This story is self explanatory. The preamble should make it clear. In reality I thought I was going to meet up with such a person during the spring months. It did not happen, sadly. However I did manage to make a visit to an old friend and we created the situation I had desired with someone new. The photo on the side is the result. No longer a thirty year old bottom, as per the story, but one that thoroughly enjoyed being whacked. One may be getting old but one can still enjoy this most delightful of perversions. Enjoy the story, even if you have to avert your eyes. Alfred Roy
The Retired Headmaster
It’s a phrase that always caught
my eye and created a tingle elsewhere. And if I followed it up, a spring
infused my steps. Retired Headmaster. Just two words, but two words rich with
special promises and pleasures. Met one or two in my time. Whether they were
real headmasters or no, I cared not, the soubriquet was enough, especially if
they looked the part. Have been hankering recently to again meet up with one of
those like minded folks who still promote themselves as such but distance and
obstacles have so far thwarted. It hasn’t stopped me thinking that such a visit
is long overdue. Headmistresses, retired or not, don’t come cheap and the male
of the species often perform their pleasurable tasks for free or just a nominal
sum. To someone who cares little who bares his behind and stings it, as long as
it is done with expertise and relish, the situation is a no brainer. So I shall
continue searching and hoping and, in the interim, muse on a Retired Headmaster
experience I had some years ago.
He was a fussy little man,
dapperly dressed in three piece suit and bowtie, and reminded me more of a
floor manager at an expensive department store than retired headmaster. But he
had a malicious twinkle in his eyes and a warming smile when he discussed the
afternoon arrangements. Both facets set me at my ease and suggested promise. We
had communicated a couple of times before meeting. I travelled a lot in those
days and his palatial detached house, so he told me, was only a short detour on
my regular journeys along the A1. The Great North Road. I could call in on my
way back south in a summer heat that was heavenly both for the warmth and the
adventure. My northern meetings had been dreary but necessary and it was only
the thoughts of our meeting that kept up my spirits. Hardly surprising. I had been
put in touch with him by a like minded friend and our couple of telephone chats
established a rapport. He liked caning bottoms and I liked mine to be caned. As
a schoolboy. We could be made for each other he said, and chuckled. His parting
words, as we confirmed my visit, lingered throughout my business trip and
haunted every free moment. I shall take down your pants of course, he said. All
boys should be beaten on their bare bottoms. Yours will be no exception. I said
I would not have it any other way. Headmaster or not, retired or not, he
certainly ticked all my boxes.
Such anticipation, of course, can
frequently lead to disappointment. It had happened to me a couple of times. I
once, famously, spent seven hours in travelling for six of the best on my
shorts. All over in five minutes. That was it. The man who did it was happy. I
wasn’t. He had not stirred from his house. I journeyed home, three and a half
hours, with a slight sting in my bottom and a strong feeling of frustration in
my head. Could this be the same? A week or so spent in anticipation for five or
ten minutes of fleeting pain and little pleasure. I sincerely hoped not. I
reckon that seven hour jaunt, and other experiences, was why I turned to
professionals. Male and female. At least with them you get your sixty or ninety
minutes. They earn their fee. But amateurs, I use the word kindly, can be
unpredictable.
I need not have worried. From the
first tentative knock on door, the house was all he said, and the warm
handshake I sensed we would gel. Long journey, he said, let us have tea and
talk. So we did. I told him my desires and fantasies and experiences at school,
the latter particularly intrigued, and he told me what he intended to do. Allow
an hour, he said, I have no wish to rush. That appealed. No seven hour
frustration here, I thought. I had bought my PE kit, white top and shorts as he
had requested, and changed into them after the refreshing tea. Leave on your
underpants, he said, you may need the extra protection. And then he smiled. Do
not worry, they will be coming down. I tingled and, hastily changed, went to
the room he indicated. A headmaster’s study in all its splendour. A large desk
and equally large leather chair. A small bench on which, attired as ordered, I
sat and lots of impressive bookcases. And in the corner, near latticed windows,
a stand full of various implements. All designed to mark a behind. I waited for
about ten minutes and, shamefully, played with myself in anticipation. Only
through my shorts and underpants but, waiting, my desire was clearly strong. I
prayed he would not see.
I should make it clear at this
stage that I looked every inch the schoolboy. I was in my mid thirties,
slightly built, and with a very young face. My love of corporal punishment had
been kindled at school and flowered through my twenties. I was, and still am,
fortunate in that my bottom matched my face. Young and boyish but deceptively
capable of taking severe cane strokes. Made me popular at the caning parties I
regularly attended in those days. In anticipation of my meeting with this
retired headmaster I had refrained from any indulgence for a number of weeks.
Most caners that I know and knew appreciate a virgin, unmarked, bottom and mine
was pristine smooth, hairless, and unblemished. Every inch checked in bathroom
mirror, and every inch ready and eager to be painted in scholastic stripes. No
wonder I was playing with myself.
He caught me. I was so absorbed
in my lower fumbling I did not hear, or see, him enter the room. His manner had
changed, stern had replaced fussy and steel supplanted warmth, and I guiltily
blushed as he bid me stand. He expressed disgust, naturally, but secretly I
reckon he was pleased that my furtive actions had introduced a verisimilitude
to our preambles.
‘Do you usually indulge in such
disgusting habits?’
‘No, sir.’
‘In the headmaster’s study?’
‘Yes sir. Sorry sir.’
‘You will be boy. You are here to
be caned as you know. Gross insubordination. In view of your unseemly behaviour
I shall increase both quantity and severity of the cane strokes. Do I make
myself clear?’
‘Yes sir.’
‘I think twelve strokes, six on
your shorts and six on your underpants will suffice for the insubordination and
then a further twelve on your bare behind for this latter offence. Do you
agree?’
‘Do I have a choice sir?’
‘Do not get glib with me boy or I
might have those shorts down straight away and give you them all on your naked
backside.’
‘Yes sir, sorry sir.’
‘Yes sir, sorry sir. How many
times have I heard boys say that when they know that their bottom is about to
be beaten. It’s too late to be sorry, too late. It is time to bend over and
take your punishment. Punishment well deserved and punishment delivered to
where nature intended. To your bottom. A bottom that will be very red and sore
by the time I have finished. Bend over and touch your toes.’
He was in full stride through all
this, pacing and pacing up and down the room. I stood transfixed and a little
thrilled. As the pacing increased he crossed to the latticed window and
selected a cane from his copious selection. It was red, medium thick, and made
for a goodly swish as he flexed it. He amplified my thoughts when he referred
to it as a senior cane, redwood, designed to sting the most obdurate of
behinds. His face was flushed and his eyes gleamed in anticipation. Bend over,
he said, touch your toes or grasp your ankles. Six strokes boy. His voice was
thick and, as I replied and did as instructed, my own was almost as breathy. I
couldn’t touch my toes but I did manage to grasp my upper ankles and keep my
legs straight and steady. I was conscious of both my upturned bottom and,
reassuringly, the fact that it was covered by both shorts and underpants. That
cane looked vicious. I was both headily expectant and slightly scared, both
feelings enhanced by the thrill I felt when large hands explored my covered
rear. He may be a retired headmaster and I a naughty schoolboy but, prior to
delivering his first set of stings, fantasy allowed a short sexual frisson that
reality would frown upon. I sighed as those hands explored all of my nether
curves. My bottom cheeks, my crack, my testicles and penis, all felt the
clothed touch of exploring hands. Did he do this when he was a real headmaster?
Did he desire to do it and resisted? Was he at last fulfilling suppressed
passions? I cared not. All I thought was do not stop, do it more, cane me, and
then when my pants are down do it again. When the redwood cane touched my
bottom for the first of my first six I was as stiff as the hardest pole.
When it landed, hard and straight
across the centre of my clothed bottom, I was not so keen. It stung like hell
and the fiery line engendered caused a shuffling of feet and a reaching
forward. Hold still, he said, clearly consumed by the corrective act. I did,
manfully and painfully. The line throbbed and I knew I had been caned. Albeit
only one stroke. Two and three quickly followed and I gasped at both the
intensity and the residual pain. My poor bottom was developing an all consuming
heat and staying down, ankles grasped, was proving difficult. Retired or not,
true or not, this headmaster certainly knew how to cane a boy’s bottom. I
readied myself for strokes four, five, and six and prayed they would be quick
and accurate. The pain in my rear was eclipsing all other thoughts and desires.
My penis had flagged, my breath had exhausted, and the burn on my cheeks was excruciating.
I closed my eyes and beseeched those prayers. It did little good. The latter strokes
stung and burned and my discomfort rose to new levels. But I remained
submissively down and pain eased as a short intermission was followed by
exploration of my ravaged backside and the gradual lowering of my shorts. That
was perverted bliss. Resting, as they were, on my ankles I was now conscious of
hands exploring my tight fitting, and thin, underpants and my increased
vulnerability. The burning bottom and eager, manly hands, returned my penis to
its earlier full state and flagged a silent acknowledgement that the second six
strokes should be delivered. He took his time. The hands explored for what
seemed an eternity. But I was not complaining. The burn in my bottom had moved
from discomfort to pleasure and the hands, and my submissive position, merely
enhanced it. As manly fingers and palms caressed filling balls and throbbing
cock of eager student, a side benefit one could say, a small and slightly
covered bottom was indicating its readiness for more of the same. Six more cane
strokes, six more as hard as you can, but this time on buttock cheeks only
thinly protected. He needed little urging. Silence was only filled by heaving
breathing. His palms stroked and lingered on my heated curves for just a few
moments longer and then, pressing my back and urging me to straighten my legs,
he lashed six fairly quick and hard strokes of his redwood cane across my ready
and upturned bottom. I gasped, I squirmed, I edged forward, I did not rise but
continued grasping ankles, I squealed out loud, and finally I rose clutching my
savaged bottom and howling. It had hurt, by God it had hurt, and I could see
from his smiling face that he was well pleased. He was well pleased and I was
well tanned. So much so that, burning rear notwithstanding, all in front had
yet again flagged. Two minutes of cavorting and vigorous rubbing ensued and
then a comment, many comments, that continued both the pain and thrill of a
heady afternoon of scholastic fantasy.
‘I see that my ministrations
have, once again, removed your erection.’
‘Yes sir. That second six really
hurt.’
‘So I see. The next twelve will
be even more painful. Over my desk, I think. I cannot see you holding ankles
for those.’
‘No sir.’
‘Especially as those underpants
are coming down. Bare bottom boy. Twelve strokes of my redwood cane on your
bare bottom.’
‘Yes sir.’
‘Yes sir, no sir, yes sir. Is
that all you can say? No matter. Your little penis will no doubt rise again, in
fact I think it already has, but twelve hard strokes across that bottom will
expunge all that. But given its manifestations I reckon it is time I saw it.’
‘Yes sir.’
‘That and your little bottom of
course. Given my exertions I have earned that right.’
‘Yes sir.’
‘Then hands on head and stand up
straight. I want no distractions.’
And he didn’t. I placed my hands
on my head, stood up straight, closed my eyes, and waited. Five seconds later
my underpants were pulled down to my ankles and large hands explored my
blistered backside and my, by now, full and urgent balls and cock. I was in
heaven. They say pain comes before pleasure, pleasure follows pain. This was
writ large in this anonymous house on my long journey home down the Great North
Road. I had been caned, a hard twelve strokes on my covered bottom by a retired
headmaster who, before this day, I had never met. And now with shorts and
underpants at my feet I was being explored in the most intimate way. I sighed
and gasped as large soft hands stroked my very private parts and then gently
turned me round to inspect and explore my lacerated bottom. Fingers
tantalisingly traced the weals on my backside, followed by a gentle rubbing of
palms on the same burning skin. I closed my eyes and drank in the twin sensual
pleasures of large hands on my bottom and twitching cock in front. I prayed I
would not spurt before the pain I had to come. Twelve hard strokes of that
redwood on my naked bottom. The thought made my penis twitch again and it was
almost with relief that I was bid to lay over the desk. It had been cleared of
all paraphernalia and the smooth leather studded top did not cause discomfort.
I stretched my arms, as instructed, and gripped the far side. The action caused
my white PE vest to rise up my back and emphasised my lower nakedness. Shorts
and underpants were still at my feet and as I waited they were removed. To
allow me to stretch my legs he said. They allowed much more, so much more. He
wanted my legs stretched wide and, lifting the vest, my back and bottom arched.
I could not see the final picture but I could imagine it. Naked, except for the
small vest now pushed to my waist, my small buttocks were accentuated and ready
to be thrashed. And in between my genitals were exposed and vulnerable. A true
boyish picture for a headmaster, retired, to fulfil his own desires. And I had
no complaints. It was all I wanted. Providing the cane, already experienced on
covered bottom, connected only with my bare cheeks, I could endure. However
painful. I closed my eyes and sensed the cold cane pressed against the centre
of my bottom. A bottom already well striped and still warm. This was it. This
is what I had travelled down the Great North Road for. This was my all
consuming wish. A savage cane to lash my bare backside, and to be done by a man
who desired the same even more. A match made in heaven. He did not disappoint.
My retired headmaster, or at least for this blissful hour or so, did what he
had promised and threatened. He thrashed that cane into my exposed bottom the
twelve expected times. Each stung like hell, each created its own particular
fire. Most across the centre of my bum, but some slightly higher or slightly
lower. But all in the area of the buttock curves and none stray enough to cause
alarm. He knew his job, he knew his target. What had he said? The area that
nature intended, or something like that. He was experienced, he was good, and
he was enjoying himself. Ten or fifteen seconds apart each vicious stroke
caused a resounding thwack on my naked skin and each made me gasp and squirm.
But I suffered it all, gritted my teeth, absorbed the pain, stared at his
latticed windows for relief, and gasped breath and shed tears. Not many, but
enough to know that my bruised behind had sent the appropriate message to my
brain. The last two were harder and quicker, he sensing perhaps my weakening
resolve, but the task completed he sighed and tapped my legs with the implement
of much discomfort. All done, he said, well done, he said. No blood. I said
nothing. I just lay there, across his desk, naked and beaten and serene.
Strange? Yes, but strange in the way only those who seek such pleasures can
understand. He understood, my retired headmaster, he understood. And I
understood him. I had taken his gift but, in doing so, had returned it. I
sensed that we were both happy even though only I, as is usual in such cases,
only I had a very sore bottom.
‘You took that extremely well.’
‘You gave them extremely well
sir.’
‘I aim to please. And call me
John.’
‘Yes sir. John.’
‘No regrets?’
‘No sir. John. No John. It was
all I wanted.’
‘And needed?’
‘Yes.’
‘Good. I must say you have a nice
bottom. Actually a lovely bottom. Could have been designed for corporal
punishment.’
‘I have often been told that.’
‘Oh?’
‘Even at school. A chemistry
teacher once told me that I had the nicest bottom he had ever caned. I didn’t
appreciate it at the time.’
‘How old were you?’
‘Thirteen.’
‘Did he take your pants down? Did
he do it bare?’
‘No sir. John. No. But I think he
would have liked to.’
‘Didn’t we all.’
‘You say we. So you were a real
headmaster?’
‘Of course.’
‘And did you?’
‘Did I what?’
‘Take down the pants of your
boys. Cane them bare?’
‘No, never. Not done, even in my
day. We could still cane, of course. Often did. But I had my fantasies.’
‘Now realised.’
‘Yes.’
‘You are very good.’
‘As I said, I aim to please.’
‘You did John. Sir. God, how I
needed it.’
‘For this relief much thanks.’
‘Hamlet.’
‘Very good.’
‘Thank you sir.’
‘Worthy of another twelve before
you go.’
‘Yes sir.’
‘Then back to my study boy and
pants off. I wish to see that bottom again.’
And he did. And I got another
twelve with the redwood before departing. Nothing else. It had been clear from
the first session that he was happy to play with a boy’s genitals prior to caning
but all else was off limits. That would have to wait until I got home. Spurting
my built up tension would be fuelled by imagination and recall. As it should
be. Headmasters, even retired ones with unfulfilled fantasies have their rules.
I and all on the Great North Road would understand. At least I hope so.
(c) Alfred Roy 2017