A Kept Woman

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Former rich boy exchanges masculinity for luxury.
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Disclaimer: This story is my intellectual property, and should be treated as such, do not plagiarize, or post without permission. If it is not legal to view writings that are sexually explicit and may have themes of bondage, feminization and other 'deviant' sexual experiences: don't read this. Don't read it, if it is not legal to do so where you live. Going any further is of your own free will, and responsibility is solely on yourself. Any similarity to real people or events is highly cliche, horrifying and unintentional.

Rules for the Subs:

(Optional fun for the free pets, if you are owned by a master or mistress, get their permission before following the rules ahead.)

Rule #1. A Kept woman is a woman who is given money and a home by a person who visits her regularly for sex. So you start by telling me that you want to be my Kept woman.

Rule #2 Coat those lips in lipstick like a good Kept woman.

Rule #3.Wear your sexiest dress or lingerie that you have, I want to kow all about it. Be sure to tell me when you write me later,

Rule #4. Be horny and arroused. Stroke, rub, jerk, and stay on the edge of that orgasm, but do not cum without permission.

Rule #5 When rules 1-4 are finished: Cum. Good Girl.

enjoy!

Mistress Dyvia presents:

A Kept Woman

By: Mistress Dyvia

Zack was born into a rich family. He had every advantage while he was growing up. His parents never had to get used clothes, he had the best tutors, and his parents had the best nannies to make sure he was doing what he was supposed to be doing.

He went to the best schools, and they pushed him to have the best grades. He had the best cars when he was a teenager, always fully loaded, safe, and they always spoke to his status. Sure he had the title of 'rich kid,' but really when you're a teenager, that's not really a bad thing. Of course that also meant that with the high grades, and the name behind him like his parents, he got accepted to the best colleges.

He dated the prettiest girls, which was probably his biggest weakness. But to make up for that, his parents still had those tutors, and checkbooks to make sure that his grades stayed up there. And in fact everything was going great until shortly after his 21st birthday, while he was a junior at his ivy league college. One day, he was called up to the admin office because his parents' check had bounced.

He had to make a call to his parents, and found out that something bad had happened. His family's company, the one he was expecting to inherit one day, had gone under. His father was traditionally very good at investing, but most of his investments in the past year had gone bad... very bad in fact. On top of that, someone hedged their investments against his father's company and they made a lot of money off of his father's failure.

And suddenly overnight, Zack was poor. His car was repossessed, he was out of college, his girlfriend dumped him, and he couldn't even make his way back to his parents who were also soon to be homeless.

Zack had to learn the hard way how to be homeless. Luckily, his cell phone plan was still good till the end of the month and he was able to Google some important things. With a few dollars he did have, he got a gym membership, that way he could at least stay showered and clean. He got a job at a grocery store. He got fired because he couldn't figure out how to do some very basic things. He got a job at a fast food restaurant: same. He got a job at a coffee shop, rinse, repeat and recycle, leaving him in a position where he was just couch surfing. Before he knew it, months had passed. Before he knew it, it had been nearly 2 years, his friends that he had gone to school with had long since graduated and found their careers. And here he was without a stable home, without stable income, and knowing exactly too much of what ramen feels like when you've had it too many days in a row... too many weeks in a row. He had long since cut contact with his parents, they never really recovered and they fought over it. He blamed them for the terrible direction his life had taken. He assumed his mother had or would divorce his father soon and would probably remarry, but she no longer communicated with Zack. She was all about herself.

He often agreed to go out with some friends, you know... if he worked it properly, he would have a place to stay that night. He stopped at the gym first, showered and shaved, and then met his friends. It was a hot dance club, he knew it was a chance to get some free drinks too. What he was not expecting was to meet... me.

To him I was the older woman, although I was only 32 at the time, but he was 23, so that made me significantly older than any other woman he had been with. My eyes laser-focused in on him, and I pulled him onto the dance floor. I could tell he was really into me, he couldn't decide whether he wanted to look at my eyes or my tits. But if you wear that perfect little black dress, that's exactly how the boys are supposed to react.

That night he did not go back to his friends, nor did he get some sleep on their couches. He came back to my house. I pulled off his clothes, and let him take off mine. I sat on his face and demanded that he lick me until his tongue was too tired to move. By then his dick was nice and hard, and I jerked him off a little bit just to get him a little more in the mood and then I lowered myself onto him and fucked him for over an hour before I finally let him cum in my pussy.

I woke up the next morning and made him breakfast. He thanked me for the food. I told him that I almost never made food for men, but he was so fucking good at everything the night before, that he had earned it. He smiled with pride.

I asked him where he was staying, and he said he was staying with a couple of friends while he was waiting for a new place to come through. I told him I had business in Los Angeles for the next week, and offered to let him stay in my house until I returned, basically he would be my house sitter for a week, but only if when I returned I could ride him like I had the night before.

There was a huge grin on his face. He agreed, he would have a place to stay for the next week without having to worry about couch-surfing. I was actually surprised that he asked if he could have a few friends over. That was pretty daring of him, but I did respond with an easy "that's fine, I honestly don't care if you have a few friends or have a raging party, just make sure the place is clean when I get back on Saturday." I handed him a card for some cleaners, call them and they'll make sure the place is clean.

He took the card with a huge grin. I also gave him a book full of numbers with services and encouraged him to use them, I'd pay for them. And I left, I had business to attend to. He got used to the high [read:rich] life again, having money, having a roof over his head, having food delivered, not just take out or anything like that, chefs that would come and deliver fully cooked seven course meals. He is living the life of a rich person once again. And of course, I returned on Saturday and we fucked.

I offered to let him do it a second week, and he agreed. And then a third week. And then a fourth week. Where I only turned up one day every week, we had sex and I would leave the next day.

Once I was convinced that he was addicted once again to the lifestyle of the rich and accessible. It was time for the deal to change. We were sitting down after dinner, "well I think it's been fun, but I think it's time for Zack to leave."

His eyes widened, he was not ready to leave, "wait, what? I thought we had something going on?"

I smiled, "I've had my fun with you, and you are good at the sex and such, but I don't-" I had to pause for a moment as if thinking it over, "well, maybe... "

"Well, maybe?" He's getting a little bit irritated, "what's that supposed to mean?"

"I'll make you a deal, and you only get this offer once. My mother was once a kept woman. I don't know if you know what that means, but a man bought her a house, gave her a nice allowance, some rules to abide by, and would be available for sex whenever he wanted. I'm willing to do that for you, so Zack, do you want to be my 'kept woman?'"

A discussion was had and I let him think about it, but I needed a decision before I left.

"I think I'd like to accept your offer. I'm not sure why you would want to call me a 'kept woman' though."

I smiled at him with amusement, "I'll have the contracts drawn up tonight, and you will be 'kept,' by this time tomorrow. I'll send a car around noon, just be sure to be ready by then.

He eagerly nodded his head and offered to shake my hand. I looked at it, took it, and shook it back daintily. His hands were rough, but not for long.

I wasn't with him when the car arrived. But given all the cameras in the car security system you can be damn sure I was watching. He sat in the car wearing loose-fitting jeans and a loose t-shirt. Same clothes or at least the same style of clothes he had been wearing all month. We would have to do something about that.

He arrived at my lawyer's office, I was there for that. I gave him a quick hug as he came in and he squeezed back. I smiled at him with a warm and doting, almost as if I were enamored with him. Let him think that he had some power here since I was attracted to him.

The lawyer put down a binder that was roughly the size of a small dictionary. Zack's eyes went wide. "Welcome Zack, my client here has graciously decided to give this house to you, sort of. It is technically still in her name, but it is yours so long as you keep up with certain contractual obligations. Keep it clean, I understand you have a monthly stipend, so whether you clean it yourself or hire others to do it for you, is up to you, but when my client comes to you for whatever services you have agreed upon in advance... the place will be clean."

"Okay that makes sense to me. No problem, what else?"

"Honestly? Your style needs to change a little bit. It is stipulated that you will need to keep your style and image updated to my client's preferences. You can be assigned to a personal shopper at your request, and at my client's expense on a weekly basis to make sure that you present the ideal image."

He looked down at himself slightly embarrassed, "okay, what else?" Echoing similar words and a similar tone from before.

My lawyer just slid the dictionary size contract forward, "that's the gist of it, if you back out of the deal though, you will owe my client her money back. If you back out within the first 90 days you will owe her the money she spent. If you back up between 90 and 180 days you will owe her double. And if you try to back out between 180 days and the end of the year you will owe her triple her investment in you."

"So it's only a one-year contract?" his voice was nervous, almost dejected.

"One year with the option to renegotiate. And you'll be happy to hear it is up to you to continue or not, not her."

"Okay, I'll sign." And without reading a single line, he signed and initialed every single line the lawyer told him to. Signed, dated, and sealed... just like his fate.

I gave him a hug and a kiss on his cheek, my lawyer shook his hand and I told him I would see him in a day or two. He smiled and told me that he couldn't wait, and he walked back down to the lobby and then out to the limo which I watched to drive away from my lawyer security camera.

I pulled out my phone and made a quick call, "he's on the way."

I called for my own car, the driver opened the door and let me into the car, and as we drove away I logged into the special app that the facility had for us. I was going to watch everything.

The limo pulled into a special garage, and the driver got out and opened the door. Zack looked confused, but stepped out as a team of seven men approached him and asked him to come with them. There was no audio in this camera, but I can guess what was being said. His body language was initially defensive, but I'm sure once they said that this was part of the agreement he signed he resigned himself and walked with them.

At first he was led down the hall, it almost seemed like an abandoned business office, or maybe a sterile hospital. But as the team surrounded him and led him down the hall he was taken to a very specific room where he was met by a scientist. To be honest, I don't know if they were a scientist, doctor or 'other,' but they sure did wear that lab coat with confidence.

They pointed to a circular area in the corner. He was told to stand in it, Zack approached it tentatively, clearly he did not want to go in there. When he tried to back up, a couple of his escorts grabbed him by his upper arms and forced him into the area. A glass cylinder came up from under him trapping him in this small area, once it was too high for him to crawl out of, the guards let go of him.

A mask lower down from the ceiling. He was instructed to put it on and he shook his head violently as if he were trying to refuse whatever they were going to do to him. He was trapped, though. He demanded that they let him go, he was pounding on the glass. And instead the scientist just pressed the button and a pink fluid started pouring in from the bottom. In under a minute it was above his knees.

He was warned again to put on the mask, and he shook his head. But by the time it was over his navel he was reaching for it and putting the mask over his mouth. But his eyes suddenly went wide as he tried to grip at the mask. You couldn't tell by watching the video what happened, but I knew... There was a breathing tube forcing itself down his throat, there's a material inflating inside his mouth, at least at the back of his mouth blocking the fluid from dripping inside of him. But it was guaranteeing that he could breathe.

As the mask pulled back, there was only a tube going into his mouth. Soon the pink fluid covered his head. He looked around as what appeared to be flakes of white slowly seemed to slow down. It awkwardly reminded me of flakes when feeding a fish. Except these flakes made their way to his skin more and more. Until his whole body had turned alabaster white.

For a long time, it almost looked like a snow globe in his little world. But each 'snowflake' found its way to his body, coating his entire skin. And as more came down it started reshaping his body.

The snowflakes even seem to change the shape of his hair. That is that it kept descending down, attaching... and reshaping things... His penis was gone, and it was still there under the white material, but it was shifting things making it impossible to see, impossible to feel. It increased the size of his hips, and ass as they were undeniably feminine. Breasts became visible after a while, given his height they were respectable, bigger than an average woman's, but definitely not humongous. They look good for his frame. They looked good for HER frame.

And after so many hours, the changes were done. The pink fluid receded, and the breathing tube in her throat seemed to shrink and withdraw from her throat. She fell to her knees and coughed. She cursed them, but even watching her on the video I could see her eyes go wide at the unexpected feminine sound that came out with every word from her mouth. But her skin was still coated in that white material. They brought her to a washroom, and that's what it was, a room just to wash. They threw some light green slime on her and then put her under a shower. The white coating seemed to dissipate into a liquid under the combination of the green liquid and the water. And in under a minute she looked like an attractive woman. Her hair was now blonde, and it was very long, right down to her ass.

Then they dried her off and blow dried her hair, then they gave her a sexy red dress in matching high heels. She had no idea what she was doing, she still cursed them but she put on the clothes. She was led to the limo and she was driven home.

All of 'his' clothes were gone. But in their place were the clothes that I had picked out for 'her.'

I arrived a few hours later. I knocked in the door, she almost immediately started to yell but I put up one finger to stop her.

"I can't stay long, but here are the new ground rules to keep this house. It was spelled out in the contract that you did not read. So you can check that in your email later. The first time you get out of bed after 8 in the morning we'll start a timer. You have one hour from that time to take a shower, and start doing your hair and makeup. Upon completion you will send me a selfie. I can demand a selfie anytime, and you are to make sure your makeup and hair always look impeccable. You may not remove your makeup unless you are changing your look until 14 hours after you sent me your selfie showing your look for the day. If I'm not happy with your makeup or hair, you will be instructed to go to a salon where they will show you how to do your hair and makeup. It's up to you how long you do this, for all I care, you can go to the salon every single day that you live in this house."

"You can't just do this..." her voice spoke with a quiver almost ready to cry.

"You agreed to be my kept woman. And a kept woman you will be. If you want to go back now, you owe me a lot of money but I'll accept it."

"I don't have that kind of money..."

"Well then, enjoy being a kept woman. At least the next 364 days."

I leaned in and gave her a kiss on the cheek leaving a pink lipstick mark, marking her as mine, and I turned on my heel and walked down the steps. "I'll be looking forward to breaking you in on Friday." I stopped at my car and opened the door, I looked back and saw she still looked shocked in the doorway, "and before I forget! Your new name is Zoe! Toodles!" And I blew her a kiss.

---

It was the very next morning that I got a notification on my phone that she was up. And just like the agreement said, I sent her a text demanding a selfie an hour later. She responded less than a thirty minutes later, with a picture of her in a dress with a pretty bad makeup job.

'Use the makeup wipes, start over again. Send me a picture when you're done.'

About 20 minutes later I got another selfie, it wasn't much better, it actually might have been worse. And again I told her to do it over again... and again... and again.

This lasted for a while until she finally asked me if she could just go to the salon and have them do it. I said that was fine as long as she brought her own makeup, and I made sure she had the phone number to a local salon that had a first rate makeup studio.

I'm sure she had no idea that I had actually paid the salon in advance to make sure that my kept woman had a retainer to make sure she would be seen right away. And whoever would be doing her hair and makeup would make sure that she was taught how to do everything that was done to her.

I was alerted to the time when she checked in, and then alerted again when she was done. Considering that she was just having her hair and makeup done, it was a long 5 hours. Which meant that whatever look she had right now, she now had the ability to do on her own.

'Send me a selfie.' I messaged.

And she responded a minute later with a much better makeup and hair job, her lipstick matched her dress, which matched her nails, and she looked like a sexy woman. Just the way I wanted her.

There was a part of me that wanted to keep teasing her, but I was satisfied for the day... I didn't want to break her on the first day. I did have her send me another selfie just before she would have been allowed to start taking off her feminine attire. Her makeup had smudged a little, so I made her redo it, which of course cut into her free time. The picture she sent back was actually pretty good, I guess her time with the girls at the salon was definitely worthwhile.