He pulled hard at Tess’ shoulder, which should have made her cry out in protest, but the tension in her muscles had not returned, and she made no sound at all as she followed him.
Dangerous. Terribly dangerous. If Tess behaved as if she were in love with him, all Jack’s tradecraft, such as it was, could do nothing. Jeffrey would figure it out, and kill her, and then Jack—because he knew he wouldn’t be able to stop himself from trying to save her. The only redeeming element of that scenario, Jack supposed, lay in the fact that his being a CIA operative probably wouldn’t be discovered.
He had no choice. He twisted her arm behind her, bringing her wrist up to the small of her back as he bent her over the fully-extended chair, upon which one of the wall-lights that illuminated the pool area shone like a spotlight. Tess cried out. Jack desperately wanted to put his mouth to her ear, say something that would get her to respond more naturally while also making it clear that he loved her and would never harm her. He had not the slightest doubt, though, that to try that would make the situation much, much worse.
“Get that ass up, honey,” he said. “I’m going to take your panties off now.”
Tess greeted this news with a little sob. Her head hung low in apparent penitence and her hair spilled all around her face. Jack didn’t think he could imagine a sweeter sight: his desperation to be the man she called sir, the man who gave her what she needed, rose so high he thought it might freeze him in his tracks.
He had taught himself the art of dominance with the help of his first real girlfriend, in his single year at college. The leading, pointed gift of a riding crop from the pretty red-faced senior, two years older than Jack, had served to guide him past his uncertainty as to whether some girls really did feel the need to submit, and even to accept discipline for things like sub-par grades and lateness. Now Jack knew a submissive when he saw one, and he had seen a very confused, thoroughly lost one in Tess, her first morning in the compound—she had mistaken Jeffrey’s heedless, rough ways for true dominance, and Jack had felt helpless to do anything that might teach her a different, better lesson.
If that first moment of recognition had posed difficulty and complications, it had had nothing on the time Jeffrey had told him to whip her. To know what Tess needed and to have to give her something completely different had burned in his mind, and left him sleepless for days. He pictured her sobbing, writhing form as he had covered her backside with curving red welts, and then he pictured what had not happened: the cuddling aftercare she should have received instead of the command to go to Jeffrey’s bed and wait for him to come fuck her, when her confusion about her erotic reaction to the belt-whipping would have left her aching and desperate.
But, now: to have to administer her first session with a butt plug represented an even worse torture. Jack tried to tell himself that it differed only in degree from the whipping, but he knew himself a liar: the intimacy of anal discipline and the way it got literally to the bottom of a girl’s submissive fantasies couldn’t truly be compared even to a severe whipping.
He had no objections to using a butt plug as a punishment, but he knew it always represented a very special kind of punishment. He would never have thought to make a girl receive and wear a plug in any public or even semi-public place like this, but Jack’s main objection didn’t lie in that quarter, because he could easily imagine negotiating a scene like this with a sub who found public humiliation arousing. He even thought it probable that Tess might be that kind of girl, if Jack could give her the training and support she deserved.
No, the reason that he had to grit his teeth as he moved Tess’ left wrist in front of her, and down to the lounge chair so that she could support herself with both palms on the sturdy blue mesh surface lay in his knowledge of just how intimate an experience a girl’s first anal punishment should be. Jeffrey had made Tess’ first anal sex an ambiguous, rough affair, Jack knew, and the frequency with which he renewed her bottom’s acquaintance with his cock must be great, judging from the way he had seen her fidget at breakfast after a night in Jeffrey’s bedroom. But anal discipline should, Jack knew, be different, if Tess’ submission were ever to be something she could fully enjoy.
It should have an essential gentleness to it, despite being intended to teach a lesson. It should proceed slowly, with every push of the punishment plug accompanied by a pull, to let the girl’s little ring close, and rest, before she must try to open it again, wider than it had ever opened before. When Jack had selected the long, ridged plug, he had done so because he thought that even though he must not take the time, or say the soothing words, the way Tess deserved, the entry of each ridge into her bottom might allow her some space to process the experience.
He put his fingers inside the waistband of the grey panties, thinking about the lace on the blue ones he had taken down to whip her, thinking about how if she belonged to him she would wear lace every day, or no underwear at all. He pulled them down swiftly and she gave a little gasp as if at the suddenness of the baring.
The party at the table had begun talking of the sailing trip planned for tomorrow, out to a tiny, uninhabited island for snorkeling and a picnic lunch.
“Step out of the panties, Tess,” Jack said quietly. “Feet a little more than shoulder width apart. Bend your knees and put your elbows on the chair. I’m going to lube you now.”
“Oh, God,” Tess whispered, as she obeyed, when she realized how very exposed the posture made her. Jack’s cock swelled in his black trousers at the sight of the sweet young pussy and the tiny pink flower that must receive the plug.
Chapter 5
Behind Tess, the murmur of conversation at the table stopped. Oh, no.
“Look at that arse,” Jeffrey said. “That’s why she’s here. I saw it walking down the street and I knew I had to get inside it.”
She gave a little sob, and she felt again the tingling in her nipples and the warmth down below that it seemed only his humiliation could bring. Shouldn’t a girl who got wet when her lover talked about her that way just accept her fate? How could it matter that the man perpetrated so much evil, when her body’s response to his brutality was panting arousal?
“You never said that about me.” Anne-Marie’s voice seemed to able to pout just in its tone—Tess had no need to see her face to know what expression occupied it.
“Darling, you know I like to fuck your arse, too, but Tess’ bottom is a very special thing—you can see that yourself. Shaped like a heart—not too big and not too small. And I just have to say that I’ve never seen an arse-hole that looks more like a flower.”
Tess’ face blazed, and as she felt Jack’s fingers touch her there for the first time she realized that although she had experienced the problem of being aroused when Jeffrey degraded her in public before, she had never known it to be so severe. It’s Jack, she thought. It’s knowing that he’s the one doing it. Oh, God.
Suddenly she imagined that every time Jeffrey had told her to spread her bottom-cheeks for him, so he could ready her, it had been Jack instead. That every time the mercenary had impaled Tess with his cock, and used her for the tightness of her smallest opening, until he found his release inside her, Jack had fucked her there instead. Jack’s muscular arms holding her in place; Jack’s bearded face rising above her, telling her to be a good girl for him. She cried out at the picture in her mind, much more moved by that fantasy than by the fingers that rubbed the lube on the surface of the little ring, only pushing a very little now.
She realized that the conversation had resumed at the table after Jeffrey’s words to Anne-Marie, because now it ceased again, and Judy said in a giggly voice, clearly trying to out-do Anne-Marie, “She doesn’t like it, does she?”
The attempt backfired on her though, because Jeffrey’s annoyance was audible in his response. “Do you want some, Judy? Tess is learning a lesson, but maybe you need one, too. Do you need a plug up your arse, Judy?”
“No,” Judy said flatly, sullenly, and without apparent fear th
at Jeffrey might follow through on the threat. Tess thought she could hear in that monosyllable—in the way it differed so vastly from how she herself would have responded—how she had come to this emotional place. She saw in an instant how and why she, who had meant to change the world, could think of herself as deserving no better than to have Sir Jeffrey Young fuck her in the ass when he felt like it, and send her to his private brothel when he didn’t.
She didn’t know why Judy and Anne-Marie were here, but Judy’s no to the question Do you need a plug up your arse? actually meant no. If Tess had been asked the question, she too would have said no, but she would have been lying. If Jack had asked the question, Tess might have said—whispered—yes. That was why Tess had stayed, that first day, before she even understood about the other girls and the bungalow, and, after she did understand that she had become a whore, for all intents and purposes, it was why she hadn’t tried to escape. Then, when she had realized that escape was probably impossible, if she wanted to get home alive, that terrible, shameful need had made it seem natural for her to get used to her lot—even to look forward to being shared with other men, as long as Jack Regensburg might be one of them.
Now Jack’s fingers pushed more firmly at the place where Jeffrey had deflowered Tess, pressed inward to prepare her for the long black thing with the thick ridges. How could it fit inside? She had thought she couldn’t take Jeffrey’s cock, and it hurt when he pounded her bottom as his orgasm neared, but his penis wasn’t as thick or as long as the plug that had made her heart quail.
She stifled another cry, biting her lip and hoping the conversation at the table would start up again, about anything other than her bottom and her punishment. Jack seemed to be going very slowly, taking much more time than Jeffrey ever did when he lubed her for anal sex. Did he, too, want the party at the table to ignore them and move on to other topics? The thought filled her heart with warmth, but to her distress it also aroused her even more with its suggestion that Jack might want her to himself.
She had seen the love there, hadn’t she? She couldn’t have imagined it.
Jeffrey said, “There’s a new restaurant in town, isn’t there?” Tess almost sobbed with relief. The sounds of silverware, of dishes being cleared and others put down, came to her ears.
Jack’s fingers moved in and out of her most private place—three of them, she thought with a whimper that she managed to keep almost silent.
“Relax, honey,” he said, into her ear. “You can do it.”
She heard a low, sobbing sound come from her throat, and she nodded her head, hoping desperately that no one at the table was watching, now. Through the first nights of anal sex in Jeffrey’s bed she had managed to learn about relaxing back there, about pushing so that it didn’t burn as much when the cock invaded her or when he thrust it in and out of her bottom. Now, though, as Jack moved his fingers, she understood that she had more to learn—that she could learn, if she had a patient teacher.
She couldn’t help it, because her pussy clenched at the feeling, and at the thought: she let out a moan.
Jeffrey said, “Don’t let her enjoy it, now, Jack, my lad. I think that’s quite enough lube on that naughty hole. Put the plug in.”
Tess let out another sob.
“Whatever you say, boss. Let’s plug this asshole and teach her to come to the table on time.” Jack said, in a nasty voice that made Tess doubt what she had seen in his eyes. But… What if he has to pretend, because of the danger? She clung to that like a life-raft on the sea of degradation.
“This is why disciplining the girls is so important,” Jeffrey said conversationally. Tess heard his chair scrape and knew he must be turning it so that he could watch her punishment.
“Why?” Ahmad asked. “Because rules are important?”
Jeffrey chuckled. “That’s true, I suppose. But it’s not the real reason—in fact, it’s actually almost the reverse. I like to have rules so that I can have an excuse to spank them and whip them—and even plug them, if I want, the way Tess is going to get now.”
“What?” Anne-Marie said. Tess had almost spoken up herself. She had wondered about this subject, and she couldn’t say it surprised her that Jeffrey thought of it this way, but it did startle her to hear him actually put it into words.
She felt something smooth and round press against her little ring, and she couldn’t suppress another moan of pleasure, which became a wail of discomfort as Jack didn’t spare her, but pushed the first bulb in, opening her and keeping her open, the way Jeffrey’s cock did, but much more insistently, much more forcefully.
“That’s it,” Jeffrey said, with his satisfaction at Tess’ humiliation and pain clearly audible. “That’s what naughty girls get, isn’t it, darling?”
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, who 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 6
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.
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