Chaldea Subjugation Organization (Fate/Grand Order)

She had watched from the shadows for a while now. Keeping an eye on things as they progressed. She was not one of her Master’s earliest Servants, but she’d been around long enough to see him bring female after female under his thumb. The young Master of Chaldea was an insatiable kind of man, she could see that much.
 
But was he truly worthy? She’d wondered for the longest time. In this world of mortals where gods and goddesses, warriors and heroes of different ages could be summoned, she’d wondered how a simple mortal Master like him could ever measure up to the others. There were male Servants she’d slaked her lusts on instead, though he did not seem to notice. All he cared about were the women, at least when it came to anything that took place outside of the battlefield.
 
Ah, but she kept herself out of his gaze, away from his none-too-tender attentions. It was best to watch and keep her distance, lest she give in to her desires and do what she did best. After all, the Master of Chaldea was still needed for other things, things beyond the bedroom. It would be inadvisable to break him too early, to take him and release her dark desires upon him.
 
But then he’d gone and done it. He’d gone and tamed the legendarily unfaithful, and utterly insatiable Queen Medb. While the ‘Queen’ did not hold a candle to herself, she still could not help but be surprised. It was almost as if he was issuing her a challenge without even knowing it. He’d thrown his glove at her feet, though perhaps he hadn’t meant to. Still, his intentions were not important. All that mattered were his actions… and her own.
 
How could she stand idle any longer? How could she hold back when he’d done so much to draw her attention? Woman after woman, dominating each and every one of them in his own way. He’d been kind and gentle one moment, and rough and vicious the next. He’d hurt, and he’d comforted, from one instance to the next. His methods had been varied and that alone had been interesting enough, but most interesting of all was the fact that he’d succeeded in every arena he placed himself in.
 
The Master of Chaldea had yet to know defeat, had yet to know true loss. He was victorious and triumphant, to the extent that all seemed to look at him as their leader, showing him respect even if perhaps they didn’t always intend to. He had swayed the denizens of Chaldea, both mortal and Servant, to his cause. He ruled this place completely unchecked.
 
Perhaps it was time for someone to check him. If an unfaithful, controlling Queen was not enough to break him, then perhaps a demonic bodhisattva was in order instead. In life, she was known as Kiara Sessyoin. In death, her name had followed her, as had her history. Ah, but even now, all of them looked her over, even now they ignored her for the flashier Servants. She was not to be trifled with.
 
The young Master would learn this. Quite soon, she finally decided. Kiara could no longer sit by and watch. No, her desires would not let her remain idle any longer. It was time to make her move.
 
-x-X-x-
 
He’s not surprised to wake up naked, nor to a woman straddling him. It’s practically par for the course, at this point. Shigure hasn’t worn sleep-clothes in months, due to fucking one Servant or another every night. Though, he hadn’t gone to bed with anyone this night. Even then, it wouldn’t be surprising for one of his lovers, slaves, or toys to sneak in for a taste of his cock.
 
However, what was surprising was the bindings holding him down to his bed. They were strong, stronger than he would have expected, and even as he tested them, he found no give, despite the enhanced power flowing through his body, despite the way his muscles flex as he pulls and pushes with all his strength to no avail. Finally, Shigure looks to see just who’s playing games with him. In the dim light of his bedroom, he finds a Servant he’s never been with before straddling him.

There’s a lewd smile on Kiara Sessyoin’s face as she stares down at him. Her hands slide up his body, over his chest, and then rake back down as she leans in close, breathing in his scent, her nostrils flaring.
 
“Hello, Master.”
 
She’s already damn near breathless, and Shigure can feel her wet lower lips grinding across his navel.
 
“Kiara… what is this?”
 
Her perverse smile remains as she lets out a slightly unhinged giggle.
 
“Ah. Is Master surprised? He shouldn’t be. How could I not come, after seeing you break so many powerful women? You’ve awoken my darkest, deepest desires Master. I can’t help but want to break you.”
 
She smiles coyly then, even as she presses a finger against his sternum.
 
“And break you I shall~”
 
Shigure scoffs openly at that, though inwardly he’s thinking on what he’ll do next, planning how he’ll get out of this situation. Best to keep up a dialogue as he contemplates his escape… and how he’ll turn the tables on this latest unruly Servant.
 
“You’ll never break me. Not like this. Certainly not with sex. Or have you learned nothing from watching me with all those other women, as you claim you have?”
 
Kiara just giggles again in response.

 
“I see through your bravado, Master. But you aren’t ready for this. Nothing and no one could prepare you for me.”
 
She moves her hips back against his admittedly hard member, and Shigure hisses as she hot dogs his length for a second between her firm butt cheeks. Then, she slides herself up a bit, until finally his cockhead is pressed against the entrance to her cunt. Reaching down between them, she takes hold of him and grins wickedly, her eyes more than a little insane as she stares down into his face.
 
“No man can withstand the mind-breaking pleasure of my Heaven’s Hole, Master. Not even you.”
 
And then she impales herself on his cock. Shigure’s eyes widen as the pleasure from her cunt immediately milks a release from him. He gasps as his seed spills into her womb without hesitation. The exertion leaves him breathless, but Kiara doesn’t stop there. Giggling to herself, the beautiful Servant begins to ride him, even as Shigure swiftly finds himself in a state of delirium, something he’s never experienced before, not with any woman.
 
But then, she’s not any woman. At the very least, Kiara is right about that much. As she milks him of load after load of his cum, her pussy walls squeezing and tightening in all the right ways, her cunt feeling like none before it, Shigure’s mind is driven deeper and deeper into a haze of pleasure, his thoughts and his plans to escape and fight back slowly overshadowed by the bliss and ecstasy enveloping his mind.
 
He fights it, he truly does… but it almost seems like he’s drowning as she bounces up and down on his cock, forcing release after release from his prick. Shigure barely has the mental capacity to wonder briefly if this is what all of the women he’s ever fucked have felt like as he plowed them senseless, fucked them silly, left them addicted to his cock.
 
Kiara’s cunt is certainly addicting. There’s something absolutely amazing about what she’d labeled as her ‘Heaven’s Hole’, and Shigure can’t get enough of it. Even if he wasn’t bound, he imagines he’d be fucking her still right now, though in positions much different than this, if only to assert his dominance over her. Alas, he is bound. Unable to escape, slowly overwhelmed with pleasure, Shigure tries desperately to claw his way up out of the ocean of ecstasy he finds himself drowning in.
 
He’s failing… up until Kiara makes a mistake. The demonic bodhisattva leans forward and cups Shigure’s face in her hands as she continues to ride him for all she’s worth. Her perverse, victorious smile fills Shigure’s hazy vision, and he finds himself focusing on her face enough to hear the words that she says next.
 
“Ah, there it is, Master. Sooo cute. How amusing, watching your ahegaoing face after you made the same expression appear on so many other women. In the end, this is true satisfaction. Breaking the man who has tamed so many powerful women, seeing him reduced to nothing more than my slave, my pet, my desperate, needy, dog.”
 
She lets out a breathless, shuddering sigh at that, her cunt flexing around his cumming cock in what might have been a small orgasm. But Shigure isn’t focused on that. No, instead, he’s focused on her words. Because though they’re fairly close to the same words he’s used on so many of his Servants before her, in Shigure, they do not provoke the same reaction.
 
He is not a Servant. He is not a slave, a pet, or a dog. He is the Master of Chaldea, and Kiara’s taunting, teasing words are enough to ignite a flame of rage within Shigure that burns away the haze trying to take over his shoulders. Though he cannot lift his arm, he can still splay out his fingers. As he does so, he activates not one, but all of his Command Seals. Rather than use them to control Kiara, rather than use them to break her as he broke so many others before her, Shigure utilizes the energy within the magical seals in a way he’s never done before.
 
He takes the power into himself, rather than using it as an outside force. Flooding his body with the magical energy of all three of his Command Seals might be dangerous under most circumstances, but Shigure has been altering himself for just such an occasion as this. He’d always imagined it would happen on the battlefield though if he’s being honest.
 
But then, wasn’t the bed just another sort of battlefield, especially when one had Servants like these? With a roar, Shigure uses his new-found strength to break the powerful bindings holding him down. Kiara’s eyes go wide at this, but she can’t move nearly fast enough to stop him from reversing their positions, putting her on her back and him over her as he holds her by the shoulders, his cock still inside of her.
 
For a moment, the female Servant is clearly surprised, even as Shigure takes control and begins to fuck her with fast, powerful, and most importantly DEEP thrusts. Her breasts bounce, and moans leave her lips as he slams into her with a wild abandon. But then the smile comes back, and she laughs into the air while he fucks her, her gaze finding his own eventually, a wicked smirk on her face.
 
“I’m impressed, Master. You were able to escape the mind-melting pleasure of my Heaven’s Hole. Or at least, it seems so. But then, if you could truly escape, you wouldn’t still be, mm, fucking me as you are now. You are trapped, even still. Ah, Master~ Fuck me if that is your wish. Fuck your Servant, oooh, as long as you like.”
 
She giggles again, as her eyes twinkle. There’s a flush spreading across her face, as now that Shigure’s controlling the pace, she’s experiencing more and more pleasure as he fucks her at different angles of his choosing, not quite giving her any time to recover. But she’s still remarkably composed beneath him, even as he rails into her body.
 
“Mm, go on then, Master. Show me how you broke those other women, if you can. Exhaust yourself on my body… and then we will discuss in great detail your new life as my slave.”
 
It’s clear to Shigure that Kiara finds the idea of him breaking her via sex as laughable as he did. But she clearly doesn’t understand what he did to break free. She knows not of the power flowing through his veins thanks to the Command Seals. The way he used the seals was certainly possible, certainly feasible… but quite unorthodox, at the end of the day. But he’d done it all the same. And now… now he would use that power to do what he did best.
 
Fucking into her, Shigure grunts as he cums again. His seed explodes within Kiara’s insides, but now that he’s clear-headed and more cognizant, he recognizes that it doesn’t ever truly reach the female Servant’s real womb. No, instead it ends up sucked somewhere else. He’s not sure where, but he knows one thing to his very core. There has to be a limit. And if that’s what he has to do, then he’ll do it. He’ll fill her with his seed until he finally reaches the real deal.
 
This is his task, this is his goal. Recognizing it, internalizing it, Shigure slides his hands from Kiara’s shoulders to her breasts, grabbing onto her tits and squeezing them with all his might as the perverse Servant gasps and arches her back beneath him, clearly enjoying his touch. But his own face has turned to stone as he fucks her and fucks her and fucks her some more. He gives no reaction save for grunts when he cums inside of her. He can’t afford to show anymore weakness, not anymore.
 
This… this is a battle like none he’s faced before it. But if there’s one thing Shigure is good at, it’s adapting. So adapt he shall. And win he shall, as well. Because the Master of Chaldea does. Not. LOSE!
 
-x-X-x-
 
At twenty-four hours, Kiara is impressed, but not at all worried. She enjoys the way Shigure continues to fuck her and continues to fill her Womb Realm with his seed, but there’s no true danger of him exhausting the space within anytime soon. And she expects that he won’t be able to last for much longer. Even with his enhancements, he’s only human. How much more can he truly keep this up for?
 
Forty-eight hours in, Kiara begins to wonder about that. He’s still fucking her, still cumming from the pleasurable flexing of her Heaven’s Hole. His seed continues to pour into her Womb Realm, but it’s only just half full now. Surely, he’s almost out of juice? Even if his face hasn’t moved a muscle in the past two days, even if he’s seemed completely and utterly emotionless all this time. He’s… he’s m-mortal. At some point, he WILL break. She sees no other way for this to end!
 
When the seventy-second hour passes, Kiara finds herself biting her lower lip hard enough to draw blood. He’s still going, even now. No longer groping her tits, though he’s left them red with both his fingerprints and his teeth marks as he mauled them to his heart’s content. Kiara wonders if she should put an end to this… but the truth is, at this point, she can’t actually stop it. She’s expended too much power by this point, and she can feel the strength flowing through his veins now that she actually bothers to look for it.
 
The fourth straight day of their fucking arrives, and Kiara is openly and loudly moaning now. Her arms encircle his neck and her legs wrap around his waist as the Master of Chaldea STILL continues to fuck her. He’s not stopped, not even once all this time. And her Womb Realm is… near full. How is that even possible? Before today, she wouldn’t have said it was possible.
 
But here they are, at nearly one hundred and eight hours later, as Kiara finally allows her to panic. Shigure has lasted far longer than she’d ever thought possible, and the four and a half days of constant fucking, along with gallons upon gallons of cum as her Heaven’s Hole did what it did best and milked the Master of Chaldea constantly, had taken a toll on her. In the end, even Shigure seems to see what’s happening.
 
His lips finally move from their set line as he smiles above her. Kiara’s eyes widen at the triumph she sees in his gaze, and her mouth opens in a small o that gets progressively larger as he thrusts forward and let’s loose one final cum shot. The load that explodes out of his cock is truly massive… and with her Womb Realm already in it’s current state, his last hurrah overwhelms and destabilizes it.
 
His seed reaches her actual womb a moment later, hitting the back of her most sacred of places before the demonic bodhisattva can even truly react. A cry leaves her lips, an ugly one, and Kiara finally climaxes as well. It’s the first time any man has TRULY cum inside of her in… far, far too long. It actually might be the first time, EVER.
 
Regardless, with as much control over her body as she has, Kiara can FEEL it as her Master’s seed inseminates her right then and there. She can sense his sperm penetrating her eggs, impregnating her on the spot within minutes of him finally breaking through and cumming deep inside of her real womb. At the same time, the orgasm she experiences is the true definition of mind-breaking. Her eyes roll up in her head and her tongue lolls out of her open mouth as she shakes and spasms beneath Shigure, seizing up from the explosive amount of pleasure that overwhelms her every thought.
 
By the time she’s come down from her orgasm, the Master of Chaldea has pulled out of her and kneels over her, his cock still hard and still leaking his seed, this time onto her exposed, naked belly as he looks down upon her defeated, writhing form like the triumphant conqueror that he is. Except it’s more than that. Kiara knows it’s more than that.

As she gazes up at her Master, the beautiful female Servant realizes the simple truth. It’s as clear as day to someone like her, after all. Not only had Shigure managed to resist the pleasure of her Heaven’s Hole, he’d then fucked her for precisely one hundred and eight hours straight, overwhelmed her Womb Realm, brought her to climax, and even impregnated her.
 
There was only one possible explanation to all of this. Shigure had transcended to some sort of sexual Buddhahood, and now that the god-like man loomed over her in silence, she could practically see the aura bursting out of him. She had to say something. She had to… she had to e-explain.
 
“Master… you… you are amazing. I-I had no idea. How could I? Until now, Master has only sated himself on lesser women. Now though, now I know the truth.”
 
Lifting a brow at that, the Master of Chaldea grunts.
 
“The truth?”
 
Kiara’s smile is as perverse as ever before, but this time it has something else to it, something… worshipful in its intensity.
 
“Yes. Yes, Master is worthy. Worthy of this one’s service. I pledge myself to you, Master! I was wrong to ever doubt you! I want nothing more then to serve you for the rest of my days, the one who has surpassed even me in the sexual arts!”
 
Shigure considers this for a moment with his head cocked to the side. Then, he sidles up her body and places his messy cock between her tits even as he responds. And after four and a half days of fucking, of cumming inside of her… Shigure’s cock is VERY messy. It lands between her bountiful breasts with a wet smack, his seed ending up all over her chest and her face as his cockhead rests on her chin.
 
“Very well. Show me your newfound loyalty by starting with cleaning up the mess you made, slut.”

The way he degrades and demeans her is completely insulting, but in the end that only sends a shiver of delight up Kiara’s mind as she reaches for her breasts and slides them up and down his cock, all while leaning in to suck his member into her mouth. He could treat her however he liked, so long as she had his affection. She needed him, needed him to want her.
 
Nothing would make the freshly broken Servant happier.

-x-X-x-

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