Threesome with the Governess - part 3

When you come at the Queen, you’d better not miss

Continued from part 2

Threesome with the Governess - part 2

He felt so naughty, and it was entirely exhilarating. 

Some think naughtiness is a moral failing, but really, it’s a state of boisterous excitement. It’s a mood made even more intoxicating by being so illicit that someone of sterner morals would definitely disapprove of it. The transgression became even more thrilling if the individual in question had the power, and the inclination, to smack bottoms, because that meant painfully real consequences for misbehaving, and getting caught.

Not that naughty boys were ever truly deterred by the prospect of a sore bottom. The buzz of mischief in the here and now always outshone any concerns about faraway futures. If anything, a smacked bum provided a worthy finale to every memorable high-jinks. A mere telling off would be a meagre anticlimax in comparison. A spanking from a powerful authority figure was an illustrious achievement, incontrovertible recognition of the perpetrator’s roguish prestige.

Even though no one grew up under the strict hands of governesses any more, the urge to challenge the shadowy arbiters of decorum still lurked deep within every mischievous mind. Ever since his first furtive fumbles with his stiff penis, he’d discovered how being naughty seemed to charge up his being with sexual energy. The bolder his imaginary crime, the greater the adrenaline rush, and the mightier the culminating climax.

It was like an evolutionary imperative. Meek little boys never amounted to much. Only rule-breakers ever transformed the world. So it was perfectly healthy for adventurous minds to mentally practise evading the rule-keepers. Disobedience kept the flame of liberty alight, no wonder we had an innate tendency to eroticise contrariness.

He knew he would be spanked for his impetuousness, but was well past the point of caring.

When he’d first met Miss Cavendish, her authoritative assertiveness had towered over him, making him feel like a little boy in comparison. Yet here she was, despite all her prestige and her dominating demeanour, bent over the bottom of his bed, completely at his mercy. To have such power over such an exceptional woman was an electrifying ego-rush.

As we grow up we learn - often to our considerable disappointment - that a natural hierarchy exists in the world. But the smartest amongst us learn all the fun lies in subverting it. How boring it would be if all the stations of life were static and unchallengeable. Perhaps that’s why our cultural lexicon is so full of stories of usurpers. Mortals defy the Gods. The talented topple the arrogant. Rags to riches. The meek inherit the Earth. The impetuous boy dares, and wins.

He was in no hurry to unwrap his gift. He wanted to savour lifting his governess’s skirt, to gradually fold the hem upwards until he’d raised the black satin over her hips, and finally laid the gathered fabric on the small of her back. Only then was what she wore underneath revealed: a pair of white bloomers, which extended all the way down to the tops of her thighs. And in the centre, there was a narrow split in the crotch, through which a tantalising flash of pale flesh could be glimpsed.

What a delight it was to pull the halves of her silky bloomers apart, and see her bare slit glistening and sticky. It was even better to know she’d greatly enjoyed their previous sessions. He placed two fingers through the gap in her bloomers, resting each precariously on the slope of both buttocks, just a slip away from falling into somewhere very intimate indeed.

He signalled to Anna to shuffle backwards, so her crotch was no longer pressed tight against their governess’s mouth, and their governess was free to be heard again.

“You two are in such trouble!” their captive exclaimed, in a tone that sounded more like a tingle-inducing promise than a threat. 

Had she really been angry, he would have stopped and apologised for crossing the line. But her tone was more melodramatic than admonishing, as if she was goading him to push the boundary of acceptability and dare to be outrageous. Because when naughty boys were bold they made their governesses wet.

.

.

.

---

* * 7 * * 

“Let me give you a little clue of what this naughty boy wants, Miss.” 

Ben pushed a single fingertip into her bottom hole, no further than the nail, just enough to feel her clench.

Those who’ve experienced it know the pressure of an unstretched bottom hole on the joint of an intruding finger is disgracefully unique. It’s a squeeze quite unlike that of suckling lips, a clench far tighter than the tightest cunt. Simultaneously resisting, yet constricting like an unseen snare, determined not to let the invader in, yet equally set on never letting the intruder go. A consensual finger in the bottom crosses an unforgettable threshold of intimacy. Afterwards, you’ll always know you’ve touched them: there.

“The other boys you discipline never get to do this, do they?”

“Most certainly not!” Miss Cavendish squirmed beneath Anna's pinioning legs, but really, they were the performative struggles of someone who never truly intended to escape.

“Such a naughty naughty boy!” she exclaimed. He puffed out his chest, how gratifying to be scolded by a connoisseur who’d surely tasted every flavour of naughtiness.

Now he could feel a faint but rapid beat thrumming within his fingertip. It might have been his own pulse, but it was equally as likely to be hers. What a fabulously filthy way to measure her sexual excitement. It made sliding a finger along a slit for signs of wetness seem wimpishly tame.

“I can feel your heart beating faster, Miss.”

By way of reply, she clenched and squeezed his finger tighter. Her response suggested she wanted him, and was quite unafraid of being stretched. For a moment he thought about reaching between her legs with another finger and stroking her in all the places, just to discover which touches made her heart race fastest. 

He sensed his governess was the kind of scientifically minded disciplinarian who’d enjoy doing measuring of her own, and who believed thermometers belonged in bottoms not mouths. Perhaps, when she took charge again, she’d slip her own elegant finger into his own tight bummy hole, and take his pulse as he obediently stroked himself. Maybe she’d insist that he wasn’t allowed to touch himself unless he had her finger in his bottom. He could just imagine her prim voice, instructing him on just the right tempo to keep him on the brink, admonishing him if his heart rate rose too high, and telling him to stop. Not so fast, young man! 

Yes. Miss would love that, being in charge of a long slow wanking with her finger in his bottom. She’d be sitting regally as he stood between her knees, or even, made to sit on her lap. And then, when he’d spurted… 

A long-forgotten memory flashed into his mind, one he hadn’t thought about in years. Of a little cotton bag, and having to masturbate on command. All the filthy details began to flood back, retrieved from the deep-level mental repository that had stored them away so faithfully. This had been such a hot fantasy once. 

Several forceful contractions squeezed his fingertip and interrupted his reverie, and the fragile vision inside his imagination popped and vanished. 

Miss must have been wondering if his intention was to tease her without moving. For a moment, he considered making up for his inattention by pushing in deeper, but that seemed like a rather ungracious act with an unlubricated digit, so he began to withdraw his finger instead. This initiated a tiny-scale tug of war. At first, her tight hole was able to cling unyieldingly to his fingertip, until he ultimately overpowered her, engaging the far stronger muscles of his arm to easily pull away.

Whilst it had been thrilling to venture through the gap in his governess’s split bloomers, and disgracefully violate her tight little hole, he was even keener to see her fully exposed. His fingertips moved to her hips, and reverently lowered her elegant underwear to her ankles, revealing a bare bottom even more gorgeous than he’d imagined. Despite her seniority, she had an enviable body, with the athletically toned legs and buttocks of a committed tennis player.

He lightly smacked the insides of her thighs, remembering how she had nudged his legs wider when she’d been the one in charge, giving her a taste of her own medicine. He cupped a hand around each cheek, paused theatrically, and then slowly splayed her cheeks apart until the hidden region within was exposed to the fullest extent. His gaze was magnetically drawn to her cute brown bummy hole, it almost seemed to be winking at him. 

He felt like the naughtiest boy in the whole world, glimpsing something he wasn’t supposed to see. If he’d been a character in a fairytale, right now he’d only be a dozen pages away from a well-deserved comeuppance and a cane tapping against his bare bottom. But it was impossible to retreat now, the pages had to be turned, everyone wanted to know how the story ended.

At the lowest part of her wrinkled hole, two raised ridges of skin continued downwards for a short distance, ultimately becoming part of her dainty inner lips. He traced the route down to her hood with his fingertip and then back upwards on the other side until he reached the brown puckered dimple again. 

He leant forward, and whispered into her ear: “It seems even governesses have a smack-bottom trail”.

He didn’t bother waiting for a response, following up his provocative observation by smacking her bum with his palm. Their captive didn’t scold or protest, she merely stretched her head forward and stuck out her tongue so she could lick Anna’s slit. As Anna was clearly enjoying the attention, he continued smacking for a while. How hot it was to be spanking the bare bottom of one’s own strict governess.

After a dozen smacks he strolled to the bedside table to fetch the pump dispenser of lube. When he returned to stand behind her, both his palm and his sheathed cock were slathered in the slippy goo. He wiped this sticky hand between her cheeks, smearing the excess lube around her bottom hole, and then violated her. This time his slick finger slid inside her so easily, when it was moving freely, he pushed in two. She squeezed the intruding digits, until he could feel her heartbeat flutter in his fingertips.

“So naughty! You two will be getting such a good spanking!” she gasped. 

When she took charge again, their naughtiness was undeniable, and the consequences would be painfully inevitable, but in the red hot heat of this moment, both miscreants were perfectly willing to pay any price.

He withdrew his fingers, and looked down at Miss’s exposed holes, both sticky and greasy but in slightly different ways. For a moment, as he took aim, he contemplated fucking her cunt, but knew her tight bottom was the forbidden vault a truly naughty boy would yearn to burgle.

He placed the tip of his cock against the dimple of her bottom hole, shuffling minutely with the coiled energy of an athlete behind the starting line. He paused briefly, then began to flex his hips, pushing inexorably forward. At first, she resisted, as all bummy holes instinctively do, until he felt her stretch. 

Simultaneously, Anna had shuffled forward to smother their captive’s moans with her own crotch, and was enjoying the gusts of hot breath being blown between her legs. As he inched forward, he looked over the shoulders of their governess and into Anna’s sparkling eyes. Do it, they said mischievously. I want to watch you do it.

He continued pushing until half of his cock had been swallowed, and then reversed and slowly withdrew, until it was just his tip inside, leaving enough space to deliver a single impudent slap to her right buttock. Then his hands returned to her hips, and he pushed in again, like he was riding a common slut.

Filthy thoughts flashed through his mind. What he was doing right now was so outlandish. How many younger men ever dared propose to a older woman: I’ll let you smack my bum if I can fuck yours. It just wasn’t done. Even putting that proposition into words made it sound preposterous, to the point of being outrageous - but that transgressiveness was what made it so hot.

When he was a boy he’d read countless fairytales of naive adolescents venturing out to explore a strange and often sinister world. The trope of the older, wiser woman had stayed with him. Often she was a beautiful siren who was secretly a wicked witch, one who tried to lure and seduce him. Now he felt the main character energy thrum through his veins, he was the fearless protagonist in a story of his very own.

He was pushing ever deeper with every slow irresistible thrust, to the point where he could now feel her soft firm cheeks pressing against his waist. Moments later, his scrotum slipped between her thighs.

“You’re so wet Miss, I can feel you on my balls.”

That was such a naughty thing to say, but he felt indomitable. He wasn’t even trying to be crude, simply candidly reporting his experience. Each time he pushed firmly against her pert cheeks he could feel her warm velvet-soft lips kiss his bare sack before he pulled away like a departing lover. Of course she was wet, sexually sophisticated women adored bottom sex. Being anally pleasured by his big thick cock, whilst having his gorgeous partner push her slit into your face would be enough to make anyone drip.

Long ago, when he’d first started masturbating, and feeling guilty for doing something so filthy, he’d often imagine himself reporting to a strict woman to be disciplined. As he grew older, his fantasies became bolder, and he began to imagine his governess examining the huge erection her spanking had produced, and musing that it would be a terrible shame to see it go to waste. He’d dreamt about doing this so many times.

As his audacity grew, he began to establish a rhythm that made his heavy sack swing back and forth, and gently slap against her wet lips. It sounded like the faint smacks of a distant spanking. He couldn’t believe he was actually slapping his governess’s pussy with his balls. He began to thrust wantonly, dropping the pretence of being some kind of skilful lover, and fucking with the famished hunger of a horny young man.

“Young man, are you going to ejaculate in my bottom?”

She said it so matter-of-factly, as if it wasn’t even a question. It might even have been an encouragement.

Despite being so crudely violated, her serene demeanour was resolutely intact. She had acquiesced to his intrusion with such stoic calmness, never wincing in discomfort, even though his thickness must have been stretching her painfully wide. Had she not been bending over, he could just imagine her finger poking under his chin right now, lecturing him with some righteous aphorism like “Pride comes before a fall, young man”. 

Yet here he was, proudly thrusting as deep as he could go, whilst his engorged cock felt like it couldn’t get any harder. Even still, she’d swallowed him whole. He was abruptly struck by the realisation that this might be the last time he ever got to do this - because once he came and was drained of his vigour, she’d take charge, and put him in his rightful place, permanently.

His governess was so clever. She’d planned all this from the very start, hadn’t she? 

Right now she must be feeling absolutely delighted. Her cute little scamp had been so eager to poke into her bottom, believing himself to be such a big boy. He thought he was in charge, but every aspect of this was only happening at her indulgence. Very soon she’d correct his delusions. Her tight bum would milk him dry, robbing him of his impetuousness. That was when she’d seize control, and when she’d finished smacking his bottom sore, she knew he’d do anything to please her.

When you come at the Queen, you’d better not miss. 

This brilliant woman had developed the perfect way of demonstrating her authority over eager young bucks. Take your best shot, young man, and let’s see who’s in charge once you’ve spurted your essence, and you’re over my knee with my hand on your bare bottom.

It was only when he was teetering on the very precipice of coming, that he realised he was balls-deep in a most elaborate trap. The foolish little sailor boy had run into her catching snare so willingly.

He recognised his predicament much too late. Not that it really mattered, he’d gone much too far to stop. He looked across at Anna, her eyes fixed on them both dreamily, had the two women planned all this together? Anna would get to enjoy watching him fuck this amazing woman in the bum, whilst having her pussy licked. Then she’d get to watch him being spanked like a naughty little boy - and Miss would get what turned her on the most, savouring the triumph of feminine superiority.

He could hear her patrician voice in his head. All silly little boys think they’re so clever! Silly little boys think they can outsmart their governesses and get their own way. He had willingly pushed his stiff cock deep into her trap, and now she was about to squeeze him dry. 

Silly little boy, didn’t your fairytales teach you? All those who dare to tickle the dragon’s tail end up scorched.

“I’m going to come, Miss”, his tone was deferential, no longer the self-assured stud of his fantasies, more a mischievous scamp who’d been caught doing something very naughty indeed.

“I know you are, young man.”

He felt her bottom clench, squeezing him. It triggered a fresh wave of hot guilt to wash over him, as if she’d just walked in and caught him playing with himself, and now had his erection in her grasp, and he was being pulled towards the spanking chair. 

“You’ve been a very naughty boy, and you’re going to be getting a good hard whacking,” she stated matter-of-factly.

He glanced over her shoulders to Anna, her head now lolling on her pillow. The rapidly escalating pitch of her moans suggested she was teetering on the brink of coming too. Their governess remained unflappably resolute, squeezing him tight as her tongue traced lazy Figures of 8 around Anna’s holes.

He gripped his governess’s hips, pushing against her firm cheeks until he felt the wet sticky kiss of her cunt. He pushed further, as if trying to push his balls into the soft velvet gap. He was grinding against her wet lips as he sensed the deep itch, and the spasms that marked the point of no return. Moments later, his cock felt like it was a fiercely burning candle as he spurted deep in her bottom, flooding his condom with a sultry gooey mess. At the very least he hoped she would appreciate the heat of his tribute.

He was going to get such a good spanking.

.

.

.

---

* * 8 * * 

Some places become forever associated by the erotic events that occurred upon them. As if the sexual essence of what transpired there had seeped across it like a spreading puddle of spilt ink, indelibly marking it with an invisible unforgettable stain. 

As he stood at the bottom of their bed he could already sense this spot would always be associated with this experience. The next time he bent Anna over here, they’d both be thinking back to the extraordinary afternoon when he’d come deep in their governess’s bum, whilst Anna spillled herself on her tongue.

He was still standing on that newly enchanted spot, his erection grasped by his governess’s tight grip, just like it had been when she’d led him out of this room by his penis. That had been barely an hour ago, it seemed like an era had passed. He could feel himself wilting as her tightness squeezed him, as if he was being softened by an intimate kind of tenderising. There was no doubt who was in charge now.

As soon as Anna had lifted her legs from her captive’s shoulders, Miss Cavendish had stood upright and he finally slipped out of her bottom. Miss had untucked and straightened her dress with imperious insouciance, and immediately ordered them both to follow her downstairs. Anna had gone first, with Ben literally bringing up the rear - staring at her pretty pale bum, which was unlikely to be so colourless for long.

Now they were standing naked in their own living room, facing the wall with their arms folded against their backs whilst intriguing rustlings happened behind them. Ben was still wearing the cream-filled condom, which now dangled like an embarrassing memento of his recent impetuousness. Neither had been permitted to clean up, so Anna’s slit was sticky with her own excitement and her visitor’s lickings.

As he waited, a weird kind of post-orgasmic shame coalesced inside his busy mind as a most peculiar scenario. He imagined Anna had smuggled him into her bedroom in her family home. They were intent on fucking, but were young inexperienced lovers, and prone to getting carried away. He’d warned Anna to be quiet as he pushed in deep, but her carelessly unsuppressed moans had led to them being discovered. He imagined standing exposed in front of her stern-faced mother, still dripping into his creamy condom, as she told them they’d both be getting their bottoms smacked. 

Silently staring at the blank wall gave him ample opportunity to fantasise about the details. He looked across at Anna, and shared furtive smirking glances. Look at what you got us into! We’re going to get such sore bottoms. You were so naughty. That was amazing. I want to do that again.

But then he sneaked a peep over his shoulder, and noticed Miss was taking something out of a little drawstring bag. A real memory blazed through his head, as startling as a flash of lightning. Despite the warmth of the room, a chill ran through him.

He’d never told anyone this, but in his formative years, long before he’d ever encountered porn, his fantasies were fuelled by the eroticism latent in the period costume dramas he watched on TV. They had inspired a recurring fantasy where he reported to his governess to be disciplined. He would imagine himself as a young gentleman, dressed in tight breeches, and when she inevitably took them down and revealed his erection, that would clearly have to be dealt with first.

His overactive imagination had devised detailed punishment protocols for his mythical disciplinary world. For instance, governesses almost universally believed it was best to spank a boy after he’d spurted, so his bum was more sensitive and she could be sure of his full attention.

In his fantasy, his governess would be seated, and he would stand in front of her lap with his arms obediently behind his back whilst she pulled his breeches down. Then, for reasons of decorum and practicality, she’d produce a little white cotton drawstring bag, and slip it over his stiff penis, pulling the string tight at the base of his erection. 

His disciplinarian would then wrap her fingers around his erection, grasping it tight, and with her other hand, smack his bottom hard with her leather-covered spanking paddle. It would be very unseemly for a naughty boy to rut into her hand, so she’d scold any movement that didn’t occur in response to a smack.

Ejaculation wasn’t the end of his spanking, merely the beginning of it. If she was in a mood to be merciful, she’d allow him to come quickly by gripping his tip. But if he’d been frightfully naughty, and deserved to be teased for a while, she’d weakly grasp the base of his penis in the little circle formed between finger and thumb. Those spankings were the meanest, he’d be so desperate to spurt, but knew that even when he did, she was just getting started, and he’d still have to endure a whacking with his sticky mess dripping into his humiliating little bag.

Afterwards, he’d stand in the corner still wrapped up. If he got hard in the corner again, the process would be repeated until his cock was finally exhausted. Only then would he be taken to the bathroom to wash his poor tender penis with cold water. Rinsing and cleaning the sticky mess from his cumming bag was his chore, after which it would be hung up to dry, awaiting duty for some future misdemeanour. His governess possessed many such bags, and was never without a fresh bag in her pocket.

And now here he was, with a real life governess a few footsteps away, who just happened to be holding a drawstring bag in her hand. It was as if fate had decreed it, but he knew the circle could only be closed if he was bold enough to ask for it. Otherwise the bag would be put to one side, and silenced by embarrassment, the moment would be lost.

There was further shuffling and rustling behind them, and then her clear, strict voice broke the silence. 

“Come here, please.”

They turned around to see Miss Cavendish standing beside the large knee-high ottoman. There were several kinky-looking implements arranged on it, huddled on one side so there was still sufficient space to sit. They approached as instructed, inching forward tentatively. When they were close enough, she reached out a hand, where an unusually shaped matte black object glimmered ominously in her palm. It resembled a musical note, a fat bulbous head on a stem that flared into a curved tail, on the top side of which was a much smaller round nub.

“I’m going to let you two into a little secret,” she confided in a whisper, the clandestine tone made amusing by being so unnecessary.

“This is my Quaver,” she whispered. “We governesses have special secret plugs we can wear when we spank naughty boys and girls. The design of this one is very clever! When you’re put over my knee, the weight of you upon my lap will push this plug in even deeper. And the curved base is specially shaped so I’ll rock on it when you kick and squirm!” 

“My Quaver is a bottom stretcher,” she explained, pointing to its fat head, before running her finger down the stem and along the top of the curved base to point at a smaller rounded bump. “This lump pushes gently against the opening of my vagina. I know some strict women prefer proper double penetrators that fill them deep, but personally I prefer not to be too distracted, I think I spank better when I’m being teased.”

“But it just goes to show, one never knows what a governess is wearing beneath her skirts. Sometimes you’ll see one walking with an unusual mincing gait, that’s a hint. I do have one with a longer curved base that pushes back my hood during very energetic spankings!”

Her short introductory lecture on covert disciplinary butt plugs was delivered with the rapid-fire passion of someone explaining the intricacies of their favourite hobby. Her audience listened fascinated and slack-jawed, and were further astonished when Miss reached down and rolled Ben’s condom off his penis. Then she carefully slipped the fat head of the plug into the cream-filled sheath, and stretched the rubber over its long curved tail, elongating the open end until it was long enough to knot it.

“I love to keep the cream of naughty boys in my bottom when I whack them,” she explained.

Then, much to Anna’s surprise, Miss Cavendish handed her the wrapped plug, and bent over at the hips, as if touching her toes.

“Be a dear, Anastasia, and put this in my bottom.”

The condom was still warm, clammy, and tacky to the touch from the lube that had slathered it. Anna dutifully did as she was told, reverently lifting her governess’s skirt over her hips. This was the first time seeing her visitor’s beautiful thigh-high white bloomers, and the narrow split in the crotch. A gap that made perfect sense if one needed to discreetly slip out of sight and push in a plug with minimal fuss. 

Anna could smell her mistress’s scent. It was not a florid perfume, but something more akin to a rich exotic coffee. Smells turned Anna on in a way lewd sights did for others. Margaret’s slit smelt of salted caramel. Hot, sweet, and salty. There was definitely the waft of cocoa and maybe even toffee. She wondered if it was wafting from a scented body lotion she’d rubbed into her mound.

Anna would have loved to bury her tongue into the gap right away. She yearned to let her tongue rove around her governess’s holes, and demonstrate her prowess at oral pleasuring. But she also appreciated she’d been given instructions, and it would be delinquent indeed to be gratifying herself when she was supposed to be getting her own bottom smacked. 

So Anna dutifully lined up the tip of the plug against the half-hidden greasy wrinkled dimple, and firmly pushed the cum-smothered plug into her Mistress’s bum. The tail at the base was just the right shape to hug the space between her holes, and the little nub at the end slipped between her lips just as described. When it snuggled into the perfect position, it prompted a little moan of contentment. 

When Anna had respectfully rolled the hem of the skirt back down, their governess stood upright again, but before she could take charge once more, Ben broke the silence and took the opportunity to speak. 

“I have a secret to share too, Miss. If I may, I’ve something I’ve never told anyone.”

“Of course you may!” she encouraged.

He told them everything, not just how he used to fantasise about having his erection put in a drawstring bag, but how he used to act it out too. Once upon a time he really did have a little cotton drawstring bag of his own, it had once been used to keep a little toy telescope safe. He described how he used to act out his fantasy in the privacy of his locked bedroom. How he’d imagine himself standing obediently in front of his strict disciplinarian, put the cotton bag over his erection, and pull the drawstring extra tight to make himself even harder.

Once you’ve enjoyed intimacy with someone, there’s no reason to wear masks anymore. He stood in front of Miss naked, arms folded behind his back, with his cock glistening with the residue of coming, and candidly explained how he used to spank himself. He confessed how his preferred technique was to grip his cock with one hand and use the other to smack his own bum with the end of a thick wooden ruler. He explained how the smacking had to continue until he’d expended himself in his cum-bag, and he always got at least a dozen final whacks before the rush of climaxing faded.

“So Miss, it would mean a lot to me if you’d do me the honour of putting that little bag on me,” he concluded humbly.

“I’d be delighted to!” her face blazed with a smile, delighted by his candour. 

Miss Cavendish plucked the bag from her collection of kinky things, and placed it over the tip of his penis, which was growing but still flaccid. She slid the bag downwards until it swallowed his scrotum too, then she pulled the drawstring tight around the base of his shaft. She stood back and admired the presentation, it looked like he was modelling a posing pouch, but without the cord around the waist.

“I love this!” she announced enthusiastically, “And so very practical too! I was going to put down a handkerchief to keep your issue from staining my skirt, but this looks perfect. I’d never thought of using these little bags like this, I must make use of them more often!”

“Now you two, it’s time to deal with your filthy behaviour,” she walked to her bag, and returned moments later with a thick wooden ruler. 

“You’re in luck, young man, I brought my own school ruler! Excellent choice.” 

Their governess perched on the edge of the ottoman, shifting and settling like a hen nesting on a pile of fresh dry hay. She gave them both a glance that wasn’t quite threatening, but nevertheless conveyed the impression that sitting was not something that would be coming easy to either of them before too long.

Her finger beckoned him to step forward, and bend over her lap. She cooed appreciatively as his weight pressed the intrusion into her bottom, then placed the long ruler against his bare bottom. She beckoned Anna forward, so she could stand behind him and watch what happened to naughty boys and girls.

“I’d like you to place both palms at the top of your hips,” she paused, and waited for Anna to comply. 

“Now point your index fingers at your hood - yes - good - now pull the skin back with both fingers. Yes, that’s it. I want you to watch this naughty boy get his sore bum with your stiff little clitoris on show. It’s not just naughty boys who have hard-ons before they’re spanked, is it?”

Her comments aroused both miscreants enormously, Anna could feel her face fizzle with embarrassment, her throbby clit felt like it had already doubled in size.

Miss Cavendish began spanking Ben with the alacrity of an accomplished tennis player. She varied her strokes, like any good player would, there was a series of powerful forehands, sweeping parallel to her lap, combined with an occasional whack from a much higher angle, when she raised the ruler high like a racket preparing for a smash.

The spanking was punctuated with scolding. What a naughty boy he’d been, buggering his governess! It was a violation of the natural order of things. He earned further tellings-off for squirming, but in reality she was greatly enjoying it. She began to emit the same involuntary moans and grunts of exertion commonly heard on the tennis court. 

Meanwhile Anna was in the perfect position to observe how this spanking wasn’t motivated by a desire for retribution, it was all about enjoying the ride. Watching Ben getting spanked turned her on, and she found herself yearning for any kind of physical stimulation. She began to surreptitiously move her fingertips, hoping her governess would be otherwise too distracted to notice - and almost got away with it, but betrayed herself by her panting breaths.

“Well, I never!” Miss Cavendish exclaimed in a shocked tone that was more theatrical than truly outraged. 

“Are you playing with yourself whilst waiting for your spanking, young lady?”

Put like that, it did sound extremely naughty. Masturbating whilst she watched her partner in crime getting his bottom whacked. Imagine the consequences of being caught doing that in the Headmistress’s study as she watched him get the ruler. She could feel the cheeks of her face flush, as bright as his bottom had become.

Miss decided Anna deserved to be dealt with immediately. Ben was told to stand and move to a quite specific spot just behind her hips, where he was told to kneel on the floor with his face on the rug and his pink bum in the air. To add to his embarrassment, he was told to reach back and hold his sore cheeks open.

Whereas Ben had been across both her thighs, Miss Cavendish had a different position in mind for Anna. She parted her legs, so her knees jutted out over the edge of the ottoman. Then she took a handkerchief from her pocket and laid it over her thigh, making it obvious where she wanted Anna to straddle. Anna shuffled over the indicated thigh, then bent over as instructed, leaning past Miss’s left hip and passing under her left armpit, holding out her palms to support her weight on the floor.

As she bent over, her face came close to Ben’s open bottom, who was instructed to shuffle backwards slightly until he could feel the tip of Anna’s nose pushing against his bummy hole. Anna was now close enough to nibble the cotton bag, and through it he could feel her rapid warm breaths on his balls.

Like many governesses, Miss Cavendish believed that putting a naughty girl over one knee was by far the best position for dealing with her bottom. She loved how she could feel the heat of the straddling girl’s mound on her thigh, and because the girl could never close her legs, she could look down between her cheeks at any time, and see how excited she was getting. But what Miss loved most was how it made a girl’s thighs squeeze her own leg as she was spanked. It felt so intimate, as if her thigh was being hugged.

“It seems watching spankings excites this naughty little girl,” she observed.

“Yes Miss,” Anna acknowledged, though her voice was muffled by the acoustics of her unusual position.

His bum was scrupulously clean, and his scent drove her crazy. It seemed like the very essence of naughtiness, how she imagined a room full of naughty boys would smell. Anna had always loved the smell of men. A favourite - but unrevealed - fantasy was imagining herself as a head girl, tasked by her headmistress to bare the bottoms of naughty boys before she arrived with the cane. In her mind’s eye she performed her duty meticulously, kneeling behind each of them, reaching around their hips to unbutton their trousers, before slowly pulling down their pants to release their thick swollen cocks and inhale their unique bouquet.

Her headmistress liked those she whacked to be as hard as possible, which was why she got a pretty girl like Anna to bare their bottoms. She savoured the sweet musky aroma of erections, and the heady masculine scent of impudence and rebelliousness. She loved when she could smell them au naturel, not masked by colognes and aftershaves, so she could sniff out the unique fragrance of boy-cum, and identify those who’d wanked as they anticipated their appointment with the cane.

On occasions, when she’d been all alone and horny, Anna had acted out this fantasy with her boyfriend’s used underwear. As headmistress’s assistant cum sniffer dog, she’d employ her finely-honed olfactory skills, moving down the gussets she’d laid out in a row to snuffle out their filthy secrets. Naughty boys who wanked got double, and afterwards she imagined their painful fate with her face buried in the best-smelling gusset, whilst her fingers were buried deep between her legs.

A sudden smack interrupted her daydreaming, jolting the tip of her nose forward into Ben’s bottom. Her initial reaction was shocked indignation, what a disgraceful way to be spanked! But her sharp intake of breath flooded her nostrils with the delectable scent of his bum and cum-coated cock, she inhaled him greedily.

Margaret had wanted to smack Anna’s pretty bum ever since they’d first met, and was determined to make the most of this opportunity. She rocked forward on her plug, feeling the Quaver push deep and the little nub tease her vagina, and served another accurate forehand into the centre of Anna’s left buttock, who squirmed delightfully. Each whack made Anna’s thighs clench against her own, so she developed a rhythm where she’d pause, let Anna relax, and then deliver another smack to make her hug even tighter.

This nose-in-bum position was by far Margaret’s favourite position for punishing partners in crime. One delinquent suffered the shame of holding their smacked cheeks open, having their bummy hole poked and prodded by the nose of their accomplice every time they recoiled from a smack. They got to feel the hot breath of their partner’s cries and moans blow between their legs.

It was even more evocative when a whacking led to tears. It wasn’t that Miss Cavendish was especially sadistic, but she did appreciate the cathartic power of a good hard spanking, and what better place to have a good sob than against the soft cushions of your partner’s warm glowing cheeks. Some naughty boys could be disappointingly stoic when they were spanked, but their hearts soon melted when they felt their girlfriend’s hot tears drip down their bums.

It had been a most enjoyable ride but Margaret believed the art of good discipline wasn’t just smacking until her arm got tired. An expert spanker matched the intensity of smacking to the recipient’s emotional and sexual needs, something made much easier to assess when their legs were kept splayed by an intervening thigh. 

Anna’s own spanking concluded with six hard smacks to her sit-spots that made her legs clench against Miss’s thigh like the jaws of a nutcracker. Whatever she howled in response was unintelligible, stifled by having her face pressed into her accomplice’s smothering cheeks.

When they were both told to stand, Margaret took the slightly damp handkerchief and replaced it in her pocket. It was embarrassing, but sometimes necessary, to wipe away a girl’s tears with the little square of fabric she’d just leaked on, and which now smelt of her cunt. But Anna had taken her spanking stoically. 

Their governess rose from the ottoman and instructed them to kneel side by side where she’d been sitting, and then bend over with their hands on the floor, and their bums in the air. This was the ideal position to conduct a quick examination. Both bums had been painted pink, with a few darker marks. It seemed only fair they got the same shade, a hot pink bum for one, meant a hot pink bum for both.

Miss Cavendish tugged their cheeks apart, Anna’s lips had swollen conspicuously and were leaking, whilst she could see the shape of Ben’s penis poking against the side of the bag that imprisoned it. Naturally, she scolded them for being so aroused.

She left them in the lunging position, and they heard her footsteps recede. When they returned a few moments later, they were accompanied by a menacing swishing sound.

“Hold hands,” she instructed.

Their neighbouring hands found each other quickly, grasping each other tight. Ben was the first to feel the cane tap against his bottom, as his governess took up position and lined up her aim. Anna heard the swish behind her, then his grip clenched her fingers at exactly the same time the whack reached her ears.  

One doesn’t need to be strong to deliver a memorable caning. Margaret’s timing and aim were impeccable, her muscle memory trained by decades of rallies. A dozen brisk strokes, half on each cheek, each one slightly lower than the last. Each stroke felt like she was splashing his bottom with scalding wax.

“I trust that will teach you not to be such a naughty boy,” she said sternly when the last of the dozen landed. 

“I don’t need to be taught that, it comes naturally” he replied cheekily, prompting a giggle from his accomplice, and a squeeze of his hand. His impertinence earned him another six whacks, but he would have suffered anything to hear Anna giggle like that. 

“I trust that will teach you not to be such a naughty boy,” she repeated, when the cane had finished swishing.

“Yes Miss,” he acknowledged deferentially. But with his face so close to the floor, she never saw the smirks they shared. 

It was Anna’s turn next to feel the cane tapping against her bottom. She felt his hand gently squeezing hers, comforting her, making her feel so safe. Soon she had beautiful stripes of her own, and it felt like her whole body was singing.

.

.

.

---

* * 9 * *

Their governess had left them in the position she’d caned them, bums high in the air, their new stripes conspicuous. They were still holding hands, their temples resting against a forearm on the floor. Behind them, she bustled around unseen.

“You may stand now,” she announced at last, before adding with surprising cheerfulness, “I’ve prepared just the thing for naughty girls and boys!”

They rose to their feet, and turned around to see a dark dildo stuck to the edge of their kitchen table, making it look like a small rhino was hiding behind it.

“Like many governesses, I believe in figging after a spanking for the naughtiest shenanigans,” she explained sternly, appreciating how their hands subtly crept back to instinctively cover their bare bottoms.

The audience knew this was a lecture, not a conversation, and kept their mouths respectfully closed.

“And I think we’re all agreed that you’ve both been guilty of the most egregious misbehaviour.”

They nodded, shame-faced.

“There are, of course, many different options for stretching and gingering naughty bums,” she continued. “There’s much to recommend the classic shaved ginger root in the bottom, as it can be worn underneath underwear for hours afterwards.” 

“Personally though, I prefer this,” she plucked a belt-like harness with a smooth phallic protrusion from the items she’d taken from her bag and laid out of the table. 

“Smearing ginger paste over the phallus is much less faff than peeling roots!” 

“Though I must admit, I was rather careless,” she continued, “and I only brought one harness. But not to worry, I’ve been able to improvise.”

Her finger beckoned Ben forward. As he approached he saw how the horn was a curved dildo, that had been stuck with a suction cup to the dining table. A chair had been placed in front of the table, and she directed him to step up onto it, turning so he faced towards them, so he was squatting over the protrusion.

“Be seated, young man,” she decreed, with an authority reminiscent of his headmistress entering his classroom. How hot would that have been, he found himself thinking, a whole class impaling themselves on her command.

The dildo did not pretend to be anatomically accurate, its greasy tip was rounded and narrow, and flared out towards its base, resembling a thin curved horn, or a demon’s fang. There was a bulge on one side, clearly designed for his own anatomy, to tease and torment his prostate as he squirmed.

The tip of the fang poked against his bottom hole. He had braced himself with his palms on the table, supporting his weight, and slowly allowed himself to descend. That was when he discovered the dildo wasn’t rubbery and wobbly, but unforgivingly stiff. It entered him easily, abruptly stretching him as its diameter rapidly widened. Simultaneously, he could feel the heat of the ginger liniment she’d smeared on it, warm at first, and getting warmer, as if the intrusion contained its own heating element.

Once squirming off the dildo was impossible, Miss grasped the chair his feet were still resting on, and whisked it away in one swift motion. With his weight only supported by his wrists, he slid down the horn in one swift smarting descent. Moments later he was sitting, perched on the edge of the table, with his feet dangling impotently just above the floor.

“I love watching naughty boys get their bums stretched,” she commented, with a tone of  contentment that he was experiencing for himself what she had felt when he’d so impudently entered her.

In Margaret’s view, being able to watch was the best thing about employing a sit-down dildo. Wearing a strap-on around the waist did provide the imperious satisfaction of striding up to a boy, and poking the tip of the horn between his soft cheeks, and sensing him quiver. It also provided the opportunity to curl her arms beneath both his armpits, and abruptly pull him backwards by his shoulders, impaling his bum in one sudden shocking motion. And it was so satisfying to be able to reach around and grasp the base of his stiff penis, and whisper scoldings into his ear whilst he squirmed helplessly against her crotch. But all one really got to see was the back of his head.

Her next action was to reach behind him and pull one of her white tennis sweatbands over one of his wrists. She held that hand behind his back, before stretching the elasticated band of towel fabric wide, and guiding his other hand through it. The effect was to improvise a pair of cuffs, and he no longer needed to worry about the temptation to rub the throbby, slowly swelling, contents of his little cotton bag.

There was a pair of sweatbands, and soon Anna had her arms pinned behind her back with the other one. But to her surprise, Miss did not fix the strap-on around her waist. Instead, she sat on the chair just beyond his flailing feet, replaced the handkerchief just beyond her kneecap, and then tightened the belt-like harness around her thigh.

Her gaze flicked from Anna’s wide eyes to the apex of the ginger-smeared protrusion: “Straddle my leg, please.”

Rather than sit square on the seat, Miss had once again spread her knees apart, so Anna’s legs could stand on either side, rubbing against the luxuriously smooth drapes of her dress. Anna felt her slit hover above the phallus, but reluctantly shuffled forward until she felt the greasy tip tickle against her bottom hole.

“Be a good girl for me, Anastasia, and sit on my knee.”

Anna dutifully bent at the knees, and let herself fall forward slightly, feeling the stiff narrow tip of the phallus push into her bottom. She floated in that position until her thighs began to tire, after which she began to slip quickly onto the protrusion, its sleek shape stretched her bottom rapidly, as surely as Miss had bent her over, and taken her with one rough unapologetic thrust.

Margaret looked up at Ben, who was in line with her left leg - just higher, as if he’d been left sitting on a tall naughty chair that was much too big for him. His little cotton bag now jutted out towards her, like the top of a miniature tent. He was close enough for her to reach out and flick the tip of his growing erection with her fingertip.

“Remember, no coming, young man,” she admonished sternly.

Margaret returned her attention to Anna who had buckled at the knees, leaving her weight mostly supported by the thigh she was straddling.

“Bounce on my knee, like a good little girl!” she encouraged.

Anna responded by riding her governess like a galloping horse, rising upwards with each bounce to the top of the phallus before letting herself sink back down again. It was reminiscent of the time when she’d first told Ben about first meeting Margaret, when she told her story one sentence at a time, alternately rising and falling upon his big rigid cock. 

Margaret loved having miscreants straddle her leg. It was so much more civilised than wearing a strap-on around the waist, and doing all that crude mechanical thrusting. When the phallus was on her knee she could sit back, and let her sitter do all the work. How delightful it was to watch Anna’s cute little breasts jiggle as she bounced. It was even better, like now, with a plug of her own in her bottom, so the rhythm of Anna’s gallop was covertly transformed into beautiful sensations between her own legs.

“Can you feel that heat deep inside?” she asked them both, “Like hot cum in your bottoms?”

They both answered affirmatively, the act of acknowledging it making it seem to burn even hotter.

To monitor her rider’s increasing excitement, Margaret had placed an outstretched finger on her lap by the base of the phallus, perfectly positioned so Anna’s vagina kissed her fingertip at the bottom of each bounce. Now she curled her finger upwards, slipping inside her entrance. That immediately seized Anna’s attention, they virtually fell into each other’s eyes.

“I think this naughty little girl needs the strict hand of a governess,” she said to Anna directly. “Do you think I should make a return visit?”

“Yes Miss, you absolutely must!” she was almost pleading.

She fixed Ben with the same gaze. “And what about you, young man? Would you benefit from my strict hand too?”

“Yes Miss! We’re yours! Please come back!”

Margaret had never played with a couple that had such infectious exuberant enthusiasm. Her entire visit had been unlike anything she’d experienced before, fun, arousing, and continually surprising. It had been a joy to feel how authority had ebbed and flowed between them so effortlessly. Both were so willing to venture beyond their comfort zones, to drop their masks and show their truest selves. 

Most of all, she felt a genuine empathy for this pair. Neither were needy individuals who’d pine for her presence when she was gone, and pester her for her attention. Margaret was a shrewd judge of people, and this couple were unquestionably generous, they both gave far more than they took. 

Margaret had fantasies of her own, of course. One that seemed particularly pertinent now was imagining herself in charge of a spirited young lady who’d just left home to spread her wings. Her charge had met someone wonderful, and she’d been thrilled to discover her new partner was such a sweet and responsible young gentleman. 

Her fantasy persona was strict, but also very progressive when it came to sexual matters. She happened to be a firm believer in regular healthy sex, not just smacked bottoms. What turned her on was the notion of entering into a special arrangement, where she’d write every now and then to ensure the new couple were "doing things properly" - and they’d write back with candid descriptions of their intimate activities. Even just the thought of that made a fire blaze inside her soul. 

Ben’s dangling feet were fluttering urgently, she’d stimulated enough prostates to know he wouldn’t last much longer. He looked so cute with his erection completely filling his little cotton bag, stretching one end so tightly she could see the curved dome of its swollen head.

He was trying to be a good boy, but it was a struggle the toy in his bum was specially designed to win. The fiery ginger paste had made his bottom burn, causing him to reflexively kick his feet, which had created the vibrations deep inside him that ultimately broke his resistance. It all happened so suddenly, his body convulsing, his feet kicking and flailing as if he was running in the air. A dark patch appeared at the tip of the bulging bag, seeping outwards across the fabric. Then his writhing abruptly ceased, as if his battery had run out.

Anna was blissfully unaware of this, as her gaze had been fixed on her governess. But Margaret knew it wouldn’t be long until Anna spilled herself too. She let her bounce until she sensed the moment was just right, then looked into her eyes and whispered her most potent magic spell.

“Be a good girl, and come for me.”

That was the last thing Anna heard before she too was swept away.

.

.

Miss Anastasia and Master Benedict looked so adorable in their little outfits. Whilst their governess had cleaned and packed away her toys, they’d been sent upstairs to shower, and make themselves presentable again. Their new clothes were a gift to keep, she told them, adding that she hoped to see them wearing them again before too long. Ben had also been gifted the little drawstring bag, which was also in need of a thorough wash.

Both were in a floaty daze, scarcely able to believe what they’d just experienced had actually happened. Even memories that were only a few hours old had a hazy unreal quality, as if they might just have imagined them.

They had eagerly agreed to their governess’s suggestion of continuing their discourse through occasional missives. They had loved the idea of receiving instructions to follow, and writing back with sexual accountability reports. Anna had skilfully negotiated a proviso to the deal, and Miss had promised she would read what they’d written whilst sitting on her Quaver. 

Now they had assembled in the hallway again, this time to bid goodbye to their honoured visitor. Their governess could see the disappointment in their faces, how they wanted her to stay, and continue to be strict with them. But all good things come to an end, but then restart again, that’s what makes them truly good things. She lifted their chins with her finger, so their eyes met hers.

“Sadly it is time to take my leave, my dears. But in the meantime, I expect you both to be good for me, and be audacious for yourselves.”

“Of course, Miss,” they agreed together.

“Will you come back, Miss?” Anna pleaded.

“Of course, I have bottoms to smack!” 

She delivered that threat with a smile, before reaching down to cup Anna’s crotch with a strong comforting hand, “Will you be a good girl for me?”

“Yes, Miss,” she answered earnestly.

She did the same to Ben, cupping him in her hand, “Will you be a good boy for me?”

“Yes, Miss!”

“Sometime this week, I’d like you both to put on these outfits. Send me a picture so I know you’re properly dressed. Surprise me.”

“Yes Miss!” they chorused together.

“Will you send a picture back too?” he ventured boldly.

“Naughty boy!” she chided, before whispering into his ear, “Of course I will, dear.”

They exchanged farewell kisses, and then she turned and slipped out of the door, closing it shut behind her. There was a distant whine as her electric car accelerated away like a departing spaceship, and just like that, she was gone.

Anna and Ben shared a conspiratorial glance. Their governess’s stern intimidating aura still seemed to fill the hallway. It was a while before they dared risk a whisper. Only then did they rub their sore bums and giggle. 

There was a new phantom presence in their lives. It felt like believing in Santa Claus again. Someone magical to answer to. Someone who knew if you’d been naughty or nice.

Those lucky enough to have a governess never quite know when their phone might buzz, when they’d glance at their screen, and see a command to pull their pants down.

Agreeing to obey a governess was like living under the care of a benevolent storm. You never quite knew when the wind might change, when your governess would be on her way, ready to sweep through your world like a hurricane.

.

.

.

@spankingtheatre 2024