The Shame Gambit

by Emily Tilton

  He whipped his petite, lovely young wife again and again, on her already very pink backside, so that Jenny shrieked in pain as her tears rained down on the bed. Her golden hair threshed from side to side, and she reared back with every agonizing stroke.

  “Well, just meanness and nastiness have got... to... stop.”

  He brought the belt down again, hard, across her bare bottom, to emphasize each word. Jenny clutched the comforter underneath her and sobbed into the sheet, her little bottom squirming uncontrollably with the fiery agony of the terrible lesson her husband gave. For the second time in a week, Jenny had had to come here to the guest room and take all her clothes off, then put two pillows in the middle of the bed and wait for Henry to come in, his long black jeans belt doubled in his hand.

  Then, with her hands at her sides and her face blazing red as her eyes seemed incapable of rising from her husband’s loafers, she had stood in the altogether as she heard him tell her for the fifth or sixth time that remarks like the one she had made at the dinner table were not going to be tolerated in his home. His very body, tall and slim and taut as the main sheet on a racing sloop, made her tremble when he towered over her, making his displeasure terribly clear.

  After that had come the too-familiar command to get herself into position for her punishment.

  “Now lay yourself over the pillows, Jenny. You have a whipping coming.”

  Now, at last, with a final hard lash of his belt, Henry stopped.

  “We both know,” he said in a much gentler voice, “that our marriage is unique in certain ways. One thing that comes with that, though, is that you know exactly what’s going to happen when you misbehave, young lady.”

  Jenny’s bottom moved over the pillows, up and down as she clenched her blazing little cheeks in a vain attempt to lessen the terrible sting of the belt. She whimpered, her face buried in the now very damp backs of her hands, and she felt her features scrunch up into the mask of woe a little girl made when her daddy gave her the lesson she needed, on her bare bottom where she needed it most.

  She had never had that, of course. She had grown up mostly in a corporate educational facility, where punishments came in the loss of privileges. When an Institute trainer had taken her from there on her eighteenth birthday and told her she would be prepared for marriage to a wealthy man, according to the traditional-gender-role standards of the New Modesty, Jenny had quickly also learned that that would mean old-fashioned discipline. Over her trainer’s knee, that very night when most girls would have been celebrating their new adulthood, Jenny had had her first spanking, for talking back.

  That night, also, she had started to learn about sex.

  “You have been enrolled,” her trainer Max had told her, while Jenny still sobbed over his knee, “in the Institute’s Thoroughly Trained program. That means that I will have the responsibility for getting you ready for your husband’s bed.”

  Then he had made her kneel down on the floor between his thighs, and told her to unfasten the button on his waistband and unzip the fly of his casually elegant wool trousers.

  If Henry spoke the truth—which he certainly did—concerning their unique marriage, the individuality of it had begun then, when Jenny had obeyed Max’s command. It had started, that is, a week before she had even met Henry, when with her poor little bottom blazing from her very first, very hard spanking, she had uncovered her trainer’s hard manhood and, at his command, had kissed it though the lewd act had turned her face as red as her bottom.

  Jenny didn’t know if every corporate educational facility instilled the same set of old-fashioned values as hers, number 715, had taught its girls. They lived now in the age of the New Modesty, however, as promoted by the government’s embrace of the assistance it got from its corporate partners, and one partner in particular: Selecta. Every book and every chair, every cup and every prepackaged, wholesome sandwich on their rare field trips, had borne the SELECTA name, in red.

  The New Modesty itself, however, was for girls eighteen and older. Kneeling on the carpet in Max’s lovely downtown Indianapolis apartment, Jenny had learned why, for the first time.

  The New Modesty, it turned out, was about sex.

  “Sex and a good many other things,” Max had said from above her, as Jenny had looked up at him with her backside throbbing painfully and her heart beating very fast. She hadn’t been able to get her mind around the fact that a man’s penis, his hard penis, stood two inches from her mouth... that she had... she had just kissed it. The disgust she had felt, which she had sort of continued to feel... the good-girls-don’t-do-that thoughts from school... something else had joined it, in her mind and, well, elsewhere.

  Max’s relative lack of height had seemed to her to make him even more formidable: his powerful arms, covered in light red hair, and still more his massive legs, had sent a quiver of unknown need through Jenny the very first time she had seen him.

  “But because you’re eighteen, now, and you’re going to be married to a man who has a right to expect a well-trained wife, it’s the sexual component that you must learn about. Open your mouth and take me inside, Jenny.” Then, when she had hesitated, “Must I spank you again? If you can’t learn to please a man with your own natural submission as a motive, you’re going to find yourself over your husband’s knee very often.”

  His knee... and the bed in the guest room, when I’ve been very naughty, Jenny thought now. Our unique marriage.

  Henry had come to Max’s apartment to meet Jenny. He had flown from New York in his private jet. Jenny hadn’t had to suck Max’s penis that day, because, her trainer said, if things went well she would have to please the man who was coming to take her to dinner. Someday, Max thought, Jenny would probably have to suck two penises in a single day, but Thoroughly Trained was in part about taking that kind of thing very slowly.

  Jenny had blushed furiously: Max had still had to spank her, at that point, before she would take his hardness in her mouth, as she had to do every day. Though her trainer’s hand sometimes seemed to linger low down on her punished bottom after a spanking with skirt up and panties down to mid-thigh, his fingers had never traveled any further. He had tucked her skirt up, while she learned to please him with her mouth, so that her bare, red bottom felt the air moving over it and Jenny’s blush deepened as she pictured Max looking down at the little cheeks he had spanked so hard.

  For the very first time, though, after Henry had sat in Max’s living room discussing the financial markets and Jenny, as instructed by her trainer, had stood awkwardly in the middle of the rug, had she received the command to take off all her clothes.

  She had stood, frozen like a red-faced statue, except for her eyes going from Max to Henry and back to Max. Henry’s tall, elegant, dark-haired form had contrasted so sharply with Max’s compact red-haired one that the command had taken her tongue away completely.

  “Come now, Jenny,” Max had said in a reasonable tone. “You have sucked the penis every day for the last week. It’s time you learned a little more obedience. Mr. Granby here is going to inspect you thoroughly, to see whether he would like to court you. To make it perfectly, clear, honey, if Mr. Granby likes you he will take you home with him tonight. It’s not a traditional courtship, but it suits your needs.”

  Court. Such an old word, but used to cover over things that Jenny had such strange, conflicting feelings about—feelings that only grew in power when a man like Max, in the company of a man like Henry, used a traditional euphemism for what a bridegroom liked to do with a bride.

  Marriage. What had Jenny known about it? Only what she read in school, which was actually, she had to admit, a great deal—but only from an objective, social and historical, perspective. From the standpoint of the history of the institution, which Jenny had for some reason upon which she could never quite put her finger studied almost obsessively, on her own, this mortifying moment when the man who wished to have her as his bride meant to inspect her without her clothing on, made an awful, undeniab
le sense.

  Not that her personal research had made it at all easy to obey her trainer’s and her eventual husband’s shameful commands, when it came to old-fashioned discipline and her submission in the bedroom. A modern girl, brought up even in corporate school to know herself as autonomous a being even as the billionaire who meant to marry her, trembled just as a Victorian maiden must have, though perhaps for different reasons, when the man who owned her told her to undress.

  Now, as Jenny sobbed atop the pillows on the bed in the guest room of her spectacular Westchester mansion, with the man she loved and who she knew loved her standing over her, his belt still in his hand, she couldn’t figure out why she kept saying mean things about a woman she hardly knew. Hannah Fong, who had beaten Jenny in straight sets on the country club clay despite Jenny having won the regional singles championship for Corporate Educational Facility 715 only the previous spring.

  Hannah was a better tennis player, and Jenny, it seemed, couldn’t bear it. She had to say to Henry at the dinner table that she had heard Hannah Fong had slept around.

  Why? Why did I say that?

  Jenny’s mind drew back from the question. She knew the answer, but she refused to let herself understand, because...

  Henry put the coiled belt on top of Jenny’s back. She gave a little whimper, and her hips bucked, because she knew what it meant. She felt her brow furrow with a deep, deep crease, as she took her lower lip between her teeth.

  “Spread your legs,” Henry commanded.

  “Please,” Jenny pleaded. “Please, not my bottom.”

  “Shh, sweetheart,” her husband said, his voice gentle again. “You know you need this lesson, and you’re going to have it.”

  Henry had started punishing Jenny anally since they had returned from Rome two months ago. Jenny didn’t like to think about that trip, despite having had a wonderful time in some very important ways. Remembering those ways, though—including the beginning of her anal discipline—made her mind shrink back just as it shrank from the question of the reason for her prudish backbiting.

  She closed her eyes very tightly, now, because she heard Henry getting the thing—the thing he used to punish her, whose naughty name Jenny didn’t like to think.

  Dildo. He didn’t use the other naughty thing with the other naughty name. Butt plug.

  Jenny felt her cheeks blaze with heat. It had started when the other girl, the one who lived as a sort of schoolgirl with the men who owned her, had to show her own butt plug on the plane to Italy. Henry, however, had decided he wanted Jenny to learn her own bottom lessons with a black thing that looked like a man’s penis. It had made her feel faint when he had first showed it to her, and she still got a little dizzy, even now, when she pictured it in her husband’s hand.

  “We’re going back to Europe next week,” he said, to Jenny’s great surprise, for Henry usually didn’t speak, once he had told her to spread her legs for the most shameful part of her punishment. The casual command in his voice sent a thrill of need through her whole body: the way he could simply tell her she would soon board a private jet to fly to Europe seemed in its own way the most arousing thing she had ever experienced. “To France. We’re going to meet more people who you may think you can gossip about. While I teach you this lesson, Jenny, I want you to think about how you’re going to behave from now on. Maybe Hannah Fong does sleep around, but I doubt she needs a big black dildo in her bottom as much as Jennifer Clark Granby does.”

  Chapter Six

  Henry put the head of the dildo against the cringing, pink inner lips of Jenny’s pretty pussy. His wonderful, sweet, pretty, naughty, young wife whimpered at the sensation. His cock felt as hard as a bar of iron, and he couldn’t help thinking, as he always did when he punished Jenny this way, that Max Weller’s advice about the ongoing training of Mrs. Henry Granby required nearly as much self-control as Henry had at his disposal.

  “You’ll get better results in the long term,” Max had said when Henry had called him for the monthly consultation required by Jenny’s contract with the Institute, “if you use the dildo instead of your cock. Jenny’s upbringing in the CEF means that she responds best to institutional behavior adjustment, followed by the comfort of personal caresses. You can fuck her then, but the kind of corrective training you’re after for her misconduct is best accomplished with an artificial phallus, after you whip her with your belt.”

  Henry leaned over to murmur in Jenny’s ear, “Get the dildo ready for your bottom, now, sweetheart.”

  That close to her, he could feel the delicious, mortified shudder that went through her body at the naughty word dildo. He pressed it gently into her, hearing Max’s words of advice echo in her ear.

  “Your wife is a true repressed submissive—one of the best-developed cases I’ve ever seen thanks to her intelligence. Her submission and her smarts are born, not made, though Selecta makes certain in their curriculum that a girl like Jenny grows up innocent, but valuing herself highly enough that when the time comes she’ll be able to handle the strength of her desires, even if she doesn’t want to admit them. Out of the thirty girls in her class at CEF 715, only half were candidates for the New Modesty, only two out of the six who applied were offered voluntary places at the Institute—and only Jenny was a candidate for Thoroughly Trained, because of the repression.”

  Henry enjoyed hearing about the theory, and he loved knowing he had purchased something very special when he invested in the lovely girl with whom he had fallen almost instantly in love. It all tended to sound like Greek to him after a while, though. He had asked Max, “So she does like being punished, despite how it seems? And she likes the kind of sex I make her have?”

  “One hundred percent,” Max had told him. “Someday—years from now—she’ll probably be able to admit she likes it. You saw even that first night how wet she was when you inspected her, and you remember how hard she came, right?”

  Henry did remember that, now, as he pushed the big black dildo inside Jenny’s pussy. With the lovely red color of her thoroughly whipped bottom, the parting of his bride’s smooth, demure, prettily pouting cunt lips by the thick shaft made an exciting sight indeed. Jenny whimpered just as she had that first night when, after Max had spanked her in front of Henry to teach her she must remove her clothing when told to do so, Henry had used a little purple vibrator between her legs while she still lay over her trainer’s lap.

  “That’s it, sweetheart,” he murmured now as he buried the artificial cock inside her. “You get this nice and wet now.”

  Jenny cried out, moving her hips helplessly with the thrusting of the dildo.

  “Oh, God...” she moaned, in a low, helpless tone. “Oh, sir, please... please don’t... don’t make me...”

  But Henry put his left hand on her tailbone, to hold her still, and he began to pump the hard silicone phallus inside Jenny’s soaking slit, in and out, in and out.

  “You know you have to come for your husband when he trains you, sweetheart,” he said. “A wife has to learn to respond properly to fucking.”

  Jenny emitted a wordless cry at the word that she thought almost the naughtiest one of all, and she reared back against Henry’s hand, the pressure of her husband’s strength holding her atop the pillow clearly intensifying the girl’s helpless pleasure. Henry thanked Max Weller inwardly once again, as he tended to do several times a day. He would never have thought that a girl could feel so conflicted about her orgasms that her husband had to force them upon her, and could actually use them as a way to discipline her, but here he and Jenny were: Max had proven the best advisor money could buy, in helping Henry to a teenage bride he could finish training as an innocent, naughty, submissive fuck toy.

  He knew precisely how to move her along, now, and to bring her to the more disciplinary stage of this final phase of her lesson for prudery and backbiting. Still leaning over her, close enough that her motions of helpless compliance with the dildo’s surges in and out of her pussy brought her sweet bare fle
sh against the fine cotton of his Oxford shirt, he commanded in a slightly sterner voice, “Where is the dildo, sweetheart? Where is it fucking you?”

  “Oh, God,” Jenny whimpered, as her movements became more frantic under the influence of the dirty talk. “Oh, sir... please... I can’t.” Then she tried desperately, “It’s in my pussy, sir. It’s... it’s... moving in my... my p-pussy.”

  Henry drove the big black shaft in hard and deep, and kept it there. “What does a man call a girl’s pussy, Jenny?”

  “Oh, I...” She closed her eyes very tightly, and the crease on her brow got very deep.

  He pulled the dildo out just a little, then pushed it back in, moved it inside her by rubbing his fingers hard and rapidly across its ebony base. Jenny gave a wailing cry.

  “Say it, sweetheart,” Henry told her. “Or I’m going to have to whip you again before you have a long dildo session in your bottom.”

  He gave a tug at the artificial cock, then pulled it further and further out, so that Jenny whined at the threat of its desertion, the threat of the belt, the promise of the dildo in her anus.

  “Cunt,” she whispered, her face so hot that he could feel her blush against his cheek. “My... my cunt.”

  Instantly Henry started to fuck her there, again, with the dildo, and Jenny began to come, the way she always did, in waves that crested and fell and crested again. She writhed under his hands, and Henry looked down in loving wonder, scarcely able to believe the same creature who had prissily accused Hannah Fong of sleeping around now cried out her disciplinary orgasms with a whipped bottom, over the pillows in the guest room.

  When the second of her climaxes had washed through her body, and a third had begun to build, Henry withdrew the dildo and put its glistening head to the sweet, tiny bud of her bottom-hole. With a sob of pleasure, Jenny went still, little breaths puffing through her nose and her whole body tensed against the shameful invasion.