Mistress Dyvia
A Kept Woman
Apr 20, 2024
A formerly rich man and college dropout due to financial issues is 'kept' by a rich woman and given a home and a generous stipend if he agrees to be feminized and available for sex.
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 this lips in lipstick like a good Kept woman.
Rule #3.Wear your sexiest dress or lingerie that you have, I want to know all about it. Be sure to tell me when you write me later.
Rule #4. Be horny and aroused. Stroke, rub, jerk, and stay on the edge of that orgasm, but do not cum without permission.Rule #5 When you finish the story, leave a comment or review.Rule #6 When rules 1-5 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.
I spent the rest of my night making the beginnings of a digital scrapbook. Pictures of Zack in the house, getting used to being in a position of wealth once again. There were pictures of Zack being transformed into Zoe from the facility. And then I took selected pictures from today and put them together. This would be fun to look at around the end of the year if she wanted to renew her contract.
The next morning I demanded a selfie again. Her hair was the same as the day before, so was her makeup. But she had a new outfit. I sent her a response saying that she either needed to change her hair and make up to match the outfit, or she needed a new outfit. She was to change it, and send me a text when she was done. And much like last time I kept making her change things until she just asked to go to the salon again. She did.
This was something that seemed to go on every single day. Should show off her new skills, and they were getting good… but she just didn't have the feminine sensibilities to match hair, makeup, and clothes.
Friday eventually came, I told her what I wanted her to wear. I would be coming that night, and I would be having my way with her. I had her send me a selfie with her dress. Told her it didn't match her hair and makeup. She went to the makeup studio and I was happy.
I arrived around seven that night. I knocked on the door and she answered. She smiled but it wasn't as warmly as I was used to, clearly she was resenting her femininity and how much I was pushing it. But I stepped in anyway, and kissed her. She kissed back. And I close the door behind me with my foot.
This wasn't the night that I was going to push her limits. But I did have that itch, and she was going to satisfy it. She used her tongue to bring me to my first orgasm. And then it was my turn.
I crawled back up after I came down from the orgasmic high. I made it with her, some pretty heavy petting and kissing.
And then I slid my fingers between her legs, teased her clit, and I could tell she liked that. She completely had no understanding of why she could feel things she did with a clit, why they felt so different than it would have on her penis but it didn't take long for me to have her writhing in the sheets. Coming in such a way that there was no white discharge, but there was an incredible orgasmic rush pulsating from her core.
I had a dildo and a strap-on harness. Her eyes went wide, and I laughed, “don't worry Zoe," I can tell by looking at her eyes that me calling her by her new feminine name was still bothering her, "I'm not using this on you, you are using this on me… at least for tonight” there was a look on her face, but a bit of nervousness when I said the last four words.
She took it from my hand, and started to put it on, but ended up completely baffled… I had to help her get the straps correct and make sure it was on her properly. The dildo itself was much larger than her previous manhood.
She started with her tongue again, making sure I was good and wet. I already was, but I wasn't complaining. I still made her use extra lube on the toy before she started to push inside of me. At least I didn’t have to worry about her cumming too soon, all I had to worry about her was running out of steam, so to speak. I got three more orgasms before I left. I just thanked her, gave her a kiss on the lips and put my clothes on and walked out. No cuddling, no after-sex reminiscing… Just wham-bam-not-even-a-thank-you-ma'am. It was completely transactional.
Of course I still rubbed a little salt in the wound of her masculine pride, later that night, I demanded a selfie since she was still in that time frame. Her makeup was still messed up from when we had sex, so I did what I had to do, told her to fix her makeup and send me a selfie when she was done. She replied nearly a half an hour later, and I told her she can get back to her night. I'm sure that I'm taking off her makeup and putting on some pajamas.
And the next couple weeks went very much just like that. If I didn't like her hair in the way it matched her outfit, I would make her redo it. It took a couple of times, but soon, it didn't take long before she was used to fixing herself so that she would get that final selfie request at the end of the night and be in pristine condition so she could relax for the rest of her evening. When I arrived I didn't push anything for her penetration, just mine.
She still had trouble matching her outfits and her looks. So I set up a new plan. Every Monday, Wednesday and Thursday she went on a shopping spree with a personal shopper.
I can only imagine how she felt on that first day. Amelia arrived at 10 in the morning, and Zoe was dressed, had her hair and makeup done, which was fine, but Amelia had criticisms. Shortly thereafter they were going to some stores, not just ones at a mall, but some upscale ones downtown.
Amelia would have Zoe try on 20 different outfits and then pick only three. Sometimes they were smart clothes, stuff she would wear to a business meeting, some for if we were on a date, things she should wear to a funeral, things should wear to a job interview… but again she only selected three outfits. Technically, she made Zoe pick the three outfits as they would go through the pics on her phone and see the complete looks.
Amelia never saw what was in Zoe's closet, then again I doubt Zoe had seen everything that was in her closet. But she was getting used to what she had, at least from what Amelia was picking for her. Then they would buy jewelry to go with the outfits, and Amelia would also make sure she got a lovely selection of perfumes to make sure she always smelled so feminine.
Zoe was getting used to taking trips to the salon and its makeup studio. But with Amelia things took a very different turn. Yes, the girls were used to having to teach Zoe everything from scratch, but she was learning faster and faster now. So she shouldn't have been there quite as long. But she was now. Amelia would have her go into the back and put on a new outfit, and then she would go to the salon and have them redo her hair to match the outfit at Amelia's instruction. Then they would teach Zoe how to do it. Then she'd be over to the makeup studio to find makeup that would match the outfit.
As if this wasn't harrowing enough for a neophyte-lady like Zoe, Amelia would have her take off her outfit in the back, put on one of the other outfits they had picked, complete with jewelry and perfume… and they would redo it. And then again. And at the end of the night, she would leave fashion magazines for her as homework.
Thursday wasn't about picking out everyday sexy outfits. It was about the intimates. Lingerie: panties, bras, chemises, baby dolls, garters, stockings, and so much more that would be used to seduce, not walk out in public. This was a bit much for Zoe, especially the first time. But on the bright side, she wasn't required to go to the salon, Amelia took her home, and made suggestions on the kind of hairstyle she should use, stuff she had already learned. And put makeup palettes with each outfit. It was a little excessive considering how much makeup they bought, but it was ready.
And then Friday came. It was time for my weekly visit.
She opened the door and I stepped inside. Her makeup was impeccable, and she wore a sexy gown that showed off her immense cleavage. I didn't even bother looking her in the eyes, I stared at her cleavage as I stepped around her.
“It's not going to be long before I forget that you're not a real woman. Or are you a real woman?"
She bit her lower lip not knowing how to answer, and then her eyes widened as if an unexpected breakthrough hit her, with a demure smile she simply said, “I'm your kept woman. It's up to you."
I laughed a jolly laugh, “yes, you are!" I exclaimed as I grabbed the back of her neck and pulled her closer to me to kiss her. It wasn't a friendly kiss, it was a possessive kiss, I pushed her back and I invaded her mouth with my tongue. She was mine, and this intense kiss was intended to remind her of that.
I had pressed against the wall as I finally broke the kiss, and then I took her hand and pulled her to the middle of the room, I walked around her… sizing her up like the piece of meat that she was. She blushed. It was one of the nice things about the material they used to feminize her, everything would seem so real, the neural transmitters conveyed everything… every touch and sensation she would have felt. If the man below the skin was blushing, so would the feminine skin.
I was standing behind her when I wrapped my arms around her waist and pulled her tits up. And as I stepped in front of her again I made a mental note that her cleavage had indeed deepened. “Zoe, you are so fucking hot."
“Thank you, you are too." She said she started to look over my body, but looked away almost as if she wasn't sure if she was allowed to.
“I am going to fuck you tonight, Zoe. All you have to do is let me know if you want me to take your pussy or your ass.” her mouth opened in shock but she wasn't exactly sure how to answer, I cut her off, “you don't have to answer right now. But when I have that strap on wrapped around my waist you will get on your knees and you will beg for me to fuck one of those two holes. Do you understand?"
She took a deep breath, it was a bit much for her, “I understand."
“Good… because here's the consequence of failing that instruction. For the next week, every day you will have a butt plug as part of your uniform. And every day it will be larger than the day before, and I'll still fuck your pussy. And next week when we have our little date night, I'm going to fuck your ass with the biggest dildo you've ever seen. Are we clear?”
"Like crystal…" she wouldn't meet my eyes, but I'm pretty sure her imagination was going wild.
I put my arm around her waist, and let her into the living room. Again I ran my fingers along her waist as I walked around her, sniffing her playing with her hair, her tits, her ass, and even riding my arms along her thighs.
Her pink silk gown was lovely, shiny, and enticing. It was bait for someone who she might want to lure into her bed. It was an invitation for someone to take her. And I was about to accept that invitation. It took all my self-control not to just pull it over her head, I wanted to see what she wore below. She was told to make sure she was wearing sexy things below. "Stay.“
She stayed exactly where she was as I left the room. I'm sure she heard the drawer open and close as I grabbed my instrument. And I returned to her with a pair of scissors. I snipped the straps of her dress. And then ever so carefully, I dug a finger into her cleavage and pulled the dress tight and snip, snip, snap… over and over until I cut a line from her cleavage to her thigh and the gown dropped to the floor.
I took a step back to take it in. Below it was a slightly lighter shade of pink then the dress. She had a cami top, with an underwire that enhanced her bust. It was Lacey with a floral pattern, and most of it was at least partially see through, though it did give her some modesty around her nipples. My eyes went down further, and she had a matching garter belt, which had garters leading down to her stockings. Granted in today's lingerie stores, most stockings had the gel inserts to keep them up, but there was something sexy about garter belts. And of course there was the matching thong. Equally pink, with the same floral and Lacy patterns that her cami top and garter belt had.
I made a sound of approval as I licked my lips. “You are a woman now, no doubt in my mind about that." I gave her a wink, and she blushed, again…
“Undress me." I said as I waited for her to approach me. She took off my blouse and my bra, undid my belt and removed my slacks, my socks, and my panties. I had less clothes on than she did, and I had no doubt in my mind that she felt more naked than I actually was… such Divine exposure.
I sat on a chair and I spread my legs, “you are hungry, slut. Why don't you come here and eat something… still wearing the lingerie, her tongue was between my folds in seconds. I wrapped my fingers in her hair, and guided her just the speed I wanted. And I did not let her stop after the first orgasm… or the second… or the fifth.
I slowly open my eyes after that last really intense orgasm. I pointed to a bag, “get that for me."
She grabbed the bag, and as I nodded my head, she opened it and withdrew a box. It was the strap-on harness, and another box inside would have a custom-made dildo. I didn't tell her, I wasn't even sure she would notice… it wasn't too big nor was it too small, and truth it was quite average. And it was a copy of Zack's penis. The irony of fucking Zoe with an identical copy of Zack's cock was a delight for me.
I stood up, and Zoe helped me put the harness around my waist and around my legs and thighs. She took out the dildo and handed it to me and I slid it into its socket. I looked down at her with a smile, would she beg?”
I didn't even have to ask her what her answer would be, "please, would you use that toy and fuck my ass? I really need to feel it in there, I'm your kept woman and I’m a really slutty slut. I think you should take my ass and save my pussy for something more special.”
I giggled a bit, "very well, pet. Why don't you be a good slut and bend yourself over the kitchen table and spread your cheeks for me.” She complied as I was lubing the faux cock up. Even as I walked up to her, I grabbed another handful and spread it all around her asshole and even pushed some inside of her with my finger, and then wiped the excess off on her ass cheeks. “You're my woman now, aren't you?"
“I'm your woman."
“Good girl, just wait to see how far down the rabbit hole goes. And I'm not even talking about this… “ I eased the phallus inside of her, nice and slow, I wanted her to get used to it and once I was inside of her I wrapped my arms around her waist and pulled her back just a bit and let my other hand find its way to her clit. "As a woman, I think you're going to like this. Say it back to me.”
“As a woman, I think I'm going to like this."
“As a slut, I think you're going to love this."
“As a slut, I think I'm going to love this." She replied without even waiting for me to command it.
“Good girl, and here's what you're going to do. Every time I pump in and out of you you're going to declare what a fucking slut you are. The only time this changes, is when you want me to go faster, and then you'll scream, “fuck me, harder…”
And for the next half an hour, my ears were delighted by the cacophony of screams such as, "I'm such a horny slut." With the occasional “fuck me harder…” and it wasn't long before she came like the horniest fucking slut with my fingers twisting circles around her clit.
---
As days turned into weeks and those turned into months, I wanted her to embrace her femininity. I wanted her to look forward to everything she did. I complimented her on her outfits, her makeup, and her hair of course. But whenever I asked her for a selfie, or I saw her in person I wanted to reinforce the behavior. I told her how amazing she looked. How beautiful she was. How feminine she was. And how all that turned me on so much. But was it enough just hearing it from me? I didn't think so, I started making arrangements so that she would get it everywhere she went.
The first time this opportunity came up, she was struggling with an outfit, and she couldn't find a hairstyle she was happy with. She went to the salon, they did her hair and makeup. She still wasn't happy, and she tried something new. She dyed her hair. It was a bright and vibrant color, and it did surprisingly well with her outfit. I was told that everyone in the salon took a moment to come over and compliment her, and she smiled and she blushed.
Four of them took selfies with her, and one of those pictures managed to find its way over to me. I had sent her a message, I complimented her look and told her how proud I was of how she was controlling her own look. She thanked me and sent me a selfie on her own. I thanked her for the voluntary selfie, and had flowers delivered to her. I don't think she'd ever had flowers given to her, but the person who delivered them to her had a body camera on and sent me the video. She was shocked, she sniffed him and almost hugged them. It was such a very feminine reaction.
When I showed up for my next session, I paused, I looked her up and down. “Zoe darling, those selfies you took have done you no justice.” I touched her hair lightly before kissing her.
She was speechless for a moment, but she said, "thank you, I'm so glad you like the look. It's taking a lot of getting used to.”
"I can imagine! But I'm suddenly thinking instead of just having my way with you tonight, I want to take you out. Show you off.”
And so we did, I took her to a place where there were more men than women, and our nicer outfits wouldn't stand out too much. She had a lot of attention. Almost every man had his eyes on her, almost every woman gave her the stink eye.
However there was a dance floor, and I pulled her out, she hadn't really learned how to dance in those heels yet. I kept it simple for her, and despite the fact that she tried to resist it, she was enjoying herself. I think she liked the fact that almost everyone of her drinks was paid for by someone else, doors were held for her. And she left with four phone numbers. There wasn't a doubt in my mind that she had any intention of calling any of them, but it did make her feel beautiful.
I brought her back home, and I had my way with her. And I could tell she was in a mood, she liked the way I wined and dined her, and she loved the way I held her when we danced. And when I put her down and spread her legs, I could see the lust in her eyes, the excitement in her body language.
I went down and started licking her pussy. I knew it wasn't real, but fuck it felt like it was. It tasted like it was, and it was wet like a woman in heat should be. I knew how the material worked, it transmitted her masculine urges into feminine sensations. She should have been hard, but the skin made her wet. So very, very wet.
Once I had her gasping, I stopped. “Stay still my sweet, I'm going to go get that sweet toy I know you love, and I'm going
to make you cum while buried to the hilt in your ass."
“No." That was one word I wasn't used to from her. It had just been enough to get me to stop what I was doing, and then she added, “I think I'm ready for you to fuck my pussy." I smiled, I had never pushed it since the night she had begged me to take her ass. But now this is what she wanted. And I was going to do it, and I was going to do it well.
Once I had the harness on, I brought my fake cock to her pussy lips, it was coated in a thick lubricant, and I slowly moved it up and down her slit, getting her excited. And when I pushed it in, easing it ever so slowly, she let out such a sound of surprise. She wasn't sure if it was going to hurt, feel good, or a little of each. No, it just felt fucking good. That's the way it was designed.
I slowly kept pumping in and out until she was ready to cum. And then I slowed down, breaking the rhythm. She started moving along my shaft, she hadn't figured out how her body worked yet,I mean I know she had masturbated liketis, but here,I was in control…. I can only imagine her frustration when she couldn't quite come, the rhythm was all wrong. But I teased her and had her on the edge so many times.
Every Friday night for weeks I would bring her straight to that edge again. But I never quite brought her all the way.
But the positive reinforcements continued. She was learning to do things for herself, her personal shopper would go with her, but it got to the point where she was more of a friend. Zoe was picking on her own outfits, she was making very good choices. When she went to the salon, she wasn't doing it because she didn't know how to do something, she was doing it to socialize or to try something new.
She was constantly bombarded by compliments, and she was getting used to it. She was starting to enjoy it. She was starting to look forward to it. Zoe had completely embraced her new identity.
She would go to the grocery store in jeans and a top that showed off more cleavage than she needed to show. It was giving her a rush when she saw the men gawking at her, and the women starring in jealousy. At least that's how she interpreted the stares.
Her body positivity was increasing. She was going out to places where she could dance or hang out with other people on her own. She was even starting to make some friends. Of course she would always leave Friday nights for me.
I was well aware of her search histories too. She was spending a lot of time learning how to do new makeup techniques, tutorials and such and how to do contouring and other things. She was doing this on her own. She spent time researching how to do her hair in newer and newer ways. She was even looking into the color theory that her personal shopper had suggested. It took a few months but she was starting to get used to this, it was almost second nature to her. People always complimented on her hair, her makeup, her style, she even had an eclectic style of jewelry. She had her nails done almost every day, she still stopped at the salon to do that, she'd made some good friends there.
It was clear to me that Zack was almost gone, and Zoe was reigning supreme. Or at the very least, she was making it look that way.
Then came a very special Friday night. I had fucked her to orgasm.. For the first time… and then followed it up three more times. I don't think that she knew she was physically capable of doing that. But then I let her fuck me. She used the same strap-on that I usually used on her, and I spread my legs and let her right on in… okay I'm making that sound like I was a little too cool with it, ‘come on in take your shoes off stay awhile!’ But it was the first time she got to penetrate someone else in months. I mean technically she still was a man below the special skin that she wore, but for all intents and purposes, she hadn't been a man in a very long time.
We spooned for a while, we hadn't really cuddled all that much. But we did that night, she slept in my arms, with one arm wrapped around her waist holding her breast gently. The next morning we woke up together, it was the first night we had actually stayed together the whole night. …At least since the deal was made.
“Do you know what today is?" I asked her.
She was still half asleep but her eyes kind of rolled in deep thought, “not off the top of my head."
“It's been one year since you signed the contract. Now you have an option, whether you want to keep staying here or not… let's discuss it over breakfast…
I was tempted to order it online, it could have been delivered about 15 minutes later. We would have sat down with our respective meals, to stay longer… But she had decided to put something together for us.
To remain would mean that she would have to stay woman, did she want to go back to being a man? Part of the contract said that it was up to her whether or not it was renewed, not up to me. Regardless, there were things to discuss…
She got up before me, she didn't even close the door when she sat to pee. Her male ego had been annihilated if she was comfortable doing this in front of me. I picked up my cell phone and caught up on some emails as she went downstairs.
I could smell the bacon wafting up. It was time to get downstairs myself, I sat down, and was surprised to see that she had made crepes. I could only assume there are from my previous day, no way could she have made them that quickly. At least not from scratch. But they tasted like they were from scratch!
She had fried up three slices of bacon for each of us. I felt again that her masculine ego had been crushed as I couldn’t help but think that Zack would have cooked a dozen for each of us and eaten whatever I did not eat.
“This is amazing, Zoe." I complimented her culinary skill.
“Thank you, I've been practicing. I never really cared too much about things like this before, now I take a little pride in it."
I smiled at that comment, “and you absolutely should." As I took a second bite.
The meal was filled with small talk, we both knew what was coming. But we decided to wait until after the food was over, and that was definitely a nonverbal agreement. We just didn't talk about it.
I helped her clean off the table while she started doing the dishes, and then we were treated to the living room. We sat on the couch and faced each other. She got right to the point, "I would like to renew our contract. My life has never been this amazing. If you would ask me 11 months ago I would have been embarrassed to admit that it was even likable. But I love being a woman. I love being your kept woman. And I will do anything to keep this position. Anything.”
I laughed, "don't feel as though you have to do ‘anything.’ just what we have already agreed to. But, the second contract is not for a year, it is for five. If you agree to be my kept woman again, you will have gone 6 years without seeing your cock.
You will have lived a feminine lifestyle for 6 years, at the end of those years, I'll offer you another contract for ten.”
There was no hesitation in her voice, “done," she said definitively. “I may as well be a woman now, but maybe a penis somewhere under this fake skin, but I'm happy to leave that behind, I love my breasts and I love my pussy. And I want to be even more feminine.”
I kissed her lips lightly, “then you are my kept woman, again… the paperwork will be dropped off Monday morning, and when I have the signed paperwork, we will keep going forward.” What she did not know was that I would slip into the contract to increase her monthly stipend by 10% every year for the duration of the five years. I wasn't going to tell her that, that would just be a fun little surprise."
We made our way back to the bedroom before we showered, the sex was good. Actually she was getting really, really good at it. So I'm going to change that and say that the sex was great.
I rolled away from her at one moment, and grabbed my cell phone, and I hit the record button. “So tell me Zoe, do you want to go back to your old life? Or would you prefer to stay in your house as my kept woman?”
She leaned in at the camera looking directly at it, she licked her lips and made sure she was showing plenty of cleavage, “I would love to stay as you're kept women. For as long as you want a woman like me."
I shut off the video, kissed her and got off to take a shower. She was still relaxing in the bed when I exited the bathroom. Put on my clothes as I always had, and told her I would see her the following Friday.
She smiled and said she couldn't wait.
The following Wednesday I had the sign documents in my hand. Zoe was mine for five more years. And the way I would mold her, Zack would be gone forever. And that suited my plans just fine.
There was a knock on the door, my assistant let me know that my appointment was here. He walked in with confidence and sat in the chair. I looked him up and down, “I'm told that you're an expert at infiltration? And a number of other espionage-related specialties?"
“I am. Truthfully, I'm not sure what to expect, so I apologize if I seem unsure whether I want to take this assignment."
I smiled, “I'm going to pay you very well to do one very simple assignment. The only thing you need to do is not be seen.
And to steal something that I give." I put three sealed manilla envelopes in front of him, “the one with the letter ‘A’ on them is your instructions. ‘1’ should be mailed from out of state, and ‘2’ will be delivered the day after it arrives, in person.”
He was already reading the instructions, "that's it?”
It was more detailed than what I had said, but the instructions in the folder were it. "That's it.”
"I don't have a problem with any of that, I'm in,” he shook my hand and left my office.
Epilogue
Joshua stared ahead as the woman explained, “Look, I asked for the burger with no pickles, and no mustard, and to add extra lettuce. This sandwich had no lettuce, it had extra pickles and the bun was not symmetrical with the burger.” And then she stopped, waiting for him to ‘make it right.’
He took her order, she insisted on extra pickles, lettuce had not been mentioned one way or the other and it typically did not come with lettuce. And looking donwat the sandwich in question, the bun wasn’t actually that bad, maybe not perfectly symmertical, but a typical person might not notice that last less-than-half-inch off. “I’m sorry Ma’am-”
“Ma’am?” she almost shrieked, “How old do you think I am?”
“I was just trying to be polite, ”Joshua politely said to the Karen. “...but as I was going to say, I can have the sandwich remade-”
She interjected, “Yes you will remake my sandwich, and remake my whiole meal since the rest of mine is probably cold by now and you will give me a refund for the time I’ve had to waste.”
‘Oh,’ was the initial thought in his head as he suddenly realied what was going on. She just wanted something for nothing. Order it one way, complain that wasn’t the way she ordered it, complain, get two meals for the price of none. He should have recognized the signs, he married a woman like that… though she was never that demanding for cheap shit like fast food.
“I just need to get my manager’s approval.” he said and as he was about to step away he realized she was practucally foaming at the mouth.
“No.You will do it now, or I’m going to get you fired, I know the franchise owner.” with such an entitled voice.
‘Sure you do…’ he thought sarcastically, “Well I’m sure she-” The owner was a man, “-will tell you I can’t type in the code without a manager’s card, so I need to get my manager.”
She rolled her eyes as if he had just inconvenienced her so much, “fine, but she will hear about this.”
Joshua smiled his best customer service smile and walked to the back to find his manager. “Hey boss…”
Cheri looked at him, “What’s up?” He filled her in, and she nodded her head, “I’ll take care of it, can you empty this trash?”
He looked at it, it was overflowing. “Sure.” and he grabbed the handle, and managed to get the bag out and into the black cart, and pushed it out the back door. He almost lost it at the curb, and let out a sigh of relief as he pushed it the rest of the way to the dumpster. He slipped the lid of the dumpster open, and lifted the bag up and as he went to ‘chuck’ it into
the dumpster it ripped and he was covered in grease, ketchup, lettuce and other leftovers… “Fuck!” he sceamed out. He picked it up and threw it away and made his way back in.
Cheri just looked at him, “You can’t work like that. Why don’t you head out.”
“I still have two hours left of my shift,” he said looking at his watch. Yeah he still wore a watch.
“Not any more. Presentation is important.”
He let out a sigh, and grabbed an unused trash bag after he punched out. He spread it across his driver’s side seat so he wouldn’t ruin the seat of the 15 year old car.
As he drove home he thought about how just a couple years ago he had money, prestige… He and his family always drove the best cars and they always had always gifted his family witht he newest ones for Christmas every year, now he was flipping burgers, he suspected his wife was having an afair, his son cut off contact when they couldn’t pay his tuition…
He pulled into the driveway, his wife was home, almost a surprise. He stepped in and she looked at him, “The floors, the maids just cleaned them today.”
“Maids?” he asked, “We can’t affored cleaning services right now.
“You’ll figure it out.” was all she said… and he went straight to the bathroom, showered… When he stepped out, she said he had mail.
The white evnvelopes with the ‘past due’ notices weren’t a surprise, but the yellow one was. From a ‘Jenny Garland.’ He was sure he knew that name. He opened it up, and there were pictures of an attractive woman. Just pictures, that was it. Attractive nothing… she was one of the most gorgeous women she had ever seen. None of them were naked, but very revealing.
He stopped, he looked at his wife, she was engrossed in some show. He slipped back into the bathroom, placed the picture above his toilet and started rubbing himself. It only took a few minutes, his wife hadn’t helped him with that in over six months… And he had his release.
As he picked up the pictures he was about to put them into the folder and his wife walked in, clearly looking to refresh her drink, with the top shelf stuff… he let out a sigh. But he put the pictures face down.
The next night he returned home, this time in better shape, no lettuce or ketchup in his hair or in his pants and there was another yellow envelope. He opened it, and there were more pictures of Jenny. He jerked off to them again, but this time as he was about to put the pictures back into the envelope he saw a folded up little note at the bottom with a thumb drive.
“Hello Uncle Josh,
When I was five my mother met you. Her name was Tabitha Wrentham.”
He stopped reading for a moment, Tabitha, he had met her before he met his wife, she was beautiful and down to earth, and could fuck like no other. He even bought her a house and agreed to pay the property taxes for ten years if she kept herself available for ten years every weekend just for ‘fun times.’ He gave her a little money every month so she didn’t need to get a job. And she had a young daughter named ‘Jenny.’
Jenny had become beautiful. Last time he had seen her she was in her early teens and had made a comment about him being a pig, and he shut her up… Maybe she wanted a similar situation? He couldn’t provide it, but maybe he could have a quick fuck and tell her she wasn’t worth it first? He looked back down to continue reading.
“You used her like a whore, but treated her like a commodity. I’m not sure if I appreciate you for that, but I still hate you for that. I still remember the last words you said to me, “If you’re rich enough, you get to keep women. They will do whatever they can to keep that lifestyle, no matter how humiliating.” and I remembered those words well. In fact, my mother used you, she lived humbly except for when you were around, made sure I got a great education and every advantage. I built a company from the ground up, and last year my company aquired yours, and a thorough forensic search into your records found blatant illegal actions at your insistance. I’m the one who exposed you, I’m the one that got you removed. I’m the one who blacklisted you from ever working in such a position again. I’m the one who cost you your retirement accounts…I’m the one who took your son away.
But getting back to the original point. I have a kept woman myself now. Just like you once did. Only my kept woman is built to fuck, I’m sure you agree. Every curve on her entices you…
As your life degrades, I want you to know that my life is perfect, at your expense.
With Love,
Jenny G”
He was trembling as he finished reading the letter, anger and despair flared. But there was still the thumb drive, he took it, placing the envelope on the table. He went upstairs and plugged it into the back of his television. It was his son being forced into a cylinder, and a time lapse video of him being covered in a fluid and transformed… into Jenny’s kept woman. The woman he jerked off to… A series of pictures showed him struggling with his feminine style, eventually accepting, and later getting very good at it… to completely embracing it… and a final video..
One clearly taken from a cell phone, the person behind the camera, “So tell me Zoe, do you want to go back to your old life? Or would prefer to stay in ‘your’ house as my kept woman?”
His ‘son’ looked at the camera, acting like some slut, “I would love to stay as your Kept Woman… For as long as you want a woman like me.”
As the video ended, there was a smell of something burning, the thumb drive caught fire. Josh put it out… but then he
went back down stairs, the back door was open and the letter was gone…
Suddenly he had no proof of anything. She had set him up to know that everything was taken from him… and his son had become his Kept woman’s daughter’s Kept Woman… He would never find ‘Zoe,’ never prove what Jenny had done.
The End.
What did you think of that? Certainly I’m sure you would like to be my kept woman, right?
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