LETTER FROM SHIPLEY TERRACE

LETTER FROM SHIPLEY TERRACE

Dear Shoeblossom:

The scene I set before you is an odd one, to be sure…but it is quite accurate. I am a Headmaster at a school for delinquent boys. Just before typing this letter, a young man was sent to me with a note from his Form-Master.

I read it with disappointment. “Yates, your Form-Master says you were impudent, and you were unable to construe your Latin this morning. Did you not do your preparation?” Yates, I am afraid, is a naughty boy. He was sweating bullets as he looked at me.

“Sir, I-I’ve done the best I could—the book of Caesar is too much for me, I think.” Yates was rubbing his hands together nervously. “Really, sir, give me another chance—”

I shook my head portentously. “Yates, here at the Ponsonby Academy, we believe that boys must earn their chances, and I am deeply disturbed that you are so stupid, so lazy as to not have studied. Take off your jacket and unzip your trousers, Yates.”

Yates looked at me with eyes of terror—his shiny, pudgy, pock-marked face trembling. It reminded me of the last time I’d caned him-when he’d been caught smoking behind the stables—and I’d used the horsewhip…what glorious welts and rips I’d left that day on his disobedient rear end!

“Sir Headmaster, I’m really trying to study more—”But I grabbed him, and boxed his right ear, and the tears came heavily to Yates’s eyes. My cock swelled in my boxers. This was what I was here for!

“Didn’t I tell you to remove your jacket and take down your britches? Get that jacket off immediately!” Yates took off his jacket, and after seeing the rage in my eyes, he sighed mightily and undid the buttons on his trousers. “It just seems, I’m a Senior Boy, sir…do I have to take my pants down?”

“You are a poor specimen of a Senior Boy, Yates.” I said grimly. “You will be treated as a Little Boy until you show some maturity in your study habits. Take down your pants and underpants, and show me your pink little girlish bottom cheeks.”

I could tell from the look on Yates’s face, that he wished I’d not phrased it this way. God I loved academia…shaping young minds, and all that happy horseshit.

“Grab your ankles, you disobedient young jackanapes.” I thundered. “You’re lazy, and common…what would your sainted father think of you, neglecting your work as you’ve done. I’m going to use the cane to remind you of your priorities here at the Ponsonby School.”

I looked over the selection of canes on my desk. The Malacca? No…not this time. I would use a nice, thick ashplant cane. I looked with pleasure at it, and then at Yates’s full buttocks as he pushed his fat belly against his legs, trying to keep aright. Perhaps I could knock him down, I thought. That would be a lesson, eh?

My cock hardened further as I gazed at Yates’s vulnerable buttocks. His scrotal sack was peeking through his legs as he held his ankles desperately. I’d had a boy in the office earlier, Upchurch, and I’d grazed Upchurch’s testicles as I’d caned him and he’d almost blacked out…what a great job I had!

I swung the ash and it landed forcefully against Yate’s tender buttocks. I swung it again. WHACK! Yates gasped, and I saw a long, thin red line crossing his bubble cheeks. “You’re too fat, Yates, ” I chuckled as I swung again. “Might be less painful if you had less of that disgusting padding.”

WHACK! WHACK! WHACK! “Repeat (WHACK!!!) after me, (WHACK!!!) Yates” I droned. “I am (WHACK!!!)a fat (WHACK!!!) disgusting lump (WHACK!!!)of lard and (WHACK!!!)unfit to pursue (WHACK!!!)a course (WHACK!!!)of study at (WHACK!!!)the Ponsonby School.”

Sobbing, Yates obeyed to the best that he could, mucus coming out of his pug nose, and I felt fine! I slashed the cane again and again, singing the boy’s rear until it turned purple.

At the classic British schools, six whacks were the maximum, but here at Ponsonby, in the year 20010 in the American heartland, you used the cane until you were tired, and enjoyed the results…a boy’s round buttocks, covered in weals and blotches!

At one point I hit a nerve, methinks, and Yates jumped away, letting go of his ankles, standing up and grabbing his butt. He looked quite the sight, dancing about with his trousers tangled round his ankles! “Please, no more Sir Headmaster!…I can’t take anymore!” But I could see his little pecker was erect, and this pleased me mightily.

For Ladislas Yates is a thirty-four year old construction magnate, probably made rich by paying off city inspectors, bribing officials and hiring cheap illegals; Yates and his fellow students, all adult men are voluntary, even enthusiastic students coming to expiate their guilt and get a few thrills at the $100,000 per month Ponsonby School…thirty days here, with discipline and sodomy, and they return to their businesses refreshed (if a bit welted) men!

“You appear to be aroused by this correction, Yates. Must I see to this disgusting tumescence as well?” Reaching over and grabbing Yates’s small penis, I twisted his testicles cruelly, and laughed as the “boy” almost collapsed in my arms. “Place your penis on the desk young sir. Obviously you have been neglecting your studies at the price of worshiping the god Onan.”

“No sir, please, not a penis punishment” Laddy Yates begged me, but his cock was getting hard as a rock, thinking about it. I could see it all—here at Ponsonby, we require boys to shave their pubic areas every day. And I go into the dormitories at six a.m., by George, and inspect!

The boys have generally just gotten over the Matron’s Inspection—we have a butch lesbian who comes in a nun’s habit and bounces a quarter on each bed, to see if it’s made to specification…and she punishes viciously with a Spencer paddle, the one with the holes, if there is anything but hospital corners!

Then I make each boy pull down his pants and I look over what is supposed to be a bald crotch area…

If a boy has even a single hair on his crotch, I pluck it out with tweezers, and if he cries, I cane him—hard! We don’t need sissies at Ponsonby. The rest of the United States is turning out worthless, weak curs…we will have MEN!

“Strip off the rest of your clothes, and place your penis on the desk, Yates.” I ordered. “I’m tired of your malingering, and you’ll do as you’re told now.” Yates, tears streaming down his chubby cheeks, obeyed me, and now he was naked, and his stiff penis was lying across the desk, ready to be chastised.

Yates had his hands by his sides. I saw that his palms were scabbed…his Form-Master had whipped Yates’s palms until they were bleeding for touching himself inappropriately, and for doodling in his copybook when he was supposed to be doing his Latin construe.

There was almost no hope for this lazy, slovenly lad, but I, as his Headmaster, would do what I could to re-prioritize his thinking, to re-adjust his attitude towards the important work we did here at Ponsonby

“I don’t trust you, Yates.” I said, and grinned widely. I spun to my desk and pulled out some Police handcuffs that I’d had since I was doorman and assistant Dom Master at the Thumbscrew Club, Shipley Terrace’s homosexual leather dungeon.

I locked Yates’s wrists together with the cuffs, and looked around at him. Yates’s eyes were streaming with miserable tears, but he k new that when the cock-whipping started, if I didn’t lock him down, he’d be grabbing his little thingie with both paws!

I cane the penises of all the males at Ponsonby, even the Form-Masters, many of whom are former clients or students. A caned penis is a dedicated penis, I’ve learned, and certainly it gives the owner pause, eh?

One of my Form-Masters, a fellow called Aubrey, has a real problem with touching himself—and orgasming, against my wishes. Aubrey’s skin is allergic, or so he claims, to the plastic and metal that make up chastity devices, so I must constantly monitor and punish him, when I suspect he has been touching himself impurely.

Often I will bind Aubrey naked to his bed…he looks so different than when he’s teaching Classics to the Lower Fifth, he does—and after I’ve bound him, I whip his cock again and again with a cut briar switch from the patch in the Head’s Garden.

The briars are filled with thorns and nettles, and they rip through poor Aubrey’s penis until he is quite unwilling to touch himself for some time!

Now, I gently massage Yates’s penis and then lie it carefully on the desk, picking up a long metal ruler. Tapping the ruler against my fingers, I relish the intense horrified look in Yates’s piggy eyes.

“So, you get rather excited when the Headmaster punishes you, eh, Yates?” I ask, lifting the ruler. Yates looks physically ill, but his cock is quite large and swelling. In fact, he is unconsciously masturbating, rubbing it against the tabletop. Disgusting.

WHACK! The ruler bounces Yates’s unruly penis against the hard desk, cruelly interrupting the masturbation. Tears squeeze out of Yates’s eyes. He is such a disgusting crybaby.

WHACK! SMACK! Yates screams, but bravely holds his position, though he is constantly trying the handcuffs behind him. I feel a brief impulse of compassion for the shackled “boy” standing at my desk, but it is truly a brief impulse!

I gaze with intense pleasure at the bright red marks on Yates’s pale penis. My own organ hardens thickly against my trousers. Oh, let’s see how much more we can do here! I lift the ruler again.

WHACK! THWACK! SMACK! The ruler does its work well, also doing damage to Yates’s testicles…poor Yates must grit his teeth and close his eyes tightly to keep his position tightly standing at the desk.

I think of my poor father who mowed the grass at the actual private school that Laddy Yates attended, and how he and his friends used to purposely drive through puddles in their convertibles to throw mud over old Mac McGonagall, the much abused school porter.

Suffering can’t just be one way, that’s how I’ve always felt.

WHACK! Yates’s head bowed low as he gritted his teeth more. Laddy Yates is a former Marine colonel, did eight years there after Harvard and before joining his dad’s corrupt construction firm. Although Colonel Yates has become obese in later life, he has tremendous abilities when it comes to resisting pain.

But generally he prefers to give it—in his business and in terrorizing his wife and children—everyone is afraid of Yates, and then he comes here to Ponsonby, where he’s taught that he’s just a nasty little naughty boy—and Marine or not, he’s going to suffer!

I lifted the ruler again. WHACK! WHACK! My family, all eleven of us lived in a two bedroom hovel in the Yates, Inc. tenement buildings, owned by Laddy Yates’s father. One of my younger brothers perished from eating a shard of broken lead paint—but hey, that’s capitalism, right?

I put my beef into the smacks. WHACK! CRACK! THWACK! Yates’s eyes were now just gushing tears and his mouth was working over time in begging. It was pitiful, but personally invigorating. I picked up a paperweight and slammed it against Yates’s balls and he screamed again.

“Do you want to take a break, Yates?” I asked, and he nodded sluggishly. I took him by the scalp and pulled him away from the desk and brought him down on his knees, and unzipped my own crotch, pulling out my long, thick penis, which I shoved in Yates’s mouth.

“Now show your Headmaster how much you love him!” I commanded…and Yates began giving me a long and sloppy blowjob. Did this mitigate the day when Yates’s father had evicted us, and we all had to go to foster homes? Probably not, but at least he was doing his best, right?

I jammed my dick hard down Yates’s throat, and thought about Voostenwalbert Morley, who had been Director of the Shipley Boys Industrial School, where I’d done eighteen months for car theft. What a nasty little man he was, and how thrilled I’d been when he’d shown up as a “new boy” at Ponsonby! Voost also knew how to give a blowjob, though I’d known his proclivities when he’d periodically strip searched and anal cavity worked us for “contraband”…pervert!

Back then I’d just been poor Ethelbert McGonagall, a dumb fifteen year old who knew little of how to avoid the pederasts that are employed in juvenile prisons! I doubt Voost Morley ever recognized me when he came to be a student at Ponsonby, but I really made up for what he put my friends and I through back at Shipley Industrial…or so I hope!

Instead of looking for contraband in Voost’s shoot, I filled it with huge metal ball bearings that had been rolled in cayenne pepper, and ordered him to keep them there while reciting the famous French poem, the “Henriade”. I think that may have paid the bill just a bit…or so I hope!

Now I shot my load into Yates’s mouth, and waited while he licked up all the semen driblets around my cock and balls. It couldn’t have been easy, with his hands locked behind his back, but then again, is life easy?

Finally I yanked Yates up by his scalp and put his cock and balls back on the table, and after I zipped up, I went and got my trusty Malacca cane. “Now you’ll learn not to be such a little pervert, you cock-sucking little faggot.” I shouted.

“But sir, that’s what you said you wanted, Sir Headmaster!” Yates wailed. But I smiled cruelly.

WHACK! CRACK! THWACK! Within a moment or two, Yates’s penis was a tiny red blotch on the desk, and his balls were completely flattened. As I say, I love my job!

I pulled Yates away from the desk by his ear. “I hope you are starting to realize that you must re-focus your energies on your studies, Yates.” I said this while he shivered, naked with his cock, quite withered, in front of him. But as I belittled him and let him know what a pathetic creep he really was, I noticed that Yates’s penis was starting to grow again…just a bit…for he was a true pervert!

I shook my head and walked over to where I had my gardening gloves and several cut nettle briar branches in a case. Putting the gloves on, I carefully picked up one of the thorniest briars…it was always good to have protective gloves on, you know…I didn’t want my precious skin to be damaged!

I stepped closer to the shivering Yates. “Cower, you repulsive insult to humanity” I said severely. “This school made such a mistake by admitting you…of course you know that, am I correct?” I laughed, swinging the briar close to him, and of course he backed off. “That’s why I make you suck off our Cricket and Soccer teams before every match…because you are a worthless little faggot, and you aren’t deserving of your spot in the Fourth Form at Ponsonby.”

I thought of the times I’d put Yates and a couple of the other boys into heavy make up and women’s lingerie and made them suck off “the cricket team” not students actually, but hired male hustlers from the Shipley Terrace red-light district.

Yates looked at the floor. He looked so vulnerable, stark naked in my comfortably ornate office. “Yes Sir Headmaster, I am aware of it.” A tear dribbled from his right eye down to his chin. “I am not worthy to be here, Sir.”

And yet you come back, four times a year, at a hundred grand a pop, eh Yates? I thought, smiling to myself. I wondered what Yates told his wife and kids…probably that he was going to a spa. After all, they’d never see the scars and welts on his body, as he didn’t have sex with his wife anymore…the human condition is amazing.

I, in my previous incarnation as poor Ethelbert McGonagall, was a waiter at Yates’s wife’s debutante ball…she was a simpering creature…and I remember watching them waltz across the floor, thinking enviously that people like that had the true life…but was I wrong!

What goes around, comes around, that’s what the Headmaster says!

Then I swung the thorny briar branch first whacking it against Yates’s flabby chest, and then again right across his nipples, and he howled! I didn’t blame him, the nettles must really have ripped through the areolas of his small nipples.

He tried to back up, but there was no balance because of his cuffed wrists, and poor Yates fell on his back. Perfect! I moved in and began whacking away at his exposed cock and balls with the thorny briar branch. His screams were poetry to my ears!

After I’ve thrashed Yates thoroughly with the briar branch, and he’s freshly sobbing a new river, I go to my roaring fire, and pick up the metal poker, touching it to the burning embers until the poker tip is glowing red.

“Yes, Yates, you are indeed a delinquent student” I say, as I step close to him. His cock, though filled with thorns and bristles, is quite stiff again…there’s just no way to keep it down! But I’ll try.

“You must learn to be a good boy, Yates. You must begin to concentrate on what’s important in life…how can we allow you to graduate from Ponsonby otherwise?”

But of course Yates would never graduate if he could help it. He has already embezzled quite a bit of cash from his father’s firm just so he can spent months at a time here, being tortured by his beloved Headmaster.

I stepped up and touched the tip of the poker to Yates’s penile glans, and he screamed bloody murder. I silently agree that it must hurt. I touched it again, and Yates began staggering to get out of the way. “Must I bind your ankles as well, Yates?” I asked sadly.

“I-I’m so sorry, Sir Headmaster” he said, with tears coursing down his round cheeks. “Th-the pain from the poker…and the burns might do perm-permanent damage, sir.”

“Yes…or I could use the poker to burn out your eyes. Then you wouldn’t have to look at the burns on that tiny, worthless little dickie-bird of yours, dear boy.” I poked the red-hot poker into Yates’s stomach, and he almost keeled over, but he stood, trying not to move away. He didn’t want to provoke me into burning his eyes out, after all.

It’s been a good five years here as Headmaster of Ponsonby School. It’s one of the best jobs, no, the best job I’ve ever had. I had bad news in spades as a kid—dyslexic, gay, no money…Shit, I’m so illiterate that I had to dictate this letter into a tape machine and have one of my “students” type it up for me.

But I’m a mean looking bastard—after I was sprung from the Industrial School, I joined the male hustlers on Mobbs Ridge Road, thinking I could at least make dinner money by sucking dick while wearing pink spandex, right?

Turned out guys began paying me to tie them up and whip them. I became “Master Ethelbert” and then got the gig at the Thumbscrew Club. And then one day someone had a job offer for me!

Two hundred middle aged men, dressed in school caps and Eton suits…waiting to be punished, and thrashed to be kept in line…and I get to get a little revenge when I can just a bit of class warfare…it’s great.

As I torture Yates’s cock and balls with the glowing poker, I remember that life just can’t get better!

Best,

Sir Headmaster

Ponsonby School for Boys

Dear Headmaster:

Education just can’t be “Beat” in this country, eh? Good luck in your endeavors, but I’ll pass up enrolling at Ponsonby. I had enough canings when I was at Eton the first time!

Shoeblossom