#cuphead tickling

Thanks to the Cuphead DLC art book, we now have actual official names for all the tertiary characters and bosses, so I can finally cook up the long-awaited-by-nobody sequel to this! I've had multiple requests for more Cuphead tickle canons over the years but wanted to wait for solid info on the new guys.

Madcap Maddie

Everyone knows and loves Maddie’s distinctive laugh…it’s deep and melodious, dotted with owl-like hoots. She doesn’t hate tickling, but is quite a squirmer and will kick you. Being married to Charlie Left Legs gives her a position of wealth and influence in the mob, but it has some awkward disadvantages too…if her husband’s getting frisky with those eight skittery limbs of his, she might suddenly burst out laughing. She’s feather-ticklish just about everywhere…that’s why she doesn’t wear a boa…but especially on her thorax.

Sergeant O'Fera

This one lives up to her battalion as a member of the “Howling Aces:” O’Fera despises being tickled and can be reduced to feral screams by even the slightest poke. None of her squad mates have ever tried it, not even the Yippers…they’re too scared of her. Even her most helpless laughter sounds condescending and venomous. That said, she’s not above using tickle torture to interrogate prisoners of war. Most ticklish on her ribs, armpits, and heels. Her first name might be Bluebell, but this is unclear.

P.S. She does, in fact, bite.

ler!devil and lee!henchman y/n 👀

OKAY I LOVE THIS PROMPT so I had to do it right away!!!! Hope you enjoy!

THE FIRST LOSS

The Devil couldn’t believe this.

Somehow, a cup had managed to interfere with his plans. And just when he thought he might have a chance to make him pay and (rightfully!) collect his soul, King Dice had lost — for the first time ever.

He was fuming, but even he knew that it wasn’t fully Dice’s fault. He’d done everything in his power to try and collect Cuphead’s soul, but things had gone wrong. Even the Devil himself had tried to re-capture Cuphead’s soul, and he hadn’t been successful. So could he really blame his right-hand man?

Of course he could.

“I heard you had your first loss today.” His tone was oddly calm, trying to lure Dice into a false sense of security. “A loss to a certain… cup.”

Dice visibly trembled, and he looked up at the Devil, sweat dripping down his face. “I… I’m sorry! But I-I tried, and I’ll do better next time, I p-promise!”

The Devil simply scoffed, twirling the pitchfork around in his hand. “Oh, I know you will… but I need to be certain.”

Dice paled. “What do you-”

He never finished his question. The Devil had pointed his golden pitchfork towards King Dice, who let out a small yelp of terror as he was pinned against the wall. Letting a satisfied smile spread across his face, the Devil manifested four more arms, holding the trident in one of his six hands as he advanced towards his right-hand man.

“You see, Dice…” The Devil slowly stepped closer and closer solely for the purpose of scaring him. “You can’t escape. This is how Cuphead should have felt, but you let him go. For that, you will suffer.”

Dice stammered out a reply that sounded like a plead, but the Devil ignored it. “It’s almost laughable, the fact that he keeps getting away. You like to laugh, don’t you, Dice?”

King Dice seemed confused for a solid five seconds before he realized what was going on. His eyes went comically wide, and he shook his head rapidly. “No, no, wait! I-I didn’t mean to let him go! It wasn’t my fAHAHAHAULT!”

The Devil wasn’t the type to go easy. His five unoccupied hands had ripped open Dice’s suit, tickling him all over. Two hands under his arms, which were conveniently pinned above his head, one on each of his sides, and one alternating between his ribs and belly. No spot was safe, and there was no moving, no squirming, no escaping. All King Dice could do was laugh uncontrollably.

“BOHOHOHOHOHOSS! IHIHIHIHI’M SOHOHOHOHO SOHOHOHOHOHORRY!” Dice had never experienced something that was this ticklish before. Sure, every once in a while, if he had a close call on a show, he’d be tickled by the Devil, but never like this… because he’d never messed up this badly before. “PLEHEHEHEHEASE! IHIHIHI CAHAHAHAN’T TAHAHAHAKE IHIHIHIHIT!”

The Devil almost seemed bored — in reality, he was enjoying himself, but he had to pretend for the sake of his character. “Oh, sure you can. In fact…” He continued his tickling as he turned his head to the side. “Henchman?”

“Yeah, boss?”

“Get his feet.” The Devil took pleasure in the clear terror that had suddenly appeared on Dice’s face. “I’m tired of doing all the work by myself.”

“NOHOHOHOHOHOHOHO!” Dice was losing control of his words. All he could focus on was how badly it tickled, and that sensation was overpowering.

“No?” The Devil raised an eyebrow. “Did you just tell me no?”

“WAHAHAHAHAHAHAIT! PLEHEHEHEHEASE!” King Dice was turning red from both embarrassment and the unstoppable laughter. He tried to jerk his feet away from Henchman’s fingers, but he couldn’t move. He was forced to just take the tickling, unable to have a say in whether it stopped or not.

“Hm… well, I suppose I wouldn’t want my right-hand man completely out of the picture,” the Devil mused, letting out a dramatic sigh. “But I’m still not convinced that you’ll truly do better next time.”

“IHIHIHIHI WIHIHIHIHILL!” King Dice was surprised he was still able to communicate somewhat coherently through his cackling laughter. “IHIHIHI SWEHEHEHEHEHEHEAR!”

“You swear?” The Devil was dragging this out now, whether he wanted to admit it or not. “Are you sure?”

“YEHEHEHEHEHES!”

“But are you sure?”

“IHIHIHIHI’M SUHUHUHUHUHURE!”

“But are you sure you’re sure?” The Devil was smirking now.

“YEHEHEHEHEHEHEHES!” King Dice was absolutely losing it, and the Devil could see it from a mile away.

“Oh, fine.” He retracted his extra arms and released Dice from his magical hold, causing his right-hand man to collapse to the ground, practically gasping for breath.

“Ugh, you’re so dramatic.” The words were spoken in the most dramatic tone the Devil could muster up. It was so much fun to mess with King Dice — just like deflecting his little comment about being his “number one.”

“Get up.” The Devil reached out a hand, easily pulling King Dice to his feet. “Put your shoes on, lackey. There’s work to be done, souls to be collected, dice to be tickled… oh, wait, that’s you.”

King Dice was blushing like crazy, but if he was called out on it, he would claim it was just from the tickle torture he’d just endured. “Y-yes, boss.”

The Devil grinned, poking Dice’s tummy one last time with the blunt end of his pitchfork before waving his hand to restore the previously-ripped suit back to normal. “Wonderful! Now that you’ve agreed, I can tickle you whenever I want! Wouldn’t that be a special episode of Roll the Dice?”

King Dice’s face turned even redder at the thought, although he tried (and failed) not to show it. Was he supposed to agree or disagree? He slowly nodded his head. “Yes, boss… b-but I’m gonna focus on Cuphead for now.”

The Devil smirked. “Good. Now, off you go.”

And with that, King Dice left the room with Henchman, leaving the Devil alone to gloat. Perhaps a similar ticklish punishment would work just as well on Cuphead…

King Dice: Litohol Guyihys! Come ohohon! Ihihit's too muhuch!

Cards: We wanna hear you laugh though! But you have a amazing smile!

Club: I'm so glad he's our boss!

Spade: He's so adorable!

Diamond: We gotta tickle him more.

Heart: Maybe without his makeup, though. It ran a bit afterwards.

D: Sure. Sure. We'll keep that in mind.

K: But none of you are getting away with it~

Cards: ahahaha plehehese! We're sohory!! Mercehey!

K: You aren't escaping this! And two of you aren't even trying to escape ~

YES GOOD EXCELLENT :D sorry this took a little while but I hope you like <3

Alpha Twin

“I win again!” Cuphead exclaimed in triumph as he pinned his and Mugman’s clasped hands to the floor for the third time in a row. “Another victory for Inkwell’s arm-wrestling champion!”

“Okay, okay…” Mugman sighed, rubbing his arm and rolling his eyes a little as his brother bowed and preened before an imaginary crowd. Their wrestling matches were fun, but Cuphead sure did let winning go to his head sometimes. “Remember, Elder Kettle said nobody likes a bad winner.”

“More like a sore loser.” Cuphead smirked, before slinging his arm around Mugman’s neck and pulling him in for a noogie. “C’mon, Mugsy, don’t be like that! It’s not easy being the older, wiser, tougher brother, y’know…”

“Ten minutes older!”

“Still counts!” Cuphead let him go, planting his hands on his hips. “Alright, fine – one last rematch! To settle once and for all who is the true alpha twin!”

He raised his fists, flexing and posing like Ribby and Croaks always did before a fight. Mugman couldn’t help but snicker at the tough-guy act – they were practically the same size, but Cuphead was scrappier and more stubborn so it was usually just easier to give in whenever they argued. Right now, though, he was kinda asking to be knocked down a peg or two.

“You’re on!”

“This match will get red hot!” Cuphead declared in his best announcer’s voice. “You ready? Three, two…”

“Go!”

Cuphead launched himself at Mugman and wrestled him to the ground almost immediately; he tried to fight back and they pushed and shoved at each other, both starting to laugh as they rolled across the floor, back and forth. Mugman was trying to avoid clanking heads, cautious not to tip over from roughhousing to actually hurting his brother, which was probably how he ended up pinned with one arm twisted behind his back.

“See?” Cuphead taunted as he squirmed and bucked, struggling to free himself. “Might as well give up now, I’m just the better fighter…!”

He let out a sudden yelp as Mugman’s free hand managed to grab his side, fingers digging in and making Cuphead jerk and swat at his hand. “Nohoho fair - that’s cheating!”

“Gee, it is?” Mugman asked, innocent tone at odds with his mischievous grin as he realised an opportunity to turn the tables. He kept squeezing Cuphead’s side until he was giggling too much to hold him down, giving him the opportunity to wriggle free as his brother fought to defend himself. “You never said that - is my big, tough, older brother gonna be taken down by a couple tickles?”

“L-lihihihike you can tahahalk!” Cuphead protested through cackles, defiant even as Mugman twisted around to reverse their positions, sitting on his legs and scrabbling under his shirt to get at his soft, vulnerable belly. “You’re way more ticklish than meheheheeee nonono Mugs not there!”

Mugman found himself laughing too as he lifted Cuphead’s leg with one hand and scribbled behind his knee with the other – he was right, he was usually the one getting tickled to pieces, but a little overdue revenge sure was sweet. “Sooo, you give up?”

“Nehehehever!”

“Okay, if that’s how you wanna play it…”

He was probably gonna get kicked in the face soon anyway, so Mugman let go of his brother’s flailing leg - only to grab his shoulders and blow into his straw, causing his head to fill with bubbles and Cuphead to collapse into hysterics. Their secret weapon, known only to the two of them and Elder Kettle – it could be dangerous if anyone else found out that felt like tickly raspberries all over their whole body, or that it made Cuphead laugh so hard his face turned as red as his nose, pounding both feet and his fists desperately against the floor until Mugman figured he’d be begging for mercy, if he could form the words.

He let up and Cuphead slid to the floor in a limp, giggly puddle, lying there for a few moments recovering his breath until Mugman offered a hand to help him up.

“Sorry, Cuppy - did I go too far?” he asked, a little guilty but relieved when his brother sat up and shook his head, wiping tears of mirth from his eyes. He couldn’t erase the lingering blush so easily, though, and Mugman couldn’t resist adding with a giggle: “What was that you were saying about the alpha twin again?”

“Alpha twin this!”

Mugman let out a startled squeal as Cuphead grabbed his hand and pulled him down in a flash, fingers attacking his sides without mercy as the room filled with peals of bubbly laughter again.

HA HA HA

[They framed Dice for tickling The Devil]

D: This is for messing with me!

K: And this is for getting me in trouble!

K: Is my poor little deck alright?

Deck: Uhuh heh heh ye-yes mmmm

K: Okay! But you're still so giggly~ I think I can cure that!

K: Pttttt

D: AHAHA