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A Headmistress’s Dilemma

Hannah sat back in her comfortable armchair in the sixth form common room with a smile on her face. Two of her colleagues, Sophia and David, were revising, and Sophia looked up.

“Come on then. Tell us. What’s amusing you?”

“I’ve had a fun lunch hour. I gave Celine Masters a good spanking.”

“And that’s fun is it?” asked David. “I thought you had a good relationship with Masters. Isn’t she a member of your swimming club?”

“Yes. We get on very well. I think secretly she has the hots for me. Not so sure now, though. Her face was a picture when I told her that I was going to spank her. She thought I was joking and then it dawned on her I was serious.”

“So what got her the spanking?” asked Sophia.

“Dropping litter.”

“You can’t spank a student for dropping litter,” pronounced David.

“She was walking along the path outside the library and a sweet paper packet fell out of her pocket. Mrs Blackburn was following her and shouted out to her, ‘Pick that litter up, girl!’”

“She picked it up, but then, when Mrs Blackburn had moved on, she not only threw it down but emptied her pockets of other sweet paper wrappings and tossed them onto the floor. Showing off in front of her mates and a couple of boys. Very disrespectful to Mrs Blackburn. I saw what happened. I let her walk on a bit then I caught her up.”

“I said, ‘Hello Celine.’ Her cheeky little face lit up when she saw it was me. ‘I have something I need to discuss with you. Tomorrow lunchtime. Meet me at the stockroom at 1 o’clock. You know where that is don’t you?’”

Hannah explained to her audience, “I’m helping Mrs Bradshaw reorganise the stockroom and so I have the key. It was the ideal place to have a discrete chat. I can’t imagine why Celine thought I wanted her, but she seemed quite keen. Anyway, sure enough, she turned up dead on time at 1 o’clock this lunchtime. I was waiting for her. She knocked on the door and I let her in. She had a definite look of anticipation.”

“Where is this story going Hannah? I’m not sure I like the sound of it,” exclaimed David.

“Shush, David. Let’s hear what happened next,” said Sophia.

Hannah continued. “Celine’s face changed from cheeky smiley to slightly uncomfortable when I raised the subject of her dropping litter yesterday lunchtime. I told her that I watched her deliberately throw litter on the pavement in defiance of Mrs Blackburn and what did she have say for himself.

“The best she could come up with was, ‘Sorry, I shouldn’t have done that. Are you going to give me a detention for throwing litter?’

“But it’s worse than throwing litter isn’t it Celine? You were showing disrespect to a teacher in front of your fellow students, I said.

“She started to look distinctly uneasy and became rather fidgety, and I was enjoying her discomfort. I told her that I had asked her to come to the stockroom because I wanted to spank her in private, thinking she would prefer that to getting a spanking in the sixth form room in front of sixth formers.”

David once again interrupted. “Hannah, this is out of order. You know that prefect spankings have to be verified and witnessed by Angela, the head girl.”

“So what happened next?” asked Sophia, who had now put down her revision notes and was listening intently.

Hannah continued. “Celine. I’m sorry but I am going to have to spank you.”

“She said, ‘But Hannah. We really get on. I help you at the swimming club. I like you. We are friends.’”

“And I like you Celine, but you have behaved badly. I saw what you did and so I have to act. I need you to lower your trousers, bend over the chair and prepare yourself for a spanking. Let’s get this done and then we can be friends again.”

David yet again interrupted. “This is getting worse. You know prefects can only spank over clothed bottoms in front of the head girl. Tell me this didn’t happen.”

“Oh it happened all right. She looked really flustered. I stood up and reached for a leather two-ply strap which I had found when I was cataloguing the books for Mrs Bradshaw. There’s a load of junk in that storeroom including some old canes and straps.”

“Wait a minute,” said David. “You said ‘spanking’ which I thought meant using your hand. What’s this leather strap? You surely didn’t use an implement on Celine’s bottom?”

Even the more broad-minded Sophia looked aghast. But she was intrigued and wanted to know the outcome.

“Go on then. What happened next?”

Hannah enthusiastically continued with her tale.

“She took down her trousers but refused to lower her knickers, so when she bent over the chair I pulled them down. She jumped to her feet and protested, saying it was too embarrassing. I explained I had seen her naked many times in the showers after swimming, so what was her problem? Reluctantly she complied. She has a really peachy bum. Not so much now.”

“How did she take it?” inquired Sophia.

“Very noisily at first, and I had to tell her to quiet down otherwise we might attract attention.”

“I can’t listen to any more of this,” said David. “You are so out of order. Just how many strokes did you land on her.”

“About ten. I lost count. That strap makes a great sound especially in the confines of the storeroom.”

“My God, Hannah!” declared Sophia. “You’ve broken so many rules. The most us prefects can dish out is four slaps over clothing. You’ve exceeded what even the headmistress gives out on a bad day. What did Masters say? How was she?”

“She was okay. Cried a bit, but she tidied herself up. I asked her if we were still friends and she said yes. I gave her a hug and sent her on her way.”

“Unbelievable. Tell me you are just relating one of your fantasies,” challenged David.

Sophia said, “You would be in big trouble if Celine says anything. And if I were you I wouldn’t tell this to anyone else. If Angela gets to hear, God knows what would happen.”

“Celine won’t say anything. Too embarrassed and she likes me,” said Hannah confidently.

The three of them went their different ways to afternoon lessons.

****

Monday lunchtime, and head girl, Angela, entered the girls’ sixth form common room.

“Hannah, can you come with me please? The headmistress wants to see you immediately.”

Hannah stood up, appearing slightly concerned, and, without looking at her colleagues, followed Angela. David and Sophia looked at each other. They were worried for their friend.

“What’s that about, I wonder?” asked Kevin, another sixth for student.

“Don’t know,” lied Sophia. “You know Hannah. Always up to something.”

Over the weekend, Hannah had reflected on her stockroom activity. She came to the inevitable conclusion that she had got carried away and her behaviour was totally unacceptable. If she was challenged, she would be honest and take the consequences.

Angela was giving nothing away on the walk to the headmistress’s office.

Janet Hurst was a young headmistress with excellent career prospects. Recently appointed as a result of some excellent work at a school in a deprived area, she was held in high esteem by the local education authority, her teaching staff and the pupils. She came across as an even-tempered, kind and caring person and inspired all those around her.

“Hannah, this morning I was confronted with a very angry Mrs Masters and her daughter, Celine. She made me take a look at her daughter’s badly bruised bottom. Any comment?”

Hannah shuffled uneasily and avoided the icy glare of her headmistress, instead carrying out a concentrated study of the carpet.

“Yes Miss, I behaved inappropriately towards Celine during Friday lunchtime.”

Hannah related the whole episode as honestly as she could and, when she had finished, Mrs Hurst thanked her for her honesty. For the next ten minutes the headmistress, calmly and without raising her voice, talked through her disbelief and anger, and ending up by explaining the steps she was going to have to take to avoid Mrs Masters going to her local councillor and the Education Department, not to mention the press or even the Police.

“I managed to convince her to drop the idea of you being expelled. But she wants you to be thrashed and I have agreed to this. She wants to witness the thrashing and I am trying to dissuade her from this. I have also decided that you will be stripped of your prefects badge and lose all privileges, including use of the sixth form room. I would have expelled you but I do not want to deny you the opportunity to take you’re A-levels and get to university.”

“I accept I’ve made a mistake,” Hannah replied. “I understand why you need to punish me and thank you for not expelling me. Can I ask the extent of my thrashing?”

“Here I have a dilemma. This leather strap that you used. I have never heard of it. Where did you get it from?”

“It was in the stockroom, Miss, along with some old canes.”

“It certainly made a mess of Celine Masters’ bottom. I think it would be appropriate for me to use it on you. Where is it now?”

“Still in the stockroom, Miss.”

“Angela?” Mrs Hurst turned to her head girl who had endured the last few minutes open-mouthed. “Please retrieve this strap and bring it to me.”

“You will need this key,” said Hannah, and she gave the stockroom key to Angela.

“Okay, Hannah. You will hand over your prefects badge to Angela. She will escort you back to the sixth form room where you will collect your belongings and you will be allocated a fifth form locker in which to put your belongings. You will now reside with the fifth formers. You are immediately stripped of the captaincy of the swimming team and you are barred from the swimming club, which will be unfortunate for several of our young swimmers. I will announce your new status to the school at tomorrow’s assembly. I will send for you to discuss your punishment, which will be severe.”

Hannah remained calm and made no effort to appeal for clemency. Although she was fearful of the forthcoming physical punishment, the loss of privileges and separation from her friends was difficult to accept, but she was grateful not to be facing expulsion.

“You may go now, Hannah. You have a lot to process and the next few days are going to be difficult for you at a time when you need to be concentrating on revision for your exams. You will need to be strong. You may not think it, but I want to support you as best I can.”

p>Mrs Hurst walked into her secretary’s office. Kate Schofield had given much needed support to the young headmistress, who was grateful for the help and advice freely offered, and the two women had developed a friendship.

“Strange request, Kate. Can you search out the old punishment registers? I want to get some information on when the strap was last used. Have you any ideas?”

“I’ve been here eight years and it has never been used in my time, but I do know that Mr Rochester used it before I was appointed. I do recall seeing references to it in an old punishment register. I’ll search it out.”

****

Mrs Hurst sat holding the strap that Angela had brought to her. The leather strap itself was black, supple and bendy, and was about 15 inches long, just less than 2 inches wide, and about 1/4 inch thick. It was attached to a polished wooden handle with a leather loop drilled through, presumably to hang it on the wall. She swished it gently backwards and forwards and wondered how much it would hurt compared with the cane. She had never received physical punishment as a schoolgirl other than an occasional slap on her legs, and as a headmistress she had only ever used the cane or slipper.

Kate arrived with two old punishment registers.

“I’ve done some research and the strap was last used ten years ago by Mr Rochester. He administered twelve what were called licks to a boy for bullying. After that, he never used the strap.”

“What was the average number of licks?” asked the headmistress.

Kate looked up and down the pages.

“I reckon five or six. I’ve only seen the one at twelve. Well, would you believe it?” Kate chuckled. “My brother, Mark, is recorded here with three licks for not bringing his sports kit on three occasions. He hated sport. Naughty boy. He kept that quiet.”

“I’m just wondering what causes the most pain. Would twelve licks of the strap be the equivalent of six strokes of the cane? Mrs Masters is keen that the strap is applied,” pondered the Headmistress. “She wants to see Hannah’s bottom finishing up looking the same as Celine’s.”

“Well, from my experience as a schoolgirl, I preferred the classroom slipper to the headmaster’s cane, which I once received, but I guess it depends on the strength applied,” suggested Kate.

Mrs Hurst then made a request.

“Kate, you wouldn’t bend over the table and let me give you just one swat with this strap, would you?”

“Really, Janet?” Kate was taken by surprise. “You’re not serious are you?”

“I just want to get a feel for this thing.”

Kate moved round to the headmistress’s desk. Now in her thirties, it was twenty years since she had last received a dose of corporal punishment as a sixteen-year-old schoolgirl. Janet stood back for a second and admired the view. That short tight skirt was undoubtedly the focus of attention for some of the older boys in the school. She wondered if Kate wore clothes to deliberately tease.

“This is beyond the call of duty,” Kate declared as she lowered herself over the desk.

Her skirt sculptured tightly around her trim bottom, offering an ideal target.

Crack!

Mrs Hurst brought the strap down with the same force as she would with a cane.

“Ouch!” cried Kate, and leapt to her feet rubbing her bottom.

“How was that?” asked a slightly concerned headmistress.

“I wouldn’t want many of those on my bare bottom,” gasped Kate, wincing, but giggling at the same time as she carefully rubbed her bottom.

The headmistress handed the strap to Kate. “Please?”

“No! Don’t ask me.”

“I really would like to know what it’s like.”

“Sorry, I won’t. I just won’t.” Kate was adamant. She would not spank her headmistress.

“Okay. Can you get Hannah up here? I need to speak to her.”

A few minutes later.

“Come in, Hannah. Please sit down. How are the fifth formers treating you?”

“I’m getting a lot of taunting, but it’s okay. Is there any chance you can let me return to the sixth form?”

“No. You will remain with the fifth formers until you leave the school. I’m afraid I have some more bad news for you. Mrs Masters is coming in tomorrow at ten o’clock to witness you being punished. I couldn’t talk her out of it. She wants to make sure your bottom gets the same treatment as you gave Celine’s. And she has the whip hand, so to speak, with the threat that she will go to the Education Department and the local newspaper if she doesn’t get what she wants.”

“Twelve strokes with this strap. Can you confirm this is what you used on Celine?” showing the strap to Hannah.

Hannah nodded in agreement. She wasn’t sure exactly how many times she’d applied the strap to Celine’s bottom, but twelve was about the right number.

“Do you want a friend to attend with you for support?”

Hannah thought for a moment. Would Sophia volunteer to support her? David definitely would. ‘I bet he would!’ she inwardly smiled to herself. “I’ll ask Sophia, Miss.”

****

“Of course I’ll support you Hannah.”

Sophia wanted to appear supportive but secretly dreaded the prospect of watching her friend being punished. From the location of the prefects sixth form room, the crack of the headmistress’s cane connecting with naughty bottoms, and the accompanying desperate yelps, could be clearly heard to the mild amusement of some of the prefects. But when it’s your good friend on the receiving end it’s not so funny. Having been asked, Sophia felt she had to put her uneasiness to one side and support her friend.

****

Next day, Hannah and Sophia excused themselves from their maths lesson and walked slowly towards the headmistress’s office for the 10 o’clock appointment.

“Thanks for coming with me, Sophia.”

“You must be scared. Are you dealing with it okay?”

“I’m going to be fine. I wished I didn’t have to be confronted by Celine’s mother, but other than that I’m okay. I was willing to dish it out, so I’ve got to be willing to take it.”

They reached the secretary’s office. Hannah, not showing any signs of nervousness, turned to Sophia.

“You’ve been a good friend, Sophia. I hope we will stay in touch when we leave school.”

“You bet,” responded Sophia.

They stepped inside the secretary’s office and were greeted by Kate.

“Would you like to go through to the headmistress? She is waiting for you.”

They entered the headmistress’s office. The reception was frosty. This was a situation that caused the headmistress much unease. She was not in control. She had been forced to hand over control in part to Mrs Masters, Celine’s mother. She had no experience of using the strap other than the one blow she delivered to Kate, and she was perplexed by Hannah’s reasoning and lack of remorse.

“I will ask you to bend over the chair similar to the way you apparently positioned Celine. I can see that you are wearing a dress that will easily lift above your bottom. It will depend on Mrs Masters if you have to remove your knickers. You will receive twelve swats. I don’t know how this is going to pan out. Are you going to cooperate?”

“Yes, headmistress,” answered Hannah.

The headmistress continued. “I’ve got to try and make sure your bottom ends up looking like Celine’s. I will meet and greet Mrs Masters in the secretary’s office. I want to keep any conversation between you and her to a minimum. I hope to get this over quickly and to Mrs Master’s satisfaction, so that the whole thing goes away.”

There was a knock on the headmistress’s door. Kate popped her head around the door and advised Mrs Masters had arrived. The headmistress welcomed Mrs Masters and shook her hand. She planned to get on with the punishment without any further conversation, but it didn’t quite work out that way.

“We have previously met briefly at a swimming gala,” said Mrs Masters to Hannah, rather curtly. “I can’t understand why you have done this to Celine. She adores you. Hannah this and Hannah that. If you set out to break her spirit, you succeeded. When I told her that you were going to be thrashed I thought it might buck her up, but do you know what she said?” She glared at Hannah. “She said she didn’t want you to be punished. Unbelievable!”

The headmistress then intervened and motioned to Hannah to bend over the chair that she had earlier positioned in the centre of the room. Hannah complied, summoning as much dignity as she could. She felt excited and was breathing rapidly, pulse racing. Her loose-fitting dress was easily lifted clear of her bottom and tucked in to avoid flopping back during the strapping. Hannah was wearing white knickers that were now stretched quite tightly across her bottom.

As the headmistress picked up the strap and prepared to apply the first stroke, Mrs Masters interrupted.

“One moment please, Mrs Hurst.”

“What now, Mrs Masters?” the headmistress asked, rather irritated.

“My Celine had her knickers pulled down, Mrs Hurst. Aren’t you going to do the same with Hannah? We agreed the two punishments would be similar punishment, didn’t we?”

“Well, yes, but I very much doubt thin underwear will make much difference.”

“Nevertheless, I thought it was agreed; a similar punishment.”

The headmistress sighed. “Hannah?”

“It’s okay, miss.”

Hannah tried to push her knickers down while still bending over the chair, but it was awkward and Sophia helped her.

Mrs Masters nodded her approval with her arms folded. She looked on sternly.

Janet Hurst’s first ever delivery of the strap to a student’s backside gave her some cheer. It was well-placed and landed with a satisfying thwack. Different to a cane stroke, of which she had delivered quite a few in her relatively short career. A wide band of a less vivid marking began to emerge on Hannah’s bottom compared with the angry red blaze typical of a well delivered cane stroke. It was immediately apparent that with a two-inch width to the strap, there would have to be much overlapping if twelve strokes were to be administered.

Sophia gasped, winced and turned away. Mrs Masters remained expressionless. More hits would have to be delivered before she could decide if her quest for retribution had been satisfied.

Taking her first ever corporal punishment, Hannah seemed up to it. She remained calm, alert and obedient. The pain level of the first lash was no more, no less than she expected, but she questioned if she could endure twelve such lashes and maintain her dignity.

The headmistress settled into a steady rhythm delivering a swat every ten seconds, which equated to the pace of her caning rituals. She checked after her sixth stroke. During a caning session, the sixth stroke would bring the session to a conclusion with the recipient invariably squirming and sobbing or crying, and there would be six tell-tale welts spread evenly over the target. She was aware of noticeable differences.

First off, there was hardly any reaction from Hannah. Was this because of her high pain threshold or were the delivery strokes too lenient?  No visible prominent welts but an overall reddening of her subject’s bottom. Mrs Masters was not showing any reaction. Certainly Hannah’s bottom was not yet showing the anguish displayed by Celine’s bottom.

Janet decided to step up the intensity. She was aware that when applying cane strokes some of her colleagues would put one at the crease between the lower reaches of the buttocks just above the upper thighs. This was probably the most painful caning stroke available, along with the infamous diagonal stroke, but she had always refrained from using it. She felt she could administer a good crisp punishment without exercising this tactic. If you had a student at your mercy, was there really a need to inflict maximum pain? Her view was that a caning should be a learning experience, not retribution.

But this strapping of Hannah was different to the caning that she was so well qualified to discharge.

‘So let the seventh stroke hit that crease and let’s gauge the reaction,’ thought the headmistress to herself. ‘Yes! That’s more like it,’ in response to Hannah’s not inconsequential gasp as the strap landed fairly and squarely across the crease with some force.

Hannah was wondering when the meaningful pain level was going to kick in. That seventh lash across the crease confirmed things were hotting up. Strokes eight and nine powered in with some vigour. The headmistress stood back and studied Mrs Masters, searching for a positive reaction, but that was not forthcoming. Mrs Masters inspected Hannah’s reddening bottom, but clearly believed there was more to be done.

Hannah was now breathing heavily and beginning to feel distinctly uncomfortable, but she remained in control of her emotions.

So far, Mrs Hurst had applied her caning technique. A strong forearm and flick of the wrist, but implement not raised above the shoulder. Time to get that strap working more aggressively. The tenth stroke came from above the shoulder and cannoned into Hannah’s bottom with a resounding crash. This took Hannah by surprise and it hurt. For the first time, she cried out, albeit very briefly. Mrs Masters smiled. At last some proper punishment. The headmistress followed up with a similar strength blow for stroke eleven. Hannah regained her composure but she was now suffering. Each shot was inevitably overlapping with previous strikes and her bottom was raw. She thought to herself that her punishment was surely exceeding that which she dished out to Celine.

The twelfth stroke brought an end to the proceedings. It was delivered with some ferocity that caused Hannah to emit an anguished cry.

Mrs Masters looked carefully at Hannah’s damaged bottom and announced she was satisfied that justice had been carried out and she had seen enough. Without any further comment, she departed, leaving the headmistress, a quietly sobbing Hannah and a shaken Sophia to ponder what had just happened.

Janet threw the strap on to her desk and spent a few seconds observing her handiwork before speaking to Hannah.

“Please remain in position for the moment and reflect on your wrong doings.”

Sophia, not quite knowing what to do, went to Hannah’s side and placed a comforting hand on her friend’s shoulder with words of encouragement. Meanwhile, Janet followed Mrs Masters into Kate’s office, seeking reassurance that the matter was now closed. Mrs Masters was talking to Kate and, although still hostile, indicated a line was now drawn and she would not be taking any further action. With that she departed, mumbling a thanks that the headmistress had sorted out that young lady.

Janet acted out an exaggerated sigh of relief to Kate before returning to her office.

“You are dismissed, Hannah. You are still in disgrace,” she exclaimed.

Janet Hurst felt reasonably satisfied with the outcome. Mrs Masters was not going to proceed with any of her threats. Hannah had been given a proper punishment, and she herself had delivered the punishment with an implement new to her. She examined the strap and came to the conclusion she could become proficient with it but confirmed to herself she would stay with her trusted cane.

Meanwhile Hannah, struggling with the intense, bruising discomfort of the strapping, dragged herself into Kate’s office with Sophia supporting her.

“That was tough,” observed Kate, matter of fact rather than sympathetic. “This might help.” She furtively handed Sophia a jar of antiseptic cream with the inference she might apply it to her friend’s bottom.

“Come with me to the sixth form room and I’ll do the honours,” offered Sophia. “Nobody will be there. They are all at lessons at this time of day.”

But they were thwarted. David was on a free period, lounging on the sofa, sipping his coffee and reading a magazine. He looked up at the two girls.

“All done?” he inquired. “It sounded quite brutal from where I’m sitting.”

“David, could you give us a couple of minutes?” asked Sophia, holding up the jar of cream to indicate the reason for her request.

David, forever the gentleman, immediately understood.

“If you don’t need my assistance, I’ve got things to do,” he said as he departed.

In a release of emotion, Hannah burst into tears and, with Sophia’s help, lifted her skirt and lowered her white knickers, before collapsing onto the sofa. The application of the cooling, soothing cream brought relief as her friend gently attended it to the very sore areas of her bottom and upper thighs.

****

Next day, in the fifth formers room, an annoyed fifth former exclaimed, “I’m not your personal assistant, Hannah. You can answer the door, you know. Celine Masters here to see you.”

“What is it Celine? What do you want?” asked Hannah.

“You weren’t at swimming last night. I missed you.”

“Go away Celine. You let me down. You didn’t have to tell your mum. It was private between us. I have nothing further to say to you.” Hannah turned away, leaving the girl standing alone.

Celine called out to Hannah that she was sorry and would catch up with her later, but the door slammed in her face. Disappointed, she walked away. Her crush on Hannah unrequited.

At the end of term, an announcement was made by Janet Hurst that, from the next term, prefects would not have the authority to issue spankings to erring students. Lines or detentions for minor offences and anything serious should be referred to her.

The End

© Robert Roberts 2022