Cuphead Casino Oneshots

+ Fluffy Encouragement +

Ship: Wheezy x Bartender Reader

Trigger Warnings: Slightly mature language

You had been working at the casino for a few months, after having lost your soul due to a casual game which went wrong. While the situation at the time felt like the worse case scenario, now you couldn't help but feel glad that that was the outcome.

You had been given the job of a bartender, working alongside Mangosteen as an assistant. In the beginning it was...certainly an interesting job. Getting used to the customers, learning how to start a conversation with them and of course learning how to make a range of beverages.

However, after a while, it became second nature to you. You became a natural at it and would have no problem covering the entire bar whenever Mangosteen had one of his moments.

In fact, that was what you were doing on that fateful day, serving costumers whilst the Tipsy Troop helped out. It wasn't too difficult, in fact there wasn't too many people. It was one of the least busiest days of the week, hence why Wheezy was able to hang out with you and Chips at the bar.

"So that girl you were hitting up-" Wheezy stated, pulling you out of your thoughts as you glanced at the men, still clutching onto the wine glass that you just so happened to be polishing.

"I was not hitting her up! I was just talking to her, that's all," Chips retorted, glaring at him.

"Oh please, she was all on you. Hell, even I could see it from over here," You defended the cigar, your eyes glistening with mischief.

"You seemed to be enjoying it too~" Wheezy sniggered at the expression that Chips gave, his eyebrows furrowing, and his mouth was left hanging.

He hesitated for a moment before sighing.

"Alright so maybe I was. Why do you care anyway? Is your lack of action finally catching up to you to the point that you're left staring at me longingly as I sweep girls off their feet," Chips smirked.

"You really think I would care about those bitches who dress up just in hopes of getting a 'good time'? " Wheezy raised an eyebrow.

"Oh, come on, it must be lonely not having someone in your life,"

"Yeah, but I would prefer to have to wait and find someone who is willing to stick around rather than just some one-night stand,"

"Oh please, like you would be able to find someone who is up for that?"

"I think you'll find that I already have-" Wheezy froze at his own remark.

You and Chips also froze, both equally surprised at his statement.

"Wait hold on, you actually have someone?!" Chips questioned, leaning forward in curiosity, analysing the cigar whose face was now a bright tomato.

"W-well no, but hopefully I will by the end of the night," Wheezy murmured.

"You're planning on asking them out tonight?! Damn I wish you luck Wheezy," You stated, a small smile rising on your face.

"T-thank you," He responded, staring down at his hands.

"Wow for the first time in a century you have finally decided to make the first move-"

"Oh, shut up Chips!"

*Time skip to closing time*

You were cleaning up the bar, wiping the counter of any crumbs or drops of whatever alcohol beverage people chose that they just couldn't prevent from spilling anywhere. I suppose they were drunk so it weren't too surprising, but you know.

Wheezy happened to be sitting in front of you on one of the stools, keeping up a vague conversation with you. Since he weren't able to lock up until you had went, he had to wait for you which was a lot more common of an occurrence than you may think.

"So...er going back to the conversation earlier, when are you planning on asking them out?" You asked, gaining the attention of the male who at that point was staring off into the distance.

"Hm? Oh err...soonish?" He mumbled.

"...that didn't sound certain at all. What's wrong? You nervous to ask them out?"

"...maybe,"

"What is there to be worried about? Rejection?"

"What kind of question is that. Of course, I am worried about rejection, who wouldn't be in this situation....look I...I just don't know whether I should actually ask them out. I mean you know me. I can be real lazy at times...I only really get involved when I have to, and I can be a massive jerk to my own mates. How the hell would I be a good partner for anyone? No one should have to put up with me being their boyfriend,"

"Well that ain't true. I mean sure you can be lazy at times but isn't everyone at some point? Plus, you're not a jerk. You joke about stuff and people laugh along with you. You can be really nice to people when you know they need it and are always there when someone like Chips or me needs you. You are an amazing people and anyone who is lucky enough to have someone like that in their life just feel cherished," You gave a soft smile, staring straight into his eyes.

He went silent for a moment, seemingly thinking over what you said.

"Also if you don't do it now, you may never have the chance to. Someone else could sweep in and take them away. You don't want that to happen, do you? And don't chuck the whole 'they're probably better than me' bullshit. My best advice would be for you to do it as soon as possible and get it done with. If they reject you then they clearly don't know what they are missing out on,"

"...ok, I'll do it," He sighed, placing a hand on his head.

"Atta boy!" You chuckle, patting his shoulder as you walked out from behind the bar to put away one of the glasses.

"Hey Y/N?"

"Hm?"

"I love you,"

"Alright I-"

You froze, for the second time that day. You span around, staring directly into the males eyes. Fear and concern circled his pupils as they flicked to stare at the ground. Giving a gentle smile, you place the glass on the closest surface and walk over to him.

Once close enough, you lean down and place a gentle kiss on his forehead, a small giggle following it.

"I love you too Wheezy,"

1059 words

Ok so I feel like I made Chips out to be a bitch- I promise you I do love him, he is one of the best characters. I just needed someone to tease Wheezy and I feel like out of anyone else there, the two of them would have some what of a brotherly friendship.