Chaldea Subjugation Organization (Fate/Grand Order)

It’s not the first time Shigure has woken up to someone sucking his cock beneath the covers, and it certainly won’t be the last. Still, even as he awakens with a smile to the feeling of a pair of lips and a writhing tongue taking care of his morning wood, his brow furrows before he even opens his eyes. Namely because… he doesn’t immediately recognize just who it is that’s blowing his dick.

THAT’S something of a new experience, and for a few moments, Shigure doesn’t move a muscle, just puzzling over who his hidden guest is. But in the end, he’s not the Master of Chaldea for nothing. Shigure, being Shigure, eventually reaches out and places his hand atop the bobbing hidden head, over the covers that currently cover up the girl in his bed.
 
Then, he starts to face fuck her, forcing her down his length while pistoning his hard-on right up into her mouth.
 
“… gulghk… gulghk… gulghk…”
 
Her gurgling and gagging is muffled by the covers, but that doesn’t stop Shigure from chuckling darkly, even as he continues to force her to deep-throat his cock.
 
“I’m feeling feisty this morning… let’s make a bet, shall we? If I can’t guess who it is before you make me cum, I’ll let you dominate me however you please. But if I do, I’m going to absolutely wreck you for being such a naughty little minx and sneaking into my bed. Sound fun?”
 
The hidden cock-sucker gives an assenting noise, before redoubling their efforts to suck Shigure’s cock, growing more and more enthusiastic as they try to get him off with their tongue, their lips, and their hot, wet, velvety mouth all working over time to try and please him. Shigure just smiles and continues to thrust upwards to meet their efforts… even as he already knows exactly who’s blowing him by this point.
 
It's all in the details, though that’s not going to stop him from playing around a little bit before they get to the fun stuff.
 
“Hm, you know, you’re not the first to do this. Or maybe you are? Could you perhaps be Jeanne Alter Santa Lily? She was so eager to please that she snuck in here, slipped under the covers, and woke me up just like this with her small little mouth wrapped around my cock… could it be you Jailter, back for more?”
 
He pauses for a moment as the sucking continues unabated. Then, he grins.
 
“No, you’re not Jailter. For one, I can feel your breasts, pressing into my thighs. That particular Jeanne doesn’t have any titties to speak of.”
 
There’s a pause at that, and Shigure just grins wider still as the girl under the covers reaches out and carefully pushes his legs a bit further apart, so the sides of her boobs are no longer pressing into his body. Then, she’s back to blowing him with as much ferocity as she can muster, redoubling her efforts. Perhaps because of the comparison. Perhaps because she now knows she wasn’t the first to think of this. Either way, Shigure groans and pushes her head further down his cock as he presses his hand through his covers.
 
“No, definitely not her… and I suppose that also rules out Anne Bonny and Mary Read. Anne, because her tits are too big, to say nothing about the rest of her. Mary, because she’s even flatter still. Mm, for the same reasons I suppose I have to disqualify Boobturia and Moedred. Scathach, perhaps? No, she’s much more experienced than you are.”

That gets another reaction from his current cock sleeve, as she once again redoubles her efforts. She’s really going all out now, and Shigure groans as he tosses his head back, thoroughly enjoying the work that his hidden bed partner is putting into things. He’s knowingly teasing her, of course. Antagonizing her, even. Grinning wickedly, Shigure looks down at the feminine lump beneath his covers, at the bobbing head under his splayed fingers.
 
“Under the same vein, I have to rule Kiara out, I suppose. And Gudako. Both of them are far too skilled at giving head to be giving such a poor showing right now. Oh, not that you’re not trying your best, darling. I know you are.”
 
And yet, despite his pathetic reassurances, she once again tries harder. Shigure’s smile is nearly from ear to ear now. He knows exactly who he’s dealing with, and it’s so very easy to push ALL of her buttons. He just can’t help himself though.
 
“Olga, is that you? I know we’ve grown close, but you really shouldn’t be sneaking into my quarters like this. You have your responsibilities, and I have mine.”
 
It’s almost as if his hidden guest is affronted at the guess. Shigure just chuckles as he feels teeth ever so lightly graze his cock.
 
“No, not Olga. She’s desperate, but not THIS desperate. Mm, whoever you are, you’re undeniably THIRSTY.”
 
He barely hears it. The whimper that comes from the mouth currently wrapped around his cock is barely audible, what with his dick meat in the way, as well as the covers. But Shigure hears it. Oh, he hears it. Licking his lips, the young man cocks his head to the side.
 
“So then… thirsty. Who do I know who’s thirsty? Medb, perhaps? Ishtar or Ereshkigal? Perhaps Xuanzang?”
 
At this point, he’s just running down a list of his conquests, not even really TRYING to put any effort into keeping up the provocation. And yet, it’s doing the trick all the same. The mouth around his cock is working a mile a minute, and its owner is putting forward a hundred and ten percent. He’s getting close now, but Shigure knows for a fact that he can hold out for a little while longer. Time to begin wrapping this up, but no need to finish things quite so soon.
 
“Perhaps you’re one of Arturia’s Lady Knights, hm? Or I suppose I should say, my Lady Knights.”
 
That gets a reaction, and Shigure grins as there’s a moment of hesitation, of indecision. His hidden guest returns to sucking his cock a half a moment later of course, and Shigure pretends not to notice. He did though, oh yes, he did.
 
“Hmm, but if you were one of my Lady Knights, come to play… who would you be? Bedivere? Gawain? Tristan? I’d suggest Lancelot, but we both know she has larger tits than what I felt before from you.”
 
And there it is. There’s the moment when she SLAMS her lips down around the base of his cock and just HOLDS herself there, forcing her throat to spasm and convulse as she chokes herself out, gurgling around his member, her lips suctioned down and not going fucking anywhere. She’s clearly trying to end this right now, and to be fair, it’s a good effort. Shigure smiles, and lets things come to a close… but of course, not before winning the bet.
 
“I suppose that just leaves one answer, doesn’t it? To think, my beloved, innocent kohai Mash would sneak into my bed and assault me while I slept…”
 
He’s amused rather than accusatory, even as he throws off the covers to reveal Mash’s singular visible eye staring up at him from behind her glasses, which rest beneath her bangs, her face red and her eye watery. He transfers the hand that had been on top of the covers to Mash’s head directly, and his fingers dig into her locks, before he pulls her back just enough so that when he cums, it doesn’t explode out of her nostrils and the sides of her mouth.
 
Instead, Shigure gives Mash enough room that while her cheeks DO puff out like an adorable chipmunk, she’s still able to swallow every last drop of his seed without fail, drinking down his hot, white spunk and staring at him the entire while. Shigure, meanwhile, is enjoying her appearance. He’d initially thought she would have snuck into his bed completely naked. But on top of the glasses, which he was impressed she’d managed to keep on throughout that rough blowjob, albeit slightly askew, Mash was also wearing a cute pink and white nightie.
 
It hugged her curves well enough that it’d honestly felt like he was feeling her tits directly before, but no, she’s wearing the dress, and probably panties besides, the little deviant. Snorting slightly, Shigure finally lets go of Mash’s hair as his release winds down. In response, the lilac-haired demiservant sits back on her haunches, her hands between her knees as she opens her mouth and lets her tongue roll out to show that she’s kept the last spurt of cum from his load within.
 
She swishes it around for a bit, before audibly gulping down his seed. Then, her eyes blazing with lust and her tongue tracing out to lick at her lips quite lewdly, Mash looks to Shigure with hooded eyes.
 
“I lost, Senpai. I suppose that means you get to do whatever you want with me now~”
 
Shigure just chuckles, before smirking as he sits up as well, getting off his ass and onto his knees. Rather than wasting time maneuvering himself into position, Shigure just reaches out and grabs for Mash, taking hold of her by the hips and spinning her around to leave her ass pressed against his still-hard cock. She mewls emphatically, and wiggles her buttocks up against his erection, even as he feels the panties, he knew she was wearing beneath the hem of her dress, which is in the process of riding up as a result.
 
A hand on the back of Mash’s neck steadily pushes her face down into the mattress, and with his other hand, Shigure flips up her skirt and then hooks two fingers into the waistband of her pure white panties, tugging them down off of her ass, and away from her sopping wet pussy. As he pulls the soaked-through garment off of Mash entirely, Shigure bunches it up and for a brief moment, considers stuffing it in Mash’s mouth as a makeshift gag.
 
He thinks better of this though and tosses the balled-up panties to the side before refocusing his attention on the prize before him. He wants to hear Mash. He wants to hear every last moment of what is to come. Licking his lips, Shigure brings his cockhead up to his darling kohai’s pussy lips and presses up against her slit until it begins to flower. Then, he stops and pulls back, only to repeat the process.
 
Mash moans at first, only to whine when she realizes he’s not FULLY penetrating her. The most Shigure ever does is tease her entrance with the tip of his member, pushing just the head of his shaft into her before pulling back again. The lavender-eyed demiservant tries to correct this by aiming to push her hips back in his direction, but Shigure still has a hand on the back of her neck, pinning her in place quite easily, and his other hand rests on the curve of her side, where her hip meets her round buttocks, sliding back and forth, rubbing her body this way and that.
 
“S-Senpai, please…”
 
Shigure just cocks his head to the side and chuckles, continuing to rub the tip of his length up and down her slit, brushing it against her incredibly sensitive clit again and again.
 
“Since when did my kohai become such a… perverted deviant, huh? Where did my sweet, innocent kohai go? What happened to her?”
 
Mewling, Mash does all she can do, which at this point, is really just reaching out and clawing at the bedding before her with both hands. Still, she does answer, eventually.
 
“S-Senpai did! S-Senpai happened to me! H-How was I supposed to stay innocent, when Senpai kept giving me e-examples of how much f-fun being lewd was? Mooouuu, Senpai can be so cruel…”
 
That provokes a laugh from Shigure. He’d known that Mash was carrying a torch for him, that she longed for him. His very first Servant… of course he’d known. She was blatantly obvious about it, about her desire for him. But that was exactly what had made him decide to wait and see. It wasn’t that Mash was undesirable or anything like that. It was more that just taking her and fucking her… it would have been boring. Conquering her outright, would have been boring, because she would have just surrendered, just like that.
 
But this? Having Mash come to him, having her initiate things? Shigure liked that. He liked seeing the fruits of his labor made manifest, liked seeing how just standing by and being himself had slowly corrupted his darling kohai over the days, weeks, and months since they’d first met. This? This was a culmination of events and plans long in the making.
 
That’s what made it so satisfying to finally sink into Mash’s drooling wet, velvety depths, and take her virginity. When Shigure finally goes from teasing her slit to pushing into Mash for the first time, tearing through her hymen and claiming her purity for himself (not that any part of the girl’s mind was pure by this point, obviously) he gives no warning, and offers no hesitation.
 
Needless to say, Mash, who’s been anticipating it but wasn’t expecting it in that moment, cums violently. The moment his cock slides into her tight, clenching, virgin depths, she’s explosively orgasming, screaming her pleasure into the bedding, biting down on it hard to try to swallow the sounds she’s making. But she can’t fully be rid of them, can’t fully stop herself from cumming on his cock in a truly humiliating fashion. Not that she cares about humiliation or anything like that. All that matters to Mash, Shigure can tell, is the fact that she’s finally, FINALLY being fucked by him.
 
So of course, he gives it to her just like she wants it. Just like he said he would, in fact. After all, ‘if’ he won the bet, he did promise that he would wreck her. That’s exactly what Shigure does. Even as the pleasure from that first mind-blowing orgasm very nearly causes Mash to pass out on the spot, Shigure is pistoning his big, fat prick in and out of her with wild abandon, rutting her hard right there on his bed.
 
His hand on the back of her neck slides along her back and up to her round, pert behind, joining its brother as Shigure grips and squeezes Mash’s ass cheeks, his fingers digging into her pale flesh and leaving red marks behind. She keeps her head down, and her ass up regardless though, and as Shigure continues to fuck her, Mash squeaks and squeals and screams into the bedding, her moans and her shrieks of pleasure filling the room, no matter how she tries to stifle them.
 
The sounds of flesh smacking against flesh joins those sounds, and Shigure’s grunts and groans accompany them as well, until they’re both lost in the throes of ecstasy. At least, until Mash suddenly pushes herself up. Forcing her hands under herself, the darling lilac-haired demiservant seems to find her second wind, because quite suddenly, she’s up on her hands and knees, pushing her hips back into Shigure’s cock and turning it from face down, ass up, to doggystyle in a heartbeat.
 
The Master of Chaldea has nothing against this change of pace though. Reaching out, he grabs a fistful of Mash’s short hair and drags her head back, forcing her back to arch as he fucks her even harder. Mash, meanwhile, looks at him, her glasses having fallen free by this point, but her beautiful lavender eyes are nonetheless focused on his face.
 
“I l-love you, Senpai…”
 
For a moment, she almost sounds like her old self, like she’s shy and demure once more. Shigure just grins and leans forward so he can kiss her, causing her face to go bright red, even redder than it was before, her eyes going wide. When he pulls back, he lifts an eyebrow.
 
“What was that?”
 
“I-I love you, Senpai! I’ve always loved you! Please, fuck me harder! Please give me m-more of your c-cock! I want it, I want it, I want iiiiit!!!”
 
As a babbling Mash declares her love for Shigure a hundred times over, he just keeps right on fucking her. Eventually, her words become gibberish as she climaxes time and time again around his cock, and in the end, she ultimately passes out from the pleasure, as Shigure fills her womb with his seed. But even as he pumps a nice, thick load of cum into her while she hangs limp in his grasp, Shigure isn’t satisfied.
 
With a growl, he begins fucking her again, grinning viciously all the while. He’s waited long enough for this, and he’s going to enjoy himself, to the FULLEST possible extent.
 
-x-X-x-
 
The next morning, Mash wakes up naked. Her white and pink dress has been removed, and a glance off the side of the bed shows its torn remains scattered across the floor. But the young woman doesn’t mind all that much. Shifting slightly, Mash lets out a soft mewing sound as she feels just how SORE her body feels. Every single one of her orifices is sore as hell and sticky with semen. But it’s WHOSE semen it is that really matters.
 
Senpai… Senpai had finally fucked her. There’d been a time when Mash had wanted nothing more than for him to fall in love with her, and to make gentle, sweet love to her in this very bed. She’d come to realize, as time went on, that the Master of Chaldea, her beloved Senpai, was not the kind of man to settle for one woman. She wasn’t likely to ever be his wife… or at least not his ONLY wife.
 
For a little while, Mash had fallen into despair over that fact. Her Senpai that she loved so much… she couldn’t have him all to herself. And in fact, she didn’t know how to have him in the first place. How was she supposed to compete with all these gorgeous female Servants? She wasn’t even a full Servant herself, stuck as a demiservant all this time.
 
But in the end, Mash had realized something. She’d realized that she didn’t have to compete, because while Senpai might compare the women he’d fucked in a teasing manner, he didn’t let that stop him from fucking each and every one of them, didn’t let that stop him from making them happy as he satisfied himself on their bodies.
 
That was what Mash had wanted for the longest time. And finally… FINALLY she’d gotten it. So yes, all three of her holes were sore as hell and sticky with Senpai’s cum, and yes, Mash didn’t remember getting butt-fucked and she wished she did… but at the end of the day, the lilac-haired demiservant couldn’t be happier.
 
She’d finally offered herself up to her Senpai. All was right with the world.

-x-X-x-

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