The first time Sir Jeffrey Young, commander of the Sons of Disobedience and dealer alike in small arms and high-powered ordnance, made Tess wear a butt plug, he did it on a whim. Tess had displeased him in a relatively small matter, failing to appear promptly for dinner and seeming to deceive him about what she had been doing. Jeffrey, probably feeling a little jaded with the usual command to one of his bodyguards to belt-whip her in front of him, said with a sadistic glint in his eye, “Let’s put a butt plug in that pretty arse, and make her wear it at the table. If she can’t show up on time, like a civilized young woman, I’ll just have to treat her the way she deserves, like a misbehaving pet.”
Jack, the head of Jeffrey’s security detail, laughed and said, “What, seriously? You wouldn’t put a butt plug in a pet’s rear end, would you?”
Perhaps Jeffrey hadn’t meant it seriously when he said it, but now he seemed both amused and aroused—as Tess might well have expected, given how aroused it usually got him to humiliate her and his other girls. He liked to degrade Tess more than the others, though, and she knew the other girls tittered about it. Tess thought it must be because although it troubled her, Jeffrey would always find her wet and ready afterward when he took her to his bed, whether he had had her whipped in front of his guests or he had made her take off her panties at dinner and give them to him.
Anne-Marie and Judy, the other two current members of what Jeffrey at least never called his harem in so many words, though Tess had heard some of his men call them that, didn’t get spanked as much as Tess did. Jeffrey never said why, but she didn’t think it could be because she didn’t behave as well—which Jeffrey used as the excuse for the frequent punishments. Anne-Marie constantly spoke of things she shouldn’t, on her shopping trips outside Jeffrey’s compound on the little Greek island where they spent most of their time, but never got spanked for it. Judy would go out dancing with visiting lieutenants of Jeffrey’s, without permission, and suffered no ill consequences. If Tess had done that, Jeffrey would almost certainly have taken her over his knee, by the pool, the next morning in front of the servants. With her bikini bottom down she would have been spanked until she sobbed out her penitence, her legs kicking uncontrollably and showing everyone present—including the other girls—the parts of her Jeffrey had instructed she keep bare, waxing them once a week.
Anne-Marie and Judy also had to wax, but Jeffrey let them keep some of their pubic curls, shaped in tight little triangles. Only Tess had to remove them all. They all saw each other’s privates often, of course, because of Jeffrey’s love of commanding them to sunbathe nude, then bringing one of them into his cabana for afternoon sex. When he chose Tess, he would always turn her face down and enter from the rear, but she knew he had other favorite positions with the other girls: Anne-Marie on her back, with her knees bent and spread; Judy on her side, from behind as with Tess, but surely less degraded than Tess felt to have her face pushed into the canvas of the beach chair, bottom high as Jeffrey rode to his orgasm without any thought for her pleasure.
When he did consider his girls’ sexual pleasure—and this held true for all three of them, as well as for Bella, a girl who had been sent away a few months after Tess arrived, after sleeping with one of Jeffrey’s lieutenants—it was always in conjunction with a spanking. Even if he had a bodyguard carry out the punishment, the girl was brought naked to Jeffrey afterward and made to bend over in front of him so he could inspect her whipped bottom, whether he was alone at the time or surrounded by other men. Then, as an explicit completion of the discipline, he would get the vibrating dildo out of his desk and work her pussy on it until she came, crying out how sorry she was for her offense.
“See how much you liked your spanking?” he would usually say. “Now go wait for me in bed.”
That happened to Tess more than it happened to Anne-Marie or Judy, but Jeffrey fucked each of them with just about the same frequency—the important difference lay in Tess’ nearly always having a spanking before Jeffrey sent her to his bedroom. The other girls got sent there unpunished, or got fucked in the cabana or in the pool house. The cause, Tess thought, lay in Jeffrey’s having decided—whether rationally or instinctively she couldn’t puzzle out—that she aroused him most, and made a better lay, when he had degraded her.
The question of how she had gotten here, and why she accepted the humiliation, was one Tess didn’t care to think about, any more than she liked to think about the specific idea that she got turned on when Jeffrey displayed her naked to his guests, or that when he made her spread her bottom-cheeks for anal and said, “Such a pretty little arse-hole,” her pussy flowed. She usually told herself the story as, “One minute I was vacationing in Greece and the next minute a rich Englishman had swept me off my feet.”
The truth of course was much more sordid, and involved the first of the many degradations Jeffrey had visited upon her for his twisted pleasure in the six months she had been one of his girls. Tess had been drinking in a little taverna with the three friends with whom she had come on a college summer trip to the Greek islands, and she had gotten mad at something Julie Taylor had said about a guy Tess had liked. She had decided, a little drunkenly, to walk back to their hotel alone.
As she passed by an elegant restaurant, a big man had detached himself from the whitewashed wall and come to say in a British accent, “Miss? There’s someone who would like to meet you, in the restaurant.”
Confused, frowning, Tess had said, “Who?”
“A wealthy, handsome man,” the bodyguard (as Tess later learned, his name was Jack) replied.
What the hell, she had thought, of course, and gone to sit at his table. Tess later learned that upon seeing her pass by, Jeffrey had had his other bodyguard take Bella home to the compound, so that Tess would receive his undivided attention. Or that represented the best face to put on it—the face Jeffrey himself put on it when challenged as to why he hadn’t told her she would be living as one of (then) four girls whom Jeffrey fucked in rotation.
That challenge, a few days later, had earned her first spanking, but that terrible punishment hadn’t been the first indication of her new ‘boyfriend’s’ intention to degrade her, or of her body’s helpless, not-to-be-examined response to it. No, Jeffrey had signaled quite clearly to her that he meant to treat her more or less as a whore from the very beginning. Tess supposed she had just felt sure he must be playing—that the stunning gold bracelet he had bought her at the little jewelry shop, after feeding her grilled octopus that tasted like the Aegean itself, must mean that when he said, “I’m going to fuck you here, tonight,” and put his hand on her backside, the arrogance in his voice covered over some essential tenderness.
He had woken up the owner of the jewelry store to come down and open the shop, and laughed with him about it, and Tess had laughed too. The sudden dirty talk, well, it had excited her, then. She had kind of always wanted to try… things, and here was a rich man who seemed to know how to try things, and wanted to give her expensive gifts, too.
Part of her reluctance to think it through, a process that might be expected to lead to her making at least some gesture toward leaving—or, rather, running away, because no one simply left Sir Jeffrey Young’s service—lay in her consciousness of how stupid she had been. Could she have left when he said, at the door of the car that had just pulled up in front of the jewelry store as if by magic, as the bodyguard held it open for her to climb in, “Time to go to my house, darling. I want to see if your ass is as perfect without your skirt and panties covering it as it looks right now”?
He had accompanied the words by lifting that short blue skirt to fondle her there, where he had promised to fuck her, his hands roaming freely over her rather sensible gray cotton underwear. She had brought some fun, lacy stuff on the trip, but she hadn’t worn it that night because she and her friends had promised not to try to fool around with hot Greek guys that night. When she felt his hands just do that—just go boldly up her skirt while the bodyguard stood there impassive—Tess had looked up into his handsome face with its two-days’ growth of dark beard, and tried to figure out why she wasn’t saying anything, when back home she would have screamed bloody murder and run for the police.
She had pretended she hadn’t heard when he had said the outrageous thing about anal sex. She had tried half-heartedly and, now, thoroughly drunkenly, to refuse the bracelet, but Jeffrey had said that what seemed a small fortune to her represented five minutes’ work to him. Then he had even said, “You’ll pay me back tonight in bed.”
And Tess hadn’t said no, then, nor had she said no when the bodyguard opened the door and Jeffrey’s hand went up her skirt.
In his bedroom, deep inside the spectacular compound to which the car brought them, its lights piercing the night sky, she had hesitated when he told her to kneel on the bed and bend over. That had resulted in his first hint that he would spank her, but, again, some part of her brain had told her that he must be playing, and her body’s response to his words seemed to draw her on without hope of refusal.
“Do as I’ve said, Tess. I don’t want to have to punish you. Face down and bottom up.”
She wondered, when she thought back on that night and the ‘relationship’ to which it had led, whether Jeffrey had seen her that night and specifically decided to try to degrade her as much as he possibly could, as a sort of challenge to himself. In that sense, Tess supposed he had actually been at play, to the extent Sir Jeffrey Young, mercenary and arms dealer, could ever be at play. The problem lay in his actually being an even worse person at heart than the man who would give a gold bracelet in a frank, degrading exchange for an nineteen-year-old’s anal virginity—always having the intention to keep her in his compound by playing at being charming the next morning when he invited her to stay.
So, taking his threat as playful, and because at that moment she had, though quite drunk, to deal with a kind of arousal she had never felt before—among other things, she didn’t feel sure she didn’t want to be punished, but she also didn’t want to think about that uncertainty—she had obeyed. She had knelt, bent, and felt the man who must be some kind of mercenary (she had guessed this with a hard gulp when she saw the armed guards patrolling the compound) lift her skirt.
He had fondled her bottom through her panties for a long time, as she gave little whimpers, so very caught in this utterly new way to do sex that she didn’t even want to ask herself whether she liked it or not. He had praised her arse, her thighs, her slender back, and he had pressed upon her, there, with his big hands, telling her to ‘present herself’ for him.
“Show me where you need my cock, darling,” he had said. “Have you had a man in your arse before?”
Tess had felt her face go bright red at that, and suddenly had known a sort of gratitude that he had made her put her face in the covers. She had shaken her head.
“Say it, Tess,” Jeffrey had ordered, his voice harsher now. “Say it in words. Have you been fucked in this arse by one of your college boyfriends?” As he had spoken, he had pulled her panties down, and then eased her bottom-cheeks apart on his thumbs.
The heat had blazed in Tess’ cheeks. The disdain this man had shown for her previous sexual experience had made her feel faint, and unmoored from the reality she had known until just an hour or two before.
“No,” she had whispered.
“Of course not,” Jeffrey had said. “That’s why you’re here with a real man, who can give you what you need. This belongs to me, now, and I’ll decide what it gets.”
Then he lubed her roughly, making her cry out, and entered her, crouching above her backside like a lion. He rode hard even that first time, so that Tess wailed in discomfort though the terrible, inexplicable arousal never departed. He came with a grunt, gripping her hips firmly, after a few minutes of steady pounding.
Then he made his one concession to tenderness that night, if it could be called that. “I’ll wash up before you suck my cock,” he said, as he withdrew from Tess’ burning ring.
Jack Regensburg had at least one more problem than he thought he could easily deal with. That problem’s name was Tess Roberts. Taking down the kingpin of the Sons of Disobedience, the once-right-honorable baronet Sir Jeffrey Young, would probably not have posed a challenge otherwise. Like the vast majority of such self-made international criminals, the man had a need for display that would have doomed him to capture a month ago, if Jack hadn’t cared about what happened to Tess in the possible crossfire or, just as bad, in the system that would snap her up with the man who had taken her captive, for all intents and purposes.
He thought he probably would have owed her that much on purely ethical grounds, even if he hadn’t fallen in love with her the moment he saw her having breakfast with Jeffrey, the morning after he had seduced her. On the sweet, mostly innocent, not-quite-perfect oval of her face, framed in the tangle of ash-blonde hair that came down in unkempt waves to her shoulders and needed to be brushed back once a minute or so, Jack had seen that the girl’s first experience of rough sex—for though Jeffrey showed an admirable variety in his appetites, his satisfaction of them was always rough—had left her terribly confused. Jack had known with absolute certainty that if somehow he had met the girl somewhere else—on a New York street or in a San Francisco café—he would have been able to talk her through it, and probably ended up in bed with her with the intent of teaching her that submission didn’t have to make you feel as ambivalent as she felt right now, after her night with a ruthless mercenary.
He had heard, an hour later, that she had accepted the invitation to stay, and had called her friends to say that she would meet them back in Athens in a week. Jack had then spent five minutes—time he should have used in figuring out how to use Jeffrey’s new infatuation against him—trying instead to figure out whether he could risk blowing his cover by somehow getting Tess out of the compound and back to her friends, and then getting all of them on the ferry. Jeffrey’s other girls, decidedly older and wiser than—though nowhere near as intelligent as—Tess, could take care of themselves, if they got caught up in the web when Jack took the mercenary commander down. Tess would have her life ruined by the inevitable public revelations, her youth slipping away as she dealt with the fallout. She could write a tell-all book, of course, but Jack didn’t see that as much consolation when Tess clearly had a bright future ahead of her, if she could only get out of here.
But Sir Jeffrey Young, bart., had killed thousands of people around the world, and would kill thousands more if allowed to go on selling arms. Jack had worked the case for two years, and had finally come close to rolling up not only the Sons of Disobedience but two other mercenary groups as well. To risk that now by incurring Jeffrey’s wrath and perhaps getting both Tess and himself killed made no sense. He might have been falling in love with Tess more every day, and longing to dry the tears he saw her cry more and more regularly as she understood her true situation as a sex toy in a paradisiacal prison, but he had no choice.
When Jeffrey ordered that Tess be made to wear a butt plug, then, Jack knew he didn’t have any way to spare her the terrible humiliation. His knowledge of how troubled and complicated her feelings about her submission to Jeffrey were made it an exquisite torture for him, though, which he pressed as firmly as he could to the back of his mind, as he used all his skill to pretend he found the idea amusing.
“Maybe you wouldn’t make a dog wear a butt plug,” Jeffrey conceded rather contemplatively, “but Tess here is a very special kind of pet—the kind who gets it in the arse. Jack, my lad, go get the toy box, would you?”
The dining area in Jeffrey’s compound lay between the enormous villa and the beautiful pool, where the sound of the pool’s waterfall could susurrate under the conversation, such as it was. Jeffrey had the benefit of a university education, like Jack himself, but the mercenary’s interests lay completely in the financial world, when he wasn’t keeping the discussion on the two matters to which he addressed himself as his vocations: combat and sex, in both of which he maintained his superiority in a cultured accent, expecting full agreement from his subordinates on every point.
He had just been telling Anne-Marie and Judy, who sat next to Julian and Ahmad, Jeffrey’s top lieutenants, at the long table, that Tess had better get her backside out here or she would find herself sleeping alone with a sore bum, and Judy would come to his bedroom in place of her. Judy, clearly sensing the possibility of gaining an advantage over Tess and perhaps enjoying a second honeymoon with Jeffrey, with all the gifts and shopping that would entail, had said, “Tess was just watching the news when we left the bungalow.”
Jeffrey called the little freestanding house the bungalow, but it might as well have been called the seraglio. His girls lived in it, when they weren’t called to his bed or, after their honeymoons, as all Jeffrey’s men called the initial part of the girls’ stay, the beds of lieutenants given express permission to summon this or that girl. Ahmad had been fucking Judy for a week now, and she—understandably, Jack thought dryly, because Ahmad couldn’t provide the luxuries Jeffrey could—obviously would rather be summoned back to Jeffrey’s bed, which Tess and Anne-Marie had lately been occupying. Jeffrey’s rotations through his girls were intended to provoke jealousy, and they did—in Anne-Marie and Judy, at least, though not in Tess.
Oh, no, Jack had thought, and then Tess had appeared, her face troubled and, Jack had thought he could discern, tearstained.
“Tess, love,” Jeffrey had called. “What did you see on the news?”
Her eyes had widened, and then her glance had darted around the table to Anne-Marie, to Judy, to Jack. Jack had kept his face impassive, though he had known that no good could come of this—and probably a lot of bad would. If only Tess weren’t so smart, he thought ruefully. He had seen the signs that she had figured out what Jeffrey did on the ‘business trips’ he made once a month or so, sometimes for a week or even two. Now he had read on her face that on the news she had probably seen something about the fighting on the Turkish border, where Jack himself had been only three days before, with Jeffrey, abetting the propagation of unspeakable suffering.
“Nothing…” Tess had said. “Just… you know, movie stars.”
She had tried a laugh, but it had sounded very false, and Judy had gone in for the kill.
“That’s not true, Jeffrey. I saw what she was watching. It was, like, war and stuff.”
Jeffrey’s eyes had narrowed. Dammit, Jack had thought, why did she lie?
Then, apparently judging it a matter for discussion at a later time and having a sudden erotic urge in response to his annoyance at Tess for being late, Jeffrey had chuckled. Looking over at Jack, who stood guard a few yards away, he had said, “Let’s put a butt plug up that pretty arse, and make her wear it at the table. If she can’t show up on time, like a civilized young woman, we’ll just have to treat her the way she deserves, like a misbehaving pet.”
Jack had managed to laugh, hoping that Jeffrey would think better of subjecting Tess to such extreme degradation. Jack could see the place of anal discipline in the bedroom, of course—as an experienced dominant who had fallen in love with Tess precisely because of the obvious strength of her need for erotic discipline, he would gladly have introduced her to the idea, and the delicious practice of imposing and receiving a butt plug. Not here at the dinner table, though, with her awful ‘rivals,’ willowy, raven-haired Judy and curvy, red-haired Anne-Marie watching and triumphing. Not in front of Julian and Ahmad and Jack himself, as well as the other members of Jack’s security team, on patrol, who wouldn’t fail to patrol nearer by as Tess’ cries and whimpers rose into the night over the splash of the waterfall.
But Jeffrey would very rarely give up such an idea once he had hold of it. Even when they were in the midst of an engagement, and his instincts told the mercenary something Jack knew to be incorrect, it was hard to get him to let go of the urge. When it came to sex, and the way he liked to see girls degraded, almost nothing would stop him in his libidinous course.
He had told Jack to get the toy box.
Tess looked wildly at Jack, and a lance of pain stabbed his heart, because he knew that somehow she had discerned, or perhaps only suspected, how much he cared about her, and she looked to him now to help her avoid this terrible whim of the cruel man who had taken her into his power. Jack had no choice: he had to leer at her, play the part of the hireling who would dearly love to fuck the boss’ woman but knows enough to keep himself in check. Jeffrey was looking at him, judging his reaction; Jack knew that beyond the slightest doubt.
Sir Jeffrey Young had true acumen in two areas: salesmanship and leadership. Both required an instinctual grasp of basic human character that Jack spent much of his time trying to fool. To show Tess the slightest degree of sympathy at this moment could doom both of them, as well as all the people Jeffrey’s arms would kill in the years to come.
But the look on Tess’ face, when she saw that her wild hope that Jack might intercede and stop this most humiliating of domestic disciplinary punishments held no promise of success, took hold of the lance that had pierced his heart and twisted it savagely. He didn’t think he had ever experienced such emotional anguish, and for a moment he almost broke, almost told Jeffrey he wouldn’t do it, that he would take Tess right now and leave the compound, so that when she wore a butt plug for the first time it would be in the privacy of a little cottage somewhere in Devon, or New Mexico, with Jack’s arms closed tightly around her as she trembled to have her submissive nature so completely exposed and so completely gratified.
Her face crumpled, and she dropped her eyes to her bare feet. The setting rays of the sun over the Aegean rendered her pale blue sundress almost transparent. Jack wondered, as he could never keep himself from wondering, what lingerie she had on. Jeffrey didn’t care much for lingerie, so his girls tended not to wear anything special, as most people would think of specialness, but Jack had to admit to finding every piece of feminine underwear special. Catching a glimpse of Tess’ gray panties, for example, when Jeffrey would carelessly and possessively raise her skirt to put his arrogant hand on her backside, could make his cock hard in an instant.
The terrible time Jeffrey had made him whip Tess with his belt three weeks ago, which he now realized must be the reason she had looked at him for help, she had worn blue panties with a lace waistband and lace around the legs in a scalloped border. His hands had lingered, for he simply couldn’t help it, as he had pulled them down. He had said very quietly, “Get ready now, honey. I’ve got to make this hurt.”
He shouldn’t have said it, Jack realized now. He had meant to let her know, as best he could, that a real dominant cares for his submissive girl. He had meant to convey to her everything it now appeared she had in fact gathered. He had meant to tell her he loved her, and he had only made matters much worse.
Now he had to undo it. He went to get the toy box.