#cuphead devil x reader

FIRST ENCOUNTER

Your friend convinces you to go to the casino-- just for fun. You’ve never been before, so you agree, figuring a drink or two won’t hurt. You’re not here to gamble, and you’re certainly not here to make deals with the Devil.

Typically, the Devil is a busy man. You won't find him at the casino (surprisingly); he's usually behind the scenes living a luxurious lifestyle while tormenting the living. But today? Today, he’s out surveying his territory, sniffing out “fresh meat.”

The moment his gaze lands on you, something inside him clicks. He knows he's found it.

He turns on the charm instantly-- silken voice, calculated smile and , casual small talk meant to lull you into a false sense of security. Just a little smalltalk will lead to something more sinister later.

“Well, well, well… who do we have here? Haven’t seen you around before.”

But you're smarter than he initially expects. You don’t bite. You're dismissive and shut him down at every turn.

Money? Not interested.

Games? No thanks.

Fame? Nope.

You’ve heard enough stories about him to know better, and the nervous glances from other patrons only confirm your suspicions.

You're obviously uncomfortable, so you finish the rest of your drink and head for the exit with your friend.

But he's insistent, and your disinterest makes him itch. The closer you get to the exit, the more his composure cracks. That smug smile starts to strain as his need to win twists into something else entirely.

“You’re really just gonna walk away? From me?”

Why is your soul suddenly so important? You're not bound to be his by contract; You’ve made no deals, no bets, no promises… yet the thought of letting you walk away feels unbearable.

You find yourself merely meters from the doors, almost to freedom, when his hand shoots out, gripping your arm. You whirl around, wide-eyed, but before he can say a word, your friend yanks you through the exit.

That was the last time you saw him-- at least, in the open. Now, he’s everywhere.

OBSESSIVE TENDENCIES

• The Devil is used to sleeping soundly in his king-sized bed, wrapped in opulence, with all his vices satisfied. But now? Now he can't have the one thing he wants: you.

• He can’t eat, can’t rest, can’t enjoy his usual pleasures-- tormenting the living, destruction, arson, basking in his own glory-- because every thought comes back to you.

• 100% stalker energy, but not in the way you may be thinking. At first, the stalking is “practical.” He learns your daily routine, your habits, your friends-- all in the name of “strategizing.”

But by day three, the plan changes. You’re no longer just a soul to claim.

• He notices the little things: Your laugh, the way you brighten up the room, and the kindness you show even when you don’t have to. How disgusting. But he keeps watching. And watching... and watching.

• Henchman spotted it first, ahead of all the demons residing in the underworld.

“Uh, Boss? You’ve been starin’ out that window for three hours.”

“…Shut it, Henchman. I'm busy.”

The way his boss is distracted, lingering, lost in thought. This sends alarm bells ringing. It’s not a strategy anymore. It’s fixation.

• The Devil uses his shapeshifting. Not to lure or scare you but to stay close-- slipping into the crowd as a stranger, perching in the form of an animal, anything to keep you within reach.

You're smiling. You're laughing. You're full of life, constantly on the move, and most importantly, you've got that sparkle and pizazz he craves so deeply.

• You’re vibrant, untouchable, magnetic. That sparkle in your eyes-- it’s addictive, and worse, it scares him. HIM-- the Devil. 'Cause this isn’t about winning a game, or even about your soul anymore. No. This is about you. And the Devil doesn’t drop the things he wants.

• He turns up everywhere you go-- sometimes casually leaning against a lamppost with that smug smirk, other times lurking in the corner of your eye when you swear you’re alone.

• It’s not a coincidence; he wants you to know you're under his watch.

• There will be some instances where you meet with him again. Especially if you are joining the cup brothers on their tirades. You see everything-- his temper, malice, and... efforts to court you?

• He will go to absurd lengths to win your approval, to appear “cool” in your eyes. Desperate doesn’t even begin to cover it.

Fancy outfits, Over-the-Top Grand Gestures, showing off his “connections”, competing for his attention.

If someone else makes you laugh, he’ll instantly interrupt with a bigger, louder joke or trick.

• Naturally, you fear him (for the most part), but you become more 'accustomed' to his presence as time goes on. There are two different paths you could go on in this instance:

Path #1: What if you actually become attached to him?

• In his eyes, this is nothing short of divine providence-- a wish he didn’t even have to trick you into making.

• He doesn't need the kidnapping, gaslighting, lies, stalking, eliminating rivals. He'll be a happy man-- however, he's going to be attached to you practically 24/7.

• Your affection becomes his greatest treasure… and his most addictive drug. Every smile, every compliment, every loving glance feeds his massive ego until he’s strutting around like the king of the underworld he believes himself to be.

• After all, someone as dazzling as you choosing him? It’s proof, in his mind, that you truly see the “magnificent heart” beneath the horns and hellfire.

• You’ll have your own bed, shower, and space; he’ll feed you anything you crave. Be docile, and he’ll rub your back, lean against you, kiss your forehead, and spend hours gazing at you with an almost unsettling tenderness.

• His favorite thing is holding you and wrapping his arm around your waist-- it's a statement for sure, but also, it takes the edge off of his 'busy life.’

• But also… HOLD HIM.

• PLEASE FOR THE LOVE OF EVERYTHING—HOLD HIM, too.

• Surprisingly a sweet and passionate lover. When you walk into the room, his entire demeanor changes. He's instantly gushing or yapping to you about something trivial that happened earlier that day.

• You are the only person (besides Henchman) that he will open up to. Emotionally and mentally-- but don't take that for granted.

Path #2: You have no romantic interest.

• Definitely has tantrums knowing that you don't seem to like him. When that realization hits, he’s livid-- ranting in front of Henchman while igniting into flames like a full-blown firenado with every furious gesture.

• The Devil is not self-aware in the slightest-- A man of immense pride, he simply cannot comprehend why you aren’t attracted to him.

Oh, by the way, he remembers how your buddy yanked you out of those exit doors. He’s not letting that go.

• He will isolate you from anyone who might get in the way of his connection to you-- including that friend.

• His methods range from sly and mysterious to devastatingly blunt. If they continue to be the barrier protecting you from him-- they have to do it just enough times to where he becomes sick of it.

• There are different ways he can go about this, from dark to mysterious and devastating. Yeah, they're gone. I don't think he'd kill them, but it is in the realm of possibility.

• If you’re connected to the Cup brothers-- whether as family or close friends-- they’ll know exactly who’s behind this, thanks to their own history with him. And yes, the Devil is still trying to steal Cuphead's soul... but he found an even better idea!

DEALING WITH THE DEVIL

You soon find yourself in a dire situation. The Cups are captured, and you’re the only one left to fight for their return.

Then, he makes you an offer-- a deal laced with poison: He’ll end his tirades against the Cups, release them unharmed, and erase Cuphead’s soul debt entirely… but at a cost. And that cost is you.

“Here’s the deal. I let the boys go, wipe Cuphead’s debt clean… and in exchange, you’re mine. Forever.”

Unfortunately, this does lead to a bad ending. Even if you play your cards right.

This was his plan all along, a perfect trap designed just for you. And he already knows your answer-- because you’d do anything for them.

Desperate, you agree. And he actually keeps his word (shockingly). The Cups are free, but now you’re the one trapped in his claws. Maybe forever.

AFTER THE DEAL

• Once you’re isolated? Oh, you’re stuck.

• Now that you belong to him, this will be an unsteady and unhealthy ride.

• Are you upset? In tears? Furious? He’ll still try to comfort you, even if you curse at him, shove him away, or spit venom in his face. No matter how many times you tell him you hate him, his delusion holds fast-- he believes you must feel the same as he does now that your soul is his.

“Easy, easy… you’ll warm up to me. You have to.”

Though, it wounds his pride when you glare at him. Hurts him, even. Seeing you upset is the only thing that dims his fire. :(

• And if you try to run? He’ll give you a head start— just enough for your hope to flicker—before appearing in front of you without a bead of sweat, looking entirely amused. “Going somewhere, hmm?”

• He’s an emotional gambler. If sweet-talking doesn’t work, he’s not above using guilt or pity. You’ll hear sighs, wounded remarks about how “cruel” you’re being and ignites the theatrics like he’s the tragic hero in a doomed romance.

• His threats, when they come, are dressed as charming little quips-- lighthearted enough to almost fool you-- until you catch the cold glint in his eyes. Spoiler: he’s not joking.

• Deep down, he hopes you’ll eventually develop Stockholm syndrome. He’ll apologize with expensive gifts, lavish meals, or soft touches meant to soothe. It never works.

• If you behave, he'll be good to you.

• He'll make sure you are well taken care of. So follow his rules, and he'll rub your back and lean against you. He'll kiss your forehead and gaze at you for hours.

• His love, when he thinks it’s reciprocated, is soft and gentle-- regardless of whether you truly care for him or not. You’re still stuck.

____________________________________________________

• Henchman may serve the Devil, but there’s a streak of goodness in him. He might help you… or perhaps you’ll have to wait for the Cups to mount a rescue.

The only people that have a sliver of a chance to help you are Henchman and the Cup brothers. Without them, you stand no chance.

You hum a tune to yourself as you sit on the boat making its way towards Inkwell Isle. Maybe you’re reading a book? Or staring off into space? Perhaps you’re playing an instrument, or you might be writing in a journal? It doesn’t matter how you pass the time, you’re still able to admire the view of your childhood home and think to yourself about everything that’s been going on.

You are Y/n, and what your little brothers call, a spy. You work for an organization to help take down criminals and your role is usually to sneak into their base and impersonate a gang member so you can infiltrate them and take them down from the inside. You’ve been told by many of your co-workers and even some of the criminals you captured that you’re a master of disguise, even a rat would think you’re one of them even if you’re clearly not.

Because of your job, you usually have to travel the world and you can’t spend much time at home, so your boss has given you some time off work, usually two weeks every two months for you to visit your family.

Who’s your family? Why, Cuphead, Mugman, and Elder Kettle, of course! I won’t specify if you’re related to them or not, either way they’re still your family.

Once you get home, you open the gate and walk into the front yard of your family’s home. Before you could make it to the front door, the door is kicked open and Cuphead and Mugman run towards you.

“Y/N!!!” Your two little brothers tackle you in a tight hug, a hug which you return.

“I missed you two lil dum dums!” You laugh with a smile.

“We missed you too!” Mugman says happily.

“Didja bring any gifts for us!?” Cuphead asks excitedly.

“Cuphead!” Elder Kettle scolds the cup with a glare before turning to you. “We’re glad you’re back, Y/n.” He smiles at you.

“I’m glad I’m back, too! I missed you guys so much!” You say as you let go of the hug with your brothers. “Now, who wants their gifts? They’re souvenirs from my last three missions!”

“Me! Me!” Cuphead and Mugman say excitedly in sync.

“Alright.” You chuckle, grabbing your bag of gifts. You take out a light blue cowboy hat with a light pink flower on it. “First is the same cowboy hat the corrupted sheriff wore when she stole from the bank, for Mugman.”

You hand Mugman the cowboy hat, which he takes and puts it on, striking a superhero pose. “Now I’m the sheriff!”

You then take out a tarot card deck. “Now this is a tarot card deck the cult leader we imprisoned carried at all times, for Elder Kettle.”

You hand Elder Kettle the tarot card deck, which he takes with a smile. “Ah, just what I wanted! Thank you, Y/n.”

You lastly take out a small orange megaphone that fits in the palm of your hand. “And finally, the megaphone the mob boss used to communicate with me and other giants, for Cuphead.”

You hand Cuphead the small megaphone, which he takes and shouts through it. “Ey, it works! Even though it’s so small!”

“Now, boys. What do we say to Y/n?” Elder Kettle asks them.

“Thank you Y/n for the wonderful gifts!” Cuphead and Mugman say in sync.

“Aw, you’re welcome!” You smile at them.

“Now, why don’t you come inside? Your room is ready for you.” Elder Kettle says as he begins walking towards the house.

“Alright!” You smile as you pick up your luggage, walking into the house with Cuphead and Mugman following you, asking about your adventures.

The next day, you’re sitting in a chair in the living room, passing the time doing your own thing. Read a book, write, play an instrument, listen to the radio; whatever you want. Elder Kettle left to shop for groceries and other stuff he needs to get. You decided to stay to watch over your little brothers…speaking of which, they’re probably outside playing with Elder Kettle’s lucky tire again. As long as they don’t lose it or break it, you don’t care.

Speaking of the boys, you get up and lean over the window to check on them… Okay, they’re not outside and it’s way too quiet. They must’ve wandered off, again. You grab your bag you always carry with you and step outside. There’s a few spots you usually check first, which more often than not is where they’re at. First, the forest nearby the house.

“Cuphead, Mugman? Where are you?” You call out as you walk.

Silence…okay, maybe they’re playing hide and seek.

“Now isn’t the time for hide and seek; besides, you guys suck at hiding.” You say, taking a glance around the forest.

No response. Usually that gets a “you’re just good at finding us!” from Cuphead, but there’s nothing but silence. They’re probably not here, you assume. Next, time to check Porkrind’s. Maybe they’re wasting all their money again or annoying Porkrind.

You turn and start walking towards the shop, enjoying the peaceful silence of the forest. The bird’s chirping, the flora as beautiful as ever…

“GET BACK HERE YOU STUPID CUPS!!!” An unfamiliar voice shouts.

“RUUUUN!!!” You hear Cuphead’s voice, then him and Mugman yelling. You rush towards the commotion as fast as you can. Oh boy, what trouble did they get into now?

Thunk!

You bump into Cuphead and Mugman, who both fall on their butts from the impact. “Oww…”

“What’s going on?” You ask them, looking down at the two.

“Y/n!” Cuphead beams with a bright grin.

“Help us, the Devil’s chasing us!” Mugman pleads.

“The Devil?” You ask, raising your eyebrow.

Sure enough, the literal Devil comes running from the bushes, approaching the three of you with a look of pure anger. Your little brothers yelp and jump up, immediately hiding behind you. You move to a protective stance, keeping a brave face and shielding your brothers from the demon.

The Devil stops in his tracks right in front of you, taken aback by both you defending them and the fearless look on your face. “Move.” He demands.

“No.” You say firmly. You would’ve pulled out a weapon, but this is the literal Devil. Even you’re not confident enough to straight up attack him.

“Wha-” He gives you a look of genuine confusion and shock. “Why not? He owes me his soul and he won’t give it to me! He’s the one not playing fair!” He snaps, gesturing to Cuphead.

You turn and give him a look. “What did you do?”

“It was an accident!” He says.

“How were we supposed to know that carnival was a trap?” Mugman adds.

“If only we had that invisible, impenetrable sweater…” Cuphead mutters, looking down in thought.

“Ha! My demons and I have it in a secret, undisclosed location that you fools will never find!” Devil laughs with a cocky smirk.

“What happened while I was gone??” You ask, mostly rhetorically.

“A lot.”

“Who even are you?” Devil asks you. He thought he knew everyone who lived in that cottage, but apparently not.

“Y/n, and that’s my little brother’s soul you’re trying to steal.” You say, crossing your arms and giving him a sharp look.

“It’s not stealing if he’s the one who isn’t playing fair! He lost the game fair and square, his soul belongs to me now!” He snaps at you.

“You’re trying to take his soul way too early, he’s still a kid!” You snap back.

Devil takes a sharp breath, taking a moment to calm himself down. It wouldn’t do him any good in getting angry…hang on, a thought just came to mind. You’re not at all scared of him, which piques his interest, and you’re close with Cuphead…perhaps he could try to befriend you to get to Cuphead, and find out more about this interesting mortal who’s brave enough to snap at him.

“You know what…how about we talk about this like adults over tea- or coffee or whatever you want, I don’t care.” Devil asks you, giving you a very obviously fake smile.

You and your brothers’ all have one single thought; “...what-?”

“You heard me. You’re…a very interesting mortal, and I’d like to get to know you. What do you say?” He asks you, putting on a charming grin to persuade you.

You…are speechless. The Devil wants to get to know you, of all people? Wow, you are so…not fooled by his act. I mean, come on. It’s so obvious he’s trying to manipulate you…although, he did say something about having some invisible sweater that would keep Cuphead safe, so what if you beat the Devil at his own game and get close to him to find that sweater.

You give him a casual grin. “Sure, why not? Sounds nice.” You say.

“Wait, seriously-?” His grin falters for a moment before he puts his charming facade back on. “I-I mean, perfect! Where shall we go…Y/n?”

“Well, there’s this cafe I really like going to; we should stop by. Chat for a while.” You reply. Your brothers give you the most confused looks, completely baffled you’re “fooled” by his charms.

“Perfect! I’ll meet you there, just tell me the name.” Devil says, hiding his giddiness over his plan actually working.

You tell him the name of the cafe and where it is in town and he nods in response. “Perfect…I’ll meet you there, Y/n!” He says, already acting all buddy-buddy with you, before hitting the bottom of his pitchfork on the ground, disappearing in a cloud of smoke.

Cuphead and Mugman step out from behind you and give you a weird look. “Seriously!? You’re a master spy, but you’re that easily fooled by him!?” Cuphead asks, still baffled by what he just witnessed.

“Relax, Cups. I knew what he was trying to do. I have a plan of my own.” You shrug.

“Oh-”

“Yeah, that makes sense.”

“Now,” You kneel down to their height. “What can you tell me about that invisible sweater you mentioned?”

“Oh, that! Mugsy made it for me! It worked for a while.”

“Before the Devil got a hold of it. Now we don’t know where it is.”

“How does it work?” You ask.

“It electrocutes him!”

“But it’s very hard to find if you don’t know where to look. Ya can’t see it, after all.”

“Hmm, interesting…” You hum in response and stand up straight, thinking deeply to yourself. This might be the most difficult mission of yours yet, but you’re determined to help your little brother.

Here’s the longer fanfic if you want to check it out:

AO3 Link:

Wattpad Link:

He’s so obsessive (which I probably said before)

He loves looking at you and he holds his chin in his hand and stares at you

Whenever your away, he watches you through a mirror like portal/crystal ball

He wants to impress you by catching the Cups

You were there when they tricked him and he was so embarrassed he swore he’d catch them both and prove to you he’s not a loser (even though you never thought that)

“Look! Y/n I caught them!”

^ “Um… They’re gone”

He looks at the Cage and is shocked to see that the cup brothers are gone

He blushes a dark red, before throwing the cage and going back to his throne room, not saying anything to you. You watch confused but shrugging it off

Each time they get away, you get there just as he loses them

“Y/n! Hurry! I’ve finally got them!!”

At this point, he’s just tired of them making a fool infront of you

When he does finally catch them he’s so excited, he’s practically jumping

He gets you immediately and you’re surprised

“Oh! They are real!” You were surprised, not thinking them to be real. “Oh, dear, you’re not going to keep him in there are you?”

He’s confused because he’s always wanted you to see him catch the brothers that have been making a fool out of him, but now you’re on his side???

He’s angry and ignores you

Gives you the silent treatment

Though, it doesn’t last long because he can’t stay mad at you for long

Though he can be a little passive aggressive

But you just brushed him off

His henchmen like you, much to his annoyance, so when he’s mad you, his henchman just take your attention and hang out with you. Which, only upsets the Devil even further and he just gets huffier, but he’s mad you’re not hanging with him, but he also is mad and wants to ignore you, but because he’s ignoring you he’s not able to be around you because that would mean you win. (God that’s a mouth full lol)

He wants you to apologize to him and practically forces one out of you

Henchman gets an earful as the Devil rants about how useless and unreasonable everyone is. The Devil asks a rhetorical question about whether he should skip the niceties and go straight to the abduction stage, and Henchman, forever the supportive fellow, tells him to do what makes him happy.

Belonging to the land of the living means that many a deal is offered by the Devil to join him in Hell. Most revolve around landing a seat next to his throne and becoming a high-level demon in exchange for serving Hell in perpetuity, but there are a few that involve staying in the Inkwell Isles and running his casino.

Rejecting one of his deals leads to catastrophes everywhere. The Devil stews over this rebuff and orders his unholy legion of demons to pillage the world, an order that he agrees to rescind if his deal is then accepted. However, there is no guarantee that he will not continue the order later out of spite.

All of Hell hears his roars when there has been an argument between the Devil and the one who he forbade everyone from addressing. Demons know better than to get involved, but the souls of the living are not always so keen to turn a blind eye. Cuphead and Mugman have intervened and lured the Devil away more often than not.

Romantic:

The Devil would like a partner in crime more than anything else, someone who revels in the chaos as he does and laughs with him when famines sweep through the land. Anyone who stymies this fun together is incinerated on the spot.

Engaging in relations with someone besides him is strictly forbidden. This rule is in effect before he even makes his intentions clear, and if it is broken, the Devil will covet this illicit relationship and seek to make the other person one of the damned.

As soon as death comes and the soul leaves the body, the Devil appears in a ring of fire and snatches it. He makes an accommodating afterlife in Hell by his standards, although he views the situation as a belated victory and demands to know why none of his generous deals was accepted.

If Stickler appears with Hell's rulebook in his hand and deems the situation an unlawful seizure of a soul, the Devil rages against his words and prepares to incinerate him right then and there. No one is allowed to question this particular action lest they face the business end of his pitchfork.

Managing to escape back to the Inkwell Isles as a ghost is a herculean task that will require help. Henchman and King Dice are far too loyal to the Devil to consider helping, so the assistance comes in the form of Cuphead and Mugman's shenanigans.

One day, the Devil is preoccupied with hunting the pair or brooding in his chambers over the fact that they escaped his clutches yet again. The elevator to and from the land of the living is left unattended, and using it has never been easier.