A Submissive Sissy free porn video

A Submissive Sissy


My sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever hopeful that I will heed his pleas and allow him to remain at home, dressed in his sissy maid attire, to do housework.

Please, Anna, my mistress,' he whispered, in his best fem voice, 'there is so much work here for me, I would love to have it all done by the time you get home today.'

'Nonsense, dear,' I said, ' today's trip has been arranged especially for you. You'll have plenty of time for chores and you know that it's a sissy's primary duty to accompany his mistress when and where she chooses. Besides, Felicia will be going with us today and she has been so looking forward to seeing you display your sissy charms in public.'

This was the first that Princess had heard that Felicia would be with us and he shuddered at the thought. He had little time to renew his protests however since at that moment the doorbell rang and Felicia appeared, obviously fully prepared for a day of fun at Princess' expense.

'Well,' she said, taking a slow stroll around my kneeling, naked husband, 'I see that Princess is not quite ready to go out. Tell, me Anna, what are your plans for him today?'

'I thought that we would take him a to a little beauty parlor downtown and give him a make over.' I answered. 'Just before you arrived, Princess was in the process of begging to be allowed to stay home. These excursions are most embarrassing for him, yet, as you can see from the pulsing hardness of his cock he is really very excited at the prospect.'

'He's quite the slut, isn't he?' said Felicia, with a sigh. 'I don't suppose you've allowed him ejaculate recently, have you?'

'Oh, no. Princess,' I said, looking down at him, 'when was your last orgasm and what were the circumstances?'

'Anna, my mistress, my last orgasm occurred 49 days ago and it happened accidentally while you were in the process of tying back my balls.'

'You made quite a mess didn't you?

'Yes, Anna, my mistress.'

'And now you're on indefinite restriction. Tell me Princess, do you deserve to have an orgasm?'

'No, Anna, my mistress, I do not deserve to have an orgasm. I will only deserve to cum when you say I am worthy and when it amuses you.'

'Very good, Princess, now let's get you ready to go.'

I turned to Felicia. 'This kind of outing is a delicate business. There should be no question of his being allowed to pass as a woman, even after his 'treatment', that would be too easy. Rather, we will adorn him with feminine things while at the same time making it clear that he is a submissive sissy male. As you can see,' I said, turning to the problem at hand, 'he is already completely smooth shaven and his legs are reasonably attractive so I think that we should show them off. A pair of very short cut offs will do nicely, no hose today I'm afraid Princess, just bare skin.'

'But,' I continued, 'That doesn't mean that we can't do something interesting with his feet. Princess, go get your panties, the cut offs and the baby dolls with the two inch heels, oh and get the pink socks with the ruffled cuffs.'

Princess sagged visibly at this partial description of his fashion statement for the day. Nevertheless, he left quickly and returned with the required items.

'Now, dear,' I said, in an instructional tone, 'put your things on and we'll see what else you'll be wearing.'

Both Felicia and I giggled as the sissy struggled into his tight pants. It was particularly fun watching him trying to manage his hard cock in a dignified fashion. The giggles turned into laughter as Princess put on his shoes and posed for us. 'Certainly, a bra is in order, wouldn't you agree Felicia?'

'Of course,' she answered, 'and then how about a top that's just a bit too revealing.'

'Yes,' I said, 'very good. Sissy, get the pink cotton top with the bare midriff and an appropriate bra.'

Poor Princess returned and donned the required items. My husband was completely humiliated as Felicia and I ordered him to show us how he would conduct himself on our trip to the salon. Naturally, we insisted that he mince about with an exaggerated wiggle of his ass and with his hands carried limply in front of him. We were so entranced that at one point Felicia ordered him back on his knees for a good tongue polish of her heels as I gave him a spanking.

'Now,' I said, at last, 'lets have a little make-up. Not too much or the folks at the salon will have nothing to do, but he really should have a little mascara and bit of lipstick. Come here Princess and I'll take care of you.'

'Yes, Anna, my mistress.' he responded, as he obediently came forward. My sissy husband presented his face for a few light strokes of mascara and lipstick. When I finished, I stood back to admire my work. Perfect, Princess had the appearance of a totally sissified male. He was feminized, but the shortness of his hair and the shape of his body made his true gender quite unmistakable. This, in and of itself was very satisfying, but the humiliation he was enduring, so obvious from his body language, made the scene doubly exciting. Again, Felicia and I laughed openly as we gathered our things and our slave and prepared to depart for Princess's appointment.

Just as we were about to leave, it occurred to me that a little extra humiliation for the sissy would be fun. 'Princess, go and get your leash and collar.' At this order, I could tell that my sissy slave was about to beg me that he not be collared, yet the resolute look in my eye stopped him cold.

'Yes, Anna my mistress, which collar shall I get?'

'Oh, the collar for your balls seems appropriate today, especially in light of your 'accident' 49 days ago.'

When he returned with the requested items he was ordered to pull down his shorts and panties and spread his legs enough to allow me access. I was about to snap the scrotum collar in place when I had a thought.

'Felicia,' I said, indicating that she should come over, 'would you like to do the honors?'



'Why, Anna, I'd be delighted.' She said, taking the collar from me. 'Now then, Princess, I'm just going to reach between your legs and pull your balls back.' So saying, the collar was put in place, a leash attached and the whole arrangement was dragged back between his legs. Of course, this caused his erect cock to point straight forward in a most obscene manner. He was then instructed to pull his panties and shorts back on and we laughed once more as he fussed over the positioning of his engorged prick.

Now we had him in a fine helpless position with the leash pulled hard up into the crack of his ass and then over the top of his waistband. With a little giddy-up flick of the leash, I had him lead me about the room as I tested his response to various tensions. I soon discovered that only a slight pull on the leash would cause my husband a great deal of discomfort.

'What do you think, Felicia?' I asked my friend, 'Does he look like an enslaved sissy to you?'

'He looks marvelous, Anna. Let's go show him off.'

It was a sunny spring day, just right for showing off a submissive male. Felicia and I strolled out onto the street with my sissy husband, Princess, leading the way. The leash I held in my hand was attached to his balls and every once in a while I gave it a gentle tug to remind Princess that I was in total control of the situation. I just love giving my husband the 'poodle' treatment and I was not disappointed in his humiliated response.

While Princess cringed and blushed at this forced display of his feminized self, he nevertheless was well trained enough to mince down the street with his best sissy posture. His hands were held outstretched at his waist, with an exaggerated, effeminate pose and his hips swayed seductively from side to side as he took each small step, one foot directly in front of the other. Of course he looked down demurely as he walked, further betraying his shame at his now permanent condition.

As we walked, I conversed casually with Felicia. 'You know,' I said, 'Princess always had a fascination for wearing women's clothes yet I don't think he quite realized where things would lead when he confessed his desires to me.'

'Were you surprised that he was a cross dresser, Anna?'

'Not really. His submissive nature was always very obvious so when he told me about his need to wear women's things, it seemed natural. I think he was the one who was surprised when I offered to allow him to act on those desires and I'm sure he didn't suspect that the price he would pay for my permission would be to submit himself completely to my control. He seems satisfied with the arrangement however. Princess,' I said, speaking up, 'tell Felicia how it feels to be my sissy slave.'

'Yes, Anna my mistress.' came his breathy response. I find it particularly exciting to hear my husband's female voice (the only voice he is allowed to use, the product of hours of practice) and now he spoke softly, but clearly, to my friend as we walked. 'It gives me great pleasure to be my mistress Anna's sissy slut and maid-in-waiting. I am really very empty headed and I am thankful for her guidance and her willingness to take control of my life.'

'Why is it that I can dominate you so easily, Princess?' I asked.

'Anna, my mistress, my cock and balls are the source of my submission. Giving myself to you, to use as you wish, to humiliate as you wish, provides me with a sexual excitement that is unquenchable. I am now utterly unable to resist you in any way. My cock is yours. My balls are yours. My soul is yours.'

'Very good, Princess.'

'Do you have any further plans for him?' asked Felicia.

'Well, I think it would be very exciting to see him sucking a real cock. Of course, he's required to practice on dildos and various other objects on a regular basis so I think he may soon be ready for the real thing. Before we cross that threshold however, he will have to show me that he can take a large strap-on completely into his throat. We'll be working on that later today, would you like to observe, Felicia?'

I glanced at Felicia as I said this and I saw that she was delighted at the prospect. 'That would be wonderful.' she answered, licking her lips. 'Have you given any consideration to who's cock Princess might be sucking when that time arrives?'

'Certainly I would want Princess to have his mouth fucked by a very large penis, but I'm not going to deliver him to just any male. Another sissy's or a she-male's cock, stuffed into his face, is the only thing that would turn me on. Why do you ask?'

'Oh,' she responded, thoughtfully, 'you've really been an inspiration to me, Anna. I've been thinking that it would be very nice to have my own sissy, who is enslaved like Princess, and I thought that perhaps you could help me identify and train the appropriate candidate. Then we could have a 'matched pair' for all sorts of activities.'

I can't say that I was much surprised by Felicia's idea. For some time, her fascination with my use and abuse of Princess had led me to think that she might be interested in having her own sissy slut at her disposal, so I was ready with my answer. I gave Princess' leash a sharp tug (causing an equally sharp intake of breath from my husband), indicating that I wanted him to stop walking, and turned to my friend, 'I've actually been thinking along just those lines and I'd love to work with you on that kind of project. You realize of course that owning a sissy slave is a great responsibility, don't you? Once a male abandons his will to yours it becomes incumbent upon you to do all his thinking for him. His days must be planned totally and, he will require a great deal of attention.

'Without a doubt,' I continued, 'a well chosen sissy will, with proper training, provide for all your physical needs, as any good servant should, but, like any pet, his care and 'feeding' must then become one of your primary considerations. I, for one, do not take these responsibilities lightly and I certainly do not support the notion that these submissive creatures are 'disposable', to be dismissed on a whim.

'Once enslaved, a sissy male becomes quite unable to fend for himself and I believe that it is unconscionable to turn him out, absent some egregious behavior on his part. As I hope you can see, my bond with Princess is based on true affection and his submission to me is only a manifestation of his own desires. It just so happens that my desires coincide with his. There, I'm done with my speech, what do you think?'

I could tell that Felicia was considering my words carefully. She was silent for a moment and then, with a serious look on her face, she answered. 'Anna, I have a incredible amount of respect for your relationship with Princess and I have decided that I want to have the same kind of thing in my life. I'm ready to be guided by you in these matters, will you help me?'

'Yes,' I said, we hugged and I was surprised at how moved I was by the moment. A casual outing had turned into something special for all of us. Not that Princess was going to be allowed to forget his place. As our embrace ended, I saw him gazing at us. 'What are you looking at slut?' I said sharply, tugging once again at the leash. 'Get going, we'll be late and I may have to blame you.' With that, Princess stepped out once again and, as a gesture to Felicia, in honor of our pact, I handed her the leash.

The salon was not far away, but distant enough that several passers-by had an opportunity to see my husband's humiliated state. Of course he blushed and quailed at each encounter, especially when a carload of teenage girls slowed and offered several derisive comments regarding Princess' attire and mannerisms. It was particularly funny when one of the girls, noticing the bulge in his revealing cut-offs, wondered aloud if it was authentic or perhaps just a sock put there to create the illusion of masculinity. This is just the kind of banter that causes my sissy the greatest embarrassment and Princess blushed a deep scarlet as he continued to mince down the street.

At last however, he gained the 'safety' of the salon, not too late, and we all joined Madame Camille in her office for the introductory consultation. I've know Madame for several years and she has, on a variety of occasions, expressed an interest in working with Princess. To this point I had not availed myself of her services, in large part because I like taking things slowly with his transformation. Much of my enjoyment at having a sissy slave is his gradual feminization. For me, each step must be thought through carefully and savored.

'Ah, Anna,' Madam said, with just a trace of French accent, 'I have been so looking forward to this day. I have seen you parading this sweet thing around town for some time now and I admit that I have had some not quite proper thoughts about him. He is obviously a work in progress. Tell me, what can I do for his appearance that would give you the greatest satisfaction?'

Salon Camille is a full service facility that provides beauty treatment and advice for hair, face and body. Diet, physical conditioning, removal of body hair, cosmetics and hair styling can all be part of a program of beautification at the Salon.

'Madame,' I replied, 'I'm interested in your opinion on every aspect of his appearance. I suppose, for starters, you could suggest some ways in which his body could be made more feminine. What sort of diet and exercise would be useful?'

'Hmmm,' Madame crossed one arm across her ample chest, propped an elbow on her hand and tapped her cheek with her index finger. 'He's not wearing much now, but I think it would be useful to see him totally nude. Can that be arranged.'

'Of, course,' I said, not unmindful of her ulterior motive. 'Princess, take your clothes off.'

Naturally, my husband was still very erect and he took an involuntary step back at this command. He's really very shy and he was most reluctant to show these women the extent of his arousal. With just a glance from me however, he straightened up and started disrobing. Shorts, shoes, top, panties and bra were soon in a heap at his feet. As he stood there, in his abject state, with his large, pulsing cock emitting a steady flow of pre-cum, I found myself loving him extravagantly and more than a little excited. It was wonderful to see how readily he gave himself over to me, an ultimate expression of trust.

'Yesss,' Camille hissed, 'he is quite developed isn't he?' Now, she walked around him, again tapping her cheek, but it was easy to see that she was very distracted by his pounding cock. She breathed deeply and, almost sadly, said, 'Perhaps we should get his organ under control, Anna. Could you do something about it, please.'

'Certainly. Princess, please soften yourself.' My poor husband. There he stood, completely humiliated and completely excited as we three women contemplated his throbbing penis. He could no more soften himself than he could jump over the moon. If anything, his cock became harder as it moved up and down in time with his pounding heart. Before long, Madame Camille, Felicia and I were all laughing at his red faced embarrassment.

'Well,' I said, with mock impatience, 'apparently, we need to use The Glove.'

'Oh, my mistress Anna, please no.'

'I'm sorry. If you can't get that thing under control then steps must be taken.' With that, I reached into my bag and drew out a leather glove for the right hand. No ordinary glove, of course, but one with the palm and inner portion of the fingers covered with plastic spikes, not so sharp as to cut flesh but sharp enough to cause great discomfort on an erect penis if the grip were strong enough.

I held it out to my husband. 'You know what you must do Princess. Be strong and it will be over quickly.'

With a low moan, my sissy slave put the glove on and, with a deep breath, firmly grasped his cock. A small cry of pain escaped his lips yet his penis continued to be hard. 'More pressure, Princess, and masturbate. Show the ladies how you please yourself.'

Slowly, with a spastic motion, my slave stroked himself with the devilish device. Still, his erection was unabated. 'Make it quick now Princess. We haven't got all day and I know you don't want me to take over the job.'

Now my slave, with true fear in his eyes, tightened his grip. The initial cry of pain became a steady wail and finally his penis began to shrink until at last it was a shriveled bit of skin in the grip of his right hand.

Swiftly now, I produced a satin penis sheath with lacing down it's entire length. 'Let go, Princess and present yourself' I ordered.

At this command, my husband released his grip and thrust his groin forward giving me easy access to his flaccid member. With one smooth motion, I pulled it through the loosely laced sheath and, just as the firmness began to return, drew the laces tight, leaving only the glans exposed. Instantly, he became hard again but now the sissy's cock was a fraction of it's previous size with the head sticking out, much like a lollipop on a stick.

'There' I said, looking significantly at the two, not unaffected women. 'Now we are ready to go to work.'

My husband, Princess, stood naked in the office of Madame Camille of Salon Camille. Naked that is, except for a tight satin sheath which held his very aroused cock in check. Camille, my friend Felicia and I were in the process of considering how my dear sissy's body could become more feminine. This assessment was a precursor to a cosmetic make-over which I had arranged for Princess.

'He is a bit chunky, isn't he?' said Camille, reaching out to pinch some flesh on my thoroughly humiliated husband. 'Of course his diet should be reviewed, Anna. I have some good, if obvious, suggestions on foods he should be eating every day as well as those which must be avoided. Certainly he should be on a regular program of exercise.'

'He works hard enough around the house,' I said, 'and I don't want him to be more muscular than he is already. What kind of a workout would you suggest, Camille?'

'Surely we don't want him lifting weights,' Camille said. 'I would recommend a program of Pilates. As you know Anna, Pilates is most useful for dancers and others who want to tone up their figure without becoming muscle bound. In addition, there are many more women than men doing this type of routine so your husband would be engaging in a program that has a distinctly feminine aspect.'

'At the same time,' Camille added, 'you shouldn't underestimate the value of a good corset. Have you done any figure training with Princess?'

'He has worn a corset on occasion,' I answered, 'but the one I've been using on him is really too large and only reduces his waist to about 30 inches. I guess we'll probably have to make yet another purchase. You do cost money, Princess.' I said sternly.

'Yes, my mistress Anna,' responded my husband, eyes downcast, 'thank you for taking such good care of me.'

'Well,' said Camille, 'I happen to have something on hand, although it's rather smaller than he might need at the moment. But,' she said brightly, 'why don't we give it a try.' With that, she stepped out of the office and returned with a pink satin thing that had more the look of a waist cinch than a full corset. Camille held it up to Princess' face, giving him a delicious whiff of the fabric.

'What do you think, my dear?' she taunted him. 'Would this feel good around that sissy waist of yours?'

'Oh, Madame Camille,' my husband whispered, almost swooning from the intense mixture of humiliation and desire, 'if it would please my mistress Anna, I would love to wear it.'

Camille turned to me and I nodded. 'Lace it tightly, please, Madame. I don't want Princess to think that this some form of recreational device.'

'Of course.' So saying, Camille approached Princess from behind and, with a practiced flip, drew the pink satin around his middle and began to lace it up. It really was too small for my little slut. The ends of the cinch were far apart as Camille finished the lacing, with an expanse of cord cris-crossing the sissy's lower back. 'Now for the hard part.' As Camille said this, she seized the two looped ends of the laces, put her knee in the small of Princess' back, and pulled with a firm, cross handed motion.

Instantly, Princess let out a gasp of breath and his waist pinched inward as the ends of the cinch began to move, inexorably, together. 'Now ladies,' said Camille, turning to Felicia and me, 'if you would assist me we will bring the sissy to phase one of the cinching process. Princess, dear, please hold onto the door there while we snug you down just a little more. Anna, Felicia, if you would each take a loop and pull, I'll make some adjustments.'

Each of us did our assigned tasks, though I must admit I became a touch concerned watching Princess struggle to take a breath as we tied the laces down. 'Relax, Anna,' said Camille, reading the look on my face, 'he'll soon adapt to the pressure and begin breathing more normally. In fact, as we take him through his treatment today, we'll have occasion to tighten it even more severely. See how nice his waist looks. Why, you could almost say he has hips and doesn't it do wonders for his ass? Princess, take a little sissy walk around the office so we can check your form.'

Obediently, but with great shame, Princess did his best prance back and forth as the three of us admired his new figure. Not only did the small corset accentuate his hips and ass, it also pushed his little titties up in a most seductive fashion. The fact that his stiff, but constricted, penis waved ridiculously in front of him as he minced about certainly added to our amusement at his predicament.

'Yes,' I said, 'you've convinced me, Camille. A good corset will be next on the list. Now then, what else do you suggest we do with him today?'

Camille took another casual stroll around Princess, pausing to run her fingernails across the swollen, exposed head of his otherwise imprisoned cock. This compounded the sissy's torment and he gasped again. 'You know,' Camille said, looking at me, 'I haven't had the pleasure of sitting on a sissy for some time. Would it be alright with you, Anna, if we all sat down, with Princess as my chair?'

'I don't see why not. All fours Princess.' I ordered. Without hesitation, Princess got down on his hands and knees and offered himself to Madame Camille. Ceremoniously, Camille walked over to him, presented the toe of her shoe for a kiss and sat astride my husband, horsey fashion, making a great show of grinding her ass into Princesses back. Felicia and I sat down and our discussion continued.

'We should do his nails first.' said Camille, decisively. 'Nothing says 'sissy' more dramatically than a nice set of long, brightly colored fingernails.' When Camille said this, I looked at Princess' face as he struggled to provide the salon owner with a steady throne. I was pleased to see him blush furiously as he considered how much more explicit his sissiness would be with a permanent set of nails attached to his fingers. Up to this point, Princess had imagined that, on various outings, his feminization had been somewhat subtle. Now, it would be impossible to hide his true nature from even the most casual onlooker.

'That sounds good.' I said, putting my own toe to the slave's lips for a gentle kiss.

'Then, of course,' said Camille, 'we should do his make-up. I thought that we would give him the full glamour treatment today but hold off on doing his hair for another occasion. That way, when you walk him home, his maleness will still be apparent but his sissiness will be just as obvious.'

'I agree. Do you like that idea Princess?'

'Yes, my mistress Anna' he said, in a somewhat muffled tone, obviously becoming concerned about the walk back to the house.

'I'm afraid you don't sound enthusiastic enough, sweetie.' I said, standing up. 'I'd like to hear a bit more appreciation for all the effort we're putting in here.' I took a quick step to his exposed backside and, with a fair degree of pressure, pushed the toe of my shoe between his legs and against his dangling testicles. He squirmed in satisfying fashion giving Camille a little jolt of pleasure. Now he spoke out, loud and clear.

'Yes, my mistress Anna, I would love to be all dolled up for our walk home. I love being your sissy. Please command me and I'll obey.'

'Good. Camille, as he is receiving his various treatments today, I hope your staff will take the time to teach him about the different techniques they are using and show him how he can apply these methods when he's working on himself.'

'Of course,' Camille answered, standing up at last, with a wistful sigh. 'We'll have Tammi do his nails, she's very experienced and I know that she'll be excited about contributing to Princess' feminization. Then, Candice will do his face. She's also an instructor in a small class we have on cosmetology, so she'll be able to show him a great many things he can do when he's at home. I know that both women will not be satisfied until your slave looks as girly as possible.'

'If that's all,' I said, 'let's get started. Get dressed dear.' Princess stood up immediately and started to put on his sissy outfit. Bra, panties, skimpy top, shorts and baby dolls all went back on. I never get tired of seeing my husband put on his frillies and both Felicia and Camille giggled as we watched Princess get himself together. Naturally, being the focus of attention for three women in this degrading circumstance caused Princess a great deal of embarrassment, and his nervousness showed in his fumble fingered efforts to hook his bra behind his back. His several failed attempts only caused more laughter from his audience and garnered several derisive comments.

Finally, he was done and we brought him out to meet the salon staff. Tammi and Candice were both introduced and it was easy to tell that they were fascinated by the challenge of further feminizing my slave. Right away, Tammi took Princess in hand and began to tell him about his manicure.

'You know dear,' she said, as she led him over to her station, 'the nails you'll be getting today are going to change your life. They'll be very long and pretty but long nails are as much of a challenge for the first time wearer as high heels. Do you wear very high heels dear? Oh good. Now, lets have a look at those hands. What a good sissy.'

My sissy husband, Princess, looked so cute as he sat at the manicure table in the beauty salon. Felicia, and I had walked him to the salon in one of his delicious sissy outfits and engaged a consultation with the owner, Madame Camille. Now, Tammie the nail technician was preparing his hands for a set of luxurious acrylic nails. For his part, Princess was utterly humiliated, both at the treatment he was receiving and in anticipation of having his sissy fingers on display for the world to see.

Right from the start it was clear that Tammie was very comfortable working on a man. Princess was not nearly so at ease. At first, it seemed as though his excessive squirming was due exclusively to the embarrassment inherent in the situation. After all, here he was being worked over by his wife, his wife's friend and assorted professional women, all intent on feminizing him in such a way as to bring him maximum shame.

I finally realized though, that the poor sissy was in extreme pain as a result of the penis sheath I had placed on him during our consultation with Madame Camille. I had cinched it very tight but in my fascination with Princess' beautification, I had quite forgotten about his confinement.

It was a mildly awkward situation since, by now, Princess's manicure and prep for applying his nails was well underway and I was reluctant to interrupt Tammie as she worked. But something, had to be done to avoid permanent damage to my property.

'I'm sorry, Tammie.' I said, 'It seems that my Princess needs to have his cock corset either adjusted or removed. Could we stop a moment to let him get more comfortable.'

'Oh, dear, we're right in the middle. If he starts fooling with zippers and such it's probably going to ruin what I've done so far. Is there any way that you or your friend could help him . . . out?'

At this, Felicia, who had been very much of a bystander for much of the visit to the salon, spoke up. 'Please, Anna, let me see what I can do.'

'Of course, Felicia.' I responded and stepped aside. 'Princess, stand up and present yourself to Felicia. I'm going to be upset if you disturb any of Tammie's work, so be careful.'

Obediently, my sissy husband stood up very slowly, keeping his hands nicely away from his body, turned and made himself available for my friend's attentions. Now Felicia took over.

'Well, Princess, let us see what we have going on,' Felicia said this as if she was addressing a four year old and it was marvelous to see the waves of humiliation pass over the sissy as he waited, helplessly, for relief. Felicia then unzipped the tight cut-offs and, in one sharp motion, yanked the shorts and the sissy's panties down so as to expose his imprisoned, twitching cock.

By now, the little scene had attracted the attention of salon employees and patrons alike and a small circle of spectators had gathered. This humiliation, in combination with the pain the sissy was enduring seemed almost too much for my husband and I thought for a moment that he might faint. Various comments offered by the onlookers added to my amusement. It's fun to step back from time to time, after orchestrating a particular set of circumstances, and watch as other women take on the role of abusing and embarrassing Princess.

'My, my,' clucked Felicia, continuing to speak as if to a c***d, 'you're little cock looks extremely mistreated.' And indeed, Princess's penis had become a limp tail of flesh that made a pained jump every few seconds or so as his sissy excitement continued to vie with the physical discomfort.

Felicia was in no mood to provide instant relief. Savoring her turn in the limelight, she was more than willing to draw the process out. 'Now Princess,' she said, 'before we release you, please show the ladies how good little sissies get their cocks dressed up by their mistresses.'

This was too much for him and, in spite of the pain and the cock sheath, the sissy's 'clit' began an inexorable rise (at least to the extent possible within its imprisonment) with a steady pulse as he stood there before his audience. The women were nicely amused by this display and I was fascinated to see a small trickle of sweat run down the side of his face.

Felicia allowed the moment to play for just the right space of time and then moved in again. 'Now, 'girl', I'm going to release you but I want no unseemly display and you better continue to be careful with Tammie's work'

Slowly, Felicia unlaced the sheath and it was remarkable to see his penis expand to fill all the available space until at last, the unencumbered cock stood up, rock hard and dripping, for all to see. Felicia then gave me a significant look and understanding her intent, I nodded slightly. Quickly, Felicia seized Princess' cock and began masturbating him with a slow, sleek, motion. Princess, knowing full well the consequence of an unpermitted orgasm, gasped and moaned as he struggled to hold himself back. A steady flow of pre-cum had soaked his pants even as the ultra tight sheath had squeezed his cock and now the delightful, wet sound of a sissy cock being stroked was heard each time he stopped grunting to take a breath.

The situation was made even more compelling by the laughter of the other women as they appreciated the intense struggle that was raging inside the sissy. After a few firm strokes, Felicia, knowing the limit for even a well trained, feminized man, let go and with another quick motion pulled up his panties and shorts, zipped him up and said, 'OK, show's over slut. Let's get back to those nails.'

In businesslike fashion, my friend walked over to the manicurists sink and washed her hands thoroughly. As she dried her hands, she turned and gave a slight bow to the other women, receiving for her efforts a brief but heartfelt ovation from the spectators as Princess sat down to have his manicure completed.

'My, that was exciting.' Felicia sighed, as she made a show of fanning herself with one hand. 'The more time I spend with you and Princess, the more I'm convinced that I need a full time sissy for myself.'

'Yes,' I answered, gazing at Princess as he sat with his hands outstretched at the manicurist's table. 'It's very addictive for women of the right temperament. And, Felicia my dear, you have the proper temperament. How would you like to proceed?'

'I'd like to just keep talking with you. Obviously, I have my own thoughts on the subject and, I'm sure, some misconceptions. But how would you go about identifying the right 'candidate?'

'A well placed advertisement in the right publication or on the right web site would certainly yield a significant response. There are many sissies out there who would be falling all over themselves to grovel at your feet. But before we open the door to that kind of stampede let me make a few inquiries. It's possible that there are some 'girls' in the area who would be a good fit for you. Tell me, if you can, what sort of characteristics you have in mind.'

'Unsurprisingly,' said Felicia, 'appearance and personality are equally important. I want a slave who looks good when he's all dolled up but also someone with whom I can be comfortable and affectionate. I've seen you and Princess together enough to understand that companionship is woven together with dominance and submission in your relationship.'

'I'm glad to hear that your not embarrassed by your desire to have a slave who looks good.' I responded. 'Let's explore that notion. Obviously, there are a great many men who, dressed and made-up, would easily pass as attractive and even beautiful women. They are, of course, a delight. But there are also men, who might never be mistaken for female who, nevertheless, are very seductive when properly feminized. I would say that Princess fits into this category.'

'Yes,' said Felicia, 'I know exactly what you mean. He's large, in good shape, and he even has some muscle but his skin is quite elegant, his legs are divine and a little make-up releases a feminine creature who is quite unexpected. He's a wonderful trophy, Anna.'

We conversed in this vein for a bit until I noticed my little whore standing silently, several paces away, waiting for the proper moment to present himself.

'Show us your sissy fingers slut' I said this, without bothering to look at him, in a tone meant for him alone.

I looked over as Princess minced carefully towards me, holding his hands in front of him in archetypal sissy style. It was funny and the slut's continuing shame at his public submission only increased our amusement. Both of us inspected his extra-long mauve nails closely. While we continued to be seated as he stood there it was easy to view the outline of his very hard cock under the skimpy shorts. A short study of his crotch also revealed an intense pulsing as the thing swelled and relaxed with each beat of his heart.

'Now sissy.' I said, sharply, suddenly, 'Cum!'

Instantly, Princess thrust his pelvis violently forward and then began to make short, urgent pushes as he emptied himself into his panties.

'Good girl,' I said, as Felicia and I both giggled, 'now reach in there with your new nails and show us how much you like the taste of cum. Don't stab yourself.'

Andrew's Conversion

The Rules Redux

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.
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.
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.
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.
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.
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.
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.
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.
As always, each chapter will commence with a Task for you which must be completed before you may read further.
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.