Kaito made his way towards the Occult Research Club building like a silent wraith. His footsteps, featherlight and his presence matched the shadows around him. A facsimile of the nature they lay upon yet different in their own way. Enough to be distinguishable to his blooming magic sense but almost imperceptible to anyone else.

Slipping through the door, he could feel the presence of a strong magic signature upstairs, in the club meeting room/Rias' office. With a small hum he walked up the stairs, sticking his hands in his pockets until he made his way into the office itself. Seeing the figure of the maid from the night before speaking to Rias. The teen smiled to himself upon realizing that both Akeno and Rias had no idea of his entrance, however the very specific patch of ice that grew on his forearm let him know that Grayfia had.

Kaito froze when he felt the ice form, a trickle of sweat beginning to well up as he paled. He hadn't even felt the maid's use of magic, and judging by Rias and Akeno's lack of reaction, they didn't realize either.

'How did-….' He thought to himself, flexing his fingers.

"Hm. If you want to know. Figure it out yourself ingrate."

'I wasn't fucking asking you.' Kaito mentally growled, just propping himself up against the wall and crossing his arms.

The ice on his forearm was still there, as if unaffected by his body heat. Honestly he would have been more surprised if it was. The mastery Grayfia would have needed to pull off what she just had; it was downright terrifying to Kaito. The idea that he could not only be found so easily but also taken out without his senses even telling him something was wrong. It scared Kaito, but more importantly, it infuriated Kaito.

In the midst of his anger though, his mana flared, alerting both his King and Queen that he was there, getting shocked looks from both.

"Oh. Kaito you're here. Excellent." Rias stated, feeling paradoxically more and less stressed at the surprisingly capable Knight's appearance.

Akeno on the other hand only smiled demurely at him.

"Oh Kaito-kun. Trying to sneak in?" She giggled, though she soon went quiet at the scolding look she got from Grayfia.

"You are the Queen to the Heiress of the Gremory family. Please act in a manner appropriate to your station."

"Yes, Lady Grayfia." Akeno nodded respectfully, nodding her head solemnly.

Kaito meanwhile could practically hear the ringing bells and angelic choir at seeing someone who could reign Akeno in. Almost considering leaving behind all of his earlier annoyance, almost.

"Yo. We're here." Issei called out as he walked in, only to falter at the sight of the buxom but stern maid "Lady Grayfia?..."

"Good. Looks like we're all here." Rias announced, standing up and getting Grayfia to turn to her, her features softening slightly.

"Lady Rias. Would you mind if I speak freely?"

However before she could answer, the scent of ash and feeling of flames exploded into the room with the majestic cry of a bird. The light irritating Kaito and getting him to wince his eyes with a scowl as the deep orange magic circle that spawned them finally flashed with magic. As the flames began to die down, Kaito focused his sight back on them properly and frowned at the sight of a blonde haired man in a very expensive suit.

The man spun on the spot, as if trying to be extra flamboyant and dramatic, his gaze locked squarely on Rias the moment she was within his field of vision, ignoring everyone else in the room.

"Ah. And Riser appears in the human realm at last. I've come to see you, my darling Rias."

'What a complete fucking prick. There's not a single world that this ends well.' Kaito thought, his gaze narrowing but otherwise not moving his body.

"Who's this douche?" Issei asked, getting a mental snort from Kaito.

"This gentleman is Lord Riser Phenex." Grayfia answered, trying to stress manners even to a Pawn "A high-Class Devil and third heir to the family of Phenex."

"And?" Issei asked rudely, he was a normal person at heart he wasn't built for dealing with nobility and royalty.

"That also means he's engaged to the Heiress of the Gremory household."

"THIS GUYS GOING TO GET MARRIED TO RIAS!?"

"Indeed. They've been engaged for some time now."

"NO WAYYYY!"

XXXxxxXXX

Five Minutes Later

Kaito scowled as he stood at the back of the rest of Rias' Peerage while Akeno served Riser tea. It was bad enough that Riser was such a fucking prick that even Kaito, who was admittedly pretty distant from half the Peerage, wanted to deck him for how he treated them. But what was more annoying was that Rias made Kaito give up his position to go stand with the rest of his Peerage.

'That prick didn't even know I was there and she gives that information up? What kind of dumbass does that!?'

"One trying to avoid complications, moron." Kaito mentally growled at Betzalel for his comment.

'With how she's acting that's bullshit and we both know it, reptile.'

"I am a Dragon and you will respect me as such."

'Kiss my ass.'

Kaito proceeded to wince at the roar that filled his mind, stumbling on the spot and getting a slightly worried glance from Akeno as she walked closer. Not that he noticed however, too busy blinking some of the spots out of his eyes.

"That's enough Riser!" Everybody's attention was drawn back to Rias once again as she stood up, crossing her arms and glaring down at Riser "I don't mind you taking on the Gremory name but who my husband will be is my choice and my choice alone."

"Rias darling. You can't truly be this selfish can you? Riser is under the assumption that your family is still in a situation where you simply can't afford to deny this generous request your father and brother set up."

"This choice was born of my father, brother and clan being entirely too hasty with the future of my life and I will not simply roll over and accept a husband just because they say so. For the final time. I will not marry you Ri-" Rias was cut off as Riser stood and held her chin almost gingerly.

"Need I remind you Rias darling. Riser carries the wishes of the house of Phenex. It would be best not to besmirch that."

In an instant Rias' Peerage all took steps forward, prepared to jump in at Rias' order. Meanwhile, Kaito finally took it as his chance to get ready for combat, focusing fully on stealth as he began to make his way around the room. The teen almost able to feel Grayfia's gaze on him for a moment before she turned her eyes back to Rias and Riser.

"And I don't care if I need to incinerate everyone in this room. You will return to the Underworld with me." Riser threatened.

In an instant the room began to vibrate ever so slightly, both Kings beginning to flare their mana. Their eyes glowing with the colour of their magic while they both stood still, ready to come to blows if the other so much as breathed in too quickly.

"There will be no need for incineration." Grayfia's voice cut through the tension like Kaito's shadow blade, cutting both Kings aura's down to nothing in a single instant.

Slowly the both of them turned to look at Grayfia as she stood respectfully off to the side.

"As you both know I am here on the orders of Sirzechs, Lady Rias, Lord Riser. Which means there will be no disruption of peace." Grayfia continued, staring at the both of them with an aloof expression.

Chuckling softly, Riser closed his eyes and shrugged in a 'what can you do?' type gesture.

"When told something so ominous from the 'Greatest Queen' even Riser feels a chill down his spine."

"Sirzechs guessed that negotiations would break down. So he has offered a possible solution."

"Of course, he did." Rias groaned in exasperation, rolling her eyes "Would you mind elaborating?"

"If Lady Rias was to continue putting her personal preferences above those of her family and clan. She is to compete with Lord Riser in a Rating Game for the fate of their engagement." Rias' eyes widened and her mouth opened a little, a minute gasp being heard from her.

"A rating game? Why's that sound familiar?" Issei asked, getting a giggle from Akeno.

"Rating games are games, or competitions if you like, that only mature Devils can compete in. Partaken by a King and their Peerage."

"Wait, does that have something to do with the chess stuff?"

"That's right. It's why the Evil Pieces are modelled after chess pieces the way they are." Akeno confirmed with a nod.

"Riser has participated in numerous games and won the majority of them. Meanwhile my inexperienced bride hasn't fought in a single one." Riser gloated a little, looking at Rias out of his periphery and seeing her scowl.

Rias wondered how quickly Riser could react if she blasted him right now. Surely if she got enough energy in the blast from this distance he wouldn't have the time to move out of the way. If she made it powerful enough she might even be able to atomize him before his regeneration was able to kick in.

But no, she couldn't do that. Not only would it be horrible for her family, despite what she said about them earlier, if she did that. Grayfia would also never allow her too. No matter how fast or powerful Rias was, she was under no assumptions that Grayfia couldn't shut her down before her magic circle even finished forming.

"Also Rias is this all the Peerage you…have?" Riser asked, beginning smug before noticing the disappearance of Kaito and narrowing his eyes for a moment.

But only for a moment, his arrogance soon overshadowing anything else running through his mind and making him just shrug and throw away his thoughts on the spiky haired brunette.

"Because if so, that's cute. Allow me to show you what Riser is working with." Snapping his fingers, a deep orange magic circle swirled to life on the floor beside him.

With the cry of a phoenix, the circle began to glow brightly and flames burst out of it. Off to the side, leaning against the wall, Kaito winced from the brightness of the fire and wondered in annoyance if all Phenex spells had to be this flashy and annoying or if that was just Riser.

From the flames rose fifteen figures, and not just any fifteen either, Kaito noticed, but all of them seemed to be wom-

'Oh fuck. Oh fuck no. Issei I swear to Leviathan…' Kaito mentally growled, looking over at his brother to gauge his reaction.

"As you can see Rias dear, Riser has fifteen servants. A full set."

"And they're all smoking hot!...I wanna be this GuuuUUuuUuUyyYyYy!" Issei began to sob while staring at Riser.

For a brief moment the tense atmosphere was once again dissipated as Rias embarrassedly explained Issei's wish to be the harem king. As she did that, Kaito began to appraise each member of Riser's Peerage. His gaze slid over each one, taking in hints based on their clothing and how muscular they appeared.

Of course there were hints that someone more experienced would pick up that would tell them a lot more. But for all of Kaito's training and trying, experience was something he couldn't quite practice, and so he'd just have to go with what he thought to look for. As best he could he tried to gauge their mana levels, only focusing on whoever his gaze was locked on.

And then he got to one of the smallest girls. A blonde with curled twin-tails shaped like drills and blue eyes that dragged over the rest of Rias' Peerage with a holier-than-thou attitude. Focusing his magic sense on her, he had to fight to not do anything that would give away his hiding place.

If his mana sense gave him a mental image of a flame, and his own mana reserves were the size of a car. Then this girls was a bus, larger even than Akeno's own mana reserves, but far….wilder? Whether or not she was actually stronger wasn't something Kaito could figure out as he was now, but still. Her power was nothing to scoff at, and yet she was still so young…

Meanwhile, said girl, Ravel Phenex, blinked out of her disgusted look aimed towards Issei as she felt someone's gaze on her. However she couldn't actively feel anyone around her, as if a phantom was watching her. Someone used to not being focused on yet immensely powerful. Someone that felt like..

'A dragon? But the Boosted Gear is crying over my broth…er….' Ravel swiveled her gaze and met the brown eyes of Kaito Hyoudou.

His eyes widened slightly as she noticed him, but soon levelled back down into a cool gaze as the both of them began to stare each other down. To Ravel, for the briefest of moments, Kaito's eyes flashed purple with draconic pupils and wings of shadow spread from his back. To Kaito, for the briefest of moments, Ravel's eyes flashed into a mixture of green and yellow, feathered wings of fire spread from her back and two lines of yellow, orange, and red plumage flowed from her back and coiled around her. Not unlike the eyespots of a peacock or like shown on many artists' interpretations of a true Phoenix.

Yet for both it was only for a moment, the phantom mirages disappearing in the blink of an eye and leaving the both of them staring at each other suspiciously.

"Hoooooh? How fascinating." Betzalel growled, Kaito practically able to hear the grin on his features.

'You going to actually explain or just stay cryptic there?'

"Watch your snark. That girl. She's the same as you."

'She has a Sacred Gear that's a pain in her fucking ass?'

"For that, you're on your own mongrel." Kaito mentally sighed as he felt Betzalel block himself off, finally having some mental peace.

Though now Kaito's thoughts were running wild with what Betzalel could mean. It could be a Sacred Gear; he wouldn't rule that out. But Betzalel had also said multiple different things about him and Kaito wouldn't put it past him to know things that Kaito didn't and was just holding onto that knowledge.

Finally, both Dragon and Phoenix looked away from each other when they heard the sound of Issei activating his Sacred Gear, getting a narrowing of Kaito's eyes. The teen preparing to move, if need be, to help his brother out. He had a habit of getting into situations over his head.

"Mira." Kaito watched a blue haired girl wielding a staff dash forward to intercept Issei before he could get near Riser.

Kaito leaned forward, prepared to fight at the drop of a hat. Only to see Ravel step back and say something to one of the many women besides her, causing her to look over and widen her eyes in alarm when she saw Kaito. And then Issei struck the ceiling, and Kaito could feel his anger coming to a rolling boil. Getting a giggle from the other girl, a brunette in a maid outfit.

Ravel however twitched and fear passed through her mind for a fleeting moment before disappearing as she scowled in disgust. Seemingly finding it below her to fear something like some random reincarnated Devil.

"Grayfia. Tell my brother….I accept the Rating Game."

"Very well, Lady Rias." Grayfia bowed to acknowledge the order.

"And Riser? I'll destroy you and your full set completely." She scowled, glaring daggers at her fiancé.

"Hahaha! Believe what you wish, my darling Rias. Until we meet again on the battlefield~" Riser grinned arrogantly before him and his Peerage disappeared in a burst of flames.

XXXxxxXXX

Two Days Later, Gremory 'Training Ground'

"Why do I have to get my ass kicked by Kiba! Asia gets to train with Akeno and Kaito's off doing his own thing!" Issei groaned, lying on his back on the grass.

"Asia is learning to better use her magic, because she's my Bishop. And Kaito is a Knight like Kiba but has a lot of magic potential. You need physical training Issei." Rias explained with a giggle, squatting beside him as he lay spread eagle "So while the both of you are with his usual training partners he's working on refining what he already knows. He's working just as hard as you are Issei~"

"Yeah but he doesn't have to get the crap beaten out of him constantly!" Issei whined, finally finding the energy to sit back up.

"You should have seen Kaito when he first started. He wasn't much better than you with a sword." Kiba said jovially, getting a surprised look from Issei.

"Really?" Rias raised an eyebrow at the look on his face and the tone of his voice.

"Does that surprise you Issei?"

"Hell, yeah it does. Kaito's super talented." Issei explained with a nod "He's always been more comfortable by himself, so I try to include him in stuff all the time. Don't tell him this though, but I'm a bit jealous of how talented he is. Physically and Mentally." Issei admitted with a sheepish grin, scratching the back of his head.

"Really? You're not bad at either of those things, Issei." Kiba pondered while resting his weight on one foot.

"I mean I try my best, sure. But I still only get slightly above the middle of the class. Kaito's always been good with that stuff though. I can't tell you how many times I got into fights trying to stop kids that were jealous of him from fucking with him." Issei laughed while wobbling to his feet.

"Huh…I never thought we'd share something in common like that…" Rias mumbled, getting a confused look from Issei.

"Huh? What do you mean Buchou?" Issei cocked his head to the side.

"Just the both of us having really talented siblings." She giggled, petting his head like a child "Now, are you ready to keep going Issei?"

"Ughhhhh, do I have to Buchou?"

"Yes~"

"Yeah yeah ok. Come on pretty boy. Let's see how many seconds I can avoid getting whacked in the face this time."

"There's the spirit Issei!" Kiba smiled and without warning rocketed himself forward.

XXXxxxXXX

That night, Rias

Rias hummed to herself, sitting at a desk with pieces of paper strewn all over it. The paper being maps of all of Riser's previous battlegrounds with hand-drawn annotations from herself marking how he's moved his Evil pieces and the potential reasons why.

"Himejima said you wanted me?" Rias jumped in her seat and yelped cutely, aiming a pout and a glare at the entirely unapologetic Kaito.

"Yes, I did tell her that. Thank you for coming." She sighed, gesturing to a seat.

"So? Why do you want to speak to me?" He asked gruffly.

"Even now I still can't get you to act respectfully?" She opened with a teasing comment to try and steer the conversation a bit more in her favor.

"You've earned some of my respect, but not that much." He shut her down with surprising ease "I'll listen to your orders in the Rating Game or in combat easily enough. Doing my own thing without running it by anyone is just detrimental in the end. But outside of that? You still have more work to do."

Rias frowned at his cold words. Because that's what they were, cold words with harsh connotations and an uncaring expression that told her he didn't care how she reacted because he believed what he was saying. But at the same time…. At the same time she knew that Kaito wasn't completely as cold as he made himself out to be. There was a warmth hidden at the bottom of the frozen tundra that was Kaito Hyoudou. So Rias thought to look at it from a different perspective, a more…pragmatic one.

"Hm. Thank you Kaito."

"I don't know what you're thanking me for. Unless you're as masochistic as Himejima." Rias giggled at that, waving a hand.

"No, Akeno is special in her own right. But I was thanking you because in your own way, you're trying to push me to be better, right?" Kaito gave no indication if she was correct or not "Not going to give an answer? That's ok. I've gotten my own answer out of it."

"Whatever you say Gremory." Kaito snorted.

"You really are different from your brother." Rias commented serenely, getting another snort from him.

"You're just figuring this out?"

"No. Just thinking over a conversation I had with Issei earlier today. Speaking of. How is your training going?"

"I'm working on a technique perfect for 'assassinations' so to say. An easy way to sneak up on a target and get a surprise strike on them." Rias blinked at the admittance to such a thing, not used to such an outlook.

Though in this situation she could absolutely appreciate it.

"You've been working on your stealth recently. I didn't notice when you'd moved during the meeting with…him."

"No one did. Save one of them. Blonde girl with drill twin tails."

"Blue eyes?"

"Yeah that's the one." Kaito confirmed with an annoyed look.

"Ravel Phenex. The younger sister of Riser and the fourth in line to the Phenex family head. Also the only female amongst all the Phenex Heirs." Rias explained, getting a click of Kaito's tongue as he leaned back in his seat.

"Damn. No wonder she's got a mana capacity like that…" He muttered, though Rias heard him.

"You can sense Mana capacities?" She asked, blinking owlishly and tilting her head to the side.

"Somewhat. Hers is large." He replied in annoyance.

"Unsurprising. She found you? Is that why you didn't rush in to help your brother?"

"Her and one of Riser's harem were preparing to do something if I did. Believe me, I wanted to cut all of them down." His glare darkened and his pupils extended ever so slightly.

'Why would Ravel be preparing to do something if Kaito moved? The rest of my Peerage were practically ready to start fighting right then and there but Ravel focused on Kaito? Interesting….' Rias thought, her mind whirring through possibilities in a couple seconds.

"Hm. Kaito? I'm curious. What do you think of your brother?" Rias asked.

Kaito, hearing this question, narrowed his eyes in suspicion.

"He's, my brother? I care for him."

"I don't mean like that, Kaito." Rias giggled, getting a roll of Kaito's eyes.

"Uh huh. I'm sure. Look, Issei's nice, helpful, he's a little naïve but if you've got his trust he'll help you however he can. He can make a friend out of pretty much anyone, something I'm jealous of." Rias' eyebrows rose into her hairline.

The words of both brothers rattled around inside her head as he stood and walked out. Leaving her in her office on her own completely.

"So…both brothers are jealous of the other? Huh, Issei has such an interesting family~…" Rias mumbled to herself, the tiniest blush adorning her cheeks.

XXXxxxXXX

Meanwhile, Phenex Manor

Serena Phenex, otherwise known as Lady Phenex, smiled softly as she made her way into her daughter's room. Prepared to say goodnight to her like she tried to do every 1-2 days. However she was met with a surprising sight as she opened the door and came across Ravel, not preparing for bed as she usually would, but sitting in the armchair in the corner of her room surrounded by books.

One of which she was nose deep in, her eyes skimming across the pages in constant motion. Finally noticing her mother and looking up, her eyes widening and her cheeks flushing a bright red.

"M-Mother!" She yelped, snapping the book shut.

"Ravel, dear. What's got you in such a mess? I haven't seen you this determined in years." Serena smiled and walked over to her daughter.

"One of Rias Gremory's Peerage…" Ravel admitted, a confused expression covering her features.

"Hm? Which one? The Priestess of Lightning?" Serena tried to guess, making a curious noise when Ravel shook her head in negativity.

"No, Mother. One of her newest reincarnations."

"Ahhh, the infamous Boosted Gear?" And Serena was once again surprised when Ravel shook her head.

"No Mother. Another one. I did some digging and I've found out that he's the brother of the Red Dragon Emperor."

"So what's caught your interest about him?" Serena wondered, leaning against the side of Ravel's armchair to look at the book in her daughter's lap.

Mythical Creatures of the Past.

"When I was looking at him…for a moment I saw a dragon." Ravel seemed confused as she told her mother, staring intently at the book on her lap.

As she did so, she missed how her mother perked up, raising a slender eyebrow at what she had just heard.

"You saw a dragon when looking at him? How interesting. He must have a draconic Sacred Gear then. Similar to his brother." Serena suggested, getting a tired groan from her daughter.

"I thought that as well, Mother. But none of the Draconic Sacred Gears have anything in common with what I saw…" Ravel mumbled, twirling one of her twin tails around one of her fingers.

"How interesting…" Serena mumbled, beginning to get as drawn into the mystery as her daughter.

"Now I'm trying to find something on the Dragon itself." Ravel admitted, gesturing to the title of the book.

"A good idea. Hopefully you can find out some information. The Red Dragon Emperor's brother seems to be just as interesting as him." Serena giggled, getting a tired look from Ravel.

"Mother…"

"You know I'm just having some fun, Ravel, dear. Now I'm sure you'll figure this out before the Rating Game. But for now you should sleep. It'll do you some good."

Ravel sighed and sat still for a moment before nodding weakly.

"Yes Mother."

"There's my girl. Now let's get you ready for bed." Serena smiled at her daughter's childish pout as she whined slightly under her breath.

But unlike her daughter, Serena was far more used to later nights or staying up all night. And this enigma had spiked her own interest as well. So, while her daughter slept. There may or may not be some research of her own Serena would partake in.

XXXxxxXXX

Five Days Later

Kaito walked into the ORC dressed not in his school uniform, like the rest of Rias' Peerage, including Rias herself, but in something new. At least to the rest of the ORC. His combat/mercenary uniform covered him, earning surprised looks from everyone.

'Todays the day. You ready to take down some Phenex's?' Kaito mentally wondered, hearing a deep, amused chuckle.

"The only True Phoenix amongst them is that blonde girl. So long as you get a proper fight with her. I'll only be happy if you eviscerate every faker you come across."

'For once I think we'll get along. That was my plan regardless.' Kaito smirked to himself, curling his hand into a fist.

XXXxxxXXX

Hey guys!

Welcome to the end of this double update and also the end of this massive month of updates! I hope you guys have enjoyed the month and the story so far.

I really love the world of Highschool DxD and believe that a lot of people write it off too quickly because of the fanservice elements which, while definitely fun, isn't the only thing the world is built around. But that's just me beginning to complain so I'll cut myself off here.

Sooooo, it's my birthday today! I'm pretty excited, because not only does it mean that we're going out to a nice restaurant for dinner. But also that I'm giving myself a small present after all of the work I've been doing.

I'm not updating during the month of December. Not a single story. Not a single chapter.

This was done to give myself a break since between Heir to the Blacksmith, and Emerald Fang (On ao3), I've been writing minimum 10K words per month to continue the monthly updates. And that's not even counting in updating my myriad of other stories. And while I love that system and want to continue it. I just need a break. And what better time than good ol' X-mas?

Now in an ideal world, I'll be back to updating during January and going forward, but if that changes I'll be sure to write an Author's Note chapter letting you guys know what's going on.

Discord: /ctMzhq3