Chaldea Subjugation Organization (Fate/Grand Order)

It’s not unusual for Shigure to be observed while traversing the halls of Chaldea, nor while enjoying himself upon the body of one of his many female Servants. Rather, it’s actually quite normal for him to be watched. After all, most of the time he doesn’t hesitate to fuck one of his many, many lovers wherever he finds them. Sometimes that’s in a public area where several others get to gaze on and even masturbate to the sight.
 
Even when he’s alone with a female Servant, in his quarters or theirs, it’s common sense that a dozen others are likely using one of their many scrying abilities to gaze in on the coupling, like the horny, slutty voyeurs they all are. Shigure doesn’t begrudge them this. He’s only one man and there’s only so much time in each day. He might have been able to get to every single woman if he cut corners and did literally nothing else day in and day out… but even a hedonistic pervert like him didn’t consider that a healthy life. He was just too selfish to be that selfless.
 
But yes, all that aside, Shigure was watched practically twenty-four-seven. So, when he said that for the past week or so he’d been getting the sense that someone was peeping on him whenever he was fucking one of his Servants, that statement might be a little confusing.
 
To elaborate, the ‘sense’ in this case was Shigure’s sense of sight. As in, this particular Servant’s attempts at being sneaky while she peeped on him have been terribly unsubtle, with her peeking being the equivalent of her poking her ENTIRE upper body around corners and through doors and the like.
 
Yes, it would seem that Abigail Williams, while normally a very GOOD girl despite her circumstances, had been quite naughty lately. And while it had been cute at first, it quickly grew into arousing, and when Shigure got aroused, well, he really only had one way of dealing with that sort of thing.
 
And so, he’d called Abigail to his quarters a little while ago. As the tepid, light knock finally comes at his door, Shigure smiles slightly before calling out.
 
“Come in.”
 
The door opens, and Abigail Williams steps inside. While this was one of several of his Servants that took on the appearance of a young girl, Shigure knew she was anything but. Even more so than some of the others, Abigail was what was called a Foreigner Class Servant. Her Existence came from outside of the Domain of the Universe. One of her Traits was even ‘Threat to Humanity’.
 
She was the Key to the Gate, the All-in-one and the One-in-All… but she was also Abi, and Shigure had long had a weakness for pretty girls. So, they had a pretty good relationship, as it were. It had just never evolved beyond platonic… until now.
 
“M-Master…”
 
Abigail blushes and averts her eyes as she nevertheless creeps closer to him. Her yearning for proximity is clear, even as it’s equally clear that she’s aware she’s been a bad, bad girl. A naughty girl, even. Shigure smiles slightly, but at the same time makes sure to pin Abi with stern, disappointed gaze.
 
“Abi. You know why I’ve called you here.”
 
“… Yes, Master…”
 
Shigure narrows his eyes, and when Abigail gets close enough to where he’s seated on the bed, he reaches out and tucks a hand under her chin, forcing the petite Servant to look up and meet his gaze.
 
“Do you remember what you told me, once?”
 
Blinking, it’s clear she doesn’t quite know what he means. They’ve had a few conversations after all. Shigure just nods in understanding, before repeating her words back to her, verbatim.
 
“You said; ‘If Master doesn’t keep an eye on me, I feel like I could turn naughty… please don’t leave me alone, Master.’.”
 
A quiver runs through Abi, before she quickly nods to show she remembers. She tries to avert her gaze again, but Shigure doesn’t let her. It’s funny, because even among the varied and incredibly powerful women of Chaldea, Abigail Williams is on a whole other level in some ways. She’s dangerous and eldritch and Other in a way most of them are not.
 
But Shigure does not fear her. He would be a piss-poor Master of Chaldea if he did, truth be told.
 
“Have I been a good Master, Abigail? Have I left you alone?”
 
“M-Master! You’ve been wonderful! You’ve been at my s-side, every step of the way!”
 
It was true. He’d made time for Abigail. Never sexually before now, but he’d made sure she wasn’t lonely, taking her on picnics, reading to her some nights until she fell asleep. And yet…
 
“Then why, exactly, do I find that you’ve turned naughty anyways?”
 
They both knew when Abigail used the phrase ‘turn naughty’ back then, she hadn’t meant it in the way Shigure was using it now. She’d meant something far worse and far more dangerous, both to his health and the health of everyone in Chaldea… if not the entirety of this universe. But Shigure has changed things up now, swapped definitions, and Abigail doesn’t seem to mind as she stares at him, wide-eyed, trembling… and blushing profusely.
 
Her lips part and she pants a little before licking them quickly with her tongue.
 
“M-Master will have to p-punish me now, won’t he? I’ve been a bad, bad g-girl. What… what is Master going to do to me?”
 
In truth, she hadn’t done anything wrong. As previously mentioned, everyone in Chaldea spies on him having sex with everyone else all the time. But it’s incredibly obvious to Shigure that Abi isn’t just VERY eager to receive her ‘punishment’, but that she was hoping for it when she started peeping on him.
 
… He doesn’t think she actually knew enough to hide unsubtly on purpose though. He’s pretty sure she really thought she was hidden all of those times she was practically protruding out from around a corner, or through a doorway. Heh, just too cute, to be honest.
 
“I think you know, Abi.”
 
Standing up from the end of his bed, Shigure forces Abigail to take a step back, but he maintains his hold on her jaw, even as his other hand moves down to deftly free his cock from his pants. Whipping his dick out, the thick throbbing rod of man-meat swings around with a hefty-
 
SMACK!
 
-as it impacts with Abi’s cheek. She cries out a little in pain as her head is turned to the side, but that cry then evolves into a moan, and she’s quick to nuzzle her cheek against his pulsing member like a cat in heat. Shigure just chuckles, fully intending on giving Abi the usual that he gives all his Servants, when their relationships evolve to this point.
 
Indeed, he’s about to start with the Key’s mouth when his eyes… his attention is grabbed by the keyhole in Abi’s broad forehead, unveiled by her parted blonde locks. He stares, because it’s not just a keyhole right now… there’s an eye staring out of it.
 
The Master of Chaldea knows all there is to know about every Servant under his roof. He would be a fool not to do his research, given the number of serious world-ending threats he both summoned and fought on a regular basis.
 
The eye staring back at him through the hole in Abigail’s forehead belongs to her patron, the Outer God Yog-Sothoth. After a moment of making eye contact with the eldritch being… the eye disappears from sight, leaving Abigail’s keyhole once more the pitch black void it usually is.
 
Except… the urge to do something wild stays with Shigure. The urge to try something new, something he’s never done with any other woman before, mostly because he can’t… it overwhelms him. If there’s one true weakness the Master of Chaldea has besides beautiful women in general, it’s trying new things with said beautiful women.
 
And this definitely counts as a new thing. So, despite any reservations or misgivings his more rational, logical side might have in this moment, Shigure once again gives in to his poor impulse control, grabbing Abigail Williams by her skull and lining his cock up with her keyhole instead of her already parted, expectant lips.
 
“Master…? Mast-eep!”
 
As he slowly pushes into it, Abigail is frozen in shock at the sensation of the dick sliding into her skull. Except, it’s not actually sliding into HER head. There’s no brain matter to be felt. That would be a step too far, even for Shigure probably. Rather, he’s putting his dick through her keyhole, which is in fact an interdimensional portal that her patron, an eldritch being from outside their universe, uses to observe her and her surroundings.
 
He can’t help but let out a moan of pleasure as his dick is impaled in what FEELS like a pussy. It was a gamble, of course. There was every chance he’d inadvertently put his cock in the cold of space, and it would freeze off or something. And for a moment, it ALMOST feels like that. But no… no, this is a cunt. It’s odd, because if there’s one thing Shigure knows, it’s pussy. Some part of him instinctively recognizes this as pussy, at that.
 
… But it’s like no pussy he’s ever fucked before. Not only does it squeeze him in ways that defy logic, swirling around his cock and wrapping it at odd intervals, it’s also searingly hot, shockingly cold… and pleasantly warm all at the same time. Despite the sheer weirdness of the experience, it’s also maddeningly pleasurable, and Shigure… Shigure simply can’t get enough.
 
Which is good, because as he fully hits himself in Abi’s keyhole and then prepares to pull back to begin thrusting, he finds himself unable to do so. He cannot pull out. Instead, small tentacles, clearly part of this… eldritch-as-fuck pussy, squirm and wrap around his cock. Each of the tiny tendrils are capped with small suckers that stick and unstick from the flesh of his member in an insanely pleasurable manner.
 
The Eldritch Cunt he’s decided, for good or ill, to fuck, holds him firmly inside of itself as it pleasures him constantly. There’s even what feels like multiple tongues licking every inch of his cock on TOP of the insanely tight pussy, and the multitude of tentacles in there! It’s all just an inch away from being too much… and that’s before Abi finally gets over her shock and decides to act as well.
 
Reaching up, the Key to the Gate wraps her thin arms around his body. She plants her small hands on his ass… and after anchoring herself, she leans in, tilting her head back and jutting out her mouth and chin. The result is that her mouth ends up on his ball sack, her tongue sliding out to swirl along his gonads before she happily, giddily even, gargles his balls to her heart’s content.
 
All while he’s buried inside of the interdimensional portal in her forehead. Yeah, Abi’s actions are definite the tipping point, and with a loud groan, Shigure throws his head back as Abi and her Patron work together to milk one of the most powerful orgasms from him that the Master of Chaldea has ever had.
 
It’s also one of the most copious, heavy, voluminous loads he’s ever dropped as well, even as it all flows DEEP into Abi’s keyhole and the eldritch pussy beyond it. He cums and cums and cums for what feels like an eternity, before finally it’s over and Abi is suckling and slurping at a pair of empty, slightly shriveled nuts.
 
With his semen successfully claimed by the Outer God on the other side of Abigail Williams’ forehead, the eldritch pussy Shigure found himself trapped in reluctantly loosens its hold on him and begins to allow him to pull out. Its still slow going though, as the tendrils and tongues both lap at his length in tandem until he’s finally free of Abi’s keyhole, his cock fully cleaned and only slightly slimy by the time he pops free.
 
A small dribble of seed drips down from the keyhole, but Shigure only gets a moment to properly admire the sight, before Abi reacts to what just happened in an… unexpected manner. With the removal of his cock from her keyhole, the Foreigner Class Servant starts spasming wildly right before his eyes.
 
For a moment, it just looks like she’s cumming her brains out… and to be fair, she is. Shigure knows what an orgasmic seizure looks like, he’s caused dozens in his Servants at this point after all. But after the moment passes, it becomes clear that that’s not ALL it is. No, her body is changing as well.
 
Her skin becomes an odd yet attractive grey, and her eyes bleed from blue to red. Her hair shifts from a golden blonde to a silvery white, and her teeth sharpen into knife-like, sharkish fangs. Shigure can only watch on, with no clue how to help her, or even if help is warranted. Eventually though, it’s over and she finishes coming down from her orgasm.
 
Those red eyes of hers flicker to him, and Abi grins a positively predatory grin, and not JUST because every smile she makes will be a shark-like one for the rest of her days.
 
“Master~ Look what you’ve done to me now! I’m a very Bad Girl who needs to be turned into Master’s Cum Dump on the double, or I just might be super naughty!”
 
Looking down at herself, this new rude, crude, and lewd version of Abigail Williams runs her hands up and down her body, up and down her dress.
 
“All of those other Servants of yours… I wonder how they would last against me. I’d break them down and turn them into my pets… and maybe if you were really good, I’d let you have one or two once in a while. How’s that sound, Master? Oooh, that frown on your face makes it clear you don’t like it! Better stop me! Better DISCIPLINE me! Better-urk!”
 
Honestly, Shigure was already more than happy to oblige, but Abigail may just have hit a trigger when she threatened to emasculate him in such a way. With a lustful growl, he grabs the Key by her throat and spins them both around, slamming her into the bed and pinning her down as he climbs atop her.
 
With his free hand, he rips off her very poofy dress and then her bloomers off as well, exposing every last inch of her stick-thin, somewhat emaciated frame. Her ribs are slightly visible against her skin, and normally Shigure didn’t go for starved girls… but in this case, he knows Abigail isn’t starving. Hell, she’s not even fully human. This is just her body type, and the Master of a Chaldea is a man of very VARIED tastes. He did just fuck an eldritch pussy through an interdimensional portal in a girl’s forehead, after all.
 
With a sharkish grin, Abi wriggles about beneath him, licking her pointed teeth and lips eagerly as she gasps and pants in expectant need.
 
“H-How are you going to punish me, Master? Huh? How are you going to make me your BITCH?”
 
Grinning right back at her, Shigure pretends like he’s considering it for a moment. Like he doesn’t already know exactly what he’s going to do. The truth is, he DOES know what he’s going to do with her. After all, he knows full well that Abi has likely been masturbating constantly to her peeping sessions involving him and other Servants. She no doubt makes a mess of her bed every night, just cumming to thoughts of him with her instead.
 
So, really… fucking her pussy wouldn’t be much of a punishment, now, would it? It certainly wouldn’t be the CORRECTION that Shigure felt Abigail’s behavior so far warranted. No, he had to go further, and occupy a hole he KNEW she had never even considered before. Excepting her already-fucked keyhole, of course.
 
And so, sliding his hands down Abi’s stick-thin legs, Shigure grabs her by the ankles, folds her body in half, and in doing so lifts her hips just enough off of the bed so that he can prod the tip of his thick, throbbing cock against her tight, virgin asshole instead of her cunt.
 
Those newly red eyes of hers immediately go wide as the Key freezes beneath him, her grin becoming a bit… forced. In all fairness to her, her sphincter is even tighter than her keyhole was. At least, the entrance is. The only real saving grace for the both of them is that her patron left his cock coated with a film of eldritch slime as he’d pulled back, a lubricant that would be incredibly crucial to these next few moments.
 
“A-Ah… um… are you sure about this, Master?”
 
Suddenly looking a lot less sure of herself, and also sounding a lot less rude and crude as she does a full one-eighty despite her changed, slightly demonic appearance, Abi looks between his face and where he’s trying to push past her virgin sphincter and into her poor, unprotected, defenseless back door. Chuckling nervously, the emaciated Servant wiggles beneath him.
 
“Maybe… maybe my punishment could be reduced to just a time-out i-instead? Or maybe… a spanking? Or even a-!”
 
Whatever she might have said next is cut off as Shigure finally makes enough progress to punch into her ass. Instead, Abi lets out a low, long squeal of pain as her butthole is slowly but surely speared and pierced by a dick WAY too big for it. But that doesn’t stop Shigure. He’s well used to sticking his dick in places it may not belong at this point, and so he forces his way into Abi’s bowels inch by inch, stretching her rectal cavity with his thick, throbbing cock.
 
Honestly, he might have been worried about actually hurting her if he didn’t understand that just this much wasn’t really enough to truly damage the Key’s existence. But also, more than that… Abi’s squeal turns into a screaming, wanton moan as she cums her brains out naught but a moment later, her unoccupied pussy squirting juices all over her legs.
 
Grinning wickedly, Shigure doesn’t hesitate… and this time around, no matter how tight Abi’s back door is, he doesn’t take no for an answer when it comes to pulling out. The eldritch pussy he’d fucked through her keyhole might have been able to hold Shigure in place against all odds, but this? He can handle a tight ass, no problem.
 
Pulling halfway back out, the Master of Chaldea chuckles as he relishes in Abi’s howl of pain and pleasure alike. Then, he punches back in, impaling her bowels once more and enjoying how she squeals like a stuck pig. Beginning to really, truly fuck her anally into the bed, Shigure pushes her legs up even further so he can take her in an anal mating press, her poor body unable to fight him off.
 
Well, maybe it could have, but despite her trepidatious words, Abi clearly doesn’t actually want him to stop. Even as she screams in pain from the rough anal fucking she’s receiving from him, the Foreigner Class Servant makes no effort to try to fight him off. She likes it. She enjoys being in pain, it would seem. She’s a masochistic little whore who’s loving having her tight, virgin asshole impaled upon his cock.
 
Of course, if Abi thinks this is the extent of the discipline Shigure has in store for her, if she thinks this is all he’s going to do to ‘correct’ her, she has another thing coming to her. Rather, seeing just how much of a horny little masochist his small Servant is, Shigure can’t really stop himself. He’s more than capable of playing most roles in the bedroom. But when presented with a tasty masochistic treat like Abi, his sadism asserts itself and he goes full tilt.
 
That’s exactly what happens now, as Shigure spins Abigail around and pushes her face first into the bed without ever actually taking her off his cock. She squeals from the sensations caused by this fast-paced rotational movement, before her noises are muffled by the bed.
 
Once she’s bent over in front of him, Shigure doesn’t hold back. One hand comes down on her ass, both cheeks, again and again.
 
SMACK! SMACK! SMACK!
 
He spanks her hard enough to likely leave bruises, especially in her newly pale grey skin. At the same time, his other hand goes to her hair, grabbing hold of the silvery-white locks that she’s now sporting, and yanking back with all his might. A sharp yelp leaves Abi’s lips as he does so. She no doubt feels the stretch of her scalp thanks to his actions, and the way her back arches is beautiful to Shigure’s eyes. Nothing snaps, to be fair. She doesn’t break any bones. But she definitely strains muscles and bends in a way that she’s probably not made to bend.
 
Fucking into her tight little asshole all the harder, spanking her and pulling her hair, Shigure almost feels like it’s enough. Feeling her body shivering and quaking under his, it’s clear that it IS enough for Abigail Williams. She’s cumming her slutty, masochistic little brains out after all, orgasming again and again for him. But… something is missing even then. He needs to do… more.
 
And so Shigure goes for broke and lets go of her hair while at the same time removing his hand from her spanked silly ass cheek. For a simple moment, Abigail hangs in place, back still arched and eyes still rolled back in her head as she cries out and squeals in pleasure and pain alike. That moment will soon end however, and she’ll begin to fall forward.
 
Shigure doesn’t let this happen, of course. One hand lashes out, circling around her head, while the other does the same, but moves around to her chest. Now, with a normal woman, Shigure would be greatly tempted to fish hook her while fucking her like this. He would have stuffed two fingers into the side of her mouth by now and pulled her head back, dragging her back by the jaw.
 
But Abi was no normal woman, and she had somewhere else for him to fish hook, didn’t she? And so Shigure’s fingers slide over her forehead, skidding over to the keyhole there… and thrust into it before curling in. Fish hooking her via her keyhole, Shigure fucks the Key even harder in the ass as she screams in new sensation. He’s not sure how yanking and pulling on the interdimensional portal in her forehead necessarily affects Abi, truth be told. Whether it’s agonizing or ecstasy, he couldn’t say.
 
But it does the job of pulling her back, of forcing her spine to arch some more while he continues to have his way with her from behind. Meanwhile, his other hand comes around to grab at her tiny nipples on her otherwise flat chest, twisting them brutally one after the other, causing her even more agony and pain… which for an eldritch masochist like her, only seems to translate into more and more pleasure.
 
With a fresh and loud squeal of pain, Abigail bucks her hips… and explodes in one last gigantic orgasm, soaking the bed beneath them both in her pussy juices. Meanwhile, her ass squeezes down on Shigure’s cock so damn tightly it feels like it might very well crush it. If he wasn’t an enhanced human being, made stronger and faster and more durable by dozens of his Servant lovers, Abigail’s incredibly tight anal passage definitely WOULD have castrated and emasculated him.
 
As it is, she manages to milk him of his release, causing Shigure to unleash a huge load of seed deep into her rectum and bowels. And best of all, thanks to his fish hooking of her keyhole dragging her head back, he’s got her back far enough to watch her face twist up in a pain-filled grimace of an ahegao, a mixture of agony and pure, unfiltered bliss spreading across her features.
 
The moment comes to an end and Shigure lets out a panting, breathless sigh as he drags his fingers out of Abigail’s keyhole and removes his hand from her chest. As she flops forward, seemingly out of it, he slowly pulls his cock out of the brat’s impossibly tight asshole. Her back door clings to his cock with all of its might, trying desperately to keep him inside, even as Abi lets out an unintelligible gurgle that may or may not have been a noise of disagreement with his actions.
 
He eventually manages to pull out of the devilish Servant’s clenching behind however, leaving her a gaping mess leaking his seed. Looking at her very bruised backside, Shigure scoffs… and rears back his hand for one final heavy swat.
 
S-SMACK!
 
Not that the damage is in any way permanent. In fact, it’s downright temporary as before his eyes, he can already see her body healing. Meanwhile, that last spanking just gets another gurgle in response from the face down Key, with Shigure shaking his head in amusement.
 
“If you remain a naughty, bad girl who keeps on misbehaving, Abi… I’ll have to punish you even harder next time. I hope you understand that.”
 
A mumble is all he gets in response. Snorting derisively, Shigure grabs her by her hips and yanks her up, depositing on her feet beside his bed.
 
“This isn’t your room. Go on, brat. Get.”
 
Shakily managing to stay on her feet, Abi stumbles towards his door. Shigure watches her go, and his cock twitches, almost prompting him to stop her and call her back. But no, the Master of Chaldea knows better. With brats like this, you couldn’t afford to second guess yourself, or even ever let them see you change your mind, at least not with the meaningful stuff. Rather, you had to stay strong, you had to stay resolute… and you ALWAYS had to stay in charge.
 
As she reaches the door to his quarters, Abigail Williams stops… and reaches down to pull up a very skimpy pair of black panties that appear out of seemingly nowhere halfway down her stick-thin legs. So sheer and lowcut, they barely cover her pussy, and leave the visible curves of her pelvis on display even once she has them up over her crotch.
 
In an instant, she no longer looks nearly as… defeated or conquered or tamed as she did a moment before. Looking suddenly strong and hale, the Key to the Gate glances back over her shoulder at Shigure and gives him a positively sharkish grin.
 
“Mm, Master… I hope you do; you know. You’ve turned me into a bad, BAD girl now, Master. So, you better take responsibility for correcting all of the naughtiness that’s going to follow. As for punishment… next time better be harsher, because what you just dished out was soooo weak~”
 
Shigure blinks, slightly taken aback by her sheer brattiness, even in the face of all he’d done to her. With a mocking giggle, a wiggle of her hips, and the sticking out of her tongue at him, the now very bad girl skips off, leaving his cock twitching and throbbing in anticipation of her next punishment session. One thing was for sure… it would likely be very soon indeed, if THAT attitude was any indication.

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