Mistress Jessie, Slave Advocate

"Because . . ." gasped Jonah, trying to avoid the answer.

"I'm listening." Her fingernails increased their pressure.

"Because . . ." His body tried to squirm out of her grasp, but she would not allow it. His legs began to tremble.

". . . BECAUSE SHE DIDN'T WANT TO BE A SLAVE!" he blurted.

Her thumb and forefinger relaxed. "See? Isn't that easier than lying?" Her fingertips gently massaged the sensitive loose skin where she had pinched it. "You wanted to be her master, but she wasn't ready for that. And you wouldn't let the subject go, would you? You thought you could talk her into it, but she didn't trust you. And the only way she would consent to come here is if she were the mistress. Isn't that right?"

"I thought that I could show her it wasn't a big deal," he admitted. "I thought I could show her how to do it."

"You hoped it would be easy for her to do something against her nature, but now I think you understand that's a little more difficult than you imagined."

She walked back around her desk and sat in her expensive chair. She opened a drawer and pulled out a clear acrylic dildo.

"Do you know why we have such an exhaustive screening process for prospective students?" she asked (although she looked only at the dildo). "It's to avoid the kind of scenario that you're in now. All the questionnaires are designed to determine what's in your nature. Specifically, whether your nature makes you better suited to be a master or a slave." She pointed the dildo at him accusingly. "I mean, it would be pretty much impossible for a dominant fella like yourself to get into the position you're in now—unless he were deliberately trying to mislead us. Wouldn't you agree?"

She put the dildo in her mouth and pursed it with pouty lips.

Jonah was going to protest.

Then he was going to confess.

Then he remembered he was talking to a lawyer, so he said nothing.

Jessie pointed the dildo between her legs, and the hand that held it disappeared behind the desk.

Jonah raised his head for a better view, but the chair that held him wouldn't allow him to see. However, the persistent movement of her arm left little doubt what it did.

She was distracted for almost a minute before she spoke again. "Is this your first visit to our island?" she asked as an afterthought. She did not stop what she was doing.

He remained silent for as long as he could.

"I'm afraid I must insist on answer," she said, never looking up. "The next time I get out of my chair, it'll be to hurt you again."

After an uncomfortable silence, he finally said, "No, this is my second visit."

"Was your first visit more to your liking?"

"Yes, mistress. Very much so."

"It must have been—for you to have been so eager to return. Was your first visit with Mistress Sandra?"

There seemed little point in denying it now. "No," he admitted.

She looked up at the screen on her desk, but continued her rhythmic activity. "Your first visit was with a girl named Isobel, wasn't it? Slave Isobel?"

"Yes, mistress."

She looked back toward her lap. "Well, then, why on earth didn't you bring Isobel with you this time?"

"We broke up."

"You left her?"

"No, mistress."

"She left you."

"Yes."

"Why?"

"Because . . ." He knew couldn't avoid answering. He had to say something. "I don't know. We grew apart, I guess."

Mistress Jessie looked him in the eyes.

She sighed heavily.

She put both hands flat on the desk (forgetting her dildo) and rose from her chair. Her skirt had slid more than a little up her thigh, but she managed to tug it to a more businesslike position before she circled her desk again.

She knelt down on the plush carpet next to his chair.

"Let's try that again," she said testily, his dick now firmly in her hand. "Why did Isobel leave you?"

"I guess she wasn't interested in B&D anymore."

She tightened her grip and poked an angry fingernail between his balls like a dagger.

It wasn't pain he felt, but a clear promise of pain.

"You're almost at the truth, Jonah. Just let it out. Why did Isobel leave you?"

It was difficult to admit, not just to her, but to himself.

"She didn't want to be my sub anymore."

"Because?"

"Because . . ." He didn't want to answer. He was terrified of how she would react. "Look, it was all supposed to be in good fun, but she said . . ."

"Yes? What did she say?"

"She said that . . . ," and he swallowed hard, ". . . that I hurt her."

"Did you?"

"Maybe I got carried away."

"If I don't get a definitive answer from you, my response will leave a permanent mark. I won't like doing it, as it may decrease your value, but you keep avoiding the question, and I can't have that. Did you hurt her or not?"

"Yes," he gasped, hardly believing that he was saying it out loud. "I didn't think that I did, but she said that I did, so I suppose I must have."

Her grip relaxed into a far more soothing touch. With her other hand, she lightly tickled his chest and stomach as a reward.

"Very good," she complimented with a sigh. "You told the truth. I know how difficult that is for a liar."

Ignoring his eyes, she talked directly to his hardened shaft—still cradled in her hands. In her high-pitched puppy-talking voice, she squealed, "You were a bad master!" As she squeaked, she bounced his shaft back and forth—as if his member were a plush toy for her to play with. "Oh, yes, you were! You tied her up too long, didn't you! Didn't you! You weren't attentive to her needs like a good master should! That's why she left you! Oh, yes, she did!"

She patted his member on its top, kissed it, and released it.

She sat casually on the front of her desk and placed her bare feet in his lap.

Her casual pose revealed a shaven pussy.

She massaged his member with her toes, and it throbbed with unabashed gratitude.

"How well do Sandra and Isobel get along?" she asked, now staring only at what her toes were doing.

Jonah was lost in her touch, but tried to sound coherent when he answered.

"With me?" he asked.

"No, with each other."

"You don't understand. Isobel and Sandra don't know each other. Isobel left me before I met Sandra."

Jessie's toes stopped their massage, to his disappointment.

Mistress Jessie leaned forward and smiled—not in a good way. Nothing good could come from such a sweet smile.

"Are you sure?" she asked.

Jonah's mind went blank.

"Remember, we live in an age of social media. There's tons of information on the internet about people like us. Well, like you, anyway. Most people have no idea how much information can be found out about themselves. You say Sandra didn't trust you enough to submit to you. Would she try to look into your past, try to find a character reference?"

Jonah waited a long time before answering.

"No," said Jonah. "She wouldn't." His answer sounded unconvincing even to himself.

"Who made the travel arrangements? For your second trip?"

"I wanted to, but Sandra said she would do it. I couldn't really argue. She said it was her prerogative as my mistress."

"And so it is." She looked at the screen on her desk. "I see on her itinerary that she bought two plane tickets." She turned the screen so he could see it. "Yet only one of those tickets was for a round trip. Isn't that weird?" She looked at him with an expression that mimicked surprise. "That's so weird!"

He stared at the screen. "No, that's some kind of mistake." Again, his reply was hollow. "It has to be."

"It hardly looks like a mistake! Becca, does it look like a mistake?"

"Nmph-nm," said someone.

Jonah's mind raced with terrible thoughts of poor choices and shattered trust.

And where the hell was Becca? He was sure the question was important, although he wasn't sure why. Was she watching on some hidden camera somewhere?

"Some of our domination students really are shy, you know. They come to our island full of potential, but when they first arrive, fresh off the boat, they're reluctant to dominate a staff slave who's a complete stranger to them. They hesitate. They're afraid of hurting the poor innocent thing.

"For such students, we have to start their training with a special kind of slave—someone who we can say with confidence isn't innocent at all. Someone who we know actually deserves it."

As her toes massaged his shaft, she slid one hand inside her own skirt. He didn't have to wonder what it was doing. He could see it with his own eyes.

"Lots of subs claim to be bad," she teased. "You really are!"

She suddenly brought her knees together and glared reproachfully—as though he had just peeped at her in the shower.

"So let's summarize your case," she said at last, reaching to pick up his file from her desk. "You're not supposed to be here. You're not really a slave, and you have to go home. You've visited the Academy twice. Once as a master with your slave Isobel, and then as a slave with your mistress Sandra—neither of whom trust you, or really even like you. Is that about right, spanky?"

There was nothing he could say that wouldn't make his situation worse. It was better to say nothing.

But Jessie insisted. "If you're not going to say anything, I might as well apply the gag."

"Yes," said Jonah at last. "Yes, mistress, that's right."

"And there's your loophole, my lovely little perv," said Jessie with satisfaction.

By now, Jonah was accustomed to not understanding the pattern of her thoughts. He prepared for the possibility of either pain or pleasure.

Jessie slid off the desk and turned a lever on his chair that made him completely horizontal. The locked manacles did not allow him to resist.

She sat on his knees and straddled them. She shook her head wildly, whipping her long hair once around, and then started to massage her own stomach, lifting her neon pink top as though the room were suddenly too hot.

Off it came. Her top landed on her chair where her coat still hung.

She leaned forward, sliding her hand down his ribs and pelvis.

"Technically, you are both a master and a slave now," she said, "but our law only permits you to be one or the other."

She lifted her short skirt a little more as she slid her weight up his thigh. She closed her eyes and whispered, to him, "Your first contract was never properly dissolved—so the slave contract you signed on your second visit was never legal. That's why you're in my office now. That's the sweet little loophole that brought you to me."

She rested her hands on his cock and scrotum and skillfully massaged him to full arousal.

"That's right. I can send you home on an itty bitty technicality." She reached a hand behind her back to unhook her bra. Within a moment, it was on the floor.

She rose once more, her legs straddling his cock. It stood to attention beneath her skirt. He waited impatiently for her to descend upon him, to surround him. He longed to be enclosed by her.

Instead, she leaned forward again, allowing her hair to brush up against his face. She positioned a knee on each side of his pelvis and straddled him on all fours.

All he could see was her.

"Our legal department hates loopholes. It'll create quite a stir if I decide to tell them about it."

He started to reply, but she shushed him.

"No talking. It's my talking time now. You see, the nice girls in legal are very thorough, but this time they missed something. They neglected to put a severance clause in your slave contract—which would have ended your obligation as a master. I caught the omission, of course, but I haven't told the legal department. So it's kind of a secret.

"You could tell someone, of course. But you're just a slave, so who gives a shit what you say? They'll only listen to me.

"I could act on this immediately, I know. But my fees are so high! And you have no money, so I have no real reason to pursue the matter."

She leaned forward and kissed him on the lips.

"Unless I accept your services as payment."

She arched her back. Her nipples tickled his ribs. "Many, many services. In my bedroom, mostly. For as long as the proceedings last. And I can make them last a long, long time."

His shaft continued to stand erect, pointing to where it wanted to go, hidden by her little white skirt.

She made him wait. "At the end, you'll get a hearing before a judge, and she'll make a ruling on whether your nature is to be a master or a slave.

"The court already knows that you're a liar. The judge's task will be to determine: Were you lying then? Or are you lying now?

"It will be crucial that when you appear before the judge, that you not try to deceive her. Lying to any mistress on the island can have severe consequences for a slave, but lying to a judge is much more severe."

"How so?" asked Jonah, forgetting himself for the moment.

"You could get the Chair."

"EXECUTED?" gasped Jonah in horror.

"What?" asked Jessie, lifting herself for a moment so she could stare at him. "No, of course not! We don't do that here. That's barbaric! The Chair isn't an execution. It's a stress position."

A devilish look crossed Jessie's face. She looked back toward her desk—behind which her coat was still hanging.

"You got the Chair," she said. "Didn't you, Becca?"

"Mmm-hm," said someone.

Jessie's tits swayed in a distracting way as she picked herself up from Jonah to saunter back to her desk. She brushed aside the neon pink top which she had left on her exotic narrow-backed chair. She picked up the coat that hung from its back and put it on over her miniskirt. The look was not quite professional (her skirt had now worked its way up to her waist) but it had definite overall appeal.

Yet Jonah was now more interested in the unusual design of Jessie's chair. With Jessie's coat no longer hanging from it, the back of the chair now looked too narrow to have been designed strictly for comfort.

And it seemed to be struggling.

"Would you like to see the Chair more closely?"

Jonah started to panic. His hurried thoughts could form no words—except one.

Fuck, fuck, fuck, fuck, fuck, fuck, FUCK!

Jonah kept this to himself as Jessie pulled her Chair out from behind the desk. Its base was on casters which allowed it to roll easily, even across red shag carpet.

In profile, the back of the Chair took on a different appearance. What he had assumed to be a head rest was too low to support a head, and resembled the shape of upturned bound feet with toes pointed at the ceiling.

"I won't go into Becca's offenses," said Jessie as she pulled the Chair around her desk. "Frankly, I don't remember now what they were, but the judge found her excuses severely wanting."

The Chair's crushed leather upholstery was actually a cunningly designed bondage bag on a low rolling base. He could not see any flesh (at first) but he could tell from the bag's shape that its occupant was on her back with her knees pressed against her chest. Her feet were pointed up, and her ass had formed the seat upon which Jessie had been sitting so comfortably. The victim's arms were not visible, but must have been restrained under her back and concealed inside the base in a way that allowed no movement at all.

Her head was entirely covered (except for her face) by the same crushed leather upholstery. Her head stuck out behind the Chair, and a ball gag filled her mouth, preventing any coherent speech. Her flustered expression gazed upward to a flat device that had been attached to the Chair's back a few inches above her face.

It was an iPad. She was able her to manipulate the screen with a stylus embedded in her gag. It was the only movement her restraints allowed.

Becca the Chair glanced nervously at Jonah from her disadvantaged position, then returned immediately to her task, which was to maintain her mistress's schedule and other clerical affairs—including opening whatever file her mistress desired to have displayed on the flat screen on her desk.

Jessie rolled the Chair next to Jonah. From that position, Becca's face was too low for him to see, but now he had a better view of the Chair's front. A single zipper could be seen running from the back of Becca's upturned ankles, down the back of her legs, down to the ass which functioned as Jessie's seat cushion.

On the edge of the Chair's seat, the zipper was slightly open. Jessie's dildo was sticking out of it.

"Did you think I was using the toy on myself?" scolded Mistress Jessie. "While discussing your case with you? That's disgusting! Shame on you for thinking that!" She put her hand around the dildo and gently probed Becca's moistened interior. "Becca doesn't get many perks in her job, but if I don't pleasure her once in a while, she loses interest."

Jessie looked from one slave to the other and relished both their reactions. Still working the dildo with her left hand, she reached toward Jonah with her right, wrapping it around his impatient member so she could pleasure both her slaves at once.

"Now where was I?" she asked, stroking them both. "Oh, yes, your court appearance. You will go before a judge. You will be carried in, since you will be too tightly bound to move without our help. And you will be naked. Trying to deceive the judge in this situation would be a very bad idea.

"That might not be an issue, however, since the court already knows you're a liar, and it is likely the judge will order you gagged for the entire proceeding. If that happens, I will have to deliver your testimony on your behalf. I promise you I'll be as persuasive as I can."

Jonah could hear Becca softly moaning in reaction to Jessie's actions. He also heard crushed leather flexing with increased vigor from the struggling of its occupant.

Suddenly a lyrical chime came from the iPad.

"I have mail!" said Jessie with some surprise. "Put it on the screen, Becca. I didn't say you could stop working."

Becca's affirmative moan trembled as she struggled to access an email program. Her cocooned feet kicked and squirmed uselessly. She would need time to open the message, since her control of the stylus had become erratic as her excitement rose.

Jessie smiled at her Chair and turned toward Jonah. "As I said, I may be called upon to testify for you, but that doesn't mean you're just a spectator. As I make your case to the judge, she will be evaluating you, determining whether your reactions are those of a master—or those of a slave. If you show any kind of positive reaction while in such a bound state—if it appears for a moment that you're actually enjoying your captivity—it will weaken your claim that you're meant to be a master."

There was a knock on the door. Without asking who it was, Mistress Jessie invited the newcomer to enter.

A breathtakingly beautiful woman stepped into the room in stilettos—the first woman he'd seen in this office who wasn't wearing some shade of pink. Her slutty black dress was incredibly short, and its neckline went straight down to her navel. Her long blond hair had been combed asymmetrically over her right shoulder where it curled over her as if trying to cup her breast.

"Here's the docket for you," said the blonde, thrusting a manila folder in Jessie's direction. "Oh," she added only a moment later. "Your hands are full."

The blonde newcomer smiled at Jonah and ran a hand through his hair as if she owned him. "May I help?" she asked Jessie.

"May it please the court!"

The "court" straddled Jonah's head. He didn't expect to see underwear—and didn't.

Mistress Jessie released Jonah's excited member so she could accept the court docket from the blonde.

Without hesitation, the newcomer leaned toward Jonah's shaft and wrapped her mouth around it, squeezing every part of it with an eager slurp. He cried out in unexpected pleasure.