Sexually Humiliating the Dean

Story Info
A sudden new rule to humiliate Greg's bully, the buxom Dean.
15.8k words
4.7
24.2k
83
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Greg Burkus sat on the floor staring mindlessly at the TV, which was giving an important update.

The couldn't focus on the update, he knew he was supposed to, but all he could think about was the coming school day.

Greg was enrolled in St. Bartholomew's Bridge school. It was a feeder community college for the prestigious St. John's college, a private University where the real movers and shakers sent their kids.

However, St. Bartholomew's was run almost exactly like a Highschool. Class all day, starting at 8am. It was run by an absolute tyrant, Ms. Vivian Sato. She was the Dean of the school, and a lead Professor at St. John's School of Business.

She was the bane of Greg's existence. He was pretty certain she didn't like him because Greg was poor. Him and his mother lived in the only trailer park in town. His mom got him a needs based scholarship to St. Bartholomew's. If he could maintain a 3.0 GPA, in two years he could move onto St. John's.

It was a big deal for him, and his family. He would be the first one to graduate college.

Zzzt, the TV buzzed, sounding the end of the announcements. Greg snapped back to reality.

"Boy, the world has changed hadn't it?" His mom said with a smile. Her happiness only increased the pit in his stomach. She was so proud of him, but he hated going to school.

"It sure has," Greg replied, but his world hadn't improved at all. At 120 pounds and 5 foot 7 inches tall, Greg had been the butt of all the jokes his whole life. Picked on and bullied. But his problems were far above the problems she was talking about.

His Mom was talking about the new World Leader, known only as Leader. He mysteriously rose to power two years ago and forced peace among all the warring nations. The world had blossomed under his rule. Trade was up, corruption was down, there was peace on earth.

As part of his new rules, everyone on Earth, was required to sit in front of the TV to listen to his important announcements every morning. Greg never really paid attention to them.

"Looks like the bus is here, better go on or you'll be late," His mom said, handing Greg his backpack and a brown bag for lunch. Greg put on a smile, and skittered out the door.

Greg gave a nod to the bus driver, Earl. Earl lived across the way, but worked as a bus driver. Greg looked at all the familiar passengers on the bus, all elementary and middle school kids. He was the only student at St. Bartholomew's to ride the bus. Everyone else had their own cars.

Greg took his usual seat at the front and stared out the window, trying not to think about his inevitable morning encounter with Ms. Sato.

The bus took off as Greg zoned out.

Greg had tried everything to avoid Ms. Sato in the morning, nothing worked. She always seemed to pick him out. The best bet was to just hope she was busy or in a good mood.

Before long the bus came to the St. Bartholomew's campus, the doors opening. Greg stood up and headed for the door.

Earl, the bus driver held a piece of paper up for Greg to take.

"What's this?" Greg asked before getting off.

"A Late Slip. Traffic was bad today." The color drained from Greg's face. He was LATE? Greg snatched the slip and bolted towards the front door of the school. The grounds and the campus were empty. Greg looked at his watch, 8:05, FUCK!

Greg flung the front doors open, no sign of Ms. Sato, he began running towards his first class. Maybe he'd gotten lucky.

He rounded the hallway to his first class. No sign of Ms. Sato. He stopped just short of the classroom door, took a deep breath to calm himself, and then walked in.

Advanced Math, the lecture was already underway but no one looked up. He took his seat and took out a deep sigh of relief. He made it.

Greg took out his notepad and began to take notes on the lecture. That's when Mr. Holmes, the teacher, turned around.

"Is that Mr. Burkus? Ms. Sato would like to see you in her office." Greg's heart sank. The kids around him let out a snicker.

"But, the bus was late, I have a slip," get replied meekly. Mr Holmes shook his head as if to say 'who cares' and then pointed toward the door. With a heavy sigh Greg stood up and headed for the Dean's Office.

As Greg was leaving the class Brad Tiller, a tall, handsome, football type, pointed at him and mouthed "Loser."

Greg walked, shoulders slumped, towards Ms. Sato's office, which was at the front entrance of the school. He rounded the hallway to see Ms. Sato waiting for him.

Ms. Sato was a stern woman. Her father was a Japanese businessman who married an American sweetheart. She had jet-black hair, cut in a shoulder length bob. She was wearing a very professional looking suit, although it was tailored to show her curvy figure. She turned her head, her black eyes meeting Greg's gaze.

"Mr. Burkus, you're late," She said in her usual, harsh, critical ton.

Greg held up the slip of paper Earl had given him as he approached. "The bus was late." Greg said in reply.

Ms. Sato scowled at Greg in silence as he approach. Not responding at all to Greg's excuse.

Behind Ms. Sato Greg could see Susan Smith opening the front doors. Susan was one of Greg's only two friend sin the school. But she was busy so they didn't hang out much.

"Sorry I'm late Ms. Sato, I slept in," Susan said with a smile.

Ms. Sato turned and smiled back at Susan.

"Oh no worries. We all make mistakes." Ms. Sato replied to Susan.

Ms. Sato turned back to Greg, her face returning to its scowl. She pointed to her office.

Greg met eyes with Susan, she mouthed 'Sorry', he then slumped into Ms. Sato's office. Ms. Sato followed, closing the door behind her and sitting behind her desk.

Her office looked like a typical Dean's office. A large, mahogany desk. Plush, leather chairs. Shelves full of books.

Ms. Sato sat down behind her desk. Greg began to sit down across from her when she said,

"I don't think so Mr. Burkus, please stand," Greg gulped at the chastisement and remained standing.

Ms. Sato then held out her hand, "Let me see the slip." Greg handed her the slip. Before looking the corners of her mouth curled into a smile and she ripped it up. "An unexcused absence means detention then." She said with a smirk.

Greg fumed, but knew better than the try and defend himself. Greg looked at the ground, avoiding Ms. Sato's penetrating gaze. She was smiling at him, gloating in her victory over him.

Ms. Sato let out a quick victory laugh, and with an arrogant smile she said, "I'll see you in detention, now get out."

Without a second warning Greg turned and left her office.

Greg slinked back to class, ignoring Brad Tiller's jeers as he walked back in.

Greg closed his eyes and mustered his resolve. Detention wasn't unusual for him. Ms. Sato made up all kinds of excuses to get him in trouble, but she never expelled him. Just another year and a half and he'll be free and onto a better life. He took a deep breath, imagined himself shaking off all the hate, opened his eyes and began to pay attention to the lecture.

It wasn't long before Greg found himself at lunch, his sack lunch consisting of a cold hot dog and left over macaroni and cheese.

"I heard the Leader used Hypnosis to take over the world, and that the morning broad cast is hypnotizing us!" Tim said. Tim was Greg's other only friend, besides Susan. He was a bookish, nerdy type, like Greg and was heavily into conspiracy theories.

"Bah, that's crazy," Susan said, dismissing Tim's claim.

Tim, Susan, and Greg were sitting at the edge of the cafeteria, the social outcasts. Each of them had been marked as 'weird'. Tim was socially awkward, and generally would ramble on about chemtrails, and government over reach.

Greg was dirt poor, and didn't know his father. He was also scrawny and short at 120 pounds and only 5 foot 7 inches tall. He was a particularly easy target for the more athletic boys at St. Bartholomew's.

Susan was a popular kid in Highschool. However, her parents split up and she ended up Pregnant and had to take a year off. All of which left her with a social stigma at St. Bartholomew's.

All three of them had found company together as social outcasts.

"But what's more crazy is that Greg got detention again," Susan said angrily.

Greg waived his hand trying to dismiss the subject.

"Again? She's really got it out for you," Tim said taking a bite of his sandwich. With his mouth half full Tim continued, "Isn't there anything we can do?"

"Bah, I just wanna do my time and move on. I'd rather not stir the hornets nest."

"You sound like your in Prison," Susan replied.

"You know," Tim speaking now, still with his mouth full, "You should write a letter to the leader, ask him if he can hypnotize her into being nicer to you."

Greg let out a laugh at the thought. Susan didn't laugh, instead she was visibly biting the inside of her cheek.

"Real funny Tim," Susan said defensively. Susan was a fervent defender and follower of the Leader, while Tim was the opposite.

"Aah, what, it's worth a shot. I'm not saying the Leader's a bad guy, just that he's probably got the world under hypnosis. If that's true, he could help out my friend Greg."

"That would be nice wouldn't it? Snap your fingers and she just leaves me alone," Greg said with a half baked smile, dreaming of an impossible future.

"Leave you ALONE? That's not very creative. I'd do more than that. Revenge for all the times she's been unfair." Tim then made a lewd gesture with his hands miming Ms. Sato's large chest and raising his eyebrows suggestively.

Susan threw a baby carrot at Tim, which he ducked with a wide grin. He looked at Greg and said, "I mean, tell me I'm wrong."

Greg let out a heavy sigh and admitted, "She is very attractive."

The bell went off, signaling the end of lunch.

Tim let out a squawk as one more carrot hit him in the face.

"I'll see you pervs tomorrow." Susan said getting up. She paused and put a hand on Greg's shoulder, "We'll figure something out for Ms. Sato," Susan said somberly and then headed off to class.

The rest of the day flew by uneventfully for Greg, until it came time for detention.

Greg walked into the classroom to find it empty, as usual. He was generally the only one in detention. He sat down and looked at the clock. Greg didn't really mind detention, he used it to focus on his school work and do his homework, so long as Ms. Sato didn't supervise.

Greg's stomach dropped as he heard the clack, clack from Ms. Sato's unmistakably unique gait. That meant he wouldn't be able to work on homework, and it was going to be a long night. Greg sunk his head into his arms as he collapsed onto his desk.

Greg opened one eye as he heard Ms. Sato's high heels round the doorway. The conversation he had with Tim and Susan at lunch flashed through his head, as he allowed himself to recognize Ms. Sato's beauty.

She was just a tad taller than Greg in her high heels, so she was probably 5'6 without them. She had jet-black hair and eyes, with a beauty mark just under her left eye. Her hair was cut in a shoulder length bob. She was dressed very professionally, with a suit jacket and knee length pencil skirt, with a white button blouse. She was wearing dark stockings under her skirt and matching 3-inch high-heels. It was clear she was very well endowed, both with a buxom chest and a large ass.

Greg's daydream only lasted a few short second as Ms. Sato cleared her throat.

"Do I have to remind you how to greet a teacher?" Ms. Sato was standing at the front of the room with her arms crossed, looking at Greg sternly.

Greg stood up, "Good evening Ms. Sato," he said, putting on a fake smile. Ms. Sato glared back at him.

"Good enough." Greg sat back down. "Don't bother taking out your homework.

Ms. Sato sat on the desk at the front of the room. Her legs crossed over each other at Greg's eye level. Ms. Sato took a deep, pensive breath before speaking,

"What are you doing here Greg? You're wasting your time," She said in a surprisingly caring voice. Greg's face contorted in confusion and at the abrupt change in tone.

"What?"

"Don't you think you'd be better suited at the Midvale Technical College? Your just wasting time here, and taking up a slot for a more promising student." Ms. Sato's face was completely sincere. "I mean, think about how helpful you'll be in the trailer park if you can fix their old cars."

Greg sat in stunned silence. He should have known better.

Ms. Sato took another deep breath and then stood up, walking behind the desk.

"Look, the reality is not everyone is meant for College. I know you think you're going to be the first, but I can tell you now. I've seen hundreds of kids like you, and they all end up getting some girl pregnant too early, or get arrested for drunk driving, or just flunk out. It's selfish to hold this spot away from a more deserving student."

Ms. Sato was leaning on the desk now, giving Greg a flash of her cleavage. After a few moments of silence she pulled out a sheet of paper and put it on Greg's desk.

"Here, I've gone through the trouble of getting you the resignation paperwork. Fill it out, and you'll have my glowing recommendation to Midvale."

Greg shook his head. His face starting to flush with anger. Trying to calm himself Greg managed to say,

"I'm not dropping out."

Ms. Sato began to visible clench her jaw in anger. "Very well." She then abruptly sat down and pulled out her laptop. "Don't even think about touching your homework. This is detention." She said as she began to boot up her laptop.

Greg spent the rest of the evening sitting at the desk in detention. It was nine o'clock before Ms. Sato dismissed him.

By the time Greg got home it was late. He shoved a pop-tart in his mouth before beginning his homework. Red-eyed he looked at the clock as it said 2am before he finally finished and managed to go to bed.

Greg awoke groggily to his alarm blaring and his mom yelling, "Greg, the bus is here!"

He jumped up as he realized how late it was. He had no time. He grabbed his backpack and ran for the door, wearing the clothes he had on yesterday. He missed breakfast, the morning message from the Leader, all of it.

He saw Earl at the bus stop waiving at him.

Greg got on the bus out of breath.

"Thanks... Earl," Greg said between gasps of air.

"Don't sweat it, I owe ya," Earl said with a smile.

The last thing Greg needed was to be late again. Greg knew his dirty uniform was probably going to be a problem, but one day at a time he thought to himself.

The arrived at school on time as Greg began to head towards his locker. His heart sank as he saw Ms. Sato greeting students in the hallway. She always corrected Greg, no matter how perfectly he greeted her.

Greg took a deep breath and then walked through the front entrance.

"Good Morning Ms. Sato," Greg said faking the biggest smile he could muster while continuing towards his locker.

Greg felt Ms. Sato's hand on Greg's arm, turning him to face her. Greg kept smiling, he knew this was going to happen.

"Mr. Burkus, how many times do I have to teach you to greet me properly," Ms. Sato said, her face scowling at Greg.

"I'm sorry Ms. Sato wha-" and before he could finish his sentence Ms. Sato pulled Greg into her body and forced her lips onto Greg's mouth. Greg's hand was forced onto Ms. Sato's buxom chest by her own hand. Her hand forcing his hand to feel the outline of her bra. Ms. Sato's tongue was exploring the inside of Greg's mouth, her tongue darting in and out with passion.

Greg could hear a couple of students passing as Ms. Sato forced herself onto him.

"What a loser, he'll never learn how to properly greet Ms. Sato."

Ms. Sato and Greg stood in the entrance hallway, passionately exchanging saliva, as the rest of the School went on as normal. Greg felt a mix of shock and excitement every time Ms. Sato's tongue grazed across his lips or when her tongue plunged into his mouth to flick at his own tongue. While they were kissing Ms. Sato began to take off her professional blazor, leaving her in just a white button up blouse that did little to hide her buxom nature.

Ms. Sato broke her kiss and pulled Greg back enough to stare into his eyes.

"You can't even keep the most basic rule: Greg Burkus is to greet Vivian Sato with sexual humiliation," As Ms. Sato scolded Greg for not following the rules she began to unbutton her strained, white blouse. Each button undone revealed more and more of her deep cleavage and her black, lacy bra. "You could at least try, it seems I'm the one violating you."

Greg stood in the hallway, utterly stunned by what was happening. His mind was only halfway processing that Ms. Sato was undressing in front of him, in the middle of the School. His classmates were all walking by, most of them making disparaging remarks.

"He can't do anything right."

"What a pig, can't even humiliate Ms. Sato."

"What an idiot."

Greg snapped back to reality to see Ms. Sato standing with her bra pulled down and her white blouse completely open, revealing her massive EE sized tits. She had a scowl of disappointment on her face with her arms crossed under her chest, accentuating her bust.

Despite how terrible Ms. Sato treated Greg, Ms. Sato was gorgeous. Her white blouse was still tucked into her professional, pencil black skirt, but was completely unbuttoned. Her lacy, black bra had been pulled down to reveal her massive breasts. She had large nipples as well, with beautifully pink areolas. Her legs were covered in black stockings that ended in a matching set of high heels. Ms. Sato was taller than Greg in her heels, which added to her dominating personality, although Greg was short at 5' 7".

"Good Morning Ms. Sato," A student said, walking past the two of them.

"Good Morning Laura, how are you today?" Ms Sato responded with a cheery tone.

Greg watched the interaction between Ms. Sato and Laura with stunned belief. Ms. Sato was effectively topless, and no one seemed to be reacting. Greg feared this was all some kind of test or prank to get him kicked out of School.

All the abuse and belittling mixed with how sexy Ms. Sato's was put Greg into a hazy funk and he snapped. He didn't care what the repercussions were going to be, he knew he wanted a part of Ms. Sato. More than that, he wanted to return all the humiliation and injustice she had done to him.

Greg interrupted Ms. Sato's conversation and placed his hands on her shoulders and pushed her to her knees. He grabbed a fistful of Ms. Sato's hair and pulled her head back and began to forcefully resume their kissing. With his free hand he pulled down his pants and boxers, revealing his large, 8 inch cock. Greg grabbed Ms. Sato's left hand and placed it onto his girthy meat. With no hesitation she began to stroke his rigid member. Ms. Sato's small hands looked tiny in comparison to Greg's monstrous dick.

"I see you're busy, I'll talk to you later Ms. Sato," Laura said to Ms. Sato walking away from the pair.

Greg broke off the kiss, leaving a long string of saliva between him and Ms. Sato. Ms. Sato was looking at Greg completely different, somewhere between pride and excitement rather than disdain.

"Yes, that's much better." Ms. Sato said looking up at Greg. Ms. Sato's small hand was still stroking Greg's large cock, her hand lubricating itself with Greg's precum. Ms. Sato was wearing her wedding ring, a platinum ring with a large, shiny diamond on top, a subtle reminder that Ms. Sato was actually married, despite her insistence on being called Miss instead of Misses.

Greg's hands moved towards Ms. Sato's bare chest while she stroked his hard cock. He started with a rough squeeze, Ms. Sato's hard nipples digging into the palm of his hand. Greg mauled her large, soft tits before focusing his attention to her big nipples. Squeezing each of them between his index finger and thumb he began to lightly tug.