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

A/N: The positive response to this story’s first chapter was as overwhelming as I wanted it to be, so safe to say that we’re locking in this fic as the replacement for The Sun Reborn in my Monday Morning slot! Enjoy more of Sky Pirate Leon~

-x-X-x-

In his previous life back on Earth, Leon had known this world he’d reincarnated into through the lens of an otome game. A dating game for women, to be exact. The details behind why he’d been forced to ‘one hundred percent’ the game aren’t important but let it be known that he HAD successfully completed the entire otome game from start to finish. And then he’d died and woken up here.

Knowing everything he knew about the otome game and its plot, Leon had been even more happy to fuck off and live the life of an unburdened, free, and independent Sky Pirate. He figured he just needed to stay away from all of that bullshit and given it was five years since the plot of the game should have begun, he felt he’d successfully managed to do so.

The problem, of course, lies in front of him now, staring at him with big doleful eyes.

Here was what Leon knew. The commoner Olivia was the main character of the otome game he played back home. On the surface, she seemed to be nobody special… but in reality, she was of course Extra Special with a capital E and S. She would slowly but surely draw the attention of five different noblemen at the Holfort Academy, these being her ‘Capture Targets’ and the greatest among them being a Prince of the Kingdom of Holfort, Julius Rapha Holfort.

Of course, opposing her was all of the ‘petty’ and ‘evil’ noblewomen who would pick on her and treat her poorly at the start of the game, all to justify the protagonist slowly but surely gathering five noblemen into a harem for herself. Technically you could just still to only stealing one of the five Capture Targets and focus entirely on a monogamous relationship, but this particular dating sim was extremely punishing if you did so, always resulting in a Bad End unless you went for the entire harem.

Which brought Leon to what else he knew about the second woman in front of him. Lady Angelica Rapha Redgrave was the daughter of a Duke and also Prince Julius’ fiancée at the start of the game. Of course, by the time Olivia was done with him, he was more than ready to toss Angelica to the curb, effectively calling off the betrothal.

Suffice to say, this did not go over well with Angelica. She did everything in her power to save her engagement with the Prince, since you know, it would reflect terribly on her if she didn’t. So yes, she would go out of her way to target Olivia and do ‘terrible villainess’ things to get the commoner girl to back off.

None of which would work, ultimately resulting in the engagement being ended anyways. She would be humiliated, discarded, and forced to marry an older man below her social standing, moved out to the countryside where she could live out the remainder of her life bitter and miserable, forgotten by everyone.

And so, on the one hand… the fact that Angelica was being sent into exile did sort of line up with what Leon remembered from the game. However, the fact that it was happening years after it should have AND Olivia was by her side was… frankly quite baffling.

Admittedly, he hadn’t heard about the war that the original game had been centered around, but to be fair Leon also hadn’t been paying much attention to politics all this time. Better to just focus on himself he’d figured. Now though… he’s left wondering what the hell is going on. If the heroine and villainess of the game are both here… where in the world are all of Olivia’s Capture Targets?!

As Leon is thinking all of this, he continues to stare silently at Angelica and Olivia. And maybe… maybe his poker face is just a little too good, because Angelica falls quiet and Olivia shrinks back, neither woman seeming to like having his intense gaze on them too much.

Meanwhile, the balding Captain of this merchant vessel that Leon has boarded seems to take his silence entirely the wrong way, smiling wickedly and perking up as Leon just stares at the two women.

“Like what you see, Devil’s Smile? They’re a gorgeous pair of women, aren’t they? Even the commoner has a rack on her worthy of your time. So… what do you say? We hand them over and you ‘deal’ with them how you see fit? So long as they never see the light of day again, I’m sure everyone will be happy!”

Pulled from his thoughts by the other man’s disgusting ‘deal’, Leon slowly turns his gaze from Angelica and Olivia over to the Merchant Captain. The man shrinks back a little at first, but quickly rallies… after all, he thinks he has Leon’s measure. What self-respecting Sky Pirate wouldn’t take an opportunity to ravish a pair of unwilling beauties, right?

“O-Oh, and of course we’ll still be sure to cut you in on a part of the payment too. Just have to arrange a place to meet with you after we get back and are paid!”

Rather than answer the man, Leon sweeps his gaze across the rest of the ship’s crew. Most of them look hopeful, clearly anticipating him taking the deal and letting him go. Maybe one or two are grimacing in distaste, but they hold their tongues. Curious, Leon tilts his head to the side.

“And are all of you men happy with this arrangement that your Captain suggests? You’re content to give these two young women over to a dastardly devil like me just to save your own hides?”

That draws at least a handful of uncomfortable looks for a moment… until the Captain speaks up again.

“Bah! Of course they are, Captain Bartfort! You should know better than anyone how bad things are back in Holfort! Noble bitches like this one run rampant, leaving men like us with no options, no path for advancement! In a fair and just world, I would be a nobleman myself at this point! Instead I’m stuck as a Merchant Captain, forced to toil away on this boat for the rest of my days for pittances of pay! It’s the same for all of us, isn’t it men?!”

There are murmurs of agreement and nods at that… from basically everyone on the ship. Even Leon knows that there’s some truth to the older man’s words. After all, he knows full well what the Kingdom of Holfort is like and how the excesses of its female nobility run rampant.

The problem is… he also knows that Angelica in particular isn’t really involved in any of that. She only ever became a villainess because she was forced into the role by Olivia’s actions. And Olivia… well, if Olivia is here and not living it up with a harem of noblemen back in Holfort, she’s likely to be even more innocent of any wrongdoing.

Slowly, Leon nods as he comes to a decision. Lifting his free hand… he snaps his fingers. Instantly, the automatons that are holding Angelica and Olivia lurch forward, stomping past him over to the ramp that has been laid between the two airships at this point. As they’re dragged towards their ‘doom’, Angelica finally seems to find her voice again.

“N-No! Please! You can’t do this! At least let Olivia g-go!”

“L-Lady Angelica!”

Leon pretends to ignore the interaction between the two young women even as he files it away in the back of his mind. Regardless, neither of them is capable of escaping the strength of his automatons as they’re dragged into Partner’s depths. He’ll deal with them later.

For now, he also sheathes his sword at his side, a pirate’s cutlass of course. The sight of this has the balding man in front of him perking up with a giddy smile while the rest of the vessel’s crew all slump in relief.

“Heh, knew you’d see reason Captain. We might not have had conventional cargo for you to take… but this ‘cargo’ is all the better, isn’t it?”

Leon, meanwhile, smiles as well as he steps forward and plants a hand on the other Captain’s shoulder.

“There’s just one problem with this deal from where I’m standing.”

Blinking in confusion, the older man furrows his brow.

“What’s that?”

“People ain’t cargo, mate.”

Quick as a whip, he draws his pistol from its holster, takes a step back, and blasts a hole in the Captain’s chest. In the same moment, every other man on the ship dies as the automatons holding them down drive swords into their bodies or simply snap their necks.

As the Merchant Captain stumbles back, holding his chest and looking bewildered and baffled by this turn of events, Leon just stares at him pitilessly until he drops to the deck, joining his crew as a corpse.

-x-X-x-

Angelica’s life was over. She’d already known that for a while of course. From the moment that bitch Marie successfully managed to get Julius on her side, it was done. After all, what was a Duke’s daughter supposed to do in the face of a Prince?

She’d tried though. She’d tried so, so damn hard. None of it had mattered in the end. Her so-called friends had all abandoned her one by one once they realized which way the wind was blowing. And to think, it was they who had advised her on how to treat her engagement with Julius. It was them who told her she needed to avoid getting too close to him, that she couldn’t be seen doing anything unladylike when they weren’t even married yet.

Angelica had done her best to juggle her desire for a marriage of love with all of their advice. She’d tried to give Julius his space while also making it clear how much she cared for him. But none of it had mattered in the end. None of it had meant a single thing once Marie Fou Lafan, a simple Viscount’s daughter, had come along and caught his interest.

And not just Julius’ interest either… no, she hadn’t been satisfied with only stealing the heart of a Prince. She’d taken him and all four of his friends, drawing them into her web and ruining so many engagements it still made Angelica’s head spin.

But what had happened when the dust had settled? Was Marie the one who had been punished for so clearly biting off more than she could chew?! No… no, it was Angelica who had been treated as the villain in the end. Abandoned, shunned, and now ultimately exiled away forevermore.

Olivia was the only one who stuck to her side through thick and thin. Angelica had never had a very high opinion of commoners before meeting the other blonde… and yet, now she knew the truth. It was her fellow noblewomen who were the real rats. Commoners like Olivia were the only people who could be relied upon to show true loyalty.

Of course, as they stand there huddling together on the deck of a monstrous pirate airship surrounded on all sides by strange men in hoods and masks, Angelica regrets ever letting Olivia accompany her into exile. She should have sent the commoner away long ago… even if she had to break their friendship to do it. She should have told Olivia that she hated her, or that she blamed her for everything bad that had happened. Anything to drive the other young woman away so she didn’t have to share Angelica’s fate.

Instead, she’d selfishly clung to the only person who seemed to believe in her… and dragged Olivia straight into hell alongside her in the process.

A gun shot rings out, making them both flinch as they all but cling to each other. A whimper leaves Olivia’s lips and Angelica looks to the other woman, biting her own lower lip.

“… I’m sorry, Olivia. I never should have brought you with me. I s-should have let you go.”

Turning wide blue eyes in her direction, Olivia is quick to shake her head.

“N-No… don’t say that, Lady Angelica! If I weren’t here… then you would be all alone! That would be even worse!”

Worse for her maybe, but not worse for Olivia. Still, it doesn’t surprise Angelica that even in her most terrified state, Olivia is thinking about Angelica before herself…

Before she can respond however, the thumping of boots draws both of their attention to the ramp they’ve just been dragged over… and a moment later the Pirate Captain who now has custody of the two of them comes into view.

Leon Fou Bartfort. Angelica knows of him… vaguely. She mostly knows him in terms of the scandal that his turn towards piracy had caused back in the day when it had first come out. His family had disowned him of course, decrying his actions to all who would listen. It was said that he continued to go by the name Bartfort afterwards solely to put further egg on their face.

He wasn’t the kind of man that she would want to have ahold of her OR Olivia. But… Angelica still had her honor. As he stalks towards them, she quickly puts herself in front of Olivia, trying her best to shield the other woman from the Pirate Captain. And then, even though she’s not feeling a lick of confidence, she stands as straight as she can and lifts her head high, feigning as much arrogance as she can possibly manage.

“Captain Bartfort. You will not-!”

BA-BOOM!

Angelica’s eyes widen as she’s cut off mid-sentence by a sudden explosion that rocks the ship a bit and causes both her and Olivia to shriek and hunch back in fear, covering their ears. Its only when there’s no follow up that they slowly uncurl from one another, staring with wide eyes.

Leon Bartfort, meanwhile, looks entirely unperturbed, smiling wickedly.

“Apologies. I had to take out the trash. You were saying?”

Angelica’s mouth opens and closes like a goldfish as she realizes… he just destroyed the airship they’d been traveling on, didn’t he? That was the only thing around that could make such a massive explosion. And the gunshot earlier… had been the clue that he wasn’t just letting anyone go.

A whimper leaves her lips as she realizes that the Sky Pirate has just killed every man on that ship. And sure, they hadn’t exactly moved heavens to try and save Angelica and Olivia from him… but it makes it clear what sort of monster they’re now dealing with. A shiver of fear rushes down Angelica’s spine as he gazes at her like a hawk sizing up his prey…

-x-X-x-

A/N: Remember to Vote, leave a Like, and let me know what you think!