Threesome with the Governess - part 2
Experiencing it for the first time, again
Continued from part 1
Ben stood in front of the mirror and stroked his stiff erection. He could see the reflection of his governess watching him from the doorway, but pretended not to notice.
He thought he’d glimpsed a subtle smirk. They say the most fastidious governesses possess the demeanour of an English summer’s day. Outwardly bright and cheerful, yet with the possibility of suddenly darkening never far away. At any moment the skies might abruptly darken, their radiant smile swept away by a reproving frown.
For now, she was content to lurk, and watch with her hands clasped imperiously behind her back. He was all too happy to show off, to give a performance and know he was being admired. He alternated between massaging his shaft between his enclosing fingers, and prolonged tugs that pulled back his foreskin, flashing glimpses of the glossy purple bulge beneath. What a rush it was to wank in front of an appreciative audience and feel empowered rather than ashamed.
He wondered if he should stop now, or whether it would please her more to continue until he came. He’d never ejaculated over anyone’s reflection before. He imagined his creamy stream dripping off her face, and flowing down her beautiful tight bodice.
It was Miss Cavendish who ultimately broke the silence. “What have you been fantasising about since we last met, young man?”
She spoke quietly, she might even have been thinking aloud. Even the way she said it suggested there was no wrong answer, that she was simply curious.
“Poking this into you, Miss,” he told her reflection flirtatiously.
That comment seemed to animate her again. She strode into the room and seated herself on the wide double bed. A long index finger beckoned him over. He turned and sashayed ostentatiously the short distance between them until he was standing with his stiff cock pointing straight between her eyes. She stared into the slit of his engorged bulge, in the manner of an imperturbable action hero staring down the barrel of a gun, before forming a ring with her thumb and forefinger and grasping it purposefully.
“Who is in charge of this?”
“You are, Miss.”
“And did I give you permission to stroke my penis?”
The way she uttered that possessive pronoun at exactly the same moment her finger tightened their grasp sent a shiver up his spine. It was indisputable that she was in charge, and this was her penis now.
“No, Miss.”
“And what happens to bold little boys who think they know better?”
“They spurt their boy mess.”
Given where his penis was pointing that was a bold statement. If he’d suddenly lost control and came now, he’d splatter his cream all over his governess’s face. But he didn’t want to appear too meek, this was an opportunity to test her mettle, to demonstrate he was a worthy sparring partner.
“No, they most certainly do not,” she contradicted primly.
She maintained her grip on his penis, keeping it in place as she delivered a sharp slap to his shaft with the fingers of her other hand, which provided extra emphasis to her correction: “They get smacked”.
He’d never had his penis spanked before. Handled roughly sure, but never slapped like that specific part of him was being told off. He couldn’t think of a cheeky retort, so held his tongue as his governess began to unbutton his shorts.
“Do you like your new clothes?” she asked, as she slid his shorts down his thighs.
“Yes. Thank you, Miss.”
She eased his shorts over his knees and let them drop to the floor, then took a moment to admire how good her choice of underwear looked on him. The garment was like a pair of thin shorts, just long enough to cover his bottom cheeks at the back, with a barely large enough posing pouch at the front.
“I love these little boy underpants. Created specially in big boy sizes from an original Edwardian design, as it happens! Goodness knows how many young gentlemen have had pants like these pulled down over the years.”
She tucked her fingers into the thin waistband, which was already half-way down his hips, and shepherded them down further until they fell of their own accord, creating a puddle of discarded clothing at his feet.
“Just so we understand each other, young man, I am quite happy for you to be hard. I would go as far as saying I expect good strong healthy erections in my presence. But a boy can be hard for me without touching - and there most certainly should not be any ejaculating without my express permission.”
“Yes, Miss,” he agreed. She was so hot when she was strict.
Now she opened her legs slightly, pushing her fingers into the fabric of her skirt, creating a little furrow.
“Your penis can go here,” she indicated. ”Bend over.”
Even just the way she said that made him crumble over her lap.
.
.
.
* * 4 * *
Her soft satin dress felt so good against his exposed flesh. Frankly, it seemed almost inappropriate that a naughty boy put over his governess’s knee would experience such luxury, rather than the discomfort of laying across a coarse material that was rough and scratchy.
Ben was pitched forward over her lap, head facing downward and palms resting on the floor. He could feel his erection cosseted in the valley she’d created for it within the fold of her skirt. It was poking between her thighs, and he could sense her own cunt was mere centimetres away. How erotic to be so tantalisingly close, without actually touching.
Had he been in charge he would have told her to close her thighs and grip him tight, so he could pump in and out of her sumptuous satin furrow. But he wasn’t, so was obliged to wait patiently as her roving hands examined his bottom for the first time. She seemed keen to understand how his body felt, and how it reacted to her experimental smacks. She massaged his tensed glutes with her palms.
“Such pert, muscular cheeks,” she observed admiringly.
Miss certainly knew how to fondle a boy’s ego as well as his bottom. She lightly slapped the insides of his thighs to encourage him to widen his stance, then splayed his cheeks apart with her palms, exposing everything within his bottom cleft to her expert scrutiny.
With his thighs apart, his scrotum dangled freely, resting on her lap. The fabric of her skirt felt so good against his bare sensitive skin. Now she was beginning to delicately stroke a fingertip across its shaved wrinkled surface.
“So well kept,” she commended.
He felt her fingers lift his balls, then another fingertip reach underneath, searching for the base of his erection, just before it plunged into the hollow in her skirt. She quickly found the spot she wanted, on the little seam of skin on the rear side of his penis. Her manipulations felt precise and clinical, driven by the necessity of examination, rather than a desire to arouse.
She began to trace along this tiny ridge as it ascended across the middle of his scrotum, and then onwards towards his bottom hole. Her fingertip circumnavigated several times, as water swirling around a plughole does. Her explorations tickled, and made his cock throb. It made the muscles of his hips tense, as if he was readying to thrust between her thighs. Only an exceptional act of self-control prevented him from commencing an unseemly rutting.
When her fingertip ceased circling, it slowly retraced its route along the little ridge, all the way to the base of his penis. Then it started moving upwards once more, all the way, until it was spiralling around his crinkled hole again.
“This little secret path is mine. Only I get to see this path,” she told him.
“Yes, Miss.”
No one had ever stroked him like this before. He’d been aware of that little seam of flesh ever since he’d begun exploring his own body, but had never thought of it as a route that would be of interest to others. But what she’d just said made perfect sense. When a governess put a boy across her knee, only then did the secret path - running from the tip of his foreskin to his bottom hole - become visible. It was indeed a route that only a governess ever got to see.
“I call this the smack-bottom trail,” she informed him, in the kind of hushed voice one might employ to narrate a bedtime lullaby.
Few would ever see this little ridge, even he had only seen his own on a few occasions, and those had required the use of a mirror. Any who revealed their secret little ridge would be presenting their bare bottom for discipline. Those who ever felt the finger of their governess tracing that intimate path would know without doubt they’d be getting their bottom smacked as soon as her finger reached its destination.
So it came as little surprise that as soon as she ceased stroking his ridge, the first smacks landed on his bottom moments later. Initially, she spanked lightly, then progressively harder, as if she was conducting an experiment to assess the right degree of force required to provoke a reaction. She continued to smack steadily for at least a minute, he didn’t feel it was especially sore, but she did spank much harder than her demure figure suggested. Not that the infliction of a sore behind seemed to be her objective.
“Do you like it?” she asked casually.
“Yes. Do you get wet when you spank naughty boys?” he asked boldly.
“I enjoy feeling the faint echo of every smack between my legs. And when naughty boys squirm across my lap, I love how they push my most intimate places against my seat.”
She increased the force of her smacks, prompting him to wriggle in response, which in turn made her emit a quiet murmur of appreciation.
“And… I know what naughty little boys think about when they’re getting a smacked bottom,” she declared, following up her statement with a flurry of extra smacks for emphasis.
“Right now…” A smack.
“... even as you’re getting your bottom spanked…” Another smack.
“You’re still thinking about putting your stiff little penis into me. Aren’t you?” Another smack.
He felt rather transparent. That had been exactly what he’d been thinking about.
“Yes, Miss,” he admitted.
His confession prompted another flurry of spanks, and then she abruptly stopped, and told him to stand again. He rose to his feet, his erection pointing upwards towards her face, as hard as he’d ever been. But far from being offended, she looked back at his arousal graciously, circling its girth once more with her finger and thumb.
“Such a big little boy”, she commended. He liked that.
She surprised him by standing and then, after taking a couple of paces forward, bending over in front of him, as if urgently needing to attend to an errant shoelace. This offered a perfect view of her marvellous bottom, with her two pert globes clearly visible beneath her vintage dress.
“Put your penis between my cheeks, young man,” she commanded.
Eager to obey, he shuffled up to her. He let his tip drift between her cheeks, like a needle following the track of a vinyl record, navigating by touch until he reached the spot which was probably just above her bottom hole.
“I was right, wasn’t I?” she asked, “A smacked bum only makes naughty boys want to push in more.”
“Yes, Miss.”
“Push it. Deeper. Do you think you can push that hard little cock all the way through my dress?”
He did as he was told, pushing and rubbing until he could feel a slight wetness on his tip, and there was a faint but audible squelching.
“That’s it, smear a little circle on my dress, just over my bummy hole. I want to put other naughty boys over my knee knowing I’m sitting on your little stain.”
He felt like such a naughty little boy, defacing her beautiful black dress with his sticky little mark.
“Give me one good reason why I shouldn’t lift my skirt right now, and have you push your big hard penis against my beautiful knickers.”
He had to admire her skill in seduction. Earlier both he and Anna had wobbled with the kind of nervous anxiety familiar to anyone who’d ever invited a stranger into the inner sanctum of their home. A worry only exacerbated by the prospect of playing intimately with someone so strict and intimidating. Yet now here he was with his cock between her cheeks, actively trying to hold himself back.
“It is Miss Anastasia’s turn first. It would be unfair to keep her waiting.”
That appeared to be the right answer. She stood up, and ruffled his hair like a beloved shaggy dog, “Good boy!”
“I do appreciate boys who are able to control themselves. We have already had a little chat about what she wants. And just so you know, Anastasia has told me she finds it more satisfying, and easier to let go, when she’s not having to direct what happens. So she has asked me to act as the executor of her wishes, but I’m sure you’ll be good, and do exactly what I say!”
“Oh, of course, Miss!”
“Miss Anastasia has also requested that you refrain from climaxing. So you can save all that hot cream for a…” - she paused ostentatiously - “... later occasion.”
With that last comment she reached down to lift his underwear back up to the tops of his thighs. His shorts followed, raised to his hips, but she only fastened the top button above his penis, so his stiff erection poked out unimpeded. That gave her something to grip. She led him out of the room and down the stairs as if he was a dog on a leash.
Halfway down the stairs she halted, dragging a finger through a grey drift of dust that had gathered on a bevel beneath a bannister.
“Do you make Anna do domestic chores dressed only in a loincloth?”
“Actually, we’ve never tried that,” he answered.
“Missed opportunity,” she whispered.
.
.
.
* * 5 * *
Miss Cavendish strode in the living room with the radiant presence of a movie star, her entourage followed one footstep behind, he had little choice in the matter, given she was leading him by his penis.
He gawped when he saw Anna, who was now dressed in her new yellow dress. She looked magnificent, like a shaft of sunlight wrapped in cotton. The style of her dress was simultaneously archaic and timeless, with a bodice of lace panels which flowed into a long straight drape from her bust to her calves. The fitted waistband and immaculately tailored shoulders seemed designed to emphasise her femininity, and with her hair already styled in a layered chin-length bob, she was the very epitome of Edwardian chic.
Most of the garment was a creamy yellow fabric, combined with ethereal panels of fine lacework in a softer paler shade. The high rounded neckline was also adorned with lace, as were the delicately puffed half-sleeves that were gathered into cuffs just above her elbows. The skirt flowed over her hips in several textured pleats, falling straight down to the floor like a sunlit waterfall. Underneath the hem she was barefoot, quintessentially elegant, graceful, and innocent.
She was blushing and was looking at him lewdly, in a manner that suggested she hadn’t spent the last fifteen minutes sitting on the sofa twiddling her thumbs. It was much more likely she’d been sitting on the stairs listening to him getting his bum smacked, rubbing herself through her new dress.
She might even have been bolder. Once their governess had entered the room, Ben had either been facing her - or the floor, so Anna could easily have been peeping around the doorway, watching everything, and he’d never have noticed. It had been Anna’s turn first, and that was exactly the kind of thing she’d ask for, “I want you to go upstairs now please, so I can spy on you spanking his bare bottom, Miss!”
Miss Cavendish escorted him into the middle of the room, her grip had been so tight that when she finally did release him he could feel the warm lingering imprint of her fingers glowing on his anatomy. The trio stood facing each other, the erotic tension palpable. Their governess broke the silence, addressing them both.
“Now Miss Anastasia, as you’re in charge first. Why don’t you tell us what you want?”
“Yes Miss!” she squeaked excitedly, it didn’t take long to compose her words, she knew exactly what she wanted to say.
“I want you to teach Master Benedict how to enter me, Miss. He’s such a shy little boy, and he’s never done it before. But I think you’d be able to teach him so much!”
Anna made her request so coyly, in the theatrically innocent voice that Ben always found so alluring. She loved sounding like butter wouldn't melt in her mouth, moments before her tongue tasted a very different kind of cream.
“Master Benedict, do you find this young lady attractive?”
His partner looked so hot. Both remarkably familiar yet beguilingly unfamiliar. A thought flashed through his mind, about how actions speak louder than words. It prompted him to Impulsively stride over to Anna, and sweep her up in a huge embrace.
“I love you,” he whispered into her ear.
They kissed passionately for a moment before he spun Anna around so she was facing their guest. Now standing behind, he pushed against her so his erection rested in the valley between her bum cheeks.
His arm reached around her chest, enveloping her in a hug, one hand cupping a breast whilst the other moved downwards to cradle her crotch. As he nuzzled and kissed her neck, he made a point of looking over Anna’s shoulder, so he could see the lust sparkling in the eyes of their watching governess. He wanted to imprint a mental image in her mind that she’d remember whenever she thought of them.
When they finally untangled themselves from their embrace, he said: “I hope that answers your question, Miss”.
“It does,” she answered. “Do you masturbate when thinking about this young lady?”
“Yes, Miss. Frequently.”
“But you’ve never seen what’s beneath her dress, have you?”
“No Miss.”
It felt bewilderingly weird to say that. Like his mind had suddenly been transported back in time, back to when he still was a teenage virgin, wanking to an imagined vision of his crush’s sumptuous nakedness.
“Then it seems I must teach you about what lies between a young lady’s legs.”
“I would appreciate that very much, Miss.”
“Why don’t you come and kneel here, Anastasia,” she suggested, pointing to the long padded ottoman in the centre of the room.
Anna did as she was told, hitching up the hem of her long skirt in order to mount the low stool, and then lowering her head to rest on her folded arms. She wiggled her bum in the air provocatively.
Miss Cavendish patted his bottom, guiding him forward until he was standing just behind where Anna was kneeling.
“Now lift up her dress, young man.”
His fingers were trembling with anticipation as they pinched the hem of her dress. He lifted it slowly, savouring the revelation of each revealed inch of her slender bare legs, and had to swallow several times to avoid drooling. It was sublime to see her anew again, to be able to admire her calves, and little dimples behind her knees, and the smooth slender beauty of her perfect thighs.
As the hem approached her hips he caught sight of her glorious French knickers for the first time. The lunging position she’d adopted had pulled the lustrous unpatterned satin so tight he found himself staring at two perfect marble globes. The legs of the garment were short, with a subtle fringe of lace around the tops of her thighs.
He pulled the hem over her bottom, and let the loose material drape over the small of her back. His assignment complete, his fingers relinquished their grip. He was still staring at her, when Miss began to rapidly announce a succession of new instructions.
“Stroke her knickers.”
“Stroke her bottom.”
“Isn’t she so pretty?”
“Doesn’t that smooth satin feel so good?”
“Now place your hand between her legs.”
“Can you feel how hot she is?”
“Stroke her there, slowly and gently.”
“That’s it. Tease her.”
“Now, pull down her knickers.”
This was what shy little boys dreamed about, their eager fingers entering the tight elastic of her waistband unchallenged, and pulling her panties down because that was what she wanted. He could feel her underwear stretch as he tugged it over her hips, revealing the true glory of her beautiful bottom. He bared her as slowly as he possibly could, relishing every moment of her exposure.
He began to glimpse the pink folds between her cheeks, it was like gazing upon the Face of God.
He was still staring between her legs as he guided her knickers down her thighs, laying them reverently to rest where she was kneeling.
“Isn’t she beautiful?”
Their governess had taken up a position standing right behind him, and was sharing his view. A swirl of possible adjectives materialised in his mind: gorgeous, fabulous, luscious, stupendous, sensuous, wondrous. None seemed to do her justice. He settled upon a single word.
“Yes.”
“Now young man, it’s important to be aware of female anatomy. So I want you to describe to me what you see between Miss Anastasia’s cheeks.”
This was an unexpected challenge. Despite seeing Anna’s pretty cunt countless times, he’d never been asked to put it into words before. It would have been a highly unusual encounter if any of his past lovers had told him: “describe me” rather than “touch me”.
He started at the top, at the point where the crease between her bottom cheeks began, like a path emerging over the brow of a hill, and descending between two gently curving slopes. He began to trace its route with his fingertip.
“I’m following a little crease, like a fold between two pages,” he announced.
“It leads to her bummy hole, which is pink and puckered like the lips of a dainty kissing mouth. I can see a dark smudge around it, its shape resembles the shadow of angel wings. It doesn’t look dirty. More like a patch of sun-tan. How strange for it to be in such a hidden nook.”
“Do carry on!” she encouraged, flashing a grin.
“Beneath her bummy hole there’s a tiny bright pink bridge that leads to another even deeper dimple. This one looks like a miniature sideways pair of pink lips. The thin lips are slightly apart, as if they’re about to speak, and they’re glistening, as if they’ve just been licked.”
“Between the lips I can see tiny glistening threads, like strands of spider-web specked with little drops of morning dew.”
“On either side of the lips are two fleshy cushions running its entire length. They look like two cheeks of a little bum, but inside her actual bottom. Mmm, these two pads feel like the softest and most luxurious velvet.”
“The pads gradually curve together like pinching fingers, I’m going to take a closer look at the point where they meet. There’s several folds of thin pink skin here, forming what looks like a little gothic arch. Underneath, a tiny glossy bump seems to be hiding.”
He awaited her assessment, already yearning for his teacher’s praise.
“Fabulous!” she commended, “So evocative. With such attention to detail too! Now why don’t you pull her bottom cheeks apart, and tell me what you can see now?”
He reached forward tentatively, placing his fingers under the curve of each buttock, at the point where they merged with the fleshy outer labia, and began to tug them apart.
“Goodness, Miss! There’s a deep sticky hole within the little lips!” he exclaimed.
He was channelling the excitement he’d felt once before. During his own memorable pioneering journey of discovery, when - for the very first time - he’d spread and gazed into his first girlfriend’s slit. It wasn’t just the sight of looking at something that had attained near mythical status in his imagination. It was the waft of her scent, so musky and intoxicating, which seemed to ignite a part of his mind he’d never realised he possessed.
“Are you enjoying this, Miss Anastasia? I bet you’ve never had your pretty pussy described so thoroughly!”
“I love it, Miss! All little boys should have to describe a pussy before they play with it!”
“There are few greater joys than being the centre of another’s curiosity,” her governess concurred.
He could feel the glow of that joy too. It was something that emerged from a deep need to be seen, not just superficially, but intimately. Yet few ever truly received this exquisite kind of focused attention. It was rare for sex to be intentionally a game of “look but don’t touch”. Their new governess was making them play by different rules, and it was thrilling.
“Do you want him?” she asked.
“More than anything, Miss.”
“Do you want her?”
“More than anything, Miss,” he answered.
“Pull down your shorts.”
He released the lone button that was keeping his shorts up, and let them slip down to the floor. His underwear was already partially pulled down so he let that fall too, until he was standing at attention, half-naked. A proud little sailor boy.
Miss Cavendish accepted his salute, placing her fingertip beneath the tip of his stiff penis.
“Now, young man, I think I’d better teach you what to do with that.”
He had not expected that being treated as a naive little boy would be so arousing. But she seemed to have a deep understanding of male psychology. She knew the sexual journey of every man began with the ignorance of immaturity. In time, they’d make themselves horny with their own fantasies, until they finally developed into wistful but eager virgins. For the initiation ceremony of Manhood, they had to learn the rules of the ritual themselves.
No one gets an apprenticeship in sex. Ideally we’d learn side-by-side with our lovers, but we’re afraid of seeming too gauche or too crude. We’re keener on making a good impression than being truly seen. So we end up learning alone whilst coupled to another, through fumbling encounters of excruciating embarrassment. No wonder once those bitter lessons were learned, it was so liberating to revisit those awkward days and pretend to be a novice again.
There was a faint crinkling, and he looked down to see her placing a rubber hat upon the head of his little sailor. Her nimble fingers immediately rolled the condom down his shaft. It felt unexpectedly cold, like she’d just taken it from the ice box. She noticed his reaction, and immediately supplied an explanation.
“It feels cold because it’s a delay condom. The best for boys who haven’t done it before, so they don’t get too carried away.”
She applied a dab of the contents of a small glass bottle to the outside of his sheath, slathering it along his length with her fingertips. It was slick and slippery, and smelt musky and exotic, like rosewater in a dusty desert souk. Then she plucked a riding crop from the breakfast bar, and swished it through the air demonstrably.
“Listen carefully, young man,” she said in a new, more sterner voice, “I am in charge of your motions.”
She tapped the tip of the crop on his right buttock. “When I smack here, I want you to push in.”
Then she tapped his left buttock. “When I smack here, I want you to withdraw, until only your tip remains inside. Is that clear?”
“Yes, Miss.”
"Now stand behind this young lady. Do you know where it goes in? Point to it with your finger."
Feeling mischievous, he pointed to the conspicuous fleshy bulge at the lowest visible region of her folds. He heard Anna suppress a snigger, which pleased him enormously.
“No, young man. That is not where it goes in. That is the clitoris,” she spoke in the manner of a patient biology tutor, “But an important place for sure. Why not give it a gentle rub?”
Anna appreciated his touch with a contented murmur.
“She likes that, doesn’t she? Why don’t you try moving your finger in little circles around it?”
This impromptu sex education lesson was unexpectedly exciting. He found himself wondering, what if everyone had a fucking coach? How would that change our attitudes to intimacy if there was a third person who watched and spoke gently to us.
“Now let’s try that again,” she encouraged. “Show me where we should put our penis.”
Our penis - he appreciated that deliberate choice of language, as if she was on his team, and wanted what was best for him. Her faith emboldened him, so much of sexual expertise was a willingness to risk outrageousness. So he pointed his index finger directly into the centre of Anna’s bottom hole.
“Such a naughty naughty boy!” she scolded. “Only the filthiest little boys put it in there!”
He knew at once her indignation was performative. She seemed to have a knack for saying just the right thing. Her voice was so intoxicating, even her admonitions made him harder.
“Try gently pushing your finger further,” she prompted.
Anna had clenched herself, and his fingertip was unlubricated, so his gentle prodding made disappointingly little progress.
“See how that little hole resists intrusion? We can not push in there, can we?”
“No Miss,” he replied sullenly.
“So, where shall we put it?”
He moved his index finger slightly lower, over a region that felt hotter, and sticky, and damp. It halted, as if it had become stuck there.
“Yes, good boy!” she commended.
“Is this where you’d like this young man’s penis, Anastasia?”
“Yes Miss. Please Miss.”
“Push a bit deeper,” she instructed. “Yes, that’s it. See how easily you slip in there!”
He slid his finger deeper, which was welcomed like a thumb between suckling lips. He continued until he could push no further, until he was completely swallowed by her warm bewitching wetness.
“Now Master Benedict, why don’t you put your penis just where your finger was?”
He did as he was told, conscientiously lining up the nipple of his condom against her entrance. Then a smack stung his right bottom cheek. He remembered at once what that meant, and thrust forward in response.
“Miss! He’s so big!” Anna squealed.
He could feel the ring of her cunt momentarily resist, then stretch as he pushed inside. It felt incredible, like he was doing it for the very first time, again.
Two more smacks followed the first, encouraging him to push in even deeper. Then there was a pause, and he felt a sting on his left cheek, and he slowly withdrew.
A rhythm began to develop. Pairs of smacks on alternating cheeks. In. Then out. In. Then Out.
A sting began to spread through his bottom, as his governess tapped out her desired tempo on his cheeks. She was quite aware whenever he exceeded his mandate, and didn’t hesitate to issue corrective whacks to the backs of his upper thighs when he decided to move without her permission. Her smacks left him in no doubt who was really in charge. He was her tool, and would do as he was told.
"And remember, no ejaculating, young man, or I’ll be sending you both to bed with sore bums!"
Her warning seemed superfluous. He didn’t feel anywhere near coming, whatever was inside his condom had by now completely numbed his penis. Whilst he was still aware of being inside her, and how her tightness was gently squeezing him, the usual sensations of fucking were absent. This, coupled with his inability to move of his own volition, contributed to the eerie feeling of being somewhat disembodied, like he was inhabiting the body of a puppet. He began to feel like he was little more than his governess’s dildo, and she was fucking Anna, not him.
The smacks continued, and like a good little boy, he moved in and out as he was told. What had Anna and their governess discussed when he’d been sent upstairs? Oh Miss, he imagined Anna pleading, I want you to fuck me with his big stiff cock!
She continued to tap out the beat on his bottom. There were times when the smacks arrived in quick succession, prompting him to pump rapidly, as if she’d dialled up the speed of a fucking machine. But there were also moments when he found himself sliding in and out quite languidly, as if she was a ballet tutor conducting the most intimate pas de deux.
A smack to push in. A smack to slide out. Her spanks were too light to ever hurt, but firm enough to remind him who was unquestionably in charge. Each imparted a pleasant sting, and by now he’d accumulated enough to make his bottom glow. He remembered what Anna had originally asked for: please teach the shy little boy how to fuck. A lesson was in progress, and he had to accept this was the tempo Miss expected.
“Would you like him to touch your clit?” she said at last.
“Oh please, Miss.”
He sensed Margaret approaching, and then stand alongside him. She grasped his hand and extended his index finger, guiding it between Anna’s legs, as if he couldn’t be trusted to find the right spot himself. She kept her finger pressed firmly on top of his, subtly nudging it until it was moving in small circles. It was her motions that began to gently tug back her hood and massage her stiff little bump.
His cock was still lingering deep inside, but not moving, as Miss hadn’t given him any permission for that. He was deep enough to feel Anna clench. It was a novel experience, loitering intimately, as if hovering, with nowhere to go, and no objective to reach.
As he daydreamed, three words materialised in his mind: Single Thrust Fuck. What if, the next time they fucked, he pushed in once, and once only, and just stayed there? He’d be pressed in so deep, she’d only be able to squirm and squeeze him. He could imagine teasing her: “Don’t be so greedy! You’ve had your one thrust. Didn’t you enjoy it?” Then he’d just lie on top of her, pinning her down with his superior strength, so she couldn’t buck against him and satisfy herself.
Miss did say she appreciated boys who were able to control themselves. Maybe after he’d given Anna a Single Thrust Fuck, they’d send her a message describing what happened, eager to hear her approval. That was a hot idea. It would be like the spirit of their governess was in their bedroom with them.
His fingertip continued its wandering massage, even though he wasn’t in charge of the steering. Its meandering path had spiralled outwards to include her lips, but intentionally avoided her clit so she wasn’t pushed over the brink too early.
“Put your other hand in her hair,” his governess whispered.
He placed his fingers onto the back of Anna’s head, sinking them into her short dark hair. As Miss teased Anna’s slit with one of his fingers, his other hand was slowly massaging her scalp. Apart from his hands, he was motionless, his governess’s deferential marionette. At times it felt like he had become an extension of her body, silently watching from behind her eyes.
Her crop began to smack his bum again. He resumed his thrusting motions as directed.
“Are you enjoying your first time, Anastasia?”
In a way, it was their first time. Their first threesome. Perhaps this had been what Anna had asked for, to be simultaneously fucked by them both of them together. A collaborative effort, Margaret’s beautiful mind and his big stiff penis. Not a tag-team threesome where two fucked and one watched waiting their turn, but three intimately mingled participants.
He felt Margaret’s hand move his finger to precisely specific places. Being made to remain so still had given him plenty of time to think, and he was wondering if these were the places his governess also liked to be touched too. Maybe this was how she stroked herself as she imagined dealing with naughty boys.
It was as if his awareness had shifted to reside in his hands. He realised he was stroking Anna’s head with the same alacrity he employed when caressing between her legs. He could feel his fingertips tingle as he combed her hair and massaged her scalp.
All the while, she delivered periodic slaps to his bottom. He had never fucked anyone this slowly before, or anywhere near this quietly. His experience of sex had always been an escalating cacophony of panting or moaning. Now though, he had a ringside seat to watch how Miss Margaret Cavendish liked to fuck a girl.
It was so easy to imagine her standing right where he was now, but wearing a strap-on, skillfully pleasuring Anna with the same well-timed thrusts and desire-kindling pauses. All while her skilful fingers roved across Anna’s body, ticking, teasing, and tantalising. When you fucked with a dildo, there was never any hurry. You could take as long as you wanted to lead her up the hill, and her legs would be wobbly by the time she reached the top.
“You’re close,” Margaret told her.
Anna whimpered her reply, seemingly incapable of forming the right words.
“Do you want to show this good little boy how a big girl comes on his penis?”
Beneath his fingers he could feel her head nodding eagerly as she moaned. Behind him, he felt a precise sequence of well-spaced slaps. He obediently thrust his hips accordingly, at the same time he felt his governess push his own finger forward. He felt the little flap of skin that cloaked Anna’s clit stretching beneath his fingertip.
“Come, for me,” their governess said.
This wasn’t how Anna usually came, with her back arched, bucking into his final primal thrusts. Now he could barely feel her vagina gently squeezing the base of his erection. It was such a weak grasp, as if she was wrapping one of her delicate fingers around one of his. She looked so tranquil, as if she was melting away beneath him, and falling into a blissful sleep.
His governess lifted his hands away from Anna’s body and placed them on Anna’s hips. The little sailor stood to attention, pressed against his sleeping beauty’s soft warm bottom as she slumbered on her own arms. He kept her steady, making sure she didn’t topple.
Miss left them joined together for several minutes, before initiating a clean up that was as fastidious as one might expect. She made him take several steps back, and meticulously wiped Anna’s messy slit, which prompted more moans of contented delight. Once Anna had been dried, Miss pulled up her pretty French knickers and lowered her dress, then invited her to stand before enveloping her in an enormous hug.
When it was his turn, Anna got to watch with a woozy grin as Miss removed his unfilled condom, and gave his flaccid cock a thorough wiping. Only then did she pull up his shorts and underwear. But it was the moment when she adjusted his red necktie and gave him a patronising pat on the head for his good behaviour that made his boy bits twitch.
“How smart you both look!” she said admiringly. “Now, how about a bite to eat?”
Anna bounced towards the kitchen, as if the floor had been replaced by a trampoline.
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* * 6 * *
In their vintage outfits, the gathering around the dining table resembled a centuries-old domestic portrait. One of those with a twee title like ‘A Scene at Supper’, or ‘Good Table Manners’. The kind of painting where a stern-faced governess dominated the frame like an ominous black cloud, whilst those beside her wore angelic expressions of respectful deference.
Anna and Ben had played this game in art galleries on several occasions. When the erotic tension within the frame had been evident, one had sidled over to the other and whispered: is it me, or does that one have smack-bottom energy? Look closely enough, and it could be seen in any scene that had a disparity of power - where the artist had not just captured the colour and detail of the subjects, and the balance of light and shadow, but also the subtle signs of order and obedience too. Those who commissioned the bygone art of yore were rich and powerful men, with their own latent visual language, clear to see for any who cared to read it.
The table bore a delicious selection of meze, so when a plate was out of reach, whoever was nearest was asked to convey it with almost theatrical politeness. That was the effect of smack-bottom energy, otherwise everyday occurrences were imbued with an exciting edge. Anyone who acted rudely, or ate too messily, knew they might not be sitting comfortably for long. The ambient mood inspired attentiveness, which had led to some stimulating conversations.
Miss Cavendish definitely had what the Italians called sprezzatura, the ability to make things look effortless. She had a silent confidence. A studied carelessness.
“May I ask you a personal question, Miss?” ventured Anna.
“Of course, you may,” Margaret assured her graciously.
“I know you find women alluring. But do you like men? Or do you just tolerate them?”
Ben felt like a roving limelight had settled upon him, and shifted awkwardly on his seat.
“What a percipient question! The truth is: I adore men,” she paused, and then corrected herself.
“More precisely, I adore a certain kind of man. One who wears a public mask of stoic self-assurance - but underneath, a hidden fire blazes within. He has purpose, and is dedicated to the pursuit of a mission beyond himself. To me, passion that’s shouted is an unsettling zealotry. But when passion is spoken quietly and fiercely, it earns my respect.”
“A man with a lust for life radiates a silent captivating power,” she continued, “it fizzes in the imagination of those who meet him. He does not steal your attention, those who meet him cede it willingly, eager to know what lies behind his facade. Allure is the source of all sexual energy.”
It did not escape Ben’s attention that Anna was subtly nodding. She was the only one who’d truly glimpsed his own vulnerabilities, and she relished knowing his secret treasure was hers alone to keep.
“Providing external discipline arouses me, as you know. But the men I most admire possess their own internal discipline. But they’re not cold and emotionless. I adore masculine men whose inner lust is as stable as a firework, but still capable of immediate ignition when the right combination of whispers light their fuse. Such men have no need to be put in the mood, they’re always in heat - but they have the inner strength to control themselves.”
It felt unnerving to be implicitly talked about, but Ben remained silent, wondering if he met his governess’s impeccable standards. He earnestly hoped he did.
“I adore men who are resilient, and stay stiff in the face of any challenge!” she chuckled.
“Strong enough to stand up to you!” Anna observed with a smile.
“Naturally! I have no desire to infantalise or emasculate the men I discipline. But it arouses me greatly to see a resolute man so comfortable with his own identity he’s willing to shed every facet of the frame that defines him to the outside world, and appear vulnerable before me.”
“Ah, that explains the cute little sailor uniform,” Anna twigged.
“It’s so erotic to have an assured adult man become the schoolboy he once was again. To be powerful but powerless, to witness him completely relinquish his ego, and experience the humility of being a novice again.”
“Uncensored and completely seen. That’s so hot,” Anna agreed.
“The erotic only exists when it’s observed. Being seen carries the risk of shame, or disappointment.”
“Jouissance,” Anna mused, her accent momentarily becoming French.
Margaret looked impressed.
“I spent a year studying in Paris. You pick up these things,” Anna explained modestly, it had been an honest contribution to the conversation, she hoped it hadn’t come across as bragging.
“Lacan did have a point,” Margaret concurred. “True intimacy is disruptive, it can be scary, it takes us to the brink of The Real, and beyond is an unknowable wildness.”
“I’ve always thought of porn as sexuality that’s been domesticated,” Anna mused. “A once wild force that’s been tamed, and is now available on demand, like running water.”
Margaret smiled at that thought. “I like that analogy. Porn is like industrialised agriculture. Endless fields of exactly what we want, without the awkward pests and the weeds. Sex without the risk of hurt feelings isn’t really intimacy at all.”
“It’s not that we never watch porn,” Anna admitted on their behalf, “but we’d much rather create it than consume it.”
“I’m very pleased to hear that! Our sexual energy is precious, far better invested in experiences and memories than frivolously squandered! Talking of which, who’s ready to make some more marvellous memories?”
Two pairs of hands shot excitedly upwards.
A short time later, Miss Cavendish was standing beside her little sailor boy, having just pulled down his shorts and underpants. His arms were obediently folded behind his back, whilst the fingers of her right hand held his penis so she could aim it towards the toilet bowl.
Before they’d resumed playing, she’d insisted on taking them both to the toilet, one by one. Anna had been escorted first, led away by her hand to the downstairs bathroom, then led back a short time later with her face flushed bright pink.
Just before he started to pee, she asked him a question.
“Have you decided what to ask for?”
“Yes, I have, Miss. I heard what you said at the table. A man should be resolute and bold, and pursue what he desires.”
“Good boy. Never blunt your own edge. If others don’t consent, you’ll still gain their appreciation by respecting their objections.”
“I do have one question though. Why us? You must have a queue wanting to play with you.”
“Anna,” she replied simply.
No further explanation was needed. Beautiful Anna had a rare ability to attract wonderful people into her life. Certainly he’d been drawn towards her like a magnet. Deep down he still couldn’t believe someone as radiant as Anna could be genuinely interested in his unremarkable ordinariness. But perhaps he had just the right kind of ordinariness.
“She is awesome,” he agreed. He could feel a surge of pride glowing inside, he was so privileged to be part of her life.
“She is. I wanted her, ever since we first met. I was quite blunt and told her, and she was interested. But she insisted you were part of it too. So we met that first evening for a chat, and you were such a cute and polite little boy! As soon as I got to know you, I knew I wanted to discipline you too.”
“That evening we met, did you masturbate thinking about us when you got home?”
“I did indeed think about whacking your bare bottom, young man, and I enjoyed it immensely.”
“Good. Because we certainly fucked hard thinking about you.”
“That pleases me greatly. Anna told me she wanted to watch you take my bottom. I told her I thought deep down, most naughty boys want to poke their cocks into the bums of those who spank them. It’s just so few are ever given that chance.”
“And you’d be willing to let me do that?”
“Only those who are willing to let go of power should be trusted to wield it.”
“You’ve seen how big I get. It might hurt,” he added cheekily.
“No more than the caning you’ll be getting afterwards, young man,” she retorted.
She emphasised her point with a hard slap to his bottom. He’d been holding himself back as they’d been talking, but now began to pee freely. Despite his earlier wiping his penis still felt numb in places from the delay gel, but now the warm stream made it feel like the whole region was thawing. When he’d finished, Miss wiped him dry, extremely thoroughly.
So his face was just as pink and flushed as Anna’s had been when he was led back to the living room. She was sitting primly on the sofa, hands folded on her lap. She smirked as they exchanged knowing glances, and he knew she’d been wiped just as meticulously too.
They took their seats, facing each other, as if waiting for a performance to commence. Once more, Miss Cavendish assumed the role of their compère.
“Now Master Benedict, as you’re in charge next. Why don’t you tell us what you want?”
He answered immediately. He knew if he hesitated, what he’d rehearsed in his mind would rapidly spoil. The echo of what he’d uttered rang in his ears, he couldn’t believe he’d actually said something so filthy. Force of habit made him steel himself for rejection, to be scolded for being so disgusting, preparing to back down and suggest something that wasn’t quite so outrageous.
But Margaret didn’t make a fuss, responding so calmly it was as if she was accepting the offer of a drink.
“That is acceptable to me.”
Ben felt a rush of energy surge through him. It was actually happening. He did his best to remain nonchalant.
“Then Anna and I shall go up to our bedroom, will you join us in ten minutes?”
“I’d be delighted.”
Ben sprang to his feet, and despite not knowing the details of his plan, Anna did the same. He took her by the hand, giggling as they dashed upstairs as if running up a gangplank, about to embark on an exhilarating adventure. Which, in every sense, was exactly what they were doing.
Exactly ten minutes later, Miss Cavendish glided gracefully up the stairs, as imperceptibly as an assassin. Governesses seemed to possess the innate ability to tread lightly, all the better to swoop upon on-going mischief like an ambush predator shrouded in black satin.
The door of the couple’s bedroom was open, just as it had been when she’d watched her naughty sailor boy proudly stroking his big stiff erection in front of the tall mirror. This time though, he was nowhere to be seen. She peered around the doorway, and glimpsed two piles of clothes on the floor, as if their occupants had suddenly been struck by a terrible curse and melted where they’d stood.
She could hear a faint moan, like the lament of a recently disembodied soul. It was only when she craned her neck around the doorframe that she caught sight of Anna’s bare foot. She was lying on the bed, naked.
Anna’s hips were writhing in slow serpentine motions. She had limited freedom to move, since her wrists were cuffed to the top of the bed. Her head was raised slightly by a small pile of pillows, allowing her to look down the length of her body. When she saw her governess appear, she relaxed, opening her legs slightly. A gesture that seemed to be an invitation to step further into her private sanctum.
“Oh Miss,” Anna said theatrically, “that naughty boy has tied me up!”
Margaret surveyed the bedroom. The navy sailor-boy outfit lay in a puddle on the floor, its recent occupant nowhere to be seen.
“You are a naughty girl,” she scolded, “sneaking off to have your pussy fucked!”
“Oh Miss!” Anna squirmed. “Will you be caning us Miss? For being so naughty?”
“I should fetch my cane right now and lift up your legs, young lady!”
“Oh Miss!”
“And when I find that naughty boy, he can lie beside you with his legs up too.”
“Oh Miss! You wouldn’t cane a girl with a dry pussy, would you? Will you please lick me, Miss, Before you make my bum all sore. Please?”
Anna splayed her legs as she pleaded, exposing her tiny pouting lips, they resembled a little puckered mouth, desperate to be kissed. Her governess stepped sideways to obtain a better look, which brought her to the bottom of the bed. From this vantage point, she could lower her head, and look up at Anna’s three hills in perfect alignment. In the foreground, the smooth bare curve of her mons, with the pink fleshy valley underneath. In the distance, on either side the peaks of her nipples, and on the horizon, Anna’s wide eyes, glowing like a pair of setting suns. Such a beautiful view. One could linger here.
Margaret leaned forward, resting her elbows in the space between Anna’s knees. The bed’s high mattress allowed her to stand without bending her legs, merely by tilting her hips. Anna had sufficient slack in the cords of her cuffs to shuffle downwards until she felt Margaret’s warm breath against her slit.
The governess pushed her hands forward and cupped one of Anna’s soft pert cheeks in each of her palms. In between planting tender kisses on her eager lips, she made Anna repeatedly acknowledge who was in charge of her pretty bottom, that she was a naughty little girl, and that she deserved to be spanked long and hard.
The thing is, if you tell someone she’s a naughty girl enough times, it’s inevitable she’ll start acting like one. As her excitement mounted, Anna curled her legs upwards, opening herself lewdly, in the hope Miss’s expert tongue might suckle her holes. Then, indulgently, she reached the point when she didn’t want the licking to stop. That was when Anna dropped her legs over Margaret’s shoulders, hooking her knees beneath her armpits, locking her in place. Anna felt her clit slide up the slope of her governess’s nose, as she pushed her needy cunt into her face.
Margaret realised at once that she was trapped, and rebuked Anna for her naughtiness. But with her mouth pushed so close to Anna’s slit, her scolding was more felt than heard, a succession of hot moist breaths and vibrating lips. As the hot muffled words hummed against her slit, Anna writhed and gasped, and began to wonder if she could be scolded over the edge.
Ben had remained out of sight in the en-suite as they’d been talking. He had rolled a condom down his engorged erection, and watched from behind their governess as their devious trap was sprung. Anna had executed her part of their plot perfectly. Anyone lured towards her irresistible little honey pot couldn’t help bending over, raising their bottom up perfectly.
He dandered into the bedroom, taking his time to appreciate the elegant black satin that was pulled taut over the curves of her bottom, and the deep dark dark valley in between. He trod so softly that she only realised he was standing right behind her when he finally spoke.
“It seems the hole I was going to fill is busy,” he declared as he lifted the hem of his governess’s skirt, “I’ll have to find another one…”
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Continued in part 3…
@spankingtheatre 2024
This is an exquisite tale, thank you for the pleasure you gave as I read and reread the passages
Very intense! Good job