On the plane they had made Olivia dress in a short lacy see-through white nightgown. By the time she woke up in that nightgown Sunday morning, her third new day in what Gabriel and the others called the breaking facility, the little nightgown had begun to seem like normal clothing, and having to take it off, or having it taken off her, seemed nearly as normal. The two other girls she had seen here at the facility both wore them.
Mostly, when Olivia had to please Gabriel or another man, or when they spanked her, or, more frequently, when they used her now-hairless pussy, they left the nightgown on, perhaps since it could so easily be raised to give convenient access both front and back, for punishment and sex. Sometimes, though, as if to indicate to her that whether she wore any clothing at all or not lay entirely within their discretion, they made her take it off before they used her or whipped her.
One of the other girls, Becky, had waxed Olivia’s pussy and rear cleavage on the first day, so that when Gabriel raised her nightgown he always said, “I’m so happy you’re bare down here, now, honey. Your owner will love the way your pussy looks,” or words to that effect. He would also tell her from time to time that she could expect to wear panties again when her owner gave them to her, but that they would be of a very different style than she had accustomed herself to wearing in her old life.
“Now that you’re nice and bare down here,” Gabriel had said the afternoon of her first day, just yesterday—Friday—though it seemed like an age ago, “you’ll look sweet in a thong, especially a really little one. Your owner will only have to pull it aside when he wants to fuck your sweet young pussy or your bottom.”
Gabriel said a lot of things like that. It had begun in the van when Olivia had learned to take his cock nearly as deep as he could thrust it; the sound of his degrading words somehow unlocked in her the Olivia who couldn’t help playing with herself no matter what she did. That Olivia—that secret girl—swallowed the semen of the three men so greedily that she earned high praise from Gabriel even before he told her to get up from the floor of the van, because they had arrived at the airport, where a private jet waited to take her wherever she now was.
As she sucked his cock and the cocks of the men she now knew as the orderlies, Dan and Steven, the answers about what sort of life they had in mind for her, with all the coarse and humiliating detail, seemed to flow around her, making her more and more wanton as she knelt before these men Gabriel said were now her masters and learned the shameful ways of their pleasure. Why, she kept wondering, hadn’t Jared just made her do this? If only he had said that he would whip her if she didn’t, Olivia knew now she would have fallen to her knees for him, too, and she wouldn’t have stopped pleasing him until his semen, like Gabriel’s, had spurted down her throat.
The way her body responded to Gabriel’s account of what would happen to her seemed to Olivia to make it terribly hard to deny how much she needed this. Listening to her captor, sucking the cocks he made her suck, her mind kept flashing back to the night in the hot tub after the party, when the thing that happened in the bathroom wouldn’t leave her mind and she had seemed to go a little crazy with Jared.
She remembered standing up, bending over, and looking over her shoulder at him. She remembered him coming toward her, entering her, his hands on her shoulders as he fucked her wildly. The way he had made her cry out and the way he had made a growling, satisfied sound in his throat. Then, later, playing with herself long into the night, thinking about the thing in the bathroom and the sex with Jared, until finally she came very hard and lay exhausted, and decided she must put a stop to it the next time it came up.
And now there she was on the floor of the van, a captive who should resist, shouldn’t give in to her body’s shameful responses, who should be searching for any means of escape she might find. Instead, she sucked men’s penises for the very first time: three of them, long and hard, until the men held her head down and made her swallow everything they gave her. And all the while, Gabriel told her of her fate.
“We will first take you to what we call the breaking facility,” he said, his tone gentle and calm, as if by performing her shameful service Olivia had earned a look at his softer side. “You will spend two or three days there, learning to be a good girl for your training. When I’m sure that you’re ready to obey your masters I will take you to the Institute itself, where you will be assigned to a training master, and undergo the rest of your instruction in serving the pleasure of your owner. After that, your owner will take you home with him. Then you will serve in his harem for as long as he wishes. It’s a place where a girl’s need to belong to a man is taken to its logical extreme, if you like. You will be punished from time to time, and you will be enjoyed sexually very frequently whether you wish it or not, but you will not be harmed.”
And the private jet, the white nightgown, a four- or five-hour journey—Olivia had lost all track of time by then—and another ride in another van with Gabriel and the orderlies, though this time without having to suck their cocks. This ride took her into an underground parking structure; out the rear window of the van she saw only a rural landscape that could be anywhere in the Western or Southern states, as far as Olivia could tell. A walk to a room like a nice hotel room, and the command to lie down and go to sleep. The lights were turned off. Though Olivia had expected to lie in bed all night in mental agony, she fell almost instantly into a deep slumber.
In the morning it had begun in earnest. Gabriel woke her up, and made her take a shower in the gleaming white bathroom while he watched through the glass of the shower enclosure, his face impassive except for the small, pleasant smile that never seemed to leave it. Olivia turned away, but he told her she must face him as she washed, and he instructed her to lather her pussy and bottom thoroughly before rinsing them.
Olivia thought she had probably never blushed so hard, but his words in the van about punishment with the strap seemed to make it difficult to disobey any command he gave. Then, after Olivia had dried herself, Gabriel introduced her to Becky, who wheeled in first a sort of beauty parlor chair with stirrups like an examination table, then a cart with everything needed to wax Olivia between her legs.
Gabriel had left, and Olivia had thought that perhaps Becky would tell her where she was, and whether it was true, but she would say nothing as she first cut Olivia’s pubic hair with clippers, then expertly ripped away the cloth strips she had applied, only making Olivia’s eyes water a little though her face felt hot. After Olivia had tried, “Won’t you at least tell me where I am?” Becky had finally said, “I’m sorry, sweetheart. I’m not allowed to tell you anything. Just be as good a girl as you can, and everything will be all right.”
When Gabriel returned, he began by inspecting Olivia between her legs, making her lie on the bed on her back and hold her knees wide open for him. If she had thought the shower embarrassing, with the command to wash between her legs and between her buttocks, this exposure seemed ten times more humiliating.
“When a master says open to you, honey, this is what you will do, wherever you are.”
Olivia’s upper lip quivered, but she held her knees apart, knowing she would be whipped if she didn’t obey.
At last Gabriel said, “You may get up and put on your nightgown, Olivia.”
Then he had sat in an armchair that dominated one corner of the room, and made her stand in front of him, while he began to ask her terrible questions.
When had she masturbated for the first time? When had a boy first touched her breasts? When had she first allowed a masculine hand to touch her between her thighs? When had a man first taken down her panties? How had all those things felt?
“We already know,” Gabriel said softly, “how very naughty a girl you are, honey. Now we want to hear about it in your own words.”
“Fine,” Olivia said, close to tears and not sure why she should be so, given how much she’d already been through at Gabriel’s hands. Why did it make her feel like crying to think about telling a man all the things she had never told anyone at all, least of all the man she had thought she loved? Shouldn’t it have made her cry when she had to suck Gabriel’s and Dan’s and Steven’s cocks? When she had to shower with Gabriel watching? When he had inspected her between her legs and between her bottom-cheeks?
She looked down at his big hands. She had definitely cried when he had spanked her, hadn’t she?
As if he could read her mind, Gabriel said, “Do you need a spanking, honey? Is that what you need, to get you ready to answer my questions?”
Olivia struggled to think of some reply that might make the whole thing stop, because it was suddenly overwhelming. She had sucked his cock, and she had even begun to accept that she couldn’t escape from this Institute place and would become a concubine on a private island—she truly didn’t seem to have any choice about that. But now to admit to Gabriel that she masturbated many times a day, thinking about billionaires and their punishment straps, on their private islands, seemed impossible, and the fact that she didn’t know why it should be so hard made the whole thing worse.
She thought that by hesitating she might buy some time to get hold of herself, but Gabriel to her surprised dismay reached out and took her around her waist. His arms felt just as strong this morning as they had in the van the previous afternoon: somehow, Olivia realized, she had fancied that it might have been a one-time thing—that she could be spanked, give oral sex to three men in a van, and then her body’s perverse needs would be satisfied.
If anything, though, the feeling of being mastered called an even greater response from her body now. She gasped as he pulled her over his lap, not pinning her legs between his the way he had the day before but just laying her down across his thighs the way daddies did with their little girls.
Olivia didn’t struggle as much as she squirmed; the bodily behavior appropriate to this position, somehow.
Gabriel said in a stern voice that somehow also had a gentle note, “Hold still, honey.” He put his left arm around her waist to enforce her obedience, and with it made her raise her backside. He pulled up the little nightgown and cupped both her bottom-cheeks in his right hand, so that Olivia whimpered. “Present this to me properly. Raise it up to tell me you know what you need, even if you can’t say it in words.”
Even if you can’t say it in words. Olivia did: she pushed her bottom up. How could she? She felt the little cheeks rise, held gently by her new master’s huge hand.
Why not Jared? Why couldn’t Jared do this?
“You never told your boyfriend how much you needed a spanking, did you, Olivia?”
“No,” she sobbed, suddenly hoping that with that one syllable the need to answer any further questions would go away.
Gabriel started to spank her.
As he spanked Olivia Rogers’ lovely little bottom, Gabriel’s mind turned to what Charlotte Elkins Nakama, academic dean of the Institute, had told him before he returned to Olivia’s room to inspect her and interview her, the first step in the breaking routine of any girl who played with herself as much as Olivia did.
He didn’t say anything as he punished his new girl, but instead just let her feel the way his hand imparted the discipline she so desperately needed. He enjoyed the bounding of the firm round apples as they quickly grew pink under the painful ministrations that made Olivia yelp louder and louder, and let his mind go over Charlotte’s words.
“Olivia’s here because the right man—or, I suppose, from her perspective the wrong man—caught her playing with herself,” Charlotte had said to him on the phone from her office at the manor house, only a few miles away from the breaking facility. “It’s very important that she not realize that, however, until she sees her owner for the first time and recognizes him. He’s insistent on that point, but from the standpoint of her training it means things are a little complicated.”
Gabriel had frowned, listening to his boss. “But her profile says that she’s ripe. Why doesn’t he just come and sample her?” Ripe was the term Institute trainers and assessors used for a girl who, though still repressed in certain important areas, had enough positive sexual experience that she didn’t stand in danger of harm if an untrained dominant like the man or woman who had purchased her enjoyed the concubine-in-training as he or she liked. Girls reached ripeness at various stages and in various ways; some, like Olivia, arrived that way.
“There are complications, is all I can tell you, Gabriel.”
“Okay. So you’re telling me that when I interview her about her self-pleasure I can’t mention that I know she got caught by a powerful man, even though it’s pretty certainly the most powerful lever I have?” He didn’t try to conceal the ruefulness in his tone.
Charlotte laughed. “Exactly. Pretty good challenge, right?”
“Right,” he responded, a little grimly.
The cleansing tears had come for Olivia, now, over his lap. Her bottom and upper thighs had assumed a nearly crimson hue under Gabriel’s firm hand, and now he stroked it, considering his next move, knowing that the most important thing was to get as much material as he could for the assessors, watching and analyzing the video and data feeds in the Institute’s underground control center.
“Please,” Olivia sobbed.
“Please what, honey?” He kept stroking her little bottom, rubbing the whole sweet, warm backside, then making a little circle with his fingertips in the wonderful, rosy place where buttocks met thighs, and the pressure would travel to Olivia’s certainly wet pussy, while making her think also about her virginal anus and what her fantasies told her happened to a girl’s anal virginity when she was sold to a wealthy man.
She didn’t answer.
Gabriel spoke softly. “When you play with yourself, honey, what happens after a spanking?” He intentionally made the question terribly ambiguous, so that the assessors could measure what happened to Olivia’s body as she tried to figure out what he meant: whether he intended to ask about her fantasies or about her atavistic instinct of shame about her masturbation.
The latter won out, it seemed. Olivia spoke to the floor in a very tentative, quiet voice. “You learn not to… not to touch yourself?”
Gabriel went with it, noting again to himself that he must not refer to her being caught, but hopeful that he had found another lever. He could circle back for the fantasies later. Either way led to the next stage for Olivia, to which he couldn’t help looking forward: her first fucking by him, her breaking master. The first time his hard cock would enter the pretty pink cunt of his new girl.
“That’s right, honey. Your master needs to punish you with his hand, his paddle, his belt, and even his cane, to teach you how to behave. A girl who can’t keep her hands away from her pussy is stealing pleasure from the man who owns that pussy, and owns her bottom, too. Your boyfriend didn’t make that clear to you, did he?”
Gabriel had accompanied his words with gentle squeezes and firm touches, especially as he recited the litany of the disciplinary implements Olivia would soon feel across her backside.
“In a little while you’re going to have a real moment of truth, Olivia. I’m going to fuck you.”
“Yes, honey. Of course I am. You’re going to stand up, and I’m going to bend you over the arm of this chair, push your face into the cushion, and fuck you the way you know you’ve always needed to be fucked.”
Silence. A tremor went through her sweet little body, over his lap.
“First, though, you’re going to answer my questions. When did you first play with yourself?”
Olivia gave a little sob. “I was eighteen.”
“Of course you were.”
“I was thinking about the coach of the football team. There was this rumor that he had spanked a cheerleader for letting her boyfriend go all the way, and I couldn’t stop thinking about it. Oh, God.”
Gabriel heard the shame take hold. “Where were you, honey?” he asked gently, so that she knew he wasn’t judging her harshly for this youthful peccadillo.
“In bed. I put my hand in my panties even though I knew it was wrong. I kept thinking about the cheerleader being punished for having sex, and then I thought about the coach spanking me, because I had my hand between my legs, and I just couldn’t stop. I… I finally had to change my panties, because the ones I had on got so wet.”
“And then?” Gabriel asked, absolutely certain he knew the answer though of course this kind of thing wasn’t in her profile.
“Oh, God. I got those completely soaked, too.”
“If only a man had been there to take you in hand that night, Olivia, and paddle you the way I’m sure the coach would have, if he’d only known.”
Olivia shook her head. “No.”
“Yes, honey. I’m going to recommend that your owner keep a paddle on your dresser.”
“Why?” she whispered, head bowed again to the carpet.
“You can guess, honey. To punish you with, when you touch yourself. You have an owner, now, who will know how to discipline you, before he fucks your sweet cunt, just as I’m going to.” Gabriel began to push his two middle fingers gently deeper in, until he could stroke her warm, wet pussy-lips. Helplessly, Olivia, pushed her bottom back to meet them, begging for more—begging her master to bestow the pleasure she instinctively knew she must not steal from him by touching herself there.
But her words tried to belie that need. “But it’s not wrong,” she whispered, as if hoping to convince herself. “It’s not. It’s my body.” Her voice lost itself in a wordless whimper, as he touched her clit, caressed it delicately.
For a few moments Gabriel let her move her hips on his hand, shamelessly, as he knew she had never done with a man before—had never shown her boundless need for submissive pleasure—but then he removed the hand and said, “What’s true for other girls, or even for women in general, isn’t true for you, Olivia. You need to have your cunt owned by a man. You’ve been begging for it since that night in your bed. You need a paddling when you forget the rules, and touch your master’s property without permission. Playing with yourself is most definitely wrong for you, from now on, and when you are caught doing it you will be severely punished.”
“No,” Olivia whispered, but even a man less well trained than Gabriel Bleigen—even the girl’s boyfriend, he felt sure—could have heard the yes there.
“When did you let a boy touch your breasts for the first time?”
“Eighteen,” Olivia whispered, her resistance to the questions gone. “School dance.”
“Did you masturbate that night, thinking about it?”
Gabriel gave her a sharp spank. “Answer me, Olivia.”
“Yes, of course! Okay? I do it… I do it so much!”
“Do you do it after your boyfriend fucks you, when he’s fallen asleep? In the bathroom, in front of the mirror, with one hand over your mouth and the other between your thighs?”
“How do you know these things?” Olivia wailed.
Charlotte might not like Gabriel coming so close to the area he wasn’t to touch, but he had seen a huge lever there, and he felt sure he could navigate the interview safely.
“When did a man first touch your cunt?”
“Please don’t call it that!” Again, in her voice, the opposite feeling came strongly through: to hear the vexatious, needy place between her legs called cunt brought out feelings Olivia had tried very hard to hide, had successfully hidden, for a long time.
“Olivia, I will call your vagina whatever I like, as will your owner. As will the other men and women who use it, and your mouth, and your anus.”
Gabriel spanked her again, and she cried out. “Answer me. When did a man first touch your cunt?”
“Ow! Nineteen. College. We didn’t… go all the way.”
“I know,” Gabriel said, beginning to rub again, so that Olivia sobbed with ambiguous pleasure. “You went all the way with the boyfriend you dated later that year, in his dorm room, with his roommates outside in the common room.” This detail the Institute profiling team had acquired from cross-referencing a blog post the asshole boyfriend had written.
Again Olivia pleaded, “Please tell me how you know all this. It really scares me.”
“Of course it does. Did you masturbate after you lost your virginity in his dorm room?”
She had reared her head back to make her plea, turned her face to try to look at him. Now she bowed it back down. “You know. You know everything, don’t you?”
“You played with yourself all night, didn’t you, thinking about the way when you said Can’t we wait? And he said No, you’re losing it tonight, and unbuttoned your jeans.” Perhaps a little risky to rely so thoroughly on a blog post written by an asshole, but Olivia shuddered at the words. The safest part was the masturbation, about which they had no actual data but was, for a girl like Olivia, absolutely certain.
“Yes,” she sobbed.
“Stand up,” Gabriel said. As she obeyed, and as he bent her over the arm of the chair, pulling her nightgown all the way up, over her sweet breasts and just under her arms, he said, “We don’t know everything, honey, but we know a lot of things. We don’t know how you felt about losing your virginity that way, or about playing with yourself after sex either that night or every time your boyfriend fucked you.”
He fondled the warm, red bottom he had spanked. Olivia had bowed her head obediently, putting her face in the chair cushion where her master had just sat and gripping its corners with her hands.
“Arch your back, honey,” he said. “Show me you want to be fucked by a man who knows enough not to let you play with yourself. Show me how ready you are for your master’s cock.”
With a little whimper, she obeyed, presenting Gabriel with the sweet prospect of her bare pussy, the little dimple of her anus just peeping out above. He put his left thumb there. Olivia started, a shudder going through her whole body.
“When did a man first touch you here, where you always touch yourself when you masturbate?”
“Never,” she whispered. “Never.”
“I’ll keep my thumb here now, as I fuck you,” he said, adding a note of authority to his tone that seemed to make Olivia tremble. “Because it won’t be long now before your owner deflowers your bottom.”
That first fuck in her cunt had been heavenly, as with his right hand underneath her hips he had made Olivia come three times, screaming her submission into the cushion. It brought her morning session to a close, as he presented her with the pink nightgown from her closet that meant she had been punished that day, and watched her change into it.
Really, Olivia Rogers didn’t need much breaking at all. That afternoon, as soon as her lunch tray had been removed by Becky, he sent Dan and Steven in to fuck her while he watched on the same video feed the assessment team at the Institute were watching, his eyes moving between the Eiffel Tower in which the orderlies engaged Olivia, deep ensconced in mouth and cunt and manfully enjoying themselves, and the stream of psychometric data that accompanied it. He was not such a datahead, as the assessors called themselves and the trainers who had an insatiable appetite for the numbers that governed everything the Institute did, as to find the measurements by which they judged Olivia’s arousal and well-being more diverting than watching two dominants fuck a pretty girl. The live notes the assessment team added to the stream as the lines for galvanic skin response and vaginal humidity flowed by, detected by a tiny sensor Becky had implanted when she waxed Olivia’s pussy, did hold a fascination for him, however. When he saw Heather, one of the assessors, add the note, Arousal 10: we could transfer her immediately, but better to give her the full two days, Gabriel sat back, very satisfied.
The next day, Saturday, Olivia would have her first butt-plug inserted, and she would exercise with it inside her, in the breaking facility’s little gym. She would write letters to her grandparents that would integrate seamlessly with the fake email the Institute had sent to Jared Wertheim. She would be allowed to go to the entertainment room to watch a movie or choose a book. She would probably have another spanking for forgetting a rule, or making eye contact, or showing reluctance to pee with a man watching, but really, they already had in her what the trainers called an angel.
Gabriel didn’t know why someone had even gone to the huge expense of having Olivia Rogers picked up. Couldn’t a man with that much money simply take her in hand, especially after what he had caught her doing? If Gabriel had caught Olivia masturbating, he would have sorted out her submissive desires then and there, instead of paying a fortune to have others do it for him.