Seduced Into Despair by UYP

by koopatroopa482

You received an invitation to visit Hope's Peak Academy, and wake up inside the school with fifteen other students and are forcibly put into a killing game by a robotic black and white bear named Monokuma, the supposed headmaster of Hope's Peak. And for some reason, Monokuma has taken a liking to you.

Ultimate.

It is a title given to people that's best described them to be the very best in what they specialize in. While it was originally called 'Super High School Level (insert talent here),' most people prefer the Ultimate title better. People with an Ultimate talent are often highschoolers, usually being fifteen to eighteen at best. Though, there are some instances that their adults with Ultimate talents.

And you just happen to be one of those people.

To get introductions out of the way, your name is Y/N; a young adult with an Ultimate talent that led you to be very successful. What is that Ultimate talent you may ask? Well, dear reader, your talent is the Ultimate Cafe Owner.

While having a talent like that would be considered to be uninteresting and lackluster to some people, there is a bit of context as to why you chose to do this profession and became the way you are now. You see, ever since you were a kid, you dreamt of opening your own business one day. Whether it be a restaurant, game store, tech stuff, or anything in between, you had an active imagination and wanted to be big and successful in the public eye. By that, you wanted to up a cafe.

You always enjoyed hanging out in that place with your parents after taking a good trip around the city or just finishing a busy day of work, the quiet peaceful atmosphere calming your nerves and eating lots of tasty sweets and baked goods too. So after spending years studying business and marketing, you finally achieving your dream of opening up your very own cafe. And to your surprise, it became a massive success. Because of your smart decision-making in investment, a wide variety of meals on the menu items (Including limited time events/collabs), and unique marketing strategies via commercials and billboards, your cafe was number one all over the world. You successfully floored the completion with other cafe restaurants for having an excellent mindset for attracting the old and new generations.

You were on top of the world in the restaurant game. And because of your overwhelming success due to your talent, you've gathered the attention of one particular school. That school was Hope's Peak Academy.

It is a government-sanctioned co-ed high school located in a private city in Japan with multiple boarding facilities. They scout individuals who primarily have their talents and enroll them based on two criteria. For already attending high school and proving that they are the best at what they do.

You find it pretty odd that this school decided to scout you in particular as you received countless e-mails and calls from the associate affiliated with that academy, not to mention your friends and coworkers constantly egging you to attend this school. To find this to be very weird cause one; you already done your education long time ago, and two, you'd stick out like a sore thumb if you're with a bunch of high schoolers. You'd be better off if you were a teacher or guidance consular or something. Another thing is that you find this to be very… shady.

You couldn't quite put your finger on it, but something about Hope's Peak just rubs you the wrong way, like something is going on behind the scenes that not many people know if they plan on attending this school. Course, you having common sense, decided to ignore the invitation and move on. But, with the endless calls, emails, and your coworkers constantly nagging, you eventually caved in, filing an application and planning a schedule to meet with the supposed headmaster of the school in the coming days.

Something tells you that you'll immediately regret making that decision further ahead.

When the day finally came, you left early and took a private jet over to Japan, heading straight to Hope Peak Academy, with the help of the headmaster's message giving the accurate coordinates to the private facility in case you get lost. After making your way through the massive school campus, you set foot upon the main entrance of the Academy. However, as you took a step forward to enter the building, you were suddenly hit with an extreme wave of dizziness and nausea. You couldn't comprehend what was happening as your vision became warped and distorted till eventually, you blacked out…

Little that you know that this would be the last time you get to see the outside world.

Slowly slipping out of unconsciousness, you wake up in what seems to be a classroom, with the windows all covered in large thick metal plates and bolted shut. Immediately, questions began piling on inside your head at the station you're in.

Why did you fall unconscious when entering the school grounds? Why are windows sealed off? And more importantly, how long were you out?

Before you can contemplate any further, you see a letter down in front of your school desk. Opening the letters, you read to message that's written out in red crayon.

'Head to the main entrance of the school building.'

Not wanting to stay in this classroom any longer, you decided to abide by the letter's message and exited the classroom, walking through the empty halls of the school, a pit forming in your stomach at the silent, eerie atmosphere. Eventually, you reached the entrance of the building and needless to say, you were pretty shocked at your seeing. The entrance is locked up by a large vault door, with numerous locks and panels that are advanced and complex to prevent you from leaving.

However, when entering this room, you're not alone as a group of students with their Ultimate talents are also locked in here with you. When talking to them, you asked how they ended up here to which they all gave their story with one in common. They all woke up somewhere in the school after losing consciousness when stepping inside the school grounds. Before you ask more questions, the school bell chime went off, causing one of the school monitors in the room to suddenly flick on, showing a static image of the Hope's Peaks emblem. Then, an unknown voice spoke through the speakers, sounding happy and childish.

"Ahem… Attention all students! Please make your way to the gymnasium so we can begin the entrance ceremony!" They said before the monitor flicked off, leaving you and the other students in silence.

As the other students began to make their leave, you stood in place. All of this feels… very weird. And you're not the only one.

Something about that announcement felt very offputting, like its one big setup or something. But, you can't deny that you and the others that curious to find out what's going on. And besides, if you stay around, who knows whether or not you'll be safe. So with no other choice, you and the remaining students in the main entrance began making your way to the gymnasium to attend the entrance ceremony, feeling an uneasy dread as you went along.

With all of you present in the gym, the announcer from before made their grand appearance, popping up on stage before you all. Needless to say, it's not what you were expecting.

They're a black and white bear whose face and body are divided by the center into two colors, kinda loosely resembling the Yin-Yang symbol. The right side of their face resembles the classic appearance of a teddy bear, while their left side shows a more sinister appearance, having a large evil grin and a red, jagged eye resembling the Hope's Peak Academy logo. Of course, the area of division for his black and white appearance that isn't affected would be his snout and belly, which has a large, produced belly button with an "X" shape mark on it.

They introduced themselves to be Monokuma, and that it, or rather he, is the school's headmaster. You and others couldn't believe what they were seeing. Seeing a teddy bear move around and talk with such a bright and carefree attitude felt really out of place. It might be one of not the strangest things you ever saw with your own eyes.

Anyways, as the ceremony commences, the black and white bear says that we students with Ultimate talents represent the world of hope, and to protect such hope that he wants us all to live a communal life together within the confines of this school, up until the day we die. This catches the students off guard, thinking that the bear is pulling some kind of sick joke. But, he's not. He's dead serious and says that the school completely cuts all of us off from the outside world. So, seeing all those metal plates covering the windows from before confirms your suspicion. You are truly trapped inside this school.

Of course, this causes all of the other students, yourself included, to voice their dismay at having to live inside the school for the rest of their lives and that they immediately want to leave this place. This confuses the black and white bear for wanting to leave so soon and he questions you about coming to this school of your own free will. You couldn't help but agree with him. You did come to Hope's Peak Academy, but it was out of morbid curiosity, that's it.

Anyways, Monokuma goes on to explain that there is one way to leave this school. He calls it the 'Graduation Clause.' To summarize in his own words, if someone were to disrupt the harmony he wants to maintain, then that said person can 'graduate'. And to do that… you have to kill someone if you want to leave.

As soon as you hear those words, you felt your blood turn cold.

'Kill…? Why do we need to kill each other to leave?' You thought.

The reason why he wants to kill each other is that you and the students are considered to be the 'hop of the world.' So he wants that hope we cling onto and crush it to make us fall into despair. In short, he sees all as an exciting game, to bring out the worst in human nature to survive. This caused an uproar within the gymnasium, begging the black and white to just let us go home instead of having to resort to murder. But, the headmaster was having none of your excessive whinings.

He firmly states that the school is permanently your home, your life, and your world. If none of us like it, then we have to kill each other to leave, simple as that. He also states that if any of us violates school regulations, such as harming the headmaster, we would be punished. He has surveillance cameras and numerous Monokuma's pastered all over around the school to monitor us strictly for having us follow the school's regulations, making sure none of us make one slip up. To close off the ceremony, the black and white bear handed us an e-handbook, a device that serves to record many digital records.

With that, Monokuma disappeared, leaving you and everyone else in a state of shock and confusion, the atmosphere within the gymnasium feeling heavy as the words of the headmaster replayed within your heads.

'You must kill someone if you want to leave this school!'

Hearing those words planted viscous thoughts within you and everyone else heads as each student looked at each other, trying to gauge onto thoughts. It made all of us suspicious of one another, wondering whether or not someone will betray us.

And with that, this is where your 'school life' truly begins. This school is one that you came to out of morbid curiosity, only to be locked in and forced to play this killing game to survive.

It has been a few days since you and fifteen other students had come and since been trapped within the confines of Hope's Peak Academy. It's been… interesting to say the least.

Considering the obvious fact of being locked inside the school for all eternity, you and the other students have food and water as well as designated dorm rooms with specialized locks to prevent anyone from breaking in. At least that gave you some sense of comfort. Everything else, not so much. Everyone is still on edge at being put into this hopeless situation and having to deal with a potential killer brewing among us, ready to strike at any moment.

However, during the time living out your daily school life, you began to notice something rather… strange going on with the headmaster of Hope's Peak Academy. And to this day, it still left you with more questions than answers.

Monokuma, all of a sudden, has taken a rather odd interest in you.

Now, why is it that a psychopathic, robotic, black-and-white bear became intrigued with you to begin with? Where do you even start on this one…?

This whole fiasco started when Monokuma called you and everyone else to the gymnasium one day because no one has made a move to murder someone out of cold blood. All of us (including you) are strong-willed and won't abide by Monokuma's rules to the killing game he started and will not fall into the so-called despair that he's constantly bragging about. So, seeing all of you still clingling onto that hope, the black and white bear decided to… spice the game up a little in an attempt to crush it.

He summoned all of us to the gymnasium for an 'important announcement,' you and others on edge about what the bear has planned. The reason he wants us all to appear in the gym is that he feels detected that no one has decided to kill each other. So, to make the game more interesting and to give motivation to anyone who'll betray the other students, the headmaster gave each one of the students envelopes which contain our deep dark secrets thanks to him doing extensive research on everyone's personal private information. Meaning, he doxxed everyone. This is his way of motivation for the killing game, and if anyone is not murdered within the next 24 hours, he'll expose everyone's secret to the entire class.

As you and the others opened the given envelope, a wide range of reactions was displayed from each student. Some are shocked, some are filled with dread, and some are downright furious. But, for your secret, it was not the kind to expected to be, not something embarrassing or dark you've hidden away in your past or anything of the sort. Instead, it left you feeling… confused. The note read:

'Y/N's got a big ol' crush on Headmaster Monokuma!'

Immediately, several questions ran through your mind as you try to wrap your head around this rather oddball of a secret Monokuma dug up from you.

' Why in the world would Monokuma think that I have a crush on him? I don't even like that creep to begin with!' You thought.

While you're still confused by the unorthodox note, you felt a sense of concern and fear settle within the pit of your stomach. You're worried that the students will take this 'crush' out of context, taking the bait that'll make them believe you're working with the mastermind to get favors out of him.

You flick your eyes up from your opened envelope to see the black and white bear's gaze linger on yours for a few seconds before giving a cute wink at you, which made you scrunch your face up in uncomfortable disgust.

This would be the start of Monokuma's so-called interest in you.

Ever since the black and white bear proudly announced everyone's secret the next day (cause no one decided the murder someone over having their secrets revealed), he's been making subtle advances toward you. Calling your pet names, flirting with you, etc. Course, you ignored them and tried to get yourself as far away from the black and white bear as you possibly can. But that didn't stop Monokuma's pursuit in trying to woo you as his once innocent and subtle advances would be dialed up to eleven.

For instance, when Monokuma would catch you all alone in an empty hallway or large room in particular, his cute and cuddly appearance would change into something more… profound. It's… how do you put this lightly? The black and white bear suddenly gained… a filled-out form.

The headmaster's new body is more humanoid-like, being slightly taller than his original look with his body proportions resembling that of a chubby short stack. Thicken limbs, an expansive male bust size (or moobs for short), a prominent but perfectly round ball of a gut jutting out from his waist by a good few inches, widen hips that are voluptuous and feminine looking, large tree trunks thighs with enough power to easily crack open a watermelon or a person's skull in general. Though, the biggest shock to you in seeing the headmaster's new form is that he has actual genitalia. It is fairly humanoid, the phallic shaft having a surprising amount of girth and thickness for a small guy like him accompanied by a pair of plump, heavy balls hanging low between his large legs, his crotch having the same black-and-white color scheme as the rest of his body.

He would use this new body in many attempts to try and seduce you with his 'charm' and whatnot. He would wear various amounts of fetish-type clothing that hug the many curves and edges of the headmaster's thick body so sinfully snugly. It ranges from crop tops, latex, tights, yoga pants, and various form of skimpy underwear, to just being bare-naked. Needless to say, it was… incredibly distracting to see the black and white bear's body jiggle and wobble immensely to his movements. But that doesn't stop there, oh no. There is more to Monokuma's shenanigans.

Every night, whenever to reside back in your dorm room, he would go out of his way to livestream himself making pornographic content straight from your room's school monitor. You were forced to watch Monokuma use various amounts of sex toys on himself, hear every moan, grunt, and very other lewd sound alright from your screen, all in 4K quality. Thankfully, his streams don't last very long. They range from about thirty minutes to roughly an hour. But still, it was… something to say the least.

You desperately want to tell that annoying, chaotic bear off as the stuff he's doing is straight-up sexual harassment. But, as he mention before, placing any kind of harm against the schoolmaster is a massive violation of school regulations, meaning you can get killed. So you can't do anything about it other than try to endure it.

But, the endurance against the headmaster would eventually break as the events that happened one night would decide the fate of you and the other students trapped within Hope's Peak Academy. Will you still cling to the hope of escaping this godforsaken school? Or will you give in and fall into the deep, dark pits of despair?

"Ugh…" You let out a heavy sigh, walking through the dark empty halls of the school before standing in front of the room door.

Inputting a custom key combination on the digital padlock, you turn the doorknob and stepped inside your dorm room, locking the door behind you. After heading to your drawer to change into your bed attire, you then tiredly walked over to your bed, flopping down onto the mattress, letting another heavy sigh into the soft cushions and silky sheets. Slowly turning on your back, you bring your gaze up to the ceiling, sitting in silence.

You felt both physically and mentally exhausted after what transpired today in this 'daily school life' of yours. Aside from Monokuma once again trying to seduce you, things have not been going so well for you and other students regarding your mental state.

Ever since the headmaster failed to spice the game up after revealing everyone's darkest secrets, he has been constantly trying new ways to get everyone to kill each other. From promising to win millions of dollars in cash to showing videos of our friends and family's lives ending in a horrific tragedy. It's gotten so bad to the point where one of the students lashed out at Monokuma, trying to cause physical harm to the robotic bear. But, since they broke the rules, they were brutally killed, impaled by numerous spears that the bear suddenly summoned from thin air till they became blood-soaked lifeless corpse dropped dead onto the floor. All of us were still shaken up by that to this day, tramuatized that one of the students was murdred in cold blood.

Since then, you and everyone followed the rules in fear of not upsetting the black and white bear, still clinging to the last bits of hope of escaping the school. But, you can tell that is not going to last much longer with how everyone's mental state is deteriorating. One of them is definitely going to betray everyone and willingly participate in the killing game, which you feared greatly. This is what Monokuma wants, to destroy our hopes and fall into despair.

But, despite the incredibly dire situation, you bring your thoughts over the headmaster himself; Monokuma. You're still trying to wrap your head around ambitions, questions quickly forming inside your head as you try to figure out the end goal in what he wants with you. Why is that bear so interested in you ever since he announced your secret to everyone? What is his motivation in trying to seduce you? Why does he suddenly have a humanoid-shaped body? And so on…

At first, you figured that Monokuma is doing this cause of your Ultimate talent. Maybe he wants your endless cafes and money since you are a successful businessman and all that. But that doesn't prove to be the case. So… what is it then…?

You let out a groan as you start to feel a headache coming on, both from stress and overthinking about the headmaster.

"Whatever. It's best not to think about it. I'll go the sleep early so l can be ready for our next breakfast meeting tomorrow. Hopefully, no one will die." You said to yourself.

Letting out a tired yawn, you got under the covers and laid yourself down on the soft bed, your eyes slowly closing as your drowsiness took hold of you before falling asleep soon after. But, your peaceful sleep was unfortunately cut short as you hear a familiar laugh, completely breaking you out of your slumber.

"Puhuhuhuhu! Heeeey, Y/N!" A voice called out to you in a sickening cheerful tone.

You let out a heavy, annoyed sigh, knowing full well who it belongs to.

"God… Damnit." You grumbled out.

'So much for getting a good night's sleep.'

Begrudgingly, you pushed the soft silky sheets off of you, pushing yourself up to see the intruder who broke into your locked dorm room. And surprise surprise, it is none other than the black and white himself standing in front of your bed.

The headmaster has unwillingly graced his presence once again in his humanoid form, as you expected from him. Only this time, he's wearing a particularly lewd attire, something far more scandalous than the many types of fetish clothing he's worn in the past. The article of clothing in question is…well, lingerie.

Donning the bear's chest is a black-laced bra that looks to be a size too small as you can see it visibly straining to contain his well-endowed chest. Monokuma's tits were fucking huge, easily the size of a volleyball as waves of succulent, doughy flesh threatened to spill out from his small top. The same could be said about his laced panties as they bite into the headmaster's waist is tight that it practically looks like second skin. The skimpy undergarments left little to the imagination to showcase that thick bulge nestled in a thin fabric punch between his fat legs, barely containing the bear's thick endowment as you see the base peeking out. Last but not least, covering the bear's large legs were a pair of black stockings, which goes as far up to his inner thighs. They squished into the fat of his thick thighs, effectively highlighting their plump demeanor.

You pried your eyes away from the black and white bear's body with a mental shake from your head, quelling the burning sensation you feel rising within your cheeks. You've seen his form many times. It shouldn't pose much of a problem to you…

"Evening, Monokuma." You greeted the uninvited bear in a grumbled tone.

"Whatcha doing?" He asked playfully, lightly rocking himself back and forth using his heels.

You silently stared at Monokuma with the deadest, blank expression on his face for a short moment before responding.

"Sleeping." You simply said. "Now, why'd you decide to break into my room?"

Monokuma sheepishly rubbed to back of his head. "Oh y'know, I just feel like I want to stop by to check on one of my favorite students since… we don't hang around much. And besides… 'breaking into someone's room' is such a strong term. I just… let myself in." He assured.

'That doesn't make it any better! And what do you mean by 'hanging out?' I have been actively trying to avoid you!'

"Uh-huh…" You hummed with a raised eyebrow, sounding not too convinced. "And to decide to come here… wearing that?" You asked, pointing at the bear's skimpy clothing.

"Yep!" Monokuma said happily with a quick nod.

"You liiiike?" He asked in a sinuous purr, cupping his barely contained breasts with his mitts, squeezing into the soft doughy flesh.

"I wanted to look my best in getting when meeting you in private again. You wouldn't believe how hard it was to fit my tits into this thing!" The bear complained before letting out a dramatic sigh.

"Haaah, having big boobs is both a blessing and a curse. While they're the main essentials for seducing people, the back pain will forever be immeasurable…" Monokuma said pitifully, letting go of his massive bosom, the mounds wobbling a bit before settling.

The black and white bear then turns himself around, bending over slightly as he shamelessly showcased his two, plump, juicy ass cheeks. You quickly looked away from the presenting headmaster as you were given a good eyeful of that butt floss of underwear tight wedged between the bear's bountiful rump. You can practically see his taint with how the underwear has sunken itself deep within the trench of his buttcrack…

"Especially this underwear here. I constantly have to adjust myself for how much this is riding up the crack of my ass. But, I still look good in it regardless, hehe~" He chuckled, giving you a cheeky wink from over his shoulder.

Reaching behind him, Monokuma pulled the swallowed thin fabric within his deep crack to undo the atomic wedgie he gave to himself, the underwear snapping it back into his fat ass in an audible smack, causing a quick hypnotic wave to visibly ripple across those bulbous black and white cheeks before settling.

"Ah… that's better." The bear let out a sigh of relief as his butt and loins no longer feels constricted by the snug, laced underwear.

You strongly exhaled through your nose, hanging your head as you annoyingly pinched the bridge of your nose, feeling the headache you've suppressed come back again. You have had it in dealing with this bear's shenanigans for far too long. It's time to finally confront him and put him in his place.

'Lord, have mercy on my soul for what I'm about to do.' You prayed internally.

"Why…?" You mumbled.

The robotic bear's ears gave a small flick as he turned himself around to face you.

"Hmm? Why what?" He questioned, placing a mitt under his chin as he tilted his head slightly, his different eyes staring at you curiously.

"Why? Why are you doing this, Monokuma!? What is your reason for being so obsessed with me?!" You exclaimed in a frustrated manner.

The robotic bear stared at you blankly for a moment, his button eye giving a couple of blinks before the expression on the headmaster's face changed.

"Puhuhuhu…" Monokuma suddenly began to snicker, his mitts reaching to cover his muzzle childishly as the half grin on the black side of his face widen almost sinisterly.

"What's so funny?" You questioned, feeling anger but also a growing pit of dread forming deep within your stomach.

"Oh, dear Y/N…" He said coyly. "Do you want to know why I'm doing all this?"

"Yes! Absolutely!" You said quickly, eager to know the bear's ambitions.

The black and white bear giggled again, his jagged red eye glowing a slightly ominous bright red, which made you feel uneasy at how much he was enjoying messing with you. He sauntered forward, coming close to the foot of your bed leaping forward, plopping himself down onto your bed mattress, catching you off guard. You quickly scooted back against the bench of your bed, wanting to get away from the robotic bear from invading your personal space. The headmaster giggled again in a more playful tone, taking enjoyment in making you feel uncomfortable. He lowered himself down onto the soft sheets and slowly made his way towards you in a seductive, cat-like crawl, making sure to stick his fat monochrome rump in the air, keeping his half-lidded eyes on you. He's like a predator, ready to strike at you, his unfortunate prey caught within his trap.

"The reason why I'm so obsessed with you is cause…" Once he got in front of your crotch from your parted legs, he sat himself up.

"I…" He paused a bit for suspense. "…Like you!" He finished in a happy tone, giving you a 'bright' smile.

Your eyes widened, threatening to bulge out of their sockets from what Monokuma has confessed.

'Did… did I hear that right? Monokuma's doing all this because… he likes me? No,… this has to be fake! A big setup to catch me off, guard! It has to be!'

" W…What?" You breathed out. "You… like me?" You asked, still in utter shock.

"Ehhh…" The bear let out an unsure noise, his button eye staring off to the side. "Weeell, yes and no." He confirmed.

"Huh?"

"You see, there's more to this story than just me going after you for a simple love confession. Allow me to explain." He said, sitting down crossed-legged as he began telling his side of the story.

"This all started when I gave you and everyone else their secret letters in encouragement to start the killing game. I was initially shocked to find out you have a secret crush on me. To be in a steamy, lustful relationship between a headmaster and his student is—ah, glorious!"

Monokuma sniffed.

"I feel so honored in being the love interest in this forbidden taboo relationship between you and me!" He said, wiping away a fake tear, fanning himself as if he was crying.

"But I mustn't! It could put my entire teaching career in jeopardy if I were you get with you. No, I shan't allow that!" He said dramatically, laying a mitt on his forehead as he turned away from you with an over-the-top flare.

You silently rolled your eyes at the black and white bear.

"Buuuuut…" He trailed off, slowly turning his head back to you. "…If you really wanna be with me, my door is always open. Puhuhu~"

"Like hell if I wanna get into a relationship with someone who wants people to kill each other for sport! No way that's gonna happen!" You exclaimed.

"And I don't think you're telling me the full truth!" You accused the monochrome bear.

"I'm getting to that! Geez, you people can't enjoy a good story, can you?" Monokuma huffed annoyingly, pouting before continuing.

"Anyways, before I was so rudely interrupted…" Monokuma stressed out, throwing an accusing eye at you, which you let out narrowing your hard glare back at the black and white bear.

"… I knew that me trying to win you over with just flirting and pet names isn't to do much for me! So, I have to take drastic measures to achieve that goal! Which is the reason why I stand before you looking like this ." He said, presenting himself.

"Puhuhu. You want to know how I got into this glorious form?" He asked.

"No. I don't." You said bluntly.

"Well, too bad! I'm telling you anyways! So shut up and listen!"

You let out a hard sigh before the monochrome bear began telling another one o his long-winded stories.

"As you already know, I'm considered by the many large masses to be a 'cute and marketable mascot character.' He said with air quotations.

"So, I wanted to transform into something that would catch your eye. Something that would cater to a more… degenerate audience." He said smugly, a mischievous glint shining in his button eye.

"Sooooo, I kindly asked my creators to help create an adult, humanoid-like body for me so that I can transform at will anytime. It took a lot of… persuasion to fulfill my request."

'Persuasion? More like he forced them to do his bidding.' You thought.

"But, after many painstaking hours of hard work and determination from my wonderful creators, Bada-bing Bada-boom, a new body is created for moi'!" He said, pressing a mitt onto his puffed-out chest.

"This glorious new form of mine is a lot more humanoid than my original appearance. Made with the finest synthetic materials, this body perfectly replicates what you humans call 'a chubby short-stack.' I call it…" He paused for dramatic effect.

"NSFW Mode!" He announced proudly, moving his arms in a 'pizazz' motion with shining sparkles in his eyes.

'NSFW Mode? Not a very creative name. But it suits him, I guess.' You thought.

"Needless to say, I'm very happy with the results! Not only sure I still maintain my cuteness factor, but now I'm a lot more soft and sexy because of it! Puhuhuhu!"He giggled, hugging himself in the giddiest manner.

"I just couldn't help myself in giving my new body a test drive, which is why a wore a bunch of skimpy clothing and flamed those erotic live streams to get your attention. Feeling how those small clothes wrap snugly around my squishy body, feeling it move around as I filmed myself… amazing. Ohhh, I'm burning up just thinking about it~" He breathed out heatedly, his cheeks burning a bright shade of red, his member twitching within his laced panties as his endowment grew to a half-chub, pushing against the confines of his undergarments.

Seeing how aroused the monochrome bear is getting made you feel very uncomfortable. But, you still feel like something is missing with Monokuma's intentions to 'woo' you. Something rather… sinister behind it all.

"Okay? But I feel as if that's something more than just trying to get me to notice you. What are your true intentions?" You questioned the monochrome bear.

"Puhuhu! Why, to make you fall into despair, of course!" He said joyfully.

"What…?" You said with disbelief.

"You see, dear Y/N, there's something about you that immediately caught my interest. And no, I'm not talking about your Ultimate talent. I don't want your money or an endless supply of themed cafes plastered all over the world! He paused for a moment, placing a thumb under his chin as a thought popped up.

"Although… it would be a cool idea if there was a cafe all centered around me. Yeah…" Monokuma muttered, intrigued by the idea.

The monochrome bear soon snapped out of it as he realized he was getting sidetracked.

"A-Anyways," He cleared his throat before continuing. "The point is you have that special something that would be beneficial for this killing game. Which is why I want to discuss this with you in private."

"Fuck no! Count me out! There's no way I want to participate in playing this fucked up game!"

"Oh, I don't think you have the power to refuse what I have to offer. After all, I'm the headmaster of this school and anything I say goes. So I'm asking you kindly to show some cooperation with me, okay?" He said with a strained smile.

"And if I still refuse…?" You asked.

"Then, I'll simply punish you for misconduct. And I'll decide whether or not I can make it light or severe. We don't want you to end up like that Fashionista chick now, would we?" He said ominously, his red jagged eye glowing a right sinister red.

You gulped, feeling your heart stutter in fear as Monokuma's gleaming red eye stared into the depths of your soul, making you feel helpless under the robotic bear's looming gaze. As much as you don't want to be part of what Monokuma has planned, you have no other choice but to abide by his rules to keep yourself alive.

"Fine," You said with a heavy defeated sigh. "What do you want me to do?" You asked begrudgingly.

"It's a simple task. I want you… to become blackened." Monokuma said.

You gave the monochrome bear a puzzled look. "The… blackened?" You asked, sounded both hesitant and confused.

"Yep!" Monokuma chirped. "You and the other students still refuse to participate in the killing game no matter how much I tried to encourage all of you to betray each other. And it's all so booring! I need excitement, anguish, and an endless amount of bloodshed splattered across the floors and walls! So, I figured that you, dear Y/N, would be the perfect candidate to help kick off this killing game strong! I'll give you all the tips and tricks in taking out the easiest target in your class and I will also go over the basics when getting into a class trial after the dead body of said student has been discovered. If you manage to win the trial without being caught as the blackened, then I will let you leave this school by graduating! If you lose, however, well, let's just say you will be punished and the game will continue without you!"

"And by punished, you mean killed, right?" You asked.

"Precisely, Y/N!" The monochrome confirmed happily. "I'm so glad you're catching on!" He mockingly praised.

"Fuck…" You breathed out.

'What do I do? I desperately want to leave this school! But, to become a killer and betray the trust of my fellow peers, ones who I barely know… I don't know if I want that…' You thought.

"But, what will happen to the other students if I happen to win the killing game?"

Monokuma perked up. "Oh, great question! I almost forgot that one little thing I should've mentioned!" He said before continuing.

"If the other students failed to identify the blackened, all of them will be punished! Thus, bringing the killing game to a dead end! Puhuhuhu~!"

Your eyes widened in disbelief as you felt your stomach drop in dread, making you feel queasy.

'All of the other students… will be killed if I win?'

You soon snapped out of your distraught daze as you hear the bear's voice call out to you.

"So, Y/N. Whaddaya say? Will you become the blackened in this killing game for me, hm?" He asked, holding out a mitted hand to you.

You flicked your eyes up and down between Monokuma's face and his held-out mitt in front of you, feeling heavily conflicted about whether or not you should take his offer. Your mind is screaming at you to not take the offer, as anyone with an ounce of common sense would do in this situation. Monokuma is a psychopathic bear who kidnapped you and other students to come here and forced you to play this fucked-up killing game got destroy any ounce of hope of escaping here. But on the other hand, you get to leave if you win the class trail. Though, at the cost of it, you would have to betray everyone's trust and become a killer, which you're heavily against. It's tempting, and not in the good kind…

"You… promise to let me go if win, right?" You asked hesitantly.

The monochrome bear nodded fully. "Of course! I promise to let you go only if you come out on top in the class trial! Would I ever lie to you?" He said in a sickly sweet tone.

You know damn well that Monokuma is lying with every word he says. You know that he cannot be trusted! But, if what he's saying is true… then… maybe… You let out a heavy sigh, hanging your head low as squeezed your eyes shut.

'I'm sorry everyone.'

You brought your head up to the robotic bear, who was staring at you curiously with a slight tilt of his head.

"Weeeell?" He says expectingly, waiting for your answer.

"I… I accept." You said unwillingly, the words in the voice sounding heavy as you slowly reached an arm out before wrapping your fingers around the bear's mitt.

"Puhuhuhu! Thank you, Y/N! Be sure to make this killing game instructing for me, ok?" He asked, his jagged red eye glaring down at you.

"I… I won't." You said with a slow nod.

The black half of the robotic bear's face grinned widely at your cooperation before he shook your hand, finalizing your unfortunate deal with him.

Immediately, you felt a heavy wave of regret surge through your system, ashamed that you betray the trust of your fellow students to become a killer. But, for some reason, you felt a sense of… happiness growing inside of your chest. Is… is this what despair feels like? Have you finally given up on all sense of hope you've desperately clung to and begun descending into the dark depths? No, no you couldn't have…

Monokuma removed his grip from your hand and lets out a content sigh. "Alrighty then! Now that that's settled, there's one more teensy little thing I'd like for you to do to seal the deal of our little agreement here!"

"Hmm? What is it?" You asked the monochrome bear.

You felt uneasy as the headmaster giggled, a mischievous look present in his eyes as he stared at you.

"Puhuhu! I want you…" He trailed off for dramatic suspense.

You braced yourself, knowing that what kind of request Monokuma has in store for you would be really bad.

"…To admit you have a crush on me!"

…

…

"…What?" You blinked.

The robotic bear snickered. "Say you like me! Come on! Do it!" He ushered playfully.

"I, wha— no! Why?" You stammered, confused yet flustered by the sudden weird request.

Monokuma let out a huff, rolling his singular button eye, and placing his hands on his sides.

"Oh, don't play coy with me, Y/N. I know that you have a thing for me! It says so on the envelope I gave you a while back!" He countered.

"But that's not true! Why couldn't you use some other type of dark secret I have and put that against me!" You argued.

"Cause the game wouldn't be interesting! I mean sure, I could've used some other personal stuff against you, like your family and whatnot. But the secret crush is an immediate eye-catcher, in my personal opinion! I just had to use it!" He said.

You let out an annoyed sigh. "God, help me…" You moaned out in dismay.

The robotic bear giggled at your frustration. "Say what you want, Y/N. But your deepest, darkest secret will always be one hundred percent true! I spent many, many hours doing heavy research on you and the others, digging up some reeeal juicy bits to pin you against each other to help encourage the start of the killing game. It was very hard and very annoying! But you? I can see it behind those pretty eyes of yours the moment I introduced myself to you all. You're just in denial. Puhuhuhu~!"

"No! I'm not in denial! I don't have a crush on you!" You exclaimed.

The monochrome bear doesn't look convinced by your rather weak defense and instead grinned smugly at you.

"Oh? Then why is your face turning red?" He asked teasingly, pointing a finger at you.

"Huh?"

You reached a hand up to touch your cheek and much to your horror, you felt the heat radiating against your fingertips as well as your skin visibly glowing a slight hue of red.

"I— ugh!" You groaned, turning your face away from the robotic bear to hide your red face, shame bellowing up inside you.

'What's going on with me?! Why do I feel myself getting flustered around Monokuma now?! This… isn't me falling into despair now, is it?!'

Monkuma snickered at you. "Well, well, well. It looks like poor Y/N's entering the five stages of grief! Wonder how long it'll be till you reach acceptance! Puhuhuhu!"

"I'm not! It's just… really hot in here all of a sudden!" You defended, huffing sharply.

"Uh-huh. Suuuure~" He drawled out with a sly grin, not buying your dendense.

You let out a low grumbled, refusing to look at the grinning ursine.

"Aww, what the matter, Y/N? Getting hot under the collar? Am I distracting you with my sexy, voluptuous body?" He said teasingly, doing a light shimmy with his arms, making his barely contained moobs jiggle with his movements.

"N-No. You're not!" You tried to keep yourself from stuttering, failing to do so.

"It's ok, Y/N. You can stare at them all if you want. I can see in your eyes how much you want to put your hands on me~"

"That's not what I'm thinking about-"

Monokuma quickly cut you off. "'Man, Monokuma's got some BIG fucking jugs! I wonder if I'm able to hold them in my hands.' Or, 'Damn, that bear has some the finest wide, birthing hips and the thickest thighs imaginable. I would love to pound that fat, fluffy round ass of his!' Am I right, or am I right?" He said, teasing you even further.

"No! Ugh!" You slammed your face into your hands with a loud groan. "I don't, and will never, have a crush on you! No matter how times to say or try to convince you that my secret is true, I won't admit to liking you! Period!"

Once again, the monochrome bear isn't buying your argument. So, instead, he doubles down.

"Hmm… perhaps I'm not being persuasive enough. Maybe I should move closer to get you to pay attention to me~" Monokuma said mischievously, his red jagged eye gleaming with devilish intent.

"H-Huh?! H-hey wai—"

Before you can get to finish your sentence, the bear quickly moved in, climbing up from between your legs and plopping his fat rear onto your lap, pressing his plush form flush against yours. You tried to lean yourself far back against the bed to least not get a single one of Monokuma's plush body from touching you, but you didn't react fast enough for that to occur. He's trapped you in his sinful embrace as his ample chest and pudgy belly squished against your torso. For a robotic bear, he felt surprisingly warm as his body heat radiated against your entire being.

"There we go." He sighed, wringing his head up to look at you. "Surely you'll pay attention to me now that I'm pressed up against you like this. Puhuhu~" He purred out, giggling.

You let out a hitched breath, tensing up as the monochrome bear wrapped his arms around you, nuzzling his face into your chest, his soft fur tickling you.

"Mmmm… you're so warm." He let out a muffled hum of bliss.

You felt your throat close up, words failing to come out of your mouth at what is happening. You don't how to feel about this, having the headmaster all up on you like this, toying with you just to rile you up. Every fiber of your being wanted to push this bear off of you. But, you were afraid to do it for the risk of getting punished. You felt helpless unsure what to do as you ran out of options. However, despite how incredibly uneasy you are, you also felt… excited. A growing kindle of heated arousal began to pool inside of your gut. You felt hot underneath your shirt as your body temperature was rising, blood surging its way down between your legs.

You sucked in a sharp breath through your nose, your eyes tightly sealed shut as you desperately tried to not get yourself aroused from the monochrome bear's presence all up on you. Though, it was incredibly difficult when he was idly shifting his position in your lap, subtly bouncing his doughy buttocks down to onto your crotch, grounding your growing bulge against those massive, marshmallow cheeks.

'Get it together, Y/N! Don't succumb to your desires! You're not attracted to Monokuma. This is just him trying to get you into despair. You can do this!' You reassured inside your head.

"P-please…" You wheezed out in an almost inaudible whisper.

"Hmm? Please what? Speak up, Y/N! Use your big boy words~" The robotic bear taunted smugly.

You take in a nervous gulp before speaking up. "Please… get off of me." You pleaded, doing your best to keep your voice from cracking.

Monokuma tapped his chin in a mock thought to ponder your meek request. "Hmmm… nah. I don't think I will. Besides, I think you wanted me to sit on your lap for a pretty particular reason. Is that it?" He asked.

"N-No! That's not it at all!" You weakly protested, dodging the question.

Monokuma raised a curious but smug invisible eyebrow at your answer.

"Oh? Then what's this I feel poking behind me?"

"Hmm!" You let out a moan, your body tensing up in a sudden jump as you felt the headmaster's mitt wrapped around your bulge.

The robotic bear grinned widely at your reaction as he tended to your producing erection, feeling every pulse and heat flow through his mitt as he slowly pumped your clothed dick up and down. You squirmed in place, your face twisting in pleasure as short but raspy grunts left your mouth from Monokuma's teasing. A mixture of arousal and humiliation floods your body. You don't want this. You don't want any of this. But no matter how much you wanted to fight it, your body reacts oppositely.

At this point, you're at the complete mercy of this sadistic bear as he took pleasure in seeing you writhe and squirm within his grasp.

Monokuma let out a pleased hum as he hungrily watched your dick grow firm and hard with each teasing stroke he gave to your producing endowment. It wasn't long till a large pitched tent pierced through the stretched fabric of your bedroom trousers, a wets spot forming at the clothed tip.

"Hehe, damn boy. You're packing some serious meat, aren't'cha? I wonder how'd you even fit this thing in your pants as you go along your measly day." He playfully commented, teasingly dragging a finger up the erect bulge, making it twitch in response to his touch.

He lets out a dramatic gasp. "And look how wet you are how just from me caressing your dick alone! I guess it shows how much of a whore you are, huh? Puhuhuhu~!" He giggled.

You cast turned your face away from the smug-ridden bear.

"Aww, don't look ashamed, Y/N." He cooed. "It's okay to have sexual thoughts about your headmaster!" He said happily.

"B-but I… I…"

"As a matter of fact, why don't I give you a little preview of what I plan to do with you? Puhuhuhu~" He said in a low, sultry voice, giggling as his button eye grew heavy-lidded in wanted desire.

Pushing himself away from your chest, your eyes cast back to the monochrome bear as he reached towards his straining laced bra, moving deliberately slowly in an attempt to excite you even further. Needless to say, it was working, much to your dismay. You watched as the bear hooked a finger over the top of the thin fabric before giving a small pause for baited anticipation. Then, in a single, smooth pull, the snug article of clothing was yanked downward, exposing his glorious mounds for you to see.

You felt your mouth turn dry as your gazed upon the gelatinous flesh of the robotic bear's chest wobbling slightly in the open air, free from their confined prison. The first thing you noticed is that Monokuma doesn't have an areola, a fleshy ring surrounding a person's nipple. Instead, it is a soft blush of pink highlighting the notable bumps of his engorged nipples on his monochrome fur, being sufficiently large to the mammoth mounds they were attached to. You wanted to tear your hungry eyes away from the headmaster's exposed chest, but you couldn't. You were far too entranced by how utterly enticing the bear's chest is.

Monokuma cupped his hands underneath the mounds, the fatty tissue overflowing in his grasp as he lift them upwards, showcasing how heavy his big honkers are. A wicked smile arched across the black half of his face as he delightfully watched you gawk at his girthy assets. The way the flesh gave in and rippled as he squeezed his massive bosom lightly, how his hands sunk deep into the gelatinous fat with ease. It was all so… incredibly arousing, a king-sized feast of pure eye candy.

"Haaah, that felt good to get that off of me." He sighed, giving his breasts a small bounce. "So, what do you think of the cubs? Pretty big, huh?" He purred, fondling his bosom sensually.

You couldn't form a proper answer as you feel your brain short circuit itself from the immense visual stimuli and increased painful feeling to have for your hard-rock erection. All of you can let out was a small, pathetic squeak, your mouth repeatedly opening and closing, words falling to come out.

The monochrome bear chuckled at your weak response.

"Hehe, feeling the neutrons in your pathetic brain spark at seeing my big boobs? You're more than welcome to give them a good feel~" He purred, dropping his plump moobs, making the fall back in place in a heavy slap.

"I-I…"

"Please I insist~," He said, grabbing your arm before tugging it to guide your quivering hand towards his chest, which you gave little resistance to.

The bear then leaned in close, pressing your palm up against his doughy chest. "Go ahead, Y/N. Give 'em' a good squeeze~" He said sensually in your ear, his voice dropping to a seductive breathy whisper.

You shivered, your cock throbbing hard within your trousers as your fingers twitched, eagerly wanting to cave in a grope Monokuma's bosom. With a bit of hesitation and internal conflict, you gave in, slowly curling your fingers in and giving the bear's chest a good, firm squeeze. A small gasp leaves you as you watched how the doughy flesh bulges between the gaps of your fingers, the tip of your digits sunken deep to where you almost don't see them anymore.

'Holy crap. They feel… so soft. It's like I'm kneading into a pile of bread dough.'

Monokuma let out a lewd groan in your ear, his cheeks burning red as he lightly shuddered, relishing the feeling of your hand groping his milk jugs.

"Mmmm… Soft, aren't they?" He asked.

You slowly nodded. "Y-Yeah," You responded. "I can barely hold them up in my hand." You breathed out, still trying to recover from your brain-dead state.

"Puhuhuhu. Well, that's the perk of this new form. Designed to simulate the feel of an actual human being, or in this case what you people call a chubby short-stack." He explained.

"And you're allowed to explore and learn every single inch of my beautiful, voluptuous body if you admit you have a crush on me~" He offered.

"Just imagine it for a moment. I would use my tits and squish them down onto your throbbing, needy dick, engulfing it into a vast velvety smooth, fat, and fluffy cushion. Then when you would desperately hump my sandwiched breasts, you'll get nice a full view of my big, bountiful chest bouncing as I... y'know... give you the sucky fucky gluck gluck! Puhuhuhu!" He giggled before continuing.

"Ooooor, if big boobs aren't doing you any good, perhaps you're looking for something more… bigger and heavier to fool around with. Puhuhuhu~"

To prove his point, he moved back a bit and turned around. Then, lowering his upper body from between your open legs, he raised this lower body high in the air, pushing his two, giant meaty globes right in your face. You let out a shaky breath, cheeks blazing red as you're given an up close and personal view of that overwhelming underwear-clad ass, making your pulsating cock spurt a dollop of fresh precum through your pitched tent.

"Ohhh! Looks like that got a good reaction out on you at seeing my big junk in my trunk, as rightfully so!" He said smugly, wiggling his butt from side to side.

Your eyes were locked onto the swaying rear, watching those monochrome cheeks wobble to and fro to his movements.

"I know how much you like staring at my ass. No matter how much you try to hide it, I can tell that you wanna stuff your face between my big, fat rump~" He purred, giving his cheeks a good slap, the impact causing a tidal wave of ripples to flow across the vast, soft furry scape of his perfectly round rear before settling.

"Would you like that? To be my personal, little chair and worshipping my meaty posterior for hours on end?"

"Y-Yes…" Those words flew out of your mouth at a breakneck pace as you grew heavily aroused by the headmaster's heavy teasing and dirty talk.

The monochrome bear chuckled darkly at your eager response before quickly turning back around to fully face you again.

"Then, if you want me to give what you oh-so desperately need to get your rocks off, admit that you have feelings for your dear old headmaster~," He said huskily, cupping your burning cheeks into his mitts as he bring his face right up against your own, almost as if he's going to kiss you.

Seeing his mischievous expression shining through his eyes made your insides melt, a sense of warmth flowing your through body being this intimately close to him. All the restraint and utter disgust to have for the sadistic headmaster has been completely diminished and instead been replaced with utter want, your head filled with heavy sexual desires.

Monokuma now has you under his control as the dark, comforting embrace of despair finally took hold of you, the last shreds of hope you once had completely faded away.

"I… I admit to having a crush on you, Monokuma." You responded in a hushed tone. The black half on the bear's face grinned ear to ear, his red jagged eye shining maliciously at you, happy that his long-running plan to seduce and emotionally manipulate you to do his bidding finally paid off in the end.

"Do you truly mean that? That your feeling towards your headmaster is genuine?" He whispered sweetly, leaning in close so that his muzzle barely graze against your lips, his warm breath gently brushing against your skin.

You shakily nodded. "Yes. My feelings towards you are one hundred percent genuine, Mr. Monokuma."

The robotic bear let out a pleased hum at both your answer and how you addressed him formally.

"Good boy~" He purred, giving your cheek a quick little nuzzle with his button nose, making you shiver at his praise.

The robotic bear smiled darkly against your skin before pulling away, much to your dismay as you desperately want to be close to your now-supposed lover. But, you held your tongue.

"Now, dear Y/N. For your cooperation in confessing your undying love for little ol' me, you're allowed to use me to your utmost desire, as promised~" He said.

He blinked as another thought came to mind. "Ah, one thing I forgot to mention. Since I'm feeling rather generous tonight, I decided to lift the rule of manhandling the headmaster just this once, of course." He announced.

"So, don't be afraid to get rough with me~," He said huskily.

You felt your heart skip a couple of beats at the news, your cock throbbing profusely in barely contained excitement.

The monochrome grinned at your trembling form, eager to get the jump on him. "Now, come and get me~" He growled out in a sinuous purr, opening his arms out wide, making himself completely vulnerable.

Hearing his seductive voice and words, you immediately took action, practically leaping from your spot as you grabbed the bear's shoulders and push him on the bed. The headmaster let out a surprised grunt as his body bounced slightly as his back hit the mattress, the bed creaking from the sudden weight shift. You quickly got yourself on top of him, your body shadowing his as you stared down at him with a flushed, lust-filled look on your face, mouth hanging slightly open as you lightly panted.

Monokuma, stared up back at you in shock from your sudden action before his face morphed into a smug heavy-lidded expression.

"My you're eager. For a second, I was gonna question lifting that violation rule cause I knew you would pull a stunt like that. Buuuut, I'll let it slide. Puhuhuhu~" He giggled, before putting his arms behind his head to make himself more comfortable.

"Well, what're you waiting for? Come give your headmaster some love,~" He growled out.

Without even thinking, you dropped down onto the robotic bear, diving face-first into his large, bountiful bosom. You let out a muffled moan as you nuzzled your face into the deep cleft of his plush breasts, squishing those soft pillowy tits on either side of your head, sinking into the vast plush form of your headmaster. It felt jarring at first considering he's a robot. But the soft warm sensation of it all was enough to render you powerful, putting you at ease.

'I can't believe I'm actually doing doing this. I believe I'm doing this with my 'headmaster' of all people. Yet, I don't wanna stop. I want to hold him, kiss him, and admire every part of his immaculate, voluptuous body. Monokuma, let me show you how much I appreciate you tonight.'

Monokuma snickered as he watched you motorboat his bountiful cleavage with an amused fascination on his face.

"Puhuhuhu! Feels nice to finally sink into the wonderful embrace of my tits, huh Y/N?" He asked.

You lifted your face from his chest with a snort and gave him a nod, still keeping those moobs squished on against your skull.

"Mhm. They're incredible. It's like I'm laying on a fluffy cloud." You softly said before burying yourself within his cleavage once again.

"Awww, I'm flattered." He cooed, giving your head a small pat, lightly ruffling your hair. "But, as much as I like seeing you stuff your face into my chest, I'm getting rather needy. So let's speed up this worshipping process by putting that mouth of yours to good use, okay?"

Hearing Monokuma's words, you quickly pulled your head out of his bosom and instead focused your attention on his tantalizing moobs. You leaned in, letting out a warm huff of breath against the headmaster's fur before latching your lips onto the bump of the bear's nipple in an audible smooch. A soft moan escaped you as you stuck your tongue out and licked around the hardening nub.

'God, he tastes so good…' Your thoughts quickly drifted to a lustful haze, clouding your inner judgment.

The robotic bear had an… interesting flavor to him. Ignoring the obvious bits of fur sticking onto your tongue, he had a sort of 'spice' to him that you can't quite put into words. But, there is a subtle tang of saltiness, almost akin to sweat of some kind. And his scent… he smells like a stereotypical perfume used by many men and women alike; being lavender. However, there is a noticeable earthy, natural musky scent added to the floral fragrance to help balance it out to be a perfect concoction.

Removing your lips from the erect bump of his nipple with a wet 'pop,' you shifted your head over to the bear's other moob, giving it the same oral attention with your tongue and mouth, all while massaging the one who got left.

"Nnnnmmmgh… yeah. That's it, Y/N. Work that mouth of yours." Monokuma breathed out.

You moaned, feeling your insides turn to mush at the robotic bear's praise, encouraging you more to please him fully. So, you used your teeth to gently bite down onto the firm nub and gently tug on it, your occupied hand squishing firmly doughy flesh of his tit, your fingers circling his saliva-coated nipple. The monochrome bear let out a soft gasp, his body jolting under your touch, causing his growing endowment to strain within the thin fabrics of his panties.

'Fuck… I can't stop myself…'

You felt like your head is swimming with clouded lust, your body moving on autopilot with the amount of pheromones you'd heavily inhaled from the monochrome bear, fresh and exotic. It made your heart thud heavily inside your chest, your body temperature rise as excitement surges through your veins and down south.

It all feels unreal. You, having sex with your mechanical, ursine headmaster. Yet, you don't wanna stop. You want to do everything you can to make him feel good, to prove you love him.

You spend a bit more time worshipping the headmaster's ample chest, highlighting his delicate skin in soft glowing bite marks before kissing your way downwards against Monokuma's body. You purred as your soft moist lips noisily smacked against the monochrome bear's round ball of a gut, your hands occupying themselves by exploring across the vast, furry dome, from the hilt to his weighty underbelly. A strange sense of satisfaction bellowed through as you played with your headmaster's stomach. You poked, prodded, squished, and jiggled the bear's gobbler belly, making sure no inch of it is left untouched. You even worshipped one of Monokuma's core features, his cartoonishly produced-out belly button. While others saw it as a weird and creepy part of his body, you find it to be a suitable look for him. Hell, attractive even. Sure, it looks silly but you can work with it.

You nuzzled your nose against the outie navel before you opened your mouth up and latched your lips on his belly button. Using your tongue, you slowly licked across the belly button, feeling the nub flicking around against your wriggling wet organ before puckering your lips to lightly suck on it.

Monokuma let out a grunt, his back aching as he bucked his navel into your mouth, making you let out a muffled moan as you discovered one of his weak spots.

"Ffffuck… you are a weird kid. Sucking off a bear's belly button like a pacifier…" He said in-between heavy ragged breaths, his cheeks flushed red as his muzzle slightly parted, revealing a long slimy tongue lolling out his maw.

"I was gonna make a degrading comment. But, hnnnmgh… it's fun watching you grovel like this! Keep up it! Puhuhuhu!" He laughed, giving your hair a slow, affectionate rub.

After lavishing Monokuma's cartoonishly-sized navel for a solid minute, you pulled away with a heated huff. You cast your eyes down between the headmaster's large legs, drawing your attention to the growing bulge within those snug-fitting panties he's wearing. You licked your lips at the sight of it, your cheeks flushed heavily as the erection in your pants throbbed to a painful degree, precum bleeding through the stretched fabric.

'I want it. I want to suck Monokuma's dick.'

Eagerly, you slide yourself down between the bear's legs, laying yourself flat down on your stomach as you pushed your head through the open gaps, getting a nice up-close view of his crotch. And boy what a view it was, far better than you could've ever imagined. Those tight-laced panties left nothing to the imagination, practically see-through as you see his cock straining against the thin fabric, barely containing bits of the exposed shaft highlighted the headmaster's sheer girth and length. Not to mention, there is a large stain of precum darkening from the clothed tip, as large balls hanging underneath. It is such a mouthwatering sight that you almost almost drooling.

"Holy shit…" You breathed.

The monochrome snickered cheekily at your reaction. "Enjoying the view, dear Y/N?" He asks smugly.

You nodded dumbly.

"Weeeell, aren't you gonna do something about it?" He teasingly ushered, lifting his hips a bit to push more of his hefty bulge into your face.

Taking a heavy gulp, you reach a shaky hand out and gently placed it upon Monokuma's dick. Its radiating warmth tingles against your skin through the see-through laced fabric, the length twitching in response to your contact. You curled your fingers inward, giving the barely covered bulge a firm squeeze, massaging the headmaster's dick through his underwear in an attempt to jerk him off. The monochrome bear let out a soft moan as you works your delicate fingers onto his cock, precum leaking steadily from the clothed tip, dampening his slimy underwear. Seeing your headmaster leak his sexual fluids through his clothing caused inside you to snap, your libido spiking to an incredible degree.

So, unable to stop yourself, you opened your mouth wide and dived forward, stuffing your gaping maw with much of that heavy package as you possibly could. While the flavor of Monokuma's underwear isn't the best per se, the fluids seeping through the stretched fabric make up for it greatly. Tasted of your headmaster's fluids were surprisingly strong and enthralling, leaving a pleasurable tingling sensation in your tastebuds that sends a heated thrill through your already foggy mind.

"Mmmph…" A low, muffled moan leaves you as you huffed a hot puff of breath onto that package before sucking and licking with your hungry maw, feeling the hardening cock twitch under your lips.

You dragged your tongue slowly over the growing thick lump, easily indemnifying where the head is as you vigorously sucked at it, your eyes threatening to roll into the back of your head as the salty n' sweet of your headmaster's precum leaked down your throat.

'Fuck me. His scent is growing stronger, more potent as I go along. I can't enough of it. His scent, as well his taste… it's all so addicting.'

Another main leave you as you lose yourself in the uncontrollable haze of pleasure. "Holy shit, Y/N. You sure got a good mouth on ya." He grunts, his hips bucking into your mouth as your lapped at his sensitive head through his panties.

"Your talent should've been the Ultimate Cock-Sleeve 'cause that's all that you're good at you little slut! Puhuhuhu!"

You shuddered in shambles of pleasure as Monokuma degraded you for being nothing but a fucktoy to him, making you feel incredibly horny.

"You humping the bed to get yourself off? Do you like to grovel at my feet and suck dick like the hungry dog you are? He asked.

You let out a moan of affirmation, removing your lips from his clothed dick as you eagerly nuzzled his throbbing bulge, your hands running his doughy belly, feeling the soft fat and fur glide through your fingertips.

"Yes! Please lemme suck your dick, Mr. Monokuma." You pathetically begged, being far too horny to even care about the words falling out of your mouth.

The monochrome grinned widely at your desperation. "Since you asked you nicely, knock yourself out. You earned it." He says, placing a mitt on top of your head, meshing your face against his bulging crotch.

Not wasting a single second, your hands quickly reach towards the waistbands of the headmaster's panties, pulling them down to his ankles in a swift yet forceful tug. The monochrome bear's dick flopped out of its snug confines from the see-through fabric, nearly hitting you in the face, which you quickly move back up to doge it. A silent breath leaves you as you stare at your headmaster in all of his utter naked glory.

'Big…' Was all you can think before your mind went blank.

Monokuma's dick was a lot bigger than you originally thought it was gonna be through his underwear. It is very humanoid, resembling much of your own with its phallic shape. The length is no joke either, being roughly around eight to nine inches long, with more girth and thickness to match a soda can. The color of his cock is the same as the rest of Monokuma's body, half black and half white, running from the base to the tip. The same could be said with his balls too as each of his huge, heavy-weighted nuts is black and white, making his entire naked body perfectly symmetrical.

"Good God, you're gigantic!" You breathed out.

Monokuma laughed at your utter surprise at seeing his massive length. "Puhuhuhu! You make a sound like it's a bad thing!"

Your face burns red in embarrassment. "I-I'm not! I'm just… surprised in seeing you packing so much heat, you know?" You bashfully asked.

The bear's let out a small amused huff, chuckling. "Well, that's another quirk of this body of mine. I can adjust the size of my dick to fit my needs! Think you can handle it?"

"Of course, I can!" You said confidently.

Monokuma narrowed his gaze slightly, tilting his head as if he was not too convinced.

"You suuure? Sounds like you've never sucked dick before. Especially with something as big as mine here~" He said smugly, wiggling his cock around

You pouted. "Yes, I'm sure. I can take it!" You said firmly.

The bear stared into your eyed for a moment before letting out a sigh. "Alright. But, if you do a bad job, this rod is going straight into your ass!"

You gulped. The thought of taking Monokuma's big fat cock up your ass made you nervous yet excited at the same time. Even though you never sucked dick before, you have to put on your best performance to please to sadistic bear if you even have a chance of fucking his plump, fluffy ass.

"I won't." You said.

"That's the spirit!" He replies. "Now, blow me away! Puhuhuhu!" He laughed before resting both arms behind his head to make himself comfortable.

You let out a breath through your nose from the bad pun before reaching out and wrapping your hand around the base of Monokuma's cock. His member throbbed in response around your wrapped fingers, heat radiated onto your soft skin as precum formed and leaked from the tip of his cock, slowly trickling its way down the pulsating shaft. You started to jerk the robotic bear off slowly, watching as the foreskin bunched up and covered the tip before pulling it back. You also used your free hand to gently cupped his big balls, rolling those heavy orbs around in your palm, pressing light but firm squeezes onto those milk makers.

"Yeah… that's it, Y/N." Monokuma praised with a moan.

You let out a shaky breath, shivering in pleasure from the monochrome bear's praise. He raised a curious eyebrow and chuckled.

"Oh? Does my little servant like being praised for doing a good job in pleasing your headmaster?"

You can only nod in response, continuing to jerk your headmaster off and squeeze his balls.

"Keep that up and I'll give you a hefty reward. Puhuhuhu~" He purred, patting your head.

Your cock eagerly throbbed hard between your legs in response.

'This bear is going to drive me crazy. Pushing all of my buttons… It's scary that he knows so much of what I like.'

You continued to jerk Monokuma off, the copies amounts of precum oozing from the tip coating the shaft in a glistening sheen from your strokes, audible wet squelches audible to your ears. Your eyes hungrily gazed at the throbbing thick pole like it was an easy slab of succulent

meat, causing you to lick your lips. You desperately wanted to cram that big, girthy dick down your throat but something was holding you back from doing so, you can't quite put your finger on it though. The headmaster has been teasing and messing with you this whole time just for you to get in this kind of position. All it takes for you is one little push to flip a switch deep inside you.

"What's the matter, Y/N? Why aren't you sucking on it yet?" He asked, his voice growing low between a purr and a growl.

"C'mon. Enough with the foreplay. I can see clearly how badly you want to choke on my big dick? You want that, don't you?"

You paused for a moment as you stared at the monochrome bear in shock, not expecting to hear something so… fitly come out of him. But despite, you were incredibly turned on by his word, your head automatically nodding on its own, failing to register the sudden motion.

The bear grinned. "Well, get to it. Let's see how good that mouth of ours is~"

Monokuma's words cause something deep inside you to snap, and a raging burning fire ignited into something fierce within the pits go your stomach. Quickly closing the gap between you and the meat pole in your field of vision, you stuck your tongue out and gave the shaft a nice long slow lick, from the base to the leaking tip. A sinful moan left as you licked the lips, appreciating the salty flavor of the headmaster's sexual fluids before opening your mouth as wide as you could. Then, you make your descent, wrapping your lips around the head as you slowly swallow the robotic bear's dick, its thickness quickly filling your mouth and stretching your jaw as you sank inch by inch.

You let out a gurgled grunt, squeezing your eyes shut.

'Fuck, he's bigger than thought.'

Tears formed at the edge of your clenched eyelids as growing pain started to form from the stretched jaw. You were worried that because the shaft is quickly clogging your throat, your gag reflex comes into play and makes this a very unpleasant experience. But thankfully, it doesn't come to affect your progress, much to your relief. You continue to push forward, working more of that big dick down your stretching air pipe while you sucked and ruined your length in an attempt to help you a little bite. All of you wanted to do was to please Monokuma. That's all that matters.

"Ohhh yeah… there we go Y/N. Just like that." He groaned. "You're almost there, Y/N." His mitts tightly gripped your hair, pushing you down to help sink yourself further into him.

You let out a muffled grunt, a stray tear streaming down your burning cheek. The taste of his shaft is a lot stronger and smoky than before, sending you into a heated frenzy. Your cock is painfully strange ing against your pajama pants, soaked heavily into your fluids that stuck to your skin. You want to pry your dick free from its prison and jerk yourself off then and there so bad. But to prevent yourself from losing focus on your headwaters cock. With one final push without Monokuma's assistance, you finally managed to take the last inch of him, fully taking his length inside your mouth.

The bear let out a long moan, his dick pulsating inside the slick fleshy interiors of your maw, your lips wrapped around his length like a snug-fitting fleshlight.

"Hooooohh whee." He breathed out, raising his head to look down at you, chuckling. "Damn, you took that like a champ. Are you holding ok? Not gagging and choking on my meat and whatnot?" He asked.

You managed to give him a weak thumbs up, your face practically within the bear's crotch as the edges of your vision start to flicker specks of black.

The monochrome ear let out a small amused huff, ruffling your head. "Glad to hear it. The thought used to pass out by now, but I was quickly proven wrong. You really are a cocksleeve! Puhuhuhu!" He laughed.

"Well, Y/N. You may continue." He said, waving a dismissive paw.

Given permission, you proceeded to suck the monochrome bear off. You slowly raised your head, your lips sliding off the thick shaft as focused on getting used to the feeling of every bump and ridge of his cock moving past your quivering tongue. Once most of the headmaster's dick is removed from your maw, you took a moment to hover at the tip by circling your tongue around the sensitive leaking head, dipping into his foreskin before coming back down. It took a bit to adjust to the size considering that you had to use the hollow of your cheeks to able better yourself up and down and gagging a bit then and there. But you were motivated to give Monokuma the pleasure he deserves.

And it seems your growing confidence in your suckle is paying off well as the robotic bear is enjoying this just as you are. Flicking your eyes up, you see his breathing coming out in heavy ragged pants, his cheeks flushed as his long serpent-like tongue hung out from his parted mouth, his body shuddering in pleasure. He would also occasionally buck his hips up ever so slightly, his grip tightening onto your ruffled hair as pushed more of a big cock down your esophagus. It was quite the sight to see your headmaster come undone like this, adorable even. Though in reality, you wouldn't say that to his face if he wanted you to. Still, it made you feel good about yourself to be able to suck dick this good for a first-timer.

"Shit, you are a slut for cock, aren't you?" The robotic bear asked between heavy ragged breaths, jolting as you licked at his sensitive head. "Ohhh, I'm not gonna last long if you keep this up. You want to swallow my hot, sticky cum that bad, huh? Fill your belly up with nothing but white love and happiness and paint your head to toe with it?"

You shuddered hard, letting out a heavy lustful moan onto his cock, swirling your tongue around the tip to collect and rink the silty precum containing to ooze out of the flaring slit. Hearing your headmaster talk dirty never fails to make you more excited than you already are.

"Sounds like you like that idea~," He said, snickering. "Then keep sucking, cock sleeve!" He said, roughly shoving down onto your dick.

You let out a grunt in response to the sough motion, roughly tugging on his big balls in relation, with got him to ease up on you. You then started to pick up the pace, putting your lips and tongue into overtime as you feverishly sucked at the leaking shaft, the lead sounds of your oral affection bouncing off the walls of the silent dorm room. You wanted to keep going, suck your headmaster's thick meaty cock for hours on end. Even though you feel the jaw muscles starting to cramp up, you're not giving up just yet. You're so close to feeling Monokuma's thick, creamy jizz fire it's way down your hungry gullet.

Hollowing your cheeks once more, you swirled your wriggling tongue around the base of your headmaster's cock. Your hand continued to fondle and play with his heavy orbs, while you used your other free hand to teasingly drag their way up Monokuma's legs, your fingers danced along his quivering inner thigh. You were rewarded with heavy spurts of precum, the salty but sweet synthetic fluid splashing down onto your tastebuds as you greedily lapped it all up.

With a couple more fast bobs and complete total suckage, Monokuma spoke up again in a breathy voice. "Haaah… Mmmnggh… I'm… I'm gonna…"

Suddenly, Monokuma tightened his hold on your hair and jammed all of his cock down the back of your throat in a forceful shove. A moan of surprise leaves you as your face is pressed roughly against his musky crotch and soft underbelly. You tried pushing yourself up but Monokuma's legs were already closed in and clamp down tight around your head, the pressure of those fat thighs creaking your skull a bit and locking you in place.

"It's coming! My pure, white, sticky seed is coming! Swallow it all!" He exclaimed, bucking his hips inside your mouth.

With one last final grunt, the monochrome bear's dick throbbed threateningly before jets of thick boiling ropes of cum started spurting against the back of your throat. You wanted to appreciate the taste of your headmaster's milk fluids hitting your tingling tastebuds. But your prime focus is swallowing it all down and milk Monokuma dry. Your leaking cock ached within your trouser as rope after cum of the bear's filled your mouth in a matter of seconds, making it impossible for you to keep up to gulp down. His seed bubbled through your tightly sealed lips, dribbling down your chin and Monokuma's cock and balls. The robotic bear's legs are shaking through his intense orgasm, his face twisted in pure ecstasy as he gritted his teeth into an expression many would refer to as a 'good nut buster.'

Eventually, the rapid spurts of cum steadily weaken and grew smaller, the bear's cock twitched a few more times to coax out the last of his climax before it went still, fluids lazily leaking out of the flared slit. You swallowed the last of his semen, a burbled moan leaving you as Monokuma's milky jizz settled within your stomach, its radiating warmth making you shudder. For a robot, you're surprised he had any kind of fluid come out of him. Even though he's already technologically advanced as said many times by him, it's still scary how easily he can replicate a person's orgasmic fluids in that form of his.

After holding you in place for a moment, Monokuma loosened his grip and pushed you away for him. You pulled back, your lips noisily sliding off of the bear's cock with a wet pop as you swallowed the rest of his jizz that filled your cheeks in a thick hearty gulp, letting out a shaky sigh afterward.

Monokuma collapsed onto the bed, breathing heavily as sweat dribbled down his forehead and the rest of his body.

"Phew! That… was amazing!" He said breathlessly before sluggishly pulling himself up with his arms.

"It feels great to blow off some steam from this whole mastermind business I have going on.

Granted, this is the first time I've ever done this kind of stuff, especially with a loyal pet such as yourself. Nonetheless, you did a pretty good job of getting my rocks off. A for effort!" He said, lazily scratching his belly, looking positively satisfied.

"Gla… Glad you enjoyed it, Mr. M-Monokuma." You said between heavy pants, looking like an absolute mess.

The robotic bear grinned smugly. "Heh. I could say the same. You seem to like the idea of being my little cock sleeve. As evidence to your little flagpole standing up downstairs~" He says, pointing a finger down at your pitched tent.

Your cheeks burned bright red. "Well, it's not my fault you make everything hot and whatnot!" You protest. "Stupid, sexy Monokuma…" You muttered under your breath.

The black and white ursine snickered. "What can I say? I'm irresistible!" He boasted, pressing a paw to his chest as laid himself out in a sexy pose.

After joking around for a moment, Monokuma sat himself up with a grunt. "Alright, kid. A promise's a promise. Your reward for going me a good nut buster is none other than…" He trailed off for a dramatic effect.

Then in a quick motion, Monokuma turned himself around, going down on all fours as he proceeded to stick his prominent backside far out at you.

"My big, fluffy round ass! Puhuhuhu~!" He laughed, wiggling his prominent tush side to side teasingly.

Your eye widened, saliva pooling inside your mouth as you feel the neutrons in your brain spark in seeing your monochrome bear's heavy-filled assets move so enticingly in full view. Monokuma peered over his shoulder, his eyes getting yours with a smug, mischievous look on his face.

"Puhuhuhu! You look like you're gonna cream your pants just from staring at my ass alone! That's no surprise considering how much of a freak you are!" He playfully taunted.

To tease you further, the black and white ursine began bucking his hips, the movement causing those giant ugly mounds to bounce up high in a wide arc before they came crashing back down. It caused those cheeks to smash together in an audible meaty clap, sending a rippling gelatinous wave that flowed across those black and white full moons before settling. You felt your face grows red as a tomato, your neglected dick throbbing excitedly at the erotic spectacle in front of you.

The grin on the black half of the ursine's face widens at seeing the utter, dumbfound on your ace in being so heavily transfixed onto his quaking buttocks, his red jagged eye glowing brightly in predatory hunger. So he intentionally continued to twerk in front of you, putting more force into his bucking hips to allow his fat doughy cheeks to bounce even higher and smack against each other harder than before. Your pulse grown into a frenzy as your negated cock throbbing painfully within your stained pajamas as you needlessly watched the beads of sweat splash from his rippling globes.

The sounds of those loud meaty claps emitting from those cheeks reverberated within the thick walls of your dorm room, deafening your ears, making your heart skip several beats. And to top it all off, hidden within the deep murky trench of the headmaster's parted cheeks was his puckered hole. The tight, puffy wrinkled hole was a dark grey color, flashing itself with teasing winks whenever those huge cheeks parted from Monokuma's ceaseless bouncing for just half a millisecond. It made your libido rise to an all-time high, threatening to burst free from your soaked pants.

"Awww, what the matter? Is the sight of me bouncing my big butt around making you horny?" He chuckled cheekily.

You nodded automatically, digging your fingernails tightly into your legs in a tempt to restrain yourself.

"You want to stick your big dick inside me, don't ya? You wanna force me down onto the bed and fuck my robotic brains out all night long till can't walk in the morning, huh? I can see how little resistance you have left~" He heavily teased.

You let a needy whine slip free from your lips as you visibly squirmed in place, trying to keep what little sense of restraint you have left. He knew how desperate you are in wanting to fuck him, and he reveled in it.

"Yes! Yes, please!" You eagerly begged.

The monochrome bear chuckled. "Well then…"

The black and white ursine slapped both mitts upon his thick doughy cheeks, sinking his fingers into the plump fat as he grabbed a good fistful in each paw, spreading them wide apart. Your neglected cock throbbed needle inside your trousers as Monokuma's tight hole was revealed to you, the grey pucker giving a teasing wink.

"Come here and eat this 'cake.' Prove to me how much to love and have your undying obedience towards little ol' me~ Puhuhuhu!" He purred out suggestively before letting his cheeks go, the full moons colliding against each other in a heavy, rippling clap.

You didn't need to be told twice. You quickly tore your trousers off of you in one fell swoop, a small relieved sigh leaving you as your rock-hard leaking erection was freed from its tight, sticky confines. Then, you quickly crawled over towards the bent-over ursine, your heart pounding quickly in your chest as you got closer and closer to those perfect round black and white moons.

"Wow..." You muttered.

Without a second thought, you lurched forward, slapping your hands onto the ursine's rear, grabbing a fistful of Monokuma's succulent, doughy buttcheeks. They felt exactly as you expected them to be; soft and pillow-like yet maintaining a bit of firmness underneath all that fat. It's like you're pressing down onto some high-quality bread dough. You tighten your grip on his caboose, taking a moment to savor this delectable sensation before using your hands to squeeze and knead into those plump cheeks, worshipping that fat round ass. You hear a small, pleasured sound come from the robotic bear, a grunt soon followed as you spread those cheeks apart, exposing that soft-looking hole in between.

You licked your dry lips at the sight of it, your head growing hazy as a rich, masculine scent wafted from between the trenches of the ursine's deep crack in your flaring nostrils. It was unlike anything you'd ever smelled before coming from the robotic bear. It was a six you've been hit with the highest known drug imaginable, succumbing to the effects happening throughout your body, making you unable to think straight. So, you leaned down, drawing yourself closer to that puckered target ever so slowly, the heat of the black and white bear's fat ass radiated off your cheeks. Before you know it, you plummeted your face deep within those mammoth-sized buttocks, squeezing those heavy mounds on either side of your head as you nuzzled against his deep crack, etching the ursine's intoxicating stench onto your skin. Then, there was his pucker. That tight grey hole was mere inches away from your nose, the fleshy orifice clenching down to kiss its 'lips' against the tip of your nostrils, begging you to make contact with it.

So, without a moment wasted, you swiped your tongue against the rim, pressing the saliva-coated tip against the wrinkled entrance. Doing so caused the headmaster to jump, letting out a heavy moan in response to his hole being directly stimulated, the entrance quivering with excitement. Continuing forward, you licked across the black and white ursine's pucker in long slow swipes, tracing your tongue along the smooth, wrinkled outer edges as you slather it under the heated warmth of your saliva. The sensitive taint responds to your diligent tongue swipes by clenching its muscles down onto your moving wriggling organ, melting its delicious musky flavor down onto your tastebuds.

"Mmmmgh.. fuck yeah~" Monokuma groaned out in a lustful growl.

"You like eating my ass, kid? Does it taste just as good as you imagined it to be? I made sure I take good care of it. Wouldn't want to disappoint ya~ Puhuhuhu!" He giggled before roughly pushing his back, slamming your tongue against his fleshy ring, further smothering you between his giant, doughy cheeks.

"Come on, Y/N. Eat my ass. Get your tongue in there niiiice and deep~"

Unable to hold back anymore, you pushed your face further between the ursine's thick cheeks, the tip of your tongue pressed firmly against the tight entrance. Your heart pounded against your ribcage, cock throbbing needily between your legs as you felt that single pucker gave a bit of resistance to your prodding. But once the headmaster's anus loosened up just enough, you immediately shoved your tongue inside the opened ring, engulfing from within its murky insides.

Your eyes roll into the back of your head as you let out a loud heated moan, to which your cries were muffled and caused a slight rumble to reverberate through the black and white bear's backside. Monokuma's slick inner walls clenched down on your tongue hard, the muscles pulling your tongue deeper into the robotic bear's organic bowels. The utterly intoxicating flavors you've tasted before are a lot stronger than before, having a much heavier and spicy kick to it. It was as if you've gone into ass heaven, a complete carnal, sinful paradise you couldn't possibly imagine yourself reaching.

Eager to put more passion into tongue fucking the headmaster's anal passage, you leaned yourself in even closer, squishing your hands into those bulbous cheeks to steady yourself as you latched your lips onto the wrinkled rim, sucking on it. Monokuma moaned loudly in response, his cock leaking coupons amounts of precum onto your bedsheets from having his asshole being worshipped and his insides being eaten out so deeply. You lost track of time as to how long to been going at it, all of the moans and dirty talk let the monochrome bear constantly spewed out of his mouth became nothing but white noise to you.

Eventually, you pulled yourself back from Monokuma's fat backside, your tongue sliding out of the ursine' asshole in a squelching wet pop, leaving a thick string of saliva that connected the end of the winking, kiss-swollen hole before breaking soon after.

"Hah…hah… fuck me. That was… the best hole I've ever eaten out…" You said panting heavily as you tried getting rest air back into your lungs, Monokuma's scent and taste lingered heavily on your face and tongue.

"I can't take it anymore…!" The black and white bear said in a hushed eager tone, his cheeks glowing bright red.

In a quick motion, Monokuma reached behind his and hooked his mitt-like paws deep into his fat doughy cheeks, spreading them apart to reveal his puffy, saliva-covered hole.

"Enough with the foreplay, kid! Shove that big dick of yours inside my hungry asshole! Destroy my robo pussy!" He said heatedly, his little nub of a tail wiggling erratically as he swayed his wobbling rump side to side, his swollen hole blowing teasing kisses at you.

Obeying your headmaster's horny request, you gripped your leaking member with a shaky hand, giving it a few pumps to cover the shaft in your fluids as makeshift lube. You know that Monokuma constantly prepared himself to take something as big as you with the number of porn streams he constantly showed you on your dorm monitor. But, just in case, you rather have this to be a smooth insertion.

You let out shaky, heated breaths, your heart pounding against your rib cage as you gripped a good chunk of ass fat from the ursine's cheek, angling your tip towards his wrinkled opening.

"What's the holdup?!" Monokuma said impatiently, snapping his head back at you. "Hurry up and fuck m—"

His orders quickly died in his throat as you suddenly thrust your hips forward. Every inch of your thick shaft slid through the robotic ursine's fleshy inner walls without any resistance, your crotch pressed flushed against his thick cheeks. You bit your lip to keep yourself from moaning aloud as the surprising warmth of Monokuma's tight depths assaulted you. His slick walls squeezed and caressed every inch of your pulsating cock, sending bolts of sickly pleasure down your spine.

You couldn't think straight at this point. Any notion of any rational thought you have quickly faded to a blank white and is replaced with heavily heated desires. With your cock throbbing needle inside Monokuma's clenching walls, A single deafening order rang through your ears; breed Monokuma senseless.

Consumed with primal lust affected by your sexy, sadistic headmaster, you pull your hips back, sliding your cock out of his robotic bear's asshole. Then, without warning, you slammed your hips forward into his quaking opening, his cheeks emitting a heavy wet clap as you plunged your cock deep into his bowels.

From there, you began your brutal rut against your headmaster with such fervor and strength. Seeing the doughy fat of Monokuma's mammoth cheeks heavily ripple with your hard thrusts spurs you to keep going and give the robotic bear your rough display of affection and devotion towards him.

"H-Holy shit!" Monokuma managed to cry out, gripping his paws into the bedsheets tightly, his body and the bed rocking to your movements.

"That's it, kid! F-fuck my brains out!" He said, his eyes completely glazed as his serpent-like tongue hung from his parted maw, staring off into space.

You grunted in response, all too occupied with your heavy breeding to even form proper sentences. As you were plowing your meat deep into the ursine's inside, you felt your glands pound something… fleshy deep inside his anal canal. Almost like a squishy walnut perhaps… But that didn't stop you from your relentless fucking. The pleasure was too strong yet still kept you going. With how Monokuma's tight hole constantly clamped down hard onto your dick was intense, each thrust of your hips growing forceful and harsher over time, reaching deep within the robotic bear's fleshy insides as far as it could. You hugged yourself close to the monochrome ursine, picking up the speed while Monkuma's screamed in ecstasy.

With the incredibly fast rate of the breeding session with your headmaster, you can feel your body grow tired as you feel a building pressure stir within your tensed balls, signifying that you're nearing your climax. Heavy breaths left you as sweat coated your body, your arms beginning to shake as pleasure coursed through your veins. But you continued to push onward, using every last bit of strong will and adrenaline to continue fucking your headmaster's robotic brains out.

"M-Monokuma, I-I'm not gonna last much longer…!" You breathed out, your throbbing cock spurting heavy amounts of precum within the ursine's tight, clamping walls.

The monochrome bear managed to snap his head back at you plowing him, his mitt wrapped around his leaking dick, stroking it roughly in time to you rutting him. "G-Good! I want you to fill me up completely. Every last fucking drop of your love and appreciation for me!" He said heatedly.

You shakily nodded, speeding up your thrusts as the pressure grew within your throbbing cock and balls growing at an exponential rate, the bear's slick walls constantly squeezed, clenched, and spasmed around your shaft. Eventually, with a few final hard thrusts, your climax hit you faster in a speed train, sending you over to the edge.

You raised your high up high and let loose a silent groan through your tightly clenched teeth, pressing your crotch firmly against the monochrome ursine's voluptuous rump as your throbbing cock buried down to the hilt. Thick ropes of your hot, gooey, sticky cum fired out from your flaring urethra right into the murky depths of the robotic bear's innards, staining his slick inner walls as they clench and massaged your dick to coax more of that semen to fill his quaking bowels. Monokuma's orgasm came right after yours as he lets out a high-pitched moan, his eyes rolling into the back of his head as fat ropes of his synthetic seed came rushing out of his spamming cock, coating your bedsheets with his fluids.

But eventually, all good things must come to an end, as the both of you have reached each other's limit. Your spurting cock fired off the last couple shots of your white-hot seed until it became just a mere trickle, your balls completely milked dry within your headmaster's insides.

You bring your head back down with a heavy, shaky sigh, shuddering lightly as the afterglow started settling in, your body tingling in pleasure. Then, after giving Monokuma's well-filled ass a good pat, you pulled yourself out, your cock noisily slurping its way out of the ursine's stretched anus in a wet, sickening pop. The ursine let out a deep rumbling purr as a hot rush of semen gushed out of his hole before reaching behind a plugged up the flow using his mitt in an attempt to keep the rest of your hot jizz inside his now bloated stomach.

You collapsed down onto the bedsheets in a heavy thud, laying yourself right next to the tuckered-out ursine as the two of you recovered in silence, relishing in the afterglow as washed over your bodies like a soothing tide.

"Phew, that was amazing… wasn't it, Monokuma?" You asked in heavy breaths.

The robotic bear let out a weak hum of agreement. "Mhm. I heavily agree with you, kid. You were incredible. Everything I could've hoped for. Puhuhuhu…" He laughed softly. "But, holy hell, you did a number on me. I don't think I can able to walk straight by tomorrow morning." He said, sluggishly rolling himself over to lay down facing you, his distended belly audibly sloshing.

You chuckled. "Well, I wanted to prove my love and devotion to you in the best way I can!"

"And that you did, Y/N. I've underestimated you. Perhaps in the future, I can call you into my office and help me blow off some steam. Would you like that?"

You nodded quickly. "Yes!"

The robotic bear let out a small snicker, reaching a mitt out to gently stroke your cheek. "Excellent. I'll be sure to keep that in mind~" He purred.

You closed your eyes and leaned your head into Monokuma's mitt, relishing in his gentle touch. Though, you were silently disappointed when he pulled his mitt away from you, the warmth you once felt quickly diminished.

"So, what now?" You asked hesitatingly, not sure what to do in this whole post-sex ordeal.

"Well, as much as I want to stay here and lay in bed with you, I gotta head back to my chamber and get ready for tomorrow morning. I can't have people grow suspicious over our little ordeal now, can't we?"

Monokuma slowly sat himself up, stretching his arms to work out the kinks in the mechanical joints he calls bones.

"You can keep the bra and panties. I'm sure you'll get some good use for them whenever you want to beat your meat thinking about lil ol' me. Puhuhuhu!" He laughed, shuffling to get off of your bed and head out of your dorm room.

But before he could make a single move, you quickly stopped him, blindly reaching out to wrap your hand around his arm to keep him in place.

"Wait! Please don't go, Mr. Monokuma! Can you stay just a little while longer? Like, we can… cuddle and such." You timidly asked.

"Sorry, but I can't. I'm a busy ear when it comes to running both a school and a killing game. I want everything to be in tip-top condition!"

"Come on, please?" You begged, giving him your best puppy-dog-eyed look. Monokuma stared at you with a grimaced look on his face before replying with a heavy sigh.

"Alright, fine. Since you're that desperate for me to appreciate you, I'll stay and cuddle with you for the night. Just this once and I'm leaving early tomorrow morning. Got it?" "Of course. Thank you, Mr.Monokuma!" You said happily.

"Sure thing, kid." He said dismissively with a huff.

With a clap from his mitts, Monokuma turned the lights off in your room, and the place shouted in pitch-black darkness. The robotic bear then laid himself down and huddled up close to you, wrapping his arms around you as he pressed his soft ample breasts against your chest.

"Rest well, Y/N. We have so much to do tomorrow now you've agreed to become the blackened for the killing game. And become my little servant~" He said huskily, nuzzling his muzzle against your chest.

You blushed, wrapping your arms around your headmaster in a loving embrace, holding him tight and never letting him go.

"Of course. I love you, Monokuma." You said, resting your chin against the top of his head, brushing your lips against his soft, fuzzy fur.

"I love you too, my favorite student. We're gonna have so much fun together. Puhuhuhu~" He laughed lowly, a dark sinister spreading across his face not visible to you.

With that, you began to fall asleep with a blissful, happy smile on your face. You've never felt this good in giving up all sense of hope in escaping this school and seeing your precious loved one again. To fall into the dark, corrupted pits of despair to be with the one you cherished the most; your beloved headmaster. Now, all it takes is to win the killing game and stay with Monokuma for the rest of your miserable life, away from the outside world.

You would lie for him, you would kill for him, and you certaintly die for him now that Monokuma will forever be your one and only.

THE END