Chaldea Subjugation Organization (Fate/Grand Order)

He’s alone, as he strolls through Chaldea’s halls. Perhaps that’s why the pair approach him. Just as Shigure is trying to decide if he should summon a new servant or get ‘closer’ to one of his currently summoned Servants, he sees Anne Bonny and Mary Read approaching from down the hall. The pair of pirates were definitely an oddity. After all, since when did a duo register as a single Servant?
 
But that didn’t really matter, in the end. Regardless of their circumstances, Shigure couldn’t deny that the two were both cute, in their own ways. Anne was tall enough that her massive tits were eye level with his head, and Mary was petite, nearly a foot or so shorter than him. Shigure could see himself enjoying either of them… but in the end, it’s Mary who seems to want to talk to him, as her blonde counterpart hangs back with a wide grin on her face.
 
Shigure lifts a single brow in the white-haired petite girl’s direction and stays silent, giving her a chance to make herself heard. Unfortunately, it’s hard for Mary to express herself, as expected. The poor darling stands before him, only a couple feet away, and fidgets shyly as she presses the tips of her fingers together, blushing and averting her gaze from him.
 
After several seconds of nothing happening, Shigure is just about to open his mouth and initiate conversation, when Anne lets out a dramatic sigh and steps up to bat, moving into position right behind her white-haired counterpart and giving Shigure quite the nice view of her barely-contained tits as she grins happily.
 
“Hey master, let’s have sex!”
 
Mary goes an even deeper shade of red, and shrinks into her large coat like a turtle as Shigure blinks dumbly, stunned for a moment by the sheer bluntness that was Anne Bonny. Honestly, the girl was a bit too forward for her own good sometimes… but this wasn’t one of those time. Recovering swiftly enough, Shigure lets out a chuckle and nods in agreement, waving for them both to follow him as he turns and begins to lead them to his room.
 
Anne’s reaction is to shout happily and leap into the air with joy, and Mary’s is to get redder still, even as her taller counterpart grabs her up and carries her along so they can catch up with Shigure’s slowly disappearing form. A glance back is enough to tell him all this is happening, much to his amusement, and slowly, the young man’s member begins to harden in his pants as he anticipates what is to come.
 
Once they’re in his personal quarters, Shigure finds himself regulated to the bed by an insistent, excited Anne, even as the blonde places herself in the center of the room, only to give him a nice, long, sensual strip show. Piece after piece of the legendary pirate’s garb comes off, until she’s pulling her top over her tits, letting them bounce free, and sliding her pantyhose down off of her hips to expose her dripping wet pussy.
 
Shigure can’t help but stare. Why hadn’t he done this before? Honestly, Anne Bonny was probably one of the most sensual Servants he had at his disposal. Perhaps that’s why? There was certainly more pleasure in the chase regarding someone like Scathach, and turning her into what she’d become. But Shigure had the feeling he’d have just as much pleasure in what was about to ensue, as Anne slowly made her way towards him.
 
The tall, top-heavy pirate falls to her knees, and then sits her fat ass right down on the heels of her feet in order to bring her tits down to his crotch level. His lips upturned, Shigure watches as the blonde extricates his hard, throbbing dick from its tight confines, stroking him up and down for a brief moment before wrapping her hefty breasts around his shaft, giving him a boobjob right then and there.
 
Shigure lets out a groan as he throws his head back in sheer enjoyment. Anne giggles at the noises she’s getting him to make, but the next thing he knows, she’s talking to Mary, her attention diverted to the side.
 
“What’re you doin’ Mary?! We’re supposed to be in this together! I guess I’ll be getting all of Master’s nice, THICK cock to myself, huh?”
 
Opening his eyes, Shigure looks over at the white-haired shorty. Mary blushes at his attention, but it seems that Anne’s words have done the trick, because the next thing he sees is the petite girl’s body as she shucks off her long coat, only to reveal she’s wearing nothing at all beneath it. The pale young woman’s blush stretches down off of her face along her neck and onto her mosquito bite tits, but she doesn’t let her embarrassment hold her back any longer, instead moving forward with determination lining her small frame.
 
Unlike Anne, Mary has the opposite problem when it comes to height. She doesn’t need to kneel like the blonde does, instead she actually has to remain standing, bending over at a forty-five-degree angle in order to grab the top few inches of his member, poking out from between Anne’s breasts as it is. Another groan leaves Shigure’s throat as the white-haired pirate begins to blow him right then and there, all while Anne goes back to sliding her huge tits up and down the rest of his length.
 
His precum, mixed with Mary’s slobber as the petite girl shows just how much of an enthusiastic pervert she is beneath the shyness, makes for excellent lubricant as it slowly slides down Shigure’s shaft, making the passage in and out of Anne’s tits all the easier as time goes on. The pair tag team him, but then Shigure had already been expecting that, hadn’t he? Grunting, the young man reaches out and grabs at the side of one of Anne’s breasts, while at the same time taking hold of Mary’s skinny little butt with the other. The white-haired girl yelps, while the blonde woman moans loudly. Shigure keeps molesting both of them of course, right up until the point where Mary finally manages to suckle the seed from his cock, his load exploding out into her mouth.
 
The white-haired girl’s eyes go wide, and she’s forced to pull back after a moment of her cheeks ballooning outwards from his sheer volume. The rest of Shigure’s load subsequently ends up all over the faces of both slutty pirates, and when the pair proceed to happily lick and lap his cum off of each other’s faces, Shigure isn’t at all that surprised by the whorish behavior by this point. He is extremely aroused though, and he watches with desire and hunger in his gaze as the girls make out right there in front of him, eager to get on with the next part of this delicious threesome.
 
Soon enough, Anne is standing up and grabbing hold of her white-haired companion. Mary lets out a squeak, which is adorable enough on its own, but she also goes with the blonde as the top-heavy pirate drags her counterpart up onto the bed with her, sliding up to the top of the large mattress, only to leave Mary spread prone over her body.
 
Shigure stands as well, and considers the duo for a moment, trying to decide which of them he’s going to fuck first. As he does so, he strips out of the rest of his own clothes, unashamed of his nakedness, even as his cock continues to stand proud at full mast, protruding from his crotch. He watches as Anne and Mary both stare at it with lust in their eyes, and he watches as Anne grins and whispers something undoubtedly salacious in Mary’s ear.
 
The white-haired girl reddens again quite nicely, and Shigure enjoys the show, even as she reaches back and spreads her small ass cheeks apart, biting her lower lip before speaking with a slight stutter.
 
“P-Please Master… w-will you p-plunder my b-booty for me?”
 
Well, with a request like that, he’d just feel awful saying no, wouldn’t he? Grinning quite wickedly, Shigure crawls onto the bed, one cock in hand as he moves up towards where the two female pirates are waiting for him. It’s easy enough to get into position atop the two beauties, sandwiching Mary between himself and her eager blonde counterpart, even as he lines his bulbous dick tip up with her spread open butt hole. His member has a hard time at first, but Shigure just grabs hold of the Servant’s ass cheek and thrusts inwards, grunting as he buries his huge dick in her small little sphincter.
 
Mary muffles her shriek of pain by burying her face in Anne’s breasts, and a moment later she’s trapped there as Shigure leans in all the way, thrusting in and out of Mary’s poor little behind, all while leaning down to capture Anne’s lips with a kiss. The legendary blonde pirate moans in response, even as he dominates her mouth with his tongue, wrestling her own into submission.
 
In and out of the petite body he goes, as he fucks Mary Read’s ass to kingdom cum. The white-haired girl’s shrieks swiftly turn into whines and whimpers, which then becomes honest moans of pleasure, still muffled by Anne’s huge tits as she is. Over and over again, Shigure plows Mary’s tight little butt, until eventually, he just can’t take the pressure anymore.
 
The combo blowjob-boobjob that the duo had given him earlier certainly extends Shigure’s next release a bit longer, but in the end Mary’s ass is the tightest hole he’s ever fucked, and though he holds back as long as he can, eventually he begins to cum, filling her bowels with white, hot seed, even as Mary screams in response, not in pain this time, but in pleasure. The pair cum together, orgasming simultaneously as Anne feels her counterpart’s small body shaking across her own form, spasming and seizing up from sheer ecstasy.
 
When Shigure pulls his tongue out of Anne’s mouth and his cock out of Mary’s ass, the exhausted white-haired Servant flops over off of Anne, escaping the sandwich that the two of them had made with her in the middle, panting heavily as she lays there with a happy, fucked-silly look on her face. Anne takes one look at her friend, and immediately spreads her legs wide, reaching up to grip her tits as she grins at Shigure with the expression of a wanton whore filled with lust.
 
“Please Master… please fuck me next.”
 
Shigure had already had every intention of doing so, of course. His member still rock hard and raring to go, the young man grins and slides forward a few inches in order to put himself right between Anne’s legs. His member, already slick with remnants of his seed, slides right into the blonde’s sopping wet cunt, and as her face twists into one of delirious pleasure, the reality of the situation finally truly hits for Shigure.
 
He’s fucking the great Anne Bonny herself, a legendary pirate… not only that, she’s his in every way that matters, his loyal and loving Servant, just like Mary Read. They’re his, and he is their Master. Anne proves it as he fucks her, vocally egging him on.
 
“Yes Master, yes! Fuck me Master, fuck me harder! Plow me, use me, rail me you hung stud! Fuck, fuck, FUUUUUCK!!!”
 
Anne cums in record time, her orgasm causing her insides to grow all the slicker, and her inner walls to in turn squeeze down around his pistoning cock. Sweating a little now, Shigure grunts and reaches up to grab hold of the blonde’s huge titties, kneading and mauling them with his hands, even as he fucks her harder and harder, trying to give it to her with as much power and force as he can.
 
He fucks her, and she climaxes again and again around his dick, but no matter what he does, Anne does not break like some of the more prudish Servants he’s violated into submission. There’s no repressed slut here though, to be fair… just a slut. Anne is completely and utterly open about exactly who she is. She loves sex, in all its various forms, but Shigure is her Master, and thus sex is most fun with him, as it should be.
 
With a wide, happy grin on her face, Anne reaches out and hooks her arms around his neck, pulling him down into a deep, tongue-filled kiss. Then when she pulls back, her grin takes on a secretive note, and there’s a mischievous twinkle in her eyes.
 
“Mm, Master, if you REALLY give it to me, I’ll tell you a secret~”
 
Shigure lifts both eyebrows at that, and with a particularly savage thrust, he brings the blonde pirate to yet another orgasm, drawing a truly explosive release from her as she cries out in ecstasy. When Anne comes down from that, she lets out a breathless laugh, her breasts heaving and bouncing and jiggling beneath his rough, tightening grip.
 
“Alright, alright! Master more than earned it with that~ In truth, Master should know something about Mary. You see, Ma-mmph!!! Mmmmmph!!! Mmm…”
 
Blinking, Shigure finds himself a little surprised when Anne’s head is abruptly replaced by Mary’s crotch. His eyes slide up from the white-haired girl’s navel, all the way to her blushing face. She’d just gone and plopped her cum-filled ass right down on Anne’s face, and judging from the gasps and the blush, as well as Anne’s muffled giggles and moans, the blonde had in turn gone right to work at eating her counterpart’s cream-stuffed butthole out.
 
Lifting a brow, Shigure leans in, invading Mary’s personal space even as the petite pirate moans and pants breathlessly right in front of him. He uses Anne’s tits as handholds, even as he cocks his head to the side, looking at Mary inquisitively.
 
“Mary? What was Anne about to say?”
 
Blushing deeply, the white-haired girl looks away, averting her gaze even as her skinny hips undulate across Anne’s face.
 
“I-I… u-um… A-Anne was going to tell you t-that I’m in l-love with you… Master.”
 
With a declaration like that, how can Shigure possibly resist? Grinning ferally, the young man leans forward, pleasantly surprising his white-haired Servant as he wraps a hand around her neck and pulls her into a deep, tongue-filled kiss. He dominates her mouth just like he dominated Anne, and Mary happily gives into him, moaning wantonly against his lips right up until the point where that becomes a cry as the pleasure of him kissing her and Anne eating out her ass brings her to another climax.
 
The white-haired pirate ends up squirting her pussy juices all over her blonde friend’s heavy chest and Shigure’s hands, and that in turn causes Anne to cum again as well, her pussy walls tightening down around Shigure’s pistoning dick with a newfound ferocity. A surprised grunt is all Shigure can manage as the domino effect continues and Anne finally milks him of his third release. His seed fills the tall blonde’s womb to the brim and then some, and he groans into Mary’s mouth as he unloads every last drop of it into her friend.
 
From there, things do finally begin to calm down. All three are more than a little tuckered out by that point, so it feels perfectly natural to each of them to lay on the bed together for a time, recovering and cuddling with one another. Anne lays in the middle, her tall, voluptuous body giving both Shigure and Mary something to do, even as she in turn uses her hands to jack off and finger the two of them respectively.
 
Shigure happily sucks on one of the blonde’s nipples, his focus completely on her breast, even as Mary does the same with the other one. The pair meet eyes over the Anne’s tits, and Shigure can see the utter devotion, love, and loyalty present in Mary’s gaze. He’s quite pleased with that, and from the looks of things, Anne probably feels the same way.
 
All three of them are content with their current circumstances… and Shigure has no doubts that he’ll be revisiting the pirate duo in the future, every intention to have more fun with the two of them running through his mind. After all, sometimes it’s fun to just have a pair of slutty girls submit to him. No Command Seals, no bondage, no pet play (Though he wouldn’t deny that Scathach was close to the top for his favorites) just some good old-fashioned fucking.
 
Yeah, Shigure could definitely use some more of that. Luckily, with the estimable Anne Bonny and Mary Read in his grasp, he would never find himself wanting for it, ever again.

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