Sans has always known it would happen. He knew that eventually Chara would lose Determination or Frisk's body would give out from all the stress of dying over and over and over... He'd grown numb to killing all of his friends and his brother in the seemingly endless loop of resets until the day came when the human's reset no longer brought them back.
With his brother's apparition by his side, urging him on, Sans continued to massacre Frisk through the apologies and Chara through the taunts. Sometimes,when he grew particularly bored of the vicious cycle, he'd let the kid get further than Snowdin Forest; the despair on their face when he met them in the throne room, the floor covered in wilted buttercups and Asgore's dust, tickled his funny bone. He hardly even noticed their red soul growing paler as he crushed it.
Then it all came to a head two years after the hell began (though for Frisk and Sans,they were reliving the same day on repeat).
It'd been months since Frisk's (Chara's) last reset. He looked all over the Underground - Waterfall, Hotlands, Snowdin, the Judgment Hall,the Ruins (kicking his way through Toriel's dust. "Heh, i guess i ruined your life." It wasn't so funny the hundredth time he's uttered it.)... - butall he found was a blue and purple shirt abandoned in Toriel's house. On it was a golden locket necklace. He took the locket as a souvenir and tore a sleeve off of the shirt, stuffing it in his pocket. It appeared that his Determination had outlasted theirs.
i did it, he thought smugly as he left the Ruins, disturbing dust with every step. i won.
He was vaguely giddy - not even an appearance from UnderHell Sans could've ruined his mood - but as he traveled through the dust-choked snow of Snowdin Forest, he finally registered the absolute silence aside from his own noisy steps. Even Papyrus wasn't around to whisper dark taunts in his ears (not that he had any).
"must've finally hit the dust,"he muttered to himself.
He made it home with a single shortcut once he reached his old sentry station, which was rotting despite the continuous resets. He flopped onto the worn couch, the springs groaning in protest, and reached for the remote, but stopped himself when he remembered that Mettaton's empty shell was rusting somewhere in the Hotlands. There would be nothing on. So he just laid there, the wind howling andrattling the windows. He couldn't fall asleep like he used to be able to and he found himself staring at the oil-painting of a bone hanging on the wall. Papyrus had insisted that it was a classic.
paps...
Sans shortcutted to his brother's room, standing in the center and looking around. The pirate flag was hanging on the wall by a single corner, the bookshelf was falling apart, and everything was layered with natural dust. Sans' fingers itched to clean up the room how Papyrus would've had it, but he didn't. Papyrus wasn't coming home. He wouldn't be around to clean the house, write sticky notes about Sans' socks, cook horrible-but-love-filled spaghetti and nag Sans about his puns and laziness. Sans' soul ached at the thought of never being able to look up to his little brother and his bright optimism.
And it wasn't just Papyrus. He'd never be able to exchange puns with Toriel. He'd never be able to tease Alphys or Undyne, or say hi to Napstablook or taunt Mettaton. He'd never be able to have tea with Asgore or flirt with Grillby. He would never hold Frisk's hand or see the sun again.
i won. no more resets.
A bitter laugh bubble up within him.
He ended up traveling across the underground, through the empty streets of Snowdin and dust-muddled fields of Waterfall, and skipped Hotlands entirely. He ended up in the Judgment Hall, the golden light peaceful - a stark contrast to his own state of mind. He passed through the throne room, then he was in the final corridor,standing inches away from the humming barrier.
"i won..." he whispered desperately, laying a phalange on the barrier.
But what did you lose? the voices of the thousands he killed murmured in his mind.
With a hoarse cry, he dropped to his knees, fingers scraping at his skull as the voices whispered accusations, growing louder until he couldn't hear his own screamed apologies, echoing down the corridor like the howls of an injured animal. He cried out for help...
*But nobody came.
Omake:
It only took a few days for Sans to come to terms with the severity of his situation. With no one to talk to and nothing to do, Sans slept(or rather, attempted to sleep, his unconscious moments riddled with nightmares that woke him screaming and more tired than before) and ate and slept some more until one day there was no more food. That didn't surprise him - the kid had eaten pretty much every available morsel, trying to survive his onslaught on them, and the resets hadn't made the food reappear. Sans wasn't too worried about it at first, since monsters could go way longer than humans without food,especially skeleton monsters who didn't actually have physical stomachs without using magic. But he'd underestimated the exhaustion wracking his bones and it wasn't long before he was hardly able to move.
if i'm going to die, he decided, it's going to be where I can see sunlight.
Sans couldn't remember what actual, real sunlight felt or looked like,since the only pacifist route that Frisk went through was a longtime ago and never repeated. But sitting against the wall next to the barrier and craning his neck, ignoring the trembling of his bones, Sans could distantly see the light. It didn't do much in the form of comfort, but Sans closed his eyes and basked in it anyway. He could almost imagine that his brother was by his side again, whole and kind instead of a cruel bust.
"hey, buddy," he thought he heard as his magic began to dissipate. "let's get you out of here."

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Nothing More Than Love and Space Dust
FanfictionSans cried out for help... *But nobody came.