Reactions to this seem to be going well so here's the first official chapter.

I own two things, Jack & Shit, neither of which have anything to do with RWBY or Undertale.


Chapter 1 – Death and Rebirth

Some wise scholar, whose name has no-doubt been long lost to the ravages of time and even more likely had been old as fuck, twice as bitter and quite possibly hung over, had once said 'Life's a bitch, and then you die', shortly before getting into a fistfight with his bar-neighbor for hogging all the honey roasted salted peanuts.

Normally I wouldn't have given such a pessimistic outlook much thought, but considering I was currently among the living impaired, I have to admit there was a modicum of truth to those drunken ramblings.

Don't get me wrong, my life wasn't all that bad. Average childhood, a loving supportive family, decent friends both online and off and a job that, while hardly well-paying, was enough to let me help out with the bills a little.

Still not too clear as to how that translated to me being the one to pay the cable bill though. I mean sure, chipping in for the electricity or internet I could understand because god knows everyone was using those, but I didn't even watch television those days, so why the hell was I paying for a service I didn't use?

Because the women in my family outnumbered the men two to one and Heaven help my dad or I if we got between them and the latest episode of 'Say Yes to the Dress' or 'Game of Thrones'.

God I miss them.

Where was I? Oh yeah, as I said before my life wasn't all that bad. Sure there were some ups and downs and I'd steadily gained weight since graduating from college and compulsory gym classes, but all of the problems I faced thus far were either work related, thankfully someone-else's fault, or could easily be solved by paying a fine, making a quick trip to the doctor or venting my frustrations through video-games.

One game in particular that had caught my interest recently was a self-aware RPG by the name of Undertale, a recently released Kick-starter game in the style of Earthbound, or Mother 2 for those purists out there, created by Toby Fox, the genius behind the unofficial 'Halloween Hack' of the aforementioned Mother Sequel.

The game followed the misadventures of a human child, Frisk, as they sought to escape from the monster-filled ruins of Mt. Ebott and return to the surface. Not that the monsters were inherently evil mind you, despite encountering most of them as traditional 'random encounters', you could opt to defeat them non-violently. Indeed, the 'True' Ending of the game could only be achieved by completing a Full 'Pacifist' Run, never killing a single monster, which could get frankly ridiculous when you considered how insane the boss battles could get.

Won't go into too many details, because in all honesty Undertale is a game best experienced blind and heaven help anyone who deliberately spoils it for others, but let's just say that because of one Boss Battle in particular I have never been able to look at muffins the same way again.

Freaking spiders…never going to be enough fire. cafe

Where was I? Ah right, so one day I'm trying to sort out some paperwork in the office that was due three weeks ago but got misfiled because our resident intern, whom everyone affectionately referred to as 'Ass-hat', spent more time on his damn I-phone seducing Pokémon waifus than earth. Stupid bastard couldn't spell to save his life either.

So there I am, watching the little bastard try to rub his pixilated balls on some electric rodent while considering my options for homicide when I get a call from two guys I would proudly declare my 'Bros' inviting me to tag along to some anime convention going down over the summer.

Of course I was hyped to go, but getting the time off would be troublesome, not only because things were getting busy for the company but because my direct superior was the kind of hardass who couldn't get a stiffy unless he'd spent most of the day making other people hate his guts.

He also happened to be Asshat's dad, which explained so much now that I think about it.

Fortunately for me, my busy schedule, and by that I meant the hours my Department spent correcting Ass-Hat's mistakes, meant I'd saved up a not inconsiderable amount of paid leave. All it took was a quick word with the boss following a staff meeting and I was free as a bird for the next two weeks while Ass-Hat was forced to clean up after himself for what was most likely the first time since his mother Queefed him out of her womb.

I apologize most heartily for the mental scarring that image may have caused you.

All I needed to do was pack a change of clothes, cash, and of course, pick out a costume. What? Don't look at me like that. It's practically a tradition to attend an Anime Convention in costume. Anyone who tells you otherwise is either a miser or a filthy casual. Or Both.

In any case most of you can probably already see where I'm going with this, but for those of you still catching up, after playing through Undertale a few (dozen) times, I found myself hooked like so much of the gaming community. So much so that no sooner had the words 'convention' entered my brain during the phone call did I realize precisely who I was going as.

From the moment he first appeared stalking Frisk when they left the safety of Toriel's home in the ruins, Sans the Skeleton had quickly become a fan favorite thanks to his sense of humor, hilarious repartee with his brother Papyrus, and the sheer mystery that surrounded his existence.

Just who was this lazy, wisecracking, ketchup-chugging skellington who could seemingly break the fourth wall, teleport, walk through walls and was considered by many to be the hardest boss in the entire game? Lord knew his theme song kicked all sorts of ass.

Fan and Game Theories aside, unless Toby Fox himself stepped up and outright and spilled the beans, it was unlikely that Sans', and by extension Papyrus', shady past would ever be clearly defined. And in all actuality that suited the Fanbase just fine. After all, half the fun of a Fanbase was making shit up to expand upon the lore of the series.

It's one of the reason the 'Soulsborne' series was so popular despite being purposefully designed by the developers to make you rage-quit, the lore of the series was simply so ripe it allowed the community to build on it from there and expand. Hell, even the butt-hurt 'Genociders' who died countless times to his Karmic Retribution loved the bonehead.

Now as much as I'd like to wax poetic about my choice of costume, to be completely honest it was also a practical decision for me to make, partially because I lacked the confidence to pull off some of the wilder looks you get from other series and partially because it was just so much easier to put together Sans' costume. After all, it was a lot easier to dress up in a jacket, shorts and slippers than it was to pull off some of the outfits other characters got away with. Plus, Skeleton masks were like a dime a dozen even when it wasn't Halloween.

My bros of course, lambasted me for my cheapness the moment they see me saunter out to the car in my costume. I simply remind them of just how much money the shelled out for their own costumes which they will most likely only wear once and the argument quickly devolves into manly posturing until some inconsiderate neighbor called the police, forcing us to book before we spent the holiday in a cell with a giant muscular psychopath called Betty.

Lesson for the day kids: Don't do drugs kids. Not even once.

The trip to the con was just the kind of thing you'd expect when you cram three guys in a car without any other form of entertainment but each other, namely well-intentioned ribbing and attempts at one-upmanship between pit-stops to refuel and unwind. We took shifts driving, swapping out at each rest-stop so that the previous driver could rest his eyes in the back seat. I was currently riding shotgun, idly flipping through a Hellboy novel when I swear I spotted something behind me in the rear-view mirror.

At first I thought it was just my pal screwing around, but nope, he was still sawing through redwoods with his back to us. Yet I could clearly see what looked like a cracked skull mask looking back at me with a creepy, yet somehow lonesome smile. I would have investigated further were it not for my wing-man's startled cry of "HOLY SHIT!" snapping me out of my thoughts. whipping round just in time to spot the massive semi-truck that was barreling towards us, having smashed through the barrier separating the lanes.

A part of me, the part not currently shitting myself or screaming like a little girl, dimly noted that I could just make out the face of the driver of the incoming vehicle, noting distantly that he eyes were bagged and bloodshot, meaning he most likely fell asleep at the wheel due to hauling that massive load around for God only knew how long.

Such thoughts were quickly driven from my mind upon impact, a light flashing behind my eyeballs as my head smashed into the dashboard before everything went dark.


Play: Dark Darker yet Darker...(Gaster's Theme)

The first thing I felt as I gradually regained consciousness was a strange feeling of weightlessness, not unlike floating in a bathtub, only without the comforting warmth of a nice hot soak. Not that I was in any pain mind you, indeed, the fact I was currently pain-free after face planting the dashboard came as something of a surprise, though by no means an unpleasant one.

What troubled me was the fact I couldn't feel anything at all. Not whatever was supporting me or anything attached to me. I could steel feel my limbs and move them, thank fuck, so at least I wasn't paralyzed. However, even the slightest movement seemed to take forever and even opening my eyes served no purpose, as all that stretched before me was darkness. So dark that it was a marvel I could even see myself.

'Well this sucks.' I couldn't help but sigh, unable to do anything but float helplessly in darkness so thick he might as well keep his eyes shut. 'Didn't even make it to the con…only upside to this is now Ass-Hat is stuck doing my work full-time.'

It was strange really, how well I was taking all this. I mean, back when the truck was barreling towards the car I am not ashamed to admit I literally shit my pants, but now it was if I couldn't care any less if I physically tried. Maybe there was something to the whole 'Glandular' thing Pratchett's Death kept going on about?

As it stood, instead of panic, anger or any other emotions one would normally expect from being dead, I found myself feeling apathetic at best, as if my doubtlessly horrible, painful death was something I'd read about in passing in a newspaper before skipping to the crosswords. Apathy quickly gave way to boredom however, but with little else to do but float in the void, for without a source of light it was hard to tell if I was moving at all, I opted to simply close my eyes and lie back to see how long this so-called 'Eternal Rest' thing worked out.

As it turned out, it didn't last very long.

Well now...Isn't this an interesting development...

I don't know how or why but much like The Voice of Death of The Discworld the 'voice' of my visitor simply popped into existence in my brain, though calling it a 'voice' wasn't quite accurate, it was more like strange symbols simply popped into existence in my head without bothering to give my retinas so much as a 'by your leave'. To make matters worse, I got the distinct impression that rather than 'seeing' the letters, I was 'hearing' them, though my ears were likewise excluded from the deal, as if someone had decided to just cut-out the middleman and dump the words in my brain directly.

But rather than alarm at their sudden presence, the only thing I felt as I opened my eyes was curiosity. After all, it isn't every day you suddenly find yourself fluent in wingdings…even less frequent so that you encounter someone who can seemingly broadcast their thoughts in it.

"Doctor W.D Gaster, I presume." I greeted the figure hovering before me, or more accurately, the leering, skull-like face, set with a crooked, black jack-o-lantern smile and two cracked, empty eye sockets. Though it was impossible to make out anything else, a pair of skeleton hands with holes in the palms hovered before the figure, giving it the facsimile of wearing a black coat over its frame.

W.D Gaster, arguably the most mysterious character in Undertale due to the fact that there was simply so little revealed about him. The only things known for certain was that he was Alphys' predecessor as the Royal Scientist, that he designed the Underground Core to power the Monster's Civilization and that he began the Determination Experiments on Asgore's orders only to mysteriously vanish.

Despite supposedly 'erasing himself from existence', he would make the odd appearance in-game, normally in the form of hard-to-find secrets that more often than not make the game crash upon discovery, so it was understandable why so many Fans had alternate depictions of the Man That Speaks in Hands.

Fascinating...I do not believe I ever introduced myself...

"What can I say? The multiverse is a strange place." I quipped, offering a lazy smile to the displaced monster "I don't suppose you're here to take my soul or something?"

Heavens no. I merely detected some new presences in the void and decided to investigate...it's been a long time since I had company after all.

"I can imagine, bumping into Frisk probably startled you outta your skin…so to speak." I mused, and I swear to whatever concept of a righteous God you may have I saw that creepy smile of his widen just a crack at my poor attempt at humour "So I guess that means we're roomies huh?"

Sadly, no. As much as I would treasure your companionship, your spirit is merely passing through the void to whatever after-life you humans believe in.

"Shame…I had so many questions I wanted to ask, but then I suppose it wouldn't be fair to the others if I got inside info but couldn't spread it online."

You are taking your current state of mortality surprisingly well...for a human.

"It's a glandular thing." I quoted, earning a curious head tilt from the displaced Monster "Sorry, Meta-humour, but it doesn't really matter in the long run. I mean, what would even be the point of getting angry? It's not like being angry can bring you back to life.

True...though the same cannot be said for Determination.

"Come again?" I asked, blinking at the Man Who Spoke in Hands in what might have passed for confusion if I could have seen my own face "What're you talking about?"

Do you want to live? Would you be willing to risk anything to live again?

"You got a plan doc?" I enquired, curiosity overwhelming my confusion as I felt a sudden pang in my heart. Not quite painful, more like an echo of something I'd been on the verge of forgetting.

From our discussion I'm certain you at least know something as to how I came to be here, correct? Then you should know that while I cannot interact with the world at large, that doesn't stop me from existing there.

"Like the door behind the waterfall or the locked room at the hotel." I concurred, recalling two notable in-game incidents where Gaster briefly manifested "What's your point."

Due to the nature of how I came to be here, I cannot exist in the material world for long, it takes immense concentration just to manifest an intangible shade. However, a human soul is different, it lingers after death even when the body is long gone.

"So, what, you're saying there's a chance I could live again?" I prompted, that strange, familiar feeling growing within me all the time.

I cannot say for certain...but what have you to lose?

He had a point. Hell even if the plan failed and I wound up in the void for all eternity it wouldn't be all that bad with Gaster for company. It wasn't as if I had anything like fear to hold me back either. What was the worst that could happen to a dead man after all? "What the hell, let's get this show on the road."

Very well. If you are determined...then give me your hand.

I'll admit, even floating in the void, with no other emotions to my name, I felt a shiver race up my spine as Gaster's skeletal hand hovered closer to me, waiting for me to cross the remaining distance and take it.

It wasn't fear or apprehension, I lacked the glands for that. It wasn't even revulsion, as aside from the hole in the 'palm' there was no difference between Gaster's hand and those of a regular skeleton.

It was only after I grasped that alien hand, felt those cold fingers grip my own in a bony embrace that was simultaneously cold and empty, that I realised the feeling welling up inside had been DETERMINATION.


Play - Mysterious Place

When I next came to my first assumption was that Gaster's gambit had failed and I was still trapped hovering in the void between life and death. The first clue I had that anything was different from before was the fact I could suddenly feel again. Not just emotions, of which surprise and confusion were paramount, but also the sensation of touch, which was currently engaged in processing the strange, alien, yet at the same time comforting feeling enveloping my body.

'If Gaster screwed me over then this isn't too bad…' I mused, giving up all attempts to open my eyes, which felt heavy as lead for some reason, in favour of savouring the strange, comforting warmth I was floating in 'Wait…floating?'

Indeed unlike the void, where I had been unable to feel anything at all, I could tell at an instant that my new location was decidedly wetter, though not unpleasantly so. To make matters even more confusing, I appeared to be curled up in a foetal position as I hovered in the embrace of the warm liquid.

Strangely enough, despite the return of my emotions, I couldn't find it in myself to be concerned about this development. Even the fact I was unable to move didn't concern me in the slightest, I was simply content to lie here, letting my worries wash away like I was soaking my soul in a hot bath.

It was an alien yet comforting feeling and yet for some reason I couldn't help but feel like I'd been here before, or a place very much like it at the very least.

'Just where did you send me Gaster?' I wondered, struggling once again to crack even a single eye open only to be met with a darkness comparable to the void, though decidedly less oppressive, mostly due to the very faint light from below, which seemed to silently call to him, like a beacon in the dark.

'Better than just sitting around I suppose.' I mused, before beginning the arduous task of turning my body towards it. For some reason nothing seemed to be working right, almost as if my muscles had the consistency of jello, but eventually I managed to get myself pointed straight down towards the light.

Play - Bird that carries you across a disproportionately small gap.

At that moment, the air was forced from my lungs as a tremendous pressure suddenly bore down on me from all directions, shoving me face first towards the light, my eyes snapping shut instinctively just before my face collided with something hard yet malleable that seemed to stretch over my head, like I was trying to force my way into a sweater two sizes two small.

After several uncomfortably claustrophobic seconds I suddenly found myself gasping in lungfuls of fresh air, the crushing pressure vanishing as I was expelled from the comforting warmth into open air, the sharp, clinical chill cutting through my confused thoughts like a hot knife through butter.

'Christ! Turn it down a notch!' I swore, glaring up at the light overhead as my vision swam in and out of focus, only literally spit as the light was obscured by a massive head, most of the blurry features aside for the eyes hidden behind a hospital-issue face-mask and hair-net.

"I-I-It's a boy!" a nervous yet strangely pleased voice stammered from the apparition, a pair of large, yet gentle hands holding me up in the air for all to see "A b-b-big, strong healthy b-b-b-boy!"

'No s-s-s-shit sherlock!' I tried to snark, but to my growing irritation my mouth had decided to follow the same treasonous example as my limbs and refuse to work properly, my irritation slowly giving way to confusion as I tried to take in my surroundings. By this point I was slowly beginning to put all the pieces together, but my mind just refused to process the sheer absurdity of my situation.

'Wait…don't tell me…!'

A sudden sharp pain near my stomach cut off all thoughts and drew my attention just in time to see a pair of bloody tongs remove what looked like a bloody sausage rope while a pair of equally bloody gloved hands tied the severed end, which was connected to my stomach, into a knot.

"C'mon now little f-f-f-fella,' the figure stammered cheerfully as she proceeded to wipe me down with warm water to remove any remaining blood or fluid "let's get you c-c-c-cleaned up.'

'Oh you gotta be kidding me…' I stammered, a growing sense of dread and disbelief washing over me as she wrapped me in a warm towel and picked me up 'Don't tell me…!'

"C-C-C-congratulations Sir!" the woman stuttered, a sense of vertigo washing over me as I was seemingly passed from one set of hands to another, decidedly stronger and less gentle set of arms. Looking up in wonderment, I found myself gazing up at yet another blurry face, though unlike the Doctor, I had the strangest feeling that this guy was silently judging me, even though the only defining feature I could make out was his admittedly badass moustache.

"Why isn't he crying, Doctor?" Pornstache demanded, his cold tone sending shivers of apprehension down my spine as he continued to stare down at me judgingly "Is there anything wrong with him?"

"I…I d-d-d-don't think s-s-s-so s-s-s-sir…" the doctor stammered, clearly just as put out by his frigid tone as I was, perhaps even more so "He seems to be breathing easily enough…I'd need to run some tests but with the other on the way…"

"Leave it for now then," Pornstache commanded, his tone dismissive even as a woman's frantic breathing rose in pitch in the background "Just focus on getting my wife through this. We'll run a diagnostic later along with his twin."

"Y-Y-Yes sir!" the doctor stammered, the sound of retreating feet heralding her departure while Pornstache turned on his heel, another wave of vertigo washing over me as I was all but shoved into yet another set of arms, this pair clad in what appeared to be metal.

"Take him to the infirmary and stand guard there." Pornstache commanded, his frigid tone brooking no argument as the person holding me stiffened "I'm holding you personally responsible for my Son's safety soldier. If anything happens to him before my wife has a chance to hold him in her arms…"

"Sir!" the figure holding me acknowledged, snapping to attention awkwardly with me in his arms before turning on his heel, and marching off, pausing only after he'd left the room we'd exited well behind to release an exasperated sigh "Oum Dammit, I didn't sign up for this to play nanny…" he glanced down at me, his features hidden behind a visor "Still…awfully quite lil tyke ain't ya?"

Even if I could have answered him I doubt I would have, as my attention was currently focussed on the image reflected in his visor, an image that, sadly, did not include myself as I was, but rather a small wrapped bundle with a baby's bald head peeking out the top.

'Gaster you Mother F-!'

Play-Unnecessary Tension

A sudden absence of noise cut me off, my eyes widening as the entire building shook, the soldier carrying me crying out in alarm as he stumbled against a wall. "What the hell was that?!" he demanded, tucking me awkwardly into the crook of his arm as he reached for his helmet "Security! What's your status!?".

Whatever he heard on the end of the line mustn't have been particularly pleasant, as he let out a string of impressive curses towards 'Damned Animals' before tucking me under his arm like a football and racing down the hall, his free hand holding a pistol. "Gotta barricade ourselves in the infirmary." He muttered, thumping what sounded like an access panel to open the door at the end of the hall "Gotta hold out till the security drones activate-!"

His words trailed off with a choke and I once again felt a wave of vertigo wash over me as we suddenly found ourselves flying backwards through the air, the soldier's back slamming into the wall opposite the infirmary door while I tumbled into his lap and onto the floor, unable to do anything but look up in alarm at the business end of the spear sticking out of his chest. "Holy Shit! Undyne what the fuck?!" a startled teenaged voice shrieked in the distance, one of many if the cries of alarm were any indication.

"Had to be done." A gruff, female voice shot back calmly, possibly the owner of the spear if her tone was any indication "He would've called for reinforcements and then we'd be really screwed."

"We were screwed the moment we set off the damn bomb!" the panicked teen from before pointed out "I told you we should've just ditched this place with the others but you just had to raid the infirmary!"

"We need medical supplies." The female, Undyne I'm assuming, snapped back "Some of us more than others, so quit your bitching and stuff those damn pants of yours with anything you can get your hands on!"

"Should've stayed at Monty Burger…" the distressed figure muttered under his breath as he moved away, most likely returning to whatever he was doing before the guard burst in "Better hourly wages my ass…never signed up for this shit…"

"Wuss." The woman called Undyne scoffed, the sound of footsteps drawing nearer before I found myself looking up at a blurry figure standing over the guard's corpse, one booted foot coming up to his chest as she grabbed the haft of her spear to yank it out of his chest before crouching down to pick up his pistol. "Of course it's fucking locked…" she swore, tossing the weapon aside with a disgusted hiss after looking it over briefly "Freaking paranoid Atlesian warmongers…hmm?"

The next thing I knew I was being picked up off the ground with surprising gentleness only to find myself gazing into a blurry face framed by shocking red hair, one eye heavily covered by bloody bandages. "Well hey there little guy." The redhead greeted with Undyne's voice, her tone torn between surprise and amusement as she levelled a cocky smirk at me, her mouth filled with unnervingly sharp teeth "Didn't know it was take your kid to work day."

"Undyne! We gotta jet!" the teen from earlier called out, several blurry figure stumbling out of the infirmary carrying what looked like duffel bags, no doubt filled with pilfered medical supplies "The security team will be breathing down our necks any second!"

"Got it, let's move." Undyne snapped, rising to her feet, spear in hand, before shoving me roughly into another set of arms "Here, hold this till we get out. I can't fight and hold him at the same time."

"What the-where'd the kid come from?" the whiny teen wondered, only to yelp as Undyne blocked a bullet aimed at his head with her spear before racing down the hall "Aw dammit I knew this would happen!"

I'd have happily shared my thoughts on the matter, but my mind had finally reached its threshold for bullshit and had decided that since none of this could possibly be real I'd be better off trying to process it while unconscious, though I wonder what it says about my state of mind that, rather than my rebirth, the guard's murder or the ensuing cluster fuck as my kidnappers fought their way to freedom, it was the cat-ears sticking out of the teen's head that made my brain go 'fuck it'.


And that's chapter 1 out of the way.

Bit of a slow start but as you can see, I'm trying to mix the worlds a bit.

Wanted to do Gaster's words in Wingdings but it won't let me for some reason.

1. Yes, the 'Self Insert' is essentially Sans, but NO. He isn't going to be a skeleton.

2. Yes, that was indeed Undyne & Burgerpants, or rather, their Remnant counterparts.

3. until the official plot starts, expect things to progress slowly, with time-skips between chapters.