A school secretary assists a new headmistress

By Felicity Warren

After leaving school with good A Levels, Jeanette Gough had sailed through secretarial college and followed her college qualification with a diploma in business administration. So, when she applied for a position as Administrator at The Lady Isabel Boarding School for Girls she was confident of success. And so it proved, as she was appointed on a good salary and joined the school during the Easter Term in 1959. She found the job interesting and challenging, combining as it did the functions of school secretary with involvement in the whole administration of the school, including management of finances, dealing with parents on non-academic matters, liaison with examination boards and the like.

Jeanette did, however, find some aspects of the school to be, quite frankly, a little lax. Prior to her interview she had read the parents’ guide that the school produced, and after a few weeks in the job it seemed the policies listed in the guide differed somewhat from the reality that she observed.

The parents’ guide was specific on the adherence to school uniform. Up to the fifth form, girls were supposed to wear the regulation navy blue gymslip, with sixth formers instead allowed pleated skirts. When outside school, girls were all supposed to wear blazers and berets and the dress code also mandated tan seamed stockings and black lace-up shoes. But a number of girls seemed to ignore these rules and, quite surprisingly, seemed to be allowed to get away with it. Skirts instead of gymslips for some girls as young as the fourth form, black stockings with white ankle socks were quite a fashion, and berets outside school seemed non-existent.

The guide also mentioned discipline, stating that mild corporal punishment was used where necessary in class and for serious misbehaviour the headmistress would use the cane. Jeanette saw no evidence of this; there had been, to her knowledge, no canings and, since her office was adjacent to that of the headmistress, she would almost certainly have known had any girl been caned. Quite frankly, it seemed to Jeanette that the headmistress, Miss Pickering, was losing interest in certain aspects of her role, perhaps thinking of retirement.

None of this directly affected Jeanette, of course, as she had no teaching responsibilities. But she couldn’t help thinking that if she had behaved in her own schooldays, not that many years ago, in the way that some of the Lady Isabel girls did, then her bottom would have received some very firm attention.

All of this changed in early June when it was announced that Miss Pickering was indeed to retire at the end of the school year, and that her replacement would be joining immediately, initially to shadow the current head, and to take total control from the start of the 1959-60 school year. The replacement was a Miss Draper, and it soon became apparent that she was as different from Miss Pickering as was chalk from cheese. As soon as the girls had left for their summer break, Miss Draper set about changing things with considerable energy, and Jeanette found that this impacted on herself in her role as Administrator, meaning a very busy few weeks before the start of the next school year.

Miss Draper asked Jeanette to write to all parents reminding them and, perhaps more importantly, their daughters, of the content of the parents’ guide. The letter stressed that all aspect of the guide should be adhered to, and as there was no specific mention of changes to the dress code or the discipline code then Jeanette felt that her own concerns might not be relevant for much longer.

One day, toward the end of July, while Miss Draper and Jeanette were having a coffee break, the headmistress suddenly asked: “Jeanette, where did Miss Pickering keep her canes?”

“Sorry, headmistress, I really don’t know. In my time here, I don’t think she ever used one.”

After the two women searched around, one old crook-handled cane turned up, though it looked like it hadn’t been used for years.

“Well, Jeanette, can you order me some more canes from the educational supplier, please? I hope I won’t have to use one, but it’s better to be prepared should any of the girls decide to misbehave. If they do, then they’ll soon be across my desk with their skirts raised.”

“Yes, of course, headmistress. The sales rep is due at the end of this week, so I’ll get them added to our order.”

The sales representative made his call on Friday as planned. Jeanette had never met him before and she had to admit he was quite a dreamboat. The old cane was on her desk and she noticed that he couldn’t take his eyes off it as Jeanette went through the schools requirements for exercise books, text books, laboratory equipment and the like.

“Oh, and can I please order three canes similar to this one, please?” she said.

“Yes, of course, Miss Gough. I didn’t know you caned girls here. On their hands, I suppose?”

“None of your business what we do here,” snapped Jeanette, then she added, as an afterthought: “On their bottoms, if you must know.”

****

In the next few days, three apparently unconnected things happened.

On Wednesday, the order from the educational suppliers arrived. Jeanette unpacked the items and transferred them to the departments that needed them. For reasons that she couldn’t quite explain to herself, she unwrapped the canes and swished one of them through the air in her office. Jeanette had the place to herself, so no one saw or heard.

On Thursday, again something she couldn’t explain; Jeanette took the old cane home with her to her flat that evening. After all, it wasn’t going to be used now the new ones had arrived, was it?

On Friday, the sales rep telephoned. He wanted to check the order had arrived correctly, which Jeanette was able to confirm. And, totally unexpectedly, he said that he was going to the local dance hall on Saturday evening and would Miss Gough like to accompany him? Jeanette was speechless for a couple of seconds; she hadn’t been asked out by a man for about six months and her last few dates had hardly been successful. But she heard herself accepting and agreeing to meet him outside the dance hall at 7.30 the following evening.

“Oh, and my name’s Tom Underwood,” said the sales rep.

“And I’m Jeanette, so you don’t need to call me Miss Gough tomorrow.”

****

Jeanette decided to go shopping on Saturday morning. While she wasn’t entirely sure about Mr Tom Underwood, she decided that she ought to make an effort; after all, he’d asked her out having only ever seen her in her work attire of simple white blouse and dark pencil skirt. She decided that for the dance she would wear her burgundy dress with the circle skirt and her frothy white petticoat, but she needed new shoes, and it took several hours around the shops before she decided on one of the first pairs she’d tried on, a simple black pair with a small heel.

She also decided to boost her confidence with new underwear, not that Mr Underwood would be seeing that, of course. A new bra and knickers, and a new girdle that pinched her waist in and improved the look of the burgundy dress considerably. She put on make-up, then a new pair of nylons, checking her seams in the mirror. A spare pair of stockings went into her handbag to allow for ladders and runs, and with her beige raincoat she thought that she looked as good as she was ever likely to.

Her evening with Tom Underwood went very well. He was an attentive escort, she enjoyed dancing with him and he insisted on walking her back to her flat. She didn’t invite him in, of course; she wasn’t that sort of a girl, but with a peck on his cheek she agreed to see him again.

****

Jeanette and Tom started to see each other most weekends, and into September the new school year started with the human whirlwind that was Miss Draper. Jeanette told Tom of her days at work and he always showed an interest, though one day he asked a strange question.

“Have those new canes been used yet, Jeanette?”

“No, why do you want to know?” replied Jeanette, looking askance at the man she now considered her young man.

“Just wondered, that’s all,” was Tom’s off-hand reply.

“I’ll let you know if they are,” said Jeanette abruptly, and both suddenly seemed keen to change the subject.

That evening, Jeanette brought out the old cane that she’d removed from school, flexed it in her hand and swished it through the air. Was Tom interested in her, or was he more interested in schoolgirls and corporal punishment?

****

The following Saturday brought a departure from the normal school life. Jeanette was again in town for the evening with Tom and had literally bumped into two of the senior girls, Lynne Singleton and Joan Black, as the girls came out of a public house.

“What do you girls think you’re doing?” was Jeanette’s immediate reaction. “You’re not old enough to go into a pub, and even if you were the headmistress would never permit it. You two are both in big trouble.”

The girls hurried off without a further word as Jeanette turned to Tom.

“I’ll have to report those two to the headmistress. She won’t be happy. In fact, I think she’ll be utterly livid with them.”

Tom had a strange look on his face, and Jeanette couldn’t help wondering if he was thinking about the canes his company had sold.

****

On Monday morning, Jeanette duly reported what had happened to Miss Draper and, as expected, she was shocked at the girls’ behaviour.

“Well, Miss Gough, from what you’ve told me I’m going to have to deal severely with those two girls. This is far too serious for lines, or detention, or even for a good old-fashioned smacked bottom. No, they’re going to get a caning each, and the little madams will deserve every stroke.”

Miss Draper disappeared into her office, only to come out again a few minutes later.

“Two things, Miss Gough. Firstly, send notes to whatever classes those girls are in telling them to report here immediately after the last lesson of the day. Secondly, I would like you to assist me in their canings.”

Jeanette was struck dumb for a couple of seconds.

“Assist you, Miss Draper? What does that entail?”

“Each girl will be told to bend over my desk. I would like you to raise her skirt and slip, move both garments away from the girl’s bottom to her waist, and check her bottom for unnecessary padding. Girls have been known to try and get away with an extra pair of knickers if they are expecting a caning, so I want you to check that neither of these two try anything so blatant. I’ll give each of them three strokes, and I want you to be ready to hold them down over the desk if they try to get up before their punishment is completed.”

“Of course, Miss Draper, I’ll be happy to do whatever you think is necessary,” was all a shocked Jeanette could think of to say.

Tom was bound to ask her what had happened to the girls, and it looked like he might get a story that he wouldn’t be expecting.

****

Jeanette could hardly concentrate on her work for the rest of that day. The administrator who had taken an old school cane home was now going to witness first-hand how the new replacement was to be applied by the headmistress to the bottoms of those two very naughty girls.

Jeanette’s mind wandered. She fantasised about being in Miss Draper’s place and caning the girls herself instead of just assisting. In her mind, she flexed the cane, took a couple of practice swishes, placed it on the miscreant’s knickered bottom and brought it down onto the inviting target.

Her mind wandered again. She fantasised about being Joan Black, bending over the desk, feeling her own skirts being raised, leaving her knickers and suspenders on public view, then hearing the swish of the cane as Miss Draper brought it down onto her bottom.

****

At 4.00 pm there was a knock on Jeanette’s office door and there stood Lynne Singleton and Joan Black. Obviously, they realised that Jeanette was responsible for the headmistress getting to hear of their misbehaviour, but however much they resented her there was nothing they could do about it.

“Go in, Miss Draper is expecting you,” said Jeanette, and the girls knocked on the headmistress’s door and disappeared inside on hearing the one word “Enter”.

The intercom on Jeanette’s desk buzzed, and she heard Miss Draper’s voice.

“Miss Gough, a few minutes of your time, please. I want you to assist me with the chastisement of these two naughty girls.”

“Certainly, headmistress,” replied Jeanette, and she followed the two girls into the inner sanctum. The cane was lying on Miss Draper’s desk and the two girls were stood, hands in front of them, staring with great interest at the floor. As sixth formers, both wore navy blue pleated skirts.

“I will punish you in alphabetical order, so you, Black, will go first. Please bend over the desk and grasp the far side. Miss Gough, would you please prepare the girl?”

Jeanette took the hem of Joan’s pleated skirt and raised the garment, revealing the girl’s white underskirt. That followed, and Jeanette took great care to fold both garments back right up to the waist. Joan’s white knickers were stretched across her bottom, and her folded white slip, taut white suspenders and the dark tan welt of her seamed stockings framed Miss Draper’s target area. Jeanette then took up position on the far side of the head’s desk, ready to hold Black down if necessary.

Miss Draper, unknown to herself, now acted out the fantasy Jeanette had played out several times that day. The headmistress flexed the cane, took a practice stroke, then brought it down with a resounding thwack onto Joan Black’s seat. The girl cried out, but to her credit didn’t move from her position. A second stroke followed, and a few seconds later a third.

“Right, Black, punishment complete, so stand up and rearrange your clothing.”

Joan moved away from the desk with difficulty, and pulled down her slip and skirt. She started to sob quietly but didn’t attempt to rub her caned bottom.

“Now you, please Singleton. You’ve seen what happens, so bend over the desk and let’s get this unpleasantness over and done with.”

Lynne bent over the desk with obvious trepidation. Having seen her friend’s punishment, she knew what was coming. Again Jeanette arranged the naughty girl’s skirts as Lynne held her breath. Miss Draper raised the cane, which swished through the air and landed on the girls knickered bottom.

“Ooowwww!” screamed Lynne, and she half got up from the desk. Jeanette placed both hands on her shoulders and held her down.

“Take your punishment without any more sound or movement. If not, the headmistress will give you extra strokes.”

Jeanette had no idea where the comment about extra strokes had come from, certainly the headmistress had never indicated this as a possibility. Swish! Swish! The cane landed twice more with satisfying thwacks as Lynne Singleton took her punishment.

“Stand up, Singleton, and make yourself decent,” said the headmistress, and a sobbing Lynne quickly rearranged her slip and skirt into something like their normal place, trying to rub her bottom as she did so.

“Right girls, you are both dismissed. And I never want to see you in this office again. If you repeat your behaviour, you will simply be expelled, and I’m sure neither of you would want to explain something like that to your parents. Now, get out of my sight.”

The two caned girls departed the office, walking with difficulty.

“Thank you for your help, Jeanette. I always feel that a caning is more effective if it’s witnessed. Someone else seeing them punished adds to the humiliation and makes it far less likely that they’ll come back for more.”

“No problem, Miss Draper, and I hope I didn’t exceed my authority by threatening Lynne Singleton with extra strokes.”

“Of course not, Jeanette, very imaginative of you. Now let’s get on with our normal work.”

****

Jeanette was hardly surprised when Tom telephoned her just before she was due to leave for the day.

“Can you talk? Did Miss Draper cane them? She looks so strict, doesn’t she? I bet you could hear the strokes from your own office.”

If only he knew! Jeanette decided that she’d tell him the entire story, and who knows, perhaps she might illustrate it with the cane she’d got at home? Tom had clearly got an obsession about a woman wielding a cane, so maybe Jeanette might show him how it had been done.

The End

© Felicity Warren 2021