Yes, Headmistress by bbbs
Summary:

The headmistress at Byron's new school is massive, vuluptuous woman who towers feet above even her tallest students and staff. As if this wasn't enough to make Byron nervous, when she looks at him, he notices something in her expression that makes the hair stand up on the back of his neck. It's too bad he's required to spend so much one on one time with her this year...


Categories: Giantess, BBW, Breast Enlargement, Butt, Crush, Unaware Characters: None
Growth: Amazon (7 ft. to 15 ft.)
Shrink: None
Size Roles: FF/m
Warnings: None
Challenges: None
Series: None
Chapters: 7 Completed: No Word count: 20369 Read: 48872 Published: November 05 2019 Updated: August 06 2022

1. Chapter 1 by bbbs

2. Chapter 2 by bbbs

3. Chapter 3 by bbbs

4. Chapter 4 by bbbs

5. Chapter 5 by bbbs

6. Chapter 6 by bbbs

7. Chapter 7 by bbbs

Chapter 1 by bbbs

Byron wasn't sure how to feel. He supposed he was expected to feel nervous starting at Maximilian Waycroft Massachusetts Boarding School today. And sure, he supposed he was a bit nervous. But the tiny blond receptionist with whom he had checked in, Byron assumed by her age that she was a student, made him seem comatose by comparison. The girl, short even to Byron who stood an unimpressive 5'6", sat behind a reception counter so tense that she was practically shaking while Byron sat calmly in the outer office waiting to meet with the headmistress.

 

His parents, undoubtedly, would want him to feel remorseful, given that his admission to Waycroft was intended as a punishment. But while Byron would indeed miss spending his senior year with his friends at his old public school, he thought it rather worth the transfer just to get out from under his parents oppressive regime. He generally considered himself a good kid, he did well in school despite not trying very hard, he had no interest in hard drugs, he was generally very well-liked by both adults and his classmates, and he had thus far avoided any teen pregnancy scares. Yet Byron's parents considered their only child a lost soul due to his total indifference to their exceedingly strict and often arbitrary rules.

 

So it wasn't much of a surprise when his parents had their pearls firmly clutched after finding pot in his room. They were waiting to confront him when he came home from school that day, his mother almost in tears and his father apoplectic with rage. They lectured him for nearly 2 hours, his father insisting now that Byron was 18 his pot possession was a felony, which Byron was almost certain was not true. Ultimately, due in no small part to Byron's total lack of contrition, his father decreed that he would spend his senior year away at a boarding school to "pound some discipline into his thick skull".

 

Byron looked around, taking in the lavish office, a huge contrast to his former underfunded public school. He briefly caught the eye of the receptionist, who convulsively snapped back to her computer when he caught her looking. He smiled. Waycroft's stuffiness conflicted with Byron's own easygoing lifestyle (his school uniform was as unkept and bedraggled as he could manage) but it could hardly be worse than his parents house. And, Byron thought with a thrill, he would meet an entirely new crop of girls. Like any teenage boy, Byron had a bit of a fixation on girls. And, being confident and rather handsome in a disheveled, homeless chic sort of way, the fixation was very often mutual. Now he would get a chance to make a run at a whole new group of girls, none of which had known him since kindergarten.

 

He smiled again. Byron had decided how he should feel. Excited.

 

The door to the headmistress's office flew open. Out strode a woman who made Byron's breath catch in his throat. He didn't follow records of any sort but he didn't need to- this was surely the biggest person in the world. Her light red hair nearly brushed the larger than normal ceilings and Byron could tell that when he stood up the top of his head would only come up to her waist. Yet for all of her size, she still maintained an air of femininity. Some of it was most certainly due to her impressive curves, hugged tightly by a modest but form fitting purple dress. On a normal sized woman, breasts of the headmistress's proportion would have been astounding yet her colossally wide hips and thick thighs eclipsed even her buxomness. It was difficult to tell due to her size and generous chest, but Byron thought she might be one of the most bottom heavy women he had ever seen.

 

"Byron Daniels?" she said loudly, looking at him. Her voice was not deep, but it boomed, rattling his bones.

 

"Yeah," he responded nervously.

 

"Please come in to my office."

 

Byron stood meekly and walked towards her door. He caught a glimpse of the receptionist and his stomach sunk. If she had been tense and nervous before, now she was petrified. She was frozen, her head was down and her eyes resolutely stuck on her keyboard. This all gave Byron a very bad feeling of foreboding.

 

The headmistress turned to go into her office as Byron approached and he nearly gasped a second time. The headmistress's butt was directly in his eye-line and, if it was possible, it was even bigger than he would have guessed given the size of her wide hips and thick thighs. It extended so far out from her back that he certainly could have rested a cup on it, probably a full sized dinner plate. Her dress was stretched over her bottom to near transparency. Bryon briefly wondered where she got her clothes, for the dress she was wearing was not long for this world. He could see the outline of panties large enough to contain her massive butt but was so intimidated he tried, and failed, to put it out of his mind. He followed her into her office, eyes downcast but the wobble of her huge butt every time her feet thumped against the oak floors was not entirely out of his line of sight.

 

Byron took a seat across from her as she moved around her desk, which might have seemed exceptionally large if you did not know who occupied the office, and thought it was safe to look up. The headmistress pulled out her chair, which looked much larger than the one Byron had taken and settled her weight into it, earning an alarming groan from the chair's supports. Despite the chair's increased width, Bryon noticed a generous portion of the headmistress's ass extended over either side of the seat.

 

"I am Bella Emery, the headmistress," she said. "You may call me Headmistress or Headmistress Emery."

 

Bryon nodded, avoiding make eye contact as much as he could.

 

"You will be expected," she continued, annoyance in her voice, "to respond 'Yes, Headmistress' or 'No, Headmistress' when I address you."

 

Byron was halfway through another nod when he caught himself. "Yes, Headmistress."

 

She smiled. It was nice to see her soften and what was more, Byron noticed that she was very pretty. Having been distracted by her size he hadn't really taken in her angular and symmetrical features, her perfect teeth, or her sharp jawline. Byron guessed her age to be at least mid thirties but her fair skin was still smooth and glowing. Now that he thought about it, most people of her size, if any could really be included in that category, were disproportionate but she merely looked like a blown up version of a very attractive, remarkably voluptuous woman.

 

"And," she said, her smile fading, "you will be expected to keep your shirt tucked in and your tie tied."

 

Bryon hastened to obey, shoving his shirt roughly in his pants and starting to tie his tie. He was not very good at it and he lost track of what the headmistress was saying as he tried to get it tied. It had not occurred to him to disobey her, which gave him pause. He despised arbitrary rules and he had never before hesitated to defy authority when he felt it was unjust. Was he really that intimidated by this woman because of her size? Byron was no coward, of that he was sure. He would return to form now that he had gotten over his shock.

 

Headmistress Emery reached down to open the bottom drawer of her desk. Her enormous chest came to rest on the surface of her desk, compressing and spilling outward as her weight settled. There was a pen sitting where her left breast had landed, there was no sign of it now, insignificant compared to her massive breast. The headmistress sat back up, having pulled out a file which she flicked open. She began speaking again but Bryon still wasn't listening, still fixated on her massive body. As his eyes slid down from her chest, he noticed she sported a slight pot belly, a bit of pudge spilled into her lap. It was a slight bulge, might not even be noticeable when she stood, but it was the sort of thing that drew the eye once you noticed it.

 

Byron realized he had been staring at her stomach, which would probably considered rather rude. He looked up, tuning back in at a good moment, because she was asking him a question.

 

"You're here because your parents found pot in your room?" she asked, not looking up from the file.

 

"Yes."

 

She looked up at him sharply.

 

"Headmistress," Byron added feebly.

 

"I assume I don't have to say it," she responded "but we absolutely do not tolerate drugs or alcohol on this campus."

 

"No, headmistress."

 

"And you're here on a work study program?"

 

"Yes, headmistress." Indeed, Byron's father was too cheap to fork over the whole tuition, so Byron was expected to work at the school so that they received a discount.

 

"All of our normal staff positions are filled," said the headmistress, looking him in the eye. Byron, remembering his intent not to be intimidated held the eye contact. "But I'm sure we'll find something you can do."

 

She smiled. Her smile as well as the way she spoke made the hair stand up on the back of Byron's neck. Still, he refused to break eye contact.

 

"You've done a terrible job with that," Emery said, indicating Byron's tie.

 

She stood so quickly that Byron flinched involuntarily. She was so big that she could have reached over the large desk and grabbed him without having to strain. She moved around the desk and Byron caught a view of her profile. The size of her curves left him stunned once again. Her chest extended so far out in front of her that if Byron was standing immediately in front of her, he doubted she would be able to see him at all. At the same time, he imagined that two, possibly even three of him would be hidden by the immense bulk of her rear.

 

The headmistress sat on her desk, the mass of her bottom spreading out to the sides and behind her, free from the confines of a chair, as is bore her weight. The desk was sturdier than the chair but Byron still thought he could hear the wood creaking. Her bare knees were next to him, each one bigger than his palm, so close he could smell her perfume. She bent down, almost double, and undid his tie.

 

"You'll have to learn how to do this yourself," the headmistress said as she lined up the tie on his neck. "I don't want to catch you with an unkempt uniform again."

 

He could feel her breath on his face. He was looking down, telling himself this wasn't because he was intimidated but because it was awkward with their faces so close together. He glanced upwards. Her nose was level with most of his face, leaving her full, smiling lips more or less even with his. He noticed she did not wear lipstick.

 

She knotted the tie and leaned back, gazing over her prodigious chest to admire her work. She was still smiling.

 

"There we are," she said. "Chin up, Byron. This isn't a prison. There are rules that we expect you to follow but if you can manage that I'm sure you'll have fun here."

 

The headmistress reached out and placed her hand on his, which were folded in his lap. Her hand was so large that it covered both of his easily and her fingers drooped down to his thigh. The weight of her hand was incredible.

 

The gesture might have seemed friendly, even maternal, but Bryon had an inkling that it was intended to intimidate him with the size and weight of her hand.

 

"Go have Lindsey, my receptionist and your new classmate, take you to your dorm so you can get settled," said the headmistress. "Classes start tomorrow and you'll want to be rested."

 

Byron went to move his hands to the arms of his chair so that he could hoist himself from his seat, but headmistress Emery did not remove her hand. Not expecting resistance, Byron had put a bit of force behind his movement but the headmistress did not seem to notice, pinning him in place effortlessly. She locked eyes with him.

 

"We'll be seeing more of each other." she said cryptically, smiling that smile again that gave Byron gooseflesh.

 

Maybe he was right the first time, he should be nervous.

 

Chapter 2 by bbbs

Byron lounged comfortably in the bleachers, watching the girls volleyball team practice. He was on his second day of classes and had just finished changing back into his uniform after PE. It was 20 minutes until the cafeteria would serve lunch and, having spotted a group of girls jumping up and down, Byron decided to cool his heels in the bleachers for a few minutes.

 

Byron was 5'6”, although he hoped to eek out a few more inches before college, so every one of the volleyball players was likely taller than him. The tallest, a raven-haired senior with thick thighs and butt nearly bursting out of her athletic shorts, was probably about a foot taller than him. This might have seemed intimidating but all of these girls seemed positively tiny compared to Waycroft's headmistress.

 

Byron had managed to avoid the massive form of headmistress Bella Emery since their first meeting but had no doubt that he would run into her plenty during the school year. He was taking senior seminar which she taught personally and her receptionist Lindsey seemed to indicate that since the normal staff positions were full, his work-study would likely consist of doing odd jobs directly for the headmistress.

 

His first interaction with her making him uneasy, he had asked his fellow students about the headmistress. There were an enormous number of urban legends about her, which Byron supposed was only natural given her noticeable uniqueness. She was in an industrial accident. She had taken experimental drugs from the army. She was a former MMA fighter. She had broken dozens of chairs at Waycroft by sitting on them (this one may not have been an urban legend). She once accidentally stepped on a student's chest and sent him to the hospital. Byron's roommate Damien, to whom Byron had taken an immediate liking, insisted that Emery had once fucked a teacher to death.

 

“Mr. Tiller,” Damien had said, “ he was here two years ago. Followed Emery around like a puppy, then in the middle of the semester just up and disappeared.”

 

“And he couldn't have quit or gotten fired?” Byron asked, skeptical.

 

“I mean he could have,” Damien responded, deadpan, “if he hadn't been fucked to death.”

 

Overall, students seemed to agree the the headmistress could be intense and domineering, but it wasn't too hard to avoid her ire. Byron wasn't entirely reassured, but was prepared to take their word for it for the time being. At the very least he was willing to chance allowing his uniform to return to a state of advanced dishevelment, in no small part due to the fact that he had yet to learn how to properly tie a tie and was too embarrassed to ask Damien to help. He had also almost unconsciously joined the other students in calling the headmistress Bella behind her back, reportedly because she hated the disrespect of being called by her first name.

 

“Yeah!”

 

Some of the volleyball team cheered as the tall raven-haired player spiked the ball hard into the ground. Byron, who watched her large ass jiggle as she landed back on the ground, also felt like cheering. The players were called to huddle up on their coach, a middle aged lesbian indistinguishable from every other female coach Byron had ever seen.

 

He stood up and made his way down the bleachers slowly, so that when he turned to head towards the cafeteria, the volleyball team was heading past him toward the locker room. He spotted the raven-haired girl, who was indeed at least a foot taller than him, and gave her a cocksure smile. For a moment she looked stunned, but recovered quickly and returned his smile with interest as she strode past him. Byron waited a few steps before turning to catch an up close glimpse of the girl's big butt. As he did he saw her already looking back around at him. She was still smiling and when she caught his eye she smirked as if she knew exactly what he was up to. Caught, he smiled sheepishly back at her and turned back around.

 

“Oof!”

 

Byron had taken 4 steps into the hallway before his belt caught him around the middle and stopped him in his tracks. Confused, he turned around to see a massive midsection, eye level with a lower stomach and stupendously wide hips. Oh. Headmistress Emery was standing behind him, a finger in his belt and a stern look on her face. He swallowed. The hallway was empty save for the headmistress and himself. Byron found himself in want of witnesses.

Emery yanked on his belt, sending him flying towards her. His face sunk into the plushness of her stomach, the sweater she was wearing soft against his cheek. His face still half buried in her stomach, he tried to look up but only saw the underside of her ample bust hanging almost a foot above his head. His mind flashed back to the day he had met the headmistress, when he thought her chest could hide him from view. So he was right. For a wild moment he considered if he could hide here in Emery's blindspot. That ridiculous thought was immediately killed as her huge hands groped blindly for him. He instinctively dodged one but the other caught him on the head, pushing him forward, back into the headmistress's pliant stomach. Under the weight of her hand, Byron sand even deeper into her soft pooch. He panicked briefly as his air supply was cut off, but a moment later Emery had slid her hand down to his shoulder and pulled him out where she could see him.

 

“I believe I told you that I didn't want to catch you with an unkempt uniform,” she said, her jaw clenched.

 

He had to crane his neck to see her face this close. Even through her anger, or maybe even because of it, Byron was struck by how pretty she was, her eyes blazing and her jaw set.

“I'm sorry headmistress.”

 

“No you're not,” she snarled. She pulled Byron's pants out from his waist and shoved his shirt down them with her other hand. Her entire huge hand down his pants, Byron felt violated but didn't think he was in any position to argue. She did the same with the back.

 

“But you will be if I catch you like this again,” she finished, pulling her hand back out of his pants.

 

He could have sworn she grabbed his butt on the way out, but he supposed even as slender as he was, there wasn't much room for her to maneuver her large hands in his pants. The headmistress kneeled down to fix his tie, but even on her knees he was far taller than he, so she settled the massive swell of her ass on her heels to lower herself further.

“I am not your mother, I will not dress you,” she said as she tied his tie.

 

He bit back his retort, that she was, in fact, dressing him right now, and allowed her to finish.

 

“There will be consequences next time,” she said menacingly as she stood, towering over him.

 

“Yes, headmistress,” he said quietly.

 

She strode past him, her steps thumping, toward the cafeteria. Wanting to give her some time to get some distance between them, Byron merely watched her go. Her tremendous, round ass shook with each step, each cheek jockeying for position, like two bean bags in a washing machine. When she had gotten far enough away, Byron walked slowly after her to ensure he didn't run into her again.

 

 

 

The cafeteria at Waycroft was as posh as the rest of the campus but complete and total chaos. For some incomprehensible reason, all 400 students at Waycroft were expected to eat at the same time. The cafeteria was big enough to hold all of them but it was always a complete fiasco.

 

Byron had picked up some fancy pork dish he didn't recognize and was trying to find a seat in the disarray, when he spotted Bill Torson. Byron had been warned about the guy but definitely hadn't needed it. He could spot a douchebag from a hundred yards and this guy might as well have carried a sign. At the moment Bill seemed to have cornered Charles Goldberg, who lived on Byron's hall. Charles was a bit of a nerd but perfectly nice and Byron liked him well enough.

 

Byron couldn't hear what they were talking about over the din but Bill was looming over Charles, who looked very uncomfortable so it was clear something sinister was going on. Byron wanted to intervene, he hated bullying. He was on the point of walking over to them when he hesitated. He didn't want to get into a fight on his second day of school. Hell, he didn't want to get into a fight ever- he was much more the 'start a band' kind of rebel than the fighting kind.

 

While Byron was still trying to make up his mind, Bill pushed Charles so hard he fell flat on his back. Byron didn't think, he just tossed down his lunch at the nearest table and started towards them. Bill reached down to grab Charles by the front of his shirt. The blood was pounding in Byron's ears. Time had slowed down. Byron was ten feet away. Bill was reeling back for a punch.

Byron felt it before he heard it. Tremors. Then thumps. Massive, heavy footsteps coming from behind him. He turned around in time to see Bella Emery charging through the cafeteria. He managed to take half a step backwards to get out of her way but it wasn't enough. As her right leg swung past him her hips swayed in his direction. He got hip checked from the top of his head to below his chest by the side of the headmistress's colossal wobbling ass cheek. The soft flesh smashed against Byron's face and chest so hard that he was knocked clean off his feet. Dazed, he rolled over just in time to see Emery dive tackle Bill off of Charles.

 

Byron got unsteadily to his feet and was quickly shunted towards the scene of the fight. Students were surging towards the commotion and Byron, having already been close, was being pushed in front. Looking down at the state of things, Byron was impressed in spite of himself. The headmistress had used her hands to tackle Bill off of Charles so he didn't get crushed under her body when she landed. She was pinning Bill with her hands and had leaned to the side so she didn't land on Charles, although it was a close run thing, Charles was quaking in the shadow of her enormous body. By the looks of things, Byron wasn't the only person she bowled over, but she had managed to do an awful lot before Bill had thrown a single punch.

 

Bill was struggling in the headmistress's grip. Her hands wrapped almost entirely around his waist. She held him fast, but it was clear that she had no leverage to use her weight or most of her strength on him. Teachers were trying to plow through the milling chaos to help. The gawking student mob was all around the scene now, increasing the mayhem and confusion. So it wasn't a total surprise when the headmistress's gigantic body started lowering on to Charles who was still lying prone.

 

“No!” Byron yelled, but his voice was lost in the racket.

 

Emery's humongous right tit was inches from Charles' terrified face. Byron bent down to grab Charles' arm and hoist him out but it was too late. As he grabbed Charles' arm, the headmistress's enormous boob consumed his head and the rest of his body disappeared under hers. Byron still had Charles' arm and pulled but stopped immediately. The headmistress was too heavy. He was more likely to rip Charles' arm off of his body.

 

“Headmistress!” Byron yelled as he dropped Charles' arm and started pushing on Emery's torso. The headmistress, distracted by the chaos and the violently struggling Bill, noticed nothing. Byron was making no headway so he switched tactics. He got into a deadlift stance and tried pulling the headmistress's side up. His hands sunk deep into her soft belly but he wasn't able to move her an inch off of Charles, who was thrashing violently as he was smothered under Emery's right breast.

 

The headmistress's prodigious ass was so large that even lying down it extended several feet into the air. Thinking this might provide him more leverage, Byron changed tactics again. He kneeled next to the headmistress's ass and drove his shoulder into the ample posterior. He sunk into the pliable flesh but soon, much sooner than he might have guessed, he met a wall of firm muscle. He pushed from his legs with all his might, trying to tilt headmistress Emery's body up just enough for Charles to grab a breath or escape. Byron made no progress. He collapsed in exhaustion against the headmistresses's massive ass, which wobbled in retaliation from his assault, shaking his body. Charles' struggles had become weaker. Byron stood shakily. He summoned all his remaining strength and yelled.

 

“Bella!”

 

The headmistress's head snapped around, enraged. Byron pointed desperately to where Charles lay buried under the headmistress's body. She seemed to follow him because she rolled onto her side. Charles gulped greedily at the air. Byron helped pull him out of the shadow of Emery's body.

 

“Sorry Charles,” said the headmistress, “are you all right?”

 

Charles, whose new reintroduction to oxygen had cause a coughing fit, raised a hand in response as he scampered away, hacking. The headmistress caught Byron's eye and gave him an unreadable expression. Byron thought he might have seen gratitude, but also something else that he couldn't identify. Emery, still clutching a struggling Bill, checked beneath her this time before rolling her body back flat against the floor. There was a whomp of displaced air as her huge body hit the floor again and the headmistress's generous rear shook back and forth with the impact.

 

Byron fought his way back through the gawking students, wondering if the stories about the headmistress he had heard were urban legends after all.

 

Chapter 3 by bbbs

A group of 25 or so Waycroft seniors milled about in the hallway outside of a classroom. Byron was sitting against the wall, trying to look inconspicuous. He, like the fellow seniors around him, was waiting for Senior Seminar to begin.

 

This would be the first time he would come face to waist with the headmistress since the incident in the cafeteria. He had called her Bella, something he knew she hated, and he didn't think she would be likely to simply let this go. Also, although he had taken special care to dress himself properly today, his skill at tying a tie still left a lot to be desired. He had managed to get his tie knotted at his neck but it looked like it had been tied by a blind toddler who was missing most of his fingers.

 

Byron's plan was to try to be as inconspicuous as possible and hope he went unnoticed. He wished he had a few allies in this class but he hadn't really met any of the people now gathered in the hallway. His roommate Damien, he knew, was also in this class but he was ditching or, at the very least, late.

 

Familiar thumps started coming from down the hall and the milling students backed up to clear a wide path for the headmistress. Bella Emery came down the hall, her thick legs moving slowly but her long stride carrying her huge body swiftly toward the classroom. The headmistress glanced at the students, the tallest of whom came no higher than her navel, as she approached the classroom (Byron tried to stay out of sight) but did not address them as she pushed open the door. For a moment, despite the doorway being quite wide, Byron didn't think the headmistress's wide hips, today encased in a tight pencil skirt, would fit through. But she didn't slow down at all, evidently having cleared this obstacle before. Headmistress Emery's wide backside pressed on both door jams, some of the bulk of her ass being compressed between them, as she strode swiftly through the door. As she cleared the doorway, her butt wobbled softly, as if shaking off the discomfort of squeezing through an opening that was not entirely equipped for it.

 

The class gave the headmistress several moments before following her into the classroom. Bryon couldn't blame them, even if he hadn't been avoiding her Byron knew to give the headmistress's hips a wide berth, having been waylaid by them mere days before. Byron tried to melt into the middle of the pack of students but, having been slow on the uptake, ended up at the very back.

Byron chanced a glance at the headmistress as he entered the classroom. To his complete shock, she smiled broadly as she spotted him. She took several steps toward him, her weight shaking the soft wood of the classroom much more intensely than it had the polished oak of the hallway.

 

“Hello Byron,” she said, putting a huge hand on his upper back.

 

This was not the first time that Byron had noticed how comfortable the headmistress was with physical contact, his observation accentuated in no small part by the fact that Emery's hand covered 2/3rds of his back.

 

“No need to be so scared,” she said with a little laugh, flashing her straight white teeth. “I'm not an ogre. I appreciate you making an effort on your uniform.”

 

Byron attempted to smile back at her, still uneasy.

 

“You still need to figure out the tie, though,” she said, not unkindly, “do they not have YouTube where you're from?”

 

At this gentle ribbing, Byron gave a genuine smile, the tightness in his chest easing, “I gave it my best shot, Headmistress.”

 

“Come here and we'll fix it.” The headmistress grabbed Byron by the tie and pulled him gently towards her desk. Byron noticed that while the chair behind the desk had been replaced with one that had a chance at supporting her, the desk was the standard desk he had seen in every classroom. The sound of straining metal filled the room as the headmistress gently settled some of her weight on the corner of the desk. Despite taking up well more than a quarter of the desk, less than half of Emery's colossal rear was supported by the unequipped furniture. Judging by the impressive muscles bulging slightly out from the headmistress's thick thighs and calves, she knew better than to overburden a desk that had been designed for normal humans.

 

For the third time in a week, headmistress Emery unfastened his tie, her big fingers surprisingly nimble in undoing the knotted mess. Byron turned slightly red, aware that his classmates' first impression of him was that of being dressed like a child.

 

The headmistress bent down to start fixing his tie, the massive swell of her bust missing hitting his face by inches. The headmistress's forehead pressed lightly on his as she considered his tie, her light red hair falling around his face, the scent of her shampoo surrounding him. It was something fruity, he thought, like mangos. Unbidden, unwanted, his teenage libido revved at the scent. Byron cast his mind around for something to distract himself. As strong as his sex drive might be, he knew what was off limits and headmistress was at the top of that list, even if she hadn't been big enough to squash him like a bug.

 

Byron failed to tamp down his instinctive response. There was something intensely sensual to him about a woman's hair, the smell of her shampoo. Emery's soft hair tickled his face. He had heard, he couldn't remember where, that this color red couldn't be replicated with dye, it only occurred naturally.

 

“All I ask for is respect,” the headmistress was saying, her mouth level with his neck, her breath a gentle tickle on his adams apple “and for you to do your best. If you can do that you'll find me very easy to get along with. You might even find me pleasant.”

 

Byron, who was looking resolutely straight ahead and casting his mind out for a sport less erotic than baseball, felt rather than saw, the headmistress smile. She synched his tie, a little firmer than he might have done himself, and straightened up so Byron was looking at her stomach.

 

“There,” she said, placing a large finger under his chin and guiding his face up until he was looking into hers. Her hand, despite it's size, was very soft. “All better.”

 

“Thank you, Headmistress.”

 

Quite ready to be away from the headmistress's nonexistent of concept of personal space and her intoxicating scent, Byron spun around, faintly red with embarrassment and repressed hormones. As he faced his classmates he was sure he noticed mocking amusement in some of the faces, especially the boys. He was relieved to see an open seat in the back corner and headed towards it, eager to escape the judgmental looks.

 

“Senior seminar!” the headmistress boomed from the front of the class. “What is it? Well, if the former upperclassmen that I'm sure you've heard from are to be believed, it's a complete blow off class.”

 

The class chuckled slightly.

 

“But no, it is not. Senior Seminar is about life after high school. It is vitally important. You will certainly be given more freedom to do things your own way in assignments, but everyone will do the work. You will do the work even if I have to sit on you and make you. And with me, that is not something students often survive.”

The class laughed again, but Byron did not. He found this statement too close to reality to find amusing.

 

“We'll cover a variety of topics, from taxes to job hunting, but we'll focus a lot on college since that will be your next step. Everyone who goes to Waycroft will be accepted to and have the opportunity to attend college. Full stop. Zero exceptions. It has been this way since the school opened and it will certainly be this way so long as I am headmistress. I can not speak for whatever bum they get to replace me.

 

But to know how to approach your college career or even which college is right for you, you'll need to have some idea where you want your life to go. So that's what I'd like you to do now. Think about what you'd like your life to look like in 10 years. You'll be 28 and I... will still be young and vivacious. You should break into groups of 4 to discuss. Bounce ideas off of each other, figure out any considerations or obstacles you may not have thought of.”

 

There was a sudden upswing in sound as Headmistress Emery headed to her chair. Byron addressed the 3 students closest to him, all girls, attempting to regain some of his swagger.

 

“Ladies, I think we should form a group,” Byron said brazenly, “I'll give you a moment to consider how lucky that makes you.”

A moment of silence. Byron's stomach dropped. It was a big swing, if they didn't bite he'd look like a real asshole.

 

Then, laughter. More, probably, than the goofy joke deserved, meaning Byron had delivered it with the necessary amount of raw confidence.

 

“Shall we?” he asked, smirking.

 

It didn't take Byron long to realize he had absolutely no idea what he wanted his life to look like. The girls- all of whom had told Byron their names, none of which he remembered- seemed to all have a pretty good idea where they wanted to be at 28, both in career and in life.

 

The floor began to shake with the headmistress's heavy steps as she began to walk around to follow up with different groups. She turned sideways to fit in between rows of desks, the round moon of her ass hanging precariously over the heads of the students behind her, while the thunder of her thighs bulged over the desks on both sides, knocking things over. Students who had been at Waycroft were apparently too used to this sort of thing to notice, not even stopping their discussions to pick up the items unceremoniously thrust to the floor by Emery's hulking thighs, but Byron, still adjusting to the headmistress's size, couldn't help but watch.

 

As the headmistress rounded on his corner, Byron tried to jump back into the discussion but still didn't have much to add. Emery squeezed between the last row of desks, her thigh knocking Byron's paper off of his desk, along with one of the girls' entire backpack. Byron was cast into shadow, the giant swell of the headmistress's butt just above his head. Although the headmistress showed no signs of being unsteady on her feet, Byron still had the feeling of being directly below a poorly hung, monstrously heavy piece of art. He chanced a glance upwards as Emery asked how they were doing. Even up close, her dark pencil skirt betrayed no details of the blimp of the headmistress's behind except it's enormous size.

 

“Headmistress Emery, what do you think of this as a timeline?”

 

Byron dodged just in time. The headmistress bent over, her huge ass expanding and lowering in a single, seam testing movement. Her butt hovered just over Byron's desk as she checked his group-mate's work, forcing him to lean almost entirely out of his seat to avoid it. Even looking right at it after it nearly accosted him, he found it hard to comprehend the size of the headmistress's massive butt. The tight skirt restricting it's size, it still overshadowed Byron's desk and chair with plenty of room to spare. The mass of the headmistress's butt floated away from him and suspended again overhead as she stood. Byron was able to straighten up out of his uncomfortable, ass-dodging position.

 

“And how are you doing? What have you got?” The headmistress was addressing him over her shoulder. Byron was surprised she could see him at all past the bloat of her own ass but he could just make out her eyes beyond the huge surface of poor, beleaguered black fabric.

 

“I- uh... I don't really know,” Byron admitted.

 

“Ok,” she said softly, “that's all right. We'll get you sorted.”

 

Her eyes crinkled over the balloon of her ass. “I'll be back to check on you later.”

 

She shuffled up the row, her steps shaking the ground and her thighs knocking things over as they squashed between desks.

 

At the end of class, Byron again got caught behind the throng of students all hurrying to leave. Before he could reach the door a huge thigh thumped down in front of him, so close that he nearly ran into it. The thigh completely hid Byron from view, he guessed it was time and a half as big around as him at his widest point. Byron's face snapped up to meet Emery's but he had to go so uncomfortably far back that he tweaked his neck. Wincing, he stepped back to meet the headmistress's eyes without having to strain. Almost in tandem with him, the headmistress stepped forward so he was still too close to easily meet her eyes. Slower and more carefully, Byron bent his head backwards to look into the headmistress's fetching face. He suppressed a stab of irritation, did she really prefer to stand so close that he had to strain to look her in the eye and she had to look over her massive chest to see him?

 

“Byron, you will report to my office on Monday afternoon after your classes to begin your work-study,” the headmistress stated.

 

“Yes headmistress,” Byron responded. “Uh, what will I be doing?”

 

“You'll be my assistant for the time being,”

 

“Like Lindsey?”

 

“No, Lindsey is a receptionist. She answers phones, makes appointments, that sort of thing.” Emery said, a note of the expression that made Byron uncomfortable appearing on her face. “You'll be helping me directly.”

 

Confused, Byron asked “What does that entail?”

 

“Oh, a little of this, a little of that.”

 

If she wants to be cryptic, Byron thought to himself, let her. He walked around the pillar of her body, looking forward to getting back to his dorm and starting the weekend. He was almost out the door when the headmistress grabbed his arm roughly. Her fingers encircled his slender arm with room to spare.

 

“Byron,” the headmistress said, no trace of malice in her expression but making a fierce amount of eye contact.

 

“Yes, headmistress?” he asked, alarmed.

 

“Don't be late.”

 

Chapter 4 by bbbs

After Senior Seminar Byron swung by the gym, even though it wasn't entirely on his way back to the dorm, because he had an inkling that the volleyball team might be practicing. A group of girls were indeed setting, passing, and spiking as he entered the gym, his detour proving fruitful. Byron hopped onto the first step of the bleachers and walked toward the far door, attempting to look casual but keeping a close eye on the court for his raven-haired friend.

 

When he reached the middle of the gym he paused. He hadn't spotted the raven-haired player, so he spent a moment searching. Just as he was forced to conclude that she wasn't there, he heard a voice from behind him.

 

“Looking for someone?”

 

Byron's heart leapt into his throat but he recovered quickly.

 

“Yeah, I was looking for someone to help me change a light bulb,” Byron said without turning around.

 

He felt someone walking in the bleachers behind him and then, although he kept his eyes fixed straight ahead, sensed the presence of someone standing next to him. “Oh, yes, volleyball players are notorious for their generous loaning of stepladders.”

 

Feeling that he had played it cool long enough, Byron looked up at the girl next to him. Sure enough, it was the raven-haired girl he had ogled when he last caught a volleyball practice, standing more than a full head taller than him, looking down at him. If he looked straight ahead, his eyeline would be just above her modest chest. He smiled his most winning smile at her and she returned it, a look of friendly mocking in it- if it hadn't already been evident that she knew he was here to see her, it was now. Caught. Again.

 

“What happened to your sexy hobo look?” she asked, still grinning at him.

 

Byron noticed that she wasn't dressed to play today, nor was she in her uniform, wearing jeans which didn't seem any more equipped to handle her bodacious lower body than her athletic shorts and a solid grey t-shirt. “I've embraced the uniform. Have you seen these pants? Puke brown and pleated? I mean it's so sexy it's not even fair.”

 

“Bella came down on you, huh?”

 

“I'll be honest, I was afraid she might eat me.”

 

“Who could blame her?” said the volleyball player, leaning closer to him so that their arms grazed each other.

 

Who was this girl? Byron was certainly no stranger to girls being receptive to his flirting, but this girl was so assertive and had taken control of the conversation so quickly that he felt like he was scrambling to keep up. Having to revise his normal role as aggressor left him feeling rather wrong footed. He even a felt little suspicious, as though she might have some ulterior motive, though he couldn't begin to imagine what that might be.

 

“I'm Byron.”

 

“Chloe.” the girl responded, she shadow of a smirk still gracing her charming features. Today, her dark hair had been pulled into a messy top knot. She wore no makeup. Her teenage skin wasn't perfect but Byron still appreciated the natural look. Byron realized that he had unconsciously been leaning slightly away from her, she had gotten so close that if he righted himself now they would be touching.

 

“Why aren't you playing today?” Byron asked.

 

“Ugh, that's JV,” Chloe said with a surprising amount of contempt.

 

“And you, of the acute jumping and slapping abilities, would not be caught dead with such amateurs.”

 

“You forgot standing, there is also a lot of standing,” Chloe said. “Anyway I'm pretty sure they don't let 19 year-old seniors play on JV.”

 

“You're 19?” Byron asked, surprised. “And they let you play volleyball?”

 

Chloe looked down at him, confused.

 

“I didn't think the school's insurance would cover a broken hip.”

 

Chloe laughed, half rolling her eyes, and gave him a playful shove. Even though the push was light and friendly, Byron could tell she had a lot of power she was holding back.

 

“Be honest,” Byron said, pressing his advantage, “they held you back a year because you're mad dumb didn't they?”

 

“No, I stabbed a mouthy new kid and had to sit out the rest of the year.”

 

It was Byron's turn to laugh. Chloe sat down, her thick butt bouncing slightly, and Byron followed suit. Even though much of her height was in her legs, Byron's head still only came up to her shoulder when they were sitting down, some of her lost height regained by the considerable cushion of her ass.

 

“Are you going to Fall-FuckFest?” Chloe asked

 

Byron had no idea what that was but he was going to make an effort to go to anything that was called FuckFest, especially if he knew a pretty girl was going to be there. “Yeah, wouldn't miss it.”

 

“Maybe I'll see you there, then.” Chloe's hand snaked onto Byron's leg. Her arm so long that she could easily rest her hand on his knee, which it covered completely. He looked at her. She made eye contact with him for a moment before looking away. “Maybe that way you'll stop stalking volleyball practices.”

 

Byron laughed again. And again he looked up into her face. This time she held is gaze. For a long moment there was silence, her hand still on his leg. Normally he wouldn't have dared in the middle of school, so soon after meeting someone, but this girl had been flirting so aggressively Byron wondered if he should try to kiss her.

 

“What's this?” came a slightly accented voice. “I leave you alone for a minute and you pick up a stray?”

 

A plump Latina was walking towards them. Byron would never have guessed that she was an athlete if he hadn't recognized her as one of the volleyball team who had been practicing with Chloe earlier in the week. She was tall, probably not quite as tall as Chloe, but she was decidedly more full figured, sporting a heaving chest and an evident tummy to match a well padded lower body. She, like Chloe, was dressed down. She stopped and stood over them, irritation on her sharp featured face. If she was messing around, it was a convincing deadpan.

 

Chloe slid her hand off of Byron's leg. “Amy, this is Byron, a sexy hobo.”

 

“He looks more like a poorly dressed ventriloquist's dummy.”

 

“I also make a lovely cake topper,” Byron said in a mock justifying voice, “I'm available to rent for parties.”

 

“Oh, he's quick,” said Amy appreciatively, still unsmiling.

 

“Yeah,” agreed Chloe slowly, “I'm not sure how I feel about that.”

 

She stood and Byron imitated her. This left him surrounded by the bodies of two girls who wouldn't even see the top of his head if they looked straight ahead. Amy was a good 2 or 3 inches shorter than Chloe but Byron was still only eye level with the nape of her neck. She had a rather slender, delicate neck and sharp jawline for someone so decidedly chubby. In fact, Byron thought, once you got over the severity of her expression she was fairly attractive- big, dark eyes, flawless light brown skin, and there was even something alluring about her scorn.

 

Young though he might be, Byron knew better than to change horses mid race, but perhaps there was a way to pursue Chloe without ruling Amy out for some later encounter after he had a chance to soften her with his charms. Regardless of how things played out from here he was pleased that his first week at Waycroft found him as the meat in an amazon sandwich. He wasn't sure if the situation would prove him extremely lucky or a terrible decision maker but his unassailable confidence drove him to recklessness rather than caution.

 

“So I might catch up with you guys at Fall-FuckFest, eh?” Byron said, wanting to make it clear to Amy that he intended to be a series regular rather than some bit playing guest star.

 

Amy raised her eyebrows at Chloe, who looked back at her, impassive. Her expression still aloof, Amy turned to Byron and considered him. “Hmm, I suppose we could use you as bait to catch some of the better fish.”

 

“I don't know,” Chloe countered, “sometimes I can't help but root around in the tackle box.”

 

Chloe draped a long arm over his shoulder. Although they had both just compared him to bugs that were intended to feed to fish, a thrill went through Byron. There was something extremely comfortable about Chloe's arm around him. He resisted the urge to collapse into her embrace. He slid his own arm around Chloe under the guise of playing up a bit. His arm fit comfortably around her waist, resting on the shelf of her protuberant ass.

 

“Oh Amy, you missed your shot. You could have had a crack at all of this.” Byron used his free hand to gesture at his small, slender body, making exaggerated feminine poses.

 

Amy rolled her eyes. “Oh please, if I showed you the slightest interest you'd be all over me.”

 

She sidled around to Byron's other side and put her arm below Chloe's on his upper back. Amy's hip nudged Byron further into Chloe. He was slightly smushed between the thick bottomed girls' haunches, the fat their saddlebags bulging onto his stomach and chest. Knowing he was playing with fire, Byron folded his arm into the plush softness of Amy's back.

 

“Not if he already belonged to someone,” retorted Chloe slyly.

 

Chloe used the arm around Byron's shoulders to pull him in closer. Amy, not to be outdone, pulled him back towards her. The girls each pulled in a stalemate, angling their hips in for leverage and smooshing Bryon further. Byron, for his part, was delighted by the turn of events. Play-acting or not, this scuffle was erotically reminiscent of one of Byron's secret fantasies- to have girls fighting over him, preferably with him in the thick of it. Keeping his body passive in the jostling, Byron's expression slipped into one slack with delight. It seemed that this did not go unnoticed by Amy because she sneered at him. “We better go before the little guy ruins his pants.”

 

“Ruins? My semen is a gift and a delight.”

 

Chloe laughed. Even Amy couldn't stop the corner of her mouth from twitching.

 

“We really should go, though,” Chloe conceded. “Hope to catch you at the party.”

 

The girls disentangled themselves from Byron, to his chagrin. He could still feel the ghost of their bodies in the warmth they left behind.

 

“Why do people always leave right after I talk about how great my semen is?” Byron asked, deadpan.

 

Chloe laughed again as they turned to go. She gave him a flirty wave over her shoulder and spoke softly. “See you later.”

 

Amy spared him only a look, it contained a lot of mixed messages but the headline was definitely exasperation. Byron stood dazed and watched them leave. He felt like he needed a cigarette. Whatever Fall-FuckFest was, he was going to do everything in his power to be there.

 

 

 

As he opened the door to his room, Byron was overwhelmed with by the smell of weed. Damien was sitting upright in bed, smoking a bowl.

 

“You weren't in class,” said Byron, unable to keep the irritation from his voice.

 

“Yeah,” said Damien, blowing out a cloud of smoke, “mental health day.”

 

Byron took the bowl from Damien without waiting for him to offer and took a long hit. He coughed slightly as smoke billowed from his mouth. “It hasn't even been a week of classes,”

“I take very good care of my mental health.”

 

Byron hesitated, not wanting to reveal his ignorance, but asked “What is Fall-FuckFest?”

 

Damien turned to Byron, eyes bloodshot and half lidded, and a broad smile stole slowly over his face.

 

Chapter 5 by bbbs
Author's Notes:

 

The halls were empty on Monday afternoon as Byron walked dolefully to the front office. It seemed odd that he had seen virtually no other people since he had left his dorm room; it was early, not yet 4 PM and Byron would have guessed students should still be hurrying to sports and extra curriculars, but Waycoft was silent. He hadn't even seen a janitor. Byron never imagined he would miss the ramshackle halls of his public school but there was something creepy about the clean, posh school with the varnished wood and expensive, if bland, frames, plaques, and art adorning the walls. The eerie, unfamiliar school did nothing to ease his foreboding about performing the task he had been set.

 

He was very fond of Damien and his friendship certainly had fringe benefits, Damien being an established social power in the school, but Byron was discovering that there was a cost to maintain this relationship. It wasn't that Damien was a bully, in fact, quite the opposite. Byron had never encountered a high schooler with social standing who was as inclusive, welcoming, and universally popular as Damien had proven to be. In every school Byron had encountered or even seen on TV, the socially powerful, often mislabeled as 'popular', were at least cold and exclusionary if not downright cruel and tyrannical. While he wasn't 'nice' in the most traditional sense of the word, Damien was easygoing and comfortable with himself, not eager to seek outside validation and always willing to reach out to someone he thought was being excluded.

 

Damien, however, had no issue asking people to do favors for him or encouraging mischief. And, likable as he was, it was very hard to refuse him. Urged on by Damien and bolstered by no small portion of a 30 rack of beer, Byron had spent his first Saturday night at Waycroft marching up and down the boy's dorm, stark naked save for a hat made from the empty beer box, passionately singing Hooked on a Feeling. He had been very nearly caught by Mr. Whiteman, who stayed in the boy's dorm on weekends to prevent them from doing the exact type of thing that teenage boys like to do when they're left to their own devices.

 

Damien's most recent request of Byron went far beyond a bit of harmless streaking. Byron had informed Damien that his work-study was going to involve some unspecified tasks for the headmistress and he could immediately see the wheels in Damien's head turning. There was a potential issue, it transpired, with Fall-FuckFest and Byron's access to the headmistress provided a potential solution.

 

Fall-FuckFest, Damien had explained, was a massive blowout party they held on the second weekend of every fall term. The party had earned its graphic name because of the high number of hookups that occurred during the course of the bacchanal. When Byron countered that this just sounded like every other halfway-decent high school party he had ever been to, Damien insisted it wasn't, that “tang just hangs from the lowest branches waiting for any hungry chump who comes along.” Disturbing poetry aside, sexual appetites were evidently raised due to puritanical summers that many students were forced to endure. Byron, it seemed, was not the only one to come from a strict household.

 

Byron vaguely wondered how they pulled this off if it was really as rowdy as Damien's hype made it seem, but he didn't want to sound like he doubted Damien's account of the event. This unasked question needed not remain a mystery, after a subsequent conversation in which he filled Damien in on his work-study details, Damien was only too eager to discuss logistics. Security was apparently not usually an issue, but they wanted to be extra safe so that tradition wasn't spoiled and Byron might be in a position to help.

 

“They're not exactly the secret service, but even blind-ass Mr. Whiteman would notice a mass sneak out,” Damien explained while trying to eek some remaining weed out of a bowl that had clearly been cashed, “But there is some sort of staff meeting early that Saturday morning, so the teachers who normally watch over the dorms get the night off. And on the weekends, no security, so we can use the Peterson building to party- which may make a mediocre school building but makes one hell of a venue.”

 

“And the teachers don't know you throw a huge party every year in a school building?” Byron asked.

 

“I think they know, they just don't really care that much. We do a pretty good job of cleaning up after ourselves and I don't guess any of them are paid well enough to bother looking into it.”

 

“You're saying Bella is cool with this?”

 

“Well,” Damien had hedged, “she doesn't know as far as anyone can tell. The headmistress's quarters is far enough away from Peterson that she'd never hear us, but she's really close to the girl's dorm so she might pose a problem if she catches one of them stumbling home drunk. That's where you come in.”

“Oh, no,” Byron protested “I don't come in. It's my first week and I'm already on her radar, I don't need anything else getting me closer inspection.”

 

Byron couldn't recall exactly how Damien had convinced him to look through the headmistress's office to find out what her plans were for that Friday but somewhere in the conversation he was sure he had been promised a hero's reception in the boy's dorm that evening, though Damien might have phrased it as 'generations of Waycroftians will write songs of your great deeds'. Quite aside from wanting to make an impression on his new dorm-mates, Byron knew how the high school rumor mill worked and thought, with a little luck, the story might get back to Chloe, hopefully with some embellishments.

 

Even at the alluring prospect of Chloe hearing a harrowing tale of him, suspended from cables from the ceiling, bravely securing crucial party-related intel, Byron's mood remained sour as he navigated the empty halls. He knew he was tempting fate, risking Emery's wrath so soon after getting out of the doghouse. He was prepared to compensate for his recklessness by trying to win the headmistress's favor- behaving diffidently and keeping his uniform remotely presentable.

 

When he hadn't been dramatically covering Blue Swede classics Byron had spent the weekend learning to tie his tie. To limit his humiliation, he had waited until he had the room to himself before pulling up videos about how to best tie a tie. Apparently, there were different knots. Who knew. An embarrassing amount of practice left him looking, if not dapper, then at least presentable.

 

Byron entered the front office to find Lindsey at the desk, looking nervous and twitchy as ever. She glanced up from her computer as he came in.

 

“Y-you can go right in,” she stuttered.

 

This was a disappointment. Now that he was on the cusp of his great calendar caper Byron was feeling distinctly anxious. His foreboding had developed into fully blown fear and he wished he had been granted a stay of execution. Denied this small mercy, he walked over to the headmistress's office door and pushed it open.

 

The massive silhouette of Headmistress Emery was blocking nearly all the light from the floor to ceiling window in her office. Her back was to Byron, leaving him, once again, looking directly at the huge protrusion of her ass. The headmistress did not turn around when he entered and, looking up, he saw that she was on the phone. She used her free hand to give him the 'one minute' sign.

 

Byron took a seat on the other side of her desk and looked down into his own lap so he wasn't staring directly into the headmistress's backside. He thought this meek position would also make it seem like he wasn't eavesdropping on Emery's phone call, which he definitely was trying to do. He couldn't hear the voice on the other end of the line and the headmistress was mostly listening, so he wasn't able to glean much from his surreptitious attempts to catch meaningful details. By taking this small action towards his goal, Byron's fear began to abate as quickly as it had come, his anxiety turning into adrenaline. The remaining apprehension solidified into an uncomfortable pit in his stomach but he otherwise felt ready for espionage.

 

The headmistress ended her call with a “That's fine, circle back with me,” and slipped her phone into the pocket of the black slacks she was wearing that day. Even without looking directly at her and with her back still to him, Byron could sense the tension in Emery and knew that she was not in a mood to be trifled with.

 

The headmistress turned, her butt wobbling indignantly, and her narrowed eyes fell immediately upon Byron. “Made yourself at home, have you?”

 

Byron wasn't moving, but he froze anyway. He wasn't sure if he was expected to remain standing until she offered him a seat or if he was supposed to interrupt her phone call to ask to sit down.

 

“And,” said the headmistress, thumping towards him, “in a polite society we knock before entering.”

 

“Sorry Headmistress, Lindsay said that I should just go in and-”

 

Emery's eyebrows raised. “So it's Lindsay's fault?” She sat on her desk, crowding him with her knees. Although she did not sit indelicately, her ass made a whoomph sound as it landed.

 

“No, I-” Byron owed nothing to Lindsey and she had, in fact, told him to go into the headmistress's office, so he wasn't sure why he felt he need to cover for her but this instinct overwhelmed his good sense. “I'm sorry, headmistress, it won't happen again.”

 

Her expression softened, the storm of her temper turning to a light rain.

 

“Good boy,” she said gently tousling Bryon's hair, the palm of her huge hand easily covering his entire head. The headmistress spotted his tie and the corner of her mouth bent into a slight smile “Oh, look who learned to dress himself!”

 

Headmistress Emery grabbed Byon's tie and tugged softly, so he was forced to lean towards her. She then used her hand to nudge him back upright and sat back herself to take him in, gazing over her immense chest.

 

“You see how much better this is? Very sharp. Very handsome,” she said, her smile growing so that he could see a glint of her straight, white teeth. Growing ever more nervous, Byron squirmed uncomfortably but the headmistress did not release him. “You're lucky you didn't go to school with me, I would have eaten you up.”

 

Byron, who imagined Emery must have been a similar size in high school, couldn't be entirely sure she wasn't being literal but it was an unsettling thing to hear from his headmistress regardless. The headmistress was oblivious or apathetic to Byron's discomfort and took her time in releasing him.

 

“So, work-study,” she said, releasing his tie at last, “you're probably wondering what I have in store for you today.”

 

“Yes, headmistress.”

 

The headmistress stood and walked around her desk, indicating to 3 large file boxes stacked along the wall as she did so. “I thought we'd start you off with something simple. I'll just need you to do a bit of filing. The files need to be sorted into curriculum documentation,” she pointed to a file drawer on one side of her desk, “budget projections,” she pointed to the file drawer on the other side of her desk, “and extra curricular administration,” she pointed under her desk where Byron imagined there was a third file drawer. “Easy, right?”

 

“Yes, headmistress.”

 

“I'll be here if you have any questions, but I don't expect you will.”

 

The task would have been inoffensive, if rather dull, if it didn't necessitate dodging around the vast body of the headmistress. As it stood, it was somewhat demeaning to crawl around mammoth thighs that entirely eclipsed him and evade giant footsteps as the headmistress took phone calls and worked at her desk, ignoring his presence completely. He kept a careful watch for any clues to her Friday plans in the headmistress's phone calls and paperwork, but all he learned is that her job seemed even more boring than the task she had delegated to him.

 

His failure to observe any helpful details pertaining to his FuckFest mission was not overly concerning. Although it would have made things much easier, he had not expected such information to be simply lying about. He planned to copy the data on the headmistress's cellphone onto a micro SD card he currently had hidden in his shirt pocket. It was only a matter of getting an opportunity.

 

Byron crawled on his hands an knees, it was easier than being constantly bent double, over to the boxes to grab more files. He took a stack of extra-curricular administration folders that he had already sorted and crawled back towards the headmistress's desk. Emery was on her phone again, standing in front of her window, so Byron took the opportunity to crawl under her desk to access the file drawer set into the inside panel.

 

The desk was so deep and tall that Byron could ensconce his entire body easily beneath the desk with plenty of space to spare. Like everything at Waycroft the desk was ornate and expensive looking, its size, Byron surmised, probably necessitated so that the headmistress could fit her thick thighs under it. He pulled open the panel drawer and began filing the stack of paperwork he had brought with him.

 

The already dim light under the desk was darkened further as the headmistress, still on the phone, thumped her way in front of the desk opening. It made him feel slightly claustrophobic but strangely cozy, to have the solid wood desk on three sides and his only potential exit blocked by the sturdy legs of the headmistress. Byron wasn't sure whether or not Emery knew he was under the desk, so he continued to file so he would look busy if she was coming to check on him. He had a sudden flash of memory- a cartoon he had seen as a child, one of the infinite retellings of Jack and the Beanstalk, where Jack had been hiding from the giant's wife. It might have been just a silly cartoon, but if the headmistress said anything about grinding his bones to make her bread he was making a run for it.

 

The headmistress settled her bulk into the chair, earning an unhappy groan from the tormented furniture as her ass bulged over the sides. Emery tucked her legs under the desk, her enormous feet landing inches from Byron's leg. One of her ballet flats (Byron thought that if there was anyone who didn't need to wear heels it was the headmistress but there were also probably no heels that had the structural integrity to accommodate her weight) was the length of his forearm. His claustrophobia spiked as the headmistress's knees, slightly above his head, crowded him against the inner wall of the desk.

 

Thinking it would be very awkward if the headmistress discovered him beneath the desk after any time had passed, Byron stopped leaning away from Emery's legs and allowed one of her calves to bump into him. The headmistress did not flinch, so he assumed she had already known where he was. He relaxed slightly, oddly comforted by the weight of the headmistress's calf leaning into him.

 

Headmistress Emery was wearing pants so there was nothing inappropriate about his view, her thighs were so thick that Byron doubted that he would have seen anything untoward even if she had been wearing a skirt, but it was a strangely intimate situation. Byron was surrounded by the headmistress's scent, she was remarkably clean for the end of the day but he still detected a natural smell beneath the soap and perfume, it wasn't foul or unpleasant but it seemed a private thing that he was spying on.

 

The headmistress shifted in her seat, promoting renewed groans from the chair, and rested her free hand in her lap. She lifted the thumb of her hand to scratch her slight pooch, the softness of her belly conforming to the shape of her finger. She tapped her foot impatiently as she listened to her phone call, the vibrations of her “Mmhmm”s reaching Byron under the desk. She allowed her shoe to slip off of her foot so that it dangled idly by her toes for a few moments before she slipped it back on again. He was so entranced by these small, private moments that he had nearly forgotten to finish filing.

 

He leaned so the headmistress's calf was no longer resting on him and started dumping his folders in the drawer a bit haphazardly. Apparently unconsciously, the headmistress's leg followed him, the tip of her foot landing in the small space between his legs. Byron's face was uncomfortably close to the headmistress's leg, it was pale and smooth, her skin flawless, he shrunk backwards but immediately discovered he had no room in which to retreat. Byron closed the file drawer to escape to the opposite side, so that he was facing the same direction as the headmistress, between the outside of her thigh and the side of the desk.

He tried re-opening the drawer but it bumped into the headmistress's leg before it opened completely. He nudged her calf, smooth and delicate looking but bigger around than his thigh, by gently pushing the drawer into it but it did not budge. He tried again, more insistently. It wasn't until he was steadily pushing with much of his strength that the headmistress's calf moved enough that he was able to open the drawer completely.

 

Byron was still wearing his uniform blazer and the body heat radiating from the headmistress was making him uncomfortably warm but, although he had to reach around the headmistress's shin, he was able to start filing again. He had just placed the last folder in the drawer when the headmistress's leg swung into him, her thick thigh knocking his head into the side of the desk with a dull thunk. Byron was dazed by the impact and didn't notice the hefty appendage continuing in his direction. Emery's leg pinned his head against the side of the desk, his face sinking in the the supple outer layer of the headmistress's bulky thigh.

 

He struggled to draw breath, most of his mouth and nose submerged in thigh fat. Even in his oxygen depleted state, Byron had to admire that, within the headmistress's plush outer layer, he could feel massively powerful muscles working. Not so impressed by her thighs that he wanted to be asphyxiated by them, he slid both hands onto the headmistress's thigh and pushed. The thigh did not move easily and more than once made a bid to envelop his face again but eventually he managed to convince it to stay away.

 

Once he had enough room to breathe properly he slammed the file drawer shut and scooted around to get clear of the danger zone. The headmistress's huge legs, however, were blocking Byron under the desk so completely that not even his small, slender body could squeeze through.

“Excuse me, headmistress?”

 

No answer.

 

“Headmistress? I need to get out.”

 

Slowly, almost grudgingly, the vast legs moved to the side. Byron was exasperated that she did not simply stand up to let him out, the space that was left to him did not allow for a clean exit and he wasn't eager to embarrassed himself further by wriggling out like a distressed eel.

 

Byron lay on his back and slid under the headmistress's chair. The straining sounds from the wood much more concerning now the he was relying on the chair's durability to keep him from being squashed. He pushed himself backwards with his legs until his head was clear. Byron found himself looking up at the headmistress's rear, a considerable amount of chub was forced through the opening in the back of the chair. It was like someone tried to force two yoga balls through a doorway at the same time.

 

Byron stood, avoiding looking at the back of the chair, and walked back to the file boxes. No sooner had he selected a new stack of files than the headmistress finished her phone call, stood, and walked out of the room. Byron swallowed his irritation at the timing of this move as his eyes fell on the desk. She had left her phone. This was his chance.

 

Byron walked quickly back to the desk and dumped the files he was holding on the floor. Fumbling, heart pounding, he pulled the micro SD card from his shirt pocket and crammed it in the port on the headmistress's phone. Mercifully, he was able to start cloning the data without having to figure out how to unlock the phone. He watched the door for any sign of the Emery reentering.

 

Outside the office, he could hear the headmistress scolding Lindsay for something. No wonder the girl was so jumpy, always under the watchful eye of Headmistress Emery. Byron glanced down impatiently, the copy was 35% complete. He wondered, given that he was likely to spend the entire year in service of the headmistress, if he was going to end up as nervous and twitchy as Lindsay. No, he was made of tougher stuff. 52% complete.

 

The headmistress's footsteps thumped towards the office door. Shit, 57%. Thinking fast, Byron snagged the phone off of the desk and stuck it in his pocket as Emery ducked through the doorway. Even though he was at the wrong file drawer for the files he had dropped on the ground, he hastened to look like he was filing. His heart was pounding in his ears. Byron did his best to appear as if he was intently sifting through the file drawer even though the headmistress was not even looking at him as she sat, the displaced air ruffling Bryon's hair.

 

She had only been sitting a moment when the headmistress reached automatically for the place where her phone had been. Byron's heart leapt into his throat. Emery searched the desk, patting down stacks of paper, confused. As she searched the far side of the desk Byron snuck the phone out of his pocket just enough to check the progress. It was complete. And not two or three moments too late.

 

The headmistress stood and leaned over the desk to check if her phone had fallen off and Byron seized his opportunity. He quickly wedged the phone between some papers, hoping she'd think she simply overlooked it. Byron pressed down on the SD card to release it. Bwonk! In his haste and panic, he ejected the memory card too hard and it shot out of the phone.

 

By the time Byron spotted the card's landing place on the chair, the headmistress was already bending back down. He could only watch as the tiny card was engulfed by the vast rear of Headmistress Emery, her butt bulging outward as it made contact with the seat and shaking slightly before settling to an uneasy stop. There was no question about the headmistress feeling the SD card, it was like an ant underneath... well, like an ant underneath the gigantic ass of a huge, voluptuous woman.

 

Byron continued to stare at the place the card had vanished for a long moment after it had been overcome by the bulging ass until he realized that to an outside observer it just looked like he was kneeling a foot away from the headmistress, staring intently at her ample butt. He glanced up at the headmistress's face to see if she noticed him staring, but she was already making another phone call with no thought for him whatsoever. Byron had some concern for the welfare of the SD card, buried as it was under a veritable mountain of ass, but it was flat, plastic, and taking only a small fraction of the headmistress's weight, which was spread over the generous surface area of her broad backside. Unlike the metaphorical ant, the card had no need of oxygen so it could remain indefinitely sealed beneath the acreage of the headmistress.

 

Byron let a folder slip from his hands and scatter papers behind the headmistress's chair so that he had an excuse to get into position to save the imprisoned memory card. He moved around behind the chair so that he was entirely out of the headmistress's periphery and very slowly began gathering up the papers. He looked up at Emery again to see if she was suspicious of his unlikely clumsiness but she was completely absorbed in her phone call, her light red hair faintly shaking as she gesticulated.

 

The headmistress leaned to the side and one great cheek started to lift from the chair. Byron froze, ready to snag the card if the opportunity presented itself. He thought he might have glimpsed the card before the headmistress rolled her weight back into place, trapping the card once again. The next time the curve of her ass raised from the seat Byron saw the whole of the micro SD card but hesitated in grabbing it so that by the time his hand was ready to strike, the headmistress was already landing back into position with a slight bounce.

 

The third time she liberated the memory card, Byron was ready. His hand snaked out and landed flat on top of the card, dragging it backwards along the chair. Eyes focused on what he was doing, he sensed more than saw the looming swell of the headmistress's backside. Byron tried to jerk his hand the rest of the way back but he was unwilling to part with the card and it cost him dearly.

 

The soft underside of Emery's ass molded around the shape of Byron's hand like a memory foam pillow. He had managed to get most of his arm out but his hand and wrist were pinned as the plump behind of Headmistress Emery steamrolled them. Panicked and desperate not to be caught in such a compromising position for which he had no good explanation, Byron's eyes shot up to the back of Emery's head. Mercifully, she chatted on the phone with no change. Perhaps because Byron's hand was flat or perhaps simply because she was so massive, she had not yet felt his hand. In fact, it was becoming increasingly difficult for Byron to feel his hand as well. While the headmistress's weight was soft and warm, the pressure was so much that it was driving the blood out of his hand remarkably fast.

 

Feeling like a trapped animal, Byron had to will himself not to yank his hand out from under the giant educator. Huge or not, she was sure to notice that. Byron managed to restrain himself but moved his arm into a more comfortable position. The round ass wobbled slightly in retaliation. The headmistress stiffened and Byron's stomach dropped, he was surely caught. But no, the Emery simply leaned her weight back and forth, alternatively crushing and relieving Byron's hand but not lifting fully off the seat.

 

After a minute that felt like a lifetime, Byron's hand was completely numb. If it wasn't for the incessant bumping of the headmistress's butt against his wrist as the effects of her animated phone conversation traveled down her body, causing a noticeable shaking, he might have been able to imagine he was anywhere and had simply slept on his hand wrong. If they were going to write songs about his great deeds, Byron really hoped they left this part out.

 

The anxiety of his predicament was fraying Byron's nerves. By the time he had been confined under the headmistress for a minute and a half, he was ready to simply yank his hand out, walk out of the room without looking at Emery, leave the school, change his name, and move to Canada. But finally, the headmistress moved. Her heavy cheek did not clear his hand entirely but covered only his fingertips. From this position, he thought he would be able to slide out from under her without being noticed and in any case was completely out patience.

 

As slowly and carefully as he could, Byron slid his fingertips from under the headmistress's bottom, which greedily reclaimed the space he had vacated. As he pulled his hand toward the edge he confirmed that he still had the card beneath his numb fingers. Predictably, given his luck thus far, before he could get the card completely off the chair, the headmistress's ass landed fully back on the chair, swallowing his hand again. He was, at least, in a much better position now, only his fingers and knuckles had been reclaimed by the meaty bum.

 

So close to freedom, Byron just yanked his hand out, the SD card falling to the floor and Emery's buttock jiggling angrily in response to his rudeness. He snatched up the memory card with his working hand while he open and closed his squashed hand. Feeling started to return immediately, mostly the feeling of pain, as the blood ventured back into his extremity.

 

“Byron?”

 

Byron's fear, which had abated somewhat with his freedom, returned with a rush that made his head swim. He hadn't noticed Emery end her phone call. He made a useless grab as some of the paper one the ground, his recovering hand fumbling it hopelessly.

 

“Are you finished?” the headmistress asked.

 

A glance upward told him that she hadn't noticed anything, she was just now twisting in her seat, trying to spot him.

 

“No, headmistress.”

 

“Well get to a stopping point, we're about done for the day.”

 

 

The headmistress looked over his work meticulously. She was bent over the filing drawer as he stood behind her, presenting him yet another view of her broad rear. It wobbled happily, mocking him. As a lover of full bottomed women, Byron would not have objected to such a view but not only did it make him somewhat guilty to contemplate an older woman with direct authority over him (never mind that his bodyweight was almost certainly outstripped by a single one of her thighs) as a sexual being, his recent adventure had left him feeling shell shocked and very wary of the vast secondary sexual characteristic stretched out before him. He felt marginally better as the thought occurred to him that, given the headmistress's size and the prominence of her posterior, this had to be a view that virtually everyone at Waycroft was extensively familiar with.

 

“Not great,” Emery said, straightening up and gesturing for him to take a seat on the other side of the desk. “I found a number of mistakes and it didn't seem like you got through all that much in the time that you were given.”

 

Byron was still emotionally exhausted from his extended panic, but was hit with a pang of disappointment. It wasn't like him to do more than the bare minimum in any situation, so this was something of a new experience for him, to regret not working harder.

 

“I'm going to expect you to do much better in the future,” the headmistress continued.

 

Byron looked at the desk, not meeting her eyes.

 

“What do we say?” she asked impatiently.

 

“Oh... yes, headmistress.”

 

 

Byron leaned against the wall outside the front office and let out a breath he hadn't known he'd been holding in a long exhale. Hands shaking slightly, he pulled the micro SD card out of his shirt pocket once again and put it in the port of his own phone.

 

With the intuitive skill of a digital native, Byron unlocked the data on the card. Feeling a little shameful, he started poking through the headmistress's files. It seemed like she didn't keep a regular calendar. Or... fuck, did Lindsey keep her calendar? Was he going to have to do this again with Lindsey's computer?

 

With increasing frustration, Byron started digging deeper into Emery's accounts. Thankfully for his conscious, the headmistress kept few personal details on her phone, so it felt less like a violation. He had been through a week of her e-mails when he saw it- a 9 pm reservation on Friday at Mulino's.

 

A 9pm restaurant reservation? That was a date. Byron briefly wondered about the kind of man who was ready to take on all that woman. He had another uncomfortable twinge as he was again forced to confront the idea of the leader of his school having a sex life.

 

But a date... that was good. He really doubted she would want to take a date back to her campus quarters. Even if she didn't go home with him, surely they'd be out past midnight if their date started at 9. That was enough to make a plan around. Looked like Fall-FuckFest was on.

 

Chapter 6 by bbbs

Filing had lost some of its luster. Not that it was particularly glamorous to begin with, but by the next Friday, his third work-study appointment, Byron had already had his fill of it. In his last go-around, he had, according to Emery, markedly improved. It wasn't much of a shock, in his first work-study he had been notably distracted by subterfuge and butt-related crises. Additionally, he found, to his own surprise, that he was making a real effort to improve his performance. He was finding that the headmistress was as good as her word- she was strict but if you managed to stay in her good graces the intensity of her attention was warm and welcoming, albeit still somewhat frightening. So for possibly the first time in his life, Byron was making an effort to do more than coast and trying to bury his instincts for mischief and antagonism.

 

Despite his mysterious new desire to please her, the frightened scratching in Byron's subconscious was growing ever more frantic when Emery loomed over him. He was currently enjoying a brief respite from her company, the headmistress had adjured to the bathroom that connected to her office. Byron had not been in the bathroom, he was an infrequent pee-er and doubted that he's have the nerve to use the headmistress's private bathroom even if he had to go, but he had seen it from the outside. It was as opulently ornamented as the rest of Waycroft and did not lack for functionality, containing a full-sized wardrobe and shower large enough even for Emery. Bryan surmised that he had a little time to himself, he had heard the shower start and it was fast approaching 7 PM, when they usually wrapped for the day, so the headmistress was probably getting ready for her date.

 

Byron had allowed his brain to go slack, knowing his filing performance would suffer but he was drained from his shift in the emotionally oppressive company of the headmistress. As was so common in the last week, his thoughts drifted into fantasy waters and sank into pleasant musings of FuckFest. Byron had only been at Waycroft for two weeks, but felt that if he didn't hook up with someone soon he would not be able to claim his preferred reputation as a charming Lothario. In a deeper, more guarded part of his mind, he was preoccupied with Chloe and was anxious to see her again. He had not run into her again; he had avoided making detours to see another volleyball practice, he didn't want to seem like he was stalking her. Initially he was concerned that she might not show up to the party, but his fears were put soundly to rest. By word of his hall-mates and the prevailing reputation of the party, no one- no one- missed Fall FuckFest.

 

Byron heard a door click and looked up from his work. The headmistress emerged from the bathroom and Byron felt his breath catch in his throat. Emery never looked anything but well put together and occasionally even stylish but it was suddenly clear that she did not put her full effort into her appearance for school. She was wearing a black dress that somehow both accentuated her curves and did not overwhelm the senses with them as was so often the case in her day to day wear. It was one hell of a dress. Or she was one hell of a woman and the dress was just the perfect textile overlook from which to view. Byron knew nothing about makeup, he had the general idea that he preferred if girls wore none as the headmistress usually did, but even he could see that her subtle application enhanced her already fetching face. The green of her eyes shone more brightly than usual, accented by dark (he wanted to say eyeliner?) makeup. The headmistress had also done something to her hair- where it was usually straight and silky, it now had a wave to it and sort of bounced as she moved. Where she usually wore only flats, today she donned heels, not that she needed any extra height, but they did something to her posture and gait that was enticing. To complete her opus, the headmistress wore a long silver necklace that gave the slightest hint of permission to stare at her enormous bust as it rested on the incline of fabric stretching to cover her chest.

 

For the first time, Byron fully appreciated how beautiful Emery was. It had always been abundantly evident that she was attractive but was an abstract fact obscured by the visceral reality of her size. Every thought about her appeal was prefaced with 'if she were a normal size'. But there could be no thought of that now. There could be no thought of anything, Byron's mind was racing around gathering up the broken pieces of his consciousness. The word 'Goddess' had sprung, unbidden, into his head and he carefully picked his way around it, trying to pretending it wasn't there.

 

The headmistress strode across the room, her usual thumping footsteps replaced with the loud staccato clack of her heels. For a brief, bizarre moment Byron was concerned for the expensive wood floors of the headmistress's office but a glance down told him that they were unmarred by the headmistress immense, concentrated weight. Byron, who was filing, ostensibly at least, was kneeling by the headmistress's desk. Headmistress Emery clacked around to the other side and started lowering her massive rear onto one of the normal sized visitor's chairs. Her descent was stopped well above the seat cushion on the arms of the chair, her thick thighs blocking the chair from view and more of her ass bulging past the bounds of the chair than was parked over it. Clearly conscious of the very real possibility of turning the chair into a pile of lumber, the headmistress only rested her weight slightly on the chair. Her face showed no sign of strain but Byron could see strong muscles pushing out of her plush thighs. The chair still creaked ominously and there was an alarming splintering sound.

 

“Byron,” she said, without looking at him.

 

“Yes, headmistress?”

 

“Come here and zip this up for me.”

 

Byron swallowed and walked around behind the headmistress, marveling at how small a fraction of her ass the normal sized chair accommodated. Her stunning look had given her an even more intense presence than before, something much more unapproachable. So it was with some trepidation that Byron stepped up behind her and melted into a wave of perfume. It was something sweet and strong but not overpowering. Byron collected himself and looked to the zipper he was supposed to be closing in the middle of the headmistress's broad back. If he stood on his tip-toes he'd be able to grab it but wouldn't have any leverage to pull it up from there.

 

Although the headmistress showed no sign of impatience, Byron hurried to drag over the other visitor's chair to use as a stool. He hopped up unsteadily and put a hand on the headmistress's side to steady himself. His hand sunk slightly into her love handle and he was struck with a sudden sense of guilt. The headmistress did not react at all to his touch, but he removed his hand anyway, as soon as he was sure of his footing. Headmistress Emery lifted her wavy hair up off of her shoulders, but missed a few strands that threatened to get caught in the treads of the zipper. Although it felt dangerously overfamiliar, Byron gathered the strands in one hand and held them out of the way. He pulled at the zipper, surprised at how heavy it was on such a fine dress.

 

He had gotten the zipper to close and was about to release the headmistress's hair when he heard the office door open. He snapped around, his face the picture of guilt. It was Lindsay. Spotting the look on Byron's face, she tried to back out of the room, but it was too late.

 

“Lindsay?” the headmistress called without turning around.

 

“Y-yes headmistress,” Lindsay answered, abandoning hope of escape.

 

Eyes on the floor, Lindsay entered the office and shuffled over to the headmistress. She handed her a piece of paper wordlessly which the headmistress took and examined.

 

“Thank you, Lindsay, you may go.”

 

Not needing to be told twice, Lindsay took the returning trip at, while not quite a run, a sort of a limping, shuffling jog. Realizing he was still holding on the headmistress's hair, Byron let it go and hopped off of the chair. He had dragged it back to its place in the room before the headmistress finally looked at him.

 

“Thank you, Byron.”

 

“Yes, headmistress.”

 

She gestured to the chair with a small smile. “We'll have to get you a step stool.”

 

Byron, who secretly hoped that would be the last time he would be asked to do something so intimate, smiled weakly back.

 

“Aren't you going to tell me how nice I look?”

 

Caught completely off guard, Byron cleared his throat to buy time. Feeling awkward, face burning, he took his best guess at the appropriate response.

 

“You- uh- look very nice, headmistress.”

 

“Oh, don't gush, you're embarrassing me,” the headmistress said dryly.

 

The headmistress's expression was entirely neutral, so Byron wasn't sure where he stood. As he was studying her for any sign of anger, he saw the corner of the headmistress's mouth subtly tighten and curl. She was holding back a smirk. She was fucking with him! A flare of anger blasted through Byron's nervousness. She might run the school. She might hold his future in her hands. She might be able to literally tear him apart. But if the game was roguery, Byron was the home team.

 

Byron queued up his best faux-sincere voice, a well practiced skill he was confident was convincing, and reached down deep to find every insecurity he had ever suspected was drilled into girls when they were little and never really went away.

 

“I didn't know you when you were younger, headmistress, but I am still convinced that you've only improved with age because I can't imagine you ever being more lovely than you are right now. I hope, wherever you're going tonight, there will not be many women because they would be hopelessly outclassed.”

 

He thought he might have laid it on a little thick but the headmistress's forced deadpan expression and unfocused eyes told him he had hit the mark. He could tell that she was genuinely flattered in spite of herself. Point for the home team.

 

Without warning the headmistress's eyes focused and she extended her arm outward. Byron, who thought he was outside of her reach, flinched involuntarily as her huge hand closed around his upper arm. Her hand encircled his arm entirely and would have had room to spare if it hadn't been closed in a vice-like grip. With no apparent effort she pulled him forward until he was inches from her. Byron was, once again, forced to look past the intimidating swell of Headmistress Emery's magnificent bust into her intense face.

 

“You should be careful, Byron,” the headmistress said softly, in almost a whisper, “someone might get the wrong idea when you say things like that. You might lead someone on and that can have all sorts of unintended consequences that you might not enjoy.”

 

She released his arm and Byron, not even realizing he had been pulling against her grip, stumbled backwards. His arm was sore where she had grabbed it, it would undoubtedly be a bruise by the next day. He fought against his desire to rub the spot where it hurt and met Emery's eyes defiantly. She had a satisfied expression on her face and Byron knew that not only did the home team not get to win, they didn't get to score. Because if they scored there would be consequences. And she had 8 more months to dole out consequences. He wondered hopelessly what he would need to do to get kicked out of Waycroft.

The headmistress dropped a foot that was at least half a yard long onto her desk. It landed with a dramatic thump that sent writing instruments and assorted knick-knackery bouncing up and down. Byron noticed that the strap in the back of her heel was undone.

 

“Now,” said the headmistress with a cruel smile, “I'll need you to fasten these for me.”

 

Chapter 7 by bbbs
Author's Notes:

OK, so here's the thing. I accidentally wiped my hard drive when, ironically, I was trying to set up a new backup drive. It wiped out the chapters I had written and was editing and my entire outline for the story. I might have bounced back in a couple weeks but then COVID hit and the isolation was extremely emotionally draining. I was also up to the first payoff after a lot of set up and I really wanted to nail it, which is kinda intimidating. By the time I was ready to try again I had forgotten what my outline looked like so I put it off.

Finally, finally, I just said screw it and started writing again. The thing is, I don't really remember where this story was going so I'm going to be winging it. Let's take this ride together.

By 8 PM, nearly an hour before Fall-FuckFest was expected to even start, Byron was already rather drunk. Martin, who lived across the hall, had stopped by to pre-game with Byron and Damien. Like many of the students at Waycroft, Martin came from a well off family and he felt it only right to generously share his families wealth by bringing several cases of beer with him to drink-ups. As much as Byron appreciated the alcohol, he wasn't sure where Martin had managed to dig it up. Usually students relied on local older siblings, bribed townies, or found convenience stores with the most apathetic staff but it was evident that this beer did not come from any of these sources. The label, to Byron's best guess, was in Croatian, the beer burned his throat, and it was (albeit it was difficult to tell with the Croatian label) somewhere in the area of 12% alcohol content.


The three boys, along with numerous others that had filtered in and out of the room as their hallmates paced out their pre-party jitters, had been playing some drinking game, the rules of which Byron had never truly grasped. A poor drinking game performance combined with his slight build left Byron not so drunk that he was in danger of being sick, but drunk enough that Martin was fairly easily able to convince him that wearing a flag with the school crest on it as a toga would be a daring fashion statement.


“Svi jedemo sir i jebemo koze!” apropos of nothing, Byron shouted a phrase he had read on the back of the beer case.


Martin and Damien were looking at him expectantly. It must have been his turn to play a card. He took a deep swig of his Croatian beer and tossed out one at random.


“This is a coaster,” said Martin, “from the... Big Texan motel? How do you even have this?”


“I think this game should be over,” Damien declared, eyebrows knitted.

He leaned over to try to tug the beer from Byron's grasp, but like the long, proud history of drunk people that came before him, Byron held on to his drink with a ferocity that belied his modest strength.

Patiently, Damien leaned closer and said quietly, “Normally I would be all for you getting absurdly drunk and making a huge ass of yourself. Trust me, I'll be the one egging you on more often then not. But if you are too drunk to enjoy tonight you're going to massively regret it in the morning.”

Although his drunk belligerence had firm control of the wheel, the tiny voice of reason in Byron's head managed to take over for the briefest moment and he let the beer slide out of his hand.


“Go take a cold shower,” Damien suggested, “I'll keep your toga safe for you.”



The shower helped. As did the next hour of abstaining from drinking. But even so, in the days that followed, when Byron would think back on the beginning of the party, he could only recall bits and pieces. It was as if every time he closed his eyes the world jumped forward in time.

They arrived at the party a little earlier than might be considered fashionably late, but it was already roaring. The hall lights were all off and colored effect lights strobed feverishly. Someone had gone absolutely ham with fog machines and a thick layer of smoke wafted over their feet to the rhythm of some tuneless EDM song.

Blink.

The lights haphazardly illuminating the smoke in the opulent hallway and the thumping bass of what might generously be referred to as music churned the Croatian beer sloshing around in Byron's stomach in an unpleasant way. But at that moment he didn't care. The energy in the party was electric. He turned around to share his excitement with Damien and Martin but they were nowhere to be found.

Blink.

The silhouettes Bryon could see moved through the party exuberantly, almost giddily; the chatter that he could pick up over the music was light and excited.


Blink.


The people he passed, people whose names he hadn't really yet learned, shouted admiration for his toga and slapped him on the back. Byron did not remember picking up a drink, but someone must have handed him one. He was delighted to find that this did not burn his throat and he drank deeply.


Blink.

A cheer went up as Byron pushed open the door to the cafeteria and it took a moment to realize the cheer was for him. Or, more accurately, his toga, but if still felt nice. He waved to his public like Caesar and a dozen hands pulled him into the thick crowd gathered on the cafeteria floor.


Blink.

At some point Byron's natural tendency towards hammery must have taken over because he was dancing exuberantly with a group of people he didn't recognize. They seemed to be edging away from him in fear of his increasingly wild arm moves. His moment was already over, people had lost interest in the novelty of his outfit and his physically dangerous dance moves but his spirit was still light. This was going to be a night, he was sure of it.


Blink.

Now dancing by himself and sweating from exertion, Byron allowed himself to coast to a stop. He tried to spot a place to refill his drink but only saw a writhing mass of bodies no matter where he looked so he picked a random direction and pushed his way into the crowd. The press of the crowd was so overwhelming that he didn't realize he was being tapped on the shoulder for several moments before he finally registered it.


Blink.


He was talking to a girl that looked a lot like Lindsay. She was small and blonde like Lindsay and wore Lindsay's perpetually terrified expression. It occurred to Byron that this might, in fact, be Lindsay, though if that were the case the fact that she was voluntarily talking to a fellow human would be out of character. Maybe-Lindsay was talking very fast and gesticulating emphatically. Byron couldn't make out anything she was saying over the pounding music. Probably-Lindsay had paused and was looking at him expectantly so he nodded sagely as if he had understood anything she said to him.


Blink.


Lindsay had her hands on Byron's shoulders and was shouting in his face but his senses were still so overloaded that he wasn't really taking in what she was saying. Her eyes were bulging out of her head and she looked like she expected to find her self on the business end of a guillotine any moment- so pretty much how she always looked.

“I completely understand where you're coming from, I kind of want to choke him too.”


Byron heard the voice from behind him clearly over the racket of the party. He turned his head and saw the statuesque figure of Chloe, head and shoulders above the crowd, her wide hips easily clearing a path her as she came to stand beside him. She looked amazing in a tight blue dress made of a soft material. She was wearing shoes with a small heel, an inconsequential addition to her height but made her already tremendous backside seem even more prominent. Her expression had the forceful confidence and mischievous playfulness that had so charmed Byron on their previous encounters... but there was something else hiding behind the poise.


Wait, wait. That was jealousy, he was sure of it! Lindsay had sensed it as well, her arms went slack on his shoulders.

Of course, of course, Byron had already blown his shot, things were going way too well for him. He wanted to explain that he regarded Lindsay more as one might an umbrella or a toaster, something you see frequently but don't really have any emotional attachment to, but he couldn't get any words out. Panicked, he stammered thinking of the right way to assure Chloe that he might not know what was happening at the moment but it absolutely could not be a prelude to anything romantic.

Before Byron even had a chance to get out a word, almost certainly making things worse, Chloe slid a long arm around his shoulder and squeezed him possessively to her side. Dazed from emotional whiplash and still more than a little drunk, he allowed himself to sink into the softness of her side. Chloe grinned broadly at Lindsay. Ostensibly, it was a friendly gesture that said “we're all friends here” but even in his cups Byron was astute enough to see the real message, “I'm not threatened by you but this is my territory and I am perfectly willing to squash you.”

Blink.

Byron was walking somewhere. He didn't know where but there was an insistent force on his upper back directing him forward. Sensing an imposing presence he looked over his left shoulder and found himself staring directly into Chloe's chest. Her right hand was centered on his spine, but big enough to cover the majority of his back.

If she had told him where they were heading his brain had pissed away the information like so much Croatian alcohol. The force of her hand was such that he didn't think he could stop moving if he tried. He chanced a glance at her face. Impassive.


The cafeteria door swung shut behind them as Chloe marched Byron into the outer hallway, the full assault of music dropping to a steady, percussive thump of bass. Away from the oppressive crowd and music, Byron scattered thoughts started to knit back together again.


The outer hallway was by no means empty. Numerous tightly entwined couples were working valiantly to earn the party's name. While nothing Byron saw was beyond PG13, it was clear where this hormone train was headed. Byron passed a girl he thought he knew from his Senior Seminar class rounding first base with a boy with a shaved head and nosiness got the better of him. As he indelicately tried to lean closer and see if it was her, the statuesque figure behind him moved around to the front.

Chloe looked down at him with an expression Byron couldn't quite read but impatience and reluctant amusement were key elements in its construction. Wordlessly, she took Bryon's hand, her larger hand enclosing his with room to spare, and pulled him along behind her. She turned into a nearly deserted side hallway and pulled Byron in front of a closed door, where she stopped.


Chloe let go of Byron's hand to pull a pin from her hair and work it into the latch of the door. Free of persistent stimulation, Byron's slack attention was immediately pulled into the swell of Chloe's butt. He could see it jiggle ever so slightly through the soft fabric of her dress as she worked the door. He was at the point of wondering if her hips were a full three times as wide as his when he heard a click and a satisfied sigh from Chloe.

“There.”

She caught his eye, winked, and pushed open the door.


“What is this place?” Byron asked, glancing around, impressed.


They entered a small, comfortable room, less stuffy and formal than most of the campus but no less expensive looking.

“Teacher's lounge,” Chloe responded. “It's one of the smaller ones, so I don't think many students know about it.”


Byron flopped gratefully onto a couch, which was as comfortable as it looked. Chloe sat down next to him, her considerable weight bouncing him briefly up into the air.


“Ah,” Chloe sighed, “I love a rager but that was getting a little much even for me.”

“I can think of some things I'd like to discuss with the deaf robot that chose the music.”

Byron noticed that she was sitting so close to him that the edge of her hip was resting lightly in his lap.


“So who convinced you to dress like that?” Chloe asked.


“What makes you think I need any help picking out my wardrobe?” Bryon shot back, a little too forcefully to be completely playful.

Chloe raised her eyebrows at him but mercifully decided not to press the matter.


“You don't have a drink, maybe I should go get us some” she offered.

Byron hesitated. “I think you might be too drunk,” he said dryly.

Chloe laughed.

“I'm going to go get us some drinks,” she said, standing, “and if any little blondes come sniffing around you can send them on their way.

She gave him a sly smile and he rolled his eyes but couldn't help but smile back.

“Don't miss me too much,” she called back to him as she left the room.


Byron laid down on the couch. As anxious as he was for Chloe to return he was drained from his overindulgence, the intensity of the party, and the emotionally fraught misunderstanding with Lindsay. He needed a few minutes just to lay down until the world stopped spinning.


Before he even had a chance to overthink how his romance was going, he heard the door handle jiggle. It was too soon for Chloe to be back. Byron sat up, prepared to shoo away any other students trying to encroach on his quiet place.


“Chloe?” came a voice. The voice had a slight accent. Byron knew that voice.


The door popped open and Amy's head peaked in the room. She frowned when she saw Byron.

“What are you doing here?” Amy sneered, her tall, curvy body following her head into the room. She was dressed much more informally than Chloe in a low cut blouse that revealed an acre of cleavage and a pair of dark colored jeans that she had somehow pulled over her wide hips and shelf of an ass. Her clothes were tight enough to reveal her muffin top and the size of her generous belly but the overall effect highlighted her hourglass shape.

“Chloe brought me,” Byron said with a smirk. He considered asking her to leave but as little as he knew about Amy he could tell that a direct request from him would only embolden her to do the opposite.


“Ugh, are you following her around like a puppy again?” Amy asked, sitting heavily on the couch next to Byron. Her wide ass took up a full cushion and then some.

“Hey, she found me at the party and I don't really think I had a choice whether or not I came with her.”

“Did you wear that,” Amy said, gesturing to Bryon's toga, “instead of developing a personality?” She glared at him for a moment and then turned away.


It was a weak insult. Of the many colorful things Byron had been accused of over the years, being bland was never one of them.


“Wait,” he started, leaning over to try to get a look at Amy's face, “are you jealous?”


Amy turned further away and spoke with her back to him.

“Ugh, shut up.”


“You are jealous, I don't believe it!”


Slowly, something clicked into place for Byron.


“Wait... are you jealous of her... or me?” he asked.

Amy turned around and looked at him. She seemed to be debating providing him with an answer when they heard the door handle shake.

“I don't know what is in this drink someone described it as domestic terrorism so it should get the job done.” If Chloe was surprised to see Amy there she was playing it close to the chest. “Oh, sorry Amy, I didn't get one for you.”


“That's OK,” Amy said flatly, “I'll just have his.”


Chloe met eyes with Byron and he shrugged. Chloe handed the extra drink to Amy and sat down on the other side of Byron. Amy made gloating eye contact with Byron as she drank deeply from the cup that was supposed to be his but she was overestimating how much he cared about forcing more alcohol into his body.


Byron leaned back on the couch feeling very cozy between the two large girls, whatever animosity or complications might be brewing. Byron wasn't touching either girl but they were separated by less than an inch on either side- it occurred to him that because both girls needed so much space for their substantial bodies, specifically their considerable backsides, it wouldn't have been possible for all of them to fit on the couch without being on top of each other if his own body wasn't so small and narrow. Not for the first time, Byron wished he was a little bit bigger.


There was a silence. It wasn't a good silence. Amy looked slowly back and forth between Byron and Chloe as if hoping to catch them passing secret messages to each other. Chloe looked directly at Amy, her face expressionless but her still, unblinking gaze obviously a challenge. From his comfy home in the back of the couch, Byron endeavored to break the tension.


“Look,” he said, “if it will make everyone feel more comfortable we can all just fuck right now and get it out of the way.”


Chloe laughed and shoved him. Amy hit him with a pillow so hard that if he had been standing he was sure it would have lifted him off of his feet.

The girls were much more amicable after that, helped in no small part by weapons grade alcohol. The three of them laughed easily together and even Amy's teasing was trending less barbed and more whimsical. Flirting was played ostensibly as a joke but light touches and held glances made it clear the jokes were a facade. The mood became so light that Byron was willing to leave the convivial, sexually charged oasis of a teacher's lounge and get them all drinks to keep things rolling.


When Byron returned with three drinks, Chloe and Amy were sitting next to each other, whispering and giggling. When they heard him come in, they turned to him. For a moment, Byron knew what a gazelle experienced when it was spotted by a cheetah.


“Whats the matter?” Chloe teased, “Come sit down.”


Chloe slid over so the middle seat was open. Slowly, carefully watching both girls, Byron walked over to the couch and sat down. On the pretext of taking one of the drinks, Chloe slid closer to him, her hip pushing into his side. She placed the drink on the side table and took another which she also set down.

On the other side, Amy leaned in and took the final drink. She sipped it inattentively and a droplet leaked out of the corner of her mouth and ran down her neck into her bountiful cleavage. Byron's eyes couldn't help but follow the droplet as it disappeared into the darkness.


“You know,” Amy purred, “you might be kind of cute if you were the size of a real boy.”


This was the closest thing to a complement Amy had ever said to him. He stared at her, stunned, until he felt a hand on his leg. He turned to see Chloe rubbing his thigh.

“I don't know, I kind of like him this size,” she said in barely more than a whisper, “much more pliable.”

Amy reached across Byron and grabbed Chloe's free hand, guiding it to her upper arm.


“And here I thought you liked girls. Big ones.” Amy said in a playfully offended voice.

“A girl can't like two things?” Chloe replied.


They both leaned in across Byron until their faces were inches apart. Their lips met. Softly at first, their tongues gently probing just inside each other's mouths, then with abandon, their bodies undulating as their lips surged together again and again.


Byron hadn't even noticed he was getting hard until his erection bumped into Chloe's hand on his thigh. He made to casually adjust himself in his seat so his arousal wasn't quite so obvious but Chloe's grip was pinning him in place.


Chloe looked at him with a knowing smile as Amy kissed down her cheek to her neck. She let out a moan of pleasure and raked her fingers across Amy's face. Amy bit down on her neck and she let out a cry of surprise before falling back into the couch, giggling.


Amy turned to Byron.


“Who's jealous now?” she smirked.


Before he could even begin to formulate a response Byron felt Chloe's hand snake around the back of his head, her large hand easily palming the back of his skull. Forcefully, she turned his head toward her.


Her hot mouth was on his before he was even completely facing her. She tasted like peaches and vodka. Her huge tongue forced it's way in his mouth as her hand pushed him into her. Byron did not feel like he was much of an active participant in this encounter but before he could try to match Chloe's enthusiasm he felt a massive thigh slide over him.


Chloe broke away from their kiss and Byron looked up a the towering, voluptuous figure of Amy as she straddled him, kneeling on the couch. Amy grabbed the front of Byron's shirt and pulled him up towards her. She leaned down and kissed him forcefully on the mouth. It was so aggressive that it challenged Byron's understanding of a kiss as an affectionate gesture. After only a moment she pulled away and let Byron fall indelicately back to the couch.


Byron looked up at the two girls, equal parts ecstatic and intimidated.

This was really happening. Somehow Byron didn't feel very drunk anymore.

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