Sir Gerald Carruthers, Bart., definitely had a problem, he reflected as he smoked his pipe in his study, in his fine Cadogan Square house, in the winter of 1862. Sir Gerald’s ward, Caroline Hollins, just eighteen and not even out, a girl he had taken in when her father, Sir Gerald’s business partner, had died and left her orphaned ten years previous, seemed intent on ruining the happiness of Sir Gerald’s household. Now, Sir Gerald awaited the household’s physician, Dr. Reginald Brown of the Royal College. Carruthers hoped that perhaps Brown could tell him what to do about Caroline’s strange behavior, since that behavior seemed to fall within the bounds of Brown’s specialty.
Sir Gerald’s household, to be sure, did not represent a very usual sort of household. He supposed that if it had been of a more usual kind, the problem with Caroline might not have arisen. The special nature, however, of Sir Gerald’s life at home—a life Dr. Brown himself, along with Charles Vance, Sir Gerald’s best friend and his cohabitant in Cadogan Square, had recommended to him—made the chief source of his contentment, and he had no intention of parting with it. Indeed, before the difficulty with Caroline had arisen, Carruthers had nearly completed laying his plans to ensure that the peculiarity of his mode of life would be enabled to continue indefinitely, though in a locale far from London. He had intended to marry Caroline off, and then to remove, in company with the other persons who presently shared his house in Cadogan Square, to an island he had purchased in the Hebrides, where they might enjoy their unique pursuits undisturbed. It was this plan that Caroline’s conduct had disturbed.
Sir Gerald, to reiterate, lived with his friend Charles Vance. Unusually, in addition to a full complement of ordinary servants, Carruthers and Vance employed two supplementary housekeepers, Anne Loomis and Charlotte Dalrymple. In reality, Anne and Charlotte were the fucking pieces respectively of Carruthers and Vance, though the girls professed to like the term ‘mistresses’ better.
Sir Gerald’s problem, put very briefly, lay in his ward Caroline’s recently having developed an insatiable, prurient interest in what Carruthers and Vance did with Anne and Charlotte at night in their bedchambers—and elsewhere, at least as occasion had warranted before Caroline had begun her near-nightly expeditions to discover what caused Anne and Charlotte to cry out that way, as if Carruthers and Vance were punishing them.
For that, apparently, was how it had begun. The very first time Caroline appeared in Sir Gerald’s bedchamber, while his cock, deep in Anne’s backside, made her cry out in the ambiguous pleasure that made Sir Gerald’s blood sing with lustful delight, that had been what she said.
Anne, still dressed, if scantily, in her silk nightshift, had been seated on Sir Gerald’s lap, facing away from him. Carruthers, mad with the pleasure of his favorite kind of fucking, helped her bounce herself up and down upon the manhood inside her tight little ring.
Suddenly, Anne gave a different sort of cry.
“Caroline Hollins,” she shouted, breathless from the bottom-fucking Sir Gerald enforced upon her with his cock and his hands underneath her pert little bottom-cheeks, where he had lifted her night shift to play with them, “go away this instant!”
At first Sir Gerald had thought that perhaps Anne was introducing a diverting new fantasy into their already perverse lovemaking—one he found far from unwelcome. He said, “That’s right, girl. Your arse-fucking shall be public knowledge, now,” and bounced her even more severely upon his cock, but then Caroline had come around the bed, in her lovely nightdress of cotton lawn with her long auburn hair gathered in a loose knot at the back of her neck, her eyes very wide, and Sir Gerald, in confusion, had stilled Anne’s motions on his cock. The front of Anne’s shift lay pooled across his thighs—that covering at least saved a little bit of Caroline’s innocence, for otherwise she would have seen Anne’s pretty cunt, with its golden tresses, and even the shameful sight of a cock going in and out of a girl’s bottom.
“Caroline,” he said, “go to bed this instant. You will be punished in the morning for intruding thus.”
“What are you doing, Sir Gerald?” Caroline asked.
“Go away, Caroline,” Anne cried, helplessly reaching out for the coverlet with which to hide her semi-nakedness.
“What we are doing is none of your concern, my dear. I shall birch you extra for the impertinent question. Now go to bed.”
A tear rolled down Caroline’s face. “I only came because I thought you were hurting Miss Anne.”
“You little liar,” Anne hissed. “I know how much you dislike me! You wanted to see me punished!”
Sir Gerald found to his surprise that far from losing his manhood’s hardness over the strange and rather confounding turn of events, he seemed to be even more aroused. He bounced Anne’s bottom upon his cock, making her cry out in discomfort, and said, “Quiet, Anne, or I shall have to birch you as well for this spiteful conduct. Miss Caroline is a gentleman’s daughter, and you are a trollop who wears fine dresses because you know your place, which is right… here…” He bounced her again as he spoke, making her scream. Anne had, in truth, sprung from the middle class, but Sir Gerald never missed an opportunity to degrade her in the throes of passion, seeing as to do so stoked the flames of passion in both of them.
Caroline said, seeming to evince real concern, “Are you hurting her, Sir Gerald?”
“No…” gasped Anne, “He’s… not hurting me… really, you silly girl.” Caroline’s eyes grew even wider at the sight of Anne going up and down on Sir Gerald’s cock, though the actual motions still of course lay hidden behind the veil of Anne’s shift.
“Go away, Caroline, or I shall have to birch you right now—and in the morning.”
Caroline’s face crumpled into sorrow. “No one tells me anything,” she sobbed, and ran from the room.
The next morning, Sir Gerald put Caroline over his desk and birched her severely, demanding as he did so whether she would intrude again. Her lovely young bottom was framed by the drawers Sir Gerald had opened to expose it for punishment, and by her ruffled petticoats, pinned up by Anne herself, before Sir Gerald commanded her to leave the room. The delicious cheeks of that rump squirmed and clenched, while Caroline cried out that she promised to be good, and that she was very sorry.
As Carruthers marked that bottom thoroughly with the scarlet stripes of the birch, he questioned her further, accompanying each question with another chastising stroke. The answers to his questions, which Caroline gave with all apparent honesty, disquieted him even as they aroused him even more greatly than he usually grew aroused when disciplining a girl.
“Miss Caroline, pray tell me why you thought it seemly to come into my bedchamber? I know it was not because you were concerned for Miss Anne, since you have heard her punished often enough.”
“Ow! Sir Gerald, please!” Caroline cried, sobbing piteously into her hands, where she had buried her face as she lay atop the walnut desk.
“Clearly, I did wrong not to engage another governess for you when Miss Standish went away, but now it is too late, and I must discipline you and keep you from ruin. Answer my question, my pert little miss!” Sir Gerald said, and birched her again.
“Ah! Because I have heard about… about those things.”
“I do not know what they are called, Sir Gerald. Oh, please… I am telling you the truth!”
“What do they concern, then, my girl?”
“Men and women,” she said miserably.
Carruthers felt real moral outrage at that, and gave her a cut of the birch in recompense. Her bottom bounced up and down delightfully. He could not deny that the idea of sending Anne away and claiming Caroline for his own had entered his mind on more than one occasion.
“And what do you know of what men and women do in a bedchamber, Caroline Hollins?”
“Only that they come together, and that men are made… differently to women?”
“How are they made differently? Do you know that as well, you hussy? Have you snuck glances at me, or Mr. Vance? Have you read dirty books?” Carruthers birched her with each of these questions, making her cry out and also making his cock as hard as he thought it had ever been, even when the prospect of bottom-fucking Anne was before him.
“No! Sir Gerald, oh, please… It hurts so much!”
“Tell me then, you minx, what you know of the difference between men and women!” Sir Gerald’s moral outrage redoubled. Caroline should be a pure young maiden, ready to come out and find a husband, whether that husband should be Sir Gerald himself or some other man who could take the girl off his hands and leave Carruthers and Vance in peace to fuck their girls just as they pleased.
Caroline sobbed into her hands. Her voice came up to his ears much muffled, but distinct nevertheless. “Only that a man has something that can make a woman happy. I heard one of the housemaids say it.”
Her grief at knowing this strange thing, now that Sir Gerald had delivered just chastisement for the possession of the forbidden knowledge, seemed so entirely genuine that Carruthers regretted his severity. He stood her up from the desk and embraced her, as she sobbed against his shoulder. “I only wanted to see if it were true, because Miss Anne didn’t sound happy, and… oh, I suppose I am just so very curious.”
“There, there,” said Sir Gerald, stroking her hair. “It is true, and indeed I was making Miss Anne happy even though her cries perhaps sounded more like distress.”
Then, hoping to assuage her curiosity, Sir Gerald committed what he later realized was a terrible error. He said, “Sometimes when a woman feels pleasure that great, it is almost a kind of pain—and sometimes even the pain of a birching can produce pleasure for a woman, if it is accompanied by his gentler attentions.”
“Truly?” Caroline asked. “Is that why I feel so warm, down between my legs?”
It required the utmost composure for Sir Gerald neither to take advantage of the situation nor even to appear to be perturbed in any way by this revelation of Caroline’s precocious eroticism. Really he wished to reach down, raise her skirts, and help her investigate the matter of that warmth immediately; to see just how much wetness accompanied it, and how quickly it might be assuaged by a man whose fingers and tongue possessed the skill Sir Gerald’s did.
He did not understand then, however, just how much he had stirred up Caroline’s curiosity, rather than putting it to rest, and he thought he could simply control himself and sit down in his desk chair so that no risk of her feeling his hardness growing in his trousers might cloud the moment. He took Caroline’s hands and looked into her troubled blue eyes.
“Caroline,” he said, “these are matters for when you have a husband.”
“Oh,” she said. “Because he will do with me what you do with Miss Anne?”
Sir Gerald suppressed a smile. “Yes, my dear. He will have the thing that will make you happy, and he will teach you to please him, and give you great pleasure in return.”
“Will he birch me, Sir Gerald?” An adorable little crease appeared upon her lovely brow, framed in her auburn ringlets.
“I do not know,” Sir Gerald replied with as much frankness as he could muster while preventing himself from saying, “He will if he knows how best to enjoy a girl like you.”
“But he may, if he likes?”
Sir Gerald nodded. “Yes, my dear. He will be your husband, and he may birch you, if you are naughty, just as I do now.”
“Will he cane me?” Something in the eager tone of the question intimated to Sir Gerald now that he had perhaps made a mistake in trying to satisfy Caroline’s curiosity this way.
“He may do that, as well, if he likes.”
“You would not stop him? If I came to you and said that he had caned me, because I would not learn how to please him?”
Sir Gerald felt his own brow creasing now. How could he close this discussion without it leading to even more such prurient talk? “I will always be here for you, my dear. If I should hear, from you or from anyone else, that by some deception on his part I had married you to a cruel man, I would take you away.”
“But what if he caned me because I would not let him do the thing you did to Miss Anne? Would you take me away from him, and do that thing to me yourself?”
“Child!” Sir Gerald said. His heart was pounding and his cock was hard as iron. Could Caroline really be saying what she seemed to say? He cleared his throat. “This sort of talk is not appropriate between us.”
“But from whom shall I hear of these things, then?”
It was true—she had no family at all, and it would hardly be right to have Anne inform her on such matters.
“Perhaps we must have Dr. Brown come and speak to you.”
“Oh,” Caroline said. “Are you sure you cannot tell me more?”
“I am sure,” Sir Gerald said, though truly he longed to tell her—and to show her—much, much more.
A year later, he would reflect that in the end, though these events were to deprive Caroline of a truly conventional married life, the fateful course of things that began when she saw him bottom-fucking Anne that night perhaps provided benefits far beyond what a conventional life could have given her. Now, waiting for Dr. Brown, three days later, he wished only to find a way to marry her off as quickly as possible. Surely Dr. Brown, author of the pamphlet that had inspired Sir Gerald to pursue his amorous pleasures to their utmost, freeing him to experience such ecstasies as requiring Anne Loomis to take his stiff cock up her backside how and whenever he chose to put it there, would know how to handle such a delicate matter.