Chapter Text
Cuphead had honestly felt a bit shaken up from the encounter with the inky demon from earlier, but he was not about to show it. Hell, that would probably boost that bastard’s ego and make him smile that dumb smile again. Cuphead sighed, annoyed. He shouldn’t think of that jerk right now though, he needed to focus on getting more contracts than him. It’s a race now to get more, and Cuphead wasn’t about to lose so easily.
Cuphead approached a shady bar in the village over from where he usually stayed at. It was nothing special from outside, it honestly looked old and needed a much needed renovation. But who was he to judge? He entered and took a quick glance around. There didn’t seem to be many customers, maybe like three or four max lounging around with booze in hand. And the bartender, who is a blue beetle toon, seemed to be busy cleaning some glass cups.
Cuphead walked over to the counter, taking a seat at the stools that are noticeably taller than he was. There was some quiet jazz that three performers were playing in the background from the stage, making the whole setting quite cozy. But Cuphead wasn’t here to have a drink and relax, he was here for an S-ranked mafia boss’s contract, but said mafia boss didn’t seem to be around currently…
“Hey,” The bartender said and Cuphead looked over to him, “no kids allowed, slugger.” He pointed to a sign that says in big, bold letters ‘NO CHILDREN ALLOWED!!’.
“Oh- uh, I’m- erm…” Jeez, okay, he needed to think of something fast before he got kicked out. “I’m actually, uh- t-twenty-two years old.” No, shuddup, he most definitely did NOT stutter.
The bartender eyed him suspiciously for a second, but just shrugged after a moment, turning his back to put the glass cup he’d been cleaning into its rightful place on a wooden shelf.
“Alright. I believe ya.” Cuphead let out a relieved sigh and took another gander around the rustic bar. Seriously, where was this so-called ‘mafia boss’?? Did he somehow get the wrong location? Or perhaps he was in the wrong bar or village…? “Say, are ya perhaps lookin’ fer someone?” The bartender asked suddenly with a strange knowing glint in his eyes.
“Uhm,” Cuphead could use some pointers on this debtor’s whereabouts… “Yeah, I am. Do you know where I can find someone named ‘Big Boss’?” Then, as Cuphead uttered out the name of the debtor, the room fell completely silent and a gasp came from some other patrons nearby. Cuphead looked around confused. Was it something he said? The bartender motioned for Cuphead to come closer to him.
“Hey, kid, I know you ain’t from ‘round here and that yer not legally an adult, but here’s some advice… Never EVER utter that name ‘round these parts. Folks here are afraid of the man.” Cuphead nodded, understanding.
“Well, I still need ta’ find ‘em.” Cuphead replied in a whisper. The bartender gave him a suspicious look of uncertainty. “I’m um.. a debt collector.” Cuphead explained, pulling out his list of debtors.
“Ha! So the Devil sent out another one o’ ya, huh?” The beetle laughed as he went back to cleaning more glass cups with a rag. “Well, I’ll tell ya right now that yer’ not gonna have a lotta luck gettin’ his contract, that’s fer’ sure.”
“Can you just tell me where he is, or not?” Cuphead asked impatiently while tapping his finger on the wood of the counter. The beetle dryly chuckled.
“Yer serious ‘bout goin’ ta get his contract?” Cuphead nodded, his expression serious. “Alright, you asked fer’ this…” The bartender motioned for Cuphead to get closer to him so that no one nearby could listen in. “Big Boss usually comes to this very bar at around 11pm sharp doin’ business in the basement. If ya can catch ‘em off guard, then snatchin’ his contract will be easy as pie.” Cuphead nodded again, his eyes full of determination. Wait, what time is it? Cuphead rolled up his sleeve but then realised that oh. Wait, he doesn’t own a watch.
“Hey, what time is it?” He asked and the bartender pulled out a pocket watch from their vest pocket.
“It’s currently 8:40.”
Cuphead groaned, slouching in his seat and thumping his head on the counter. The beetle chuckled.
“Ya’ came a bit early, bud.”
“I noticed.” Cuphead replied dryly, his voice slightly muffled. The beetle toon just chuckled again then went back to doing his job serving customers drinks.
Cuphead hadn’t even realized he’d dozed off to sleep when he was abruptly woken up by a shove that caused him to fall off of the bar stool he was sitting on, hitting the wooden floor harshly on his bottom. He regained his bearings then realized that a bar fight was happening. There were a bunch of toons fighting and punching each other chaotically all around him. It seemed as though more customers entered the bar while he was out.
Cuphead stood to his feet and turned to ask the bartender what the hell happened while he was asleep. But before he could even ask, he already answered him.
“Yeah, it’s a Friday night. This sort of thing happens regularly. It’d honestly be weird if it didn’t happen.” The beetle chuckled as he handed a beaten rabbit toon a glass of beer, he chugged it then punched the person beside him and they quickly started fighting.
“Wh-“ Cuphead stammered, confused as he watched the rabbit exchange punches with the other toon beside him. “Why??” The red cup only gets a cackle as a response.
“By the way, it’s 11pm now.” At that, Cuphead perked up and looked at the watch that the bartender is currently holding up at his face. “Good luck.” The beetle said as he placed the watch back into his pants pocket. Just then, the door opened with a loud bang and everyone’s attention was now focused on the entrance. Their movements froze temporarily.
The moonlight cast a huge, looming shadow of a big pug toon in an equally as big brown coat with a cheetah print on the fluff. Two other dog toons stood behind him on each side, with one of them holding a heavy suitcase — Cuphead presumes they were his bodyguards. The pug stood there with a wicked grin, shining his bright and shiny golden tooth in the moonlight.
The pug lit a cigar then walked into the bar, each step that he took making a creaking noise from within the floorboards. It was so quiet that Cupheads could even hear the labored breaths of the men who were brawling with each other just a moment ago, now quiet with their attention fixated on Big Boss. Well, Cuphead assumes that it was Big Boss. He certainly looks like he fits the name perfectly.
The pug approached the counter, and the bartender, like clockwork, handed the intimidating toon a key to the basement. He didn’t say a word as he motioned for the two other dog toons to follow him down the basement. Everyone stayed quiet as they listened to their heavy footsteps descend down the creaky, old wooden stairs. Then, when they can no longer hear a thing, everyone begins to whisper amongst themselves.
Cuphead sat back on the bar stool with a hundred yard stare filled with fear. The bartender noticed this and went to give Cuphead a drink. Cuphead stares at the offering confused, wondering if this dude really just gave him alcohol.
“It’s apple juice, c’mon, I wouldn’t give a child alcohol.” After hearing that, Cuphead chugged the drink then slammed the cup back down. Whoops. He actually didn’t mean to do that. His nerves were just- uhh- OKAY HE’S SCARED, ALRIGHT? Did you see that guy?! He was like- he had to be at least eight feet! And that’s extremely tall considering Cuphead was barely even four feet.
“Cold feet?” The beetle asked as he refilled Cuphead’s drink with more apple juice. He slid the drink to the teen and this time Cuphead takes his time sipping it. At the older toon’s question Cuphead looks away with a light blush on his face as he taps his finger on the cup.
“…no.”
“Then what’re ya wait’n for? Go get ‘em!” Someone behind Cuphead said, pushing him forward and off of his seat. He glared back at the man when he regained his footing, to which he then realized that everyone in the bar was staring at him expectantly. A bead of sweat rolled down his face.
“Aren’t you here for Big Boss’s contract? A debt collector from the Devil?” Another person from the crowd asked, to which the others agreed and mumbled quietly to themselves. Cuphead gulped, turning towards the door to the basement. The other patrons watched anxiously with anticipation as Cuphead walked to the door and carefully opened it. He took a second to gather himself, then he entered through and a small click! sounds, signifying that it shut.
…
“He’s so dead.”
“Yeah, there’s no way that pipsqueak is coming out alive.”
You’ve fought bigger debtors before, like Cala Maria! Or Dr. Kahl’s Robot! Chef Saltbaker! THE DANG DEVIL! There’s no reason you should be worryin’ ‘bout some mutt… Cuphead tried to convince himself as he descended down the stairs as quietly as he could, cringing to himself every time he heard a creak.
Mafia boss... like in the movies. And, now that he thought of it, Big Boss did look a lot like how a mafia boss would- y’know, look like in the movies. Uh- but anyways. He needed to focus.
The sound of voices talking amongst themselves made Cuphead freeze and proceed down much slower. He stayed on the stairs, crouching as he peeked through the wooden rails. He was glad that there was no light from where he’s hiding from. Or else they’d immediately see his bright red shorts and nose, then he’d be mincemeat. Or worse, dead.
The voices seemed to be talking about trading goods— maybe liquor or drugs? Cuphead didn’t quite know, nor care. Then suddenly, a deep rumbly and boisterous voice spoke up.
“Those assholes will fucking PAY! NO ONE rips off Big Boss. NO ONE.” He roared and Cuphead could see the other people practically shaking in their boots at his sudden rageful outburst. Cuphead himself nearly jumped out of his skin too.
A shaky voice tried to de-escalate the situation, attempting to reason with the big pug, but as he rambled on and on, his voice quivering and lowering to a whisper as his confidence diminished, Big Boss approaches the scared person, his huge form easily towering over their smaller one. Cuphead couldn’t quite see what happened next, but by the spine-chilling scream and blood splatters a moment after, then the sound of a gunshot, he can probably take a good guess.
“Anyone else wanna spout nonsense?” Big Boss turned around, holding up his revolver as a silent threat. Everyone shook their heads and the dog ruffed with an evil, satisfied smirk. “Alright, I want my goods and money back. You two…” He sat down at a small round table that had a briefcase full of cash, an ashtray and a couple of beer and wine bottles scattered about on it. The dog proceeded to explain his plans but Cuphead basically had it blocked out of his head by the time he started talking.
He should probably go now while he’s busy and distracted with boring business stuff… Cuphead equipped his smoke dash, then cautiously descended down the stairs once more, crouching as he did so and using the dark lighting to his advantage. He finally reached the concrete floor and looked around for some sort of cover. Scouring the room quickly, he spotted an open wooden crate and rolled over to it. His heartbeat was basically thrumming out of his chest from adrenaline. He steadies his breathing, gulping down his anxiety.
It kind of felt good, though. To have such high stakes.
Cuphead took a peek from the side of the crate. They’re still talking. He threw a smoke bomb onto the table and in the flash of an eye he was then aiming his gun right at the pug’s pink nose with a dark, serious glare on his face.
“I’m here for your contract.” He simply said. The two bodyguards stood to their feet, pulling their guns out and aiming them at the intruder. Big Boss seems to be taken aback by this random newcomer’s appearance, but all he does next is bark out a couple of loud, boisterous laughs. Cuphead frowned in confusion.
“Oh boy, this is fantastic.” Big Boss cackled as he wiped away a stray tear from all of his laughing. He leaned back against his seat, resting a hand against his round belly. “The Devil really sent a damn kid for my contract? Seems Lucy is gettin’ desperate, boys! Haha!” The bodyguards exchanged a confused look with each other and shrugged, but they too let out a couple of laughs along with the pug. Cuphead’s glare hardened, his cheeks growing as red as his nose by anger or embarrassment, he had no idea. Might be both.
“Shut up! I’m not a kid.” A blue flame ignited on the cup’s fingertip as a warning. “Your contract.” Cuphead said again, his tone ever so serious. Big Boss leaned forward with a nasty grin plastered on his face, shining his gold tooth. Cuphead could smell his awful, wretched breath that smells of booze and cigarettes, and he scrunches up his nose in disgust.
“If you know what’s good for ya, you’d better skedaddle back on ta’ yer parents, kid.” Cuphead gritted his teeth and he aimed fire beside Big Boss’s head, the magic bullet hitting the wall behind him with a loud bang. Everyone freezes. The sound rang loudly through everyone’s ears in the silence after.
…
…In all honesty, Cuphead really hadn’t meant for it to be that powerful. Perhaps his anger affected the outcome in some way? But, maybe now this jerk will take him seriously.
Cuphead huffed through his nose, his glare sharpening. “I’m not a kid.” Big Boss glared up at Cuphead. A deep, low rumble from his throat sounds. Growling. It somehow just made the teen feel better about himself and he suppressed a smirk.
“Heh… You’ve got guts, but I kind of hate that ‘bout you... Boys, leave ‘em to me.” The bodyguards nodded, then excused themselves and proceeded to the stairs, taking the other guests with them as they did so. Cuphead didn’t take his gaze off of the pug. Not even for a second. The danger of the whole situation feels somewhat exhilarating, giving Cuphead an adrenaline rush that he knows all too well of.
“Your weird magic alone won’t save you, debt collector.” Big Boss rised from his chair, fixing his fluffy brown coat. Cuphead flinched as he did so, keeping his aim locked on the mafia boss’s face. The pug lit a cigar he’d pulled from his front pocket and blew the smoke in Cuphead's face. The teen squinted his eyes from the smoke and resisted a cough, to which the dog just laughed at, reeling his head back slightly. However, the next thing Cuphead knew was he was being punched right in the gut. The force of the blow flung him over to the wall behind him, creating a big dent with cracks all over. The impact shook the building.
Cuphead coughed and grimaced while clutching his stomach tightly. Something sharp almost punctured his stomach. Cuphead’s gaze panned up to see Big Boss flexing his fingers, his hands adorned with shiny golden brass knuckles.
Ah, hell. Cuphead wasn’t good at close combat. And don’t bring up those hedgehogs— that’s a completely different story.
Cuphead bounced back up on his feet, equipping spread and crackshot. Just in case he missed a couple of shots. HEY! He’s good at aiming! It’s just- an extra precaution… OKAY, SHUT UP— he’s focusing!
“Yer fancy guns won’t help!” The pug charged forward, punching the wall but Cuphead managed to duck on time. The whole building reverberated from the contact and Cuphead could hear the patrons from upstairs shouting out in alarm. The debris from the wall fell onto Cuphead’s baggy black sweater and he stayed frozen in place. “Think fast!” Big Boss gave the cup an uppercut, shooting him all the way up into the ceiling, and making a big hole in the process. The pug looked up at the ceiling satisfied but his grin was quickly wiped away when he felt a series of burns hit his body and he shielded his face with his paws.
“Think fast!” Cuphead yelled from the ceiling directly above Boss. Using his EX shot, he shot it directly on top of the pug who yowled out in pain. Cuphead smirked then ran to another area for cover when he heard Boss roar in anger. For once in his life he was glad he was so short, or else he wouldn’t have the ability to run in this tiny confined space so freely.
He clutched his stomach with one arm, hissing out in pain. The other arm being occupied with firing at Big Boss through the wooden ceiling. He felt like he was gonna puke from being punched in the stomach twice with such strength that it should’ve broken his bones, it sure as hell felt like he did though and he wouldn’t be surprised if it had.
“You BRAT!” Uh-oh, puppy is angry. Big Boss grabbed the table, throwing it up at Cuphead’s general area, which was pretty spot on because the next thing Cuphead felt was the sensation of falling and then the painful feeling of hitting the hard concrete floor. It was muffled, but he swore he could’ve heard the porcelain on his chest and knees crack. He goddamn hoped that doesn’t leave a mark. He weakly cried out in pain as the sensation of his skin literally cracking started to set in. A shadow peered over him, accompanied by a low growl. Oh crap.
Big Boss cackled maniacally. “You lil shit. You play dirty, y’know that?.” He knows. And that’s what makes fighting these debtors so fun. But what wasn’t fun was being the one getting beat up.
“Heh, you want this?” Boss crouched down to Cuphead’s level (the best he can) and waved his contract in his face tauntingly. Cuphead glared at him and tried to sit up. “No, no. You stay there, alright?” He pressed his paw on the cup’s back, holding him down. Cuphead tries to resist. Get up, GET UP! His mind and instincts yelled at him. Big Boss only cackled menacingly at his futile efforts, stuffing his contract back in his jacket’s pocket.
Cuphead raised his hand, shooting at the dogs’ eye and the dog toon finally let Cuphead free from his grasp to hold his hands at his bleeding eye. “ARGHH, F*CK-“The teen takes his chance to get away from Big Boss.
Cuphead smirked, then winced when he felt a sharp pain in his cheek. He gently touched the tender spot then realised it was cracked there as well, and it was deep gash too. He could already see that disgusting red staining his glove and he gulped.
Big Boss glowered at the cup while covering his eye with one hand. Crap, Cuphead should probably really run right NOWW- A chair was suddenly thrown his way and hit the rails from behind him, both the rails and chair breaking on impact. Cuphead just stares at the destruction.
Click!
Cuphead turned to see Boss holding a revolver while aiming it square in his face. “Ya wanna fight fire with fire?” BANG! Cuphead screamed out in agony while holding his right arm. Blood seeped through the fabric of his sweater. “Yer’ just a kid. Ya’ never had the guts to go into this line of work.” Boss approached Cuphead, crouching down in front of him. “Because if you did, ya wouldn’t be cryin’ right now.” Cuphead? Crying? Wh-when… Cuphead raised a hand to his face, feeling a dampness on his fingertips. Oh.
Big Boss grabbed Cuphead’s head firmly, smashing it against the staircase behind him.
CRAACKKkk…
Cuphead desperately grabs hold of the dog’s wrist to pry it off of him.
CRRAck craAckle…
It hurts.
CrAAckK.
But Boss didn’t stop smashing his head over and over. Cuphead weakly kicked his stomach with what strength he had left, but he was unyielding. It was as if it didn’t even affect him one bit. It probably didn’t, or if it did he didn’t show it. The cup’s vision went hazy, he didn't even realize the other stopped his abuse and picked him up for another round of punches. Probably in the stomach. That seemed to be his favourite place to hit him.
—
“AHHH-“ Cuphead shrieked as he was being thrown up into the ceiling again. But this time he went through another layer of the building’s wood. He was now laid in the middle of the bar, bloodied up with bruises and scrapes all over his everything. Ohh his body aches all over… Cuphead looked at his surroundings, but all he could gather was a bunch of blobs around him and muffled voices talking. He’ll just- he’ll just lay here for a bit… and… rest his body…
The patrons stare at the beaten cup with a look of pure horror and terror with their faces as pale as paper. They could hear roars coming from the basement from Big Boss and his bodyguards rushed downstairs once they heard him. When they were finally gone and out of earshot, everyone instantly rushed to the teen’s side.
“Oh shit he’s dead!” One of them shrieked as they held their head with shaky hands, their eyes dilated as they started to hyperventilate.
“He killed a kid!” Another cried out, literally, they had tears streaming down their face. They looked away from the bloody scene and rushed to the restroom with a green face. The rest of the group talked and whispered amongst themselves while staring at Cuphead.
The bartender managed to push through the crowd, yelling out, “He’s not dead, you idiots! Stop being dramatic. Look, he’s breathing.” He said as he carried Cuphead in his arms. “He’s just tired, is all.” Everyone let out a relieved sigh.
“What’re we gonna do with him?” Someone from the crowd asked and everyone else started to wonder the same thing. The bartender sighed.
“I dunno know… I’ll search ‘em to see if he has any contacts on ‘em so we can call someone to pick him up. Get him anywhere but here.” Everyone nodded and agreed with that. “I think I’m gonna have to kick you all out though. This has nothing to do with you.” Everyone then booed but the beetle however just paid them no mind. He pushed past the crown to take Cuphead to one of the cushioned seats. He then set him down in a comfortable position. With that, he then turned to his patrons to shoo them out of his bar. They all continued to boo at him but exited the building anyway.
The beetle returned to Cuphead and began to search his pockets. But all he could find are contracts and- oh, wait? What’s this? He fished out a little piece of paper, bringing it up to his face. It has a phone number with a name on the back, presumably the caller’s name. Bingo. He quickly runs to his telephone by the counter and dials the number.
“Come get yer’ kid! He’s all beat up from a fight!” He didn’t want to say anything more than that in case his dad didn’t know that he was a contract collector. That’d probably create even more problems for the poor fella. The beetle can hear the toon from the other end let out a deep sigh.
The bartender finished up with the bandages and wiped away the last of the blood stains. It was the least he could do. After all, he had encouraged the boy to fight Big Boss. Which just seems rather foolish now… SLAM! His gaze shoots over to the door and it lands on a tall pig with an eyepatch standing at the entrance, who he assumes was the toon on the phone a couple minutes ago. Porkrind’s gaze swept through the whole bar until his eyes landed on two small brown shoes and familiar red shorts laying down at one of the tables. He rushed to the cup’s side instantly.
“Cup…” The pig said as he took in the teen’s appearance. He gently caressed his face.
“I did all I could to clean his wounds. But his head is kind of um…” He sighed then took out a small bag from his pocket. “This was all I could gather from the scene. ‘Hope it helps.” He handed the other toon the bag and Porkrind gladly accepted it, storing it away in his pocket.
“Thanks.” Is all he simply said as he very gently picked up Cuphead into his arms and promptly left the bar without another word.
The bartender stood there silently praying that the cup wouldn't come back, for his own sake. He then sighed, “I hate bar fight Friday…”
—
The door to the bar creaked open and the bartender glared at the wall. Ugh, he was just about to close… And to also put salt onto the wound, he’d finally managed to convince Big Boss to leave for the night so he could do repairs. The beetle turned to look at the door but freezed, his face paling.
The Ink Demon…
The demon whistled as he took in damage while he slowly walked further inside the bar. He then spotted the bartender behind the counter and approached him, to which the beetle visibly tensed up at. Bendy grinned and took a seat at one of the bar stools while leaning his arm on the counter.
“So… What exactly happened here?” He asked simply, his gaze lingering on the huge hole in the floor. The bartender gulped and began to prepare a drink to calm his nerves, but his movements were shaky and a bit sloppy.
“Uhm, a fight.” Bendy hummed thoughtfully and leaned his face on his hand, looking bored or… sad? No, that’s not… that’s not right. He looks more like he’s disappointed?
“Ah. I just missed it, huh?” The beetle nodded and finished up the drink, sliding it over to the demon. Bendy eyed the cup for a moment. He picked it up, swishing it around then took a sip. He hummed again, then stood up and the bartender flinched. The Ink Demon walked over to the hole to inspect it. “I’m assuming it was a fight between a cup and a dog?” He questioned idly as he grabbed a little porcelain shard from the rest of the debris and inspected it closely.
“Y-Yes…” How does he know that? Does this guy somehow know the cup? “That is correct.” The demon stood up, placing the shard in his suit pocket then turned to sit back at the bar stool.
“Hmm, it's a shame I missed out on all the fun… But you may be able to help me entertain myself.” He grinned darkly, and the beetle gulped nervously, clutching a knife behind his back that he’d nabbed while the demon wasn’t looking. Bendy leaned closer to the beetle. “Tell me where that cup went, and I might just spare your life.”