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The Headmaster Canes Gabriele
Self-pity was the very last thing that I could have imagined for myself after all the years of careful preparation and slogging away through the ranks of "the system" to have finally reached my goal, Headmaster of a small, but nonetheless very proud and successful British public school, St. Sebastian's.
Maybe it was because I was so young. Maybe I had simply grown up in the wrong era, a man too old-fashioned for modern times, nonetheless, I felt cheated, deprived and remained with nothing but bitter regret. When the board of directors chose to pre-empt the emerging inevitability of public schools without corporal punishment, I was not the only ones of my colleagues to have chaffed and raised our voices in a collective roar of "No!!"
But I may have been the only one to have written too hasty a letter of retreat. It was a very simple, "I quit," and that was that. Was I not dedicated to education of the boys under my care? I was. Then what was the problem? Frankly, I didn't know what the problem was. Quite possibly I had chosen the wrong vocation in the first place. Quite possibly, the fact that my family had enough money for five other families assisted me in following a line of education that simply allowed me to rest on my laurels and not pursue something quite honorable, but less automatic.
I simply had been used to it all, the forms, the ranks of pupils up through the sixth. Most assuredly I had been very used to the canes and straps, the things that keep boys "between the wickets," if you will. Maybe I had grown so used to those things both for myself, then later for my own pupils that to stray from them in any manner frightened me to my core. Was I that shallow? Yes, quite possibly, I was that shallow, so my departure from St. Seb should be regarded as a mercy for all involved.
* * * * * * * * * *
My family owned a marvelous villa on the Amalfi Coast of Italy. My family had several such places and seldom utilized many of them for any length of time and hired a property management company to rent them out in between our wants and needs. All I had to do was lift up the phone, make a simple call and Casa Villa Rosa de La Palma was mine for any length of time I wished it and I indeed wished it, for a minimum of three months, the length of time I would need to pout and lay blame, then reflect and plan.
Some Headmaster I was, hey? Pouting? Blaming? What kind of man is that to lead boys? Well, I knew worse, a lot worse, men whose entire Head careers were spent at public school scheming, leering and pretending. They were supposed to be the best, some of them the best of the best. Give me a break.
At least I knew who I was. Maybe I leered at bare boy bottoms, caning them with great delight and gusto. But none of those boys ever knew of my interest, not one and never did they know what I did with myself after caning them though I did know what the boys often did among themselves. I had done the same. I was well trained for that aspect long before the pupil became the master, and then the Headmaster, <sigh>, water under the bridge.
* * * * * * * * * *
The Villa had available to me a part-time houseboy of sorts. His name was Gabriele, a beautiful boy, the kind of boy that had seldom crossed my path either growing up or at university or later when I was on the giving end of education. The lines, the curves of his eighteen year old boy were attractive in a way that one always hears about, but seldom is allowed to see up close and here he was, this picture of beauty, the servant of the Villa's and my needs.
He presented himself to me almost arrogantly that first day. I thought he might be some kind of reluctant employee, but it turns out his English was perfect, not even heavily tinged in his native Italian. I asked him where he was educated and indeed, he had spent a great deal of time at a rival public school in my native land.
It turns out that his family owned the property management company that kept the villa in perfect working order and things began to make sense. He was on a journey to become more than just the current manager of several such villas, he wanted to outright own the entire business one day. He was ambitious, but in a way that also seemed patient, if not a tad languid, which was not uncommon of younger Italian men in those days. He addressed me as "signore," the Italian word for "Sir," and I drank in his facial expression when he said it. It was tinged with a submissive countenance that I doubted that he allowed many others to see. He knew that I had "retired" from my educational career, that I had been a Headmaster, but none of the details.
Gabe, as he instructed me to call him, would come over early in the morning, three mornings per week for the first two weeks and bustle about, making sure that the housekeeping staff were on their toes, that the pantry was full and that the swimming pool company was keeping my watery gem in top condition. Then he would seek me out and ask me with a comfortable smile,
"Signore, is there anything that I can do to make your stay more comfortable?"
Where upon, I would smile, drink his linen clothing covered body into my memory once again and say, "No Gabe, I am quite comfortable, thank you," then he would turn, showing me his Italian backside, something that even his loose linen pajama-like leggings could not conceal its perfect shape and form and walk away, at times very slowly, leaving me with an urge, a need to cane that backside more than any other male backside that I had ever an occasion to cane!
All I could do was sigh, use the visions later for my personal enjoyments and dream of a fantasy time or universe when such a boy or boys would flood me with offers to "Headmaster" them through their young vibrant lives, using the cane as a source of motivation as well as for pure pleasure.
* * * * * * * * * *
A short time later, I left the Villa for a few days to go home to Britain and take care of some business matters and when I returned and sought the comforts of my swimming pool, the thing was full of some very nasty looking debris from a spate of wind gusts that had swept through the area for an unusual length of time. Gabe happened over a short while after my discovery and upon my showing him the pool, stood there and blushed. His skin was only a very light brown and the blush was confined to just his cheeks and accented his skin color in a spectacular way,
"I am so sorry signore! This is my fault! I don't know how this has gone uncleaned!" he said and then looked at me, "I will do this myself and fire the man who was supposed to be attending to this pool while you were gone!"
His ire excited me. His taking the blame doubled it. I wished like hell that he could read my mind. As I took to a deck chair and watched him procure the pool's cleaning equipment and get to work, I pictured Gabe's lithe youthful body, entirely naked, over the back of a pool-side chair, a stout rattan cane in my fist.
He would have finished his cleaning chore and then marching resolutely into the villa, procured a strangely present cane and marching back, he would have handed me the cane and begged me, "Please signore! Punish me! Punish me as I know only an experienced ex-Headmaster can!" then flung himself over the back of the chair, entirely divested of any clothing whatsoever.
In fact, as he did so, would I also see that his Italian pride was fully erect, even wet and drippy with excitement? Of course I would and then I would lay into him, making him count out twelve hard strokes in his native Italian no less! But that was not all. That would not be the end of it. He would stay there, in place, twelve beautiful purplish welts adorning his strong, muscular bottom cheeks. I would stride over and gently rub my fingers across the welts, forcing him to moan,
"Signore! Don't stop there, keep going, take me, take your new pupil as I know you wish to!" and I would comply, gladly and mount my young Italian stallion's caned backside, using him fully to sate my lusts.
It was not easy to conceal my physical excitement as I sat there with that fantasy and others like it about Gabe. He had stripped off his shirt and was wearing a gold chain that glistened against his hairless chest in the morning sun and as he worked, he developed a mist of perspiration all over his body, more on his forehead below his lush black hair that hung in moist locks that kept him shaking his head to move the hair out of his eyes. I so loved the modern hair styles of such boys.
When finally he was done, he came over to me, stood over me in fact, his linen leggings clinging some to his strong legs for the accumulate moisture, "I am done and I apologize again Signore, I will make sure this never happens again."
I smiled and even winked, "See that you don't Gabe, see that you don't!"
He looked down at me an extra moment. I had thought that I had done a very good job of concealing my excitement. He looked up, nodded, turned and then left, left me to self-administer my self-lusts, which I immediately set about to satisfy after a cooling dip into the now clean swimming pool water.
* * * * * * * * * *
For the next week, Gabe was not around. A female member of the family that owned the property management company, a sister of his, I think, had taken over, though she said he would return. I have to admit, she did a wonderful job, but she was not Gabriele, her beautiful brother.
So I spent the week rather impatiently awaiting his return, my fantasy lusts about him increasing to such an extent that at times I felt that I was inappropriately obsessed with Gabe, his body and the desire to have him for myself in every way possible. I had never been with a man or boy. Most thought me just an ascetic single man, devoid of such passions. I never dated women, but had lots of them for friends. Men my age did not interest me either in that way, but I had them for friends as well.
When Gabe finally did return, I was not sure that I wanted him to continue on. I was confident that I was going to say or do something so inappropriate now in his presence that I would have to leave the villa in humiliation. I prepared a gallant speech to him in my mind, an excuse to comfortably retreat; but when we were finally face to face, he was holding two things that I adored, a bottle of the best Italian wine, he knew as my favorite, the other, three perfect rattan canes.
I stood with him there in the entryway to the villa, my jaw dropped as he said,
"This one, the wine, is a present to help to excuse my absence signore. I had to visit your home country upon my father's request for business purposes. These, the canes I brought back with me, are to provide us with a means to … how shall I say it … finally consummate what both of us have been thinking, dreaming for weeks now. I have never been touched with a cane, ever. You, on the other hand Signore, are the perfect man, one that knows about such things, but were cruelly deprived if its pleasures, please, take them both."
I was trembling. I had never trembled before any man, any person. I took the bottle and the canes, my mind in a swirl of confusion, thinking he had not said what I heard him say. I just stood there then, dumbly. He smiled gently at me, came up to me and took back just the wine, "Come, let's share a glass of this wonderful delight, then, you will show me how to properly take a sound thrashing. That is the word in your country, is it not? "Thrashing?"
I was to learn that Gabe was not a neophyte in the bedroom. He had experience with boy girls and boys, something that seemed so natural for him in my eyes. I envied him that, but he did not hold it against me, not at all.
So we shared just one glass of the wine each, it was just right to smooth my nerves. Then we went to the large anteroom that opened to the swimming pool deck and he bade me to teach him my skill with the cane. From the get-go, he insisted that I treat him as I would any other pupil that I had punished over my years, only with him, to treat him in the way that my fantasies and lusts dictated, holding back nothing.
As I was also wearing a thin linen outfit, I took off my shirt and then bade him to strip naked, completely showing himself to me. He did and when he did, it was quite obvious that his young member had the same goals as mine, which I did not try to adjust or hide from him.
I even let my hands stray to between his thighs and fondle his testicles and flirt with his penis, then upwards to allow one finger to gently rub about his rosebud. All of those seemed to make him sigh and moan all the more, hopeful signs of what might transpire after his thrashing.
After my manual meanderings, I re-acquired the cane and stepping back, tapped his near hip, drew back my cane and struck, hard and sure through the center of his gorgeous cheeks. I watched his body tense, his head throwing back, his face showing surprise, but he sought no explanation from me for what he was feeling. I watched the first line rise up, it was perfect and my pelvis thrilled with the sight of it.
I tapped again, twice actually, drew back and gave the next cut lower, but not harder. This time, he was ready and his body flinched a little, but his head did not move. He did groan and I appreciated his mettle. The ability to stay still and not move or vocalize does not come naturally to most boys, certainly not ones new to the cane.
I gave him a third and then a fourth, each time harder and with more heft, as it were. His head came back and his face contorted and he mouthed an undecipherable complaint to himself. The fifth and sixed cuts were higher and I gained his feet and legs lifting and kicking, just a little. His voice growled, but remained uncommitted to words.
I had not committed to a certain number of cuts beforehand, but decided on eight or ten depending on his bodily reactions, but when on the eight he finally blurted, "Signore!!" I stopped. Eight beautiful lines were enough, quite enough actually.
He looked back at me and I nodded, "Well done Gabe, you made get up if you wish!" then he just slowly lowered himself to his knees in front of me, rather than standing.
Now it was his turn and his hands sought that my garments were lowered and I stood and watched as his mouth did not hesitate upon finding my entirely stimulated organ ready for whatever he had in mind. Gentle licks and furtive kisses upon my swollen member led to oral stimulations the likes of which I was unfamiliar.
Now he taught me the art and skill of a young experienced Italian lover, expressing a common but very ancient theme of the region that describes the perfect meaning of the phrase, "age before beauty." He drove me nearly to tears just by his present actions, then playfully stood up and ran outdoors to the swimming pool and dove into it, me closely after him. I captured him in the shallows and he unabashedly kissed me! I had never been kissed, my God! Here was this Adonis, this Italian man-child that could have anyone else on the planet he desired, but just then, he wanted me, so I kissed him back, and found my abilities to be frighteningly good and he smiled, "You are a beautiful man signore." I replied, "And you are a beautiful boy Gabriele."
From the pool, he took me to the ante-room and to the comforts of the large wrap around couch along the back wall and there he taught me about making love to a boy like himself. I had no idea, but his gentleness required nothing of me than to lay back and allow Gabe the freedom to seek out that which he sought for himself, the pleasure of the older man entering the younger, so simple and yet so profound and ultimately transforming. I would never be the same again, and didn't wish to be.
* * * * * * * * * *
Over ensuing months and even years, I never left Casa Villa Rosa de La Palma, there was no need. Gabriele increased in his family's business and hired others to do his managerial duties. One does not keep a boy, now a man, like Gabriele for himself. He belongs to the rare world that he inhabits and must be free to acquire those persons and experiences that he desires for himself, but he never left me without his frequent friendship as well as the companionship of other young willing males, one after the other.
How could I refuse his offer to privately tutor certain boys from many cultured and wealthy sources, beautiful young men that needed temporary assistance to plug not only the holes in their academic records, but to fill up other gaping needs as well, including the need to bend over the back of my chair from time to time. What could I say? Life was full and never dull.
Every once in awhile however, Gabriele would visit me by himself, walk into the villa's entryway with a bottle of my favorite wine and say, "Signore, it has been too long, shall we?" and then we would revisit those very first moments, duplicating each cane stroke, each kiss and later, each gentle, then lustful caress on the way to the inevitable coupling that always left me feeling as if I lacked nothing and missed nothing from my prior life and career.
If I was still a Headmaster, then it was inside of an invisible school of experience and feeling now, no board of directors to usher me out or tell me that things had changed for the worse or even for the better. I would never retire.
© Copyright PJ Franklin July 18, 2009
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Last updated: July 18, 2009