The Black faction had losing many assets in the holy grail war, most notably their homunculi. In fact, they've had lost an amount of roughly five of them per night over the course of an entire week straight, meaning a total of thirty five. All of whom were exclusively female with their hearts, among with other intestines, missing.
Unbeknownst to the Black faction, this was Jack and Raven's work. Raven called their plan, Operation: Pitch Black Sabotage, with the main objective being to (as self explanatory as the name suggested it was) sabotage the Black faction. Mainly by removing their main source of security, the homunculi, while at the same time collecting hearts for Jack to use later.
But this time, Jack didn't come to the Yggdmillennia castle to collect hearts, she went there to scout out the competition on the side of the Black faction for Raven. For that particular reason, she had a special camera that her Big sister had enchanted with her. The camera was an old Polaroid, a type of camera that printed out the photos as soon as they were taken. And through Raven's enchantment, the camera Jack was carrying would also print out the name of the person in the photo below the picture. That is if you knew that you were supposed to read the text on the photo backwards. Raven had rigged the enchantment to print out the name of the person in the photos backwards as a form of safety precaution. Meaning that unless you knew that the text was supposed to be read backwards, it was nothing more than incomprehensible nonsense.
While the actual infiltration was as easy as it had been for the past week for Jack, getting the pictures was a bit more challenging for Jack. Especially the ones that Raven requested of the girl she already had some pictures of, Fiore Yggdmillennia. The request for the pictures of her was, the less clothing the better. The others were a bit easier for Jack to snap.
One Servant she managed to get a picture of was a blond woman with red eyes, who was talking to Fiore while sharing a bath with the other girl when Jack snapped a few pictures. The text on the pictures of the blonde woman read: F-A-retlA hsemagliG. Or if read backwards: Gilgamesh Alter-A-F. The fact that she and Fiore were having a conversation in a bath made one thing obvious, Gilgamesh was Fiore's Servant in this greater grail war. While Jack might be young (or as young as a Heroic Spirit, who would never age, at the physical and mental age of ten-ish could get), she wasn't stupid enough to try and eliminate an opponent several times more powerful than herself. Observing them from a relatively safe distance however was something she was more willing to do though. After snapping a few extra pictures of Fiore and Gilgamesh, Jack left to find another Servant.
Fortunately for her, she didn't really need to go far to do so. In fact, she didn't even need to leave her hiding spot on the rooftop as a rather short (and feminine) figure entered the courtyard of the Yggdmillennia castle. Though through the way they moved, it didn't seem that they had permission by their master. The figure had their hair in a braided ponytail… and said hair was pink. A few quickly snapped photos revealed two things about the Servant. One, their true name was Astolfo, and two, Astolfo wasn't a female who hid her gender, Astolfo was a guy who chose to dress like a girl.
"Hey sis!" Exclaimed Jack over her telepathic connection.
"Yeah? What is it Jack?" Answered Raven on her end.
"Nothing really, just a heads up regarding one of the Servants of the Black faction."
"Okay… shoot."
"One of the Servants true name is Astolfo… and he's a crossdresser."
"… I guess that crossdressing figures of history and legend aren't limited to the females. Huh, the more you know. By the way, I'm gonna take a wild guess and say that he's their Rider. Anything else to report?"
"Not really, and we don't think we'll be able to snap any more pictures. Shall we head back for tonight?" Asked Jack over the telepathic link, before noticing something. "Never mind, the Black Servants seems to be up to something that requires their presence outside the castle. Should we follow them?"
"Sure, go ahead. Just make sure that you get neither spotted nor caught. If you do get caught for some reason, you have my full permission to unleash your Noble Phantasm, The Mist, to cover your escape."
"Got it Big Sis!" Exclaimed Jack as she started following the Servants of the Black faction from the treetops.
After a few minutes of shadowing most of the Servants of the Black faction, except for Gilgamesh, who remained at the castle with her master, which made Raven suspect, after Jack notified her about it, that Gilgamesh was the Black faction's Archer, Jack managed to snap a few pictures of three new faces, revealing their true names in the process.
The first one was a blond man in his 30s(ish) with yellowish eyes dressed in black clothing. Beneath his picture read the text, sepeT III eht dalV. Or if read correctly: Vlad the III Tepes. The infamous ruler of Romania once known as Vlad the Impaler, and after his passing through rumors, myths, legends and fiction, Count Dracula. He held himself like a king on his horse, meaning that this version of him was more focused on the ruler-aspect of his legacy.
The second one was a young red haired woman dressed in what looked like a classic wedding dress. In one of her hands, and on her right shoulder, rested a mace-like weapon. The photo revealed that her true name was Frankenstein's monster, with confused Jack slightly. Weren't monsters supposed to be scary and not… well… pretty(?). The fact that she seemed to at least try and (sadly) failing to communicate with the others through grunts made Jack (and after relaying the information, Raven) suspect that Frankie (as Jack had somewhat affectionately nicknamed her) was of the Berserker-class.
The third and last one was a man, who was wearing an outfit along with a cape and a featureless mask in gold and various shades of purple in color, who Jack (as unbelievable as it seemed) felt genuinely afraid of. In fact, she wanted to run back home to her Big Sister's warm comforting embrace as soon and fast as possible. And that's what she did, while trying her best not to get noticed.
By the time she had reached the old vine cellar, which Raven had managed to convert into not only a fully functional workshop but also a home over the course of the few weeks the greater grail war had been going on, Raven had just walked out of the newly… acquired shower, wearing nothing but a towel. Upon seeing Jack's frightened face, she rushed over to her little sister figure, who unceremoniously hugged her, accidentally making the towel fall off Raven's body and onto the floor. Rendering the green eyed Sorceress completely naked with the only thing preventing her privates from being seen being the little serial killer hugging her.
"Jack, what's wrong?" Asked Raven as she carried Jack, who had started crying into her shoulder, over to the bed the two of them had been sharing ever since Raven… acquired it a couple of weeks ago, while closing the door behind her with a word- and motionless spell.
"Servant of Black. Scary. True name, Avicebull? No Abrasive? No Advisable?" Said Jack between sobs while struggling to pronounce the Caster of Black's true name.
"Avicebron?"
"That's the one! He's scary."
"Come on Jack, it's been a long day and night. Let's go to sleep, okay?"
"Okay." Said Jack happily as she fell asleep with her head resting on her big sister's chest.
"Good night Jack. Note to self: acquire required materials to convert shower into a bathtub big enough for both me and Jack later." Whispered Raven mostly to herself as she and Jack entered the realm of dreams, not even bothering to put Jack into her pajamas nor that she was still naked, not that she would have kept the clothes on by the time she went to bed as she preferred to sleep in the nude.