Going to work for the headmaster of your old school can prove awkward

By Pat Greenham

“Perhaps I should cane you again.”

The Headmaster was cross with me as I again arrived late and just before he was due to go into the 9.05 assembly. For a full three minutes he gave me a massive ‘telling off’ saying that, after initially being a diligent secretary, I had slipped into bad ways, reminding me that my hours were 8.45 to 4.45 in the afternoon.

The reason for arriving in good time in the morning was to make sure that everything he needed for assembly was ready. He reminded me that my predecessor, Mrs Higgins was always in by 8.30 and had a cup of tea on his desk by 8.45 with the briefing for assembly. He also added that recently he had noticed mistakes in the letters that I gave him for signing which he now felt duty bound to check, something that he had not had to do with Mrs Higgins.

He also said that my tardy timekeeping in the morning was matched by my swift departure at seconds after 4.45 without so much as a goodbye. To make me feel even worse he added that Mrs Higgins always came into his study before she left around 5 to check there was nothing else.

As he was giving me this massive telling off, I was desperately trying to get everything he needed for assembly together and was apologising profusely. I handed him the papers and reminded him that late the previous day two boys had been reported for fighting and that he wanted to see both of them at morning break to be caned, and it was this final comment that prompted him to add: “Perhaps I should cane you again, to see if you can mend your ways.”

This comment was not made in a serious way but more from his exasperation. As he departed for morning assembly I felt that I had really let him down.

By way of background, I had attended the school as a pupil before leaving to attend Secretarial College. As luck would have it, when I left the College there was a vacancy for an Assistant Secretary back at my old school, which I applied for and was successful in gaining the post. I had worked for two years as assistant to the Headmaster’s secretary, Mrs Higgins, before she retired and I was promoted in her place.

Initially I had clearly worked well, but that morning I was left in no doubt that I had let my performance slip and had fallen into bad ways. The Headmaster was normally very ‘laid-back’ but I had clearly pushed him to the limit.

As I sat at my desk whilst he was away taking assembly I was shell-shocked, not about his threat of a caning (which in any case was not made in a serious way) but about his ‘telling off’ and I knew I had let really him down. In truth I absolutely loved my job and had adored Mrs Higgins, so to be compared to her in such a bad light was awful. I knew that if I were to keep my job I would have to change and change quickly.

His reference to ‘caning me again’ was a reference to the one and only time I received the cane when I was at school. In the lower sixth I was caught smoking and warned if I was ever to be found smoking in my school uniform again I would risk being sent to the Headmaster. Stupidly I chose to ignore the warning and two weeks later I was spotted smoking at the bus stop on my way to school by one of the teachers. At morning break I had to report to the Headmaster and asked why I had not heeded the warning given? Of course I had no answer and moments later with my skirt removed I received six strokes with only my knickers between his cane and my bottom. This was six years previously and every so often, when I was in his study taking dictation or going through papers, I recalled the time when I had been caned.

But back to my predicament; I knew that I could not ignore what the Headmaster had told me and that I had to make some urgent changes. I would have to get out of bed earlier and not leave everything to the last minute. But could I repair the damage without making a bolder gesture? He had talked about caning me again, but in jest.

I remembered being caned when I was in the lower sixth and that I have never touched a cigarette since. Throughout my life I have a history of ignoring warnings and perhaps a short sharp shock was just what I needed. I thought about the idea of telling him that I was very, very sorry and if he felt that I would merit from being caned again as my way of showing him just how sorry I was to have been such a poor secretary, I would happily comply – or would he think that I was being ridiculous?

Whatever, I felt that I needed to come up with something to say to him before he returned from morning assembly.

When he returned, he walked straight past me without acknowledging me, and closed the door to his study, which made me feel even worse. I thought that I would make him a cup of tea and see if he would give me the opportunity to apologise. Minutes later I nervously knocked on his door before entering with a mug of tea and placing it on his desk, as he looked up and said that he was sorry for having such a go at me, but adding that I really need to think about whether I wanted this job.

I had my opening and told him that he should not be saying sorry to me; it was me that should be apologising to him, and I knew that my performance was well below what was expected. I thought about my earlier thoughts and decided to ‘go for it’ and make a big gesture.

Now nervous again and hesitating, I said to him: “Are you serious about your earlier suggestion? Perhaps I would benefit from a short sharp shock.” It was as though I had started and could not stop as I told him: “When you caned me six years ago, when I was a pupil in the lower sixth for being caught smoking for the second time after I had ignored a previous warning, I think it did me good and I have never smoked since. I have you to thank for that, and again I am feeling that I have ignored countless ‘little’ warnings about me being in late in the morning and not having everything ready for you in good time for morning assembly. When you were in assembly I thought about what you said and have to admit that being compared so unfavourably with Mrs Higgins was hurtful, but that everything you said was true.”

I paused for breath, before saying: “I cannot apologise enough, but if you felt that your suggestion about caning me again to see if I can mend my ways would be both merited and give me the short sharp shock I clearly deserve, I will happily accept whatever you think is deserved.”

That was it, I had said it, and actually felt relieved that I had got my little speech out. The Headmaster looked at me and told me that I was full of surprises. He paused and said that maybe, just maybe, my suggestion held merit, and that a short sharp shock might just work and mend my ways.

He said he was due to take a class as the second period of the day (despite being Headmaster, he also taught Pure Maths at sixth form level) after which he had the two fifth formers to punish during morning break. After that, if I still wanted to make this bold gesture, I should see him immediately after the break as the school started the third period.

Again pausing, he also said there are three key differences if I were to submit to being caned compared to the time I was beaten as a pupil six years previously. Firstly, when I had been caned for smoking, it was something that I did not have a choice about. Secondly, he had to adhere to Education Authority guidelines in that there was a maximum of six strokes. And thirdly, again with the guidelines set, a pupil had to retain a minimum of one layer of clothing. Now, six years later, I was effectively offering myself up for a caning of my own free will and that as an adult the guidelines set by the Education Authority did not apply. Therefore he said that as I had effectively asked to be punished, I should also determine exactly how the caning would be administered.

The Headmaster left shortly afterwards to take his Maths set, leaving me to think about what had been said. I was relieved that he had accepted my suggestion as a bold gesture, but equally perplexed about him wanting me to determine the format. When I had been caned six years previously I had to remove my skirt before getting six strokes across my knickers. He, having mentioned the Educational Guidelines that applied when I had been a pupil, seemed to have implied that he was expecting something more severe, which either meant more than six strokes or the horrifying thought of being caned without the protection of my knickers.

I concluded that if he was thinking more than six strokes, he was probably thinking double, or alternatively caning my bare bottom. In truth I had not given this any thought at all, simply anticipating that if he accepted my ‘bold gesture’, it would be the same as last time. However, I was where I was, and knew that I had to come up with a suggestion ‘outside the guidelines’ he spoke about. It also occurred to me, was he thinking both more strokes and bare bottom?

Putting that horrifying thought aside, I decided it was either twelve across my knickers or six to my bare bottom.

Morning break came too quickly, and the two fifth formers, Smith and Colman reported for their meeting with the Head. Smith was marginally younger and was called in first, leaving Colman alone in my room looking nervous. We could both hear the Headmaster talking to Smith before a pause and the faint sounds that could only mean he was taking his trousers off. A minute later there was the unmistakable sound of the cane cracking into Smith’s bottom and the normal grunt. Thirty seconds later there was a second crack and Colman’s mood had not improved. Smith’s caning took about three minutes and after another pause as he presumably replaced his trousers he came out of the Head’s study with the look of a boy that had just been thrashed, a look that I had seem many times before. It was Colman’s turn and over the next three minutes Smith and I were treated to the sound of a second caning, after which the Head emerged and told Smith and Colman to shake hands and go back to their studies.

Looking at me, the Head asked if I still wanted to make my bold gesture, to which I nodded and followed him into his study. On his desk was the all too familiar cane and he asked me what had I decided concerning format. In truth, I had not decided between what I thought were the two options. Stalling for time, I told him that from his earlier comments I assumed he was felt that as an adult I should expect a more serious caning from the one I received six years earlier, to which he nodded.

I knew it was time for a decision and asked if he felt six strokes given to my unprotected bottom would suffice? I could not bring myself to say ‘bare bottom’, but concluded that twelve across my knickers, which in any case were pretty skimpy, would be worse.

He replied that he had told me to decide and if six across my bare bottom was my conclusion, then so be it. He told me to take off whatever was necessary as he said that he thought he should lock the outer door as we didn’t want to be disturbed.

I kicked off my shoes before unzipping my skirt, which I then stepped out of. I was wearing tights that came off, one leg at a time, before I stood in front of him in just my extremely skimpy knickers. As he looked me up and down he remarked that if I had been considering more than six strokes with my knickers retained I had made the right decision, as clearly the knickers I was wearing would give little protection. We both knew what was next as I peeled my knickers down and off, and stood in front of him naked from the waist down and making no attempt to cover myself. I felt him focus on my pubic area with my neatly trimmed triangle at the junction of my legs.

He then told me to bend over the stool that had been recently used for the two fifth formers. I did as he instructed and reached down to hold onto the crossbar. This was the very same stool I had bent over six years previously, although this time it was my bare bottom on display and presented to him.

I felt the cane tap my bottom a few times before it ominously stopped. I instinctively knew he had taken it back before I received my first stroke, which was a real shock. I thought I knew what to expect, but this was much worse than I remembered. Whether I had simply forgotten, or whether it was so much worse without my knickers, or whether he was just caning me harder, I did not know.

Thirty seconds later I received the second stroke, another real cracker across the middle of my bottom. What had I been thinking when I suggested this?

The third came all too soon and my bottom was on fire. It was all I could do to hold onto the crossbar of the stool. I felt certain that I was being caned significantly more severely than six years previously and wondered if he had upgraded the cane itself. Or maybe he was just so cross with me that he was putting everything into this caning. Whatever, I had never previously experienced pain quite like it.

As the fourth cracked into my poor bottom I knew I had to hold on for just two more, as I lay over the stool with my damaged bottom on full show and my legs quite possibly spread wide apart.

The fifth was lower down, not far above the crease, and seemed even more sensitive, but as I lay there knowing that I had only one to go, the Head told me that I had done well and hopefully this little event would persuade me to mend my ways and become a diligent secretary again.

He left a longer gap, tapping my bottom several times before thrashing my bottom for the sixth and final time with what was probably the hardest of all. I heard him put the cane back on his desk as he told me that I could stand up. He asked if I was still pleased that I had made such a bold gesture.

I told him the caning was worse than I remembered, but that I had fully deserved it and hoped that it would remind me to take more care and be a better secretary. He told me he had probably caned me harder than previously, adding that when I had been seventeen and getting my first ever caning he would have been quite moderate, more in line with a middle-school punishment. However, as a twenty-three year old adult, the caning was be more in line with a proper sixth-form caning.

As this discussion was taking place, my bottom felt very hot and was stinging as I faced him completely nude below the waist. I again felt him looking me up and down and focussing on my wispy triangle at the junction of my legs. He told me that I should put my clothes back and go back to work.

He was quite flirtatious with me during the rest of the day, and before I went home I made sure that everything was ready for the following morning’s assembly. At just after five I put my head round his door to ask if there was anything else, to which he smiled and said: “No, but thank you for asking.”

When I got home, I went to my bedroom to look at the damage and was astounded by the six cane marks, each perfectly positioned across my bottom. When I went to bed, I altered my alarm clock to wake me up 30 minutes earlier and the following morning I was at my desk by 8.30. I had a cup of tea for him when he arrived. He thanked me and asked how my bottom was. I told him it had a perfect set of stripes and asked him if he wanted to see for himself. He smiled and told me he had assembly to prepare for, but perhaps later?

The End

© Pat Greenham 2016