Sissy Sisters Schooling
- 2 years ago
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Strict Schooling 2 free porn video
“Right Johnson, I'm Mr. Jones. You have been sent to us for six weeks' disciplinary training, and it starts now. So bend over the horse. Right over and get a grip on the crossbar in front.”
The instructor flexed his rattan cane into a semicircle, eyes on the backside filling a snug pair of shorts. “Six strokes, boy, and these are going to hurt. It's not a punishment – you've done nothing wrong yet – but an exercise intended to leave you eager to shape up and avoid any future encounter with this instrument.”
He measured the rod an inch below the crown of the buttocks and raised it over his head.
THWUP!
“Ow!”
THWUP!
“Ow!”
THWUP!
“Oww!”
With three pale lines etched into the blue cloth, the instructor positioned his cane to lay on a fourth. For a novice, the boy was taking it well. The sharp cries and the dance of the bottom-cheeks in the wake of a stroke showed his pain, yet he remained locked to the bar.
Then five cut him low into the crease between buttock and thigh, and he jerked up, hands clutching at his seat. But before the caner could open his mouth, the body was back down, and its grip resumed.
“Sorry, sir.”
“All right, Johnson. I'll let you off this time. But in future, that will earn you extras.”
“Yes, sir.”
The final stroke delivered, Mr. Jones waited until the squirming had stopped to view with satisfaction the six parallels crossing the boy's seat.
“Okay, up lad. Now, as the rules require, you'll take your stripes to Matron for examination. Next door down to the right.”
“Yes, sir.” Then as he turned to go the instructor caught a glimpse that widened his eyes in surprise. There was no doubt about it: the boy's shorts were bulging with a sizeable erection. And with a horrid queasiness, he realised the thought of that thing on the boy he'd just caned was causing a stiffening of his own...
oOo
“So let me get the right file here. You're Alan Johnson, just sixteen and never been caned before?”
“That's right, Matron.”
She smiled at the attractive lad in front of her. “And, for the record, the usual six strokes on arrival.”
“Yes, Matron.”
“So Alan, if you drop those shorts, we'll have a look at the damage.” She bent to inspect the plum-coloured welts that crossed the breadth of the otherwise pale buttocks in horizontal lines.
“Hmm. A tidy man with the cane, Mr. Jones. Some of them you wouldn't believe, all over the place. Even cutting down here.” She touched his leg well below the undercurve of the bottom.
“Indescribably painful. And quite out of order. But now, young man, what do we have here?” She straightened up and turned him to get a full view of the penis standing stiffly to attention.
“Well, everything seems to be in working order over here. And there's no need to blush. I have seen one of these before. But when exactly did this fellow begin to swell? I know for a fact that a boy just caned isn't typically in this state.”
“Straight after the last stroke, Matron. I had to stay down for a minute, and when I was let up –”
“He was up too.” She gave a chuckle at her own quip.
“Well Alan, the stripes on your bottom will heal themselves. No call for intervention on my part. But I'm reluctant to send you out in an obvious state of full tumescence; who knows, older boys might try to take advantage. So I'm prescribing some hand relief if you'd find that acceptable.”
He was looking more than a little surprised. “You mean, Matron, that...”
“Yes, young man. I'll manipulate the organ until it ejaculates its semen, at which point it should deflate to normal size. It's a process boys rather enjoy, I'm told.” She kept her expression deadpan, and he stared for a full second before stifling a giggle.
“Yes, Matron, that's so. Though of course, my experience of it is only limited.”
“Of course. Then this should be an occasion to savour.” Taking a silver bowl from the shelf she flashed him a stage wink and placed it on the table. Then she positioned him facing it and took the swollen organ in her hand. Visibly it stiffened yet more, and he gave a little gasp as she exposed the tip that was already lubricating.
“Splendid. Now we can get it all nice and juicy.” And with undisguised relish, she worked the shaft up and down until the whole thing glistened under her slippery fingers. Before long he was breathing hard with small guttural moans, and Matron surmised that the end was near.
“Here we go, boy...” Raising the bowl in one hand, she pumped hard with the other and was rewarded with a succession of streaky white spurts that jetted on to the metal surface. As he subsided into deep sighs, she squeezed the final drops from the spent organ that now lay flaccid in her hand.
“There, young man, job done. Go and give this one a wash and he'll tuck discreetly away.” While he busied himself at the basin, she eyed the contents of her bowl.
“Quite a discharge here, Alan. I'm wondering how long a quantity like this would be in the making?” He was fumbling with his shorts, blushing scarlet and she laughed out loud.
“Oh lad, if you could see your face. I know fine most teenage boys could repeat a performance like yours every couple of days or so. Though to be serious, I'm told more than three times a week can impair the intensity of the thing.”
He was nodding. “It's a good rule, Matron.”
“Well Alan, much as I'd like to quiz a good-looking boy on his habits of masturbation, I've got to be elsewhere in five minutes. But I look forward to meeting again, though you should try to keep out of trouble. You know your bottom will get a minimum of twelve stripes the next time?”
“Yes, I do. And thank you, Matron. That was, um –”
She stopped him with a finger to his lips. “My pleasure, boy, my pleasure...”
oOo
“Well, you're back, Johnson.”
“I'm afraid so, sir.”
“Then you'd better get into position.”
“Yes, sir.” Mr. Jones watched as the boy lowered himself over the horse, the close-fitting shorts pulling tighter around the delicious arse. He had thought of little else since the caning of a fortnight before, and now he was all a-quiver with anticipation.
“Twelve strokes, boy. I did warn you the last time.”
“Yes, sir. I'm sorry sir.”
The instructor tapped his cane to the target then raised it and brought it down with force.
THWUP!
“Ow!”
THWUP!
“Ow!”
THWUP!
“Oww!”
As the boy's buttocks clenched with the pain, Mr. Jones put a hand on the small of his back, all too aware of the stirring in his trousers. “Three down, boy. Hold on.”
By the time the count had reached nine, the erection was straining uncomfortably against his underpants, but it did nothing to diminish the gusto with which he laid on the last three strokes.
THWUP!
“Ow-ow!”
THWUP!
“Oww!”
THWUP!
“Owww!!”
Once the writhing body lay still the instructor was unable to resist exploring the seat of the shorts with his fingers to feel the raised welts beneath. “You did well, boy. Now you can get up.”
His emotions were already in turmoil, but when the boy stood up, he got the shock of his life.
“You'll be hard, sir. From caning my bottom. Please, let me...”
Quite unable to resist, Mr. Jones watched him drop to his knees and unzip his trousers. As if in slow motion he saw the hand probe inside to release and withdraw the stiff shaft. And then the boy took the head of it into his mouth and began to suck...
The climax was like no other he had known and when it was done the boy made a show of licking him clean. Then with the organ replaced, he zipped up the instructor's trousers. Back on his feet, he felt his bottom carefully.
“Ouch. You did lay it on, sir. But now I'd better be off to Matron.” Looking down in a daze, Mr. Jones saw the erection that distended the shorts from crotch to thigh then the boy was gone...
oOo
“You know, Alan, that Mr. Jones is really rather struck on you.”
“Mmm. When I saw how he was after the caning I did give him some – what did you call it? – relief.”
She gaped at him. “Relief? You mean...”
“Well, not by hand that time, Matron.”
After a moment of incomprehension, the penny dropped, and she gave a short bark of laughter. “Oh, you are a naughty boy. The poor man will be besotted. I think what you need is a good spanking.”
“Perhaps the bottom's a bit on the tender side right now, Matron.” He was grinning, and she couldn't suppress a chuckle.
“Speaking of which, let's have a look at those stripes.” Obligingly he bared himself and leant across the examination table. It was quite a sight, even for one accustomed to viewing the aftermath of corporal punishment. From the crown of the buttocks to the top of the thighs close-grouped weals coalesced on the right into a single band of angry colour.
“Well, he may fancy you, but he's given you quite a going over, Alan. You won't be sitting comfortably anytime soon. But I do see that elsewhere you're distinctly perky.” Standing him up she took the erection in her hand and squeezed.
“Um, Matron, please don't be offended, but you are acquainted with him, and I was wondering if you, um, just might...”
“Want him inside me? Oh boy, yes, please. And if you hadn't offered, I was going to ask.”
Now he was the one open-mouthed as she took charge and moved him aside.
“You'll be far too sore to have me on top, so I'll go over here. If it's to your taste to be viewing an older woman's arse.”
Hoisting up her white coat she lay forward on the table, displaying her nakedness from the waist down. She felt his fingers explore between her legs and heard a small gasp.
“Oh lady, you are wet.”
She chuckled and rubbed herself against his hand. “Mr. Jones is not the only one to be turned on by a handsome teenage boy...” Then the hand was there no longer, and his hardness drove into her.
“Yes, boy, oh yes. I want that cock.” His hands held her hips, and the long, measured thrusts grew slowly faster until she was lost in a welter of sensation as, buried to the hilt, his shaft jerked out its load...
Ten minutes later he was lying face down on the examination table while Matron oiled the welted buttocks. “Good fuck, Alan boy. Quite a work-out for the cunt.”
Head turned he raised an eyebrow at her. “I know, not the language you expect from a medical person. But there are times when medical terms are just not enough.”
When she finished the gentle rub, he eased up on to his feet to display an organ once more standing firm. Matron gave it a little smack. “Not even you, boy. Not even you can be ready to fuck me again.”
“Wanna bet, lady?”
He took her arm, and in a quick movement, she was on her back on the table. Then her legs were swung up and parted, and he was on top, straddling her. She took hold of his erection and pushed up her hips towards it.
“Okay, boy. Go for it. Cock, give me cock...”
oOo
So, Alan, you're off in what will it be? Ten days?” The school secretary smiled up at the boy sitting on the edge of her desk, swinging a leg.
“That's it, Mrs. Rudge.”
She eyed his trim figure, shorts snug around the thighs and gave a sigh. What a good-looking young man. There were rumours about Matron, but then she had the opportunities not granted to one stuck behind a desk. Tending the stripes of boys who'd been caned. The thought of doing that for Alan made her feel quite weak.
“And what a good boy you've been lately. I haven't seen your name in the punishment book for weeks. Your bottom will be getting quite out of practice.”
“I'm afraid so. But I'm going to ask Mr. Jenkins if he'll give me a parting six. Unofficially, of course.”
“Oh, he will be pleased about that. Like a leaving present. Though he won't be happy when you've gone.”
“Well, about that, Mrs. Rudge. I heard there's a new boy coming who's a bit wild. Going to need a really firm hand. Briggs is his name.”
“And you thought he should go to Mr. Jenkins. Mmm, let's have a look here.” She opened a bulky folder and ran her finger down a list of names. “Yes, here's his sheet with a lot of history. But in the photo, he looks quite the charmer.”
“If he's caned hard from the word go that might just do the trick.”
“And it will keep Mr. Jenkins nice and busy. Right, Alan, I'll see if I can get that organised. Young Master Briggs can look forward to a very sore bottom...”
oOo
“Ah, Johnson. I wasn't expecting to see you.” He looked up from perusing the files on the new intake expected in a couple of weeks. Two were promising, and one, in particular, could be just the thing to take his mind off the boy who'd done what he only before ever dreamed of. And here he was in the flesh.
“Sir, I wondered if you could do something for me? Since I'm leaving.”
“And what would that be?”
“Um, six of the best, sir.”
“I dare say I could oblige, Johnson.” It was an effort to keep his voice level.
“And I could take them bare bum. If you'd like, sir. Since it would be off the record.”
His organ stiffening at the prospect, Mr. Jenkins made a further decision.
“Right lad. I'm going to make this a caning you will remember.” He went to the cupboard and took out a long waxed rod that quivered in his hand.
“The forty-incher. And whippy as hell. What do you say, Johnson, are you up for six strokes from this?”
There was a moment's hesitation then the boy's mouth set in a line. “Yes, sir.”
“Then let's do it.”
The boy stripped off his shorts and lowered himself over the horse. Then with legs spread he reached back and pointed between the buttocks. “I took the liberty of getting lubed, sir. So when you've finished with the cane...”
For a moment the instructor stared, at a loss. Then he saw that the ring of muscle was oiled and glistening and was struck with a jolt of comprehension. Pulse racing, My Jenkins measured up the rod and delivered the first stroke. The boy bucked wordlessly as the red welt sprang up across the whole breadth of the posterior.
At three he paused and viewed the startling lines standing out from the white flesh. How the lad could stay down for such punishment was beyond him, but he was in the grip of a heady rush that drowned out sympathy.
So he raised his instrument and laid on the last three hard and fast. Then deaf to the cries of pain he pressed the boy's back firmly down until he lay slumped over the horse.
In a welter of emotion, Mr. Jenkins unzipped and released his rampant organ. Free of clothing it angled upward engorged and throbbing. He ran hands over the ridged buttocks then pressed his shaft up to the slick opening. With a thrust, he felt the muscle relax, and he was in to the hilt. It was a breathtakingly close fit, and he moved slowly in and out to prolong the exquisite sensation. But all at once it was too much, and he was racked with spasm after excruciating spasm as his pent up fluid discharged into the boy's bowels...
oOo
Matron stood examining the ferociously wealed buttocks of the boy face-down on the examination table. “Oh my God, Alan. We're going to need some ice.”
While she busied herself with a cold compress, he admitted that having the forty-inch cane applied with force to his bare bottom might have been a step too far.
“Well, he certainly got his money's worth. And I can't believe that you actually invited him...”
“To stick his cock up my arse? Nor can I really. That is if we're still speaking plainly, Matron?”
She chuckled, tucking the ice-laden cloth carefully round the welted cheeks. He gasped at the cold shock then began to murmur his satisfaction. “Ooh...that feels so good...”
“Right, we'll let the arse cool off for a few minutes. Then marks like that are going to call for some special lotion.”
Half an hour later, with a bolster under his belly to raise the bottom the analgesic cream was put to work and in a very few minutes he was enough at ease for Matron to broach a subject lately on her mind.
“You may remember that I've said this before, Alan. Well, I'm going to say it again. A boy who plays sex games with his instructor is a naughty boy who needs a spanking. For one thing, it is quite against the rules.”
“As opposed to, um, sex games with Matron?” He was looking up at her with a small smile, and she put on her most stern expression.
“What happens here is medical, Alan. To aid a boy's recovery from a dose of the cane.” But then at the sight of his raised eyebrow her pretence at severity dissolved into giggles.
“Okay, Matron, so what do you have in mind exactly?”
“Well you have another week, right? By the end of that, these stripes should have faded a fair bit. In fact just enough for a good spanking to colour them up again.”
“I see, Matron, I see.” Now he was grinning broadly.
“So on the day before you leave us, I'm going to take your shorts down, put you across my knee and smack your bottom until it's cherry red. Then I'm going to suck your cock until it's done spurting, and once it's hard again, you are going to fuck me with it. As a parting treat. Have you got that, boy?”
“Yes, ma'am. It's a date...”
“But for now we have other business.” She put a hand under the erect organ between his legs and with the other exposed the bulging head. At once it leaked beads of clear fluid into her palm which she began to stroke along its meaty length.
“You just lie there and relax. Because to complete the recovery from your ordeal I'm about to give you a lovely slow wank...”
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