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

A/N: Leon is just trying his best, guys.

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He was only human. No, more than that, Leon was just a man. Once you got past the fearsome reputation as a Sky Pirate and the disconcerting connotations of having a moniker like ‘Devil’s Smile’… Leon was, at his core, just a straight, hot-blooded young man.

That’s why… he’s not exactly saying no right now. Not when Olivia had every opportunity to keep her clothes on and her head down. After all, he’d already told her she didn’t have to do this. Hell, he’d told her that he would help without her having to do anything!

At this point, Leon was undeniably committed to assisting Angelica Redgrave in taking control of the Isle of Tortuga. A suicide mission if he was anyone else, but with the resources at his disposal, it should be doable. The numbers they were up against would be obscene… but they didn’t have to kill every pirate to take over the island, now did they?

But back to the matter at hand… Olivia didn’t have to do this. She didn’t have to wait for her Mistress to fall asleep and then come looking for him a second time. She didn’t have to strip naked before him, giving Leon an eyeful of her beautiful body. She already got everything she wanted from him… so really, maybe she was actually telling the truth?

And if she truly wanted to do this now, with no strings attached… Leon simply isn’t the type of man to deny her. As she steps towards him, her gorgeous tits jiggling slightly with every motion, her hips swaying with a womanly sway… Leon doesn’t say no. He doesn’t tell her to stop. He’s not going to-

“W-WAIT!”

The intense connection between him and the naked blonde is abruptly broken as the door is pushed open and a certain Lady Redgrave, wearing nothing but her bedclothes, comes barging into the room. Olivia whips around and yelps at the sight of Angelica, before hastily trying to cover herself with her hands.

“L-Lady Angelica! It’s n-not what it looks like!”

Leon resists the urge to snort derisively at that. It’s… exactly what it looks like. Although he can already feel his ardor calming down with Angelica’s arrival. Nothing like a shrieking noblewoman to ruin the mood, right? He girds himself in preparation for Angelica’s upcoming accusations, knowing beyond a shadow of a doubt that she’s about to point the finger at him for ‘making’ Olivia do this or something.

“Olivia, you don’t have to explain yourself to me. I understand. But you don’t need to do this… if anyone is going to be rewarding Captain Leon for his bravery and loyalty… it s-should be m-me, not you.”

Wait, what? Leon stares at Angelica as the noblewoman, rather than throwing a hissy fit… goes red in the face and quickly starts bunching up her nightgown, clearly intending to pull it over her head entirely. Before she can do so, a sputtering naked Olivia races over, grabbing her wrists.

“D-Don’t! Lady Angelica, y-your modesty!”

But Angelica just scowls, shaking her head and fighting back.

“My modesty? What use is my modesty at a time like this, Olivia?”

“But Angie…”

The two of them fall into a quiet murmuring that he can’t quite hear as Leon just sits there staring, his face now blank. What the fuck was going on? It was one thing for Olivia to be a little bit of a slut, he figured. After all, this is the woman based on a game character who would up with a reverse harem of five men in the ‘true ending’. So her being horny… well, he could accept that. Just as he’d been willing to accept her ‘gratitude’ in the form of her body.

But Angelica Redgrave? She was supposed to be a Duke’s daughter. Such a woman should definitely not be offering herself up to a Sky Pirate the day after they’d met, no matter what he’d promised to do for her. Especially when he hadn’t made any sort of sexual favors contingent on him helping her!

Angelica and Olivia have their heads together now, their foreheads literally touching as they hold each other and talk quietly. Leon isn’t sure what to do… on the one hand, the view is nice considering Olivia is still naked. On the other hand, he should probably put a stop to this… right?

But… he kind of doesn’t want to? So long as Angelica isn’t yelling at him for ‘defiling’ her maid, he’d rather see where this all winds up going. Even if the right thing to do might be to send them both back to bed… Leon doesn’t want to do the right thing. He IS a pirate after all. They’re generally allergic to ‘doing the right thing’.

Finally, Angelica and Olivia pull apart and look to Leon… and he feels a bit pinned into his chair by their gazes. Why does it suddenly feel like he’s the one in danger here?

“Captain Leon… we’ve come to a decision.”

He blinks as Angelica proceeds to shuck off her nightgown after all. And then she removes her shift as well, exposing her own naked body. Side by side, the two blondes are beyond a shadow of a doubt the most gorgeous pair of women Leon has seen since arriving in this world.

And with a few more years to age… well, they’ve aged like fine wine, easily eclipsing the beauty of their game counterparts as well. In this case, the artwork from the otome game has NOTHING on the real deal.

The blondes step forward as one when Leon doesn’t say anything. They walk right up to him as he watches them both quietly, curious to see what they’ll do. Then… Angelica drops to her knees in front of him and Olivia drops down as well right behind her. The blonde commoner whispers in her Mistress’ ear and Angelica blushes and nods before leaning forward to begin hesitantly and amateurishly extracting his cock from its confines.

Well, he’s certainly not going to stop this now. As his cock, already rock hard, comes popping free and Angelica lets out a cute little gasp at the size, Leon decides he’s in too deep. Fuck it… he might as well enjoy himself. More than that though, he’s intrigued by Angelica’s words. What was the ‘decision’ they’d come to?

Apparently, it involves Olivia helping Angelica wrap her tits around his cock, even as Olivia presses her own tits into her Mistress’ back. The blonde noblewoman is blushing profusely as she slides her breasts along his shaft, clearly not having a clue what she’s doing.

But Olivia knows. Apparently, she’s got some experience with this kind of thing, because she whispers instructions into Angelica’s ear while physically assisting her lady in pleasuring him with those beautiful, bountiful breasts.

Leon lets out a shuddering breath as Angelica’s tits glide up and down his cock. Angelica, meanwhile, bites her lower lip for a moment, staring down at his dick and then up at him.

“This… is all you will get of me for now, Captain Leon. I will… p-pleasure you with my chest and prepare you for Olivia. Then, she will allow you to have your way with h-her. Only… only after we take the Isle of Tortuga may you do the s-same to me.”

Leon just stares, the pleasure and all the blood rushing down below making it hard to think. Eventually though, he fully processes what Angelica is saying. It takes every fiber of his being not to scoff at her. Was that how she was justifying all of this lewd behavior? By making it all part of his ‘reward’? Tch… he’d already agreed to help her take Tortuga and Port Paix in exchange for the letter of marquee and a fair share of the plunder held there.

He didn’t need these two to throw themselves at him in order to convince him to help! They should both be able to admit that they’re doing this simply because they want to!

… But alas, Leon is a bit of a coward. While he should confront them on that and force them to tell the truth about why they’re both doing this… that runs the risk of having them come to their senses and decide this shouldn’t happen. And with Angelica Redgrave’s breasts wrapped around his cock, the last thing Leon will abide by is stopping this now.

With that said, he just decides to stay quiet instead. It’s worked so far, right? And after a moment of silence, of him just staring at her, Angelica flushes and looks away in shame. No doubt, she knows just as well as he that she’s using flimsy excuses at this point.

Still, she’s right that a noblewoman’s virtue shouldn’t be given up quite so easily. Even if Olivia was probably the one who had to convince her of even this much. Grunting as his cock throbs and his balls churn, Leon can feel himself getting close now, his member pulsing in between Angelica’s pillowy, soft, warm mammaries.

Olivia suddenly pulls her mistress back, causing Angelica to squawk in surprise.

“Wha- Olivia?!”

“My turn, Angie… he’s getting close~”

As Angelica’s breasts fall away, Olivia’s head comes forward… and she traps his cock in between her lips in one smooth motion. Staring up at him with those bright blue eyes of hers, the beautiful blonde maid sucks hard, her hands sliding around the rest of his member and stroking up and down.

Tch… this woman was just too much! With a loud groan, Leon’s hips lift up into the air half an inch and he shudders his way through the resulting release. His seed flows into Olivia’s mouth… but she’s ready for it and with just his tip between her lips, there’s plenty of room for her to collect his seed and swallow it down. She gulps and gulps until his balls are emptied and there’s nothing left.

Of course… there’s never nothing left. His cock doesn’t even fully go soft as Olivia continues her ministrations, making sure he stays hard. Once Olivia is confident he’s fully erect again, she pulls back and gives him a wide, wicked smile as she climbs from the floor… into his lap.

Leon’s hands instinctively go to Olivia’s hips as she straddles him in the chair, her cunt lips suddenly grinding against the underside of his cock. A little moan leaves her mouth while she loops her arms around his neck and leans forward, her bountiful bosom pressing into his chest in turn.

“Please, Captain Leon… take me… I’m yours to claim~”

Whether she’s acting it up or speaking from the heart… Leon honestly doesn’t care anymore. Gripping down more firmly on her hips, he lifts her up until the head of his cock is caught between her pussy lips. Then, he brings her down, sliding her wet sex onto his dick with a grunt.

The biggest surprise for Leon is when he takes her virginity a moment later. On the one hand, he should have expected it… on the other hand, her knowledge over the past little while had convinced him she’d been around the block.

Now Leon realizes the truth. Olivia isn’t some experienced wanton woman. No, she’s an inexperienced wanton woman. All of her ‘experience’ comes second hand, likely from seeing things she shouldn’t have. As she’d mentioned before, her mother had made… sacrifices.

A little cry leaves Olivia’s lips as she loses her ‘virtue’, but she must have been preparing herself ahead of time, possibly with her fingers while Angelica was giving him a boobjob, because she’s too wet for it to hurt too much for her.

Still, that doesn’t stop her from leaning forward and resting her head on Leon’s shoulder, mewling directly into his ear in an undeniably cute way as her inner walls flex and clench around his cock.

Meanwhile, Angelica is still kneeling on the floor and clearly doesn’t know what to do with herself now. Her hands fidget and twitch as if they want to move towards her body, but despite what she’s just finished doing, her own sense of propriety won’t let her masturbate to him and Olivia fucking.

Leon makes eye contact with Angelica over Olivia’s shoulder as she rests her head in the crook of his neck. The blonde noblewoman freezes up, staring back at him while he shifts his grip on Olivia’s hips down to her ass and begins to lift her up and down, fucking her on his cock right then and there in front of her Mistress.

… He’s not in danger here. These two might be lewd, wanton women, but they’re still girls at heart. And he’s the big bad Sky Pirate. Hah, he might have felt like he was the prey for a moment, but no… never!

PLAP! PLAP! PLAP!

Still, they’re not the prey either. He’s no predator or anything like that. But they did offer themselves up to him… and Leon certainly isn’t going to turn anything down. Just as he’s also not willing to focus solely on his own pleasure at the expense of Olivia’s.

Leon holds himself back from cumming, something made easier by the fact he’s already had one release. He restrains himself as he fucks Olivia into her first and then second orgasm. Every time she moans into his ear, every time she shudders on his cock… he catalogues those climaxes, searing them into his brain.

Until finally, her third orgasm makes it impossible for him to hold back any longer. Her inner walls clench down and milk him for all he’s worth. Leon wishes he could say he’d actually given any thought to where he was going to cum… but truth be told, he got too caught up in everything else to consider it.

However, he knows he definitely shouldn’t be cumming inside of Olivia. Commoner that she might be, its not his intention to knock her up on their very first time together!

He lifts Olivia off of his cock as she’s mid-orgasm, right as his balls tighten up… and then proceeds to unload his seed right onto Angelica Redgrave’s face and tits. It’s not intentional. She’s just still kneeling right there in front of the chair, watching them fuck like some pervert!

So yes, he cums all over Angelica. Even as Olivia spasms in his grasp, clinging to him with all her might, Leon’s ejaculate lands all over a frozen Angelica’s face and chest, coating her from her forehead down to her rock hard nipples.

When all is said and done, Leon expects the noblewoman to rage. This, at the very least, deserves a righteous fit, right? He’s even ready to apologize.

… But maybe he should have expected Angelica to reach up, scoop some of his cum from her body, and bring it to her lips as if in a daze.

Tch… wanton women. Leon is surrounded by wanton women!

-x-X-x-

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