A Submissive Sissy

Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !


A Dominatrix returns

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Andrew's Conversion

The Rules Redux

  1. You are my sissy-slut. Your sissy-clit is mine. Your sissy-pussy is mine. Your sissy-titties are mine. My voice will be in your little head constantly. In every phase of your life you will constantly ask yourself, 'Would Mistress Katherine approve?' You will behave accordingly.
  2. You may not ejaculate more than once in a 48 hour period and you may not read what I have written here (or anywhere) unless it has been 48 hours since you last came. If you come while you are reading, you must put it aside until 48 hours have passed. You must be anxious and excited each time you explore your enslavement to me.
  3. At a minimum, whenever you read something that I have written, you must be wearing some frilly, feminine article of clothing. It must be something which constantly reminds you of your sissy-slave status even as you strive to pass as 'male'. Stockings and bras are preferred since their feel is unmistakable and perpetual. If panties alone are worn, they must be extra-tight thongs so that you constantly feel them imprisoning your sissy-clit while they apply pressure to your sissy-pussy.
  4. Whenever possible, when you read these chapters, you must be fully feminized. Wig, make-up, high heels, nail polish, corsets and breast forms must be part of your ensemble. If you do not currently own these items you must make plans to obtain them. The more humiliating the circumstances of their purchase, the better.
  5. Facial hair is forbidden. You must shave daily. Imagine that I may appear at your door, unannounced, at any moment, and imagine the punishment you would endure if I were to touch your cheek and feel the offensive sandpaper texture that is the result of neglecting this basic responsibility. Feminine facial creams must be used daily. Trim your eyebrows.
  6. You must own a butt plug of a size that fits your maximum 'capacity'. As your sissy-pussy stretches, you will purchase larger plugs. A plug that slips out easily is too small. You will endeavor to have your plug in your sissy-pussy as often as possible. You will make an extra effort to have your plug 'in place' whenever you read what I have written.
  7. When you are not masturbating or bathing you must, at all times, wear a ribbon or leather collar around your sissy-clit. A commercial chastity device is certainly appropriate. This will be your ultimate reminder that you are my sissy-slut.
  8. As always, the rules may change according to my whim, in some cases only subtly. You must review them carefully upon each new publication and you must obey the most current version.
  9. As always, each chapter will commence with a Task for you which must be completed before you may read further.
  10. The Task - 'Make a Purchase.' : In accordance with Rule #4, make a purchase of some feminine article which requires you to interact with a sales person in a way which makes your sissy predilections explicit. A visit to a lingerie store is always good for your sissy education. Asking for help at the cosmetics counter of a large department store is even better. If you are a typically shy sissy then it is acceptable to order something by mail but. . .you must at least have a live telephone conversation (e-mail is not sufficient) with a sales person in order to complete the purchase and you must reveal that the purchase is for your own personal use.

Now, you may read about Andrew's predicament.

Since my last writings regarding my professional life I have taken a less formal approach to my work with individual sissies. Yes, I still prefer to referrals from women who have particular goals for a particular male but I no longer insist on long-term programs of feminization. Lately, I have been taking on certain sissies for little package called Maid-in-Training. As usual, I most enjoy working with males who's sissy desires have not yet come to full flower.

Such was the case with Andrew, the 34 year old husband of Jennifer Rosemont. This couple had been together for about 3 years when Ms. Rosemont contacted me seeking an interview. It seems that her work as an upper level telecommunications executive had become far more interesting then her relationship with Andrew.

Andrew though had long been obsessed with Jennifer. So obsessed in fact that he was willing to do anything to remain with her. Even it seems, to the extent of allowing the essential nature of their relationship to be changed. Per my usual practice, the three of us met for an application/orientation session in my office.

Upon first meeting the pair it was easy to understand Andrew's attraction to his wife. Jennifer was an extremely good-looking woman in her mid-thirties who displayed all of the self assurance necessary to her professional role while at the same time showing a warmth which made our conversation relaxed and productive from the start. After seating Jennifer in one of several large, comfortable chairs I directed Andrew to sit in the single, straight-backed chair and began the discussion.

'When we spoke on the phone, you said that you thought it was time for you and Andrew to 'move on', I believe was the phrase you used. Tell me a little more about what you have in mind.'

'Well,' Jennifer responded, 'Frankly, I'm just not satisfied with Andrew as a partner. His love making is ordinary, we don't seem to have much to talk about any longer and his career has stalled. I still have, let us say, a brotherly affection for him but I was about ready to call an end to the relationship when he begged me to consider finding an alternative which would allow him to remain in my house.

'Upon consideration I knew that any such arrangement would mean that he would have to submit to me explicitly. So, for the last six or seven weeks he has taken on the role of a house servant and yet I now think that I'd like something just a bit more unusual.

'I did some research, and I thought more about it and decided that he could stay if he agreed to allow himself to be feminized.'

'What a nice decision,' I said, 'Obviously, this is an area of extreme interest to me. Would you mind answering a few more personal questions?'

'Alright. If I'd rather not answer I'll let you know, but there's no harm in asking.'

'Wonderful. First, before this came up, did you have an interest the feminization of males?'

She thought a moment, 'Not exactly, but I admit that I've always found female impersonators to be . . . tempting.'

'Have you ever been intimate with a male who was wearing something feminine?'

'Oh, I had a boyfriend who put on my panties once or twice but he was so butch it never occurred at the time that he might be into cross-dressing. Since I've read up, I know it happens all the time.'

'Yes,' I said, 'Now that you're looking for them you'd be amazed to see where panties and lipstick turn up. And what about Andrew? Did he give you any reason to think that he would make a good sissy?' As I said this I glanced at the object of my question and was rewarded with a distinct wince on his part.

'He seems to get a bit turned on by my panties too, but other than that I never got the feeling that he was interested in actually wearing them or any other women's clothing.'

I appraised Andrew directly now, for the first time. Silence filled the room as I studied his face and physique. I stood up, towering over him in my customary 5 inch heels, and walked slowly around him. Jennifer showed no impatience with this pause in our discussion seeming to understand the juncture we had reached.

I found myself pleased with my observations. Andrew was a moderately good looking male with none of the hyper masculine features which characterize so many 'men'. As such, I saw good possibilities for a classic transformation process. He was a bit over 5'10" and his body also showed potential for a change in the right direction; not too muscular and not running to fat. Ahh . . . for nice legs.

Andrew's reaction to this scrutiny was of as much interest to me as his appearance. His response to being studied was a nice mixture of embarrassment, excitement and exasperation. As I reached down to grasp his thigh through his jeans, he pulled away instinctively. My reaction was to make no further effort, rather, I looked significantly at Jennifer who said, 'Andrew!' sharply, whereupon the husband sat up and returned his leg to where my hand was waiting.

Gripping his leg firmly I leaned forward and gazed into his eyes. 'Thank you, Andrew.' I said, softly, 'I think that you have very nice legs.'

This close contact allowed him to smell me, feel me, hear me and it gave him an chance look directly at my full, luscious breasts. He sought to resist but it was no use, he was transfixed.

'Well, Andrew,' I said sitting down, 'how would you feel to be left in my care for a while as we work on the changes your mistress would like?'

Instead of answering me directly, the poor thing looked back and forth between us, finally whispering, 'Please Jennifer. I'm confused. I want to be with you so bad. I want to do what you wish but don't make me do this. Please.'

I cut in, 'Are you really so conflicted dear? Let me tell you my plan. You are going to follow my commands and, together, we are going to explore your feminine side. We are going to shave your body hair completely and you are going to keep yourself shaved. You are going to learn every aspect of seductive feminine dress. Bras, panties and stockings will be worn by you on a daily basis as I restrict your ability to wear male clothing. And, soon enough, you will own no male clothing.

I stood up and paced back and forth before him, 'You see how nicely I carry myself on these heels? You will have heels of your own, many pairs, and you will learn to carry yourself just as nicely. But differently. Whereas I walk like a woman, you will walk like a feminized male, a sissy. You will learn to wiggle your hips and carry your hands limply in front of you.

'You will be given elaborate lessons in make-up. There will come a point when you will feel naked unless you are wearing a deep rich coat of lipstick and dark slutty eyeliner and shadow. False eyelashes will be in place daily. Naturally, you will have to learn to beautify yourself while wearing extra long nails which will always match the color of your lipstick.

'Perhaps you will be permitted to grow your hair or maybe you will be forced to rely on an assortment of wigs. I find it fun to shave my sissies' heads and require them to parade around in public with their full make-up and sissy wiggle. Won't it be nice to beg me to allow you to wear one of your wigs.

'Oh, and your body will undergo some important changes. I will feed you and work you so that you have the most feminine form possible. And when there is no more change that can occur, you will wear corsets with padding in the appropriate places. You may even be lucky enough to get breast implants. Just think, Andrew, won't it be sweet to have big titties just like mine that can be fondled, pinched and imprisoned.

'Of course, your sissy-clitty will not be neglected. Mostly, it will be bound up so that you can't abuse yourself without my permission. But, when you have been good, when you have shown your commitment to your sissy training I will let it loose and I will be pleased to watch you as you masturbate at my command. Perhaps I will have friends over and surely you will perform slutty demonstrations for your beloved Jennifer. Will you be allowed to come? Who knows?

'All the while that you are evolving into the ultimate sissy you will be learning the lessons of maid service. Proper domestic posture and responses to commands will become instinctual. Anticipation of Jennifer's needs will be the driving force in your life.

And there is so much more. I will train your mouth to do more than eat and breath. I will train your sissy-pussy expertly. . .aggressively.'

As I spoke these words, Andrew's breathing became deeper and his body began to undulate as he sat, gripping the sides of his chair. He stared at me as I continued to walk about the room. Then I stopped talking. Except for the labored gasps of my victim, silence returned to the room for a moment.

I approached my new sissy. 'Stand up slut.' He stood, quickly. 'Pull down your pants, now.' He fumbled urgently at his waistband and as the jeans fell away his rock hard erection sprang forth, bouncing with each beat of his pounding heart, oozing a steady stream of pre-cum.

'No sissy, I don't think that you are conflicted at all.' And Jennifer and I both laughed. The fun had just begun.