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Author’s Notes:

(1) This is chapter 5. Read the first 4 please.

(2) This is fiction.

(3) This man is weak and broken and vulnerable. This woman is strong and broken. Could this happen? Sure it could. Don’t get too tied up with that though. It’s just a story.

(4) Oh, and some of this stuff is unsafe sex. Don’t do this at home.

(5) Slavery is illegal. Reality would tell us that he would be in a mental hospital, she in jail.


Jack was sure he wouldn’t sleep at all that night. There was just too much to think about, too much to do. Even if he was completely prepared, he was far too excited to sleep, and he was far from ready, sitting at his kitchen table scribbling notes for Geoff. There was the landlord’s name and number, what was owed, the telephone details, cable TV, Internet…on and on, and it surprised him how complex his life was, as small and insignificant as he felt in the world. In listing possessions and bill payments, he wished he owned a car though, because he really did not want to be driven away by Geoff in such a final manner, dependent and vulnerable. But, on the other hand, he knew that was part of the excitement and the arousal.

Finally, he had finished. His cash matters were easy; there was no money other than the $135 in his pocket. Thirty years old and his net worth was clearly negative.

Now he had all his clothes carefully laid out on the bed, bureau and floor, and he was terrified. It was crap. He had three dresses, three skirts, and three blouses, all bought on the Internet without proper sizing and color matching. The underwear was easy because he had lots of it, and it was just that: under-wear. He chose black panties, a black pantie girdle, black garter belt with matching stockings and a full support black bra, and put it all on with care. The plastic water bags dropped into the cups of his bra and he felt that initial surge of sexual energy as they bounced and pulled at the straps on his shoulders. He had done a fresh shave of his entire body, so he stood looking at himself in the mirror with his head full of excitement and fantasy.

She said she would get him all new clothes that fit and suited him, even some corsets. He felt his belly and pushed his waist in with his hands just above his hip bones to see what a corset would do, tilting his head and wondering. Turning around he felt his girdled bum and reflexively squeezed his sphincter.

What would it be like to be a slave? When the hell had he started fantasizing that anyway? After all, when he was a child, he wanted to own one to rub his back before he went to sleep at night. His mother had stifled a smile and told him that was bad thing to say.

Now he wanted to BE a slave, and even the thought of erotic humiliation began to appeal to him. When had things taken this turn? But just like the cross dressing itself, he didn’t know; it was just there, seemingly guiding his path now like a light through the forest at night. The simple fact was that he fantasized it. But what would the reality be like? She said he would have to suck cocks and be a woman, and that made him shudder with revulsion at the same time that his penis said otherwise. It was the same with anal penetration. He had never allowed himself to put anything up there; it pushed him over that line which he had drawn in the sand, never to tempt fate that he might like it. Now he tried to imagine it, on all fours dressed as a woman, while a man fucked him like he was a woman. And his penis twinged again.

What had happened to him, he wondered?

Then there would be beatings, but he expected those to be symbolic in nature, and even though they were not fantasies of his, the domination by Mistress Johanna would make them seem like fantasies. The human toilet? Would she really do that to him? He realized that taking this “job” was worth the risk. All his dreams, and perhaps some of his nightmares, were about to come true, and even if she forced him to swallow her urine, he knew he would do as she said. He would allow all those clicks of locks, and then it would be up to her to do with him as she wished. And in his mind right now, he fantasized that he would spend the rest of his life as a woman and slave to Mistress Johanna.

And it excited him. It felt so good that he started to rub the front of his girdle so that his penis grew and hardened, pointing straight up to his belly button. Remembering Mistress Johanna’s phone sex instructions, he laid on the bed and thrust his hips into the mattress until he heard her voice like she was there in the room.

She said, “Now listen carefully Jackie and repeat after me. If you say exactly what I tell you to say, I’ll allow you to come. Is that clear?”

“Yes Mistress!” He smelled her perfume.

“Tell me that you’re a woman Jackie. Tell me. Say it Jackie!”

“Oh, please allow me to come!” He smelled the leather of her corset. But there was a block somewhere. He couldn’t come and he started to tire, the thrusting becoming weaker.

“Say it Jackie, say it. You can’t Ataşehir Escort come until you say it!”

He started thinking it. Then he started saying it, and hands seemed to reach to him out of his darkness, pulling him into the fantasy. “Mistress Johanna, no, please, no, I can’t, please…Mistress Johanna, no! Oh my God, I…I’m a woman!” In the groan of orgasm he forced the words out as commanded, “Oh no, no, I’m a woman, no, no, no…oh God, no! Oh Jesus!”

Jack soaked the girdle and bed in continuous streams of ejaculate, moaning and thrashing as if he had been in normal intercourse, but as soon as he caught his breath, reason prevailed and he realized this was far from normal. As always, the guilt and shame settled in hard, like a steel top closing on a steel coffin.

“What have I done?” he said out loud, “What the hell am I about to do?”

Without even bothering to change out of the damning clothes, he walked to the kitchen and poured a glass of wine, slammed it down his throat, poured another glass, and went out on the balcony where the cold late Autumn air stunned him, but not in the way he thought it would. He had thought it would clear his mind so he could stop this ridiculous adventure. Instead, the cold air on his silky stockings made him aware of his femininity once more, and he became Jaqueline again almost instantly.

It was then that he realized there was no escape; he had to have this, no matter what the cost, no matter what the risk.

Again he talked to himself. “Oh my God!” he said, “I want this! I really want this. Tomorrow…no, today, I am going to be a slave to Mistress Johanna. I want it, and I can’t stop myself! I won’t stop myself. This is going to be real!”

He turned back inside and closed the balcony door. There was no draft of air tonight. The door seemed to slam shut for the first time ever. The door to the bedroom beckoned him, shining with light, and he marched in to choose a different girdle and panties to wear tomorrow. He took his soiled ones off, washed himself, and put the new ones on. Now that the big choice was made, the choice of a dress was easy. It was blue, with long tight lacy sleeves, a tight bosom, and a flared skirt to give the illusion of female hips. He put his only pair of high heels on and sat down to do his makeup. It was 4:00 AM by the time he put his wig on and brushed it out.

Standing in front of the mirror, he fantasized that Jaqueline stared back, and hoped she was good enough. He made some coffee, sat at his desk and waited, going through Mistress Johanna’s website for the thousandth time. Soon he would be a player on that website. Soon.

He awoke to a buzzing sound and was confused. What had happened? Looking at the clock on the desk he panicked; it was 8:05, and the buzzer went on relentlessly.

Jack ran to the door and pressed the intercom. “Yes?” he said.

“This is Geoffrey. I just talked to Mistress Johanna and she says that if you’re not down here in five minutes, the deal is off. Bad start sir.”

“Oh my God. Geoffrey. Yes. Oh shit, umm, let me just use the bathroom, and fix my, umm… Uh, I’ll be down right away. I’m so sorry; I fell asleep. Is that okay? Don’t leave, please don’t leave.” For some reason he just could not say to another man that he had to fix his makeup.

“Okay, that’s fine Jackie. I’ll wait, but Mistress Johanna is not happy with you. Already, I might add.”

“Be right there.”

Rushing to the bathroom Jack pulled his girdle and panties down and sat on the toilet to pee. While he did so he looked for smears or flaws in the makeup that he had applied just before he had fallen asleep. When he tucked his penis away and pulled up the underwear again, he checked for a bulge and there was none. Next he powdered his face lightly and applied another layer of lipstick, a light unremarkable color that he hoped would not clash with his dress and the subtle shading of his makeup. Standing back, he let out a deep sigh, blowing air deeply out of his lungs in a pressure relief valve sort of way.

It was 8:07. Grasping the suitcase containing all his female identity by the handle, he wheeled it to the door and did a deep sigh once more before he opened it and stepped into the hallway and into his future. He knew there would be people there, and there were. A Middle Eastern couple stood at the elevator, she with a Hijab and standing obediently one pace behind a well-dressed man with a brief case. As he approached, wheeling the suitcase, he felt his breasts bounce in the bra, but more than that, he saw the disapproving looks of the man as he stared at Jack’s jiggling breasts, short dress and high heels. The woman stared straight ahead.

The silence was overwhelming, but the tension got worse when the elevator door opened with a ding. There were three young women, probably in their early twenties standing there, clearly friends, as they all stood together to one side.

Jack felt like he was a turkey being basted by critical eyes. They all smiled and looked at one another discreetly, Bostancı Escort but not discreetly enough. Nobody analyzes a woman and her attire more than another woman. And they knew right away.

It was many things. His guilty and terrified look, his bitten fingernails, the wobble of his heels, all gave him away, and then there was the fact that he didn’t have a coat to wear outside.

One of the girls spoke, “Wow, you’re brave today.”

He just smiled, not wanting to reveal his deeper voice, even though he knew they had nailed him.

“It’s minus 10, and no coat. Gonna be chilly. Cute dress though.”

One of the other girls turned around abruptly and pretended she was rifling through her purse, but the shake of her shoulders gave it all away. The third girl just made a tight line of her lips, not wanting any part of the barely concealed mocking.

Jack sought out the third girl with his eye contact, and he hoped the thank-you message got to her. It must have, because when they reached the main floor, she reached out and touched his tight lacy sleeve, saying, “It’s okay. You look fine. Have a great Monday.”

Again he smiled, following her out, his knees now shaking uncontrollably. He was a fool to think he looked like a woman, to even think he ever could, no matter what. Why was he being so foolish? But as he walked toward the revolving front entrance door where a man stood, he felt the cold air hit his nylon-clad legs and swirl up and around his panties. One last giggling look from the rude girl, and he felt it: the bizarre erotic nature of his humiliation, the fact that he was doing this because Mistress Johanna had told him he had to do it. In full-on fantasy, he felt his legs swish past each other, and the satiny cool feel of his dress on his thighs and calves, and the compression of the girdle on his penis. He shuddered in an astonishing desire to orgasm. It was right there, ready, just one more step way in the high heels. But then he reached the door, breathless and still on the edge, where Geoffrey reached out his hand to take his luggage.

“It’s 8:11. I have to tell her you know.” His look was serious as he turned to walk away, through the moving door, into the cold.

Jack assumed he was to follow, but it wasn’t exactly an introduction. A Lexus awaited in the wind and buffeting snow flurries and his suitcase was placed in the trunk which closed with a thud. The back door of the car was open, so he climbed in, trying to settle his flying skirt. Another man walking by slowed his pace and waited for glimpses of panty or better, and he got it, as the skirt flew up to Jack’s chin revealing his girdle, garters, and nylon hose. He brushed it all down and glanced at the man who smiled and nodded his head in approval.

After he closed his door, Geoff’s door closed and the engine was started, bringing much needed heat to the chilled air. Silence ensued until Jack asked politely, “What do you mean by having to tell Mistress Johanna?”

“You were not only late,” he said, “but you were late again when you told me five minutes to get down the elevator. She won’t like that.”

“Why? I wasn’t THAT late, for cryin’ out loud.”

“Jackie, it’s disrespectful to be late. She won’t like that, that’s all. I’ve learned never to be late.”

“Jeez, it’s not like I was half an hour late or anything. Does she deduct pay for being late or something?”

Geoff glanced with a puzzled look into the rear view mirror, shook his head in amazement at Jack’s naivety, and started another conversation. “It takes about half an hour to get to Mistress Johanna’s house. She lives in the southwest, in the foothills, and it’s pretty isolated. Are you warm enough back there? That dress looks a bit light. You look good though.”

“Yeah, I’m fine. And thanks. But I feel a bit like an idiot.”

“Just so you know,” Geoffrey said, “so you don’t dig your hole any deeper, we’re being recorded. You’re always recorded from now on.”

“I see. Why?”

“No deeper dumbass. Don’t dig deeper. Relax and enjoy the scenery; it may be awhile before you see any of it again, from what I can tell.”

Jack felt that draft again, that shiver of cold excitement and fear, and he shifted in his seat, feeling his satiny things slip and slide. The seat belt crossed between his breasts and kept them separate as two mountains.

“I’m kinda scared Geoffrey,” he said hesitantly.

“Don’t be, okay? There’s wine in the armrest beside you. I know it’s morning, but just relax and trust in Mistress Johanna. She knows what is best for me, uh, for you. Just trust in that.” The car pounded through a pothole like a period at the end of a sentence, and that was the end of the conversation.

Trust, he thought. Yes, there was that. And he could always leave if it didn’t work out.

One last question. “Geoffrey, how long have you been with Mistress Johanna?”

“Four and a half years. She’s owned me for four and half years.”

Owned, he had said. As if it was nothing and everything and ordinary. Kadıköy Escort Well, that was Geoffrey, not him. He was Jack, and Jack could always leave any time he wanted. She told him he could, and he trusted that.

They traveled south along 24th street, then west toward the Tsuu T’Ina Indian Nation, and south again along its boundary to highway 22X, and then headed west. This area was what he often called “The Shire”, in honor of his imagined view of what the hobbits’ homeland would be like, a pastoral and tranquil mix of forest and ranch land nestled in the foothills with the Canadian Rockies in the background. Houses grew more spaced with distance from the city.

He reached for the Shiraz in the protected compartment beside him and poured a bit into a glass, swirling it slightly to release the bouquet. Beautiful. The taste expanded in a slow crescendo in his mouth and he smacked his lips slightly. Wow! That was real wine; it even had a name, something he couldn’t pronounce. He poured some more and relaxed while staring at the mountains, still and placid in the distance, capped with masses of early winter snow. In fact, as they travelled west and gained elevation, the ground became white with snow, unblemished except for occasional coyote or deer trails. His spirits lifted, like a boy in a toy store.

Unexpectedly however, he started feeling anxious and began to drink the wine a little more quickly. Alarm bells in his head started out with a distant “tinkle” and were now clanging wildly. What the fuck was he doing? What in the fuck was he doing here, in this car, going to live in an unknown house, employed by a strange woman…to be a slave or prostitute? He hadn’t even told anyone where he was going. That was stupid. What if this was some sort of setup? He had visions of the doors being locked from the outside and he was now trapped.

He quickly activated his cell phone and brought up his contact list, but then realized with despair that there was no one emotionally close enough to him that really cared. Who the hell would he phone, his brothers that he hadn’t seen in years, his former work acquaintances, his gamer friends in Japan or England? And what would he tell them anyway; to come and get him if something went wrong with his new job as a slave to a dominatrix?

The phone went back in his lap, cradled by the web of his skirt. He took a deep breath and let it out slowly. Relax. Let the world take you. Let her take you. This was no setup. All he had was his body and his fantasies. These two things were his and his alone, and could not be owned. He could always leave.

The car slowed and turned north on an oiled gravel road. They were riding a ridge, and there was a view of the distant city skyline ahead on the right, with the desolate mountains on the left to the west, both miles away. The road was uneven now and often quite bumpy, and it forced Jack to be careful with his drink as he didn’t want to spill anything on his dress. His heavy watery breasts bounced and jostled in his bra, constantly alerting him as to his illusion of femininity. The wine had left him with an imaginative edge, and he was feeling like her. He was Jackie now.

The gravel turned to pavement once again and he could see that they were traversing the ridge, losing elevation to the northwest, and then due west so that the ridge appeared to grow higher to his right, now obscuring the city view. Abruptly Geoffrey slowed once more and made a sharp right and a very large 3-car garage faced them immediately, nestled into the side of a snow covered escarpment with scattered gnarled pine trees, bent by winter winds. The far left door opened remotely. Jack’s head bobbed about as he tried to see a house, but there were only large spruce and aspen trees on a large lawn to his left, the garage to the front and the rising snowy escarpment to the right.

The garage swallowed them up and the door closed with a firm and audible clunk. He felt that same feeling of shock one gets outside the car when the door locks at the precise moment one sees the keys in the ignition, a finality, the “oh shit” moment. There was confused chatter in his head as his conflicting thoughts tried to make order of this strangeness, but he was loving every nanosecond of it.

Geoffrey opened the door for him and said, “Here we are. Sorry for bringing you in through the garage, but the front doorstep isn’t shoveled yet. Was the wine okay?”

The contrast of the clarity, civility, and normality of this small talk with the bizarre nature of this whole event was utterly confusing, like someone shaking you while having a bad dream, it merged together, both of them real, or both of them dreams, or one of each.

Jack looked around. The garage was cavernous. A silver colored Infiniti G-37x convertible with its top up occupied one of the spaces. It had “fender-bergs” and was dripping wet and filthy as it had recently been driven in the cold and was warming up to the garage temperature. The final space at the end of the garage had been transformed into a large workshop with an enormous selection of tools on the far wall, a compressor, and even a welding generator for arc welding. Windows to his left revealed the doorstep with at least six inches of snow, and for the first time he saw an oblique partial view of a grey stucco-sided house.

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