Chaldea Subjugation Organization (Fate/Grand Order)

He’s feeling pretty damn good about himself as he makes his way down the hallway, humming in satisfaction. But then, to be fair, he just had sex, and the post-coitus glow has yet to fade away, that’s for sure. Shigure smiles, pretty damn well pleased with his position as the sole-remaining Master of Chaldea. He may not actually be in charge officially or anything like that, but he doesn’t need to be… everyone knows he’s basically got all the power, so being magnanimous is pretty easy, to be fair.
 
For instance, he’s coming up on Olga’s room right now, and she’s a perfect example of his ever-abounding mercy and deference to Chaldea’s original power structure. Olga Marie Animusphere had been Chaldea’s Director when Shigure had first come on board, and she’d always acted a bit… well, calling her a bitch would have been an understatement, to say the least.
 
But then they’d encountered Lev Lainur and found out the truth about Miss Animusphere. Olga was already dead, due to a bomb that he’d set off when he’d turned traitor, killing her, much of Chaldea’s Staff, and leaving the other potential Masters in critical condition to the point that they were cryogenically frozen. The revelation of her death (and utter failure) combined with the subsequent imprisonment of her soul within CHALDEAS had certainly taken her off the field for a good, long while.
 
Luckily Doctor Roman had been up to the task of stepping in as interim Director. Quite luckily in fact, Shigure had seen some of the paperwork that came with running Chaldea, and he had no desire to get involved with that. Still, Roman had a pretty good head in his shoulders, and with some help from Da Vinci and several more Servants summoned by Shigure in the long-term, they’d actually managed something amazing.
 
They’d extracted Olga Marie’s soul from CHALDEAS’ core relatively intact and actually transplanted it into a homunculus body, identical to her original body, which was provided by Paracelsus. The procedure turned out to be a complete success, and Olga, albeit much changed, walked Chaldea’s halls once again… after more than a little Physical Therapy of course. Getting her used to her new body had taken some doing, but she was nothing if not obstinate. There was a reason she was Chaldea’s Director, after all.
 
Some time had passed since that, and Olga had reintegrated quite smoothly into Chaldea, relieving Roman as Director and retaking the position. Shigure had been slightly worried that her attitude would clash with his own personality, given how he liked to do things around Chaldea, but so far there’d been absolutely no issues at all. Olga had been changed by her experiences, not quite diminished… but certainly different. She wasn’t nearly as brash or judgmental or proud anymore. Oh sure, she still had her own pride, but it was tempered by what she’d been through, and she seemed much more capable of recognizing his value as Chaldea’s Master then she had been before.
 
This was good, because Shigure had had some ideas for what he might do to her, to take revenge for her shitty behavior towards him. If she’d remained the same, if what had happened hadn’t changed her at all, he just might well have taken things into his own hands and done something drastic to assert dominance. But that had proved unnecessary, and as he passes Olga’s door, the smile on his face remains and he holds his head high.
 
At least, until he hears noises coming from within. They sound… odd and catch his attention easily. Shigure stops, slowing down and then turning around altogether as he moves closer to the door. His smile disappears in exchange for a concerned frown, and his ear twitches as he tries to hear exactly what’s going on. He can’t quite make it out through the doors though, and unable to help himself, Shigure decides he’s going to investigate.
 
… This is something that Olga doesn’t know he has. Pulling a very special card from his pocket, Shigure overrides the security on the Director of Chaldea’s door, letting himself enter with ease. He’d asked for this from Roman back when the man had been interim Director, declaring that he needed to be able to move around Chaldea without being impeded, just in case of emergency.
 
Whether it was because of who Shigure was, or because Roman actually trusted him with such power, the good Doctor had given him the card regardless, a Master Key that overrode every door in Chaldea, allowing Shigure access to each and every room… including private quarters like those belonging to his female Servants… or Olga Marie Animusphere.
 
Stepping into the Director’s bedroom, Shigure is quiet as he watches her in her bed. She’s asleep, thankfully… and alone as well. Truth be told, he’d half-wondered if she was getting some late-night relief from one of the male Servants he’d summoned, but that did seem slightly out of character for her. Regardless, she IS alone… but that doesn’t seem to be doing anything for her, because Shigure finds the Director thrashing in her sleep, obviously in the midst of a violent nightmare.
 
“N-No… no… noooo…”
 
As Olga moans out the word in her sleep, she tosses her head back and forth, her face contorted in unconscious horror, fear, or hatred. Perhaps a mix of all three. Getting closer and closer, Shigure frowns as he looks down at the young woman, something hitting him in the chest, like a pang of empathy. Huh, that was somewhat new…
 
He couldn’t leave her like this. She looked so distraught, so heartbroken, so… lost. Grimacing, Shigure reaches out and grabs Olga by her shoulders, shaking her awake.
 
“Director! Wake up, Director! You’re having a nightmare!”
 
This does indeed do the trick of waking Olga Marie up, but it also causes her to awaken in an outright panic, which leads to her starting to violently flail as her eyes snap open and a shriek leaves her throat. Shigure barely misses getting clocked in the jaw, and reacting on instinct, he goes in, rather than pulling away. Dragging Olga into a tight hug, he traps her arms by her sides to keep her from assaulting him any further, even as he tries to tell her its him, tries to let her know that he’s there to help, not hurt.
 
“Hey! Whoa, it’s me, Olga! It’s me, I’m not going to hurt you! It’s okay!”
 
As his voice hits her ears, Olga tenses up, freezing in place. Her struggles die down, but it takes him rubbing soothing circles into her back before she finally relaxes into his embrace. Her forehead presses into his chest thanks to their height difference, and after a moment she turns her head to the side, pressing her cheek into his front.
 
“… Thank you, Shigure.”
 
Truth be told, that might have been the first time she ever called him by his name. Maybe it was preempted by him calling her by hers first, but then, to be fair, the fact that she hadn’t reprimanded him yet for doing so was a first in and of itself. Olga’s hands come up between their bodies and grab at his shirt, and she clutches at him, as if using him for comfort. But to be perfectly honest, Shigure doesn’t mind that all that much. Continuing to rub soothing circles into the Director’s back, Shigure clears his throat.
 
“So… that, uh… that happen often?”
 
There’s a pause, a beat of silence, and Shigure wonders if she’s not going to answer. Or perhaps if she’s finally realizing that he shouldn’t have really been able to gain access to her quarters in the first place. Honestly, there’s a lot of ways this conversation could go wrong at this point, and he’s beginning to wonder why he came in here in the first place when she finally answers in that uncharacteristically soft voice of hers.
 
“… Yes. I was not… unaware, during my time trapped in CHALDEAS. I lived every moment of that crippling isolation in unending agony. E-Ever since I’ve returned to the real world, I’ve been having nightmares. They’re… they’re inescapable.”
 
Shigure frowns at that, looking over Olga’s head at the far wall, but not REALLY looking at it. He’s staring off into space, considering what that must be like, trying to imagine even a fraction of what she’s gone through.
 
“Roman hasn’t been able to help?”
 
Olga lets out a bark of laughter at that before falling silent again, and truth be told, that’s really all the answer Shigure needs. He knows this woman, after all, he knows Chaldea’s Director… and she’s likely never allowed herself to be as vulnerable as she’s being with him now with ANYONE. She hasn’t told Roman about the nightmares, likely hasn’t told a single soul besides Shigure himself. She’s not the kind of woman to seek help unless forced to, not even now.
 
Suddenly, she’s pulling away from him, though not all the way, just enough so she can tilt her head up to look at his face, to make eye contact. Shigure is surprised by the emotion he sees in her glistening gaze… it’s a lot more than he would ever have expected from her, but then, given the circumstances, he supposed it made sense.
 
“Shigure… will you help me?”
 
Blinking dumbly at that, the Master of Chaldea is more than a little taken aback. After all, he’d just gone done thinking that Olga was the kind of woman who would never seek help unless forced to. And yet… he wasn’t forcing her to do anything, was he?
 
“Please… I just need to feel good. I just need to… to feel something besides the pain and agony and the isolation. I was so alone in there, but now I’m out here and I STILL feel alone. So please… help me not feel alone.”

And then she moves up on her tip toes and lays her lips on his in a kiss that makes her intentions crystal clear, even if her words were a bit of a rambling mess. Shigure, meanwhile, isn’t the kind of guy to look a gift horse in the mouth. There’s a handful of things that he’s learned recently he’s actually got a knack for. Sex is one of them, so if this is what Olga needs to recover, then he just might be her guy after all.
 
As they kiss, the kissing quickly turns into a full-on make-out session, with plenty of groping as things get more and more heated. Shigure’s tongue pushes against Olga’s lips and encounters no resistance as she opens up and lets him slip it into her mouth. As their tongues intertwine with one another, he takes this as a side of her complete consent, and his hands slide down her back, moving to her ass, where he gropes her through her pajama bottoms.
 
She’s dressed in a pajama top, pajama bottom combo, nothing all that sexy or seductive, completely comfy and functional more than anything else. And yet, she’s still very beautiful, and Shigure is more than happy to give her exactly what she needs. Eventually though, the two do have to separate, though they leave a thin string of saliva connected between their lips as they both stare into one another’s eyes, breathing quite heavily, panting openly.
 
Olga finally does pull away entirely, and Shigure lets her go, watching as she pulls off her pajamas to show a body clad in a matching set of bra and panties. He can only imagine that the bra has none of that painful metal in it, otherwise she would never wear it to bed. At the same time, a position as important as hers meant she was always on call, so it only made sense that she would find a way to wear such a garment at all times to avoid inappropriate incidents.
 
Regardless, as Olga reaches up and begins to nervously pulls off her bra and then shimmy out of her panties, Shigure also starts to strip down. His shirt comes off first, and she shyly admires his chest, but her eyes go REALLY wide when he pulls down his pants and boxers next, letting his growing erection jump out of its confines, springing upwards though not quite at full mast yet as it droops a little, still pointing in Olga’s general direction.
 
The Director of Chaldea gasps at his cock size, clearly astonished, and Shigure smirks a little, a burst of pride filling him. Why yes, he did have a big dick, thank you for noticing. Chuckling lightly at his own thoughts, Shigure take a step towards Olga, now that they’re both naked.
 
“You look beautiful, Director.”
 
Olga blushes and glances off to the side, not doing anything to hide her naked form, though she’s clearly embarrassed.
 
“W-Well, it is a replacement… they obviously enhanced certain aspects…”
 
She sounds like she truly believes that, and Shigure can only imagine that its adding to her insecurities, to her stress. But Shigure is being completely truthful when he steps up and takes her by the shoulders again, this time bare.
 
“No, Director. You were always this beautiful. They didn’t change a thing.”
 
Her head whips back around, and she stares at Shigure with wide eyes, as if trying to assess the veracity of his words. He just smiles at her and pushes Olga back onto her bed, moving with her and over her as she tenses up, blushing still all the way. As he straddles her and leans in, Olga stops him for a moment, swallowing nervously as he raises an eyebrow at her.
 
“Um… please call me Olga, like you did before. I like that better.”
 
Shigure’s smile grows a little at that, and Olga blushes even harder than before. She’s cute like this, very cute in fact, and truth be told, imminently fuckable.
 
“Very well… Olga.”
 
He makes sure to rumble her name out in a deep, husky tone. Olga’s eyes go wide again, and she shivers as she trembles beneath him, a quiet mewl leaving her lips before he even touches her. And then he’s on her, his mouth on her neck and jaw line, and his hands on her body. One goes to her chest to knead one of her perky B-cup breasts, while the other slides down even further, moving between her thighs and rubbing against her pussy for a moment before slipping two fingers into her.
 
As he suckles at her soft neck flesh, rolling a nipple in between the pads of his fingers and gliding two digits in and out of her cunt, he listens… and he gets exactly what he’s hoping for. Playing Olga like a fine musical instrument results in his ministrations and his hard work eliciting cute moans from the Director of Chaldea. She squirms, but she doesn’t struggle, and the more he plays with her, the wetter she gets as he serenades himself in her voice, in the melodic noises he draws out of her lips.
 
Spending a few minutes on this, Shigure only stops when he can sense that Olga is getting close, her hips beginning to hump at the air, trying to follow his fingers every time they pull back inside of her. She’s moaning, and she’s so damn wet… but Shigure wants her first climax to be at the end of his dick, not at his hands. After making sure she’s more than wet enough for him to insert his sizable length into her, Shigure pulls his fingers out and brings them up to his own lips as he draws back from her neck, sucking her pussy juices off of his digits right before her eyes.
 
She watches him do it too, staring at him in wonder and awe and deep, deep need, Even as he licks his fingers clean and gives her a raunchy smile.
 
“Tasty.”
 
Olga’s face goes even redder and she very nearly covers it with her hands, but Shigure’s next action cuts through the embarrassment, as he brings his fully erect cock to bare on Olga’s needy pussy lips. She gasps at the feel of his cockhead pressing into her entrance, causing it to flower open around him, and she places a hand against his chest, stopping him briefly.
 
“P-Please… be gentle. I’ve never… d-done anything like this before.”
 
Of course not. Even ignoring the fact that she has a new body which, if it is anatomically correct WILL have a new hymen, he can’t imagine Olga Marie Animusphere of all people, even before all of this, having a particularly active sex life. Smiling down at her reassuringly, Shigure nods. Olga nods in response, almost covering her face again from sheer embarrassment, even as he slowly drives his cock up into her, listening to her soft moaning and mewling all the while.
 
When he finally hits her hymen, the evidence of her virginity, Shigure leans forward and pulls Olga’s hands away from her face, holding her wrists over her head and locking his lips with hers. He kisses her, even as he pushes forward, piercing her hymen and driving inexorably deep into the Director right until he hits her cervix. She cries out into his mouth, and moans as well, and Shigure stops the moment he feels the barrier that represents the entrance to her womb, pausing to let Olga adjust to the size of his cock, now buried inside of her.
 
After a few moments of this, Shigure pulls back and lets go of her wrists, intending to ask her if she’s ready to continue, only to be surprised when Olga immediately wraps her arms around his neck, nuzzling her face into the crook of where it meets his shoulder and murmuring to him. But even if it’s a murmur, he hears every word.
 
“… S-So amazing… you feel so a-amazing inside of me…”
 
Shigure chuckles softly at that, and holds her back, wrapping his arms around her back as they enter a lover’s embrace, if he’s ever been in one. Eventually, having decided that she’s adjusted enough, Shigure begins thrusting in and out of her, listening for any signs of pain or discomfort, but getting only moans of pleasure. After some minutes of slow-paced lovemaking, Shigure ramps up his fucking.
 
This results in him eventually piercing Olga’s cervix, entering her womb directly with the size of his massive member, eliciting a long, drawn-out, continuous moan from the young woman. He continues to fuck her like that, slamming into her true depths with around half of his might and half of his force, even as her pussy contracts and squeezes around his cock, her legs locking themselves around his hips, and her inner walls rhythmically tightening as she finally does cum, and not just once, but again and again.
 
Eventually, her orgasms milk him of his seed, and Shigure groans as he fills Olga’s womb directly with hot, sticky semen. The two of them are lost in the throes of pleasure for a moment, still in that lover’s embrace from before, perhaps even more so now with Olga’s every limb wrapped around Shigure’s body, holding him close.
 
In fact, when he tries to pull back, to pull out, Olga doesn’t let him. She grips him tighter with both her arms and her legs, and once he looks at her, once she has his attention, she bites her lower lip and makes a request.
 
“Stay with me for the night, Shigure? We… we both have our duties, but can you just hold me? Just for a while longer…”
 
Shigure inclines his head in agreement, and they move into a bit of a more comfortable position, his cock ultimately slipping out of her, but him staying in the bed as he ends up on his back and she curls into his side, her upper half draped over his chest as he rests his chin on top of her head of white hair. The two of them fall asleep like that, though before Shigure finally nods off, he could swear he hears Olga murmur ‘I love you’.
 
But when he looks, her eyes are closed, and her breathing has evened out. She probably didn’t say anything at all…

-x-X-x-

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