Summary: Papyrus doesn't always die. Maybe that's what makes it all the worse.
The very first time Papyrus dies, Sans is watching from the shadows. He hadn't trusted the human, despite his promise to the woman behind the door, and the moment Papyrus turns into dust, Sans feels something inside him break.
He's not the only one breaking though.
The human was scared. They'd only lashed out in fear. They start crying as they realize what they've done, and they run away in shame.
When their footsteps peter away into nothing, Sans forces himself to move, stumbles as far as his legs will take him, and falls to his knees right in front of the pile of dust that was his brother just moments before.
He stays there for a long time.
The third time Papyrus dies, Sans realizes the hysteric sobbing after the human disappears is coming from himself.
It echoes all throughout Snowdin, mournful and desperate.
For a short while, there's a respite. Sans doesn't trust it, but he's thankful for it, even if it puts him on edge all the more. His brother's oblivious, of course - Sans prefers it that way. No one needed to shoulder the knowledge he did but him.
He watches from the shadows as Papyrus becomes friends with the human, and breathes a sigh of relief.
Papyrus doesn't always die.
Maybe that's what makes it all the worse.
The eighth time Papyrus dies, Sans tries, with shaking hands, to scoop up the dust that was once his brother, and breaks down anew when the dust keeps slipping through his fingertips.
His ribs feel like they're going to splinter and break. His breathing is ragged, his head feels like it's going to split in half.
He wishes the human would just come back and kill him too.
The tenth time Papyrus dies, Sans finally learns to get back to his feet, and carry the dust back home.
He only gets as far as the door before he trips, sending Papyrus's dust all over the floor. Sans lies there, realizing he couldn't even give his brother a proper funeral, and laughs at his uselessness.
It doesn't take long for the laughter to turn into tortured sobs.
He lies there for a long time.
The fifteenth time Papyrus dies, it's to a human who Papyrus believes wholeheartedly in. A human who he says just needs to try a little harder.
The human crushes Papyrus's skull underneath their foot.
Sans feels something inside himself snap into pieces.
The twenty-second time Papyrus dies, Sans spreads Papyrus's dust all over his favorite things.
He saves a little for himself, even though he's sure a miserable failure like him couldn't possibly be one of Papyrus's favorite things now.
The thirtieth time Papyrus dies, Sans starts wearing Papyrus's dusty cape and follows the human into Waterfall.
He's going to make them pay.
After a while, Sans stops keeping count. Thirty really is too many, isn't it?
But every new death hurts just as much as the first did.
It would be easier, sometimes, if he didn't care. But Sans knows he can't do that - he loves his brother too much.
Even if he can't do anything to help him.
When they finally reach the surface, Sans breathes a little easier.
But just a little.
At any point, they could end up back underground again.
And Sans doesn't know if he can watch his brother die over and over all over again.