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


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

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