The young reporter meets an old acquaintance

by Alison Short

For the next two months, the Wolds School and its extraordinary martinet of a headmistress, Hilary Underwood, played no part in my life, although they were never far from my thoughts.

My first two encounters with Miss Underwood, both of which had ended up with me being caned, with my full consent, had not just been pretty mind-blowing, but left a host of unanswered questions. What had possessed me, a young woman of twenty-three, to bend over and submit to a classic ‘six of the best’ as routinely administered to schoolchildren of that generation?

The first time, I could plead journalistic inquiry. I had been sent to interview Miss Underwood, who had offered to demonstrate her application of traditional English school discipline. The second time, summoned to her study because my article about the school had incurred her displeasure, I had been practically begging for further chastisement. Why?

I can see now, from the perspective of late middle-age, that I was simply spanking-curious, as the saying goes. But nobody used expressions like ‘spanking-curious’ in the late 1960s. I was a traveller in a strange land.

Then there was the riddle of Charlotte Forbes, Miss Underwood’s young secretary, whom I had met on my second visit to the school. Not only had it transpired that, by mutual consent, she subjected herself to corporal punishment from Miss Underwood when she stepped out of line. She had also been asked to witness my caning and, from what I could judge, enjoyed every second. Again, why? What was going on?

As the weeks passed, the riddles receded, although they did not completely go away. I remember one amusing incident that took place a few days after my second visit to Miss Underwood’s study. For some time, I had been conducting a flirtation with Dave, a fellow hack at the newspaper where I was working. In due course, we ended up sleeping together and he spent the night at my flat.

As I slipped out of bed the next morning to go to the bathroom, I got the shock of my life when he suddenly said, “Have you been a naughty girl, Emma?” I had completely forgotten that my bottom still bore the fading marks of the stinging six-of-the-best caning which Miss Underwood had administered.

“Well, it’s a long story,” I said, with a laugh, stopping to admire the stripes in the mirror myself, as I had already done many times, admiring the accuracy of Miss Underwood’s aim. “You thought not much happens in Lincolnshire? Get a load of this.”

“Bloody hell,” said Dave, after I had given him a blow-by-blow account and sworn him to secrecy. “You do live, don’t you?”
Dave was a nice enough bloke, but our fling was soon over and, a month later, he moved to another job in a different town, leaving me to get on with my life as a jobbing journalist on a local paper. Life moved on, summer turned to autumn and it was only a chance encounter in a café in Lincoln that brought the Wolds School back into my life.

I had time to kill, after a magistrates court hearing I was covering had been adjourned unexpectedly, so I was treating myself to a sandwich lunch in a little café which had a splendid view of the cathedral when something about the woman at the next table caught my eye. She was about my age, with a shock of red hair, and she seemed vaguely familiar. Then it suddenly registered. It was Charlotte, Hilary Underwood’s secretary!

She had her back to me, so I spotted her before she had spotted me, and, as she was on her own, I saw no reason why I shouldn’t say hello for old times’ sake.

“It’s Charlotte, isn’t it?” I said, tapping her on the shoulder.

She looked completely blank for a minute, then made the connection.

“I’m sorry, I don’t think…? Of course, I remember you now. It’s Emma, yes?”

“Do you mind if I join you?”

“Of course not.”

A few minutes later, we were sitting opposite each other looking slightly sheepish, like two people who shared a guilty secret, which I suppose, in a way, we did.

“You’re not at school today?” I asked.

“It’s half-term.”

“Of course. I’d forgotten. I was wondering why Miss Underwood had let you off the leash.”


“Only joking.”

There was a longish pause. I was starting to regret the reference to a leash, which had been meant ironically but seemed to have hit a nerve. But I was damned if I was going to pass up on such a golden opportunity to satisfy my curiosity about Charlotte and her madly unconventional relationship with Hilary Underwood.

“Tell me if this is none of my business,” I said, plunging in, “but I have to say that Miss Underwood is one of the most impressive women I have ever met. She seems to take no nonsense from anyone, but her heart is obviously in the right place and, if I were you, I would be only too delighted to work for someone like that. Your little, what shall I say, understanding about what will happen to you if you step out of line must be very reassuring, particularly if you have been quite erratic in your behaviour in the past. Well worth the odd sore bottom,” I added, my voice dropping to a whisper.
What happened next took me completely by surprise.

“You’ve certainly hit the nail on the head there,” she whispered back, wriggling in her chair to make herself clear. “My bum’s still sore after I got into trouble yesterday. Miss was hopping mad with me for spilling a cup of tea.”

“Do you want to tell me about it?”

At this point, the couple sitting at the next table got up and left, which allowed Charlotte and me to continue our conversation without any risk of being overheard. And, little by little, with odd embarrassed pauses and the occasional giggle, the whole story of their extraordinary relationship came out.

As soon as Charlotte had agreed in principle that she was prepared to submit to corporal punishment at the hands of Miss Underwood, if her behaviour fell short of the standards expected, Miss Underwood had drawn up a ‘Schedule of Sanctions’, or SOS, for different categories of misbehaviour. Minor offences would be dealt with by an over-the-knee spanking, more serious ones by a caning, with intermediary ones punishable by the strap or slipper. Spilling that cup of tea had fallen under Gross Carelessness in the Schedule of Sanctions, Charlotte explained, and been punished by twelve whacks with the slipper.

“Miss Underwood got me to type out the SOS, then sign it at the bottom,” she added, with a wry smile. “We both have a copy and we could probably both recite it by heart. And you know what? It has brought a real sense of structure to my life that wasn’t there before. I used to be a bit of wild child, a tomboy. Now, because I know where I stand, and what the consequences are if I step out of line, I have never been happier. Does that make sense?”

I nodded, my mind racing. Yes, it made sense, at one level, but it was also so damn weird that I had to ask the obvious question.

“When you have, um, been naughty and Miss Underwood, um, chastises you, do you, um, enjoy yourself?”

“Sometimes,” she said coyly, averting her eyes. “Well, I mean not actually enjoy, in the way that you might enjoy an ice cream. But there must be something about being punished by an older woman which I secretly quite like or I wouldn’t let myself in for a sore bum quite so often. Would I?”

“And Miss Underwood? Does she enjoy herself?”

“Oh, she definitely enjoys herself,” Charlotte said, flashing a cheeky smile at me. “She acts cross, and says how disappointed she is with me, but if you ask me, she is never happier than when she’s got me at her mercy. It takes all sorts, eh?”

Yes, I agreed, it took all sorts. For a few minutes, neither of us said anything, although I suspect we were both thinking the same thing. If two could play at this extraordinary game of crime and punishment which Hilary Underwood and Charlotte Forbes had devised for themselves, why not three?

“Perhaps we should both do something to incur Miss Underwood’s displeasure.” I blurted out, throwing caution to the winds. “Then we’d both be for the high jump!”

Our eyes met and, fifty years later, I can still remember the guilty conspiratorial pleasure of the moment. In no time, we were drawing up a battle plan and, by the time we went our separate ways, half an hour later, we knew exactly what we were going to do.

* * * * * * * * * * * * * * *

It was exactly a week later that Charlotte and I put ‘Operation Extreme Peril’, as we jokingly referred to it, into action.
Miss Underwood was a practising Anglican, Charlotte explained, and attended morning service every Sunday at St John’s church in the village closest to the Wolds School. After church, weather permitting, she would walk the short distance to her cottage on the outskirts of the village. What if we were to somehow lie in wait for her and let ourselves be caught behaving in some loutish way which would incur her displeasure?

It was the sort of idiotic scheme which might have been dreamed up by two particularly silly schoolgirls, not two grown women in their mid-twenties. But that, of course, as I was fast learning, was the whole point. For adults, of either sex, who secretly crave to be spanked, it is the temporary regression to childhood, and the application of sanctions appropriate to a child, which is an essential part of the attraction.

As Operation Extreme Peril was put into action, and Charlotte and I lurked up a side lane, waiting for Miss Underwood to pass on her way back from church, we were giggling like 12-year-olds. We each had a cigarette in one hand and a bottle of beer in the other and, if that did not draw a stern response from Miss Underwood, nothing would.

At first, she just stopped and stared at us.

“Charlotte? What on earth? Oh, it’s you,” she said, taking a minute or two to recognise me. “Is this some sort of game? I have never seen such unladylike behaviour. Smoking? Drinking? And on a Sunday morning, when people are at church! What are you thinking of?”

“I’m very sorry, Miss Underwood,” Charlotte stammered, stubbing out her cigarette.

“I’m very sorry, Miss Underwood,” I said, following suit.

There was a lengthy pause and I could almost see the cogs of Miss Underwood’s brain turning as she planned her next move. Then, in that distinctive icy voice of hers, she spoke.

“What you do at the weekends if your business, Charlotte. I have no authority to discipline you for anything you do outside the school grounds. I just think you should have reflected that, by behaving in this slovenly manner less than a mile from the school, you are setting a very bad example. As for you, young lady.” She gave me an absolutely withering glance which I can still see, all these years later. “You can be glad I’m not your mother, as I would give you a damn good hiding.”

There was another long pause, and I could feel my mouth drying.

“I may be a bit old-fashioned,” Miss Underwood resumed, “but I am not a fool. I am assuming that our meeting like this is no accident. I suspect that you wanted me to catch you and that you knew I would be angry with you. Am I right? Well, you have got what you wanted. I am angry with you. And if you want to present yourselves in my study at four o‘clock this afternoon, you will find out just how angry. Whether you choose to take up that invitation is entirely up to you.” With which she turned on her heels and strode off down the road.

“Wow!” whispered Charlotte, when she was out of earshot. “I’ve never seen her so mad. I suppose we’ll just have to take our medicine. Do you agree?”

I gave a nervous nod. Charlotte and I had embarked on Operation Extreme Peril in high spirits, treating it like a party game, but there was only one way this game was going to end! I suddenly felt that distinctive mixture of fear and pleasurable anticipation which spanking fans the world over will recognise.

It was nearly four hours before our appointment with Miss Underwood, so we repaired to a pub in the next village to have a bite to eat and get some Dutch courage for the ordeal ahead. We were dressed informally, in jeans and T-shirts, and discussed whether to put on something a bit smarter, but decided against. Then, as four o’clock approached, we made our way to the Wolds School in my car. Neither of us said much, but the tension was electric.

We knocked nervously on the door of the headmistress’s study and were told to enter. Not greatly to our surprise, she was wearing her black academic gown; her ‘flogging get-up’, as Charlotte jokingly referred to it. But what happened next took both of us aback.

Instead of dealing with us in her study, she marched us off down a corridor. It was a weekend, so the school was completely deserted. Two minutes later, we found ourselves in one of the classrooms. There were around twenty desks, laid out in rows, and a blackboard, on which someone had chalked what looked like a maths lesson in multiplication. Row after row read: 6 + 6 = 12. Looking back, the significance of the calculation was not too difficult, but do not forget I was still a novice in this strange world of crime and punishment.

Beckoning at us to sit down at desks in the front row, Miss Underwood surveyed us coldly.

“You both know why you are here, and you both know that you are here entirely of your own volition. You are grown women, not pupils in my charge. But now that you are here, you must face the consequences of your, frankly, juvenile behaviour this morning. If I caught one of my pupils smoking, there would be only one sanction; six of the best with the senior cane. The same sanction would apply to a girl caught drinking. Two lots of six, equals twelve. I hope I make myself clear?”

We nodded in nervous unison.

“Charlotte, I want you to go back to my study and fetch the senior cane. Emma, you may stay here. If you look behind you, you will see that there is a gym horse in the corner of the room. Kindly bring it up to the front of the class.”
I did what I was told, dragging the small pommel-horse across the floor. So this was to be the place of execution! I could feel myself trembling, but was also strangely elated. The whole proceedings had an air of ritual that spoke to something deep inside me.

The only outstanding question was which of us would have to face the music first. I both hoped it was me, and feared it was me. And, when Charlotte returned with the cane, it was not long before I was told it would be me.

“Bare and bend,” Miss Underwood said quietly, tapping the top of the pommel-horse with the cane. There was certainly no surprise about the requirement to bare! I quickly slid down my jeans and underpants until they were around my ankles, then bent across the horse as far as I could reach. I felt horribly, deliciously exposed. Out of the corner of my eye, I could see Charlotte standing at a safe distance, watching intently.


The first stroke came fractionally before I was expecting it and, as the pain exploded in my rump, I let out a low animal moan. Eleven more to go! And I had asked for this! Literally!

Strokes two, three and four followed in rapid succession, stroke five was a real stinger, and stroke six was the worst yet, searing into the fleshiest part of my bottom.

“You’ve taken those very well, Emma,” said Miss Underwood, a compliment to which I clung on gratefully as the beating continued.

As anyone who has ever graduated from six of the best to something more serious will testify, the strokes of the cane quickly start to land flush on parts that are already sore and throbbing. After one stroke, the ninth, I was in so much pain that I screamed out loud and kicked both legs in the air, all modesty gone. But I hung in there, with gritted teeth, until I heard Miss Underwood say, “That will be all, Emma. You may get dressed now.”

Red-faced and red-eyed, I now had a ringside seat as Charlotte took my place, bent over the horse, with her splendidly rounded bottom on display. I had quite a sheltered upbringing, and neither at home nor in school had I watched anyone actually receive corporal punishment. That my first experience of what I now regard as one of life’s great pleasures should involve a cane, a naked bottom and a woman in her twenties was riches indeed!

I watched hypnotised as Miss Underwood, coldly and savagely and with well-practised aim, decorated Charlotte’s bottom with a dozen of the very best. She reminded me of a squash-player, deftly cocking and uncocking her wrists rather than relying on brute force. The swish as the cane whipped through the air, followed by the sharp crack as it hit its target was indescribably thrilling, as was the rapid emergence of angry red stripes on that squirming, bucking bottom.
Charlotte took it well, better than me, I would have to say, but I noticed she was sobbing by the time her ordeal was over. When she had eased her knickers and jeans back over her throbbing bottom, Miss Underwood gave another of her wintry smiles.

“That concludes your punishment, ladies. You have stepped out of line and been taught a lesson. Let that be the end of the matter.”

Somehow I knew that it would not be the end of the matter, and that this thrashing was not the final chapter, but the beginning of a long journey on which I am still travelling.

“Welcome to the club,” Charlotte whispered, as we went our separate ways half an hour later. Given my lifelong membership of the ‘club’, and my blossoming friendship with Charlotte, it would prove a prophetic comment.

The End

© Alison Short 2020