Trained by the Trillionaire Read online

  Master Greg sighed. Cynthia couldn’t help looking into his face, though she dropped her eyes again immediately. He had seen the glance, though, and he didn’t delay anymore: he stepped forward again, took hold of her left shoulder, spun her around, and bent her over.

  Now Cynthia could do it, she found, as if his manhandling had activated her muscles. She kicked the sweatpants away frantically. She danced lewdly to make the panties fall off her knees, then kicked them away, too, imagining all the while that he stood next to her, over her, with the horrible black cane raised high.

  But if he had it raised, it never fell. Instead, he spoke, and she heard a smile in his voice.

  “Good girl.”

  Chapter Seven

  The magic words had the same effect on Cynthia that they had on a huge percentage of submissive young women. She gave a little whine, and she lowered her head, which she had raised and twisted desperately from side to side as she at last found the presence of mind to get out of her panties.

  She had wanted to see the cane coming, of course—though another part of her had most certainly not wanted to see that terrible sight. Now that she knew she would not feel its special searing sort of education across her sweet little bottom just yet, her mixed emotions would be turning her inward, processing Greg’s words and actions, and her body’s and heart’s reactions to them.

  A moment before, when he had turned her around and prepared her for a thrashing of a kind she had almost certainly never imagined, Heather had said, “Recalibrator.” That had meant that the number ten in the upper right of Cynthia’s video feed had flashed: she had just experienced more sexual arousal than the assessor team had yet observed from her.

  Recalibration happened frequently during a pickup of course, since a repressed submissive almost by definition has never allowed herself to feel the full potential of the combination of sexual stimulation and fantasy of which she’s capable. Even a frequent masturbator like Cynthia used her sessions of self-pleasure as a kind of escape valve, letting her relatively mild fantasies, like the ones she must have had about the sci-fi show she had watched before bed, keep her need off the boil, as the trainers sometimes called it.

  The threat of the cane, however, had raised the heat in a way Cynthia Hall had never experienced, and her body had responded beautifully—at least from Greg’s perspective. It would be more difficult to see it as a pleasing development from the girl’s viewpoint, however, he knew.

  Now Heather said, “Holding at ten with a downward bias. She clenched at good girl, level three.”

  I noticed, Greg thought, with a smile: he had parted Cynthia’s knees just enough when he spun her around that he could get a view of her contracting pussy-lips through the crisp black thatch of the pubic curls he would remove once he got her to the breaking facility, a few hours from now. Those glistening coral folds looked so paradoxically demure, despite saucily emerging from the modesty of Cynthia’s outer labia that it made Greg’s cock jump in his pants. The familiar alpha need to have his cock sucked by the girl he was breaking grew in urgency: easily controllable for an experienced trainer like Greg Sampson, and always a welcome addition to his engagement in his work.

  The contraction of Cynthia’s vagina had produced her whine, and the strength of it—level three, the upper end of the scale on which Institute assessors measured such arousal spasms—had, Greg felt sure, made her hips give another of the marvelous riding movements so characteristic of pillow humpers like her. She had trained herself through her special kind of masturbation to ride any stimulation down there, even when the stimulation came from her own body’s inner workings, like a pussy clench. Greg had no doubt her owner would enjoy both making her ride his cock and holding her still to train her simply to take the fucking he was pleased to give her.

  “Nine. Eight.”

  He had expected, and in fact awaited, this dip. Everything she had experienced in the last few minutes, above all the way she had responded to the threat of the cane, had surged into her mind. Greg needed to give her time to think, and he needed to help her order those thoughts in the proper direction both for her training and well-being as a submissive and for Operation Relegate.

  The moment was crucial. If Greg screwed it up he could set the operation back—ruin it, even. He needed to build the buffer that would keep her from rejecting her breaking not in the sense of rebellion against the cravings characteristic of most repressed submissives but in the sense of repudiating her body’s needs entirely. If the Institute assessors saw Cynthia doing that, they would abort the pickup in the interest of keeping her from psychological harm.

  If Greg handled Cynthia correctly now, he would have further moments, here in her apartment, with the memory of this one as a sort of cushion, a strange and almost perverse sort of trust between the girl and the man who had invaded her home to begin her sexual training. Should he for example, two hours from now, fail to enforce his will consistently, Cynthia would return to the words and actions Greg had provided in the wake of the threatened flogging, both in her conscious recall and in her body’s very special sort of subconscious memory. If her arousal dipped then, this earlier treatment would come to her mind and her pussy, and keep her from the kind of rejection that posed a constant threat to a girl’s early training.

  Greg wouldn’t have that buffer, though, if he failed now to speak to Cynthia, and to touch her, in a way that began at least to resolve her conflict, or at least to bring it to heel. She would have the ambivalence with her for a good long time. Most concubines reported that it never truly went away—nor did they want it to, because it represented a never-ending source of arousal. Feeling naughty, lewd, wanton, wicked… feeling in need of the discipline they craved—that depended on the very conflict that once, when their training masters broke them, had felt like it would tear them apart.

  “Good girl,” he said again, this time even more softly, but bending over so that he could say it into the lovely curve of her ear, as with his right hand, still holding the acrylic cane, he gathered the hair that had fallen around her face. She shivered at the touch of the disciplinary instrument as Greg moved the hair across her back, smoothed it over her right shoulder so that he could see her high cheekbones, her long-lashed left eye. He watched her chin twitch as Cynthia almost turned to look at him and then remembered she must not.

  “Eight,” Heather told him. “Looks steady.”

  “Cynthia,” he said, still bending so that his lips nearly touched her ear. “I’m going to put down the cane, now. Then I’m going to sit on your bed, and you’re going to lay yourself over my knee. It’s time for your spanking.”

  “Nine.” Heather spoke even before the whimper came from Cynthia’s mouth.

  Moving very deliberately, Greg straightened up, taking his time to survey the naked, bending girl with the ruins of her t-shirt messily atop the neat binding of her wrists he had effected. Her knees bent and slightly parted, her sweet, pert bottom well presented: she had already begun to absorb that lesson, unconsciously, because of the arousal it brought when she felt his eyes evaluating her submission, her fuckability.

  Very nice. He dropped the cane onto the bed, atop the naughty pillow, and saw her move her chin slightly as her eyes went to it. The emphasis he placed on the instrument of her self-pleasure that way would sharpen the conflict as it reminded Cynthia of the reason announced for her punishment: the crime of stealing her cunt’s delight from the master to whom she had belonged even before she knew she would become a wealthy man’s bed girl.

  Greg moved slowly from Cynthia’s left side to stand directly behind her, his eyes on the lovely, tender inverted vee of her thighs and the very special place at its apex.

  “You’re very beautiful, honey,” he said in a warm voice. “Your owner will be a lucky man, to get to claim you completely. I might not be quite as lucky to get your first blowjob, in a little while, but I’m still going to enjoy myself a great deal.”

  Another whimper came from her bent
head, a tiny one.

  “Ten,” Heather said. “Level one clench.”

  “First, though,” Greg continued in the same warm voice even as his words began to contrast with it, “we have to help you learn a very important lesson.”

  Cynthia bounced her knees at that, a little, though she clearly managed to keep her hips from disgracing her yet again.

  “Level two clench,” Greg heard in his ear.

  He took another step, to Cynthia’s right side, closer to the foot of the bed. Her gray panties lay at his feet; he stooped to pick them up with his left hand. The he turned and sat on the edge of the bed, six inches from Cynthia’s pale, trim thigh. Then he waited, with his thighs spread so that he could get her over the left one, with her torso just at the end of bed and her face hanging a little over.

  Silence fell in the loft, except for Cynthia’s harsh breathing and very occasional late-night street noises. A distant bar had just closed, it seemed, and cheerful drunken yells could be heard as if from out of a haze of urban renewal.

  “Eight. Seven. Six,” Heather said, the numbers coming in rapid succession. Greg let the silence linger, knowing what the dropping arousal meant for Cynthia’s emotional state and her thought processes. A new dimension of the conflict had begun to occur to her, and he had to wait until he could manipulate that realization to his advantage.

  “Five,” Heather said. Cynthia’s breathing had quieted a bit, now. Greg’s most important moment had come. He spoke in an even tone, letting the authority build as he delivered the little speech that would start the girl on the proper path.

  “Honey, this is going to be a lot easier for you if you start to obey me without having to be threatened. I want you to do as I said and lay yourself down over my knee.”

  “Six,” Heather said.

  Greg continued, “You know you have a spanking coming. You’ve known it since you started to play with yourself, on your eighteenth birthday. Girls who play that way—girls like you, anyway—understand that sooner or later they’re going to have to learn the lesson they’re asking for. Your time has come.”

  “Clench level three. Seven.”

  Cynthia whimpered and with her head still hung low she moved the small distance necessary to find her way between Greg’s legs. Once she got there, he helped her bend so that her bound wrists wouldn’t make it too awkward. Having arrived there, she wriggled at the unaccustomed though long-imagined feeling, until Greg quietened her motions with his left hand on the small of her back.

  “There. Good girl.”

  “Eight.”

  “Further over, now. Your bottom higher. Spread your knees.”

  “Nine.”

  Each command brought a new whimper from Cynthia now, as she struggled to obey. With his words Greg had effectively countered a prospect he must not speak, and Cynthia could not acknowledge. The cooling of her arousal a few moments before had presented to her the possibility that her training master might not spank her. As terrible as her mind told her it would be to go over a man’s knee and be punished for playing with her pussy, her body’s unquenchable need to submit to a man’s pleasure and discipline could not but win out, when a trainer like Greg knew the words to release her from feeling she had chosen to obey him.

  At that moment Greg had in truth broken her, because she would obey him now without an immediate threat of punishment, secure in the knowledge that she would nevertheless pay the price—an idea that paradoxically freed her to submit to him and, soon, to her owner. Cynthia Hall now wore the Institute’s famous chain of the heart.

  Greg put his right hand on her pert little bottom, perfectly upended over his thigh. He squeezed right in the center of it, low down, so that he could rub firmly at her pussy with his two middle fingers, right in the spot where Jules Herrier’s cock would enter her, provided the sale proceeded as it should. Cynthia gave a little cry as he found out her wantonness yet again.

  “Now, honey,” Greg said softly, “we’re going to talk about this sweet, wet cunt, and how naughty you’ve been here in this innocent-looking little bed of yours.”

  Chapter Eight

  Cynthia felt her brow crease so deeply she thought it might leave a permanent mark.

  If only I were still gagged, she thought, and he had to do all the talking.

  Then, immediately, she felt she must be losing her mind. She had suspected she had gone crazy a few moments before, when she had decided she had no choice but to obey Master Greg’s command to lay herself over his knee: this newest thought confirmed it.

  The idea only got stronger when Cynthia realized some part of her found it comforting: if she had lost her wits, she truly had no other option but to do as this man said, since she couldn’t trust herself to make rational decisions.

  He’ll give me the cane if I’m not a good girl. I have to obey him.

  I wish I were gagged, so I didn’t have to say anything.

  Maybe Master Greg would still just lecture her, and he wouldn’t…

  His left hand had moved her long, straight hair over her other shoulder, so that if Cynthia craned her neck she could look at him, above her and in complete control of her body. As if to emphasize the control, she felt him move his right thigh to entrap her just above her knees, so Cynthia wouldn’t even be able to kick. She heard a little sob come from her throat.

  Why didn’t he start talking… about the thing he said he would talk about?

  His left hand moved again, and now he held it in front of her face, and she realized to her horror that he had her panties in that hand, and he was holding them a few inches from her eyes so that she could see them.

  Oh, no. Please.

  “Cynthia, honey, what are these?”

  No.

  His terrible right hand stopped the awful squeezing, then left her bottom.

  Oh, no.

  She felt a puff of air, and then she heard the sharp sound and then, a fraction of a second later, she felt it, and she yelped, but she had no time really even to think I’m being spanked. A man is spanking me, because Master Greg had already given her another tremendous swat, so that now the pain got very bad, and she was trying to get away but without the slightest hope because of his right leg across both of hers.

  She twisted her torso as she shrieked out the stinging, shocking pain of the second hard spank, trying somehow to get her bottom out of the way of the third one she knew must be coming. Master Greg… oh, how can he?… put the panties in his left hand against her face, her nose and her mouth, though Cynthia tried to turn away. He controlled her thus, easily, and he did give her a third, terribly hard spank, so that Cynthia screamed into her dirty panties, the panties she had dirtied herself because she had been so naughty in the night—even before she had pulled her panties down, she had made them lewdly fragrant, so that now she had to breathe in her own musky aroma, the way she did when she felt extra wicked and sniffed her pillow just a little, in the morning.

  Never because someone made her, though. Never because a man had decided to rub her nose in her illicit pleasure. Never because she had to learn her lesson.

  “What are these, Cynthia?” he asked again. His voice sounded so much calmer than his huge spanking hand seemed to say her training master actually felt. The contrast startled her, widened her eyes, as the pain from his discipline coursed through her body. It kept her from responding, though she had almost decided that saying the terrible things he decided she should say lay in the realm of things about which she had no choice.

  Her bottom clenched, surged, trying to ease the smart before the next swat came, because she knew that it would come, because she hadn’t answered yet.

  It did. She screamed into her panties, bucked against his hand and his legs, felt her bottom on fire as he followed it with another tremendous spank, all in the same place, right in the middle, right where she sat, on the metal chair at the café on the corner, when she had coffee with Addie.

  I won’t be able to sit there for a long time, Cynthia thoug
ht, and felt her body respond to the thought with a warmth down below her tummy that made her breathe in another scent of her naughtiness even as it renewed her conviction that she had gone crazy.

  No, Cynthia Hall wouldn’t sit in a Williamsburg café again for a very long time, if at all. All the irony of her life, the disaffection she had shared with Addie and their other friends, the nostalgia for a time when you could feel things… well, David, definitely not a hipster himself, had enjoyed laughing at it, hadn’t he? Not to ridicule her, or even her most hipster-ish, always stoned friends—just because he thought it made sense at least to live like things mattered.

  And Cynthia had tried to tell him that of course things mattered to her, and to those who—ironically—accepted the stupid hipster moniker. Some of the biggest stoners also created amazing things with their hands and their brains—things that might change the world, if they could scale.

  But always she had known that a part of her she kept hidden from all her friends and especially from David simply couldn’t ever be lived, and this irony, specific to Cynthia Hall, made her feel that she at least couldn’t ever really find a life that mattered, because it wouldn’t matter to her.

  “What are these, Cynthia?” Master Greg asked.

  “My panties!” she cried out into them, into their naughtiness, their un-ironic disclosure of her wanton self-pleasure.

  She knew, despite everything her mother had said, that masturbation was healthy. She had read a great deal about it, having fears that came on the one hand from her conservative upbringing and on the other from the nature of her fantasies, the way they seemed different from most other people’s, the way they seemed to paint a world of dark masculine powers and yielding feminine submission.