I'm too tired to sleep

300 Years - Nightmare

Killer and Nightmare made a good team. At least, that was what Killer thought anyway. Secretly Killer looked up to Nightmare. After all, Nightmare was the one who gave him his freedom, and the best job ever, and an amazing place to stay. Killer just wished Nightmare was a bit more friendly, a bit more open. After 100 years of working for Nightmare he only knew two things about his history;

1. He was from Dreamtale

2. He had a brother

Pretty pathetic huh? Every time Killer tried to pry too much, Nightmare would just use a tentacle to pick Killer up by the hood of his jacket, and move him away. Nightmare's tentacles were strange, and Killer wondered where they'd come from (Nightmare was a skeleton after all). They seemed to behave as another limb, but also changing with Nightmare's mood. After a bad day, they would flick and twitch like an angry cat's tail, and when he was tired or bored they would sway lazily. Naturally, Nightmare denied all of this.

He also had suspicions that Nightmare heard voices, from the way he would stop at random times, as if listening to a voice Killer couldn't hear, or when he would make faces randomly as if in response to something someone said. But hey, Killer wasn't one to judge.

As much as he enjoyed his new life, sometimes Killer wished there was someone to really talk to (Nightmare had once said that small talk was just a waste of time created by people trying to be polite when they really didn't care what you said) . So when Nightmare mentioned that they should think about 'recruiting' another Sans, Killer was eager to help.

They went to Aftertale first, specifically to the Save Screen, to find a Sans named 'Geno' (short for Genocide, Killer supposed). It didn't go quite as well as they hoped. Turns out Geno only wanted to destroy his AU to stop the suffering of everyone in it, and he wasn't very pleased at the idea of a job that was causing more suffering.

Killer expected Nightmare to kill Geno before they left, just incase Geno decided to stop the suffering of other AU's at Nightmare's hand, but he just mumbled something about 'stubborn Sanses, all think they need to do the right thing or whatever'. When Killer asked, Nightmare said that because of the nature of Geno's soul, he was pretty much dead anyway, and you can't kill a corpse. It was the first time Killer had ever heard Nightmare admit he wasn't strong enough outloud and so clearly.
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After the failure of Aftertale, Nightmare was feeling sour. He really wanted to just jump into the nearest AU and start causing chaos.

Reckless destruction will get you no where, you'll only feel bad again afterwards.

As usual, the voice was right. What if Ink or Blue was there and caught him by surprise? What if Error was destroying that AU? What if it was a genocide run? (those AU's were practically dead in between the human's resets).

Nightmare took a few breaths and reasoned that they could just try another AU tomorrow. Nightmare had seen the way Killer's skull lit up when he'd suggested a new recruit, and the way it fell when he realised Geno would not be joining them.

Why are you even thinking about that?

Again, the voice was right. Nightmare should not care what Killer thought. They weren't 'friends' or anything.

Says the one who claims to acknowledge his feelings.

Nightmare pretended not to hear that.

After a little bit of speculation, Nightmare went to find Killer for another try at recruitment. They would go to Dusttale to find a Sans called 'Dust'. Nightmare found Killer sitting on the sofa and eating a chocolate bar.

Creators above. Are all 'evil' Sanses obsessed with chocolate?
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You guys know how it goes from there right? Welcome to the gang, Dust! We are getting so close to 500 years guys!! I'm so excited!

Sincerely, a haunted wardrobe