Chaldea Subjugation Organization (Fate/Grand Order)

“Mastaa-dono!”
 
There’s only one Servant in all of Chaldea who addresses Shigure in that particular tone in that particular accent. And it’s not one of the handful that are currently on his bad side, so the young Master of Chaldea stops and turns around, smiling as the vision of beauty that is Ōi Hokusai skips up to him. And she really is beautiful. From her neck-length hair with flower ribbons of differing sizes interspersed throughout it, to the flowing kimono she wears that sometimes reveals more of her skin than one might expect.
 
As she comes to a halt in front of him, Ōi has a bright smile on her face, as she always does. But… Shigure can tell that there’s something bothering her, something she’s hiding behind that smile, buried in her gaze. Hm, if he had to guess, it’s probably art troubles of some sort, given what he knows of Ōi’s hobbies. Perhaps she’s in a bit of a slump, or something? Either way, he gives the beautiful Servant his full attention, already contemplating just how he might get into her pants… or lack thereof, as the case may be.
 
“Yes, Ōi? What is it?”
 
“Mastaa-dono! Please allow me to capture your naked form as a timeless work of art! It must be quite enthralling, if you’ve managed to charm so many of my fellow Servants with it!”
 
Hm, well, she’s certainly blunt about her desires, isn’t she? Now, Shigure, incredibly vain as he is, immediately leans towards agreeing on the spot. He does find himself wondering if she knows how vain he is and is leaning into that, or if she’s simply completely naïve to just how well she’s already managed to push his buttons. Either way… he’s definitely going to fuck this Servant before the end of the day.
 
Grinning wickedly, Shigure gives a nod of assent and gestures with a hand.
 
“Sure, that sounds like a lot of fun. Go ahead and lead the way, will you?”
 
Ōi brightens considerably, nearly standing on her tip toes as she turns around and skips off, proceeding to do just that. As Shigure follows after her, he reflects that no matter what happens next, this will certainly be interesting…
 
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… He takes it back. Sprawled on his side on a couch, stretched out and nude, Shigure is pretty sure he’d have developed a visible sweat drop by this point of this were some sort of anime or something. They’re back in Ōi’s art studio, which of course also doubles as her quarters… and the Servant has pulled out various tools, as well as a truly massive block of wood.
 
“I’ll need you to stay still for the next twelve hours so that I can get the carving juuuust right, Mastaa-dono! So, from here on out, don’t move a muscle!”
 
“Ōi! I can’t possibly spend that long just sitting here. You know how important my duties as the Master of Chaldea are! Not to mention meals and bathroom breaks would be a must at the very least… but no! I do not have time for you to make a wood carving of me! What, are you not a good enough artist to paint on canvas?”
 
Let it not be said that Shigure doesn’t know how to manipulate people. Not that anyone was saying that. In fact, most people who knew the young Master of Chaldea closely knew just how good he was at manipulation. Regardless, his taunt lands perfectly, causing Ōi to pout at the insinuation. She tries to level a faint protest, but Shigure just levels a raised brow at the female Servant until she relents, silently telling her with his gaze that if she didn’t capitulate, he was going to leave.
 
The big block of wood is snatched up and put aside, as are her carving tools. Ōi exchanges those for a canvas, easel, and paints, still pouting slightly, but already starting to get that interested look in her eye again, even as she begins mixing some of her colors together, eyeballing him and preparing lots of different fleshy tones to properly convey his nude, defined body.
 
“Okay… here I go. Stay as still as possible, Mastaa-dono!”
 
As she begins to paint, Ōi focuses on her work, getting a determined sort of look on her face, one that spoke of seriousness and concentration. She even sticks her tongue out a little bit to the side. Occasionally, she leans out from around her easel to examine Shigure’s body before returning to the painting. This happens quite a bit, but to Shigure’s surprise, the Servant is nothing but professional as seconds turn into minutes and minutes slowly turn into half an hour, and then an hour.
 
It was almost as if she HADN’T been speaking in innuendo when she invited him here for a nude portrait. Unable to help himself, especially after the first hour of painting comes and goes, Shigure decides to tease Ōi a bit. So far, she’s not reacted in any visible way to Shigure’s admittedly attractive body. He KNOWS how attractive he is, to put it bluntly.
 
So, casually, the next time Ōi peeks out from around the easel, Shigure teases her, shifting his hips slightly and giving her a grin as he nods down to his cock.

 
“So… what do you think of it?”
 
To his surprise, Ōi immediately smirks at him, almost scoffing as her eyes twinkle with mischief.
 
“I’ve seen bigger, Mastaa-dono.”
 
It takes him a second to comprehend what she means, because really, not only is he preeetty sure she hasn’t, he’s not sure how she COULD these days, with him having the only dick in all of Chaldea. But he figures out what she’s talking about, and it causes him to let out a bark of laughter as he grins wickedly at the female Servant.
 
“And was it made out of flesh… or wood?”
 
Ōi blushes a bit at that and immediately retreats back behind her easel and canvas, letting Shigure know that he’s right on the money. Anything bigger that she might have seen was almost certainly either a carving of some sort, or a wooden dildo. Deciding that he loses nothing by pushing his luck, Shigure continues the banter, even as Ōi hides behind her easel.
 
“I bet that I’m bigger than even those ones… when I’m erect. Right now, I’m completely soft. It’s not a fair comparison, now is it?”
 
That gets a reaction from her. Ōi leans back out from behind the easel again and while she’s blushing lightly, she also scoffs at him.
 
“I doubt it. You can’t get that much bigger than you already are, Mastaa-dono…”
 
Hook.
 
“Oh? Well, I could show you… if you show me. I need a bit more than just the presence of a beautiful girl to get going, really.”
 
Shigure just leaves it at that, and for a moment Ōi doesn’t look like she’s going for it. Then, Katsushika makes his presence known, the small floating squid creature that Shigure knows is also Ōi’s father (somehow) floating and bobbing around in the air next to Ōi. It’s obvious that he’s speaking to his daughter telepathically, and though Shigure can’t HEAR him… he’s definitely animated about whatever he’s saying.
 
The young Master of Chaldea gets an idea of just what that might be when Ōi, blushing even more than before, reaches up and lets her kimono slip down a bit, flashing Shigure with a tit, which she then leaves revealed as she averts her eyes from his face, clearly embarrassed. Not so embarrassed that she’s averting her gaze from his body altogether though, instead, her eyes seem focused solely on his cock.
 
Shigure, grinning at Ōi’s minor bout of exhibitionism, watches her reaction as his cock starts to harden from the pretty girl currently exposing herself to him. Ōi’s blush deepens with each inch that his cock grows, and her jaw slowly drops open in shock as her eyes widen slightly. Shigure doesn’t even need to hear her say it. It’s quite obvious that he IS in fact bigger than the ‘other ones’ Ōi has seen.
 
As a bit of drool runs down her chin, it’s obvious to Shigure at least that she’s beginning to realize just how he managed to charm so many of his other Servants. And more than that, he can see in her eyes that she wants to take him for a ride. That’s perfectly alright with him, given that he’s been wanting to fuck her since they arrived back in her quarters… nay, even before that.
 
Standing up in something of a daze, Ōi abandons her painting for the time being, stepping out from behind the easel and canvas altogether. Her kimono slips down even further, but she pays it no mind, allowing both of her gorgeous titties to be revealed, even as she reaches down and pulls the skirt of the Japanese garment away to reveal the fact that she’s not wearing underwear… and to reveal her dripping cunt.
 
As she walks towards Shigure with single-minded intent, Ōi doesn’t notice her father taking her spot at the easel as he picks up her paintbrush with his little octopus appendages. Shigure does, just barely, but he’s far more focused on the utter vision of beauty in front of him to care about that. Moving from his lounging position on his side to laying out across the couch on his back, Shigure presents himself to Ōi just as she arrives in front of him, taking her by her waist and helping her up as she climbs aboard and crawls into his lap.
 
He doesn’t force the situation or anything though, much preferring to just sit back and watch as Ōi takes hold of his cock and positions it underneath her. She’s still blushing mightily, and her breath hitches slightly as she slowly impales herself on his dick, pressing the head of his massive member into her dripping wet pussy lips and then forcing herself to sink down on his meaty shaft.
 
To her credit, even as it’s obvious that she’s struggling, Ōi never gives up. She never once pauses or hesitates either, as she’s burying his cock in her drooling quim, and stretching out her pussy over his girthy length. Despite this being the biggest phallus Ōi has ever seen or taken, be it fleshy or wood, the artist handles his shaft with aplomb… well, as much aplomb as she can manage.
 
Lying back, Shigure plays a somewhat passive role, as Ōi finally fits almost all of his cock inside of her, only stymied just a tad by the fact that she’s bottomed out, his cockhead now pressing up against her cervix and the entrance to her womb. Once she hits that end point, Ōi begins the process of pulling herself back up his shaft again, her inner walls positively clinging to his shaft, and milking him for all their worth.
 
She hasn’t even gotten started yet, and already Shigure finds himself having to hold back a groan from the feel of her wet, clenching insides around his shaft. He does it though, not wanting her to think that she’s getting to him in any way this early on. Instead, Shigure keeps his cool, while Ōi visibly and steadily loses her own. She starts with riding him, once she’s gotten the first few impalements down and her insides are a bit less tight. Bouncing up and down on his cock, Ōi’s exposed tits do the same, bouncing and jiggling with every thrust, right in front of Shigure’s eyes.
 
There’s no denying that the view is hot, but still Shigure keeps himself under control, his hands resting on Ōi’s hips, but not gripping too tightly. He’s not in control here, she is… and that’s just fine, for now. Eventually, Ōi lets out a gasp and climaxes atop his member. Falling forward, the beautiful Servant plants her hands on his chest and hangs her head for a moment, her bangs obscuring her face. Eventually though, she looks up, biting her lower lip and flushed with arousal.
 
“A-Ah… your cock is much better than any of the toys I’ve used, I-I’ll admit. Mastaa-dono has the biggest dick of all… I should not have doubted you…”
 
With that admission, Shigure gives Ōi a bit of a wicked grin, and promptly tightens his grip on her hips. Then, he begins to thrust upwards. Ōi’s eyes widen as she finds herself going from riding a tamed mount to bouncing up and down at a faster and faster pace on a bucking bronco. She yelps, and she eeps, and she moans wantonly as she’s fucked from below by the very cock that she’d just proclaimed, ‘the biggest dick of all’.
 
Shigure can’t deny enjoying watching her face contort in pleasure as he pulls orgasm after orgasm out of her. But he also can no longer deny himself those glorious titties right in front of his face. Reaching up with one hand, Shigure grabs and squeezes one of the female Servant’s big fat breasts, groping it and kneading it for a moment before giving it a gentle smack and moving onto the next.
 
Each time he does so, Ōi cries out, tossing her head back and pushing her bouncing, jiggling titflesh all the closer to him. Seeing this as an invitation to do as he likes, Shigure moves BOTH hands to Ōi’s chest, grabbing hold of her breasts and molding the soft boobs in his hands, before ultimately leaning up even as he draws her down, so that he can place his mouth over each of her tits, suckling and slurping and lapping at her nipples.
 
All the while, he continues to thrust up into her from below. Though, with his focus now divided between fucking her and sucking on her tits, Ōi is able to get a bit of her self-control back, and soon it’s a mixture of her riding him and him thrusting upwards, the two of them engaging in mutual, hot cowgirl sex for the next little while. Both of them work up quite the sweat like this, as Ōi’s insides clench and squeeze around his cock, and Shigure’s member slams up against her cervix, until finally, he busts right through it, and directly into her womb.
 
Ōi climaxes on the spot as this happens, her eyes rolling back in her head and her tongue sticking straight out of her mouth in a temporary ahegao. It’s in that moment, with Ōi’s battered but still insanely tight cervix constricting the fuck out of his dick right alongside the rest of her insides, that Shigure tips right over the edge and cums as well, her pussy milking his release right out of him.
 
His seed paints her insides white, his cum filling her womb to the brim, and together the two of them reach the heights of nirvana for a long moment, before finally coming crashing down at the same exact time. Reaching up, Shigure slides a hand through Ōi’s hair and pulls her into a deep, tongue-filled kiss, before letting her go with a cheeky grin on his face.
 
The female Servant returns that grin, even as she climbs off his dick, completely satisfied for the time being, and undeniably addicted just like every other Servant that Shigure has fucked at this point. As she slides off of his lap, he moves back onto his side and lounges on the couch with his spent cock resting against his thigh, watching her go. With her kimono still bunched up around her waist, he gets to watch as her heart-shaped butt jiggles and her hips sway with every step. His seed is already starting to drip down her inner thighs.
 
Of course, focused as he was on the Servant’s bountiful behind, he notices the moment that she freezes up upon coming around to stare at the front of her unfinished painting. Or at least, it was supposed to still be unfinished. Judging by the wide-eyed expression on Ōi’s face, Shigure was going to want to see this. Grinning lightly, the young Master of Chaldea hops up onto his feet and begins making his way over.
 
He arrives just in time, because Ōi has become extremely flustered by the time he walks up, and she’s even reaching out towards the canvas, likely to hide it or something. But she’s not fast enough, Shigure sees what’s happened while she and he were busy enjoying one another. In the time that Ōi has been gone from her station, Katsushika has gone ahead and completed the painting in her stead… while also adding Ōi into the painting in a rather compromising position atop Shigure, riding him to kingdom cum.
 
Before Ōi can snatch the painting up and either hide it away or destroy it (probably the former, Shigure thinks she’d like it if she could have it all to herself) Shigure reaches out and snatches it away instead, using his height to pull the canvas right off of the easel and over the short-stack of a Servant’s head. Ōi lets out a noise of protest in the back of her throat as she whirls around to look at him, finally noticing his presence, but Shigure just makes a big show of eyeing the painting and admiring it for a long moment before grinning wickedly.
 
“It’s perfect, darling. In fact, I think this masterpiece belongs on the wall in my quarters. Thank you for the exquisite afternoon, Ōi.”
 
“A-Ah… you’re welcome, Mastaa-dono…”
 
It’s clear that Ōi is both immensely embarrassed, and fairly pleased by his response. After all, at least half of the painting IS her work. Meanwhile, Katsushika is just all pleased, judging by the way the little floating octopus creature is flying and zipping around. Shigure just chuckles and shakes his head, making his way out of Ōi’s quarters and back down the hallway towards his room, freshly finished painting in hand.
 
It was always fun to break in a new Servant… and always nice when they brought something new to the table like Ōi and her artwork did.

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