(Every character depicted in the story below is a consenting legal adult over the age of 18)

A/N: Olivia makes her move.

-x-X-x-

Everything proceeds precisely as Olivia expects it to. The food and drink provided are actually quite tasty, and there’s even a room with a full bath and toilet attached to their room that they can use to freshen up and relieve themselves.

After Angelica finishes with her bath, she tries to keep her eyes open but it becomes all but impossible as the events of the long, long day catch up to her. Olivia makes sure to hold her until the noblewoman falls asleep, at which point she tucks Angelica into bed and asks one of their guards to go and speak with the Captain.

The speed with which her request is granted and she’s escorted to see Captain Bartfort assures Olivia in a way… but also makes her more nervous than ever before. Even still, she suppresses that nervousness, forcing it down as determination and resolve takes its place.

Finally she arrives before the Captain himself, who is sitting back in a high back chair with a book in his hands. He looks up as she’s presented to him, tucking a small marker into the book and then closing it and setting it aside.

“Olivia, wasn’t it? You wished to speak to me?”

Olivia swallows hard, even as she clutches at her skirts and bows at the waist.

“Yes sir. Thank you for allowing me this audience.”

The Pirate Captain makes a noise in the back of his throat at that but says nothing else. After a long, awkward moment, Olivia straightens up only to freeze at seeing the intense gaze he’s leveling in her direction. Honestly, it’s only slightly better than when he smiles… when he smiles, she wants to piss herself in fear and run for the hills!

Still… the intensity with which he’s staring at her makes his expectations obvious, or so Olivia figures. She knows what a man like him wants after all. If he wasn’t going to take it from them… it was only because he was the sort who preferred it to be ‘offered freely’ instead.

Plastering a smile on her lips, Olivia reaches up to begin unbuttoning her maid uniform.

“I appreciate your gentlemanly conduct so far, sir. And so does my Mistress. There is no need for you to act the part of the boor either… because I’m m-more than happy to-!”

“Stop. What are you doing?”

Olivia freezes a few buttons in, blinking as the Pirate Captain cuts her off with a raised hand and his words. She looks down at herself and then back to him with a blank expression for a moment before shrugging helplessly.

“Ah… undressing f-for you, sir? I promise you’ll like what you see. There’s no need to bother my Mistress when you and I can come to an arrangement between just the two of us that will see her to safety…”

He stares at her with an unreadable expression for a long, silent moment. Finally, Olivia takes that as her cue to continue, moving on to the next button. Only…

“Cease. Now.”

She freezes again, a tendril of fear running through her. He sounded angry, or at least very terse… but what had she done wrong?

“Keep your damn clothes on. Didn’t I already say I wasn’t that type of man? Didn’t I say I have standards?”

Olivia swallows hard, more confused than anything.

“O-Of course sir… but this would be f-freely given. I assumed that…”

But she trails off, seeing him shaking his head. His jaw is clenched and his eyes are flinty as he glares at her.

“You would only be doing these things to buy my favor. I’m not interested in laying with a woman who thinks they have to sell their body to keep their life. Do you understand me?”

Her mouth opens and closes wordlessly for a moment… before she blushes furiously and hastily does back up the buttons on her front. What had she been thinking? Now that he’d shot her down… she can’t help but be horrifically embarrassed and mortified by her own behavior. And yet, at the same time… is anything really resolved at all between them? Or between him and Angelica?

“If that was the only reason you wanted to see me, I’ll have you escorted back to your rooms now.”

“N-No, wait… please…”

The Pirate Captain… no, rather, Leon narrows his eyes at that.

“Yes?”

This time around, Olivia doesn’t just bow… she goes down to the floor, prostrating herself before Leon and planting her forehead on the ground.

“I am deeply sorry for my assumptions. Please, if you are insulted, take your punishment out on me and not my Mistress. But also… if I could beg for just a moment more of your time to speak about the future, I would appreciate it.”

This time, Leon just sighs.

“Stand up. It’s fine, I’m not going to punish you or Angelica for this… misunderstanding.”

Already talking about Angelica in such f-familiar terms. Olivia swallows as she gets back to her feet. Leon raises a brow at her once she’s standing again.

“What exactly do you want to speak about then?”

Right… okay, she could still do this. She could still be of use to her Mistress.

“L-Lady Angelica has been through quite a lot, sir. She has suffered greatly at the hands of those she thought closest to her and ultimately been sent into exile as a consequence of everyone else’s actions rather than her own. And… they were going to k-kill her and me… until you stepped in.”

Leon hums, looking thoughtful. Taking that as a good sign, Olivia goes for the kill.

“H-Help us, please. Tell me what it will cost, tell me what I can do to convince you… and I will do it. My lady has no friends, no allies, no resources… save for me. I’m all she has left at this point… so it falls to me to find a way to assist her.”

The Pirate Captain seems to mull over her words for a long while. Olivia chooses to view that as a good sign as well… after all, if he didn’t care he would have already dismissed her outright, right?

“… You don’t have much to offer me. I’ve already told you I have no interest in women who sell their bodies for their lives.”

Olivia swallows.

“B-But what of a woman who wishes to offer her body in exchange for assistance? Is that not better? It’s… simply prostitution. Except I can guarantee I’m cleaner than any whore you’ve ever been with, sir.”

Staring at her, Leon snorts derisively.

“You’re quite eager to whore yourself out to me, aren’t you Olivia? All for your Mistress.”

Olivia blushes and fidgets… only to stiffen at his next words.

“… Has Angelica had you do so before?”

Eyes widening, jaw dropping open, Olivia is stunned by the horrible question for a moment… before growing outraged a second later.

“What?! No! Lady Angelica would never ask such a thing of me! She’s a good woman and a good Mistress! She has always looked after me, p-protected me!”

Just as quickly as the outrage comes, it peters out as she realizes she’s yelling at their very dangerous, very violent captor when she’d come here with every intention of buttering him up. Flushing, Olivia ducks her head, getting ready to kowtow and apologize again… but Leon just chuckles in response.

His amusement makes her shoot him a cautious look… he’s not quite smiling as evilly before, but he certainly has a wicked sort of smirk on his face. It sends a shiver down Olivia’s spine, even as she speaks in a much quieter tone.

“… It was my mother. She was… she did her best, but to make enough for both of us to survive, she had to make sacrifices. Those sacrifices were what helped me grow up, and what kept me alive long enough to get into the Academy. I never begrudged her for them… and I cannot bring myself to look down on any woman who must… do such things. As such, I cannot say I’m unwilling to offer my body to you in exchange for your assistance, Captain Leon.”

For a long moment Leon just stares at her in silence again. Olivia fidgets under his gaze, until finally…

“If you wish to help you two with your future… then my price will be for you to tell me about your shared past.”

… What? Olivia blinks, completely caught off guard by the strange request.

“I-I’m sorry?”

Leon just rolls a hand in the air.

“I’m curious how your Mistress secured a servant with as much loyalty as you have. And you mentioned the Academy… I’m equally curious how a commoner like you made it into the Holfort Academy. So tell me your story, Olivia. Tell me what the years have held for you and Angelica… and I just might consider helping you both out.”

He just wanted her to tell their story? On the one hand, that was a far cheaper cost then giving him her body, Olivia supposed. At least on the face of it. Because on the other hand… it’s actually an incredibly daunting prospect, isn’t it?

When she looks back at the last five years of her life, from the moment she joined the Academy to now… it’s not exactly a happy tale or something she necessarily wants to revisit. Sure, it had its happy moments here and there… but they’d grown few and far inbetween as time had gone on after she entered Angelica’s service.

And yet… Leon is sitting there, watching her patiently, clearly expecting her to agree to his very generous offer. Even if it was only a ‘might’… she should just tell the story anyways for the slightest chance that he’ll be moved to assisting her Mistress afterwards.

Swallowing hard, Olivia slowly nods.

“Very well… I’ll tell you.”

Leon smiles at her again, sending another shiver down Olivia’s back. Then, he really catches her off guard by gesturing to the chair across from him.

“Have a seat then and let’s begin.”

Olivia stares at the offered chair for a long moment before moving to sit down, perched on its edge. She can’t help but be grateful… after all, this was going to be a long, sordid tale. One best not told while on her feet if she could help it.

Opening her mouth… Olivia begins to speak. And to her surprise, Leon seems like he’s well and truly hanging off of her every word.

-x-X-x-

Curiosity killed the cat, but satisfaction brought it back. That was the full saying that most people cut off at just the first part. Leon’s curiosity regarding what was going on in this world with Angelica and Olivia had begun to burn from the moment that Olivia had come before him and started trying to offer him her body.

What sort of loyalty could Angelica have engendered in the other blonde to make that Olivia’s go-to method? More than that though, how in the world had Angelica wound up exiled now… five years after the events of the otome game should have begun and run their course?

That, more than anything, was what Leon wanted to know. He wanted to know why Angelica and Olivia were together and why Angelica wasn’t exiled years ago while Olivia went on to be the big bad harem protagonist she was supposed to be in the original dating sim.

Fortunately… Olivia is a wellspring of knowledge. And what Leon learns is very, very interesting.

For one, there was another girl. Marie Fou Lafan, a Viscount’s daughter. The name doesn’t ring a bell and trust Leon when he says that he would recognize every major and minor character from the otome game even after fifteen years in another world. There was simply no doubt in his mind… this Marie Fou Lafan was not from the original game.

Which made it all the more wild to listen to Olivia unknowingly explain how Marie had apparently usurped the entire position of harem protagonist from her. Obviously, Olivia had no way of knowing what she was supposed to become, but from the sound of things, this Marie had stolen her destiny from her.

Not that Olivia had even been involved at first. Much of the early stuff was things she’d had to put together after the fact with the benefit of Angelica’s ranting and plenty of hindsight. Put simply, Olivia had just been an ostracized commoner at the Academy. She’d gotten in on a scholarship and all of the nobility had hated and shunned her for it, if they weren’t outright harassing her and kicking her around.

Instead of one of the five main ‘capture targets’ from the game coming to her rescue, however, it was Angelica Redgrave who had eventually taken pity on her and taken her under her wing. And all while at the same time dealing with the machinations of Marie Fou Lafan, to hear Olivia say it.

It… sort of made sense, Leon supposed. Angelica never came across as a truly terrible person, even in the game. Rather, she’d been desperate more than anything, a desperation born from the player using Olivia as the main character to steal Angelica’s fiancée and four other men besides to create her own reverse harem.

With Marie stealing Olivia’s role in this world, Angelica had no reason to dislike the commoner woman… and so she’d eventually stepped in, stopping her peers from continuing their harassment of Olivia, and put her under her protection.

And that should have been that… but of course, it wasn’t. This though, was where things really got weird. As Leon well knew, the plot of the otome game was definitely less than a year from start to finish. You would play as Olivia, seducing and ‘capturing’ all of your male suitors and fighting off attempts from the villainess Angelica to get you away from her man… the literal Crown Prince of the Kingdom.

It all happened very quickly, in the span of mere months… possibly even weeks? It was a little unclear, as time tended to be in those types of games, but one thing was certain… it definitely didn’t take longer than an Academy Year for the Olivia in the game to ‘win’ and take the hearts of all her capture targets.

… But this wasn’t a game. This wasn’t a dating simulator. This was a living, breathing, and most of all real world. Leon hadn’t thought about what that really meant until hearing Olivia tell her and Angelica’s story. But once she’s said it all, he now understands.

Even someone like Olivia wouldn’t have been able to seduce Crown Prince Julius and his four friends in the space of one year, probably. And this Marie chick, to hear Olivia tell it, was certainly not ‘main character’. She’d done it anyways of course… somehow. It had just taken her longer. Years, in fact.

Over the course of their entire time at the Academy and then for a bit after, Marie Fou Lafan had slowly but steadily wormed her way into the hearts of every one of the game’s original capture targets. The Crown Prince Julius Rapha Holfort, formerly engaged to Lady Angelica, of course… but also Brad, Greg, Jilk, and Chris, the rest of his friends.

This Marie had played the long game and it had apparently paid off for her, because Angelica had been made to look so much the villainess that her betrothal had been broken off and she’d been exiled from polite society. All the while, it was apparently an open secret that Julius and his four friends were all deeply, madly in love with Marie Fou Lafan.

It sounded ridiculous… because it was. Reverse harems didn’t actually happen in the real world in Leon’s humble opinion. Then again, he also knew the personalities of the five capture targets inside and out from how much he’d been forced to play the stupid game.

… So yes, he could easily believe they’d all fallen for this Marie chick like the absolute idiots they were, even if it had taken five years for the results to fully materialize instead of less than one.

In the game, everything had moved rather quickly, probably because the creators had no real concept of time or scale. Or they just didn’t care enough since it was a dating game made for horny women.

Still, as Olivia finally runs out of disparaging things to say about Marie and her story starts to wind down, Leon finds himself at a crossroads. Really, he should just wash his hands of this whole situation. It has nothing to do with him, slowed down ‘main plot’ or not. And yet… the hopeful look in Olivia’s eyes is really tugging at his heart strings…

-x-X-x-

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