Erotic writer, focusing on transgender chastity, spankings, and all-around hot sexy things. I do commissions, and I'm always looking for new writing prompts. Feel free to reach out.
Emily wasn’t sure exactly how long the professor had been standing there, but it was very clear that he had seen enough for her to be in big trouble. She had been, quite intentionally, a million miles away in her head. Doing her absolute best to tune out the world around her and the rather ugly truth that she was spending all of her pocket money to cheat her chastity cage in a public bathroom, surrounded by gawking strangers.
The illusion was utterly shattered now, and her fingers went numb with shock, dropping the vibrator which chattered across the tiles next to the toilet, as though trying to escape. The thought of fleeing herself flashed through her mind, but the professor was between her and the door, and running would ultimately make things even worse. The bathroom door closed behind the last of her fleeing audience with a whisper of hydraulics from the transom closer and a gentle thump as the door met the frame, leaving her completely alone with the professor.
Trouble had a habit of following Emily around. She didn’t think of herself as a troublemaker, just frequently trouble-adjacent. It was seldom for anything too serious; a few minutes late to class here, a low mark on a quiz there, being caught in bed with a fellow student on a not-infrequent basis… Small time stuff, by the standards of the school. This was most certainly not small time stuff. This was breaking the Golden Rule: Good girls don’t cum.
Professor Anson seized her elbow, and pulled her off the toilet. Ignoring her apologies, begging, and pleas to at least let her have her panties back, he all but dragged her out of the room. Being marched across campus, naked from the waist down, cage exposed, and getting prodded sharply between the shoulder blades with a vibrator any time she so much as hesitated was a new and awful experience for her. Worse yet, every so often she could feel something wet and sticky drip onto her thigh meaning that her cage was slowly dripping out very obvious evidence of why she was in so much trouble.
Worst of all she knew exactly where they were headed. She had positively begged Professor Anson to deal with her punishment himself, however he wanted, but he was having no part of it. Break the Golden Rule, you answer to the Headmaster. No exceptions. Her face burned scarlet as her walk of shame took her across the central plaza and up to the administration building. Even in a school as strict as Rattangrove the sight of a student being marched half naked across campus was an extremely unusual sight. Emily tried not to notice the stares and gasps as they walked, but she saw as the other girls pulled into tight groups to whisper and laugh.
They went through the heavy wooden doors of the administration building and climbed the stairs to the third level, drawing ever closer to the Headmaster’s office. Professor Anson didn’t say a word to the Headmaster’s secretary as he entered the office. He placed the large vibrator on the desk, gestured at his ruined pants with a grimace, then turned on his heel and walked away. The secretary gave Emily a small smile, showing some sympathy for her plight, but sadly not enough to loan her some panties, or even a towel to wrap around her waist. The receptionist met Emily’s nervous gaze with a tired expression and her eyes flicked towards the hard wooden bench that lined the far wall. Emily took a seat, the polished wood of the bench cool against her bare skin, and awaited her fate. She knew it would be the last time she would be sitting comfortably for some time.
It was a long wait. At first, her wait was alone and in silence, with the tapping of the receptionist’s fingernails on the keyboard, the hum of the fluorescent lights, and her own nervous heartbeat her only company. After a time Professor Anson returned, this time with Carla and Aurora in tow. He leaned over the desk and held a whispered conversation with the receptionist, who glanced at the guilty-looking pair and coolly extended a finger towards the bench Emily sat upon. With a look of dread and resignation the two girls took a seat on the bench; Aurora beside Emily, and Carla beside Aurora. The three sat in uncomfortable silence. Emily knew that they had most certainly seen her without panties, but she still tried to hide her cage with her hands. With the new arrivals, the office was filled with nervous shuffling of feet, twisting of skirt hems, and a little bit of pre-punishment sniffling.
Fae was the last to arrive. Eyes downcast and mute, she tried to join the guilty trio on their bench, but instead was escorted straight into the Headmaster’s office. Emily caught the flash of panic in her eyes as she was lead inside and her own stomach twisted in fear and sympathy. The office was soundproofed well enough that she couldn’t hear any of the conversation between Fae, the Professor, and the Headmaster. Unfortunately, she could hear all too well when the talking ended and Fae’s punishment began. Fae was a very small girl but she had quite a set of lungs on her, and the sound of leather snapping deep into quivering flesh, as well as her crying, pleading and finally begging left all three of the waiting girls squirming in place.
Aurora in particular seemed to be in some discomfort, twisting and squirming on the hard wooden seat. At first Emily assumed it was just fear; her own bottom was tingling and itching in anticipation too. But Aurora’s flushed cheeks and glazed eyes led Emily to think it might be something more. Aurora all but confirmed her suspicions when she reached down and nudged the ring of her own cage through her skirt. It was a nearly unconscious motion that Emily herself had done hundreds of times: sliding the metal ring down to create a little extra “room to grow”. Emily smirked at the knowledge, but focused her eyes at her bare knees, not wanting to let on that she knew. The receptionist sighed and sipped her coffee; she had seen and heard all of this so many times before.
Eventually the snap of leather and the tearful apologies of a very sorry girl concluded, and Emily’s stomach sank. Her legs felt watery and her palms were slick with sweat, with no skirt to wipe them on. Looking over at Carla and Aurora, both were pale and trembling, Carla’s cocky assuredness had fled; she stared past the receptionist, awaiting her fate anxiously. It was a few agonizing moments more before Professor Anson came to collect the three of them together.
Emily had thought that between the bathroom, the march across campus, and waiting all but nude in the office had been enough public humiliation for one day. She had assumed that her punishment, however painful, would be a private affair between the Headmaster and herself. Unfortunately, she had thought wrong. The three girls were escorted in together. The Professor held the door open for the three of them, and having ushered them to their doom quietly excused himself, leaving them alone with the Headmaster.
The Headmaster’s office was surprisingly large, nearly the size of a classroom; with an imposing wooden desk and a trio of filing cabinets standing at one end of the room where the Headmaster worked. A pair of small chairs faced the desk, the seats oddly low to the ground so that nearly anyone, regardless of height, would be looking up at the Headmaster. The walls were adorned with professional certifications, class photos, sun-faded sports ribbons, and medals from tournaments long past. A pair of elegant leaded-glass windows allowed plenty of light into the room, with photographs and even paintings of earlier Headmasters going back over a century hanging in places of honour. However, it was the other end of the room that drew Emily’s eye.
Apart from a large fireplace, empty and cold with the unseasonably warm fall, as well as the red-bottomed and still crying figure of Fae cooling off her cherry red behind in the corner, this side of the room was surprisingly empty. While the rest of the office had the homey, lived-in look of a room that had served as the workspace and meeting room for well over a century of Headmasters, this side of the room was entirely utilitarian.
Apart from a leather-covered, thinly padded punishment bench, the room to the right of the doorway was empty, though dozens of corrective implements hung from brass hooks on all 3 walls. Paddles, whips, canes, brushes, tawses, quirts, and several painful-looking devices that Emily didn’t recognize hung in terrifying abundance on the wall. Some were clearly new, being PVC or Lexan, others looked as old as the school itself, their venerable wood darkening slowly over time, having been used to correct hundreds, if not thousands of wayward girls.
The Headmaster himself was indefinably middle-aged, with a wardrobe that ran from tweed to perhaps hound’s-tooth if he was feeling risqué. His clothes were well tailored and immaculate: neither a burr nor an errant thread could be seen, and his shoes were polished to a nearly perfect shine. He was tall, lean, scrupulously well-groomed, and dour. A strict man, he had never struck Emily as being spiteful or mean spirited, though she would never have described him as being particularly merciful. Emily figured he could have been anywhere from a tired-looking 45 right up to a sprightly 60. His face was largely unlined apart from well-defined crow’s feet around his eyes, his hair greying at the temples and flecked with silver throughout, though it retained the thickness of a man half his age.
He walked slowly, but there was no hesitation of waver to his movements and his back was perfectly straight. Every movement seemed deliberate, considered well in advance, and executed with precisely the amount of effort required and no more. Even his words seemed to have been carefully considered and weighed before he opened his mouth. Each one precisely chosen and given careful and deliberate inflection, never rushed or hurried; she had never once heard him stammer or trip over his words. He carried himself with an effortless authority and presence, felt even by very well-behaved girls who had never made a mistake large enough to be summoned to his office.
“So… Carla, Aurora….” His eyes narrowed as he turned to look in Emily’s direction, who quickly looked down at her toes, suddenly noticing a rather telltale stain on her right shoe. “…and Emily. I’m sure you all understand why we are here. Professor Anson informed me of his suspicions, all of which were confirmed by your classmate.” He motioned towards Fae, who bunched her shoulders and seemed to be trying to disappear. “After some thorough… motivation, she was quite willing to fill in any missing details.” He frowned and pointed to Carla and Aurora, crooking his finger to motion them forward; “Let’s begin with you two: Skirts and panties off, and lay over the bench, girls.”
Carla stepped forward before Aurora, who was momentarily rooted in place; she was lying over the bench, resigned to her fate, before Aurora even had her skirt off. It further confirmed to Emily that Carla was the mastermind, and Aurora decidedly the follower; she understood Aurora’s hesitance. Her own stomach was already in knots. Emily could see the pink steel ring of Aurora’s cage wrapped tightly around the base of her scrotum, and she found herself feeling a little sorry for the poor girl. Emily could fully understand the desperation that must have driven her to this. She was surprised to see a small drop of precum drip from the tip of her cage as she settled over the bench. Had she enjoyed hearing Fae being punished? Just how deep did her voyeurism run?
Carla on the other hand, not being trans, had no “intimate jewelry” to display as Aurora settled in beside her. Emily didn’t feel particularly sad about seeing her in this state; Carla was an opportunist and a bully, and while Emily had needed the relief that she could offer, she felt none of the empathy for her that she did for Aurora, whose motivations she understood. The Headmaster paid the pair no mind as they waited nervously in position over the bench. He seemed a world unto himself, walking up and down past his broad assortment of punishment tools. He appeared to be in no hurry, musing for a time in front of the canes, before selecting a particularly nasty looking black-painted cane from the wall and swishing it through the air several times, reminding himself of its weight and flex.
“So… smoking on campus, skipping class, not to mention running a black market in my school…” he listed off the offences with a detached air, walking behind the two trembling young women. Gently, with the very tip of the cane he tapped the steel ring of Aurora’s cage, and Emily could see her knees nearly buckle. “Very likely some other indiscretions as well, I should think. Impossible to prove at this time, sadly…” He paused, and brought the tip of the cane up to his face, thoughtfully. “I think two dozen strokes apiece should suffice. And Miss Aurora, I do believe that moving you over to a yellow cage is appropriate under the circumstances. Anything to say in your defence before we begin?”
His question hung in the air, neither of the girls daring to answer, though Emily suspected that Aurora had already begun to cry silently. They had both been very thoroughly caught in the act, and any attempts at justification were almost certainly a waste of breath. Besides, as bad as this was going to be for them, Emily strongly suspected that they were both very relieved that they weren’t in as much trouble as she was. The Headmaster smiled primly as he gave them a few more moments to squirm, not relishing their anxiety and humiliation, but understanding its necessity. Everything below the waist exposed, minds fully on both their actions and the consequences before he began their correction. Real learning, he felt, was happening right now.
Swish-CRACK! The first strike landed across Carla’s bottom from right to left, and it became immediately clear why they had heard so much of Fae’s punishment. The headmaster didn’t believe in a slow buildup, he went straight for a full-power strike right from the first swing. The impact with Carla’s bottom echoed like a gunshot in the enclosed space. Carla had been holding her breath and it burst out of her with the first strike of the cane, coming out as a rushing exhalation that pitched up into a simpering whine. Her body shuddered with shock and pain but her hands gripped the bench firmly, keeping herself in position.
The Headmaster did not move on to Aurora immediately, but focused his attention on Carla for the next five strokes. Each from right to left, striking backhanded across his body to land directly across both of Carla’s ample cheeks; the motion seemed effortless and fluid, so well-practiced was the Headmaster. Carla was sniffling after the very first blow and was openly crying after the sixth, but she held position.
“Very good, Carla,” the Headmaster intoned, his face stony, but with a tiny spark of encouraging warmth in his voice. “You held position quite well.” He turned to Aurora next, and tapped the cane across the centre of her bottom. Aurora let out a low mewl that wasn’t quite a whimper and wasn’t quite a mumbled apology just before the cane came down.
CRACK! The cane snapped down, left to right, clearly the preferred angle for the right-handed Headmaster. She wasn’t sure if he simply swung harder from this side, or whether Aurora had a lower pain tolerance than Carla, but the poor blonde girl was dancing on her toes from the very first swing. While Carla had taken her strokes as stoically as she could, Aurora danced and twitched, and squeaked out frantic apologies through hers. After the first set, both girls wore nearly identical six-stripe patterns across their bottoms, though they had taken them quite differently. Unfortunately, the Headmaster did not approve of a girl moving too much during a punishment.
SNAP! Aurora shrieked as an unexpected stroke fell across the tops of her thighs. Emily winced, knowing how much that had to hurt and her eyes opened in shock as she saw Aurora’s hand reach back in pain. Putting a hand back was a bad idea with any professor, but Emily would never have dared try it with the Headmaster. Emily gritted her teeth as the cane swung down again, the wood digging into the fleshiest part of Aurora’s palm. Aurora let out a broken yelp and drew her hand back, hiding it protectively against her chest.
“Do attempt to keep both feet on the floor for your punishment, and do NOT interfere. If you cannot remain in position, I will add extra strokes to your thighs. If you attempt to reach back again it will go very hard for you.” His words were gentle, barely scolding, but they carried a tremendous weight.
“You had an opportunity to defend yourself with words, which you declined with your silence. If you cannot defend yourself with words, you absolutely will not defend yourself with your hands.” He paused a moment for her to reflect before stepping back towards Carla. “It is entirely for your own safety Aurora, and if necessary, I will restrain you.”
His face remained impassive as always, but Emily swore she could see the shadow of a smile in the way his eyes crinkled when he was inspecting his handiwork, bright crimson lines freshly branded into the pale skin of both Carla and Aurora. Was he enjoying this? Or was it simply the pride of a master craftsman? Whatever the reason, the punishment continued: six stokes for Carla who bore them surprisingly stoically and then six for Aurora who didn’t take them nearly so well, back and forth until all 24 searing strokes were delivered. Aurora was a mess; she had earned an extra half dozen penalty strokes across the backs of her thighs, though to her credit she had not reached back again.
Finally, it was done. The Headmaster stepped back to let both girls cry it out. Carla’s bottom was a mess of hot red wheals; the lines cutting horizontally across the widest part of her bottom, right down to her sit-spot, occasionally crisscrossing each other, each crossing point a place where she would still feel it sharply tomorrow. Aurora’s bottom was in even worse shape. Her constant squirming and kicking meant that even the Headmaster’s experienced hand hadn’t been able to prevent nearly every stroke crossing at least one immensely sore red welt, and her upper thighs were marked with penalty strokes. Carla was sobbing, her shoulders moving rhythmically, broken and sagging over the bench; deeply relieved that it was over. Emily wasn’t sure Aurora even knew that it was over, as she was still repeating the same apology over and over in between her own ragged sobs.
Leaving the girls in position on the bench, and without giving them a second glance, the Headmaster pulled one of the small chairs from in front of his desk into the centre of the room. He motioned for Emily to stand next to the chair as he walked over to his collection of corrective implements. Emily walked to the patch of carpet she knew he would expect her to be standing on. From experience she knew he was right-handed, and that he would take her over his lap right-to-left.
She hated being over anyone’s lap, but especially that of the Headmaster. Certainly, it was humiliating as he could see everything in excruciating detail. She was also worried that there might be a little cum left in the tube, and she didn’t even want to think about what would happen if she ruined his pants as well. The far more pressing issue, however, was that Headmaster delivered the most severe punishments exclusively over his knee. For these most serious of corporal punishments he needed to be able to feel her every breath, squirm, shudder and kick, to hear every last whimper and cry, and to be able to see up close just how much more her poor bottom could take. She had been bent over his lap once before and it had been by far the most painful experience of her life. She was dreading what was coming next.
The Headmaster let her stew for another few minutes, finally selecting an oval ebony hairbrush from the wall. It was clearly an antique, small yet heavy, carved from a single piece of ebony, with fine and feathered boar’s hair bristles, and a beautifully lacquered finish that had yellowed with time. It had to be nearly as old as the school, and must have visited the scorched bottoms of dozens of girls before Emily. It was old, hard, heavy, and utterly unforgiving.
It would bite deep into the muscle, leaving behind an ache that would linger for days, giving the poor girl a reminder of her misbehaviour every time she sat down for nearly a week. As much as Emily saw it as a thing of dread, the Headmaster handled the brush with reverence. It was clearly a favourite of his, and he treated it as gently and carefully as a mother might a newborn child. He ran his thumb along the bristles, too brittle with age to be useful, and along the smooth wooden back, before bringing down into his palm with a resounding WHAP!
Satisfied with his selection, the Headmaster walked back to the chair and sat down. Emily saw no point in begging, or trying to explain, or even trying to run. She laid herself meekly over his lap, making sure that the cage lay between his thighs, for both of their comfort. She could feel his eyes on her as he used his fingertips to gently guide her hips to the precise position he wanted her, her bottom as high in the air as possible, her legs slightly apart. Her palms were flat on the floor, but the toes of her trainers barely touched the carpet.
She knew he could see everything; her bottom-hole, which she desperately hoped was perfectly clean, the ring of her cage candy pink against her pale skin, some errant leg hairs on the back of her thighs that she always seemed to miss when she shaved her legs. She was no stranger to being in this position, but she never stopped hating it. Finally satisfied with her position, he tapped the back of the brush gently against Emily’s bottom, eliciting a sharply inhaled breath, followed by a low and miserable whine.
“Do I even need to explain why this is necessary?” the Headmaster’s voice was ice cold.
“No S-Sir.” Emily tried to make her voice as apologetic as possible. She doubted it would make any difference at all, but she was willing to do almost anything if it meant even one less strike of that fearful brush onto her vulnerable posterior. “G-Good girls don’t cum. I b-broke the rule, and I’m very sorry, S-S-Sir.” She could feel the tears coming to her eyes as she said it, and she hated how obvious her fear was in the way she stammered. She was certain he could feel her shaking, her bottom perched high and vulnerable, and she was already truly, deeply sorry. That wouldn’t save her though.
“Precisely.” The Headmaster affirmed. “Your apology is accepted, though we still have some business to take care of first.” He paused, letting that statement take hold.
“You understand that you will be fitted with a red cage for the remainder of the semester.” It was a statement not a question, and Emily knew that it was beyond argument. Any attempt, even a failed attempt to cheat the Golden Rule meant the red cage for a first offence and the black cage for a second. Any girl foolish enough to get caught a third time was simply expelled.
Thankfully, this was a first offence, but those consequences were bad enough. She tried not to think about the lost monthly milkings or the more severe discipline that lay ahead any time she was caught for the smallest infraction; the present had its own pressing problems. She felt the Headmaster’s left hand press firmly into the small of her back, meaning the spanking was about to begin. She squeezed her eyes shut against the tears, gritted her teeth, and waited. She felt the cool wood of the brush tap against her right bottom cheek as the Headmaster reacquainted himself with the weight and feel of the cherished instrument of correction. Emily shuddered at the sensation.
CRACK! Emily’s breath exploded out of her as the first strike landed on her right cheek like a scalding brand. Emily had been spanked by a remarkably large number of people; from her parents, babysitters, teachers, coaches, and principals… the list went on. Nothing had hurt like this. The brush seemed to be made of molten iron as it came down for a matching strike on her left cheek. The tears that had accumulated nervously in the corners of her eyes raced down her cheeks and dripped down onto the carpet. The spanking had finally begun.
The Headmaster may have walked quite slowly, but he spanked hard and fast, with every swat designed to be felt not just in the moment, but for days afterwards. He could see exactly how dark and red Emily’s bottom was getting in real time, and he had decades of experience in administering this sort of correction. He knew the telltale white marks that showed that a particular piece of skin had taken all it could, and he moved the brush blister to places that could still take more. From the middle of her cheeks down to the middle of her thighs, the hairbrush did great and terrible work. Emily tried to keep position, knowing well from watching Aurora that struggling would only make things worse, but her bottom went from warm, to sore, to excruciating, to intolerable in what felt like seconds.
Emily had no way to count the time as it passed, or each stroke of the brush as it slammed into her body. They came too hard and too fast, and the pain did not plateau, but intensified with each moment. Soon she was drumming both her hands and feet on the floor and begging for the spanking to end, she would promise anything if the pain would just stop. For his own part, the Headmaster was glad that Emily was so petite, and when she inevitably reached back with her hand to interfere he had it pinned to her lower back in a trice. Now she could kick and struggle as hard as she wanted, but he was firmly in control.
Squirm and kick and struggle she did though, as with every few swats the pain reached new and wholly encompassing level of pain. There was no point in begging, but it didn’t stop her.
“No! Please stop…” her voice was cut off as WHAP! The brush hammered down into her right bottom cheek. Emily regretted everything. The cage, the school, the vibrator, her toy at home, everything.
“I’m so sorry! Please…” CRACK! The heavy polished wood swung down again, and the pain flowed deep into the muscle, and radiated back out. The pain was excruciating, and laid bare her innermost soul; blasting it pure and clean once more in its excoriating white heat.
Lying over the punishment bench, their own bottoms cooling slowly, Carla and Aurora could hear what was happening to Emily and even Carla was moved by the girl’s sobs and wails. Both of them had been over the Headmaster’s lap themselves, Carla once and Aurora twice, and both knew how terrible an experience it was. Listening to their classmate be so thoroughly chastised made their hearts sink, and both were deeply relieved that it was her and not them in that position.
Carla was incredibly sore, her bottom felt scalded and she longed to reach back and rub some sting away. Aurora was also thinking about rubbing a part of her anatomy, but despite her recent ordeal her mind was already in the gutter. Hearing Emily spanked had her mind running away, and her cage running a clear stream of precum. She felt a little guilty for enjoying it so much, but listening to Emily beg and apologize and whimper already had her incredibly worked up. She wondered if Carla had another toy stashed away somewhere…
Finally, after what felt like an eternity, the Headmaster gave the brush one last mighty swing before resting the brush on Emily’s back and letting her cry it out. It took more than two full minutes for Emily to stop squirming, begging, and kicking; for her mind to accept that her ordeal was truly over.
Broken, exhausted, and in a world of pain she sagged bonelessly over the Headmaster’s lap and sobbed without reservation or care. He released her wrist, and stroked her back gently, letting her get it all out. He knew how much punishments like these hurt, but he also knew that Emily, while a bit of a brat, almost never broke a serious rule. He hoped that such a stern punishment would mean it never had to be repeated.
He let her finish crying completely, laying limp across his lap, but his mind was already focused forward; onto the next step of the girls’ punishment.
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The Bathroom: Part Three
Emily wasn’t sure exactly how long the professor had been standing there, but it was very clear that he had seen enough for her to be in big trouble. She had been, quite intentionally, a million miles away in her head. Doing her absolute best to tune out the world around her and the rather ugly truth that she was spending all of her pocket money to cheat her chastity cage in a public bathroom, surrounded by gawking strangers.
The illusion was utterly shattered now, and her fingers went numb with shock, dropping the vibrator which chattered across the tiles next to the toilet, as though trying to escape. The thought of fleeing herself flashed through her mind, but the professor was between her and the door, and running would ultimately make things even worse. The bathroom door closed behind the last of her fleeing audience with a whisper of hydraulics from the transom closer and a gentle thump as the door met the frame, leaving her completely alone with the professor.
Trouble had a habit of following Emily around. She didn’t think of herself as a troublemaker, just frequently trouble-adjacent. It was seldom for anything too serious; a few minutes late to class here, a low mark on a quiz there, being caught in bed with a fellow student on a not-infrequent basis… Small time stuff, by the standards of the school. This was most certainly not small time stuff. This was breaking the Golden Rule: Good girls don’t cum.
Professor Anson seized her elbow, and pulled her off the toilet. Ignoring her apologies, begging, and pleas to at least let her have her panties back, he all but dragged her out of the room. Being marched across campus, naked from the waist down, cage exposed, and getting prodded sharply between the shoulder blades with a vibrator any time she so much as hesitated was a new and awful experience for her. Worse yet, every so often she could feel something wet and sticky drip onto her thigh meaning that her cage was slowly dripping out very obvious evidence of why she was in so much trouble.
Worst of all she knew exactly where they were headed. She had positively begged Professor Anson to deal with her punishment himself, however he wanted, but he was having no part of it. Break the Golden Rule, you answer to the Headmaster. No exceptions. Her face burned scarlet as her walk of shame took her across the central plaza and up to the administration building. Even in a school as strict as Rattangrove the sight of a student being marched half naked across campus was an extremely unusual sight. Emily tried not to notice the stares and gasps as they walked, but she saw as the other girls pulled into tight groups to whisper and laugh.
They went through the heavy wooden doors of the administration building and climbed the stairs to the third level, drawing ever closer to the Headmaster’s office. Professor Anson didn’t say a word to the Headmaster’s secretary as he entered the office. He placed the large vibrator on the desk, gestured at his ruined pants with a grimace, then turned on his heel and walked away. The secretary gave Emily a small smile, showing some sympathy for her plight, but sadly not enough to loan her some panties, or even a towel to wrap around her waist. The receptionist met Emily’s nervous gaze with a tired expression and her eyes flicked towards the hard wooden bench that lined the far wall. Emily took a seat, the polished wood of the bench cool against her bare skin, and awaited her fate. She knew it would be the last time she would be sitting comfortably for some time.
It was a long wait. At first, her wait was alone and in silence, with the tapping of the receptionist’s fingernails on the keyboard, the hum of the fluorescent lights, and her own nervous heartbeat her only company. After a time Professor Anson returned, this time with Carla and Aurora in tow. He leaned over the desk and held a whispered conversation with the receptionist, who glanced at the guilty-looking pair and coolly extended a finger towards the bench Emily sat upon. With a look of dread and resignation the two girls took a seat on the bench; Aurora beside Emily, and Carla beside Aurora. The three sat in uncomfortable silence. Emily knew that they had most certainly seen her without panties, but she still tried to hide her cage with her hands. With the new arrivals, the office was filled with nervous shuffling of feet, twisting of skirt hems, and a little bit of pre-punishment sniffling.
Fae was the last to arrive. Eyes downcast and mute, she tried to join the guilty trio on their bench, but instead was escorted straight into the Headmaster’s office. Emily caught the flash of panic in her eyes as she was lead inside and her own stomach twisted in fear and sympathy. The office was soundproofed well enough that she couldn’t hear any of the conversation between Fae, the Professor, and the Headmaster. Unfortunately, she could hear all too well when the talking ended and Fae’s punishment began. Fae was a very small girl but she had quite a set of lungs on her, and the sound of leather snapping deep into quivering flesh, as well as her crying, pleading and finally begging left all three of the waiting girls squirming in place.
Aurora in particular seemed to be in some discomfort, twisting and squirming on the hard wooden seat. At first Emily assumed it was just fear; her own bottom was tingling and itching in anticipation too. But Aurora’s flushed cheeks and glazed eyes led Emily to think it might be something more. Aurora all but confirmed her suspicions when she reached down and nudged the ring of her own cage through her skirt. It was a nearly unconscious motion that Emily herself had done hundreds of times: sliding the metal ring down to create a little extra “room to grow”. Emily smirked at the knowledge, but focused her eyes at her bare knees, not wanting to let on that she knew. The receptionist sighed and sipped her coffee; she had seen and heard all of this so many times before.
Eventually the snap of leather and the tearful apologies of a very sorry girl concluded, and Emily’s stomach sank. Her legs felt watery and her palms were slick with sweat, with no skirt to wipe them on. Looking over at Carla and Aurora, both were pale and trembling, Carla’s cocky assuredness had fled; she stared past the receptionist, awaiting her fate anxiously. It was a few agonizing moments more before Professor Anson came to collect the three of them together.
Emily had thought that between the bathroom, the march across campus, and waiting all but nude in the office had been enough public humiliation for one day. She had assumed that her punishment, however painful, would be a private affair between the Headmaster and herself. Unfortunately, she had thought wrong. The three girls were escorted in together. The Professor held the door open for the three of them, and having ushered them to their doom quietly excused himself, leaving them alone with the Headmaster.
The Headmaster’s office was surprisingly large, nearly the size of a classroom; with an imposing wooden desk and a trio of filing cabinets standing at one end of the room where the Headmaster worked. A pair of small chairs faced the desk, the seats oddly low to the ground so that nearly anyone, regardless of height, would be looking up at the Headmaster. The walls were adorned with professional certifications, class photos, sun-faded sports ribbons, and medals from tournaments long past. A pair of elegant leaded-glass windows allowed plenty of light into the room, with photographs and even paintings of earlier Headmasters going back over a century hanging in places of honour. However, it was the other end of the room that drew Emily’s eye.
Apart from a large fireplace, empty and cold with the unseasonably warm fall, as well as the red-bottomed and still crying figure of Fae cooling off her cherry red behind in the corner, this side of the room was surprisingly empty. While the rest of the office had the homey, lived-in look of a room that had served as the workspace and meeting room for well over a century of Headmasters, this side of the room was entirely utilitarian.
Apart from a leather-covered, thinly padded punishment bench, the room to the right of the doorway was empty, though dozens of corrective implements hung from brass hooks on all 3 walls. Paddles, whips, canes, brushes, tawses, quirts, and several painful-looking devices that Emily didn’t recognize hung in terrifying abundance on the wall. Some were clearly new, being PVC or Lexan, others looked as old as the school itself, their venerable wood darkening slowly over time, having been used to correct hundreds, if not thousands of wayward girls.
The Headmaster himself was indefinably middle-aged, with a wardrobe that ran from tweed to perhaps hound’s-tooth if he was feeling risqué. His clothes were well tailored and immaculate: neither a burr nor an errant thread could be seen, and his shoes were polished to a nearly perfect shine. He was tall, lean, scrupulously well-groomed, and dour. A strict man, he had never struck Emily as being spiteful or mean spirited, though she would never have described him as being particularly merciful. Emily figured he could have been anywhere from a tired-looking 45 right up to a sprightly 60. His face was largely unlined apart from well-defined crow’s feet around his eyes, his hair greying at the temples and flecked with silver throughout, though it retained the thickness of a man half his age.
He walked slowly, but there was no hesitation of waver to his movements and his back was perfectly straight. Every movement seemed deliberate, considered well in advance, and executed with precisely the amount of effort required and no more. Even his words seemed to have been carefully considered and weighed before he opened his mouth. Each one precisely chosen and given careful and deliberate inflection, never rushed or hurried; she had never once heard him stammer or trip over his words. He carried himself with an effortless authority and presence, felt even by very well-behaved girls who had never made a mistake large enough to be summoned to his office.
“So… Carla, Aurora….” His eyes narrowed as he turned to look in Emily’s direction, who quickly looked down at her toes, suddenly noticing a rather telltale stain on her right shoe. “…and Emily. I’m sure you all understand why we are here. Professor Anson informed me of his suspicions, all of which were confirmed by your classmate.” He motioned towards Fae, who bunched her shoulders and seemed to be trying to disappear. “After some thorough… motivation, she was quite willing to fill in any missing details.” He frowned and pointed to Carla and Aurora, crooking his finger to motion them forward; “Let’s begin with you two: Skirts and panties off, and lay over the bench, girls.”
Carla stepped forward before Aurora, who was momentarily rooted in place; she was lying over the bench, resigned to her fate, before Aurora even had her skirt off. It further confirmed to Emily that Carla was the mastermind, and Aurora decidedly the follower; she understood Aurora’s hesitance. Her own stomach was already in knots. Emily could see the pink steel ring of Aurora’s cage wrapped tightly around the base of her scrotum, and she found herself feeling a little sorry for the poor girl. Emily could fully understand the desperation that must have driven her to this. She was surprised to see a small drop of precum drip from the tip of her cage as she settled over the bench. Had she enjoyed hearing Fae being punished? Just how deep did her voyeurism run?
Carla on the other hand, not being trans, had no “intimate jewelry” to display as Aurora settled in beside her. Emily didn’t feel particularly sad about seeing her in this state; Carla was an opportunist and a bully, and while Emily had needed the relief that she could offer, she felt none of the empathy for her that she did for Aurora, whose motivations she understood. The Headmaster paid the pair no mind as they waited nervously in position over the bench. He seemed a world unto himself, walking up and down past his broad assortment of punishment tools. He appeared to be in no hurry, musing for a time in front of the canes, before selecting a particularly nasty looking black-painted cane from the wall and swishing it through the air several times, reminding himself of its weight and flex.
“So… smoking on campus, skipping class, not to mention running a black market in my school…” he listed off the offences with a detached air, walking behind the two trembling young women. Gently, with the very tip of the cane he tapped the steel ring of Aurora’s cage, and Emily could see her knees nearly buckle. “Very likely some other indiscretions as well, I should think. Impossible to prove at this time, sadly…” He paused, and brought the tip of the cane up to his face, thoughtfully. “I think two dozen strokes apiece should suffice. And Miss Aurora, I do believe that moving you over to a yellow cage is appropriate under the circumstances. Anything to say in your defence before we begin?”
His question hung in the air, neither of the girls daring to answer, though Emily suspected that Aurora had already begun to cry silently. They had both been very thoroughly caught in the act, and any attempts at justification were almost certainly a waste of breath. Besides, as bad as this was going to be for them, Emily strongly suspected that they were both very relieved that they weren’t in as much trouble as she was. The Headmaster smiled primly as he gave them a few more moments to squirm, not relishing their anxiety and humiliation, but understanding its necessity. Everything below the waist exposed, minds fully on both their actions and the consequences before he began their correction. Real learning, he felt, was happening right now.
Swish-CRACK! The first strike landed across Carla’s bottom from right to left, and it became immediately clear why they had heard so much of Fae’s punishment. The headmaster didn’t believe in a slow buildup, he went straight for a full-power strike right from the first swing. The impact with Carla’s bottom echoed like a gunshot in the enclosed space. Carla had been holding her breath and it burst out of her with the first strike of the cane, coming out as a rushing exhalation that pitched up into a simpering whine. Her body shuddered with shock and pain but her hands gripped the bench firmly, keeping herself in position.
The Headmaster did not move on to Aurora immediately, but focused his attention on Carla for the next five strokes. Each from right to left, striking backhanded across his body to land directly across both of Carla’s ample cheeks; the motion seemed effortless and fluid, so well-practiced was the Headmaster. Carla was sniffling after the very first blow and was openly crying after the sixth, but she held position.
“Very good, Carla,” the Headmaster intoned, his face stony, but with a tiny spark of encouraging warmth in his voice. “You held position quite well.” He turned to Aurora next, and tapped the cane across the centre of her bottom. Aurora let out a low mewl that wasn’t quite a whimper and wasn’t quite a mumbled apology just before the cane came down.
CRACK! The cane snapped down, left to right, clearly the preferred angle for the right-handed Headmaster. She wasn’t sure if he simply swung harder from this side, or whether Aurora had a lower pain tolerance than Carla, but the poor blonde girl was dancing on her toes from the very first swing. While Carla had taken her strokes as stoically as she could, Aurora danced and twitched, and squeaked out frantic apologies through hers. After the first set, both girls wore nearly identical six-stripe patterns across their bottoms, though they had taken them quite differently. Unfortunately, the Headmaster did not approve of a girl moving too much during a punishment.
SNAP! Aurora shrieked as an unexpected stroke fell across the tops of her thighs. Emily winced, knowing how much that had to hurt and her eyes opened in shock as she saw Aurora’s hand reach back in pain. Putting a hand back was a bad idea with any professor, but Emily would never have dared try it with the Headmaster. Emily gritted her teeth as the cane swung down again, the wood digging into the fleshiest part of Aurora’s palm. Aurora let out a broken yelp and drew her hand back, hiding it protectively against her chest.
“Do attempt to keep both feet on the floor for your punishment, and do NOT interfere. If you cannot remain in position, I will add extra strokes to your thighs. If you attempt to reach back again it will go very hard for you.” His words were gentle, barely scolding, but they carried a tremendous weight.
“You had an opportunity to defend yourself with words, which you declined with your silence. If you cannot defend yourself with words, you absolutely will not defend yourself with your hands.” He paused a moment for her to reflect before stepping back towards Carla. “It is entirely for your own safety Aurora, and if necessary, I will restrain you.”
His face remained impassive as always, but Emily swore she could see the shadow of a smile in the way his eyes crinkled when he was inspecting his handiwork, bright crimson lines freshly branded into the pale skin of both Carla and Aurora. Was he enjoying this? Or was it simply the pride of a master craftsman? Whatever the reason, the punishment continued: six stokes for Carla who bore them surprisingly stoically and then six for Aurora who didn’t take them nearly so well, back and forth until all 24 searing strokes were delivered. Aurora was a mess; she had earned an extra half dozen penalty strokes across the backs of her thighs, though to her credit she had not reached back again.
Finally, it was done. The Headmaster stepped back to let both girls cry it out. Carla’s bottom was a mess of hot red wheals; the lines cutting horizontally across the widest part of her bottom, right down to her sit-spot, occasionally crisscrossing each other, each crossing point a place where she would still feel it sharply tomorrow. Aurora’s bottom was in even worse shape. Her constant squirming and kicking meant that even the Headmaster’s experienced hand hadn’t been able to prevent nearly every stroke crossing at least one immensely sore red welt, and her upper thighs were marked with penalty strokes. Carla was sobbing, her shoulders moving rhythmically, broken and sagging over the bench; deeply relieved that it was over. Emily wasn’t sure Aurora even knew that it was over, as she was still repeating the same apology over and over in between her own ragged sobs.
Leaving the girls in position on the bench, and without giving them a second glance, the Headmaster pulled one of the small chairs from in front of his desk into the centre of the room. He motioned for Emily to stand next to the chair as he walked over to his collection of corrective implements. Emily walked to the patch of carpet she knew he would expect her to be standing on. From experience she knew he was right-handed, and that he would take her over his lap right-to-left.
She hated being over anyone’s lap, but especially that of the Headmaster. Certainly, it was humiliating as he could see everything in excruciating detail. She was also worried that there might be a little cum left in the tube, and she didn’t even want to think about what would happen if she ruined his pants as well. The far more pressing issue, however, was that Headmaster delivered the most severe punishments exclusively over his knee. For these most serious of corporal punishments he needed to be able to feel her every breath, squirm, shudder and kick, to hear every last whimper and cry, and to be able to see up close just how much more her poor bottom could take. She had been bent over his lap once before and it had been by far the most painful experience of her life. She was dreading what was coming next.
The Headmaster let her stew for another few minutes, finally selecting an oval ebony hairbrush from the wall. It was clearly an antique, small yet heavy, carved from a single piece of ebony, with fine and feathered boar’s hair bristles, and a beautifully lacquered finish that had yellowed with time. It had to be nearly as old as the school, and must have visited the scorched bottoms of dozens of girls before Emily. It was old, hard, heavy, and utterly unforgiving.
It would bite deep into the muscle, leaving behind an ache that would linger for days, giving the poor girl a reminder of her misbehaviour every time she sat down for nearly a week. As much as Emily saw it as a thing of dread, the Headmaster handled the brush with reverence. It was clearly a favourite of his, and he treated it as gently and carefully as a mother might a newborn child. He ran his thumb along the bristles, too brittle with age to be useful, and along the smooth wooden back, before bringing down into his palm with a resounding WHAP!
Satisfied with his selection, the Headmaster walked back to the chair and sat down. Emily saw no point in begging, or trying to explain, or even trying to run. She laid herself meekly over his lap, making sure that the cage lay between his thighs, for both of their comfort. She could feel his eyes on her as he used his fingertips to gently guide her hips to the precise position he wanted her, her bottom as high in the air as possible, her legs slightly apart. Her palms were flat on the floor, but the toes of her trainers barely touched the carpet.
She knew he could see everything; her bottom-hole, which she desperately hoped was perfectly clean, the ring of her cage candy pink against her pale skin, some errant leg hairs on the back of her thighs that she always seemed to miss when she shaved her legs. She was no stranger to being in this position, but she never stopped hating it. Finally satisfied with her position, he tapped the back of the brush gently against Emily’s bottom, eliciting a sharply inhaled breath, followed by a low and miserable whine.
“Do I even need to explain why this is necessary?” the Headmaster’s voice was ice cold.
“No S-Sir.” Emily tried to make her voice as apologetic as possible. She doubted it would make any difference at all, but she was willing to do almost anything if it meant even one less strike of that fearful brush onto her vulnerable posterior. “G-Good girls don’t cum. I b-broke the rule, and I’m very sorry, S-S-Sir.” She could feel the tears coming to her eyes as she said it, and she hated how obvious her fear was in the way she stammered. She was certain he could feel her shaking, her bottom perched high and vulnerable, and she was already truly, deeply sorry. That wouldn’t save her though.
“Precisely.” The Headmaster affirmed. “Your apology is accepted, though we still have some business to take care of first.” He paused, letting that statement take hold.
“You understand that you will be fitted with a red cage for the remainder of the semester.” It was a statement not a question, and Emily knew that it was beyond argument. Any attempt, even a failed attempt to cheat the Golden Rule meant the red cage for a first offence and the black cage for a second. Any girl foolish enough to get caught a third time was simply expelled.
Thankfully, this was a first offence, but those consequences were bad enough. She tried not to think about the lost monthly milkings or the more severe discipline that lay ahead any time she was caught for the smallest infraction; the present had its own pressing problems. She felt the Headmaster’s left hand press firmly into the small of her back, meaning the spanking was about to begin. She squeezed her eyes shut against the tears, gritted her teeth, and waited. She felt the cool wood of the brush tap against her right bottom cheek as the Headmaster reacquainted himself with the weight and feel of the cherished instrument of correction. Emily shuddered at the sensation.
CRACK! Emily’s breath exploded out of her as the first strike landed on her right cheek like a scalding brand. Emily had been spanked by a remarkably large number of people; from her parents, babysitters, teachers, coaches, and principals… the list went on. Nothing had hurt like this. The brush seemed to be made of molten iron as it came down for a matching strike on her left cheek. The tears that had accumulated nervously in the corners of her eyes raced down her cheeks and dripped down onto the carpet. The spanking had finally begun.
The Headmaster may have walked quite slowly, but he spanked hard and fast, with every swat designed to be felt not just in the moment, but for days afterwards. He could see exactly how dark and red Emily’s bottom was getting in real time, and he had decades of experience in administering this sort of correction. He knew the telltale white marks that showed that a particular piece of skin had taken all it could, and he moved the brush blister to places that could still take more. From the middle of her cheeks down to the middle of her thighs, the hairbrush did great and terrible work. Emily tried to keep position, knowing well from watching Aurora that struggling would only make things worse, but her bottom went from warm, to sore, to excruciating, to intolerable in what felt like seconds.
Emily had no way to count the time as it passed, or each stroke of the brush as it slammed into her body. They came too hard and too fast, and the pain did not plateau, but intensified with each moment. Soon she was drumming both her hands and feet on the floor and begging for the spanking to end, she would promise anything if the pain would just stop. For his own part, the Headmaster was glad that Emily was so petite, and when she inevitably reached back with her hand to interfere he had it pinned to her lower back in a trice. Now she could kick and struggle as hard as she wanted, but he was firmly in control.
Squirm and kick and struggle she did though, as with every few swats the pain reached new and wholly encompassing level of pain. There was no point in begging, but it didn’t stop her.
“No! Please stop…” her voice was cut off as WHAP! The brush hammered down into her right bottom cheek. Emily regretted everything. The cage, the school, the vibrator, her toy at home, everything.
“I’m so sorry! Please…” CRACK! The heavy polished wood swung down again, and the pain flowed deep into the muscle, and radiated back out. The pain was excruciating, and laid bare her innermost soul; blasting it pure and clean once more in its excoriating white heat.
Lying over the punishment bench, their own bottoms cooling slowly, Carla and Aurora could hear what was happening to Emily and even Carla was moved by the girl’s sobs and wails. Both of them had been over the Headmaster’s lap themselves, Carla once and Aurora twice, and both knew how terrible an experience it was. Listening to their classmate be so thoroughly chastised made their hearts sink, and both were deeply relieved that it was her and not them in that position.
Carla was incredibly sore, her bottom felt scalded and she longed to reach back and rub some sting away. Aurora was also thinking about rubbing a part of her anatomy, but despite her recent ordeal her mind was already in the gutter. Hearing Emily spanked had her mind running away, and her cage running a clear stream of precum. She felt a little guilty for enjoying it so much, but listening to Emily beg and apologize and whimper already had her incredibly worked up. She wondered if Carla had another toy stashed away somewhere…
Finally, after what felt like an eternity, the Headmaster gave the brush one last mighty swing before resting the brush on Emily’s back and letting her cry it out. It took more than two full minutes for Emily to stop squirming, begging, and kicking; for her mind to accept that her ordeal was truly over.
Broken, exhausted, and in a world of pain she sagged bonelessly over the Headmaster’s lap and sobbed without reservation or care. He released her wrist, and stroked her back gently, letting her get it all out. He knew how much punishments like these hurt, but he also knew that Emily, while a bit of a brat, almost never broke a serious rule. He hoped that such a stern punishment would mean it never had to be repeated.
He let her finish crying completely, laying limp across his lap, but his mind was already focused forward; onto the next step of the girls’ punishment.