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.