Sissy Assignment Reports!

by rachel varga

I was aghast to think my young fiancee had just signed me up for a course in cosmetology. I really don’t remember expressing any interest in that subject.

Of course I always admired the way Janice was beautifully groomed. Her make up and clothing were always perfect. And of course with her trim athletic figure and entrancing eyes she was the most beautiful woman I have ever seen.

In fact, it was difficult for me to understand what she saw in me. I’m certainly no prize winning specimen of masculinity. At five eight, I’m rather small boned and have rather rounded features for a guy. But my skin is very soft and white. I’ve tried to take care of what I have.

I’ll never forget the time we first met. I was so overpowered by her beauty that I didn’t even notice she was three inches taller than me. Her long golden hair fell in soft curls to the middle of her back. It looked lovely with the black velvet ribbon which matched her dress. Now as we sat on the couch in her living room, her penetrating blue grey eyes looked lovingly down at me. I was massaging her nyloned feet. She understood that I was having serious reservations about attending the five day cosmetology seminar.

“Now Kim, I know how you feel. But you must always remember that when we decided to get married, I was going to be the bread winner. And your job, honey, is to stay at home and take care of my needs and the house. Surely your not backing out of our agreement before we even take our vows.”

“But Janice,” I heard myself begin, “cosmetics are for women. I’ll bet there will be no other men in the class. I’ll feel so silly – the only rooster at a hen party!”

“Maybe so” she giggled thoughtfully, “but I’m afraid you are just going to have to get used to that. After all, you’re going to assume the traditional housewife’s role in our relationship and I don’t want you to go through life regretting it. As my obedient little housekeeper, your going to have to be supportive of my career. Your efforts, though mostly behind the scenes,are going to contribute to my success as an attorney. Whether you are ironing my clothes, or helping me with make up, or just simply mopping the kitchen floor, I want you to take special pride in each little task, knowing that you are contributing to my success and our happy home.”

I found it very difficult to argue with Janice. Her arguments are usually very sound. With her being three years older and a law school graduate, I almost always come around to seeing things her way. Also, we had agreed early in our relationship that she would make the decisions and that I would always do my best to live up to her expectations. As proof of my love and trust, I had in effect given her authority over my life.

After I finished with the other foot she smiled a loving “Thank you honey, that was nice.”

Knowing it would make her happy, I went to the bar to refresh her drink. Except for just a sip to test hers, Janice didn’t allow me to drink alcoholic beverages. I used to enjoy an occasional after dinner cocktail, but giving it up was worth it.

As I returned, she casually reached under her skirt and lowered her panties and pantyhose.

“Here, Darling” she smiled, trading me her soiled lingerie for the vodka martini. “Go up and rinse these out, and then get ready for bed.”

Jan knew that she didn’t have to tell me to perform this nightly chore. But I think she took a secret delight in exercising her authority. I stood on my tip toes to give her a loving peck on the cheek before hurrying off to do as she asked.

We each had separate bedrooms with a private bath. Hers of course was much larger than my own. I thought that was as it should be, but I kind of resented having to rinse and hang her lingerie in my own bathroom. Jan didn’t like the clutter in hers. As I gently squeezed soapy bubbles through the thin nylon, I thought back on our little conversation. “Yes” I thought, “I do take a special kind of pride in taking care of my beloved lady. It’s so nice to see her going off to the office in a smart business suit, knowing that I had pressed the pleats of her skirt perfectly. And that underneath the suit, she was comfortable in freshly cleaned undies which I had also pressed after carefully washing and drying them.” With a warm feeling of love, I hung her things over one of my towel racks to dry.

Since moving in with Janice, most of my own pajamas had become worn and gone by way of the trash can. Now practically all my nightwear consisted of Janice’s cast offs. Most, because she had tired of them. But a few she had given me as gifts on special occasions. At first I was quite embarrassed to be seen in a sheer nighty, but Janice always seemed more loving and attentive when I wore them. “And besides” she would grin with a twinkle in her eyes, “you really don’t have a choice, do you?” And she would playfully tweak one of my little nipples through the soft sheer nylon.

Each morning I wake at least an hour before Jan. She likes to have her breakfast served in bed. After getting used to the routine, I enjoy it too.

Its nice to wake her up with a soft kiss to the smell of coffee and crispy bacon. While she eats, I lay out her clothes and lingerie as we talk about her plans for the day. Also she never hesitates to let me know what I need to take care of before she gets home. Sometimes she’ll let out a low whistle as I busy myself with her clothes. She likes to kid me about my legs when I’m wearing a baby doll. She insists that I keep them shaved and always wear at least three inch heels around the house. Most of the sleep sets she’s given me include matching heels.

As she brushes her teeth I start her bath. One morning, I was wearing a very short pink satin baby doll. As I bent to draw her bath water, she pinched me hard on the bottom through the matching panties. With a loud shriek I jumped straight in to the warm scented bubbles. She could tell by the angered look on my face that I was not amused. But with complete disregard she stepped out of her ankle length nightgown and joined me in the large tub.

“Soap my shoulders and breasts first” she directed, continuing to ignore the upset look on my face. Perhaps it was a test. My pretty satin nighty and matching panties were soaked. Not to mention the matching high heels which felt so soggy now still on my feet. With only a slight hesitation I took the sponge she offered and gently began the task of bathing her. She smiled knowingly as the tears welled up in my eyes. Before I finished I heard myself apologize for becoming upset with her. I turned on the spray and we both rinsed off before stepping out of the tub. The pretty satin and lace of my nightwear clung wetly to my body as I dried Janice with a big fluffy towel.

“Your such a little sweety” she smiled. With a soft pat of her hand on my cheek she took the towel and wrapped it around her marvelous body. “Hurry and get dry now Kim. I want you to help me dress.”

My knees felt so weak as I submissively obeyed.

During the week of cosmetology classes, I learned quite a bit about women as well as make up. I was the only male in the class. After the first embarrassing day I didn’t hesitate to let Jan know how upset I was.

Sitting on the couch, she just smiled and motioned for me to take my place on the floor at her feet. Then, completely ignoring my tantrum, she had me tell her what I had learned so far.

Well, I guess by the time I finished I had learned quite a bit. Enough that, after much practice, I even surprised Jan. She would frequently bring her secretary, Julie, home with her so I could get more practice. Julie thought it was a “real blast” to have her hair and face done by her boss’s future husband.

The first time was a little embarrassing for both Julie and I. Me, because, Janice insisted that I wear a very short nylon beauty operators smock. Actually, it was just like a tight fitting dress. Through the thin nylon one could easily see the fancy lace embroidery of my matching chemise and full cut panties. I blushed madly when Julie complimented me on my legs with their white four inch heels.

I got my revenge when Janice had Julie slip out of her dress so as not to get it wet. At first she declined, knowing it wouldn’t be proper with a man in the room. Janice sensed her concern.

“Oh, don’t worry about Kim” she said. Then she walked up to me. Her hand toyed with my ear lobe as she looked directly into my eyes. “Just think of him as one of the girls” she grinned. “That’s why I had him wear the uniform.”

With that, Janice turned and had me undo the back buttons of her own outfit. Dressed only in her matching lingerie of gleaming grey nylon she went to Julie and helped her out of her dress. Though not as fancy as what Jan wore, I was happy to see Julie wore a pale yellow set including panties, half slip and lacy brassiere. It felt strange to be fully dressed in the feminine uniform with both of these lovely creatures in just their thin undies. Janice had me fix them both a drink before starting on Julie. Strangely, as I worked, and the girls chatted about their day at the office, I didn’t feel at all out of place.

Afterward, Janice had me help Julie back on with her dress. I blushed as I knelt to straighten the hem and smooth the full skirt over her thighs. She stooped down and gave me a sisterly peck on the cheek and slipped a five dollar bill into the opening of my uniform. Before she left, Julie thanked me with a big smile and did a little pirouette which afforded me a good view of the pretty yellow lace of her slip.

Janice told me that Julie would be coming home with her on Mondays and Thursdays to have her hair done. Of course I didn’t really mind doing these things for my lovely fiancee. But it was quite another matter serving an almost complete stranger. As her husband to be, I felt it very demeaning to serve as a beautician for someone else. I let Jan know how I felt.

“Well, Kim, hopefully you won’t feel Julie to be such a stranger after a fewweeks of giving her beauty treatments. As my personal secretary, she helps me out tremendously at the office and its important for her to look nice. From now on I want you to show Julie the same courtesy and respect that you show me. If you think about it Kim, you should be the one to thank Julie for helping you keep in practice.”

The following Thursday I used all the tricks I had learned to make Julie as attractive as possible. It really wasn’t that difficult. She was naturally very attractive. Once again, Jan had insisted that I wear the thin nylon uniform. “It will make Julie feel more comfortable” she smiled “and I think its really cute the way your pretty underthings peek through the thin materiel.”

After I finished my work on Julie that evening, I helped her back in to the slim skirted business suit. Once again she had worn a matching set of lingerie. This time in soft powder blue. As I helped her into the narrow skirt, I took a secret delight tucking in and smoothing the pretty blue half slip around her soft bottom and firm thighs. After zipping her up in back,I knelt and lifted the hem of the skirt. Gently I tugged at the lace trim of the slip until it hung neatly.

Remembering Jan’s words, I heard myself thanking Julie for the privilege of working with her. It wasn’t until I saw the knowing sparkle in her deep blue eyes that I realized that I had unconsciously executed a very feminine curtsey. Holding the skirt of my short uniform, I had displayed a generous amount of lace at the hem of my pale green petticoat.

A broad smile came to Julie’s features as she complimented me on my lingerie. I blushed deeply when her fingers toyed with the straps of my slip and bra through the translucent nylon of my uniform.

“Kim is really a darling, isn’t he?” asked Janice as she moved next to me and rested a hand on my narrow waist.

Without waiting for a response, she said that Julie would be staying for dinner and asked me to freshen their drinks before starting on the meal.She said they needed to discuss a contract they were reviewing at the office.

After I served dinner and cleaned up in the kitchen, Jan had me come in to the living room. They were still discussing business. Without missing a syllable of her conversation, Janice simply glanced at me and pointed to her feet. I blushed as I realized she wanted me to massage her feet while they continued their discussion. Dutifully, I knelt at her feet and removed her high heels. I felt so humiliated having to perform this menial task in front of Julie. I wished the earth would open and swallow me up!

It was perhaps twenty minutes later when Jan moaned pleasurably and thanked me for a wonderful foot massage. She reached down and playfully pinched my ear lobe.

“Now its Julie’s turn” she smiled.

I knew better than to resist. My cheeks were aflame. Still on my knees, I turned to Julie. I desperately tugged at the hem of my uniform which had ridden up above the middle of my soft rounded thighs. My nyloned knees were pressed tightly together. As if she expected me to obey, Julie casually lifted a foot and let it rest in my lap. The three inch heel of her pump pressed firmly into my thigh through the thin nylon of my skirts and pantyhose. Completely humiliated, I removed the delicate shoe and slowly began. Neither of the ladies seemed to be even slightly aware of my humiliation as they continued their discussion.

I worked conscientiously. The sounds of their conversation drifted as I thought about the lowly position I had assumed. A position where my complete obedience was expected. My lovely Janice, and now her secretary Julie, merely accepted my subservience as though it were the most natural thing in the world. As I worked with Julie’s soft nyloned feet a feeling of warmth coursed through me. Perhaps this is the way it should be. I don’t know how long my thoughts wandered. Julie’s soft hand on my cheek brought me back to the present.

“That was very nice, Kim” she smiled down at me. Lifting her nyloned foot from my skirt, she handed me her glass and suggested that I refresh their drinks.

“Yes, Ma’am”, I automatically responded. It wasn’t until I had gathered both glasses that I realized what I had said. Why had I used such a tone of respect? Julie was certainly no older than myself. Indeed, I thought her to be a few years younger. My thoughts were in turmoil as I returned with the drinks.

Janice informed me that Julie would be spending the night.

“It’s getting late Kim. And I want you on your best behavior in the morning. Go and get ready for bed now, honey, while Julie and I finish our drinks.”

Thank goodness, I thought, she’s not going to humiliate me in front of Julie by having me rinse her under things.

“Put on your pretty yellow sleep set.” she added as I headed for my bedroom,”and then come and give us a good night kiss.”

“Us?” I wondered. What did she mean by that? And why had she told me to wear my yellow outfit. It was definitely the prettiest set I had. But the see through nighty was so short. It merely highlighted the soft yellow lace of the sleeping bra that I wore underneath. And the ruffled hem ended above my slim waist. My little belly button was bare for all to see above the high waist line of the matching nylon briefs. Janice had me embroider a small satin “K” above the left leg opening of the panties as well as just above the left breast of the nighty. Knowing I was going to be put on display in front of Julie, I tucked myself neatly between my legs before pulling up the soft panties. The set also included a wide yellow satin ribbon which I tied in my shoulder length brown hair. The big fluffy bow exactly matched the smaller ones on each of the four inch slippers. After checking my appearance in the mirror as Janice had taught me, I self consciously teetered back into the living room. I noticed that both girls had moved to the large couch.

The silence was sudden. Julie let out a low whistle. Janice was the first to speak.

“You look absolutely lovely, Kim. Come closer and turn around” she motioned.

I felt so strange. My cheeks burned as I slowly turned.

“Simply remarkable” breathed Julie. Her finger touched the little “K” on my panties. “You have such fantastic legs, Kim.” She turned to Janice as her hand continued boldly down my left thigh. “Jan, I think Kim should have been a girl. She’s beautiful! And I can’t get over how well you have her trained.

You’ve just got to lend her to me one of these days.”

My eyes were locked with Jan’s. “Yes, she is a little doll” intoned my fiancee. She reached for my hand and slowly pulled me down to the couch between them. Gently, she pushed me back until I lay with my beribboned head resting on Julie’s skirt, at the juncture of her thighs. Jan’s eyes penetrated my very soul as she lowered her lips to mine. Beneath the thin nighty, she toyed with my sensitive nipple through the thin crisp lace of my pretty sleeping bra. Her firm warm tongue pierced my lips. Her hungry kiss pressed me firmly into the feminine mound beneath my head. It was almost as if Jan was using me as an instrument to intimately caress her pretty young secretary. Julie moaned softly and slightly raised her hips. Julie’s soft fingers played at my ears with threatening familiarity as I submitted to Jan’s attentions. I was breathless.

After several minutes, Jan broke the embrace. Her eyes sparkled with loving dominance. As the sexual aggressor, she had demonstrated her mastery over my body and mind. Julie continued to fondle my ears possessively. She somehow seemed to understand how I felt, surrendering completely to the will of my beautiful fiancee. With my head still resting at the vee of her thighs, I could feel the heat rising. I felt betrayed by the look of disappointment in my eyes when Jan lifted me once again to a sitting position. Then standing, she pulled me to my feet. With a knowing grin she straightened my nighty and repositioned the waist band of my pretty panties.

“Now tell Julie good night and run along to bed. You’ll need to prepare breakfast for both of us in the morning, dear. Oh, and lay out an extra nighty on my bed. I think Julie would like the blue one.”

Blushing furiously, I bent to give Julie a peck on the cheek. Thankfully, she accepted the gesture and sweetly bid me good night.

Before leaving, Janice handed me two pairs of crumpled pantyhose and two very pretty but wrinkled pairs of panties. The light blue ones I realized were the perfect match of Julie’s half slip.

“You know what to do with these, dear.” she smiled, sending me off with a firm pat on my yellow pantied bottom. “And Kim, don’t forget, in the morning you’re going to have double duty. So be sure to get a good nights rest.”

Janice, my beautiful fiancee, had been right. Soon I came to accept her young secretary, Julie, as just another facet of my new life. Although she was actually two years younger than myself, Janice insisted that I treat her with the same respect and courtesies to which she herself had become accustomed.

I served tea while Janice explained our relationship to Julie. My cheeks burned with embarrassment and I wanted to retreat to the kitchen. Jan insisted however, that I remain. I stood facing them as my fingers toyed nervously at the frilly hem of my short feminine apron. My eyes were lowered to the floor. I wished it would open up and swallow me as I listened.

“You know, Julie, that Kim and I live a somewhat different lifestyle. As my secretary, you will necessarily become more involved in my personal life. Its important that you understand our relationship. I enjoy being an attorney and I intend to be a very successful one. I am entering a world of men.

Powerful men. Do you know how they got that power, Julie?”

I heard a soft “No, Ma’am” as Janice continued.

“Because they are smart and cunning, and ruthless when necessary. And because they have a sweet little wife to go home to. Someone who will be true and loving no matter what happens outside, in the legal jungles. Someone who willingly dedicates her life to the success of her mate, taking pride and yes, cherishing his accomplishments. My sweet Kim has agreed to do this for me. He will become my loving little housewife. Always eager to love, honor, and obey.”

At this, she reached for my hand. I stepped forward to where she sat, the toes of our high heels nearly touching. At her indication, I slowly knelt. My downcast eyes couldn’t help but admire her strong nyloned thighs where they emerged from the slim stylish business skirt. Secretly I recalled the pride I felt when I had pressed it this morning. Her cool hand softly caressed my burning cheek as she resumed.

“Naturally, its not easy for Kim. Assuming a traditionally feminine role would not be easy for any male. But I am very proud of him. He is trying very hard and I am doing all that I can to help him. I expect you to help also, whenever the occasion arises. We want to reduce or eliminate his masculine tendencies while encouraging his nurturing, supportive femininity. I thought it was sweet of you the other day to refer to Kim using feminine pronouns. That’s nice, but it is also necessary to keep him mindful always that he’s really just my sweet little feminized boy. Its important that he always remember his proper position.”

She paused momentarily, handing me her empty cup. As gracefully as possible in the three inch heels, I rose and hurried to refill it. I felt the eyes of both ladies on my loudly rustling skirts. After also filling Julie’s cup I returned to my kneeling position.

“Kim understands that I expect him to be obedient and pleasing to you also. You will let me know if he ever incurs your slightest displeasure. As my personal secretary, I intend to keep you very busy. We will work out a schedule for Kim which will allow him to help you around your apartment. He needs all the practice he can get with dusting, laundry and other household duties. Also, I want Kim to learn how to entertain. There will be times when I have guests, both ladies and gentlemen.”

Jan’s hand went to my chin, lifting it to where our eyes met.

“I think our little Kim secretly enjoys submitting to women. But he may be somewhat reluctant to please the gentlemen.”

I couldn’t believe what she was saying. She grinned broadly at the shocked expression on my face. Though I couldn’t see her, I knew Julie could not suppress a similar grin. My eyes were locked in terror to her own soft gaze as she continued.

“Most young girls experience these things nowadays before getting married. That’s why I’ve hired an escort to help him learn some of the finer points of womanhood. Charles will join us next Friday evening here at our home.”

These last few months of conditioning to assume the feminine role had not prepared me for this! I certainly did not like the idea of another man in our home. Especially not as my “escort”. I started to object. Julie boldly took it upon herself to interrupt my protest.

“It won’t be so bad Kim. All girls experience an initial rejection response. But once they see how nice it is to have a big strong man around, they love it. You just wait and see. Soon, you’ll yearn to be in the arms of a handsome young man, eager for the masculine attention he will give.”

Her broad smile did not convince me. Before I could continue, Janice once again took control.

“Kim, sometimes a young girl will secretly long to be in the tender embrace of a handsome man. She’ll spend hours day dreaming about their first encounter. Sometimes writing his name over and over again. These are important feelings in the development of a young lady and something I don’t want you to miss. After you clear the tea things, I want you to get a pad of paper and a pen. You will write the name of your new boyfriend one thousand times. Each time will be in as neat and as feminine a script as you can manage. All the while you are writing, I want you to think about your first encounter. Imagine how you will feel preparing yourself for him. Think about what pretty dress you’ll wear. And perhaps which slip or petticoat. One that can charm him as you secretly reveal just a hint of lace at the hem of your pretty skirts. And think how you will feel, so soft and pliable as he takes you into his strong manly arms.”

I was awe struck by her words. However her soft finger at my pink lips accorded no room for further argument.

Almost two hours had passed. I sat dutifully at Jan’s big desk, carefully writing. I tried to dispel the thoughts she had planted in my head.However,the more I tried, the more vivid they became. Charles, I thought, such a strong name. I wondered what he would be like. And more, what would he think of me? Would he treat me warmly as if I were an attractive young lady? Or would he be disgusted by my feminized state? How would I react if he got to close? Or worse yet, if he touched me? I was revolted by that thought!

The firm touch of Julie’s hand on my shoulder jarred me from my thoughts.I looked up into her broad smile and sparkling eyes as she inspected my work.

“Have you decided on a dress yet, Kim?”

I steamed inside. What gave this young girl the right to ask such a question? I resented the familiarity of her hand as it moved lower on my back,coming to rest at the closure of my brassiere. Her fingers made gentle little circles around the fastening as if to remind me of my status. She continued to smile patiently into my glare, waiting for a response.

“No Ma’am”. It was almost a whisper.

I’m sure she could feel my disgust but I tried not to let it show. Thoughtlessly, (or was it with a purpose) she continued the conversation.

“I remember my first date just like it was yesterday. I was so excited. And a little nervous too.” she giggled with a mischievous, conspiring tone.

Her hand remained at my back softly tracing the outline of my bra as she continued with great detail. I blushed but tried to show a polite interest in her sometimes intimate discourse. I found it tremendously embarrassing that she was so comfortable in sharing these feminine feelings with me.Something I’m sure, no man would ever hear from her lips. Yet here I sat under her caress, a man indeed. A feeling came over me as she talked.

I became more aware of my soft, yet restrictive clothing. The thin dress with its narrow skirt. The secure feeling of my bra as it gently cupped the roundness of my immature breasts. The delicate high heels, how they lent an attractive curve to my thin ankles yet enforced a shortened stride and a slight sway to my hips. I felt the soft rustle of my nylons as I crossed my legs in the feminine manner that had now become habit. A strange feeling of kinship overcame me. I felt sort of a closeness to Julie.

Later that nite we were all in Jan’s bedroom. I was helping them get ready for bed before returning to sleep in my own room. I guess Jan had been right earlier when she mentioned the idea that I secretly enjoyed my subservient role in our relationship. But as I unzipped Julie and helped her out of her smart business suit, I realized something was different. I was no longer overcome by embarrassment as I gently slipped off her pantyhose and delicate mint green nylon briefs. As I helped her into her pink baby doll nighty, I felt a special closeness. Sure, I realized that I was obliged to obey her just as I obeyed Jan, but it was almost as if we were sisters.

Jan smiled down at me and gently tousled my beribboned hair as I knelt before Julie, pulling the matching pink panties snugly up on her hips.

“Kim, you’re such a darling little sissy” she smiled. “I just know you’re going to make the best little housekeeper and maid a woman ever had!”.

I blushed. But there was little I could do. Both of these marvelous women realized the truth of her words. Julie stooped down. Enfolding my face in her soft hands, she pulled me to a standing position. Pulling me closer, she planted a warm lingering kiss on my forehead. I felt the hard tips of her breasts press firmly against mine through the thin nighty. After ending the embrace, she handed me both her and Janet’s lingerie.

“Now bid your lovely fiancee good night, and to bed with you, Sis!”

Had she read my mind? I had little time to dwell on the thought however. As Julie jumped into her side of the large Queen sized bed, Jan took my arm, spinning me into her strong embrace. Even in my three inch heels I had to raise my lips to hers. She was such a powerful woman. I moaned in sweet surrender as her warm searching tongue pierced my lips. Julie giggled softly when I lifted my right foot high behind me and pressed my nyloned thighs tightly together in a typically feminine gesture.

Before sending me off to my own room, Jan told me once again to think of which dress I was going to wear for Charles. She wanted an answer by morning.

That night sleep was very slow to overcome my thoughts. What would I wear? Charles, I thought, such a strong, masculine ring. I wondered if he would be anything like his name. How would I react in the manly arms of a stronger, more powerful male? Would my first date be like Julie’s? Should I wear the white chiffon cocktail dress? Oh no, I thought, the skirt was much to short. And it was so terribly feminine. Oh, what would I wear for Charles? His name repeated itself over and over as I slowly drifted into a restless slumber.

My great dread of Friday evening naturally made the days disappear swiftly.

The time arrived before I wanted it to. The mere thought that I, a man, was to be femininely prepared as another man’s date sent unnerving chills through my small frame. I had been nervous and edgy all week despite encouragement from my beautiful fiancee and her lovely young secretary, Julie.

Janice and Julie were both bubbling with excitement as they helped me get ready for Charles. It felt rather strange being on the receiving end. Usually it was I who helped them with their things. Both of these lovely women were so enthusiastic as they prepared me to meet with Charles – especially Julie. She carried on a one sided conversation, recalling once again her own first date as she plucked relentlessly at my already thinned eyebrows. Jan brushed my shiny shoulder length hair molding it into a soft page boy style. I felt strange sitting there passively in the silky set of lingerie that Jan had given me for the occasion.

It was all in a soft shade of pink. Unconsciously, I admired the way the lacy bodice of the slip molded itself perfectly over the gently swelling cups of the matching bra. Through the slip my shiny pink fingertips traced the outline of my full cut panties. They presented a smooth feminine front thanks to the restraining device. It held me tightly back between my legs. Jan had begun insisting that I wear it at all times. Even under my slacks. She called the cruel garment my ‘streamliner’ and with a big smile would frequently ask if I was wearing it. Although I preferred pantyhose, both Julie and Janet said nylon stockings would make me feel more ‘special’ for Charles. It was much later that evening before I blushingly realized what they meant.

Jan approved once I had doubtfully suggested the white cocktail dress.

“It’s perfect, Kim. So virginal”, she grinned, “just like you!”

The skirt was very short. It fell to just below mid thigh barely covering the pretty lace hem of my slip. Above, the material was so thin one could easily see the pink outline of lace and the straps of the slip and brassiere. I blushed when Julie playfully swished the full circle skirt showing more than a hint of pink lace. The three inch heels gave a sexy inviting turn to my slim ankles. They were the same shade of pink as my lingerie. There were butterflies in my tummy as I turned before the mirror. My pink nails contrasted softly with the snow white skirt as I tried to prevent it from flaring and showing my underthings. Jan had tied a pink satin ribbon in my hair, finishing it with a big floppy bow. The streamers tickled my back thanks to the open back styling of the pretty dress. Giving in to the wonderful feminine feelings, my eyes absorbed the pretty reflection in the mirror. I felt like a fluffy feminine doll. My cheeks were aflame when I noticed both of the girls pick up on the secret look of admiration in my eyes.

Such a contrast I made to both of the girls who had elected to wear jeans and sweatshirts. Jan had explained that this was my big evening and they did not want to steal any of my limelight in front of Charles. In fact, Jan had already briefed Charles on what she expected. She had also extracted a promise from me to behave in a passive, obedient manner with my date, saying that she would get a full report. I was to act as though Charles was an important business associate of hers. And woe to me if I incurred his displeasure.

Jan attached dangling dew drop ear rings to my lobes and Julie had just finished spraying me all over with perfume when the door chimed. My knees felt like rubber as each of the girls took one of my hands, leading me to the foyer. I felt so vulnerable as I listened to the swishing whisper of my nyloned thighs beneath the too short skirt.

Charles was a surprise! The handsome roguery of his tanned features belied the impeccable tuxedo which he wore as comfortably as if it were a jogging suit. He was tall, but athletically proportioned. I imagined rather than actually saw the bulging muscles of his biceps beneath the expensive material of his suit.

“And you must be Kim” he boomed in a rich masculine voice.

My fingers played nervously with the hem my short skirt. I was lost for words as I looked up into his dark brown eyes. Somehow I managed a shy smile and a soft “Yes”.

“No need to be shy, little one” he smiled placing his hand at my waist. I didn’t like the feel of it. His smile, however, was natural and reassuring. Gently, he led me back in to the living room. Somehow, I felt so weak and utterly feminine being gently guided by his big strong hand. The swish of skirts about my thighs nearly caused my knees to buckle.

“You two have fun” grinned Janice as she and Julie exited through the front door. I had never felt so stranded in my life! It wasn’t until later that I realized one of the girls had put soft romantic music on the stereo.

“You’re a very pretty young lady, Kim. Why don’t you have a seat while I fix us a drink?”

I was intrigued by his masculine confidence. How nice it was to have someone else fix me a drink. Such a change!

He released me to the large couch. I sat carefully with my nyloned knees pressed tightly together in a desperate attempt to keep the pink lace of my slip from showing. Strangely, as I watched him move to the bar, I still felt the warmth of his manly touch where his hand had been. Nervously, I crossed my legs in the most feminine way I could manage. Did he know that I was a boy? How would he react if he knew? How am I going to react if he touches me again? These thoughts raced through my head as I sat waiting, hoping this was all a very bad dream.

He returned with the drinks. I felt his eyes surveying my nyloned thighs and ankles. The sparkle in his eyes did not prevent me from recognizing the animal lust of his gaze. I was the weak prey sitting at the mercy of this strong male predator. I watched in a trance my own small hand accept the drink he offered. The pink polish of my nails glistened in the soft light. After a small sip, I sat my glass on the end table. The pink imprint of my lower lip on its rim secretly reminded me of my soft underthings.

Charles sat his own glass down without taking a sip. Still standing, he reached down, silently beckoning me to stand. Before I realized what I was doing, my hands were in his. Gently, he pulled me to my feet. I was surprised at his strength. Never, had I stood so easily in the three inch heels. Puzzled, I looked up once more into those deep brown eyes.

“It will be easier to talk while we dance” he smiled. I was conscious of my swishing skirts and the soft tapping of my heels as he guided me onto the hardwood floor. And then I was in his arms.

At first I tried to resist. But he was much too strong. The closeness. His masculine scent mixing with my own seductive perfume. The soft rustle of my thin clothing as he pulled me closer to his own hard body. I felt the powerful tendons of his muscles relax slightly as he sensed my submission. Gently his hand guided my head to where it rested on the broad expanse of his chest. The strength of his embrace left me little choice. With a deep sense of surrender my own soft arms encircled his massive neck. It was then that I heard the soft dance music.

“That’s my girl” he whispered, “just relax and enjoy.”

Time lost meaning as he led me skillfully about the dance floor. He made me feel so small and so very feminine in my little white dress. With one hand at the closure of my brassiere, he held me closely. The soft mounds of my small breasts crushed against the masculine hardness of his chest. His other hand at my lower back held us tummy to tummy. I felt the strength of his thigh muscles through the thin material of my skirt and lingerie. As if expected, my own thighs parted slightly in welcome. Silently, we conversed more effectively than words would allow. At the feminized juncture of my thighs I felt his growing masculine need. Silently, I thanked Jan for my “streamliner”, even though it was becoming increasingly uncomfortable. And then it happened.

His powerful hand vacated its reassuring caress at my back. Gently, I felt his fingers beneath my chin, lifting to where our eyes met once more. No, this could not be. Surely he won’t… But my thoughts were confirmed as he slowly lowered his lips to mine. They were so hard. Not like Jan’s at all. I was repelled. It made no difference. He held me tightly. And then I felt the warm wetness of his powerful tongue. Probing. Seeking entrance between my own soft painted lips. Jan had long ago taught me to part my lips in acceptance of her own sweet kisses. But this was so different. How could this be happening? As if power of habit gained control, my lips slowly parted, surrendering to the invasion of this powerful male animal. He tasted so… so wet, so firm,so…masculine. He explored me deeply. Slowly I melted, opening fully, accepting, yes even welcoming.

Before the night was over, Charles taught me the joy of eager feminine surrender.

Both Jan and Julie were delightfully surprised when they returned in the wee hours of the morning. They hadn’t bothered with the doorbell.

“How sweet!” giggled Julie with amused delight.

My sleepy eyelids blinked to a wakeful state at the sounds of their entrance. I had fallen asleep nestled in the embrace of this big male animal. My small hand still rested on the fur of his chest through the open front of his shirt. I had opened the buttons myself. Memories of the evening flooded back into my sleepy brain. It was then that I realized Charles’ strong hand still rested on my bottom, through the thin pink nylon of my panties. My skirts were at my waist where they had been much of the evening. Suddenly I felt naked in front of the girls.

“It looks like you two had a fun evening” Jan grinned.

Julie couldn’t suppress a knowing smile as she agreed, “I think our little Kim needs to get out with the boys more often.”

Suddenly the nature of my situation crystallized fully, destroying the sleepy cobwebs of my mind. Quickly I was on my feet straightening the pretty dress. As I smoothed my skirts down over my soft nyloned thighs, I was secretly thankful that my “streamliner” was still painfully in place.

Charles awakened to my scurrying. Slowly he sat up, a big cheshire grin on his handsome face. I had just slipped back into my heels when I felt his strong hands pulling me back down. With a plop, my skirted bottom landed squarely in his lap. How ashamed I was to be held like this by another man in front of my fiancee and her pretty secretary.

As if to demonstrate his control to the girls, Charles took my soft chin in his big, strong hand. Our eyes met. Despite our audience, that warm melting feeling pervaded my tummy as his rough masculine lips grew close. I knew I could not resist. Without will, my own soft pink lips parted invitingly. That warm feeling of surrender overcame me as his big wet tongue explored me deeply. His powerful hand freely caressed my now sensitive breast.Unconsciously, I shifted my soft pantied bottom on his hardness. Time and place lost meaning. I knew only that I was being possessed by this powerful male. And that I was fulfilled by lovingly submitting to his will.

At the point where Charles felt my total submission, he broke the embrace. I heard the girls whispering to one another. My cheeks were red. I felt betrayed and used. But I could not bring myself to remove Charles’ hand which still rested on my small breast. Angrily, I tugged at the hem of my skirts. As Charles possessively continued to fondle my breast, we both knew that we shared the secret of his hardness beneath my soft bottom. Jan came closer. I felt the coolness of her soft hand on my fiery cheek. A knowing smile was on her full red lips.

“I’m happy for you, Kim. Don’t be upset, darling. Tonight you have found a new part of yourself. Something that every girl must know about herself.It will bring you much joy. I want you to thank Charles for helping you to discover and enjoy your new girlish feelings.”

My vocal cords were swollen and paralyzed by the humiliation of her command. Tears welled in my eyes. The words would not come. Jan sensed my total inability to form a word. Gently, her cool hand guided my face closer to Charles. Knowing that it was inevitable, my lips once more parted. I could not stop my tummy from melting. His firm wet tongue entered me deeply. This time there was almost an eagerness in my submission. Slowly, a tear trickled down my rosy red cheek.

THE END

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i have only been a member for a few short days and have found myself wondering why i hadnt joined much earlier. Truth is i was very scared and worried to face my sissy desires. Now i find those fears… Read more “sissy cindy”

This sissy doesn’t know what sh.e would do without The House to come to. This sissy has been so much happier after sh.e joined and has met a lot of sissy sisters that sh.e can relate to and confide in.… Read more “stacey”

This gurl thanks the Superiors of the House for allowing he.r to be here, and enjoys the company of everyone here. S.he want the Superiors to know that s.he is here at anytime to serve as required of he.r and… Read more “danigurl”

I wanted to thank you for the insight into TransGendered Persons. As a Psych student doing a thesis on Gender Issues In Counseling your information helped to clarify and reify my own position with regard to gender identification psychology. I wish… Read more “Todd”

This sissy is with You now for off and on 3-4 years and slowly but surely she gets Your program and discovers her true nature. In the beginning she was just a sissy on occasion and at “certain” times. But… Read more “sissychelle”

I have found more relevant info on this site than the rest of the web put together.

This submissive sissy congratulates you on this fabulous website. s.he admits that at first i was wary and looking to see where it was another rip-off – as most of us are used to. However, your fantastic – with all… Read more “patty jane”

i can not tell you how much i am enjoying your sissify site. Seeking to be trained as a sissy slave is my greatest adventure. Thank you so much for being out there for little panty slaves such as myself.

This sissy is finding this site to be more and more exciting, stimulating, enlightening and educational with each visit. This sissy is just discovering the value in contacting other members and discussing concerns and insights. This site is doing more… Read more “barbie”

i wish to offer my thanks for your website. It has helped me start down the road toward being the girl i know i was meant to be. Please know how much i appreciate all that your service does for… Read more “kara denise”

This sissy is so fortunate that Madame Stewart has allowed he.r the privilege of joining this fabulous site. Although a member of the House for a relatively short time, s.he has learned so much and is making progress toward becoming… Read more “chanel lacy”

i am so happy to have found your site, my Master sent me here. i am looking forward to becoming the perfect sissy slave, trained for the pleasure of others. Your site has given me real hope of achieving this… Read more “sissy slave domonique”

Once when I was about 7 or 8 I accidentally wet my pants in public. Upon seeing this, my Aunt (who I was staying with for the day) took me back to her house, had me undress and put my… Read more “little mickie”

This sissy wishes sh.e had found ‘The House of Sissify’ sooner. You provide a special haven for us sissies and, without You, no sissy would be able to truly complete he.r sissy journey. This sissy has only joined recently, but… Read more “brandie love”

i think this is the best site on the internet and it is an invaluable resource for all sissys. it is an honor to support this site.

WOW I have to say,.. That although I do not participate in this particular lifestyle,.. (being far too dominant in set in my ways to desire such an experience) I feel you deserve enormous kudos on the design and layout… Read more “ishmael”

i just wanted to express my gratitude for accepting me in Your sissy training and hope i can learn how to be a better sissy for my Wife.

It has only been a week but what a week this site is awesome and the Staff is so wonderful to deal with i am an older sissy and sadly my wife could never know. that’s sad because our life… Read more “lola”

Thank You all so much for providing such a lovely home and training ground for sissies. Please allow me to help in any way You deem appropriate. This sissy looks forward to many hours of training under Your guidance. The… Read more “trish”

The House of Sissify has encouraged me to be the real me and experiment with all sorts of idea’s. Before I started I would rarely dress up, now I can’t go a day without wearing at least panties. I would… Read more “Jess”

What a beautiful web site, with so many contacts and active chat going on. My frilly lacy panties always get very moist under my maids uniform!

This sissy is infinitely grateful that you have welcomed her into the House and given her a safe haven among like-minded people. Although she has only been here for a short time, she has made tremendous progress in her deep… Read more “sissy fraenzi”

I instructed my sissy, amandacecilia, to join your wonderful site a few days ago after I did a brief perusal here myself, with instructions that she show me anything she felt especially useful or insightful here. Needless to say, the… Read more “Mistress Monique”

The House of Sissify is absolutely the best sissy site on the web. This sissy has learned so much since joining. The advice and support are wonderful. s.he has learned how to love, honor, obey, and worship h.er Superiors and… Read more “stephanie kimberlie prince”

I have to say what a truly wonderful site this is. It has come like a warm comforting glow that has started to lift me out of a world of darkness. Many thanks to the wonderful Staff at The House… Read more “bobbiegirl”

Thank You, House, for being there so that us closet “sissies” have an avenue to express ourselves. This service is invaluable to us sissies so that we may express our sexuality.

It so comforting to be a member of this community, (you are all my sweet sisters) to know this sissy is not alone, in my exploration into what it is to be a sweet pathetic sissy, who’s only desire is… Read more “sally”

Just in passing – your site is an absolute inspiration, a joy to giggle through. The endless parade of those 1950’s tucked and bobbed pink-petticoated good-little-housewife cartoons is both mood-lifting, delightfully nostalgic in a delightfully non-serious way, and strangely gratifying… Read more “missy messy maso”

Thank you so much for providing us with your wonderful website! I was feeling so lost and lonely, until I discovered you. I am so eager to learn more about your happy community. In the mean time, I promise to… Read more “freddie”

This sissy just wanted You to know that although s.he has never been involved in an educational experience so personal, this is exactly what s.he needs. You and your Staff must be geniuses. When s.he stumbled into the Sissify site… Read more “robyn”

Joining The House has been the best thing ever for this sissy. It has been about a week since joining and already sissy feels a tremendous turnaround in the way she feels and acts. she most certainly feels more feminine,… Read more “bobbiegirl”

I just wanted to thank you for having such a wonderful service. I have been looking for years to find someone to help me make this transformation. Again, let me say thank you.

i would just like to thank all the wonderful Women who have created this site. This little sissy has found a place to feel pretty, safe and secure. i look forward to learning more and more about becoming a Woman.

…I would also like to add, that i am gaining quite a bit of information from your site, and thank you for a well constructed web site that is very informational, and is providing quite a bit of insight into… Read more “Pat”

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It is now almost three months since my Wife and i have begun reading your site, and it has made a radical difference in Her approach to my feminization. She has decided, much to my humiliation, that i must be… Read more “sondra”

Thank You for accepting my application and allowing me the privilege of entering the interior of Your site. It has indeed had a profound effect on my psyche. i view myself as transgendered, and i have been progressing along the… Read more “jamie”

The House of Sissify is the best site that this sissy has found. she has spent hours in it just reading and learning. This sissy humbly thanks all the Sissify Staff

This sissy has just finished he.r second month with House of Sissify! I am amazed at how friendly and helpful everyone has been to this new sissy! Jamie is on chat almost every day for an hour or so catching… Read more “jamie”

i would like to thank you for the information and amusement Youve given me. This really is a mind teasing site. informative, educative, seductive and fun at the same time.

This sissy wishes to thank her Superiors for providing the opportunity for learning. This sissy is so happy at being able to learn how to be a better sissy.Thank you for providing such great insight, and for allowing this sissy… Read more “sissy michelle”

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This sissy must confess that the House has changed and enlightened he.r life. Becoming a sissy is not a dream any more. It’s reality. She just needs Your excellent guidance and work. Hard work that is rewarded not only with badges and helpful… Read more “megandelux”

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This worthless little sissy-slut-wannabe is dropping You a note to let You know what a fine job i believe You are doing with Sissify.com. i had already mentioned to Mistress Jennifer how much i enjoyed the Site and Your continued… Read more “christine”

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I’m one of your loving, grateful sissies…..You have given me the gift of knowing I’m not alone.

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i want to be a flower i want to be pretty and delicate delightful to look at but easy to bend and easy to break i want to make a real Woman happy through my service and devotion and poor… Read more “lauren renee”

Thanks for the chat room You have provided for us sissies. The help from my sisters has been wonderful.

Thank you so much for your wonderful Sissify.com. i have been enjoying it for some time now. i especially enjoy the little stories that follow each day in the wanking schedule…… my collection of panties is growing day by day.… Read more “cindysilk”

may i request permission to speak freely from the heart? upon finishing chapter one of “Girlfriends” by Vicky Tern……oh, my, God…Mistress, i just don’t know what to say. oh my God, this really is home! God in heaven i’m going… Read more “danielle”

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This is the greatest find to date. Thank you, Superiors.

It seems the House of Sissify has loosened the ground up beneath me and im descending, in free fall, accelerating by the vast gravitational attraction of Femininity.

The House is there like a beacon in the darkness.  You have done, and are doing, so much for the community and this sissy is very grateful.

Sissify.Com is alive! i can feel the pulse of your heart and the heart of the Staff every time i log on. The passion that You and the Staff put into this program seems incredible to me. i can feel… Read more “sissy robyn”

my Wife has ordered me to write You again and tell You how much She enjoys Your site and the ideas it has given Her. She says She never realized how nice it would be to have a sissy maid/slut… Read more “kelli ann”

I hope that I am not an intrusion to say that you have created a terrific website. I just wanted to express my admiration for you. You must receive lots of e-mails like this so I will trouble you no… Read more “gwenn”

The House provides endless pleasure to everyone.

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i just wanted to drop a line to say that Your web-site, “The House Of Sissify” is an artistic masterpiece (mistress-piece?) . .. it is alluring, entrancing, enchanting,exotic, exhilarating, breathtaking, mystifying, and sanctifying. Every page opens ones mind, heart and… Read more “michaela”

This site is SOOOOO cool. Very well done & intelligent. Great graphics & a great staff. I even met someone & we are going to get together soon thanks to the International Sissy Network

It was really great to know this site. i have obviously missed a lot not getting onto this site before. your suggestions will definitely make this slut a better maid and keep her Mistress happy and satisfied forever. this whore’s… Read more “diana”

A short note of thanks for providing a complete community for sissies, a place of refuge and resource from the harsh world, and the House *genuinely* seems to hold sissy’s interests at heart: no exhorbitant joining fees = loyalty for… Read more “hayley”

Once again I would like to deeply thank all the Staff of Sissify for just being there for me and others like me. As I am more or less confined to my house (physical problems), and this service is one of my… Read more “justina”

This sissy is sooooooooooo glad to be in the community. she is learning so much and hopes to get much more training to be a better sissy slut, she loves to submit and please and talk with her sisters.

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This site is so cool. All of the lovely photos are inspirational to this sissy’s development. The personal stories help this sissy to believe that anything is possible.

Having just managed to get up the courage to join your website, it is already clear that this sissy should have done so a long time ago, already you have made he.r wonder why s.he was so nervous. With so… Read more “heather-louise”

just wanted to thank you for allowing the pansies and sissies of this world to serve such beautiful and domineering women as yourselves–i only wish i could get my wife to do this but her idea of kinky lifestyle or… Read more “a happy pansy”

sissy jimmie wishes to humbly say thank You for sissify.com. This site has become sissy’s refuge. sissy can be free here. sissy can find sisters here. sissy loves he.r sissify site. sissy visits the House every day. the house has… Read more “jimmie”

The unworthy apprentice sissy writing this has written You many times asking for help. You have always made he.r life better. The House has been the very foundation of he.r life. Thank You again for Your efforts.*curtsey*.

Thank you again for everything that you do. You may never know how important you are to the members of this site.

…and i must say that Madame Stewart is right, even in a distance of 3000 km, She made it possible to make me impotent.

Discussion?

  1. rubyjo

    rubyjo is looking for a time where s.he will experience a similar passing and submit easily as kim. Hoping to transition and put into practice the needed girlish traits to allow the experience that kim went thru to occur in rubyjo’s future.

Something to share sweetie?