Mr Hennessey’s Boys 4. Timothy’s story

used master

Previously in Mr Hennessey’s Boys

Episode 1, Howard’s story

Episode 2, Noah’s story

Episode 3, Ethan’s story

 

 

Mr Hennessey has a stable of young men who for a price are willing to offer their backsides to corporal punishment enthusiasts. Here, Timothy goes back to the classroom …

 

“Boys like you need to be punished or you’ll never learn. Stand up Kennedy. This will be a lesson you’ll never forget.”

Mr Higgins waved his cane threateningly at me, almost in my face.

I scrapped back my chair and rose from my school desk and prepared for the order, “Bend over and touch your toes.”

I was in an actual classroom and Mr Higgins was a genuine schoolmaster and I’m pretty darn certain ‘Kennedy’ was a real schoolboy too.

Mr Higgins had put me in the detention class at [name redacted] an actual boarding school. The real pupils were on holiday and we seemed to have the building to ourselves. Higgins was a schoolmaster at the school. Either that or this was the most spectacularly blatant guerrilla movement ever. A stranger just moved into the classroom as if he had every legitimate right to be there.

I think Higgins had a beef against three pupils in particular. Maybe they gave him a hard time in his classroom and he couldn’t do a thing about it: corporal punishment having been abolished.

That evening I kicked off as ‘Turner’, found guilty of cheating in his history class test.

“Turner you will write out fifty times in your neatest handwriting, ‘I must not copy out the work of other boys in a test and then pass it off as my own.’”

It was incredibly tiring and by the end my wrist was as sore as it’s ever been; even after one of my marathon wanking sessions.

The classroom was a mixture of the old and the new. The lighting and air conditioning was definitely of ‘today’, but the school desks were from a time long gone by; those individual ones they had that opened from the front and had a hinge. As I was soon to discover the slope from the back to the front made an ideal platform for a schoolboy to bend across and offer his bum up for the kiss of the cane. Kiss? Who am I kidding? The SWOOSH! THWACK! OUCH!! of the cane I mean.

I was wearing an authentic blazer from the school, a rather natty royal blue number with yellow braiding. I rather admired it to be honest.

Mr Higgins had a traditional academic gown and again I’m pretty certain that it was the authentic one he probably wore in his daily life. The whippy rattan cane he was brandishing was the real deal too (I can give personal testimony to that), but I suspect it had to be taken out of mothballs for that evening, since caning in schools had been abolished a generation ago.

He looked through my lines and was dissatisfied.  “Pah! You call this neat handwriting, Turner?”

“Stand up and bring your chair with you.”

He took my straight backed wooden chair and put it against the back of another.

I climbed on one chair and bent over the combined backs and placed my hands palms down on the seat of the other. I’d never seen this position before, but it turned out it was all the fashion eighty or more years ago. It certainly placed my bum at the perfect angle for him to slash his cane into the seat of my trousers. Which he then proceeded to do.

They were six real stingers and I could feel the cane had made welts across my buttocks, but I’m pretty resilient and took it like a champion.

“Stand in the corner, Turner. Hands on head.”

That was end of part one.

There was no commercial break; I was just left standing, until Mr Higgins rearranged the furniture.

“Probert,” he called to me. “Sit in that desk.”

He then gave me a stern lecture about my misbehaviour in the history lesson. I was always playing the class fool.

“Take fifty lines. ‘I must always remember that nobody in the class is the least bit interested in my attempts at comedy.’”

It took me nearly an hour and by the end I was ready to soak my wrist in a bowl of cold water. Soon I’d be happy to bathe my arse there as well.

“Probert, you think you can make a fool of me, but you can’t. I am going to demonstrate that now. I am going to beat you like you have never been beaten before.” He said it with such conviction, I really felt sorry for the real Probert, whoever he was.

“Take down your trousers and bend over the desk.”

I hesitated. I figured that was expected of me. Trousers down? We were moving away from reality, here.

“Now, Probert. Do as you are told or I’ll double the number of strokes.”

I stood in front of the desk, let my trousers fall and leant across the desk. The sloping lid made a wonderful platform, presenting my bum as the highest part of my body. Mr Higgins pulled the waistband of my white underpants tight. I winced as the cotton rubbed against the raw welts left on my buttocks, courtesy of Turner.

He laid six strokes into me, at intervals of thirty seconds. I couldn’t see his face, but I knew he was relishing every cut of it. It genuinely hurt and by slash number four I was groaning, but I kept in position.

He left me hanging over the desk for what seemed like an age, while he admired my tight buttocks. I don’t know what was going through his mind; was he lusting after the genuine Probert, or me? To be honest, I’d rather not know; sometimes with the gentlemen it’s best not to.

After a session in the corner, Probert morphed into Kennedy. I never had the opportunity to meet the boy, but I rather wish I had. He must have really pissed Higgins off. The lecture went on for ever; his rudeness, insolence, impudence and disrespect of authority. Yep, Kennedy did not like Mr Higgins. I wonder what he would think about this crazy game being played out in his name?

We didn’t do lines this time but went straight to the action. “Stand up Kennedy. This will be a lesson you’ll never forget.”

I walked as instructed to the front of the room. “Boys,” Mr Higgins intoned to an imaginary class, “I want you all to witness this. I will not tolerate insolence and any one of you who has the audacity to take me on, will befall a similar fate.”

There was a glassy faraway look in his eye as he swished the cane through the air. I think he was beginning to lose it.

“Trousers and pants down, Kennedy. Bend over and touch your toes.”

As anyone who has ever heard that dreaded command knows, the bending over and touching toes isn’t the hard part. The hard part is staying down after the slash of the rattan has taken half your arse off. If you are bending over a chair or a desk, you have something to grab hold onto for dear life. But, when you are touching your toes, you are on your own.

My bum was still throbbing and quite scarred from my previous two canings, so when Mr Higgins flogged the first cut, and I do mean ‘flogged’ it into my bare buttocks, I yelped like a dog and shot up to clutch at my roasting cheeks.

“Over Kennedy. Don’t be a coward. Take it like a man,” he stressed the word “coward” in a way that sent a shiver down my spine. This guy truly hated Kennedy and wanted the real boy to be there that evening, but that was impossible, so I was to be his whipping boy instead.

I bent down again, grabbing hold of the trousers that were crumbled at my ankles. Slash two whipped against my arse, it came with such force I’m sure he was trying to cut my body in two.

Number three was worse. I was howling like a wolf. If there had been anyone else in the building surely they would be running to the classroom to see who had been killed.

Was Mr Higgins still in control of himself? How could I be sure? I had never called off a session mid-way, but that evening I came pretty close.

I took the full six and was in some distress; so, it seemed, was Mr Higgins. His breathing was erratic and his eyes were rolling in the back of his head. I’d never seen anything like it before or since. Was he in ecstasy? Like those religious fellers who speak in tongues?

In extreme agony, I dressed myself and waited for him to come back to planet Earth, but he was in lunar orbit and wouldn’t be coming home for a long time yet. I felt the used bank notes in my pocket and realised there was nothing to keep me there. I collected my bag and left, still wearing the rather nice royal blue blazer.

My backside was twice its natural size and when I admired it in the mirror at home, there were eighteen very distinct welts; six of them were as thick as my finger. It wasn’t too bloody and after I gently massaged ointment into the wounds the agony slowly turned to a glowing throbbing.

It is a cliché of spanking stories that the punished boy is in so much pain that he has to sleep on his stomach at night and he can’t bear being touched by his bed clothes. It isn’t like that in real life in my experience, but that night for me it came mighty close.

That night I couldn’t sleep too well, not because of the pain in my buttocks, real though that was. I was tossing and turning trying to work out Mr Higgins. I was certain he really was a schoolmaster at that boarding school and Turner, Probert and Kennedy were real boys, either his current pupils or from his past. Had his session with me been some kind of exorcism for him?

I was intrigued by the man and I longed for him to contact me for another session. Months passed, the memory faded and I had to accept that I would never meet the man again.

Then, one summer’s day I got a call from my agent Hennessy. Mr Higgins asked did I mind letting him teach a friend the art of caning using my backside as his prop.

The man is bonkers, absolutely bonkers. I told Hennessey, Yes, I replied and arranged to meet Mr Higgins at his apartment.

But that’s another story.

 

Other stories you might like

Trouble at the mall

The Gafffer of The Academy 2. In the chill of the night

The coach and the schoolmaster

 

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

 

Mr Hennessey’s Boys 3. Ethan’s story

Previously in Mr Hennessey’s Boys

Episode 1, Howard’s story

Episode 2, Noah’s story

 

Mr Hennessey has a stable of young men who for a price are willing to offer their backsides to corporal punishment enthusiasts. Here, Ethan encounters a sweet gentleman

 

Mr Wilkins was probably the weirdest of my gentlemen, but also one of the nicest. He treated me like a son, almost literally.

I would visit him at his house, always at the same time: 3.45pm; just as the schools turned out. His thing was for me to come home from school and behave like his little boy. He liked me to dress in a scarlet school blazer and would have me dress in really short, short trousers.

Then I would have to play with my toys for a while and then he would find an excuse to pick up a slipper and spank me.

I have done a few “domestic” scenes for my gentlemen; but mostly they aren’t father-and-son stories. People seem to prefer to play as “uncle and nephew”. Strange that: I don’t know why, it might be having me play their “son” is a bit too close for comfort, especially if they have real-life sons of their own.

Mr Wilkins treated me like his son. I never asked him if he had any real sons, I thought that was too dangerous. But, he had lots of toys for me to play with, so where did they come from?

Usually, as soon as I got home from school I would get the toy box out and find something to play with, just like an ordinary boy might. One afternoon he fed me fish fingers and chips before play-time. That really freaked me out.

He made me a bit nervous another time I visited. I was crawling round on the floor playing with miniature “Matchbox” toy cars. He had quite a collection from about fifteen years ago, with some models of cars that you never see on the roads today. I was on the carpet, going VROOOM! VROOOM! pretending to rev up a car’s engine when Mr Wilkins got on the floor with me, took one of the cars, and whooshed it across the carpet.

“Come on let’s have a race.” He wanted to play together just like we were eight-year-olds. So, we did.

I didn’t want to think what the heck was going through his mind. Despite the number of hours we spent together me and Mr Wilkins never had much of a conversation, so I couldn’t tell if he was a bit simple.

We played like that for twenty minutes or so before he stopped suddenly, lifted his head theatrically, and said, “Oh, is that the telephone?”

It wasn’t of course. It was pretend. But it was a pretence that would bring us both back to the real purpose of my visit.

He left the room for about five minutes, before returning with a stern look on his face.

“Well, Peter,” he said. Who was Peter? That’s not my name, but he always called me Peter.

“Well Peter that was Mr Knight on the phone.”

I took my cue and gave him a suitably alarmed look.

“Do you know what he wanted?”

No, actually, but I was sure Mr Wilkins would soon get around to telling me.

“Well, Peter?”

I gave him my best abashed eight-year-old child’s look as if to say, “I’ve been a very naughty little boy” and let him get on with the story.

“You’ve been firing your catapult at his cat, again. What have I told you about that?”

So we went through the story. I was a bad boy who had been warned more than once about annoying the neighbours. What had I to say for myself? (Not much) And so on.

Mr Wilkins strung it out for quite some time. He always seemed to enjoy this part of the evening even more than what was to follow.

Eventually, he said, “Peter, go fetch my slipper.”

I picked up his bedroom slipper from next to the fireplace where it had been left to warm and handed it to him.

“You have been a very naughty boy, haven’t you, Peter?”

I agreed that I had.

“I am going to spank your bottom with my slipper, Peter.”

I tried to look suitably alarmed.

“Go and stand by the arm of the settee.”

I did as I was told, while he smacked the slipper into the palm of his hand.

“Peter, this is going to hurt me more than it does you.”

Oh, per-lease…

“Take down your shorts and bend over the arm of the settee.

They were down in a jiffy and I was in position.

Mr Wilkins came and moved my blazer away so that my white underpants were fully exposed.

Then, he spanked me. Six whacks with the slipper. I hardly felt a thing. I never did when Mr Wilkins did it.

He made me lay across the settee for about twenty seconds, before he said, “I’m sorry to have to do that Peter, but you are a very naughty boy. You can stand up now.”

My face was red (from being over the arm of the settee) but I knew if I inspected it later my bottom would be unblemished.

“Sorry,” I sniffed, although I was nowhere close to wanting to sob.

“Get dressed. It’s over now.”

And, it was. Mr Wilkins looked genuinely upset that he had been forced to spank me. He ruffled my hair a little and with a weak smile, said, “Go to your room now.”

I changed my clothes in the hallway and picked up the bag of Liquorice Allsorts he had left for me on the telephone stand. I didn’t need to check, I knew there would be five used bank notes hidden among the sweets.

I opened the front door and closed it gently behind me.

Yes, Mr Wilkins was very nice to me the few times I saw him. It was a pleasure to be his son Peter, if only for an hour at a time

 

Mr Hennessey’s Boys episode 4, Timothy’s story is here

 

 

Other stories you might like

 

The housebreaker

Where’s the paddle, hon?

When Dad got home

 

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

Mr Hennessey’s Boys 2. Noah’s story

Mr Hennessey has a stable of young men who for a price are willing to offer up their backsides to corporal punishment enthusiasts. Here, Noah dresses up for Col Sanders.

Mr Hennessey’s Boys Episode 1, Howard’s story is here

 

My handler, Mr Hennessey said he would pick me up at my place at 2pm to take me on an adventure and he arrived on the dot.

He brought with me a full Boy Scout uniform; complete with khaki shorts and a wide-brimmed hat.

“Put these on before we leave. There won’t be a chance to do it later,” he handed me a paper package.

No way! I couldn’t risk people seeing me dressed like this. I was very anxious. From the first time he suggested this job, I had my doubts. Now this. Parading around my own manor dressed like a nineteen-thirties Boy Scout. No way. I might just as well walk around with a placard round my neck: ‘Boy for Sale.’

Mr Hennessey understood. He was always great like that. He was a businessman, but he never forced any of his boys to do something they didn’t want to.

“Ok, ok,” he shrugged his shoulders, “We’ll find a layby on the way. You can change there.”

Minutes later we were in his Ford Escort and on the road travelling out of town.

When Mr Hennessey first suggested this trip I said, “No. Emphatically, no.”

“Look”, he had told me. “There’s this client I have. Calls himself Col Sanders. I know! I know! I don’t think he’s even a real colonel. If he is he must be retired. He’s old enough. Lovely, man. You’ll love him.”

It was the Hennessey soft sell. His job as an agent was to match up the client and the boy. One wanted to do the spanking and the other was willing to oblige: for a fee.

This job was no different to any of the dozens of others Mr Hennessey had arranged for me in the past. Except that it was.

“He wants to watch while I spank you,” Mr Hennessey said it as if it were the most natural request in the world.

I’m not sure what my objection was. But, I didn’t want to do it.

“It’s just like those videos you do,” he flashed me a grin and flung his arms wide, “Except there are no cameras.” He laughed at the absurdity of his own argument. “A bit like the theatre, then. A live performance.”

Looking back, I think it was Mr Hennessey who was the problem. He was my business manager, not a client. I didn’t think he was interested in taking part in a spanking session. Like most of his boys he was in this for the money. It was purely business. But I loved being punished by older men. If I let him spank my arse, the ‘relationship,’ if that’s the right word for what we had, would change.

I thought he wasn’t into spanking, but I had heard reports that there was one lad that he saw to regularly. He was a well-known television actor with a big part in a soap opera. I’ve no idea if he was gay but there were rumours. Why is it that only cute good-looking boys are ‘accused’ of being gay? People never talk about the possibility that a pug-ugly fat blob is gay.

So, maybe Mr Hennessey had hidden depths himself.

No, I said, sorry, this was one gig I was turning down.

Then he told me the fee.

“How much?” My jaw probably literally dropped. Greed is a terrible emotion and it can get you into a lot of trouble. That’s how a week or so later I was sitting in the car with Mr Hennessey with a Boy Scout uniform on the back seat on my way to meet Col Sanders.

Traffic was light and we made good progress through the afternoon traffic. Then, without warning, Mr Hennessey pulled into a parade of shops. He disappeared into a green-grocer’s and emerged with a brown paper bag of fruit.

“Here,” he handed me four apples. “We’ll need these later.”

Out of town we found a secluded spot and I hid behind a hedge. In the blink of an eye I was transformed into a nineteen-thirties’ Boy Scout. The khaki shorts fell three inches high of the knee, ideally emphasising my great legs and cute bum. The greenish shirt was made of heavy cotton and when I rolled up the sleeves to my biceps it clung to my muscular gym-honed torso. There were merit badges sewn on to the shirt. They looked authentic to me, but what would I know. But the thing I adored most was the black-and-red striped neckerchief that when swirled up and tied around my neck dangled down my chest. I would love to wear this all the time. It would turn the boys’ heads in the bars.

Mr Hennessey gave me a cheeky wink and a thumbs-up when I returned to the car. “Oh yes! You never fail to deliver. You are going to make a happy man very old today.”

I cheered up considerably in my scouts’ uniform. You had to hand it to Mr Hennessey; he always knew how to dress his boys. I felt very proud to be part of his team. We delivered the best.

We drove on for a few more miles in companionable silence. Then Mr Hennessey piped up.

“This is the deal. You are the naughty boy in the village and I am your father. I have caught you scrumping, you know stealing the colonel’s apples, and I take you to him. That’s it really. Then we play it by ear. Or do I mean by ‘rear?’” He laughed at this. Mr Hennessey was a great businessman, but he had no future in stand-up comedy.

So, it was an improvised sketch. My part was to be a small kid and as in real life I had no say in what was going to happen. If my ‘father’ decided I was going to get a dose of his leather belt across the bare arse, then so be it.

“What’s with the scout uniform?” I asked lovingly fondling the neckerchief.

“I think we are re-enacting something real from his past. I’m not sure. I find it better not to ask too many questions.”

Soon, Mr Hennessey pulled up in front of a large detached house. Col Sanders certainly seemed to have a lot of money; why shouldn’t he spend some of it on me?

We got out of the car and I was approaching the front door when Mr Hennessey pulled me back.

“Wait,” he stooped down and took a small handful of dirt from a flower bed.

“Authenticity,” he said, as he smeared my knees with the dirt. For good measure he dipped his finger in the soil and put the merest trace on my left cheek. The man was a pro. Now, I really looked like that naughty boy who had been climbing trees and stealing apples.

Mr Hennessey led the way to the door and rang the bell. Showtime had begun.

Col Sanders opened the door himself. Somehow, I had expected a butler or a housekeeper. I was a little disappointed. The colonel was a slight figure, with stooped shoulders. He had once been tall, strong and erect but age had taken its toll. Liver spots spread across the flesh that was visible and extended to the top of his head which was completely bald.

His once sparkling, but now dull, hazel eyes looked at me hungrily. There was definitely something very sexy about that neckerchief. His gaze lingered on the garment and I followed his eyes as they moved from my throat down my chest and came to rest at the buttons of my short trousers. Absurdly, for a moment I thought he had seen my flies were undone. He might have wished that was the case, because, even at his age, he was lusting after the contents of my pants.

“Col Sanders. Good afternoon,” Mr Hennessey broke the silence. “I don’t know if you remember me, my names Noah. I’m from the village,” the little playlet had begun.

I stood head bowed, looking suitably abashed as my ‘father’ recounted my misdeeds. Naughty Noah had climbed the wall to the colonel’s orchard and stolen apples. He was very sorry, but here are four that were saved. Bad, bad Noah had eaten the others.

Soon we were inside the house and standing in a room that might have been a living room, or maybe a study, or even a library. I had little experience of large houses having been raised in a tiny council flat. The low-ceilinged room contained a number of leather armchairs positioned around a handsome, but now never used, fireplace, a table and a couple of straight back chairs. There were two windows that looked out into an expansive garden. It was immaculately kept: the colonel must have employed a gardener full time.

Like all children I knew I must only speak when spoken to, so I stood patiently drinking in the splendour of the room while the ‘adults’ discussed my future.

“He needs a darn good spanking. That’s what he needs.” It was the colonel who brought up the idea.

“Indeed he does. Indeed he does.” I tried not to smile. Mr Hennessey sounded like an actor in a television adaptation of a Charles Dickens novel. I half expected to hear him to say, “I’m ever so ’umble Col sanders; ever so ’umble.”

Then the spotlight turned on me.

“What have you got to say for yourself Noah?”

Startled, I stumbled on my line. I really had no answer for the colonel and found myself mumbling, “Nuffink.”

“Nuffink? Nuffink?” Where did that come from? I was usually the posh upper-class schoolboy in these scenarios. That, and the blue-and-gold school blazer, was my brand so to speak. Why had I suddenly assumed the position of a working-class urchin? It must have been that bloody Charles Dickens again.

“Pah!” the colonel was not amused. “You are nothing but a thief. A despicable thief!” The colonel’s dull eyes suddenly flared as he verbally laid into me. There was real passion there. What event from his past was he recalling?

He turned to my ‘father.’ “He needs a damned good thrashing, that’s what he needs. What do you say Noah?”

Unsurprisingly, Noah agreed. It was only now that I realised we had not discussed this part of the play. A “thrashing” the colonel had said, not a spanking. What did the old man have in mind?

Suddenly, I found my eyes darting around the room, searching out a clue to his intentions. There was no obvious instrument of my punishment on display. I could see no birch rods or whippy canes. Maybe they were under wraps somewhere, but again I could see no apparent hiding places.

“Might I suggest colonel,” my ‘father’ said, “that you take the boy across your knee and give him his just desserts.”

I shuddered under the gaze of the colonel. Once, he must have been a powerful man whose stare struck terror into strong men. Now, he was a wizened old man, stripped of his physical power. But in that stare I could see lust. He didn’t want to thrash or spank me: he wanted to have me, to rip down my shorts and pants and haul me over the back of the chair and have his way with me.

Mr Hennessey saw my shudder. I was in terror of this old man. I knew he did not have the strength to fulfil his lustful desires. If he made a move for me I could sock him on the jaw and walk out the house. I knew that, but still I was rooted to the spot stunned. What if he and Mr Hennessey had arranged this specially? I could take on the old man definitely; but I might not be able to defeat the two of them together. What if they over-powered me and tied me down across the large oak table. Each of them could quench their thirst on me.

Mr Hennessey and I exchanged glances. It took only a nanosecond. Now, I understood.

“No, you are his father, Noah. You should punish him.” The colonel still appeared to be following the script.

“As you please, colonel.”

I realised Mr Hennessey had been in this house before when without instruction he left the room and returned almost immediately. In his right hand he held a small rectangle of polished wood, with a smooth, well-worn handle which he methodically slapped against his large open left hand.

I was back on familiar territory. Mr Hennessey moved to sit on an upright wooden chair and pointed to his thighs. With my best sullen expression fixed on my face, I stood and allowed my short trousers and underpants to be dropped, before lowering myself to the expected position.

It was going to be plain sailing from here, I thought. How wrong I was.

I felt the firm, cold, smooth paddle move slowly and silently across my bare curves. It was heavier than I imagined. I felt it move away as if it had identified its target and then like a bolt of lightning it returned with a smack that tore the breath from my body. So sudden and so startling was the impact that I surprised myself by letting a yell of protest burst out from the back of my throat. My whole body arched and stiffened in alarm, and my fingers clawed at the carpet pile.

Instinctively for self-preservation my buttocks clung to each other. Then I heard the colonel’s authoritative voice order me to unclench.

Slowly, I relaxed my stinging cheeks, only to be propelled once more into defence mode as the smooth polished wooden paddle landed with tremendous accuracy and force on the very same spot and delivered another slab of pain which sank deep into my backside.

My cheeks tightened into hard muscle. The air escaping through my closed teeth made a high-pitched whine and my feet rose up from the carpeted floor.

Then nothing happened. Mr Hennessey was waiting.  Very slowly and painfully, my buttocks regained their softened form. Then for the third time the sound of the wooden paddle bouncing into my soft flesh resounded around the room. This was where I lost it.

My throaty cries merged with my tears. Snot poured from my nose. My body heaved across Mr Hennessey’s lap. My arms flailed, my legs kicked. Every part of my body attempted escape, but Mr Hennessey possessed a strength I had never before knew he had. He held me forcibly face down across his lap. I was going nowhere; not until the colonel had been given his money’s worth.

I don’t remember how many times that paddle was flogged into my arse but my previously creamy-white buttocks were transformed into two twitching, flaming red mounds of flesh.

It was over. The colonel’s eyes were almost as moist as mine. He watched intently as I performed the dance of the spanked naughty boy, hopping from foot to foot to try to make the pain go away. It didn’t work.

His bony hand caressed my stinging buttock cheeks. Only then did I notice how paper thin his skin was. The agony in my arse was turning into a glowing pain and soon that would become a hot glow. Every square inch of my buttocks and some of my thighs was blistered and the outline of the paddle was clearly visible in many places. The whole area was the colour of deep burgundy and blood vessels had broken in one or two places. When I got home I would have to use a wet sponge to soak off my underpants where the blood had dried and stuck them to my body.

“Stand and face the wall. Hands on your head.” It was an unexpected command from the colonel. I thought we were done, but evidently not. I was fully dressed now and ready to leave, but what did I know, perhaps this was part of the show.

The two adults left me in the room for at least ten minutes. I had plenty of time to reflect on the day. I had taken one hell of a spanking and I was very proud of myself. I had not known that Mr Hennessey could pack such a punch; clearly he did have more experience at this than I had credited him with.

Mr Hennessey returned to the room alone and we left the house. We drove home in silence, but it was not companionable.

That night, I masturbated furiously as I wriggled my sore bottom against the bed sheets and recounted how Mr Hennessey had torn my arse to shreds. The red and black neckerchief hung on the back of a chair and an envelope stuffed with banknotes was tucked away safely in a drawer.

It had been a successful day, but I vowed I would never see the creepy colonel again. And I didn’t. Two days later Mr Hennessey told me the colonel’s body had been found by his daily cleaning woman. He had died moments after we left. I consoled myself that he had died a very happy man.

Mr Hennessey’s Boys episode 3, Ethan’s story is here.

 

Other stories you might like

Winker Wilson’s visit

The Private Tutor: 1

In the farmhouse

 

More stories from Charles Hamilton II are on the MMSA website

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

Mr Hennessey’s Boys 1. Howard’s story

Howard Hannah studied the reflection of his bum in the bathroom mirror.  It surprised him how much damage a hairbrush could do. The pain had gone hours ago and his cheeks were no longer swollen, but some marks remained. Gingerly, he touched a purple bruise in the centre of his left buttock. He winced. It was tender to touch and it would be like that for some time to come.

He had to get into the shower quickly or he would be late for school. It was geography first period. The A-level exams started in less than three weeks, and then school would be over for good.

And then what? He had planned on going away to university, but now he wasn’t so sure. He was on to a good thing here. He would lose it if he moved away. Maybe, he could find a course closer to home.

He towelled off and climbed into his school uniform. The blue-and-yellow blazer was getting a bit tight. That was a shame, some people said they adored to see him wearing it.

He padded down stairs. His younger brother Mike and his mum were arguing; again.

“Howard, there’s some cornflakes,” his mum called from the kitchen.

“Don’t want any.”

“You must have something, how about some …”

“Bye mum,” Howard closed the front door behind him.

It was a ten minute walk to King Edgar School. He wouldn’t be late.

His phone vibrated. It was Mr Hennessey. Howard smiled. Mr Hennessey always had good news.

“Hi Howard, how did last night go?”

Howard laughed. Last night. What a hoot.

“Great. He had me dress like a Boy Scout. From about a million years ago. Y’know, khaki short trousers, long socks, neckerchief. The works.”

He drifted into silence and let Mr Hennessey do the talking.

“Can you do a call out on Friday?

“Dunno, Mr H. That’s the day after tomorrow, I don’t know if the bruises will be gone by then.”

“He asked for you specifically. You’re getting a good reputation.”

Howard blushed, he was glad Mr Hennessey wasn’t there to see him.

“If it goes on like this we can charge a premium for you. You’ll make a fortune.”

Howard was nearing school; there were too many people around for him to continue this conversation.

“Sorry, Mr H. Give me a call later.”

It had started just before Christmas, shortly after Howard’s eighteenth birthday. A group of them were drinking at The Lilliput, a pub were they weren’t too particular about a customer’s age. Timothy, a lad who had left King Edgar’s a year or so back, was on a recruiting drive.

What impressed Howard most was how matter-of-fact about it Timothy was. As if it was the most natural thing in the world to charge men a lot of money to spank your arse. Timothy explained there was a man called “Mr Hennessey” who arranged spanking parties. He had one lined up where lads would dress up as schoolboys.

When he started the school role-play meetings Hennessey hired sex workers to be the naughty schoolboys. It was a disaster. The rent boys were all tweaked and dependent on drugs and could hardly speak. They were rubbish at role-play and could not do much more than simply offer up their arses.

Undeterred, Hennessey started looking for ordinary lads who would be up for it. It surprised him how many were: almost all were straight youngsters happy to earn extra cash. Soon word spread and friends of the lads came forward and asked to sign up.

Timothy was one of Mr Hennessey’s regulars and said even though it was as kinky as hell, the money was fantastic and Hennessey made sure they came to no harm. Nobody had to do anything they did not want.

It suited Hennessey as well. He did not plan it but he had formed a small community of young men willing and able to satisfy the desires of his clients.

Perhaps too much beer had been drunk that night, but Howard and two other lads put their names down. Howard said he was not into corporal punishment; he was not even gay. He would do it entirely for the money.

Howard could laugh about it now but when he started he could not stand the pain. They had abolished caning in schools thirty years previously and dads did not spank their sons (even when they thoroughly deserved it) so teenagers had no personal experience of corporal punishment.

When Hennessey gave him a try-out – two whacks of a traditional crook-handled whippy rattan school cane moderately delivered across the seat of his trousers – Howard jumped up from the back of the armchair rubbing his buttocks in agony. Now, he could take the full monte: twelve, twelve and twelve. That is a dozen on the trousers, then another twelve on the pants with the final ones on the bare. He could take it quietly, teeth clenched tightly shut, or he could holler the house down, or he could go anywhere in between: whatever the client preferred.

The school party had been a great success. Howard wore his King Edgar blazer. The school’s a well-known posh independent school and the clients immediately recognised it. When Hennessey let it drop that Howard was the Real McCoy and was actually a pupil there the old queens blew a fuse.

What surprised Howard was that most of the men didn’t want to give him the traditional “six-of-the-best” with the cane. They preferred him to bend over their knee so they could pat and preen and knead his bum before they spanked him with the palm of the hand. He didn’t even have to take down his trousers.

That was when he discovered it. It came like a bolt from the blue. He was turned on by being spanked. It had never occurred to him before; he had never fantasied about it. He wasn’t gay; he was sure about that. He didn’t have a girlfriend, but he was no virgin. Girls came on to him; he was very good looking in a dreamy dark brown eyes kind of way.

The party was a revelation. He couldn’t keep his cock under control. Perhaps this was an occupational hazard, Howard wasn’t sure, but he found it could be a tad embarrassing sometimes.

Now, Howard was a regular with Mr Hennessey and often did solo gigs; just he and the client. Hennessey had arranged for him to see “Mr Reddington” in his study that Friday.

He stood hand firmly on top of his green-and-black school cap, nose almost touching the wall. He could feel the beautifully tailored mid-grey short trousers hugging the contours of his buttocks. He caught a whiff of dry-cleaning fluid on the crisp green-and-black striped school blazer. He reckoned he looked every inch a prep school boy in his grey shirt, green-and-black striped tie, a grey V-neck jumper with green-and-black trimming and long grey socks with a green hoops around the tops.

The blazer had a special badge on the breast pocket. Hennessey said it was the uniform of a real adult school. Adults would dress up as boys and girls and go to this place in the country where they had built a real school. Then for days on end they would do lessons and behave like schoolkids. Of course, there were lots of spankings, strappings and canings for the naughty boys and girls. It was mainly women on men, apparently.

He waited patiently. He had already been standing hands on head for twenty minutes and his arms were aching like mad. But, he knew the pain would be as nothing compared to the agony he would have in his backside by the end of the evening.

What was Mr Reddington doing? Psyching himself up he supposed, getting into the part, relishing the prospect of whacking Howard’s arse with a cane. Jerking himself off?

Eventually: “Butler! Come in!”

Who the hell was Butler? Howard wondered. Nonetheless, he knocked on the heavy wooden door marked “Headmaster” and entered the study.

It was a huge room dominated by an ancient heavy wooden desk. Two comfortable wing-backed armchairs were placed at either side and smaller armless straight-backed chairs were against the oak-paneled walls. Cupboards and bookshelves ran along three walls and the fourth was dominated by a large picture window. To the left of the desk was an umbrella stand and dangling from it were at least a dozen curve-handled school canes of various lengths and thicknesses.

“You are late, boy,” was his opening gambit. Howard wasn’t, but like any schoolboy up before his headmaster he thought it wise not to argue the point.

“Stand there boy,” he indicated a spot on a faded brown rug in front of his desk. Howard shuffled to the spot and stood with his hands in the pockets of his short trousers.

“How dare you!” Mr Reddington’s roar was so unexpected it took Howard by surprise and he rocked backwards.

“How dare you stand in front of me with your hands in your pockets! Stand up straight.”

Every time he spoke it was as if he were barking out a command to a parade ground full of soldiers.

Howard removed his hands, but this wasn’t good enough for Little Hitler.

“Straight, I said boy! Stand to attention!” Howard did, but it was more difficult to stand like this than he imagined.

“Back straight, thumbs in line with the seam of your trousers, you nasty little boy!”

Then he told Howard why he had been summoned to his study. It was the three detentions scenario. Put simply, three detention slips equals six stinging red welts (or however many) on the bum.

Howard “yes-sirred” and “no-sirred” as he went through the list of the crimes that had resulted in his detentions. Smoking (an old chestnut that one), being out of bounds (ditto) and being caught masturbating in the charging room after gym class (a new one on Howard).

“I am going to give you six strokes for each detention, Butler. That is eighteen strokes in total!” he barked. Thank you, Howard thought, but I can do the arithmetic myself.

“This time you will receive all strokes on your clothed bottom. If I ever have to deal with you again for similar offences, you will not be so lucky!”

“Yes Sir,” Howard felt he had to say something but in these situations it can be hard to come up with anything original.

“Fetch me that cane, Butler!” He pointed behind Howard to the armchair. Howard stepped back three or four paces and reached for the cane. It was about three-feet long and quite thin. With his growing experience of such matters, he knew that a rattan cane did not have to be thick and heavy to be effective; in the right hands this thin specimen could make a boy howl in agony leaving his bottom severely marked. He was relieved that he wasn’t going to get thrashed on the bare bum with this one.

Howard handed the cane to Reddington who then instructed him to return to the chair and turn it around so its back was facing toward them.

While Howard was doing this, Reddington stood up from behind his desk and came to stand beside him.

He swished the cane once or twice to get its measure, although as the teenager was about to discover, he was no stranger to this rod. He was an expert with the cane.

“Right Butler. Take off you blazer and hang it on the door!” Howard did so and it was only then that he noticed hanging on the door there were two more crook-handled canes, one thicker and one thinner, than the one he had handled.

“Stand up close to the chair, Butler!” Howard did so.

“Now bend over, reach out and grip the front of the cushion! Spread your legs wide! Head right down and raise your bottom as high as it will go!”

Howard was a very supple young man, but it was still a struggle to comply with his orders and he had to go on tip-toe before Mr Reddington was satisfied.

Howard felt him tug his crisp white shirt away from the waistband of his short trousers, exposing bare flesh at the base of the spine. His heart began to race faster. Any moment now he would feel the lash of Reddington’s cane on his taut young arse and his buttocks would swell up to feel as if they were twice their normal size. Fortunately, since he was fully clothed the inevitable swelling in the front of his trousers wouldn’t be so readily noticed.

Mr Reddington took his time before he lashed down cut number one. He was admiring the sight of Howard’s tight, gym-honed torso, stretched across that chair. In this elevated position the buttocks and legs were positioned to perfection.

Swish! Howard heard the sound of the rattan before he felt it. It landed and there was a delay of a second or two before the searing pain spread from the initial point of impact on his bottom and travelled all the way down both legs.

He let out a genuine yelp. Sometimes, with other gentlemen, he might play up a bit and give them a bit of show for their money, but he couldn’t do that with Reddington. After he had swished three or four cuts into Howard’s bum he was in genuine agony.

Reddington swished the rod against the teenager’s buttocks twice more and then halted. Howard had so far received six of the very best cuts. Each of the strokes had fallen a centimetre below the other, getting lower and lower with number six landing right on the crease where the buttock meets the thigh.

His backside was on fire and it felt like he had sat on a barbecue. He knew deep welts had formed and they were almost certainly already seeping blood. There was a bulge in the front of his trousers which was pressing into the back of the chair, giving him a very pleasant sensation. He was worried that Reddington might have changed his mind and decided to give him strokes with his trousers down. How would he react to seeing his huge erection?

But he didn’t need to worry. Reddington was only taking a breather. He laid the cane across Howard’s buttocks, rubbed it back and forth to get his aim and then thwacked stroke number seven into the bum. They were off again.

Howard jumped and only just managed to hold his position as the next stroke landed in the lower part of the buttocks.

Then he started again at the top of the buttocks and worked his way down until the twelfth stroke landed right on the crease of the bottom and thighs. By now Howard was bucking and kicking. He held onto the chair cushion for dear life. He had never been thrashed so hard before in his whole life.

Howard’s buttocks told him he wanted it to stop. The pain was so intense it was searing through his whole body. But, his cock told him to keep going. It was throbbing hard against the chair and he knew that he was close to orgasm. And, that’s what he wanted to happen, despite the humiliation he knew he would suffer if Reddington discovered he had ejaculated in his underpants.

It didn’t matter what Howard wanted, Reddington was in complete control.

Once again, he sliced the cane methodically across every part of the proffered buttocks from the top to the thighs. Each lash was carefully aimed, precisely timed and delivered with devastating force. They had Howard twisting and turning. He was out of control and his feet danced a jig in a fruitless effort to curb the torment.

He was racked with pain and his fingernails dug into the chair cushion. His knuckles were white as shafts of pain chewed up his buttocks. His torso humped the back of the chair and the inevitable happened: he shot a load, just as the eighteenth stroke landed diagonally across both cheeks, igniting further agony as the cane cut across a dozen or so welts.

It was over. Howard lay across the chair, exhausted and sobbing. He didn’t know if the tears were of agony or of ecstasy.

“Stand up, Butler!” It was an order, once again barked. Howard regained a semblance of composure and rose from the chair. His arse felt like Reddington had assaulted it with eighteen cuts of a red-hot poker, not a thin, swishy, rattan cane. The front of his trousers was full of spunk and he knew that the agony in his arse and the cold cum in his pants would make it extremely difficult to walk properly.

He was ashamed for Reddington to see him like this. He didn’t mind that he saw he had reduced him to a trembling wreck with a thrashing: that’s what he’d paid for, but Howard didn’t want him to know how much he had enjoyed it.

He stood up, holding his hands held in front of his crouch, hoping that Reddington would not see his stained trousers. He need not have worried. He looked across at Reddington just as he wrapped his academic gown tightly across his body: he too had a secret he didn’t want to share.

 

 

More stories from Charles Hamilton II are on the MMSA website

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

 

Mr Hennessey’s Boys, episode 2, Noah’s story is here

 

Other stories you might like

Never too old

First day of term

Warren’s awakening

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

COMING SOON: Mr Hennessey’s boys

Mr Hennessey has a stable of young men who for a price are willing to offer up their backsides to corporal punishment enthusiasts. Meet Howard, Noah, Ethan and Timothy.

Starting on Friday 3 June and continuing for the next three Fridays, follow their adventures as they provide their unique service across town.

 

He stood hand firmly on top of his green-and-black school cap, nose almost touching the wall. He could feel the beautifully tailored mid-grey short trousers hugging the contours of his buttocks. He caught a whiff of dry-cleaning fluid on the crisp green-and-black striped school blazer. He reckoned he looked every inch a prep school boy in his grey shirt, green-and-black striped tie, a grey V-neck jumper with green-and-black trimming and long grey socks with a green hoops around the tops.

  • Extract from Howard’s story

 

I felt the firm, cold, smooth paddle move slowly and silently across my bare curves. It was heavier than I imagined. I felt it move away as if it had identified its target and then like a bolt of lightning it returned with a smack that tore the breath from my body. So sudden and so startling was the impact that I surprised myself by letting a yell of protest burst out from the back of my throat. My whole body arched and stiffened in alarm, and my fingers clawed at the carpet pile.

  • Extract from Noah’s story

 

I picked up his bedroom slipper from next to the fireplace where it had been left to warm and handed it to him.

 “You have been a very naughty boy, haven’t you, Peter?”

 I agreed that I had.

 “I am going to spank your bottom with my slipper, Peter.”                           

 I tried to look suitably alarmed.

 “Go and stand by the arm of the settee.”

 I did as I was told, while he smacked the slipper into the palm of his hand.

 Extract from Ethan’s story

 

I climbed on one chair and bent over the combined backs and placed my hands palms down on the seat of the other. I’d never seen this position before, but it turned out it was all the fashion eighty or more years ago. It certainly placed my bum at the perfect angle for him to slash his cane into the seat of my trousers. Which he then proceeded to do.

 

  • Extract from Timothy’s story

 

Mr Hennessey’s Boys starts Friday 3 June 2016

 

Other series of stories you might like

The Gaffer of the Academy: 1. Beginnings

Max of the ‘Champion’ 1. The policeman

The Private Tutor, episode 1

The Tyrant Headmaster Episode 1

 

More stories from Charles Hamilton II are on the MMSA website

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com