Gorgon, Mash, Nightingale

Gorgon

-x-X-x-

As Shigure watches Gorgon gorge herself on some monsters, he can't help but smile slightly. She's something like a particularly unruly pet, one he has to feed regularly so that she doesn't try to pull on the leash too hard. Of course, he hadn't quite understood her at first, but eventually, she'd spelt it out rather bluntly, something Shigure found himself appreciating very much.

"The mana consumption of this body is intense. The fuel efficiency is poor, in other words. You insensitive contractor. It means I'm hungry."

With that blatant explanation out of the way, Shigure had decided to put more time and effort into Gorgon's growth. This meant lots of these little solo trips, allowing her to feast and gorge herself on however much meat she wanted. That in turn had resulted in her slowly transforming from her original, humanish form into a larger, slightly more monstrous form. Her legs had melded into a massive snake tail that made up the lower half of her body now, and she'd added several snakes to her hair as well, though of course, plenty of it was still the normal purple locks he was familiar with.

Regardless, the changes were obvious, and the increase in her size and power was as well. So far, this had been a good move, allowing her feed and feed, and then for good measure, feed some more. Still, it WAS getting a little late now. Probably best to start heading back.

"Gorgon, go ahead and finish up that last meal, and then we're leaving."

The moment her name leaves his lips, the snakes in her hair whip around to look at him. Eventually, she side-eyes him, but doesn't say anything. Shigure just raises an eyebrow in response, smiling casually as she finishes her meal and then turns to face him fully. Slowly, the massive monstrous Servant slithers her way over to him. Once she's in front of Shigure, their different in size is much more noticeable, with her towering over him by a good few feet.

It's obviously that she's TRYING to be intimidating though, in the way she purposefully looms over him, using the thick, long snake tail that is her lower half to rise herself up into the air a bit more. The snakes in her hair are all spread out, angled to stare at him just as Gorgon herself is, while her arms cross under her chest, accentuating her truly massive breasts.

"Hmph. Perhaps it's time we had a talk about our… arrangement, Morsel. I see no reason why a being as magnificent as myself should be taking orders from someone as tiny and weak as you. Honestly, I could just as easily eat you up as I eat this unsubstantial prey, if I so desired."

She sounds almost flippant, but he can see the hunger in her eyes. Even still, Shigure didn't get to where he is by being easily cowed, now did he? He's not one to balk in the face of aggression, especially not from one of his Servants. He still has all three of his Command Seals after all, though whether Gorgon is in the right frame of mind to be considering those or not… well. Shigure just smiles up at the monstrous snake-woman, cocking his head to the side and making a show of eyeing her up and down.

He's ogling her quite openly, and though she refrains from preening TOO much under his gaze, at the same time, she can't help basking in the attention, too proud and too vain not to. Chuckling lightly as he enjoys the up-close sight of her VERY thicc body, Shigure eventually gives Gorgon a wicked grin.

"I wouldn't mind eating you up myself, Gorgon."

Gorgon's eyes widen just a fraction, and even the snakes in her hair pull back for a second in surprise, before drawing closer once more. She leans in, clearly very interested. The overt flirting does wonders for inflating her already large ego, and she licks her lips as she in turns eyes Shigure up and down next. Eventually, she lets out a derisive snort.

"Hmph. You aren't much, Morsel. It's not like I would be able to feel your tiny dick anyways… but perhaps I can indulge all the same."

Shigure is just opening his mouth to respond, but Gorgon doesn't give him the chance. Her hair snakes lunge forward as once, and rip off his clothing before he can react, drawing a grunt from the young man's lips as he's then dragged up into the air by those very same hair snakes wrapping tightly around his body. Initially, Gorgon traps his arms up against his torso, and as she pulls him in close, Shigure wonders if he should use at least one Command Seal to turn things in his favor.

… It wouldn't be the first time he's made sure that the Servant enjoyed every last bit of the experience a hundredfold, after all. But something stops him from going through with it, even as Gorgon uses one of her real hands to spread her slit open and force him inside of her. His cock penetrates deeply, probably deeper than she's expecting. Judging by the look on her face, the monstrous Servant isn't actually prepared to feel anything, not thinking he'd ever be able to reach very deep inside of her.

Just goes to show that she hasn't done her homework. Shigure was plenty big to begin with, but life among so many insatiable Servants has left him less than human in more than one regard. As Shigure's first involuntary thrust goes deeper than Gorgon is initially expecting, her breath hitches, and though she manages to bite back the gasp, the snakes that make up her hair do loosen their grip on him quite a bit.

That's all the invitation Shigure needs, in the end. Reaching out with his now freed arms, Shigure wraps them around Gorgon's torso as best he can, gripping at her wide hips with both hands and squeezing down hard. Then, he begins to go to town on her, plowing into the monstrous Servant with all his might. And judging by her reactions, it feels better than she thought it would. Her moans fill the air, and her inner walls squeeze down HARD around his cock. She's tight despite her size, and wet on top of that, making the passage in and out of her gripping cunt all the easier and faster as time goes on.

And yet… she's not reaching orgasm as quickly as he would expect. Sliding one hand up off a hip, Shirou reaches for Gorgon's breast instead. He watches as she reacts to this with a gasp, her face slightly red and his fingers digging into her jiggling mammary as he rubs his palm against her rock-hard nipple. She looks down at where he's touching her chest, and then up at him… before stubbornly turning her head to the side.

"A-As I thought, I can't feel a single thing. You'll have to try harder than that, Morsel."

He's not one to take her words at face value, when she's clearly acting like a classic tsundere, but at the same time, he can feel that she's right at least in one way. She might be feeling it, but she's not feeling it enough. He DOES need to try harder. So that's what Shigure does. Gritting his teeth, he thrusts forward with all the might he has to offer, which given the number of Servants who have boosted his physical attributes in one way or another since he became Master of Chaldea, is quite a lot.

"I'm, ah, not even enjoying this, Morsel. You aren't even trying, mm, are you?"

She's lying, he can tell that. It IS working… it's just not working like he needs it to. He can tell that Gorgon is winding up and up, can tell that she's getting closer and closer to the edge… but no matter how hard he fucks her, no matter how he gropes and squeezes her breasts, he can't seem to push her over into the abyss that would be her orgasmic breaking. He knows if he can just get that first climax out of her, then it'll be a foregone conclusion, but how to go about doing that?

It takes a strange licking sensation across his balls for Shigure to finally realize that the key is staring him right in the face. Despite Gorgon's all around tsundere attitude, despite the fact that she herself is looking away and pretending not to enjoy everything… her hair snakes seem to have a mind of their own. They've unwound from around his body completely by this point, for one thing, and now… now they're acting as if they love him, as if they want nothing more than to be with him.

A couple are licking at his balls as they smack into her again and again with every thrust. Others are nuzzling against his body in various places. The lot of them are acting like affectionate cats of all things, leaving Shigure to simply blink in the realization that, even if Gorgon herself isn't being totally honest… the snakes that make up her hair ARE.

Pulling his hand away from her tit, Shigure snaps it out and grabs hold of a hair snake with lightning fast movement. Before either it or its sisters or even Gorgon herself can react, Shigure is taking the gamble… and snogging the hair snake right on its mouth. His tongue intertwines with the forked snake tongue, and Gorgon goes absolutely still, to the point that Shigure wonders for half a moment if she's somehow petrified herself.

Then, the monstrous female Servant cums, and oh is it a spectacular orgasm. Her eyes very nearly roll up in her head right then and there and her mouth forms into the cutest little o as she moans and mewls wantonly. He has her now, obviously. Shigure even slows down the way he's fucking her, as he plays with the hair snake, he's grabbed up instead.

It seems that this is her weak point. Gorgon is completely and utterly vulnerable at the moment, as her face goes absolutely red and she even hides behind her hands, while all of her other hair snakes hide behind her head, only to peek out at the one that's still got it's tongue intertwined with Shigure's.

Thrusting up into Gorgon's cunt… it doesn't necessarily feel any different now, but there is a much greater amount of responsiveness, that's for sure. The monstrous Servant cums again and again around his cock, now that he's striking at her most vulnerable spot and using her to his whim. She's all but gurgling at this point, making incomprehensible noises from behind her hands as she hides from him.

Hm, well, he's not going to let that continue forever. Leaning up, Shigure lets go of the hair snake for a moment, and even as it wraps itself snugly around his waist, practically hiding its face in his hip, he reaches up and grabs Gorgon by her wrists. Pulling her hands away from her face isn't EASY, per say, but with his enhanced strength and her squirming and writhing and altogether distracted state, it's far from impossible.

Exposing her blushing features, Shigure just grins as they make eye contact, causing Gorgon to gasp and bite her lip, knowing she's been completely and utterly beaten by this point. Even still, she's not entirely willing to give up…

"D-Don't think t-this, ah, means anything M-Morsel. I still… I still…"

Letting go of her wrists, Shigure reaches back behind her head and grabs two more of her hair snakes, pulling them forward and giving them both paradoxical kisses, ones that are both chaste… and incredibly lewd. Gorgon squeals, and her eyes do fully roll back in her head this time as she ahegaos on the spot, her tongue even lolling out of her mouth quite lewdly.

Her entire body shakes and spasms beneath him, and her pussy walls milk his cock for all they're worth. But Shigure isn't done with her yet, so with a shit-eating grin on his face, the young Master of Chaldea continues to fuck Gorgon through more and more orgasms, even as the sounds from her lips take on more and more submissive qualities. She's constantly mewling and moaning and whimpering at this point, her eyes rolling around in her skull, her tongue sliding this way and that.

Her hair snakes don't seem to know what to do, beyond the one he originally snogged. As he plays with all of them in various ways, finding out what makes them tick, the original hair snake remains firmly wrapped around his waist, clearly doing its best to keep him inside of its mistress' body. Or is it more like the hair snake is just another part of Gorgon? They certainly seem to have minds of their owns, but perhaps that's not entirely true. Perhaps they're just expressing the subconscious desires of the monstrous Servant that they're part of.

Regardless of how he wants to philosophize it, in the end, it's obvious that the hair snakes were her weak point, either an expression of her true inner thoughts, or just straight up tattling on her. And Shigure had never been one to play fair, so he was more than happy to use and abuse that weakness to its fullest extent.

Now, he had a monstrous Gorgon laying beneath him, cumming her brains out and unable to stop ahegaoing as he fucked into her again and again. After the umpteenth orgasm on her part, Shigure figured it was probably fine to finally let loose. And so he did, filling her with his seed, pumping the thickest, largest load of cum he ever has directly into the Servant's womb. He's rarely held himself back for as long as he did this time around, and it shows in just how viscous and unending his flow is. He's hosing down her insides with his cum for a good solid minute, before finally, he's done.

Looking at Gorgon's completely fucked silly expression, Shigure nods after a moment, deciding that he's done enough. He's most certainly proved his point by now. Pulling out of her however, the Master of Chaldea DOES encounter some meager resistance, namely in the form of the original hair snake he snogged. It's the only one not currently comatose on the floor, splayed out around Gorgon's head just like their mistress, and it's still wrapped around his waist, doing its damnedest to keep him buried inside of the monstrous Servant.

Even now, even with Gorgon unconscious, her hair is trying to fulfill her true desires. Chuckling, Shigure nonetheless has no problem whatsoever in dragging the hair snake off of his waist and pulling out all the same. It wiggles a little in his grasp, but in the end, it's still quite weak from the rough fucking that its mistress has just received.

Getting to his feet, Shigure takes a moment to let the satisfaction of this latest conquest wash over himself. There's no denying that he feels damn good about this one. Gorgon really was becoming a problem in more ways than one, if he was being honest. But at the same time, he didn't want to curtail her growth. Power… power was what he needed in order to save the world, but more importantly, to remain on top at Chaldea. Making Gorgon strong and then making her his bitch… that was a necessary step of his dominance of all that laid before him.

Of course, now that that was done with, Shigure found himself looking down at Gorgon's unconscious form appraisingly, enjoying her monstrous appearance as well as her curves. She was very different from most of his other bedwarmers. The female Servants that he'd had before her… perhaps the only one he could even try to compare her to was Passionlip, and even then, that was… well, he'd say they only had the fact that they were both somewhat monstrous in common. Otherwise, they were two entirely different women.

Gorgon was a new thing, and Shigure so did love new things. Yet at the same time, she was still very much a woman… and Shigure loved women as well. Staring down at her well-fucked form, he finds himself growing hard at the sight. Really, in the end, what else was he going to do while he waited for his Servant to regain consciousness?

Grinning, the young Master of Chaldea begins to move forward, cock in hand as he climbs aboard…

-x-X-x-

Waking up to her Master riding her and fucking her tits would, under normal circumstances, upset the one known as Gorgon immensely. Especially since she hadn't ever truly viewed him as her Master… at least until now. Until now, he had simply been Morsel to her. A bite to eat that she allowed to hang around, just in case she ever got truly peckish. Oh sure, he had those pesky Command Seals, Gorgon wasn't an idiot… but if she really wanted to, she was sure she could bite his head clean off before he ever even got to use a single one.

Now though… now in her hubris, she'd been beaten. Master was fucking her tits, using his hands to grope and squeeze them together as he pinches her nipples… and Gorgon could only blush as she watches his leaking cockhead poke out of the top of her cleavage, inches from her face, again and again. She's been beaten, soundly. There's no denying that. And really, she only sees one path forward at this point.

"Master…"

He stops for a moment, raising an eyebrow as he looks down at her in mild surprise. Gorgon just blushes and looks to the side for a moment, instinctively trying to cross her arms under her chest, but all she ends up doing is wrapping them around his waist, pulling him in deeper and causing that thick fat cockhead to press against her chin.

"I suppose I will continue to eat your enemies, for you, Master. A-And I suppose, if you ever want to eat me again in the future, you have proven that I am the Morsel, and s-so it would be your right."

Averting her gaze as she is, Gorgon doesn't see the big, wide grin that spreads across her Master's face. She does hear him chuckle though, even as she continues to blush and let him fuck her tits to his heart's content. And when he finally begins to cum, if her hair snakes dash in to lick and lap up his seed while she doesn't go anywhere near it with her own mouth… w-well that's just good personal hygiene, right? So what if she can taste everything that her snakes can taste? It's not like she likes it or anything…

-x-X-x-

>>>>>>>>>>>>>

Mash

-x-X-x-

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-

>>>>>>>>>>>

Nightingale

-x-X-x-

As Shigure steps into the Chaldea Infirmary, looking around, he's a little bemused by what he sees. There's no one at all inside of the infirmary… save for the Servant put in charge of it. Florence Nightingale, once of the British Empire, sometime around the eighteenth to the nineteenth centuries. She was a woman of conviction… but it was her nursing skills that had put her in charge of Chaldea's infirmary, leaving her to take control of those who needed their wounds patched up.

Of course, Shigure didn't have any wounds. He hadn't been hurt by anyone at all. And yet, Nightingale had called him in for a check-up all the same? Lifting an eyebrow but smiling slightly, the Master of Chaldea walks with confidence towards the expressionless female Servant. He thought he had a pretty good idea of what she REALLY wanted from him.

"Well, here I am. Shall we begin?"

Bobbing her head, the Servant gestures towards a medical bed for Shigure to sit upon.

"Yes, Master. Please, have a seat."

"As you wish."

Shigure sits down, curious to see how Nightingale intends to… initiate things. But for the time being, he ends up sorely disappointed. She starts by doing all of the normal things one would do in a check-up, and she does it without displacing a single ounce of emotion or interest. She checks his eyes, his ears, and his reflexes. She checks his breathing, and his heart-rate, and all of that stuff.

Truth be told, by the time she's done, Shigure is a little annoyed. He'd thought that something interesting was happening here. Why had Nightingale very clearly kicked everyone else out of the infirmary in order to meet with him, if it wasn't her intention to get it on with him? He had come into this check-up expecting some form of doctor-patient sex play, to be perfectly honest.

As she fills out information on a clipboard, likely for his file in the Chaldea Archives, Shigure stares at Nightingale's ass while she's turned away from him. He contemplates going over and just grabbing it. Or even perhaps using a Command Seal to get some loving from the Servant. But before he can make up his mind one way or another, because no matter what, he's going to fuck this woman, the nurse turns back to him, and her eyes finally, FINALLY slide down his body, to his crotch.

"Now we will begin the more in-depth part of this physical exam, Master. Please remove your pants so that I may check your virility."

For a moment, Shigure is speechless. Incredulous, even. So, he can be excused for how he responds.

"Are you… are you serious?"

It's not just that she's asking him to strip down and show her his cock. He's been asked that by a LOT of women since becoming Master of Chaldea, and he's well-used to it by now. What he's NOT used to is the matter-of-fact, emotionless, and utterly professional way that Nightingale is asking for it. It has to… it has to be an act, right? It has to be a façade.

And yet, even Shigure, who has gotten really good at reading women since becoming Master of Chaldea, can't see through the mask, if it even is a mask and not… actually how she's feeling about the subject. Lifting an eyebrow at him, Nightingale simply nods.

"I am quite serious, Master. Your health is critical to the continued success of the Chaldea Mission, and the ultimate resurrection of the world. If you fall ill, or if you begin to suffer from… over-exposure, then reality itself is in danger."

Over-exposure. She's talking about him potentially fucking too much, isn't she? Shigure almost scoffs in her face at the very idea, but in the end, he thinks better of it. This is what he wanted after all, right? And if he doesn't like how things are going, he can always turn them around and just have his way with Nightingale until her emotionless façade cracks. For now, though, he'll play ball.

Sighing, the young Master stands up and kicks off his shoes, before unbuttons and unzips his pants, pulling them down and kicking them off as well. He then removes his boxers for good measure. In the meantime, Nightingale is not standing there idle. He almost wishes she was, because it would mean she was ogling him at the very least. But no, the emotionless nurse is instead lathering up her usual white gloves with lotion.

Once he's sat on the bed again, this time naked with his cock exposed between his thighs, Nightingale steps forward, and then kneels between his legs. Shigure watches her, looking for any sign that she's taken aback by his size, or at the very least slightly intimidated by it. But no. Taking hold of his cock, the female Servant examines it like one would if one were a medical professional. She shifts it this way and that, making sure that there's nothing untoward, Shigure supposes.

And then, once she's decided that he's clean of disease, she begins to jerk him off. One hand slides up and down his shaft most expertly, while the other slips down to his ball sack, massaging and kneading his nuts. Shigure groans and tilts his head back as he enjoys Nightingale's ministrations.

"Oh fuck… you're VERY good at this."

"I appreciate the compliment, Master, but let's keep this strictly professional. I am merely performing this checkup to make sure of your virility and your health."

His head snaps back down, and he watches her even as she stares, fixated, at his cock. She's REALLY maintaining this act… and truth be told, the longer it goes on, the more it works for him? He's definitely rock hard now, and his balls, still being massaged by her gloved, lotioned hand are churning with a need for release. He's getting closer and closer, and Shigure can barely contain himself as he groans loudly.

He doesn't warn her though. Perhaps it's a bit petulant, but he doesn't warn her. All too soon, he's ejaculating without a single word, all over her hair, face, and hands. Maybe he imagines that this will get a reaction out of her. As his hot, thick jizz splatters across Nightingale's light-pink hair, as he covers her features, he stares down into those red eyes of her, waiting to see if she does anything, anything at all. Even expressing displeasure at the mess he's made would make him happy at this point. Hell, even if she got angry, he could always use command seals to have his way with her anyways.

But no, none of that happens. He cums all over the female Servant, and in response, Nightingale proceeds to take some of his seed into her mouth, swishing it around quite visibly as she looks off into the distance to the side of him for a moment. She then swallows and smacks her lips.

"The thickness and volume of your cum makes it clear that you have a very high sperm count. There is no doubt in my mind that you are incredibly virile, Master."

Well, that's a bit of an ego booster, now isn't it? Not that Shigure didn't already know there was absolutely nothing wrong with his dick or his seed. Still, having the extremely professional, completely emotionless Servant on her knees before him say as much was nice. Staring down at her as she looks back up at him expressionless… Shigure can't help but admire her body. So much so, that he takes a second to eventually recover and respond with a somewhat lame rejoinder.

"Ah… well… that's good to hear, I guess."

Rising gracefully from her knees, Nightingale takes his cock in one hand, before pushing him onto his back with the other. She guides him so that he's laid out along the medical bed, rather than across its width, and she continues to stroke his cock, staring down at it, still seemingly emotionless. As Shigure gets hard again, he frowns slightly.

"And what exactly are you testing now?"

Nightingale slides her red eyes back up to his face, speaking in the same professional monotone as before.

"Now that I've ascertained your virility, it is important that I check your fertility. As I am currently the only available female on the premise, I will have you ejaculate inside of me, and we will see if you manage to impregnate me."

Shigure just kind of… stares. Gawks, really. How she manages to say that all without an ounce of visible arousal, without blushing or averting her gaze or even biting her lip… it's like she's carved from marble. But Shigure knows better. As emotionless as Nightingale might be, or might just appear, she's still a woman with a woman's body. When she goes to climb aboard, he stops her.

"If we're going to do that, it only makes sense that we both strip completely naked, wouldn't you say? We wouldn't want our clothes to get dirty unnecessarily, after all."

For a moment, she pauses. Shigure half expects the Servant to disobey him… but then she begins to unbutton her red overcoat and strip down to her birthday suit. Shigure is quick to do the same and finished much faster than she is given that he's only wearing his shirt at this point. Regardless, soon enough, the very naked, yet still completely emotionless Servant is climbing up onto the medical bed, and up onto him as well.

Shigure takes in her voluptuous body, even as she grips his cock in her lotioned, gloved hand and guides it up between her legs. Even now, even naked, she's the picture-perfect image of professionalism. Shigure had no idea that such a thing could be so… so erotic. The absence of visible lust, arousal, and desire… it's a turn on in and of itself, in a way.

And yet, she is wet, when she finally impales herself on his cock without even a hitching of her breath. As she fills herself with his meat, Shigure's eyebrows raise at just how slick her cunt is.

"You're very wet."

Nightingale just looks at him, seeming utterly unperturbed, even as she continues to sink down his length, gyrating her hips around his member.

"Of course, Master. All studies show that without proper lubrication, chafing might occur, and the experience will not be pleasant for either party. In the interest of seeing you ejaculate inside of me so that we can be certain of your ability to impregnate a fertile female, it is best that my body be sufficiently aroused to accommodate a length the size of your member."

Hearing her explain that she'd essentially gotten herself all nice and wet to make the experience more pleasurable for him, but in such calm, clear terms… well, it was hot. There was no denying that it was hot. Swallowing thickly, Shigure reaches up and takes hold of Nightingale's hips, watching her as she finally begins to ride him, bouncing up and down on his cock.

Her naked tits bounce and jiggle with her of course, but her face… her face never changes. Still dripping with the remnants of some of his cum, the emotionless Servant's features never once shift out of their expressionless look. It has to be a façade, right? But what if it isn't? Well… that's fine too. In fact, it's more than fine. This whole experience is something Shigure is rather unfamiliar with. And he's enjoying it, quite a bit too.

With a grunt, he starts adding some of his own strength to the fucking. Nightingale might be maintaining her calm, professional demeanor, but that didn't mean Shigure was just going to lay there like a dead fish. He also wouldn't mind if his own participation finally provoked a reaction from the red-eyed Servant. It doesn't though, of course. Even as he fucks Nightingale from below with all his might, even as she bounces up and down on his cock, riding him like a bucking bronco… not once does he see so much as a faint blush from her. Not once do her lips open in a breathy moan.

It's interesting, watching just how much control she has over herself. Shigure is convinced by this point, that Nightingale is not truly an emotionless robot. He doesn't imagine she would have come up with this entire silly charade if it wasn't in fact exactly that, a charade. He MIGHT have been convinced if she'd just left it at the handjob, but deciding that in order to 'test' him she needed him to try and impregnate her?

Yeah, this was all an act to get him to fuck her, Shigure knew that. And yet, despite knowing it deep down, he doesn't see a single crack in her façade the entire time. Not once does she break, not once does she moan wantonly and beg for more. It certainly sets her aside from many of the other women that Shigure has fucked into oblivion since becoming the Master of Chaldea. Far, far apart.

In the end, her tightening, clenching inner walls, the only real evidence of her enjoyment of the act, milk Shigure of his second load. He fills Nightingale's womb directly with his seed, pumping it up into her, nice and thick. For a moment, he's lost in the throes of ecstasy, of orgasm, his entire length buried inside of her, and his back arching off the bed as he groans.

Then, it's over and she's pulling off his cock, climbing off the bed. Shigure sits up just in time to watch her slap an adhesive, liquid-resistance bandage pad over her entire cunt before even a single drop of his cum can escape her body. And then she begins to get dressed again, like nothing had happened. Shigure thins out his lips, but follows her lead, remaining silent as he too gets dressed.

Then, having not heard anything from her otherwise, he begins heading for the door. The entire experience had been surreal, and while he'd enjoyed it immensely, he now finds himself in need of a woman with more emotion that he can bend over and fuck, or perhaps press up against a wall… and fuck. However, before Shigure can quite get to the door of the infirmary, he's stopped by his Servant's voice.

"Master."

Shigure turns back around, only to stop dead in his tracks when he sees it.

"While it is very likely that I am pregnant now, it may be necessary to schedule follow-up appointments, just to make sure."

She still sounds cool, calm, and collected. She still looks extremely professional. But as said before, Shigure had gotten REALLY good at reading women since he came to this place. Most others might not have even noticed it… but Shigure does. He sees the very slight blush that betrays her otherwise calm, emotionless exterior. He sees the crack in her façade.

Grinning, the young Master of Chaldea waves a hand dismissively.

"Set it up, and I'll be here. Thanks for the check-up."

Then he turns and leaves for real, a wide, wicked grin across his face that doesn't go away for quite some time.

-x-X-x-