by Emily Tilton
How could he call her darling? Tess had wondered it before, but never quite so forcefully. Darling meant someone was dearer to you than anything. How could it be that when Jeffrey said darling, Tess heard whore, but when Jack said honey, she heard darling?
She cried out again, because Jack had pushed on the plug, so that the second thick ridge opened her anus. She couldn’t. She just couldn’t… “Please…” she sobbed, sure that he would have mercy on her and withdraw the thing. But he kept pushing, made her take it until the narrow part came again and she had two bulbs of the awful thing inside her bottom.
“Do you think you’ll be late again, Tess?” Jeffrey asked with cruel mockery in his tone. How could she ever have found him charming?
“No,” Tess sobbed. Her bottom squirmed and clenched uncontrollably, helplessly trying to expel the rubber intruder, but Jack held it inside her firmly, still pushing, but more gently now. How many more ridges? One? Two? Her bottom felt much too full, and her anus burned to be held open around the plug. The picture in her mind, through Jeffrey’s eyes, made her feel faint with shame: her little bottom full of the lewd disciplinary shaft meant to teach her to behave.
“That’s why I spank them,” Jeffrey said, his tone conversational again as he picked up the thread of his discourse. “They need to understand that they’re here to do as they’re told, whether that’s to be charming and prompt at dinner or to spread their legs and raise their knees in bed, so that my cock can have its way. It’s all about attitude.”
Julian and Ahmad chuckled politely. Judy and Anne-Marie held their silence, and Tess wondered whether they were pretending to find this arousing—the way she herself couldn’t help the clench her pussy gave at the degrading words. Or perhaps even though they never seemed to respond the way Tess did, they couldn’t help feeling the awful pull of Jeffrey’s dominance. As Jack moved the plug gently back and forth in her bottom, perhaps waiting for Jeffrey’s command to push it in further and perhaps wanting to help her get used to it—or perhaps both—she imagined again, helplessly, that Jack had said the thing about spreading her legs and raising her knees. She bit her lip to keep from crying out, as her pussy clenched again, and her bottom with it, and suddenly the discomfort seemed to become something more, something like pleasure.
“You fucked Judy last night, Ahmad,” Jeffrey said. “What did you think? Have the spankings paid off?”
Ahmad chuckled. Tess thought she sensed just a bit of tension in the sound, but she knew that Jeffrey’s lieutenants would never think of disappointing him in such matters. “Definitely,” he said. “Judy was a very good girl for me.”
“Jack, lad,” Jeffrey called then with a grandiloquent note in his voice, as if reasserting his right as master of all he surveyed, including above all Tess’ backside, “what are you waiting for? Give her the rest of it.”
He doesn’t have a choice, Tess thought. He doesn’t have a…
Then she lost the ability to think in words, for a long moment, because Jack obeyed his commander and pushed firmly. Tess’ hips bucked and she bounced up and down, her elbows pressed hard into the mesh of the lounge chair and her eyes watering. She wailed, and then she screamed, because the man who kept her had commanded she must have this big black thing up her bottom, and it hurt.
Then the third ridge was in, and Tess thought for just a moment that she would be given a respite at least for a few seconds, but Jack… He has no… he has no…
She screamed: the fourth ridge, the thickest ridge, pressed for entry. “Please… please…” she begged, but Jeffrey laughed, and Jack kept pushing. Her bottom was full, much too full. She tried to straighten up, following some instinct to flee, but Jack pushed her down with his left hand on her back, and kept pressing the plug inside her until at last the final narrow place allowed her little flower to close around it, and she had the whole thing up her narrowest, most private place.
Tess hung her head and sobbed. She had never felt so exposed, degraded, possessed by a man who wanted her only for her use as a sex toy that might as well go into the toy box with the plug at the end of the night. Nor, if Jeffrey carried through on his threat, would it end now, for he had decreed that she must kneel before the men and suck their cocks.
Perhaps, though, Jeffrey had felt the tension in Ahmad’s answer about Judy, for—as happened relatively often—he changed his mind.
“Take her to her room and whip her, Jack,” he said. “I want to see some nice welts on that bottom tomorrow. Remember that the plug stays in all night.”
Chapter Six
Jack leaned down to grasp Tess’ upper arm and help her up. She cried out pitifully as she straightened, her hips weaving in an unintentionally lewd way that stiffened his already hard cock still further.
“Pick up your panties and your dress,” he said, hating himself. He didn’t have a choice, though: if he picked them up for her, Jeffrey would surely find Jack’s treatment of the miscreant too lenient, and change his mind again. Right now, he just wanted to get Tess back to the bungalow and spare her more cruelty and himself more risk.
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. But Jack could see in her eyes as he kissed, and pulled back to smile at her, and kissed again, she 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.
“Alright. 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 toward 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 toward 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.
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, and, 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 knees 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 Seven
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.