Spanked And Caned By The Headmaster

Whilst living in Cape Town I made several contacts through the SpankThis Hookups web site. One was a "Headmaster" in his late forties, whose favourite spanking and caning role-play scenario was to punish naughty adult schoolboys whilst they wore tight fitting Speedos.

As I am into Speedos and sexy, tight fitting briefs, the thought of being spanked and caned by him had great appeal. So I wrote him an invitation to visit me and to use my study as his Headmaster's study. I also included the following:

"Dear Headmaster

I wonder whether you could help me in a personal matter that actually happened and which has troubled me for many years?

Decades ago whilst at Grammar School in Essex I failed to own up to some serious classroom vandalism that a friend and I were responsible for. After an announcement in next morning’s assembly that the perpetrators had better own up or be expelled, he owned up and got six of the best in the Headmaster's study.

I kept quiet, got away with it and to this day I still feel like a coward in need of catharsis for what I did.

I believe that a visit from you for me to experience expertly administered authentic scholastic whackings, with slipper, tawse and cane, on my bare bottom, would finally relieve me of this feeling of guilt.

I also suspect that you would gain some pleasure from doing what my Headmaster should have done all those years ago. You will no doubt also increase the punishment as a kind of interest, accumulated over the years, for me failing to pay the penalty at the time of the crime. I would love to oblige you and submit to a series of extremely satisfying spanking sessions. As can be seen from the attached pics I am fit, trim, muscular with a pert bottom badly in need of attention. If this opportunity to help me achieve atonement appeals to you why not consider visiting me for a long and serious CP session?

Yours obediently

Spockings, B - Lower Sixth Form "

He visited the following weekend and catharsis was achieved! Subsequently I wrote the following to him:

"Dear Headmaster

This is the first opportunity I have had to communicate with you since I visited your "study" and I thought it might be helpful for any future sessions to put down my considered thoughts on the event.

Firstly I must congratulate you on your ability to put me at ease and accommodate my various limitations - this probably reflects your considerable experience in such matters. I also admired your ability to assume, chameleon-like, the mantle of an old fashioned Headmaster in a totally realistic and controlled manner. You were authoritative, masterful, demanding respect and, not least, extremely intimidating. You really made me feel once again like a recalcitrant schoolboy who had been found out and was now about to face the music.

The interrogation and dressing down you gave me was as good as it gets and certainly as good as any I received at school. Skillfully you gradually changed my initial professed innocence and denial of guilt into a full blooded confession of my crimes. When you had finished I really felt remorseful and was ready and willing to accept any punishment you considered appropriate. Certainly I expected to be caned and six or even a dozen of the best applied to my bare bottom would not have seemed unfair.

You were indeed the quintessential Headmaster, feared through the ages by all naughty schoolboys, a paradigm of authoritarian pedagoguery. Yet previously you had written “I do role play if the sub wants to but usually I just administer the CP", implying that you are disinterested in or possibly not comfortable with role play. From my previous experience with others sharing our interests and who enjoy role play, none of them any way matched your performance – you could easily have been an actor if you had needed an alternative career to that of the legal profession.

You pronounced sentence - an OTK hand spanking over my school shorts, a serious OTK spanking over my Speedos with several “tools of the trade” and finally twelve strokes of the cane bent bare bottomed over your desk - and then you carried it out - professionally, skillfully and with, I suspect, considerable personal satisfaction. The last comment reflects an earlier one of yours -"I suppose I just like attending to bottoms be they young, old, male or female!"

In the event my bottom certainly was well attended to! You started with admirable restraint and circumspection. As agreed, a gradual warm up was applied to properly prepare my buttocks for the eventual, inevitable caning. Following an initial solid OTK hand spanking I was ordered to place my hands on my head and nose to the wall and, with my bottom still smarting from the hand spanking, I was given plenty of time to contemplate the error of my ways and ponder on the punishment to come.

After an agonising wait you ordered me to keep perfectly still and brought things to a head (in more ways than one!) by slipping my tight, bottom hugging schoolboy shorts down to my ankles leaving my bottom only protected by my tight fitting Speedos. As directed I kicked off the shorts and I did not resist you guiding me back over your knees for what I expected would be a prolonged and severe spanking.

You did not fail me. For at least ten minutes you belaboured my increasingly reddening cheeks with a variety of spanking implements. As I recollect these included a ballet slipper so well used its sole had a shiny patina; a long stiff leather paddle with "Bum Chum" lovingly imprinted on it; a stinging French martinet; two black leather Scottish tawses, one supple and sweet the other stiff and tart, and finally the diminutive Newlands cracking cricket bat, signed by Paul and Simon two spanking friends of note, who are both well aware of the painful pleasure gained from hitting a six with this bat.

Considerately you then soothed, massaged and kneaded my burning buttocks, apparently deliberately unaware of the seven inches of throbbing masculinity trapped between your muscular thighs. To your credit my arousal was purely pain induced with no additional manual manipulation needed on your part. And so you continued. Following a further ten minutes of "hands on head, nose to the wall", my glowing buttocks afire, I heard you select one of several canes in your extensive collection and several times you swished it ominously through the air, wordlessly warning my trepidating buttocks of their impending thrashing. Then I felt you gradually lowering my skimpy Speedos and the elastic of the waistband stretched as it crossed my hips and buttocks. My suddenly growing frontal protuberance briefly impeded their downward passage but the elasticity of the material allowed the Speedos to pass over my pulsating penis and slip to the ground.

Then came those fateful words.

"Right boy, bend over the desk - it's time for you to receive your just desserts - the kiss of the cane. A dozen painful kisses to caress and imprint on your bottom a lasting reminder of what will happen if you misbehave in future.”

I obeyed. Red faced and red cheeked I turned and walked to the flat desk, stretched over it and grasped its far side. Naked from the waist down my vulnerability was absolute and, incredibly, my organ continued to assert a will of its own, erect and throbbing, anxious for sexual discharge.

Your cane taped my inner thighs. "Legs wider apart, boy, and raise your buttocks higher. They need to be well presented to gain maximum benefit from this caning!"

I strained to obey and now on tip toes, with my bottom pushed out and upward, I awaited your pleasure and my deserved and now, admittedly, much needed cathartic pain.

Expert caner that you are I did not have to wait long for the first flash of lightening to strike home with a blinding, agonising searing slash across both buttocks. Tap, tap, tap stroked the cane as you judged distance, amplitude and target before raising and flashing the cane in a downward arc, cracking with gunshot precision and accuracy into my vulnerable buttocks. The delayed pain response lasted milliseconds and immediately thereafter I felt the full impact of the first seriously applied stroke of your cane. I had been caned dozens of times previously but I cannot remember anyone approaching your ability to apply the rattan with such profound effect. White heat inflamed my bottom and the agonising fire reverberated through my flesh, causing tears to flow from my eyes. And this was only the beginning!

I will not bore you with a stroke by stroke account of you administering the subsequent eleven cuts – you know how well you did. Suffice it to say that the delay between strokes was sufficient to allow the full impact of the previous stroke to “sink in”, maximising the painful aftermath of each stroke. Also I could not stop myself crying out each time the cane landed and the tears that were evident when you had finished were real and demonstrated both the severity and effectiveness of my punishment. Subsequent private examination of my buttocks revealed the depth of your skills as a caner. The twelve strokes had been evenly spaced apart, forming a series of horizontal red and bruised tram lines, none overlapping and all producing a similar crimson glow in my otherwise pale pink bottom. Four of the strokes had drawn blood where the tip of the cane had landed. All in all the caning was a profound and proper punishment for my errant school boy activities and I thank you for doing your duty both rigorously and, I might say, not without some enthusiasm.

After the twelfth stroke had landed I remained in position whilst you allowed me to regain my composure after receiving what I know was the severest thrashing I had had in my life. I was now experiencing that warm afterglow that many a naughty school boy is familiar with after a visit to the Headmaster’s study. The heat in the buttocks gradually spreads from the nether regions to the groin resulting in the dichotomy of painful pleasure as the erectile tissue of the penis becomes engorged with blood, causing the organ to swell and elongate. In my case the “little head” had remained erect throughout the caning and now was ready to burst, with pre-*** oozing from its tip.

However you heightened its excitement by admiring the results of your exertions with gentle tactile probing along the weals and tender squeezing and massaging of each buttock. Rock hard, throbbing and near to ***********, my penis now cried out for attention and manual relief.

But you had a better, more sophisticated, and for me frustratingly unique answer to my plight. Wordlessly you continued massaging my bruised and battered bottom and then, without warning, fingered my anus, gently probing and easing a forefinger through the sphincter. This aroused me even further but the hand was withdrawn and instead of more massage you took up again the leather paddle and proceeded to spank each cheek in turn, applying at least ten moderate spanks to each. I then felt that delicious cold sensation of personal lubricant being squeezed between my buttocks, which you then parted before again easing you forefinger into my rectum where its penetration produced erotic feelings I had not previously encountered. As it searched for my prostate your digit gently eased itself further and further into my rectum and then stopped. With your finger still in place, your other hand you recommenced the paddle spanking, causing me to raise and lower my buttocks to welcome each spank and maximise the pleasure of this extraordinary turn of events.

Now you began to finger **** me in earnest. Each time as I raised my buttocks anticipating the spank of the paddle you thrust your finger in deeper, withdrawing it as I lowered my rear after each spank. Your finger had quickly located my prostate and skilfully massaged it every time my bottom muscles pushed upwards in anticipation of another spank from the paddle.

Men who have experienced their prostrate being massaged until it ********** will attest to the fact that it is an uncontrollable emission on the part of the person being massaged. It is totally different from the orgasmic *********** caused by penile stimulation and many male submissives accept it as a means of ****** control by their dominant male or female partner. While the prostate massage is very pleasurable, most men are unable to ****** by prostate massage without some kind of penile stimulation. Once a sufficient amount of ejaculatory fluid has been drained, insufficient fluid pressure to trigger the ejaculatory reflex will remain, and no amount of penile stimulation will result in ******. Thus a submissive male may be denied the pleasure of ****** for months on end by daily milking of his prostrate.

In my case there was no penile stimulation and the painful pleasure of your dual, simultaneous attention to my buttocks and prostate evolved into an unforgettable, stimulating experience. I did not experience normal ****** but after a few minutes of your expert stimulation I ********** copious quantities of fluid, far more than I produce following normal ******, resulting in a very wonderful feeling of submission and relief. It was an exquisite sensory experience I will always remember and no doubt one that I will want to repeat……..

So perhaps I had better own up to a few more schoolboy pranks and mischievous activities that I got away with as a teenager, which at the time would have undoubtedly resulted in several thrashings by the Headmaster?

Yours respectfully

Spockings, B Lower Sixth Form

P.S. My buttocks have now completely healed and appear to be in need of some attention."
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1 Response Jul 12, 2012

what a wonderful story.
Has given me some ideas for when i next visit the Head Master's study