Trained by the Trillionaire

by Emily Tilton

  Greg delivered this more or less classic formulation of the life into which a new bed girl has been taken and the nature of her training in the authoritative but understanding tone of a classroom teacher. He saw in Cynthia’s eyes that the message had hit the target: what her training master had just said was something he expected her to find strange and new, but that unfamiliarity didn’t carry with it any excuse for her refusing to do as he instructed.

  Her lips had parted again, but Greg knew that Cynthia wouldn’t be able to find anything to say: her mind had just become much too full of mingled fantasy and emotion, and above all of the conflict for which he had thoroughly laid the groundwork before shocking it awake with words like belong, wealthy, and deflower… let alone spanking, knee, and property.

  “Ten,” Heather said over the comm link. Greg watched in satisfaction as Cynthia’s hips moved, involuntarily against the pillow between her thighs, jerking desperately to soothe the need he had awakened down there. Even more satisfyingly, her face then turned bright red as she realized what he had seen her do, with all its implications, all its interweaving with the terrible things she had just heard him say.

  A tiny whimper came from her throat, and her forehead creased very deeply. She shut her eyes tightly, as if to exclude his presence and above all his probing gaze from her universe.

  “Naughty girl,” Greg said, though, and that made her eyes fly open, let her give verbal shape to her conflict, though the words came out in inchoate, barely comprehensible monosyllables.

  “I’m… please…”

  “You want me to go away, Cynthia,” Greg said in the same didactic tone. “I know that. You don’t want to face the reality that you will soon be a wealthy man’s sexual plaything. But I also know a good deal more about you than you think. I know how very much you need a spanking, for a start. Now get out of bed and finish taking off your clothes. I’m going to inspect you before I spank you.”

  The noise Cynthia made fell somewhere between a whimper and a cry. Her hips bucked again, and the blood that had started to drain from her face came rushing back. She had probably thought she had felt the conflict of her submissive sexuality as strongly as she could possibly feel it, on Saturday night with her boyfriend, when the data stream had shown the Institute’s assessors just how good a candidate she was for pickup. Greg had just demonstrated to her that she could feel it much more exquisitely than that, when an experienced training master stood over her.

  Just wait until I touch you for the first time between those trim thighs, Cynthia, Greg thought. You’ll start to understand then how difficult it’s going to be to admit that you crave mastering, and yet how very much you need it nonetheless.

  Chapter Four

  The rational part of her mind kept suggesting that Cynthia was just having a very, very vivid dream. That corresponded at least a little to previous experience: occasionally when she drifted off with her pillow still between her legs, she would have a dream that reflected the unassuaged sexual tension. When that happened, though, she would generally wake up around three a.m. to find herself already riding pleasantly to one of the tiny orgasms that would let her fall asleep again until the alarm went off at seven. The dream itself would be a follow-up from whatever she had been watching or reading before she went to sleep, generally something that took place far, far away from Brooklyn.

  In this case, she should have been getting a spanking or even an English-school-style caning from the time traveler in the recesses of his time machine. He would have flogged her thoroughly, and then put his hand between her legs to see just how naughty she could be, and how in need not only of correction but also of firm guidance of a different kind. He would have inspected her thoroughly before he took out his hard cock and made her ride it until she screamed that she needed to come so much, could she please come, please, please, please…

  Then she would have woken up, to find that she had almost got there, and only a few more movements of her hips, a few more complicated, half-rough, half-smooth glides over her soaking pillowcase, her labia parting just enough, her clit pushing just enough, would do it. Would do so very nicely, even though she never had a really big one like that, but only just enough to send her back to a dreamless sleep for a few hours.

  But this dream was happening in her apartment, and it involved elements Cynthia didn’t think she had ever thought of before, despite also possessing certain essential themes that ran through all the terrible fantasies she saved up for what she called, to herself, pillow time. She didn’t, the rational part of her mind said, remember ever having imagined being sold into sexual service. At least not when she rode her pillow at night, or even in the morning when her fantasies tended to reach for stranger scenes that made her face go hot when she thought of them later: whips and chains and rooms full of strangers who planned to have her everywhere a man’s hard penis could go.

  And in a dream, would the man have said that he knew more about her than she thought she did? That sounded like the sort of metacognition that dreams couldn’t achieve, didn’t it?

  Oh, God. Why am I thinking about metacognition when this big, frowning stranger has just told me to take my clothes off so he can inspect me and spank me? Has just said that I’ve been sold to a wealthy man?

  “This is your last chance, honey,” the man said, that same strange note of compassion sounding in his voice that she had heard before, when he had said that he knew she wanted him to go away. “Take the pillow away, so I can see your little virgin cunt, for starters.”

  Cynthia gasped at the terrible word, at the shameful adjectives he had used with it. They never said that in her dreams, or even in her fantasies. They said pussy, or sometimes snatch. The men who put her on the table would often ask one another if they were enjoying Cynthia’s snatch, as they fucked her so very hard.

  She looked up at him, breathing so hard through her open mouth that she began to feel faint, even began to wish she would faint, to make the awful turmoil, the horrible rending inside her just stop.

  He reached his right hand out.

  Oh, God, he’s going to grab me, isn’t he? He’s going to take hold of me, drag me out of bed, bend me over the bed, rip my clothes off for me, take me…

  Cynthia gave a little cry and shrank back toward the wall, but the man’s hand didn’t take hold of her, but rather of her pillow, and for a moment, despite it seeming even then completely irrational, that seemed much worse to her. For just as she had seen his hand reach out, had taken in the vision of his big, lean body in black t-shirt and jeans, tall, dark, and handsome, leaning down to restrain her and to force her to obey, she had gushed, down there.

  Even more mortifying, as he pulled the pillow free from her closed thighs, opening them so that Cynthia knew he could at least for a moment see all of her, down there, the view even your husband should never have, the friction caused another stab of heat, another flow. If he looked at the pillowcase, if he inspected it, she would die… it didn’t matter that all the other things he had threatened seemed from a reasonable perspective so much worse. Pillow time was the thing no one must ever, ever know about.

  She had gotten her back all the way to the wall, and she had her hands, which had clutched at the pillow in vain as the man took it away, in front of the place where he wouldn’t now be able to see anything but the dark brown pubic hair she refused to shave or even to trim no matter what Addie said. Cynthia took a little solace from having her big red t-shirt still there, and she used her left hand to try to pull it down, so the man wouldn’t see anything at all except a little thigh.

  He smiled, as he took the pillow in both hands, and she could see in the smile that he knew, somehow, exactly what was going on inside her. He knew that part of her, the terrible part of her, wanted him to look down at the pillowcase. How could she be so frightened and so… that… at the same time?

  He looked down, brought the pillow closer to his eyes.

  “Oh, no,” Cynthia whispered. “Please, no.”
>
  “I don’t really even need to inspect your naughty cunt, do I, Cynthia?” he asked, glancing up from the white fabric where Cynthia could see even from the bed that a dark spot betrayed her wantonness to his eyes. “I have enough evidence right here that you’re a girl in need of firm guidance and thorough correction.”

  Her pussy clenched between her thighs, and her arousal flowed again. How could he say those things, just say them? Those things that she knew David would never say, because no one could say them in real life, so really she should just get over it and take Addie’s advice and go to Vermont and get herself fucked by a man she loved, who loved her? It wouldn’t be what she saw in her fantasies, but that was a good thing. Your husband should love you and respect you, and never raise his hand to you—especially when you were better educated than he, and knew a great deal of feminist theory.

  Your husband should never give you firm guidance, let alone thorough correction. He should never even give you guidance at all, for God’s sake.

  The man brought the pillow even closer to his face.

  “Oh, no,” she whispered again, more urgently. “Please… I… please, don’t…”

  She knew exactly what he meant to do. She knew it because this did make an important part of her fantasies, because she herself, when she had restored the pillow to its proper place at the head of the bed, did it.

  He took a long sniff.

  Cynthia whimpered, and her pussy clenched again. The hands that clung to the hem of her t-shirt now wanted to move, wanted to help make it better, wanted to give her something to ride, the way she sometimes did when she felt a big climax coming and she wanted to make it even better: she would pull the pillow from between her thighs and put her wicked hands there, one in front and one behind. She would even put a finger in the worst place of all, and sometimes she would even whisper, playing the part of the man in the mask in the room with the table, I’ll have her here now.

  She would put the pillow right in front of her and the man in the mask would make her smell her snatch, and ask her if she liked it, would she like to taste another girl, while he fucked her little bottom-hole.

  Oh, no. Please.

  “You have a lovely fragrance, Cynthia, but I think you already know that.” He lowered the pillow and looked her right in her wide eyes, his dark pupils seeming to glitter with a menace that made her heart jump. “Before we leave here tomorrow, I’ll make a video of you riding your pillow. The Institute will use it to attract bidders for your virginity.”

  Another whimper broke from her throat. It couldn’t be true; it just couldn’t. The wild thought arose in her mind that if she had fucked David… even if she had just said yes to Vermont… this wouldn’t be happening, because they wouldn’t be able to see her virginity, would they?

  But that didn’t make sense, because she had decided she wouldn’t have sex with David, because for that one moment he had looked like he might… like he might guide her firmly to let him have his way with her. Like he might thoroughly discipline her, for taking his hand from between her thighs, where only her pillow had gone.

  She had very nearly decided she would break up with him for that look.

  That look she saw in this man’s eyes as he loomed over her, as he dropped the shameful pillow at the foot of the bed. The look that made her brow crease with the terrible conflict among her barely rational head, mystified heart, and wayward pussy.

  The look that said that Cynthia Hall had run out of last chances, and would now learn what it meant to keep a man waiting for the pleasures to be found in her nineteen-year-old body.

  “My name is Master Greg, Cynthia. From now on, you will call me that, and you will acknowledge each of my commands by saying Yes, Master, and then obeying me, or you will be punished. Now, take your sweats and your panties all the way off, and get out of bed, please.”

  Her lips opened. She looked up at him. She knew she wouldn’t, couldn’t say it, let alone do it, as simple as both the words and the action were. Yes, wriggling the rest of the way out of her sweatpants and her underwear would be terribly undignified, and he would probably see more of her than she wanted him to, no matter what contortions she employed, but…

  What the hell? Why am I even thinking about trying to keep myself covered, when he’s made it so very clear…

  She watched wide-eyed as Master Greg bent to get something on the floor, something she couldn’t see because it lay too close to the bed. She heard rustling—he must have a bag down there? A bag full of… Oh, God. Things. Those things.

  He straightened. He had a length of rope in his right hand. White nylon, a quarter inch thick: the kind you used on a little sailboat, to raise the mast. Halyard, her mind thought dully. You used that kind of rope for the halyard.

  He reached out then, again, with both hands, and now she knew there was no pillow between her legs anymore, for him to touch instead of her. He would ask again, though, wouldn’t he? He would give her one more chance.

  Master Greg didn’t give her any more chances. Still looking into her eyes, he took hold of Cynthia’s upper arm, her left, and pulled her toward him, using the right, in which he held the rope, to grab behind and under her t-shirt-covered torso and flip her onto her tummy.

  Cynthia cried out, but with a speed that astonished her, since Master Greg had seemed to be doing everything so very deliberately up until that moment, she found he had tied her hands behind her and had the dishtowel over her nose, so that she had to open her mouth to breathe because of all the struggling she was doing in vain, and he could gag her again.

  “Naughty,” he said. “Very naughty.”

  Oh, no.

  Chapter Five

  RBg7: What are you hearing from Garnet?

  SBo6: Emerald says it’s all nominal so far.

  RBg7: When will they start shopping her to Goshawk?

  SBo6: Emerald already has an email out to him.

  Emerald was Charlotte Elkins Nakama, academic dean of the Institute, who handled the private sale of concubines, whether the girl were, as often these days under the corporate laws, sold before she had even had her data stream analyzed for submissive tendencies, or like Cynthia Hall she were picked up on spec with the intention of selling her as soon as a suitable buyer could be found.

  The twist in Oriole’s case lay in the involvement of the Guard, through their liaison Jessica Logan—codename Garnet. Jessica, herself trained at the Institute and married to the Guard’s head lobbyist Kevin Logan (codename Mustang), had worked closely with Sarah for three years now on the cases of girls like Cynthia Hall.

  Cynthia might well have received the Institute’s attention in the ordinary course of their acquisition of bed girls, as her frustration grew and her online habits betrayed her repressed submission. Neither Sarah Bennett nor Jessica Logan would have been involved with her pickup, but the girl who had become Oriole to them would have been taken to the Institute and trained to serve a master’s cock or a mistress’ pussy, or both, and had at least a year of service that would have brought her great pleasure and great knowledge, and made her wealthy at the end of it.

  Occasionally a concubine at some point in her training or service came into contact with sensitive information or clandestine dealings, simply through her exposure to the rarified world of wealth and power to which the men and women capable of purchasing bed girls belonged. Charlotte would bring in Jessica—or Jessica, since with Kevin’s help she watched the Institute feeds for anything in which the Guard might take an interest, might make contact with Sarah, and Sarah might tell her to get in touch with Charlotte. Whatever operation resulted would be run from inside the Institute, with Sarah consulted along the way.

  Sometimes, however, the Guard involved itself from the very beginning of the Institute’s pickup and training process. Then, the circumstances changed—especially when, as in this case, the pickup itself represented the linchpin of a covert operation, and the entire mission in which the girl would find herself embroiled compr
ised a sort of honeypot on steroids: a supercharged update to the old-fashioned idea of a lovely young woman gathering a powerful man’s secrets with the help of the intimacy that eventually lowered the guard of every human possessed of a Y-chromosome, and many not so possessed.

  Cynthia Hall, Oriole, would certainly make a very fine honeypot in any century. But with the assistance of the Institute’s data-driven training and the corporate laws that allowed for Cynthia’s involuntary pickup, transfer, and breaking to the life of a submissive concubine and the pleasure of a billionaire of the Guard’s choosing, she would represent the ultimate operational tool in the Guard’s toolbox.

  If they could train her properly, and sell her on to Jules Herrier without him suspecting that he had acquired a lovely mole: a girl who would, even as he bared her bottom for a sound whipping on some pretext of being late to dinner or failing to obey the housekeeper, be gathering intelligence with the intent of loosening his grip on commercial applications of nuclear fusion.

  Sarah kept one eye on the feed from the cameras in Cynthia’s apartment as she attended to the textual comms that flowed down the right side of her screen. Cynthia now lay on her tummy on the bed with the gag in her mouth and her wrists bound behind her. Greg Sampson, codename Black Bear, stood over her, taking his time now that he had the girl in the beginnings of bondage, allowing her arousal, and her ambivalence about it, to build.

  Most of Sarah’s attention, however, focused on the chat Herrier had just opened with Charlotte, in response to the email she had sent only three minutes before, with a picture of Cynthia’s face, a nude of her in the shower, and a five-second clip of her humping her pillow.

  Hi Jules! Any interest? I know you mentioned last month in Davos that you were looking for a hipster girl to educate in proper behavior. This one’s actually in Brooklyn! She needs a good deal of discipline, don’t you think?