Trained by the Trillionaire

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Trained by the Trillionaire Page 9

by Emily Tilton


  Moreover, and more important for Sarah’s purposes, the suite of sensors designed in by the Institute had received a substantial Guard upgrade, the additional capability focused not on measuring the arousal of the girls receiving erotic training but on the men who used them to seek their dominant pleasure. As much of the Guard’s equipment installed on the plane pointed outward from its wings and fuselage as inward on the cabin: Goshawk was unlikely even to enter the plane’s interior, let alone spend enough time there to provide the Guard with robust data, but they would at least get high-resolution audio and video of him and any associates he might bring. That could aid the operation in ways hard to foresee but quite possibly crucial in reaching an outcome acceptable to the Guard: knowing the identity of a single henchman had on occasion made all the difference between success and failure in such affairs.

  And if he did decide to get Oriole off the plane himself… if he decided he couldn’t wait to begin her training even so long as to get her in his limousine…

  Well, the Guard’s equipment in the plane’s cabin could make Black Bear’s job as the girl’s handler a good deal easier, as it gathered the special kind of biometric data that told of a subject’s vulnerabilities not only in the sexual arena—the Institute’s specialty—but also in such further flung fields as politics and finance. The correlation between verbal communication, body language, and changes in heartrate and oxygen intake remained a kind of dark art, proprietary to the Guard just as the Institute’s arousal algorithms had stayed a closely held secret on their side. Good fences made good neighbors, even when the neighbors were a purveyor of living sex toys and a clandestine organization bent on saving the world through illegal means.

  Sarah also checked the hidden weapons cache that would represent Greg’s—and the flight attendant, a fifth degree Ostia initiate—last resort if things went sideways on the ground in France. The likelihood of some kind of standoff on the Institute’s Cessna was very remote, but the Guard hadn’t kept itself in business by taking risks.

  “You’re good to go, agna,” she said to Holly, the flight attendant, using her Ostia title, which signified she had gone through the appropriate initiation rite: in this case being bound to a bench to be used anally by seven men.

  “Thank you, capta,” Holly replied. Sarah’s initiation to the rank of capta had meant being secured, naked, by her new husband to a pole in the Guard’s senior common room. For a night and a day she had served the lusts of any guardsman who wished to employ her body for his pleasure. At evening Robert had come to loose her from the pole and carry her home in his arms. Whenever anyone called Sarah capta, she tended to shiver at the memory of that most frightening, most pleasurable thirty-six hours of her life.

  As she watched the plane taxi, Sarah thought about Cynthia Hall, and how she would react when told, as Greg Sampson would have to tell her when the operation reached the crucial stage, that she had been inducted as a member of the Order of Ostia. Sarah had sought out the order as part of a CIA counterintelligence operation that had in the end resulted in her changing sides. Oriole would have even less choice in the matter than Sarah had.

  As her driver, a second-degree nymphus of the Guard, headed Sarah’s car back to the city, she called Jessica Logan in the Institute’s liaison office in DC.

  “Garnet,” Jessica answered.

  “Hi sweetie,” Sarah said. “Could you send me what you’ve got on Oriole’s boyfriend? Go ahead and codename him Osprey, please.”

  “Okay,” Jessica said, lengthening both syllables to express mild puzzlement. “Do you want to tell me why?”

  “I need to run it by Jupiter first, but I want to have a dossier ready.”

  “Are you worried about Oriole?”

  “A little?” Sarah said. “I’m not sure we should rule out some happier kind of ending for her. Provided Jupiter agrees.”

  “You know I love happy endings,” Jessica said with a giggle.

  * * *

  Back in her office, Sarah pulled up Cynthia’s feed, which showed her saying goodbye to the other girls and to Miss Charlotte in the grand foyer of the Institute’s manor house. A location tracker for Greg indicated that he was in the car waiting to take Cynthia to the airfield.

  Jessica’s rather slap-dash compilation of their data on the newly christened Osprey—David Mancini—arrived in Sarah’s encrypted mail a few moments after she had sat down, having taken off the dress she had worn out to the airfield and put on her cuffs and collar. Ostia initiates weren’t allowed panties except when dressed in them by their masters on specific occasions, so Sarah now sat in her black garter belt and nylons and her black lace bra.

  Robert’s instructions on her ‘work outfits’ were clear: if Sarah were coming from something to which she had worn lingerie, she must keep the underwear on after she removed her dress. Otherwise, she must be naked at her desk. Always as she sat in her leather desk chair for the first time when beginning to work, her lips twitched in an irrepressible smile as she remembered that she belonged to a man who liked to specify with regard to such matters.

  Was David Mancini, perhaps, that kind of man?

  Robert walked in, and Sarah couldn’t help the heat that came to her cheeks at the thought that he would certainly now discover the little project on which she had just embarked, with Osprey, and her diversion of precious resources in that direction. She should have run it by him before even asking Jessica for the data, she knew.

  He came to stand behind her, his right hand on her shoulder, and bent to kiss the top of her head. Sarah had to fight the impulse to close the window on her computer desktop containing the dossier under the new codename. Maybe Robert wouldn’t notice, his attention diverted by the video feed of Cynthia now getting into the limo to sit next to Greg, looking extremely fetching in her pink nightgown with the anal harness just showing deliciously through the sheer fabric?

  Maybe Sarah should confess? Well, she should definitely confess, but that would mean a spanking right here and now when she had better things to do, but on the other hand if she didn’t…

  “Who’s Osprey?”

  Her heart sank. Now all she could do was make her punishment less severe, and perhaps negotiate for a more convenient time, and a place—their bedroom—where Robert might have more of an impulse to proceed to fucking than he would if he decided to paddle her here in her office.

  “Oriole’s boyfriend, sir,” she said, looking up and turning her head to try to decide how seriously her husband and master would regard Sarah’s misbehavior on this issue. She got a glimpse of an evaluating expression she knew very well, and her heart sank further: the slight tension in his jaw meant that he knew very well his wife had done something worthy at least of a spanking, if not the paddle or the cane.

  “Was that in your brief, sweetheart?” he asked with a deceptive gentleness that made Sarah’s heart flutter.

  “No, sir, but—”

  “No excuses, Sarah. You know you’ve got a date with your paddle.”

  Sarah felt herself clench down below, though she knew that Robert would make sure he drove her arousal away the old-fashioned way when he decided the time had come to teach her the oft-renewed lesson of staying in her own lane, when it came to the Guard’s intelligence operations.

  His eyes went from her face to the screen, and Sarah knew he was judging whether the current operational status of Relegate demanded her attention, or whether he could discipline his wife and capta right away. Robert favored firm, consistent, quick punishment, and Sarah knew that despite her hyper-intelligence and her modern attitudes—really she had a good deal in common with Cynthia Hall despite shopping at Prada and Saks rather than in thrift stores—her master’s old-fashioned approach to guiding his girl’s conduct kept her life on a blessedly even keel. They might be working desperately against the clock to preserve civilization, but thanks to Robert’s dominance and Sarah’s submission, they had no reason to dwell on the bleakness of the duty they had undertaken.


  Turning her own gaze to the shot from inside the limo of Greg talking softly to Cynthia, Sarah searched desperately for something she might offer as a reason Robert couldn’t tell her to get the paddle from its place atop her dresser right away. She found no help at all in the speech-to-text captioning.

  Oriole: How long will the flight be, Master?

  Black Bear: About ten hours, honey. Your owner will be waiting for us at the airfield. He’s a very important man, but a very private one.

  Robert said, finally, “Tell me why you codenamed the boyfriend, Sarah. Then you’ll get your paddle and I’ll punish you over your desk.”

  Sarah winced as she turned around again to look up at her master. She could at least see curiosity in his face vying with his dissatisfaction at her misappropriation of resources. But Robert seemed to read her mind.

  “It doesn’t matter to me how good an idea you have, sweetheart. You knew very well you should have cleared it with me first. You’ve got quite a paddling coming.”

  Sarah bit her lip to prevent the “But” from emerging and making it worse for herself.

  “What if the boyfriend were Guard material?” she asked quietly.

  Robert frowned. “Are you trying to give her a happy ending?” he asked, shaking his head. “Sarah, you know that’s not your job.”

  Sarah’s pursed mouth twisted to the side. She hoped desperately the expression proved as irresistible to her master as it usually did.

  He sighed. “Alright. You may go ahead. You’re not to spend more than hour on it. If you have a plan after that, you may present it to me. Now go get your paddle.”

  Sarah glanced back at the screen. Cynthia was kneeling on the floor of the limousine, demonstrating her oral skills to Greg.

  “Get going,” Robert said, his voice growing a little stern. She looked up at him again as she rose slowly from her desk chair, trying to beam her newfound hope into his eyes. To her relief, Robert smiled. “I’ll watch this while you’re gone. Who knows, I may decide to fuck you after, with this for inspiration.”

  The leather paddle that had Sarah’s name and degree of initiation engraved on it came down very hard, and very fast, on the apple-like cheeks from which Robert pulled aside her garter belt’s suspenders. The arousal she had felt at the familiar sight of the disciplinary implement, and at the humiliating duty of carrying it to her husband so that he might punish her, of kissing it before she handed it to him, of bending over her own desk for her bare bottom to pay the price of her misbehaving, all went away as Robert did in fact make her very, very sorry for waiting to ask permission to put her idea into action.

  But with the arousing sight of Oriole going down so skillfully on Black Bear in the limo, as they waited for the plane to touch down, in his line of vision as he paddled Sarah, Robert did yield to his dominant desire, and Sarah did receive the ambiguous reward of a very hard fucking, without being allowed to come.

  Chapter Fourteen

  The flight to France quickly took on a dreamlike quality that didn’t spring entirely from the way they flew through a dark night toward the dawn in the East. Master Greg had come in Cynthia’s mouth just as the California twilight had turned purple around the windows of the limo where he had made her kneel before him while he took out his cock. The head of his softening but still firm penis had been in her mouth, while she drew from it the last drops of his semen, when they heard the roar of the small jet as it came in to land. Cynthia still had the burning, but rather sweet, taste of him on her tongue as she preceded him up the steps into the plane’s luxurious but strangely menacing cabin, with the long bench clearly fitted for the restraint of misbehaving concubines.

  She had climbed those steps, entered that cabin, wearing something she could never have imagined wearing outdoors, let alone to an airfield, let alone on an elegant private plane to Europe. The pink nightgown, that everyone who mattered—Cynthia caught herself thinking this way not with astonishment but with a dreamy sense of rightness—knew meant she had received discipline on her bare bottom that day. Under the nightgown, the horrible harness, that everyone knew meant she would soon have anal sex.

  Everyone could see the belt that buckled behind, and the three straps that held the plug in your anus while leaving your pussy available for fingering and even tonguing by your master. Or, worse, by other girls when your master decided you needed to pleasure and be pleasured by a fellow concubine.

  The harness… the way it felt, girding her between waist and knees, training her for her owner’s pleasure, opening her more and more with the passing hours she must wear it. The way it looked in the mirror that adorned the front wall of the plane’s cabin, dark leather showing through sheer pink silk.

  It seemed to create the fitful dream of that flight. It seemed to tell her, and Master Greg, and Holly the flight attendant, that Cynthia Hall wasn’t the sort of private-jet passenger who got a glass of champagne when she came on board. Master Greg got one of those, while Cynthia was told to sit on the long bench seat, and had her seatbelt fastened by her trainer over the nightgown and over the harness. The seatbelt had a lock, so that only Holly or Master Greg could release Cynthia from the bench.

  After takeoff, cruising at thirty-five thousand feet, Master Greg did release her, because the truly dreamlike part was about to begin.

  Holly said, coming over to refill Master Greg’s champagne, “You’re going to go down on me now, Cynthia.”

  Master Greg reached over and used his key to unlock Cynthia’s seatbelt. “Lay her down on the bench and ride her face, Holly,” he said, as if first class passengers did that all the time. “You can play with her butt plug and even reward her clit if she’s well-behaved under your cunt. Make sure she tongues your anus, too. Her owner’s going to make her do that frequently, we think.”

  Really these instructions didn’t differ very much from what she had heard every day at the Institute for the past two weeks. But air travel had always seemed like its own world to Cynthia, even when she had flown to Hawaii or Bermuda for family vacations when she had been young. Strange things, it had always seemed to her, could happen on planes—should happen on planes, perhaps.

  “Please…” she murmured, as Holly took her hand to raise her up from the bench. “Please, not the butt plug.” She had no hope at all that the pretty red-haired stewardess would honor the request, but she knew she must make it. She hated to have the plug inside her, and she hated it almost more when someone, master or fellow bed girl, touched it and reminded her about how her owner had decided to make her his anal girl.

  “Cynthia has trouble with anal,” Master Greg explained simply to Holly.

  “I’m sorry, honey,” Holly said. “But you know it’s better for me to do as your trainer says, don’t you?”

  Cynthia bit her lip and shook her head, frowning. She cast her eyes down to the blue pumps of Holly’s flight attendant uniform, which consisted of the kind of coat dress that could be unbuttoned down the front to show what underwear the stewardess had on. This Holly did now as she looked at Cynthia, to reveal that she had a red garter belt on, with no panties, and a matching lace bra enclosing her big, perfect breasts.

  “Do you need a spanking, honey? I can see you’ve already been punished today.”

  Master Greg confirmed Holly’s impression. “She’s had to be spanked every day, to get her to spread her buttocks.”

  Cynthia couldn’t help raising her eyes to see what the flight attendant made of this information. She found Holly’s face sympathetic. But the stewardess spoke not to Cynthia, but to her trainer.

  “Doesn’t she know her owner will cane her, if she refuses to show him her anus?”

  Cynthia turned anxiously to see Master Greg shake his head in a concerned manner. “She does, but it doesn’t seem to help.”

  The dreamlike conversation stopped, then, as if Holly and Master Greg had said everything they needed to say to one another, and neither had any interest in what Cynthia might think about the subject. They made
her lie on her back on the bench, and then Holly got over her, straddling her face.

  Whoever owned Holly allowed her to keep some of the red curls around her pussy. That made Cynthia feel faint, because all the girls at the Institute were bare between their legs just like Cynthia herself was now. She had learned, with fluttering heart and butterflies in her tummy, to bend her head to kiss a clit, and to taste with lapping tongue. Master C had made her kiss and tongue anuses too, just as the other girls had to do. Cynthia had had to use dildos and vibrators on Gwen and her other hall-mates, and in Feminine Pleasure class she had sixty-nined with various fellow students for a whole hour, learning how to combine fingers and tongue in various ways to wring orgasm after orgasm from another girl’s pussy. She had never kissed a girl who had pubic hair, though, and though once she had watched Miss Charlotte queen Gwen like this, mounting over her face, it had only been a demonstration.

  The darkness down under Holly’s cunt and bottom, and the musky smell, and the wetness, all made Cynthia feel faint. Holly’s movements, though, and the sounds of need and satisfaction and greater need as she rode, seemed to call forth a lightheadedness much more intense than the mere shortness of breath enforced by the moist private parts pressing onto Cynthia’s face could do. She felt, more intensely than she had even with Master C at the Institute, herself detached from her body, almost looking down at Holly posting up and down on Cynthia’s little face, crying out in command, to make sure Cynthia didn’t neglect the pink, wrinkled button of her anus.

 

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