Trained by the Trillionaire

by Emily Tilton

  Holly pressed the butt plug, and Cynthia whimpered up into the rubbing lips, the pressing clit. So much wetness there, so much fragrance. Holly kissed Cynthia’s clit, and the girl underneath, observed from above, tried to do the same, begging with her lips and tongue for any reward, any resolving pleasure the flight attendant might provide: the stewardess, her uniform stripped off, controlling her wayward passenger, demanding pleasure as she bucked her hips to seek Cynthia’s chin, her nose, her whole face for a stimulating saddle.

  Holly did kiss, and did finger. Cynthia moaned in gratitude. Holly came, and came again.

  Master Greg’s voice seemed to float down, then, just as Cynthia began to build toward her own climax, hardly daring to hope Holly would finish her off, wouldn’t stop in order to leave her needy for her owner.

  “Cynthia likes to ride her pillow in her bed at home, you know, Holly. The way you’re humping her face now is pretty much what she used to do when she played with herself before she understood what she really needs.”

  The orgasm started, then, and Cynthia gave a cry. It would happen… it would…

  But Master Greg had stopped Holly’s ride, and was helping her dismount.

  “No reward for you, naughty girl,” he said. “Show your owner how eager to you are to please him, and he’ll reward you.”

  Cynthia closed her eyes as a sob of frustration came from her chest. She felt the air moving over her damp face, the heat of Holly’s cunt cooling on her cheeks.

  “Get up, Cynthia. Holly will take you to the lavatory and watch you pee. Then you’ll go to sleep so that you’ll be rested for Monsieur Herrier.”

  “Monsieur what?” Cynthia asked, swallowing hard.

  “Monsieur Herrier—your owner.”

  Being watched on the toilet represented an everyday occurrence at the Institute, but it had never become routine for Cynthia. To have to pee with the door open here on this luxurious private jet with Holly, now back in her stewardess’ uniform, watching felt much more embarrassing. She couldn’t meet the flight attendant’s eyes as she wiped herself and flushed the toilet, and she jumped at the roaring sound of the pee being sucked out and away to wherever it went. She tried to think about that, puzzling out where her urine had gone, rather than about the man whose name she now knew, as she tried to quiet her thoughts after Master G had frustrated her so cruelly on the bench.

  He fastened her seatbelt in one of the regular passenger chair, which reclined almost level with the floor to serve as a fairly comfortable bed. Then he secured her hands to the armrests with cuffs she hadn’t noticed before.

  “No touching Monsieur Herrier’s property,” he said in a warning voice.

  That, too, gave the flight a dreamlike quality: to lie almost immobilized in the comfortable seat bed, trying to keep her thoughts from all the things that made her heart race and her limbs want to struggle against her bonds: the anal harness, Holly’s cunt looming over her, peeing with the door open, and being so very needy between her thighs.

  Why did he bind my hands that way? He knows I never use my fingers. Only my pillow, the way Holly used my face.

  Cynthia didn’t think she’d ever get to sleep—real sleep, anyway: she thought she’d lie there in that irresistible dream of being sent into sexual servitude forever, because time had ceased to have meaning, and it was just being there, naked under the pink nightgown except for the belt and the straps and the horrible plug in her bottom that meant that all her fantasies were going to come true.

  She awoke to find sunlight streaming in the plane windows, and realized she must have slept at least six or seven hours from the stiffness of her limbs as she again found them restrained.

  “We’re almost on the ground,” Holly said, as she pushed the button that raised the back of Cynthia’s seat. Master Greg adjusted the cuffs on her wrists, and tightened the strap that secured them to the armrests, so that Cynthia’s hands lay bound atop them.

  Cynthia looked at him as he sat down next to her, careful not to look him in the eye but hoping to catch a glimpse of his expression. He looked very thoughtful—pensive, even—and she wondered why. To her surprise, he patted her hand on the armrest between them.

  “Look at me, sweetheart,” he said in a warm voice that Cynthia found soothing despite all the anxiety of the moment. Cynthia did, and found the same warmth in his eyes. “I’m here to take care of you. You don’t have any choice about how your new master is going to enjoy your body, but I promise to keep you safe while I help him train you.”

  Cynthia bit her lip, and when she saw that Master Greg waited for a response, she said, surprised to find that she meant it, “Thank you, Master.”

  Chapter Fifteen

  Herrier’s limo did indeed stand waiting for the jet’s arrival, to the side of the airfield’s single runway. Greg watched the driver open the passenger compartment door, and saw Goshawk himself step out, in an impeccable dark suit that shouted Givenchy, a sky blue tie at his throat to match the blue eyes that glittered under his mane of dark brown hair. The man had an imposing air, at 6′ 2″ and with all the self-possession that extraordinary wealth always gave a true alpha.

  He looked like the sort of man you could never take down with anything so simple or so crass as a honeypot.

  Ah, but Oriole is no ordinary honeypot.

  Jessica Logan’s voice came over the comm link. “Black Bear, Garnet here. Relegate is go. We’ll switch your comms to satellite in a moment, but don’t rely on voice since it’s likely to cut in and out because we have to keep your link’s gain turned down to escape detection. We’ve got drones in the area, but Goshawk’s security net is top notch, so we can’t do much close in. You’re not on your own, though.”

  You’re not on your own, but you are on your own. Herrier had taken the precautions of the trillionaire recluse against the high-tech measures on which the Guard—and the Institute—usually relied.

  “Remember that Oriole’s sensor array is your last resort.”

  Greg felt his mouth turn down. Of course he remembered that. The key to Operation Relegate, beyond Cynthia herself, lay in the Institute’s requirement that they be allowed to fit Herrier’s chateau and other residences with sensors and communications equipment that could assure them the girl remained safe and unharmed. The price, of course, had been Goshawk’s tech’s access to the whole data stream. When the time came for Greg to use that utterly reliable channel of communication, he—and Cynthia—would have mere minutes before Herrier’s henchmen closed in upon them.

  “Last thing. Arno has started another operation that’s going to be attached to Relegate if it pans out.”

  What? Greg struggled to keep his frown from deepening, changed it consciously and with difficulty into a smile so that he wouldn’t disturb Cynthia. She currently had her eyes obediently lowered but would soon he knew try again to steal glances at her trainer’s face, looking for cues.

  “Operation is called Heatsink. If you do end up having to worry about it, it would only be when Goshawk takes Oriole to Paris, so your comms and our drones would be fully online. If Goshawk never takes Oriole to Paris, Heatsink is irrelevant.”

  Now the frown threatened to break out again. What the fuck did it mean?

  “That’s all. Switching you to satellite. Godspeed.”

  Greg noticed a soft, tinny buzz in the micro-speaker implanted under his ear, and then Jessica said again, though she sounded much less distinct, “Testing. Touch your forehead if you can hear me.”

  Greg raised his hand and rubbed his forefinger along his hairline. The action attracted Cynthia’s attention, and she looked over at him nervously before again dropping her eyes.

  “Cynthia, sweetheart,” he said. “Look at me.”

  He managed the smile that he knew would help her, then, and let the operational concerns of the mission fall away. Really at least for the next few days he had only one job—the one that both his target and his agent expected of him… the one at which Greg Sampson knew himsel
f to be one of the best in the world.

  The saving of civilization by means of covert operation would wait: he had a lovely bed girl to train to the specifications of one of the most powerful men in the world.

  The jet taxied to a stop. To Greg’s surprise, Herrier came from the side of his car toward the jet. He looked over at Cynthia again, to see that she had fixed her gaze out the airplane window.

  “Is that… him?”

  “Don’t speak unless spoken to, Cynthia,” Greg said sternly.

  “Seven,” came Heather’s reassuring voice in his ear, over the satellite now but still his anchor in the storm of Operation Relegate.

  “Keep him on the plane as long as possible,” Jessica said.

  Holly had unbuckled and moved now to open the door, lower the little stairs. “Monsieur Herrier,” she said with a flight attendant’s beaming smile, and then Goshawk had come aboard, his eyes directed only at his concubine. He stood still, across the open part of the cabin from where Cynthia and Greg sat, a little smile on his face that Greg thought very French indeed: suggesting that he owned the world but he didn’t care, and would rather be sipping Bordeaux on the bank of the Seine than enjoying the more material part of his good fortune.

  “Champagne, if you please,” he said to Holly, without taking his eyes off Cynthia. “We’ll spend a few minutes here, if it’s alright with the girl’s trainer.” His accent, pure Parisian, matched the smile.

  “Of course, Monsieur Herrier,” Greg said smoothly. Relegate had gotten off to an extraordinary start.

  “Eight,” Heather said. “Nine. Check her eye line, Black Bear. We can’t quite see it.”

  Greg looked over and saw that Cynthia’s gaze rested on Herrier’s shoes, but that she also couldn’t help flicking it up higher. He waited until he saw a slight upturning of her chin, as she desperately and nearly involuntarily broke the rule to try to soothe the turmoil inside.

  “Eyes down, Cynthia,” he said, with a severity that made the color rush into her face. He looked over at Herrier. “I’m sorry, Monsieur. The girl knows better than that. Would you care to spank her, or shall I?”

  Cynthia emitted a tiny whimper to hear herself referred to in so objectifying a way, in her own presence.

  “You shall, by all means,” the tycoon said. “But not until we get her home.”

  Holly brought him a flute of Heidsieck, and he sipped it meditatively as he kept his eyes on the trembling, blushing girl he had purchased. He glanced over at the long bench to his left. “Put her on her knees, there, and bend her over. I’ll inspect my property before we go to the car. I need to see how my hipster’s cul is coming along.”

  He pronounced hipster in a way Greg didn’t think he could ever truly imitate no matter how long he might have to practice, though he considered himself a fair impersonator. Most of the rest of Herrier’s English had only a light Gallic lilt, albeit with the unmistakable Parisian drawl. In general, he pronounced his h’s, unlike the vast majority of Francophones, and he stressed the correct syllable most of the time, rather than the final one.

  When saying hipster, however, that all fell away: Herrier pronounced it ‘eepstAIR,’ with the second syllable drawn out for what Greg felt sure must be almost an entire second. He felt his lips twitch, sure that the Guard would get some invaluable intel from that particular quirk. More important, it demonstrated just how crucial this aspect of Cynthia’s profile would be.

  As if to emphasize the point, the short, inimitably French cul, following that mocking, loaded ‘eepstair,’ confirmed the potential of the honeypot set by the Guard, as well as revealing the danger involved. Herrier had just revealed himself to be as obsessed as they had hoped with civilizing his countercultural possession in a way that could pose a grave risk to her, should the magnate get carried away.

  “Six,” Heather said, confirming the drop that Greg had felt sure must come, as Cynthia turned wildly to him, her eyes now on the buttons of his dark blue Oxford.

  Greg unbuckled his own seatbelt and rose. Leaning down over Cynthia, he unfastened the cuffs from her wrists, and then unlocked her seatbelt. The trembling in her limbs had grown into real shaking, and she breathed through her nose in little puffs. He wished he could get a sense of what the jet’s sensors had picked up about Herrier, or even just know where the Frenchman’s eyes had gone now as he watched his concubine’s trainer help her up, so that he could usher her over to the bench where her intimate secrets would be at her new owner’s command.

  “Seven,” in his ear.

  No, he thought regretfully. I have to reinforce the fear, if we’re going to get Goshawk where we need him. Cynthia couldn’t be allowed to relax into the erotic dimension of the scene.

  “Kneel,” Greg said gruffly, pointing. “Right there, facing the bench. Monsieur Herrier’s going to inspect you. Monsieur, what will you be looking for? It will help your concubine to know.”

  No, it won’t: it will make her more afraid of the night to come. Greg felt a pang, but he had absolutely no choice in the matter: he needed to ratchet up Herrier’s response with Cynthia’s fear. Some of that fear would be limbic flight-or-flight response that would ensure that Cynthia was wet despite herself when the time came. The reasoned dread above it, though, which would keep that helpless arousal in check, represented the tool Greg needed to employ, as hard as it would be on his agent.

  Cynthia hesitated, unsure whether to kneel right away or to wait for her owner to respond to her trainer’s question. Herrier, clearly stimulated by her uncertainty, decided the matter for her. He shifted his champagne to his left hand, and then took a step forward, extending his right. Cynthia cowered back toward the bench a little, but her owner moved too quickly: he had his hand in her hair, pulling her head back, as she gave a little cry of frightened surprise.

  “Eight,” Heather said over the satellite link. Fight-or-flight.

  “Look at me, eepstair girl,” Herrier growled.

  “Seven.”

  Greg watched Cynthia focus on the tycoon’s face, six inches away from her own, as he bent a little over her, looking almost like a vulture.

  “You will kneel when you are told to do so. You will kneel very often. You are not in Brooklyn any longer. You belong to a man who knows how to teach you to behave properly, and knows how to enjoy you as a lovely young lady like you should be enjoyed.”

  “Eight.”

  Wait for it, Greg cautioned himself.

  Herrier used his grip on Cynthia’s hair to turn her to the wall and force her to her knees, then pressed her face into the bench.

  “Nine.” Heather sounded just the slightest bit worried now.

  Wait for it.

  Herrier handed the champagne to the waiting Holly, and shifted his grip on Cynthia’s hair to his left hand, so that he could raise the pink nightgown with his right, and tuck it up to show the shameful harness his bed girl wore. Not losing a moment, he laid his hand on the base of the butt plug, and pushed.

  “Eight. Seven.”

  “Cynthia, ma fille, why are you wearing this harness?”

  “Oh, please, no,” she whimpered. “Please.”

  Herrier pressed harder.

  “Six.”

  “What am I going to do with this little cul, to teach you to behave?”

  Cynthia gave a little sob. “Please don’t.”

  “You have a good deal to learn, ma fille,” Herrier said. “Maître Gregoire, I’d like this harness off, please, so that I can finger her anus. My eepstair needs to understand “

  “Oh, please. I’ll say it. I’ll say it. You’re going to fuck my bottom! You’re going to put your penis in it!”

  “Five.” Heather sounded much more sanguine now.

  “Too late,” Herrier said smoothly. “Don’t be sad, Cynthia. You were going to have my fingers up your cul very soon anyway.”

  Greg bent to undo the buckle at Cynthia’s back. The process of pushing out the big plug opening her would certainly drop her arousal further,
which would set up the next phase of Herrier’s taming of his modern girl quite nicely.

  “Push now, sweetheart,” Greg said, tugging gently at the plug. “Your bottom knows how to do this.”

  Cynthia sobbed as she tried to obey, her little bottom surging with the shameful effort.

  “You can do better than that,” Herrier chided. “I thought you didn’t like having the plug inside. Push harder.”

  She grunted and tensed her flanks, presenting a degrading spectacle that made Greg as hard as iron in his pants. He helped her expel the intruder, but not too much, so that the moment would have the proper effect on both owner and concubine. At last, with a tiny scream, Cynthia managed to push the big black plug out, with a shameful sound that Greg knew she must find as humiliating as Herrier found it arousing.

  “Four.”

  Just where we want her.

  Chapter Sixteen

  Cynthia didn’t know how she could survive it. She had thought that maybe, with all the training she had gotten at the Institute, she would come out alright. But now even the idea of the submission she knew she couldn’t now escape made her heart try to pound out of her chest. She didn’t know if she could even hold herself in position over the bench, despite fully grasping that if necessary Master Greg would hold her down for Monsieur Herrier’s terrible inspection.

  This wealthy, powerful, and—she saw now—handsome man meant to take, here on the plane and then in his chateau and then, she supposed, all over the world, a nearly professional interest in mastering her anus. He meant to teach Cynthia Hall to regard that part of her as his to use as he pleased, despite everything she had decided she believed about the parts of her that should be yielded up to a man and the parts that shouldn’t.

  Master C had tried, and Master Greg had tried, and she knew that every Institute concubine who went through the regular training had her ass night at the end of it, before going home with her owner. Monsieur Herrier, too, they had told Cynthia before she had even known his name, would put her through an ass night of his own design, here in France.