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’ grey 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.
Chapter 3
Tess hoped for one wild moment that Jack would do something. Ever since he had said the strange thing about having to make it hurt, as, trembling, she felt her panties taken down for a public whipping, she hadn’t been able to escape the feeling that he understood her terrible dilemma more deeply than she did herself. Now, desperately, she looked at him, filled with the certainty that he must stop this awful thing that seemed to make a mockery of Tess’ confusion and conflict, her struggle against the dark force of her relationship with Jeffrey.
Three weeks ago, when Tess had heard Jack say that he had to whip her hard, her newly-exposed pussy had clenched, and she had felt the wetness flow so urgently that her face blazed like the sun, but she had had not the faintest idea why. When he had told her to take hold of the opposite edge of the table, and begun to bring his belt down, it had felt so different from when Jeffrey had spanked her or whipped her. Something in his voice, something in the hand he laid on the small of her back, controlling her, seemed to say that while Jeffrey punished her only to take out his aggression and for an erotic thrill, Jack had something different in mind.
I have to make it hurt. That was what he had said. He had seemed to mean that he knew the necessity of complying with Jeffrey’s command that Tess be thoroughly punished for speaking out of turn. But she had never been able to rid herself of the feeling that Jack had really meant something else. She couldn’t push that feeling away even now, when he had gone to get the toy-box that held the vibrating dildo with which Jeffrey brought the girls to orgasm after disciplining them but whose other contents Tess had never known. She kept thinking, despite everything, He loves me.
“Tess, darling,” Jeffrey said in the cultured voice that always conveyed more menace than she thought the roughest lower-class accent from the London docks might have done, “take off your dress.”
It had happened enough already, to Tess and—though less frequently—to Anne-Marie and Judy with Tess watching, that she thought she should have been able to endure it without weeping and even without blushing. Every few nights Jeffrey found an excuse to make one of his girls take her clothes off at dinner.
This was the first time since he and his most important men had returned from their latest business trip, though. Tess supposed she had almost gotten used to the less fraught life the girls lived when the only men in the compound were the security detail. Judy and Anne-Marie constantly joked when Jeffrey was away, and dared each other to do this or that thing that might earn a spanking on his return if reported, like flirting with the bodyguards, but Tess kept to herself, reading and watching movies.
Tess fixed her eyes on the pool and shrugged her shoulders out of the straps of her sundress, so that it fell in a pool of pale blue around her feet, the color barely distinguishable in the twilight. She rarely wore bras, and wasn’t tonight, so her little breasts were exposed to the view of those at the table, their pink nipples stiff and tingling with the arousal humiliation always seemed to bring.
“Come here, darling,” Jeffrey said. “Let me feel those sweet little tits.”
She had no choice, of course. The way he could arouse her with his casual degradation made it worse, but the basic fact of having no alternative to obedience remained the same. When he did this kind of thing to Anne-Marie or Judy, Tess always wondered whether they could somehow simply accept it as the way he liked to act. Maybe as long as he kept letting them go shopping and live here in his walled paradise, it didn’t seem terrible.
The fact that it made Tess’ nipples stand out like little sentinels, made the pussy he had bared for his pleasure clench, seemed now unbearable. She had never really enjoyed it, she supposed, despite the erotic hold it had over her, but she had borne it—before the words from Jack, and the whipping. Before the knowledge that another man could make her feel submissive, without making her feel worthless.
She stood next to Jeffrey’s chair now, and he reached up almost idly to fondle her breasts. “I like these tiny peaches,” he said to the table. “Maybe not as much as I like your melons, Anne-Marie, but these little tits are fun to squeeze.”
He squeezed, as if to prove the point, and Tess cried out. Judy giggled. Julian leaned back in his chair. “She’s wet, I’m sure,” he said.
“Of course,” said Jeffrey. “Tess always gets wet when I show her off and discipline her.”
Tess gave a little whimper.
“Don’t you, darling? Ever since that first night, when I raised your skirt.”
She bit her lip and shook her head. She ran a terrible risk, she knew: Jeffrey might grow truly angry, as he had once before when she had refused a command to suck the penis of a dinner-guest, and whip her savagely himself. Tess couldn’t help the denial, though: she just felt it impossible to admit the power his cruelty had over her.
Jeffrey thrust his hands between her legs, and pulled the grey cotton gusset of her panties aside. His middle fingers sought her wetness.
“Let’s try that again, darling. Are you wet, or not?”
Tess felt her brow furrow so deeply her forehead almost hurt. She nodded, knowing that he would make her say it, now, and not knowing how she possibly could.
Jack saved her from that at least, though, returning at that moment holding the wooden box with its hinged lid that usually sat in the bottom drawer of Jeffrey’s desk. He put it in front of Jeffrey on the table, where the servants had just served the salads. Tess sought Jack’s eyes, but to no avail at all, as he seemed to look at the pool, at the horizon where the sun had now vanished into a pink glow as night rushed in from the East, at the bungalow where she lived with Anne-Marie and Judy.
Where she had watched the news, and seen the images from the Turkish border. She had snooped, and now she knew that the news had concerned Jeffrey and his Sons of Disobedience. If she had thought Jeffrey had whipped her terribly that time she had refused at first to give the blowjob he had ordered, she knew his vengeance for her snooping might go far beyond a whipping. If she showed knowledge of what she had seen in his office, the fate Tess felt certain had actually befallen Bella—death and burial in an unmarked grave—might well befall her, too. The towns on the border where so many people had died were the same towns she had seen on the itinerary on Jeffrey’s desk.
She couldn’t get away. She knew that. She didn’t see how she could have been fooled, that night when he gave her the bracelet, or the morning after when she had called her friends and told them to go on without her. She definitely hadn’t been taken in when he told her to mail her parents and her college and tell them she would be in Greece for the next year, but she had known by that time that she
had to pretend to be, or Jeffrey would spank her—by that time, Tess had received more hard spankings over Jeffrey’s knee than she could count.
She still hadn’t known, then, that the man who kept her and two other girls and fucked them in rotation actually did real evil in the world—of a kind Tess would have had difficulty imagining a person with a British accent (a real-life person, as opposed to a movie villain) could actually do, before Jeffrey had taken her. Taken me as one of the mercenary commander’s captive whores, she had thought bitterly as she watched the report. That had only come with the snooping, and the itinerary, and the news.
Jeffrey opened the toy-box, and Tess saw into it for the very first time. The sight drew another little whimper from her, because the things inside all seemed so big. Some of them were in friendly pastels, but many more were of black silicone, or black rubber. Tess didn’t understand how there could be so many, or how they could all have such different shapes—every shape seemingly more frightening than the one before.
“Let me see,” said Judy, in a nasty, giggly voice, getting up and leaning over. She took a risk, doing that—Tess wondered if the dark-haired girl even understood Jeffrey’s moods well enough to see the danger. If he decided that Tess’ punishment should be something the other girls must watch as an example to them, Judy could find herself getting the same or worse for presuming to treat the toy-box as something at which to giggle.
Tess herself certainly didn’t feel like giggling, but Jeffrey chuckled, and turned the box around to show everyone at the table its contents. Tess sought out Jack’s face, but he had turned it to look out at the pool, as if trying to make sure his men stood at their posts, or patrolled the compound as they should.
“I haven’t used these on the girls as much as I should have, I guess,” Jeffrey said to Julian and Ahmad. “Maybe that’s why I keep having to spank them.”
The lieutenants chuckled politely. They knew their commander’s moods backwards and forwards—knew that if they remained respectful they would have the privilege of fucking his girls if Jeffrey deemed it appropriate to send one to them, as Judy had been sent to Ahmad the previous night.
At least Jeffrey hadn’t sent Tess to a lieutenant—yet. The very extremity of the degradation, as she had thought about it when she first learned about Bella and Anne-Marie and Judy, that second night here, when Jeffrey had had Bella brought to his bedroom and sent Tess to the bungalow, had seemed to her a hedge against its being true. He couldn’t actually treat women that way. He was British, for God’s sake! Judy had told her casually that night that Tess wouldn’t see Anne-Marie until the morning, because Jeffrey had sent her to a bodyguard as a performance bonus. Tess had laughed. She had literally felt certain that it must be a joke, and that because it was a joke, things couldn’t be the way they seemed.
“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: 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. Tess moaned. “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.
Chapter 4
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 Ahmed 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.” 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 not far removed from dropping out of college to join the CIA (or, from his parents in Kansas’ perspective, to become a bum who managed to support himself overseas s
omehow) 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 side, 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 towards 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.
Hero Undercover: 25 Breathtaking Bad Boys Page 131
