A wild idea had just occurred to him, too, and he needed to think about whether it had any promise.
Tess whimpered as she bent to pick up the panties from the pool deck. Anne-Marie’s high giggle floated across from the table. “She looks like she learned her lesson,” the red-haired girl said nastily.
“She does, doesn’t she?” Jeffrey replied amiably. “Tess, darling, I’ll fuck you in the morning. Sweet dreams.”
Tess gave a little sob as she walked to where the dress had fallen. The sight of the plug deep in her little bottom as she stooped moved Jack so greatly he thought he might just pull out his gun and try to make a break for it, dragging Tess away as if he were taking her hostage. Maybe his men would be too confused to do anything, and he could get out the gate before anyone figured out what was going on.
But the chances of getting very far—even onto a boat, for example, that could get them to Crete—were so small that the attempt would amount only to throwing away his chance to take Jeffrey and the Sons of Disobedience down in exchange for a bullet in the brain, if he got lucky and didn’t find himself tortured to death. The “plan’s” only redeeming characteristic was that Tess, when she found herself right back in the compound, probably wouldn’t be tortured or killed.
That mad dash, however, wasn’t the wild idea seething at the back of his brain—the one he didn’t want to think about before he got Tess back to her room, because the roiled waters might turn to steam and vanish.
Tess had her dress, and she cried out, softly and pitifully, as she straightened up, holding it.
“Come along, honey. You’ve got a whipping coming,” he said, trying to make his voice as severe and patronizing as he possibly could, like that of a school headmaster bent on taking out his sexual frustration on an unfortunate pupil’s bare posterior with the school strap.
She gave another cry, and looked at him. Jack didn’t have time to look away before their eyes met, and he saw to his alarm that she had seen through him completely: she, too, seemed only to want to get back to her room—because there, her eyes said, she would be able to pour out her heart.
Dangerous, Jack thought, dismayed. Much too dangerous. He reached out and grasped her upper arm, and pulled in the direction of the bungalow, so that Tess had to take a hobbling step that made her wail at the fullness in her backside. At least Jeffrey seemed to want his sweet dreams to serve as his dismissal, and the table-talk had turned once again to the day-sail the following day.
He marched her at that hobbling pace, bent over and emitting a little sob with every step, to the door of the sprawling bungalow. He got Tess through the door and closed it behind them. If they were lucky, Judy would go to Jeffrey’s bed and Anne-Marie’s to Julian’s, and Jack and Tess would be left alone at least until very late—but counting on such luck didn’t make for success. He needed to think things through, and put the plan into motion, if he wanted it to have any chance.
And if he did set it into motion, there would be no going back: he would have committed both himself and Tess to live free, or to die, as well as hazarding the mission to take down Sir Jeffrey Young and his organization on a single throw.
But though the steps of the plan—the transformation of the wild idea into a list of tactically-organized moments that would make it real—had barely begun to coalesce in his mind, when he turned to look down at Tess’ pitiful face the world stopped, and he made the decision without intending it. Her eyes turned up to his with a sorrowful, pleading expression that said, Now? Will you tell me that you love me, now, at last?
Then he had started to kiss her, though she whimpered with the discomfort of his pulling her to him, straightening her when the terrible disciplinary implement in her bottom made her want only to bend and ease the agony of its invading presence. “I love you,” he whispered. “Oh, Tess. I love you.”
She didn’t say it back, nor did he expect her to, knowing how very complicated her feelings must be now, when she must feel affection for the henchman of the cruel man who had made her his whore—the henchman who had whipped her, had plugged her bottom, and must now whip her again. Who now said that he loved her despite all those actions. Who, Jack could see in her eyes as he kissed, and pulled back to smile at her, and kissed again, believed him without knowing why.
Instead, she said, “Help me. Please, Jack. Help me get out of here.”
He felt his stomach clench. This part of the plan might well kill him with remorse before he could even begin to take action. He didn’t see any other way, though.
“I can’t, honey. We can’t leave. He’d never let us go.”
Her face crumpled. “Oh, God,” she said. “I… I know.” The hopelessness in her voice broke his heart. His consolation lay in the fact that if he told her what he intended, revealed everything to her, it would only be harder for her if they failed—and she would know more for Jeffrey’s men to torture out of her. Lying exceptionally well constituted the most important part of his job, and he had never regretted it until now, when he must take away the fleeting hope Tess had cherished.
She bit her lip. “But… but you’ll take care of me? A little? When… I mean, when you can?”
Jack nodded, looking into her face with an expression he hoped would convey just how hard he would try, tight brow and tight lips showing his concern and his care. But then he said, because he had no choice, “I have to whip you now, though.”
Tess’ nose twitched as the tears welled up in her eyes. “I know. It’s… it’s okay. You have to.”
He nodded again. “Go to your room and lie on your tummy, honey. I’ll take the plug out before I whip you, and put it back in afterward.” Part of him cried out to tell her why, really, it must be thus, and what he intended it should lead to, but if there were the slightest possibility that the unfolding events looked like play-acting, the whole tissue of the plan could fall apart in an instant.
“Oh,” Tess said, her eyes going wide and a little worried. “But… Jeffrey said…”
“I have to mark your bottom thoroughly, honey. You’re going to move around a lot during the whipping, and I don’t want you to hurt yourself. If Jeffrey finds out, somehow, and gets mad, I’ll take the blame. I promise.”
Her blue eyes remained troubled, but she nodded.
“All right. Get going. I want you on the bed and ready for punishment,” Jack said, using the warm disciplinary tone he loved to adopt when the time came to give a lesson to a girl he loved. The affectionate note differed starkly from Jeffrey’s casual cruelty, and Jack could see in Tess’ startled eyes how clearly she had heard the contrast.
“Yes, sir,” she said softly. The sir threatened to melt Jack’s heart, and he couldn’t help bending to kiss her again, before he turned her towards her bedroom door. He put his left hand on the end of the plug, and Tess gave a little whimper just at that light touch. She shivered, and started towards her room.
Jack went to the living room, to get a firm bolster from the couch, and to take the irrevocable step that would end either in joy or in death. On his cell phone, he opened the calculator and entered the thirty-two digit code he had memorized a year before and now recited to himself in bed every night.
The encrypted app, undetectable—the CIA hoped, at least—to any cyber expert to whom Sir Jeffrey Young might have access, opened. He typed the message he had planned and pressed send. Then he restarted the phone, wiping away all record of the message along with the encrypted app itself.
Jack picked up the bolster, upholstered in real leather and very firm—perfect for the purpose he intended—and went to Tess’ bedroom. He found her just as he had commanded, and the sight swelled his cock and warmed his heart: his sweet girl—he couldn’t help thinking of her that way no matter how he tried—naked on her tummy with the very naughty black end of the punishment plug peeping out between her bottom-cheeks.
Her arms were extended to the end of the bed and her cheek rested on her pillow, her face turned to look at him.
&nb
sp; He carried the cushion over to the bed. “Raise your hips, honey,” he said gently. Tess bit her lip and gave a little kitten sound as she obeyed, as the plug moved inside her. Jack put the bolster under her hips, but, though Tess made a surprised little sound, not across the bed but lengthwise down the middle.
“Spread your knees,” Jack ordered. “You’re going to ride the cushion while I whip you.”
“What?” Tess said. “I don’t…” But Jack used his hands to insist on the posture he wanted her in—the classic pillow-humping posture of the furtive masturbator. As her clit touched the leather of the bolster, rubbed against it just a bit, she gave a different sort of cry than she had given yet that night. “I can’t… he won’t let me…” she protested weakly.
“I’m in charge tonight, Tess,” Jack said sternly. “This is how I want to punish you. You’ll ride the bolster during your whipping. Now let’s get that plug out of you so I can punish you properly.”
As he removed his hands from the knees he had spread, the motion brought Tess’ pussy against the bolster, and, as if unable to stop herself, she bucked her hips to rub more firmly there, giving a moan of shame and pleasure that made Jack’s heart take wing and his cock press against the front of his trousers.
Don’t get too caught up in this! he warned himself. You have to be able to think straight.
He put his hand on the base of the plug and gave it a little tug. Tess whined at the sensation.
“Push for me, honey. Hump the cushion and push like a good girl.”
The whine turned into little whimpers as she started to obey, moving her bottom like an animal in heat as she desperately sought the pleasure of the bolster’s already-slick surface. “Oh, God,” she whispered. “Oh, God… oh, God.” She cried out as he pulled the first ridge from her anus, and then she pushed the whole thing out in a rush, riding the bolster faster and faster, obviously close to coming.
Jack put the plug on her nightstand and swiftly yanked his black leather belt from its loops, doubled it, and brought it down hard on Tess’ bottom. She screamed, and he kept whipping, as she rode on and on, her bottom’s clenching and relaxing the sexiest and most marvelous thing Jack had ever seen.
Tess came for the first time, with her head rearing up and her back arching, and he knew he had to do what he had planned now, even if it turned out to be only a fool’s hope. He dropped the belt, then stripped off his trousers and boxers and climbed onto the bed, his feet on either side of Tess’ hips.
“Keep riding, honey. Keep riding,” he said softly as he slid his hard cock inside the velvet grip of her pussy.
Chapter 7
Oh, God. Jeffrey would kill him. Jeffrey would kill her. What was Jack thinking? But Tess couldn’t deny her body’s need for him. She couldn’t deny that suddenly all her shameful urges, all her embarrassing responses to Jeffrey’s cruel mastery, had transformed themselves into something else: sobbing, submissive gratitude for what Jack had started to demonstrate to her. Tess knew now, beyond the shadow of a doubt, that her submission could mean something very different than it had meant with Sir Jeffrey Young.
He did love her. Did she love him? He had done Jeffrey’s bidding so terribly—he had undoubtedly killed people, on the Turkish border and in many other places. Could she love a mercenary?
She cried out, pushing her burning bottom, the bottom he had so thoroughly punished, against his sinewy hips, and ground her clit into the leather bolster. The pleasure seemed to explode outward, upward, downward, inward from that place. He had put the pillow there. He had told her to ride it. How could she not love him for that? For caring about her pleasure—for somehow knowing that she needed this kind of pleasure like she needed air, and that she had been suffocating all her life?
Could she love him, though… the way you loved the man with whom you’re supposed to live happily ever after?
Tess cried out again and again, and it didn’t matter whether she did love him, or could love him, because that level of rational thought had utterly disappeared inside her mind, and all she could feel was how much she wanted him—how much she wanted him to keep fucking her.
She felt like a bitch in heat—completely degraded and completely in need of masculine mastery, riding and riding and riding the bolster to show Jack how his hard fucking was no more than what she required to learn her lesson. He held her hips and fucked, and his cock inside her made her feel like she belonged to him and would always belong to him. His hips pressed hard on the cheeks that bore his belt’s marks, driving her forcefully against the cushion and bringing her so close to coming that she screamed.
Would they hear, out on the terrace? They must… but they would think it was the whipping, wouldn’t they, and Jeffrey would be happy that Jack had undertaken to punish her with the utmost severity.
The way I deserve. The way I need. The thoughts that had seemed so insane when Tess had had to think them about the sociopathic mercenary commander who had taken her prisoner as one of his disciplined whores suddenly seemed to make much more sense, with Jack whipping her and Jack fucking her. They seemed almost healing, now… as if a part of Tess that she had always pressed back into the darkness had crept out into the light so that she could cherish it, and hold it close, even though what it wanted was, strangely enough, to be put over Jack’s knee and spanked.
Just as Jack will… Oh, please… please, will he… over his knee… his huge hand coming down on my little bottom…
On the absolute edge of her orgasm, she sobbed, “Jack… please…” She meant, though it made no sense at all, that she wanted him to take her over his lap right then, like a naughty little girl, and make everything all right again.
“Shh,” he said, and then to her distress he pulled his cock out of her pussy. For a moment she thought he had read her mind, and she wanted to say, No… I was wrong… keep fucking me… please don’t stop!
But then he said, “Tess, I’m going to fuck your bottom now. Open up for me like you did for the plug.”
“Oh, God,” she said. “Please… Jeffrey will…”
She knew that if they were discovered that way, with Jack’s cock in her ass, the consequences would be more terrible than she could probably imagine. Torture, not discipline. Real death. Jeffrey had told her that her ass belonged to him, and she had known somehow even on the first night that he had meant he would kill anyone who tried to steal its pleasure, and would kill her in the bargain if she showed any complicity in the theft.
But could she deny that a part of her at least would rather die than live like this? Would rather die than not have that shameful, special part of her stolen from the man who had first ravished it and so cruelly punished her there, so arrogantly fucked her there night after night.
In that strange moment, hovering between rationality and the irresistible ecstasy of the pleasure just out of reach, Tess remembered being over Jeffrey’s knee, for saying, oddly enough, the word fuck. It had happened on her third day in his compound, by the pool, before she had known the sometimes quirky rules under which she and his other girls had to live.
“Tess, darling,” he had said from his seat at the table where his tall Amstel rested, “that’s not a word a lady says. Come here. You have a spanking coming.” He had patted his left knee,
“What?” she had said, but she had known immediately that he meant it, and the horribly ambiguous feeling in the pit of her stomach had told her that she would go over that knee, because… because he had mastered her, and he had guessed what she had always needed.
“You better go,” Judy had said, feigning sympathy. “It’ll be worse if he has to come get you.”
As Jack put the head of his cock at the little ring of her anus, and Tess instinctively pressed down with her clit against the lovely leather-covered firmness of the bolster, she recalled how it had seemed both right and wrong to have Jeffrey upend her, and pull down her bikini bottom, and start to punish her, saying, “Naughty girls have to learn their lessons, darling.”
Now, though… now she very nearly begged Jack not to put his cock there, though she felt desperate for that thorough claiming—that stealing—too, but rather to claim her by taking her over his knee and spanking where the marks of his belt would make it hurt so much, so much.
But when he pressed with his hardness, patiently—not forcefully like Jeffrey, even that first night—and said, “Good girl,” and Tess felt herself open to him like a flower, so well prepared by the horrible black plug that she could see, sitting there on the nightstand now like a reminder of the difference between the two men who had fucked her bottom… well, she still wanted that spanking, especially if they were both going to die at Jeffrey’s hand, soon—in the ecstasy of that moment of claiming Tess could almost giggle at death itself—but Jack had chosen to fuck her bottom, and Tess knew he had made a good choice, since she instantly started to come, as the cock in her anus caused her to push her clit one more time against the bolster, and the world seemed to go away completely.
She was screaming with pleasure, and submission, and discomfort, in a way she had never cried out before, and… Oh, no. She had screamed his name. She had screamed “Jack, oh God. Please…”
As she came, though, the giggle at death she had almost let out before became something more existential: laughing in the face of danger, or… not laughing but… but coming, in the face of danger, and death, and Sir Jeffrey Young, Bart. Coming, and coming, and coming, as Jeffrey himself did burst through the door, did see Jack Regensburg, head of his security team, with his cock in the ass Jeffrey had claimed as his own.
Hero Undercover: 25 Breathtaking Bad Boys Page 133