“Jack,” Jeffrey said, “come here a moment and help me choose.” He reached into the box and brought out a thing that made Tess’ knees turn to jelly: long and black, ridged down its length. Six inches, at least, and an inch-and-a-half thick at the final ridge, before the narrow part and the base that would…
That will keep it inside me. Deep, deep inside me. Oh, please. She spoke it out loud: she couldn’t help it. “Please, Jeffrey. Please, no.”
“Hush, darling,” Jeffrey said. He reached out his left hand again and probed between her legs, where her panties still lay askew, exposing the bare furrow of her pussy.
“See?” he said to his audience. “She’s still wet as a five-quid whore.”
He left his hand there, still possessively fondling, and reached into the box again to bring out another black object—much shorter, but also much, much thicker. Tess gave a little cry. The idea that one of the two horrible things must go into her bottom seemed somehow much worse than simply seeing a single plug on its own.
“What do you think, Jack?” Jeffrey asked. “She needs to learn a lesson—we can all agree on that. Which one will teach her to come to dinner on time?”
“Well, sir,” Jack said, running his fingers down the long, ridged one, “I think that depends on how you plan to handle the rest of the punishment.”
Jeffrey chuckled, as if appreciating his security man’s suggestion that Tess shouldn’t get off too lightly. Tess, however, felt her eyes widen. Just as when Jack had said the thing about needing to make her whipping hurt, she thought she had heard another meaning, meant just for her. Jack seemed to say that a different kind of man would know how to handle a girl’s first experience of anal discipline.
A man like Jack.
He hadn’t even meant to do it again: the words had just come out, shaped by his dominant instinct. Jack didn’t know what else he could have said, really, but it wasn’t the actual words that posed the problem, but the tone, and perhaps even the measured cadence, in which he had uttered them. The part of him that wanted Tess to know, as foolish as the wish must inevitably prove, that he loved her and, in another world, would teach her how wonderful sexual submission could make her feel—would help her forget all the pain and conflict wrought by Sir Jeffrey Young, bart.
“You think we should whip her, too?” Jeffrey asked.
Of course he would think that Jack meant Tess needed more punishment. He hadn’t truly hoped that his employer might understand that preparing a girl for her first time wearing a butt plug, and the amount of time she spent with it inserted, in what circumstances, and above all what happened when the plug came out, should have a bearing on which plug he chose. No, he supposed he had hoped Tess would realize, or sense, something about such matters: would she be sent to wash the plug, like a naughty girl? would her master’s cock immediately replace the plug in her anus? or would she have to wear it all night, sent to bed without supper?
But now he had no choice: if he went down that path, he would risk showing everyone here how he felt about Tess. He laughed, unable now to look at Tess but picturing the expression of betrayal on her face and feeling the blade in his heart twist again. “Sure,” he said lightly. “If you’re planning to whip her, too, you’ll want the thinner one, with the ridges.”
“Jack, my lad,” Jeffrey said, using the endearment that signaled his greatest satisfaction, “I like how you think.” He looked around the table and saw that no one had started eating yet. Jack watched his commander evaluate the interpersonal possibilities, feeling he watched a wolf deciding how to approach maintaining his dominance in a pack full of potential alphas. Jack saw, and knew Jeffrey must, too, that he stood in some danger of losing his audience. Julian and Ahmad certainly didn’t object to the displays of sexual dominance Jeffrey put on, but when dinner was waiting the show would quickly lose some of its appeal.
“Take her over by the pool—not too far away, mind you; that lounge chair that’s got the light shining on it—and put the plug in, while we eat. Tess will go to bed without her dinner.” A thought struck him then, as it would any dominant man. “Or I suppose she’ll have a different kind of dinner, with a good deal more protein in it, when she sucks all the cocks at the table.” He chuckled.
His hand had remained between Tess’ legs the whole while, and now another of Tess’ helpless, submissive whimpers rose above the waterfall’s gentle noise. Jeffrey pulled his hand away and turned back to the table. Theatrically he dried his fingers, wet from Tess, on the napkin in his lap, winking at the lieutenants and the other girls. Then he lifted his retsina. “Bon appetit, gentlemen,” he said, and they started in on the salads, as Jack put the two black plugs back in the toy box and removed it from the table.
He turned to Tess, standing with her panties still pulled aside, and now he couldn’t help meeting her eyes and seeing the pain there, along with the helpless arousal. She seemed to search his face, as if looking for some way to understand the contradictions Jack couldn’t help portraying despite his covert-ops training. Being only twenty-three, and having dropped out of college to join the CIA only three years before (or, from his parents in Kansas’ perspective, to become a bum who managed to support himself overseas somehow) Jack supposed he hadn’t had as much experience in tradecraft as he really needed. Still, he didn’t feel sure that they could have told him, in the training camp in Kansas or the one in Turkey, how not to fall in love, or how to pull yourself out of it.
How the hell was he going to get through this without making the situation worse?
He thought he knew how it had to start: he reached out his right hand to take hold of her left shoulder, to lead her to the nearest lounge chair, right where she had dropped her dress. Tess had her arms at her sides, slightly bent with her hands raised just a little, balled into fists, as if she were trying to keep herself from covering her pussy, or her bottom, with them. Jeffrey always punished that. Jack’s hand closed firmly around her bare shoulder.
He meant to say, Come on, let’s get this over with. The words froze in his throat, because he felt Tess’ whole body relax at his touch, felt the tension go out of her. His eyes had been turned toward the pool, but at the sensation his hand passed on to his mind, he snapped them back to Tess’ face, absolutely unable to help himself.
Her eyes said, You love me.
He swallowed, hard. If anyone had been watching that moment of pure weakness—Jeffrey above all—Jack had not the slightest doubt that everything would have gone sideways in an instant. His own eyes replied, Yes.
Then he managed to say, because now he knew that as awful as the consequences might be, hypothetical dead people in the Middle East had no chance of laying a claim anywhere near as strong on his heart as this single, lost, submissive girl did, “Come on, let’s get this over with.” He spoke the words in a rough, careless tone that drew a chuckle from Jeffrey.
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 spilling 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 gray 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.
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