Chaldea Subjugation Organization (Fate/Grand Order)

Jack the Ripper was adorable. There was just no other way to describe her. It wasn’t how Shigure thought he would be describing a ‘Heroic’ Spirit that’s legend was steeped in serial killing, but that was just how it was. Jack might not have been his curviest or his sexiest Servant, but if there was one thing the Master of Chaldea could admit, it was that she had the absolute best ass in all of Chaldea.
 
Plump and ripe for the groping, the kneading… mm, it made Shigure’s mouth salivate just thinking about it. And on top of that, her buttocks were excellently accentuated by her wide, child-bearing hips and her positively THICC thighs. It was simply the best, most amazing rump he’d ever laid eyes on. Ah, but Jack was… well, she was youthful. One couldn’t truly call any Servant summoned from the Throne a child. At least, Shigure didn’t think so.
 
They were spirits of immense power more often than not, the results of legends passed down through hundreds of years. There was nothing child-like about them… save for some of their appearances. Still, Jack was definitely one of his more innocent Servants. Or so he thought. He believed her oblivious to his stares… but that wasn’t entirely true.
 
Jack was a lot more observant than Shigure thought. She knew all about his obsession with her butt, but she didn’t mind one bit, mostly because she’d decided that the Master of Chaldea was her daddy. And if her daddy wanted to look at her body, how could that possibly be wrong? That was why Jack put a bit of an extra sashay into her step whenever she was around him. She’d gotten some tips from a few of her fellow Servants and learned all the most exciting ways to tease her daddy with her delectable derriere.
 
From shaking her butt with shimmying little dances right before his eyes, to bending over to pick something up that she’d ‘accidentally’ dropped off the ground… to even grinding her butt against his genitals whenever he allowed her to sit on his lap at one of the massive, communal dinners that the Master of Chaldea sometimes held for his Servants.
 
Of course, Jack wasn’t the only pint-sized Servant who fit on Shigure’s lap, so she didn’t always get to monopolize his crotch space. But when she did, she made sure to remind him of just how amazing her cute butt was every moment of that time. Of course, all of her efforts only seemed to be frustrating him. Jack realized she’d have to step it up a notch.
 
Shigure had no idea of course. At least, not until he stepped into his private quarters to find her waiting for him there. He was practically beside himself with desire by this point. The Master of Chaldea couldn’t even truly explain WHY he was holding back in regard to Jack anymore. So, when he saw her laying on his bed, her ass jiggling as she shifts, not at all contained by her tiny, skimpy thong, Shigure finally snaps.
 
It seems so blindingly obvious now that Jack has been toying with him. He’s across the room in half a second, and on the bed in half a second more. His cock is out and hot-dogging Jack’s ass before she can even fully turn to acknowledge his presence, a side effect of the numerous power-ups he’d gotten from his other Servants no doubt. Shigure was fast now, when he wanted to be. And this was one of those times.
 
His action elicits a ‘surprised’ gasp from Jack, followed by a cooing noise as she turns her head back to look at him, a teasing smile on her face.
 
“Daddy? Why are you doing naughty things to my butt?”
 
Shigure snorts derisively. He’s not stupid. Jack definitely knows what she’s been doing to him all this time. Which means that all of his holding back… it was just silly on his part. Waiting this long to play with his ‘little girl’s’ derriere was just stupidity, plain and simple. Well, Shigure wasn’t man enough that he couldn’t admit when he’d made a mistake. And he was more than capable of correcting this mistake, as far as he was concerned.
 
“Jack… you’ve been a bad, bad girl. And bad girls get punished.”
 
Lifting up his hand, Shigure flashes his Command Seals at the pint-sized Servant for a moment. Then, he intones his command and one of the seals flares up and vanishes as his words take hold.
 
“Everything you feel through your sweet, succulent bubble butt will be increased a hundredfold!”
 
Perhaps not the most reverent of Command Seal commands, but it has the effect Shigure wants from it as Jack’s eyes widen… though not with surprise, but instead with delight. When his hands fall atop her buttocks a moment later, his fingers digging into her cheeks, Jack cries out and her entire body shakes from the IMMEDIATE orgasm that rocks her small frame. Of course, this causes more pleasure around his cock, which is still hot-dogging her delicious butt crack as well.
 
And that in turn causes JACK more pleasure, as her flesh hits against his throbbing, pulsating rod of man meat time and time again. In the end, Shigure lets go of her buttocks for a moment and lets Jack recover as he instead moves his hand to her thong. It tears away easily. So easily, in fact, that Shigure finds himself wondering for a moment just how it hadn’t snapped off from her walking around. Her plump posterior should have seen this thong tearing ages ago with how much delicious weight it has to it.
 
No matter. Shigure isn’t going to be denied anymore. The Master of Chaldea has come for his due from Jack the Ripper, as he has for many Servants before her. With his cock still sliding up and down her ass crack, sending spasms and spikes of intense pleasure via the intensified sensitivity of her butt and through her body, Shigure reaches in and slips a finger into her asshole.
 
She’s tight of course, just as he expected. It’s not as if anyone else’s finger has ever been here before. Jack moans loudly and cums swiftly as his finger pushes in and out of her asshole quite slowly. With her sensitivity increased to a hundredfold, there’s just no way for the pint-sized Servant to ignore the pleasure Shigure is visiting upon her.
 
And if one finger can provoke that sort of reaction… Shigure adds a second finger, and then smiles as Jack’s eyes roll back in her head right there on the spot. The white-haired Servant arches her back and her tongue sticks straight out of her mouth, even as her butt cheeks clench around the length of his cock and her anal passage squeezes tightly at his two fingers.

Her pussy juices are soaking through his bedding at this point, but Shigure is well-used to his female Servants making a mess of his bed. He’ll have arranged for new fittings before the night is out. Right now, that’s not important. All that’s important is Jack and her delectable derriere, sitting right in front of his eyes.
 
How can he possibly resist at this point? It’s RIGHT THERE. Removing his fingers from Jack’s ass, Shigure pulls back entirely, sitting up on his knees for a moment. Jack barely gets out half a whine of disappointment before his hands descend upon her butt cheeks once more, sending her back into convulsions as she moans like a wanton whore instead of the pint-sized Servant she is.
 
This time however, though Shigure DOES grip her cheeks as tightly as he did before, his purpose isn’t entirely to molest and tease her. No, instead he pulls her perfectly round ass cheeks apart and exposes the tight little rosebud within. As her sphincter falls under his gaze, Shigure leans forward, the tip of his incredibly hard cock lining up with Jack’s back door.
 
It takes him a moment to find purchase. Jack is glistening with sweat at this point, the fingering of her butthole, the hot-dogging of her ass crack, and the groping of her delicious rump causing her no end of seizure-inducing pleasure. She is like putty in his hands as he plays with her. And as such, his cock slips and slides back and forth along her ass crack for a moment, before finally his dick tip presses into her slightly loosened back door.
 
He pauses as he very carefully spreads just the entrance of her asshole around his cockhead. Jack lets out another loud, guttural moan as her legs kick up and down behind him. Then, slowly but surely, Shigure begins to push his cock into her ass. This gives him another moan, this one a long, drawn out affair as she shakes and shivers and shudders beneath him.
 
The pint-sized Servant cums more than once as he hilts himself inside of her ass. Shigure takes his time doing it too, disappearing inch after inch into her bowels, but never speeding up. He goes slowly, and Jack FEELS that. She feels every bit of his cock as it spreads her open more and more. Her daddy’s dick fills her to the brim, and all Jack can do is moan lewdly all the while.
 
Only once Shigure is fully hilted inside of Jack’s ass does he pause for a moment. He stays still, and Jack slowly starts to recover, though it’s definitely hard for her, impaled as her rump currently is on his cock. Of course, it becomes much harder for her to recover when after that moment of thought, Shigure rears back with one hand and gives Jack a mighty smack across her left butt cheek.
 
A cry leaves the pint-sized Servant’s throat, and her eyes roll up in her head AGAIN as she cums explosively from the sudden sensation. One spanking… but multiplied a hundredfold by the Command Seal he’d used on her. Needless to say, Jack is just barely coherent when Shigure leans in and whispers in her ear.
 
“Naughty, naughty girl. You like this, don’t you? Not much of a punishment if you’re enjoying it, sweetling.”
 
He gives her another fierce smack across her ass, this time her right butt cheeks. Shigure loves the way Jack’s plump bubble butt jiggles and bounces under the kinetic force of his blows, even as it reddens with the outline of his handprints. She is after all, so very pale. Jack never has gotten much sunlight… and it shows in the way she goes red so very easily, both in blush and from the impact of his spankings across her derriere.
 
Mewling, Jack nods eagerly in response to his words.
 
“Y-Yes daddy! I’ve been bad, I’ve been a naughty girl! I need… I need to be punished MORE!”
 
Shigure just laughs at that.
 
“I couldn’t agree MORE, darling! Well, here it comes, my sweet Ass-assin!”

Shigure delivers another two intense smacks to Jack’s butt cheeks, and then he begins to fuck her ass. Jack squeals and then screams in pleasure as he pounds into her from above. Prone-boning, Shigure thinks they called it. He’s prone-boning his sweet pint-sized Servant in her tight little asshole. Though, not tight for long. Still little of course, but his big fat dick is currently stretching Jack’s back door to the brink as it clenches and squeezes and clings to his thrusting member.
 
The Master of Chaldea growls as he fucks his ‘Ass-assin’ some more, ramming into Jack with all the might he can. Ah, but something is missing with it. He wants… he needs to punish her for playing with him. Jack is probably one of his only Servants who’s managed to actually TRICK him, for a time. He thought her so innocent, so oblivious, so naïve… but no, a Servant based off of a legend like Jack the Ripper would never be so unobservant.
 
Jack had played him, and now he was getting his own back from her, though obviously the pint-sized Servant was enjoying it immensely. But still… Shigure’s hand comes back down on Jack’s ass as he realizes THAT’S what’s missing. He hasn’t been spanking the naughty little girl continuously while fucking her silly!
 
With a growl, Shigure proceeds to do exactly that, intensifying Jack’s already-immense pleasure by several magnitudes as he forces orgasm after orgasm after orgasm out of the white-haired girl, plowing her from behind while alternating smacks across her bright-red butt cheeks with each and every thrust of his massive cock into her oh-so-tight butthole.
 
And while he does so, he finds himself commenting on just… everything that makes Jack so fucking superb.
 
“I should have known my little girl was a naughty, naughty slut. After all, look at this ass. Look at how bouncy and jiggly it is, while also being just slightly firm. It’s perfect. The perfect ass doesn’t belong on an innocent, naïve, oblivious maiden.”
 
By this point, Jack isn’t really in a proper state to respond to his words. It’s almost as if Shigure is talking to himself. But he’s not, and he knows she hears him. From the way her body reacts, from the way she moans or mewls in a particular way. Her anal walls clench down on his cock in the most delightful of sensations as Shigure continues to spank the pint-sized, plump-reared Servant while fucking her ass to his heart’s content.
 
“And then there are these hips… child-bearing hips, if I ever saw them. Well Jack, would you like it if your daddy made you a mommy?”
 
THAT was most definitely a trigger for the girl. She was already cumming her brains out thanks to the Command Seal he’d used on her, so Shigure hadn’t expected much beyond some extra twitching and trembling. But no, it’s incredibly obvious that Jack can hear and understand what he’s saying, because she practically comes back to LIFE from his words. The petite Servant thrusts upwards with every bit of strength that remains within her. She moans wantonly, and her head bounces up and down so rapidly that it takes Shigure a moment to realize she’s nodding in response to his suggestion.
 
Well, that’s for another time. Perhaps if Jack hadn’t teased him so badly, perhaps if she hadn’t gotten one over on him, he’d have been happy to fuck her tight little cunt silly right here, right now… but no, that’s not going to happen. And he tells her as much, even as he leans in and deposits his first load deep inside of her bowels.
 
“… No. I don’t think so. Not today, Jack. Remember, you’ve been a naughty girl. And naughty girls don’t get rewards until they’ve been good girls. So, for today, I’m going to fuck your delicious bubble butt until you can’t think straight. And maybe tomorrow, if you’ve been good, I’ll consider pumping your womb full of my thick, hot seed.”
 
A cross between a whine, a whimper, and a wail leaves Jack’s throat at that, and she hangs her head, even as Shigure gets right back to fucking her cream-filled asshole. She’s nice and slick in her back door now, perfectly stretched out for his thick length and completely lubed up so that his passage in and out of her is easier and faster than ever before.
 
It’s like he’s turned her ass into a cunt of its own with his fluids, and Shigure groans as he tilts his head back, his hands coming down to grope her butt cheeks again rather than spank them. Of course, a mere groping is still more than enough to send Jack over the edge time after time. Her reddened derriere is like jiggly putty in his hands as he kneads and molds her butt cheeks with his grip, all while continuing to have his way with her.

Eventually though, his hands go down to her thighs. Her delicious, creamy, pale-white thighs. He can’t help but grope them as well, even as he keeps right on plowing her tight little asshole. In comparison to the moment they’d shared regarding her hips, this seems a lot less consequential… but in the grand scheme of things, Jack’s thighs are still one of her best features, hands down.
 
“I love my little girl’s creamy thighs. Mm, they accentuate your ass so well, Jack. Love watching you walk down the hall, your bubble butt jiggling and your thigh gap showed off predominantly. And you knew it too, didn’t you? Knew that you were having such an effect on me. Knew that you could tease daddy and he wouldn’t even realize you were doing it on purpose! Naughty, naughty girl…”
 
Jack’s response is more moaning, and Shigure reaches out to grab a fistful of the pint-sized Servant’s white hair as he drags her head back and looks at her face. She’s ahegaoing pretty blatantly by this point. Her eyes roll around in her skull as her tongue lolls out of her mouth. Grinning at the state of his ‘little girl’, Shigure releases his grip on her hair, letting Jack flop down so that her tongue is once more just rolling across the bedding beneath her, her drool making a puddle near her face as much as her pussy has made a puddle down beneath her crotch.
 
Her hips are still rising to meet his thrusts as he plows her ass even now, but it’s clear that its happening mostly on automatic at this point, and much slower than the frenzied behavior she was showing off at first. Still, Shigure isn’t satisfied. Not even a little bit. He wants… he wants more.
 
“Its clear to me now that I need to make sure you’re thoroughly punished for your actions. So, settle in… here I come.”
 
The next several hours are more of the same of course. As Master of Chaldea, Shigure has to be able to keep up with all of his female Servants. Jack isn’t even near the top of the list when it comes to his most willful, defiant, and headstrong girls. In the end, by the time that he pulls her up the length of the bed to a mostly clean spot on the large mattress, holding her close and cuddling her to his chest as he lays back, Jack is completely insensate.
 
Or so Shigure thinks anyways, even as he keeps her ass impaled on his cock, while beginning to drift off to sleep. But before he can truly fall asleep, Jack’s voice reaches him, a soft mumble that she barely manages to get out.
 
“I-I love you, daddy…”
 
Shigure just smiles and holds his pint-sized ‘daughter’ all the closer.

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