Don't Miss
Home / Samples / Trained by the Trillionaire by Emily Tilton – Sample

Trained by the Trillionaire by Emily Tilton – Sample

Chapter One

RBg7: Sweetheart, do you have the Relegate dossiers ready for me?

SBo6: Yes, sir. I’ll send them now.

RBg7: Is Oriole still the obvious choice?

SBo6: I think so, sir. But Chaffinch and Sparrow have traits worth considering.

RBg7: Alright. Thanks. Have the pickup team ready for tonight at one a.m. I’ll make my decision by close of business.

Sarah James Bennett, sixth degree initiate of the Order of Ostia, submissive wife of Robert Bennett, himself a seventh degree initiate of the Pretorian Guard and head of the guard’s American branch, started the software to encrypt the three dossiers into a single compressed cabinet file. As she watched the progress bar fill up, she thought about the choice her husband now had in front of him.

Three lovely young women, all rated A+ for repressed submission according to the general assessment team of the Institute, close partner of the Guard for purposes of the very special sort of recruitment one of those girls would undergo in the early morning hours. One in Brooklyn, one in the San Francisco Bay area, one in the Pacific Northwest. Oriole, Chaffinch, and Sparrow, in the codenames attached to them by the guard to protect mission security on Operation Relegate.

One girl to bear unwittingly the burden of saving civilization, as other submissive young women had before her—as Sarah herself had in her own rather odd way, in the course of events that led to her turning from CIA analyst to field operative to double agent and finally to bound, whipped, and blissfully happy wife of Robert Bennett. One of these bird girls would be tasked, without her knowledge or, at first, her consent, both with learning what it meant to belong in every way to a dominant man and with infiltrating the household of a sworn enemy of the Pretorian Guard.

All for the cryptic purpose of saving civilization; of minimizing the damage that would soon enough be done by the worldwide economic collapse the Guard knew couldn’t be averted. When Oriole, Chaffinch, or Sparrow emerged from the deep cover Robert and Sarah Bennett would soon force on her for the good of the world—if she emerged, Sarah thought with a wince—she would learn what she had done, and why. She would, like Sarah, become an initiate of the Order of Ostia, the coven of submissive women—neophytes, acolytes, and priestesses—who served the men of the Guard.

She would by then have seen too much to leave her as a contented concubine, as the Guard had done with previous bed girls they had employed in their clandestine efforts. The nature of the mission that Oriole—for there really existed no question but that the Brooklyn girl best met the criteria for this operation—would carry out would expose her to the deepest levels of the true workings of the global economy. A more sinister organization might simply have planned to put the girl permanently out of the way, but the Guard had been founded by a cardinal of the Roman church. Despite its twisted sexual ethos, from the perspective of most of the world, the preservation of life represented its highest value. The girl chosen would have to join the Order of Ostia, and that meant that she needed not just to meet the requirements of a bed girl, but also of an Ostia operative.

Oriole: Cynthia Hall. Nineteen years of age. On a gap year from an Ivy League college, where she planned to major in classics, having displayed an extraordinary talent for both Latin and Greek at prep school in Massachusetts. Already, thanks to her family’s prominence, on the CIA’s radar screen for potential recruitment, though the Guard’s mole in the basement at Langley would be easily able to erase that from the agency’s files.

Curious—perhaps, she reflected, morbidly curious—Sarah double-clicked the icon on her computer desktop that opened Oriole’s feed. Icons for each of the three bird girls had occupied a central position there for the past week as Sarah had prepared the dossiers. Now, she knew, she didn’t really have any reason to see what Oriole was doing, since if Robert did indeed choose Cynthia, the girl would then fall under the jurisdiction of the Institute pickup team, which included a Guard liaison.

Sarah opened the feed anyway, telling herself that if Oriole came through her training in good shape she would then once again become Sarah’s responsibility, at least in part. Sarah needed to keep tabs on her, didn’t she? Her curiosity didn’t have anything to do with any sort of niggling doubt about the Guard’s ability to keep Oriole safe. Did it?

The video feed from the surveillance drone that spent most of its time on the roof of Cynthia’s brownstone showed her at an outdoor table of the café a block away from her apartment, sipping a café latte, her favorite beverage, in the company of her best friend Addie Jacobs.

Well, Sarah thought, if Robert does choose you, at least you got to have your favorite kind of afternoon.

She clicked on the muted audio and the sounds of Brooklyn, captured with rather stunning clarity by the drone’s parabolic microphone, came from the speakers in Sarah’s home office high atop the Guard’s Fifth Avenue headquarters.

“…and you’re still saying no to David?” Addie asked. “About going up to Vermont? Cyn, you’re going to lose him!”

Cynthia’s mouth twisted to the side, and she tossed her long dark brown hair over her shoulder dismissively. Having watched her for a week now, Sarah knew that the gesture didn’t mean exactly what Addie almost certainly thought it did—what even Cynthia clearly felt sure it meant. It didn’t mean that Cynthia could take David Mancini or leave him, but rather that he had stirred in her needs she would much rather not think about.

“Addie,” Cynthia said in an exasperated voice, muted fire flashing from her dark eyes, “how many times do I have to tell you that I’m going to lose it when I’m ready to lose it?”

“But, Cyn, you’re nineteen…”

“Just because you want company in the I-fucked-a-boy-I-didn’t-really-care-about-to-get-it-over-with club, doesn’t mean I have to let David Mancini lay me down somewhere north of Boston and have his way with me.”

The number in the upper right of the video window jumped instantly from three to six. Sarah couldn’t suppress a smile. She had access to a very robust data stream of biometrics covering Cynthia’s arousal from the degree of curve in her smile to the galvanic response of her skin, but Sarah had come to trust the overall arousal number to tell her all she needed to know.

The Institute, from which the data stream came, did fine work. Paired with the Guard’s nano-drone technology, something they still unfortunately felt it necessary to keep in house and not inform their partner organization about, that meant that the preparation for this kind of delicate operation could go much more smoothly than it had in the past. Only a year ago the implantation of one of the Institute’s perineal sensors between Cynthia’s vagina and her anus would have required suborning one of the staff at the reproductive health clinic where she had recently acquired an IUD, and then calling her back in for a checkup.

That highly unreliable, as well as time- and labor-intensive method had given way to a modification of the sensor itself into a nano-drone that had, ten days ago, crept up Cynthia’s skirt, under the elastic leg opening of her modest gray panties, and into position. Sarah had told Jessica Logan, her liaison at the Institute for these joint operations, that a Guard operative had gained entry to Cynthia’s apartment and installed the sensor, and given Jessica the tiny thing’s IP address, from which it had already begun broadcasting highly encrypted data about Cynthia Hall’s current arousal.

That data, just like the data from the two other girls who had undergone the harmless process on the same day in different geographical locations, showed multiple daily episodes of masturbation. One of the more conscious reasons Oriole, like Chaffinch and Sparrow, had remained virgins was that she had always, since at least her eighteenth birthday, been able to find solace with her fingers and her well-worn pillow. The often-washed pillowcase of that faithful friend disclosed on its removal stains, right on the pillow itself, that always made Cynthia look away even as her cheeks burned hot. Her blushes raised her facial temperature enough to show up on the Institute’s data stream in red, courtesy of sensors placed in the molding of the girl’s apartment while she had sipped a latte with Addie.

That self-pleasuring capacity represented a double- or even triple-edged sword for Cynthia’s peace of mind, however, as Sarah would have known from her own experience even if the Institute’s modeling hadn’t nailed it in the first report from the assessor team assigned to joint Guard/Institute operations.

Subject Oriole comforts herself with pillow humping at least once a day, and usually twice: upon waking and before falling asleep. From her net activity, especially the penumbrous scrape…

The term always made Sarah giggle, but Institute jargon never lacked a point: the penumbrous scrape constituted the sum total of minor details in the way a girl behaved when interacting online, from her apparently random motions with her fingers on her phone screen to keep the phone from locking to the speed with which she scrolled through certain suggestive images.

she has the submissive fantasy life characteristic of the A+ with frequent masturbation. The self-pleasuring generally occurs after seeing an image of domination or reading one of the passages she has read so many times before, from the books on the syllabus of the ‘Fiction and Sexuality’ course from which she seems to have withdrawn after the first lecture. (One wonders if Oriole even sat through that first lecture, and one wishes one had biometric data from the seat out of which she perhaps fled in the middle of it.)

Should she be acquired for training, due attention will have to be paid to Oriole’s guilt about the masturbation, arising from her conservative upbringing, to the way she has detached it from the rest of her life and in particular from her romantic relationships, and to the theory of herself as without erotic need created by that detachment. None of that should pose a challenge to her trainers, but if Oriole is to develop into a valuable asset, her training will have to assist her in working through the dismantling of her most fundamental ideas concerning who she is, and will be.

“Bitch,” Addie said shortly, clearly wanting it come out as a joke, but actually at least half-meaning it—and Cynthia, as Sarah would have expected from a girl who rated a nine out of ten on the Guard’s empathy scale, picked up on it instantly.

“Look, I’m sorry,” Cynthia said, her brow creasing with her genuine regret at having bruised her friend’s feelings. “But you need to stop pressuring me on this. If David can’t wait, then he’s not the right guy.” Her mouth twisted again. “I mean, I guess I’m far from sure that he’s the right guy even if he can wait.”

“Seriously?” Addie asked, taken aback. “You’re such a great couple! I mean you finish each other’s fucking sentences, like in a movie.”

The arousal number in the upper right had descended now, from the moment when Cynthia had inadvertently sparked a fantasy in her libidinous imagination with the offhanded reference to submitting to her boyfriend in Vermont. She stood at two as she frowned down at the table, obviously searching for a way to explain to her best friend something she couldn’t even explain to herself.

Sarah thought again of the assessor team’s report.

Oriole’s boyfriend doesn’t help matters, being himself a repressed dominant. Observed sexual activity shows him fighting his urge to take Oriole in hand. Those mixed signals only make the problem worse for Oriole and cause further detachment of her real life, nearly chaste, erotic relations with her boyfriend from the active submissive fantasy life in which she indulges with her faithful pillow between her thighs.

During the week of surveillance, David Mancini had come up to Cynthia’s apartment only once despite their eating dinner together nearly every night. Some of that could be explained by the need for him to wake early to get to the construction site where he worked as a foreman and management trainee, but even that excuse begged the question: why hadn’t he pressed the issue just the little bit that might have awakened Cynthia to her need for his dominance? If he had acknowledged to himself just how much he wanted to spank her for her actual occasional bitchiness, perhaps Oriole wouldn’t now stand on the brink of being picked up and forcibly recruited into the sexual service that would awaken her fully to needs her boyfriend actually did want to satisfy.

If the assessor may be permitted to express her opinion, Oriole and her boyfriend are, sadly, very good candidates for the Extreme Marriage program. One almost wishes the Institute could use some of its endowment to fund a scholarship.

Chapter Two

Cynthia tried desperately to keep her mind off what had happened with David Saturday night. If she let herself see the look on his face, as she once again gently but firmly removed his hand from between her legs, she knew she would show Addie exactly how conflicted her heart had become in the last two months, since things with David had gotten ‘serious.’

‘Serious’ meant that if Addie had been the one dating David, they would have long since had sex.

They would be fucking like rabbits.

Damnit: Cynthia’s face had gotten hot, now. Maybe her tan, from the day with David at Coney Island, would hide it?

No such luck.

“Cyn, you’re blushing, aren’t you? Oh, my God, you have to get this over with. Isn’t he right enough for that?”

Yes, but…

Saturday came back in full, despite her best efforts. The way he had looked at her, and for a moment she had seen in his eyes that in a different world he would have forced the matter. That he wouldn’t have let her take his hand away.

That he would have told her to stand up and take down her jeans and her panties so that he could finally see the place where he would take her, claim her, deflower her.

And it came back to her, mortifyingly, so fully that here at the outdoor table, across from Addie, she felt herself gush into her panties the same way she had when she saw that look in David’s eyes, just a moment before the look had vanished and become resentful.

Before he had said, “Well, I’ll see you tomorrow, I guess? For the ballgame?”

Cynthia and David watched the Yankees together every Sunday. She liked the way it made her think of her dad, who had passed away last year.

Usually David, who also reminded her of her dad, spoke of watching the game with a sort of half-boyish, half-manly delight that made Cynthia feel like she had found a man with the perfect combination of intellect and playfulness: an Ivy League graduate who like to work with his hands and had the physique to match. Broad-shouldered and light-brown-haired, with blue eyes that lit up when he talked about baseball, or architecture, or superheroes.

On Saturday, after Cynthia had moved his hand, he spoke of the ballgame as if it were a chore, or last prize in the contest for the frozen heart of Cynthia Hall, perpetual virgin.

Not the frozen heart.

The frozen cunt.

She felt the blood rush to her cheeks anew, and she knew she had to say something or Addie would start to pry, and Cynthia just couldn’t deal with it. She didn’t know if things with David were in fact falling apart or not. She didn’t know if she wanted ever to have sex, if sex meant…

If sex doesn’t mean…

That. What she thought about when she put her pillow between her legs, the place from which she had taken David’s hand away because good girls didn’t let their boyfriends do that until…

Until when? Until he tells me to show him how I ride my pillow every morning and every night, thinking about him spanking me?

“That’s enough,” she said, managing to look up at Addie, hoping her friend wouldn’t see that Cynthia’s eyes were brighter than they should be, any more than she could tell that Cynthia would have to go back to her apartment to change her panties and maybe even her jeans.

Addie frowned, her face full of concern that felt to Cynthia even worse than the jocular annoyance she had seen there a moment before. Cynthia rushed ahead, hoping the stream of words would cover over the awkward moment.

“I have to go, anyway. I just remembered I have to get some proofs to my boss by four.”

That deepened Addie’s frown, but Cynthia had at least established previously that, one, she took her job at the small publisher where she worked seriously, and, two, that her work schedule was crazy and easy to lose track of.

“Okay,” Addie said regretfully and a little doubtfully. Cynthia could tell that she hadn’t entirely fooled her friend, and that made her obscurely glad. She would never tell Addie the humiliating truth, about how Cynthia would probably never have sex, since sex for her apparently couldn’t be what she needed it to be, but it helped a little to know that Addie sensed the trouble in Cynthia’s heart and soul. At least when she finally had to break up with David, as she felt sure she would, and maybe even this week, Addie would know that it hadn’t come out of the blue.

Cynthia did have proofs to get done; they just didn’t have to get done that afternoon. She did them anyway, on her laptop at the little desk that stood in the brightest corner of her tiny studio apartment. She ate some ramen. She watched a sci-fi TV show.

On the show, to her chagrin, the older man who gallivanted around the universe and its timeline spoke to his younger female companion in a didactic, even an admonitory way. He told her to do something she had refused to do, and he made it sound like he might spank her if she didn’t. Like he might be very British indeed, and use a school cane across her naked bottom, if it seemed necessary.

Cynthia swallowed hard. She was sitting in her desk chair in the sweats and big t-shirt she wore as pajamas, watching the show on her laptop. She cast a glance at her bed, five feet away. She could, as she had many times before, unplug the laptop and carry it to the bed.

She did.

On Cynthia’s bed sat an old teddy bear with slightly sad eyes. Since at least Cynthia’s eighteenth birthday, she had witnessed the lewd scene that would now transpire many, many times. Sometimes Cynthia, only half playfully, turned her away, into the corner within whose angle her bed nestled. Sometimes she said, “Corner time for you, naughty bear.” Sometimes she just felt the heat in her cheeks, and down below, as she considered what she had resolved to do, from which she might still nevertheless turn her path away—away from shameful self-gratification and toward virtuous chastity.

She lay down, with the laptop in front of her on the bed.

Cynthia’s bed had two pillows on it. One, which spent the days on top of the other, had come from the bedding store only a few months ago. The other had come from home. Firm, and very well-filled with resilient foam rubber that made it uncomfortable for her head but perfect for the purpose it really served in her life, it bore a plain white cotton pillowcase made of Egyptian cotton with a very high thread count. Cynthia had blushed even when buying the pillowcase, to replace a less luxurious one that had served her shameful lusts well but had begun to fray from all the laundering it had received.

She started up the show again. Now she would see… she would just see, the way she told herself was alright, whether the time traveler would say something else, like what he had said before, about how his pretty companion who really looked quite a bit like Cynthia had to stay in the time machine.

Whether he would have that look on his handsome, older-but-not-too-much-older face again, that said that in his day, on his home planet, he had taken many a girl across his knee to teach her a well-deserved lesson about respecting the authority of the man who had taken it upon himself to take care of her when he had the whole universe about which to think.

Whether he would look like David had, for one moment on Saturday night, when it had seemed he might have had enough. Might put his foot down. Might say that Cynthia Hall had a great deal to learn about what it meant to have a tall, handsome boyfriend whom she had kept waiting much too long. To whom she belonged… all of her… especially…

Especially the place from which she was pulling down her sweatpants, but not (never) her panties. Panties got dropped in the laundry basket in the morning, usually after Cynthia had had one of her little morning climaxes in them. Dirty panties, that a man like the time traveler would inspect, and find indicative of a serious problem… a problem in that shameful place where she had soaked through, onto the pillow against which she moved, because she had, yes, reached for it, and nestled it into its familiar naughty place down between her thighs.

But… the time traveler got into trouble with aliens. This was the problem with what Cynthia called, to herself, watching TV in bed. The aliens weren’t the slightest bit sexy, either. Utterly relaxed, if still vaguely needy down below, a state she thought of as a pleasant side effect of her shame and one that almost excused it because it kept insomnia well at bay, she watched to see if things on the screen would command her hips to move again.

They didn’t. Cynthia closed the laptop when the time traveler had defeated the aliens and delivered a speech about compassion, which his pretty companion drank in with her winsome smile showing how much she had learned over the course of the episode, and the eerie theme music had begun.

Should she? She closed her eyes and moved a little against the pillow. Her panties were damp, now, but they were also warm, and she could finish in the morning, couldn’t she? Cynthia had fallen asleep this way many, many times, feeling terribly naughty but also very happy because she had her own apartment and she could… you know… whenever she wanted and for however long she wanted.

Yes, in the morning. She opened her eyes, stared into the dark of her cozy little home to reassure herself that all was well.

She closed her eyes, thinking of the time traveler, then of the man, yes, she loved. Older than she, by three years. Just enough, she had thought the first time she had realized she might be falling in love with him. She moved again against her pillow, feeling the slight stiffness of the cotton through the softer cotton of her sensible panties. Not never, really, did she lower her panties… but not often. She rode the pillow a little. Yes, she would have to pull down her panties, just not quite yet…

David, please… please… like the time traveler… your big thigh… your big hand… your big…

Alright, yes, she would have to pull them down now, wouldn’t she, because it would feel so very good. She moved the pillow, hooked her thumbs in the elastic, tugged awkwardly, doing her best to ignore her own body’s lewd actions. Then, as she returned the pillow to its place…

Oh, God, that moment, that first bare moment… oh… but then the lassitude returning. She would finish in the morning, or… maybe…

David, can’t you… can’t you just… take me…

“Cynthia, wake up, please.”

Heart racing, she opened her eyes to find her apartment dark around her, only a hint of the lights from the street outside showing behind the heavy shades. Her laptop lay closed on her comforter, under which she had her sweatpants down and her pillow between her thighs, details that seemed much, much too relevant because a man stood over her, looming, visible only in outline as a dark shape with a deep voice she had never heard before.

She opened her mouth to scream, part of her stepping outside herself to marvel a little that waking up to find a strange man in your apartment actually did make you scream.

Both the scream and the thought were interrupted by the man deftly inserting something… a cloth of some kind, maybe a dishtowel?… into her mouth, completely muffling the beginning of the sound and then silencing it entirely thanks to Cynthia’s shock at what was happening.

“Please don’t scream again, Cynthia,” said the man. His voice didn’t sound harsh or cruel. It sounded like the man might actually be a sane, even a sympathetic, person. It also, however, had in it a sort of authority that made her whimper around the gag just hearing it. Like the time traveler, talking to his companion, but exponentially greater.

“I’ll take the gag out if you promise not to scream. Nod if you promise.”

Only now did she start to wonder why he was in her apartment. Something about the way he spoke, the tone and the accent that had an educated quality one couldn’t feign, made her think that whatever his intent, she could reason with him. She would give him what he wanted, as long as…

Cynthia swallowed hard. Her mind, strangely, wouldn’t go beyond that as long as. She nodded frantically, as a way at least to gain a little time.

The man pulled the dishtowel from her mouth, paused with it just an inch away from her face, clearly waiting to see if she would trying screaming again, then removed it entirely, putting it in the pocket of his jeans. Watching that occur she realized her eyes had adjusted to the dark, and she looked up at him with wide eyes as she took in his size, his muscularity in his black t-shirt, and the chiseled look of his jaw.

“Good girl,” he said, and, reaching down, threw back the comforter as at the same time, somehow, he turned on the lights.

Read More Info and Buy!