Trained by the Trillionaire

by Emily Tilton

  Cynthia had learned that she played with herself more than most girls did, but that she shouldn’t be ashamed of it.

  That hadn’t helped: her face still got hot if she even thought someone visiting her loft might look over at her bed and see the special pillow she used for pillow time.

  Master Greg pulled the fragrant cotton away from her face, held it again in front of her eyes. “How did those stains get there, honey?” he said in the same calm voice that seemed to mix sympathy and accusation in equal measures.

  Cynthia bit her lip and gave a little sob.

  “If you don’t answer, Cynthia, I have to keep spanking you,” he said, and then he did, even though she had thought he would wait to see if she spoke, and she had intended to speak.

  “No, please! It hurts!” she cried in a pitiful voice as more and more swats landed, all over her backside now: right, left, up, down. Her bottom clenched and unclenched, but the whole region seemed on fire, and wouldn’t he stop soon? Wouldn’t he say It’s supposed to hurt?

  But he just kept spanking, and Cynthia was screaming now at the pain, and she understood that she really did have no choice.

  “I played with myself!” she sobbed. “I… I… rode my pillow!”

  The spanking stopped. Looking down, she saw she had made a little puddle of tears on the hardwood underneath her face, and her eyes felt swollen with the weeping she had done. Something inside her, though… something felt… clean? She had a sudden fear that he would make her tell him about that feeling, and she knew with a strange clarity that no amount of spanking, whipping, or caning could ever drag that out of her.

  “Was that so hard, honey?” Master Greg said, and then he put his right hand back on her burning bottom-cheeks, and he started to rub.

  Nonononono. Oh, it was so much worse than before. The heat was so much greater. She had never felt anything so awful and so good, and she cried out as her too-well-trained hips bucked, moved her desperate pussy just a little over the denim of his jeans.

  “You’re old enough to play with your pussy, aren’t you, Cynthia? Men like me, and the man who will buy you—or the woman—understand that. Are you a big girl who likes to play with your pussy in bed?”

  “Yes, Master,” Cynthia sobbed. How could she disobey him now, at all? How could she fail to say, Yes, Master?

  His fingers descended, pressed, caressed. Oh… no, please… she could hear how wet she had gotten, instantly, the moment he had begun to rub her bottom.

  “But you’re the sort of girl who needs to know that this part of you belongs to someone else.”

  Not a question. She didn’t have to say she was that sort of girl, and of course she wasn’t. She wasn’t. No matter how much pillow time and how many fantasies about the time traveler, Cynthia would never be that sort of girl. She bucked against him, tried to get away, without even willing that resistance.

  But then she whimpered with arousal, again, because the writhing movement made him take firmer hold of her pussy, and that made her gush shamefully down there. She sobbed again in shame.

  “From now on, Cynthia,” Master Greg said, seeming to take no notice of how she had just disgraced herself, “if you masturbate without permission you will get the cane. It’s as simple as that. The pleasure locked in your sweet cunt belongs to your masters, and we do not wish you to think that you can borrow your cunt from us whenever you like.”

  “Oh, no… please,” she moaned.

  “You’re going to kneel before me and suck my cock now,” he said in a matter-of-fact voice that made the words anticipated but impossible to prepare for, even worse. “To thank me for spanking you, and to demonstrate that you are learning obedience.”

  She couldn’t—that she couldn’t do. She had touched David’s penis, but it had frightened her, and she had felt strangely glad to be frightened by the way it moved, how it had hardened under her touch just as they had told her in sex-ed but you how could you tell anyone how that felt? She had thought, she remembered now, that time she had touched David down there, that her mother would be glad Cynthia was afraid of her boyfriend’s penis, and that had somehow been both infuriating and comforting. She hadn’t done it again, and instead resolved that for the time being she would let him kiss her all he wanted, and touch her breasts, which actually felt nice—especially when he just did it, while he kissed her.

  Yes, in her fantasies, girls did that with their mouths, but how…

  Master Greg took his hand away from her bottom. He opened his legs. He moved Cynthia onto her knees. With her hands bound behind her she could do nothing, nothing, to stop it.

  Oh, no.

  His left hand twined in her hair, held her head in place. Not painfully, because she could tell somehow he knew exactly how to take enough of her hair in his hand so that it felt controlling without feeling sharp and distracting. With his right hand…

  She tried to turn her head away from the sight of him unbuckling his belt, unbuttoning his jeans, unzipping his fly, but he held her there firmly, six inches away from where he exposed himself to her. He didn’t ask, the way David had once asked, and been allowed, that one time.

  She closed her eyes.

  “Open your eyes, honey,” Master Greg said. “You need to get used to the sight of your master’s cock.”

  Chapter Nine

  Sarah had a view only of the back of Cynthia’s head, but she knew exactly what the girl’s face looked like. The nine in the upper right said that she had cooled off from the three quick recalibrations she had undergone only a few moments before, as of course she must with the pure limbic fear response holding her briefly in its grasp. As Sarah watched, the number went to eight, then seven.

  Cynthia would misattribute that bodily fight-or-flight sensation, though, in just a moment—the very moment she opened her eyes and saw an erect penis for the first time. Sarah had an excellent view of Greg’s skillful twisting of the girl’s dark brown hair in his left hand: he made a rope of it, a single rein with which to contain her movements so that he could bridle her; get his cock, her new bit, where he wanted it inside her inexperienced mouth. Sarah watched him give a small but precise and very significant twist with that hand, as with his right he brandished his hardness, to show it to arrogant advantage when his subtle hair-pulling accomplished its purpose.

  A whimper demonstrated that the tightening of his hand in Cynthia’s hair had done the job: she had opened her eyes, and the conflict of her arousal had taken firm control of her responses again. Eight. Nine. Greg held her head patiently, waiting for the right moment: Sarah didn’t know the Institute protocols backward and forward the way she knew the Guard’s, but she felt certain Greg would wait until he had Cynthia back at ten before he issued his next command.

  The Ostia initiate’s attention flickered briefly over to the private chat between Charlotte and Herrier. Their messages had proceeded sporadically through Greg’s inspection of Cynthia and his threatening her with the cane if she didn’t take off her pants and panties. They had come faster as soon as the training master commanded the girl to lay herself over his knee.

  61423: How much?

  MissCharlotte: We’re setting the reserve at 3.

  Three million dollars, for a year of service. One million to go straight to Cynthia, deposited in an escrow account about which she would know nothing until she had served out the year in Herrier’s bed. Of course, if Operation Relegate went to plan, her exit would be more complicated than that of most Institute concubines, but the transfer of funds would remain the same.

  As an initiate of the Order of Ostia, Cynthia Hall would already be financially secure for life: the Guard took care of its submissive girls even better than they took care of themselves. Cynthia would if she wished live in the lap of luxury both as an operative and later as an emerita, whether she wanted to work a desk job in aid of civilization or simply to retire to a nation of her choosing. The extra million, though, would serve both as a symbol and as a nest egg, if she decided to st
art a family with the lucky master who won her heart.

  61423: I’ll open there.

  MissCharlotte: Lovely. Are you enjoying the stream?

  61423: Need you ask, Miss Charlotte?

  MissCharlotte: lol I suppose not.

  Then, a minute later, just as Greg put the well-spanked Cynthia on her knees:

  MissCharlotte: Jules, we have another bid at 3.1.

  It wasn’t true, but one of the characteristics of Institute practice most congenial to the Guard’s interests lay in the secrecy that shrouded the bidding process. In any legitimate auction situation, buyers would never stand for the manipulation, of course, but when sexual psychology and money intertwined with one another, techniques most bidders would consider outrageous came easily into play. Here, the object wasn’t to get more money out of Goshawk, but rather to increase his emotional investment—and the raising of his bids would serve at the same time to gauge how effective Relegate had been so far.

  Instantly:

  61432: 3.5.

  A very quick, very big raise: trying to intimidate the (nonexistent) competition.

  Emerald to Arno

  The pop-up opened in the lower left of Sarah’s screen. She typed.

  Arno here

  Well?

  I think we have him. Come back with 3.6, and then wait ten and say he’s got her, whatever his bid.

  On the other side of Sarah’s screen, Cynthia’s arousal went to ten.

  “This is my cock, honey,” Greg said gently. “You’re going to suck it now. Open your mouth.”

  MissCharlotte: 3.6 from your rival.

  61432: Let me check something.

  Herrier, no stranger to auctions, had clearly decided to ice the rival he thought might steal his hipster girl out from under his nose.

  MissCharlotte: You have ten minutes.

  Cynthia gave a gasping sob. “Please,” she whispered. “I’ve never… I…”

  “I know,” Greg said. “And it’s hard when your first time is like this, with your hands bound behind you…”

  The ten flashed.

  “…and your master holding your head this way, so that I can fuck your face just the way I want.”

  Another recalibration.

  Sarah wished she could see Cynthia’s face—she wished even more that Goshawk could see it. But she knew, too, that he could very well imagine it, and that picture in his mind’s eye would probably…

  61432: 4.

  MissCharlotte: I’ll get back to you in a moment.

  Charlotte icing Herrier, now: not to raise his bid but to make him nervous, increase Oriole’s value as he watched her with her trainer’s cock in her mouth, imagined himself training his new bed girl that way. Institute clients had described the experience of bidding as they watched a girl broken as porn heroin.

  Even in the very early days of the Institute, when the net hadn’t yet made real-time bidding possible on concubines undergoing breaking, the Institute’s first dean, Anne-Marie Ney, had laid the groundwork for what Goshawk now experienced: video of early recruits’ playing with themselves and/or having sex with their callow boyfriends had gone out on encrypted CDs via courier, with updates on the girls’ progress by fax, and bids faxed back. The feeling that a dominant man or woman could own the girl they saw had proven nearly irresistible to a great many wealthy individuals over the years.

  On the video feed, Greg had used his grip on Cynthia’s head to move her closer to his cock. Sarah could see both from the movement of the girl’s neck and from the arousal number that dipped to nine for just a moment how complicatedly welcome that pressure felt to Cynthia. Sitting in her office, in her own powerful master’s penthouse, Sarah swallowed hard, remembering only too well the way Robert had forced her face toward his erect penis, that first time: forced, but without violence… communicated to her the necessity of learning the shameful lesson he had to give, in pleasing a man the way her body cried out to do.

  Sarah had to shift in her ergonomic leather chair, knew she would leave a wet mark there for Robert to find if he came upstairs anytime soon, for as usual when working Sarah had to be naked, her neck and wrists adorned with the leather bands of her initiate’s status. She wasn’t allowed to touch herself any more than Cynthia was.

  Without hope and only wanting to feel him a little nearer, she messaged her husband.

  SBo6: Permission to play with your wet little cunt, sir?

  RBg7: Ha. No, sweetheart. I’ll be up in half an hour. Do you want to do what Oriole is doing?

  SBo6: Oh, so much, sir.

  RBg7: Do you think you can suck my cock well enough to earn a reward of your own?

  Sarah felt a smile spread from ear to ear.

  SBo6: I’ll try, sir.

  He’d say it, wouldn’t he? Say it, type it, kiss it into her forehead, her nipples, his own warm pussy that she kept for him and those to whom he gave her. Sarah lived for the words she knew would come next.

  RBg7: Good girl.

  Sarah’s heart felt like a balloon filled with helium as she turned back to Oriole’s feed.

  She could just see the way Greg moved his cock with his right hand, now, though not the cock itself. Her craving to see that enormous penis—for all Institute trainers possessed that essential qualification—made her face go hot, and stirred a momentary fantasy she had rather often, that Robert, a little dissatisfied with her progress as his bed girl wife, might send her to the Institute someday.

  Not seeing it, though, didn’t keep her from understanding from the body language of both Greg and Cynthia that he had started to rub the head over her face, very deliberately, letting the degradation of this kind of fellatio sink in very deeply before he went further.

  Cynthia’s ten flashed again.

  “Open up, honey,” Greg said. “Let the cock in. Let me have my way.”

  That did it, of course: Sarah saw the girl’s brunette head bow a little further, heard the lovely wet sound of an erect penis being sheathed deeply in a submissive mouth. Cynthia gave a little cry of alarm as Greg sought the recesses of her mouth, but he knew her limits, and moved her head only a little, though in a definite rhythm, to get her used to having her face fucked before he began truly to use her for his pleasure.

  “Shh. That’s it, good girl. I know it’s big, but you can take it. Oh, there we go. There we go. That’s nice. Just like that, nice and open so my cock can enjoy being in you.”

  61432: Well?

  MissCharlotte: She’s yours. Congratulations.

  “I’m going to hold your head still and thrust in now, Cynthia. It will scare you a little, but I’ll come in a few moments, and it will be all over then, and you’ll have a tummy full of semen.”

  A desperate noise from Cynthia, then, so arousing Sarah felt herself gush onto the leather of the chair, felt her own level three contraction. Lucky girl, she couldn’t help thinking despite knowing just how deep the conflict inside Cynthia’s heart and body were right then.

  “Oh, so good. Oh, such a good girl.”

  Cynthia almost gagging, saved by Greg’s skill, his rapid motion as he hammered deeper and deeper, certainly now touching the back of her throat, the way that always seemed to make Robert come like a freight train.

  Greg grunted in satisfaction, held himself only a little ways into Cynthia’s mouth, only between her lips, really, stroking himself as his hips jerked out his climax. Little sobs from Cynthia marked the unfamiliarity of the taste, of swallowing something so viscous.

  “That’s it, honey. Swallow it up. I’ll hold myself inside you until you’re done.”

  61432: Thank you. Down payment sent. I’ll specify training protocols later today. I’ll want her intact until she arrives in France.

  An unusual request, but one that the Guard had in fact counted upon: Jules Herrier’s famous reclusiveness would keep him from coming to the Institute to sample Cynthia, or even to carry out her anal defloration in the traditional style of the ass night—really for Jules, if he were to en
gage in it, to be known by Anne-Marie’s French term, nuit a derriere.

  MissCharlotte: Of course. Will you want a trainer in situ?

  The other crucial part of the Guard’s plan: with any luck, Goshawk himself would make the suggestion that would prove his undoing.

  61432: Bien sur. Is this Master Greg available?

  Yes. Into the trap.

  MissCharlotte: Let me check his schedule.

  A pause, during which Sarah opened yet another chat window.

  Arno to Garnet

  Jessica Logan typed back immediately,

  Garnet here

  Have assessors inform Black Bear transfer to breaking facility to be made ASAP.

  Sarah thought she saw Greg’s eyes twinkle a little as Heather gave him the news over the comm link that Sarah herself couldn’t access herself, in order to keep its security as tight as possible.

  Jessica sent:

  Done. Jupiter all ok?

  Jupiter was Robert’s codename.

  Indeed, Sarah typed back, thinking of what would happen when Jupiter came through his penthouse door. All ok.

  Chapter Ten

  Cynthia awoke to the strangest sensation she could ever remember having felt: strange, and very wicked, in the way her naughtiest dreams could seem sometimes—shameful, but in a way that felt liberating, because at last, in the dream, she seemed able to tell people that she needed terrible things done to her.

  Like having her legs held open on a medical exam chair, knees held fast in stirrups and arms belted to her sides, with a strap also around her shoulders just above her breasts, and another around her neck.