Chapter One: Despair

Upon the wings of night he descended, slowly drfting his way towards the ground his torn black robes fluttering around him, enveloped as he was in the shadows of death he felt no elation or joy as the sensations of the world around him took form once more. For more years than had been written he had followed a path that had set him here many times and many times he had acted out his part to play in the world he was forced to dwell in.

From the clouds to the surface he felt nothing but the need, the need to do as he had been created to do since before time began, since before intelligence had blossomed in the minds of the people he had been assigned to shepherd. Oh yes, his duty was ever present in his thoughts, for it was all he had...

That and jam sandwiches.

He liked the blueberry kind, the kind with the little bits that forced him to chew twice as much before he was able to swallow and move on to the next bite. Life was like that for him now, since the dawn of a new age, the dawn of peace and prosperity amongst the ponies of the world, since Her Blazing Whiteness arrived with her Lazy Good For Nothing sibling and ruined it all for everyone.

It had gotten boring after that and now only the small pleasures in life made him feel alive. Which when one thought about it was perhaps not the greatest life in the world, where the only goal was: 'get souls, make sandwich, go to sleep watching terrible sitcoms with lousy actors and cheap budget.'

Oh yes... life was bright and glorious for everyone... that was sarcasm in case you missed it...

It was all made worse by their apparent lack of being known... or remembered... or even feared as now everything was so happy and dandy only poorly designed and oddly shaped bad guys made anypony quiver in terror.

Was he jealous?

Of Course He Was Jealous!

He had once been worshiped as a God! He had once carved bloody swathes in whole armies with but a single swipe of his massive scythe! Now he had been reduced to being the symbol of a minor league foal's dodge ball team and the image of an ill conceived advert for a funeral home!

Yet he didn't complain, it was just the way his cards had been dealt, though he had a feeling that the one who had dealt the cards had been hiding a few aces up their sleeve... He checked his list, the dried ancient roll of paper materialising before him and unrolling to reveal the names written in lines upon its inner surface.

As he read the names he knew them, as he knew everypony in the world, it was the curse of his job and one he had been forced to live with since it had been forced upon him by two war hammer wielding maniacs who had gone to town on his body until he relented... yet even so he still missed his mother and elder sister, for all their faults they had been... acceptable, in an odd way.

At least he still kept in touch with his brother's and youngest sister, who like him had been pushed into roles that the world had needed at the time. Again life was like that and nowhere better was this proven than by one's own family.

As his eyes swept through the names he came to a stop, a chill running down his spine like a hacksaw across iron. Suddenly he felt very unwell, that horrible feeling of anxiety took over and a drop of cold sweat began to roll down his forehead.

He looked over the name again, double checking before lifting his eyes up from the paper in a dramatic moment of 'This cannot be!?' similar to the 'Oh no you did not!' look developed by cheesy action movies where the hero discovers his girlfriend has just been kidnapped by the villain after reading the note left behind in her ransacked apartment.

It wasn't the pony in question that was the problem... no, in fact it was the location. For said pony dwelled in Ponyville!

Ponyville... oh how he despised Ponyville... he had been there before, a couple of times in the recent years. Oh sure he came with every death that occurred anywhere there were ponies its just that in Ponyville, since the arrival of one certain mare, things had not gone according to plan. It wasn't as if he answered to anyone/pony/thing, in fact he didn't even really have to do it, it was just something he did.

Like a damned compulsion or an addiction that couldn't be broken... it dominated his entire life and made him feel awkward...

For one thing he got this weird pleasure out of collecting the souls of those who died and taking them to the source where they would one day be reborn. It wasn't that bad really, in fact he liked that tingly warmth that seeped into his shoulders and neck every time he did a good job...

It was what happened when things didn't go according to plan that he disliked.

It was horrible then, he became irritable, his organs would play up and he would suffer terrible indigestion, he would then get fluish and suffer random bouts of constipation followed by hairballs for weeks. Have you ever seen a grown stallion coughing up hair that came from the stomach of death? Do you even want to imagine the slimy noxious vile leaking ball of fur that convulsed and groaned before rolling away and hissing at anything it neared with a heartbeat?

Do you want in your head to see it randomly exploding in a mass of green acidic puss that would fly in all directions infecting everything it touched with some terrible illness which would most certainly involve migraines warts and loose bowels?

Do you really want to?

If yes then please see a specialist or go to youtube for future viewing needs.

Ponyville... he groaned deeply and went to his job, following the list right down to that specific name that was sure to cause problems and skipping that one without hesitation. He wasn't going to leave it, no way no how! He was just going to save it till last, which was the smart thing to do for he had not done so once and it had been a very eventful night at a certain banquet in Canterlot, where a surprise ball sized guest appeared screaming its ways around the nobles before leaping three feet into the air and spreading itself out in a wide radius, painting the walls a new shade of lambent green.

Oh yes... good times...

Eventually however the names dried up and he was left with one.

Resigned he appeared on the outskirts of Ponyville, the town was empty as the dead of night had claimed the sky and ponies lay in their beds asleep. Mostly asleep anyway, a few had a habit of staying up late and doing... weird things that he did not like to think about.

The living were a very strange bunch.

Oh yes... he was dead, he had been sure he had mentioned it but obviously not, perhaps he should edit this to clear that up but right then he felt the chances of his remembering to do so were lacking any real effort. Yes, dead, that was what he was, were not the war hammers mentioned earlier? Yes they were, did you remember? Yes? Good, lets move on.

His robes concealed his entire body, its essence swarming around him like a cloud of darkness revealing only slightly the shape of his body underneath. It was a grand display, one that would make him appear an all powerful force of darkness that none could ignore.

Sadly they could for he was invisible to all eyes bar the ones he had come to claim and the completely insane.

Sucked to be him but there you go. He began the slow walk towards the structure wherein waited the soul that was his duty to take. Every step was a hollow thud that echoed across the town like a deadening call to those still alive, in the hearts of those who dreamed there was a flutter of fear, a tingle of dread, their souls knew him even if their minds did not and in their dreams they shivered like foals.

Not that it really mattered because in five minutes or so he would have reached his destination and the whole process would end with everypony rolling over and dribbling into a more relatively peaceful dream. None would remember it either, the most that would happen is some child may wake from their sleep before collapsing back into a state of mindless oblivion.

It bothered him to say the least.

Finally he reached the door and was about to lift a hoof to knock, which was customary, yet he hesitated at the last moment, sudden realisation striking like a bin liner filled with rotten custard across his face. He should not have made his usual entrance, though he always felt sheepish creeping his way through the streets he had forgotten his one cardinal rule when dealing with Ponyville:

'Shut up man! You'll wake her up!!!'

Of course it had been written down in a self berating form but still he took the rule seriously because when he forgot (and for some reason he would always forget) then it was almost a certainty that one particular pony would appear to make things difficult.

Yes... he had made a category for her in the Rider's Manual, a thing reserved only for the most dangerous of foes. He considered this one had more than earned the right to appear there, his brothers and sister had at first mocked him for doing so but even they had changed their tune when they had come across... Her.

Yes... Her... The Pink One!

He shuddered and wondered if the Walk O'Doom had gone unnoticed, sometimes the Pink One would be too intoxicated or exhausted to make an appearance but then again it would always remain a surprise. For some reason, though he knew who she was if not what she was, he could never tell where she was.

No other being in the world had that kind of power.

It made her dangerous, so much so he had even attempted to enlist his fellow Riders to join forces against her, yet that option had been abandoned, the others did not wish to involve themselves further in anything to do with the Pink One. In fact they had black listed her from all further doings related to their work.

He guessed he could do the same but he was unwilling to be bested by her, she had challenged him on any number of times and had always come out on top. How she knew where he was confused him, it was as if she had this extra sense that somehow directed her every waking moment.

If only he could master that all knowing power, then she would no longer be a problem!

He looked over his shoulder to see if anypony was behind him before slowly passing through the wood of the door like a ghost. This was a breach of etiquette but under the circumstance he was sure he could get away with it.

Perhaps he was just a little too polite sometimes... It was a failing, he had been raised on good manners (for the most part, there was the whole violence and brutality thing that was abundant in the family) and a proud form of sophisticated wordings (Once again... for the most part).

He looked about the house, it was the simple kind he had gotten used to in many villages and towns across Equestria and the lesser known lands to the east north and south. The structure was mostly white walls with dark oak beams holding the roof up. It had that old quality to it that made him feel truly ancient for he had been there before such a style had even been invented.

He even remembered the first ponies to come into being, how they had stumbled out of the primordial ooze only to blindly roam around stupidly searching for food sources in places that had not ever been designed to contain anything but death.

Fun times.

He wondered on why life did this to him, why it had its downs and even deeper downs, why it had always deemed fit to drop gravel down upon him while he stood in a one block wide twenty block down hole in the ground. This was perhaps natures way of punishing him for being innocent of any real crime he supposed.

He crept through the house, moving from the living room to the bedroom behind it. At least it was a one story house, he hated stairs with a dark passion, they liked to creak and give warning to his prey. This time things might just go smoothly however, at least he hoped, he didn't want to let his guard down again.

He came to the bedroom door and drifted through it, he would perhaps make a show tonight, with the chinking chains and the power of a gale force wind summoned into existence behind him to give life to his robe. It did well to remain in character that was all, he was determined to make the world remember... though it was a poor plan on his part as the only one who would see it was the one about to die.

The bedroom was warm, in the corner a small heater buzzed keeping the chill out of the air. He looked to the bed and saw his target, one Spinster May, ninety three years of age and known to be a rather forgetful pony who had recently lost the ability to hear or see very well.

He sighed and prepared to use his really loud voice, he was sure he would have to repeat things but he was a stickler for custom... whenever he could act upon it.

He took a massive breath in preparation, the air in the room flowing with some force to fill his trans dimensional lungs which were in truth as bottomless as the darkest depths themselves. (Though this was still in speculation as nothing had ever reached the bottom and yelled back up)

He felt the click of his spine informing him that he had enough to begin his display of unearthly power, his pale blue eyes began to glow brightly through the darkness of his wide hood. The air began to grow cold and the warm lighting pale and become grey. As life began to fade from the surroundings he made his move to begin,

"Howdy Doodie, Pear!" It called like the All Powerful Banshee of the east.

The air expelled from his lungs in one long rush, his chest deflating and his powerful countenance dissipating like snow under the full force of the blazing sun. It took a while for all this to happen, as the colour had to return too and as every supernatural being knew colour was the laziest most easily distracted thing in the universe.

As all returned to its natural state, including colour which rushed in towards the end with a blush on its cheeks. He wondered why life was so cruel and why it took a perverse delight in seeing his night ruined at every turn. He turned slowly, like a creaking door slowly opening, as he came to face... Her!

He felt that uneasy sickness already building up in his gut.

"Pinkamena Diane Pie." The dead pony of death boomed in hollow tones.

"How's it going Pear?" Pinkie Pie giggled warmly, sat on her haunches with a lantern beside her (he had wondered where the light had come from but had not thought to look) her forlegs up and actively shuffling a deck of cards that made the pale rider physically shudder. The Pink pony noticed this with a grin.

"Despair." He corrected with a groan, already he could take no more. "My name is Despair!"

"I know your name silly." She chuckled, holding the deck of cards in one hoof and somehow magically flicking them all one by one to the other in a matter of one and a half seconds. Despair shook his head with confusion, it wasn't bad enough that she was able to negate some of his abilities but she was able to violate the fabric of reality with her hooves.

"What do you want Pinkamena?" Despair growled, his voice filled with electricity.

The old mare on the bed snorted and rolled over, ignoring their presence with a profound ability. Pinkie Pie rolled her eyes at him. "Oh come on Pear we've been through this before." Her eyes were filled with mirth. "I mean, wouldn't you just like to talk to somepony once in a while? I mean, being a rider of the apocalypse must be a lonely job."

"It goes with the occupation." He answered shortly. With a heartfelt mutter of depression he lowered his hood, revealing a face that had once been handsome and full of life but was now rather scarred and filled with an immortal grumpiness that had been developed professionally over thousands of years, His coat was a white with the slightest of green tints to it, his mane also white was short and straggly. However he still appeared young, though his eyes had sunk into their sockets giving him a similar appearance to a drug addict with really wide unblinking unnaturally pale blue eyes.

"Oh come on." Pinkie attempted with her most pleading expression. "I'll make a cup of tea and we can sit down and have a chat."

"I would rather you just go away." He stated before asking in the politest voice he could muster. "Would you please go away?"

"You and I both know that's not going to happen Peary Weary Woo." The wild pink maned pony answered with a twisted grin, the cards flicking once more to the free hoof. Suddenly a new expression took over her face, one he understood as her business face. "Now lets cut to the chase shall we."

Muttering something very unpleasant under his breath the pale white stallion nodded. "Please do."

A table was suddenly produced, two uncomfortable wooden chairs too. He found himself sitting on one suddenly with... Her, taking a place opposite the small circular table. Their eyes locked in a manner of extreme suspicion. Even though he had never been able to find proof he knew she cheated, there was no way her luck was that good.

"Once again I must state the issue of payment." Despair began in his dead tones. "A soul for a soul, if you win Miss May will be spared and she will gain one extra year of life, if you lose..."

"...and if I lose my soul is yours." Pinkie Pie cut in, her tone a mocking semblance of his own. Returning her voice to normal she grinned at him. "So what do you want to play? Five Hoof Bluff? Hoofer? Blind Pony's Stumble?"

"Blackjack." He answered.

"Filly Go See? Celestia's Gambit? Lock In, Lock Out?" She continued without appearing to have noticed his answer.

"Blackjack." He stated again, in the exact manner he had spoken before.

"A World Of Elephants? Star Swirl's Beard?"

"Blackjack."

"Go Fish? Go Rabbit? Go Salmon?" Pinkie Pie began to pipe suddenly, waving her fore hooves in the air. "Ooh! Ooh! I know I know! How about Snap?"

"For the last time..." He sighed deeply. "We are going to play Blackjack."

"Blackjack?" Pinkie Pie blinked, confusion on her face. "Not Fiddle Me This?"

"No." He answered.

"Not even Snap? Oh come on I know you like Snap, we played it last time!"

He remembered, the event had left him ill for two weeks, "We are going to play Blackjack." He stated, his voice becoming short.

"You sure?" She asked with an unsure frown.

He fizzled, or at least his eyes did, their translucent blue tones slowly beginning to glow in an unearthly fashion. "We Are Going To Play Blackjack." He spake onto her, spake in the voice of death.

"You're sure you wouldn't rather play something else?" Pinkie Pie smiled awkwardly. "It doesn't even have to be cards I could get my Monopony if you want instead maybe?"

"No."

With a long drawn out sigh Pinkie Pie relented, lowering her head. "Alright..." She elongated the I with a touch of doubt. "I'm not very good at Blackjack though."

"Good," He grinned, his sharp pointed canines revealed and flashing in the light of Pinkie's Lamp which had taken residence on the left hand side of the table.

"Well lets see..." Pinkie frowned. "Shall we take turns being the dealer?" Despair just wanted this over and done with so agreed with a nod. "First to three wins?"

"Your terms are acceptable." He nodded.

Pinkie flashed a bright smile and began shuffling the deck of cards still in her hooves. They sailed back and forth in odd flips and arcs that never ceased to surprise him, how she managed to do that with only two hooves to work each individual card was a secret only she knew, perhaps he should bargain for her secrets. As the cards danced so too did his eyes, following each one with an eagle's eye, he watched for signs of anything untoward, the proof he desired that would put this earth pony in her place.

He wanted vengeance for all the horrible incidents she had caused.

She stopped suddenly and quickly laid out the cards, two on her side two on his, both his cards revealed while only one of hers was on show. Her turn first to play dealer obviously. He looked at his cards, a ten and an eight. He looked up into Pinkie Pie's eyes, she had a jack, which made him wonder.

"Hit." He answered, forgoing the 'Me' just in case she actually did attempt to punch him, she had a habit of making such mistakes.

"Okey Dokey Lokie!" She answered, laying another card down on his side.

He smiled, a two, he could deal with that. "I will stick with that thank you very much." Twenty was a good number to have in this game, a safe number.

She nodded and flipped over her card. "Blackjack!" She declared.

He resisted the urge to grind his teeth, there indeed was the offending Ace adding to her Jack, the combination thereof did indeed create the Blackjack she had so joyously called. Part of him immediately doubted this pony and her declaration of having little luck in this game, once more he felt he had been cheated somehow.

She shoved the cards back into the deck and handed them to him, he took them with a scowl and began to shuffle, or at least as best he could, he could never get the knack right and he always made an unprofessional display that had led to many an embarrassing conversation. She only smirked at his clumsy attempt, which grated on his nerves somewhat.

He laid out the cards, both looked expectantly to discover what had been revealed.

"Blackjack!" She cried happily.

He facehoofed, dragging said hoof slowly across his face, was he doomed to repeat this every time he made a visit to Ponyville? Was he doomed to suffer unending misery at the hooves of this mad mare with no sense of reality? Was he really the punchline of some cosmic joke written by the drunken sleep deprived mind of some lunatic who had nothing better to do with his life than make Despair's miserable for the amusement of a few Pony fans!?

Well? Was he!?

"My turn!" She giggled, making his eyes twitch uncontrollably. "And one more win means I win the jackpot.... um, Pear, your eye's doing that thing again."

"I know." He stated. "You didn't have to point it out."

She shrugged. "Just thought you should know."

As she shuffled the deck he watched with blazing eyes, even going so far as to watch with senses mortals did not have. He needed to know how she did it, he needed to discover the truth no matter how confusing it be, no mortal was this lucky, no mortal defied the rules of fortune and fate as she could!

She laid out the cards, turning them over.

Oh good. He smiled inwardly, this time her one card visible was a nine, while his were both kings. He felt more confident now, he would at least see one victory tonight and even if it may be as hollow as his voice it would at least make him feel like he had tried his best.

"Stick, thank you." His voice heavy like lead.

She nodded and flipped her face down card. A five, fine then, she still had a chance. She took out another card and slapped it down.

Despair stood and began moving hurriedly to the door, already his stomach beginning to churn. "You sure you don't want that cup of tea?" She asked.

It was worse somehow, before it had been slow to develop but this time it came out in waves of nausea. He struggled to keep his balance and even crashed through the door instead of phasing through it. Almost collapsing he forced his legs to carry him, all four limbs feeling like jelly. He began to hiccup silently and his vision blurred.

He then met the front door fully in the face.

He went through it, there were many splinters to be found on his muzzle, there wasn't much in the world that could stand in the way of Despair, Rider of Death and Bringer of the End, let alone wood. Yet in his state it had felt like concrete. He fell to the ground, his teeth finding dirt as he groaned, his innards shifting uncomfortably.

"Are you alright Pear?" Her face was lined with worry, she had not seen him so pale before... and that was saying something!

She! She had the gall to ask such a thing after what she had just done... she probably had a smile on her face too! Could his day get any worse? Did she have to gloat as well?

He made to stand, a witty reply already on his lips...

Oh no...

Well aren't you readers lucky, I guess you do get to see it after all...

He began to crawl forward, his face pressed to the dirt and his eyes screwed tight, he felt his spine cracking as if he had not moved for an eternity. As he reached the centre of the small road between the buildings his natural instincts took over. It was then that you truly got to see him as he was, as he had been born. Though his species were related to the pony they were very much different. For one thing his kind ate meat, or did eat meat until the day they had gone extinct.

They were also far more feral and their wings bat like, his robe fell apart and his large muscled body was revealed, along his sides were lines of translucent colour, pale blue, giving him a more alien appearance. He did not have a cutie mark but instead his entire body was covered in what appeared to be tribal tattoos.

All this hardly mattered though as any semblance of demonic power evaporated as he lowered his forelegs, raised up on his hind and began gasping and choking with a hacking cough. His eyes widened and his ears flattened, his wings splayed out and stiffened painfully. He began to wheeze terribly and sweat profusely.

All the while Pinkie Pie watched with fascination, thinking that Flutterhsy would have wanted to be here to examine this strange specimen and its odd peculiarities. She felt bad for Pear, things never went right for him, which was why she called him that, after the quote involving said fruit and shapes of which that were similar.

She didn't have the heart to tell him this however, he was having a bad enough day as it was.

His hacking increased until finally he began to make a strange sound similar to gagging and slurping. He began to rock his head forward and back, his chin rising up and then lowering till it reached the ground. Finally he gave one almighty heave before forcing a thick globule similar in size to a tennis ball out of his mouth and onto the ground.

He collapsed.

Pinkie Pie shook her head, that was indeed strange but not the strangest thing she had ever seen, poor Pear... Her eyes widened in shock however as she heard a savage squeak from the ground. Looking she spotted the now violently rolling ball of green hairy slime. It spun and leapt about as if it were possessed by a team of athletes all fighting for lead position.

She watched as its charge across the road, taking in its surroundings with senses she did not understand. Finally it took note of her as it rolled past, halting in its progress to hiss at her like a serpent... or a cat with a throat infection.

"Daww?" Pinkie asked herself questioningly, raising her brow as she tried to decide whether or not even she could find such a thing to be cute. Confused with how to feel but attempting communication anyway she moved closer, till she was perhaps half a meter away. "What's the matter little fella, you don't have to be scared of little ole Pinkie Pie..."

BOOM! WOOSH! SPLAT!

And somewhere in the lost senses of Despair's fading thoughts he felt a smile form upon his face and subconsciously a word appeared.

Justice!!!

Author's Note

Oh yes, this is only the beginning, soon all of the four will meet with one of the six.
And none shall be spared.
Oh yeah, and I knocked this up in about half an hour while struggling with the contents of my stomach, filled with enough alcohol to down a buffalo.

I think I need to lay down for a while...