Her Shameful Training

by Emily Tilton

  Her former employer had told Joanna should be terrified of the degradation of being made to take the penis, but here in Lord Stephen’s tower room Miss Joanna Middleton had, a little while since, received the prick of a nobleman in her young cunny—and before that she had had to have it in her mouth. The shameful things Mrs. Mund had darkly accused Joanna of desiring had taken place: a man had fucked her, over a bolster, his hardness surging in and out of her wet cunt, his hips pounding the bottom he had flogged to teach her a terrible lesson in obedience. Joanna had begun to undergo, she could not deny, precisely what Mrs. Mund had predicted she would—and indeed precisely what the widow had caused by driving her young companion away with that final naked spanking—when Mrs. Mund had told Joanna all about the brief marriage in which Mr. Mund had used her with his penis in such a cruel and careless manner. Miss Joanna Middleton should, she knew, feel debased and sorrowful at the way Lord Stephen had made a woman of her with his thrusting cock, but in her heart—and in her cunny—she felt quite the opposite.

  The device in Doctor Brown’s hand, however, made all the feelings of shame she had known over Mrs. Mund’s knee come rushing back into her mind. Her cheeks blazed hot as she recalled the widow describing the wedding night in which Mr. Mund, after riding her cunt for a time, had withdrawn his prick. How he had very casually informed his young bride that she must bend over the side of the bed and put her hands behind her, to part her bottom-cheeks and show the tiny hole between them. How he had whipped her with a punishment strap when she refused, until Mrs. Mund had gotten out of bed, trembling with shame, and obeyed, spreading her painfully punished backside so that her bridegroom could anoint her there with an oil that would ease his cock’s passage in and out. How he had made her beg for his penis in her bottom rather than a renewal of the strap’s visitation, and had then thrust in, telling her how pretty she looked that way, bending to give her husband this ultimate conjugal right—one he intended to exercise every night between her young bottom-cheeks.

  Over Mrs. Mund’s lap, with the ivory hairbrush spanking her own little bottom again and again, Joanna had heard this tale from the widow’s lips along with the news that her employer considered it much too probable that Joanna herself would be made by some seducer to receive a prick in her own bottom-hole. Mrs. Mund intended to do everything she could, the woman had said, to prevent it, but she feared Miss Joanna Middleton’s base birth would make such efforts unavailing. The widow had stopped spanking, and parted the round halves of Joanna’s backside painfully, to assist in delivering her opinion. She had placed her own finger there, and declared that such a little anus would undoubtedly hurt a very great deal when a man elected to use Joanna there, as must surely befall the girl, since her origin carried the taint of bastardy.

  “No...” Joanna said, now, looking beseechingly at Lord Stephen. “No, please, my lord. Not in my bottom?”

  “Hush, Joanna,” said his lordship, reaching out to stroke her cheek. Joanna smelled the wicked smell of her cunny’s need upon his fingers, and the memory came rushing back of how he had touched her on the inside and made her spend so strongly she had thought she must swoon. That made her blush, but in her secret thoughts she could hardly deny how much she had liked it. Could he not fuck her there again, as he had said he would take care of her should she conceive? He continued, looking into her eyes, “I have told you several times already that I must have your bottom. Doctor Brown is going to prepare you to give me my way there. It will be uncomfortable at first, but you will grow to enjoy it as I train you to take the penis deeper and deeper in your sweet bottom.”

  “But... my lord... why?” Joanna begged. “Why must you... why there?” Her face blazed as she whispered the final word, her eyes going helplessly to the black thing in the doctor’s hand, to which the Scotsman now applied a viscous liquid from a little vial in his other hand. It must be the sort of oil Mrs. Mund had meant, when she had told Joanna about her wedding night, her bridegroom’s peremptory preparation of his young wife’s anus for the prick.

  “Hush, Joanna. I do not wish to have to punish you again,” Lord Stephen said a little more sternly. “The trainer must go in your bottom now. You do not have a choice in the matter: I desire that you be made ready there, because I desire to possess you there with my cock.” He turned to Doctor Brown and nodded once. Joanna writhed again, sobbed in fear and shame, tightened her bottom desperately as she felt the narrow, oiled tip of the awful thing press against her tiniest, most private place.

  “Try to relax, Miss Middleton,” the doctor said. “His lordship’s words might not seem helpful to you in that regard, but it is better that you should learn to give your master his way with a full understanding of his right of the phallus when it comes to your fundament, as I often like to term this part of a young lady undergoing sexual training.”

  “My... my what?” Joanna sobbed.

  She tried to lift her head, shamed and startled as much by the new word as by the strange feeling of the plug pushing into her. She felt her brow crease and she bit her lip at the discomfort, but something in the way the physician spoke, perhaps even merely in the tone of his voice, when she remembered also the manner in which Lord Stephen had just declared his humiliating intentions where her virginal bottom-hole was concerned, made it feel different to what Joanna had expected.

  “Your fundament, Miss Middleton,” Doctor Brown said in a matter-of-fact tone, pressing again upon the thing so that Joanna gave a whimpering cry and arched her head back against the mattress, her buttocks once again trying to close, to push the awful trainer out and away. The doctor, to her dismay, pushed back more firmly, and she sobbed at the feeling of the device entering her further, filling her bottom more completely.

  “Oh, no,” she whispered, closing her eyes against any sight of the lascivious scene, for though the shaft hurt as Doctor Brown pressed it into her backside it also felt... pleasant... and... submissive, in that way she found herself wanting to yield to Lord Stephen’s lewd attentions.

  A little mewling sound escaped her throat. The trainer went in further. Joanna remembered that the doctor had said they would use another one, too... a larger one... and then an even larger one for... for discipline... in her poor little bottom... her poor little fundament...

  “I like to use that term,” she heard the doctor say, though his voice seemed now to come from far away, “because according to my philosophy of a natural man’s right of the phallus, the act of coitus in a young lady’s anus represents the fundamental gesture of his possession of her. My lord, what does Anti-Brown opine on the subject, if I may ask? If others who have read his treatise may be trusted, my rival agrees with me on this matter at least.”

  “Indeed, Doctor.” Lord Stephen’s voice sounded closer to Joanna’s ear, and warmer. She wondered, cheeks blazing with embarrassment at the thought of him watching the hard, black rubber thing invade her bottom, whether the warmth came from seeing his girl’s fundament trained for his stiff cock. The idea made her sob again, and almost in spite of herself relax that shameful part of her, so that Doctor Brown gave a satisfied noise, and pushed the plug in so far that now Joanna could feel the broad base of it against her punished bottom-cheeks.

  She thought his lordship must mean to say more, but perhaps he had grown so enraptured by the spectacle of the black trainer in his young lady’s bottom, seated at full length under the pout of her cunny, where he had thrust so hard and for so long over the bolster, that he had grown distracted. Thinking of his eyes on her that way, in that place, made Joanna feel she might never have the courage to open her own eyes again.

  “As you say,” Lord Stephen finally went on, “Anti-Brown considers anal intercourse the most essential element of a gentleman’s pleasures with a girl he keeps as a fucking piece. I don’t believe he calls it fundamental, precisely, but he certainly recommends that a girl receive the penis there as often as her master wishes.”

  The mewling came from Joanna’s chest again, for Doctor Brow
n had begun to move the plug gently inside her, twisting it slowly as if to ensure she remain as aware as possible of her bottom’s humiliating repletion with his trainer.

  “You are to become used to having in your anus what the man who owns you decides to place there, Miss Middleton,” the doctor said. “In a moment I shall remove this trainer and insert one that will accustom you more fully to something the size of his lordship’s erect male member.”

  Lord Stephen spoke again. “How tight is she, Doctor?” he asked. “Will she need much training before I lend her bottom to other men?”

  Joanna bit her lip, remembering Mrs. Mund’s terrible story again, the sharing of the young bride’s bottom, and yet hearing something in his lordship’s words that seemed to contradict the widow’s tale, at least as it applied to the nobleman who had deflowered Miss Joanna Middleton. For if Mrs. Mund had truly abhorred the sharing of her body by that terrible husband, Mr. Mund must not have made it so clear, in the way he spoke of the shameful idea, that he wished to share something of immense value to him, in order to enjoy it more greatly himself. Mrs. Mund must not have become warm in her bare, openly displayed cunny at the thought of being shared that way—as Joanna, to her chagrin, just had.

  Chapter Twenty-Two

  John Eliot had shared girls with several men, beginning with Miss Philippa Burns, the young lady he had disciplined while still a fusilier of Colonel Lourcy’s regiment. When the time had come to find Miss Burns a husband, her father had allowed John a free hand in assisting the process, and so several gentlemen had come to call on the lovely and by that time sweetly obedient girl. John had instructed Miss Burns to remove her clothes, and to gratify each of her suitors fully, participating himself insofar as had seemed advisable, in order to show the callers for example how hard Miss Burns needed to be fucked, and how deeply one might sound her young bottom with one’s prick.

  Too, it had proven helpful to supervise these prospective husbands in flogging Miss Burns for the infractions she had still committed from time to time, for the girl despite her progress had retained some haughtiness of manner. John had maintained—and Mr. Frakes, the merchant who had finally wed the girl had agreed entirely—that regular caning, as well as being often shared with other men, would produce the best results both in the marital chamber and out of it. Mrs. Frakes, therefore, when last John had heard from her husband, had learned both to go meekly over the whipping block in her bedchamber and to kneel respectfully before the pricks of her lord’s friends in the drawing room.

  John knew, then, that with a submissive young lady such as Miss Joanna Middleton, the course proposed by his lordship would certainly produce satisfactory results. The look upon the girl’s face, however, as she no doubt contemplated having her anus given to another man—first, John imagined, Mark Shepard, and then in all probability John himself, for Doctor Brown would wish to observe Miss Middleton’s conduct under his valet’s penis—stirred something in the former soldier that made him think not only of Miss Burns but also of his residence at the duke’s school.

  The girls under Miss Halton’s care there at Panton Castle all had fallen in some shameful amorous way. Most of these eighteen-year-olds had already received thorough chastisement for allowing a young man’s hand to travel beneath their petticoats, or for touching their little cunts in bed at night. Innocent as their society had kept them of erotic matters, they had had those terrible thrashings—usually the first of their lives—without truly understanding why. At the duke’s school, on the other hand, as these fallen girls’ bare bottoms became well used to the regular application of the punishment strap, they learned of fucking, and they underwent it—first under the cock of his grace himself and then enjoyed by his guests.

  In the eyes of those pupils John had seen a consciousness of both their sin against polite society and their need to sin again. Something about being whipped before they understood the nature of their offense had brought about a special understanding not shared by young women who had not fallen in that manner. The first stirrings in her virginal cunt of such a girl’s longing for the prick had felt only like an itch that could not be scratched, and yet she had received a terrible thrashing for yielding to it, her bottom made an agony to her by the strap or the cane or even the horsewhip.

  Then, at the school to which her benighted guardians had sent her, she was punished again, after she had learned to what majestic part of a natural man she must submit mouth, cunt, and anus when told to furnish her young body for his pleasure. The process made the duke’s girls’ blushes and protests at the thought of what their master might require of them provocative indeed. John had, while at Panton, often found himself compelled to take many a young lady over his knee in preparation for a night of being shared with another man, and spank her until she sobbed that she would have as many pricks in her bottom as the fusilier decided should enter there.

  Miss Joanna Middleton, John thought now as he beheld her countenance upon the display of the second, larger bottom trainer that must receive into her anus and upon the hearing of his lordship’s question concerning the sharing of her tight little bottom-hole, had in her eyes that same consciousness of punished shame, with more punishment, and more shame, to come. John could not say, though, that he had seen in the duke’s girls a flushed cheek, a creased brow, or a bitten lip as moving as those upon Joanna’s face. Mrs. Mund’s terrible tutelage had wrought in her erstwhile companion an alarm at the idea of a man’s lewd way with a maid that could not have contrasted more urgently with her need to experience the exercise of her master’s phallic rights in their most extreme form.

  Joanna looked at Doctor Brown intently, pleadingly, as if in hope that he might declare her bottom too small for sharing. The Scotsman did not respond to Lord Stephen’s question for the moment, but laid aside the second plug and turned his attention to the removal of the first, a procedure John found nearly as moving as the girl’s blushing visage—for of course Joanna’s blushes grew all the fiercer as she felt what the physician did.

  “Now, Miss Middleton,” the physician said, “most girls find this element of their anal training rather embarrassing. Do not be ashamed, if you can help it. You must help me remove the device by pushing, as you would upon the commode. I can assure you that you will soil your trainers only very rarely, as you will learn when you begin to clean them yourself—as his lordship will no doubt require, if you should remain with him.”

  “Indeed,” affirmed Lord Stephen, obviously content to wait for the answer to his question as to the sharing of the girl’s anus in order to enjoy the observation of the arousing little ceremony now underway. Joanna looked from her master to the doctor, her face now crimson to the neck. She emitted a sharp little cry as she felt Doctor Brown pull firmly upon the base of the plug.

  “Even when you do dirty them, Miss Middleton,” the doctor said, “soap and water will make them good as new—and you will know that you should ask your master to administer a cleansing enema before he uses your anus with his penis that day.”

  The physician pulled more insistently, and Joanna emitted a little sob as she did as she must, and expelled the black plug with a sound that made her close her eyes and bite her lip.

  “That’s it, Miss Middleton. Well done. Now, before you forget that feeling, I shall insert the next size. There. Absorb it now. Yes, you can do it, my dear. I know it causes discomfort, but you will grow used to it in time.”

  Joanna gasped and whimpered, arching her head back onto the mattress. Her anus had begun to learn, though, and John could see that she would receive the plug, about as thick around, at its broadest part, as his own sizable prick.

  “My lord, she does well, does she not?” the doctor asked. “Rub the clitoris gently if you would, to reward her and to encourage her.”

  “By all means,” said his lordship, reaching his hand down and caressing the adorable little cunt.

  Joanna gave a different sort of cry and, just as John had felt certain she would, relaxed
her bottom so that Doctor Brown could seat the bigger trainer firmly inside. The girl’s breath came in short pants, and John found that the look in her eyes of mingled need and humiliation, when she realized she had the whole thing in her bottom now, stiffened his cock to iron in an instant. Her backside surged, and she moaned in what seemed equal pain and pleasure.

  “Well done, Miss Middleton,” the doctor said, his tone highly approving. “I would advise allowing her a climax, my lord. She is quite near to orgasm, unless I miss my guess.”

  John glanced at Lord Stephen to see the nobleman’s face turned down, eyes alternating between Joanna’s face and the cunt that had made his fingers glisten in the twilight that had gathered as the girl’s anal training proceeded. His lordship addressed Joanna with his response, rather than Doctor Brown, saying softly, “Spend for me, now, darling. Spend with the trainer up your arse.”

  The young woman’s spend grew very close, to judge from the helpless motion of her body and her sharp cries. To John’s surprise, the doctor spoke again, just before the final paroxysms of Joanna’s climax took hold of her.

  “To answer your question concerning the lending of Miss Middleton’s anus, my lord, I must inform you that in accordance with the discretion granted me by the Society for the Correction of Natural Daughters, who have consented to take responsibility for her future happiness, I intend to bring Miss Middleton to London once you have deflowered her anus. I happily acknowledge your provisional right of the phallus over her, but her case is an interesting one, and I think she should be thoroughly used by several experienced men, in the convenient setting of the society’s clubhouse and under my close supervision—and under yours, of course, as well. Whether I recommend that she stay with you or be given to another natural man will depend upon my observations on that occasion.”