Trained by the Trillionaire

by Emily Tilton

  SBo6: Thanks. Let me know.

  GEo4: Offer email will go out within the hour, and I’ll let you know if she bites. If she’s going to, it will happen fast.

  Sarah turned her attention back to Cynthia’s video feed, a shot from a drone high above but with good enough resolution to see Goshawk’s car entering the drive of his chateau. In the upper right, Cynthia’s arousal had quieted to five. The ticker in the chyron showed she had been rewarded with not one but two orgasms.

  Sarah wished she could see inside the limo’s passenger compartment: whether the concubine had been made to remain on the floor or she had been allowed to sit next to her master on the car seat would give a good deal of information about the progress of the operation. Some of the data from the jet’s sensors had seemed to show that Goshawk might be falling in love with Oriole much more quickly than the operational plan had anticipated: if he were, he would probably raise her up to sit next to him and look out the windows at the passing countryside.

  To her surprise, a chat from Grace popped up.

  GEo4: I’m not sure I’ve ever seen a girl book a trip so fast. Arrives CDG Saturday 9:02 Paris time.

  Sarah smiled. She typed back:

  SBo6: Alright, codename her Sparrow, please. She’s Asset 1 of Operation Heatsink.

  A pause as Grace presumably reviewed the rest of what Sarah now sent her.

  GEo4: Clever, capta mea.

  SBo6: Too clever, maybe. But Jupiter says I can try.

  GEo4: And I’m sure you’ll pay a penalty if it doesn’t work. ;)

  SBo6: But of course.

  She opened a chat with her husband, her heartrate increasing noticeably. Theoretical speculation about Heatsink was one thing, but now Sarah backside’s capacity for sitting comfortably represented the least of her worries: she would risk the safety of two innocent people now, in a high-risk bid to get Oriole’s story to end more happily. The value of the operation, should it succeed, stood in no doubt—not just for Cynthia’s future happiness but for the Guard’s European efforts. Sarah couldn’t suppress a swelling of pride in her chest at that thought, but she also couldn’t deny how nervous she felt about telling Robert that she had declared the operation ready to proceed.

  SBo6: Sir, Heatsink is go. Asset 1, codename Sparrow, will be in Paris next week.

  RBg7: Put me on the chat queue, please.

  Sarah swallowed hard: it meant that Robert would watch in real time as Sarah attempted to use all available resources to bring Addie Jacobs where she must go, if Heatsink were actually to get off the ground.

  SBo6: Yes, sir.

  RBg7: What does the modeling say about when Goshawk will be ready to take Oriole to Paris?

  He knew how to cut directly to the uncertain heart of every scheme Sarah had ever launched for the Guard’s benefit. The series of events that would lead to Cynthia’s presence in Paris for the furtherance both of Relegate and of Heatsink was far from a certain proposition.

  SBo6: If Black Bear can implement the plan, we can drop the stimulus Sunday.

  RBg7: If.

  Sarah grimaced, then glanced at Cynthia’s video feed. The limo had just pulled up in the porte-cochere.

  Chapter Eighteen

  Cynthia had grown up comfortably among the big houses of the upper middle class in the Boston suburbs. Even the mansions along Commonwealth Avenue—even the brownstones of Boston and Brooklyn—had not prepared her, though, for what she saw now. For all her habitual hipster jadedness she simply couldn’t keep her jaw from dropping as the limo drove up the drive toward Monsieur Herrier’s chateau.

  Sitting next to him on the leather seat, across from Master Greg, to her dismay she blushed at that feeling of wonder—the girlhood fairy-princess marvel she couldn’t suppress. At least Monsieur Herrier would take the pink in her cheeks, Cynthia felt sure—indeed she hoped, because the alternative discomfited her even more—as a sign that he had evoked a becoming modesty in his new bed girl.

  Cynthia blushed, she hoped he would suppose, because she had been whipped over the bench in the plane: he would think she felt the awful soreness in her bottom and thighs, worse even than the cane because her owner had specified that the whipping be very harsh and go on for a very long time, and knew herself to be the property of a man who would discipline her thoroughly when he deemed it necessary.

  Or he would suppose that her face had gone red because he had just made her suck her master’s cock in his car, or because he had tucked her nightgown up to show her bare pussy in front and her plugged bottom behind to anyone who cared to look: to Holly the stewardess, to the limo driver, and to whoever waited in the chateau. He would see her blush and he would even perhaps think that he had won her shame through the two orgasms Master Greg had forced on her, wanking her pussy vigorously as she showed she could take her master’s thick penis deep in her mouth, her nose buried in his wiry pubic hair for long seconds as he enjoyed himself with his cockhead against the back of her throat.

  Cynthia might well have blushed about those things, too, if she hadn’t had the chateau to look at, occupying almost the entirety of the horizon as the car approached it. Her blush would have dismayed her in that case, too, she supposed, since she hated the way her trainers could still play upon her shame to enjoy mastering her seemingly unquenchable innocence.

  But the true reason for the blood’s rush to her face seemed worse to her, since to feel such wonder at the sight of what amounted only in the end to someone’s house seemed like a betrayal of everything she had meant to stand for. So when Monsieur Herrier spoke to her for the first time in several minutes—since he had said, “You look pretty with a cock in your mouth, ma fille”—and showed from his first words that he knew precisely why Cynthia had blushed, it made the crimson spread from her face all the way down her neck.

  “You would like to come here as a princess, I think, ma fille,” he said softly in her ear, mockery infusing his voice though to Cynthia’s surprise it sounded more like gentle teasing than like true ridicule meant to humiliate.

  “No, monsieur,” she protested, because she couldn’t help speaking out to deny precisely what she knew in fact as incontrovertible truth, so embarrassing did it seem to her.

  “Cynthia,” Master Greg warned. “You know better than to speak out of turn.”

  “It is alright,” Monsieur Herrier said. “I addressed her, even if I did not ask a question.”

  She had felt a bizarre thrill of hope when Master Greg reprimanded her—she might even rather have a spanking on top of the terrible whipping than to have to discuss the fairy-princess feeling. All the erotic degradation she had undergone from the moment Master Greg had woken her up in her loft seemed to have touched her soul less than this unguarded moment of wonder at the sight of her owner’s baroque chateau, with its seemingly endless wings and its ornate architectural sculpture of angels and animals.

  Maybe they would go on discussing her as if she weren’t there, talking about her mouth and her cunt and her anus, and how Master Greg would make sure all three were as pleasurable as the owner of such an expensive concubine deserved, when the time came for him to have his way inside her. They had spent a good deal of time engaged in that sort of conversation while Cynthia had demonstrated her progress in fellatio, cheeks burning as she heard the waxing of her pussy described, and the blowjob she had had to give Master Greg in the shower afterward. Monsieur Herrier, it appeared, had watched all that somehow, and he had told Master Greg that Cynthia’s demure clitoris, exposed to view when he bared her, had thoroughly affirmed his wisdom in making the purchase, even if it would be her anus in which he spent most of his time.

  Again she wished the heat in her cheeks now had arisen from the same reason, rather than from the more shameful, girlish desire to wear a lovely gown and dance in marble halls.

  “Cynthia,” Monsieur Herrier said now, dashing that latest hope, “you will be a princess here if you wish, though of course a princess of a very special sort.”

 
Oh, no. How could he? As she had contemplated the possibility of the conversation going in another direction, she had felt the blood begin to recede from her face, but now it came back, giving her the momentary impression that she must actually shine like the sun, so hot did the sensation feel.

  Now she took refuge in her trainer’s reprimand. Monsieur Herrier hadn’t asked a question, so Cynthia didn’t have to answer. She looked out the window, wondering suddenly why her owner had invited her to sit next to him after she had swallowed his seed, rather than leaving her on the floor as seemed to her—especially now—more suitable. If she had stayed on the floor, she wouldn’t have seen the palace on the hill. She would only have seen the porte-cochere under which the car now pulled up, the stunning grandeur of the rest of the chateau fully hidden from view. The stonework in this porch was gorgeous, to be sure, but it wouldn’t have overwhelmed Cynthia the way she still felt overwhelmed at what she had seen when the car had turned into the drive.

  But her owner could somehow read her mind, it seemed, at least when it came to finding the perfect method to humiliate her.

  “Would you like to be my anal princess, ma fille?” he asked softly.

  Cynthia gasped at that, turning to look him in the face despite all her training in this most basic rule. The blood surged in her face again as she saw on Monsieur Herrier’s face the knowledge of just how terrible a conflict he had just set raging in her body and her heart. She dropped her eyes to his waist, to the trousers and the belt still undone from when he had taken out his penis for her to suck until he had spurted his seed down her throat. She saw a stirring there, and she gave a little whimper.

  The whimper became a startled cry, for her owner had reached his hand out swiftly, arrogantly, and put it between her thighs, seizing the top of the left one as if he were handling a piece of meat he meant to braise with wine into an elegant boeuf bourguignon.

  “Answer, if you please, Cynthia.”

  She bit her lip, hoping still that she might be spanked instead of subjected to this man’s penetrating perception of her weakness.

  Instead of putting her over his knee, though, Monsieur Herrier began to speak again, in the same teasing tone that seemed to say he knew her true shame, her true betrayal.

  “In the olden days, as English would have it, real princesses taken from enemies in distant lands might find themselves brought to France and made into concubines such as you. They would lie upon their faces in this chateau’s lovely beds, and learn to yield their bottoms to a lord’s hard penis deep into the night. Their ideas concerning their royalty, their power, their independence, would all go away, as they were whipped until they spread their hind-cheeks for a vigorous fucking there, where they never expected a man would demand their service.”

  Cynthia’s breath came in little pants now. A sob burst from her chest, and her whole body shivered as her owner’s hand forced itself further up, his thumb seeking out her clit, already sore from Master Greg’s urgent masturbation during the fellatio.

  “Over and over the lord would take his fallen princess’ bottom, his blood on fire with the very idea of invading her most private place, of teaching her of her new status as his fucking piece—and, when he had again entered her so shamefully, with the thrilling tightness of her little round bottom. She would wear a harness every day, just as you do, to help her learn her place, and to ease the narrow path, making it more pleasurable for her master when he fucked her there at night.”

  “Oh, please,” Cynthia whispered, not even knowing what she meant. The thumb rubbed, she whimpered.

  But then, abruptly, Monsieur Herrier pulled his hand away and put it to her face. He rubbed her shameful fragrance on her mouth, her nose. She remembered Master Greg bringing her panties to her face the night he had come to her loft, but this shame seemed much worse, happening in a limousine in the porte-cochere of a massive chateau, with her nightgown tucked up and her harness girding her between waist and knees.

  “Ma fille,” Monsieur Herrier said softly, the teasing gone now, “you will be my anal girl before long. You have no choice. The cock will go up your bottom tonight if I have to whip you until you beg me to take you there. The only question is whether you will also be my anal princess—a fallen princess, like the one in the little story I just told you, but a princess nonetheless.”

  Cynthia bit her lip. He hadn’t asked a question, really, had he? He had only pointed one out.

  “Is not that princess of the olden days’ position similar to yours in more ways than simply her being made a concubine and made to have a penis in her bottom when her master decides he wants a bottom-fuck?”

  “What?” The interrogative burst from Cynthia without her even willing herself to speak. What is he talking about? I’m not a princess, no matter what stupid fairytale desires I have left over from kindergarten.

  “Look at me, ma fille.” He had kept his hand, with its shameful aroma, at her face until these last words. Now he put his fingers upon her chin, turning and tilting her face toward his.

  Startled, Cynthia did gaze into his ice-blue eyes.

  “Is not a modern girl, an eepstair like you, a sort of princess? Does she not think she has a right to say non to a man’s putting his penis in her bottom?”

  “She does have that right!”

  Cynthia felt sure she would be punished for the instant retort, but the conflict inside had risen so high that she could not have held her silence. To her astonishment, though, Monsieur Herrier smiled.

  “Mais, oui. Bien sur. She has that right. But do you have that right, Cynthia? Not because I have purchased you, and I will whip you if you refuse me. Rather, because you do not have the right, as I see it philosophically, to deny yourself what you truly need.”

  Oh, no. He still held her chin, but Cynthia couldn’t meet his eyes anymore. She dropped her gaze.

  “Look at me, ma fille,” her owner said again.

  She tried to shake her head, but he held her chin fast, and she did glance up, feeling her forehead furrow very deeply.

  “I will dress you in silk and lace, my modern girl, instead of denim and flannel. You have no choice about that, any more than you have a choice about whether I will fuck you as often as I like, and whip you when you deserve it—or when I feel like it.”

  Cynthia chewed the inside of her cheek, willing him not to put his hand between her legs again because of how very wet he would find her.

  “You have a choice, however, in whether you wish to be more to me. You will never be wedded mistress of this chateau, but you may certainly be a treasured fallen princess whom I can take to Paris and show off as this house’s current lady, and the lady of my heart.”

  Chapter Nineteen

  Greg could scarcely have imagined the operation going better, thus far. The data collected on the jet about Herrier might already have been worth the resources spent on the mission. Now, to see in the magnate’s eyes that he had indeed started to fall hard for his hipster girl not only gave confirmation of Operation Relegate’s potential but also reassured Greg that Cynthia did in fact fit the bill—in the flesh, as it were.

  At the back of Greg’s mind, as he knew also at the back of Sarah Bennett’s, had lurked the possibility that as compelling as the theory behind Relegate might be, it would prove unworkable in the field. They had gambled big that Goshawk would focus the obsession the Guard had identified in him—his dominant craving to put modern culture in its place—on the girl they had chosen. They had picked Oriole as the perfect repressed submissive representation of hipster cultural forces, and with the help of the Institute provided her to Goshawk as a perfect honeypot, because he had purchased her for himself.

  But the consummation of the plan lay in human chemical forces that even the Institute couldn’t model beyond 90%, even with the abundance of data they usually had, and Herrier had done as good a job as a notable man could do concealing himself from the harsh glare of the digital age’s social media floodlights. Now Goshawk stepped from
the limo and extended his hand to help Oriole out after him, for all the world like a prosperous gentleman escorting a lady to the opera, despite the lady in question having on only a lacy pink nightgown tucked up to show that her gentleman had elected to train her shamefully for his sexual use. That gesture, combined with the expression in Herrier’s eyes as he took in Cynthia’s renewed blush, told Greg that they had gotten over one big hurdle, and now the true danger lay ahead.

  Cynthia would be deflowered anally tonight: he had no doubt about that. Greg would ensure that the experience would in the end further the girl’s progress toward a happy life as a self-confident submissive, in touch with her body’s needs. He also needed, however, to bring it about that Herrier felt himself to have conquered her, subjugated her, tamed her. The full value of Operation Relegate lay in Cynthia consenting to be Herrier’s anal princess, but at the same time not losing her inner resistance to the ultimate act of his mastery: only thus did the models show that Herrier would feel he must take her to Paris, to display her subjugated anus to those whose opinion the magnate valued most—the other four members of the Groupe Synergistique, as it seemed they jokingly called themselves, though the Guard’s knowledge on the matter remained maddeningly spotty.

  No real bodily risk was attached to this ordeal for Cynthia. Greg’s attendance on her and her owner’s pleasures would see to that: anal would be uncomfortable for her at first, especially when Herrier shared her bottom with his powerful friends, but the training she had received at the Institute, as unwelcome as it had been, would ensure no harm came to her. She would cry out as her master rode her, especially this first night when Herrier would probably want to have her bottom more than once, but Greg would be able to enforce a rest if necessary before her next compulsory anal session.