Trained by the Trillionaire Read online

  Cheers,

  Charlotte

  All of Sarah’s preparation, the casting of a digital net that stretched coast to coast to find girls who would fit into that sliver of the Venn diagram that lay within the three circles hipster, highly intelligent, and repressed submissive, came down to this email. She had found three strong candidates in living situations that made Institute pickup possible, but only one in Brooklyn. She felt reasonably sure that Robert had chosen Oriole as much for that address as for the slightly finer quality of her East Coast education.

  If Herrier failed to bite, Cynthia could certainly be sold to another dominant man or woman. All the extra expense and effort of Operation Relegate, as Robert had codenamed the project intended to eliminate Herrier’s threat, would however go to waste. The Guard’s agreement with the Institute stated clearly that Sarah’s organization would bear all the costs associated, despite the probability of Cynthia’s producing something like 1.5 million dollars in pure profit.

  Sarah might have worded the email differently, and made it more salacious—more of a naked honeypot—but this was Emerald’s job, and her expertise. Herrier’s remark in Davos, at the Institute’s customary annual party, had sparked a furious race in the ranks of the columbae of the Order of Ostia, who usually analyzed broad cultural trends rather than individual behavior, for data about Herrier that could then be sent to the Institute’s assessors. As a foreign national and a notoriously private man who kept his digital footprint as small as he possibly could, Herrier had an immunity to the Institute’s top-level datamining: only the Guard’s efforts with tidbits gleaned from intercepts could generate the information needed to determine whether the target might actually be susceptible from that direction.

  Emerald herself had made the final call, after reading the one-page report her assessors had managed to produce: very scanty evidence in comparison to the thick file the Institute kept on each of their clients and each of their concubines. It was only fair she should have full control over the contact—and, more important, she had the finely tuned instincts and the consummate skills that had placed her atop the world’s premiere organization for the training of submissive girls and the satisfaction of dominant desires.

  And of course, in the event, Goshawk had bitten. Hard.

  The assessors had used his diction in business communiques utterly unrelated—at least on the surface—to anything sexual. Sarah shared the Institute assessors’ opinion that for powerful men especially, nothing lacked an erotic dimension, but though she had started out as a first-degree columba analyst in the sub-basements of this very building, she still marveled at what the assessors could do with juxtapositions like mountain and energy.

  Sarah felt more amazement in this case, because the ask of the Institute team had been so very specific—that they figure out whether Herrier would pay top dollar for, and more important become deeply emotionally invested with, a hipster girl to be named, and abducted, later. The brief final report had contained language that Sarah would have found ridiculous if she hadn’t respected and trusted these men and women so deeply.

  Based on the three adjective-field/noun-field juxtapositions found multiple times in the intercepts (clean and discipline; dirty and culture; modern and woman) and given the reports of his participation in dominance-and-submission activities, we judge subject Goshawk at least 70% likely to invest in a concubine he identified as a ‘hipster girl.’ He would do so with the intent to ‘reform’ her, and if she were sufficiently well trained we estimate the chance at 90% that he would experience a romantic attachment that would make him susceptible to an extensive intelligence operation, and if warranted to an intervention aided by the concubine.

  Charlotte had declared the operation a ‘go’ from the Institute side, based on that report. Robert had hesitated, and then pronounced it a ‘go’ from the Guard side, and Sarah had started to look at the Institute’s data streams, scanning for candidates among the many girls previously flagged in the system for submissive tendencies in their online activity.

  It had led, eventually, to the dispatch of the joint pickup team, at whose head stood Greg Sampson, Black Bear, the first and so far only Institute trainer to receive initiation into the Pretorian Guard, where he stood at the third degree, that of Miles—soldier. If he could break Cynthia the way both the Guard and the Institute hoped, he would run Operation Relegate in the field.

  Sarah glanced back at the video feed to see that Greg had begun his inspection without taking off Cynthia’s panties and sweatpants. She smiled—she had rather hoped he would prolong the process. Greg now manhandled the girl onto her knees, gray panties still just above them and sweats around her ankles, then pushed her face down into the naughty pillow he had returned to its proper place—not so as to suffocate her at all, and even with the implication of comfort despite the shame of having her nose rubbed in the damp, fragrant signs of her self-abuse, as she surely thought of her masturbatory habits. Cynthia gave a muffled cry through the gag as with his hands between her thighs he urged her to show herself to him further, her virgin cunt with its sparse black thatch showing pink and beautiful on the video feed, just a hint of her coral inner lips peeping out to invite Herrier’s interest.

  For Goshawk, of course, was now watching the feed.

  61423: She’s beautiful. Even in sweatpants.

  61423 was Jules Herrier, anonymized by the Institute’s chat server.

  MissCharlotte: Or without them?

  61423: haha yes without them too

  MissCharlotte: Interested?

  61423: bien sur but I will need to see more of course

  MissCharlotte: mais oui. Here’s the link to her private feed. Password is your Institute client number.

  A complicated URL followed.

  61423: any other bids so far?

  MissCharlotte: no, not yet, but plenty of interest as you can imagine. You aren’t the only billionaire who’d like to take this sort of girl in hand ;)

  61423: I imagine not. A lovely young lady like this one should be wearing lace, not that terrible cotton.

  Sarah smiled. She remembered her first nights with Robert, the way he treated her modernity—of which Sarah had had a good deal less of a veneer than Cynthia Hall did—as something that rendered Sarah liable for a sound spanking at a moment’s notice, should she manifest a knee-jerk negative reaction for example to some facet of capitalism. Her master had quite memorably bound her to a post, her hands above her, in the subterranean mastering chamber that had made the scene of her first initiation to his service. Then he had whipped her bottom and thighs with the three-tailed, knotted leather mastix until she had danced wildly on her tiptoes and screamed out her penitence. All to adjust her attitude after Sarah had questioned the sovereignty of market forces.

  On Cynthia’s video feed, Greg used his left hand, under her bound wrists to press firmly, but without real force, on the small of the girl’s back.

  “Present yourself, Cynthia,” he said. “You’ll soon be spanked for the first time, and I want to see the lovely bottom I’m going to punish to its best advantage. More important, I want to be able to take a very good look at that sweet young cunt of yours, and that pretty little anus. You’ll need a great deal of training in both places, and I want to get you started properly. It won’t be long before it’s your owner you’re presenting your cunt and anus to.”

  Chapter Six

  Cynthia heard a wild, whimpering sob come from somewhere, and she felt at the same time that her chest had contracted in exactly the way it would if she, Cynthia Hall, had produced the sound. The remaining shreds of her rationality connected the two, but those shreds also voiced to the rest of her a strange refusal to acknowledge, even in the face of such strong evidence, that she, Cynthia Hall of Williamsburg, Brooklyn, New York City, had made that kind of sound: the kind you heard in art films that depicted sex in an edgy, though always in some way ironic, fashion.

  She, Cynthia Hall, watched those films. She, and Add
ie, and the other friends who, unblessed by the trust fund that allowed Cynthia to live alone in her loft, still scraped enough money together to afford rent-controlled apartments in groups of four, not in Williamsburg maybe but nearby. They watched those films, and talked about them in cafés, lamenting with supercilious glances at the prosperous thirty- and forty-year-olds how they, the younger Brooklynites, had missed the real flowering of the culture they practiced.

  How the millionaires and the billionaires had spoiled it all, with the gentrification of the authentic neighborhoods and the corporatization of the music they didn’t simply destroy through their control of the channels of distribution.

  How even the thrift stores were being driven out by chains, and the people you saw in the cafés were dressed like fucking preppies.

  How, really, only when you watched those films with your friends—your hipster friends, as your conservative aunts would say sarcastically and mildly disapprovingly—did you feel like you could put your own troubling fantasies in their proper perspective: fantasy, on the screen, made real but not actual, or maybe actual but not real, but it didn’t matter because you could go back to the café and talk about how ironic it all was.

  Ironic: having a meaning different from the apparent one.

  Not, Cynthia Hall whimpers, sobs, moans when a man she must call Master teaches her to present her wet cunt for fucking, her young bottom for spanking.

  Not, There is a man somewhere, a wealthy man, one who might live in fucking Park Slope, or in London or Paris for God’s sake, and he will buy Cynthia Hall, so that he can fuck that wet cunt, spank that young bottom.

  She heard the sound again, at the thought, at the bold, lewd, possessive touch of Master Greg’s hand between her legs—on her virgin pussy, the first man ever to touch her there without her panties, without her jeans. She heard herself, Cynthia Hall, hipster, moan around the dishtowel in her mouth, under the nonconsensual touch of the fingers of the man who had invaded her home.

  Nonconsensual. I don’t… No means…

  She felt his hand in front of her face, and he had tugged the gag out of her mouth, but she couldn’t scream, for some reason, but only sob, “No, please. Please.”

  “Please what, Cynthia?” Master Greg asked in a very low voice. His fingers… she had never let a boy, or even David, who was really a man at this point, now, and Cynthia liked that even though she couldn’t even tell herself why… but Master Greg’s fingers, now, there, moving gently, making her not just whimper but whine… not just whine, but, worse, move, the way she knew she had practiced much too much with the shameful pleasuring pillow he had put under her face so that her nose, her cheek, were damp, besmirched with her own wickedness.

  “Please don’t… please don’t spank me. Oh, God… oh, no… please, don’t… I don’t want to…”

  “But, honey,” he said in a horribly sympathetic voice, “can you really say you don’t need this? My inspection has already discovered that, at least from my perspective as the man who has to get you ready for fucking…”

  Master Greg emphasized his words by pushing the two middle fingers of his right hand further inside than he had before—not very deep, but enough to make Cynthia think it would hurt in a moment, the way it would hurt, she knew, when a man’s hardness entered her at last. She gasped, but Master Greg clearly knew exactly what he was doing, and he stopped before she felt any pain. At the same time, with those fingers still inside her, he moved his thumb in a firm circle further up, around Cynthia’s clit, so that she gave a wild cry, her pussy contracted around his probing fingers, and she pushed back against his hand in lewd desperation.

  “…you need a spanking as badly as any naughty girl has ever needed one. You need to know that I, like the man who will buy you, take your pleasure very seriously. We know that only by controlling it, and by giving you its opposite with a firm hand and the other things with which you will be punished when you earn it, can we enjoy you as you should be enjoyed.”

  His hand moved only a very little as he delivered these terrible words, but that made Cynthia disgrace herself utterly. For the words, along with the way Master Greg minimized the stimulation to her pussy and her clit as he spoke them, made her start not just to move herself on his hand but positively to ride it, as if she wanted to show him exactly how correct his ideas about her were. Cynthia Hall, female animal in heat, unable to control her need for a man’s cock, for a man’s firm guidance in keeping her wild cravings at bay, even as he satisfied the darkest, most twisted of them as he saw fit and as he deemed best for her.

  The other things. Canes like, she remembered with a flash of heat to her face, she had imagined the time traveler using on his companion, before she had fallen asleep in flagrante with her pillow between her thighs. Paddles like the old sorority ones to which her eyes always went in antique stores, as if by a magic that made her heart race and her face grow hot as she turned away and refused to look. Straps… punishment straps that hung on teachers’ walls, on trainers’ walls, on masters’ walls.

  She cried out: she was going to come, but she couldn’t come… she had only ever had a climax with her pillow, and she knew that even if she loved him very much, and let him take her to Vermont so that he could fuck her, and Cynthia could get it over with, she wouldn’t come under David. Cynthia Hall couldn’t ever let a man do to her the only things she knew would make her body respond the way it responded to her pillow and the things she saw in her mind while she rode it.

  Things she couldn’t let a man do, because the man, the master, had to… had to… Had to bind her hands behind her, just the way Cynthia’s hands were bound. Had to put his other hand on her back and make her present her pussy and her bottom for reward or punishment or both at once.

  Master Greg took his hand away, just as Cynthia’s hips moved back, knowing that with one more movement she would come. She made a shameful, mournful sound, but it was lost in the movement of her body Master Greg now brought about, as he pulled her from the bed and stood her next to it, facing him.

  For a moment she looked him in his handsome, bearded face, but then she couldn’t, and she looked down, and saw his bag—an ordinary-looking black gym bag. She watched him stoop and pull out blunt-nosed scissors—to cut the rope at her wrists? But that didn’t make sense.

  No. Oh, no.

  To be placed against her sternum, the cold silver metal making her start and shiver, and to begin to cut down the front of Cynthia’s red college t-shirt. Master Greg’s left hand held the fabric, and his right made quick work, as she cried out in protest. She loved that shirt, the one she slept in almost every night, the sign that she would absolutely go back to school after this gap year.

  He pulled the remnants of the shirt off Cynthia’s shoulders, reached behind her to leave them as a limp cotton bundle around her bound wrists. She tried, instinctively, somehow forgetting that her wrists were bound, to bring her hands forward to cover her little breasts, but she only succeeded in seeming to present them to him, naked, with their tiny brown nipples stiff from the awful, lewd things Master Greg had done, and promised to do.

  He took a step back, and dropped the scissors into the side pocket of his bag from which he had taken them just a moment before. He kept his eyes fixed on Cynthia’s face, and the little pause in his actions made her realize that she had turned her own attention to his eyes, his mouth, his hard jaw, as if to see whether he found her nearly naked body to his liking.

  “Eyes down, Cynthia,” he said in a stern voice. “From now on, you may not look a man in the eye without permission. You are a concubine, now, and you will learn to behave submissively, or you will be punished much more severely than I am about to punish you.”

  She did as he told her, feeling her face go bright red in the process.

  “Now take off your panties and your sweatpants,” Master Greg said matter-of-factly.

  “But—”

  Cynthia meant to say that she couldn’t, because her hands were bound, but
he interrupted, in a mocking voice that made her tummy flutter and for some horrible reason she didn’t even want to contemplate, also got her warm again, further down, where things had cooled off in the flurry of activity since Master Greg had taken his tormenting hand away and pulled her upright.

  “I don’t care if it’s awkward, honey. Get out of those panties right now or as much as I think a girl’s first spanking should be with the open hand, over a man’s knee, I’ll get out the cane and start you out that way.”

  He couldn’t really have one. He couldn’t. Cynthia found herself panting frantically through her mouth as she looked again at the gym bag. How could it be long enough to fit a cane? They were long, thin things made of bamboo, weren’t they?

  Master Greg reached down again, into the bag, and pulled something else out. It was straight, black, and thin, about two feet long, with a red handle at the end.

  “No,” Cynthia whispered. She had never imagined a cane like that.

  “It’s made of acrylic, honey. It’s perfect for causing a great deal of pain without harming a girl’s bottom at all. The welts last a good long time, and you won’t sit comfortably for a day or two if I have to cane you, but you’ll be just fine after that, and you will have learned your lesson.”

  He raised it to shoulder height, then whipped it down through the air so that it made a terrifying whistling sound. Cynthia cowered back against her bed and nearly fell, unbalanced as she was by having her hands bound behind her.

  “Take off your panties and your sweats, Cynthia,” he said, “or I’m going to turn you around and bend you over and flog you until you beg me to let you strip naked for me and suck my cock.”

  Cynthia couldn’t move, even so much as would be necessary to step out of the sweats, so she could start to work the panties down around her knees so that they would drop to the floor. She had seen in her mind’s eye how terribly lascivious that dance would look, how it would make her thighs move, show the wetness glistening on their slick inner reaches. But she would do that now: of course she would, if only she could move her body and shake free of the fear, somehow.