Archive of Our Own ^beta

Chapter Text

Cuphead jumps forward, rolling low to the sleek wooden ground of the stage, then ducks as a thin razor-sharp blade swooshes above his head, slightly grazing his straw. He jumps up onto a floating cloud platform just as his opponent — a nutcracker — charges forward with a thin sword.

He is so close this time to actually getting their contract. This nutcracker isn’t even the main boss, he’s just one of the goons of the actual debtor, which is an annoying porcelain ballerina. Cuphead rolls his eyes at the thought of her. But he can’t take his focus off of the fight right now, not when he’s so close to the last phase. Cuphead fires at the nutcracker, ever slowly chipping away at his sturdy wood.

Just as the nutcracker falls to the ground in defeat while waving a white flag, strings come down from the roof and attach and tie themselves onto Cuphead’s arms tightly. The red cup groans in discomfort. This is the part he’s having trouble with… These strings limit his movement and sometimes he isn’t even in control, letting the ballerina get a few good hits in.

“OHOHOHOHOHO!” Cuphead grimaces as a shiny porcelain ballerina gracefully descends from above the roof, a devilish smile adorning her sleek white face. She lands on the floor but doesn’t give the cup teen a moment to prepare for her attack. Here we go again…

…

Cuphead tsks painfully while dabbing a damp cloth on his bruised arm. Rina really didn’t hold back this time around… He hates that ballerina so much. He’ll try to get her contact some other time, he can’t handle her cruel taunting today, or ever. Cuphead finishes up by wrapping a bandage around his already severely cracked arm. That’ll hold the pieces together until they fully heal.

Cuphead stands to his feet from the log he was sitting on and treks into the forest. This is one of the more peaceful areas on this island, where Cuphead could finally catch a break and bandage up from a fight. He’d been going at it all day ever since he got here two days ago. Cuphead reaches into his pants pocket, pulling out two slightly torn contracts. So far though, he’s been unsuccessful in collecting these new debtors' contracts, only racking up two out of the twenty-eight he needs to collect before the month ends.

The teen puts the contracts back into his pocket and kicks a rock on the small dirt trail while grumbling frustrated to himself. The Devil might’ve warned the debtors that he was coming. That bastard. Oh well. He’ll defeat them all the same, just like he did a few years ago back in Inkwell Isles.

Cuphead grimaces at the mention of his home, stopping in his tracks momentarily. He shoves his hands into his pockets and continues on the dirt trail, glaring at the ground.

The trees and bushes open up into a clearing where a little village is. This is where Cuphead would stock up on supplies and get some well deserved sleep occasionally (if he had any money to spare for a night at the motel). Cuphead approaches the quaint village, walking straight to Porkrind’s Emporium. Seriously though, Cuphead thinks to himself, it’s like this guy’s shop is everywhere. How does he do it?

“Damn, ya look like shit, Cup.” Cuphead shoots the pig a glare, but the older isn’t at all intimidated by the teen. “Healing potions again?” Cuphead nods. “Yer’ quiet today, bad fight?” The pig turns his back to grab two healing potions, he then turns back to the counter and places them on it, opening his hand for the coins. Cuphead doesn't give Porkrind an answer as he hands the pig four gold coins. The red cup gives the older a nod before promptly leaving. “Tch, teenagers.”

It’s not like he hates Porkrind, it’s just that it’s none of his business. Also, since when did that guy care? Cuphead scoffs to himself.

Since he just purchased two healing potions for the price of four coins, Cuphead can’t exactly afford a room at the motel. Dammit… But surviving is better than comfortability so he definitely made the right decision. But, if only he had Mugm-… No, actually, he’d rather not finish that thought. He can handle himself. He doesn’t need someone else to make sure he doesn’t do anything stupid. Not anymore. He’s sixteen now and that means he’s mature and serious.

But anyway, the game plan for finding a place to sleep — he has no idea. Actually, he does have one but it doesn’t sound too fun… Cuphead thinks back on to last night when he camped out in the forest. He’d been abruptly woken up to bugs in his head, crawling in there for a midnight drink. Eugh… He shivers just thinking of it. But does he really have a choice? Cuphead sighs, but just as he’s about to go back into the forest…

“Hey, you brat, if ya needed a place to stay ya could’a just asked.” Cuphead turns to see Porkrind leaning at the door of his shop with his arms crossed. The teen thinks to himself for a moment, thinking it over. “Get over here before I change my mind.” Cuphead quickly nods and rushes to the shop, following the pig inside. “I’ve got some sleeping bags in the back, don’t get ‘em dirty.” The teen nods and heads toward the back of the shop.

“… Thanks, Porkrind.” Cuphead disappears into the back of the shop before the older can grumble out a ‘you’re welcome’.

Cuphead takes out a sleeping bag and lays it down onto the floorboards. It is surprisingly cushiony, which is a plus. The teen lets out a small grin, sliding in the sleeping bag he closes his eyes and rests his head against the soft pillow. Maybe Porkrind does care after all. The red cup drifts off to sleep fairly quickly, giving into exhaustion from today’s battles.

—

Cuphead is up and early in the morning, he doesn’t wanna burden Porkrind any further than he already has so he leaves before the pig notices and goes on to battle the next debtor.

Cuphead stops at the gate of a big mansion, looking down at his map to make sure that this was the right place. He looks back up and stuffs the map into his pocket then enters.

…

Surprisingly, that fight with the spooky ghosts was easier than Cuphead had originally anticipated. It was just like when he freed Ms. Chalice at the Mausoleums all those years back, he just had to perry them. And now he’s got three contracts! Not bad.

Cuphead travels to the next one, which is a four group of hedgehog thieves. Eh, should be easy ‘nuff.

… Is what an IDIOT would think.

Cuphead plucks out a big quill from his hip, his eyes watering as he did so. He wipes his eyes with his sleeve and heaves in a breath to prepare himself to pluck out another quill from his arm. Thankfully, he found most of the pieces from his porcelain, so these wounds will heal in no time.

Those hedgehogs do not go down easily…

He was so close to defeating them, though! Once he heals up he’ll get right back into battle and get those damn hedgehog’s contracts. It’s personal now. Cuphead downs his healing potion, his wounds instantly healing up and his body feeling like brand new. The teen stands up and walks back into the den in the ground.

“Hey, guys! The little teacup wants some more of our fury!” The blue hedgehog says and the others laugh along with him. Cuphead’s eye twitches at the stupid nickname.

“Let’s show him that we won’t go down so easy!” The pink one adds.

“C’mon, fight us!” The white one says after her.

“I hate you guys.” The black one says.

They all corner Cuphead, quills in hand. But this time Cuphead knows their dirty tricks and goes for the white hedgehog, tackling him to the ground harshly. The pink hedgehog immediately goes to help but Cuphead uses the white one as a shield.

“H-Hey! Let me go! That’s no fair!” Cuphead smirks and throws him at the pink hedgehog. Knocking them both out cold on impact.

The blue hedgehog charges at Cuphead while rolled up in a ball, knocking Cuphead into the wall. But he knows better than to sit around for too long. Cuphead ducks down when he sees the black one charge at him with a quill like a sword, but the quill gets stuck in the wall. Cuphead kicks the black one in the stomach as hard as he can while they’re distracted and they fall to their knees clutching their stomach tightly. Cuphead grabs him by the scuff and twirls around and around and around, picking up speed like a mini tornado he throws the black hedgehog to the pile with the white and pink hedgehogs.

Cuphead huffs, trying to catch his breath before finishing off the leader of their small group, said leader is the blue hedgehog that is currently cowering in fear before the red cup. Cuphead heaves in a few ragged breaths then goes into a fighting stance, his eyes filled with determination.

“You-!!” The blue hedgehog charges at Cuphead with his special move that he calls a ‘spin dash’ but Cuphead stays in place and catches the speedy blue spiked ball heading his way. It burns, it hurts, but this is the only way to defeat this last one. Cuphead groans, the dash pushing him back but he stays grounded, digging his feet in the soil he pushes back. Push back. Cuphead‘s hands start to bleed through the yellow fabric of his gloves. Don’t stop. His knees feel weak. But he’s stronger. Cuphead tightens his grip on the spiked ball and he pushes it down into the soil. It digs into the ground and when the hedgehog stops spinning, he’s stuck.

Why isn’t Cuphead shooting at them? Oh, well, he learned the hard way that his gun doesn’t work on them because of their armour (quills), so now he’s resorted to dirty tricks.

Cuphead backs away and stares at his bloody hands. He just sucks in a sharp breath and gulps. He lets his hand out in front of the hedgehog stuck in the dirt. The blue one just growls, but he knows he’s lost this fight so he just gives in.

“Just take it!” Cuphead smirks and reaches into the hedgehog’s quills carefully so as to not scratch up his hands even more than they already are. He takes the contract and stuffs it into his pants pocket.

“This teacup-“ Cuphead huffs, “can fight like a *%#$@“ He huffs again, “jerk.” Cuphead walks away, leaving the blue hedgehog in the ground as payback for calling him a teacup and badly injuring his hands.

—

“Geez, kid. Ya’ really ruined yer’ damn hands fer’ a couple of petty thieves?” Cuphead glares at Porkrind as he finishes drinking a healing potion.

“They had contracts. They weren’t just any petty thieves.”

“Still, they should’a been nothin’ to ya’ with those weird powers of yers.” Porkrind crosses his arms, giving what Cuphead would only recognize as a look of disappointment mixed with worry. Cuphead waved him off.

“Eh, I ain’t too worried ‘bout it. ‘Sides, it didn’t even work on ‘em. Their stupid dumb quills protected ‘em from the blasts.” Cuphead grumbled as he bandaged up his hands.

“You really have no self preservation…”

“It keeps me alive.” Cuphead says and Porkrind’s face contorts into one of worry. Cuphead rolls his eyes, tightening the bandages on his palms to keep himself distracted from the older man’s concerned look in his eyes.

“It’ll be the thing to get you dead.” Cuphead pauses and he looks up, but the pig has his back turned, washing some bottles in a bucket. Cuphead looks off to the side. No, it won’t, Cuphead thinks to himself and his brows furrow. He doesn’t know what he’s talking about. “Well, get goin’ to another debtor.” Porkrind sighs, “I’ve got healin’ potions galore fer’ you here when ya get back.” Cuphead nods even though the other can’t see him and he hops off of the bar stool and exits the tiny shop.

It went on like that for the whole day and then the days after that. Cuphead collecting more contracts one by one. Some of the bosses were more difficult than others, and then the next is easier than the rest. He’s still having trouble with Rina Balleta… She plays dirty, okay? More so than Cuphead himself when he’s in a tough spot.

But he’s been able to successfully rack up a total of seven whole contracts in that time! He’s going to clear this island’s debtors in no time. And then he’ll finally be able to fix everything.

However… there’s one thing that just wasn’t adding up… Some of the debtors he didn’t even beat up were already defeated. Which was… odd. To say the least. Cuphead is supposed to be the only debt collector here from what he knows. Did the Devil send out another? Why would he do that when he knows Cuphead needs all twenty-eight to get his end of their deal?

It’s almost the end of the day, and the sun is already starting to set. Every debtor he comes across has already been defeated. This crab better not have gotten a visit from that damn thief.

Cuphead walks up to a defeated gigantic crab stuck on his side in the sand with his little crab goons laying down beside him. Cuphead clenches his fist tightly, his cup fuming until he finally bursts into a rageful fit of anger. He kicks a seashell into the ocean then picks up a tiny crab and throws it into the water as well. But then immediately regretting it because that poor crab didn’t deserve that. He slumps down to the sand with his elbows on his knees and his hand cupping his face.

“Are you angry that you didn’t get my contract first?” Cuphead doesn’t answer, he just stays glaring at the sand with his head steaming. “That demon boy took it if you’re wondering. We debtors hadn’t anticipated another debt collector coming to help you.” Cuphead snapped his head up at that.

“Help me? No, it’s the opposite! I need all those contracts! All twenty-eight! And he’s stealing them!” Cuphead stands up while shouting at the gigantic crab. But the crab doesn’t react which only makes Cuphead fume even more. “Say something!” The crab just stares at the teen silently. Cuphead grits his teeth and he just gives up and starts walking away from the crab.

“You’d better be careful when facing that demon, he’s a sneaky one.” Cuphead continues to walk away without as much as a second glance at the giant creature.

He’ll keep searching, even if it’s the last thing he’ll do. Porkrind won’t be too happy that Cuphead is going yet another night without rest, but that pig isn’t his dad. Cuphead doesn’t have anyone, he can do what he wants.

—

Cuphead approaches a flower field where The Tulip Trio was supposed to be, but there they lay on the grass, defeated, heaving and huffing with their petals scorched and burned. Hm. The teen approaches the flowers to which they flinch and cower beneath him when they see the angry scowl on his face upon seeing them.

“We don’t have it!”

“Yeah! We really don’t!”

“The other guy already took it!”

Cuphead furrows his brows. “The other guy?” He asks, stomping on one of the triplet’s leaves and they shriek under his intimidating glare.

“The demon boy!”

“The one who fights with blue flames!”

“The Ink Demon!”

Cuphead lifts his foot off of their leaf, the beaten tulips sighing in relief when he does so. The Ink Demon… Cuphead puts a hand to his mouth as he thinks to himself. He doesn’t know if he wants to face this guy who’s stealing his contracts. No matter how mad he may be. He doesn’t exactly have a good track record when it comes to demons.

“Thank you.” He says finally then he departs into the forest from where he came from.

“You’re most welcome!”

“You’d better show that no-good demon what’s what!”

“You have to! Oh, you just have to!”

Cuphead rolls his eyes. They don’t have to tell him twice. He’ll find that bastard stealing his contracts.

But, for right now, he so desperately needs to rest. Walking all day around the whole island without sleeping for days is really taking its toll on his body, and he’s not sure about how long he can stay awake. The cup walks through the forest, fighting to stay awake, his eyes fluttering close every second or so but he wills them to stay open for a little longer.

Ah, hell. Whatever. He’ll just take a nap right here. No one is around. Cuphead lowers his body down to the lush grass and rests his back against a tree, his legs finally giving out to exhaustion. The teen lets out a laboured sigh and his shoulders release their tension. A little nap wouldn’t hurt… Just for… for… a few… minutes… Cuphead’s eyes flutter close and in a second he’s off in dreamland.

—

A demon with a sharp tail and horns emerges from some thick bushes, stepping over them carefully. He looks back from where he had come from and his expression sours. He looks down at the contract in his hand and his gaze softens. The demon clenches the contract tightly in his fist, stuffing it into his suit and going on his merry way, probably to deal with another debtor.

Another one down, only a dozen many more to go. He'd honestly lost count at this point.

It was strange though, some of the debtors had already been dealt with. No one but him should be the only contract collector on this island. The demon hummed in thought. Or perhaps someone else — another debt collector like him — was here unbeknownst to him.

As the demon walked along, he observes the lavish green forestry all around him. Tree’s shading him from the warm sun rays from above, it's comforting light seeping through the tree’s leaves. The grass and moss like a soft carpet with each step he took. It’s peaceful, calming. Quiet with the exception of the birds chirping and regular forest noises. This type of scenery never gets old.

The demon passes by a thick tree, looking to his left, he sees someone laying down beside a tree. He keeps walking- WAIT… He stops dead in his tracks. Then he slowly walks backwards to take another look. The demon hides himself behind the thick tree and peeks an eye out, his tail swishing lightly behind him with keen interest.

A cup boy who looks to be about his age is sitting down leaning his back against a tree while resting peacefully. He looks… exhausted. And pretty beaten up, If his rugged clothes and bruised up face were anything to go by. They’re stained with mud and grum, tethered with small rips and holes in his baggy black sweater and red shorts.

The demon cocks his head to the side, curious of this strange yet intriguing cup boy. Their guard is down, and they could easily get jumped by a debtor in the area if he wasn’t careful.

The demon emerges from his hiding spot and quietly approaches the cup, being careful at watching where he steps. He kneels down to take a closer look at him. Now that was a view to behold, he thought to himself. The boy was pretty attractive, one might even say cute or handsome. The demon watches their steady breathing, chest rising up and down in a slow and steady motion. Now taking a closer look he can see visible dark circles under the other’s eyes.

Is he staring too much and for too long?

…

This is probably really weird to see in an outsider perspective. But the demon can’t really find it in himself to care.

The boy grumbles, furrowing his eyebrows, he yawns, putting a hand to his mouth and slowly blinking as he stirs awake.

Oh no, this isn’t good.

He could run away right now… but this boy has piqued his interest in a way no one has before in a long while. So, he decides to stay still as the other wakes up. The red cup rubs the tiredness from his eyes and sits up straight, then he freezes, tensing right up as soon as he sees the demon in front of him and waaay too close for comfort. The demon grins.

“Mornin’.” The boy backs up into the tree as if the other was going to attack him. Ah, it’s because he’s a demon, right? Made sense, that’s usually the response the demon got whenever someone saw him. Or that reaction was because he is uncomfortably close. That too. Perchance.

The boy stays completely still, not daring to move even an inch. He shifts a bit and the demon notices some familiar looking yellowed paper peeking out from their pants pockets. Contracts. Ohh… It’s all so clear now. This is that Cuphead kid the other debtors warned the demon about when he arrived on this island.

“Wh-who’re you?” Cuphead aimed his finger like a gun at the demon. A vibrant blue energy radiating from his fingertip. The demon’s pie-cut eyes widen a bit at that. Things just got even more interesting! The demon grins widely and the red cup glares at him.

“Ya’ don’t know me? Now, that’s interestin’. I’m pretty well known ‘round these parts.” The demon responded casually, resting his hand against the side of his face, taking no mind at the gun currently being pointed at his face.

“Answer the question.” The other teen’s serious gaze sharpens and the blue glow from his fingertip shines even brighter, the raw energy crackling quietly almost like thunder. Fascinating!

“Now, now. Don’t get so feisty, sunshine. I'll tell ya, alright? I’m Bendy. The Ink Demon as some like to call me.” The demon toon offered his hand out for a handshake, Cuphead tenses up, staying in place like a statue. “Tough crowd, huh?” Bendy retracts his hand back.

Then, Cuphead’s eyes widens at the title ‘The Ink Demon’. This is the guy who’s been stealing his contracts! The one who the tulips and crab were talking about! But suddenly any emotion is quickly swept away from his face as he processes what the demon had just called him.

“…Sunshine??” Cuphead gives the intruder a puzzled and unamused look, and if you really looked close enough, you could see that he is slightly blushing. Aw, how cute, Bendy thinks to himself, grinning.

Bendy hums. “Yep! ‘Cause yer just an absolute ray of sunshine.” Cuphead gives a ‘really?’ look at the other. However, the demon’s grin just gets wider at that. This is more entertaining than it probably should be. Bendy giggles and Cuphead seems like he’s resisting the urge to roll his eyes at the teasing joke.

“Why are you… here?? No, wait, lemme rephrase that. Why were you watchin’ me sleep?” Bendy stands up to his feet and Cuphead tenses up again, the energy from his finger going ablaze once more.

“Relax, toots. I’m not gonna hurt cha’.” Cuphead doesn’t ease up. He doesn’t trust him. “I only needed this. Nothing more, nothing less.” Bendy lifts his arm with a contract in hand. Cuphead stares for a second confused, then his face contorts into one of shock and he frantically searches his pockets. Empty… He looks back up and basically gives the demon toon a death glare.

“If looks could kill, haha!” Bendy jokes playfully. Cuphead stays silent.

“Give that back.” He cautiously stands up, still aiming his finger at the offending demon. Bendy puts his hands up, but doesn’t look at all threatened by the other teen.

“I don’t think I will, thank you.” He puts the contract in his suit’s pocket then melts into a puddle of ink into the forest floor. Cuphead stands there while staring bewildered at the ink puddle before him.

“Over here!” Cuphead snaps his head around, spotting the ink demon sitting on a branch from the tree he was resting against earlier. His gaze hardens and he fires at the demon, but the toon sinks into a puddle of ink again. Cuphead tsks, whipping his head around to try to figure out the other’s next move. He feels a tap on his shoulder from behind and spins around to see Bendy way too uncomfortably close for his liking. Again. Seriously what is with this guy?! Cuphead’s face grows warm and Bendy to barks out a laugh at that.

“Just wanted ta’ say goodbye before I go! It was nice meeting ya, Cuphead. I’m sure we’ll be seein’ each other again very soon.” Bendy gently takes hold of the red cup’s hand and kisses it. That did it for the hotheaded cup and now his head is boiling over with little bubbles dripping down his head, too flustered to even utter a word as he stares at the Ink Demon baffled. Bendy just grins a big toothy smile then sinks into the ground for the last time. Disappearing in a second.

Cuphead stands there completely still. His head dizzy and swirling by how hot it was now.

The red cup holds the hand Bendy kissed and stares at it. His face getting redder and redder by the second as he replays the scene in his head over and over again. He glares at his hand and huffs. Stupid emotions… They made him lose a damn contract! Ugh, this is so stupid… HE is so stupid! How could he let that even happen in the first place??!

Cuphead shakes his head, trying to cool it off and trying to also push away any embarrassing thought that invades his brain. He wasn’t thinking straight. Okay, he’s definitely going to kill that guy. He doesn’t care if that douchbag isn’t on the list, when Cups gets his hands on him…

Cuphead grumbles, checking the contracts to see which one that damn Ink Demon had stolen from him.

“That debtor isn’t even a top grade… So why…?” He stands there puzzled. Cuphead could only wonder what that strange demon’s motives are.

Yeah, he’s definitely not sleeping outside again. He’s learned his lesson.

—

“Ya look a li’l out of it, Cup. What’s wrong?” Porkrind asks as he cleans a glass beer cup with a rag. Cuphead blinks and looks up at the pig when he’s taken out of his troubling thoughts. The pig raises an eyebrow as if asking his question again. Cuphead’s mind wanders to the… encounter.. he had with a certain demon a few hours ago. His face flushes a bright red and he swivels the bar stool around to hide his blushing face.

“N-nothing. It’s none of yer’ business.” Cuphead folds his arms across his chest. Porkrind gives the cup a skeptical look, but he doesn’t press the issue any further. He then mutters something under his breath about teenagers and how they’re complicated and then walks to the back of the shop.

…

Bendy walks towards the three tulips, his face emotionless and unmoving, so very different from his usual whimsical and teasing personality. He harshly stomps on one of the triplet’s petals and they shriek in pain and begin to cry.

“So…” He starts, a grin growing on his face as he glares down at the flowers, “Tell me more about this ‘Cuphead’ guy.”

Chapter Text

Cuphead tosses and turns, trying so desperately to lull himself to sleep but it’s useless. With all of Porkrind’s snoring and his mind running a mile a minute, there’s no way he can get a good night’s rest. So, the teen sits up from his sleeping bag and carefully crawls out, being sure to stay quiet so as to not wake up the grumpy pig from his slumber. Cuphead grabs his shoes from the side of his sleeping bag and slips them on, then he leaves the small shop as quietly as he can.

He just needs to clear his head, he’ll be back in a bit to take a quick nap to replenish his energy.

“An’ where do you think yer’ goin’?” Cuphead stops dead in his tracks, frozen. After a second he then turns to face the pig standing at the door of his shop with his usual arms crossed and an unimpressed look on his face.

“I’m just goin’ on a walk.” Cuphead replies, but he supposes Porkrind didn’t like his tone because after he said that he got a mean glare.

“No yer’ not. Get back in ‘ere.” Cuphead looked off to the side and rolled his eyes, but the teen does as he’s told anyway and drags himself back inside the tiny shop. He’s seen Porkrind angrier than this before, and it ain’t pretty. Porkrind points at the back room as a silent demand telling Cuphead to go back to bed.

He knows that the older toon is only looking out for him since Cuphead lost everyone he loves in the span of one night, but he doesn’t have to act like his dang dad.

Cuphead takes off his shoes before tucking himself back into his sleeping bag. Great, now he’s alone with his thoughts again. But maybe he would’ve been either way, he just didn’t want Porkrind to see him when he’s most vulnerable… That’d be bad for his ego.

Porkrind walks into the back room, sitting down at his own sleeping bag. The pig lets out a grumbly sigh and Cuphead has the itching feeling that he’s about to have a serious talk with him.

“Alright, Cup. What’s the matter?”

“Nothing. I’m alright.”

“I don’t believe that. Tell me ‘r else I won’t stop buggin’ you ‘bout it.” Cuphead groans quietly and he proceeds to turn his back on the pig and pull the blanket over his head.

Porkrind sighs again and rubs the back of his neck almost sheepishly. “Okay, I get it. ‘M sorry for bein’ nosy.” Cuphead stays quiet, Porkrind continues, “But you bein’ all… sad ‘n shit is… it’s worryin’ me.” Cuphead slowly pulls the blanket down a bit, just enough so that his eyes are peeking out and he listens intently. “So what I’m tryna’ say is… ugh, I’m tryna’ comfort you dammit.” Cuphead snickers softly and comes out from under the blanket and faces the older toon.

“Yer’ really bad at this.” He jokes with a small grin. Porkrind rolls his eyes and huffs out through his nose.

“Yeah, yeah, ya’ don’t need’a rub it in.” Cuphead chuckles dryly, Porkrind manages a smile at that. “But seriously, kid. What’s got ya’ all pent up?” Cuphead sighs heavily and holds his face in his hands.

“…Everything. I just- I’m such an idiot…”

Porkrind gets up from his spot across from Cuphead and goes to sit down beside the teenager. He pats his back lightly, and a bit awkwardly, but it doesn’t go unappreciated by the red cup.

“I…” Cuphead starts to fidget with the hem of his yellow gloves, trying to find the right words. “I was bein’ dumb an’ sold off my soul at the Dev’s casino. Again. And somehow I sold off Mugsy’s soul as well. But I just wanted to help! I- I really did..! I needed the money to help Elder Kettle with his illness…” The teen tries to compose himself, already feeling himself getting worked up just talking about the mess he’d made.

Porkrind hums thoughtfully, Cuphead continues, his voice getting a bit quieter and quieter the more he confides in the pig. He tries to hide the way his eyes start to swell and the way his voice croaks ever slightly the more he talks.

“When I had to fight all of those debtors back in the isles… I- I dunno… I wasn’t the same, I guess… I started havin’ nightmares about the Devil and fight’n my friends… And now I’m- I’m going through it all over again!” Cuphead shudders, fighting back the tears that threatened to spill. You can’t cry, you can’t cry, he repeated to himself in his head.

“Sounds rough. How’ve you been handling it?” Porkrind doesn’t point out how Cuphead turned away from him to compose himself.

The red cup sniffles and wipes his nose with his sleeve. “I dunno… I’ve just kinda been- tryna’ not think ‘bout it and focus on getting contracts as fast as I can.” The pig hums again.

“Yeah, ya’ see, stop doin’ that, none of that anymore. Look, I know I’m no expert but I know enough to understand that ignorin’ serious issues like that isn’t the best way to solve ‘em.”

“Okay, wise guy. What should I do then?” Porkrind flicks Cuphead’s forehead. “AH- hey!”

“Don’t give me sass, kid.” Cuphead sticks his tongue out, blowing a raspberry. The older just rolls his eyes and lightly shoves him, to which earns a chuckle from the teen. He knows Porkrind isn’t actually mad or annoyed at him, that endeared grin on the pig’s face tells it all.

“It’s all ‘bout what works fer’ you. An’ clearly we’re two different people, so whatever I do might not work out fer’ you.” Cuphead nods, not really getting it but he’s willing to listen in order to understand the best he can. “Hmm… ‘kay, how ‘bout this? You try ta’ confront yer’ feelings and trauma, understand ‘em and accept that, yeah, it sucked, but what matters is how you’ll react to it. Will ya’ keep sulking like a baby or do something ‘bout it?”

Cuphead ponders on this, looking down at his hands. His mouth thins into a straight line and his brows furrowed as he thinks long and hard about the advice. It seems a bit impossible, Cuphead never was great at confronting his emotions, so this seemed like a rather daunting and intimidating task to overcome.

The pig pats the teen’s head, effectively breaking him out of his thoughts. “You can think ‘bout it in the morning. Go to bed, yer’ gonna need it.” Porkrind stands up, doing that old man groan that old guys always seem to do whenever they sit up and he walks over to his sleeping bag and lays down. Cuphead does the same, fluffing out his pillow before resting his head down.

It’s a lot to take in, but tomorrow is another day, so he’ll have plenty of time to think about it. Porkrind is right though, he needs to get as much rest as he can so he’ll be able to take on those debtors.

It isn’t long before Cuphead’s eyes are fluttering close and sleep pulls him in it’s comforting embrace. He feels like a weight has been lifted off of his shoulders, and he can finally be at peace, if only for a little while.

—

The Devil said Cuphead had a month to collect all of the contracts, which was awfully generous of him considering the last time Cups worked for him he’d only given him a day. Cuphead wasn’t complaining though. He’s already collected six contracts out of the twenty-eight needed, he’d lost the seventh one from that annoying demon (Bendy he said his name was?) the other day, and he plans on getting it back and figuring out WHY they are stealing the other ones and if he’s another debt collector like him. Which would be a big problem for competition.

Walking on a dirt trail beside some green pastures with trees to his right shading him from the sun, Cuphead looks over his list, his eyes quickly skimming through all the names. Already defeated that guy… those guys too… her as well… He’s got six contracts right now out of all twenty-eight so that means he just needs twenty-two more. But if you count the ones that the stupid Ink Demon already took then that would be… sixteen. Good, okay so that demon has only collected six so far, which was already pretty bad but it could be worse. Cuphead will just have to steal them back from him. He doesn’t know how strong this guy is but he’ll take him on anyway, he’s fought the literal Devil (and won, mind you), so surely some imp or whatever should be a walk in the park.

Cuphead spots a crow up ahead on the old wood fence beside the dirt trail. Its eyes follow Cuphead as he approaches. The teen then stops in front of it, eyeing it curiously while tilting his head to the side, with the crow mimicking his movements. Cuphead reaches into his sweater’s pocket, fishing out some sunflower seeds and carefully offering them to the ebony bird. The crow looks down at the seeds then at Cuphead with interest. After a moment it eats the offering from the teen’s hand.

He didn’t think it would actually eat straight from his hand, but he’s a big animal lover so he doesn’t mind at all and he lets out a small smile. Once the crow is finished eating the sunflower seeds it caws at the red cup and flies away into the forest, Cuphead watching intently as it does so.

“Didn’t really take ya’ for someone who likes crows.” Cuphead whips his body around to see the ever annoying Ink Demon behind him wearing that stupid grin on his face. Cuphead glares daggers at the other and ignites a blue flame on his fingertip, just in case the other tries anything. “Whoa, whoa, calm down, sweet cakes. I only wanna talk.” The demon puts his hands up as a sign he was friendly. For now. Cuphead gives a look to Bendy at the strangely affectionate nickname, who in turn just grins wider at the red cup’s expression.

Cuphead untenses ever slightly, furrowing his brows he studies the demon for any signs of deceit, but he can’t really tell anyways so he just opts to hear what the other has to say for now.

“What is it you wanna talk about?” Cuphead asks finally.

“I just wanted to get some things straight that’ve been buggin’ me ever since I heard about a cup stealin’ my contracts.” The demon explains and Cuphead frowns at that.

“YOUR contracts?? No, no, those are MINE. I dunno know who ya’ think you are but I need all those damn contracts ta’ get rid of my own debt.” Bendy puts a hand to his mouth, thinking silently with his tail swishing lazily behind him.

“Wait, so… the Devil sent ya’ here too?” Cuphead hesitantly nods, but then it clicks, his eyes going wide. “Well, that sure is weird. You said ya’ needed all of the contracts but ya’ see, I need all of ‘em too.” Cuphead shifts his gaze down at the rocky ground, trying to wrap his mind around this- predicament that they’re both in.

“Only one of us can get them all.” He says after a quiet moment of silence and meets the Ink Demon’s gaze.

“And so it seems. Welp, I reallyy need those contracts so I’ll give you the chance to hand them over peacefully,” Bendy grins and outstretches his hand for the papers but Cuphead glares at him, going into a defensive stance.

“Last chance, Cupsy.” Something inside Cuphead snaps upon hearing that absolutely idiotic nickname and the next thing he knows he’s rapidly firing his finger gun at the sly demon who in turn just dodges all the bullets with swift ease. Bendy is light on his feet and Cuphead just can’t seem to land a hit and it angers him to no end. Then in the blink of an eye Bendy has disappeared from sight.

“Look-“ Cuphead shrieks and shoots at the demon who appeared beside him from an ink puddle below, but the bullet goes right through Bendy and the colour from Cuphead’s face drains. The demon merely snickers and melts into a mush of ink before Cuphead’s very eyes then TWO Bendy’s appear beside Cuphead.

“You can’t shoot ink, silly!” Cuphead punches one of the clones and they too melt, little bits of the black liquid stains his glove. It’s a little inconvenience really, but it still does the job at getting him angrier by the second. “I really like you, cupface,” Cuphead growls in frustration and punches the other clone, it splatters like a tiny ink explosion, the black liquid staining his sweater. OH JUST GREAT! How’s he gonna wash that out?!

Cuphead is clearly outnumbered and at a disadvantage, who knows what other tricks this demon has up his sleeve? Heck, with an ability like that he can probably do a bunch of different terrible things! And to top it all off it seems like his powers don’t even work on the guy!

Cuphead darts his eyes around, trying to search for the real Bendy.

“We can come to a compromise, yeah? You give me the contracts and I let you go alive, how ‘bout that?” Cuphead twists around and there the demon stands with his stupid smile and his hand outstretched once more. Cuphead stares at the other teen’s hand then his face then his hand again, contemplating. No, he can’t accept a deal like that! He has his brother Mugman and Elder Kettle to save! Cuphead glares at the other and slaps his hand away.

“No.” He simply says, but it for some reason just makes the other’s grin grow wider. As if this was all just some game. “You may have your reasons for dealing with the Devil, but I also have mine.” Bendy stares for a second, quiet. Then he snickers. And all Cuphead can think is how horrible that sound is.

“Okay, then so be it. But I'll be taking this one fer’ now. Try taking it back if ya can.” Bendy waves a contract in his hand and Cuphead takes a moment to process but then it finally does and in the next moment he’s frantically searching all of his pockets. Cuphead looks up glaring at the sneaky demon and Bendy only grins a cheeky smile before disappearing into a puddle of ink. Cuphead is left there fuming with his fists clenched and his head boiling.

He really hates that demon.

—

Bendy jumps up from an inky puddle in the grassy forest ground. He dusts himself off a bit then climbs up a decently sized tree, his movements resembling that of a cat. He leans his back against the trunk and crosses his legs onto each other with his arms resting on the back of his head.

He’s having way too much fun teasing that cup, isn’t he? The way Cuphead gets easily angered is truly a funny sight to the demon, and just thinking of the other teen’s reactions at the nicknames Bendy calls him makes the Ink Demon let out a satisfied grin.

Okay, okay, that’s enough fun though. He needs to focus on business. Bendy sits up straight and takes out the yellowed papers from his suit If his math is correct, (it rarely ever is) he currently has seven contracts, meaning that Cuphead now has five. Bendy thinks back on his visit with the hot headed cup. He honestly could have taken all of the contracts easily. But he didn’t. Hm. No, no, it doesn't mean anything. He’s just been super bored lately and Cuphead just happened to be the most interesting thing to cure the demon’s boredom.

Bendy is pulled away from his thoughts when he senses something coming. It isn’t anything dangerous, no, it’s actually a friendly crow. Bendy holds out his arm and the crow lands on it and caws. Bendy giggles and pets the crow gently on its tiny head.

“Got anythin’ good fer me, buddy?” The crow caws and Bendy’s grin grows wider. “Really?” It caws again. “Alright, alright. Thanks for yer service.” The crow bows its head politely then proceeds to melt into a jumble of ink, to which Bendy absorbs through the fabric of his clothes. “Maybe fooling around for a bit wouldn’t hurt, right? I’ve got a whole dang month to get these contracts. I’ve got time.” The Ink demon says to himself then jumps off of the tree and walks off through the woods.

Chapter Text

Cuphead honestly feels a bit shaken up from the encounter with the inky demon from earlier, but he’s not about to show it. Hell, that’d probably boost that bastard’s ego and make him smile that dumb smile again. Cuphead huffs annoyed. He can’t think of that jerk right now, he needs to focus on getting more contracts than him. It’s a race now to get more than the other, and Cuphead isn’t about to lose so easily. 

Cuphead approaches a shady bar in the village over from where he usually stays at. He enters and takes a quick glance around, there doesn’t seem to be much customers, maybe like three or four max lounging around with booze in hand and the bartender, who is a beetle toon, cleaning some glass cups. Cuphead walks to the counter and takes a seat at the stools that are noticeably taller than he is. There’s some quiet jazz that three performers are playing in the background from the stage, making the whole setting quite cozy. But Cuphead isn’t here to have a drink and relax, he’s here for a mafia boss’s contract, but said mafia boss doesn’t seem to be around currently… 

“Hey,” The bartender says and Cuphead looks up at him, “no kids allowed, slugger.” The bartender points at a sign that says in big bold letters ‘NO CHILDREN ALLOWED’. 

“Oh, uh, I’m- erm…” Jeez, okay, he needs to think of something fast before he gets kicked out. “I’m actually, uh- t-twenty-two years old.” No, shuddup, he most definitely did NOT stutter. 

The bartender eyes him suspiciously for a second, but then shrugs and turns his back to put the glass cup he’d been cleaning into its rightful place onto a wooden shelf. 

“Alright. I believe ya.” Cuphead lets out a breath he didn’t realize he was holding and takes another gander around the rustic bar. Seriously, where was this so-called ‘mafia boss’?? Did he somehow get the wrong location? Or perhaps he’s in the wrong bar or village…? “Say, are ya perhaps lookin’ fer someone?” The bartender asks 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 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 replies in a whisper, the bartender gives him a suspicious look of uncertainty. “I’m um.. a debt collector.” 

“Ha! So the Devil sent out another one o’ ya, huh?” The beetle laughs as he goes back to cleaning 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 asks impatiently while tapping his finger on the wood of the counter. The beetle dryly chuckles. 

“Yer serious ‘bout goin’ ta get his contract?” Cuphead nods. “Alright, you asked fer’ this…” The bartender motions for Cuphead to get closer to him so that he can whisper so that no one nearby can 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 nods intently. Wait, what time is it? Cuphead rolls up his sleeve but then realizes that oh, wait, he doesn’t own a watch. 

“What time is it?” He asks the bartender and they pull out a watch from their pants pocket. 

“It’s currently 6:52.” Cuphead groans and slouches in his seat. The beetle chuckles. 

“Ya’ came a bit early, bud.” 

“I noticed.” Cuphead replies dryly. The beetle toon chuckles then goes back to doing his job serving customers drinks. 

… 

Cuphead hadn’t even realized he’d dozed off to sleep when he’s abruptly woken by a shove that caused him to fall off of the bar stool, hitting the wood tiled floor harshly on his bottom. He regains his bearings and realizes that a bar fight is happening. There’s a bunch of toons fighting each other chaotically all around him. It seems as though more customers entered the bar while he was out.

Cuphead stands to his feet and goes to ask the bartender what the hell happened while he was asleep. 

“Yeah, it’s a Friday night. This sort of thing happens regularly. It’d honestly be weird if it didn’t happen.” The beetle chuckles as he hands a beaten rabbit toon a glass of beer, he chugs it then punches the person beside him and they quickly start fighting. 

“Wh-“ Cuphead stammers confused as he watches the rabbit exchange punches with the other toon beside him. “Why??” The red cup only gets a chuckle as a response. 

“By the way, it’s 11pm now.” At that, Cuphead perks up and looks at the watch that the bartender is currently holding up at his face. “Good luck.” The beetle says as he places the watch back into his pants pocket. Just then, the door opens with a BANG! And everyone’s attention is now focused on the door. The moonlight casts a huge shadow on a big pug toon in an equally as big fluffy brown coat, with two other dog toons standing behind him on each side — which Cuphead presumes are his bodyguards. The pug stands there with a wicked grin, shining his bright and shiny golden tooth. 

The pug lights a cigar then walks into the bar, each step that he takes making a creaking noise from within the floorboards. It’s so quiet that Cupheads can even hear the labored breaths of the toons 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 looks like he fits the name perfectly. 

The pug approaches the counter, and the bartender, like clockwork, hands the intimidating toon a key to the basement. He doesn’t say a word as he motions for the two other dog toons to follow him downstairs. Everyone stays quiet as they listen to their heavy footsteps descend down the creaky stairs. Then, they can no longer hear a thing, everyone begins to whisper amongst themselves. Cuphead sits back on the bar stool with a hundred yard stare filled with fear. The bartender notices and goes to give Cuphead a drink. Cuphead stares at the offering confused, wondering if this dude really gave him alcohol. 

“It’s apple juice, c’mon, I wouldn’t give a child beer.” Cuphead chugs the drink then slams the cup back down. Whoops. He actually didn’t mean to do that. His nerves are just- uhh- OKAY HE’S SCARED, ALRIGHT? Did you see that guy?! He was like- he had to be at least 7ft! And that’s extremely tall considering Cuphead is barely even 4ft. 

“Cold feet?” The beetle asks as he refills Cuphead’s drink with more apple juice. He slides the cup to the teen and this time Cuphead takes his time sipping it. At the older toon’s question Cuphead looks away embarrassed. 

“…no.”

“Then what’re ya wait’n for? Go get ‘em!” Someone behind Cuphead says, pushing him forward and off of his seat. The cup glares back at the man, to which he then realizes that everyone in the bar is staring at him expectantly. A bead of sweat rolls down his face. 

“Aren’t you here for Big Boss’s contract? A debt collector from the Devil?” Another person from the crowd asks, to which the others agree and mumble quietly to themselves. Cuphead gulps, turning towards the door to the basement. The other patrons watch anxiously with anticipation as Cuphead walks to the door and carefully opens it. He takes a second to gather himself, then he enters through, 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 tries to convince himself as he descends down the stairs as quietly as he can. As quiet as a mouse. He thinks to himself. 

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, like in the movies. Uh- but anyways. He needs to focus. 

The sound of voices talking amongst themselves makes Cuphead freeze and proceed much slower. He stays on the stairs, crouching as he peeks through the wood rails. He’s glad that there’s no light where he’s hiding from, they’d immediately see his bright red shorts and nose, then he’d be mincemeat, or worse, dead. The voices seem to talk about trading goods, maybe liquor or drugs? Cuphead doesn’t quite know, nor care. Then, a deep rumbly and boisterous voice speaks up. 

“Those assholes will fucking PAY! NO ONE rips off Big Boss. NO ONE.” He roars and Cuphead could see the other people practically shaking and quaking in their boots at his sudden outburst. 

A shaky voice tries to de-escalate the situation, trying to reason with the big pug, but as he rambles on and on, his voice quivering and lowering to a whisper as his confidence diminishes, Big Boss approaches the scared person, his huge form easily towering over their smaller one. Cuphead can’t see what happens next but by the blood and toe-curling scream then the sound of a gunshot, he can probably take a guess. 

“Anyone else wanna spout nonsense?” Big Boss turns around, holding up his revolver as a silent threat. Everyone shakes their heads and the dog ruffs with a satisfied smirk. “Alright, I want my goods and money back. You two…” He sits down at a small round table that has a briefcase full of cash, an ashtray and a couple of beer and wine bottles scattered about on it. The dog continues to explain his plans but Cuphead has it basically blocked out of his mind by this point. 

He should go now while he’s busy distracted with boring business… Cuphead equips his smoke dash then cautiously descends down the stairs once more, crouching as he does so and using the dark lighting to his advantage. He gets to the concrete floor and looks around for some sort of cover. Scouring the room quickly he spots an open wooden crate and rolls over to it. He huffs, his heartbeat thrumming out of his chest. He tries to calm and steady his breathing, breathing in and out. 

Cuphead takes a peek from the side of the crate. They’re still talking, okay, good. Cuphead throws a smoke bomb onto the table and in a flash he’s then aiming his gun right at the pug’s nose with a serious glare on his face, as if to try to hide his true fear of the bigger toon. 

“I’m here for your contract.” He simply says. The two bodyguards stand to their feet and pull their guns out, aiming them at the cup. Big Boss is taken aback by this random newcomer’s appearance, but all he does next is bark out a couple of laughs. Cuphead frowns in confusion. 

“Oh boy, this is fantastic.” Big Boss cackles as he wipes a stray tear away from all his laughing. He leans back against his seat and rests a hand against his big belly. “The Devil really sent a damn kid for my contract? Seems Lucy is gettin’ desperate boys, haha!” The bodyguards let out a couple of laughs along with the pug. Cuphead begins to fume, his face growing red by anger or embarrassment, he has no idea. 

“Shut up! I’m not a kid.” A blue flame ignites on the cup’s fingertip as a warning. It isn’t actually a flame, rather an illusion of one of sorts, it doesn’t affect anyone or anything unless fired. But oh, Cuphead wishes it burned this jerk’s nose to a crisp. “Your contract.” Cuphead says again. Big Boss leans forward with a wicked grin plastered on his face, shining his shiny gold tooth. Cuphead can smell his awful wretched breath that smells of booze and cigarettes and he scrunches up his nose. 

“If you know what’s good for ya, you’d better skedaddle back on ta’ yer parents, kid.” Cuphead grits his teeth and he aims fire beside Big Boss’s head, the magic bullet hitting the wall behind him with a loud BANG! 

Everyone freezes. 

…

…In all honesty, Cuphead really hadn’t meant for it to be that powerful. Perhaps his anger affected the outcome. But maybe now this jerk will take him seriously. 

Cuphead huffs, his glare sharpening. “I’m not a kid.” Big Boss glares up at Cuphead, a deep, low rumble from his throat sounds, growling. It somehow just makes the teen feel better about himself. 

“Heh… You got guts, but I kind of hate that ‘bout you... Boys, leave him to me.” The bodyguards nod then excuse themselves and proceed to the stairs. Cuphead doesn’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. 

“Your magic alone won’t save you, debt collector.” Big Boss rises from his chair, fixing his fluffy brown coat. Cuphead flinches, keeping his aim at the mafia boss’s face. Big Boss lights a cigar he pulled from his front pocket then blows the smoke in Cuphead's face. The teen squints his eyes from the smoke and resists a cough, to which the dog just laughs at. The next thing Cuphead knows is he’s being punched right in the gut which flings him over to the wall behind him, creating a big dent with cracks all over. Cuphead coughs while clutching his stomach. Something sharp almost punctured his stomach. Cuphead looks up to see Big Boss flexing his fingers, his hands adorned with shiny golden brass knuckles. 

Ah, hell. Cuphead isn’t good at close combat. Don’t bring up those hedgehogs— they were his size, if not a little smaller, but this guy is like seven feet tall. Cut him some slack! 

Cuphead bounces back up to his feet and equips spread and crackshot. Just in case he misses 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 charges forward, punching the wall but Cuphead manages to duck on time. The whole building reverberates from the contact and they can hear the patrons from upstairs shouting out in alarm. The debris from the wall falls onto Cuphead’s baggy black sweater and he stays frozen in place. “Think fast!” Big Boss gives the cup an uppercut, shooting him up all the way into the ceiling and in the process making a big hole. The pug looks up at the ceiling satisfied but his grin is wiped away when he feels a series of burns hit his body and he ducks his face. 

“Think fast!” Cuphead yells from the ceiling directly above Boss, using his ex shot he shoots it directly on top of the dog who screams out in pain. Cuphead smirks then runs to another area for cover when he hears Boss roar in anger. For once in his life he’s glad he is so short, or else he wouldn’t have the ability to run in this tiny space freely. 

Cuphead then clutches his stomach painfully with one arm, the other occupied with firing at Big Boss through the wood ceiling. He feels like he’s gonna puke from being punched in the stomach twice with such strength that it should’ve broken his bones, it sure as hell feels like he did though and he wouldn’t be surprised if it had. 

“You BRAT!” Uh-oh, puppy is angry. Big Boss grabs the table then throws it up at Cuphead’s general area, which was pretty on point because the next thing Cuphead felt was the sensation of falling then the painful feeling of hitting the hard concrete floor. It was muffled but he swore he could’ve heard his porcelain on his stomach crack. He goddamn hopes that doesn’t leave a mark. He cries out in pain then a shadow peers over him accompanied by a low growl. Ugh… Fuck. 

Big Boss cackles maniacally. “You lil shit. You play dirty.” He knows. And that’s what makes fighting these debtors so fun. “Heh, you want this?” Boss crouches down to Cuphead’s level (the best he can) and waves his contract in his face tauntingly. Cuphead glares at him and tries to sit up. “No, no. You stay there, alright?” He presses his big paw on the cup’s back, holding him down. Cuphead tries to resist. Get up, get up! His mind and instincts yell at him. Big Boss only cackles menacingly at his futile efforts then stuffs his contract back in his jacket pocket. Cuphead raises his hand and shoots at the dogs’ eye and it does the job at getting him to let Cuphead free and the teen wiggles out from his hold and rolls away. “ARGHH- FUCK-“ Cuphead smirks, then winces when he feels a sharp pain in his cheek. He feels it and realizes it cracked there too, and it’s a deep one too because he can see that disgusting red staining his glove. He gulps. 

Big Boss glowers at the cup while covering his eye. Shit, he should really run right NOWW- A chair head his way and hits the stairs behind him, both the stairs and chair breaking on impact. Click! Cuphead turns and sees Boss holding a revolver while aiming it square in his face. “Ya wanna fight fire with fire?” BANG! Cuphead screams out in agony holding his right arm. Blood seeps through the fabric of his sweater. He trembles and tries to resist the tears that threaten to fall from just how much it HURTS. “Yer just a kid. Ya never had the guts to go into this line of work.” Boss approaches Cuphead and crouches in front of him. “Because if you did, ya wouldn’t be cryin’ right now.” Cuphead? Crying? Wh-when… Cuphead raises a hand to his face and feels a dampness on his fingertips. Oh. Big Boss grabs Cuphead head firmly and smashes it against the staircase behind him. Over and over and over and over and over again. 

CRAACKKkk…

Cuphead desperately grabs hold of the dog’s wrist to pry it off of him. 

CRRAck craAckle… 

It hurts. 

CrAAckK. 

But Boss doesn’t stop smashing his head over and over. IT HURTS. STOP! Cuphead kicks his stomach but he’s 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 teen’s vision is hazy, he doesn’t even realize the other stopped his abuse and picked him up for another round of punches. Probably in the stomach. That seems to be his favourite place to hit the cup. 

—

“AHHH-“ Cuphead shrieks as he’s being thrown up again into the ceiling. But this time it goes through another layer of the building’s wood and he’s laying in the middle of the bar bloodied up with scrapes and bruises all over his body, oh and a black eye. With stray pieces of porcelain scattered about around the boor boy. Ohh his body aches all over… Cuphead gazes at his surroundings, but all he can gather is a bunch of blobs around him and muffled voices talking. He’ll just- he’ll just lay here for a bit… Rest his body a bit… and… take a little… nap… 

The patrons stare at the beaten cup with a look of pure horror, their faces as pale as paper. They can hear roars coming from the basement from Big Boss, his bodyguards rush downstairs to the basement once they hear that. Once they’re finally gone everyone rushes to the teen’s side. 

“Oh shit he’s dead!” One of them shrieks as they hold their head with shaky hands, their eyes dilated as they start to hyperventilate. 

“He killed a kid!” Another cries, literally, they have tears streaming down their face. But then look away from the bloody scene and rush to the restroom with a green face. 

The rest of the group talk and whisper amongst themselves while staring at Cuphead. But no one goes to his aid. 

The bartender manages to push through the crowd, yelling out ‘Out of my way!’ and ‘Move it!’. He finally gets to the middle of it all and he sharply sucks in a breath. Everyone watches the scene sorrowfully. No one knew the cup personally, but, well, he’s young. Everyone who had a hat on took it off and held it to their chests. The beetle crouches down at Cuphead’s side, he grabs his wrist and checks his pulse carefully. Everyone stays quiet with a bated breath. The bartender lets his wrist go, letting out a relieved sigh he puts up a thumbs up. Everyone looks at each other for a second, silent. Then they cheer and hurrah and put their hats back on. 

“Shut up!” The beetle shouts and everyone falls silent. He huffs out annoyed and mutters obscenities under his breath as he lifts Cuphead up in his arms. 

“What’re we gonna do with him?” Someone from the crowd asks and at that everyone else starts to wonder the same. The bartender sighs. 

“I don’t know… I’ll search him to see if he has any contacts on him so we can call someone to pick him up. Get him anywhere but here.” Everyone nods and agrees with that. “I think I’m gonna have to kick you all out though. This has nothing to do with you.” Everyone then boos but the beetle pays them no mind and takes Cuphead to one of the cushioned seats and lays him down in a comfortable position. 

With that, he then turns to his patrons and shoos them out of his bar. They all continue to boo at him but exit the building anyway. 

The bartender returns to Cuphead and begins to search his pockets. But all he can find are contracts and- oh wait? What’s this? He brings out a little piece of paper up to his face that has a phone number with a name on the back, presumably the caller’s name. Bingo. He runs to his telephone by the counter and dials the number hurriedly. 

Riiinnggg… 

Riiinnngggg…

Riiiiinnnnnngggggg….

“Goddamit! Pick up, you piece of!-“ Click! 

“…Hello? This is Porkrind-“ 

“Yeah, yeah! Come get yer kid! He’s all beat up from a fight!” He doesn’t want to say anything more than that in case his dad doesn’t know he’s a contract collector.  That’d probably create even more problems for the poor fella. 

The beetle can hear the toon from the other end sigh. “Ah, shit… How bad is it?” He says which just makes the beetle angrier. 

“Does it matter? Get over here! The address is…” 

… 

The bartender finishes up with the bandages. It’s the least he could do, after all he encouraged the boy to fight Big Boss. Which just seems rather foolish now… BANG! His gaze shoots up to the door and it lands on a tall pig with an eyepatch standing at the entrance, who he assumes was the man- er… pig, on the phone a couple minutes ago. Porkrind’s gaze sweeps through the whole bar until his eyes land on two small brown shoes and familiar red shorts laying down at one of the tables. He rushes to the cup’s side. 

“Jesus christ… Cup…” The pig says as he takes in the teen’s appearance. He gently caresses his face. The beetle approaches the two. 

“I did all I could to clean his wounds. But his head is kind of um…” He sighs then takes out a small bag from his pocket, “this is all I could gather from the scene. ‘Hope it helps.” He hands the other toon the bag and Porkrind accepts it and puts it in his pocket. 

“Thanks.” Is all he simply says as he gently, very gently picks up Cuphead into his arms. But before he leaves he turns to the beetle. “He’ll be back ta’ fight ‘em.” The beetle’s face looks at him flabbergasted and he frowns. 

“He shouldn’t! He’ll die for real next time!” But the pig just shakes his head with a dry chuckle, he turns to the door to leave. 

“He won’t. And no, he won’t listen to me.” the pig says then promptly leaves the bar. The bartender stands there silently praying that the cup boy won’t come back, for his own sake. He then sighs, “I hate bar fight Friday…”

—

The door to the bar creaks open and the bartender glares at the wall. Ugh, he was just about to close… And to also put salt onto the wound, he finally managed to convince Big Boss to leave for the night to do repairs. The beetle turns to look at the door but freezes, his face paling. The Ink Demon… 

The demon whistles as he takes in the damage as he slowly walks further inside the bar.  He then spots the bartender behind the counter and approaches him, to which the beetle visibly tenses up at. Bendy grins and takes a seat at one of the bar stools while leaning his arm on the counter. 

“So… What exactly happened here?” He asks simply, his gaze lingering on the huge hole in the floor. The bartender gulps and begins to prepare a drink to calm his nerves, but his movements are shaky and a bit sloppy. 

“U-uhm, a fight.” Bendy hums thoughtfully and leans his face on his hand, looking bored or sad? No, that’s not… that’s not right. He looks to be almost disappointed? 

“Ah. I just missed it, huh?” The beetle nods and finishes up the drink, sliding it over to the demon. Bendy eyes the cup, he picks it up and swishes it around then takes a sip. He hums then stands up and the bartender flinches. The Ink Demon walks over to the hole to inspect it. “I’m assuming it was a fight between a cup and a dog?” He questions idly as he picks up a little porcelain shard from the rest of the debris. 

“Yes…” How does he know that? Does this guy somehow know the cup? “That is correct.” The demon stands up, placing the shard in his suit pocket. He then turns 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 grins darkly and the beetle gulps nervously, clutching a knife behind his back that he nabbed while the demon wasn’t looking. Bendy leans closer to the beetle. “Tell me where that cup went, and I might spare your life.”