Chapter Text
Cuphead was only four hours into his shift and he was already starting to feel completely drained of all energy. His body felt limp and devoid of emotion. All he wanted to do was go home and take a long, long nap and forget about all of his responsibilities as an adult entirely.
He had only started his new job as a maid a month ago, but so far his position seemed nearly too much to handle. He worked for some wealthy demon named ‘Bendy Darling’ who had made his riches from his impressive career within the entertainment industry. Cuphead was thrilled upon hearing that he had successfully earned his position to work under such an extraordinary man- not to mention the pay for being one of his maids was an extreme plus- but only after meeting his new boss face to face did he begin to develop cold feet.
The demon was shorter than him by a significant amount, but exuded a striking sense of power and prestige. He had pitch black eyes and matching dark horns, which contrasted greatly to the pure white that was his face. He wore a sleek pair of rectangular rimmed glasses and was almost never seen without his signature black bow tie. He was so alarmingly put together and composed that Cuphead would always have trouble making eye contact with this man. And sure, the imp was a bit intimidating, but that was the least of the cup’s complaints.
Instead of calling Bendy by his name, Cuphead and all of the other servants that worked in the imp’s estate were strictly instructed to call him ‘Master’, which in itself wasn’t exactly a large issue, (being that most maid positions have the same preferences when addressing their employers,) but it was more at times that Cuphead felt as if the imp was specifically targeting HIM…
Every time a spill or a mess was made, it was always CUPHEAD that had to clean it up… whenever Bendy was to be served his meals, it was always CUPHEAD that had to serve them to him. It was always CUPHEAD that was especially instructed to take on the most tasks. There were TONS of other maids working under the imp and yet it was CUPHEAD who had to do EVERYTHING. It had gotten to a point where the cup noticed how Bendy wasn’t even trying to hide his obvious disdain for him. Whenever Bendy instructed Cuphead to take care of a mess or fetch something for him, it was always said with an incredibly sly smile. The demon’s annoying behavior dug deep underneath the cup’s skin every time. It made him nearly seethe with anger whenever Bendy would demand for him to call him Master to his face at random times or even kneel upon seeing him. Cuphead had the suspicion that Bendy wasn’t only targeting him, but seeking to completely humiliate him whenever given the chance.
Today was just the same, with Bendy finding frivolous and mindless tasks for Cuphead to complete. The cup couldn’t even stand on his own for a measly second before his boss was already demanding for him to take care of some other mundane task that he needed to take care of.
Luckily for him, the cup seemed to finally get a chance to relax if not for a moment, leaning against one of Bendy’s large shelves in the imp’s office as the demon took care of some paper work at his desk near where the cup was standing. Bendy had a habit of demanding the cup to ‘assist’ him in his office while he took care of some personal business, which was really just his way of making the cup stand around and do random tasks for the next 2 hours while he needlessly critiqued him from his desk. From what Cuphead could tell, though, Bendy seemed far too involved in his work to bark any more orders at him. He sighed to himself, hoping the imp was just getting tired.
Cuphead fidgeted with his fingers as he closed his eyes to relax a little, drowning in the calming sound of Bendy’s pen scribbling away effortlessly on his papers, the strong scent of the demon’s office permeating his senses. Even though Cuphead had a strong dislike for his boss, he couldn’t help but admit that the colognes and air fresheners he used were perfect for creating such a tranquil feeling. Cuphead’s nose stung a little as he inhaled the sharp scent of pinewood and mint.
The moments passed by as Cuphead began to feel his body grow heavier. Just as he started drifting off to sleep, the scribbling sound of Bendy’s on his paper came to a sudden halt. Cuphead hadn't realized how necessary the sound was for him to relax until it had ended. With his supply of white noise coming to a stop, the cup immediately opened his eyes to see his boss staring back at him, his chin resting in his palm.
“...So you think sleeping on the job is okay?” Bendy asked smugly. Cuphead instantly stood up straight, composing himself quickly before clearing his throat. His eyes stung from having to keep them open. It was as if he could almost feel how dark the circles underneath them had gotten.
“Uh- no, sir, I'm sorry.” Cuphead responded. He clenched his teeth as he watched Bendy sit up straight.
“Is that what I told you to call me?” The demon said, tone completely flat. Cuphead sighed heavily. He refused to make eye contact as his hands curled into tight fists, gripping the fabric of his pants.
“No…..’Master’...I'm sorry.” He muttered.
Out of the corner of his eye, the cup could faintly see a smile of satisfaction appear on the imp’s face. It made his eyebrows furrow in anger. He had never wanted to punch a man more in his entire life.
“I didn't hear a lot of enthusiasm in that sentence.” Bendy snarked.
Cuphead responded vaguely in an attempt to not let his frustration show. “I'm just a little tired.”
“Do you wanna take a nap?” The imp asked. The question caught Cuphead off guard a little. A nap? Was he messing with him? He was barely rewarded with a break during work hours, so being given a nap out of nowhere seemed a little suspicious.
“I HAVE been working you a little bit too much.. I hope you don't take any offense to it.” The demon smiled. Cuphead clenched his jaw, barely managing to keep his polite expression.
“No…it's alright. Anyway, if you're offering…maybe a small break would do me some good.”
Bendy crossed his legs as he turned around in his seat, keeping his eyes on Cuphead.
“...Sure. I could let you use the spare room until dinner. You leave at ten tonight, right?”
Cuphead nodded, thinking about his shift hours. He was always instructed to present Bendy with his food during mealtimes, and according to his schedule if he were to take a nap now he might be able to get a good two hours of rest before dinner.
“Mhm…yeah I'm here until ten.” He agreed. Bendy adjusted himself in his chair before leaning forward.
“...Would you mind kneeling for me?” The imp asked. Cuphead took a moment to fully process the question before sighing. It really wasn’t that abrupt for Bendy to randomly ask the cup to take care of such a request. With a slight scowl, he slowly began descending on one knee in front of the imp. He reeked of embarrassment.
Bendy shook his head at seeing the cup’s current position. “No, no, on both knees. Completely on the floor.” He said, pointing his finger downwards.
Cuphead hesitated a little before lowering his other knee, sitting completely on the floor now. For some reason this felt much more humiliating.
Refusing to make eye contact, Cuphead kept his eyes towards the floor before feeling a cold, sleek leather shoe lightly grace the bottom of his chin, lifting his head up. Cuphead involuntarily had no choice but to look upwards at the demon, his face growing hot at the sudden contact. Bendy simply stared down at him with that same satisfied smile as he lightly bounced his foot, causing the cup to groan in a slight frustration.
“Aw, don't be like that.” Bendy cooed. “I'll let you go in a second- I just want to hear you ask to be let out properly.”
‘Ask to be let out properly’?? What was he talking about??
“I…uhm…I don't know what you mean.” Cuphead muttered. His flustered emotions flurried within his chest so furiously it made it difficult for him to speak.
“Yes you do!” The demon grinned back. “C'mon, Just ask me nicely. Surely you can do that, right?”
Cuphead fidgeted with the hem of his uniform as he avoided eye contact again. He was used to the constant orders and tasks, but something like this needed much more time to get used to.
Sighing heavily, Cuphead kept his voice low. His face was a crimson red with embarrassment as he struggled to cough his words out.
“M…may I…take a break…M…master..?”
The cup choked out. He always felt so vulnerable whenever he was forced to say that stupid word, but something in his chest seemed to heat up at seeing Bendy’s happy reaction. It was almost as if he somewhat enjoyed pleasing someone by being so docile…
Cuphead shook his head vigorously. He tried his hardest to get rid of the strange feelings that clouded his mind. He didn’t like this! He couldn’t! Bendy was just abusing his position as Cuphead’s boss! That’s all this was!
Bendy continued to smile, resting his foot slightly as he hummed quietly to himself. It almost seemed like he was basking in the satisfaction of successfully managing to dominate the cup for what must’ve been the millionth time. Before Cuphead could fully process his boss’s movements, the imp had already slipped his foot out from underneath the cup’s chin, the cold leather leaving a chilled spot on Cuphead’s flesh. Bendy stood up straight, towering his maid.
“Good enough. You may use the spare room until I see you at dinner.” The demon grinned. Cuphead swiftly picked himself off of the floor and hurriedly giving a quick ‘thanks’ to his boss before rushing out of the office and across the elongated halls of the manor and making his way into one of the many spare rooms, shutting the door behind him.
Kicking off his shoes and flopping down on the bed, he let out a heavy and long sigh. God, it felt so good to close his eyes. His chest flurried at the immediate comfort he was met with at simply laying down on such a luxurious bed. The sheets were cold and silky with the comforters warm and plush. This felt MUCH better than the dingy mattress he often slept on at home.
Cuphead quickly got comfortable, snuggling underneath the covers, looking around for something to help him keep track of the time. On a glorious wooden nightstand beside the bed stood a small analogue clock to which the cup immediately set a timer on to wake him up for later. As he adjusted himself in bed, he stared up at the ceiling, trying to think of something to get him to drift off.
…He found it a little strange that Bendy would offer him something so convenient to him out of nowhere. It wasn’t like his boss to be so…well…nice. Cuphead’s thoughts ran as his body stilled, face beginning to flush.
…Maybe this was some type of reward? For doing every stupid little thing asked of him without any push back? Whatever the reason, Cuphead definitely wasn’t complaining. Sinking further under the covers, he felt his chest heat up. The image of the demon towering over him was stuck in his mind. In all his life he had never been in such a position where he was required to be so…docile. There might be a tiny itty bitty part of him that even thought it was…nice??
Cuphead bit his lip. He hated that he thought that! No, no, no! It’s not nice! It isn’t!
He tossed and turned under the covers as he clenched the comforter in his arms, burying his face into it. It almost scared him how comfy he was feeling at that moment. He started coming to the conclusion that maybe this WAS a reward. The thought made Cuphead’s mind flurry with slight excitement.
Reward…he liked rewards. He liked being rewarded for good work. He liked being praised and honored and thought about…
As much as thinking about him made Cuphead scowl, Bendy had taken the time to notice his drowsiness and even offer something to help. For a moment Cuphead swore that he felt a small swirl of something whirl in his chest. He liked the idea of being thought about…Maybe the only reason he hadn’t quit was because he enjoyed Bendy’s attention.
Cuphead sprung awake, the sound of his alarm beeping in a clear, crisp tone. It was already late in the afternoon! He didn’t even remember falling asleep!
Slipping out of bed and putting on his shoes, Cuphead hastily adjusted the sheets to their original perfect form, all the while thinking about how wild his thoughts had become while drifting off to sleep. He couldn’t enjoy Bendy’s attention as much as his mind was trying to convince him, right? Cuphead frowned. His head was suddenly filled to the brim with images of the demon’s stupid grin. The thought of the imp’s dumb smile made the cup grind his teeth. His face grew hot as he exited the spare room and made his way downstairs. He didn’t like Bendy. He didn’t like his attention. He didn’t like being docile or meek or taken advantage of. Absolutely not.
.
.
.
.
“Oh, there you are.” Said a feminine voice from behind Cuphead as he made his way into the employees only hall near the dining room. The cup turned around to see his coworker Chalice standing with a tray of what looked like appetizers in her hand.
“Hey, Chalice.” Cuphead greeted before immediately being handed the tray abruptly.
“You know what to do with that.” The grail said, wiping her hands on her apron as Cuphead sighed.
“Yeah…I know.” He muttered before walking out into the dining hall and being met with that same, idiot, shit-eating grin he was haunted by sitting at the end of a long table dressed in a white table cloth.
Cuphead strolled over to where the imp was seated quietly, setting down the tray and properly handing out the plates of food for the demon. As he began organizing the silverware, the cup heard the imp clear his throat before speaking.
“So, how was your little nap?”
Cuphead clenched his jaw again before looking up at his boss.
“...It was good. Thank you for letting me use the spare room. I know it wasn’t very professional, but I really appreciate it, sir.”
Bendy cleared his throat loudly, eliciting a sigh from Cuphead.
“...I really appreciate it, MASTER.” The cup corrected. Bendy grinned and nodded in response.
“You’re welcome! I could tell you needed it. So tell me what I have on my plate tonight, will you?” The demon said, resting his chin in his palm as he leaned forward in his chair.
“Um…I’m sorry, si- master- I’m not really sure.” Cuphead shrugged. “I think it’s…appetizers? I wasn’t told what they were exactly.”
Bendy shook his head disapprovingly.
“Goodness, Cuphead, you MUST get better at knowing how to serve me. Y’know that Chalice girl tried to serve me my dish earlier and I had her sent back into the employees room? I make it perfectly clear that I only want YOU to serve me.” The demon grinned, a smile plastered proudly on his face. “-I want to make sure you have your work cut out for you!”
Cuphead sighed, struggling to keep his polite demeanor. “...Thank you…Master…how thoughtful.”
Bendy nodded before waving his hand, motioning for Cuphead to continue with presenting his meal. The cup continued to quietly retrieve a bottle of wine sitting on the table and proceeded to open it, tilting the bottle of the liquid over the imp’s glass and carefully pouring the drink. In his attempt, however, Cuphead quickly found his fingers slipping, the heavy bottle of wine suddenly flailing for his grasp and dropping onto the table below with a loud thud, spraying crimson, red wine all over the pure white table cloth and even swiftly managing to splash over Bendy’s clothes.
The moment had gone by so quickly that neither Cuphead or Bendy fully had time to process the mess in front of them. The cup stood in shock for a moment, eyes widened and nearly terrified. Holy shit he was about to lose his job. No, no, nonononooo nononoonononononoononononon-
“OH! Jesus, I am SO SORRY!” Cuphead flailed as he hurriedly began wiping down the table cloth to no avail. The red liquid was already sinking into the fabric quickly, settling in with an alarming speed. As Cuphead profusely apologized and attempted to clean up any mess possible, Bendy was sitting with a shocked expression of his own, body completely still as he watched the cup struggle to clean up his sorrowful mistake. The imp looked down to see red wine sinking into his own clothing and frowned.
“Cuphead.” The demon said, tone completely cold and empty. The cup immediately stopped apologizing as he looked towards his boss with a horrified expression. Bendy’s face was deadpan and even slightly angered as his pitch-black eyes shot daggered at the cup, that sly smile nowhere to be found.
“...I’m not very happy with you.” The imp stated. A fat moment of silence drowned the two before Cuphead stood up straight, fidgeting with his hands.
“...I know.” He started, voice full of embarrassment and shame. “I’m so, so, so, sorry…master. I’m so, so, sorry- I- I can have this cleaned up right away-! I-”
Bendy lifted up a hand, instantly silencing the cup.
“No, YOU’RE going to clean this up, and you’re going to do it NOW.” Bendy said. Cuphead nodded swiftly, aiming to lift up the tablecloth to take the fabric into the washroom before the demon halted his movements once again.
“No.” said the imp. “Get on your knees and suck the wine out with your mouth.”
Cuphead paused.
“I…exucse me…?”
“You’re excused.” Bendy said as he pointed down to the floor. “Now get on your KNEES and suck the wine out with your MOUTH. You don’t want this to set in, do you?”
Cuphead slowly shook his head before carefully descending down onto his hands and knees. His head was near boiling with humility at this point. He was so filled with shame and embarrassment that he couldn’t even have the capacity in him to be mad at such an odd request.
The demon gripped some of the wine-stained cloth and held it up to Cuphead’s mouth, his free hand gripping his maid’s handle roughly. Cuphead groaned a little before placing the fabric between his teeth, using his tongue to lick around the stained cloth. He had never felt more embarrassed in his entire life. This was beyond any kind of humiliation he had faced before. He hands gripped onto the material of his pants as he took in the taste of the sour expensive wine mixed with the bland flavor of cotton.
“...Look up at me. I want you to look at me while I punish you.” Cuphead heard a cold voice say from above him. He slowly looked up to see Bendy’s expression- angered and deadpan before shifting into that of slightly satisfied upon seeing the cup’s immediate obedience.
“Good boy…now suck it out faster. If that wine sets in, I’ll take it out of your paycheck.” The demon hummed before gripping the cup’s handle even harder and pushing more of the cloth down Cuphead’s throat.
Cuphead couldn’t help but strain out a groan as his face heated up immensely. Every part of his body felt weak and vulnerable. He hated his thoughts for trying to convince him that something about this felt…right. Like this felt GOOD.
The cup’s head reeled back onto Bendy’s words. ‘I want you to look at me while I punish you...’ ‘Good boy…’ God, something about the way he said that intoxicated him severely. He could feel his arms shake as he hummed into the cloth, groaning slightly as he forced more of the fabric into his mouth. His tongue shamelessly licked more and more furiously, saliva coating the cotton tablecloth. Bendy’s eyes widened momentarily as he watched one of Cuphead’s hands gently grasp his own, softly touching it as his maid moaned softly into the cloth. The sound of Cuphead being gagged and the way his body shook made Bendy bite his tongue. He couldn’t stop staring.
“My…you’re…eager. I’ve never seen you this excited to please me, before.” Said Bendy, his tone quieter and gentler. Cuphead groaned into the cloth as a response, sucking out as much wine as he possibly could. Before long, Bendy suddenly pulled the cloth out from Cuphead’s mouth before sitting back in his chair, looking at the progress Cuphead had made.
Saliva and red wine coated Bendy’s fingers as he stared at the fabric beneath him before letting the tablecloth go.
“...You’ve barely managed to clean up any of that.” The imp said disapprovingly.
“I- I’m sorry, master…” Cuphead whined. His thoughts immediately chastised him for his tone. What was WRONG with him?? Was he THAT desperate not to get fired?? Bendy grinned slightly upon hearing how desperate Cuphead’s voice was, causing something in the cup’s chest to burn.
“It’s alright…It’s a big mess, anyway.” The demon cooed, reassuring Cuphead as he gently caressed his maid’s cheek. The gesture made Cuphead’s head spin. Why wasn’t he pulling away?? Why was this starting to feel nice???
“Why don’t you just work on something a little smaller, hm?” Bendy said before motioning to his pants and shirt. “Some of it got on my clothes, see? I’m sure that’ll be MUCH more of an easier clean for you~”
Cuphead slowly crawled closer to Bendy, his hands resting on the demon’s thighs as he bit his lip nervously. Gripping the imp’s shirt in between his fingers, Cuphead carefully places his tongue on the fabric, trying his best to clean out the stain. Above him he can hear the satisfied chuckle of Bendy, who gently places a hand on the back of the cup’s head to keep him in place. Cuphead continues licking out the stains on Bendy’s shirt until they’re nothing but faint pink-ish blobs. Bendy uses his hand to force Cuphead away from his body as he stares down at the slightly cleaned fabric.
“Well…It’s still noticeable, but you DID make better progress on THIS than the tablecloth…” Bendy hesitated. Cuphead kept his place on the floor. His mouth was crowded with nothing but the taste of strong wine.
Bendy looks down at Cuphead, motioning to him with a hand for him to come closer. Cuphead, doing as told, inches near the demon, who uses a hand to bring the cup’s face closer to his. Cuphead hesitates, staggering for a moment. He had never been this close to his boss before. From here he could faintly smell that same cologne that lingered in his office. The imp’s skin looked so smooth and soft…and his lips looked so warm…
Cuphead suppressed the urge to shake his head again. Why was he THINKING like this?? He hated that it felt so good and that he couldn’t even deny it anymore!
“...How about I give you a reward for doing such a good job?” Bendy said, his fingers gently caressing the bottom of Cuphead’s chin. Cuphead nodded in response, a slight smile that he couldn’t hide appearing on his face. He was sick of pretending that hearing Bendy praise him filled him with hatred, even if he wasn’t exactly ready to fully accept such a fact.
Bendy carefully pulled the cup closer to him, causing Cuphead’s eyes to widen at the close proximity. He could feel the heat emitting from Bendy’s body as he gripped onto the imp’s legs for support. He swallowed hard before feeling the demon’s soft breath on his lips.
“...Is it okay if I do this? I could always reward you with something else…” Bendy said softly, his voice barely above a whisper. Cuphead thought. Hard. What was he doing?? Was this actually happening??
Cuphead’s face subconsciously moved in closer towards the imp. His mind was reeling with confused and anxious ideas and thoughts, all of which were too jumbled to control. His mind flurrying so heavily made his headache, and before he knew it, his lips were barely inches away from the demon’s. Bendy carefully grasped the cup’s face a little harder for more support before fully going in, bringing Cuphead into a swift and soft kiss.
Cuphead was surprised- but not disgusted. It actually tasted really…sweet. Like mint candies. Enjoying the flavor, Cuphead forwarded his mouth onto the demon’s a little more. Oh, God, what was he doing??? Not only was this an absolutely absurd thing for Cuphead to do- it was also completely inappropriate!
As the cup’s mind continued to be overlapped with jumbled and anxious thoughts, the demon carefully moaned into his maid's mouth, causing the small sense of vibrations to force a chill wash down Cuphead’s spine. It was exhilarating to say the least. The excitement almost made Cuphead calm down as his limbs shook. His hands gripped onto Bendy’s legs harder as his tongue perfectly responded with the imp’s, their saliva washing over one another. Against Cuphead’s warm lips, Bendy could taste the lingering flavor of the wine that he had forced his maid to extract from the tablecloth fabric and his shirt only moments ago. His skin was so soft and hot…He had been fantasizing about a moment like this for ages. It was so cute teasing Cuphead- and now he had the cup’s tongue wrapped around his in such an inappropriate manner that riled him with such ecstasy that it forced a thick moan from his mouth. The demon’s free hand almost instantly moved towards the cup’s face, grasping Cuphead’s soft skin as he put more pressure onto his lips, his tongue moving forcefully in the cup’s mouth.
Cuphead was alarmed by the speed, but again, was surprisingly content with the feeling. Hearing the moans coming from Bendy and feeling his rough fingers against his skin made the cup close his eyes in desperation as he returned the forwardness of the kiss, tongue eager and swift against Bendy’s. His hands moved to wrap around the imp’s back, moving his fingers gently to fully grasp the feel of the demon’s body shape in his palms. He was wonderful. This was wonderful. As soon as those jumbled and confused thoughts had entered his brain, within a moment they had left just as quick. Cuphead savored the flavor of Bendy’s saliva, secretly wanting more as he felt his body completely give up and submit to the demon. Fuck, this felt so good. He breathed heavily as he groaned into the imp’s mouth. Bendy pulled away for a moment to allow the cup a moment of much needed air. For a sharp second Cuphead could swear he saw a string of saliva connect their mouths before Bendy had forwarded his tongue back in between the cup’s lips, the two continuing their rough and steady make-out session.
Within a moment, every drop of held-back tension and need flooded over like a dam breaking. Cuphead’s hands could only grip onto Bendy’s body while the demon could only moan words of praise towards the cup, enjoying every single reaction given to him in response.
“...Such a good boy, Cuphead...” Bendy groaned before instantly pressing his mouth back against the cup’s. “Such a good, good boy for me…You’re taking my reward so well…”
Cuphead flinched with excitement every time Bendy offered him lovely words of praise, his rational thoughts drowned out by the sound of the imp’s voice calling his name so sweetly.
For what seemed like the final time, Bendy pulled away from Cuphead, this time slow and deliberate. The cup heaved, taking in much needed air as his body shook furiously. His hands remained on Bendy’s back as he stared at the demon’s lips. He wanted to face-palm himself for acting so stupid- but at the same time it felt as if his body was completely enthralled with being handled the way it had by the imp.
Bendy gently held Cuphead’s face again, forcing him to look up into his eyes. It wasn’t until the imp snickered that Cuphead had snapped out of his excited trance.
“Heheh….and here I thought you HATED me!” Bendy chuckled to himself. Cuphead’s eyes widened as he immediately straightened himself up.
“Not HATE- just…Ugh let’s just pretend this never happened.” The cup muttered in response. Bendy paused for a moment as he kept his gaze on Cuphead, his sly smile returning.
“Well, if you want. But just so you know, I wouldn’t mind if you’d let me reward you more often.” He teased.
Cuphead hesitated before huffing out a breath. For some reason he was having trouble instantly denying that he ever wanted to do anything like that with Bendy again.
“...Whatever you want, ‘Master.’” Cuphead smiled sarcastically. Bendy gripped the cup’s chin gently before planting a small kiss on his maid’s cheek, causing the cup to put on a more genuine smile out of excitement.
“...That’s what I love to hear!”
Da end Chalice mentioned bcs I love her and whatever.