I'm a Retired Headmaster

**happygolucky** · 02-05-2014, 11:53 AM

This story is just that: A story. It is wholly untrue and contains not one jot of a fact. It contains scenes of heavy duty punishment and gay man to man sex and is quite explicit.

Latterly and just before my retirement I was headmaster of a boarding school and I come from the era when boys were properly behaved and properly punished – I believe these factors are related. I took a great deal of pride in the accuracy of my swing, in the temperance with which I accompanied each beating and in the mentoring style of our educational system.
Life was all made the absolute pleasure it became by my penchant for male bodies. For me, they were a work of art and something that gave me seriously worrying stirrings in places I’d prefer not to admit. The solution was simple – I never touched any of them and I ensured that no punishment administered or sanctioned by me was as a result of any misfeasance. I played it completely straight and am proud of my record. This was set to change and the events that led to my ‘road to Damascus’ alteration in course I will outline here.
It was a bit of a surprise when one of the boys from the last days of beating being allowed got in touch through an ‘old-school’ forum and asked me out to lunch. I do stay in touch with a number of ex-pupils so it didn’t seem too strange however, and I’ll cut to the chase, he had a very interesting proposal. The lunch was in London near his house – I live in Sussex and had traveled up by train and he took great pains to stress that this was his treat. He had, he said, made a lot of money through the wonderful start our school had given him and he simply wouldn’t notice the cost. Lafitte at £120.00 a bottle is well outside my normal range so when he ordered the second I knew he wasn’t bluffing.
As the coffee arrived he started to unfold his proposal. He leaned close to me in a sort of conspiratorial way and almost whispered.
“I miss the beatings you used to dish out, they were simply the best, far better than prep school and I can still feel the tramlines stinging me to sleep. I used to stay on my back and push myself into the bed to make them even more intense and those horse-hair blankets, well, rub them a few times and wow.”
I was a little taken aback but retained my composure and merely asked him how he would like things to progress.
“I’d like us both to go to my house now, to show you where everything is in my study and then to leave while you get acquainted with it all then knock at the door, be told to wait and eventually to enter. I’d then like you to punish me and to do whatever you’d like to me. To, use me.”
Till the last part I was content but I couldn’t be sure how he would truly react if I did what I really wanted to. I tried to explain.
“The last part might shock you and may be unwise as I might do something you will regret.”
“It’s alright Sir” he interjected and his use of the title sent a small shiver throughout all corners of my being “I know you longed to touch us, I always saw the little readjustments in clothing halfway through. I so respected you for not giving in.”

Ten minutes later we were inside his house, a large detached property in Primrose Hill and he led me to his spacious and very sumptuous study. From just about every cupboard he produced instruments of chastisement and then, was gone. I picked each cane up in turn and then noticed an open book on the desk. It was clearly there for my benefit and as I turned the pages the contents made me aware that is was a punishment book. It was, in almost every way the same as the one I used to keep among the school records. I was so engrossed that I hardly noticed how much time had elapsed and was taken by surprise by the timid knock at the door. What a naughty boy he’d been.
“Wait.” I barked, slipping effortlessly into the role I once relished. There was a gown on the back of the door and I quickly donned it then walked to the window and gazed at the lazy suburban scene outside, a cane tapping against my leg. I let him stew for all of two minutes.
“Come.” I heard the door open and him walk in.
“You sent for me Sir?” I remained motionless.
“Yes Wilson. The punishment book tells me we have quite a lot of catching up to do, wouldn’t you say?”
“Yes Sir. Sorry Sir.”
“Normally I only cane boys but I think we’re going to have to be a bit more imaginative today and I expect you to take your due punishment in the true manner of an English schoolboy. Is that clear?”
“Yes Sir.”
At this point I turned and saw a young man now dressed in school uniform, not shorts but smart, sharply ironed long trousers, an old school tie and jacket. It all still fitted him very well and I was transported back through all those years.
“Move to the centre of the room then bend over and touch your toes.”
“Yes Sir.”
“We’ll start with six strokes of the senior cane across the seat of your trousers. This is a warm-up and for no particular offence.”
“Yes Sir.”
“Count them out boy.”
I measured my distance, cleared my head of all thoughts save the task in hand, took a couple of practice taps then let rip. Six evenly spaced and beautifully timed strokes were applied to that delicious rump and he hardly moved a muscle.
“Six thank you Sir.” He said at the end.
“Now drop your trousers then resume the position.” His white Y-fronts were quickly exposed and the lump inside them told me how much he’d grown up. He bent again, this time grasping his ankles. I selected a nursery cane and again tapped my practice dance.
“Six strokes with a nursery cane for stealing from your former employer.”
“Yes Sir.”
I laid these on heavily as, although called a nursery cane it’s a misnomer as it hurts like hell especially if applied hard. But through his underpants I reckoned he could take it and, besides, this was punishment. I made the first stroke the second hardest, the last being a real wrist wringer.
“Take your jacket and underpants off then lean against the desk with your hands gripping the edge.” In this position He was leaning forward with his arms taking his weight and my strokes would be more of a downward movement. His bottom was hairless and pure white with no sign of fat or flab. This time I chose a junior cane.
“Six strokes with a junior cane for not declaring the perks you used to receive.”
“Yes Sir, thank you Sir.”
With each stroke I saw his semi-hard and rather large cock bouncing a little further into view and my own reaction was purely instinctual – I caned harder, saw more of it and grew yet harder myself. I moved next to him and, slipper in hand announced his next ordeal.
“Thirty six with the slipper for cheating at cards.”
“Yes Sir.”
This time I moved in; close and personal, allowing his thigh to meet my crotch and knew he could feel the meat of the leg I never walk on. I put my left arm around his waist and pulled him in tight. The walloping was thorough and very severe and by the end of the thirty-six he was dancing a merry little jig and rubbing against me in a very stimulating fashion. His bottom was bright red all over and I could tell he was enjoying himself but being more than a little stretched. I left his side and stood silently taking it all in.
“Stand up in the middle of the room.”
I walked towards him and then circled till behind. I moved closer to him and then reached round and undid his blazer buttons. I pulled the garment from his shoulders and let it fall on the leather sofa. I did another circuit of his body this time stopping in front of him.
“Remove your tie.” He did so and I then moved closer and started to slowly unbutton his shirt. Each one revealing a little more of the ‘boy’ within, his semi hairless chest, his taught tummy, his raging hard-on. I gripped it hard and slowly pumped.
“What’s this boy?” I demanded.
“Sorry Sir, I can’t help it Sir, - it just happens.”
“Does it indeed well we’ll be getting rid of it one way or another; won’t we boy.”
“Yes Sir.” I continued my ministrations and watched his face intently as he squirmed, his eyes screwing up with pain or pleasure or perhaps both. With my other hand I pushed his shirt from his shoulders and gazed in awe at the lovely site before me. An erect and upright and now, big ‘boy’ with an erect and upright cock, a room full of toys and book full of sins – heaven comes in many forms.
“Kneel.”
“Yes Sir.” He dropped before me.
“You know what to do.”
“Yes Sir.”
He quickly made his eager way through the folds of my gown and found the buckle, the catch and the zipper of my trousers. He undid them and then, in that gloriously anticipated moment, fished inside and found his reward, the lollipop he longed to lick, the stick he dreamed of beating and the cock he knew he would swallow. And, swallow he did, in one deft and accomplished movement from tip to base. ‘You’ve had a lot of practice at this’ I found myself thinking. It wasn’t just the up and down, or the in and out movements that were so perfect it was the little tickling touches he made with his tongue as his head traveled that completed the perfect blow job. I knew this was going to end in me coming very quickly if I didn’t stop straight away so I pulled him off. I had other plans. He seemed genuinely crest-fallen.
“Lean over the desk and grip the other side.”
Naked and beautiful, tall and erect in every sense he did exactly as I had told him. I had to stop and drink it all in. This was about as good as it could get was all I could think and as I drank in the sight I looked at his already bright red buttocks knowing this would be his final beating for today.
“You’ll get six strokes with the senior cane. This is to punish you for continuously breaking the speed limit.”
“Yes Sir, thank you Sir.”
I had already decided to go top to bottom so to speak and to finish with the last stroke, the hardest stroke being applied to the upper thigh, just below the nates. There were two reasons for this decision. The first was entirely physical, the last would be the one that, on this sensitive spot would really sting like crazy. The second was entirely psychological; as he would know the direction I was heading and would be fearfully anticipating the denouement he fully, and correctly expected.
I selected the heaviest of the three senior canes and took up my position. The first landed with a hiss and a loud crack. His head jolting upwards was accompanied by a sharp intake of breath. I waited as the tramline started to appear, his breathing returning to almost normal. I like a final caning to take about six or seven minutes so you can work out for yourself just how much ‘head time’ I was giving him
“One, thank you Sir.”
The next landed an inch and a half below the first and was every bit as hard but was in the meat of the buttock so bit into a thicker wedge of flesh
“Two, thank you Sir.”
Again I let him suffer whilst congratulating myself for my undiminished prowess in accurately applying welts to a supplicant’s backside. This time I decided to try my old and trusted technique, unused and rusty though it might be. Alerting a miscreant to the likely timing and positioning of a particular stroke has always struck me as a big mistake. If the only sound preceding the arrival of rattan shaped hell is the swoosh as it cuts through the air then why give the wretch any warning by tapping one’s intended target. ‘Trust your eye my good man’ I thought. So I did. I mustered all my powers of concentration and focused in on the exact spot I craved and let it fly. Wow. The effect was electric his whole body jerked as though hit by 240 volts of pure welting pain.
“Three, thank you Sir.”
‘Follow that’ I thought and raised the memory laden stick of fire above my shoulder, higher than ever before and watched as though an observer at a Morris dance as the feet landed between the swords and my delightfully supple cane yielded its buttock raising, breath inducing and totally magical effect upon my willing victim.
“Four, thank you Sir.”
By now I was dangerously close to my final stroke position, that place of agonizing intent I fully meant to leave as a lasting memorial to my skill. ‘Get this right and even if I die tomorrow, it wills all have been worthwhile’. This time I took aim; the gap was so small I had no choice. I tapped, forewarned, educated, and his gasp was audible – he knew this was going to hurt and he knew it would be as nothing compared to the last. I brought mister five home with the unerring skill of all my forty years apprenticeship and, as though coming home watched with baited breath as that beautiful, hard pressed body arched in exquisite recognition of the skill and mastery he had allowed into his home.
“Five, thank you Sir.”
All of my years of beating boys bottoms had been tempered with the absolute conviction that I would never abuse my power; would never be unjust or wicked but here, in this extraordinary circumstance I was suddenly free. Free of all notions of child abuse – this was a man, a fully grown thirty five year old man who desperately wanted what I was delivering, free of the onerous responsibilities of my former position and free of the mentoring role that is so exhausting. This was my moment to enjoy and savour and, as I eyed that sweet spot just below the crease of the buttock, where the thigh is most prone and the flesh most taught I knew that I would need all my skill to make this mine. Again I tapped. Alerting him to his fate and, as I did so he winced, knowing this was to be a lasting monument to our relationship. I raised the cane, heard its supple song as I swished it back and forth then placed my eye on the target, held my breath and let my arrow fly. It was pure unadulterated poetry. It caught exactly where I wanted it to and found that most tender point that raised a howl from my supplicant like a dog locked in a kennel alone and defeated. His body arched as though trying to rub away the growing embers of flame that had been ignited in his very being by waving his torso at the air. It wouldn’t work – it would be a week before he forgot this one.
“Six, thank you Sir.”
I waited and watched as his bottom as, filled with a life of its own, it waggled a hopscotch dance, first this way, then that as he tried to resist the all powerful and demanding urge to rub and to rub and to rub. Then, in kindness and in a haze of lust I obliged: first one welt, then the next; each in turn till I reached the sixth, rubbing them with my greedy forefinger and, as I did so I saw his buttocks flinch and contract, then open slightly in that inviting way.
“Wilson” I said as he lay twitching, “I’m sorry about this but I’m going to rodger you.”
“Yes Sir.” Was the only response.
I wasted no time, dropping my trouser and underpants and plunged heavenwards and quickly up to the hilt. His smooth and perfectly formed bottom contained all of my dreams, all of my hopes, all of my abandoned fears and my rampant lust and, as I thrust, dallied, parried and ploughed he wriggled his horny and haranguing response with an equal thirst to my own. I must admit to becoming clumsy – I literally banged the boy with increasing fervour as though trying to knock him into the next room but my own lust was angry, was paramount and was greedy. I, in truth didn’t care about him. Getting my ‘end away’ was all that I cared about and, as I tugged at his hair, pulled against his shoulders and felt my essence becoming one with him an enormous sense of relief gushed forth with it. I was free.
Tragedies are born of fatal errors and, happily I had never made one. I had remained the purest of the pure; when all around me were the demonic representatives of the worst of the demons in humanity I had stood proud and aloof yet tempted and turned on. Somehow I stood clear and maintained the me that I know exists inside, so now, having ploughed my adult ‘victim’; having ridden him like a man possessed and as I had felt my prick finding his prostrate I had let go with all of the un-protected urgency of my forty years of alone-ness. He was filled and I had squeezed out every last drop.

My control was gone but my lust was in tact. His arse was in ribbons but my lust was in tact. My come was spent but my lust was in tact. My lust was in tact and his arse, his body, his person was still mine.
I turned him around, making him lean back against the edge of the desk and dropping to my own knees I felt my little prep-school training coming to the fore as I swallowed his engorged protein producer from tip to base and stayed there, exactly where I knew I loved being; rewarding my beaten boy with the orgasm of his life. I’d done it in all of my fantasies and just about every other one had come true this afternoon so why not this one. He filled me. Filled my mouth with his cock, my sense of smell with the animal olfactory contribution he dumped everywhere, my hair with his hands as he pulled me home, my awareness of me with his beautiful body and warm hands rushing everywhere and then, as he exploded in my mouth and I slapped his sore, welted buttocks he dumped all of his frustration into my eager throat and I swallowed, licked, swallowed and licked, sucked and swallowed some more and he slowly gave me what I craved and allowed my adult soul to emerge.

So, here I am. Wickedly perverted and yet, wholly decent, completely trustworthy. I could baby-sit a five year old with no danger to either and yet I have a toy; a mature but beautiful toy to call my own who needs me to penetrate him and beat him, to abuse and worship him in equal measure. He is mine and retirement is bliss. The taste of his cum is as though a chateaubriand were being served with that Lafitte he lavished so generously upon me in that lovely restaurant and I am his but he is mine.

Life renews itself around the cycle of the seven stages and I am young once more.