Authors Note: Decided to give it another try with the Highschool DxD stories. This time using the other story line I had brainstormed at the same time of my previous work. Looking back now, wish I had gone with this one instead, but I digress XD

Despite the fact that I was blessed with both the rank and power that many would give their right arms to possess, in truth my current position ranged from tolerable to extremely irritating.

Not because I had to deal with regular mountains of mind numbing paper work.

Nor was it due to the fact that I had to regularly deal with those that continued to believe that their family`s adherence to the traditional values of their race gave them the right to make their voices heard. Though I suppose I should be grateful for this since it means that they are more unwilling to back down from the almost ritualized way most families settled disputes nowadays.

No. My less than appreciative views regarding my position stemmed from the fact that my 'superior' was cursed with not only the mentality of an excitable child, but also with the power to wipe out a descent sized country.

"Pleaeeeeaassssse Dante. Just do this one tiny thing for me, and I promise I won't ask you for anything else".

Maintaining an unimpressed look as I stared into the pouting expression of my so called master, I ensured that my tone was firm as I, once again, refused her request.

"For the thousandth time Serfall my answer is no. Its bad enough you have me waste my time doing a good portion of the paperwork your supposed to have done yourself. But under no circumstances am I going to embarrass myself by becoming a character on your rip off of Sailor Moon".

Hating myself for even having enough knowledge to make that comparison, though at times I didn't actually mind having a rather impressive knowledge of well known western and eastern animations, I allowed more than a hint of disbelief to cross my features as the pink eyed Satan Lord tried to refute my suspicions.

"That's not what I wanted to ask you".

Maintaining my unimpressed glare, I was entirely unsurprised by the look of guilt that came over her face.

"Okay. Maybe only a little. But that's only because I'm concerned about your image. It's mostly my fault that you got stuck with that unfortunate title, if only because you were being meaner than usual that day. But if you started becoming a little more...personable, people would stop calling you the 'Cruelest Queen', and perhaps start calling you the 'Cutest' one instead".

Having no desire to revisit that particular topic, for it tended to sour my impression of what would otherwise have been a ideal moniker, I released a sigh as I decided to, not for the first time, feign interest in the immature scheming of the woman whose was in charge of my adopted race's foreign affairs.

"Moving past the...unfairness of my unofficial title, what was it that you wanted Serafall? If its about that rather...surprising offer from Kyoto, rest assured that I have yet to come to a decision".

Enjoying the brief scowl that appeared on the pig tailed Devil's face, though in truth I still had no idea why she was upset since she was the one who suggested that I help her improve relations with the ruling members of the Youkai nation, I had to confess that I was momentarily caught off guard by her next question.

"How...would you like to take a bit of a break from your 'official' duties as my Queen. I know I don't say it often enough, or express it in a manner that you can appreciate, but I truly appreciate all that you've done for me since I added you to my peerage".

Though shocked by this serious and genuine admission of gratitude from my usually childish master, part of the reason why I was so successful in my current station was because I never accepted things at face value.

"Your gratitude is appreciated. However, I assume that there is some sort of catch to this...offer"?

And just like that, the girl whose power had allowed her the right to adopt the name of one of the most powerful leaders in Devil history reverted back to her usual self.

"Welllll, sort of. Your break is more like a working vacation really. You see, I'm worried that my dear Sona might be...".

At this point I decided to block her out. For while I could appreciate the importance of strong sibling bonds, partly because I no longer had any of my own, Serafall's obsession with her younger sister was something that I didn't really want to think about.

But sadly, I was prevented from allowing my mind to wander to more pleasant things, like say the chance to temporarily do without the hassle of an overly excitable child trapped in the body of a woman, thanks to a rather heavy blow to the head.

"I can tell when your zoning out on me Dante. Just because you don't share the same loving relationship with Sona that I do, doesn't mean that I won't trust you to keep her safe. And Rias too now that I think of it".

Rubbing the part of my head that had been hit by that ridiculous prop of hers, I tilted my head in confusion as I sought to clarify what she meant.

"And why would it be my responsibility to look after Lord Lucifer's sister when he has...other agents to carry out his brotherly duties"?

At this point, Serafall once again adopted the persona that was similar, if milder, too her younger sibling.

"Because unlike myself, Sirzech's peerage is more afraid of his wife than they are of the man they call master. And since Grayfia is more willing to put duty ahead of the personal desires of those close to her, Sirzech's needed someone who is not only an outsider to the arrangement between the Gremory and Phenex Clans, but also has the power to put a certain flame grilled chicken in his place should he decide to become more...insistent in his desires".

Nodding my head in agreement with my master's viewpoint, for everything she had said was true, I found a small smirk spreading across my face as I was presented with a rather rare opportunity.

"Of course your first priority during our time apart is towards my sister. Sona must be in such a dreadful state since I can't be with her. Especially since I have just learned that she has added a boy to her peerage in order to make her feel more confident about her body. But since Rias has also achieved a similar important milestone, one that sadly signifies that she is becoming more independent, my colleague also wishes you to do the same for him as you will for me".

Leaning back in my chair as I considered this request, I nodded my head in reluctant agreement before I began to spin this to my advantage.

"If both you and your fellow siscon are so adamant about this, I do not see how I can possibly refuse. However, I do have some conditions".

Though my words earned a frown from the black haired Devil, I nevertheless received a nod in order to list what it would take to ensure that I fulfilled the role of babysitter with my usual competence.

"First, and this is non negotiable, while I'm fulfilling the role of your proxy stalker, I will only be doing a fraction of my usual paperwork. If there are unexpected emergencies, like say a diplomatic crisis that could lead to the Three Factions resuming the War, I will do my job. But if it's something like sorting through your fan mail, or dealing with the casting list for Miracle Levithan's next season, I will not be happy".

My words earning pouting nod of acceptance from Serafall, I continued my demands.

"Secondly, when it comes to my role as 'protector', I am allowed to use any means necessary to ensure the well being of both your 'Darling Sona' and her more buxom friend. If that means I have to break the taboo of disciplining their peerage, or using methods that you would find 'mean', both you and your fellow can't get too upset about it".

At this point, Serafall expressed her displeased agreement in a more verbal manner.

"Fine. But under no circumstances are you to lay an angry hand on either Sona or Rias. Though I suppose when it comes to Rias, if she tries to seduce you like some of those Youkai women, I guess it would be ok if you spanked her. But not Sona. If your going to be doing anything like that with my sister, I have to be present. And even then you'll have to wait your turn".

Deciding it wasn't worth my breath to once again explain that I had no interest in the younger Sitri sibling, or some of the more forward court members of Kyoto, mostly because it would inevitably lead to another clumsy attempt to make me emulate the example of the Underworld's 'Strongest Queen', I moved to my last condition.

"And lastly, I want to continue making contracts. I realize that at this stage the power I gain from completing one is miniscule, but its something I find enjoyable. So I trust that you don't mind if I do something that is technically below your station

For a moment, Serafall said nothing as she thought over my last condition. But soon enough, she shot me a smile as she nodded her head.

"I don't see why not. But only if your willing to deliver personal messages from me and Sirzech's to our sisters on a regular basis. Fair enough"?

Releasing a snort of amusement at this rather simple demand, if only because it would provide me with sufficient entertainment from both heiress's, I felt another annoyed frown spread across my face as Serafall decided to take advantage of our arrangement in order to ignore my previous warning.

"Now that we have that out of the way, lets decide what your cover is going to be. It will be good training for you once you finally decide to join my show".

...

Despite the fact that they didn't really need to attend school, one of the benefits of belonging to one of the more influential families that ruled the Underworld, both heiresses nevertheless enjoyed their time posing as regular students.

Albeit for different reasons.

For the next head of the Gremory Family, it was a chance to experience what it was like to behave like an ordinary girl without having to worry about the responsibilities and hardships that came with her position. At least temporarily

And for the heiress of the Sitri Clan, it was an opportunity to learn all that she needed in order to ensure that her dream of opening her own school became a reality.

However, despite the fact that they were only attending Kuoh academy in order to provide a cover for their real duties, the 2 pure blooded Devils were nevertheless quite happy with their current lives. Even if they had to deal with the occasional occurrence where their true duties interfered with their covers.

"So you finally decided to have a boy on your 'team' Sona. I must admit that is rather progressive of you considering your previous stance".

Shooting the smirking red had a slightly amused look from behind her spectacles, the Sitri heiress was well prepared to make her own observation regarding Rias's situation as they waited for their class to begin.

"And I for one am surprised that you decided to recruit one of the members of the infamous trio into yours. I know that you have a bit of an...open mind when it comes to members, but surely someone of Hyoudou's nature will only cause problems for your group dynamic".

Shrugging at her friend's concern, though in truth she had considered it before she had used all of her pawns to return Issei to life, Rias was prevented from commenting thanks to the sudden intervention of her best friend.

"Fufufufu. And I suspect the same could be said of your newest council member. He might hide it better than most boys, especially ones like our newest member, but if you look closely enough, you can tell that that he also has a rather high interest in the female gender".

Conceding the point with a curt nod, for she too had seen the way Saji's eyes had briefly behaved before he had managed to get a hold of himself, Sona found a small smile gracing her features as her own Queen decided to offer her opinion.

"That may be so, however I suspect that our newest member will at least be able to reign in his desires far more effectively than yours. Because unlike the more, and I use this term for anything better, likeable member of the Perverted Trio, Genshirou doesn't constantly declare his love for all things breast related".

Nodding her head to show her agreement with Tsubaki, the pink eyed Devil was reminded that while her right hand Devil enjoyed many similarities to Akeno, the pony tailed queen of Rias Gremory was perfectly willing to cross certain lines that even her sister refused to do.

At least on purpose.

"Considering the...variety of measurements he will soon be working with, I suppose that it will be some time and effort before he is as honest about his feelings as my newest club mate is with his".

Unsure if she should be more annoyed with Akeno or her master, who had taken the opportunity provided by her queen to silently remind her of their...differences, Sona was prevented from doing more than glare thanks to the unexpected arrival of the school principal.

"Attention students. I apologise for the interruption but I have some unexpected news. It appears that Kuoh's English teacher, Mr. Miyoki, has decided to retire early this year due to an unexpected windfall. But the good news is that a substitute is immediately available to take his place for the rest of the term. I am confident that as 3rd year students of Kuoh Academy, you will ensure that this won't effect the quality of your work. With that being said, it is my pleasure to introduce you to your new English teacher, Mr. Inumbro".

While the news of a new teacher caused mix reactions amongst the human members of the classroom, mostly disinterest along with some slight anxiety since they would have to get used to the teaching styles of a new educator, the reaction of the 4 Devils, both pure and hybrid were remarkably different.

Especially when their new 'teacher' entered the classroom.

...

Though I was able to effortlessly maintain the mask that had ensured a rather successful career as one of the Underworld's chief dealers, I nevertheless allowed some of my amusement to leak into my eyes as I took note of the expressions of both the heiresses and their servants.

The look of dawning horror that was currently being worn by Serafall's sister was understandable, though in this case completely unwarranted since my arrival did not signify that her more excitable sibling was about to burst through the door. Though I somehow doubt that she would treat my solitary presence with anything but uneasy suspicion despite the fact that I have treated her more or less amicably since her sister...rescued me.

The carefully guarded expression of nervousness that was currently being worn by her queen was also understandable since Sona had no doubt shared one or two stories of what I was like when I was feeling particularly spiteful.

Sirzech's little sister was currently shooting me an expression of carefully guarded wariness though I couldn't tell if that was because of my reputation, or the fact that my appearance wasn't exactly what she was expecting.

And as for her pony tailed servant, I was uncertain if I should be flattered or concerned with the look she was sending me. For while I was not a stranger to the expression known as bedroom eyes, especially when I was forced to attend various social functions where the females are from a society that still clings to the rule of 'survival of the fittest', I was pretty sure that receiving such a look from school girl was unacceptable. Especially when one enjoyed a position of authority.

However, thanks to Serafall's decision to have me pose as a teacher while I enjoyed my little 'vacation', I would have to deal with the quartet later since it was time to play the part of a high school teacher.

"Good afternoon class. As your principal has already graciously explained, I will be taking the place of your previous teacher for the term. To ensure that this...transition isn't too disruptive, I will continue to follow Mr. Miyoki's lesson plan until I have a better grasp of your capabilities. By which time I am certain that I will have enough insight to start deviating from what had been the original plan".

Earning a look of acceptance from the academy's human administrator, who then proceeded to leave the classroom once she determined that I had everything in hand, I allowed a slightly predatory smile to spread across my features as I did what all students hated.

Asking a question at random.

"Now, can anyone tell me which is the most published book in the English language"?

...

Despite the mixed reactions the female Devils had experienced upon learning the identity of their new substitute teacher, none of them could say that their black haired teacher wasn't an effective educator.

Though they each silently agreed that his methods were a tad more...brutal than what they were used to.

For while it was clear that he knew the material, and displayed a level of patience for those who had some difficulty in grasping newly introduced topics, he was far less forgiving when it came to material that had previously uncovered.

And this was best showcased at the end of the class.

"For those of you that have failed to properly translate Shakespeare's most lengthy tale into its more modern form, you have 1 week to not only write an essay summarizing the key elements of the story, but also a report identifying why you failed to use the knowledge you had gained in previous classes to accomplish this in class. And, you will write it all in English".

Grateful that the passive abilities of their race, not to mention their private tutoring, had allowed them to escape such a punishment, the two pure blooded Devils were largely unsurprised when they were told to stay behind.

"Ms. Shitori, Ms. Gremory, if you could remain behind for just a moment. I promise it won't take long".

Forcing polite smiles onto their faces as the rest of their classmates left the room, Sona, and to a far lesser extent Rias, were partially prepared to deal with their new teacher's sudden change in demeanor.

"Since you two are no doubt burning with questions, I suggest you ask them now. Though I suspect I already know what the first one is. So to save us some time, the answer is yes. Serafall not only knows that I am here, but it was also her suggestion".

Releasing a tiny sigh of relief, for in truth she had been slightly worried that her sister had finally driven her ill tempered servant into becoming a Stray, Sona nevertheless wore a frown as she asked her next question.

"And why would my sister suggest you come here Inumbro? While I cannot speak for Rias, I can assure both my sister, and Lord Lucifer that my peerage and I have done our utmost to fulfil our responsibilities here in Kuoh".

Shooting her friend a slight glare for essentially throwing her under the bus, Rias opened her mouth to declare her own success in managing their territory when she Serafall's queen held up his hand in a placating gesture.

"And I can assure the pair of you that both of your siblings are content with how you are managing your responsibilities. I'm only here because the two biggest siscons in the Underworld decided to place some conditions on my well deserved vacation. So you can rest easy that the arrangement of governing this territory has remained unchanged".

Sharing similar flushes of embarrassment as they were reminded of the more immature tendencies of their more powerful siblings, the buxom heir of the Gremory clan narrowed her eyes as she raised a question of her own.

"And what conditions would these be"?

Earning a snort from the male Devil, though they were unable to tell if was one of amusement or irritation, both heiresses released their own sighs of annoyance as Dante listed them.

"Well for starters, I am to act as a messenger for your siblings whenever they wish to convey their...feelings for you. Originally they wanted this to happen every day, but in order to spare myself the headache that comes from being reminded that our leaders have an unhealthy obsession for their younger siblings, I managed to convince them to do this once a week. I trust that you both find this to be agreeable"?

Though grateful that the black haired Devil had managed to reduce the amount of time they would have to deal with their needy and powerful siblings, Sona and Rias nevertheless quickly glared at the uncaring male as he listed the other conditions.

"The rest are relatively straight forward, though their nature is a tad difference considering the individual circumstances you both find yourselves in. For you Sona, I am to ensure that nothing...inappropriate happens between you and your latest acquisition. Personally I could care less if you decided to do away with that chess rule of yours, but since Serafall still seems willing to cross that particular line, I'm afraid that there isn't much I can do to ensure that your first time isn't with a blood relative".

Unsure if she should be embarrassed or angry at the way Dante was talking about her sister, for while blunt nothing what he said was untrue, Sona was grateful for the reprieve as her sister's servant turned his disinterested gaze towards her friend.

"And as for you, your brother has instructed me to ensure that neither party of your...arrangement does anything to violate it's terms".

His words causing the crimson haired heiress to clench her hands in anger, Rias found herself somewhat surprised as the queen of Serafall Leviathan proved to be more understanding of her situation than her own sister in law.

"Of course since I honestly approve of your distaste with your chosen fiancé, why your parents thought it was a good idea to set you up with the weakest member of the Phenex Clan is beyond me, I actually care little for what you do to escape it. Though there is probably one thing you should watch out for".

Blue eyes narrowing as she tried to determine whether or not the Devil in front of her truly meant what he had said, though judging from what Sona had told her about him in the past she had to concede that he was probably telling the truth, the buxom red head managed to keep her voice even as she asked a rather obvious question.

"And what precisely would that be".

And it was here that Dante's expression changed from disinterest to one that could almost be labeled genuine concern.

"The fact that your efforts to free yourself from being shackled to that flaming bird brain might actually cause that unhappy date to happen sooner rather than later. For while I have...permission to deal with your fiancé should either he, or his harem decide to interfere with your current life here in Kuoh, I'm afraid there is relatively little I can do if the head of the Gremory and Phenex Clans decide to move the wedding to an earlier date. Something that may very well occur if they believe that your being a bit...frivolous with your chess pieces".

Accepting the warning with a frowning nod, Rias was momentarily caught off guard by Dante's change in persona.

"Then we are done for the moment. I trust that as accomplished members of this fine institute, I can rely on the pair of you should I need an extra pair of hands"?

Though kindly worded, neither Sona or Rias misunderstood that they had a choice in the manner. Thus they simply nodded their heads as they made their way out the classroom.

"Oh and Ms. Gremory. Please tell Ms. Himejima that while I am flattered by her attention, this is neither the time or place to forget the nature of our roles. And while I suspect that it will take some time for that lesson to truly sink in, you should inform her that there are other ways to enforce compliance that don't involve the usual methods of sadomasochism".

And with a casual wave of his hand, the door to the classroom barely missed hitting the 2 heiresses as they stared at the Devil who would either prove to be a help, or a hinderance to both of their peerages.

...

Annnnnnd I think this is enough of an intro chapter for now XD.

Again, when I first contemplated doing a Highschool DxD story, one of the ideas that I had was having my OC as a member of Serafall Levithan's peerage instead of him becoming a member of Rias's. Some of the really good HDXD stories that I have read on fanfic are the ones were Serafall gets a new servant, who wither acts like a shy kid, and thus willing to do whatever she wants, or ones where her servant is resistant to her childish antics.

The attitude would be the same, the abilities/backstory I initially envisioned would be the same (though greater in scope since he is not only older, but in a better position than he was in my orginal story). But his status would be much different.

Also, having him belong to the peerage of a Maou would ensure that other story elements that I had intended to eventually reveal in the other story would happen much earlier here.

Anyways, hopefully you all enjoyed this chapter.

Plz review. no flames. Keep any criticism polite and reasonable XD

And til next time

Ps.

Have decided to maybe go back and continue my 'orginal story', but that wont be for a while