been moody, submissive, and preferred to stay shut up in his room, perhaps because Cecilia treated him as her servant, heedless of the fact that Gilbert had become the son and heir of House Sylvie.

While his age, overall look, and expressions did not match up with her memories of the character, his hair, as black as a wet raven’s wings, and eyes of obsidian were unmistakable.

And then memories of her previous life flooded in one after another…

But there, Cecilia changed her mind, reminding herself that there was no way that was possible.

Which was understandable. Ordinarily, no one would have believed her. Yet, those undeniable memories of her past life brought a swift end to her selfish behavior.


The month after Gilbert came to live with the Sylvies, her distinct sense of unease was wholly validated. It happened when she first made her high society debut, accompanied by her father.

There, she met another love interest from the game…

Oscar Abel Prosper.

The son of the king of Prosper. In other words, the crown prince and the man who was set to become Cecilia’s fiancé in two years.

The moment she learned the identity of this arrogant redhead, she collapsed, frothing at the mouth.

As for why, there was the fact that she’d witnessed with her own eyes that the unreal was actually very real. But there was also her despair for her own fate—which was probably the most accurate explanation.


None of the endings for Cecilia Sylvie in Holy Maiden of Vleugel Academy 3 were happy ones.

The only lots that awaited her were a painful death or a quick death.

The second she realized she might die at seventeen, she made a grand decision to stave off her looming fate twelve years hence.

“Okay, then. I’ll become a boy!”


Yes, Cecilia Sylvie decided to dress as a boy to avoid her tragic fate.





CHAPTER 1

Selection Ceremony

Vleugel Academy had its very own prince.

He had hair of translucent gold and eyes of sapphire blue.

He was long-limbed, with an androgynous face that could charm anyone.

He glided silently through the halls with all the grace of a single white rose.

If a girl tripped in front of him, he would smoothly offer her a hand and whisper to her in his mellifluous voice with his beautiful features, “Are you hurt in any way, my princess?”

That was when squeals of joy would rise up from out of nowhere.


The prince was named Cecil Admina.

The alter ego of one Cecilia Sylvie, the seventeen-year-old daughter of a duke.

***

“Mmm, why did things end up like this…?” Cecil, or rather Cecilia, grumbled as she gazed up at the glazed glass roof of the academy greenhouse. Next to her on the bench sat her sixteen-year-old younger brother, Gilbert.

They were the only two people in the standalone greenhouse, which was her one and only haven in the school, the only place where girls would not call out, “My prince!” and pursue Cecil.

“I just wanted to blend in and keep to myself here, so why have I become the school prince…?” She sighed.

“That’s because you’re a nitwit, Sister,” answered Gilbert.

“Guh!”

His words cut like a dagger to the heart.

Gilbert was supposed to have grown up to be dour and moody under Cecilia’s heel, but now—twelve years after they’d first met—he’d transformed into a sharp-tongued, sassy little thing. That was more or less to be expected since she hadn’t bullied him like in the game, but still, she wished he’d grown up to be a little bit cuter…

Undaunted by his sister’s glare, Gilbert threw her an exasperated look. “What was that ‘Are you hurt in any way, my princess?’ nonsense from this morning, then? You sure seem to spout the most cringeworthy lines as if they were nothing.”

“Hey, I can’t have anyone noticing that I’m really a girl. Obviously, I have to act even manlier than a normal guy!” she protested.

“That’s your idea of manly?”

“If you want to know the most popular type of character in the dating sims I played for eighteen years of my last life, then yes, that’s it!”

“…Yeah, which is what caused all this,” Gilbert deadpanned once again.

In Cecilia’s past life, she’d been Hiyono Kanzaki, a high schooler who’d been a major fan of dating sims featuring casts of handsome men.

Hiyono was the type to blow almost all her allowance on dating sims, and if she didn’t have enough money to snap everything up at once, she would work a part-time job to cover the rest. Staying up all night gaming until dawn broke the dark night sky was an everyday occurrence, and she often spent weekends holed up in her room.

She’d been a member of the theater club at school and had put her all into it with her fellow club members, and she’d liked fashion, too. But dating sims were far and away her favorite hobby.

Holy Maiden of Vleugel Academy 3 was one of the games Hiyono had played back then.

“So you’re telling me you were really chosen to be the Holy Maiden?” Gilbert went on. “I mean, yeah, the current one’s been there a long time, and I heard her powers are starting to wane. But for you to get chosen as the representative of the most squeaky-clean and pure of maidens, I almost wonder if the world’s gone mad…”

“Wait, Gil, do you hate me?”

“Not at all, I love you. I just think that someone as rough and careless as you wouldn’t really be able to fulfill the position’s duties.”

“You’re so mean to me!” she squawked indignantly.

As Gilbert broke into a grin, Cecilia buried her face in her hands.

As the title implied, Holy Maiden of Vleugel Academy 3 was the third game in the Holy Maiden of Vleugel Academy series.

In this world, there is a Holy Maiden who protects and guides the people. Even the king cannot disregard what she says.

The protagonist, Lean Rhazaloa, raised as a commoner, and the villainess, Cecilia Sylvie, become candidates to receive the title of Holy Maiden and compete with each other at Vleugel Academy. That’s the gist of the narrative.

“I didn’t want to get picked, either…”

“Why do you sound like it’s already too late?”

“The night before last, a rose-shaped mark appeared around my chest…,” she revealed.

Picking up on what she was implying, Gilbert’s face froze as he murmured, “Oh…”

A special feature would manifest on the bodies of potential Holy Maidens to signify their candidacy—the mark of the rose, in Cecilia’s case.

In the game, the story begins when Lean discovers a snowflake-shaped mark on the back of her hand. The following day at her new school, Vleugel Academy, she learns that she has been selected as a Holy Maiden candidate.

Today was probably when Lean would transfer in. It takes place a week after the senior students’ entrance ceremony in the dating sim. That meant her mark must have appeared on her hand the night before.

“So I guess it’s a done deal, then. You’re a potential Holy Maiden,” Gilbert noted.

“Exactly! And I need you to back me up! You’re seriously the only one I can rely on! Help give your big sister a bright and peaceful future!”

“Yeah, fine, I got it! Hey, don’t start hugging me!” he yelped, pushing her away by the head as she attempted to launch herself at him the way she had when they were younger. A flush formed on his cheeks, likely out of embarrassment.

Cecilia, the villain to the protagonist, meets a tragic end. She dies in every single route—the normal route, the romantic endings, and the bad ending. It doesn’t matter. All that changes is the way she expires.

Thus, Cecilia had decided to become a boy. Not only were they fundamentally unable to become Holy Maidens, but as a male student, she could also fade into the scenery as an unremarkable background character. That being said, she didn’t actually plan to live as a man from here on out. It was just about blending in at the elite boarding school that served as the setting of the game…

But there were limits to what she could accomplish alone.


HiroroAkizakura
Hiroro Akizakura

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meccharakkii
meccharakkii

Top comment

Wow light novel chapter costs 477 ink😯wowee

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Cross Dressing Villainess Cecilia Sylvie
Cross Dressing Villainess Cecilia Sylvie

14.7k views269 subscribers

🌞New Release Event: Bonus Ink!

After being reincarnated as the villainess of her favorite dating sim, Cecilia Sylvie realizes she’s slated for an untimely demise no matter how the game’s story unfolds.

Convinced she can cheat death by assuming a new identity, she becomes Cecil Admina, the dashing son of a baron. Unfortunately, Cecilia adapts to the role a little too well-and ends up replacing her brother as one of the knights who protects the heroine! To top it all off, the prince betrothed to Cecilia is now catching feelings for her alter ego…?!

This villainess will do whatever it takes to achieve a carefree life, but if her guise ever slips, it’s Game Over!
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42 episodes

Volume One: Part 1

Volume One: Part 1

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