Breaking the Rules

By Flatfish

Antonia Woodfield, Toni to her friends, wound down the window of her Mini and blew a cloud of pale smoke out into the late evening air. The school carpark was almost empty. All the students and the rest of the teaching staff had gone. She knew smoking in the school grounds was forbidden but what the hell, who was going to know. Rules are for fools, she thought. She smirked and took another pull on her cigarette.

She had only worked at the school for just over half a term and it was her first teaching post. A few weeks earlier she had still been a rebellious college student, always at the centre of any protests and demonstrations. She loved to be anti-establishment. Four years before that she’d been a pupil herself, a troublesome brat at another of the city’s former comprehensives, now turned into a struggling academy. So it was ironic that in the end she had chosen a career as a teacher, a job that lived and breathed rules. And of all the schools in the city, she had landed a job here, at this school, where the headmaster, Mr. Cox, governed with an iron grip. He had laid down strict rules for the students and equally strict "guidelines" for the staff - don't be late, don't smoke, dress as follows blah blah blah. Toni grinned and blew another grey cloud out of the window.

In the few weeks since starting at the school, Toni had built up quite a backlog of unmarked assignments. Some she’d had for a month despite staff guidelines stating that assignments should be returned to students within a fortnight, and this was the reason she was sitting in the carpark at this late hour. She had needed to force herself to stay back after school and catch up; a sort of self-imposed detention.  And with much of the wearisome task now done she had been happy to finally climb into her car and reward herself with a relaxing smoke. She put the cigarette between her lips and reached down to turn on the ignition then stopped. Better call Alison, she thought. Alison, her "very sensible" flatmate had been the one who had pushed her into staying late to sort out her marking. She had promised to prepare something good to eat when the job was done. Toni dipped into her purse for her phone.

“Damn it!” she muttered. Earlier in the day she had taken her mobile with her when she had slipped out of school at lunch time. Careless of the time she had just managed to rush back to her classroom as the afternoon lesson bell rang and she hadn’t had chance to return to the staffroom for her bag. And then, conscious of the possibility that the latest iPhone might tempt a light fingered student, she had locked the phone in the bottom drawer of her desk - and that’s where it was now, back in the classroom.

With an exasperated sigh she pushed open the car door and swung her shapely legs out taking care not to catch her high heels. She hitched up her black stretch jeans and headed back towards the school. Toni was an attractive twenty two year old, five foot five, slim yet curvy with pretty features and long straight dark hair. In her brief time at the school she had already become the source of many teenage fantasies. She zipped up her short leather jacket as protection against the cold November breeze and with her cigarette held between her elegant fingers she hurried across the carpark.

At this time in the evening most of the school buildings were in darkness or economy lighting but if Toni had been paying attention she might have noticed that the Headmaster’s office was still fully illuminated, and if she had noticed then she would have stubbed out her cigarette before swiping her access card and entering the school.

Harold Cox, the sixty two year old Headmaster, heard the staccato clip of Toni’s footsteps as she passed his office but that wasn’t what grabbed his attention, it was the unmistakable smell of cigarette smoke. He stopped writing and frowned. He replaced the cap on his fountain pen. Surely no one would have the nerve to smoke in his school.

Cox left his office and sniffed the air, there was no mistake, someone was in deep trouble. He angrily turned and marched down the corridor, following the invisible smoke trail. When he came to Toni’s classroom the light was on and the door was wide open and he knew he had found the culprit. He entered the classroom and stopped. Toni had her back to him, or more accurately, her delightful backside. She was stretching over her chair with one hand holding the chair arm and the other grabbing the phone from the lower drawer at the far side of her desk. The temptation to slap her hard on the bottom was almost unbearable, especially when he noticed she was wearing jeans - another flagrant defiance of the staff rules. But with steely determination he resisted and brought his anger under control. He coughed quietly.

Toni nearly jumped out of her skin. She scrambled upright, spinning around quickly, and hid the cigarette behind her back, an automatic reflex from her teenage past; it was too little too late.

“Mr Cox!” she squeaked.

 “Miss Woodfield,” said the Headmaster with a disappointed shake of his Head. “I should have known. Smoking! Yet another blatant disregard of the school rules.”

Toni’s cheeks flushed. She nibbled her bottom lip nervously and studied her shoes, unsure what to say. She hadn’t been aware that the Headmaster had been keeping an eye on her behaviour; she might not have been quite so laissez-faire with the rules if she had known.

“Extinguish that cigarette at once Miss Woodfield,” he snapped, “and report to my office. We will be having words.” He turned and marched away, knowing full well the impact his words would have. It was an approach he had been taking with children for years and it would work just as effectively with this badly behaved young teacher.

A lead weight hung in Toni’s stomach as she made her way to the Headmaster’s office, conscious that this was her probationary year and her place at the school was not yet secure. You stupid, stupid, idiot, she thought, four years of study to become a teacher, just thrown away because of a bloody cigarette.

When she arrived at Mr Cox’s office the door was closed. She paused for a moment, not daring to enter then gathering her courage she timidly knocked.

“Come in,” came the gruff reply.

Trembling, Toni pushed the door open and stepped inside.

“Take a seat,” said Cox, not even taking the trouble to look up from the document he was studying.

Toni sat down and waited… and waited. Eventually the Headmaster closed the file and slipped it into a drawer. Then he stared hard into Toni’s eyes. Toni looked away, she didn’t know if she was expected to speak first. Her mind raced, searching fruitlessly for any excuse she could offer for her behaviour.

When Cox began his lecture his tone made it clear that he was furious. “Smoking, Miss Woodfield, as I’m sure you are aware, is extremely bad for your health.”

“Yes Sir,” said Toni.

Neither Toni nor the Head seemed to notice that she had started calling him “Sir”. It wasn’t the normal way for a teacher to address the Head but Cox was used to it from his pupils and because she was so intimidated Toni had automatically dropped into a contrite naughty schoolgirl mentality.

“And it is a very serious breach of the school rules,” Cox continued.

“Y… Yes Sir,”

“It presents a very poor example to the children and you are supposed to be a role model.”

“B… But Sir, there were no…” Toni didn’t finish. The look on the Headmaster’s face was enough to let her know that this was not the time to argue even if all the kids had gone home.

“And furthermore, young lady,” said Cox, raising his voice angrily, “by smoking in a public building you were breaking the law! Are you starting to appreciate just how much trouble you are in? Let’s face it Miss Woodfield, this school relies on the cooperation of students and staff to obey the school rules but since you arrived here you have committed one infraction after another and this time you have gone way too far. I am going to have to raise this with the board of governors and I really think, on top of everything else, this could mark the end of your teaching career. ”

“Oh no Sir, please! I won’t do it again.”

“I’m quite sure you won’t but the damage is already done; the offence already committed. You were smoking in your classroom. This final affront to my authority and total disrespect for the school and its values is something that can’t be ignored. This sort of behaviour cannot be allowed to continue.”

“But please don’t fire me,” Toni begged. “I’m really sorry. Isn’t there another way? I’ll agree to anything but please don’t report this to the governors.”

Toni looked like she was going to burst into tears but the Head was resolute. She was not going to get away with this. She had crossed way over the line and he was determined to teach her a lesson she wouldn't forget. He thought back to earlier and the sight of Toni bending over the chair in her classroom and how he had felt like spanking her there and then. He was just as furious now. His mind raced through the arguments as he fought with himself. It really would be a shame to end this girl’s fledgling career, despite her frequent bad behaviour, and she did say she’d agree to anything. But surly he couldn’t… could he... a paddling or maybe even a spanking?

Cox made a decision. It would mean putting his own career at risk just by making the offer but he was willing to take that chance.  Miss Woodfield really needed a serious attitude adjustment, one that would leave her unable to sit down. He opened a desk drawer and pulled out an old school paddle; fifteen inches of punishing polished hardwood. “Do you know what this is?” he asked.

Toni paled as she realised where this conversation was going. She nodded and swallowed nervously. “Y… yes sir,” she said, “but surely you can’t be thinking… I mean I’m an adult, a teacher, I’m not a pupil. And even if I was its illegal isn’t it?”

“I bought this many years ago while on holiday in the USA,” said Cox. “It’s a genuine American school punishment paddle. It served me well in the past but sadly you are correct, since the government’s ban on corporal punishment it has been reduced to nothing more than a historical curiosity. But it occurs to me that there is one context in which it could still fulfil its original purpose and that would be if it was used to punish a consenting young adult; an adult who has been behaving like a spoiled child.” Cox looked at Toni and raised his eyebrows.”

Toni’s eyes opened wide. “No Sir… No way! I… I could never submit to … to… that.”

“I see,” snapped the Head. “So you think you can behave how you like, breaking rules, breaking the law but you don’t think you should be punished when you are caught.”

“No Sir I’m not saying that, but…”

“So you agree you should be punished?”

“Yes, I suppose but… but…”

“Well I think you are absolutely right. I believe you said you would agree to anything to save your career.” Cox patted the paddle fondly.  “Well we can do as you wish, avoid involving the school governors and settle this matter here and now. I’ll fetch the punishment book.”

Toni was stunned. What… what just happened? Had she agreed to this? Cox pulled a dusty red book from a nearby bookshelf and put it on the desk. He opened it up and Toni could see it was set out like a guest book with columns of hand written text. Cox turned the book around and pushed it over to Toni and she could read what had been written. The columns were headed date, name, offense, punishment, signature and teacher. It hadn’t been used for decades but in its day corporal punishment had apparently happened very frequently. Toni noticed Mr Cox had been dishing out between one and four swats of the paddle. She started to think the idea wasn’t so crazy. If she could swallow the horrendous humiliation then how bad could it be? Three or four swats, it should be over in seconds. Surely that had to be better than being hauled over the coals and fired.

Cox offered her a pen and she frowned, puzzled.

“Surely you don’t expect me to write my punishment in this book. What if someone reads it?”

“I can assure you that no one is going to read this book,” the Headmaster answered. “The book is for my personal records. It will be of no use to my successor when I retire next year and I will be taking it with me. But for now it will serve as a contract between us; evidence of your agreement and reassurance for you that your punishment will only extend as far as that written in the book.”

Toni took the pen and with a trembling hand and butterflies in her stomach she wrote the date and printed her name ‘Antonia Woodfield’. She looked at Cox and he dictated “Offense is Smoking in the classroom, flagrant disregard of the dress code and frequent flouting of school rules.” Toni wrote in the offenses, cringing at the reference to the dress code; she thought she had got away with wearing black jeans in place of the permitted tailored trousers. “Punishment,” said Cox, “needs to reflect the seriousness of the offences and also to take account of the fact that you are an adult. Put three…”

Toni breathed a sigh of relief but it quickly turned to a gasp of shocked disbelief as the Headmaster continued.

“…dozen with the paddle.”

“You’re not serious,” said Toni. She had never been paddled, in fact she had never even been spanked, but thirty six sounded like a hell of a lot and it was way more than anyone else in the book had received.

“I believe three dozen would be appropriate,” said Cox, “to save your career.”

Now feeling very conscious of her bottom and worried about what she was agreeing to, Toni reluctantly wrote the words and signed the entry.

Cox checked and closed the book and put it back in its place on the shelf. Returning to his desk, he picked up the paddle and tapped it against his hand. “Please move your chair out of the way, remove your jacket and bend over the desk.

Toni’s legs felt weak as she stood. She moved the chair over to the side wall, removed her jacket and laid it across the seat and then she returned and placed her palms on the desk.

“I’m afraid that won’t do,” said the Head.

Toni gave Cox a worried glance but she lowered her forearms onto the desk and adjusted her stance, stretching her jeans even tighter; she had never felt so vulnerable. Cox patted the paddle against her bottom, positioning himself for a good swing.

He had never paddled an adult but this girl had really earned it and he saw no reason to restrain himself. It was only fair that she should feel the full force of his anger.  So taking careful aim on Toni’s sit spot, he drew back the paddle and whacked hard! 

“Jeeeezzzzzzz”, Toni hissed through gritted teeth as pain flared across both cheeks. The Headmaster gave her a few seconds to fully appreciate the eye watering sting before swinging back his arm and delivering second and third even harder swats in rapid succession to exactly the same place. If Toni thought the first swat had been a stinger, she knew now there was much, much worse to come. Tears sprang from her eyes and dripped onto the desk. Her bottom was stinging and throbbing at the same time and after only three she didn’t know how much more she could take without bawling like a baby. Before she could recover, the fourth and fifth whacks seared across her bottom increasing the pain yet again and she cried out and started to blub. Cox gave her a moment and allowed her to reach back and briefly rub her bottom. She managed to choke back her sobs and brace herself ready for the next smack but she knew for sure she would never be able to take the full three dozen.

Cox was surprised and a little disappointed that Toni had managed to stay in position for five. He wondered if he was losing his touch. It had been many years since he had paddled anyone but he reflected that he had stayed fit over the years. He could still give a good performance on the squash courts and his forehand smash in tennis still had plenty of power. Maybe it was time to direct that power to the seat of the wayward Miss Woodfield’s tight jeans. He took a step back, swung back the paddle and powering from the shoulder he delivered an almighty thwack that cracked round the room and down the corridor like a pistol shot. Toni howled and leapt to her feet clutching her bottom. The sting was unbearable.

“Oh my god! Oh my god!” she yelled, pacing about frantically. “Fuck, fuck, fuck.”

The pain just wouldn’t let up and in desperation, oblivious to the shocked look on the Head’s face Toni unfastened her jeans and wriggled them down below her bottom cheeks revealing deep-red plump flesh peeping from white cotton panties. Releasing the pressure of the tight jeans seemed to help and she slipped her hands down the back of her panties to cool her burning hot skin.

As Toni regained her composure the Head realised that here was an opportunity to deliver an even more personally gratifying punishment to the girl who thought so little of his school rules.

“Well Miss Woodfield, I don’t believe six of the best is anywhere near sufficient punishment for your transgressions, do you? I think you had better pull up your jeans and return at once to your position over the desk, or perhaps you would prefer to leave your jeans around your knees and take your remaining punishment as you are.”

“No… no… I can’t. I can’t take anymore. It hurts too much. Please, haven’t you done enough?”

“You’re attitude reminds me of my daughter’s when she was a teenager,” said the Head with a sigh, “and to be honest, if she had behaved the way you do I wouldn’t have used the paddle to punish her. She would have felt the weight of my hand.”

Toni knew she couldn’t take anymore from that damned paddle so she proposed a compromise. “Maybe we could agree not to use the paddle then Mr Cox,” she said pleadingly, still rubbing and squeezing her bottom. I’ll go back over the desk and I’ll leave my jeans down if you wish and you can give me the rest of the smacks as we agreed but just use your hand.”

“No, I’m afraid you have misunderstood, Miss Woodfield,” said Cox. “When I said I would have used my hand I didn’t mean over the desk, I meant I would have put my daughter over my knee and spanked her. If you are asking me to treat you the same way then I will agree but a spanking may not be quite the reprieve that you seem to think. For one thing it will be hard and it will be for an indeterminate length of time. And furthermore, and I think this may come as a shock; it will be on your bare bottom. Is that really what you want?”

“On… on my bare bottom? Are you serious?

“Absolutely serious Miss Woodfield, so if you’d rather preserve what’s left of your modesty and dignity then…” Cox pointed at the desk with the paddle and gave a couple of practice swings like a keen golfer perfecting his stroke.

Toni’s hopes were dashed. She knew she was trapped. Accept the official penalty for her actions and possibly lose her career, bend over the desk again and be thrashed mercilessly with that bloody wooden paddle or be put over the Headmaster’s knee with her pants pulled down to be spanked like a naughty teenager, no good options at all – how the hell did she get into this mess.

Half an hour earlier the prospect of allowing her boss to see her bare bottom, let alone spank it, would have been unthinkable but now she was already halfway there. She was standing in front of the Headmaster practically in her underwear and with her bottom stinging like hell after allowing him to paddle her.  Defeated, she stared at the floor and mumbled her reply. “I… I’ll have the spanking.” She said.

Cox suppressed a smile. He placed the paddle on the desk and changed the entry in the punishment book to six swats of the paddle plus a spanking. He retrieved the chair from the side wall, removed Toni’s jacket and sat down. “Come here,” he said sternly.

Toni shuffled to his side and looked with trepidation at his waiting lap. After a little hesitation she lowered herself reluctantly over his knee. Cox helped her adjust her position until her bottom was over his right leg and her feet were off the floor. Then he grabbed the waistband of her knickers and yanked them over her sore bottom and down her thighs. 

Cox looked down at Toni’s beautiful round naked bottom. The effect of the paddle was clearly visible. He took a firm grip on her waist and raised his hand.

Toni, red faced with the excruciating humiliation, squeezed her eyes shut and gritted her teeth.

“Now young lady,” said cox, “there have been many occasions in my long career when I have had to deal with a persistent offender but I have never encountered a member of staff with such a comprehensive disregard of the school rules. Your behaviour has been childish and irresponsible and it will give me a great deal of satisfaction to finally be able to deal with you in the manner that you so richly deserve. You are going to learn that there are consequences for failing to obey the school rules because I am going to spank you until you can’t sit down for a week.”

Toni had barely a moment to wonder if she had made the wrong decision before the spanking was unleashed savagely upon her sore naked bottom.

Cox was almost as good as his word. He smacked and whacked mercilessly. Toni howled, kicked and cried. She tried to reach back and cover her bottom but Cox just moved her hand away and continued. Toni’s lower cheeks which had suffered most from the paddling immediately reignited into searing fire and the rest of her bottom stung and reddened more and more with every smack. Toni wriggled and writhed but she could do nothing to deflect the unbearable sting of the Headmaster’s anger. Cox lectured her as he smacked, often driving home his words with extra hard slaps. On two occasions Toni thought the punishment was ending but Cox had only paused briefly before bringing up some new rule infraction and spanking on with renewed fury. 

By the time the punishment finally came to an end Cox’s anger was satiated and Toni just lay over his knee bawling. The Head tugged Toni’s panties back up as much as he could and helped her to her feet. She choked back her sobs and reached back with trembling hands to gently stroke her bottom before painfully dragging her tight jeans over her stinging cheeks.

The Head handed Toni her jacket. “The rules in this school are to be obeyed,” he said. “I hope I have made that clear.”

“Yes sir,”  sniffed Toni tearfully.

Cox took her by the arm and guided her towards the door, resisting the temptation to help her on her way with a well-placed slap.


The drive home was torture. Toni’s bottom was burning like a furnace and her mind was a maelstrom of confused emotions. The Headmaster had dealt with her as though she was a disobedient child; completely taking away her control by pinning her over his knee so firmly she couldn’t possibly escape and leaving her no choice but to take her bottom blistering punishment until he was satisfied that she had learned her lesson. She should be furious so where was her resentment? Where was her anger? Why did she feel it had been something she really needed and thoroughly deserved?

Toni’s father had disappeared before she was born and she had been raised as an only child by a mother who had never really embraced the responsibilities of parenthood. Where her playmates had rules and guidance she always had complete freedom and a sense of abandonment. Initially envious of other children and feeling that no one cared about her, she had eventually turned her resentment into a rebellious contempt for rules.  But deep inside there had always been an empty space where a lost little girl needed to feel that someone was there to guide her in the right direction. And now someone was finally fulfilling that role. Mr Cox cared about rules, cared about the school and cared about Toni and her bad behaviour. That spanking had been pure hell. It had been inappropriate and wrong but far from hating Mr Cox, the punishment had left her with a strange sense of respect and maybe even gratitude.

When Toni arrived home she immediately eased down her jeans and slowly lowered her tender bottom onto a soft cushion then she excitedly poured out the whole story to Alison. Alison was incensed with the Headmaster and Toni spent the rest of the evening persuading her not to call the police.


The next day a cold November fog hung over the school. Mr Cox sat in his office mulling over the evenings events. He was troubled. It wasn’t that he was concerned about anyone finding out what had gone on. He was sure Miss Woodfield would be discreet and would not want the incident to become public knowledge. But he knew he had gone way over the top in punishing the young teacher. He had allowed weeks of growing anger to drive his actions. A written warning would have been sufficient, but a spanking? Was he insane? Had he really put a member of staff over his knee, pulled down her knickers and smacked her bare bottom until she couldn’t sit down? He knew he shouldn’t have done it but he couldn’t deny it had been very, very satisfying. He suppressed a smile and massaged the palm of his hand which was actually quite bruised. But what was really troubling Cox was the effect that spanking might have had on Miss Woodfield’s personality? Had he crushed her spirit and individuality? Would he lose those fresh innovative ideas that made her a valuable asset to the school? Could it be that her persistent naughtiness was really an essential part of what made her who she was.

He needn’t have worried. There was a quiet knock at the door and Toni entered. She was dressed in a brightly patterned sleeveless mini-dress and opaque black tights. The dress was inappropriately short and Cox looked her up and down and immediately wondered if the spanking of the night before had actually made any impression at all.

“Miss Woodfield,” said Cox, “erh… shouldn’t you be with your class right now taking morning registration?”

“Yes, yes, I’ll be there in a moment,” she said dismissively, “but I needed to see you Mr Cox. I’m trying really hard to obey your rules and I’m even trying to give up smoking, but I need to know what will happen if I fail?”

“If you fail to obey the rules?”

“Yes. I… I’ve been breaking rules all my life. I don’t know if I can change overnight but I don’t want to lose my job.”

“Miss Woodfield,” said Cox quietly, “are you asking me to spank you again if you break the rules?”

Toni blushed.

“Very well young lady,” said Cox. “This has to be strictly between you and I but if I ever catch you breaking the rules again then your name will go straight into the punishment book. Have I made myself clear?”

“Y… Yes Sir,” said Toni with a hesitant smile. Just hearing the Head’s stern words had sent butterflies through her stomach and had made her still sore bottom smart.

“Good,” said Cox standing up and reaching for the red book. “Then I suggest you go to your classroom immediately and do your job before I find my pen.”

Toni’s eyes open wide in panic. “I’m going, I’m going,” she squealed. “I'm sorry; please don’t put my name in the book.” She spun around and scampered from the room.

Cox smiled and rubbed his palm again.

Toni hurried down the corridor to morning registration. Rules are for fools, she thought with a grin but maybe I’d better try and follow them… at least for now.