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A PERPLEXED HEADMASTER

by Clifford Dorset


My Dear Amelia,

I apologise for sounding so incoherent on the phone last night. When I called you, Caroline Alexander, the School Bursar, had just left me, and I felt rather disoriented, not to say confused! The whole day, in fact, had been so perplexing that I was very much in need of a sympathetic ear.

As brother and sister we have always been very close, even on intimate matters, and you have very kindly listened to my problems, personal and professional, many times over the years. In my emotional confusion I failed to appreciate that it was most inconsiderate of me to call you at 3a.m., when you would almost certainly be in bed. I do apologise, and I would also like you to convey my sincere regrets to the young lady who was with you when I called. Even if the girlish giggling that I could hear in the background indicated that your companion was not seriously inconvenienced, I accept that interrupting you was unforgivably impertinent.

Part of your superbly soothing advice was that I should write down an account of my encounter with Miss Alexander, as a means of taking stock and setting my thoughts into some semblance of order. The remainder of this letter is the result. As you suggested, dear sister, writing this account has helped me understand the course I must adopt, and I hope that my words will also help you understand the predicament I felt I was in when I called.

You will remember, I'm sure, the many times our dear departed father used to opine that the course of true lust never did run smooth. I'm starting to realise now the wisdom underlying what seemed, at the time, to be simply his off-hand jocularity. It was, without doubt, based on his own, rather rash, entanglements with various ladies rather than the experience of matters amatory that he gained during his marriage to our highly respected mother. In this regard, I have frequently wondered over the years about the role played in his busy life by the surprising number of unaccounted-for ladies who appeared at his funeral. Even though they maintained a respectful distance during the proceedings, I remember remarking at the time how colourful, even jolly, they all were.

There now follows my account of my meeting. After this, you will discover my current assessment of my position as I see it, and I suggest that you forbear reading this until you have assessed my account of the events.


My Meeting with Caroline Alexander - Preliminary Information

Miss Alexander had always been an exemplary employee in her role of Bursar; highly efficient, and in fact very attractive. Not that I had allowed her appearance to influence my choice of her for the post, of course, but being well dressed and friendly in manner is always an important advantage for one who is often the first member of staff seen by prospective parents when they visit us. Her academic qualifications are also beyond reproach, rather better than some of the teaching staff, in fact.

However, her behaviour lapsed rather dramatically on the day you happened to choose for young Lucy's appointment here, at which I subjected your protégée to a severe caning, as you know. (Thank you, Amelia, for your subsequent email, indicating your satisfaction with my chastisement of Lucy.)

When Lucy had departed, I discovered Miss Alexander indulging in what is perhaps most politely described as an intense episode of self-gratification involving partial nudity of the female parts. And in her office! The episode seemed to centre around a brief item of Lucy's intimate apparel, treated as a fetish object, and I considered her actions to be a clear breach of the confidentiality and decorum that I expect from my staff. Shocked as I was by this discovery of such a sensual aspect of Miss Alexander's character, and on school premises too, I felt I had no alternative but to punish her for this breach. I believe it was Miss Alexander herself who suggested that her punishment should involve a caning, and one of a severity that matched the chastisement I had given Lucy earlier.

Events quickly accelerated from that point, and almost before I knew it, Miss Alexander had divested herself of almost all her clothing and she was bending over my desk, presenting her superbly rounded - and completely bare - buttocks for a hard spanking, followed by twelve salutary strokes from my favourite cane. Perhaps I should add that, as we amicably negotiated the manner and extent of her punishment beforehand, Miss Alexander expressed heartfelt sympathy with the difficulty I was experiencing, as a man, in needing to balance my obligation to discipline her while I was suffering considerable sexual arousal at the prospect of exercising this obligation on her particularly attractive and nubile feminine bottom. In these discussions she left me in no doubt that she desired to effect some practical method of relieving my difficulty at some stage. Being fully aware, my dear sister, of your own erotic nature, I feel I need hardly be more explicit regarding the options available to her for such relief.

So it will not surprise you to hear that, very shortly after the twelfth stinging stripe inflicted by my cane had started to ripen into a crimson swollen glow across Miss Alexander's gyrating buttocks, my stiff male part had entered her natural haven rather forcefully, and was being exercised vigorously within her sublimely slippery depths.

Following the inevitable climax to such exercise, being the mature professional adults we are, we parted amicably, and immediately resumed our scholastic duties. As you know, I have never been one for expressing affection, particularly of the impetuous variety, and my practice following episodes of intimacy has always been to restore a sense of normality. Miss Alexander appeared to concur with this. I am prepared to admit to you alone, dear Amelia, that I found the episode hugely enjoyable, and that I thought a lot about Caroline during that night and the following day. For my part, I found her submission to my authority, however stern and painful it was for her, to be most invigorating, and I suppose that, in my subconscious, it wasn't long before I was musing on ways in which we might repeat the experience. The following day I certainly found it difficult to take my eyes off her rounded derrière as she worked with me on tedious paperwork in my office.

Experience, however, has taught me the pitfalls attendant on being over hasty with developing relationships, associated with raising unrealistic expectations in a woman's mind of possible long-term stability. It's preferable, I've found, to risk annoyance and frustration than to appear 'over-keen' to women with whom I've shared certain intimacies.

The fact that Caroline had clearly demonstrated her bisexuality, in her undeniable lusting after Miss Lucy and in her more than enthusiastic participation in the activities I had myself promoted, reassured me that her feelings for me would consequently be less prone to inappropriate escalation. It seemed to me quite reasonable to suppose that I would be able to insert myself into Caroline's seemingly varied erotic schedule to our mutual satisfaction, without displacing any of her female 'inamorati'. I believe it is common for males to find stimulus in the contemplation of erotic activities that simultaneously involve more than one female; perhaps I allowed such intriguing thoughts to cloud my judgment in this instance.

I'm reasonably confident that my strategy would have worked as well as it always has, had it not been for a passing observation I made a day or so later, when Caroline had been called away from her desk. Just before her screensaver took over, her screen caught my eye and I found she had been spending time on a website devoted to the birching of young ladies' naked bottoms. I made a note of the web reference - as evidence, you understand - and a few minutes investigation using her computer showed me that she must have been spending some considerable time on these salacious pages. Incidentally, my dear Amelia, I would not be surprised to learn that her quest for birching materials had been aided, if not actually initiated, by young Lucy ... or perhaps by some other member of your household whom she'd met during her French-teaching duties!

Departing Caroline's office, I found myself in a quandary. Caroline had breached one of the school's cardinal rules in using her official computer and the school's network, for personal use. Although I had resolved not to ensnare my Bursar into furtherance, or even simply a repeat, of our earlier dalliance, I felt obliged to take vigorous and timely action. I left a message for Caroline, detailing the disciplinary charges against her and instructing her to attend later in my study, so that she might present whatever defence or mitigation she believed appropriate. I also instructed her to make use of the birching information I had detected on her machine for the construction of a birch rod that would form the basis for her punishment, should she be found guilty, of course.

At that stage, despite my planned assignation being much sooner after our first delightful romp than I would have preferred, for the reasons detailed above, I was confident that, whatever took place, I could maintain our status quo. My equanimity was shattered, however, by Caroline's response to my instruction.

In her reply to my message specifying her shortcomings, she acknowledged her culpability regarding the misuse of her computer. Indeed she surprised me in the alacrity with which she not only agreed to construct a birch, but specifically requested 'a sound birching on (her) bare buttocks. She even included the somewhat racy detail that she would present herself wearing custom-made 'whipping drawers'. To cap it all, she included in her message a wealth of salacious information, provided at considerable length, regarding some bare-bottom birchings she had experienced at a school she had once attended that was run by an uncompromising disciplinarian by the name of Mrs Verwoerdt.

This heated detail was accompanied by similar minutiae concerning the offences that were felt to necessitate such punishment at the said school. These included certain of Caroline's amatory escapades with a younger female, and her message intimated that this female, known as Adèle, and whom Caroline specifically refers to as her 'slave', is currently domiciled with Caroline!

I consider that such information is certain to engender highly distracting thoughts in anyone, such as myself, who enjoys a predilection for chastising the plump rotundities of young ladies. I'm sure that Caroline was sufficiently cognisant of my tastes in this vein, following our earlier naked encounter over my desk, for her to understand, very well indeed, the probable effect of her message on my more excitable sensibilities.

Taking all of these factors into account, I felt convinced that Caroline's intentions at the planned disciplinary interview would be, in her mind, much more amatory than punitive. I felt my authoritarian control slipping away as I read her descriptive material. But it was the closing words in her message that chilled me to the bone. She related the advice of Mrs Verwoerdt that she, Caroline, ' ... would need someone who would correct me whenever I so fell from grace.' She went on to inform me that 'I think I have found that person in you, my dear Headmaster, with which state of affairs I am extremely happy.'

Leaving aside the ambiguity (and grammatical lapses) of this sentence, I'm sure you can appreciate, my dear sister, that I understood that it represented a clear and serious threat to my long-established bachelorhood!

But that is not all! Her message artfully delayed mentioning what is perhaps its most momentous matter until its final paragraphs. The effect on me was akin to what the popular press tends to call, rather whimsically, a 'bombshell'.

Somehow Caroline had uncovered our school's plan to admit female pupils in the near future, a plan of which you are aware but which has remained predominantly secret until this apparent and unfortunate leak. The discussions I have had with you, Amelia, regarding this proposal have been, of course, in the strictest confidence, relating specifically to a possible invitation to you to become a member of the school's Board of Governors. Your potential role in establishing whatever changes prove necessary to the school's disciplinary procedures could, in my opinion, play a major part in the success of this venture. The possibility that the leak is in some way related to Caroline's recent involvement with your household has occurred to me, and needless to say, I would take a very dim view of this, should it be proven. However, I will of course accept your personal assurance that the possibility of this having happened is negligible.

Nevertheless, the damage has now been done, and I have impressed upon Caroline that if further leaks can be traced to her there will be dire consequences, possibly involving dismissal from her present post.

To return to Caroline's message of reply, however, I must tell you that she specifically requested that I appoint her to the post of Vice-Principal in the mixed school, 'with special authority over the girls'. Her 'request' was couched in such terse language as to sound like an ultimatum, and she followed it immediately with the following sentence:

'At all times I am prepared to submit myself to your discipline when you think it necessary for me.'

In the context of the overweening presumption that characterised her demand for promotion to the exalted position of my deputy, I could not but see her words as an inducement, involving the offer of her sexual favours in return for the post. Further consideration made me wonder, indeed, whether her words might also imply a subtle threat, based on the power that her knowledge of my predilections might allow her, were they to become public knowledge.

Caroline concluded her message with some thoughts on disciplining her female charges. I will not grace them with repetition here; suffice it to say that her ideas indicated a less than mature attitude to discipline, one in which her own gratification appeared paramount.


The account to which I refer above, of my interview with Caroline Alexander, will follow shortly.

My Meeting with Caroline Alexander

Caroline appeared in my study on time, birch in hand. I must tell you that her appearance was little short of stunning! Presumably inspired by my instruction that she acquire old-fashioned 'whipping drawers' for her punishment, she had adopted a costume redolent of the old, formal style of girls' finishing school. It was, without doubt, simple, elegant and admirably practical, comprising merely three items: a skirt of quite stiff, coarse black material, of such a length that her shiny black court shoes merely peeped shyly from beneath it; a simple white linen blouse, long-sleeved and voluminous, although it failed to completely hide the impertinent outward thrust of her firm breasts; and on her curled locks a straw boater, trimmed with the single splash of colour in the ensemble, a plain ribbon of crimson silk.

She entered, her skirt rustling busily, and locked the door in anticipation of the personal nature of what she fully expected to ensue. Carefully placing the birch rod on a seat by the door in silence, she dextrously removed her hat and its restraining pin.

As she approached, eyes modestly lowered, it was with definite pleasure that I watched her elegant, girlish movements. Her clothes well concealed her trim body and perfect limbs, but somehow they also enhanced it, making my imagination race. I could well imagine a crocodile of a dozen or so young ladies in such attire, progressing gracefully and silently through the gates of a traditional Ladies' Academy, preceded by a black-bonneted matron of superior mien, on their way to an improving visit at some local museum or gallery of art.



© Clifford Dorset
Not to be reposted, reproduced or distributed, in part or whole.