Chaldea Subjugation Organization (Fate/Grand Order)

As much as Shigure wished it were so, his days in Chaldea were NOT spent completely fucking around and railing his female Servants until they were pregnant. He did have other things to take care of. Like paperwork. The dreaded, eternal enemy… paperwork. Letting out a sigh as he fills in yet another box, Shigure rubs his forehead, groaning a bit.
 
There’s a pile beside him, but luckily for his sanity, it’s a pile of finished work. This form that he’s currently doing right now is the last of the dreaded paperwork… at least for today. Who knew what tomorrow would bring? Who knew what the next day would bring? Shigure had delegated as much of his paperwork duties to Chaldea’s remaining staff as he could, but all in all, if he wanted to be in charge, if he wanted to be the Master of Chaldea and answer to absolutely nobody, there were some things he had to do himself.
 
Still, as he finally finished the last page before him, Shigure had a vicious sense of satisfaction as he placed it atop the stack that made up his ‘done pile’. Standing, he clips the papers together, slips them into a folder, and slides that folder into a nearby hole in the wall. It’s almost immediately transported away, to be digitized in the main frame.
 
Why he couldn’t do all of his paperwork through a computer… Shigure didn’t know. Wait, why couldn’t he? Frowning slightly, the young Master of Chaldea endeavors to find that out, eventually. And if he finds out it’s because someone’s cheating him, oh there will be hell to pay for sure! Now though, now that he’s done with his paperwork, now that he’s got some free time, there’s only one thing Shigure wants to do.
 
It rhymes with “bucking merchants”… sort of. A slight grin on his face, Shigure hums to himself as he exits his room and begins to walk the halls of Chaldea. After all, half of the delicious Heroic Spirits he’d fucked into submission so far had been found in these very halls, on one of his enthusiastic walks! Shigure decided then and there that the next woman he saw was getting fucked. He didn’t even care if they were a Servant or not, shit, he’d fuck one of the female techs at this point.
 
Yeah, he was a little horny… but then, he figured he deserved a reward for getting his damn paperwork done, right?! He was entitled to a fuck! Would it be someone new? Shigure didn’t know, but the anticipation was building as he continued his walk. To his surprise, he didn’t run into anyone for the next ten minutes. Not even anyone male, who he would have passed by anyways for not having the right genitals.
 
Where… was everyone?
 
“S-Senpai!”
 
Shigure blinks and then grins as he turns around to regard one Mashu Kyrielight, the demi-Servant who had been with him since the very beginning. Mash runs up to him looked fairly flustered, while Shigure finds himself eyeing her up and down and licking his lips greedily.
 
“Mash! Just the girl I wanted to see!”
 
She didn’t need to know that he was actually looking for literally any girl at this point. And really, why HADN’T he fucked Mash yet, after all this time? Honestly, it was just a bit of a silly oversight on his part, wasn’t it? Well, no need to concern himself with that much longer. Shigure very nearly has his hands out making grabby motions to Mash’s breasts as she approaches.
 
“A-Ah, really Senpai? Ah but no… Senpai, I need your help! There’s a situation that I think o-only you can truly assist with.”
 
Shigure lifts an eyebrow at that, and smoothly shifts gears as he straightens his spine and squares his shoulders, looking down at Mash with a gentle smile.
 
“Very well. What sort of senpai would I be if I didn’t help out my kouhai? Lead the way, Mash.”
 
The pink-haired demi-servant goes positively scarlet at him playing along with her little senpai/kouhai dynamic. All the same, she turns to do so as Shigure steps up beside her, easily keeping pace with her due to his enhancements. A big grin on his face, the young Master reaches down and cups Mash’s ass as they walk, much to her enjoyment, pleasure, and blushing embarrassment.
 
If this situation isn’t something sexual to begin with, Shigure figures he’ll deal with it in short order and then he and Mash can go off somewhere quiet to enjoy themselves. Or perhaps Mash was an exhibitionist, and she’d prefer somewhere public? ‘It was always the quiet ones’ was a saying for a reason, but Shigure honestly didn’t know for sure.
 
Regardless, one way or another, Mash was getting fucked silly. He was going to teach his kouhai the joys of sex at the end of his big, fat dick.
 
-x-X-x-
 
“You’re all my Servants now! I’m taking over this shit! Hehehe, and first order of business is for you all to take off your clothes and armor! Let’s have one big orgy, right here and now!”
 
Shigure stares at the unstable red-head as she rants and raves about the Command Room, her eyes wild and crazy. She’s sort of cute… but also absolutely bonkers from the looks of things, her words fairly nonsensical as she runs up to this or that Servant, trying to grope them, only to get blasted back again. No one had truly hurt her yet, but then that probably had to do with no one understanding how an unknown human could end up in Chaldea when the rest of humanity was still incinerated at this point.
 
And she was definitely human. Shigure could tell these kinds of things at this point, thanks to his enhancements. This was not a Servant. In fact, if he didn’t know any better…
 
Any plans Shigure had before were fully derailed by this point. Wetting his lips, Shigure steps forward and clears his throat, drawing both the attention of the crazy girl and the attention of the rest of the room’s occupants.
 
“You! I knew you’d come soon enough! Finally, I can-!”
 
“Everyone, leave.”
 
Shigure cuts into the crazy girl’s ranting with a clear, concise order. The red head stops still, her nostrils flaring as if she can’t possibly believe he’d interrupt her like that. Then, a moment later, she’s at it again.
 
“Yes! Yes, everyone leave so that we can have our epic showdown! And then, once I’m done dealing with this miscreant, I can-!”
 
“I’ll handle this, alone. I want the Command Room cleared and sealed. Go on.”
 
Once again, Shigure cuts the girl off. Once again, she silently fumes. This time, everyone obeys him, though a few were already moving to do so when she started ranting and raving again. There’s relative silence as the Servants and Chaldea staff depart the room, pretty much all of them confident that they know what’s going to happen next to the mysterious girl. And none of them raise much of a fuss about it, having a pretty good measure of their boss by this point.
 
The last one out of the room is Mash, and Shigure completely misses the murderous, jealous look that the normally quiet demi-servant gives the red head as she departs. Mostly because the door is behind him, so he simply doesn’t see her face. Regardless, he hears the door seal shut and he knows that he and the girl are alone now.

 
Frowning, Shigure crosses his arms over his chest and cocks his head to the side.
 
“Who are you? How did you get here? How did you even survive the death of humanity?”
 
He’s got some idea of the answers to all those questions, but he wants to hear it from her if possible. Luckily for him, the unstable red head is very much willing to blab everything as she strikes a Shonen pose and points a finger in his direction as menacingly as she can.
 
“I… am GUDAKO! And I have been watching you, my alternate, genderbent self! I am a Master of Chaldea from another world, and I’ve come here to KILL you!”
 
Shigure lifts his brow at that, his lips thinning out into a line as he considers the overtop girl. She’d be amusing, if she hadn’t just threatened to kill him.
 
“… And why exactly have you decided to kill me, Gudako?”
 
Scoffing, the red head does a little twirl and then points at him again as she throws her head back. Honestly, she was already starting to annoy him.
 
“Didn’t you hear me?! I’ve been watching you!”
 
Frowning, Shigure furrows his brow, before snorting derisively.
 
“What, upset about what I’ve done to some of my Servants? You came all this way to whine over me using my toys?”
 
“No! I came all this way to take your toys from you!”
 
Now Shigure is a little bewildered. Luckily, Gudako is happy to explain.
 
“I’ve come to kill you and steal all your Servants, because my Servants are useless and I’ve yet to unlock a single H-scene from any of them! But you… you’ve unlocked so many lewd scenes that it’s ridiculous! I won’t stand for it another moment! Prepare for death!”
 
It’s at that point that Gudako pulls out a literal shank and lunges at him. It’s also at that point that Shigure reaches the end of his rope. Easily dodging to the side, Shigure grabs hold of Gudako’s wrist and squeezes, forcing her to drop the shank with a cry. Of course, the insane red head isn’t done at that point, and her other hand comes up with yet ANOTHER sharpened implement as she tries to drive it into his side.
 
Key word, ‘tries’. Simply put, Shigure is too tough at this point for any baseline human to penetrate his skin with a plastic shank. Even a girl with Gudako’s conviction… finds her weapon skidding off of him as he growls and grabs her by the neck with his other hand, before choke slamming her into the ground. He goes down with her, and Gudako struggles mightily to her credit, even as he looks her over with a wicked, slightly maniacal smile of his own.
 
Reaching out to stroke her face, Shigure chuckles darkly.
 
“You’re rather pretty, you know that? And your hair color… it gets me all fired up. Honestly, looking at you… you look like you could be my sister, if I’d ever had one. And that’s going to make playing with you all the more fun, in the end.”
 
Gudako’s eyes go wide as Shigure proceeds to forcibly kiss her, his tongue diving into her mouth even as she struggles to move her head away. But he’s got a firm grip on her throat, and a moment later he’s got a firm grip on her hair as well. With her hands free, Gudako tries to beat her fists against Shigure’s enhanced body, but it has no effect as he kisses the red head for all he’s worth.
 
Only Shigure gets the end the kiss, and when he does he makes a show of licking his lips as he stares down at the dazed young woman pinned beneath him.
 
“Mm, thank you for the kiss, imouto.”
 
Gudako’s eyes go wide at what becomes a rather perverse title given what he’s doing to her.
 
“Y-You… you incestuous f-freak!”
 
Growling, Shigure stands, dragging Gudako up with him by her hair as she lets out a yelp of pain. His other hand ventures down to his crotch, and he begins to pull his cock out of its tight confines, even as he grins wickedly at her.
 
“You know, you might be correct… but I still don’t appreciate the insult. Luckily for the both of us, I’ve got a far better use for your naughty little mouth.”
 
The next thing Gudako knows, she’s back on her knees and he’s pulling her hair hard enough to make her cry out again. This in turn gives Shigure leave to push his thick, meaty cock right into the foreign Master’s mouth, and in turn right down her throat as he begins to face fuck her right then and there without mercy or hesitation.
 
“Gagkh! Gagkh! Gagkh!”
 
Gudako’s eyes immediately begin to water under the oral onslaught, and Shigure watches on with an evil smile on his face as the tears finally begin to fall. The red head had made a mistake, in coming here. Not only had she only watched Shigure during his lewd ‘H-scenes’, and not the in between times where he was enhanced by his Servants, she’d also completely misread him. It takes crazy to combat crazy after all, and Shigure was very good at being crazy.
 
The foreign Master’s teeth slide along Shigure’s cock, but they do not find purchase. Even then, Gudako just doesn’t have the strength to break skin, and it actually hurts her more than it hurts him to try to bite his shaft. Ultimately, the crying red head is forced to do nothing but open her mouth as wide as possible to lessen the pain, even as Shigure groans and finally begins to pump a load of seed directly down her throat.
 
She chokes on it of course, but Shigure could care less as he makes a ruin of her face, his cum exploding out of her nostrils. Releasing his grip on her hair, the young man grins wickedly as she falls to the floor, hacking and coughing and panting. Gudako is still trying to regain her breath when Shigure kneels down and grabs her by her hips, flipping her onto her stomach right then and there.
 
A yelp leaves the red head’s throat, followed by a squeal when he pulls back on her hips, forcing her bottom up into the air and pulling her arms out from under her, causing her to face plant on the cold, unforgiving floor of the Command Room. A whimper leaves the girl’s throat as he flips up her cute little skirt to reveal her pantyhose, which are slightly damp with her juices at this point.
 
She’s not wearing panties, the little slut. Grinning ferally, Shigure leans in and pulls with his fingers and his teeth, tearing a small hole in the crotch of her leggings that in turn becomes a big one as he works his digits into it and begins to pull it wider and wider. Her cunt lips are revealed in no time at all, gushing wet at this point despite Gudako’s sobbing and clawing at the ground in front of her.
 
When he lines up with her pussy, his cockhead brushing against her slit, Shigure leans forward and pulls Gudako’s head back by her hair.
 
“Anything to say, imouto?”
 
Whimpering pitifully, Gudako shakes her head as best she can in his grasp. Then, she begins to whine, practically bawling as she blubbers and stammers her way through her denials.
 
“I-It’s not f-fair! It… it wasn’t supposed to go this way! I w-was supposed to beat you, t-take all your cute 5-stars, and g-get all the H-scenes I c-could ever want! I’m the Heroine of the s-story, d-damnit!”
 
She really is insane. Shigure can’t help but enjoy that about her. He’d never been one to listen to warnings about not sticking his dick in crazy. Grinning viciously, the young Master of Chaldea happily plays into her delusions as he murmurs in her ear.
 
“You chose the wrong story branch, imouto. Now you’ve hit a Bad End, and there’s no New Game+ for you to take.”
 
Then, he thrusts forward, plunging into her cunt. Gudako’s jaw drops open, but no sound comes out as Shigure penetrates his female doppelganger. She’d called HIM the genderbent version of her, but Shigure rather liked to see her as the genderbent version of him instead. And really, there were only two things one could do when confronted with their own clone, weren’t there?
 
Gudako had chosen to try and kill him… but Shigure was clearly the bigger pervert, because he was going to fuck her until kingdom come! Grunting, Shigure begins to thrust, picking up the pace quite quickly as he rams into the red head’s cunt again and again and again. Gudako squirms beneath him, sobbing and struggling ineffectually even then, but there’s just no way for her to escape his cock or his grasp as he pounds her into the ground, ramming into her as she’s forced into the humiliating and degrading face down, ass up position.
 
Eventually, Gudako cums around his cock. The first climax is reluctant, but Shigure isn’t about to stop any time soon. The next release she experiences from his constant pounding of her pussy isn’t quite as reluctant. Slowly but surely, as Shigure hammers into Gudako from above, the combination of pleasure and the utter failure of her plans leads to Gudako’s already unstable mind snapping even further.
 
This time though, the crazy goes in Shigure’s favor, and Gudako begins to moan and mewl beneath him, even pushing her hips back into his cock as he fucks her and fucks her. Her world is shattered in those moments, and when it comes back together, Gudako has a new reality to believe in, a new existence to embrace with all of her trademark zeal.
 
“O-O… Oh… O-oniiiii-chan!!!”
 
Shigure nearly stops what he’s doing as the address erupts from Gudako’s throat. But in the end, he keeps it up, fucking her even harder as he listens to what she has to say.
 
“P-Please, Onii-chan! Fuck your dear i-imouto even harder! Fuck me, Onii-chan! Fuck me, fuck me, fuck meeeee!!!”
 
As she climaxes along his length for the umpteenth time, Shigure chuckles a little.
 
“That’s the plan, imouto. Go on then. Take my cock like a good little sister SHOULD!”
 
Moaning louder and louder, Gudako does just that as her eyes roll back in her head and her tongue hangs out of her mouth.
 
“Yessss, Onii-chan! Fill your cute imouto’s pussy with your hot, virile cum! Stuff me with your seed, Onii-chan!”
 
It’s enough to send him right over the edge, in the end. With a roar, Shigure does exactly that, his cock penetrating Gudako’s womb in his final thrust as his cum paints her inner walls white before filling her to the absolute brim. Gudako’s jaw remains wide open, and her tongue hangs out of her mouth, but once again no sound leaves her throat as she experiences true nirvana on her ‘Onii-chan’s’ cock.
 
Catching his breath, Shigure pulls his cock out of the well-fucked red head, tucking it back into his pants and zipping them up as he stands. Gudako is quick to join him, her eyes sparkly and… dare he say it, heart-shaped? Shigure blinks, but between one second and the next, it’s gone. He’s not sure if he truly saw it or not, but as she sandwiches his arm between her breasts and gives him a lewd smile, Gudako no longer seems to have the heart-shaped pupils he could swear he saw a moment before.
 
“Will we have lots more H-scenes together soon, Onii-chan?”
 
Chuckling, Shigure nods his agreement.
 
“I suppose we’ll have plenty more, imouto. So long as you’re a good girl.”
 
Gudako cheers and pumps a fist into the air before placing a big smooch on his cheek.
 
“Yay! I love my Onii-chan SOO MUCH! Thanks for teaching me my place~”
 
Shigure just smiles and shakes his head at the red head’s antics, even as they depart from the Command Room. She’s much more endearing now that she’s not so much of a nuisance. He really does intend to have quite a few more ‘H-scenes’ with the cute, foreign Master. It was fun, fucking baseline humans sometimes. They were even easier to manhandle than his Servants…

-x-X-x-

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