Chaldea Subjugation Organization (Fate/Grand Order)

Sitting behind his desk in the office he’s claimed for himself, the young Master of Chaldea watches as Cleopatra steps into the room, a clipboard in her hands and held close to her chest. This particular Servant was an odd one, to be sure. He still hadn’t fucked her yet, though not because she was ugly or anything like that. In fact, Shigure would say that, of his Servants, Cleopatra was easily in the top ten. Though in all fairness, practically all of his female Servants, which after Merlin’s tomfoolery was ALL of the Servants in Chaldea, were in the top ten. There were a lot of ties.
 
Regardless, Cleopatra had taken it upon herself to appoint herself as Shigure’s secretary, which meant that every single morning, they met in his office so that she could read out his schedule for the day. It was… fine. Even if Shigure was pretty sure he was going to bend her over his desk one of these days and fuck her like a porno secretary…
 
As prim and proper as ever, Cleopatra stops at the side of his desk, and looks down at her clipboard.
 
“Now then, Master. I shall read out the day’s schedule. Ah, but first!”
 
And then, as if she’d read his mind, Cleopatra proceeds to set her clipboard down for a moment, hook both of her thumbs into the waist band of her shorts and drag them down her legs. She slides them to her knees and then does the same with both her tights and her panties, before bending over his desk right then and there, her elbows pressing into the wood and her hands holding out her clipboard in front of her.
 
Her back arches, and her cute pale tushie sits high in the air as a result, wiggling back and forth a little as Shigure just… gapes at her. HAD she read his mind, somehow? Was she teasing him or something? He didn’t think psychic was in her list of abilities, and now he was a little concerned. Best to just play dumb, he ultimately decides.
 
“… Cleopatra, what are you doing?”
 
The dark-haired Servant looks up from her clipboard rather innocently, blinking at him in surprise.
 
“Well Master, I’ve been researching how a proper, modern secretary performs their duties. In all the videos I’ve watched, the secretary almost always, without fail, ended up bent over their superior’s desk, being fucked by said superior! As I’ve appointed myself to be your secretary, I consider it my duty to emulate modern secretaries. If I’m not properly doing my job, then what am I even here for?”
 
Giving him a wide smile, Cleopatra wiggles her ass again.
 
“Go on Master! Go ahead and stuff both my holes while I read out your schedule for the day, alright?”
 
For a moment, Shigure hesitates… and then of course he stands up and begins unbuckling his belt. Cleopatra’s smile only grows wider at that, and she looks back to her clipboard, even as he gets into position behind her. She has the cutest little behind, and on top of that, the most gorgeous thigh gap. Shigure licks his lips and then applies some saliva to his fingers before bringing them up to her mound, checking to see just how wet and ready she is for him.
 
As it turns out, Cleopatra is VERY wet and ready, his saliva not even needed as he slicks his fingers across her drooling slit and pushes them in for a moment. The self-appointed secretary lets out a soft gasp as he does so, followed by a throaty moan. But she didn’t ask him to finger her, she asked him to FUCK her. And even if Cleopatra’s idea of what a modern secretary was had very obviously come straight from the copious amounts of secretary porn that could be found on the internet, Shigure wasn’t the kind of man who was going to say no to sex.
 
Bringing his fingers back, Shigure grasps his cock and places the head of it at the entrance to her cunt. Then, he thrusts in. She’s nice and tight and hot, and he groans as he grabs her by the hips to hold her steady while he sinks into her, inch by fucking inch. Once he’s truly, properly buried in her, Shigure begins to thrust, moving in and out, pounding into Cleopatra’s cunt, fucking the Servant just as she’d asked of him.
 
Only once he’s buried in her sopping wet quim does Cleopatra actually start to read out his daily schedule.
 
“Mm, t-there we go, Master. My body is yours to use as you please~ Fuck my holes however you like! Now then, onto the daily schedule. First up, as always, is an hour of administrative paperwork. Of course, now that I know I’ve been failing in my duties as your secretary, I’ve gone ahead and made sure to spruce that up a bit…”
 
As she continues on, Shigure is man enough to admit that he tunes her out. To be fair, he almost always tunes her out anyways most days. After she’s done telling him what his schedule for the day is, Cleopatra leaves behind the paper she’s been reading from on his desk, allowing Shigure to just consult it all day long to find out what he’s supposed to do next. Truth be told, these little morning meetings have mostly just been so that he can stare at her tits while she’s speaking, and her ass and thigh gap as she walks away.
 
At least now he has a better reason for not bothering to pay attention to her reading off of her clipboard. He’s buried inside of her tight, hot cunt, and giving it any less than his utmost attention would just be plain RUDE. Shigure grins as he grips tightly and fucks harder. There’s something to be said about fucking his secretary in his office while she tries and ultimately fails to maintain her composure. He notices that, of course. He may be barely paying attention to the actual words coming out of her mouth, but at the very least, he listens to how her breath hitches, how moans cut her off in the midst of what she’s saying, how she has to start and stop time and time again to try to get the words out.
 
Shigure just keeps right on fucking her. After all, he was INVITED to fuck her. He was told that this was what a modern secretary did for her boss. Well, Shigure was all too happy to help her with that, and all too happy to take advantage of Cleopatra as the Servant bent over his desk and read off her clipboard. Eventually though, she gives up on it. Or maybe she just finishes with his schedule. Normally, this part of the morning takes about ten minutes, altogether. Needless to say, Shigure isn’t the kind of man who only goes for ten minutes, and he never will be.

 
“O-Oh, you’re still… s-still going, Master. Mmph, please, a-ah, don’t take t-too long, I do have, ooh, other duties to, hah, attend to.”
 
Shigure scoffs at that and reaches forward, taking hold of Cleopatra’s hair, as well as the cross between a headband and a crown that she wears atop her head. Gripping tightly, Shigure tugs back, forcing her to arch her back as her head is tilted upwards. His other hand comes down with a light swat on her pale, exposed butt cheek, and then it’s followed by another swat, and another. As he spanks and fucks his secretary to his heart’s content, Shigure leans in close and growls in the Servant’s ear.
 
“Tell me, my dear, in all the videos you’ve watched, do the secretaries EVER try to order their bosses around?”
 
A whimper leaves her throat, and her cunt tightens up quite noticeably around his cock. When she answers, its with a breathless tone.
 
“Mm, some do, Master… they always get punished right afterwards, though.”
 
Snorting derisively, Shigure leans back again, letting go of her hair and going right back to fucking her as he bends her over his desk. Cleopatra moans, and she even climaxes around his cock a couple times. That’s what finally puts him over the edge, the fact that she’s enjoying this as much as she wants to pretend that it’s only for his benefit. With a low growl, Shigure proceeds to unload deep within Cleopatra’s cunt, pumping a nice thick load of seed right up into her hot, wet pussy.
 
She moans throatily and arches her back again, before collapsing forward as he slides his messy cock out of her. For a moment, she just lays there on his desk, collecting herself. Then, she tries to stand up. Shigure is waiting for this, of course. He plants a hand between Cleopatra’s shoulder blades, and presses his secretary back down onto his desk, while using his other hand to hook up under her hips and hike her cute little ass higher up into the air.
 
“O-Oooh! Master~”
 
“You did tell me to stuff BOTH of your holes, sweetheart. Did you think I would leave the job only half done? As you said, this is a VERY important part of the modern relationship between a secretary and her superior. If it’s not completed to the letter, well, who knows what might happen?”
 
And then, rather unceremoniously, Shigure shoves his lubed-up prick right up Cleopatra’s asshole. She squeals in a most satisfying way as he does so of course. As he’s discovered, even most Servants aren’t really prepared or used to anal. But luckily for her, his dick is already covered in a copious amount of cum and pussy juices. Meaning, even as tight as she is, that Shigure is more than able to slip his way inside of her, splitting her back door open on his fat cock.
 
“Oh! Oh, oh, oh! I-I didn’t know that it would be like this, Master! A-Ah, you’re much bigger than most men I’ve had! The biggest I’ve ever had in my ass~ Don’t stop, Master! Don’t stop!”
 
Shigure doesn’t, of course. He has no intentions of doing so. Though, as he fucks Cleopatra’s anus, the self-appointed secretary still bent over his desk, he does find himself growing a little suspicious. Reaching forward again, he once again drags Cleopatra’s hair and gold headband backwards, forcing her to arch her back most delectably so he can look down into her eyes.
 
“… Is talking up the size of my cock and pretending not to be familiar with anal something you also learned from those videos of yours, Cleopatra?”
 
In an instant, her face goes from an ahegao to a bright smile as her eyes roll forward in her head again and she looks up at him.
 
“Mm, yes Master! I hope I’m doing a good job! In the videos I watched, the secretaries didn’t actually sound all that convincing. I’m fairly certain I’m a better actress then all of them though, by far. What do you think?”
 
Given she had him fooled for a few seconds there, Shigure can’t deny that she definitely did a better job then most pornstars could have hoped to achieve. Chuckling, the young Master of Chaldea just shakes his head and pushes Cleopatra back down. Then, he settles in and proceeds to give his tasty little treat of a secretary the butt-fucking she deserves. She moans and groans and squeezes down on his cock with her anal muscles as often as she can, and Shigure can’t deny that he has the time of his life, fucking the sexy, tarty minx nice and hard. He pounds into her extremely tight ass just like he pounded into her cunt, and after a little while longer, he eventually cums inside of her, pumping a nice, thick load of seed right up into her ass.
 
With both of her holes well and properly stuffed, Cleopatra once again moves to stand up, this time, Shigure doesn’t stop her, though he also doesn’t sit down immediately. Instead, he steps back and watches, curious to see what she’ll do. Without a single ounce of hesitation, the self-appointed secretary reaches down and pulls her panties, tights, and shorts back up her legs and over her pale bottom, in that order. She doesn’t seem to overly mind much that his viscous seed is already slowly dripping out of both her slit and her back door, making her crotch almost certainly sticky.
 
It’s rather hot, watching her commit to ruining her clothes and holding his seed inside of her for the rest of the day. Shigure grins as he moves back to his desk and prepares to tuck his cock away, but before he can do so, Cleopatra speaks up.
 
“Ah, what are you doing, Master? You might as well leave that out, given your next task is administrative paperwork.”
 
Shigure blinks, and lifts an eyebrow at his self-appointed secretary, rather proud of himself for silently conveying his question most clearly. Or at least, he thinks he does. Cleopatra on the other hand looks rather nonplussed at him, before pouting mightily.
 
“Did you not listen to my reading of your schedule, Master? Ugh, that’s so typical!”
 
Then she claps her hands, and the door to his office opens up once more to admit another woman. But not one of his Servants. Rather, instead, Gudako walks into the room, and the orange-haired, extra-dimensional lewd girl is certainly dressed to impressed. Wearing a set of red lingerie that cups both her ass and her tits beautifully, Gudako sashays her way inside, looking like a strong, seductive woman… until of course, she opens her mouth.
 
“Gudako here to service her Onii-chan’s needs! It’s up to me to suck Onii-chan’s cock and keep his libido in check for the duration of his administrative paperwork! That way he doesn’t wander off to fuck someone else when he should be working!”
 
On top of that, she strikes a pose as well, giving a peace sign and showing off a mixture of a side profile and her ass as she presents herself to him, grinning wickedly. The orange-haired doppelganger is as crazy as ever, of course, but Shigure has long since gotten used to that, as well as learned how to put that crazy to good use. However, now it seemed that Cleopatra had learned it as well. When he looks to his self-appointed secretary, she seems inordinately pleased with herself.
 
“As your secretary, part of my duties are also to keep you on task, Master. I’ve noticed that more often than not, you have quite a lot of difficulty getting through all of your administrative paperwork when it needs to be completed. And more often than not, that’s because of your entirely insatiable libido. Now, before I thought that as your secretary, your sex life and taking care of THOSE sorts of needs was not my concern. But now with the research I’ve done, I realize I’ve been slacking in my duties!”
 
She takes a deep breath, and then continues.
 
“Essentially, I’ve failed to properly take into account your needs, Master, but now that I know better, I’ve gone ahead and assigned Gudako here to give you head while you do your paperwork, so that you won’t get distracted and wander off like usual! Please, have a seat. Gudako will join you under the desk.”
 
Shigure… isn’t sure how to feel about all this. While yes, he did tend to skip out on the paperwork sometimes to go and find a Servant to fuck instead, he didn’t think it was that big of a deal. And he certainly hadn’t expected Cleopatra to go this path when trying to make sure he got all of his work done on time. Slightly nonplussed, but undeniably aroused once more by Gudako’s general appearance, the lingerie skimpy and flowery and lacy in all the right ways, Shigure moves over to his desk and sits down.
 
Gudako all but prances over, a big wide grin on her face as she hurries to where he’s sat and then sinks down to her knees. Leaning forward, the red head takes Shigure’s cock in her mouth all the way to the base, and THEN scurries under the desk, turning him with her as she goes so that she never quite loses his juicy member. Once she’s properly ensconced beneath his desk and his seat has been pulled in by sheer virtue of her inhaling her ‘Onii-chan’s’ cock down her throat, Cleopatra steps up to his side. She takes the piece of paper outlining the day’s schedule off of her clipboard and places it on his desk, making sure to stretch blatantly, putting her chest right in his field of view as she does so.
 
“Aaaand, here you go, Master. Mm, as always, I’m happy to be of service! I’ll be back the next morning to give you your daily schedule once more, and to have my holes stuffed with your cock and cum yet again. Until then, Master.”
 
Before she can walk away, Shigure reaches out and gives Cleopatra’s ass a firm spank, turning it into a grope afterwards as he first smacks, and then squeezes her ass cheek nice and hard. His fingers, digging into her shorts and her flesh, can already feel a bit of dampness as his cum soaks through her panties, tights, and shorts.
 
When she gasps and looks down at him, blushing slightly, Shigure just grins up at her.
 
“You’re the best secretary ever, sweetheart. Thanks for everything you do for me.”
 
That puts a proud smirk on Cleopatra’s face, and she wiggles her ass in his grip for a moment longer as she holds her head high. Shigure lets her go a second later, and she lets out a soft ‘hm’ sound as her eyes sparkle with pride.
 
“Well, of course I am, Master! Though it’s nice to hear you say it~”
 
Then, she circles around his desk with her trusty, now-empty clipboard in hand and begins heading for the day, swaying her ass back and forth as she goes. Shigure watches her leave for a moment, before groaning as Gudako hits a particularly sweet spot with her tongue, his cockhead currently tickling the back of her throat.
 
Leaning forward, Shigure begins working his way through the administrative paperwork in front of him. As it turns out, Cleopatra’s tactic for getting him to finish his work is quite good indeed, though perhaps not entirely in the way she thought it would be. Oh sure, Gudako’s throat feels very good, wrapped around his throbbing cock. But in the end, what motivates Shigure to finish all of his paperwork as fast as possible is so that he’ll have more room on his desk for when he lays Gudako across it and fucks his darling ‘imouto’ to kingdom cum.

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