I wish I could say I wrote this, because it’s a pretty good example of some faux Victorian flagellant porn. Alas, I’m not the author. That honor goes to Jean Marie, another author whom I have run across in my frequent travels in the Wayback Machine. As usual I have little information as regards origin of this story.
It was exactly the position Bertram had hoped and worked for most of his young life. All of his meticulous matriculation had finally paid off; at twenty-four he’d been hired by the wealthiest widow in all of Suffolk County, Chelthingham, England to tutor her two daughters in academics, the nearest school for girls being too far away from the vast manor estate.
The handsome young man was just what Lucinda Ballingbrooke was looking for. No, not for herself, although the thought of that made her blush hotly and experience the vapors beneath her floor-length crinoline gown. He was for Trish and Marie. The piece de resistance was the fact that this Bertram Ware, besides graduating top of his class from the normal school for teachers, had also spent a year in a theological college, considering the priesthood. Lucinda sensed in young mister Ware a moral rectitude that was refreshing. It might rub off on that spitfire of an eldest daughter of hers. Patrician Ballingbrooke was eighteen years of age chronologically, but a toddler in terms of manners and decorum. In many ways the baby of the family, Marie, at just ten, was Patrician’s superior in maturity. They’d be a handful for Master Ware, more of a handful than any female tutor had been able to manage. And if the young educator was not able to resist the considerable charms of Lucinda’s eldest daughter, she concluded, at least he was gainfully employable and properly brought-up, unlike the parade of past suitors for Trish’s affections, from a stable lad to an itinerant repairman of the slate roof to the son of the former downstairs butler.
This new school marm of a man was just what Trish was looking for, as she spied him shake her mother’s hand in the main entrance courtyard, mount his horse, and canter out the manor gate and down the long, straight road that led, eventually, to the small town of Chelthingham. Because her third-floor boudoir window was as expansive as the teenager was narrow-minded, she could watch him ride for long minutes after her mother had congratulated him and bid him adieu. Trish continued what she’d been doing, with one hand down the bodice of her gown, pinching each of the achingly erect nipples in turn, while her dexterous right hand was up underneath the hem of said gown, teasing the bedewed pubic curls of her aroused and bloomerless sex. Now Trish had a visual stimulus, the dashing man who appeared to be an expert horseman, to match her mental and manual ones, and her masturbatory efforts became more fervently focused, until the pretty, perspiring blonde attained release with a series of gasps and moans. I hope he’ll mount and ride me as energetically, she thought to herself, as the rider disappeared over the far horizon.
“What are you doin’?” Marie exclaimed accusingly as she barged into her sister’s boudoir.
“Just straightening my gown,” Trish countered as modestly as her flustered countenance could muster, “and I’ll thank you to knock before entering from now on.”
Marie looked askance at her elder’s jism-coated digits before Trish could wipe them on a linen handkerchief, and wondered if those fragrant fingers had knocked before entering forbidden folds, but only said, “I just came to warn you that Mummy is on her way up to talk to us…”
Trish’s look turned appreciative, as she countered, “What about?”
“I think you know; we’re gonna get a new tutor, a man this time,” said the prepubescent red-head.
“That is correct, Marie,” intoned the imperious matron of the manor as she swept into the room, “and I’ll thank you both to treat him with respect, unlike the parade of tutors that you two have worked your way through in the past. He’ll be returning with a carriage of his belongings to sign a contract and move into the cottage this evening. Your lessons will start tomorrow.”
“Yes, ma’am,” answered Marie dutifully.
Neither mother nor daughter was sure about the expression on the other girl’s face; was it a pout or a smirk?
As if Lucinda was prescient, that is exactly what transpired. Master Ware arrived just after eight that evening, as supper was being cleared from the informal dining alcove by the staff, with a small carriage containing all his worldly possessions.
Trish should have taken it as a portent when the man signed his employment contract as “B. Ware,” instead, by way of first impression, she looked askance at his only trunk and muttered, “You haven’t accumulated much in life, have you?”
Without missing a beat, the tutor replied, “A wealth of knowledge and fine manners, which, outside of an unearned inheritance, is more than you can claim, young lady.”
All in the drawing room silently acknowledged that the pedagogue had won that repartee, but the lady of the house wanted to seal the deal.
“Allow me to tell you a story that I heard from my late husband. It seems that Lord Ballingbrooke once hired a man to break and train his head-strong horse. He informed the trainer that he didn’t want the well-bred filly harmed in any way in the training process. The man nodded, but then hit the unsuspecting animal hard across its head with a club. Lord Ballingbrooke exclaimed that he’d just forbidden that type of behavior, to which the trainer replied, “Yes, but first you’ve got to get their attention.”
“Lord Ballingbrooke told me that story on our wedding night,” she continued, “when I was making excuses, due to the stress of the day and fatigue and apprehension for not joining him in our marriage bed to perform my conjugal duties. He also produced this,” and she took from off the desktop a long box, out of which she produced a long, thin rattan cane. “He used that on me that night. I’m sorry to say that when he died, I wrapped it up and put it away. I should have used it frequently and ferociously in your upbringing,” she said to her two daughters. “Perhaps it’s not too late, I bequeath it to you to use as you see fit,” she concluded to the new employee, handing him the implement by the curved handle. “These two fillies of mine need training; the younger one is too smart for her own good, but otherwise a thoroughbred, I can’t say any of that about the older. Be strict with them, and good luck.”
“Yes, ma’am,” he answered and cut the rod through the air with a fearsome swish. “I’ll see you two ladies in this room at eight o’clock sharp tomorrow morning,” he said, looking from the wide-eyed red-head to the sultry-eyed blonde.
Mr. Ware was in the drawing room preparing his lessons at seven, Marie arrived punctually an hour later, Trish strolled in several minutes after that, thumbing through a large volume studiously. The incongruity of the picture of her sister with an open book raised Marie’s eyebrows; her tardiness raised the tutor’s. Before he could say a word, however, Trish piped up.
“I was wondering, do you know the proper name for a group of African lions?”
“Yes, a pride.”
“And what is the answer for a mathematical division problem called?”
Trish was flipping through pages, looking for a subject that would stump the man, Marie began filing through her mind for something similar, when Ware cut them off.
“I’ve passed your mother’s tests for employment; that will have to satisfy you two, as well. Now to begin, I’d like you each to write an autobiographical essay as an introduction. Tell me…”
Marie was conscientiously getting out parchment and quill, but her sibling merely produced an attitude, “Can’t I just tell you my life’s story? I hate to write!”
“That’s part of the benefit of the lesson, this will…”
“Oh, god, I can see how this is gonna go…” Trish interrupted impertinently, as she slammed the thick book down on the desk.
She knew that she’d erred as soon as she saw the storm clouds pass over his here-to-fore sunny disposition. As quick as lightening, he seized her by the wrist.
“You can inform your mother this evening at supper that it took all of a minute and a half to earn your first chastisement,” he said as ominously as a thunder clap. “Because your offenses haven’t been that serious, the first lesson will just be a spanking, in hopes that we can forestall a caning…”
He sat on the edge of the desk.
“You wouldn’t dare!” Trish exclaimed with a shout.
Contradicting her, her adroitly pulled her across his lap, twisted her struggling arms behind her back, and pinned her kicking legs between his own. His free right hand wrestled the rustling long gown up from the floor to rest on her lower back, presenting her bare and bouncing behind to Marie’s and the man’s gaze.
“Why am I not surprised?” he commented about her lack of bloomers to no one in particular. It was an onion of an arse, he thought, so sweet and succulent, it nearly brought tears to his eyes. It was fair complexioned, fulsome and round, as cheeky as its owner. He ran his hand over its curvature, appreciating the cool smoothness, the musculature of its marble-like stature paired with the softness of its baby-fat resilience. The heel of his hand pressed into the firm flesh, parting the globes and giving him a glimpse of the nether valley between the orbs, at her puckered rosebud and engorged sex. He lifted the hand, letting the cheeks spring back together.
“Please don’t do this…” Trish pleaded in a barely audible whisper, “I shan’t be able to stand it…”
“That’s for being late…” and he laid on ten resounding spanks that tinged her tushy a bright pink.
“And that’s for the unlady-like lack of knickers…” and ten more brisk swats reverberated off her rump, the sound ricocheting off the walls.
“This is for questioning me…” and twenty stinging wallops turned her upturned ass a dusky rose.
“And this is for the incredible impertinence that I’d better not see again soon….” And Bertram Ware began to spank her bottom in earnest. He intended to administer about another twenty or so punishing smacks, but when he had, there was still defiance in her demeanor, so he continued. He spanked her until she quit fighting him and gave in to her fate, spanked her until she began to cry big crocodile tears, spanked her until her backside was glowing magenta and hot to the touch, until his anger was dissipated, her attitude extinguished, and her wrongs absolved.
Before he was done, Trish had cried out all her tears, and Marie was crying in sympathy for the sister who had been so cruel to her for ten long years.
Ware stood the stunning, if stunned, girl on her feet. Her hands shot back to rub her abused bottom before her gown could fall back into place.
Trish soon discovered that rubbing didn’t extinguish the fire in her flesh. “May I be excused to go wash my face in cool water, sir?” she inquired to the floor between sniffles.
“Yes, but don’t be gone too long; you still owe me that writing piece.”
In the sanctity of her boudoir, Trish raised her skirt again and looked over her shoulder at her smoldering derriere reflected in the mirror. The vision was the fulfillment of a life-long fantasy, and so, instead of applying cold cream to her apple-red cheeks or cool water to her tear-streaked facial cheeks, the wanton blonde parted her sex to expose her eager clit, licked her fingertips, and masturbated herself through a series of explosive orgasms.
A half hour later, Trish returned to the drawing room.
“Where’s Marie?” she whispered in a voice thickened with lust that she tried to make sound chastened, if not chaste.
“It seems your sister was quite upset by the spectacle of seeing you properly thrashed. She couldn’t stop weeping. I sent her to her room until she could settle down.”
“Did she write her autobiography?”
“A feeble attempt,” the tutor responded, waving a tear-spattered half page of writing in the air.
“That says it all!” Trish shot back. “That little snot gets off scott-free, and I get punished for the first offense, yet Mother thinks her a saint, and condemns me to hell as the devil incarnate.”
Bertram decided not to correct her that it was the third offense that got her spanked. Instead he changed the subject. “You don’t look like you rinsed your face…”
A look of guilt mixed with determination flashed across her features, “No, I bathed my senses in sin instead. The spanking inflamed more than the flesh of my bum, it inflamed my libido, and I fingered myself to ecstasy. Are you going to punish me again for it?”
Far from being put-off by her show of willfulness, Ware was impressed with the head-strong maiden who so readily admitted to her other strong affinities.
“Would it do you any good?”
“Probably not,” she smiled.
“Then I’ll wait.”
The coy blonde broke off his direct stare as she arranged a fresh parchment, quill, and ink bottle on the desk before her. “My bum smarts too much to sit upon; if I did, all I’d think about was how much it glowed, how much I need a proper fucking…” With this she hoisted her skirt up yet again, until her saucy curves were revealed to the naked eye once more, then bent over at the waist to lay prone, face-down upon the desk top. “You’ve seen it all before,” she said with a nod of her head over her shoulder at her exposed backside, “and I really can’t sit yet… It’s not like my bum is any different than every other girls’.” She arched her bubble of a butt out provocatively, as if asking him to pop it. Bertram didn’t do a thing, but he disagreed with her assessment of her derriere’s desirability vehemently. “In this posture, if I get writer’s block, you can cane me until I’m over it,” she cooed. She then dipped her quill in the ink and began writing.
Bertram was powerless not to stare at her perfect pink posterior. Indeed, his hand, as if magnetized, was drawn inexorably to her tush, to massage the surface he’d spanked a short while ago. “I probably punished you harder than you deserved,” he mumbled apologetically. Another appendage was drawn to her as well; his pole strained to point due North, too, but his codpiece contained the massive erection, if just barely.
The man tried valiantly to restrain his lustful longings. In a quavering voice he said, “You speak as if you crave punishment, young lady. Did you enjoy your spanking?”
“It confirmed that a dream I’ve held since before I can remember was not just fantasy,” she admitted tentatively, then couldn’t help but smile. She was enjoying talking openly about something that had always been secret. She was enjoying the tender ministrations of his hand, as well; much like a cat luxuriates in being petted. The pussy purred beneath her up-turned bottom, inches from his tender touch.
“Then would you like to be caned?” he intoned resonantly, letting his dominant side have free reign for the first time in twenty-four years. It thrilled him to give voice to his most secret desires, as well.
“I fear it,” she said with an involuntary shiver, “but I’d be a liar if I said no. I’ve read about fair maidens having their bottoms caned in the smut books of my father’s in the library. I confess that it excited me as much as terrified me.”
“I’ll remember that for whenever I do cane you.”
“Have you caned as many women as you’ve spanked?” she inquired, sure that by the masterful way he’d spanked her, he’d spanked scores of sweet young things.
He paused dramatically, “…When I administer your first caning, the total will come to an exactly even number of women, yes… Exactly one.”
The blonde froze for a moment, threw her quill down and stood bolt upright, pivoting on her feet to face the man of her dreams. She pressed her length to him, feeling the compliment of his rampant erection throb against her tummy. “You mean,” she sighed, “I’m your first?”
As he nodded, they kissed. The kiss contained all the passion usually expressed with the words, “I do.” Tongues were exchanged, as was a copious quantity of saliva. Other bodily fluids would have followed suit, if his cool intellect hadn’t intervened.
“We’ve only just met… and I’m supposed to be your tutor…” he said in a whisper bordering on a whimper, so vehement was his lust.
“Yes, we ought to wait,” she agreed, sounding unconvincing. “Look what I wrote for my autobiography…” and she handed him the parchment, the ink still as wet as her besotted thighs.
“Dear Sir,” he read aloud. “I have ne’er done well in school-work, I think because I ne’er applied myself. When you applied your strong bare hand to my bared bottom, I felt inspired for the first time in my life to apply myself as resolutely to learning as the spanking was applied to my deserving backside. This is my solemn vow. Thank you for your efforts of correction on my behalf.
I regret to confess that I have been promiscuous in the past, letting a total of three different boys touch my breasts and sex with their hands. I am highly-sexed, and letting them go just that far was a triumph of sorts, I suppose. The fact that none of the three expressed the least interest in my bottom, the seat of my sexuality, made it easy for me to cut off each relationship after the first tryst. I long to give myself completely to the man who can subdue my passions, dominate my will, and quench my lusts. I think that I see just such a man in you. It certainly seemed so a minute and a half into our first lesson, when I got my own special session of tutoring.
I long to learn all manner of things from you, cerebral and carnal, as much as I yearn to share myself, my charms, and my whole heart and soul with you.
I feel like a competent student for the first time in my life under your marvelous tutelage. Teach me.
I feel like a complete woman in your masculine presence, for the first time in my life. Touch me.
I feel like my mother’s afore-mentioned thoroughbred filly before your masterful precepts. Train me.
The eloquent teacher was dumbfounded, for the first time in a long time his verbose nature was silenced. He folded the paper and put it in his breast pocket. Trish didn’t know it, but he held her words in his heart from that day forth.
She proved an apt and obdurate pupil, as perseverant as she was perceptive, often outdoing the more gifted Marie in diligence. On his first day off, six days later, Bertram ventured into Chelthingham and purchased a sheep-skin condom, much like the one that Casanova had written about using.
They’d had to make do with stolen kisses, quick caresses, and furtive looks for a week. Patrician’s unrequited passions were about to boil over. Mercifully and magnanimously, Lucinda announced that she desired to take the girls on a shopping excursion to London, to be gone a fortnight, leaving at dawn the next day. Unfortunately, Trish felt ill the morning of departure and decided not to go at the last minute, foregoing a wealth of new trinkets. She was about to be rewarded with something more prized; first-hand experience in matters of the flesh.
She arrived at the drawing room early the next day, just after seeing her family off on their spree. Her tutor closed the double doors behind her and locked them, seconds before she finished unbuttoning her bodice and letting the gown fall to the floor. The eighteen year old virgin was as naked as the day that she was born, and even more beguilingly beautiful than any new-born, in her full blush of feminine ripeness.
“Goodness, how clumsy of me!” she mock-protested, putting one alarmed hand to her mouth, the other in front of her frothy blonde pubic bush.
“Yes, clumsy…” Bertram repeated, “…but more astounding is the fact that you still haven’t learned to wear knickers or a corset! One would have to assume that you’re a brazen harlot, in need of easy access to your nether charms…” He took her by the slender wrist and felt her pulse pounding in his grasp.
“My mother always said I was as stubborn as I was slatternly, whatever shall we do about it, sir?”
“Spank you; long and hard and without remorse…” he pronounced as he sat on the edge of the desk, the very spot where she’d been disciplined a week before.
“Oh!” she gasped while fairly diving into position across his knee.
Bertram administered just as vehement a thrashing to her innocent if chubby hindquarters with his calloused hand as he had the first time, made much more bearable by the frequent fingering of her slick slit. The conflagration he ignited across her exquisite ass was awesome to behold, and hold her burning bottom she did as she arose from off his lap some time later. Like a phoenix rising from ashes, Trish stood up with her fanny on fire; her buttocks singed by spanking, her loins about to combust with lust. She ripped the clothing off her lover, not caring if buttons were lost or fabric torn. When she yanked his breeches down, exposing his rampant manhood encased in its protective hood of supple sheep leather, Trish began to softly cry; both at the thoughtfulness of the gesture of his wearing it, and at the terrifying size of his ominous thingy beneath the mask.
He scooped her up off her feet, laid her down on the carpet, and kissed her passionately. He enjoyed the softness of her bosom and the resilience of her hardened nipples. He took special care to play with her buttocks, kneading them like bread loaves roughly and caressing them gently. He parted the fleshy hillocks and tickled the delicate rosebud that flourished in the valley there. Then, when both of them were aroused to a heightened state, he skillfully played at the entrance to her pudendum for a moment to lubricate his head and accommodate her sensibilities to the prospect, then shoved his sword home to the hilt in her scabbard and fucked her. He fucked her like a veritable bull in the barnyard. He thrust her through more orgasms than she could count. He turned her over like a griddle cake and fucked her with fresh energy from behind. He fucked her like an inexhaustible machine, pistoning her pussy relentlessly. She was on the brink of losing her mind from all the climaxes, but also sensed that their spirits were flagging from the prolonged carnal romp, and guessed that he was so full of endurance due to a lack of sensation through the condom. She wanted the fireworks show to reach its pinnacle dénouement, to have him come inside her. She wanted to fall asleep in the arms of this man of her dreams and drift off into heavenly slumber together. Direct action was called for. Trish steeled herself for what she was about to say.
“If I were to take that condom off your marvelous cock,” she whispered seductively in his ear, “then put my lips to your manhood like a common whore, and take the stiff sword down my throat as I sucked upon the glorious tool, would you cane my outrageous naughtiness for me with a memorable lesson across my needful bottom?”
She felt his blood surge, and his penis lurch lustily inside her, giving her the only answer she needed. She withdrew the valiant charger from her wet womb of a stall, untied the leather hood that covered its head, and stroked the length of his thickness as she spoke again.
“And after my caning, would you put this lovely cock inside me again, inside me without benefit of its desensitizing cloak, inside me someplace nasty, but somewhere that won’t get me pregnant, say, someplace like up my tight, virginal arse-hole?”
The bird in her hand fluttered its keen interest by stiffening all the more, and Trish knew what she was in for.
“Then let’s prepare the orifice for penetration, so that right after my whipping you can roger me fast and deep…” she whispered hotly, then turned to present her rump. “What’d we have in the house that’s slick enough?”
“There might be some axle grease in the carriage house…”
“Too far,” she said dismissively.
“Some cooking oil in the kitchen?”
“The servants will see us,” she shook her pretty head.
She reached into her purse, “This’ll have to do…” she muttered as she withdrew her lipstick. The tiny paintbrush that she’d used on her bee-stung lips so often with the metal compact of red pomade looked useless; Trish threw it aside along with the top of the canister. “Work a good finger-full up my bum,” she instructed, getting atop the desk and putting her head down and her ripe pear of an ass up high in the air.
The instructor did as instructed, lubricating the tiny aperture thoroughly.
“Ummmm, that feels so good…” she sighed lasciviously, reaching to stroke her pussy as his finger corkscrewed her now-slippery rectum. The anal-erotic submissive played at her sex’s portal, as her lover penetrated the puckered portal an inch away, until yet another orgasm, like a wave sweeping over her entire being, buffeted her about. It left her drenching wet and renewed for what was to come.
“Now to earn my stripes,” Trish said as she clambered down off the table to kneel at her master’s feet. She licked her lips hungrily as she took his engine in hand. She looked up into his eyes as she kissed the circumcised head, then took the thing into her warm mouth. Her tongue swirled expertly around the onion-like helmet, and then she admitted the length of the monster down her throat. Bertram shuddered and closed his eyes. She regurgitated his manhood with a slurp, kissed his head once more as it exited her oral orifice, and admonished, “Now don’t you dare ejaculate in my mouth, lover. I’d welcome that another time, but today I want you to take my anal virginity.”
Seeing that he was primed for this, she turned and bent over the desk, “Please cane me hard, sir.”
He lifted her, turned her to face him, and looked deep into her eyes.
“Are you sure you want this?”
“With all my heart,” she answered, turning her heart-shaped derriere back over the edge of the desk and sticking out at him with an inviting wiggle.
He took the cane from out of its box and took aim.
“I was very bad,” she said in a voice cracking with emotion. “I foolishly let others enjoy my femininity without waiting for true love. Cane me for it.”
Bertram raised the whip and brought it down unerringly across the summit of her unblemished buttocks with a resounding crack. The hapless girl yelped, clutched at the fiery welt that now bisected both bum cheeks, and danced an impromptu jig. He was sure with that one wicked stroke that he’d cured her of any desire to be caned further. But surprisingly, as soon as the lass regained control, she bent full over in the international signal known by all dominants and submissives the world over to say, “Please, sir, I want more…”
“I let boys defile my purity with their dirty hands,” she whimpered as she thrust her rump out again.
Trish cried out, composed herself, offered her backside to the lash anew.
“I let one teach me how to give head…”
Bertram thought that she was being far too hard on herself. She was good at the act, after all. She didn’t have any communicable diseases; no harm, no foul, in his considered opinion. But he also understood human nature and the nature of guilt.
“How I wish I’d known that you were in the world!” she pleaded remorsefully.
“Now that I do, I want to be purified…”
“Purified in the fire of a sound whipping,”
“At my lover’s expert hand,”
“I love you, Master Ware… please cane me harder,”
Her sobs obliterated the following words, but her arched arse’s message was unmistakable.
She tentatively stuck the pretty, plump pillows of her posterior up and out again. They quavered and trembled, near exhaustion.
“Thank you, sir,” she blubbered, “I’ve learned my lesson…”
Bertram put the cane down next to her shaking form on the desk, sunk to his knees and softly kissed each of the marked cheeks in turn. Ten vivid wheals burned across the surface of her otherwise porcelain-white pulchritude. “And I love you, Patrician Louise Ballingbrooke,” he breathed, nuzzling his face against her wounded roundness. He stood and kissed his way up her spine, stopping to nuzzle her neck before their mouths joined. She thrilled to feel his hardness align itself up the crack of her bottom as he hugged her to him from behind. As soon as their lips parted she sighed, “Take me…”
He stood to do so, but she continued from her supine posture like a randy lady-of-the-evening.
“Possess me up my ass… Ride me bare-back… Fuck my tightness with your condom-less cock… Cum in my bowels…”
He cut off her raunchy rant with a sound spank. The slap reawakened the pain of all ten stripes simultaneously.
“You need to curb your scurrilous tongue, young lady,” he pronounced with another swift spank, Smack! “You need to make requests, not issue orders,” Smack! “You need to remember who wears the pants in this relationship,” Smack! “and who never remembers to wear her pantaloons.” Smack, smack, smack! The spanking hurt incredibly, but turned her on even more.
The balance of power thus righted, Bertram parted her smarting butt cheeks with a firm pinch of each orb and revealed the painted and winking anus to view. He pressed the head of his rampant lance to her pulsating pucker-place. She pressed back into him, impaling herself with a soft gasp. His length slid into her private pleasure-passage, filling her, stretching her, occupying not only her ring of muscle, but her mind, her consciousness, her entire being. Being butt-fucked wasn’t so much different than being spanked, she found; a certain friction transformed into heat, the pain translated readily into pleasure. She found that she liked it.
When his short and curled pubes tickled her engorged ass-hole, and he was buried to his base within her fundament, he enwrapped her in his arms. She spied over her shoulder at him with nothing but trust and warmth.
“I feel honored to be the one to first experience the exquisite tightness of your backside,” he enunciated as he withdrew and re-inserted his tumescence.
That’s a hell of a place to stop, but yes, the story does stop there. An HEA ending? I don’t know, but I think we can safely assume the happy couple will be HFN (happy for now).