Trained by the Trillionaire Read online

“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.

  “Pl
ease 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.

  Chapter Three

  “Down to four,” said Heather James in his ear. “Mostly just the temperature, I’m guessing… ah, there we go. Six. Seven.”

  Greg Sampson looked down at Cynthia Hall’s lovely body, arranged in the very compromising but also in its own way sweetly chaste position with her sweatpants around her ankles, her panties around her knees, and her pillow between her thighs. He had fixed his eyes purposefully on the naughty sight of the lowered panties and Cynthia, as her eyes adjusted, had seen the focus of his attention. That almost certainly accounted for the rise in arousal Heather had just reported.

  The sudden illumination from the apartment’s recessed ceiling fixtures, triggered remotely by Greg’s team in the van parked outside, had probably also accounted both for the drop in Cynthia’s arousal and for the rebound, once she understood how clearly he could see the compromising position in which she had fallen asleep mid-masturbation. And then, of course, there was the fear Greg saw in the girl’s eyes as he returned his own attention to her face.

  Like every Institute trainer, though, Greg knew how very complex a girl’s fear in such a situation could be. At its root in the fight-or-flight response, fear had an essential relation to sexual arousal that a man like Greg could play like a musical instrument. Layered atop that essentially hardwired bodily reaction to a situation of perceived danger, Cynthia had a reasoning dread of specific harmful outcomes—things like robbery and murder and rape that she could have named if Greg had demanded she put the feeling into words. That part of her terror needed to be dealt with gently, tamped down with consistent reassurances and demonstrations that no real harm would come to Cynthia, provided she did as she was told.

  Provided she behaved herself and started to learn the shameful new things Greg would teach her over the next few hours.

  And the way Cynthia Hall, codename Oriole, had already begun to learn those things, as she felt her body respond against her conscious will to her new training master’s eyes, lay in the realm of an even higher order of fear. Here, deeply conditioned by the repression bestowed on her by her upbringing, lurked the fear of erotic punishment, and also of excessive erotic pleasure. Here existed the triggers for Cynthia Hall’s wanton sexual arousal, bypassing her dread and awakening her body to the submissive needs that made her an A+ candidate for forced concubinage.

  “Five,” Heather, sitting in the basement control room of the Institute’s manor house in far off California, said.

  Cynthia’s breath came in ragged pants, now. Her hands, which had already been down below her waist, had gripped the pillow between her thighs, as if she could somehow cover over the obviously lewd intent of the place into which she had thrust it before falling asleep. Greg couldn’t see even a hint of her dark pubic hair, of course, thanks to the pillow’s presence, but he knew the weight of his eyes upon her hands and their clear desperation to hide the evidence of her self-pleasure produced exactly the same effect they would have had if the girl had been fingering herself in a more conventional style.

  The drop in arousal came from the dread of specific harm, and Greg knew exactly how to deal with it. He waited, as Cynthia looked up at him with a face puckered with fear and confusion. He looked down into her eyes, and he formed his brow, his eyes, and his lips into the expression of interested disapproval that had the best chance of progressing her toward the erotic response he needed, before he truly began.

  “Six. Seven,” Heather said over the comm link. Greg could hear the smile of approval in her voice.

  Cynthia opened her mouth, but for a moment no sound came out but her panting breath, calming slightly now as the fight-or-flight response started to transform itself within her psyche, and to slide into the realm of sexual arousal. Her eyes widened a little as she waited for Greg to say something. When he didn’t, she favored him with the lovely sound of her voice for the first time.

  “There’s… there’s some money in… in my wallet,” she tried. “It’s on the desk, and… and you can take the credit card? And I won’t… I won’t report it in for…”

  He watched her face move as she tried to work it out, and he saw there what her arousal as reported by Heather had already told him, that she knew he wasn’t here for money, even knew deep down that he wasn’t here for murder or rape. The way he had thrown back the covers, and the way he stood looking at her, despite the utter unfamiliarity of it, the complete lack of correspondence to anything Cynthia Hall had experienced in real life, had informed the girl at an almost bodily level that the man who had broken into her apartment had come for something else.

  “You can take the laptop?” she tried, glancing at where Greg had put it on the nightstand before waking her.

  “Eight,” Heather said, though Greg would have known of the uptick just from the blush that spread across Cynthia’s cheeks before it vanished an instant later. The memory of what she had done while watching her sci-fi show, and its connection to the pillow between her legs had linked up, in her imagination, with the disapproving expression in Greg’s eyes. The fantasies that had played lewdly upon her mental stage as she drifted off, doubtless promising herself to finish up her orgasm in the morning, of an older man who gave well-deserved spankings to naughty girls, had surfaced if only for a moment. For an instant, Greg knew, Cynthia Hall had wondered if the man standing over her bed had come here to spank her for playing with herself.

  Then, of course, she had dismissed the idea.

  Oh, honey, Greg thought, that’s one notion you’re going to have to stop putting out of your mind so quickly.

  “I’m not here to rob you, Cynthia,” he said, making his tone slightly impatient—the voice one might use with a child slow to learn her lesson.

  “Nine,” Heather said, sounding satisfied. “She’s wet.”

  Greg expertly concealed a smile: he could have told simply from the way Cynthia had bitten her lip that the pillowcase had just received a renewed infusion of arousal from the girl’s untried pussy.

  Cynthia took three rough breaths through her nose. Greg had a brief worry about hyperventilation, which had its uses, but would be counterproductive now. Heather would warn him, though, of any possible danger of that, since she could see a dynamic reading of Cynthia’s oxygen saturation from the perineal sensor.

  Then the girl’s lips parted again. “Please… please, can you cover me up again? I’ll… I’ll do what you tell me, if…”

  Greg could practically see the fantasies come rushing into her imagination, and he couldn’t stop himself from feeling a little pang of sympathy and a newly stirring affection for Cynthia Hall. In particular, he could see the contradiction betwe
en his covering her up and the rest of what she saw in her mind’s eye as if it were engraved verbally on her forehead: This is the sort of girl who needs to be told when it’s time to fuck, and whipped when she pretends she doesn’t want to please her master’s cock.

  “No, Cynthia,” Greg said in a much softer, much gentler voice that he knew would bank the fire of the erotic needs that had started to rise out of her fantasies and into the reality of the situation she had awakened to find unfolding in her apartment. “I won’t cover you up. Actually, you’re going to get out of bed, now, and take off the rest of your clothes. Then I’m going to punish you for masturbating.”

  Cynthia’s mouth opened, and she took a great, gasping breath.

  “Probably won’t scream,” Heather reported. That corresponded to Greg’s opinion, but he got the dishtowel out of his pocket and ready to gag the girl all the same.

  “But…” she said. “But…” Her brow puckered and her nose wrinkled. Tears appeared at the corner of her eyes. “Why are you here?” she finally pleaded in a voice that was half a sob.

  Greg heard in the question everything he wanted to hear from a girl at this stage, informed that she would now be punished for her self-pleasure exactly as she had always fantasized she should be punished, in the world of lascivious imaginings to which she gave free rein in bed, at night and in the morning, but never, ever anywhere else. To put it in terms less complex than the ones a well-educated girl like Cynthia Hall would use as she humped her pillow, Greg heard that Cynthia had for a moment believed something coincidentally close to the truth, that the man in her apartment was the masturbation fairy who eventually came to all naughty girls to make them pay with their bare bottoms the painful price of all the pleasure they had stolen from the pussies that rightfully belonged to their never-yet-seen masters.

  “I’m here to start your training, Cynthia. You’ll soon belong to a wealthy man, who will deflower you and enjoy your body in every way you can imagine and some you can’t. That begins with the spanking you’re about to have over my knee for playing with your future owner’s property.”