Chaldea Subjugation Organization (Fate/Grand Order)

It’d been a tough battle, but nothing truly special. In the end, Shigure was far more invested in what came after the fight, since he’d finally managed to obtain enough Material to Ascend one of the cutest of his Servants to her Fourth Stage. It was a little amusing to consider that he hadn’t touched her yet, given just how adorable he found her, but in the end, it was true.
 
Kuro gasped as the light surrounded her, swirling this way and that. It was just him and her in the ritual room as he Ascended her, and once it was all over, the petite, dark-skinned girl squealed with delight as she bounced this way and that.
 
“Thank you Master! Thank yo-!”
 
Her voice immediately cuts out as she notices his amused look. And just like that, the tiny little Servant is all business as she lifts her nose and adopts as solemn a tone as she can manage.
 
“Hm. To think you’d bring me this far… you really are a persistent one, Master.”
 
Then, she blushes a bit as she looks to the side.
 
“F-Fine… just this once, I’ll let you have a peek.”
 
Shigure raises an eyebrow at that but doesn’t otherwise respond. When Kuro sneaks a glance to see his reaction, she blushes even harder under the sight of that lifted brow.
 
“J-just… let’s go to my room first, okay?”
 
She doesn’t want for him to agree, instead the short Servant dashes forward and grabs him by the hand, blushing all the more profusely as she interlaces her fingers in his. Shigure grins, as amused as ever as he lets her guide him through the halls of Chaldea, all the way to her bedroom. Once they’re safely ensconced in Kuro’s quarters, only then does the dark-skinned Servant step away from him, moving to the center of the room as she begins to remove her coat and her armor.
 
Heh, she’d already been dressed in a rather risqué manner to begin with. That skimpy leather armor, that billowing cloak that did nothing to hide the amount of beautiful, caramel flesh she liked to have on display at all times. Ah, but without it Shigure could admit that she was even sexier. Her cute little front-tied bra over her tiny tits was even smaller than her leather armor tube-top, and her side-tie panties revealed much more of her delicious thighs and slightly curved hips than the battle skirt she wore did.
 
Yes… this was worth the wait. While he probably could have had Kuro at any time, like he’d had so many other female Servants… there was just something about her that had him taking things more slowly. Like he had to earn her or something. She was quite pure, in a way. Innocent… cute as all hell. Licking his lips, Shigure moves forward as Kuro stands there, blushing lightly and shifting under his gaze.
 
She’d told him it was just a peek, but Shigure wasn’t the kind of guy to settle for such a thing… he wondered whether or not Kuro knew that when she’d offered it, whether she meant for him to take more. In the end, it didn’t matter, though when he placed her hands atop her flat chest and slowly massaged her bra-clad tits, she didn’t try to stop him. Instead, the girl moans in an incredibly sultry manner, squirming in place but not making one single movement towards escaping his grasp.
 
With the nonverbal consent obvious, Shigure sees no reason not to take things further. One of his hands leaves one of her small breasts, and Shigure tugs almost reverently at the bowtie holding her cute little black bra together. Sliding the string out, and undoing the tie, he grins all the wider as he lets go and watches her bra fall off to reveal her small boobs and her cute little pink nipples.
 
The dark-skinned Servant blushes deeper still, her lips parting and her breath hitching as he casually plays with her now-exposed chest outright, kneading her miniscule tit flesh and tweaking her nipples as he likes. She’s panting in short order, staring down at his hands, squirming in place, her inner thighs rubbing together in a way that tells Shigure exactly what’s happening down between her legs.
 
Still, he’s taking things slow and enjoying things in his own time. That means not skipping ahead. He spends the next few minutes simply enjoying Kuro’s small chest, and only after she’s whining and squirming much more in his grasp does he acquiesce to her desires, trailing his hands down off of her tiny tits to move along her sides, all the way to her waist.
 
His fingers ghost across her caramel flesh and Kuro shivers, even as Shigure watches her, taking in every reaction, every blush and moan, his fingers find the side-ties of her panties. Just as reverently as he had with her bra, Shigure pulls, tugging gently until finally the bowties come undone there as well. Kuro’s last garment falls to the ground without a fight, and her tiny, leaking pussy is on full display as Shigure watches her drip onto her already soaked panties that now later on the floor at her feet.
 
He’s just getting ready to draw her in for some more foreplay with Kuro finally does pull out of his grasp, slipping from his hands with ease, since he hadn’t truly been trying to keep her in one place. The corners of Shigure’s mouth turn down slightly in a confused frown, but Kuro’s intentions become clear a moment later as she practically flounces over to her bed, plopping her cute little ass down and spreading her legs wide as she runs her hands down her thighs.
 
The cute little Servant gives Shigure her best sultry grin, and a moment later, beckons him over without a word. Shigure doesn’t need words though, not to go to her in this moment as he already most certainly wants to. His clothes fall off of him in short order, dropped in a trail as he makes his way from the center of the room over to Kuro and the bed she’s waiting upon for him.
 
By the time he crawls onto the mattress and over her, he’s naked and the dark-skinned imp is staring down at his cock, her lips parted and her tongue slipping out unconsciously to lick at them. Shigure moves so that he’s on top of his teeny, tiny Servant, and then he reaches down with one hand and guides his thick, throbbing prick to the entrance of her small slit.
 
Leaning in with his other hand planted palm down next to her head, Shigure captures Kuro’s lips in a kiss, even as he thrusts into her tiny, virgin cunt. The Servant squeals for a moment and at first, Shigure has the upper hand… or tongue, in this case, as his flexible mouth muscle slips in between Kuro’s lips and into the beautiful girl’s mouth.
 
But if there’s one thing the Servant does know (and she knows it quite well) it’s kissing. In truth, all of Kuro’s sexual and romantic experience can come down to kissing and kissing alone. As soon as she’s recovered from the experience of having Shigure inside of her, fucking her, Kuro begins to give as good as she’s getting, her tongue wrestling with his as she applies her extensive kissing experience to give him the best makeout session of his life.
 
Her small arms wrap around Shigure’s neck, and her tiny legs try to do the same with his waist, though she’s too short to get her ankles locked together behind him. Shigure doesn’t pay much attention to that though, focused solely on his cock filling Kuro’s cunt, piercing through her cervix and into her womb with each and every thrust.
 
As a Servant, she was made of hardy stuff of course. There was no pain, after the initial breaking of her hymen. All there was in that moment was pleasure as her Master finally paid her the attention she deserved. Kuro moans into Shigure’s lips, and he in turn grunts into hers as he slowly increases his pace, fucking her with harder, deeper thrusts that stretch her womb almost like a condom around his cock.
 
Eventually, the two of them break their kiss, as Shigure needs air. A strange of saliva still connects them, even as both of them pant heavily. Kuro’s eyes are quickly glazing over with lust, while Shigure’s are hooded as he stares down at the cute little Servant.
 
“You… you are an amazing kisser, Kuro.”
 
It’s the right thing to say, going off of Kuro’s answering blush and beaming smile, even as she answers him between the moans and grunts as he continues to fuck her.
 
“N-Not… so bad… mm, you’re a good kisser t-too, Master… oooh, but I’m not full yet~”
 
Her arms, which had loosened around his neck when he’d pulled back, tighten up again as the teeny, tiny Servant brings him back down to her for another kissing session. Shigure just chuckles as she goes back to draining prana from him through kissing. He’s connected directly to Chaldea and all the prana that comes with it, so the young man isn’t too worried about her draining him dry.
 
In fact, rather than getting pissed at Kuro’s audacity, what with her controlling actions and the way she was latching onto him and wrapping herself around his form and refusing to let go, Shigure finds himself enjoying her boldness as he returns the kiss once again. Normally, he might have been annoyed or even irritated. He might have even tried to get even.
 
But this was coming from a good place, and he knew that. Kuro was too innocent to really understand power dynamics or politics or anything of the like that could play a part in how someone acted during sex. Her thoughts were more along the lines of ‘I want to be fucked and kissed more, so let’s make sure the man fucking and kissing me won’t escape’.
 
Shigure could respect such simplistic desire. More than that, he honestly kind of loved it. Reaching down as he continues to tongue-wrestle with the cute little Servant currently impaled on his cock, Shigure grabs hold of Kuro by her hips and pushes her body up just a bit off the bed, using the leverage and the slight change in angle to thrust even deeper down into her tight cunt. His cockhead slams into the back of her womb with every thrust, and in no time at all, Kuro is experiencing her first orgasm… and then her second and her third and…
 
Well, she’d already been close when he changed things up a little. It wasn’t too surprising that his new position would leave her fucked silly by his giant cock. Shigure grunts as he pounds into the dark-skinned Servant’s womb, feeling her walls, her pussy lips, her cervix, and even her womb itself tightening and squeezing down around him.
 
Slowly but surely, Kuro’s tongue gets less and less active, as do her kisses. He’s not giving her much time to recover after all, and in point of fact, he’s actually fucking her harder, deeper, and faster than ever before. Shigure watches from mere centimeters away as Kuro’s eyes roll back in her head. He can feel her tongue hanging out of her mouth, lulling around in his own as he slides the slippery mouth muscle this way and that with HIS tongue.
 
That’s around the time when her pussy walls and her hot, wet insides finally milk his release from him. Shigure’s seed fills Kuro to the very brim and then some, pumping into the tiny Servant’s equally tiny womb until her small abdomen is more than a little bloated. By the time he pulls out, Kuro is already looking just a tiny bit pregnant, and the young man can’t deny how hot that is, even as he rolls off of her to lie beside her.
 
There’s no words exchanged between the two of them as they simply rest at each other’s sides. There doesn’t need to be, not at this point. Basking in the afterglow, Shigure simply smiles as Kuro presses up against him after a moment, curling into his side and cuddling with him. He wraps an arm around the sweaty, dark-skinned Servant’s small frame, and just lies there, enjoying her company as she enjoys his.
 
By the time the door to the room opens a little while later, both Shigure and Kuro are resting lightly. Their eyes open to the sound of the door though, and both of them look to it as a cute little gasp sounds out. Along with Kuro, Illya and Miyu might be Shigure’s youngest appearing Servants. The cute magic-wielders stop dead at the sight of him and Kuro sprawled out on the bed, both of them naked and sweaty, with Kuro’s pussy leaking cum and Shigure’s cock in plain view.
 
The two sport atomic blushes in unison, but Shigure notes that neither appears to want to run away, or even look away for that matters. Its clear as they fidget and squirm in place, that they’re aroused and intrigued by the sight before them. Well, he’s more than happy to take advantage of that. Before either can decide to flee, Shigure covertly preps two Command Seals, and then looks each of his delicious, petite Servants in the eye as he smiles casually and activates them.
 
“Well? Are you going to join us?”
 
He’s not sure if any of them notice that its an order. Though in truth, once the Command Seals kick in, only Kuro would have been able to tell. Still, it looks quite natural, at least to Shigure’s eyes. There’s a moment of hesitation as Illya and Miyu both blush even deeper shades of crimson. Then, they catch each other’s eye and seem to have a silent conversation for all of a moment before turning back to the bed that Shigure and Kuro are on and nodding.
 
“Y-yes…”
 
“O-Okay…”
 
The two cute Servants move forward and Shigure grins wickedly as they both crawl onto the bed. Kuro moves aside and watches with a wide-eyed blush of her own as her ‘sister’ and their friend take up position along either side of Shigure’s body, working together to pleasure Shigure almost instinctively. It was the Command Seals at work, almost definitely, but that didn’t make it any less delicious as Illya and Miyu worked at his cock and balls with their gloved hands.
 
Eventually, as he grew thicker and throbbed all the harder in their grasp, the two added their mouths and their tongues and their lips to the mix as well, and Shigure watched in blissful enjoyment as the pair of cute, petite Servants plays with his genitals like they were a pair of upper-class whores. It could be said that they were dressed like whores to. Maybe cosplay whores. Heh, with a wide grin on his face, the young man slips a hand under Illya’s skirt and into her panties on one side, while using his other hand to move past Miyu’s leotard-like outfit on the other.
 
He fingers the two cuties most brazenly and they moan into his cock even as they lick and kiss and stroke at his member from either side. Things get even more interesting when Miyu seems to finally work up the courage to go beyond just what Shigure wants of them. She leans over and captures Illya’s lips with her own, surprising the cute white-haired girl as they continue to stroke Shigure’s thick, pulsing shaft.
 
Shigure watches as the two makeout, right then and there, over his dick. That, more than anything else, is enough to send him over the edge, the sight of the two cuties tongue-kissing just too much with the sensation of their gloved hands going up and down his member at the same time. A grunt escapes Shigure’s throat as he cums, and his seed covers their gloves in short order, spurting up and dripping down their hands as they finally part to stare down at his ejaculate all over them.
 
This time it’s Illya who takes initiative, grabbing one of Miyu’s gloved hands and bringing it to her lips. Seeing what her friend and fellow Servant is doing, the other girl does the same, and the pair proceed to lick each other’s gloves completely clean right there in front of him, slurping down Shigure’s seed off of one another’s hands with surprising gusto.
 
Shigure watches this with mild amusement and major arousal, his cock barely even softening partially before it’s back at full mast, standing straight up between them. When Illya and Miyu are finally finished cleaning each other off, it’s Illya who notices his dick is still hard, and the white-haired Servant blushes as she takes initiative yet again, moving away from her dark-haired friend and positioning herself by his side.
 
Lifting an eyebrow, Shigure sits up finally as Illya gets on all fours. His fingers leave Miyu’s cunt as he does so, and the cutie falls onto her back, blushing deeply and biting her lip as she replaces his digits with her own, masturbating until her turn comes as she knows it will. Meanwhile, Illya reaches back and flips up her skirt, exposing her cute little ass, clad in pink and white panties as she kneels there on all fours, blushing deeply and looking at him with clear desire in her gaze.
 
“D-Do it Master… fuck me like you d-did my sister!”
 
Well now, that was probably a latent desire buried deep in the darling girl’s psyche. After all, it wasn’t covered under the Command Seals he’d used, just like Miyu’s decision to kiss her white-haired friend wasn’t either. In truth, the Command Seals he’d used so far had been rather weak commands in general. It was possible both Miyu and Illya could have easily resisted… if they’d wanted to.
 
Smirking slightly, Shigure gets onto his knees and moves into position behind the waiting Servant, ready and willing to give her exactly what she wants. Slipping down Illya’s cute little panties, he takes in the sight of her petite, perky posterior for a moment, and the glistening, puffy pussy lips between her pale, white thighs.
 
Before he can do more than bring his cockhead to her entrance however, Kuro is there, draping herself over him from behind, and whispering in his ear. Shigure listens to what the dark-skinned girl has to say, and for a moment marvels at the relationship between sisters that allowed such a cute, innocent girl to come up with such a… wicked idea.
 
Grinning mischievously, Shigure decides to take Kuro up on her suggestion. He’s quiet, as he uses his last Command Seal to increase Illya’s anal sensitivity. Before she can quite ask him what he’s doing, Shigure has his cockhead pressed against the small girl’s anus, lubed up as it still is from their tongues and the remnants of his recent load, as well as from fucking Kuro.
 
“W-Wait… Master, that’s not… that’s the wrong h-hoOOOOOOOOLE!!!”
 
Shigure cuts her off by fully sheathing his lubed-up prick in her tight, tiny little ass in one single thrust. Well, he doesn’t cut her off so much as cause her to elongate that last word as she immediately responds to his penetration of her anus by ahegaoing on the spot. The Command Seal had done its work, and Illya’s eyes roll back in her head, her tongue hanging out of her mouth as she orgasms EXPLOSIVELY around his dick.
 
Her pussy juices squirt out of her empty cunt and onto the bed beneath her, while her butt muscles try to tighten around Shigure’s dick, trying to push him out or at the very least hold him in place. They fail, ultimately getting stretched out and loosened considerably as Shigure pulls out of his petite, white-haired Servant, only to slam back into her ass once more a moment later.
 
Illya’s tongue hangs out of her mouth constantly, and even when they roll back down her eyes remain unfocused and glazed over with lust. She squeals and moans and cries out as he begins to truly fuck her back door, but it’s clear she’s confused more than anything else.
 
“Nnngh, w-why does it f-feel so good in my b-butt? Dicks aren’t supposed to g-go there…”
 
Shigure laughs and gives her a smack across her petite, pale ass cheek, grinning all the wider as she moans loudly. Another mischievous thought runs through his head, and given Illya’s clearly suggestible state… well, he just can’t resist.
 
“Isn’t it obvious, Illya? It’s because you’re my tight little butt-slut, aren’t you? Mm, my hot, ready-and-waiting anal whore…”
 
Illya moans but doesn’t try to deny it. He fucks her for a few more thrusts before she begins to nod in agreement.
 
“Y-yes… yes! That m-must be it. I can’t… it’s soooo good Master! It’s so good in my butt! P-Please Master, please! Fill my slutty little b-butt with your hot, creamy jizz!!!”
 
She climaxes again from her own crass, slutty language, and with her ass muscles trying to squeeze the life out of his cock, Shigure is more than ready to oblige the cute Servant. Gritting his teeth and grunting as he grips Illya’s petite derriere with both hands, the young man fucks the white-haired girl into the bed beneath them with as much ferocity as he can muster, plowing the durable Servant as hard as he can until finally, he cums deep inside of her ass, filling her ‘slutty little butt with his hot, creamy jizz’ just like she’d demanded of him.
 
Upon sensing this, Illya outright loses it, her back arching and her eyes rolling back in her head one last time as her tongue sticks straight out of her mouth. The resulting orgasm is more explosive in nature than any before it, and by the time she’s come down from the pleasure high, Illya is face down on the bed, collapsing forward off her hands and knees, Shigure’s cock slipping out of her cum-stuffed little behind.
 
Enjoying the view for a moment, Shigure simply stares at Illya’s face down body and licks his lips, quite happy with himself. When Kuro leans in and begins to clean off his cock, he doesn’t even flinch, nor does he react as she slurps and licks him clean. However, when she pulls back he does glance at her, an eyebrow lifted in surprise that she wouldn’t keep going and hog him all to herself.
 
The dark-skinned Servant just smiles and directs him to Miyu. Of course, Kuro was a caring, and giving friend. What a cutie. Chuckling, Shigure turns to the last of his cute little Servants. Miyu blushes deeply at suddenly being the center of attention, but she doesn’t try to hide the lusty look in her eye. She’s panting heavily by that point, and beyond her blush, she’s also flushed with arousal as she pistons three fingers in and out of her cunt.
 
Crawling forward on his knees, Shigure moves to where the cute, dark-haired Servant is masturbating. She stops as he gets close and pulls her gloved digits out of and away from her pussy, leaving her leotard to slip back into place over her sopping wet cunt lips. Bringing her hands up to her small chest, Miyu doesn’t try to resist when Shigure grabs her by her ankles and pulls her legs up. Folding her in half is no problem at all, and as her ankles end up wresting by her ears, Shigure leans over her and rubs his cock directly against her barely-covered cunt as he stares down into her blushing, eager face.
 
Of course, before he can fuck her, he wants to know just how much she enjoyed the show. Finding that out is easy though.
 
“So then… how do you want me to take you sweetheart?”
 
Miyu’s gaze immediately shifts to the side as she glances to her white-haired friend. Illya, face down as she currently is, has her head turned towards Miyu, giving the dark-haired Servant a nice, full view of her friend’s fucked silly face. Blushing all the deeper, Miyu looks down at Shigure’s cock when she answers him, rather than up into his eyes.
 
“I want… I want to b-be your tight, little b-buttslut too…”
 
Shigure laughs at that and slips her thin ankles into one hand as he reaches down and pulls the part of her outfit covering her crotch completely to the side. In the position he currently has her in, with her legs pushed so far back, her cute little rump is already a couple inches off the bed… and it’s the work of moments for Shigure to line his thick, throbbing cockhead up with Miyu’s asshole before plunging in.
 
He’s just as lubed up, if not more so, than he was when he fucked Illya. Kuro was an attentive dick cleaner after all, and she’d left more than her fair share of saliva behind before guiding him to Miyu. Perhaps the dark-skinned girl knew that her friend would want this. Either way, Shigure’s passage into Miyu’s tight little ass is slow going for all of a few moments before he’s buried deep inside of her and moving back and forth to get her looser and looser.
 
Fucking a cute little Servant like Miyu up the ass while in a mating press position is something that Shigure just can’t get enough of, especially when she squeaks with pleasure with every single thrust he makes. Well, when she’s not crying out from orgasm of course. The dark-haired Servant is soon cumming from the anal pounding she’s receiving just like Illya had, and her pussy juices squirt out of her gushing cunt and all over his abdomen as he forces climax after climax out of her.
 
Shigure doesn’t mind though, he has three tiny tongues ready and waiting to clean him up when all is said and done. For the time being, the young man simply luxuriates in fucking yet another of his cute Servants right in the ass, pounding down into her from above as Miyu cums again and again around his cock.
 
Looking down at the dark-haired girl’s blissed out face, Shigure can’t quite help but lean down to capture her lips in a kiss. He spreads her legs wide now that he’s buried deep in her ass, a hand wrapping once more around each ankle as he pushes them back but out of his way. His tongue does its level best to clean Miyu’s tonsils as he dominates the shy cutie’s mouth with a kiss, all while fucking her ass with his cock as hard as he can.
 
It’s in the midst of that impromptu makeout session that Shigure finally cums, his tongue trying to get deep down Miyu’s throat, even as he pumped yet another load of white, hot seed into her tight asshole. He groans into her lips as he fills her bowels with his cum, pumping a nice, thick load of his ejaculate inside of her before he finally pulls out and rolls over into the middle of the bed, panting heavily.
 
He was still human after all, even if his girls weren’t. As Heroic Spirits, they had stamina that he couldn’t always lay claim to. Resting from his veritable sex marathon, Shigure just lays there until Illya, having recovered somewhat from her fucked silly state, climbs atop him.
 
Her pussy juices leak across his abdomen and make his body all the messier as she leans in and bites her lower lip, blushing deeply.
 
“Do I g-get a kiss too?”
 
A slightly tired chuckle leaves Shigure’s mouth, and he laces his fingers through the pale girl’s white locks, before dragging her down to lock their lips together. His tongue slips into Illya’s mouth and he dominates her in the same way he did Miyu, even as she squirms against his chest, grinding her tiny slit and her cute little clit down into her abdomen the entire while.
 
Eventually, Shigure is just plain tired, and ready for a nice long nap. He breaks the kiss and Illya leans back, smiling happily and panting breathlessly as her tiny little chest heaves up and down. Then, she snuggles into his chest even as Kuro and Miyu make their presence known again by snuggling into his sides. As the three cuties cuddle with him, forming a rather warm and messy ‘blanket’, Shigure just smiles contently, and begins to drift off to sleep.
 
Kuro, Illya, and Miya all do the same, quite happy to be so much closer to their Master now. Not a single one of them has any regrets. Not a single one of them would change anything that had happened today. They’re just as happy, just as content as their beloved Master.

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