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It was a normal saturday night. The street lights were buzzing, the sweet sounds of gang and crime activity outside, and the amazing smell of booze and smoke filled the bar. A short red cup sat in one of the chairs at a bar, obviosly drunk- and was at his third bottle for tonight. Cuphead, who was alone drinking (who the fuck even left this short bitch alone?) was talking nonesense and trying to start a fight too but you suddenly caught his attention. There you sat near him, holding a half drank bottle of whiskey on one hand and a half broken phone on the other. And you looked like a sext hot-mess. You had went here to drink your problems away after you got into a fight and broke up with your toxic partner.
And so there you were drinking your life away while black dried mascara ran down your cheeks not noticing the red cup eyeing you up, or he had eyes on the five-grand of cash that was sticking out of your purse. He went over to you (totally not to rob you or anything-) and spoke trying not to slur over his words
"Heyy babycakees, you wanna go to my place and, uh- count some cashh?" (I FUCKING LAUGHED AT THIS FOR A FAT MINUTE WHILE PROOFREADING THIS SHIT)
You looked at him confused for a few seconds before laughing hystericaly making the short cup turn red like his nose
"Pffft-hahaha! That- that was the worst joke ive ever heard!" You said while a few tears ran down your eyes while Cuphead akwardly laughed with you, the alcohol was not helping his emberrasment at all right now-
"Shit- uh. So.. whaddya say? Wanna go back to my place- and um, go down to town in bed with me?... shit i did it again-" Cuphead swore under his breath while you kept laughing harder you literally felt like crying, in a good way-
"Pffft- god- your pathetic-" You said brushing tears off your eyes while trying not to choke on your own spit.
"L-look i dont know how to flirt okay!? And drunk so shuttup and lemme fuck you" "God damn your that horny..? Well okay then-"
And so you two went into Cupheads apartment and just went straight into it, not caring about the mess- or the huge ass hole on the wall. Cuphead hoped Mugman was asleep right now because this was gonna be hard to having to explain what happend in the morning but that was the least of his worried right now because Cuphead had no idea what the fuck to do. He didnt think this far- all he wanted was that five-grand in your purse. But it was too late now because you just pinned him down on the bed, both of you are half naked, and Cuphead cant think of an excuse or escape plan right now. So he made one pathetic excuse.
"U-uh can you take the lead tonight? I-ive never done this before-" He mentally faceplamed for how pathetic he sounded and probably looked right now. He was a drunk mess and didnt know how to feel in the moment.
"Oh- uh s-sure, ive never been top but i'll try." You said before unbottoning his pants, at this point Cuphead was literally shaking and he was gripping his bed sheets like his SOUL dependent on it, and his face was bright red and he felt like his head was almost boiling at this point, literally.
You pulled down his pants and boxers and Cuphead nearly screamed when his cock sprung to life with a bead of pre-cum on the pink tip, for a very short person (or cup?) he was pretty average, not big and thick like you wanted but enough to get the job down. He tried all of his might to be quiet but he couldnt hold out the delicous scream that ripped out of his throat when you took him fully in your mouth and his willpower flew out of the window when you started sucking him. Now he REALLY hoped Mugs cant hear him.
"H-holy- motherfucking sATAN-! Fa- fAste-AaH!!" Cuphead moaned out when you quickly complide and went faster, He never felt so much bliss and pleasure at once in all his life until now. And Cups didnt care how much of a pathetic and horny mess he was right now. All he cared about that he was getting the best blowjob in his life.
Just when he was about to reach pure bliss you took your mouth out of him and Cups whined loudly and looked up at you while you positioned yourself ontop of him.
"Whu-? What're you doing?" Cuphead said still drunk and horny as fuck.
"Oh-hoho- im not leaving myself out of this!" You said before slamming yourself down onto the little cup getting a loud moan from him, and he lets out more moans and whines from him while you kept ridding him like you were chasing bandits in the west with your trusty horse.
Cuphead had no idea what to do with his hands so you guided them to your hips, Cups thanked you for a short moments before going back to whinning, moaning and drooling over your tight hole. You both soon got to your climax and you milked his dick til he couldnt cum anymore. After a few minutes of trying to get some air you pulled him out of you and cringed of the feeling of his cum pouring out of you like a faucet, and soon collapesed next to Cuphead and promptly passing out with him.
The next day Cuphead woke up with the worst headache and hangover he had in his life and noticed you werent there with him in bed anymore, and guessed that you left long ago. After several minutes Cuphead lazily puts on a shirt and his boxers and walks out of his room and bumps into Mugman who had had bags under his eyes.
"Brother, who the fuck did you sleep with?"