About to leave school for university, a girl is called to see her headmistress

By Kenny Walters

“You wanted to see me, Mrs Darby?”

The headmistress looked up from the report she was writing, saw the blonde-haired girl nervously peering round the corner of the door and promptly put aside her work.

“Yes, Jennifer. Do come in.” The grey-haired headmistress stood up and gestured to the slim pretty girl wearing tight black leggings and a white blouse to take one of the three comfortable armchairs set to one side of the spacious study. “I’m having a chat with all the Upper Sixth form girls who will be leaving us tomorrow, it being the end of the school year. With all the formalities, there might not be time for me to see everyone after today.”

“Oh I see.” The relief was evident on Jennifer Milson’s face. “I thought I might be in trouble when Miss Turner told me I had to report to your study.”

Mrs Darby smiled, not a common event by all accounts. “No, Jennifer, you’re not in any sort of trouble. In fact, I don’t think you’ve ever been in trouble during your whole time at this school, have you?”

“No, Mrs Darby.” It took a brief wave of the hand before Jennifer felt sufficiently relaxed to sit down on the right hand one of the three armchairs, the headmistress taking the one next to her.

“I’m absolutely sure I’ve never had to cane you. Have you ever had the slipper from one of the teachers?”

“No, Mrs Darby.”

“A detention, perhaps?”

“No, Mrs Darby.” Jennifer smiled shyly. “I did once have some lines to do, but that was when one of the teachers punished the whole class for being too noisy when she left the room.”

“And probably not you to blame, I would guess.”


“Well, Jennifer, I just wanted to say what a pleasure it is to have had you at this school and to wish you all the very best for your time at university and in your future career. You’ve been a most exemplary pupil. Thank you, too, for all the hard work you’ve put in serving as one of our leading prefects.”

“Thank you, Mrs Darby.” Jennifer came close to blushing with all the praise, again unusual for the headmistress.

“So, are you all set for university? Oxford, isn’t it?”

“Yes, I’m very lucky. I got my first choice of college too.”

“Nothing more than you deserve, Jennifer. Would you like some tea?”

“Um, yes, that would be lovely. Thank you, miss.”

As Mrs Darby left her briefly to ask her secretary to organise some tea, Jennifer reflected on the fear and awe she’d held for this formidable headmistress, even though the good lady had never so much as raised her voice to Jennifer, as well as the liking and respect that had grown as she came to know the headmistress better. When the tea came, it was with fine porcelain cups and teapot on a silver tray, complete with a small plate of biscuits.

“So, what plans do you have for the holidays, Jennifer.” Mrs Darby asked as she poured the tea.

“We’re having a family holiday in Greece for three weeks. My parents have organised a villa there.”

“Sounds wonderful. I’m off to the south of France myself.”

The amiable small-talk continued while they drank the tea. Finally, the headmistress brought the conversation to a close.

“Well, Jennifer, as before, my very best wishes for the future. If there’s ever anything I can do to help you, you have only to ask.”

The headmistress had intended her words as a sign for Jennifer to stand up and leave, but the shy pretty girl remained seated. Her complexion darkened slightly, but that was enough for the eagle-eyed headmistress.

“Was there something, Jennifer?”

Jennifer didn’t answer. Leaning forward in her chair and looking down at the thick pile carpet suggested there was.

“I did mean it when I said I’d give you any assistance you needed, Jennifer. You really do only have to ask.”

“It’s difficult, miss.”

“Okay.” Mrs Darby frowned with concern. “There’s no rush, Jennifer. Would some more tea help?”

Jennifer nodded, and Mrs Darby poured fresh cups for them both.

“What is it that so concerns you, Jennifer?” The headmistress asked as she handed over the replenished cup. “I can’t help unless I know what the problem is.”

Jennifer took a sip of the tea. “This will sound weird, miss, but how often do you have to punish a girl, here in your study? This is where you do it, isn’t it?”

Mrs Darby frowned yet again. “By punish, do you mean cane?”

Jennifer nodded.

“Oh, I don’t know.” The strange question had thrown the headmistress off-balance. “Perhaps once a month, something like that.”

“Right.” Jennifer nodded thoughtfully. “And how many strokes do they get?”

“That depends. Sometimes I think a short, sharp shock is all that is needed and it might be just two strokes. Sometimes it’s four, sometimes six when something more is required.”

“When they’ve been really naughty, I suppose.”

“Exactly. Why do you ask?”

Jennifer chuckled. “I’ve always regretted being such a coward, I suppose. There’s been times when I’ve really wanted to do something outrageous like some of the other girls and not mind facing up to the consequences.”

“Which is why we retain the use of corporal punishment, of course. It keeps the vast majority of the girls on the straight and narrow.” Mrs Darby peered discreetly into Jennifer’s cup of tea to see whether she’d finished. She hadn’t.

“So, if I’d been really naughty and cheated in the mock exams, or something, what would have happened to me?”

“Well, you’d undoubtedly have been sent to me by the teacher who caught you and you’d stand in front of my desk while I read the report on what had happened.” The headmistress paused as Jennifer looked across at the large desk and the empty area of carpet just in front. “I’d ask you if there was any good reason why you felt the need to cheat.”

“To see if I had any good excuse?”


“And if I hadn’t?”

“Naturally, I’d check the records to see if there were any other signs of disobedience or other offences, to see if a pattern was emerging.”

“Like if I’d been insolent to a teacher, for example?”

“Yes, things like that.”

“And if I had?”

“Then it would be hard to find a reason not to cane you, Jennifer.” Mrs Darby smiled.

“How many strokes would I get?”

“Four, I would imagine, Jennifer.” Mrs Darby thought for a moment. “Yes four, since it would be your first caning.”

“Suppose there were other things I’d done wrong.”

“Then it would be six of the very best, Jennifer!” The headmistress said forcefully, albeit retaining some humour.

Jennifer thought carefully about the answer. “If you were going to give me six of the best, how would you do it?”

“Probably across your bottom, Jennifer!”

Jennifer blushed. “Yes, I know. But how exactly would you do it?”

“Well, first I’d tell you to come over to these chairs and remove your shoes and your trousers, and of course your blazer if you’d been wearing one.”

“My shoes and trousers?” Jennifer pictured the scene in her mind.

“Yes, your shoes so that you can take your trousers right off without struggling to get them over your shoes, and your trousers because, well, I just find it less restrictive when you have to bend over my desk.”

“So, I’d have to bend over your desk? Whereabouts, exactly?” They both looked towards the desk, and the mass of paperwork that seemed to make such a move rather impractical.

“Obviously, I’d have to clear my desk first.” Mrs Darby smiled. “Don’t worry, that wouldn’t take me long.”

“And then you’d tell me to bend over, would you?”

“You’d probably be waiting here by these chairs having removed your shoes and trousers. If your top covered up your knickers, I’d tell you to fold it up above your waist. While you were doing that, I’d finish clearing my desk and then go and choose a cane from the cupboard over there.” The headmistress nodded towards a tall cupboard in the corner of the room.

“Do you have lots of canes, miss?” Jennifer sounded eager to learn.

“Five or six of varying lengths and thicknesses.”

“Can I see them, please miss?”

“I suppose so, Jennifer.”

The two females went over to the corner cupboard and Mrs Darby opened the door revealing six canes hanging by their crook handles on a row of hooks.

“Which one would you use on me, miss?”

Mrs Darby thought briefly, then selected one of the longer, thicker canes that was next to the end cane on the right. “For a serious offence committed by a senior girl, I would go for this one Jennifer. It’s quite a robust cane but still with enough suppleness to give a really sharp sting.” She handed the cane to Jennifer.

“Ouch!” Jennifer cried, after giving herself a tap on the palm of her left hand.

“It smarts, doesn’t it?”

Jennifer nodded as she continued to examine every inch of the three foot long implement. “I bet six strokes would really hurt.”

“Indeed it would, Jennifer. Perhaps we ought to put it away?” Mrs Darby held her hand out for the cane to be returned to her, but Jennifer held back.

“Miss, you said if I ever wanted anything then I had only to ask. Is that right?”

“Yes, that’s quite correct, Jennifer.”

“This is going to sound strange, miss.”

“That doesn’t matter.”

“Miss…” Jennifer hesitated. “I want you to cane me, miss. I want to have the full six strokes.” By looking straight into the headmistress’s eyes, Jennifer both pleaded and demanded her request be complied with.

“Why, Jennifer?”

“Because I need to know what it feels like to be dealt with in the same way as those more daring girls that I envy so much.”

“I’m not sure you’d be quite so envious after six strokes, Jennifer. Perhaps we could just give you one?”

“No, miss. It has to be the full six just like the others got it. Please, miss.”

“Very well, Jennifer.” Miss Darby could see the girl was determined to have her own way. Her voice strengthened. Go back to the chairs and remove your shoes and trousers.”

“You will give me six good strokes, won’t you miss?”

“Do as you are told, girl!” The headmistress roared.

The sudden change of mood shocked the pretty eighteen year old so that her legs were like jelly as she silently went over to the comfortable armchairs. Amidst a mixture of fear and anticipation, Jennifer kicked off her shoes and thumbed her thin black leggings down off her hips. Her white blouse had quite a long tail that kept her underwear covered until she bent down and picked the leggings up.

“Roll your top up so we can see your knickers, girl!”

Now the fear was overtaking the anticipation, and Jennifer felt quite scared as she obediently rolled her cotton blouse up to expose her brief white panties. At first, the blouse didn’t want to stay up and she had to re-roll it up more tightly to ensure her panties remained on view.

“Over here, girl!”

Jennifer looked round and saw that Mrs Darby had cleared her desk of all the paperwork and was standing by one end with the cane in her hand. The eighteen year old’s heart pounded as she approached the desk.

“Stand there, girl!” Mrs Darby pointed to the carpet by the end of the desk.

Jennifer went to the spot indicated and stood looking fearfully up at her headmistress.

“Face the desk, girl.” The voice suggested annoyance at the girl for stupidly not doing just that in the first place.

Jennifer turned ninety degrees to her left and looked down at the polished surface of the desk, then felt the tip of the cane in her back as she was pushed closer.

“When you are told to do so, you will bend over the desk and get right down. Thrust your bottom out and make sure the tail of your blouse cannot impede the punishment in any way. Is that clear, girl?”

“Yes, miss.”

Jennifer waited, the fear and tension proving almost too much to endure.

“Bend over.”

The eighteen year old dutifully leaned down and rested the top half of her body on the uncomfortably hard wooden surface of the desk. It took some wriggling and a slight bend to he knees before she was able to thrust her backside out and offer it for punishment. It was necessary, too, to tug the blouse a bit further up before she felt certain it would not fall back down and cover her bottom.

“Are you ready?” The voice contained more than a hint of sarcasm.

“Yes, miss.” Jennifer replied humbly.

“Then you will hold perfectly still while I apply the six strokes to your backside and you will remain in position until you are told you can get up. You are not to touch your bottom or try to avoid the full force of each stroke in any way. Extra strokes will be applied if you do. Is that clear?”

“Yes, miss.”

Aside from a little movement from Mrs Darby, all Jennifer could hear was an uneasy silence as she waited to discover what would happen next. When the cane struck her sharply across both buttocks and a loud crack filled her ears, she suddenly realised being caned was an extremely painful matter.

“Ow! That really hurt, miss.”

“Silence! And stop fidgeting!”

“Sorry, miss.”

“I told you to keep quiet, girl! Any more and there’ll be extra strokes!”

A tear trickled down Jennifer’s face. This wasn’t how it was meant to be. An informal demonstration of six whacks with the cane that maybe would sting a little was all that she had anticipated.

Another crack nearly deafened Jennifer as a second punishing stroke landed across her backside, and she had to summon all her strength to remain still and not cry out again. She wanted so much to explain to Mrs Darby this wasn’t what she meant the caning to be, but the headmistress had already convinced her that any such attempt would simply get the caning extended.

“Uunn!!” Jennifer couldn’t help but grunt as a third stroke whipped across her buttocks. As the eighteen year old gripped the edges of the desk she half expected another rebuke from Mrs Darby, but thankfully that didn’t happen.

“Uuuhh!!” The cane lashed Jennifer’s backside again she wondered why on earth she’d ever asked to be caned, certainly not by a headmistress well practiced in its use. Why couldn’t she have asked a friend to do it, if indeed she really did need to experience such a thing.

“Aaah!!” Another hard, painful swipe across her buttocks stung and scorched parts that were already aching and sore, yet still the eighteen year old clung to the desk and kept her bottom thrust back for the punishment to be applied.

“Eeeeeeesh!!” The cane struck yet again, sending yet more spasms of searing, burning pain spreading like wildfire across Jennifer’s bottom. She wasn’t sure, but the eighteen year believed she had taken the full six strokes. What if she had? What would happen now? She recalled Mrs Darby telling her to remain in position until told to get up, so Jennifer kept her bottom poised.

The seconds ticked by and nothing happened. No further strokes, no word from her headmistress. What was happening? What was going on?

“Very well, Jennifer, you can get up and retrieve your trousers and shoes.”

It was indeed all over. Jennifer slowly lifted herself up from the hard wooden surface of the desk. A gentle, oh so gentle, exploration of her backside confirmed there were ridges and weals to mark exactly where the cane had fallen. Jennifer’s legs felt stiff and weak making it difficult to turn and shuffle back to the comfortable chair where her black legging trousers awaited her.

It was painful bending to feed the trousers onto her feet, all the more so when it came to pulling them up and back into place around her sore bottom. The eerie silence was uncomfortable, but nothing compared to the feeling of Mrs Darby watching her every move. Just as Jennifer was threading her feet back into her shoes, she felt a hand on her shoulder.

“So now you know what it is like to be caned, Jennifer. I hope that satisfies your curiosity.”

“Yes.” Jennifer half turned towards the headmistress. “Yes, miss. Thank you for doing that.”

“Perhaps you wish you hadn’t asked for such a thing to be done to you?” Mrs Darby turned the girl fully round so they were face to face and placed a hand on each of her shoulders. “Any regrets?”

“Oh no, miss. No regrets.”

Jennifer lied. Secretly inside, she regretted she would never again be able to ask Mrs Darby to cane her.

The End