The room belonging to two young cups was lit by nothing but the full moon rising over the Inkwell Isles.  The household was settling down to go to bed.

The two boys were snuggled into their bunks with their drooping, weary eyes. For weeks they've been struggling to get a good night's sleep. How could they sleep knowing that the Devil could appear at any moment and reap Cuphead's soul?

The door cracked open and their cheery Elder Kettle's face peeked through, "Good night, boys!"

Cuphead yawned and flopped his hand in an attempt at a wave. He didn't make eye contact with their caretaker.

Mugman lifted up his head weakly, "Night.." His head fell against his pillow quickly. Everything felt so heavy.

Elder Kettle closed the door and frowned. He knew something was going on with them, but they would never tell him. The idea of camping there and eavesdropping on them ran through his head. The kettle shook it off, ashamed of himself for even thinking that and headed off to his own bed.
—
As soon as Elder Kettle was out of sight, Mugman climbed down the bunk and sat beside Cuphead in the bottom bunk.

Cuphead pulled a notebook out from underneath his pillow and handed his brother a pencil. He drew in a tally on the front page, "Twenty five days Devil free."

"I figured he'd be back the day after we electrocuted him on the Obliterator." Mugman cocked his head to the side, "Why is he waiting so long?"

"Maybe he forgot?" Cuphead severely doubted that was true, but it was a comforting to thought to him.

"I don't know, Cuphead." The mug took the notebook and scribbled a drawing of The Devil in it, "This is the Devil we're talking about. It just doesn't make sense. Why would he obsess over getting your soul and then not show up when he has an opportunity?"

The two sat in uncomfortable silence as Mugman was drawing. Cuphead watched curiously, while his brain flooded with anxious thoughts.

He was overridden with guilt and fear. All he wanted was to have fun at a carnival with his little brother, how did he end up owing his soul to the Devil?

"Cuphead?"

And Mugman was so desperate to save his brother's soul that now he's losing sleep and stressing just as much, maybe even more.

"Cuuuphead?"

Cuphead hated seeing Mugman in so much despair, it hurt him so much.

"Cuphead!"

Cuphead just wanted everything to go back to normal. He hated lying to Elder Kettle, he was terrified of the uncertainty of his fate, and he missed getting a full night of sleep.

"CUPHEAD!"

Cuphead was snapped out of his thoughts by his brother's panicked voice, "What happened?!"

"Are you okay?"

Cuphead noticed he was breathing heavily. He had fallen so lost in thought it didn't occur to him that he was visibly panicking. "Uhh, yeah! Never better!"

The door swung open and the face of their Elder Kettle appeared, "Boys?! Are you okay?!"

The two scrambled under the blankets, "Yes, dearest Kettle!"

"Mugman, I heard you scream Cuphead's name, what happened?"

"Uhh.." Mugman drew a blank. He was terrible at lying to Elder Kettle.

"I was havin' a nightmare and Mugsy was waking me up!"

"Another nightmare? Cuphead, you've been having one nearly every night." The kettle sat on the end of the bed, "What are you dreaming about? Did something happen?"

Memories of the Devil's menacing smile flashed through the cup's mind. Every time he closed his eyes the Devil's face was there.

"Nah, I'm fine! It's nothing."

"You sure?" Elder Kettle didn't buy it. He didn't want to leave until they confessed.

"Cuphead, can we tell him?" Mugman asked, his eyes were pleading to Cuphead.

"There's nothing to tell, Mugsy. Just a weird pattern of nightmares."

Elder Kettle caught a glimpse of the notebook and picked it up, "Oh, are you boys drawing?"

Their pupils shrunk. That notebook included drawings and notes and diary entries about everything they didn't want Elder Kettle to know.

"N-NO!" Cuphead covered his mouth, realizing how loud he shouted. "It's empty! We haven't drawn anything in it. At all. So." He was drenched in sweat. They were done for.

"Why are you so nervous? I'm sure you two are great artists!" Elder Kettle chuckled and opened up the notebook.

The first page was the twenty five tally marks. Luckily, they didn't label what they were tallying so they had room to lie.

"Those are.. um.. how many days into summer vacation we are!" Mugman piped in.

"Oh, Mugman, we're much further than that into summer." Elder Kettle turned to the next page.. which was exactly what they were worried he'd do.

Elder Kettle sat quietly, unable to process what he was looking at. Was this just one of those morbid drawings that all children draw for unexplained reasons or should he be very concerned?

The brothers were desperate for their caretaker to say something. Anything. His silence scared them more than his anger. "Elder Kettle.."

Elder Kettle closed the book and left their room without another word. He brought the book with him, despite how afraid he was to discover what other messes they got into.

Mugman burst into sobs and reached to hug his big brother. "Oh, we're dead!"

Cuphead returned the hug, patting Mugman's back, "Hundred percent."

—
my first fanfiction that isn't trolls wowowow i've loved cuphead for years but the show gave me motivation to finally write about it.