Trained by the Trillionaire

by Emily Tilton

  Like having something warm spread down between her legs.

  Like hearing a man say, “This is going to hurt a little, honey, now that you’re waking up.”

  Pressure: light fingers, down there. That didn’t hurt. The warmth cooling a bit.

  Who was he? Where was she? Her eyelids still didn’t seem to want to open.

  Then pain, sharp but just for a moment—also, though, down there where a well-brought-up girl like Cynthia Hall should not be spread open with a man—Master Greg, she remembered suddenly—doing something. Doing anything at all, really, but most important nothing that felt like that, and made that strange ripping sound as he…

  She understood, and her eyes opened at last to see him there on a stool between her widespread thighs, gaze fixed on her pussy and her anus. She saw the little pot of warm wax, the cloth strips. Addie had told her about how it worked, had told her she should do it for David.

  “I mean, the feminists say it’s infantilizing, but it’s so fucking hot, Cynthia.”

  She had cleared her throat, then, and told Addie she couldn’t ever get even the lowest level of bikini wax, let alone the filthy suggestion her friend had just made. Down below, she had caught fire, unable to get the image out of her head, of David looking at her bare pussy, telling her how pretty she looked, how tight she would clearly be for him, when he fucked her.

  But of course she couldn’t, for how could she possibly go into an establishment that carried out such shameful procedures? Maybe she could tell herself as she entered that she wanted her eyebrows waxed—which hurt badly enough, for goodness’ sake—but then she would have to tell the receptionist what she had really come for, and there would be other people in the waiting room who would know that her boyfriend had sent her to the aesthetician to make her cunt more pleasing.

  Or, no, of course not—he wouldn’t have sent her, but it would feel that way? Cynthia hadn’t understood her strange reaction to Addie’s suggestion, and she hadn’t wanted to: she had changed the subject and ignored the dampness in her panties. Later, riding her pillow that night, she had remembered, and wondered what it would feel like and what it would look like in the mirror, and perhaps she had imagined a man in a mask inspecting her down there after her wax, telling her he would have to punish her unless she kept herself smooth for him. She couldn’t really remember now, could she?

  How could she remember when the man between her legs didn’t wear a mask at all, but was the same man who had invaded her home, had bound her, had spanked her?

  Had told her, just before he made her take the powerful sedative, that a wealthy man had purchased her.

  He ripped another strip away, and she gave a cry that she couldn’t seem to attribute: the pain, or the sight of Master Greg down there between her forcibly spread knees, or the memory of him telling her that she belonged to a billionaire and would soon be his sexual plaything. For a moment, without willing it, she writhed against the webbing straps that bound her to the exam chair. She could move no part of her body more than an inch, and that realization made her cry out again, even more pathetically.

  Master Greg lifted his head, with a smile that seemed meant somehow both to reassure her and to make clear that she had no more choice in this procedure than she had in any other aspect of what he had done, was doing, and would do.

  “Hello, Cynthia,” he said in a warm voice that to her surprise did make her feel a little better. She supposed that when the universe has fallen apart the slightest sign of affection can captivate you.

  “Wh-where am I?” Cynthia stammered.

  “You’re in a secure location that we call a breaking facility.”

  “B-breaking?”

  “I’m going to make sure you’re ready to start your real training for your new life as a bed girl. We call that breaking.”

  Cynthia’s mind reeled at the word. “Why?” she whispered.

  “Well, you’ll find out, if you decide you have to try resisting me as I prepare you the way your owner wants. I’ll teach you about what you will wear and how you will behave as a submissive concubine, and you may decide you need to learn those lessons in a more painful way, with my cane across your bare bottom. Usually, a virgin bought by a client has her pussy deflowered here, too, but your owner isn’t going to come to this country—you’re going to be sent to him, and I’ll be going with you, to help him finish your training. By that time, you probably won’t need the cane to help you spread your legs for your owner, and bend over when told, but if you do you’ll certainly get as much discipline as you deserve, since that will be after you spend a week at the Institute.”

  “The Institute?” Cynthia felt a deep crease furrow her brow, and she wondered at the power of single words, otherwise innocuous, to make her heart race and, worse, her pussy get warm for the worst reasons.

  Master Greg smiled again. “You’ll see.” He took the paddle from the wax pot and began to spread more, between her bottom cheeks so that Cynthia gave a disgraceful little whimper. “You won’t have a real ass night, I’m afraid, when your owner takes you anally for the first time in front of all your new friends and your training masters, but I think he’ll be able to make your first bottom sex special.”

  “Oh, no. Please,” Cynthia breathed, but Master Greg paid her no more attention as he continued the preparation of the place she still called, in her inwardly blushing mind, her private parts.

  Preparation. Another innocent word turned terrible. As the next hours unfolded, the full, shameful meaning of preparation for Cynthia Hall became much clearer.

  Master Greg let her get up from the exam chair, after he had finished waxing her completely smooth, but then he made her stand in front of the mirror while he fondled her down there, showing her how sensitive she would be, now, to her trainer’s touch.

  “Look at yourself, Cynthia. Look at how your cunt doesn’t belong to you anymore,” he said softly in her ear, as he made her explode into orgasm. Cynthia gasped, and shuddered against the arm he had put around her waist to hold her up. She closed her eyes despite his order, her face turning bright red. Then, to his delight, as if afraid he might spank her, she opened them, and saw, and her forehead developed a wonderfully deep crease as she whimpered at the sight of his hand on the bareness between her thighs.

  Then he took her to the shower, and took off his clothes, too. He made her get in, under the hot water, but he wouldn’t let her wash herself. She whimpered as he cleaned her from head to toe, and then she had to kneel on a towel, in the shower, and suck his cock again.

  “You’re being such a good girl,” he said, after he had come down her throat. “Let’s see how you do with your new clothes.”

  In the closet of the room, which seemed except for the medical exam chair an ordinary hotel room, she saw three lacy nightgowns on hangers: one white, one blue, and one pink.

  “You’ll wear one of these most of the time at the Institute,” Master Greg said. “The white one when you get up, and the blue one after you’ve been punished. Put on the pink one now.”

  She looked up at him with frightened eyes. “What does the pink one mean?”

  “It means you’ve had a cock in you today. So everyone will know.”

  She gave a little gasp at that, but she let him lower the pink nightgown over her head. It felt so silky against her skin that she caught herself wondering if she should have a spanking just for wearing such a short, sheer nightgown—especially with nothing under it to conceal the smoothness between her legs. Master Greg demonstrated how a trainer could lift the nightgown’s hem to play with Cynthia’s pussy or bottom whenever he chose. She shied away from him a bit, then, but a warning word brought her back to stand still as he found out her wantonness yet again with his skillful fingers.

  With one hand in front and one hand behind he mastered the girl in the pink nightgown, and made her watch in the mirror as she rode his hands shamelessly, the way she had once ridden her pillow.

  He touched her anus so boldly
that she cried out, but he said, “We’ll plug you here very soon, to start getting you ready for anal sex.” She wanted to say no, then, but she thought of the cane and only whimpered as he taught her to respond to a master’s touch.

  Even when he showed Cynthia, in a little suitcase that she would apparently carry with her to her owner’s house, the lacy white lingerie she would wear when the time came for her defloration, she didn’t rebel. It made her feel very fluttery, and rather warm, because she had never had lacy lingerie before, but though Master Greg became very explicit about how her owner would make her keep her panties on while he fucked her pussy from behind, pulling the narrow strip of fabric to the side, his bloodstained cock surging in and out of her and perhaps staining the pristine lace forever, Cynthia only bit her lip and whispered, “Yes, Master,” when he said, “Do you understand, honey? Are you ready for fucking, a nineteen-year-old like you?”

  But when he told her the time had come to begin her anal training, Cynthia found the resistance she had seemed to lose with her pubic curls.

  “Get back in the exam chair, Cynthia, please,” Master Greg said in a matter-of-fact voice. “I’m going to plug your anus now.”

  As she watched, he opened another part of the suitcase and took a black thing from it.

  Addie had told her about these, as she proclaimed her refusal to comply with her boyfriend’s request that she wear one. Cynthia realized suddenly that she must have repressed this memory—and she knew why, because her face glowed like the sun as it came back to her.

  “Look,” Addie had said. “There’s nothing wrong with anal for anyone who wants that kind of thing, but it’s so degrading. Any girl who calls herself a progressive would have to be crazy to let her guy do that, with his cock or with a butt plug.”

  Cynthia had looked down at her latte, face burning then as it burned at the sight of the tulip-shaped thing Master Greg meant to insert in her tiniest orifice.

  Girls who lived in Williamsburg in their own lofts didn’t do that kind of thing. Cynthia took a step back, her hands moving behind her unconsciously to cover herself, protect the little flower between her bottom-cheeks.

  Master Greg held the thing out, in his palm. His eyes had narrowed slightly: she could tell that he had anticipated that this might be the flashpoint—the moment Cynthia would need… breaking. She thought of the cane, but the picture and the aural memory of that terrible sound didn’t have the same effect, now, because girls like Cynthia just didn’t do that. Even Addie had said so.

  As if he had read her mind, Master Greg said in a soft but terribly menacing voice, “Hipster girls don’t get their bottoms trained, do they, honey? Or at least you definitely don’t think they do, do you?”

  “N-no,” Cynthia stammered. Then, “P-please. Please don’t make me. Can’t… can’t he… the… the owner… can’t he just do other stuff?”

  Master Greg shook his head almost sadly. “No, Cynthia. He can’t. Your anus belongs to him, and he’s going to fuck it whenever he wants. I need to start getting you ready, so that he has the ride in there that he’s paid for, and so that you don’t get hurt when he starts using you there daily.”

  Chapter Eleven

  “Daily?” Cynthia breathed, a look of panic crossing her face.

  “Eight. Nine,” Heather said in Greg’s ear.

  In the mission briefing thirty-six hours before, as the pickup team got ready to jet from the small airfield near the Institute to wherever the hipster girl the Guard had chosen needed to be abducted from, Charlotte had emphasized the importance of this moment.

  “The assessors are unanimous in thinking that whichever of these girls we pick up, anal is going to be the place you find the resistance you need to focus on. They don’t call themselves hipsters, as you probably know. They call themselves progressives, in general, or alternative lifestyle, or counterculture.”

  Charlotte had looked around the briefing room, and clearly seen the same puzzlement on other faces that Greg had felt on his own.

  “You’re thinking, these girls should love anal, right? Progressive submissives?”

  A chuckle had gone through the team: Greg, the two support men who would wait in the van to transfer the chosen girl to the breaking facility, the five key training masters, and the two assessors assigned to the operation—Heather and her colleague Mark. Glancing at the assessors, Greg had seen that they of course weren’t puzzled, but they obviously had appreciated the irony nonetheless.

  Charlotte continued, “That’s the paradox that’s going to make this operation go. These are repressed submissives. That means that the messages of their body get all tangled up in the upbringings from which they’ve freed themselves culturally and politically but can’t get rid of psychologically. Then you add messages from progressive culture about egalitarianism in sexual relations, and things get thoroughly confused. Take Oriole, for example.”

  Charlotte had touched a key on her laptop, and a picture of Cynthia at a café table with her friend Addie had appeared.

  “Her best friend, a perfectly nice vanilla girl who happens not to care for anal, has thoroughly mixed poor Oriole up with respect to why she would or wouldn’t want a man’s penis in her bottom.”

  Greg had almost chuckled at that, too, but he could see on Charlotte’s and Heather’s faces a deep sympathy that stopped him. Cynthia Hall, if she proved to be the girl chosen for Operation Relegate, would go through serious emotional upheaval before she came to terms with her need for anal submission.

  “We need to use that, to get at Goshawk,” Charlotte had said, then, a little grimly. “The Guard would probably say that the end justifies the means…”

  You got that right, Greg had thought. Being a member of both the Pretorian Guard and the Institute faculty gave him a unique perspective sometimes.

  “…which is not a philosophy I will ever embrace when the welfare of submissive young women is at stake. Thankfully, though, we at the Institute can be comfortable with it, even though we feel for these girls’ inner turmoil, because at the other side of the struggle lies a life that all our data suggests will make the girl we choose happy, and not just wealthy.”

  Greg had nodded along with the other trainers. All his experience with dominance and submission told him the Institute’s way of doing things did exactly what its dean believed of it.

  Charlotte had touched her keyboard again, to bring up a covertly taken picture of Jules Herrier at a leather party in Davos, watching a young woman bound naked to a discipline frame caned by her master. Greg had recognized the look in the tycoon’s eye immediately: Herrier wanted to do that himself.

  “Goshawk,” the dean had continued, “wants to train a hipster girl. His own cultural proclivities—social, political, even economic—make girls like Oriole this man’s personal Kryptonite. The challenge for us is to ensure that he gets a girl who shows him some resistance, because our models suggest that progressive submissives tend to de-repress very rapidly. Without special handling, Oriole might have some hang-ups about anal for a while, but she would quickly become a young lady grateful for the opportunity to please her master exactly as he chose.”

  Heather had spoken up, then. “Which is why we have never considered that demographic a serious source of candidates except for clients who want angels. Goshawk needs a low-level brat, if the operation is going to work.”

  “Why?” Greg had asked, frowning. “Isn’t the point simply an emotional connection? Aren’t the endorphins going to kick in when he spanks her and fucks her, either way?”

  Charlotte had nodded to Heather, allowing the assessor to take the lead. “Yes and no,” Heather had said. “It’s not impossible that the operation would succeed if the girl was allowed to go angel, but our models say that Goshawk is much more likely to fall hard, to use the popular terminology, for a brat. If he falls hard, the operation succeeds at higher than 90%.”

  Charlotte had picked up the thread of the briefing, then. She had spoken directly to Greg, usi
ng his codename to protect the firewalls between the assessors and the support staff and between the Institute and the Guard. “From the moment you introduce the lucky girl to anal training in a concrete way, Black Bear, you have to build up her defiance even while you seem to be breaking it down. Goshawk will be watching, as you know. He will take her anal virginity, of course—but he also has to feel that he has tamed his hipster girl that special way.”

  Mark had broken in, then, in a very dry tone. “Not to put too fine a point on it, as it were, but Goshawk has to feel he’s fucked the counterculture in the ass, when he claims his concubine that way.”

  Heather had agreed, nodding. “That means overcoming resistance and bringing her around to begging for it. Can’t be faked.”

  Greg had nodded, too, feeling that he understood both in his head and in his balls, for of course he had something of the same desire: hipster girls like Oriole, he couldn’t help thinking, needed a good ass-fucking to help them come to their senses.

  Now, in the room with Cynthia, he acted swiftly: he reached out for her left shoulder so quickly that the girl only had time to widen her eyes before he had spun her around and start to march her toward the coffee table.

  “I’m sorry I have to do this, honey,” he said grimly.

  “What? What are you…”

  “Eye movement says she noticed the straps on the table,” Heather said in Greg’s ear.

  “You know what I have to do, Cynthia.”

  She twisted wildly, then, and tried to get away. A wordless cry of fear came straight from her chest.

  “That coffee table, as I think you can see now, is less ordinary than it looks.” Greg spoke right into her ear, filling his voice with the threat that he had now to fulfill, no matter how close the girl might actually be to compliance.

  “Seven.”

  He had to get her further down. When he caned her, he had to set up a new battleground in her conflicted heart: he couldn’t just drive her arousal away with the cane—he needed to start the punishment cold, as Institute trainers called it. Cynthia had to regard her resistance to anal training as a settled fact, and only a terribly sore backside could do that now, reminding her at every step that she had defied her master.