Mistress Psyche's Feminization Fantasies


Sissy Girl Stories


Subjugated Step Sissy

Part Two 

By Miss Priscilla Bouffant

(Sissy Ronnie/Rhonda’s adventures with her step mom and the Cassandra Sisterhood continue. What ever will she do?)

Six: The four T’s, or Tied, Teased, Trained, and Transformed

Note: We left our Rhonda lashed in a styling chair at the salon in her stepmother’s home. Her face, eyes and lips are just so gorgeously, and lavishly made up! Her hair is up in hot rollers. The stylist, Nanette, was in the process of masturbating our little “damsel in distress.” Let’s have Rhonda tell us what happened...

I knew I was nearing the apex of my pleasure. Nanette actually began to nip me on my nose with her teeth and give me little kisses on my forehead. When I turned to kiss her back though, she warned me, “No, no princess. You look straight ahead at your pretty reflection. I’m running this show.” 

Suddenly I erupted with a breathy, “Oh no!” Shivering and shaking I writhed in pleasure, squirting my juices into a warm, wet washcloth Nanette had provided, having used the hot roller tray to heat it. She milked me to the last drop. As I smiled, she cleaned me up and put my slacks, penis pouch and panties back in place before she began to remove the rollers form my hair and comb out my hairstyle.

“Thank you so much Miss Nanette,” I said politely. She smiled and said, “That little exercise will be our secret.” She needn’t say more. Taking each small brush roller and pin out, she handed these to me, to put back in the tray case. She began to finger style and pick comb each curl until I had this cap of tight ringlets atop my head. After she applied some hair spray she added a small red bow on the right side.

She let me look at myself for a while before freeing me from my tight cape encased prison. I looked like a real sissy now, but at the moment I had been too chastened for any rebellion. I allowed Nanette to put me through some walking practice and such before we went to find my “mother” and Ginny. At least I felt relaxed. 

They were both in the living room, so Nanette announced me before we entered. I did my very best to contain myself, while doing a prim sashay prance about the room as Nanette narrated my clothing, such as “Miss Rhonda is wearing red spandex slacks and velveteen anklets. Her hair is done in a bubble cut by Miss Nanette.” 

Mother and Virginia smiled as I was finally presented to them. “Do you like the cut, color and style Rhonda?” Nicole asked. I absentmindedly reached up and patted it, taking my hand away as I realized this action could be discerned as a “primp.” All noted and smiled. Finally Nicole took me over to a mirror above a desk and I could see myself from the shoulders up. 

I think so,” I said. Nicole frowned and said, “I think you look fabulous. Look again. The color is perfect for your skin tone, the length is perfect for your face and neck, and the top curls send the message I want all to get when they see you,” she said, turning and looking me in the eye for effect. I knew what she meant.s="MsoNormal">  

Until I complied, until I acted like her daughter, until I accepted this transformation as my fate, she would present me in public as a sissy, her sissy, Nicole’s step sissy. Mustering all the courage I could, I said, “Yes I like everything about my hair. The makeup is nice also.” 

Mother looked at me suspiciously and said, “We’ll see next week. Won’t we ladies?” It was getting late and Nanette had to be home. After supper I was given a hairnet to wear to bed. I lie under the covers more relaxed then usual. Maybe Nanette was right. Maybe I should masturbate at night, regardless of what I was wearing. As long as I thought about girls, why would I care? 

I’d put it off, as I was sleepy. Thursday my main job wash scrubbing and washing all the panties in the house, hanging them out to dry and folding and putting these away. I was being bombarded with female stimuli in the hope I would cave in. All in all it was an okay day, but the whole weekend, starting with Friday afternoon was tough.  

That afternoon Natasha, “Tasha,” as she was sometimes called, and Anna arrived for aerobics. I’d done aerobics Thursday and was told I’d be doing them often, for weight loss and waist slimming. 

I was also doing exercises at night for “bust enhancement.” As embarrassing as these were, the aerobics I’d done with Nicole and Virginia were humiliating because of the way they insisted I move while doing them. I was to follow their lead exactly, and shake, shimmy, wiggle, prance and flutter around like an overly fun loving girl intent on putting on a show while slimming down. 

They expected the same performance when we exercised with Anna and Tasha. The five of us were in the exercise room of my special suite. The sauna was getting hot, as I was expected to have an intense steam bath after all my workouts. I was to undergo treadmill exercises Saturday. All the women, plus myself, were in appropriate garb. My sneakers, tights and headband were pink, my leotard, white. 

The program began with Nicole as leader. I did my very best to emulate a female intent on getting a good workout, looking cute, and having fun. I wiggled my tush, shook my upper body as if I had breasts, and held my hands and wrists limp, fingers open as if I had on wet nail polish. I occasionally flapped my hands and arms, and snapped my fingers, just like the ladies did.  

I knew I was being watched. At the end of the intense routine I was told to undress in front of everyone, wrap a towel around me and spend another 45 minutes in the sauna, “steaming off a few more pounds.” 

“It’s okay if you strip in front of us Rhonda. After all, you are just one of the girls,” Nicole teased, bringing smiles to her friend’s faces. In the sauna, I liked how I felt. New age music was piped in and I was relaxed. After my shower, shampoo, condition and powdering, I went to my room to put on a ruffled panty brief and await Ginny for my dreaded lacing. 

I was surprised and concerned as well to find Anna and Tasha seated in my bedroom, wearing body stockings. When I asked where Ginny was I was told by Tasha, “We will be doing your lacing. Your mother wants us to fit you for a training bra,” she smiled, adding, “Grab hold of the lacing trapeze, we have work to do.” 

I hesitated a moment, causing Anna to remind me, “We hear you upset a good friend of ours named Nanette. We wouldn’t want anything like that to happen, would we?” I knew exactly what she meant so I latched hold of the trapeze. First they secured my hands and wrists to it and they raised it slightly. Just enough so they could put a garter belt, white hose, pink anklets, and a pair of pink heels on me.

Then before they put my corset on, Tasha raised me a little more. Anna measured my waist and said, “Let’s try for a 26 inch measurement. Then we can put a bra on her.” Wow! Did they ever cinch me in! They pulled and tugged at the laces until I thought they’d sever me at the waist. 

I whined, cried and pleaded with then to take some pressure off my torso by lowering me a little. “Please? It’s much to soon to pull me in to 26 inches!” I mewled. They merely laughed and swatted my butt with a hairbrush, saying, “Quiet you spoiled little bitch!” 

Once they did finish the cinching and had lowered me to a tolerable position, I figured they’d leave me for a while as Ginny often did, so I asked, “Are you going to put a panty on me?” Both women stood in front of me and looked me over. “My, but she is a modest little bitch, isn’t she?” Tasha stated. “Let’s doll her all up and have some fun Anna,” Tasha smiled.

When I asked them to get Ginny or “mom,” Tasha gave me a quick slap to the face and said, “Listen girl. Your mom and Ginny asked us to give you a little tune up in preparation for Saturday’s discipline session. Kind of a reminder that you shouldn’t mouth off as you did to Nanette. Before we begin your little motivational exercise, we want you looking nice and cheap. Like a street walking hooker.” 

She squeezed my cheeks together, saying, “So hold still while we pretty you up, slut.” She began by outlining my lips with a brush before giving me a nice double coat of rich, creamy red lipstick. She did my eyes really heavy with mascara, shadow, and gave me big arches with a pencil. After she blushed my cheeks, she used a hot comb, blow dryer and plenty of spray and mousse to tease up and curl my tapered bob. 

Moving from in front of the mirror, she said, “Voila!” She was right. With the make up, tease job, heels, hose and corset, I was the image of a sleazy tramp. Except that this sleazy tramp had a penis. “What are you going to do to me?” I asked pleadingly. “We are going to screw you with this strap on dildo, honey. Both of us are. I’m going first,” Tasha announced. 

“Oh no! Please? Not now. I’ve been pretty good since the Nanette incident,” I implored. It did not change a thing however. While Tasha fastened the artificial penis to her lush body, Anna began prepping me with a jelly lubricant. I gasped as her gloved and lubricated finger went into my anal cavity. She wiggled her finger around and as she did I involuntarily wiggled my ass too. 

“She’s ready Tasha. Look at her gyrate!” Anna cried out. Tasha got behind me a said, “Give me some of that love jelly Annie. I want to lube this joy stick up really good.” As she began to poke my rear, I moved a little out of apprehension. “No you don’t little missy. You hold real still for Tasha. Tasha is going to treat her girl real good,” she said as she used one hand to guide the dildo into me and rubbed my right breast with the other.

“Don’t worry little Rhonda. Once we’ve banged you into sexual bliss, we’ll clean you up and put a training bra on you. Then you can redo your face and hair, and get dressed all pretty to see mommy,” Tasha teased as she whispered in my ear. She distracted me long enough with her whispering and petting of my chest to push the slippery faux penis up inside of me. 

“Yow!” I moaned. Oh my goodness! I had never had a real one up inside me so I had nothing to compare this to. Nevertheless, it was very uncomfortable. I saw my reflection in the mirror and my face had a pleading, helpless look to it. Tasha locked her hands and arms at my waist and began to undulate her hips and pump her fake cock in and out. 

I started to moan and mewl softly. “Relax baby. Just move smoothly with me. It won’t hurt as much that way, probably not at all. Just get into the rhythm. That’s a girl,” Tasha encouraged as I tried to relax just to save myself some discomfort. I did begin to move with the swaying, jiggling motion she employed and it did work to relieve some of the irritation.

Between the way I was dressed and dolled up and the helpless nature of my bondage, I was quite the sight. The embarrassment of my situation was increased by the woman behind me, balling me at her whim. I could see Anna’s reflection in the mirror. She sat, disinterested, filing her nails and occasionally glancing up, as if awaiting her turn. 

“Annie lover. Help me out a minute. Get me some sort of love lube. Nanette tells me, this sissy of our’s likes her button rubbed,” Tasha teased. Anna responded by slathering a good-sized dollop of cocoa butter creme on my penis. Tasha began to slowly manipulate my cock with her skilled fingers and hands. 

As I became erect I seemed to like being screwed a little more and both women mentioned it, much to my embarrassment. I’m uncertain how this whole strap on assembly was designed; however it must have made provisions for the female wearer’s pleasure by stimulation of the clitoris. As my desire intensified so did Natasha’s. She began to grip my stomach, digging her long talons into it. 

She ceased to manipulate my organ. Her pleasure became tantamount. Before long she was writhing and grinding her entire torso and hips into mine, causing the dildo to press against my sphincter. I began to weep and whimper. She ignored my pleas. I felt used, sluttish, and ravaged. 

As she came, her excitement intensified and she pounded my butt unmercifully. When she was finally finished she let go of me, pulling the dildo from my anus quickly. She lie on my bed laughing and gasping with pleasure, as I stood, still tied to the lacing trapeze, my makeup mussed from my crying. 

Anna lay down beside her friend, petting her face. Tasha smiled at her and she and Anna hugged. Tasha kissed her lightly on the lips and said to Anna, “Your turn honey. Remember, this is a Slut Boy Gang Bang. The little whore is all excited and ready to go. Besides, we promised her mother we’d get her home, safe and sound.” 

They both laughed at the pathetic humor in that, and Anna took the strap on to my bathroom for cleaning. “I’ll douche her up while you get ready Annie girl,” Tasha added as she gave me a cleaning with toilet paper and gave my butt hole another lube job. By this time, I was too defeated for the moment to say a thing. I simply continued to sob, totally humiliated by my debasement. 

Anna was actually more gentle then Tasha, and even paid a little more attention to my penis. However when I made sounds as if I were close to an orgasm, she stifled me by squeezing it really hard and saying, with clenched teeth, “Don’t you dare, my little fairy boy. Mistress Annie comes first.” I heeded her warning. When she did burst forth, I was rocked not quite as hard as when Tasha had her orgasm.


Just as when Tasha finished, I was left hanging, physically, emotionally, and sexually. As before, the two women lie on my bed cooing to one another, before rising, freshening up and dressing, acting as if I weren’t there. I was too spent to say a thing, and simply stood there, helpless and trussed up, too shamed to view my sorry self in the mirror.

Without a word to me, they unclasped me from the trapeze and sat me on my bed, using a warm wet washcloth and a towel to wipe and dry the exposed portions of my body, before freshening me with an assortment of lotions, powders and perfumes. Still listless and scared, I was led to my bathroom where they rinsed all the goo from my hair and face and began to make me up, vividly, but half way tastefully.

I wasn’t so sluttish, but on a female the make over would have been considered sexy, possibly a little “come hither”. They then toned it down a little by contrasting the colorful cosmetics, with a simple and cute, but fetching hairstyle. They simply blew dry my bob and brushed it behind one ear and over the other, pinning it in place with barrettes. Lastly, clip on, pink ear bobs were fastened near my piercing studs.

After being fitted with my first slightly padded training bra, I was helped into a white silk blouse. Posed in front of my full-length mirror in my room, I viewed a painted, and mocking schoolgirlish reflection, with three inch pink heels, white stockings and pink ankle socks. The contrast was clear and meant to be. No matter how cute they tried to make me, my height told the story. Sissy boy.

Until I dressed in adult female clothing I would never pass. I hated to admit it. However, I was not going to appear to be a real girl! “Are you horny Ronnie? Would you like some sexual relief? Annie? We were both so into ourselves we forgot all about poor Ronnie here,” Tasha remarked.

I was so surprised and flattered, that I could only emote a breathy, practically tittering, giggle of   “Oh yes please, that would be nice.” I was so tongue tied at the moment that it actually came out, in an accidental lisp,  “Oh yeth pleath, that would be nith.” This irony was not lost on my mentors or tormentors, as it were, and they laughed as they told me I could finish myself off. “You want me... to... masturbate in front of you?” I asked both surprised and embarrassed.

Tasha put her hands on her hips and said emphatically. “Well yes honey. We don’t want you to sneak around beating off. Do you think we are like Nanette? No dear, we are not going to do it for you. Sorry my little Bloomer Boy. You said you wanted relief and you will relieve yourself. Now!”

She walked over to the CD player and put a selection on. It was a Latino female group, Wicked Sisters, doing their greatest hits. Both Tasha and Anna began to snap their fingers and roll their hips, dancing to the frenzied rhythm. They danced over to me and began to shake, shimmy and rub lightly against me.

Anna chimed in. “Okay doll face. Time to play, choke the chicken. If you know what’s good for you, you’ll get some of that cocoa butter and start creaming up. Work your cock and balls. Let’s rock honey or we will see you pay the price.” I knew better then to not comply, so I got some lotion and began to stimulate myself.

The shame, degradation and embarrassment of that moment stayed with me for a long time. First off I had been butt reamed by not one but two domineering females while dressed like a Victorian era harlot. Now I was done up as pseudo preppie mommy’s girl with a bit too much make up. My heels, white hose, silk blouse, barrettes, and stylish bob said sorority girl, but my height, flat chest and erect penis said sissy boy.

As the music played, and the ladies danced, I was relegated to a sort of marionette, as they demanded I finger my penis, jiggle my hips and shimmy my upper body to the music. It was really amusing to the both of them, as I followed their orders to the letter. My arousal mounted in spite of my shame.

Funny thing about being erotically stimulated, one will finally reach a point where they can’t turn back. As ridiculous as I felt looking the way I did, I still was so turned on that I began to beat my meat harder and faster. With the women now touching me and brushing against me I started to wiggle my ass and feel sexy doing it. When I finally shot my load, it splattered spectacularly against the mirror.

Between the earlier festivities, my awful degradation and the stress of the whole afternoon, I crumpled to the floor, exhausted and burst into tears. “Oh look Tasha, Rhonda is crying tears of joy from her orgasm,” Anna said mockingly. Tears of shame would be more like it. I wasn’t to get a break either. They had me clean the sticky sperm off the mirror and my fingers, before finishing my outfit off with a black leather miniskirt.

“Now we are going to show you how to walk proudly, as a sexy woman would,” Tasha announced. After a time I sashayed or strutted, would be more like it, into the living room, presenting myself to Mother and Ginny. I was wearing my pink heels, and anklets with a white blouse and matching hose. My hair in that dolly boy bob, and make up and nails vivid.

“Well Rhonda, you have the walk of a pleasure ridden female. With that leather mini, I’d say you were trying to make a statement. What gives, ladies?” Mother Nicole asked. “We had a little fun with your little sissy slut, Nicole,” Tasha smiled.

“Rhonda, is this true?” Nicole asked. I was speechless! She knew what had been going on! She ordered it up to further shame me. I looked at her, mouth agape. Before I could say anything, Tasha began explaining.

“She really came on to us during her cinching. We decided to take her cherry while we had her on the lacing bar. She loved it! So much so that when we let her down she begged us to pull her off. We refused but allowed her to jerk off in front of the mirror,” Tasha said shrugging her shoulders.

“Rhonda I’m surprised at you! You act as if you hate dressing, but I think you secretly enjoy it. Why else would you display such sluttish behavior? I don’t want to hear another word about it. Get into the kitchen and get everyone some iced tea. Seeing you enjoy being a slut, continue to prance like one. You may proceed to walk in the wanton way you entered the room!” Nicole intoned emphatically.

All four women glared at me so I knew there was no sense in arguing. I jiggled my way into the kitchen and returned with the serving cart, a pitcher of iced tea, sweetener and glasses. Each time I served I punctuated it with a well-executed curtsey, just as I’d been taught. I got another tongue lashing from Nicole after Tasha and Anna left.

“Your father would be so upset with this behavior. He’s hoping to return to a sweet demure daughter, not a hussy. I think that the next few evenings you should think about this,” Nicole added. When I tried to explain to her that the ladies had told me that she had wanted them to bugger me, Nicole flipped!

 “How dare you accuse my friends of forcing themselves upon you! You will definitely be punished for this!” She insisted. I spent the next three evenings, through Sunday, tied spreadeagled to the bed and wearing diapers and rubber panties, because I “couldn’t be trusted,” she said. Saturday evening would be particularly interesting.

In the meantime, Saturday morning after breakfast I was treated to treadmill exercise. Again I had to emulate an exaggerated female by being really prissy in my motions and mannerisms, while on this machine. After a long day of doing Nicole’s and Ginny’s hair, polishing their high heels and serving by the pool, Ginny made me ready for bed, bindings, diapers, rubber panties and all.

“You did a nice job on my hair today baby,” she said as she looked at me, with my wrists             lashed helplessly to my bedposts. “I wish you really would come around Rhonda. She’s only going to leave you tied up to the bed one more night. After that I could make things interesting for you if you’d cooperate,” Ginny added. My curiosity became sparked.

I gave her a puzzled glance, which prompted her to say, “I mean interesting like this,” she said as she mounted my helpless form. She lifted her nightgown to reveal a shaved vagina. Seating herself down on my face, she said, “Time to eat honey and you’d better do good!”

I began to lick, lap and kiss her vaginal area trying to pay close attention to her clit, which she exposed by using her fingers. I was hoping of course to please her enough that she would do the same for me. Ginny was hot, maybe not as hot as Nicole, but younger, more my age.

Long blond hair, turned up at the ends and a lean, long legged, fashion model’s figure. Her puss smelled so sweet! I could feel her getting close, and when she did let go she popped like a cork. She came in waves, writhing around and laughing. She lies beside me, and gave me a light kiss. Then she got up and said, “Goodnight, I’ll see you tomorrow.”

“What?” I asked. “What about me, Ginny?”

She then explained to me, “I’ll take care of you, anytime I hear Nicole say that she was pleased with your performance on that particular day. You are going on a little outing with her tomorrow. Should you please her, I’ll be in at night to take care of you. I won’t untie you but you’ll be satisfied. Behave in the future and I’ll make sure you are taken care off. Misbehave and you can play with yourself,” she laughed.

“One other thing. Don’t expect it every night. Nicole is not stupid. She cannot find out. Understand?” she asked. I confirmed that I was with her. She left in a flash, her pussy juice still on my face. I wondered what this Sunday “outing” was all about. I had trouble sleeping but finally got rested. I awoke Sunday morning and awaited Ginny to untie me. I was happy because for two straight evenings I hadn’t peed my diapers. My shame knew no limits.

                                                     Seven: Salon Swish


My outfit and appearance for my Sunday outing with Nicole were thus far unrivaled, in their sissified exaggeration! My day began with very careful bathing, shaving, powdering and perfuming, followed by the meticulous painting of my nails in pastel pink coral. My blush, eye shadow and lipstick were made to match my nails.

My complexion was done with a translucent powder to make my skin appear a pale ivory white. Ginny took great care to set my hair, tightly pin-curling my tresses atop my head, leaving the sides and back straight. Then she used small rollers to set the sides and back. She covered my head with a tight, burgundy stretch turban, with a bow in front.

 Having me remove my satin bathrobe, Ginny helped me into a pair of multi-tiered, palish yellow rhumba panties. Very carefully, she had me tuck my penis into the pouch in the panties. My outfits become more femininely obscene by the minute. Then I was shown how to put on, and lightly pad, a white cotton-training bra. After I was cinched in, to 26 inches with one of my usual heavily ruffled white corsets, I was made to step into a form fitting, pastel yellow mini dress. It matched the rhumba panties perfectly.

The hem of this hideous creation was so short it barely covered my crotch, showing off the lacy edges of the panties along with the heavy flounce on the last few tiers of gauzy veiling. The hem also flared out, just enough to give the impression one was wearing petticoats or an even more embarrassing set of diapers and rubber panties.

The short sleeves of the mini dress were puffed, the front done in frothy white lace, and the edges of the puffed short sleeves were also trimmed in a gauzy fabric. It buttoned up the back, had a high frilly collar and tied just above my behind with a butt enhancing white sash bow. My stockings and two and a half inch heels were also white as were my gloves, ear bobs and dainty hand bag.

My hose only came to just above my knee and were held in place by pale yellow, ribbon decorated garters. The shoes had a double ankle strap, and a strap at the instep, for extra ankle support, due to the ultra slender stiletto heel. My mouth fell wide open when I viewed myself in the mirror. I looked as if I were wearing a baby dress! Were it not for my height, I could very easily be an eight-year-old girl going to a birthday party.

Instead of course, I was a twenty two year old, forcibly sissified male, going to an undisclosed destination with his dominant stepmother. In the heels, I was a half-inch over six feet. Were I wearing an empire waist gown, or a sleek hobble skirt, I would certainly be able to pass for a tall, but elegantly attired, appealing young lady. However, under the circumstances it would be obvious to anyone that I was a young male undergoing extreme petticoat discipline.

Ginny noted the crestfallen look I displayed and said, “Remember, please your mother and we can have some fun, Rhonda. Pleasing her will mean, calling her mother, liking the way you look, behaving like a obedient girl, doing little things for her, and wanting to do more stuff with her. So smile, and I do mean smile. Smile pretty, act pretty, look pretty, and walk pretty. Got it?”

I nodded, forced a “pretty” smile, and allowed her to lead me to the vanity to have my hair “done” and “adorned”. She began by removing the turban, then the rollers and pins. My hair was still quite wet and shiny from the washing and the setting jell. She carefully and almost lovingly began to fashion my hair using a combination of her fingers, a pick comb, and a warm blow dry.

Her movements were deft and fastidious. I could see it mattered to her how I looked. She then told me as much. “Rhonda, I am going to make you look oh, so pretty today. Your mother will be so pleased and I am going to be so hot for you tonight, if you are good of course. Now today you are going to visit Ms. Suzanne Herndon and her special niece, Simone. Simone is special because she is like you,” she added, letting that sink in.

“Before we leave your room I will show you how to act and what to expect. Now lets finish this “do” of yours,” she ended. So, I was going to visit some woman and her sissy nephew? That should be a barrel of fun. My daydream was broken by Rhonda saying, “Voila!” What had she done to my crimson locks?

Upon the top of my copper tinted pate was a two to three inch high bouffant of swirls and coils. My bangs were slightly puffed. The sides and back were meticulously sculpted ringlets, which closely hugged my cheeks and the back of my head. On the right side of my head was a small bright yellow bow. On the left side was pinned a gauzy, ruffled, pompom.

The coiffure was so fastidiously, sleek, shiny and contrived, that along with the adornment and the outfit, my entire aura said, “Look at me. I’m mommy’s big sissy boy!” Miss Virginia (she had just told me to refer to her as such, from here on) would see to it that my mass of coppery curlicues stayed in place. Having me close my eyes she employed a generous sampling of sweetly scented hair spray.

Then I was given my instructions for the day, along with lessons in comportment, and an eye opening discourse on the very mysterious Cassandra Sisterhood. By the time I was presented to Mother Nicole, I had been sufficiently enough chastened to be able to strike the accepted “presentation pose” of a “Cassandra sissy”.

As I had primly minced my way into the parlor, I had been able to view my lovely stepmother. Though I had kept my eyes respectfully lowered, I still had to raise my head slightly in order to navigate the room and it’s plush furnishings, therefore I could see the stunning Nicole. Her resplendent strawberry blond hair was done up in a carefully coiled up sweep.

As always her makeup was tasteful, though vivid red at her lips and nails. She wore a cream colored, “ladies who lunch,” Chanel suit with matching heels. Her classic simplicity, contrasted sharply with my overdone fussiness. I stopped a respectful distance from where she sat. Now I fully and demurely lowered my eyes and eyelids.

Grabbing the edges of my yellow taffeta mini, I quickly dipped a curtsey, before assuming my passive position. Both knees were slightly bent, the right a bit more then the other. I was perched on my heels, my weight more on my toes. My fingers just did touch the edges of my dress hem. The short, patent leather strap of my prissy handbag was looped over my right wrist.

Most submissive about my stance and demeanor, were my demurely lowered eyes and eyelids. I stood with my head hung abjectly, as if in complete shame. I held this pose saying in the sweetest most girlish voice I could muster, “Good morning mother. I am so thrilled about today’s outing. I do hope you like the way I look.”

As I held this pose, I realized that if I were to be a part of this Cassandra society I would always pose this way in the presence of any female who might be talking to me. Most any female, I should say who might be remotely connected to the Cassandra Sisterhood. By “most any” I mean any female aged 6 or older. How terribly humiliating!

I waited as I heard Nicole’s heels tap slowly on the polished oak floor as she came toward me. I could smell her perfume and I could sense when she was but a few scant feet from me, circling and scrutinizing me from all angles, as an art lover, analyzing a sculpture.

I knew Miss Virginia was standing off to my left. I wondered if she was also holding her breath. Did she breathe the same sigh of relief when Mother Nicole said, “I absolutely adore the way you look, Rhonda! Of course, I knew I would. Excellent job Virginia! I’m so pleased with my decision to permit you great latitude in the selection of Rhonda’s coiffure, apparel and cosmetics today. I’m sure Suzanne will be as pleased as I am.”

On the way to the Herndon estate, as Miss Virginia drove, she and mother chatted. I was seated in the back, my knees pressed together, little purse in my lap, hands folded over my purse. Of course I was smiling. They chatted and gossiped about this and that. Whenever my name came up, they’d act as if I weren’t there, not as much as giving me a glance.

They spoke of me in the feminine always now, using, she, her and Rhonda interchangeably. The way they spoke of me, I may as well been a piece of furniture they had just purchased or a new pet. For this reason, I had much time to contemplate what I’d been told about the mystifying Cassandra Sisterhood.

From what Miss Virginia had told me I was involved with an old, established, very effective secret society. The Cassandra Sisterhood had been launched at the very first all female college founded in England. It was named after its originator, Cassandra Winthrop, a wealthy socialite, who had been jilted at the altar by her philandering beau.

Apparently, this young man had been the first “victim” of the sisterhood, having been forced by a lawsuit, to wear female attire for nearly a year. So effective had been the wealth and the strength of this sisterhood in bringing about this knave’s demise, that they started to experiment on philandering and wayward males, in their own families and for anyone who was interested.

Because of the wealth at their disposal the women bought an expansive “safe” house off campus where these contrary young men were disciplined and transformed into docile, obedient panty slaves. The growth of the society, though steady, was slow and limited to the upper class.

Once it reached North America, the upper class members agreed to allow reasonably well off and well to do businesswomen in, as long as they had an interest, and/or the skills that would promote these transformations. I’d already been told by Miss Virginia that any mention of this group to my father or Brent would result in a truly severe penalization.

Arriving at the Herndon mansion, mother said to Miss Virginia, “I’ll call when we are ready for you to pick us up. Go and have a nice time shopping Virginia.” I minced daintily alongside mother, holding her hand and making sure my carriage was erect and my steps prissy. We were greeted by the Herndon’s maid, Hanna, a buxom, attractive German woman.

Led into the front room, I had to wonder what Mr. Herndon did for a living, or if indeed there was a Mr. Herndon. I would find out there wasn’t. Suzanne Herndon had been wealthy before marriage. She’d married well and divorced even better. Her nephew Simon had been given over to her by his divorced mother, Suzanne’s younger, half-sister. I braced myself upon entering the sitting room. Mother was greeted with an emotive hug and kiss by Ms. Herndon.

Then, I was introduced. I did my most charming curtsey, and assumed what I had begun to think of as “the pose.” “I’m so very thrilled to meet you Ms. Herndon,” I expressed in a very excited, breathless, girlish voice. On our way into the room I had been able to get a look at the very attractive Ms. Suzanne Herndon.

She was about 5' 8" and beautifully slender. Her dark brunette hair was done in a long page bob that just touched her shoulders. Her hair was sleek, shiny and rich looking. Like my mother she wore a “ladies who lunch” Chanel suit, but in a snow white, instead of cream. Her heels matched the suit. She wore sheer seamless hose identical to mother’s.

As I posed, she circled me in much the same manner as mother had, pausing to make comments about my outfit, hair and posture, even fingering the exposed lace of my panties. “Very, very nice Nicole. I must say, I am impressed. May I?” she asked.

Apparently she was speaking to mother, who answered, “Of course.” With that Ms. Herndon gripped my chin gently and lifted it slightly, saying, “Well my sightly child, do you like your new pretty clothes, and your novel, sweet, girlish lifestyle?”

I knew exactly what to say, and to say it sweetly and softly. “Oh yes Ms. Herndon. I like my new clothes and being a girl very, very much!”

“Yes, I thought as much. You may call me Ms. Suzanne, my pretty, swishy one. You also may seat yourself there, on that couch, after mother is seated, of course. Hanna is putting the finishing touches on Simone. Once they arrive, we’ll enjoy our brunch,” Ms. Suzanne added.

After we were seated, Hanna, the maid, entered the room with Simone close behind. I was startled, but I should not have been. Simone looked to be as much of a girl as I appeared to be a panty clad sissy. Though she was attired as childishly as I was, her bearing and demeanor were much more confident then mine.

She minced daintily, but seemed more certain that she was accepted. She wore her hair in a more feminine and less sissified hairdo then mine. Her paged bob, much the same length as her Aunt’s, was a striking platinum blonde. Even more striking to me was that her outfit was identical to mine, except some of the colors were different.

Her babyish dress was a powder blue, along with her rhumba panties and hair bow. The rest of her outfit and accessories were white, just as mine were. I can tell you right now, that from the very first, I never have thought of Simone as anything but a girl. At the time, even in the pecking order of “Cassandra’s sissies” she was already a “girly”. Myself I was a mere “sissy”.

In the society, one could go through different stages, from “sissy” to “girly” to “ladies maid” to “maiden” and finally “trophy miss”. If one actually had a sexual adjustment the title of “missy” was given. I hoped I would not find it necessary to “advance” at all before getting away from these women.

One of the moments I had dreaded was about to take place. I had been prepped by Ms. Virginia but really nothing could have made it appealing. After Simone had said her pleasantries to mother and Ms. Suzanne, she struck the “pose” and mother inspected her, heaping praise on both Simone and her aunt, and of course Hanna, the maid.

Of course, Simone did not acknowledge me. One sissy acknowledging another was impermissible behavior. Once mother had completed her inspection, she motioned for me to come hither. “Rhonda, you must meet Simone. I’m sure the two of you will become the best of friends,” she smiled. I arose and tiptoed daintily toward mother and Simone.

Ms. Suzanne watched from where she was seated and Hanna observed standing off to the side. This was no test for anyone but me. Sissy Simone could handle this easily. All eyes were on “your’s truly.” I stopped a respective distance from mother and grabbed the hem of my dress. Simone did likewise. Smiling we curtseyed and greeted one another with an adorable, “I’m very pleased to meet you.”

It wasn’t over yet. Actually it was far from over. “You two give one another a nice big smooch on the lips. Then make sure you hold hands all day when walking together in the house or on the grounds,” Ms. Suzanne ordered. Actually sissies in the society had to hold hands when walking anywhere together.

It was all I could do to approach Simone, take the tips of her fingers in my own, press my body against her body, and touch my lips to her’s. With my eyes close I joined her as we gave each other a big kiss right on each other’s painted lips. The ladies clapped and giggled as we both smiled.

Walking to the sunroom where the brunch was served, holding this effeminate creature’s hand, I took in what was obvious. Simone was a few inches shorter then myself and much, much, more slender. Her diet and exercise, probably no different then mine, was obviously working quite well. I hoped against hope that I would not become so perfectly svelte.

Her hormone treatments appeared to be working also. Compared to my lightly padded bra, her bust was that of a properly mature 15-year-old female. I guessed her to be my age and I was correct. I noted that my sissy partner squeezed my hand and looked up at me batting her eyes and smiling, just before she seated herself. I’ll admit if she had been a true female I would have been flattered. Under the circumstances I was quietly disturbed.

During brunch, both Simone and I ate silently while the ladies chatted. After the splendid meal, we were given permission to leave the table and after the perfunctory bowing and dipping we were sent off to Simone’s room, hand in hand by Ms. Suzanne. Simone was supposed to show me her room, clothes, dolls, and photo albums.

Once we entered her femininely appointed room, I released myself from the tight grip she had on my hand. “What’s wrong Rhonda, don’t you like holding hands with me?” She asked almost tearfully.

“Please Simone. You’re not serious are you? I mean, after all, do you actually like being dressed up like this and treated as some sort of pantywaist puss?” I asked, instantly realizing I had erred. The little sissy sized me up before squinting her eyes and hissing, “Okay. I get it. Downstairs was a big act for mommy dearest. You’re just a big fake, putting on a show. I can tell you this, Rhonda. With the Sisterhood, that’s very dangerous.

She meant every word, too. “If I were you, I wouldn’t tell too many other sissies about your negative feelings. Not too many of us would agree with you. In fact, you’ve just made a big mistake my sissy sister!” She added, before walking to the far end of the room. Peering out the window she told me of her immediate intentions.

“Right now, in fact, anytime we are together, I would expect you to play things my way. After you leave today, Auntie Suzanne will ask for a full report of our private time together. She will pass the contents of that report to your stepmother. Trust me, anything I say will be believed. So Rhonda, do you want to play nice, look at my dolls and clothes as well as the rest of my living spaces?” She asked quizzically.

I balled up my fists. What a little brat! She turned to me smiling and stuck out her hand, “Shall we hold hands Rhonda, or do I tell auntie that you are still a dissident participant?” she queried. I knew she could really screw things up for me. Reluctantly I accepted her offer and soon she was giving me the “grand tour” of her sissyish living spaces.

Simone was truly in her element. After looking at her plush bath, her overdone canopied bed and her closets brimming over with all sorts of exciting (to her) creations, we wound up, still holding hands, seated on her bed. She proceeded to breathlessly describe for me, her last “exciting” visit to Nanette’s “Salon Demure”.

During this lengthy discourse she took the liberty of not only leaning closer to me, but also placing her other gloved hand on my bare thigh and proceeding to gently rub this exposed portion of my leg. Not wanting to upset her, I acted as if this were nothing to me. Big mistake. Simone took this as a signal to go further.

Wrapping her arms about my waist she used her slender form to push me back onto the bed, before smothering me with passionate kisses to my lips. She had begun to probe my mouth with her tongue before I recovered enough to gently resist her and have her release me momentarily. “What are you doing Simone?” I asked politely, but actually shocked.

“I’m having fun,” she smiled, before stating her agenda. “I think you want to have fun also but you are scared of what people may think. So, I’m going to make it easy for you. You let me kiss you and do some other things and I won’t tell everyone downstairs that you tried to put the make on me. Trust me, they’ll take my word over your’s,” she said as she got up to lock the door.

“Don’t think I won’t do it Rhonda,” she said, staring at me intently. I knew she was serious and I didn’t want to risk the ramifications of the scene she could cause. I gulped, and quizzed, “What sort of other things?” Smiling, she coyly sashayed towards me.

“Let’s just say I won’t expose my penis, nor will you have to touch it in any way. I want to mostly kiss and fondle you and expect some reciprocation on your part,” she explained as she came to the bed and snuggled close to me. Meekly I answered, “Okay, just stick to what you promised,” before being pushed to the bed and then covered with her overzealous French kisses.

At first, I was a semi passive party, though, when I began to imagine her to be a true female, my interest and my stimulation increased. I will say this for Simone. She was passionate. Her kisses were deep and probing. The little squeals of delight she gave when I responded and reciprocated were genuinely kittenish. She was “all girl” in her heart.

When she slithered down my front and began to probe my panty brief I became alarmed. Before I could object she retorted. “I said I wouldn’t use my penis. We did not mention your’s. Relax. You’re obviously erect. Lie down and enjoy me,” she stated as she pushed me onto my back. By this time I was too far gone to complain.

She slid my panties down and plopped my dick in her mouth and began to suck and fondle my surprisingly, very erect member. I couldn’t believe I had become this enkindled by lovemaking with a painted lady boy. One never knows.

This wanton little minx slurped and sucked me voraciously. My penis felt so huge and swollen in her mouth. I never knew I could get so hot from a blowjob given by a sissy boy. When I got very near my apex my dolled up pantywaist lover sensed it and began to massage my balls along with the oral ministrations. 

All this became too much for me to take. I could hold back no longer. I grabbed hold of Simone’s beautiful platinum coiffure and pulled her towards me even more. I bucked and undulated my hips and pelvis. Gasping, I blew my wad into this pansy’s mouth, as she gurgled and slurped, swallowing every drop of my gooey spunk. 

At this point she sucked greedily as if it were her last meal. Wow! What a blowjob! There was still some boy left in me at the time, and the boy in me really liked Simone. Unfortunately, I was dressed as a Nancy boy and Simone was a sissy princess. Such luck! It wasn’t until she had drunk every last drop, that Simone slithered up my body to rest her head on my shoulder and rub my flat chest. 

It was then that I noted that Simone’s blond tresses actually were a wig! I had pulled it off in the excitement of my climax. I decided to say nothing. Looking at the smiling Simone, I determined I wouldn’t bother to tell her for a while. She appeared so contented. 

Why bother? Even if this little sissy slut had a boyish sort of haircut, even shorter then mine, what did I care? It wasn’t until Simone sat up in bed that she noticed. She faced the mirror to sort of fix herself and primp. The freaked out look on her face, when she realized her wig was off, said a lot.  

Her real locks were dark brown, like her aunt’s and done in a razor cut, sort of duck tailed coif that might be worn by a boyish female or in this case, a feminine boy. Our feminine boy freaked. Holding his dainty hands either side of his head he shrieked, “My hair, my wig!” Covering his mouth with his hands, he then hid his face, embarrassed. “Oh no!” He cried. “Where is my wig?” I was startled that Simone would be this upset, so I apologized profusely before handing the hairpiece to her. 

This prissy little princess then ran to her bathroom in a flood of tears. It took some time for the sobbing to stop before she returned to the room. She’d put the hairpiece on, obviously brushed it, repaired her makeup and straightened her clothes. Seating herself on the bed, she began to explain her uncharacteristic, boyish cut. 

“Auntie had Ms. Nanette give me that awful hairstyle as a way to punish me for complaining that my much longer hair was so hard to care for. Now, when we go to parties and outings with the Sisterhood, I stand out as a mocked sissy. She’s even had me appear publicly in a dress and heels with that hideous coif. Can you believe it?” She asked incredulously. 

When I responded with a shrug of my shoulders she grimaced and said, “I’d much prefer to pass as a young lady. I mean, look at yourself in that very elegant, but highly dated, bouffant bubble. No girl your age would wear an elaborate hairdo like your’s. It’s part of your humiliation,” she explained.  

“Even in the clothing of a female your age you’ll stand out. Why, at the Cassandra club you’d be the object of everyone’s derision,” she added as she helped me up from the bed. “In polite society, you’ll be mocked and sneered at, as if you were in a 17th century stock,” she stated. Taking me over to the vanity she helped me clean myself, pull up my panties and then sat me down to help me with my hair and makeup. 

I then went along, following her, and giggling for effect, as we returned to the parlor, where the adults were seated. “Did you two children have fun?” Ms. Suzanne asked. “Oh yes auntie, Rhonda just loved my clothes. She can’t wait to wear some really adult stuff,” my lying sissy friend said. 

“Why Rhonda, I’m very pleased to hear that. By the way dear, get ready to say goodbye, Virginia will be here shortly,” mother stated. After saying and curtseying my pleasantries, I had to once again kiss Simone, in a sweet sissy goodbye smooch. On the way home, mother filled in Miss Virginia on the day she and Ms. Suzanne had. 

Miss Virginia filled mother in on the shopping she’d done. Thankfully no one asked me much of anything. After I had showered and been cinched, Miss Virginia tied me spreadeagle to the bed. Instead of diapering me as she had the two evenings prior, she immediately crawled atop of me and seated herself on my face. 

As I’d done the night before, I began to stimulate her with my mouth and tongue. She must have enjoyed it as she had a shuddering, shaking orgasm. She then started to manipulate my penis, but it was to no avail. I’m still uncertain whether it was my orgasm of earlier in the day, or the shame I felt from having been stimulated, spent and having sex with a sissy boy. 

Whatever it was, Miss Virginia was not happy. “What on earth is the matter with you, you little pansy? I come to your room, to reward you for being good today, and you can’t even get a hard on! What an insult! Well little miss pantywaist, we’ll see about this,” she said as she went to my dresser for a hairbrush. I was blubbering excuses, but she didn’t want to hear it. She released me from my bonds and pulled up a chair near to the bed. “Get over here you impotent pussy. I’ll get you aroused!” she ordered. 

I jumped out of the bed and tiptoed towards her, stopping in front of her. “Over my lap you fairy boy. Get over my lap now, or I’ll tell your mother you made a pass at me,” she hissed. I didn’t want any trouble with mother so I lay across Miss Virginia’s lap. She immediately began to smack my ass cheeks liberally. She didn’t even have to tell me to kick and whimper. 

One blow after another fell sharply on my butt and thighs. I can’t explain why, but when she spread her thighs some, and reached underneath to grab my penis, I began to get an erection, even with the humiliating spanking I was getting. This was surely a defining moment for me. I could have resisted, even though, at this point I wasn’t a match for mother and Virginia.  

I did not resist though. All I could imagine was the whole group, along with Anna, Tasha, and Nanette, all ganging up on me. I became aroused enough from the excitement of the spanking that Ms. Virginia ordered me back to bed, and had me lie on my back. She began to ride my rigid pole, smiling and taunting me. “Don’t cum you little puss. Not if you know what’s good for you.” Once she was satisfied she lay atop me, sucking my neck, my penis still embedded in her. “Want to cum, precious? Good. Here’s what you have to do.” 

We both lay on our sides in a 69 position. While she slowly masturbated me, I was made to rub, suck, lick and kiss her feet and toes. Literally she made me adore her feet. While I paid them homage she had me vocalize my adoration by telling her what lovely feet she had. It was in this submissive atmosphere that I experienced my second climax of the day. 

My ejaculated sperm was all over Virginia’s hands. “Lick puppy,” she commanded and I didn’t hesitate, as the day’s events had really subjugated me. Diapered and in plastic pants, and again bound spreadeagled, I spent another evening wondering what was really going to come of me. 

My next two weeks, plus, were spent in even more intensive feminization training. Mornings of course were strictly for housekeeping. Virginia had made sure that I now handled the lowliest of housemaid tasks. My “realm” of responsibility included the scrubbing of floors, tubs, sinks and especially toilets. Often I was referred to as the “toilet girl” or “potty maid”. 

Hand washing of lingerie, especially soiled panties was one of the favorite duties she assigned me. In addition, my lessons in personal body services were expanded. At first these services had covered hair and nail care only. Now I would perform the more intimate tasks of massage, shaving legs, and giving baths to both Virginia and Nicole. 

The even more intimate and embarrassing responsibilities of giving a douche and changing their sanitary napkins were also a part of my training. Their goals were obvious, even to me. First they were keeping me in a constant state of frustration, submission and embarrassment, while additionally enveloping me in a restrictive but highly feminine atmosphere. 

Anna, Tasha and Nanette kept this regimen going with my exercise, charm, comportment and personal appearance classes. My figure training, exercising, hormone treatments and collagen shots continued. I began to note a change in my body shape. My bust area had begun to develop; my hips were more defined in relation to my waist. My lips appeared swollen and “bee stung”. I now walked with my buttocks swaying, keeping my steps small and placing my feet, one in front of the other. 

The throat spray and my speech lessons completely changed the timbre of my voice to a higher pitch and a more expressive tone. My movements and motions were more precise and gentle. I realized one afternoon, when I had had some free time, that what they were doing was actually working. Bored and listless, I decided to paint my nails. Mid way through my left hand it dawned on me that only a girl would think to do this to find a release from boredom! 

Other then Sunday outings to visit Simone and her aunt, I pretty much was confined to our house and grounds. During these Sunday visits, Simone would try and take the opportunity to “play”. Usually she succeeded. Of course I was ashamed to have participated; however, the occasional evening tryst with Virginia was enough to keep me in constant denial of my rapid transformation into the strange androgynous creature I had become. 

To keep me absolutely in line, the Saturday evening “progress evaluation” meeting was the capper of the whole week. There I would appear before my five mentors. While I posed in lightly padded bra, panty brief and heels, they evaluated my weekly performance. My “transgressions” would be dealt with by this imaginative quintet, using the most inventive methods of discipline. 

Sometimes, of course they simply applied a time honored bare butt hairbrush spanking. Other times though they let the “Discipline fit the misdeed.” If my offense had been walking clumsily, I may have to do all my walking for the next few days in ultra high spiked heels or with my thighs hobbled. When my make up was judged to be improper, or my coif was determined to be lacking in style, I might be made to wear and maintain an elaborate coiffure with vivid, lavish, overdone makeup. 

I had become so dominated, that one evening during one of our trysts, Virginia untied me and had me roll over, telling me ahead of time she would be sodomizing me. As insulted as I was, I was also fearful of disobeying. From then on my butt would be fair game for her well-lubricated dildo.  

On a Tuesday evening, slightly more then three weeks after my enforced feminization had begun, mother told Virginia to prepare me for a Wednesday outing to Nanette Leopold’s Salon Demure. This was more in line with Mother Nicole’s original plan of Wednesday and Sunday outings. So far my time away from the house had been limited to Sundays at Simone’s. 

“Virginia, also make certain Rhonda has an appointment the following Wednesday with my gynecologist Giselle Bordeaux. Of course, this evening, there will be no need to have Rhonda set her hair,” mother added. Virginia nodded to mother and smirked at me in relation to the gynecologist visit. The good news was I did not have to set my hair. 

For the past week and a half, every night before bedtime, I had to either sit in front of my vanity, or in the living room with a portable mirror and roll my hair onto small-brushed curlers. After putting on a hair net and some face cream I would have the choice of snuggling with Mother Nicole to watch a DVD, or head off to bed. 

If I wanted to stay up, snuggling with my stepmother was my only choice. Actually it wasn’t bad. Nicole could be very affectionate, especially when I pleased her. I noted that the day after one of these snuggling sessions, she was always more friendly towards me. To her it was a real mother/daughter thing. For me, it would always make me more ready for Virginia’s nighttime visits. 

In bed I would at first have the hardest time sleeping with the rollers in my hair. I’d toss and turn for a while trying to rest my head just right on my heavily perfumed pillow. At least this evening I’d be more comfortable, although all I had to look forward to was a beauty salon trip and an appointment at a women’s doctor. 

I believe the most significant failing on my part was when I began to masturbate on evenings Virginia did not show up in my room. I would lie on satin sheets, my head on a perfumed pillow, dressed in filmy lingerie; my copper locks up in rollers and a hair net. Slowly but surely I’d bring myself off into a really introspective ejaculation. I never knew how much this meant I was giving in. 

My salon appointment that Wednesday was at 10 AM. Miss Virginia had dressed me in a pair of skintight candy apple red slacks. These fit my cinched in waist and newly rounded hips like a glove. At my ankles the snug cuffs were frilled with filmy tiered white lace. I had on an unusually restrictive panty brief and black panty hose. 

The gaff and tight slacks made me really flat in front. I also wore a form fitting, short sleeved, white satin blouse with pearl buttons. Underneath was my new lightly padded bra, a 36A. I was given a red bolero jacket to wear over the blouse. The jacket buttoned in front with a tight fit and the cuffs were ruffled. Completing this sissified ensemble, were black ankle boots with 2-inch heels, and a matching patent leather clutch bag with dainty shoulder strap. 

Though Virginia styled my hair into a pert bun at the nape of my neck, I was made to apply my own makeup. She insisted I do it lightly for a casual daytime outing look. My piercing studs were removed and replaced with one inch round silver hoops Nicole had bought me. Though I felt ridiculous, by this time I had no idea what to do. I only hoped my father would react so negatively to my appearance he would force stepmother to release me from this feminine charade. 

I just knew he would do it if I could convince him I’d learned my lesson. During the drive to the salon, I paid little attention to where we were or to the conversation between stepmother and Virginia. Once we arrived in a trendy, upscale section of town, Virginia began to look for a place to park. When she found one, Nicole declared it “perfect.”  

Though I had no idea where we were or what to do, Nicole began to explain to me our location and her plans for my day. “You know Rhonda; nearly 3 weeks ago you said you would soon ask me to take you in for a hair appointment. Everyone agreed that would show your willingness to comply with this little plan of mine. The fact is, you haven’t done anything unless you were ordered to do it,” she said, letting this all sink in.  

Then she really began to unveil her plan. “So today you will learn to keep your promises and realize its more fun to have your hair done with mother in attendance. Salon Demure is two blocks down the street. You’ll be going there in about 5 minutes or so. Prior to that you will sashay, and honey I do mean sashay, to the front of that gorgeous clothing and specialty shop,” she smiled. 

I looked to where she had pointed and saw a large window with the name, Cassandra’s in script lettering across it. In the window was a mannequin wearing a French maid’s outfit. I shivered as she continued. “That’s right dear; the store is owned and staffed by the sisterhood. It provides clothing for transvestites willing and unwilling alike. You will appear to be window-shopping for our amusement of course, as well as anyone else who may realize you are a sissy boy. We’ll all have fun.” 

I look at her pleadingly but saw her shake her head and tell me, “Get out of the car and do as you are told. Once we give you the word, you may then walk two blocks in that direction to Nanette’s. You can’t miss it. Once inside you ask for her. She’ll call us on my cell when she’s done with you. Get going sugar. You don’t want to be late for your appointment.” 

Leaving the car I “walked pretty” as mother often referred to the exaggerated slither and glide which she and her friends had taught me. Glancing back I saw Virginia gesturing for me to hold my wrist limply and place a hand on my hip. This exaggerated “sissy strut” could be a real attention getter. From the date underneath the store name, I could see Cassandra’s had been in business at this locale for some time. 

This meant the regulars in this area full well knew that transvestites shopped here. I peeked into the windows and looked at the glamorously clad mannequins. I read the titles of some of the books in the showcases. Though I tried not to look any passersby in the eye, it was difficult not to notice women pointing at me and smiling, while men would shake their heads in disgust. 

I was becoming terribly self conscious of how I appeared when Mother Nicole put her head out the window of the car and said, “That’s enough fun for one morning Rhonda. Don’t fret. We’ll be back and you can shop and maybe pick something up. Hurry to Nanette’s dear, you don’t want to be late. Keep your little pose intact and walk pretty darling.”  

For two whole blocks I really must have put on an eye-catching show for the onlookers. I noted more then a few stares and comments. I was so relieved to get into Salon Demure that I forgot how I was posturing. The receptionist raised her eyebrows and glanced at two other women in the waiting area, before smiling and cheerily saying to me, “Well hello sweetie, and just who might you be?” She ended this question by dramatically placing both hands on her hips. 

As all three women broke into laughter, I answered, “I’m Rhonda and I’m here for a ten o’clock appointment with Nanette.” I was so glad I didn’t slip up and call myself Ronnie or Ron. It seemed like ages since I’d thought of myself as such. The young woman picked up a phone and sang to Nanette, “Oh Nanette, your 10 o’clock is here. She’s incredible darling. A real Sissy Mary.” After hanging up she said, “Nanette will be right here sweetie. You can sit down. There are some peachy fashion and hairdo magazines for you to read if you want.” 

Her emphasis of the word “peachy” wasn’t lost on me or the other two ladies. They giggled as they buried their faces in their literature. As Nanette arrived I jumped up and nearly collided with her. Taking my hand she practically drug me from the reception area into the main portion of the salon saying, “My but we are eager today aren’t we? Well first you’ll have to meet some of the other girls and then we’ll get reacquainted in my office.” 

She took me through the salon to an area where three women were seated in front of mirrors. They had foil in their hair for apparent highlighting. A colorist stood behind each lady, busily applying the hair care products. The three customers, two female stylists and one male employee were all talking animatedly about a television show of the night before. Nanette stopped, obviously to introduce me. I really felt as if I were intruding. 

“Ladies and of course Antonio, this is that Nancy Boy, Ronnie/Rhonda whom I’ve been telling you about. Ronnie I want you to meet some people you’ll be seeing regularly if you continue to come here,” she said as she made introductions all around. The ladies all half smiled and half laughed, wiggling their fingers at me, while saying “Hi sweetie!” 

I was really embarrassed as I said hello back to them, especially when Antonio said to me in accented English, “I am so very pleased to meet you. I hope you don’t mind me asking this; do you prefer to be called Ronnie or Rhonda?” Stumped for the moment I looked at Nanette, who whispered to me, “Rhonda.”  

“I like Rhonda, sir,” I said, as he winked at me and hungrily eyed me up and down. It was an obvious come on. To a real female Antonio would have been considered to be quite handsome. All the ladies picked up on this and gave one another knowing glances.  

Nanette continued my trip through her salon winding up at her office. Before entering she cautioned me, “You’re about to meet my top two employees as far as assisting me with transformations are concerned. The three of us work together as a team. This will be a sort of little interview, where we assure ourselves you’re ready for a salon experience and you won’t be any trouble. I expect you to greet them properly.” 

I knew this meant a curtsey, so I prepared myself. Entering the office I saw two well groomed, very womanly figured (full figured) ladies. Nanette introduced them as Lauren and Claudia. They both arose as I politely curtseyed to them, holding my hands out, fingers daintily spread before dipping demurely. They both approached me and began a detailed inspection of my appearance. 

I just felt so timid, alone, and afraid that when Claudia asked me if they needed to paddle me to assure my obedience I began to cry out, sobbing, “Oh no, please don’t, I’ll behave like a perfect little lady!” The one called Lauren laughed and said to the other two women, “She appears to be sufficiently scared girls. I think we can forego the perfunctory trip to the lacing bar for a paddling.” 

Claudia gave pause and said, “I don’t know Laura. If we skip the paddling I want some type of assurance. What do you say we at least use one of those restrainers?” Both Lauren and Nanette agreed that a restrainer would be wise and Claudia left and returned with what looked like a pink salon cape. The big difference was that this one had straps inside that fastened to my elbows. Nanette took my purse and the cape was lowered over my head. 

Once the straps were tightened and in place, the women connected two straps on the outside of the cape and made these snug behind my back. This effectively made my arms completely useless as if I were wearing a straight jacket. Lauren made a brief check to see that my hands were accessible for nail extenders and a manicure. Satisfied that I wouldn’t be any problem Claudia mince marched me back into the salon proper for a shampoo. 

I made quite the sight, wiggling and wobbling on my heels and under her complete control. She did massage my neck and shoulders during the shampoo. She worked really deep as she was trying to get me to relax. “If you don’t stop stressing Rhonda we’ll give you a tranquilizer and knock you out. I don’t think your mother will be very pleased with you if she shows up and her daughter is like a little zombie,” she warned me.

After my shampoo I sat in a raised styling chair as Nanette fingered my hair, checking the texture and the color. “You should learn to color your own hair. It’s only been three weeks so it’s too early to do it today. Unless you have the time to come back in two weeks I’d suggest buying a good quality color and doing it by the instructions,” she recommended.

“I’ll leave it up to Nicole,” she added, explaining she’d have Claudia work up a color chart for me so that I could select the right products for my make up. She began to snip and trim my hair with her scissors, stopping to comb and check on the progress. When done with the shaping and combing she had given me a short nearly pixyish style that hugged my slender face.  

My bangs were wispy and feathered. My sides were cut to my ears and curled up with tendrils. She showed me the layered back that came to a point just above my collar. For a girl it would be described as cute or perky. On a boy it was quite daring in a very sissyish sort of way. “Some people call this a Peter Pan cut. I like to think of it as the Prissy Pan look,” Nanette teased. 

I had no idea what was in store for me so I tried to speed up my leaving. “Mother wants you to call her when you’re done so she and Virginia can pick me up. Ouch!” I yelped as she pinched my cheek.  

“Not so fast Little Miss Prissy pants. I know what to do. You are going to be here quite a while. You still have a manicure with nail extenders coming. Then of course you need collagen treatments for those sexy lips of yours. Then the real treat that mommy and I have been discussing for some time now; a pretty permanent wave! Sorry honey, you’ll be here much of the day,” she laughed as she rolled over a cart with lots of stuff on it.  

She sectioned my hair until she had all the top hair in a pile. Then she began rolling sections of it onto plastic curlers with attached rubber bands. When she was complete I saw in the mirror that my hair was set atop my head and the small pink rollers were covered with some sort of filmy white papers. None of the rest of my hair had been rolled up. 

Nanette then took a gauzy wrap and tied it tightly around this pile of hair and rollers. Stuffing a towel into the collar of my cape she called Lauren over. “Why don’t you wipe the stray solution while I apply this perm lotion,” Nanette said. She snipped the top from a plastic bottle and applied an extremely pungent smelling lotion to my rolled up hair.  

As Ms. Nanette applied it, Ms. Lauren used a damp washcloth to dab at my forehead and keep the odorous lotion from getting in my eyes. “There,” she said as she dabbed, “We don’t want any of this smelly Sissy Perfume to get in your eyes. You’re already tearing up from the odor,” she added. I didn’t realize it, but I’d be living with the residual scent of this “Sissy perfume” for what would seem like weeks to come. 

Once my hair and scalp had been saturated, my soaked locks were covered with a plastic wrap and I was taken to another area and seated under a hair dryer. As the dryer whirred the scent of the lotion became stronger and the waving rods seemed to tighten. Ms. Lauren repositioned my cape so she could begin a manicure.

For what seemed like quite some time she worked on one hand before Ms. Nanette had me get up for a rinse in the shampoo sink and the application of another foul smelling substance called neutralizer. While it took, Ms. Lauren manicured my other hand before the neutralizer was rinsed and I was given a conditioning treatment. 

Back at the styling station Ms. Nanette began to pick, comb and brush my tresses before spraying my hair, using a warm blow dry and fastening something to the sides and front of my head. She had me turned from the mirror. Assisted by her and Ms. Claudia, I stood up and they untied me from my bonds and seated me back in the styling chair. 

They then spun the chair to have me facing the mirror. “Eek,” I squealed as I saw my reflection in the mirror. My hair was even more sissyish then before. The cap of curls atop my head was set off by a small red bow in front at my wispy feathered bangs. The back and sides were nearly smooth with a slight wave, and spit curled tendrils where my sideburns had been. The sides were set off by smaller red bows each side of my head. 

When I squealed again and put my hands up beside my head and went to cover my face, I realized my nails were now candy apple red two-inch talons! I began to cry but Ms. Claudia squeezed my shoulder, warning me, “We have cry baby sissies parade around the salon in bra and panties. If I were you I’d get over to the makeup area and you and I can play with some cosmetics.” 

Knowing better then to resist, I accompanied Ms. Claudia to a vacant makeup station. The first thing she did after seating me was to tilt my chair back and begin getting a collagen shot prepared. “Just relax and pucker those pretty lips honey and I’ll fix you right up,” Claudia smiled. She inserted the needle at several points about my lips, before emptying the contents. After putting Vaseline on my puckered mouth she sat down next to me to give me a makeup lesson. 

“When you leave here Rhonda, I want your look to be vivid and daring. With your height, your figure, your coppery hair color and your new coif, you are real sex object material. We’re going to see to it that your full potential is realized. Now once you have finished your makeup, I want you to stay seated at this mirror and primp to your hearts content. It’s the only way you’ll fully realize just how feminine you’ve become,” Claudia pointed out. 

I wasn’t thrilled with what she had said, but at this point I was truly at a loss as to what to do about it. So as she instructed me on fixing my face, I followed her directions to the letter. She had me use more foundation then ever before and then had me “powder it down.” Mother had “cleaned up” my eyebrows one evening while watching a movie and these were now thin and severely arched. 

I was made to pencil these in to “open” my eyes up. With some shadow and mascara, my eyes were given the really vacant, wide-eyed look of an airhead fashion model. I then was told to apply a burgundy-tinted blusher to enhance my cheekbones. With my recent dieting, this showed off my svelte face. Along with my new “do” my slender neck was also shown off to good advantage. 

Finally she had me apply my lipstick. First I did the outline with a lip brush, then I filled in with a lipstick tube of, “Very Black Cherry.” Finally I used a coat of Vaseline. When this was complete my mouth literally shimmered with a “come hither” pout, and my entire face was covered with a vivid, lush mask of cosmetics. Left at the mirror to primp, I was warned not to leave the station until mother actually spoke to me. 

Even then I was instructed on what to say to her and how to act when she did speak to me. For quite some time I sat there, primping and fussing with my hair and face while clients and employees alike strolled by for their amusement. Happily I saw mother enter the salon proper, but before she got to me she stopped to speak to Antonio. 

After some time she continued to where I was, finally saying, “Well there you are; and I understand you behaved very well!” That was my cue. As long as I said the right thing I’d be out of here and on my way home. Practically leaping to my feet, I pranced towards her, giving her a big hug and saying gleefully, “Oh yes mother! I had the time of my life! Do you like the way I look?” I asked as I patted my coiffure, and did a little twirl for her.

“Yes I do and I know someone else who thinks you are lovely. In fact I’m sure your father would enjoy this moment. Stand away from the mirror and I’ll take some photos,” she instructed. For the past couple of weeks she had been taking shots of me with her digital camera. She sent most of the shots via email to dad in Europe. 

More embarrassingly she had also put the photos in a file on the PC’s at the house. Now all of our computers had my transformation brilliantly documented on a screen saver slide show. Ms. Claudia came up to us to give me my color chart for purchasing my hair color and cosmetics. Unfortunately Mr. Antonio made a really big deal out of the way I looked, blowing me a kiss as we left. 

Ginny said she really adored what they had done to me at the salon. Mother wanted to go shopping at both Cassandra’s and the Cosmetic Corner, but I somehow begged off, promising to ask to go this coming Sunday afternoon. Then she hit me with the real shocker.

While Ginny grinned in the rear view mirror, mother informed me, “In case you didn’t notice, Antonio absolutely adored you. I gave him our phone number. Don’t be at all surprised if he soon calls you up for a date. Sunday you may want to consider getting something really alluring at Cassandra’s just in case he takes you somewhere very special.”

Even through my brilliant makeup I’m sure I blanched white as snow. I could not believe her! Now I had one more thing to stress about. Not only did I have an upcoming gynecologist visit to fret over and my father coming home in a month; but along with shopping trips to a transvestite shop, and a crowded cosmetic store, I had to concern myself with a homosexual hairdresser asking me out!

I wanted to scream but I was all out of girlish reactions for one day. If this continued someone was probably going to have to put me on Prozac. The ride home was uneventful, especially in light of the recent day’s activities. I really was in much more deeper then my worst nightmare. Bedtime could not come soon enough. 

Will Rhonda go out with her handsome admirer? How will her father react? What will Doctor Bordeaux do to our heroine? We at least hope she has fun shopping for makeup and clothes. We’ll all find out in part three of the story. Prissy.


Sissy Girl Stories