A/N: Here's the new Chapter! Which also means the next four chapters are up on my Patreon for early access as well as the chance to vote on the direction of the story!

Shirou fucks Sakura and Medusa. The Second Singularity gets underway~

-x-X-x-

Flushing under her blindfold as Shirou awaits her response, Medusa hesitates for only a moment longer before letting out a shuddering breath and making her decision.

“Please… take us both, Master.”

Humming, Shirou shoots Sakura a quick glance but his darling kouhai is still recovering from having three digits inside of her pussy at the moment. Looking back to Medusa, he peers at the Rider-Class Servant closely.

“Is that truly what YOU want, Rider?”

Blushing at his questioning tone, Medusa nods her head.

“It is. I promise. I didn’t understand before, but I get it now. And… I want it. I just don’t want it at the expense of my Mistress. That’s why I want you to have us both together. So that Mistress and I can both be happy with you, Master.”

Sakura gasps and it’s at least in part because of her Servant’s words because when Shirou looks over at her again, she’s staring at Medusa with wide eyes. Still, Rider has spoken and that means its up to Shirou to see it through now.

Pulling his fingers out of Sakura and rising from where he’s sat on the edge of the bed, Shirou turns and gestures.

“Get up there, both of you.”

In his head, he doesn’t have to say anything more than that. After all, he’s done this twice before, right? First with Saber and Saber Alter and then with Jeanne and Jeanne Alter. Really, he’s becoming old hat at fucking women simultaneously by this point. Which is why he’s taken aback a little bit when they don’t just automatically climb on top of each other for him.

Instead, Sakura hastily crawls up onto the bed and lifts her legs up into the air, bending them at the knees as she spreads her thighs apart and exposes her drooling pussy to her Senpai. And Medusa… well, Medusa quickly follows suit, mimicking her Mistress to a T and coping her pose on the bed despite how embarrassing her reddened face implies she finds it.

For a moment, Shirou just stares at them both blankly, almost ready to tell them they’re doing it ‘wrong’. But is there really a wrong way to do anything here? In the end, he just steps up to Sakura instead. Pressing his cock against his kouhai’s slit, he watches her face contort in pleasure as she moans for him. The shadows that Sakura can call on are nowhere in sight as he sinks into her inch by inch. Right now she’s just a simple young woman, or at least trying to be as close to one as possible.

At the same time as Shirou begins fucking his kouhai, he also reaches over and slides two fingers into Medusa’s pussy. The blindfolded Servant gasps as she’s filled up alongside her Mistress. Fucking them both at the same time… this works too, doesn’t it? Driving his digits in and out of Rider, he makes sure that she gets as close to the same experience as Sakura is getting as is possible. He matches his pace damn near perfectly, fucking his fingers into Medusa’s cunt at the same time that he’s thrusting his cock deep into Sakura.

But… it’s not perfect. Not by a long shot. And Shirou can do better. He knows he can do better. After all, he’s the ultimate faker, isn’t he? With that said… Shirou pulls his fingers out of Medusa and activates his Magecraft.

“Trace on…”

It’s not easy. His element is Sword after all. Making anything BUT a sword, especially something based on something else… well, it’s difficult. Still, at the end of the day… he manages to create a pretty close approximation to his dick. A dildo, if you will, though made of prana rather than any real material like plastic.

Certainly, it’s better than just his fingers. Medusa seems to agree as he drives the traced copy of his cock into her pussy. Holding it at the base, he pushes it in and out of her, once again trying to match the same pace he’s fucking Sakura with.

Both purple-haired women moan at this, shivering and quivering on their backs before him. Laid out on the bed next to each other, he gets to watch all of their contorting facial expressions and enjoy their wanton cries. He can only see Sakura’s eyes because of Medusa’s blindfold of course, but even blindfolded the Rider-Class Servant is incredibly expressive as she’s fucked by a fake cock.

Still, best to… test things. And so Shirou switches things up halfway through. As Sakura and Medusa are moaning up a storm, he abruptly pulls out of both of them and swaps positions. Before they can truly register that he’s even moved, Shirou is already back inside both his kouhai and his summoned servant. But this time he’s filling Sakura with the dildo and Medusa with the real thing. He can’t help but wonder if there’s a difference.

There definitely is, he quickly reveals. Both Sakura and Medusa react to the change in their own ways. Medusa’s groans grow louder now that she’s getting the real thing. Meanwhile, Sakura is still moaning, still pumping her hips against his copied cock… but she’s definitely not enjoying herself quite as much anymore. She even leans over to Medusa and hisses to her.

“Be grateful, Rider. Master has seen fit to grace you with the real thing. You best thank him properly.”

Shirou is just about to reprimand her for that when Medusa hurriedly nods, moaning up a storm and clawing at the bedding beneath her.

“Y-Yes! Thank you Master! It… it feels good! Please don’t stop!”

Well… hm, he’d let Sakura slide this time. After all, Medusa was still HER Servant. That meant she had to be allowed to give her orders, so long as they didn’t cross a line. And in this case, telling Rider to thank him wasn’t too bad, especially since she seemed to appreciate the reminder.

Smiling slightly, Shirou continues to drive in and out of Medusa for a little while longer before pulling free of her tightly clenching cunt again and moving back over to Sakura. The two women stay on their backs the entire time as he alternates between their cunts. He’s still fucking them at the same time, but with a bit of a twist this go around.

Finally nearing the end, Shirou decides to give Sakura a reward for being such a good kouhai. As he tips over the edge, he makes sure he’s inside of her, cumming deep within her and making her squeal and climax all over his cock as a result from the explosion of pleasure. Her eyes roll back in her head and her mouth hangs open as she shudders and shakes.

Meanwhile, Medusa watches all of this despite her blindfold, biting her lower lip as she slips a hand into one of Sakura’s and squeezes it. Together, the two women ride out the tail end of Shirou’s orgasm as Shirou groans and does the same. Then… it’s over. Beyond the clean up and what not, they’re finished after that. Which means its time to return to the others…

-x-X-x-

Everyone hadn’t just waited around for them to come back, thankfully, so it takes a little bit to gather back up in the Rayshift Chamber. But soon enough, they’re all ready to go.

“Well then. As I said before, all we know so far about the Second Singularity is that its located in Europe around the time of the First Century in the heart of the Roman Empire. We’ll be sending all of you to go and check it out of course. Any questions?”

As Dr. Roman looks around at them all with a raised eyebrow, Shirou looks around as well. No one says anything for a moment… but then Saber steps forward.

“I have no questions. However, I and my… Alternate have discussed matters and I shall be accompanying Shirou on this particular quest. Going forward, she and I will trade off, so to speak.”

That causes Shirou to stare for a moment, even as Saber Alter nods when everyone looks to her for confirmation. And so, as they prepare for the Rayshift, he finds himself with his original Saber by his side as the two of them line up with Rin, Ritsuka, and now Sakura as well as their respective Servants.

Despite summoning Jeanne just the other day, Ritsuka is still taking only Mash with her, curiously enough. Shirou wonders what’s going on between those two, if anything. He would swear he’s caught Mash giving him some strange looks more than once, but whenever he looks over at her she’s glancing away so maybe he's just seeing things.

Though, as they’re all getting ready to go, Mash does suddenly seem to remember something, raising her hand like a student asking to be called upon in class.

“Ah, wait! I did have one question!”

The Acting Director gives her an encouraging smile and a nod as she hesitates for a moment, tilting his head to the side curiously.

“Oh? Go ahead, Mash. What is it?”

“W-Well… we encountered a great number of Servants in the First Singularity. Most were hostile, but one… Ruler Jeanne was not. She was actually on her side. Is it possible we’ll run into more Servants willing to work with us in these Singularities going forward?”

Beaming, Dr. Roman clasps his hands behind his back.

“An excellent question, Mash! From the look of things, it’s entirely possible. In fact, since Servants in general are predisposed to being Heroic Spirits overall, there’s potential that most of the Servants you encounter in these Singularities will be willing to work with you so long as you don’t aggravate them unduly.”

Shrugging, Dr. Roman sighs.

“Indeed, the hostile Servants are likely those somehow seeded by Lev Lainur himself, put in the Singularities to cause chaos and wreak havoc. Obviously we’re still working on everything, but you should never attack first just because you run into a Servant. Be on your guard, but also be on the look out for potential allies in your quests!”

Leaning forward with a twinkle in his eye, the Acting Director raises a brow at Mash.

“Does that answer your question?”

Mash nods her head rapidly.

“Ah, yes sir! It also answers my second question, which was going to be whether Chaldea has any method of identifying allied Servants for us. But it sounds like there isn’t one…”

Sighing again, Dr. Roman shakes his head regretfully.

“I’m afraid there isn’t, Mash. At least not yet. For the time being, you’ll all have to determine that status for yourself.”

“Yes sir!”

With that, Mash’s questioning is done and they’re ready to go. With Dr. Roman and Da Vinci working together at the console, things quickly get underway and the Rayshift is soon started up. Beaming at them all, the Acting Director hums.

“Prepare for Rayshift! We’ll be aiming to have you all arrive at the Imperial Capital of the Roman Empire, circa 60 AD! Good luck, all of you!”

And with that, a blinding flash of light carries them all to their next destination.

-x-X-x-

When the Rayshift is complete, Shirou blinks spots out of his eyes… only for the first thing he notices to be a certain very fluffy white fuzzball.

“Er… was Chaldea’s mascot supposed to come with us?”

Fou bounces up and down a few times, prancing around and taking in their surroundings. Ritsuka, meanwhile, just shrugs.

“Actually, he came with us last time as well, but then ran off almost immediately. At this point, I don’t think it’s worth worrying about.”

Huh. That was good to know, Shirou supposed. Both the fact that Fou was stowing away on these adventures of theirs… and the fact that Fou was male. He hadn’t had any idea. Still, that was interesting but…

“Hang on, didn’t Dr. Roman say we were supposed to wind up in a city? The Imperial Capital, right?”

The Acting Director himself answers that one, his voice coming over their communication devices.

“Indeed! It would seem we’ve discovered the first historical incongruity! Despite setting your arrival coordinates for the heart of Rome, I’m now reading that you’ve all landed in an outlying piece of farmland right next to the Imperial Capital. You’re not too far from the city, but it’s still strange that the position of said city has somehow moved…”

Shirou and the others all exchange looks at that, with Ritsuka eventually asking the obvious question.

“Um… Acting Director, sir… isn’t it more likely that you just… missed?”

“Ahem! Well, while that’s a distinct possibility, that’s not what the readings are showing over here! In fact-!”

Before Dr. Roman can continue on, everyone goes still as the sound of clashing finally reaches their ears. A battle is raging nearby, though not too nearby. There’s a massive hill between them and the sounds of fighting, but now that they’re listening… well, it certainly sounds very violent.

“Aha! Another historical anomaly! You lot are supposed to be in Sixty AD, during the prosperous and more importantly, the PEACEFUL reign of Emperor Nero Claudius! Proper history dictates that no battle should be being fought this close to Rome’s Capital in this year or indeed any other year close to it. You lot better go check that out!”

With nothing better to do and no other leads to go on, they all hurry up the hill. It’s on the large size for hills, and Shirou is glad he can reinforce his body as they move. Rin and Sakura wind up using magecraft to fly up to the top of the hill while Mash insists on carrying Ritsuka on her back. The others… well, the others are all Servants.

Regardless, they all get up to the top of the impressively large hill and find themselves overlooking an incredible sight. Two armies are facing off on the field down below, but one is much bigger than the other. And yet, the small one is holding its own as the large one tries to overtake it. The reason why is immediately obvious after just a quick glance. It’s impossible not to notice the swordswoman at the head of the small army, or the way she’s practically singlehandedly holding a battlefront all on her own.

“Hang on a second… is that you, Saber?”

Rin’s incredulity is obvious even as she uses magecraft to enhance her eyesight and get a better look at the blonde swordswoman currently fighting like a hellion. The woman is dressed all in red in stark contrast to Saber’s blue but there’s simply no denying it… she has the face of Artoria Pendragon. Or wait… does Saber have her face? Isn’t this time period BEFORE the time of Camelot and King Arthur?

Oh no. Shirou was going to get a headache from all of this…

[ ] Hold off for a second, what if its an 'evil twin' situation? Watch for a bit to see how things unfold - 20%

-x-X-x-

If you'd like to read more of my work not seen on this website, check out Hentai-Foundry.com and QuestionableQuesting.com where I have over a thousand stories!

If you'd like to contribute to funding my writing at all, check me out on Patreon.com/Cambrian

Thanks for reading!