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Pain and Pleasure 4: Boys will be Boys

Boys beaten for masturbating are shown by Lady Vernon how to do it properly

Crossing the school yard at a brisk pace, she came face-to-face with the Headmaster dragging a pupil in his wake.

“Oh, Lady Vernon. Can I help you?”

“I was just heading for the gym to find your Sports Mistress. Though it looks like you're in the middle of something, Headmaster?” Released, the boy stood scowling at the ground while his captor offered an explanation.

“I was coming from the gym myself when I spotted this one behind the changing rooms. With his back to me and an arm going like a piston.”

“Ah, I see. Masturbation. A habit not unknown among teenage boys.”

“Indeed, Lady Vernon. But one whose practice on school premises incurs a penalty.” He looked at her as if weighing something up. “Now since you have taken Alison in, you may have learned of our little experiment.”

“Mmm. The return of the cane. A penalty that she herself –” Lady Vernon broke off, seeing the man glance pointedly at the boy and changed tack “– um, did tell me about. I have to say I thoroughly approve, sir, and you can be assured of my complete discretion.”

“I'm glad to hear it, Lady Vernon. This lad has just turned sixteen, and thus qualifies for such treatment. And perhaps you might be interested in witnessing the penalty in action.” Receiving her nod of assent, he seized the culprit and set off. “Then follow me...”

In the study she was directed to a seat on the couch as the scene began to unfold.

“Right, boy. Jacket and trousers off. And be quick about it. Then we'll have the upright chair out here.” While the pupil did as he had been told the Head selected a cane from his cupboard and passed it over for inspection.

There was always a frisson in handling a rattan rod and in weight and flexibility it was the equal of those in her own collection.

“Fine weapon, Headmaster.” She smiled her approval and handed it back.

“Over the chair, boy. Hands here.” He tapped the front of the seat. “And don't let go.” When the lad bent over as directed the disciplinarian lifted the tail of his shirt up clear of the target.

The white underpants clung enticingly to the buttocks and to have seen him beaten on their seat would have been stimulating in itself. But the Headmaster had a surprise for her.

“You understand that since this punishment is off the record we are not bound by considerations of propriety that would have prevailed in the past.” He leaned over the boy and gripped the waistband of the pants, his eyes on her. “So Lady Vernon, if it won't offend you I am going to take these down.”

“Far from it, sir.” She struggled to suppress a chuckle. “Please proceed.”

Once the bottom-cheeks were revealed the Headmaster stroked his cane back and fore across their surface. “Masturbating, six strokes; in a public place, another six. Twelve strokes in all and any jumping up will earn you extras. And you'll stay down till I tell you at the end. Got that, boy?”

“Yes, sir.”

The visitor on the couch watched with bated breath as the rod sliced through the air to bite into pale flesh and spring back quivering. As the double-edged stripe blossomed into view, two more strokes followed in short order. Yet save for a sharp intake of breath at each point of impact the boy had made no sound. He was shaping up to be a candidate for one of her own disciplinary scenarios.

The silence was preserved through six, then nine, until at ten he let out a sharp “Ah!” and the knuckles whitened. After two more, and two more small cries, it was done and as instructed he stayed in place.

“Oh, well done, lad!” The words were out before she could stop them and Lady Vernon looked apologetically at the Headmaster. “I'm sorry, sir, that was out of order. But I can't believe you'll have many boys who'll take a stiff caning with such aplomb.”

“Well, this is a new regime, but if memory serves most sixteen-year-olds used to make a lot more fuss than this one.”

“In that case, Headmaster, I wonder if you'd indulge me here. I grew up with an elder brother who was always in hot water at school and received early training in the application of soothing oil to a striped bottom. Since those days, I've always carried a vial in my bag, and this does rather seem like the right occasion. A small reward for exemplary deportment.”

She had in the past used her position as a school benefactor to extract small favours, but this time the Headmaster was looking distinctly discomfited.

“Lady Vernon, you're proposing to oil a caned boy's backside. In my study.”

“Where else, sir? None of this is really happening precisely because we are in your study. And can I remind you that you did bare that backside in the first place.”

She could see him struggle with the logic then yield with a hint of exasperation. “Very well, madam. Then I shall leave you to it.”

With that he was gone and the boy straightened up with a grin. “Were you serious, um, Lady...”

“Lady V is becoming what young people call me. And I certainly was. But for us to do this you'll have to bend over again.”

“Sure thing, Lady V.” Once he was back across the chair she broke open the tube and deposited a blob on each side just below the small of his back. Then she knelt behind him and used her palms to spread the viscous liquid around both of the meaty buttocks while he moaned soft 'oohs' and 'aahs'.

Slick with oil, the plum-coloured weals stood out from the pale flesh, merging into a solid bruise on the right. “My boy, that was a real caning. And I hope the bottom is the better for a rub. But what I said about my brother was only the half of it.”

Easing a hand between his legs she found what she had been hoping for and gave it a squeeze. “Yes, the surprisingly common consequence of a striped arse, and one magnified by a little massage.” She squeezed the erection again and stood him up on his feet. “Let's have a look at what we've got here...”

After a few minutes' work, Lady Vernon eyed the organ with a sigh of satisfaction. The distended shaft glistened in her hand and from the foreskin the glans bulged, leaking beads of the boy's arousal.

“You like, eh?”

“Ah... oh... yes... ah...” In between gasps he managed to communicate his approval.

“Now, boy, you were caught pumping hard and fast and that –” she caught his eye with a reproving look “– that is not the way. Get this fellow juiced up with a lot of slow action first, okay?”

“Aah... ooh ... okay... aah...”

“And then, when he's really primed –”

“Lady V... aah... aah.. .if you... aah... keep on... aah... doing that... ooh... I'm going... to...”

“Yes lad, that is the idea. But we'd better not make a mess.” So saying she moved him quickly to the washbasin which caught his first jet just in time. Then amid his harsh gasps another and another splashed against the porcelain until she was left to coax a last milky dribble from the spent organ.

By the time she had washed and dried him he was again stiff but she gave the cock a little smack. “Down boy. Get this guy back in your pants before the HM comes back.”

“Yes, ma'am.” He obeyed with a grin then zipped up his trousers.

“Now, lad. You'll have a name?”

“Harry, Lady V.”

“Well, Harry, I don't know your tastes but we have a lad your age works in the stables. Maybe you two would get on. And perhaps you could pay him a visit before those marks have disappeared completely...”


“I can still count twelve so if this was nearly a week ago they must have been good ones.” The stable boy stood up from inspecting the bottom. “And he's not just brought back the cane, it's the bare arse gets it now.”

“Yeah, and it stings like fuck but I'd rather that, Johnny, than suspension. Especially if there's aftercare thrown in.” He flashed a wink that made his companion blush and giggle.

“The Lady believes if you take your punishment well you're due a reward. And, fuck, does she know how to handle a cock.” At that they both laughed.

“I couldn't believe it at first. When I felt her hand between my legs. And I've never cum so hard. Ever.”

“Looks like your cock remembers it well, Harry.” He reached out and squeezed the stiffening shaft.

“Don't tell me yours doesn't, Johnny. So let's have a look, eh?”

The stable boy dropped his trousers and pants and before a minute had passed each was handling the full erection of the other. “Nice and easy does it, Harry, or we could be in for a row from you-know-who.”

“Ha. And that wouldn't do, would it?” He considered for a moment then took the plunge with a question.

“I say, Johnny, have you ever had one of these, you know, up the bum?”

The stable lad shook his head. “No. But the idea is hot.”

“Me neither.” Harry pulled the other boy to him by his cock and squeezed the base of the buttocks with his free hand. “Though I could really fancy this one and if you've got any lube handy –”

“What do you boys think you're doing? That is disgusting.” The groom was spitting outrage and they gaped in shock, unhanding the embarrassingly erect organs.

“Right. I am going to teach you two a lesson. John, make yourself decent and go cut me some switches. You'll bring me four of them at least two feet long. And you –” he glared directly at Harry “– will remain here as you are till my boy returns. Then you will each receive a good whipping. Unless you want me to contact your Headmaster.”

Harry shook his head dumbly and stood hands covering his genitals. As if such a gesture at this stage was going to undo the damage done...

Five minutes later the boys were arrayed side by side over a sawing horse that had been covered with a rough blanket. Harry reached out to his companion and they clasped hands against what was to come.

“I'm going to take one of these –” he swished the hazel wand through the air “– and lay on with it across both your backsides until it's worn out. And then I'll take another. And then, if you're lucky, the punishment will be done. So brace yourselves...”

He lashed the thin rod hard and fast with several cuts in turn to each of the exposed behinds. At first the only sound beyond the relentless swishing was the groom's heavy breathing as he worked, but that was soon accompanied by the yelps and squeals of the two victims. And when the second switch was brought into play the stable room began to ring with anguished cries.

At last that rod too was cast aside in shreds and the whipped buttocks inspected with a grunt of satisfaction. “If I ever see such indecency again, I'll be going for a fully-fledged birching. Judicial style as was. Now stay there and think on that for a while...”


“Hello?” She pushed open the door of the stable boy's quarters to find him lying face down on his bed. He jumped up with a look of surprise, hands to his exposed genitals.

“Lady Vernon.”

“Oh boy, so modest. I have seen it before, you know. More than once.” He blushed, uncovering himself and she moved over to sit on the bed.

“I just heard about this afternoon and I'm sorry. The man is a first-rate groom that I cannot do without. But old-fashioned, to put it mildly. And to his way of thinking, boys found 'abusing themselves' need to be taught a lesson. Now I hope you've learnt a rather different lesson from that intended. No cocks out – especially stiff ones – where Mr Dodds might happen upon them.”

She grinned at him and he grinned back, if rather ruefully. “Got it.”

“Good. So let's have a look at the damage.”

Once he was placed across her lap she studied the mass of fine weals extending from the crown of the buttocks down to an inch or two of upper thigh. The colour was fading but it was plain that in the aftermath of the whipping the whole area would have burned an angry red.

“I guess those switches pack quite a sting.”

“Pure murder, Lady Vernon. But it doesn't last long.”

“Mmm. Unlike the cane. And please, I'd prefer Lady V. If we're going to be pals. Um, Johnny, isn't it?” He nodded an OK and she took a package out of her jacket pocket.

“Well, Johnny, seeing you like this reminds me I'd promised you a smacked bottom. But clearly that is going to have to wait. For now, a little lotion won't go amiss. And then I've got a present for you...”

With the buttocks glistening ripely and his erection hard against her thigh, Lady Vernon pressed a slippery finger to the boy's anal ring. At once he pushed back with a grunt and she probed further.

“Mmm... you like that, Johnny. But am I right no cock has made it in just yet?”

“Um, no...”

“Then we'll think of this guy as blazing a trail, eh?” She held out for inspection a length of black rubber that was a replica of an erect penis. If not quite the impressive size of the boy's own.

“Oh, wow.” He looked up at her open mouthed. “Lady V, you're going to stick this up my bum?”

“Only, dear boy, if you fancy the idea.” With the help of more lubrication she worked him with two then three fingers and he was groaning hoarsely.

“Oh God... oh God... yes... please...”

Stretching the slick opening with her hand she positioned the head of the dildo and pressed hard. “Now, Johnny, push down, come on, push...” And all at once the shaft was gone and the muscle closed on its tapered neck to pull the thing tight in. All that was visible was a round base-plate that peeped out of the cheeks of the boy's arse.

She stood him on his feet and stared up into a face wearing that inward expression of one whose insides have just been rearranged by a sizeable foreign object. His organ strained at her with a vein pulsing down its side and she pulled him closer.

“Oh boy... this is something... I just... have to do...” Lady Vernon breathed the words at him and gripped the cock to draw back its foreskin. Then she tongued the clear droplet welling up from the tip and took the whole bulging head into her mouth...


“Oh fuck! Lady V, you didn't...”

“I think the word is 'suck' rather than 'fuck', Alison. And oh yes, I did...” She sat up in the bed and pursed her lips. “These cocks are becoming an addiction.”

“Well you know my feelings about the nasty spitting things. But if they keep you happy, then...”

“But what about the boy in question? A lad of his age should be out and about fucking, sticking that stiffie wherever he can find a taker. He needs to experiment.”

“And you think you're holding him back, Lady V?”

“Well, I don't want to give him up, but...”

“So what about this new girl in the kitchen? She looks really hot. And I don't reckon she's into girls, so...”

“Aha. Because she didn't respond to your come-ons?” Seeing Alison trying to hide her blushes, Lady Vernon chuckled. “You, my girl, are an open book. But good idea. See if we can't invent some job for her that would need a stable boy's help. Or the other way round.”

After a moment she leaned over the figure lying face down beside her and handled the fleshy rear cheeks this way and that.

“You know I can't find a single mark on this delicious arse of yours. And it so happens that when I met up with with Miss Brown this morning she expressed concern that your school work has shown signs of slipping.”

“Oh, did she?” Alison looked up all innocence and Lady Vernon wagged a reproving finger at her.

“Yes, my girl, she did. And I have been given the loan of her special implement so that your bottom can be well and truly spanked.”

“If you must, Miss...”

“Oh yes. Tomorrow I shall attend to the naughty schoolgirl. Who will understand that it's all for her own good. However, in the meantime, I want my young lover to turn over and spread her legs. Mmm, knees up and wide. After these boys I'm pining for a taste of that sweet cunt...”


This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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