Trained by the Trillionaire

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Trained by the Trillionaire Page 11

by Emily Tilton


  She couldn’t say she hadn’t been informed of the need to prepare herself for what would now happen: Master C had fingered Cynthia’s anus often enough that she should be used to it. But still, even for him, a man she had come to respect and like, she had never spread her bottom-cheeks without needing a spanking.

  Please don’t, she thought. Please don’t make me.

  But then she heard him say exactly that, in the accent that seemed to stir such conflict inside her, between thoughts of the old world and of the new—above all in the way he kept calling her his eepstair. He spoke the word as if he had acquired Cynthia for the precise purpose of subjugating the sort of girl who had thought no man could ever do that.

  Who thought no man would ever say to her, “Reach back and spread your derriere open for me, ma fille. Show me where my cock goes.”

  But it doesn’t. Not even your finger goes there!

  She gave a little sob, into the tan leather of the bench, but she didn’t move. She had just had to push out her awful butt plug: surely he couldn’t mean to make her go through this as well. He must know she had trouble with anal: Master Greg would keep this all in check and maybe she would get used to it by the next time Monsieur Herrier demanded this awful sort of service from his new bed girl.

  “They taught you better than that at the Institute, did they not, ma fille?” the magnate said in a mocking voice. “Whip her, please, Maître Gregoire, as you would whip a stubborn animal on the farm.”

  A lightning bolt of fear seemed to go through Cynthia’s whole body. She felt her limbs not just tremble, but shudder as if they had an actual electric current inside them. She couldn’t have found the coordination to do as Monsieur Herrier had ordered her now even if she had had the will. She cried out in wordless panic, as she heard, to her astonished terror, Master Greg’s response.

  “With pleasure, monsieur. I’ll just get the punishment strap.”

  Cynthia tried to get up and run, then. In her mind, she made it to the airplane’s door, ran onto the tarmac, screamed for help that even in this clearly remote part of the Paris suburbs would surely come for a beautiful girl in a lacy nightgown that showed so clearly how men had taken advantage of her.

  In reality, Monsieur Herrier noticed her beginning to rise, and put his strong left hand on her back to hold her down. His right… oh, no. His right hand began to spank her bare bottom, as she whimpered. Six spanks on the right, then six on the left, and she was yelping pitifully, like that whipped animal, at the end.

  And then his fingers between her cheeks, touching, pressing, not deeply—not yet, anyway.

  “You must learn, ma fille.” He spoke in her ear, bending over her. “I know how hard it will be, a spirited eepstair girl like you, but that is why you are here. You will learn to receive what I have for you, just as I please to give it. You will learn to obey me, especially when I decide to subjugate you like a beast of the field, for that is what you have made of yourself, with the ways you think so modern.”

  The words… they felt much harder to bear than his big hand spanking her so hard that she knew she must have the red prints of his fingers displayed there now, with much worse to come.

  You didn’t whip a beast of the field. Everyone knew that. There were organizations, societies, charities, and everyone knew, whether they lived in Brooklyn or Paris or wherever…

  Surely a man this elegant and refined would never whip an animal, in this modern world they both inhabited.

  No, he wouldn’t, she realized with a feeling like ice water had just coursed through her veins. He wouldn’t whip an animal. But he would whip a girl who needed to learn a lesson about her body, and his rights. Her owner meant to teach his bed girl a lesson just as old as the kind of discipline animals once received but no longer got, because it didn’t work.

  A girl got that kind of lesson, still, though, it seemed, even today. She got it if she had ridden her pillows with her panties down. If she had been caught at it, and taken to a place where masters knew how to get her ready to serve in the bed of a wealthy man.

  If the wealthy man who owned the girl meant to fuck her bottom, and she refused to spread it for him to begin his training of her tiny passage, her unnatural passage, her primitive passage: the place girls of the olden days only whispered about, to tell one another that their husbands used them there, whipped them if they didn’t spread their bottoms open, as they whipped the mule or the draught horse. For in those days—the days to which it seemed Monsieur Herrier wished to return his new bed girl, hipster Cynthia Hall—a husband trained his wife’s bottom-hole, if he had a yen for wicked, unnatural fucking that would spare him a growing family. His wife heard his command to kneel on the bed and bend to put her face in the covers, and she knew she would feel the strap across her backside if she did not obey when he told her to reach behind her and spread her rear-cheeks so that he might enter the thrillingly tight ring she would show him.

  “You never thought a man would use you here, did you, ma fille?” he said softly, and he did push, and his finger did enter.

  Cynthia sobbed into the leather, “No.”

  “You may call me monsieur, eepstair girl,” he said as if she had meant to answer his question, and not merely to refuse his finger.

  But she couldn’t: she stayed silent.

  The finger pushed in farther. “Oh, please. No. Please, monsieur. Not in my bottom.”

  She heard a smile in his soft voice. “There. That’s lovely. So tight back here, and yet you can’t keep my finger out, can you? My cock is going to have such a lovely ride, very soon. I almost think I should take the virginity of your derriere before I take that of your con. Would you like that, ma fille? To learn what it means truly to serve as you should? If I did that, you would be my anal girl forever, wouldn’t you?”

  “No! Please, monsieur! Oh, no… please…” The finger moved in and out now, and as she heard a swish behind her that must be the strap, in Master Greg’s hand, she felt much more strongly the thing she had avoided the night he had taken her from her apartment—which she avoided also at the Institute, letting her daily spanking for failing to open her bottom properly somehow excuse her.

  The finger felt good. She hated the way it made her wish for her pillow, for a girl’s face, for a man’s hand… for a cock, up front in her untried pussy. It didn’t feel good to have the plug, and it wouldn’t feel good to take a hard penis: she could assure herself of that, couldn’t she? Those things hurt, didn’t they?

  But that wasn’t the point: the point was that to have a finger, or a plug, or a cock in your bottom was unnatural and wrong, and above all degrading, especially when the man doing it made it clear that he meant it to degrade her.

  “Well, now you will be whipped, ma fille. Consider how you will behave the next time I ask you to show me where my cock goes.”

  Another sob wrenched itself from Cynthia’s throat as Monsieur Herrier pulled the finger from her anus and stood up.

  “Whip her very severely, Maître Gregoire,” he said in a jaded kind of voice. “She needs to know I’m not a tolerant man when it comes to a concubine’s duties. I’ve paid a good deal of money for that anus, and even an eepstair girl like this one should understand that when she belongs to a wealthy man he will enjoy her just as he pleases.”

  That made Cynthia, momentarily free of the pressure of her owner’s left hand, once again try to rise. But the hand returned, even more forcefully, and when she flailed her arms, Master Greg said, “You had better hold her in place for the whipping. We’ll need to keep her hands still, too, I think.”

  They made her wear a collar, then, with cuffs attached to a strap that descended her back and immobilized her wrists. If she tried to move her hands, the collar tightened around her neck, so she had to keep them twisted up behind her, as Monsieur Herrier easily held her steady over the bench, moving to her right side so that Master Greg could stand to her left and bring the strap down across her bottom. They discussed these arrangements with
a dispassion that made Cynthia feel like she, too, stood looking at the naughty girl who wouldn’t do as her owner told her, who needed a whipping to learn her lesson. Her heart felt like it had literally come into her throat as she listened to her masters.

  “Will you be able to whip the whole bottom that way, Maître? Shall I sit on the bench myself?”

  “You had better, monsieur. If you want her whipped severely, I’ll need to swing a little more freely.”

  Little whimpers seemed to come from somewhere else, but Cynthia knew they were hers. She had been caned, she told herself, but something about this session with the strap seemed much worse.

  “I’ll do it!” she tried again. Her hands moved of her own volition clutched desperately in an attempt to get her bottom-cheeks on her fingers so that she could show Monsieur Herrier the anus trained for his cock. The collar tugged at her neck and that, too, gave rise to a horribly ambiguous feeling.

  “Too late, ma fille,” he said, and the satisfaction in his voice seemed as bad as his comparing her to a domestic animal. “But you certainly will do it, very soon. Go ahead, Maître Gregoire, if you please.”

  She heard the whistling and the crack, and she started to scream even before she felt the searing pain of the first lash across her poor bare bottom.

  Chapter Seventeen

  Sarah winced as she listened to Cynthia’s cries of agony. Occasions when the happy development of a submissive girl’s sexuality conflicted with a mission run by the Pretorian Guard came rarely, but they never failed to make Sarah feel guilty. If the need to develop Herrier’s obsession with ‘civilizing’ a modern girl hadn’t been so great, Cynthia Hall’s feelings about anal training and her master’s approaching possession of her bottom would certainly have progressed without such harsh punishment.

  The Ostia capta told herself sternly first that her job wasn’t to spare her agent the whipping that now made a fiery network of red across her bottom-cheeks and upper thighs, but to save civilization. Cynthia’s screams and writhing struggles under Herrier’s hand and in the webbing collar and cuffs she wore would not permanently harm her, and they would in the end bring about her development as a happy submissive.

  Indeed, the point of the way Sarah had designed Operation Relegate lay finally in Goshawk’s coming around to be a better master for Cynthia. The subtle bonds that would ensnare the Guard’s wiliest enemy were growing even now, as the sensors on the jet told her.

  Herrier’s eyes fixed on his girl’s bottom as he watched the punishment, and the slight shifts in his body temperature throughout his limbs told a tale the Guard’s algorithms could analyze as growing desire not just to subjugate a hipster but to subjugate Cynthia Hall, the girl on whom he had spent so much money. The correlations they analyzed between his words and the unspoken messages of his stance and his facial expressions told Sarah, as she watched her analysts report via text chat, that it had begun to work. If Greg managed the next few days correctly, the Guard would be able to use Cynthia to get them all the intelligence they needed to reduce the market share of Herrier Energy.

  They kept Cynthia bending over the bench, weeping over her punished bottom. Her arousal had gone all the way down to one, but now it ticked up to three.

  “The nightgown will stay tucked up,” Herrier said, “when we depart, to show everyone in my household that I know how to reward a naughty girl, and to teach you that I will display you as I like. Now…” He loosed her wrists from the cuffs. “Reach back and spread this bottom. Show me your anus, ma fille.”

  Cynthia gave a sob, and then she cried out as her fingers touched the tender surface of her well-whipped bottom-cheeks. She spread them, her breath coming harsh and fast from her mouth.

  “Et voici,” Herrier said. “I like a girl to hold herself like that while I fuck her, don’t you, Maître Gregoire?”

  “Of course,” Greg said dryly. “It’s a sign of respect… she knows she must make her bottom as pleasant for the cock as she can.”

  Cynthia whimpered into the leather against which her master held her face. Herrier ran his right hand up and down her back, under the nightgown, moving finally to hold the back of her neck in its black webbing collar.

  “Isn’t that so, ma fille eepstair? Do you know that your anus must please me, or you will be whipped again and again?”

  Cynthia’s agreement sounded like it was wrenched from the bottom of her soul.

  “Yes, monsieur.” In the upper right of the video feed, she went to five.

  “Keep yourself spread while your maître puts you back in your harness,” Herrier commanded. “You will suck my cock in the car on the way to the chateau, and Maître Gregoire will press upon the plug as you do. If you suck well, I will tell him to play with your clit, too, and you will have an orgasm.”

  The harness looked very moving indeed, encasing such a painfully punished backside. Cynthia whimpered, but her arousal went to six as Greg skillfully inserted the plug and buckled the belt. Then he helped her rise on shaky legs. Each step brought a soft cry from Cynthia as they made their way from the jet out onto the tarmac, all of the new bed girl’s charms displayed to the limousine driver as he opened the passenger doors.

  Sarah felt sure he had taken a good look at Cynthia’s lovely little virgin pussy, waxed bare and accentuated by the lifting of the nightgown’s hem and the lascivious framing of the straps that ran along the crease of her thighs to hold the plug in her anus behind. It was usual in such aristocratic households for the servants to be told they would be allowed to fuck the concubine once their master had deflowered her and enjoyed her for a honeymoon season.

  Now the robustness of the Institute’s sensor data would decrease drastically. In the car, only Cynthia’s perineal sensor, accessed via satellite through Greg’s comm link, would tell them anything. If matters became dangerous, a drone could be dispatched from high above, but Sarah had to rely on Greg now. Of course that had always been necessary, she reflected, but knowing the playing out of events in real time made her feel much more in control.

  She imagined Cynthia on her knees now in the limo, seeing Herrier’s cock for the first time, her head probably pulled down roughly atop it, in keeping with the man’s need to subjugate his hipster girl. “Baise-moi,” he had undoubtedly already said, using the indescribably dirty, degrading French expression that actually just meant “Kiss me.” When the aristocratic Frenchman said it, though, it didn’t mean that he wished a chaste kiss upon his lips: it meant rather the humiliating service of a bed girl’s mouth below his waist, full of stiff, thrusting penis, and so what was otherwise innocent became demeaning, and incandescently hot.

  On the video feed, which remained fixed on a shot from the jet of the car driving away, Cynthia’s arousal went to eight, and then to nine. Ten, flashing.

  The number turned red, flashed again, and the pre-orgasm alert appeared.

  Sarah smiled. That was fast. She allowed herself a sigh of relief, and then she turned to Operation Heatsink.

  David Mancini, codename Osprey, definitely had a good deal to recommend him as a recruit for the Pretorian Guard. The construction company he stood to inherit had contracts with the city of New York that could prove extremely advantageous when manipulated for the benefit of the Guard’s mission. Moreover, his college transcript showed a mind very open both to the potential of technology to change human capabilities—he had a minor in Computer Science to go with his major in Psychology—and a suspicion of culture’s too-rapid advance.

  Prime Guard material, but recruiting him had to be accomplished in association with Operation Relegate, because any tampering with Osprey that didn’t involve Oriole in a natural-appearing manner could alert Herrier that all was not as it seemed with his concubine. On the other hand, bringing the recruitment of David Mancini into close association with the turning away of Herrier Energy from competition with the Guard could make Relegate a slam-dunk. If Herrier thought he had gotten the better not just of Cynthia’s hipster culture but also of h
er more straitlaced former (and maybe future) boyfriend, the honeypot would truly become a sort of Venus flytrap.

  The difficulty would lie in finding a way to bring Osprey onto the scene without letting him in on his being used by the Guard until the operation had fallen into place. There was no time to train David as an operative: all his responses had to seem utterly natural.

  Sarah had only a single idea, but she considered it a good one. Addie Jacobs, Cynthia’s best friend, had always wanted to see France: now that Cynthia had disappeared, Addie’s wanderlust would naturally increase.

  Sarah reached out to her top agna analyst.

  SBo6: Grace, how hard would it be to create a targeted travel offer in Air France’s system?

  GEo4: You mean for a single recipient? As a lure?

  SBo6: exactly

  GEo4: Dead simple. It will look like the offer is going to thousands of people but it will really only go to the subject. The targeting itself is the hard part: success rate is about 80% even with good data on the subject.

  Sarah pondered, then shrugged. Eighty percent would have to do.

  SBo6: I’m sending you the trace for a girl named Addie Jacobs. See if you can lure her to Paris within the week. Hotel in the Faubourg Saint-Honore.

  The trace represented Addie’s basic identifying information within the vast virtual universe of the world’s networks. Every piece of data in existence that had anything to do with her, whether because her face popped up in a picture on social media or a surveillance camera, or because her IP address logged into a server in the Philippines, would go straight to Grace’s desktop. More important, the Guard’s metadata scraping would tell her a very great deal about Addie’s triggers for impulsive action.

  GEo4: This is reasonably good. I’ll up your chances to 90% because she’s impulsive generally, and pretty independent.

 

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