Chaldea Subjugation Organization (Fate/Grand Order)

After another long night of dealing with horror movie cliches in this Summer Camp Singularity, Shigure is just about done. He’s exhausted and at this point downright frustrated at the whole situation. Honestly, was it too much to ask for something easy for once?
 
As he lies on the bed in one of the rooms in the cabin his Team has commandeered, the Master of Chaldea hears light footsteps outside of his door. Narrowing his eyes, he sits up on the edge of his bed, ready for this to be another horror movie cliché. Maybe a doll, from how light the feet are? But there aren’t any creepy giggles to accompany it so…
 
The door to his room finally opens, revealing who’s standing on the other side. Illyasviel von Einzbern enters the room with a blush on her face, and Shigure quickly catches on that this isn’t a part of the Singularity. No, this is something else. He raises an eyebrow and watches Illya for a long moment… and then keeps watching her as that long moment turns into several long seconds which extend all the way into a minute… and almost to two minutes before Illya finally begins to stammer and stutter.
 
“A-Ah, u-um, I-I…”
 
As she stumbles over her words HARD, Shigure… doesn’t mind all that much, if he’s being honest. Rather, he lets her get there at her own pace. Normally, he might not be so generous. Especially when he’d been dealing with all of the drama of the last couple days with this dumb Singularity. This was supposed to be a fun vacation and instead… but no. With Illya, Shigure can be patient.
 
This is partially because of her youthful appearance. Even though he knows that she’s a Servant just like all the rest, meaning she’s effectively ageless and far older than him, that young-looking face of hers is enough to make him give her and those like her all sorts of allowances back at Chaldea. But to be clear, even that isn’t the real reason he’s willing to let her stand there blushing and stuttering and stammering up a storm.
 
No, the real reason… is because of what she’s been wearing, not just now, but this entire time they’ve been in this shitty Summer Camp Singularity. Illya’s rain coat… is completely see-through. And that means Shigure can see her entire petite form, scantily clad in a really cute pink bikini that doesn’t leave much of anything at all to the imagination.
 
… Yeah, Shigure is a lecher. What, did you think he was letting Illya waste his time out of the kindness of his heart alone? Nope, he was enjoying ogling her practically naked body, and he would continue to enjoy ogling her practically naked body until she either managed to get to what she wanted to say… or she fled the room and tried again another day.
 
Shigure gave it good odds either way, but what Illya ends up actually doing, he never in a million years saw it coming. Eventually, rather than getting her words together or running away, Illya just closes her mouth, shuts her eyes nice and tight… and reaches down, pulling open her rain coat right there on the spot. Shigure blinks, staring at her nonplussed.
 
Wait… there was no way, right? If… if her rain coat weren’t see-through, then she would effectively be flashing him right now. But surely Illya understood… she’d been flashing everyone this entire time? Her coat had never covered up a single thing! Everyone could see her bikini-clad body the whole way through the Singularity!
 
Completely taken aback by the thought that Illya might not actually understand this fact, the Master of Chaldea continues to sit on the edge of the bed and just stare at her. Finally, after a couple of minutes of nothing happening, the white-haired Servant opens her red eyes to see him looking at her with an eyebrow raised. She freezes for a moment under his gaze, before finally managing to stammer out a complete sentence.
 
“W-Why aren’t you d-doing anything, M-Master?!”
 
Shigure’s second eyebrow raises to join the first, and he leans back a bit as he crosses his arms over his chest.
 
“Am I supposed to be doing something, Illya?”
 
Whimpering and whining, Illya continues holding her rain coat open in front of him.
 
“Y-Yes! I’m flashing you my s-sexy bikini right n-now! Shouldn’t a l-lustful deviant like you be unable t-to resist?!”
 
Shigure just stares at her for a long moment, wondering if she’s truly serious. The answer, as best he can discern… is yes. She is serious. She seriously thinks that if she opened her coat to him, he would be struck by the irresistible urge to fuck her right there on the spot. Truly, she thought the absolute worst of him, didn’t she? He might be a pervert! He might be a lecher! But he was also the Master of Chaldea! He knew how to exercise self-control with the best of them, thank you very much!
 
Of course, Shigure doesn’t say any of that. He’s not going to allow one of his Servants to put him on the defensive here, no sir! Rather, he instead gives Illya a VERY dry look and a deadpan stare.
 
“Illya… your rain coat is see-through.”
 
Red eyes blink at that, clearly not comprehending what he’s getting at. He’ll have to spell it out for her, it would seem.
 
“Illya… open or shut, your rain coat reveals all, at all times. Everyone has always been able to see your bikini the entire time. If you think this constitutes flashing… then you’ve been flashing the lot of us the entire Singularity. So, if I really was as bad as you think I am, I would have already pushed you down and had my way with you by this point. Alright?”
 
Illya’s eyes go wide, and her face goes atomic in terms of blush. Her mouth opens and closes for a few seconds, before she shakes her head jerkily.
 
“N-No! T-That… that can’t be true! That’s impossible! M-My rain coat is supposed to cover up my adult swimsuit! L-Look!”
 
She quickly closes the see-through coat again, clutching it tightly over her body as if its covering anything up at all. Shigure just ogles her for a moment longer before locking eyes. Unable to resist, he shakes his head with a rueful smile.
 
“Search your feelings, Illya. You know it to be true.”
 
A low whine emits from the youthful Servant’s lips, and she begins to tremble in place. Shigure can’t help but feel a little bad for her. She’s really acting her appearance, at the moment. Exactly what was she hoping to gain from all of this anyways? Before he can ask, a third party speaks up… Illya’s constant companion Magical Ruby.
 
“Oh my, Illya! Talk about a failed seduction attempt! What are you going to do now, huh?”
 
Illya whips her head towards her Mystic Code. Whether it was Ruby’s intention or not, drawing her wielder’s attention actually knocks Illya out of her moment of frozen indecision.
 
“Ruuubyyyy! Y-You were the one who said this would w-work!”
 
Scoffing, the Mystic Code wiggles for a moment.
 
“Don’t be ridiculous! I said it would work if you didn’t hold anything back!”
 
“B-But I didn’t! I showed all of myself, d-didn’t I? And still Master didn’t actually do anything!”
 
“You think revealing yourself in a sexy swimsuit is not holding anything back?! You think opening up your already clear rain coat is how you’re going to manage to get your Master to have sex with you?!”
 
Illya whimpers some more, as Ruby flashes brighter and faster, clearly getting agitated right back with her wielder.
 
“If you want the D so badly, stop being a wimp and TAKE it already!”
 
Shigure’s eyes bounce back and forth between the two. He won’t lie… their antics are fairly amusing. Sure, he’s not getting any sleeping with all of this going on, but Illya makes a fine piece of eye-candy, and from the sound of things, this MIGHT all culminate in him getting laid tonight if he exercises a bit of patience. And there’s a lot that the Master of Chaldea is willing to go through in order to get laid.
 

Not to mention, Illya’s petite, scantily clad form is still on display underneath her coat even now, so really, the view is nothing to scoff at. At Ruby’s words, Illya clearly doesn’t have a response. She’s floundering for a bit, almost another full minute… before she finally seems to find her resolve. Shigure watches Illya steel and gird herself in real time… before beginning to walk forward to where he’s sitting on the edge of the bed.
 
Thanks to her size, the petite Servant doesn’t even have to kneel down. She just bends over, giving him a single glance before going for his crotch.
 
“P-Pardon me…”
 
As she excuses herself, she pulls Shigure’s cock out of his pants. Now, it should be said… he could have very well been rock hard by this point. The situation was tantalizing enough for it. But he’d not allowed it. He had complete control over his bodily functions as a result of some of the enhancements that made him more than human. Practically a Demi-Servant in his own right… if not stronger than a Demi-Servant.
 
Regardless, he could control his blood flow, which meant he could control his arousal. His cock wouldn’t get hard unless Shigure allowed it to get hard, full stop. And poor Illya in her see-through rain coat and adult bikini… well, she was just so fun to tease. So fun to fuck with, even. Shigure watches as she wraps her small hands around his dick. He watches as she begins to jerk his limp member up and down.
 
He also watches as her frustration begins to visibly mount when nothing happens. She doesn’t dare look at him again, her red eyes focused solely on the task at hand. Sliding her hands back and forth, she makes no progress whatsoever, all because Shigure is a bit of a bastard. But then, to be fair… she deserved it for interrupting his sleep! Yep, that was his excuse, and he was sticking to it.
 
Illya finally goes for the mouth, which Shigure will admit, he’d been waiting for. She closes her lips around his cockhead and begins to swirl her tongue over his glans. Then, when even that doesn’t work, she begins to gobble his dick, sliding her small head down his member, bobbing away at the soft piece of man-meat she’s holding aloft in her hands.
 
Even completely soft, he’s downright massive, to be clear. So it’s not like Illya is having an easy go of it, even without a hint of arousal on his end. Still, she’s working hard and doing her best… and Shigure figures it’s just about time to end the game and stop fucking with her. After all, while he’s fucking WITH her, he’s not actually fucking her, and that’s a travesty and a half, ain’t it?
 
Just before he stops controlling his blood flow and allows Illya’s increasingly frantic efforts to actually start something however, Ruby speaks up again, the Mystic Code wand brightening beside Illya.
 
“Wow. You’re really bad at this, aren’t you Illya? Sheesh, your lack of sex appeal has your Master’s dick completely soft even when you use your mouth!”
 
Illya whimpers and whines, the noises muffled around Shigure’s cock. Meanwhile, the Master of Chaldea can hear something… leading in the Mystic Code’s tone. Ruby is going somewhere with this, and so he continues to control his blood flow, holding off on getting hard for a moment longer to see what the Mystic Code has in mind.
 
“You know… I COULD help you out a little bit… if you wanted.”
 
That causes Illya to blink and pull off of his cock, still holding his soft noodle in her hands as she looks over at Ruby, blinking owlishly.
 
“H-How so?”
 
You think she’d sound more suspicious. Even Shigure was suspicious, and he wasn’t the one attached to the conniving Mystic Code at the hip. But Illya sounds legitimately hopeful for a moment… until Ruby brightens and lights up excitedly.
 
“Oh! I have the perfect concoction for this! Just let me administer it to you, and I swear you’re going to have him rock hard in no time!”
 
Ah, there it is. Shigure nods his head, well aware of Ruby’s infamous mystery drugs. Illya is even more aware of them, and blanches as she immediately shakes her head.
 
“A-Ah, um… n-no thank you! I’ll be fine! I’ve got this!”
 
Shigure finds himself curious, however. And so when Illya looks back down at his cock, opening her mouth to take him back between her lips, the Master of Chaldea speaks up.
 
“You might want to consider it, Illya. Otherwise, we can call it a night here… try again when you have more experience.”
 
From one con artist bastard to another, Shigure sees Ruby flashing at him, clearly catching what he’s doing. The two share a slight nod, even as Illya looks from his cock to him and then back to his cock, seemingly realizing he’s right… she can’t do it on her own. Or rather, Shigure is refusing to let her do it on her own, not that SHE knows that.
 
Reluctantly, the youthful Servant turns back to Ruby with a sigh.
 
“A-Alright… d-do it…”
 
“Wonderful! You won’t regret this!”
 
As Ruby injects Illya with the mystery drug, Shigure finds himself wondering if the Mystic Code had engineered this entire situation JUST to be able to talk Illya into this. Had she convinced Illya to try and get with him solely so that she would be forced to accept the drug? But then, how could Ruby have possibly known he would toy with Illya like he had?
 
Ultimately, Shigure concludes that the Mystic Code didn’t. There was no way for Ruby to have known… rather, it was more likely Ruby was simply being the opportunistic shit it was and waited for the right moment to present itself.
 
Regardless, it’s too late for Illya to back out now. The drug is injected… and both she and Shigure watch on as her previously flat washboard of a chest suddenly balloons out, causing her see-through rain coat to pop open again, and her bikini to dig into the soft boobflesh as it barely managed to cover the nipples of her expanded breasts.
 
By the time they’re done growing, each of her tits are bigger than her head, and Shigure has to admit… it’s a hot look on her. She’s gone from petite and youthful, to a short stack in just a few moments. She doesn’t look so innocent anymore, not like this. No, rather, she looks like a little fuck doll trying to PLAY at being innocent.
 
Stunned by her sudden extreme breast expansion, Illya doesn’t move from where she’s stood right in front of her Master. All the better for him, as he finds himself intrigued. Surely it wasn’t just growth on the menu, right? Curious, Shigure reaches out and grabs one of Illya’s tits right then and there. It was fine, she still had her hands on his cock, after all.
 
The reaction is immediate and just as extreme as the physical transformation Illya had just gone through. The white-haired, red-eyed Servant’s mouth turns into a big wide O and she lets out a half-squeal, half-shout as her body shakes and spasms… and she explosively orgasms on the spot. Shigure pulls his hand back for a moment in wonder, glancing between it and her tits as Illya shivers, slowly recovering from cumming just from having one of her tits groped for half a second.
 
They both meet each other’s eyes at that point. Illya’s gaze becomes panicked, and she shakes her head with a whimper, knowing what Shigure is going to do next. Shigure, meanwhile, just nods and grins… and then reaches out, his arms moving like a pair of coiled snakes as his hands latch onto Illyasviel’s breasts and he begins to grope both of them on the spot.
 
“NNNNNGH!!!”
 
Illya’s attempt to stop him with an aborted ‘No!’ is cut off as her eyes roll back in her head, her new knockers proving to be EXTREMELY sensitive. Even this simple groping is enough to send her through multiple orgasms, her body shuddering, her short legs shaking beneath her. Indeed, after just a handful of moments, it becomes clear to Shigure at least that she’s only even standing because of his grip on her new fun-pillows.
 
These tits are certainly quite the treat, but the true prize is Illyasviel’s face as he gropes them. Not just contorting in pleasure, but full-blown ahegaoing in under half a minute. As he plays with her tits, Illya goes through climax after climax, and just seeing that is enough for Shigure to finally get hard. He allows himself to of course, but he doesn’t have to do anything more than that. None of it is forced, his newfound erection is fully natural and based entirely off of watching Illya cum her brains out from his fondling of her chest.
 
With his member throbbing in need and Illya’s tits right in front of him… Shigure just shrugs and yanks her forward, impaling her chest upon his cock like one might impale an enemy upon their sword. Indeed, his meat ‘sword’ drives deep into Illya’s boob valley, penetrating quite far and ramming up against her ribcage.
 
She’s a Servant with a Servant’s durability, so there’s no actual impalement, mind you. Still, he definitely doesn’t let her give him anything approaching a normal boobjob, preferring instead to use her massive mammaries and the soft tightness created by her tits as a ‘hole’ for him to fuck in and out of with reckless abandon.
 
Not that Illya was in any state to give him a proper, normal titjob regardless. She’s still ahegaoing from the pleasure, still experiencing a nonstop, endless barrage of orgasms from the ‘attention’ her massive new knockers are receiving. Illyasviel has never had a chest this large before, for one. She’s not ready to deal with such massive fun bags whatsoever. But also… no woman’s breasts should be THIS sensitive. She is, effectively, at a massive disadvantage.
 
But then, that was just the way the Master of Chaldea liked it. Ravaging and ravishing her at the same time, Shigure grins wickedly at the completely mind broken expression on the youthful Servant’s face. Eventually, after a lengthy period of time in which Illya is given no respite, no mercy, and no break from constantly cumming from her tits, Shigure lets out a groan.
 
He cums all over her bust and the valley between her breasts, covering her massive pillows with his seed… which in turn causes her chest to shrink back to normal size, as though a load of white hot cum was exactly the antidote that Ruby’s mystery drug required in order to reverse its effects. And honestly? For all Shigure knew, it might be.
 
Except, when he places his hands elsewhere on Illya’s body, grabbing her by the hips to keep her from collapsing to the floor… the petite white-haired Servant spasms her way through another orgasm, exposing an interesting factoid. Namely, while her breasts had shrunk back to their normal size of nonexistent… her body’s dramatically increased sensitive remained.
 
Grinning ferally at this, Shigure lifts Illya’s light form off of the ground and pins her to the bed. Disoriented as all hell from all of the orgasms she’d already experienced, Illya doesn’t fight back for even a moment as he pulls away her rain coat and yanks off her bikini, removing her garments piece by piece until she’s entirely naked.
 
Finally, he slams home into her, his cock filling Illya right there on the spot. As he fucks her, her mind is continually bombarded by the extreme pleasure brought upon by the increased sensitivity Ruby’s drug had caused, wearing her down further and further… until her mind completely overloads from the pleasure and just shut downs.
 
Shigure won’t lie… he doesn’t even notice at first. To be fair, Illya’s eyes were already rolled back in her head. Her tongue was already lolled out of her mouth. She was already ahegaoing like crazy, so it wasn’t on him that he didn’t automatically notice the change come over her. Still, there IS a change. She’s still looking fucked silly, but also… she’s completely rag-dolling.
 
He’s got her little legs pushed up to her chest, her feet resting on either of his shoulders as he fucks her. But her hands WERE grabbing at the bedding beneath her at first. Now, they’re flopping all over the place, her toes curling and her legs bouncing along with him. She’s completely broken down, not even the orgasms really getting through to her anymore, except to make her twitch or tremble every once in a while.
 
Indeed, as he continues fucking her, his pistoning prick feeling amazing in her tight cunt, he only gets the occasional weak and pitiful moan from her lips, and her climaxes are very, very weak.
 
It’s fun for a little while… but after a time, begins to get boring. If Ruby’s mystery drug made her a fuck doll short stack, now it’s made her an unresponsive fuck toy… and that’s no fun, not when you can have any woman you want. And as Master of Chaldea, Shigure pretty much can.
 
Feeling a little disappointed, he grunts and begins to pull out of Illya, intending to go and find another member of his Team to satisfy the rest of his lust. However, before he can pull out all the way, Ruby floats up, glowing brightly.
 
“Bored? I’ve got just the thing for that! Give this to Illya, she’ll be back at it lickity-split!”
 
Shigure blinks as Ruby offers him another of her mystery drugs. He considers it for a moment. And then, with a shrug, he doesn’t hesitate to inject Illya with it, watching her for any sort of reaction. It takes a moment… but then she’s coming back to life, her eyes rolling forward and a gasping moaning exulted cry leaving her lips as she regains all of her energy… plus some extra. It’s like a straight shot of adrenaline to her system, and Shigure watches as Illya regains her cognizance, recognizing the situation they’re in for what it is.
 
As she becomes acutely aware of how her tight little pussy is stretched around his cock… the youthful Servant’s cunt proceeds to clamp down around his dick with the force of a hydraulic press. Shigure, who had been mid-thrust back inside of her, burying himself to the balls in her tight cunt, goes wide-eyed as her pussy milks his member right on the spot.
 
He lets out a hoarse groan and has to plant his hands palm down on either side of Illya’s head as he cums deep and hard inside of the girlish Servant, damn near doubling over as her insanely tight pussy refuses to let up for even a second. Her cunt milks and milks, squeezing rhythmically up and down his length. He honestly feels a pull from behind his balls in his taint that he hasn’t felt in a long time, as he’s positively DRAINED of every ounce of jizz his nut sack contains.
 
Panting heavily as one of the top ten most intense orgasms of his life finally finishes, Shigure gives Ruby a grateful nod.
 
“Yeah… that WAS just the thing, heh…”
 
He looks down at Illya, who is now wide awake and cognizant once more beneath him… and also blushing up a storm as he just creampied her so extremely that her abdomen is slightly distended from the sheer amount of seed he dumped in her. Not to mention his massive cock is still buried in her incredibly tight cunt.
 
That’s about the time Shigure tries to pull out. However, her pussy hasn’t let up on the pressure even a little bit… and to his irritation, his cock is trapped inside of her. On the one hand, this does mean that not even a single drop of his seed is able to drip out of Illya, the suction is too tight for that. On the other hand, he has places to be and things to do, so…
 
With a frown, the Master of Chaldea tries his damnedest to extricate himself from Illya’s impossibly tight pussy. He does everything he possibly can, even using his enhanced strength to try and tear himself free. In the end, all of this results in one thing and one thing only… embarrassed moans from the petite Servant wrapped around his cock. Whimpering, mewling, quivering, Illya squirms under him, looking so very ashamed of herself.
 
“Master, I- Oh… I see.”
 
That’s about when Yu Mei-Ren enters the room, looking for them. The brunette Servant freezes for a moment at the sight of the two in their current situation, before clearing her throat and regaining her composure.
 
“Master, it’s time to continue the investigation of this Singularity.”
 
Shigure nods his head in understanding, which prompts Illya to let out an admittedly cute yelp down under him.
 
“W-What?! B-But we can’t! I’m… I’m stuck on Master’s c-coooock!!!”
 
As Illya whines, Yu looks between them two for a moment… before scoffing at Illya upon seeing Shigure’s unconcerned expression.
 
“That’s your problem, Illyasviel. Everyone is already waiting for you. Besides… it’s not like it’s anything the lot of us hasn’t seen before, given how you’ve been dressed this entire time.”
 
Illya sputters at the reminder of her see-through rain coat and her skimpy bikini, which she had been forced to acknowledge was on display this whole time. She keeps sputtering right until Shigure, with a shrug of his shoulders, gets off the bed with Illya still impaled upon his dick. Seeing how he didn’t actually get undressed at all save to take his cock out in the first place, he’s all ready to go… even as he holds Illya with one hand on her ass, the majority of her weight held up by his powerful, throbbing dick.
 
Technically… he could have just ended the erection. He had the ability to do that after all. But hey! Who knew what would happen to his dick if he did so? Would Illya’s pussy get even tighter and crush his softened cock? Shigure couldn’t risk that, could he? Yep, that was his story, and he was sticking to it.
 
With a wicked grin on his face, the Master of Chaldea heads out of the bedroom and into the cabin’s center area, despite Illya’s rapid and numerous protests as she tries to get him to see reason.
 
“M-Master! Master please-! Surely not-! No, we’re almost there already!”
 
As they meet up with the others, Illya is damn near ready to combust from embarrassment… but it’s as Yu said. Not only has Illya been unknowingly dressed like a little slut this entire Singularity anyways… this is something they’re all already used to. Not a one of them is surprised by their Master’s proclivities, not by this point.
 
Normally, Shigure tries to avoid mixing business and pleasure… most of the time anyways. Okay, some of the time. Okay, when it’s really, REALLY important, he avoids mixing business and pleasure. Except for once or twice.
 
But anyways, there’s nothing to be done about it! So long as Illya’s cunt is so tightly clamped down upon his cock, they’ll just have to deal. And so the group heads off for another day of investigation with their smallest member firmly stuck on Shigure’s dick. Illyasviel babbles nonsensically from extreme embarrassment, while Ruby floats along with them, glowing brightly and smugly though not saying a word. The Mystic Code has had its fun, after all. No need to push it, heh.