In the heart of Inkwell City, there stood the city orphanage. A place where children without families can play, learn, and live until the day they are adopted into a new family. That's usually how some orphanages are but, in some ways, this orphanage was more like a workhouse.

Inside the children were not allowed to play games, listen to music, crack jokes, or anything at all that was considered fun. All they did all day was work, eat, and sleep.

The female penguins who ran the orphanage made sure that the children abided by the rules. They carried rulers that they used to punish the troublemakers with a slap to the wrist. And when that's not enough they... well, you'll find out later.

Thanks to these rules, the children were not happy but none of them had the nerve to complain or rebel.

'Guess who always got the worst chores at the orphanage.'

She was six years old. She had her black, long-sleeved top, white gloves, and orange shoes. She had a dark teal skirt that was ratty at the bottom, and it had a mismatched patch on it.

'Yeah, that's me, Little Ms. Chalice. Been in this dump for as long as I could remember.'

Chalice entered the laundry room pushing the canvas basket truck. She grunted as she pushed the heavy canvas. She stopped and sat down, intending to take a short breather, but then she heard the slow tapping.

Next to her was none other than Head Penguin Jen. The head of the penguin colony and, without a doubt, the meanest penguin boss the orphanage has ever had. She looked down at the chalice girl with disapproval and lightly tapped her ruler against her flipper.

Chalice giggled nervously before she got up again and pushed the canvas along.

'Yepp, this place was the pits. Somethin' was missing in my life. Somthin' that made me happy, I just didn't know what it was. Until...'

Chalice paused when she heard water splashing rhythmically.

"Huh?" the girl said.

That sound was coming from other children washing clothes against the washboards rhythmically. And it didn't stop there. The way the lines strummed, the sheets flapped, the towels flapped.

'The way it all came together, it sounded like music. And I liked it.'

Chalice started tapping her feet to the sounds.

'With those first steps, I had found that thing that made me happy. Dancin'!'

Chalice closed her eyes and tap danced on the floor. She wiggled her fingers and smiled.

"Ehem!" came a throat clearing.

Chalice opened her eyes and saw Head Penguin Jen glaring down at her and she stopped her dancing.

"Ms. Chalice," Head Penguin Jen said. "what's our number one rule in this orphanage?"

"No fun of any kind." The other children answered in unison.

"And why do we have this rule?" Head Penguin Jen asked.

"So we don't grow up to be criminals," The other children said.

"Exactly."

RING RING RING

"That's lunch." Said one penguin.

The children clamored as they ran to the mess hall.

"Oh, lunch!" Chalice said with a nervous chuckle. "I'd love to stay and chat, but that gruel isn't gonna eat itself." She was about to walk away but the head penguin stopped her.

"Not so fast." Head Penguin Jen said as she dragged Chalice to the restroom. "Lunch is only for children who abide by the rules." She gave the chalice girl an old toothbrush. "Now, scrub that floor until it shines." Then she waddled away with a huff.

Chalice sighed before she got on her knees and started scrubbing. She scrubbed rhythmically. A spark lit up in her eyes before she laughed and started tap dancing.

Head Penguin Jen heard the tapping and when she found the chalice girl dancing, she picked her up, dragged her away, and gave her wrist a hard smack with a ruler.

'From that day on, I kept accidentally findin' more ways to bring back the rhythm and start dancin' instead of doing chores. Working on the washboard, the line, the towels, the scrubbin'. Didn't matter where they sent me, I always found a way to dance to my own beat. Then they'd squawk, drag me away, smack my wrist with the ruler, and then set me to work on somethin' else.'

One day, Chalice got so distracted with dancing, that Head Penguin Jen dragged the girl to 'The Detention Room'. A small closet-sized room with nothing inside. Here is where they send the most troublesome children, where they would have to sit for hours in the dark.

After smacking Chalice's wrist with the ruler again, the head penguin decided to give the chalice girl a stern talking to.

"Ms. Chalice, do you know why we have our no-fun rule?" Head Penguin Jen questioned.

"So we don't grow up to be criminals." Chalice quoted.

"That's right." Head Penguin Jen said. "Have I ever told you about what the orphanage was like when I first worked here?"

"No, do tell," Chalice said sarcastically. "for the other dozenth time in a row," she muttered and rolled her eyes.

"I was a young penguin woman, working as an assistant for Head Penguin Erin..."

FLASHBACK

Many years ago, the orphanage was a more cheerful place. Children laughed and played, and no one wore rags. The penguins didn't carry rulers or frowned at the children.

'The head penguin at the time was soft-hearted. Too soft for my liking. She let the children play and dance and sing and any other unconstructive things they liked.'

SHATTER

Head Penguin Erin waddled towards the sound and found a little lamb child next to a broken glass cup on the floor.

"I'm so sorry," the lamb said meekly. "I was dancing and then I bumped against the table."

"Don't worry, little one, it was an accident." Head Penguin Erin said. "Jen, fetch the broom and dustpan please,"

"Yes mam," Penguin Jen said.

'Oh, yes. She was kind to all the children... and some took advantage of that.'

One day, Head Penguin Erin and Jen were watching the children play outside in the backyard. All the children were having fun playing games with each other. But in one corner of the fence, one little boy had his back to everyone which was a little suspicious.

'That little boy's name was Charley Piper. And he was a troublemaker.'

Head Penguin Erin and Jen approached the boy and gasped at what they saw.

Charley had a butcher cleaver in his right hand and had a frightened little caterpillar tied to a chopping block.

Charley was wearing a newsboy hat, white shirt, brown pants, and black shoes. Freckles dotted across his face.

"Okay little guy, just hold still," Charley said as he raised the cleaver.

Head Penguin Erin caught the cleaver just before Charley swung it down. The boy hit his hand on the block.

"Yowch! Who the hell—!?" Charley yelled before he turned and saw the head of the orphanage and her assistant behind him. "Oh... Head Penguin Erin and Miss Jen. How long have you been standing there?" he asked with a grin, a missing tooth in his smile.

"Charles, where did you get this?" Head Penguin Erin asked as she held the butcher cleaver.

"I... borrowed it. From the kitchen." Charley said.

"You know you're not allowed in there," Jen said. "And release that caterpillar this instant!"

"Miss Jen, please, we don't raise our voices to the children." Head Penguin Erin said. "But Charles, do let the little insect go."

The little boy pouted before he untied the caterpillar and let it crawl away.

"Now Mr. Piper, you know you're not old enough to handle culture and you shouldn't be so mean to little insects."

Charley pouted his lip and looked down in shame. "I'm sorry Head Penguin Erin," he said.

"Thank you for apologizing." The head penguin said. "But promise me you won't do anything like this again."

Charley lifted his head. "I promise," the boy said with a big smile as he took off his hat and a halo appeared over his head.

"Very good," Head Penguin Erin said. "Come along Miss Jen."

Jen followed her boss but glanced back.

The halo disappeared and the boy smirked devilishly.

'Erin was so naïve. She thought all her children were little angels, but that boy was more like a demon. I wish I could say he was the only one, but he wasn't. Soon his troublemaking influence spread like a weed in a garden. Next was Barley Fisher.'

Little Barley had short blond hair and headgear over his face to help with his crooked teeth. He wore a sailor outfit, tube socks, and a sailor hat.

He would stomp on children's feet and steal sweets from the kitchen for Charley and himself.

'And lastly was Edgar Striker, the spider boy,'

Edgar was small and he had a blue bowtie around his neck.

One day, during a child's birthday party, Edgar jumped out of nowhere on the table and hissed at the children, scaring them away with his fangs. The spider stole the cake and took it for him and his friends to enjoy alone.

'Pranks, vandalism, tricks, stunts. Their attitudes never improved no matter what Head Penguin Erin tried but she was never forceful enough with them. Things went from bad to worse until the day they ran away and never came back.'

END OF FLASHBACK

"And do you know where they ended up? In Prison!" Head Penguin Jen said. "They will spend the rest of their miserable lives rotting away in The Slammer because they didn't live by the rules. When I became head penguin of the orphanage, I vowed that I would raise my orphans under strict rules and authority, and I would nip the bud of any troublemaking weeds in my orphanage so that they don't become like those wretched, lose some bottom feeding butcher boys."

The head penguin held onto the door.

"Consider this a taste of the life you'll have if you continue to behave like a troublemaker!" Head Penguin Jen squawked before she slammed the door closed and locked Chalice inside.

The Detention Room was quickly engulfed in darkness save for a small sliver of light under the door. Chalice sat on the floor and hugged her legs.

'She used the Butcher Gang as an example to scare us into following her rules. But it still doesn't make sense. Just because those guys were jerks as kids the rest of us gotta' suffer? And they did bad stuff sure, but all I did was dance. Was it hurtin' anyone? No. That stuffy old bird just hated me for not followin' her rules and as I sat in that dark closet, I knew it was time for a change.'

The Next Day...

Chalice did her best to act as well-behaved as possible. No dancing, no laughing, just working all the while secretly stealing the rulers from the penguins. Along with some rope, a bed sheet, and some wire. She had successfully taken the rulers from all the penguins... except one.

Chalice was about to take Head Penguin Jen's ruler, but the penguin caught her and smacked her wrist.

"Ow!" Chalice exclaimed and held her wrist.

"And just what do you think you're doing?!" Head Penguin Jen exclaimed.

"Uh..." Chalice before she took the canvas and ran off.

"Stop her!" the head penguin ordered.

The other penguins squawked as they chased the chalice girl.

Chalice drove the canvas towards an open window. She dove into the canvas and then jumped on the windowsill with a bed sheet wrapped around her.

"Young lady," Head Penguin Jen said. "you have just three seconds to get down from there. One, two..."

"Three!" Chalice exclaimed before she leaned back and fell out the window.

All the penguins squawked before they looked out the window.

With the stuff she had stolen, Chalice had constructed herself a pair of makeshift wings. Before she hit the ground below, she spread her wings and flew up into the sky. As Chalice flew in the open sky, she couldn't help but admire the sight of the city.

'It seemed like things were startin' to look up. Yes, sir. Everything was finally comin' up Chalice... Until they weren't.'

Chalice admired the view that she didn't see where she was going and slammed against a billboard. She screamed as she fell to the ground until she landed in a trash can. The chalice girl managed to land without any damage, that was the good news. The bad news was that now she was all alone in a drafty alleyway, covered in garbage and hungry.

Chalice grunted as she picked the garbage off her body and held her hands over her rumbling stomach until she found a can of beans. A single bean landed on her hand, but that bean turned out to be a bug and it crawled all over her hand.

"Ew, ew, ew, ew, ew, ew!" Chalice exclaimed as she tapped her feet and shook the bug off.

Suddenly a coin fell into the empty can the chalice girl was still holding. She looked up and saw a well-dressed birdman standing next to her.

"What a charming little dance." The bird said before he walked away.

'And just like that, everything changed. That's when I realized all I had to do to survive out here was to turn up the charm.'

Chalice started tap dancing for a random bug woman.

"With a tickety-tap tap, And a wink of the eye~ I can get anything, By turnin' up the charm~" Chalice sang.

"I'll do whatever it takes~ To get what I need~ And really, what's the harm?~"

Chalice used her charm and dance talents to get food and whatever else she wanted.

"I was down-and-out done for, Life had me licked~ Then I batted my eyes, Flashed 'em a smile~ Suddenly something clicked~"

Chalice soon found that along with dancing and charming, she also had a knack for thievery that she used to get extra money.

Three Years Later...

Chalice was still homeless but had become an excellent dancer and charmer except now she was no longer wearing rags.

"Now I'm free as a birdie, Flyin' high and flyin' low~ The world is my "erster" Hey, it's a one-person show~" Chalice sang.

She danced through the streets and stole from some unsuspecting people.

"I'm lookin' out now for number one, I don't need friends to have my fun~" Chalice sang. "With a tickety-tap-tap And a wink of the eye~ I'm charming~ And disarming~"

Chalice stepped into the middle of the street and danced.

"I'm lookin' out for number one!~"

Suddenly, an Inkwell trolley came up the road and hit Chalice.

The chalice girl groaned as she slowly opened her eyes. Or maybe they were still closed because all she could see was darkness.

"What happened? Where am I? I feel so strange." Chalice said as she lifted her hands. Her hands were... glowing and see-through! Chalice looked down and noticed her whole body was glowing and her feet had been replaced with a ghost tail. She gasped.

"I'm a g-g-g-g-ghost!" Chalice exclaimed.

Suddenly a spotlight shined overhead... but not over Chalice. The light shined over a desk with a big red chair.

Henchman stood next to the desk and The Devil was sitting on the chair.

"That's right." The Devil said. "You're a g-g-g-g-ghost. I'm afraid it was just your time."

"What? My time?" Chalice asked. "But that's not fair. Everything was finally coming up Chalice!"

"File." The Devil said as he held out his hand. When Henchman didn't respond, the big devil tried again with a snap of his fingers. "File."

"Oh!" Henchman exclaimed before he picked up the heavy file and placed it on the desk.

"Yes, yes. Pity. Let's just take a look at your file, shall we?" The Devil said before he summoned a pair of glasses to read. "Ooh! What's this?" he said when he saw something interesting in the file. "Charming people into giving you things for free through song and dance."

Chalice chuckled nervously.

"You know, I'm a bit of a song-and-dance man myself." The big devil said. "Impressive, Ms. Chalice."

"It's just this little thing I do." The chalice girl said. "Hey, listen, I really should be going."

Chalice was about to try to escape but then a wall of fire surrounded the area.

"Stay a while, won't you?" The Devil said before he made the glasses, file, and fire disappear. "After all, how do you expect to dance without feet?"

"So I'm gonna be like this forever?" Chalice asked.

"Mm-hmm." The Devil hummed with a nod. "Unless you'd like to make a deal? I could offer you a second chance." He said.

"To be normal again?"

"Well, you'd still be a ghost, but you'd have the ability to turn into your living form any time you want."

"Okay! Sure!"

"There is one more thing. You'd owe me a favor to be named at a later date. Deal?"

The Devil extended his hand out to the ghost chalice girl. Without thinking much of it, Chalice extended her hand.

"Deal!" Chalice said.

They shook hands. The big devil's hand turned red.

SIZZLE

Chalice yelped and tried to pull her hand away.

The Devil smirked and kept a stronghold for a few seconds before finally letting go.

Chalice blew on her smoky hand before her ghost tail shook and her legs reappeared. She gasped before she started tap dancing. She changed back into a ghost and flew around the demons before turning back to normal.

"Hey, it works!" Chalice exclaimed happily.

"Of course." The Devil said. "But don't forget you owe me a favor."

"Well, I best be hittin' the bricks," Chalice said with a chuckle as she walked away.

"Uh-uh-uh. Wallet." The big devil said as he held out his hand.

"Aw, you got me," Chalice said before she pulled the devil's wallet from her pocket. She chuckled awkwardly.

The Devil took his wallet back with a chuckle.

"Yes. I've got you." The Devil said. "Oh, and by the way, another part of our deal is that you won't be able to tell anyone about it."

"What happens if I try to?" Chalice asked.

"Feel free to. See what happens." The big devil said with a cackle. "Okay, off you go." he snapped his fingers and Chalice disappeared in a puff of smoke.

The Devil chuckled.

"Uh... Hey, where's my wallet?" Henchman wondered.

Back in Inkwell...

A small crowd gathered around the chalice girl's fallen form.

"Poor little thing." Said the trolley driver.

"Ah, what a shame." Said an ant man.

Chalice suddenly opened her eyes and sat up. "Hiya!" she said.

The group of people gasped.

"What's everybody lookin' at?" Chalice asked.

The group of people screamed before they ran away.

"Ain't you never seen anyone come back from the dead before?" Chalice said as she brushed herself off and tapped dance off the street. She suddenly remembered the deal she made with The Devil and wanted to test it. Chalice looked around and spotted someone walking by. "Hey kid!" she said.

Bowlboy turned around. "Who me?" he asked with a dapper expression.

"Yeah, you wanna know a secret?" Chalice asked after she got over the creepy feeling she got from the boy.

"Sure!" Bowlboy said.

Chalice opened her mouth to speak but as she looked Bowlboy in the eye, the image of The Devil flashed in her eyes and her breath hitched in her throat. She took a step back and after breaking eye contact, she was able to breathe again.

"So what's the secret?" Bowlboy asked.

"Um... they're selling ice cream for half price on Third Street," Chalice lied.

"Oh boy!" Bowlboy exclaimed before he ran away. "Thank you!"

'So, The Devil put a curse on me? Greeeat.'

Chalice then snatched an apple from a fruit stand and took a bite.

'Well, other than that little hiccup, everything was comin' up Chalice.'

"Hey!" came a booming voice.

Chalice spat up the apple pieces from her mouth as a whistle blew.

"You gonna pay for that?" said the bee officer.

"Ah!" Chalice exclaimed before she ran away.

"Get back here!" The officer ordered.

Chalice ran away and managed to hide in the alleyway next to the glasses store. When the cop was gone, Chalice tap-danced into the Optician.

"Click your heels, go, go, go, And dance across a rainbow~" Chalice sang as she exited the building with new sunglasses.

After she left, Cuphead, Mugman, and Bendy poked their heads out of the store.

'That was the day I met the two ding-dongs cup and the little devil. 'Course back then I didn't know he was a devil, I thought he was a kitten before I accidentally discovered his secret. Maybe it was a big risk to trust Bendy but I'm glad I did. Since then I started lookin' out for someone who wasn't number one. Bendy, Cuphead, and Mugman are my best friends. Heck, they're my only friends. And as time passed and we got closer as friends, Bendy started crossin' my mind more and more. I feel like he and I are a lot alike. We're both kids with paranormal powers, mischievous nature, dance in our steps, and songs in our hearts.'

In Present Time...

Chalice blushed as she became lost in thought as she remembered that time she and the little devil danced at the queen bee's party.

'Speakin' of hearts, I'll admit that I kinda started having feelings for Bendy Devil. Like I said we're a lot alike and whenever he catches me in his arms or dances with me, I feel alive again,'

THUD

The sudden shift snapped Chalice out of her thoughts and her blush faded.

RING

"Uh, okay, we're here," Henchman said. "Good luck."

That's right. Chalice was in the elevator to the Underworld and apparently, she was expected. The chalice girl gulped before she stepped out of the elevator and walked the long way towards The Devil's throne. As she approached the throne, she smiled nervously.

"Hey again, Devil. Been a while." Chalice said. "Say, you look fantastic. You seem to be getting younger and younger." She chuckled nervously.

The Devil was nonchalantly filing his claws.

"Ms. Chalice, charming as always." The Devil said with a smile. "Looks like you've been having quite a time up there. I see you've made some friends. One of which is my son."

"Who Bendy? Yeah, we're friends, he's great. Must take a lot after you."

"Yes, but he's not what I wanted to talk to you about. It's about your cup friends."

"Oh, them, the ding-dongs. They're great too. You'd love 'em."

"Oh, I'm sure. But moreover, Ms. Chalice, it's time to cash in on that favor you owe me."

"Sure. What do you need?"

"I need you to betray the ding-dongs."

The Devil brought out a floating mirror that showed an image of Cuphead and Mugman.

Chalice gasped.

A/U; Now some of you might be wondering where Bendy is? Well, worry not, he will be found a rescued in the final chapter.

And just to get you guys extra excited, here is next week's chapter title.

"The Angel, The Devil, and Ms. Chalice"