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It had been about four weeks since Cuphead had turned to tutoring in order to ensure he not only had the chance to leave his Sophomore year behind to transfer into his Senior year, but to also make sure he graduated high school at all.
Tutoring was never Cuphead’s idea of a fun time, but he couldn’t help but admit, the last three weeks spent in the school’s library writing and reading were actually…entertaining.
It wasn’t the large improvement in his grades he was excited about- or the fact that he was learning things that never even crossed his mind- it was more so the little ‘perks’ given to him by his tutor and best friend, Bendy.
Bendy was an imp who was a bit on the shorter side. He wore framed, square glasses and was almost never seen without a signature bow-tie. He made a strong effort to do well in school and be known to his teachers as a ‘good kid.’ And he was, in fact, a good kid.
However, something most teachers- or students- didn’t know about the demon was his heavy and outlandish attraction to one of his best friends, who just so happened to be Cuphead himself. It wasn’t extremely unbelievable, though. After all, Bendy and Cuphead DID seem like a close pair of friends….
But from the demon’s raging attraction to the cup, it was obvious he wanted a little more.
And his willingness to eventually express his wants to Cuphead made his friend realize that it might not be so bad to get to know one another on a more…closer level.
Just like any Friday after school, Cuphead and Bendy were seated in a study booth cooped in a semi-hidden corner of the school’s library. The soft scent of books and strong herbs flourished in the still air. The library was pretty much always dead during this time of day considering not a lot of students required mandated tutoring- so to Cuphead and Bendy’s excitement, they often had the tranquil space to themselves to study.
Most of the time, like now, however, they were in fact, NOT studying.
Cuphead’s tongue moved gently with the demon’s as Bendy sat in the cup’s lap carefully, making sure to keep their bodies close to one another as they kissed. The imp’s sharp fangs often grazed Cuphead’s lips as they softly moaned into one another’s mouths. Cuphead’s heart was thumping furiously in his chest as his palms pooled with sweat. He gripped the back of Bendy’s sweater vest harshly as the demon continued to kiss him with rough and passionate movements. It was hard to believe Cuphead had realized his more than friendly emotions for his friend only a few weeks ago. Now that he was so used to making out with Bendy in such a way, it was hard to imagine his life without such a sensation.
Though the thumping of his heart was the only booming sound Cuphead could hear echoing in his mind, he didn’t want this to stop. He didn’t care how uncomfortable he was- how the sweat from his body caused his clothes to cling to his skin or how he felt a scared thrill chase up his spine whenever he could feel Bendy’s sharp teeth- he felt as if he’d go insane if this ever stopped.
Bendy seemed to be returning Cuphead’s strong emotions as he gripped onto the cup’s shoulder with one hand, keeping his other dangerously close to squeezing Cuphead’s throat. Cuphead squirmed as they continued to kiss. This touching was addictive- but also insanely overstimulating.
To make things worse, every time the two broke apart their lips to catch small breaths, Bendy had taken it upon himself to mutter things like ‘good job’ and ‘well done’ in a soft tone that made Cuphead’s head spin. He gritted his teeth as Bendy let out such remarks, craving more words of praise while also feeling strongly embarrassed about enjoying them.
Still, the thick sense of pleasure continued as the pair made out. They could’ve kept going until the library closed for the day if it wasn’t for the sound of footsteps coming toward their study booth.
Cuphead jolted as he heard the sound near, and almost at the exact same time, so did Bendy. The imp nearly dived off of the cup’s lap and into his own seat, hurriedly fixing Cuphead’s mangled and disheveled collar before the school’s librarian came to their table.
It wasn’t hard for Cuphead to act as if nothing was wrong. He had a poker face blessed to him by God himself. It was Bendy that seemed more worried and unregulated.
Sweat poured from the imp’s face as the librarian smiled at the two, small trails of black ink dripping down the demon’s forehead. Bendy nervously fidgeted with the hem of his sweater vest as he greeted the school’s employee.
“Hi, Miss Brightney!” Bendy greeted with a wide smile. If it wasn’t for Cuphead’s smooth expression, the librarian would’ve for sure gotten more suspicious than expected.
“Hello, you two.” Miss Brightney, the school’s librarian responded. Her eyes were slightly skeptical from behind her thick glasses.
“I just came over to check on you…I noticed it had gotten really quiet.” She stated, looking over to Cuphead, who just stared back nonchalantly.
“Oh! Whoops! Sorry!” Bendy stammered, obviously worried.
“...You don’t…you don’t have to apologize.” Miss Brightney responded, causing Bendy to stutter a tirade of make-up remarks.
“Oh! Oh, yeah, I mean- we’re fine. We’re doing alright here.” The imp said, brushing lingering ink from his face. To Cuphead’s glee, he seemed to finally be relaxing. Miss Brightney shrugged slightly as she nodded, sighing a little underneath her breath as she began to walk off.
“Alright, then. Just be sure you two are actually doing work.” She ended. Cuphead could’ve sworn she had glanced at his exposed neck, which was undoubtedly covered in bruises from previous ‘study’ sessions.
Lucky for him, she did nothing but walk away.
Bendy visibly relaxed when the librarian was out of view, sinking slightly into the booth’s comfortable seats. He was embarrassed enough as it was, and it didn’t help that Cuphead almost immediately started laughing at him.
“Wh- WHAT???” Bendy semi-shouted, keeping his voice stern but moderately quiet. He was obviously upset at being teased as his face flushed. Cuphead snickered his words as he attempted to respond.
“You looked so stupid.” he chuckled, hand covering his mouth as he let out hearty snickers.
Even though he was being made fun of, Bendy couldn’t deny that Cuphead was always so adorable when he laughed…the sight of his friend’s pretty smile and brightened expression eventually caused him to snicker as well, despite his efforts to hide his amusement.
“Whatever. I tried! And how was I supposed to know she would come over here?” Bendy argued. His smile was just as wide as Cuphead’s.
“It’s HER library, idiot.” Cuphead retorted. “Maybe you should stop trying to kiss me in public so much.” He snickered.
Despite Cuphead’s words being unserious, Bendy felt his heart jump. He had fantasized about kissing his best friend for years. The fact that they were so openly stating that they were now closer in a way Bendy could only dream of was a little jarring, but nonetheless exciting.
Unable to keep his hands to himself any longer, Bendy softly took hold of Cuphead’s shoulder, feeling joy sweep over him as he reveled in the feel of the cup’s warm skin underneath the layers of fabric blocking his soft, gray, porcelain skin.
Bendy wanted to ruin that skin in any way he could physically manage.
“...You like it when I kiss you.” Bendy responded, returning to his usually charismatic persona. Cuphead continued to smile, but stopped snickering as his face flushed. It was so cute how even after weeks of kissing, he was still riled up by the smallest amount of physical touch.
“...Maybe.” The cup said, grinning slyly. The two silently went back to doing actual work, flipping through textbooks and writing down notes as Bendy gifted the cup small pecks on the cheek and words of much-needed praise after every job well done.
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“Will you be my boyfriend??” Cuphead asked, his tone a little pleading as he put on a hopeful expression. To his dismay, His brother Mugman and best friend Chalice simply stared with judgmental looks.
“...That…that’s a start.” Chalice muttered sarcastically, adjusting her cyan-tinted glasses as she raised an eyebrow. Mugman simply groaned as he rubbed the bridge of his nose.
“Every single attempt before this was ‘a start’” Mugman bluntly pointed out before looking at Cuphead.
“I’m just saying you sound a bit whiney.” Mugman stated, rolling his eyes. Cuphead always expected his brother to be judgmental over the smallest things, but as he looked towards Chalice for a second opinion, he was only met with an expression that screamed ‘I’m sorry, but he’s totally right.’
Cuphead groaned. He and Bendy had been on plenty of dates before- which were events only he, Bendy, Mugman and Chalice were aware of- but now he was sure that he wanted things to be more ‘official.’
He wasn’t the most romantic person- he never really cared about that stuff- but Bendy made him feel…safe. Bendy was familiar. Bendy was someone he WANTED to kiss. For years he had been a confidant and a friend…but now, Cuphead kind of wanted him to be a lover, too…
“I’m TRYING.” He let out, his head hanging low. The three of them were standing in the hallway of their school, staying close to the lockers as multiple kids passed. “I’m really, really TRYING. But to be fair, it’s kind of hard to be serious when I’m asking this question over and over to well…YOU guys.”
Cuphead heard Chalice grumble under her breath.
“...Why do I ever go to this school…” She questioned, her face in the palms of her hands.
“Yeah, your life sucks.” Mugman smiled slyly as he answered Chalice’s rhetorical grumbles. “You only ever go to school like- twice a year and you chose the day when Cuphead’s complaining about being homosexual.”
“I’m not-” Cuphead interrupted before being cut off by Chalice.
“I can LEAVE whenever I want- but I DON’T because I’m THAT GOOD A FRIEND.” She argued. Mugman only scoffed in a jokingly mocking tone.
“I like it better when you do that thing where you turn into a ghost and we just forget you exist.” Mugman said. “That would be such a funny thing for you to do right now. You should make us all laugh.”
“WHAT???” Chalice questioned, her voice a little too loud. Cuphead was about to step in between their petty joke-argument before the blaring chime of the bell echoed throughout the halls, signifying the start of class. Cuphead grumbled angrily before he remembered his next period was the only one with Bendy. He didn’t have tutoring today after school- so it looked like he’d have to try and make today count.
“Y’know what? I have my next class with Bendy.” Cuphead said as he watched kids scramble through the halls to their next classes, Mugman and Chalice grabbed needed books from their lockers.
“I’m just gonna ask him then.” He said, voice reeking with confidence.
Unsurprisingly at the same exact time, both Mugman and Chalice looked at Cuphead as they slowly sucked air through their teeth before making an ‘ooooooh’ sound, obviously implying they thought the idea was stupid.
In response, Cuphead lovingly kicked them both in their shins jokingly, showing off his pretend anger.
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As usual, Cuphead took the seat right next to Bendy in the back row of the class, the demon greeting him with a smile. During class, Bendy would often do small things that would get Cuphead riled up, like brushing his foot close to his under the desks or ‘pretending’ to accidentally brush his hand against his. The demon loved to tease, and he knew everything he tried worked on Cuphead flawlessly.
It was close to torture the way Bendy would act like he wasn’t doing anything. He masked his emotions in such a way that from a bystander’s glance, it was just a pair of friends being friends.
It drove Cuphead wild.
…He loved it.
After a while of pretending to take notes, (Bendy was the only person who could get Cuphead to actually learn anything-) their teacher had cleared the blackboard with an eraser as they reached for another stick of chalk. To their surprise, there was none left. They looked over at their desk and around the blackboard for any lingering pieces before they sighed, realizing they would probably have to get more.
“Cuphead, would you get some chalk from the cupboard back there, please?” The teacher asked. The materials closet was right behind the cup, who nodded as he got up and searched the cupboard. To his surprise, the space where they kept the chalk was empty.
“... there’s none left.” He said, closing the cabinet. Their teacher did nothing but sigh in response.
“...Great. Well, since you all know I can’t continue the class without any chalk, who here would like to travel down to the office to get another box for me?”
No one raised their hands.
“....Alright. Cuphead, could you go, please?” the teacher asked, voice worn and tired. As much as Cuphead didn’t want to go, he did nothing but sigh and nod as he headed out the classroom, entering the school hallway.
As Cuphead trudged towards the office, he heard footsteps come up behind him. Turning around, he was face to face with Bendy. Cuphead smiled as his heart jumped slightly.
“...The teacher asked me to go with you.” Bendy said, smiling up at Cuphead with a sly grin. “..To make sure you actually GET it.”
“Oh well.” Cuphead shrugged in response, smiling passively, not at all caring that his teacher thought he was so much of a delinquent that he couldn’t even be trusted to get a box of chalk. “I guess we're walking to the office together.”
Bendy didn’t say anything. A thick moment of silence passed before the imp suddenly took Cuphead by the hand, leading him towards a set of stairs that descended to the lower floors of their school. Cuphead felt slight confusion rise in his chest considering that the office was on their floor, but also a slight sense of joy with the fact that Bendy was holding his hand.
“I- isn’t the office that way?” Cuphead asked, not objecting as Bendy walked him down the stairs. They descended multiple times until they were at the very bottom floor of the school, making sure to stay clear of hall monitors. It wasn’t until Bendy had led Cuphead down another set of stairs he didn’t know existed onto a more dimly lit floor that was devoid of anyone else.
Immediately, Cuphead noticed how this floor didn’t have overreaching hallways that stretched on and on. It also didn’t have any classrooms in sight. In fact, it was more like a large room built at the bottom of the school than a floor. The staircase down was only a few steps, so even though the room was dark and it’s lights were completely off, there was still light shining from the floor above. Cuphead tilted his head softly.
“..Where are we?” He asked. Bendy gently let go of his hand as he made his way through the room and sat on a bench. Stepping closer, Cuphead could see two vending machines (turned off, sadly) resting behind a row of benches.
“It’s just a small hangout spot.” Bendy responded. “Some kids like to come here to chill during lunch. It's also the only place in school with vending machines. They only work during lunch, though.”
Cuphead stared in awe. He had no idea such a place existed. It really was just a hidden area he never even knew existed. Still, it was nice. It was comfortable. The lack of lights and soft blue hue of the tiled floor made the area tranquil and peaceful. Cuphead sat down next to Bendy, looking at him with a small smile. There was a bit of nervousness behind his expression, but Cuphead was hoping the demon wouldn’t notice.
“...I just figured…” Bendy started, scootching closer to the cup as his tone softened. “...Since there’s not gonna be any tutoring today after school…we could get our lessons in now.”
Cuphead’s throat tightened. Bendy looked at him with a gaze that made his mouth dry up. His legs felt weak and useless. He kept absolutely quiet as Bendy neared closer, softly holding Cuphead’s cheek with the palm of his hand, using his thumb to stroke the cup’s skin softly.
“...I wanna show you something new I came up with…I think you’ll like it.” Bendy smiled. Cuphead did nothing but nod silently. He felt completely at the demon’s mercy, already willing to do anything asked of him.
That was exactly how he liked it.
Bendy neared his lips towards Cuphead’s slowly before stopping, their mouth’s inches away from each other’s. Cuphead waited for when the imp would close that distance, but the moment never came. He looked at Bendy with a confused glance, wondering what was taking so long.
He was only met with a snarky grin.
…Bendy was teasing him. Again.
Cuphead scoffed as the two locked eyes, neither one of them moving.
“...You don’t seem too excited.” Bendy commented, causing Cuphead to smile.
“I don’t?” He asked. Bendy shook his head ‘no.’
“I want you to be desperate.” He admitted. The remark made Cuphead’s heart jolt in his throat for a minute. “It’s not fun if you’re always expecting me to kiss you. Predictability gets boring. I want you excited so you get the most out of the experience.”
Just as Cuphead was about to respond, he felt Bendy’s hand move to his neck, gently pulling down the collar of his shirt as he softly stroked the cup’s throat.
“...So…I’m gonna make you REALLY want this.” Bendy sighed.
Cuphead’s chest flared up with heat. Immediately, he tilted his head back, allowing the demon to do as he wished with his neck.
“Good job…” Bendy praised, instantly causing Cuphead to smile as his face flushed. “...At least you’re obedient.”
Bendy continued to sooth the skin on Cuphead’s neck, the touches more sensitive than usual considering the skin on this area was covered in bruises and hickeys left by the demon himself. Bendy simply stared at the marks. It was almost as if he was admiring his own work.
Cuphead had never taken the lead before. He always waited for Bendy to kiss him first before they made out. But now, he was contemplating whether or not he should take the first step. This slow-burn was clawing away at him.
He had often thought about kissing Bendy on his own before and what he would do- but now that he was in a situation where such a thing could be carried out, he felt nervous and unsure. He liked that Bendy was the more dominant one when it came to them kissing- but sometimes he wondered how it would feel to be the enabler.
His heart pounding, he softly wrapped his arms around Bendy’s back before slowly tilting his neck down again, causing Bendy to move his hand out the way. Cuphead felt his head boil before he neared closer to the demon, closing his eye and aiming to kiss the imp before-
“No.” Bendy said sternly, pushing Cuphead’s face away. Cuphead gave a sad glance to the demon, but didn’t argue.
“I think it’s cute how you already want to kiss me so badly- but I want to drag this out a little longer.” Bendy smiled. Cuphead was beginning to see a sadistic glint in the demon’s grin. It scared him.
….Unfortunately In a good way.
“But-” Cuphead stammered, wanting to argue. He could feel his legs shake. Swallowing hard, he steadied himself as his confidence came back to view.
Leaning over, Cuphead slowly positioned the two in such a way that Bendy was laying back on the bench, the cup looming overhead.
“...I want to kiss you.” Cuphead muttered. It was hard to admit, but he knew being upfront was the only way to get what he wanted at this point.
“..REALLY badly. I want to kiss you so, so much.” Cuphead sighed, seemingly giving up. He held his head down and shut his eye tight as his breathing became rigid. Bendy stared up at him wide-eyed, taking note of how the cup’s desperation started seeping through.
“Please?” Cuphead breathed. A fat moment of silence came between them before Bendy adjusted himself so that he was no longer laying down, sitting face to face with the cup. He smiled widely as he crossed his legs, cradling Cuphead’s cheek in the palm of his hand again. Immediately, Cuphead leaned into the touch.
“...You’re so good for me.” Bendy praised. “You want me so much you’re willing to BEG?”
Cuphead nodded fervently, his head close to a boil. It was a miracle how Bendy’s hand wasn’t being scalded by the heat emitting from his face.
“...Fine.” Bendy grinned. “Do it. Kiss me.”
Cuphead’s entire body went limp before he swiftly swooped in, instantly closing any distance between his and Bendy’s mouths. He loved being teased, but he loved this much, much more. He didn’t hesitate to wrap his arms around Bendy again, gripping the demon’s shirt as he made sure to move his tongue as rough and as passionately as he could. God, he loved this. He loved Bendy. He wanted nothing more than to taste Bendy’s sweet breath and feel his soft tongue rub against his until they went numb.
Bendy broke the kiss as he allowed Cuphead to breathe, a string of saliva connecting their mouths. It didn’t take long before Cuphead immediately went back to kissing the imp, gripping the fabric of his clothes and moaning into the demon’s mouth. The imp quickly returned the cup’s excitement, his own wants coming into play as he roughly gripped Cuphead’s collar, yanking it down before swiftly breaking the kiss again to bite and nip and lick at Cuphead’s sensitive throat. Cuphead groaned out of soft pleasure as Bendy chomped down hard on his neck, causing him to let out a sound of pain, though he didn’t want this to stop for one second.
Cuphead allowed Bendy to make a mess out of his skin, marking up his neck even more. His sharp teeth felt like Hell and Heaven all at once. He breathed heavily as he squirmed underneath the demon, with Bendy quickly kissing Cuphead again in an attempt to silence his loudening groans.
Cuphead’s mouth quivered from overstimulation as Bendy deepened their kiss, only to back away suddenly. Cuphead heaved and filled his lungs with air before attempting to kiss the demon again, only this time Bendy covered the cup’s mouth with his palm.
“...We should probably get that chalk.” He smiled. Cuphead stared at him with slight annoyance, but knew he was right. If they took too long making out, their absence would become extremely suspicious.
“Fine.” Cuphead grumbled, causing Bendy to snicker.
“Awww you’re so upset! I bet you’d just LOVE to kiss me all day, huh?” The demon teased. Cuphead smiled as his face became completely red. Bendy was pretty much spot on.
“Well, this little ‘lesson’ was only to tide you over until the next time we meet up for tutoring. You’ll be fine til’ Wednesday, right?” Bendy asked, already standing up and making his way towards the staircase.
Cuphead stood up after him, his throat tight again. He felt like he was choking. Finally, as Bendy was making his way up the steps, the cup spat out his question.
“Do you wanna be my boyfriend??”
Bendy paused. He looked back at Cuphead with a wide-eyed stare. It was a shocked look he’d never seen on Bendy before. Like he was genuinely caught off guard.
“...You…you what?” Bendy mumbled. His tail stiffened. Even in the dim lighting, Cuphead could see Bendy’s face change to a slightly darker shade.
“....Do you wanna be my boyfriend?” Cuphead repeated, only this time more quiet and soft. Bendy stood still for what seemed like forever until a small smile appeared on his face.
“...Sure…yeah, yeah, sure. Like…officially?”
“...Yeah…”
“...Do you wanna go on a date with me?” Bendy asked softly, his smile widening as that familiar ink dripped down his forehead.
Cuphead smiled brightly, his smile growing uncontrollably.
“...Sure..!”
They held hands in public for the first time and were both very nervous :)