November 16th 2016 edit: I re-edited this a lot. I hope that it is a whole lot better than what was previously written.

Disclaimer: I do not own the Diamond/Joker/Clover/Heart no kuni no Alice franchise. I do, however, own some OCs who will be appearing soon.

Prologue

Nightmare put down his pen and leaned back in his chair with a sigh as he closed his eyes. Or eye in his case as one of them was already closed and hidden underneath the eye patch that he was required to wear per the Rules.

It was nighttime and the ruler of the territory of Clover Tower had been working for eight time periods straight (last time he counted). Despite the temptation to turn in and continue later on, he still had quite a bit of paperwork to get through and he would not be satisfied until it was all done.

Though a small break wouldn't hurt; his vision was starting to blur from reading and signing papers for so long, and his hand ached from having to write out his signature over and over again. Not that anyone could have denied him the break anyways. He was the most powerful individual in the country after all and was therefore his own boss who decided not only his own work schedule but everyone else's as well.

"Lord Nightmare?" Nightmare's single grey eye snapped open and he sat up straighter in his seat as his head jerked sharply towards the door. Everyone else had retired to their rooms for the night, leaving Nightmare the only one in the work office. Seeing who the owner of the voice was, he relaxed slightly.

"Gray." The ruler of Clover Tower stated neutrally when he visually confirmed that it was his assistant/second-in-command/bodyguard, Gray Ringmarc, who had called out his name. "It's late. You should have gone to bed like everyone else."

The way that Nightmare phrased his last sentence made it clear that it was a statement and not an inquiry.

Nightmare couldn't help but eye the man in disapproval. His normally neat pressed second-in-command looked as if he hadn't slept, or taken any breaks for a long time. There were bags underneath Gray's golden eyes, his dark coloured hair was no longer combed neatly in its usual style, and the way his body slumped underneath his rumpled clothes indicated that he was exhausted.

At that exact moment he bore such a strong resemblance to his younger self when he was still an assassin out for Nightmare's head that it took the latter a minute to remember that the man was working for him now and had been for a while.

The ruler of Clover Tower frowned at the next observation that caught his eye.

Gray was smoking. There was a cigarette held between his fingers as he eyed his boss with concern. Judging from the strong scent of nicotine that was permeating the room, Gray had quite the number of cigarettes before coming into the office.

Nightmare knew that meant he was stressed out about something. Or just stressed in general. The second admission made Nightmare feel guilty since he had a feeling that he was a huge source of that stress, but he also had no idea what to do about it either. They hadn't been on good terms for a while and it felt out of place for him to correct the other man when their long time friendship was so strained.

He also seemed to have lost a bit of weight. Not a lot, but enough to be able to tell. Though whether it was from how thinly stretched out he was juggling all of his responsibilities, his habit of running all over Clover whenever he had the time, or both had yet to be seen.

"I could say the same to you." Gray pointed out, looking right past Nightmare. He inhaled his cigarette, shortly exhaling smoke as he ran a hand through his dark hair, messing it up even further. The simple action emphasized even more just how stressed out he was. "I know you have been working non-stop for the past twelve time periods. You should be more careful and aware of your own health."

Nightmare just stared at him. Gray was the last person who should have been calling his boss out on unhealthy habits considering how much he had been pushing his own limits lately if the rumours circulating about him were true. As well as indulging himself from time to time in some of his previous bad habits.

"I thought it was eight." Nightmare grumbled, not really put out by the miscalculation of how tired he was. "And I'm the ruler of the territory here; I make my own rules so if I want to work over time, then I shall. No one but myself would be able to order me to take a mandatory break. By the way, Gray, I insist that you get to bed. That's an order."

"That's not funny." Gray said, but there was no real anger behind that statement. Just exhaustion, weariness, and resignation.

"Well I thought it was." Nightmare shrugged as he picked up the pen he had temporarily discarded earlier and started on his remaining paperwork again. Break time was over and he needed to finish the remaining unsigned sheets. The pile of unfinished work had dwindled significantly from when it first arrived at his desk, but he preferred finishing the previous stack of paperwork before heading to his room before the next stack of papers was due.

An awkward silence settled in between the two of them as Nightmare signed papers and Gray just stood there and watched. The only source of noise in the room came from the 'scritch-scratch' of Nightmare's pen and the occasional flutter of thin paper as the man in question placed a newly signed sheet on the pile of his other signed works.

If one had told the Lord of Clover Tower that he would actually willingly do paperwork in the past, the man who held the role of Caterpillar would have looked at them like they were crazy before bursting into laughter. But now the fact that Nightmare was willingly signing his paperwork and using it to distract himself from things in general was darkly ironic considering his previous working habits of not doing it at all. Once upon a time, Nightmare hated performing any of his responsibilities and would have ran away at any mention of it, forcing Gray to track him down and make him do his work through heavy supervision. And even then Nightmare had made sure to be as difficult as possible through methods such as procrastination and hiding.

But he had to admit that there was something cathartic about doing paperwork. Nightmare discovered this through sheer chance when he needed a distraction, any distraction as his own wounded emotions threatened to tear him apart from the inside out. That time his emotions fluctuated between anger, despair, and hurt at himself, Wonderland, and the people around him, his eyes had landed on the large stacks of paper that were surrounding his working desk then by chance and that was that. Since then, working had become an addicting outlet and distraction much to the shock of everyone around him. It wasn't as if he suddenly found that doing actual work was fun, but it served as a great way to channel his bubbling and overflowing emotions. Unlike a lot of his fellow Roleholders, he was not a fan of taking out his anger and frustrations on his subordinates- though that one time with Gray had been an exception. An exception that had been justified in his opinion.

And it wasn't as if Nightmare had been the only one who changed. Nightmare had heard rumours about the others and compared to them he seemed to be handling his emotions better.

The silence in the office had become heavy and suffocating, but Nightmare was unsure of how to broach it like all of the other times the two of them conversed. He also suspected Gray was dealing with the same dilemma. While the new strained relationship between him and his assistant had, for the lack of a better term, improved compared to their previous discussions, there were still too many things between them that had become minefields of pain and disappointment... and guilt.

There was a lot of guilt on both sides for numerous and varying reasons. Topics that neither of them broached in fear that it would result in a controlled, but vicious passive-aggressive argument between them both in which one would storm off in anger (often Nightmare). The arguments often left them both hurt and unable to communicate for multiple time periods until there was something that needed both of their attentions.

Lost in his thoughts, it took Nightmare a few seconds to realize that his subordinate was still in the room. Gray hadn't moved or made any noise; instead his gaze seemed to be focused on a particular spot in the wall, his eyes completely blank. Nightmare wondered what the man was thinking about; he was one of the only few whose minds he could not read since Gray had mastered the technique of blocking him from his thoughts long ago.

The silence between them was suffocating, but the Lord of Clover Tower knew that Gray was not going to break it. He had been passive as of late and often completely deferred to his commands these days. Nightmare decided that it was up to him to break it since he was Gray's boss after all. Looking up, he opened his mouth to say something when his gaze landed on something brown that sat on his desk.

His mouth clamped shut with a loud clack as the memories began to flood through him. Memories he was trying to bury deep within his mind... but couldn't no matter how much he tried.

Sitting on top of his desk right, almost mockingly, was a fluffy brown stuffed teddy bear that had a bright pink bow wrapped around its neck. It had a coal black nose and shiny onyx black eyes that seemed to stare right through him.

The bear had been a bit of a prank gift. Nightmare could almost hear the gift giver's voice exclaiming, "Since you seem to fall asleep everywhere, I thought I would get you someone to keep you company!". The soft stuffed toy was shoved right into his arms before the girl who had given him the bear took off running and laughing at the same time.

Once upon a time the bear had just been a stuffed toy that a good friend had given him as a joke and a source of amusement.

Now it was something that he treasured, but also couldn't stand to look at; one of the few things that reminded him that she had existed at some point in this world where everything eventually became meaningless.

Time always moved forward after all and she had long ago become another casualty of the past.

"Lord Nightmare?" He found himself snapped out of his musings a second time. Looking away from the sentimental stuffed bear, Nightmare turned to face his second-in-command again. When gold met grey eyes, the former immediately looked away, gaze being quickly redirected onto the floor again.

"What is it?" Nightmare asked him, making sure that his voice was level.

Seeing the bear had reminded him why he had been angry with his second-in-command all over again; angry and disappointed to the point that it had taken everything within him to look at Gray after what initially happened. But as the new anger surged within him, a small voice in the back of his head also reminded him that there was no point in dredging up old wounds. Doing so would just be out of petty spite that was completely and utterly pointless and would only result in even more awkward silences in the future.

Besides, he knew that Gray was sorry. During that time when Nightmare's fury towards Gray had been at an all time high, his second-in-command had actually gotten on his hands and knees and begged for his forgiveness. The action had surprised him so much, that the rage he had planned on unleashing on Gray had died down somewhat.

Because Nightmare knew. Because despite what happened when Gray abandoned her when he had been strictly ordered to look after her, the second-in-command had never meant for anything to happen to her. Even if there was always tension between Gray and her, the latter had never wished for her tragic fate. The way that Gray was still unable to look him straight in the eye after all this time was all that needed to be said about how he felt and just how sorry and remorseful he was over it.

Nightmare's anger and disappointment had steadily cooled down the more time had passed... but there was a part of him that was still angry. That revelled in the fact that Gray had become quieter; less inclined to call him out because of what happened and afraid of incurring his wrath.

"Do you think that another Outsider will end up here?" Gray's voice was quiet.

Nightmare was surprised by the question. Were his thoughts that obvious? Perhaps Gray had sensed the shift in demeanor when Nightmare had addressed him; while Nightmare could read minds, Gray was an expert in reading people- it came with the territory of being one of the highest ranked assassins in the past.

Between the two of them, Gray was often seen as the more intimidating of the pair due to his status as a former career killer and the only one who could beat the Knight of Hearts in a physical fight. But it went unsaid that he also feared Nightmare to a degree, just like everyone else. A fear that Nightmare had heavily reinforced time periods ago shortly after... what happened.

As a result, Gray had became more cautious and wary around Nightmare when it came to their few interactions all the while maintaining a polite air.

Like now.

But his question made Nightmare pause as it was a very good inquiry. It crossed Nightmare's mind several times, but the ruler of Clover Tower never stopped to really think about the possibility. It was just too painful to even consider it.

"...I hope not." Nightmare finally said.

"I see." Though Nightmare's reply hadn't answered his question, Gray did not ask him anything else. He must have sensed that any further discussion on that topic was over. "You're right; it's late. Sorry for disturbing you."

Giving his boss a short bow, the second-in-command turned on his heel and exited the office. Nightmare listened to the 'click-clack'ing of his heels, hoping that his assistant would go straight to his room and actually get some proper rest and a good meal. But he couldn't tell with Gray lately. It was highly unlikely though.

Nightmare stared at the innocent looking bear one last time before returning to signing his paperwork with a tired sigh. Though that little interruption had extended his break further, he felt even more exhausted than he previously did.

He meant what he had said; he didn't want another Outsider to come to Wonderland. Not when it ended up with the Outsiders coming to mean everything to them before being brutally ripped away from their lives and leaving them picking up the pieces.

But Nightmare had an uneasy feeling- one that he couldn't ignore no matter how much he tried. A feeling that things in this crazy world were going to be flipped upside down again soon.

And that the cause of this would be an Outsider.

It has taken two days, but I am finally finished this! Yay!

This is the new prologue for my story formerly known as 'Angel of Death'. I was unsatisfied with how the last prologue was written and decided to re-do it. Funnily enough, I first started typing out what I thought would be the prologue but ended up being the first chapter. I started writing this up yesterday and even if it ended up painstakingly so, I managed to finish this at around 4 PM Pacific time.

So I bet you all have a number of things to ask. Like why Nightmare of all people is doing paperwork and why the friendship between the two of them is extremely strained. As indicated, stuff happened and it changed the citizens of Wonderland... not so much for the better. What were the incident and the event that affected so many things? Stick around and find out.

Like with Alice, our heroine is not going to be meeting with Nightmare or Gray until Clover. But I thought I would use these two as insight that something has changed in Wonderland and not necessarily for the better. Anyways, I hope you enjoyed this because I've been working on this for about a third or fourth time and it wasn't easy.

While I said a number of things that bordered on being a spoiler, I don't think I showed my complete hand. This is just the prologue and you will get to meet the protagonist of the story in the actual first chapter.

December 31st: Did some really heavy editing. Again.

November 16th 2016: Edited. Again. Hopefully last time.