Mistress Psyche's Feminization Fantasies


Sissy Girl Stories


Subjugated Step Sissy

Part Three

By Miss Priscilla Bouffant

(When we left her, Rhonda had more on her plate then she could handle; Daddy’s return in about a month, and a dashing but probably gay admirer. In addition, she fretted over an impending gynecologist visit coupled with outings to a transvestite clothing store and a makeup boutique. Let’s find out if she really had anything to worry about.)

Eight: Like Mother, Like Son?

The planned Sunday outings came much too soon. The inevitable call from Antonio came even sooner. Mother had tried to prepare me early that Saturday morning. “By the by Rhonda; Antonio is not the stereotypical swishy hairdresser. In fact he is not gay at all. He can be very masculine and women are attracted to him. He dates and beds quite a few gorgeous ladies,” she said, trying to convince me to date him.

“Like many very international men; Europeans especially; he is very bi-curios. In your case the attraction, from his standpoint, is probably the fact that your are a stunningly striking, androgynous, effeminate beauty. You can’t blame him for being smitten. You also have tremendous potential as a lovely female and the cosmetologist in him sees that,” she added.

Late Saturday evening, I was finally permitted to shampoo my hair. It was more then 72 hours after my perm had been put in, a precaution I was made to take so as not to ruin the permanent wave. I was told to merely towel it dry and use a leave on conditioner. Then I was corseted, and put into a long, very romantically styled pink satin negligee. After being made to apply vivid cherry red lipstick and dark eyebrow pencil I stepped into a pair of tall, 4 inch, pink spike heeled slippers. Then Ginny had me put on a pink satin turban.

She styled my bangs in front, then the tendrils and curlicues at the sides, so that they peeked out from underneath the stylish headpiece. The turban was decorated with a bright red, ersatz ruby at the forehead. When I entered the living room, mother instructed me to lie elegantly on the divan so she could take photos. It wasn’t until Virginia positioned and posed me that I realized I was done up and postured to replicate a Hollywood ingénue.

While mother took the pictures, Gin put on a CD of torch songs and Broadway show tunes by Barbara Streisand. They both smiled as mother put me through my paces as if I were a starlet. During a short pause, the phone rang. Miss Virginia answered it and said to Mother Nicole, “It’s for Miss Rhonda, ma’am. A Mr. Antonio Molino is calling.”

I began to arise from the divan to object but mother put a stop to this by holding her hand up to me. She motioned for Rhonda to chat with Antonio and stall, while mother approached me, saying, “You will take this phone call and be pleasant and chatty, young lady. You will recline on this divan as a young female whom is chit chatting with a potential suitor. Disobey me and you will regret it. You need not make a date this evening but you will agree to explore the possibilities.”

Frightened, I lie on my side and took the phone. It wasn’t until I began to speak that I realized I was facing one of the PC’s with a slide show screen saver of my transformation. The newest photos, those of my salon visit, were being featured. Until I saw these, I had not realized how truly feminine I appeared.

I was now so much more slender, my weight being only 135 pounds upon my 5’ 10” frame. My natural waist was a mere 26 inches. With a corset it was 23. The day of my salon appointment, with my red pant suit with the ruffled cuffs on both the pants and jacket, and my permanently waved hair, I looked much the part of a freshly groomed poodle.

Now with torch music playing, dressed as a jilted diva, lying on a settee, watching a pictorial of my transformation unfold before me, I had little chance to be anything but pleasant to Antonio. I couldn’t kid even myself. At most I could postpone a date and possibly use this smitten Romeo to aid me in an escape.

“Hello. Antonio? This is Rhonda. How nice of you to call,” I crooned, hoping to please my tormentors. He responded in kind and we began to chat, first discussing my salon trip. My smile seemed to please both stepmother and Gin. He talked sexily, telling me how very attractive I was and how he wished that one-day he could beautify me. I hardly noticed that this being courted by a man somehow intrigued me as I idly twirled one of the strands of hair peeking out from under my turban.

While he chatted, it came to me how I might use him to aid in my escape. I’d have to be coy and sexy to do it but I was determined to pull it off. When he finally asked me about a casual date, I hesitated and said, “Let me check my calendar.” Pausing a moment I added, in a sultry voice, “Antonio could you call me during the middle of the week. I’m busy until Wednesday and don’t know what mother has planned after that. Yes. Wednesday evening at nine would be scrumptious, dear. Goodnight to you also. Thank you so much for calling,” I said as I coyly hung up and winked at Ginny and mother.

They both grilled me before bedtime and mother assured me she would see to it I was free for the weekend. My plan was for a casual lunch first. Then I would see how father responded to my appearance and my dating of a man. I was certain he would be appalled and have me freed from my feminized slavery. However, if not, I would have to string Antonio along, ultimately coercing him into aiding my flight.

I was hoping he’d be so intrigued with dating me, that in exchange for a few dates he might help me flee to my real mother, and she would be so angered with my father, she’d not only have me return to a normal lifestyle, but also sign the papers allowing me to draw on my trust fund before I turned 26. For the time being though, I had other things to deal with, namely the visits to both the Cassandra store and the make up boutique, followed by a Wednesday doctor’s appointment. 

Sunday I was surprised by the very feminine outfit Ginny put me in. I wore a poodle skirt with rumba panties, spike 3 and half-inch heels with a light but very fluffy pink short-sleeved sweater. My hair was swept back and up in a daring heavily jelled spiky style similar to the type of “do” Anna would sport.

My earrings were pendant style and gaudy. I was fitted with sheer seamless hose. A fashionable bow in my hair completed my girlish ensemble. Though I felt strangely comfortable walking to the car, and also during the drive, I became mysteriously ill at ease as we entered Cassandra’s. It was for good reason. As we strolled in, myself following Ginny and mother, a tall well-groomed female approached us.

Ginny tittered and mother spoke with a smile, “Now Virginia, don’t tease. Lulu looks simply ravishing today.” I should have known. The hobble skirt, the tall five inch spikes, the glistening bee hive hair do, “Lulu” was one of the sissified cross dresser employees. “Oh my, Mistress Nicole and Mistress Virginia! How wonderful to see you!” Lulu gushed as she minced her way delicately to the front of the jewelry counter.

Posing hand on hip with one hand exquisitely in the air she then covered her mouth in mock surprise before adding, “Pray tell, and who is this tasteful creature you have brought to our lovely shop?”

Mother smiled and said, “This is my new and improved step daughter Rhonda. We want her outfitted with some clothing and costumes, which are more adult looking. Now Lulu, if you would, tell Mistress Anna we are here.” Lulu curtsied properly and skipped off to find Mistress Anna. Once Mistress Anna arrived, Lulu in tow, I was sent off to the “fitting and change” area of Mistress Anna’s office.

With much trepidation I followed my fellow sissy. Closing the door behind her, Lulu pointed to a curtained stall and said, “Go in there and strip down to panties, bra, heels and hose. Don’t dare hesitate as if you do I will be obligated to tell the ladies. Of course you’ll be punished. I’m certain you are familiar with the lacing trapeze,” she said, motioning dramatically to that dreaded apparatus.

I did not need for her to repeat anything. When I exited from the dressing room she again gestured stylishly, this time saying, “You will please stand stock-still on the posing pedestal. I imagine you are well versed in posturing penitently. Then by all means please do. The mistresses will want to get a good look at you and expect you to be severely self-conscious,” she said as she helped me up the three stairs to the pinnacle of the aforementioned “posing pedestal.”

Lulu then assisted me by positioning me in the expected repentant stance. We were just in time as the three ladies entered the room chatting gaily, oblivious to our discomfort. Lulu immediately curtsied and stood off to the side her head bowed as that of a rebuked lady’s maid.

Mother, Anna and Ginny fell silent which only added to our discomfort. Anna spoke first. “Seeing how Rhonda will soon be masquerading as a true female instead of loudly proclaiming that she is actually a sissy, don’t you feel we should gaff her more stringently? After all, what if her new man was to take her swimming? Would she be able to pass scrutiny in a bikini?” Ms. Anna questioned.

Mother and Ginny concurred and Ms. Anna called out to her feminized assistant, “Lulu! To the gaffing area with her! A Novice sized mini-miser for the young maiden,” Ms. Anna proclaimed.

We minced off with Lulu in the lead, entered a curtained area and I was shown to a dressing table. “Relax while I slide off your rumba briefs. Then we are going to chill your genitals and carefully tuck them inside of you. After that we’ll slide the proper ‘mini-miser’ up onto your hips and thighs dear,” she said as if this was something one did every day. Then she asked me an embarrassing question, as if I weren’t sufficiently mortified already.

“Have you ever been with another sissy or male in a sexual situation? If so, tell me. I’ll either milk you off or you can milk yourself. It’s best to do it before I start to handle you. Once you’re chilled it’s nearly impossible to get an erection to go down,” she said calmly. Blushing I admitted to having been with Simone and tried to explain. Lulu quickly silenced me.

“No explanation needed honey. We’ve all been there. The choice is yours. I milk or you milk you. You need to decide quickly. The ladies are expecting us soon,” she added. With tears in my eyes I turned my head away and quietly sobbed, “Go ahead, you may as well do it.” Out of the corner of my eye I saw Lulu shrug, again acting as if this were a regular part of her day. Reaching for some ointment she started to finger and massage me and I was quickly erect. Her ministrations were businesslike and efficient.

Even more humiliating was that fact I was certain all three women knew of my milking. As she milked me off, Lulu hummed a tune and then began to sing quietly but huskily, “Hush little baby have you heard? Momma’s going to buy you a mockingbird.” As she sang I relaxed and when I finally did “blast off” I was put into a dreamy introspective state. As Lulu, chilled my genitals and pushed them up inside me I giggled and tittered as if she were tickling me.

Once the sleek latex gaff was in place she slipped my rumba brief back on me and assisted me from the table. It wasn’t until my spike heels touched the floor and I began to walk that the true discomfort that a first time “mini-miser” wearer experiences, finally hit me. Wow! Lulu noted the look on my face and in my eyes and commiserated.

“That’s okay honey it takes some getting used to. Stand there and watch me. You should walk like this until things settle into place,” she said as she walked oh so ever gingerly about the room. “It will be a dead giveaway to most any mistress and just about any ‘mini-miser’ wearing sissy that you are truly and tightly gaffed. It’s worth it though. Especially when you have a swim suit or hot pants on,” she emoted enthusiastically.

As I tottered ever so carefully back into the main room assisted by Lulu, the knowing glances and smiles of the three ladies said it all. Once upon the posing pedestal I did not need to act penitent or contrite. I was as realistically subservient as I would ever be. Soon the comments of what I should be made to try on began.

Mother of course wanted something to make me look “special” on my “forthcoming” date with Antonio. Ginny chimed in that I really didn’t have an “intimate occasion” maid’s outfit for special evenings when I would serve stepmother and father, or Brent and one of his favorite girls. Miss Anna insisted I needed something to wear to please “daddy” when he arrived home. I didn’t argue.

They even decided to include Lulu who nearly fainted from glee when asked her opinion of what she would put me in. “Oh my goodness,” she stammered, taking a breathe and placing her hand over her bust. “Why not a really classic luncheon outfit for afternoon dining with the girls,” she smiled.

I was made to model each piece of apparel, following Lulu’s lead. She would walk in front of me and I was expected to mirror her every move, turn, gesture and facial expression. First came “that little black dress” as women refer to it. Mine was sleeveless with spaghetti straps. I was shown how to seat myself with someone holding a chair for me and to walk linked arm in arm as I would with Antonio.

The maid’s outfit came next. A sheer black chiffon creation with frilly heart shaped apron and tiara headpiece. I pantomimed serving at a table for two, quietly and modestly. After this I modeled a purple taffeta mini with stiff starched petticoats beneath. This I would wear for “daddy” and Brent when they came home. I dreaded Brent’s reaction worse then father’s. I had not made life easy for Brent.

Lastly I showed off a ladies luncheon suit in a cranberry color. The jacket was of the waistcoat style. Of course I’d need shoes and accessories to match everything. Leaving Cassandra’s I heard Anna say to mother, “Say hello to Phyllis at the Cosmetic Corner for me, Nicole.” Mother turned and smiled and said back, “I wonder if she will recognize Rhonda?” 

This intrigued me and didn’t bode well so I asked while transiting in the car, “Who is Phyllis and why would she recognize me or not, mother?” Nicole turned and said, “Don’t tell me you’ve already forgotten Phyllis Lane? Goodness, the two of you dated for almost three years. I guess you don’t think of girls much these days’s do you? I’m certain she hasn’t forgotten her Ronnie though. Not after the way you jerked her around and cheated on her,” Nicole said turning away from me. 

Oh my goodness! This was not going to be fun at all. If she figured out who I was Phyllis would be the first person from my crowd, old or new that would find out what had become of me. She could easily spread it around. I’d have to be convincing. It was not to be my lucky day, however. 

We entered the store supposedly to buy hair color and cosmetics for me, intending to match everything to the color chart Claudia had made up for me. Nicole inferred the sales lady might need to do a makeover while she was at it. If I got that close to Phyllis she’d almost certainly figure out whom I was! 

Nearly right away, mother and Ginny walked right up to the counter where Phyllis worked. She was now in grad school and working part time. She recognized Nicole and Ginny right away. “Nicole, Virginia, why it’s been ages! I am so glad to see you! What brings you here to Cosmetic Corner?” she asked in her usual pleasant tone. 

“Hair color and some cosmetics Phyllis and it’s wonderful to see you,” Nicole said just as pleasantly. Phyllis smiled and paused, finally saying, “Well I guess I should ask right now to get it out of the way. It’s inevitable. How is Ron doing? I still occasionally think about him even though he really gave me a raunchy deal,” Phyllis added almost laughing. 

“You’ll be interested to know Ronnie is doing quite well. More or less turned over a new leaf,” mother spoke in a matter of fact tone. Phyllis looked puzzled and then smiled. I got really nervous. Mother continued, “I’m not surprised you didn’t recognize him or I should say her, she added gesturing towards me. Phyllis looked more puzzled so mother continued. 

“You see Phyllis, Ron became so much trouble for us we decided to try some petticoat discipline. We were only going to dress him as a girl for a couple of months to teach him a lesson. It seems once we began dressing our Ronnie in earnest, she really began to enjoy it. So much so that she dresses all the time now and is very happy and content to be our Rhonda. She has really found herself,” mother concluded. 

At first Phyllis stood there with her jaw dropping, then she smiled a huge brilliant grin. “You don’t say? Then our Ronnie has become a real sissy girl? Rhonda, huh? I suppose the hair color and make up is for her then?” She asked facetiously. As I hung my head mother agreed whole-heartedly with my ex-girlfriend. 

“That’s correct honey, and what I’d like to know is if you would like to help your ex make a smooth transition from sissy status to full fledged womanhood. Would you enjoy helping us pick out the hair color and make up and give Rhonda a real fashion makeover? You’ll make a really nice commission to boot,” mother grinned. 

Phyllis went and got the hair color suggested on the color chart and then pointed to a rotational type stool that one might see at a bar or lunch counter, “Have a seat little missy, and we’ll get you all nice and caped. Then we’ll get going on that pretty face,” she said as I was assisted onto the stool by Ginny. 

“Isn’t that cute? She’s such a girl she needs help getting up on the stool. Is Ginny your mademoiselle, honey? You seem a little big to have a governess though,” Phyllis implied as everyone but me laughed. She excused herself momentarily, returning shortly with an explanation. 

“Every once in a while we get a boy/girl in here that wants us to pretty him up. All the girls enjoy it. I was just letting my friend Andrea know that Rhonda and I once dated. She couldn’t believe it. I hope you don’t mind, Miss Nicole?” Phyllis said mock innocently. 

“Not at all Phyllis. Rhonda needs to ‘come out’ with her old friends. It’s the only way she’ll become accepted. She can’t hide. I was hoping you may forgive Rhonda and help her get acclimated to being a girl,” mother requested as I nearly sank into the floor. 

“I’d love to! I’ll even come over the house and help her with stuff. Especially if you’ll introduce me to that hunky son of yours, Brent!” Phyllis said with enthusiasm. First she placed the makeup cape over my shoulders and fastened the clasp in front. By the time she had begun to put skin cleanser on me and begin my foundation, her friend Andrea must have told everyone in the store what was going on. 

As Phyllis started putting powder over my foundation, customers and employees alike began to cruise by to get a really good look at me. I felt uncomfortable enough on the elevated makeup stool. My only makeovers thus far had been done on vanity benches or salon chairs with chair backs. This stool was not only high in the air but had no backrest. The only support I had besides the seat cushion was a small, attached footrest. 

The way I was balanced on the seat, with my hands neatly folded in my lap and my back perfectly straight, I was sure I made a perfectly prissy picture for all those observing me. Then Phyllis stepped back to view her handiwork and I saw myself in the mirror. Oh wow! What an absolute prissy missy I appeared to be!

My ex-girlfriend worked diligently to paint me up to be the picture of overdone fussiness. She carefully arched my brows with dark pencil to give me a truly wide-eyed, “doe in the headlights” appearance. My cheeks were blushed with a flamboyant glistening shade of wine-red blush. The tone of the hair color stepmother had purchased was close to the hue of this blusher. 

Finally my lips were decorated with a velvety maroon gloss. Satisfied with my face, Phyllis coated her palms and fingers with some sculpting cream and began to work it into my tresses. She then used a pick comb to tease my tousled mane. Smiling she sprayed my locks liberally with heavily scented hair spray before stepmother added the finishing touches with a decorative barrette and a good dosing of Jean Nate’. 

“My you are so lovely Rhonda, look at yourself!” Phyllis exclaimed as she helped me down and propelled me to the mirror. Removing my cape she held me with her arm at my waist, close to her and added, “I never dreamed when we were dating that you’d have made such a lovely female. Does she have a boyfriend yet, Ms. Hampton?” She asked, turning to Nicole. 

“She has an admirer, Phyllis. Antonio Molino, who does hair at Nanette’s Salon Demure. They should soon be dating, possibly this weekend. By the way Phyllis, Brent always thought quite well of you. He never could believe the way that ‘you know who’ treated you. I’ll see to it that he knows you have shown an interest,” Nicole said. 

“Oh, wouldn’t you know it! Of course she has a hairdresser for a beau. What little fashion queen wouldn’t,” Phyllis chimed. “Of course I’d love for Brett to call me. Maybe we could double with      Rhonda and her man,” Phyllis added.

I looked so overly sexy and decorated. I was the personification of a slut trolling for a guy. By the time I reached the register I was sure everyone in the store knew the whole story and indeed the cashier, the woman in front of us and the lady behind us in line all commented to Nicole on her “very chi-chi daughter.” Nicole loved it. 

From my crimson upswept fashion cut, to the tips of my high-heeled clad toes, I looked the embodiment of a style queen showing off for the world. Late that same evening, sleeping in a fussy negligee, my hair netted, my face creamed, my pillow perfumed I awoke in a cold sweat after dreaming of being in Antonio’s arms, hugging and kissing with him! What on earth was happening to me? 

Even scarier was the fact that I had a partial erection! Was I? Had I actually become female at heart as Simone had? I lie awake determined to convince father I had completely reformed and that this feminization had to desist. He would be home in a couple of weeks. Failing that, I then would have to convince Antonio that after a few dates I could make it worth his while to assist me in an escape. 

I finally cried myself to sleep dreading my trip in three short days to the offices of Dr. Bordeaux. I wondered what humiliations awaited me there. I knew I would soon find out. I was certain the day of the visit would prove embarrassing. I wasn’t wrong. 

As I was told during the ride to the doctor’s office Giselle Bordeaux, was a specialist in transgender treatment. Though known as an excellent ob/gynecologist her practice was not limited to that. In this area she served as the top consultant used by the Cassandra Sisterhood for transformations of varying degrees of severity. 

Technically, in Sisterhood jargon, the degree of my transformation was considered, “permanent, with no sexual adjustment.” That was a relief, of course, at least the part about “no sexual adjustment.” I absorbed this information when the nurse read my chart to Dr. Bordeaux as I lie on her examining table. 

Wednesday was more or less transgender day at Dr. Bordeaux’s. At least I wasn’t the only feminized freak in her office that morning. When the receptionist called out, “Miss Rhonda Hampton,” Nicole and I rose to follow her into the examining room. From there, Nurse Collins took over, instructing me to give a sample and then undress behind a curtain leaving on my garter belt, hose and heels. I had not worn my highly restrictive “mini-miser” gaff to the doctor’s. That morning I had put on a stylishly frilled brief. 

After I hung up my other clothing neatly, I was given a filmy, thigh length negligee to wear during the examination. It tied in front with a sash and did little to hide my budding pubescent breasts and my “not so large, any longer” genitalia. 

 As I walked from behind the curtain to the table Nurse Collins let out a wolf whistle and Nicole laughed. “Could I give my stepdaughter a hairnet to wear during the exam? She is just so fussy about her appearance and she’d just die if she left here with mussed hair,” Nicole said to the amusement of the nurse as she carefully arranged the filmy net over my stylish coiffure. 

“My goodness yes. They all get so fussy after they get transformed, don’t they? Most of those we get in here are much worse then the most prissy of females,” the nurse added. After I was positioned for my exam, Dr. Bordeaux entered. 

First she discussed me with Nicole as if I were a house pet and Dr. Bordeaux the vet. Then the Nurse read my chart, while the Doctor took my blood pressure and temperature. Finally the Nurse and Nicole left, leaving me with the doctor. 

Giselle Bordeaux was petite and very attractive. Unlike many female doctors she wore heels and was smartly and chicly dressed under her white exam coat. She wore subtle makeup and her collar length hair was done in a pretty curly perm. Her perfume was enchanting to say the least. 

“Do not be nervous Rhonda. I understand your step-mother gave you a little something to calm your nerves this morning?” She said, halfway inquiring. Looking at my chart she added, “You’re quite fortunate. Quite a large percentage of ‘my girls’ are administered a much higher dose of estrogen then you are. It renders their ‘plumbing’, so to speak, quite useless.” 

She went on for my obvious discomfort, “Your dosage is maintained at a slightly higher then minimal level for several reasons. First of course, it curbs your offensive boyish behavior while decreasing your sexual aggressiveness. Your sex drive is still there but your partner being aggressive will activate it. Though you are still passionate and adoring, your drive will come from being submissive and subservient,” she smiled, and then seemed to wait for my response. 

With no response forthcoming she continued. “Additionally, the hormones will aid your mind and body to become more feminine. Your hair will grow differently, hopefully thicker. Your body hair will become sparse. Your buttocks, hips, thighs and breasts should become fleshier. The development of your breasts will be that of a young teenage girl, however the basis of a foundation will form to aid possible breast improvement implants,” she said quite professionally. 

“Lastly your mood swings and your girlish attitude towards everything will become more pronounced,” she added. “For instance do you find yourself daydreaming when watching television or reading?” She asked. It was true and I agreed. Besides, Nicole only permitted me to read fashion, hairdo and housekeeping magazines. My only choice in literature in book form, at this time, were those soppy, romance novels that Ginny and Nicole insisted I not only read, but report to them on. 

Television shows and videos were no different. All the talk shows I was made to watch were from a feminist angle. The movies were all “chick flicks” and even the comedy programming and music programs were strictly female. They loved for me to watch and report on my “favorite” soap. The women’s angle was the only one permitted me. I had noticed my responses, especially to stress situations being more emotional and dramatic. 

The doctor then took me by surprise when she reached and untied the sash on my negligee and let it fall open, exposing my delicate orbs. Reaching for one of them and then touching both individually she whispered dramatically, “My land, but aren’t these beautiful?” She then put some sort of cream on her fingertips and began to toy with my nipples remarking, “Let me know if they appear sensitive to you.” 

My nipples were indeed sensitive, and I initially grimaced, as she gently rubbed my aureoles. I then relaxed as her masterful handling of the situation both chastened me and then aroused me. “Well what do we have here?” she commented, first looking at my obviously flushed and blushing cheeks and then at my mildly stimulated penis. 

“I need to perform a test on your genitalia anyway, Rhonda. Your apparent excitement at my ministrations makes this quite possible.” She then covered my breasts by closing the robe and folding my arms across my chest. I defensively wrapped my arms tighter over my chest and shivered to her noticeable delight. Smiling broadly she used both hands to begin to administer the inevitable “milking.” 

“Most of my girls enjoy this portion of the exam. You’re acting as if you are enjoying it also. Do you want to be one of Dr. Giselle’s girls Rhonda? If so, why don’t you tell me?” she smiled broadly as my response to her nurturing became obviously positive. As my breathing became deep and receptive, my eyes misted up and I felt chilled and flushed at the same time. 

My pleading look told her everything she needed to know, but she insisted I emote my feelings verbally. “Come on girl. Give it up baby. Tell Doctor Giselle what you want. Give it up girl. I’m waiting,” she encouraged. From the depths of my broken soul all the frustration and emotion of the prior weeks and months came to the surface. 

Sobbing and twisting my body in fervor I whispered, then cooed the words from my lips; “Oh yes! Oh please, oh yes! Oh yes, I want to be one of your girls. Please do me oh so good? Please make me feel so good,” I cried as the tears streamed down my cheeks. 

She increased her stimulation of me and my back arched and my stomach muscles contracted in excitement I let out a banshee’s wild squeal. At this very moment she inserted a surgically gloved and lubricated finger into my rectum and wiggled it rapidly against my sphincter muscle. 

“Yow! I was like a crazed creature, writhing and twisting in a wild display of eagerness. Wanting more and more gratification, I seemingly felt insatiable. As I plummeted from my precipice the Doctor rubbed my tummy as if she knew my insides seemed scrambled. I cuddled up to myself in a selfish display of childishness and rocked back and forth as I sobbed and blubbered. 

“I want mommy. I want my mommy,” I sniveled quietly as I drifted off into a sort of dreamy state. I’m uncertain how long I stayed like this, however my next realization was Dr. Bordeaux properly and quietly saying to me, “It is time to get dressed Rhonda. When you are done, knock on that door and come into my private chambers for a brief consultation,” she said, pointing to an entry to the rear of the exam room. 

I felt so sated as I put my clothing on, though I was also feeling humbled and slightly shamed, that I’d let her handle me so freely and had lost all control. Knocking meekly and entering the aforementioned room I was greeted by the smiling doctor and my smug stepmother, Nicole. 

“Sit down Rhonda we were just discussing your hormone therapy. I want to give you a booster in a few days, possibly here on Monday. Until then we want you to stop taking the hormones. It will give your body time to adjust to all the changes it’s going through; not to mention the emotional changes you are experiencing,” the doctor said in explanation. 

She instructed Nicole to make the necessary appointment and after we left the office Nicole and I headed to the estate. Later that evening the expected call came from Antonio. I handled it as well as I could. I felt certain that with very little manipulation I could convince him to help me. I was desperate that dating a male meant little in the long term. 

If I were merely a curiosity to him and he wasn’t gay, he wouldn’t want sex from me anyway, would he? I thought not. A few dates to show me off and then I would approach him for help. I probably need not even have to do that. I was certain father would revolt when he finally faced the full reality of my circumstances. 

After I let Antonio make some romantic talk, I cheerily agreed to a Sunday evening date at an impressive eatery in the same, up market district, where both the Salon Demure and Cassandra’s were located. Ginny and stepmother Nicole could barely contain their enthusiasm at my impending rendezvous. 

I had mixed emotions, though I did fall off to sleep quite quickly. On one hand I was apprehensive about Sunday evening. On the other I was fully sated from my encounter, which had been disguised as an exam, by Dr. Bordeaux. Little did I know that I’d have several restless days and nights in the very near future. 

I felt fine Thursday morning but my afternoon began with a mild nervousness and some intermittent cramps. By early evening I was getting hot and cold sweats and flashes with the feeling of being bloated. What on earth was going on? When I finally told Ginny of my symptoms and asked to be excused from both housework and supper she dashed off to find Nicole. 

Nicole entered the kitchen gleefully with a glass of iced water in one hand and a large oblong pill in the other. “Here’s some nice cool iced water and a nice big Midol, baby. It seems our big girl is finally having her first period! We are all so happy! Wait until I tell all our friends and family!” She added with delight. 

My look of shock did not fetter her optimism as she sat me down and practically forced both the pill and the refreshment down my gullet. Once I had imbibed of the medication she offered the forthcoming explanation. 

“Taking you off the hormones will always give you the symptoms of a menstrual cycle. We’ll do it every 30 days or so for about 4 or five days. Of course you won’t have the discharge a real female has,” she added as if this were going to make me feel so much more at ease. 

“We’ll be able to stop the discomfort by having you get a booster shot and continuing with the pills. The booster is more or less like the ‘fix’ a drug addict gets for withdrawal,” she said as a way of further explanation. I could hardly believe my ears and I knew from past experience that no amount of begging or pleading would discourage my wicked stepmother from her agenda. 

According to her own words, I was going to be her “period girl” until Monday. Goodness. What about my perceived date with Antonio? I suffered horribly from the increasingly worse symptoms until early Sunday morning when I actually got on my knees and pleaded with Nicole to call Dr. Bordeaux so I could get an emergency booster. 

“Please mother? Won’t you please call her? I’ll be such a bitch and a wet blanket for my date with Antonio. You don’t want him to think I’m a little prig do you? Please mother, just this one time? Oh, please? Pretty please? Pretty please with sugar on it? I promise to do anything you say. Please, only this time?” I couldn’t believe what a fairy I’d become, but I was willing to do anything just for a little relief. 

Nicole acted perturbed and looked at Ginny who thankfully, nodded her assent. “All right Rhonda. I can see you’re going to make such a big deal out of a little period. We real women go through this once a month. Not only are you a failure as a male you are a miserable excuse for a female. However we can’t dwell on that point,” she said pointing across the room. 

“Crawl over to that end table and get me that portable phone. Oh my gosh. I hope Giselle isn’t out on her boat. I’ll be so terribly embarrassed,” Nicole said as I edged over to get the phone, moving agonizingly slow on my hands and knees. Returning, I handed the phone to her, staying on my knees, fearful she would change her mind if I did not remain completely remorseful. 

“Hello, Giselle? Nicole Hampton. I’m fine dear. How are you? Where did I find you darling? You’re on your patio? Well I feel a little better. Well Giselle, it appears our little Rhonda can’t take another day of her cycle. Yes, that’s correct. She’s begged and pleaded with me to call you for a booster shot,” she told the doctor, looking down at me with contempt. 

“Really? That’s so very understanding of you. An hour? I should hope she could survive that short a period of time. Thank you so much Giselle,” she said as she handed me the phone in disgust. “Giselle said that most all of her sissies fall completely apart during their first period. You are in good company Ronnie,” she sang facetiously. 

I crawled back over to put the phone in its cradle and returned to my stepmother to hang my head in shame in her lap. I bawled my eyes out and profusely thanked her for her kindness. She sighed as she massaged my neck and told me to “Get it all out,” and “Cry those big sissy boy tears for mommy.” I didn’t let her down for a minute. I sobbed and whimpered just like the simpering pansy I’d become.

Mercifully, Dr. Bordeaux arrived as scheduled. Right in the middle of the living room, Ginny pinned up my miniskirt and I lowered my ruffled rumba panties to my knees. My transparent “mini-miser” made me quite girlishly flat. Then with my panties still restricting my knees Doctor Bordeaux requested we escape to the privacy of my bedroom. 

Waddling due to the restriction of my panties at my knees, I made my way to the bed and was helped by my stepmother to kneel sideways on the bedspread, my feet dangling over the edge. I’d been in this humiliating position many times before for various paddlings and other indignities. As I looked around the room in apprehension. Ginny smiled and fingered the paddle that hung menacingly on a peg near my large full-length mirror. 

Doctor Bordeaux gently turned my head to look away and felt my butt for a bare spot away from the elastic gaff. Finding a spot she dabbed it with alcohol and inserted the syringe in my butt. After a brief prick like feeling, a soothing, cool sensation came over me. I quivered in delight. 

Nicole was not about to let me off so easily, however. “I hope you are happy Rhonda. All that fuss and Doctor Bordeaux having to be taken away from a lovely Sunday morning breakfast. Besides a world of thanks, I believe you owe her a contrite apology, young lady.”  

I both thanked her and apologized to the good doctor in a profuse manner. “Don’t worry Rhonda. Your first period is always the worst,” Dr. Bordeaux added. This was no encouragement to me. As long as I stayed in this situation this would be happening every month. 

Shortly after I was give a Midol, a Prozac and was told to take a nap. “We’ll awaken you in a few hours for a light lunch. Then we will prepare you for your date with Antonio, at Caesar’s, stepmother added. I slept soundly, though I had another disturbing dream. 

In this dream, or nightmare, I was again made love to by Antonio. I was on the bed kneeling as I was when given the hormone shot. In this case though I had on a ballet outfit complete with pink tutu, slippers and tiara headpiece. My hands were tied behind my back and I was gagged with a white chiffon scarf. 

I had a terror stricken look on my face and was squealing like a piglet through the scarf. Antonio was smiling ear to ear and his penis was in my rectum as he pumped and pumped away to the rhythm of Ricky Martin’s “La Dolce Vita”.  The dream was so realistic I could feel him inside of me. 

The feeling was quite discomforting. I could even feel him squeezing my breasts as he screwed me. Then he freed my mouth from the gag and I began to pant and screech. Finally to my chagrin I began to enjoy the action enough to begin pumping back into him as he slapped my buttocks. My panting reached a frenzy and my dream lover pumped his semen into my anal canal as I came profusely also. 

I awoke in a cold sweat and this humiliating feeling came over me as I realized my panties were full of big sticky gobs of my own love juices. I had actually had a dream of being screwed by a male! The humiliation was so intense I began to cry. I was determined not to let this happen in real life. 

After changing panties and cleaning myself off I went back into my nap until Nicole woke me for a light lunch taken with her and Ginny. Then it was into a steaming, perfumed bubble bath followed by a close shaving of what little body hair I had left, including that hair around my pubes. 

Because of my recent  dream I didn’t even get aroused when Ginny handled my shriveled love stick. She smiled as she noted it. Now it was time to dress, have my hair and nails done, and then my face would be made over. I started by putting body lotion over, on and in, every nook, cranny and crevice of my feminized form. 

That completed, I next powdered myself over the lotion before putting on a white garter belt, sheer seamless hose and a pair of 3-inch open toed pumps. I immediately went to my lacing platform and grasped the trapeze, expecting a severely restrictive corseting. I got exactly what I’d expected. 

Ginny and Nicole put their hearts and souls into cinching me down to a perfectly feminine 21 inches, my natural waist recently being measured at 25. This time I really noted how the corset helped reshape and enhance the size of my hormonally induced breasts. After they put me in a black pushup bra and a scalloped       brief, my new “little black dress” was dropped over my head and smoothed into place. 

I asked about wearing a gaff and the ladies laughed. “You’re going on a date with Antonio darling. We want you to be as accessible as possible to him,” Nicole smiled. She then bade me to seat myself at the mirrored vanity so Ginny could begin my nails and Nicole my hair. While Ginny gave me a manicure Nicole rolled my freshly shampooed hair onto hot rollers. While I waited for the polish and my hair to dry, Nicole coached me on what to say and how to act with Antonio. 

I felt like a piece of meat for sale. My rolled hair was finally dry enough to style. Nicole decided that an upswept ‘do’ was the ticket. With long dangling earrings and upswept hair my slender neck and equally slender figure was highlighted. “Antonio will be devastated darling. I believe you are in for quite a date,” Nicole said. 

My makeup was done in smoky, sultry tones around my eyes and cheekbones. However my puffed pouted lips were a gleaming shiny red. Sprayed heavily with perfume I was seated in the hall adjacent to the living room to await Antonio’s arrival. 

When Antonio arrived, Ginny greeted him and seated him in the living room. Then Nicole and I made our entrance. She was absolutely charming towards him. Then she stepped back and motioned for me to greet him. I did so with a curtsey. “Enchanted,” Antonio said as he took my hand and kissed it. 

After some refreshments, which I served, we took a tour of the house. While in my living spaces, Antonio remarked on the impromptu hair salon adjacent to my bedroom. 

“Oh, do you like it?” Nicole asked. Perhaps you’d enjoy coloring and styling Rhonda’s hair one day. Quite possibly next month, when my husband and I take some quiet time together at our beach house, you and Rhonda could get to know each other much better. I know Ginny will be visiting some friends and possibly Brett will take off. You’d have the house too yourself,” Nicole said teasingly to our hairdresser. 

“Oh, I think I’d love to beautify Rhonda. More or less make her over to my tastes,” Antonio remarked. Stepmother bade us to go into the living room so she could take some photos of “The Happy Couple” for father to see. I couldn’t wait. It wasn’t until Antonio, with mother’s prompting, put his arm around me and held me cheek to cheek, that I become conscious of just how weak and kittenish I had become. 

Although Antonio was no Hercules, he was definitely strong and fit. From conversations I had overheard at both the salon and the estate, he lifted weights, ran, and played racquetball. I on the other hand never lifted anything heavier then a basketful of wet laundry. As for exercise, all I did was to flatten my tummy, and firm up my boobs abs and hips. 

I was 5 foot ten and weighed a prissy 125 pounds. One would say I was willowy. Even with my heels on, Antonio was an inch or two taller then I and a solid 75 pounds heavier. At this point in my life an average sized male would frighten me, if one had made a pass at me. Where someone Antonio’s size were concerned I was absolutely horrified. 

I’d never felt so vulnerable or intimidated by a human being in my life. With him squeezing me against his body and pressing his cheek to mine, I was of the opinion that he could pick me up, carry me off and throw me down helplessly upon a bed. Even more humiliating was mothers comment to him and his reaction to the comment as we left. 

“Please Antonio. Rhonda is not to have any alcoholic beverages whatsoever. I must warn you; if she does she turns into a slobbering, dizzy slut. You’ll be absolutely mortified by her behavior,” stepmother warned. Antonio laughed and patted me on the but saying that he would keep me in line. 

On the drive to the restaurant he told me about himself. It was going to be difficult using money to get him to assist me. He had owned a salon in Italy and sold it before coming to the U.S. He had invested the handsome profits wisely. His position at “Salon Demure” was that of silent partner, consultant and financial advisor to Nanette. 

At the restaurant we were treated like royalty. I was “Miss Hampton” and he was Mr. Molino. All of the help and many of the customers knew I was Antonio’s date and somehow related to Patrick Hampton   of the Hampton Estate. 

After dinner he asked if I would enjoy a ride along the beach. I agreed and planned to use this time to approach him about his assistance. As the car glided along the coastal road I began to ask him what his designs were concerning me. 

“I find you an enchanting creature. I would say that I would like to date you, court you, win your favor and of course have a loving affair and relationship,” he smiled. 

“Do you mean you would consider an encounter with me?” I gulped. 

“Of course I would. Why? What were you thinking of?” 

I paused momentarily considering my options. If my father failed me I would need this man as a back up. “Well Antonio, I’d consider it, especially if your heart was set on it. Not this evening of course but at a later date. However, I would expect something in return,” I added coyly, with an air of mystery and coquettishness. I wanted to puke. 

His eyebrows raised, he glanced at me with a smile. “Well, I did not think you would give up so easily. What I am interested in, however, is your price, so to speak. What do you expect in return?” He asked. 

Calmly and choosing my words carefully, I said, “I would want your assistance in escaping the clutches of my stepmother and her friends. I want you to help me to get away to my real mother and escape my feminized slavery. I will reward you handsomely with money from my trust fund,” I added for effect. 

At first I thought I had shocked him as he seemed to shiver and shake. Then he composed himself and said, “It could be arranged, but not right away. We would have to have several trysts. Not only for my pleasure and satisfaction, but to impress your parents that we are a serious couple and that we can be trusted to go away together for a few days. It’s the only way, Rhonda.” 

It seemed to make sense. We discussed the various options and decided to wait. I was glad for that. I still had to work on my father. Then, possibly, I wouldn’t have to prostitute myself. Arriving at the front of the mansion, Antonio pulled me to him and said, “We should kiss my pet. We have to begin our charade. Trust me. The ladies are watching.” 

Closing my eyes and praying this were a nightmare I not only let him French kiss me, but I tried my best to convince him and anyone watching that I was serious. Both Nicole and Ginny, teased me unmercifully as I entered the house. I spoke to them as long as I could before lying about having to use the toilet. Rushing into my room, my heels clicking on the parquet flooring I closed the door, threw myself on the bed and cried my eyes out. 

This had to be the worst night of my ordeal and it would only get worse if my father would not come to my rescue. Time would tell and the time for his return was less then two weeks off. I had no idea how he would react to me being “daddy’s girl.” 

Nine: Run, Run, Rhonda! 

My father had flown into the nearest major airport late on a Friday afternoon. He would spend the night before resuming his trip home Saturday. He arrived at our airport, mid morning Saturday. Nicole had been picked up by the company limo driver and went to the airport to meet him. 

I had been dressed in a bright burgundy mini dress, with white polka dots and built in petticoats. My waist was cinched to the max. My hair was in a curly bubble like bouffant with a large white bow. My white heels and sheer hose completed this fussy ensemble. I was truly made to appear as “daddy’s girl!” 

Ginny and I awaited his return at the mansion. I was seated again in the hall, adjacent to the sitting room. From here, on cue, I would make my grand entrance. Just prior to father’s arrival, Ginny added two more accessories to my glorious confection. It wasn’t bad enough that my dress had short, puffed ruffle sleeves a lacy froth in front and a gauzy frou-frou at the hem. 

No, of course not. Ginny had to add a teeny drawstring purse, the drawstring of which she fastened to my right wrist. Over my left wrist she put a sissified wrist corsage, christening me, “Little Miss Sissy Wrist Ribbon” when she was done. 

I stiffened when I heard father, stepmother, Brent and the driver enter. After sometime the driver left and my family seated themselves in the living room. After some chatter I heard father say, “Well Nicole, I think it’s time I meet this new daughter of mine.” Nicole said, “Why of course Patrick I’ll call for Ginny.” 

Ringing the servant’s chime that she kept handy, Nicole called out for Ginny. Virginia bade me to remain seated and entered the living room. Referring to me Nicole said, “I believe it’s time your charge was presented to her father.” Retuning to the hall Ginny helped me up and had me follow her a couple of steps behind as a proper young lady would follow her mademoiselle prior to an introduction. 

Mincing behind her, both my wrists held limply in the air, I felt quite the fool. After entering the living room and at a prearranged spot, she stopped and said, “Miss Rhonda Hampton of Hampton Estate’s everyone.” She held out her hand in a dramatic gesture as I curtseyed and greeted both my father and stepbrother. 

“Father, Brent, we are all so thrilled that you are back. I hope you both like the way I look. I’ve been preparing myself all morning and I’m so excited,” I exclaimed in an “I do declare,” southern belle fashion. I ended up with my limp wrists, daintily at my sides, posing and preening by turning my upper torso and head from side to side, this way and that. 

What a ridiculous overdone sight I must have made! I could barely make eye contact with anyone but I saw that although father was taking this in stride, Brent was aghast that I could appear so femininely compliant in such a short time. Father got up. My mentors had told me what I might expect him to do. I was prepared. “Well let me see. Let me take a good look at you Rhonda. My but you have certainly become a pretty young lady in my absence!” He said as if her were the proud papa. 

Nicole prompted me, “Rhonda, pirouette for your father darling so he can get a good look at you dear. Fix your hair in back baby.” I complied immediately as I always seemed to lately, finishing off my pirouette with a flourish and fussing with my coiffure in back with my left hand, fingers spread. This gesture was accompanied by me batting my big blue eyes and smiling at daddy. 

Posing insecurely directly in front of him I nearly dropped in my tracks when he moved towards me took me into his arms and pecked me affectionately on my cheek. “You look fantastic Rhonda. The clothes, your hair, your makeup. Your behavior is impeccable. Nicole, Ginny, you did a fantastic job!” He exclaimed, hugging me again and pointing for me to sit next to Nicole. 

Ever the loving stepmother, Nicole patted my knee and also gave me a peck on the cheek and a hug. Brent stared open mouthed before breaking into a grin. Nicole then had my put my little clutch purse next to her on the couch before sending me off with Ginny for refreshments. Returning I served father, Brent and Nicole before being given permission to sit and imbibe with everyone else. 

My fare was slightly different. First off my helping of finger food was half of what anyone else had as I was “watching my waistline.” Also I had mint-iced tea and everyone else had white wine. Nicole didn’t want to have a drunken whiny slut on her hands. Brent said nothing to me directly as he and father recapped some of their European adventures. 

I said nothing to anyone. I felt like an air headed bimbo. On the other hand, both Nicole and Ginny showed great interest and when the time was right, interjected both intelligent questions and comments to both men. I sat there stupidly, nodding my head and smiling, offering nothing to the conversation. 

What a relief when I was sent off to the kitchen much later to put on an apron, and cook and serve dinner. Not until bedtime did Brent say anything to me. Even then it wasn’t nice. I was brushing my hair and seated in front of the vanity wearing a lacy peignoir when he entered my boudoir and seated himself on my bed. I shivered in apprehension, knowing this was going to be stressful. 

“My but how the mighty have fallen. This is unbelievable. When we got to Europe and your father told me the plan, I never dreamed for a minute it would be a success. I was nearly blown over though when he said it was not only working but that you had succumbed in record time,” he smiled, before going on. 

“Look at you! They turned you into an absolute screaming, prancing queen with hardly any effort! Are you some sort of fag? Well, I for one am thrilled. By the way Sis, I hear Phyllis Lane is hot for me. Well the feeling is mutual. What a pleasure that will be, dating her while you frolic around in your frilliest apparel and we kiss and neck right in front of you. Mom is going to have you cook and serve dinner to us,” he said with glee before leaving the room. 

This did it! All dad had talked about was the great job Nicole and Ginny had done. Well, I couldn’t bide my time any longer. Tomorrow I was going to confront him. Boy, did I ever confront him. He was in his study, Sunday afternoon when I knocked daintily and asked, “Daddy, could I speak to you a moment?” He actually answered me, “Why of course princess, as long as it’s important.”  

I certainly looked the part of a rich man’s “princess”, what with my poodle skirt, white neck scarf and a big bow in my feathered hair. I began by telling him that I had really learned my lesson and that I thought it best that I now be allowed to go back into society as a male. He frowned almost immediately before telling me it was out of the question. 

“You’ve hurt to many people in the past. Too much time and effort has gone into this. I think you should go to your room and read so women’s magazine and we should not tell your stepmother about this,” he said before I made the mistake of raising my voice. 

“Father, I don’t believe you! Has Nicole told you she’s having me date a man? He’s a hairdresser, of all things. You can’t be supportive of that can you?” I asked before Nicole entered the room to ask what was going on.

“Rhonda is misbehaving Nicole. She’s trying to talk me into letting her return to the status quo. As far as I’m concerned, she will remain Rhonda for two more years, until she is 26 and she can have her trust fund. As for dating men, that is what females do, Rhonda. Would you please take her to her room and discipline her?” He asked as he dismissed me with a wave of his hand. 

Ginny had heard the commotion and I was soon half struggling and half crying on my way to my room. To add to my indignity, this time they hog tied me and gagged me with a soiled pair of panties before paddling me. They even invited both dad and Brent to watch. Neither was much interested, though they observed for a few minutes before laughing and joking about “leaving the girls alone while they have fun.”

I was put to bed, diapered, in rubber panties and tied spread-eagled for the evening. I knew full well now that Antonio was my only resort. For that I would have to pay the price of my virginity to a man. I was willing to withstand this worst of indignities for my freedom.

Already I was planning on getting Antonio over the house for that hair-coloring thing Nicole had mentioned. I was disappointingly certain that the encounter would be only the first of several sexual trysts before he was willing to aid me. I fearfully wondered how many would be enough for him? 

End of Part Three 

Please be patient. Part 4 will complete the story. It won’t be long in coming. So stay tuned for the surprise climax of the “Subjugated Step Sissy.”


Sissy Girl Stories