Trained by the Trillionaire by Emily Tilton – Extended Preview

The Institute would almost have been bearable, if it weren’t for the anal harness, Cynthia thought to herself at least once a day during her training. She didn’t get caned again, thank God, but she hated the harness as much as the other girls on her hall seemed blushingly to love it. Master C always had to paddle her to get her to obey him when he told Cynthia to reach back and spread her bottom-cheeks, so he could insert the training plug that felt so degrading that it never failed to make her sob. And the leather straps and belt that attached to the plug, to keep it firmly inside, getting her used to being open and to having something invading her bottom-hole almost felt worse, since everyone could see them under the blue nightgown into which she always had to change.

Cynthia thought maybe she should have felt more embarrassment about being one of the few virgins in training at the Institute. She had to wear a special white silk ribbon around her neck, like a choker, most of the time, to tell the masters that some of her lessons required modification to keep her hymen intact. It should, she sometimes thought, have mortified her almost as much as the anal harness did—or even more, because most of the girls had to wear the harness sometimes, since it was a rare owner who didn’t wish his bed girl’s bottom trained to accommodate him as readily as possible.

But in fact she found that she wore the white ribbon almost as a mark of pride: something that set her apart. For, if Master C had told her the truth, Cynthia was indeed set apart, as the property of a man who would have her sent to him, with Master Greg as her on-site trainer. That meant that Cynthia’s owner must, the other girls told her, possess more wealth and power even than the average Institute client.

So though a part of her couldn’t help envying her hall-mates’ pleasures as they received regular fucking from the tall, handsome, hugely endowed Master C, while Cynthia only knelt to obey his command of ‘mouth,’ she didn’t really mind. The Institute had special fittings for the various implements that usually received a dildo or a penis-shaped vibrator: Cynthia had to ride these knobby protrusions while her new friends had their toys deep inside their pussies.

That part did have some embarrassment for her, as she found out her first full day at the Institute. Her senior hall-mate Gwen, a lovely blonde with more curves than Cynthia had, brought her to aerobics class. Gwen had patiently explained that Cynthia must take off her nightgown and put on the blue sports bra that hung in her cubby. Then she had shown the new girl a strange sort of firm cushion, with a slot in the top.

“This is your pleasure saddle,” Gwen had said. Looking to the left and right, she saw that all the girls were getting out their own saddles.

That had made her face burn, but it got worse. After the ordinary kind of aerobics, done with their pleasure saddles in front of them, Master K, a cultured red-haired Englishman in the black master’s robe but nothing else, made an announcement to all the girls present, naked but for sports bras.

“Our new girl Cynthia,” he said, “likes to ride her pillow in bed. It just so happens that as you can see from her white ribbon she is still a virgin. I think it makes good sense for her to demonstrate the technique she’s developed.”

Cynthia, still panting from the squats they had just finished, watched with wide eyes as Master K advanced, his huge cock swaying semi-erect between his thighs. She hardly remembered not to look him in the eye—she had already gone over Master C’s knee twice for that, spankings that atop the healing welts of her terrible caning had made her weep with the agony. As her eyes traveled everywhere in their attempt not to look up, she saw that in his hand he had a little device, a sort of bullet-shaped purple thing that he pushed a button on, to make it buzz.

“Take this, Cynthia, and put it in your saddle. Since you still have your virginity, this is what you will ride in my class, while the other girls ride their dildos.”

Looking wildly around, she saw that all the other girls had the abstractly penis-shaped things out, and were kneeling in front of their pleasure saddles, preparing the toys in their mouths to enter their vaginas.

“Kneel, girl,” he said, and Cynthia knelt on the special mat that had her name on it, reversed so that he could read it easily but she could not. She took the little vibrator in her trembling hand and put it in the slot.

“Now ride,” said Master K in an indulgent sort of voice. “Show us how you do it, naughty girl. Someday soon your owner will fuck your bottom while you ride a saddle like this one, I’m sure. Today you will suck my cock, while you are in the saddle, to learn a lesson in who owns your pleasure.”

She had managed to straddle the awful thing, had managed to ride, and to cry out once before Master K’s hands were on her face, stroking her cheeks to open her jaw so he could thrust himself inside and enjoy her.

“Go ahead,” he called to the other girls. “Ten minutes on your dildos, girls.”

Even that incident, though, seemed not so terrible, since Cynthia over and over saw the girls around her suffering the same kind of erotic ordeal every day. She found that knowing from the moment she met her hall-mates, and the girls from other halls, that they all shared the shameful needs Cynthia had thought sometimes must belong only to her, made her bond with them very quickly and very intensely. She wasn’t sure, by the time Master C in her morning training session told her that she would leave that day for France, that she didn’t feel closer to Gwen than she had ever truly felt to Addie.

“You’ve probably been wondering,” Master C said, as he buckled the belt of the anal harness behind her back, just above the beginning of the crease that led down to her shamefully opened anus, “what your family and friends think happened to you.” Cynthia lay over his lap, as she had every morning, for this part of her training.

Her face got hotter than the bottom her training master had just paddled because she had once again refused to spread her buttocks for him to put in the plug. The conversations he had with her while he put the harness on her, one-sided but for the responses he required she make, seemed almost worse than the thing in her bottom. Master C gave the plug—the largest in his leather-covered case—a little wiggle then, and Cynthia cried out and rethought her ranking of discomfort.

“Yes, Master,” she sobbed.

“Stand up and look at me,” her master said. He helped her to her feet, and she stood between his spread thighs, knowing that in a moment she would have to kneel on her special mat again, and pleasure his huge cock with her already well-trained mouth. The heat in her pussy at the thought made her feel lost: shameful and wanton.

When he reached around, though, and tugged again at the horrible plug, she seemed to find in his wolfish, appraising eyes the reason to resist the way she always had resisted having her anus trained for his, for Master Greg’s, for her owner’s pleasure. Yes, she had ridden her pillow every night and every morning, but, no, independent girls didn’t allow anal.

Master C kept his hand there, slowly and gently wiggling the plug, as he spoke, “Your new friend Alexa has told everyone…”

Frowning not only at the shameful feeling in her bottom but at this strange news, Cynthia shook her head almost involuntarily: she knew not to interrupt, had seen Tia, a hall-mate, caned for interrupting. But it didn’t make sense!

“You’re thinking you don’t have a new friend named Alexa,” Master C said with a smile.

“Yes, Master,” Cynthia sobbed, relieved to be allowed to use her voice at least, to deny it.

“It certainly came as news to Addie,” said Master C, “but of course Alexa knows a very great deal about you, and the evidence of a spontaneous trip to Europe was there in your apartment for anyone to see. Alexa must be your new best friend, of course, because you asked her to settle everything with your landlord, and to sublet the apartment.”

“Oh, no,” Cynthia couldn’t help whispering, then. That last faint hope that someone might find her had flown away.

“Since you’re a hipster, you can imagine, no one thinks very much of your having decided to find inspiration abroad. And Alexa is very good at explaining these things.”

“Wh-who is she?”

“You know better than to speak out of turn, Cynthia,” Master C said sternly. He put his hands on her shoulder and forced her down onto the mat already waiting in the proper place. “We’ll just have to keep you quiet, won’t we, while I finish telling you what will happen now?”

He held her by her long hair as he moved her mouth up and down on his cock. Cynthia kept her mouth wide open as Master Z had taught her in Masculine Pleasure class, and heard the wet chucking sound that meant she had widened her throat enough to give the cock its way. Her untried pussy burned, as it always seemed to do while giving head, especially after a spanking and in the horrid harness. Something about knowing that her voice and her pleasure didn’t matter at all to the man using her mouth seemed to do that, which only stiffened her resistance to the harness.

She didn’t know what she would do if Master C had threatened her with the cane as punishment for not spreading her bottom wide, but she had come to see her brattiness, as he called it, in this regard as a sort of declaration. Cynthia Hall would never willingly receive the awful device and wear the awful straps around her waist and thighs that turned her anus into a receptacle of her master’s cock, of his seed, of his pleasure.

“Good girl,” said Master C. “Look into my eyes while I fuck your face.” He held her head still and began to thrust up from his leather master’s chair. “That’s it. Your owner will spend a lot of time in this pretty mouth.”

His eyes glittered as his hips flashed up and down filling her and emptying her alternately. The wet sounds came faster and faster, and Cynthia felt the odd kind of pride she usually did in knowing that she had caused her master’s pleasure to master him. Master C’s voice sounded rather thick as he delivered the rest of his news about Cynthia’s impending transfer.

“You’ll wear your harness on the plane, under a very pretty dress, and your owner will meet you in a car at the airfield. He lives outside Paris, in a chateau. He’ll take you straight there and deflower you in just about twenty-four hours.”

Master C gave a grunt, and Cynthia felt the semen shoot out of his cock and into her throat. She swallowed as quickly as she could: the masters punished their girls if they wasted a drop. He held her head tightly in place as the spasms of his loins subsided, and then he said, with the head of his penis still in Cynthia’s mouth, “He will be in your bottom, I would guess, as soon as Master Greg tells him you’re ready for the cock there. I would hate for your owner to have to cane you to get you to give him what he’s purchased, so I want you to think on the flight over about saying yes to your harness, and to your master’s penis back there, too.”