Exit Strategy

Now the simple details of what I want: either a cash settlement of $3,000,000 or $50,000 every six months for life. Simple.

Now, watch the video.

Jade

Jacob broke out into a cold sweat. Then he watched the video of the perverted transvestite being fucked in the ass and coming all over his own face, then eating it.

It wasn't a dream. Somehow, he had been drugged. It was real. It had happened. That fucking bitch! She couldn't get away with this. He would have her killed. He stood up and grabbed a stack of papers and threw them on the floor in a rage.

Trying to calm down, he thought about phoning the police right away and showing them this email. It was all here...very incriminating. She would be arrested.

The trial would be public. And so would the video. Jesus. He needed to think. Think!

The bell rang on his computer again.

Jade

FWD: Re: New arrangements. See video.

Jackie,

Oh, I forgot to mention, the first installment (or the whole thing) will be expected in one week when we meet at the hotel. Book the whole day off please. You will arrive with your usual women's clothing and be fully dressed before I arrive at 11:00 AM. I will book the room. I intend to have some fun feminizing and humiliating you as much as I can because I know how much that turns you on. But of far more importance, I enjoy it immensely!

Don't deny it. I'm the only one who knows your secrets. Think of your future. You can have it all: political power...AND slavery to me. Ooo, doesn't that make your spine tingle? You want it...don't you?

Jade

And he did. He fucking did. But he couldn't let this happen. He just couldn't. She had to be shown who was boss. So he sat down and tried to think again.

She was bluffing. He had used her services for several months now, and there was no hint of this, and he paid her well. There was no way that she would do this, or was capable of doing this. With the resolve of a quick thinker and decision maker, he picked up the phone and dialed a number.

"Jimmy, my good buddy, I need you to pay a visit to a friend of mine this evening and let her know who is boss. No violence; just some words of wisdom to back off...yes I have her address, apartment 1706, 204 Marlborough Crescent...yes, you can break in discreetly if you want, but no violence to her...not yet."

He hung up and smiled uneasily, rubbing his sore ear lobes where Jade had attached the earrings last night. Suddenly he found himself longing for her domination, her tightening of his corset, the lipstick and mascara on his face. He shuddered and went to the back of his office, opened a door and entered his private bathroom. There, he unlocked a cabinet, took out a bra, garter belt, and stockings. Within five minutes he was masturbating in the mirror, unable to stop thinking about Jade and the domination she was exerting over him. Finally he gave in to it and his submission washed over him with wave after wave of contractions, ejaculate arcing over the sink.

He swayed in front of the mirror staring at Jackie scooping up his cum and sucking it off her fingers. She was real and she said, "I like the taste of cum. Oh my God, I like to be dominated, don't you Jacob? Mmm, I like a penis in my mouth...I certainly do, do you Jacob? Oh and the corset and high heels, I love them so much, don't you Jacob? Jacob? Jacob?"

Jackie's image and words faded away and he saw Jacob with a bra on. It was not pretty, and the reality of this situation slapped him in the face.

"No...no, no, no, what am I doing? What is happening to me?" he whispered while stripping off the bra. When he was nude, he stared at himself and said, "What the fuck is wrong with me?"

He got dressed and phoned his wife. "Honey?"

"Hi Jake. What's up? You never call in the morning."

He didn't know what to say. "I love you; you know that, right?"

"Umm, yes. Jake, are you all right? What's wrong?"

He remained silent for some time and then laughed artificially, saying, "I just felt like telling you; that's all. Sometimes I think I don't say that enough."

"Baby, it's ok, I love you too. Are you sure you're ok?"

"Absolutely! Just a sensitive side to me that you were unaware of I guess. I'll see you tonight." He hung up, feeling weak and foolish.

She held the receiver for a while and felt worried. He was under some sort of business or political stress and it was clear she needed to do her duty. She decided that she would wear some sexy lingerie for him tonight and give him a good time. She never abandoned herself totally to sex, but at least it seemed to make him happy whenever she did allow him to make love to her, so the marriage kept on ticking in one form or another. And that was important to her social status and related commitments.

She would take care of this.

CHAPTER 3

Carol did her obligation for him tonight. He knew it; she knew it; it was mechanical, and it was such a shame. He had never figured out how to awaken passion in her, and he had come to the realization that there was none there to awaken. She could love, but she could not free herself to have uninhibited sex, even of the vanilla variety. Her garter belt and stockings with the lacy bra were all she had on the spicy side of life, and even then, she laid herself back and simply let him take her. It got emotionally exhausting to pretend that this was fun, but each of them did, because they actually did love one another in some type of form. Sex was just not their thing...at least with each other.

The call came on his cell phone long after they had finished making love. He had left her asleep in the bedroom while he went downstairs for a glass of wine so he could sleep.

"Jimmy! How'd she react?" he asked urgently.

"She wasn't there, but I got in and snooped around a bit. She actually left her door unlocked, can you believe it? This girl's a freak, neat as a pin, nothing layin' around, no computer, no notebooks, not even panties in a mess on the floor, no nothin'. It was almost like a hotel room before a guest arrives. Weird."

"So, what did you do?"

"What could I do? I stayed for a while and waited, but she didn't show, so I left. Want me to try again tomorrow?"

"Shit! No. I mean yes. I don't know. Yes!" His nerves were becoming frayed. He hung up without saying good bye and chugged the full glass of red wine in his hand. He knew it would give him a headache, but it would also get him to sleep, so he poured another one.

He woke up in the den on the leather sofa at 4:30. He showered downstairs and sneaked into the bedroom, getting his clothes and leaving for the office. He just couldn't face Carol this morning.

At the office, he shaved and actually tried to do some work, but the stress was too much. Exhausted, he fell asleep with his head on the desk waking up to the sound and feel of his cell phone vibrating on the desk under his chest.

"Hello!" he said gruffly.

"Well, hello to you too, you old grump!" Carol said, tongue in cheek, "You forgot to leave a thousand dollars on the dresser when you left my bedroom last night. I guess you just love'em and leave'em, do you?"

Jacob sighed with stress and fatigue. "Sorry babe, I just couldn't sleep, so I came in early. What's up?"

"Well, one of your assistants just sent me an email with a video attachment saying you told her to send it to me."

"What? Don't open it! Whatever you do, don't open it! Jesus!" Jacob stood bolt upright and was shouting.

"Too late. Jeez, what's the problem? It was the cutest cat video I've ever seen on YouTube. Thanks honey; it was as nice as a bunch of flowers." She paused, worried once again.

"Are you ok?" She could hear him breathing hard, and his heels pounding on the slate office floor as he paced.

"Oh! Umm, oh, that video. Oh yeah, uh, that was nice wasn't it? I guess I felt guilty leaving you like that last night."

Just then the bell on his computer chimed, indicating an email. He casually looked at the sender and said, "Look, I'll call you back, ok? Something's come up. Love you."

Jade

Re: Video

My darling Jackie,

I'm living with friends for the foreseeable future. I don't like strange visitors. Now I have him on video too, except he isn't wearing a corset. Does he like women's clothes too?

By now, you may have realized how close you are to fighting a divorce case. It really was a sweet video I sent her. I've attached it. You might want to watch it so you know what she's talking about. The next video I send her won't be as sweet. I think you know that now.

So, in review, the first installment (or the whole thing) will be expected in five days (that's Tuesday) when we meet at the hotel. Book the whole day off please. You will arrive with your usual women's clothing and be fully dressed before I arrive at 11:00 AM. I will book the room. You will be feminized and enjoyed by all.

I bet you're just shaking with anticipation right now, aren't you? Really...I bet you are...because I KNOW you; I know everything about you.

Now, watch the video, like a good girl.

Jade

Jacob stared at the email in shock and rage. Jesus! Tuesday! Fuck! What did she mean by him being feminized and enjoyed by all? No, no, and no...

He rubbed the back of his neck and picked up his phone. "Jimmy, don't bother. Just forget the whole fucking thing."

"You sure boss?"

"Absolutely fucking sure, yes." He hung up quickly and opened the email attachment. There were no cats. It was a shortened version of the original video, with him dressed as Jackie, moaning in pleasure and eating his own ejaculate while being fucked by a strap-on in the ass.

Jade had him so off-balance now that he felt he had run out of options. He dialed his receptionist and said, "Melanie, cancel all my appointments for Tuesday. I'll be away."

Those arrangements had been made, so he sat down, putting his head in his hands, feeling completely cornered and beaten. He muttered over and over to himself, "Fuck, fuck, fuck, fuck..."

He was scared to death, so why was he so hard in his panties. What the fuck was happening here? Was this even real? He wished he had his corset here; it always made him calmer when everything seemed out of control. The bra, garter belt, and stockings in the bathroom would not cut it for this kind of stress; he needed the corset.

CHAPTER 4

The room was booked under Jade's name. It was 9:30 on Tuesday and it must have been booked for two nights because 9:30 was well before the check-out time. He placed his suitcase and briefcase down and started to remove his male clothes. He couldn't believe he was here being blackmailed like this, but he really didn't see any way out. He would watch for mistakes and act at the appropriate time in the future. Somehow.

Twenty minutes later Jackie stared at himself in the mirror, and the sweet tightness of the corset and bra hugged him like a cocoon. He knew that Jade would tighten the corset far more than he had been able to, so he began with his makeup, the foundation, highlights, eye shadow, mascara, and lipstick. The blonde wig followed and he brushed it out as he contemplated what he was about to do. His financial people had been puzzled but said little when he had withdrawn $50,000 in cash. Jesus, that was a lot of money, he thought, but it was far better than being exposed as a transvestite that liked cock. After all, his last speech had not only been critical of the neutral washrooms in the transgender debate, but critical of the whole transgender culture. If that video got out, he was ruined. Carol would sue him for divorce, and he would be finished in politics and any future social and financial dealings.

He stood up and slipped his stilettos on. It was 10:15 and he waited. She said 11:00, so he paced, getting used to the high heels. He found that he felt more at ease dressed like this, like he was somehow meant to be a woman. He sat down at the desk and drummed his nails in boredom and stress. Looking at his nails, he wondered what they would look like painted red and shiny, and then he looked at his profile in the mirror, marvelling at his large breasts. What would it be like if they were real? He shook his head as if shaking out cobwebs. Stupid thoughts.

Like a cold draft when a door opens, the fantasy blinked out, and he was left feeling ashamed and very much alone. "Fuck!" he said out loud.

She was paying for the room; she could pay for his bar fridge usage. He pulled out a small bottle of white wine, unscrewed the top, and poured it into a plastic glass. When he took a long drink the residue of his lipstick stained the rim of the glass. He needed more, more time to think, more time to drink, so he drank until the glass was empty. He filled it again and cracked open another bottle, but this time set it on the desk beside the TV.

He could just leave. Just give her the fucking $100,000 every year and never see her again. Fuck! He wanted this; that's what was really bothering him; he wanted this. He needed this so badly that his stomach flip-flopped in excitement at the mere inkling of it.

The door buzzed as the key card unlocked it. Jade walked in.

"Hello Jackie. You look pretty this morning," she said cheerfully, "Let me get my clothes changed and then I'll tighten your corset for you. I got a nice dress for you to wear too. You don't look happy to see me. I think you should address me as you've been trained to, don't you think?"

"This has to stop," he said gloomily.

"Baby, it can stop any time you give me the full $3,000,000. As long as it's only $50,000 every six months, we get to have visits. I suppose you could stop that too, but then you'd become an even more public figure. Now, how do you address me?"

"Good to see you too." He paused, having difficulty with the next part. "Ma'am," he muttered. As much as he was humiliated by saying those words, he knew there was no use fighting. It wasn't her; it was him. He had to have her. The girdle he had on was barely concealing his desire. Saying no to any of this meant that he would never have this fantasy escape ever again, and at the same time he would be publicly shamed and ruined.

She came out of the bathroom dressed in leather and with a pair of handcuffs in her hand. "Am I your wildest dream come true? Am I?"

"Yes ma'am." It was becoming easier to say.

"Good girl. Stand up while I tighten your corset." While pulling on the laces, she surveyed the room. His male clothes were in a pile as usual, and she noticed he had been drinking what looked like wine. The glass on the desk was full, but it had lipstick on the rim, so he must have refilled. She smiled.

Fifteen minutes later, the corset was tighter than it ever had been before and he said between shallow breaths, "It's too tight ma'am. Can't. Breathe."

"There's no such thing as too tight for a corset on a sissy. That's like having too much fun. Can't happen. Anyway, put this dress on; it should show your new curves nicely."

It was a tight stretchy, rose colored dress with a high neckline and long sleeves all with a black lace overlay. When he pulled it on he had to work it past the wide points on his new feminine curves, and it felt like a girdle over top of everything else. The hem came to about mid-thigh, and it was so tight that when he walked it either slipped up his legs or restricted his gait if it stayed down. He immediately sensed that the hem should stay down, so he shortened his stride to a more feminine one. His first easy lesson.

Jade walked back toward him from the desk and smiled at his preening. She had a glass of red wine in her left hand and his glass of white in her right hand.

"I see you've had a bit of wine already. Are you nervous or something?" She passed him his glass.

"You bet I am."

"Well, here's to finding a solution to our little problem. I think it's simple: you pay me, I use you for sexual services. You don't use me ever again."

Jacob smiled wryly and said, "Well, I'll drink to the sex part of that."

They drank full gulps and Jade came closer to him so he could smell her and even feel her heat. He felt that fear and excitement she could generate in him and he drank some more while she walked around him like a cat playing with a mouse. It made him nervous. He finally set the glass down, empty.

After what seemed to be minutes of silence with Jade circling him, she said, "Today I want to introduce you to some bondage. Put your hands behind your back please."

"No way."

"What?"

"I said no. You drugged me once. It won't happen again."

"Hmm," Jade said with a Mona Lisa smile, "It seems you don't trust me. That's something we have to work on. You see, this relationship should be simple; you pay me what I want, and you get what you want. The only thing different here is that you're paying me far more than you were before. Oh, and I have a video that could ruin you. I'm like a parasite, and a perfect parasite never destroys its host, so why wouldn't you trust me now? What could I do to you that is worse than what I have done?"

The wine was starting to relax him. She made sense. Maybe he should just let this go, flow with it, just let this go, and go, and go. The air in the room felt strange, like it was misty and warm. He watched Jade's face and it tilted to one side as she reached out to touch his face. Her touch was electric and he pushed his cheek against her hand like a needy puppy. He closed his eyes and when he opened them, he somehow found himself sitting on the bed waiting for something, but he didn't know what.

"You certainly are not cut out for competing against me are you?" Jade said, "You're probably feeling rather strange right now, aren't you?"

He looked up at her standing in front of him with her legs spread apart and her hands on her hips. "Yeah," he said, "I feel weird. I feel, you know..."

"You shouldn't have had so much wine I guess. The drug will last long enough to get a few more videos of you so I can lock this up, lock you up, forever. You'll forget I am telling you this. In fact you'll forget most of what is going to be done to you this afternoon. It may seem like a dream, and you'll enjoy every second of it, because it's what you want, deep down inside your mind."

Jacob smiled. He felt so good. He touched his penis through his girdle and started to rub until Jade ordered him to stop. He felt like a little boy being directed by his mother. He needed to obey every command.

He wanted her. That's all he could think about. He would do anything to have her, but he also knew it had to be on her terms. He shuddered with a rush of adrenalin, like an orgasm. A dominatrix was standing in front of him. How long had she been there, he wondered? He watched her set up a camera at the base of the bed and he stared into it and smiled. This was going to be fun.

"What are you going to do to me?" he asked innocently. The red light blinked on the video camera as Jade walked to the door between the adjacent hotel rooms and opened it, knocking on the opposing door. It opened and two young women entered, smiling warmly at Jacob.

Both women were slim and striking, although the white one had very small breasts. They each wore corsets which seemed to create feminine waists from their boyish figures.

"Good morning Mr. Finning," each of them said, with voices deeper than they should be.

Jacob stared at the three women lined up by the wall and momentarily thought about running to the door, but his thoughts always seemed to disappear like soap bubbles in the air, leaving no trace of the source. There was only the moment he was in, and the present never lasts. The confusing and frightening part of this scene was that each of the newcomers had rather large penises to go with their breasts.