Subjugated Step Sissy (Part 4)

Ten: Hair Today 

Getting Antonio to the house would be easy. The rest, especially the lovemaking, would be difficult. At the time, mother and father were preparing for a getaway to reacquaint with one another after father’s long absence. Ginny was planning on visiting family. Brent and Phyllis Lane, who had been dating for a month or more, were also going off for a four-day fall weekend.

Because it was still felt that I was no longer trustworthy, Nicole had discussed hiring a Sisterhood professional mistress named Kimberly to keep me in line during everyone’s absence. She’d been talking this woman up ever since I’d served dinner to Phyllis and Brent a couple of weeks before.

Because of my scene with daddy the day after he’d arrived home, I’d been put on what the Sisterhood called “indefinite behavior modification.” I was restricted to the house, and made to perform the most menial and undignified tasks that could be found for me to do.

For instance, a few days prior to Phyllis and Brent’s dinner date at the mansion, Ginny took me to the laundry room and pointed to a basket on the floor and said, “All of those under things and hosiery are to be hand washed, line dried and put away Rhonda.” Hand washing of ladies intimates was nothing new to me so I didn’t bat an eye until I’d picked up the basket.

The underwear and “hosiery” were men’s socks and underpants and belonged to Brent and father! How awfully humiliating! A while later I was positioned over the washbasin scrubbing stains out of underwear belonging to the two “real men” of the house. The socks were no less smelly or degrading to wash. In addition, once finished with these items I was marched to the sunroom where I was given several pairs of men’s shoes and the appropriate shoe polish.

“Sissy Suzie the Shoeshine Girl,” Ginny christened me as she laughingly went her way. Worse yet it was made known to both Brent and father that I’d performed these demeaning tasks. Father was actually complimentary on the shine in his shoes and the cleanliness of his underpants. Brent however used the information to embarrass me even more.

The night of their dinner date, I was dressed in my fussiest taffeta maid’s dress. I’d been made to fix my hair in kinky, springy, jelled curls. The dining was intimate and I was instructed to speak nary a word or pay terrible consequences. I minced about the table serving my ex girl and my stepbrother. Phyllis remarked on what an “exquisitely girlish servant” I made. Brent of course told her that the socks and underwear he wore had been hand scrubbed by none other then little old me.

“Oh how nice! What a wonderful sister you are Rhonda!” Phyllis exclaimed. “Brent? Should we ever get a place together might we hire Rhonda for a day or two a week for some housekeeping?” Brent didn’t miss a beat, showing Phyllis his shoes and remarking, “She puts a nice shine on a pair of shoes also. Why don’t you drop off several pairs of yours the next time you’re in the neighborhood? I’ll see to it she puts a nice spit shine to them,” Brent recommended to his new lover. It was with much trepidation that I approached Nicole about a weekend “date” with Antonio.

It was right after Tuesday breakfast. The family was planning on leaving for their weekend excursions Friday of the following week. “Mother Nicole? May I have a word with you?” I inquired politely. She stared at me for a short while before saying, “This had better be good Rhonda.”

“May I ask if it would be all right for Antonio to come to the house and do my hair next weekend? You had mentioned it once before and I think it would be a fun time especially if he stays for the entire holiday,” I asked cheerily.

Nicole again scrutinized me before asking, “Do you really want Antonio to come here, or are you trying to avoid a weekend of chastisement with Mistress Kimberly?” She asked.

I didn’t want to make her suspicious so I said, “Some of each I think. I do miss Antonio, though, and think about him a lot. He really was fun to be with on our only date and I’d love to see him again if you and daddy approve.”

She waited a while longer and said; “I’ll do the phone call to him. You just be patient. He may not be able to come for the whole weekend. It would do you good, anyway, to spend some time with Kim. She’s a very stringent authoritarian and I think you’d appreciate how easy you have it here after she was done with you.”

Nicole let me sweat, and finally Thursday after breakfast she told me, “You are a very fortunate young lady. You are just so lucky to have Antonio for a boyfriend. Not only will he be here for the entire weekend; he is rescheduling quite a few appointments to give you his undivided attention. He must really think quite a bit of you, Rhonda.”

I’d also be spared any sort of “seminar” with the very exacting Ms. Kimberly, though not other indignities. I was told that a visit to the mansion by Dr. Bordeaux would be necessary. Apparently, “special” girls like me need unique preparations before being with a man in an intimate way.

The doctor arrived on the following day with another “special” girl named Katy. Katy and myself went into my room where she told me what it would be like to be with Antonio and why this distinctive preparation was needed. By the time she had finished my head was in her lap and I was bawling. My emotional dam had burst.

Once Katy got me under control she went to get the doctor, Nicole and Ginny. After I had changed into a very brief Teddy, I was helped to mount the massage table and Ginny began an enema. I was filled to nearly bursting before I was allowed to hold it in for five minutes, and then permitted to run to the bathroom to expel it.

That wasn’t all. To make sure my colon was fully cleansed, I was then given a thorough extensive colon cleanse. It took quite some time before Dr. Bordeaux to pronounce me “completely evacuated.” Now the next portion of my “prep” would take place. After an extensive lubrication of my rectum with petroleum jelly, performed by Ginny with a surgical glove; Dr. Bordeaux instructed Katy on inserting a “training plug” in my anal canal.

It was not very comfortable but it finally went in. Then the good doctor let me in on the rest of my torture. “We’ll increase the size of this butt plug very couple of days. We’ll also put you on a strict diet so you won’t need to go until Friday morn.” Oh, great, I thought. During the next week, my plug was removed, I was allowed to evacuate if needed and a new, bigger, heavily lubed plug was inserted.

This took place every two days, on Sunday, Tuesday and Thursday. On alternate days, Ginny came in my room each evening, wearing a strap-on and had me suck away to my hearts content. In the words of any Sisterhood member I was being “Slut Trained”.

“A slut trained sissy maid is a valuable commodity in the Sisterhood,” Nicole explained. “None of us really like to perform oral or with a male. That’s why all the ladies would rather have a slut-trained maid. When their man gets randy and wants some oral or, the sissy can serve as a surrogate lover and perform these necessary duties as part of her obligations,” she stated.

Antonio arrived on Friday morning just prior to everyone else’s departure.  My plug had recently been removed and I had taken a bowel movement. He shook hands with dad and Brent. Father even told him to “take care of my little girl.”

Both Ginny and Phyllis winked at me as they left and even Nicole had some kind advice. “Take good care of your man Rhonda and he’ll take care of you,” she whispered in my ear as she pecked me on the cheek. Once everyone was gone, Antonio took me by the hand and we went to his car. I was dressed in a taffeta hoop skirt, high collared white blouse, with dark stockings, garter and panties, three inch heels and of course, no gaff, as to be “accessible” to Antonio.

My hair was actually netted as I’d slept with a leave on conditioner in my hair in preparation for my coloring. The makeup I wore was subtle with regards to getting a makeover. “Okay my little maid, you may help me with my luggage,” he said as he opened the trunk to his Mercedes.

He had two small suitcases, an overnight bag and his hairstyling valise. It seemed like quite a bit for a 4-day weekend. I was given the valise and overnight bag. When I asked where I should put them he laughed.

“Put them in your bedroom my princess. You don’t think I came over just so we could sleep in separate beds? You belong to me for four days my dear, silly girl and I intend to make it interesting for both of us,” he chortled. I had extra dresser and closet space so I put his things away after we’d reached my room.

Almost immediately after I’d unpacked his things he said, “Let’s get started on those lovely tresses of yours my little Bambi. Now let’s see, where do you keep your capes? There? Ah, this looks like an interesting one,” he said as he held up the very restrictive style cape that Nanette was so fond of using.

I gulped and asked politely if we could use a normal style. After all, I’d been the one who had shown him where to find the capes. “No Muffin. I don’t think so. No, if I were you I’d put that cape on right now. No hesitation my dear. You don’t want to wind up over your Antonio’s knee getting spanked now, do you?” He asked, holding the cape out towards me.

This was ridiculous! The silly little nicknames he’d been calling me. Now he wanted me to wear that dreadful cape. In the past I would have at least tried to resist him. At least insist he show me some respect. However, my most effeminate physical condition, combined with my docile mental state disallowed any struggle.

I meekly took the cape and lowered it over my head, sliding my arms into the built in, hidden, inner sleeves. Turning my back to Antonio I timidly capitulated to him as I presented myself for being cinched in. He tied the sash in the rear of the cape most tightly, restraining me in as if secured by a straight jacket.

“Now, that’s much better. I really don’t like girls who put up any kind of fight. My type of female is one who submits dutifully to my every whim. Good choice, Missy. You know how to please your Antonio already. Let’s shampoo that head and tint those curly locks of yours. After we make you beautiful for your Antonio, I’ll show you how to please me even more,” he chuckled.

Placing his hand at the small of my back, he carefully guided me over to the shampoo sink. I fairly wobbled on my tall spikes, especially since my arms were highly immobile and unable to provide balancing stability. Reaching the chair in front of the wash sink I slowly pirouetted, before carefully sitting in the lounging chair. My loving stylist gently propelled me back further into the chair, before removing my hairnet and turning on the rinsing water to begin my shampoo.

The warm water and his strong hands relaxed me as he massaged my shoulders and my scalp. Once my hair had been shampooed and crème rinsed, he wrapped a towel over my head before seating me in front of the vanity. He again massaged my neck shoulders and scalp, before he initiated my cutting.

As he snipped and sectioned my hair he very casually told me how attractive he found me. He also kept bussing my cheek with his lips and finally took little pecks at my lips. I was getting scared. Then he asked me if I’d like a little herbal iced tea that Ginny had mentioned leaving in my icebox. After I sipped a good portion of the glass it dawned on me I had been none too wise.

I was 100% correct. I’d been mildly drugged. Drugged to the point at which his advances seemed cute and romantic. As he foil wrapped my hair he proclaimed loudly about the beautiful iridescent burgundy shade he’d chosen for my dyeing.

As he painted it on, the drug from the herbal tea indeed relaxed me. So much so that when he sat me under the dryer I fell off to sleep until the buzzer woke me. After a condition and rinse he began my blow-drying. By now I had had a second and third cup of this wonderful tea and the whir of the hand held dryer, the warm air and the perfumed scent of the hair color all added up to a sensual feeling.

These things and the attention Antonio paid me made him desirable for the moment. He dried, sprayed and styled my hair into a teased and windswept pouf. The burgundy hue shimmered in the light of the vanity. Then he did my makeup, making certain it was luxuriant, flamboyant and striking.

Standing me up and posing me in front of the mirror he said, “How very beautiful. Look at yourself Rhonda. You are a lovely girl. You were born to be my girl. I want you very much! Shall I take you now, bound and helpless as you are? Or do you want to please me by participating? I understand you’ve been sufficiently prepped, though I have a few things I could teach you.”

I could barely believe what I next did or said, as I turned from the mirror. Facing him and in my inebriated state I pushed my breasts into his upper body, saying in a sultry flirtatious voice, “You can have me tied and vulnerable or you can unbind me and I can show you real pleasure. You may teach me anything you like.” Nicole had been correct. Put any type of mood altering substance in my system and I became a wanton hussy.

I was as brazen as they came. Antonio smiled and reached underneath the cape and unbound and released my arms. He helped restore circulation by massaging my arms back to life. Putting my arms around his neck I asked him nicely, “Please be patient. I’m very new at this.” He picked me up and carried me to the bed, depositing me on my back and unbuttoning my blouse.

I had no idea I’d become such a slender waif that I could be picked up and helplessly deposited like that! Opening my blouse he turned me on my side, unfastening my bra. Removing it he returned me to my back before he climbed atop of me and mouthed one breast, then the other. My nipples had really become sensitive!

My back arched in surprise and Antonio laughed before smothering my heavily painted mouth with kisses, and sticking his tongue practically down my throat. I found myself getting hot, and didn’t try to resist as he took off my shoes, panties, and bra, pushing me full up on the bed.

Kneeling on the bed himself, after removing his slacks and underwear he motioned for me to come near. He was fondling his very large penis and I knew instantly what he expected me to do. “My princess, you should pleasure your prince now. Put those creamy red lips of your’s around my organ and begin tasting me. Come along now; Please your man, my angel,” he said as if I did this every day.

Tentatively I crawled to him, positioning myself yogi style before taking him first in my hands and guiding him into my mouth. Even under the drugs, this would be difficult, but I knew it was necessary. In order to convince him to help me, I’d need to please him fully.

I began to suck, lick, and fondle his penis and genitals. I slurped it in and out of my mouth as Ginny had taught me. I paused to take it out, kiss his balls and look up into his eyes sexily. He was quite big and as I sucked him off he grew bigger. He began to pant heavily and said to me, “Don’t worry my sweet. I don’t intend to cum in your mouth this time. We’ll save that treat until later.”

He held my head from behind and guided me through the every step of the way. Stopping me he then directed me to face the headboard of the bed and hold on to it. I knew what was coming and I tensed. “No, no princess, you need not fear me. Even though I’m absolutely huge, you’ll be well lubed and so will I,” he cautioned me.

I felt his jellied finger enter me from behind and lubricate the walls of my anal cavity. Then he stepped off the bed and covered his penis with the same creamy jell. Getting back on the bed he mounted me, wrapping his arms about my breasts as he entered me from the rear. He did it slowly but when I stiffened momentarily he swatted my butt.

I yelped and as I did he entered me, pushing his member inside me to the hilt. Slowly and carefully he rode me, alternating between massaging my breasts and my own genitals. I whimpered enough when he touched my genitals that he said, “Oh, so you like that? I’ll keep it up then.”

Our passions increased together as I started to thump my rear against him. I sensed him getting close and hoped he didn’t finish before I did. Luckily for me, when he stiffened and his penis swelled to max proportions the pressure against my sphincter was enough that I popped like a cork. He spewed forth his semen at the same time and I ground myself into the mattress as he pumped for all he was worth into me.

When he rolled off of me I went to him crying, half out of shame the other out of pleasure. No longer was I a virgin with a man. After a time we both arose and took turns cleaning up. I fixed myself instinctively as any female would and dressed in the clothes I had worn earlier.

“You look very pretty Rhonda. However, after today you will wear around here unless I state otherwise. Along with your you will also see to it that you are in heels, makeup and dressed hair of course. Do you understand me clearly my pet?” He asked with seriousness.

I was beyond rebellion and answered meekly, “Yes Antonio, of course I understand. It will be my pleasure to gratify you. Your wish is my command my darling.”

For the rest of the day I fed him, massaged his feet, danced with him and made sure he was happy. At bedtime he picked out a really frilly bright red teddy for me to wear. As soon as we were in bed he took my hand and placed it on his penis. At first I used saliva to lubricate him, then switched to baby oil.

Once he got really hard he changed position and pushed away the covers, pulling me towards him and pushing my head to his penis. “Suck me carefully angel and when I spurt I want no mess made. You will swallow every drop my lamb. Do you understand darling?” I agreed that I did.

I did as he ordered and as he swelled I closed my eyes telling myself I was doing this to gain my freedom from feminized slavery. He grew larger and larger and my slurping became noisier. His breathing picked dup and I sensed an imminent ejaculation. I was right.

He swelled to the same gigantic proportions as he had when he’d butt reamed me. My impulse was to back away but he was ready for me. “No you don’t my prissy one,” he said as he placed both hands on the back of my neck and head. He wasn’t kidding. He made sure I sucked down every drop of his semen until he was drained completely dry.

“No, you don’t my prissy one”

The rest of the weekend I spent as his sex object, play toy, love dolly. I wore nothing but scanty, frilly, and plenty of tall spike heels, makeup and perfume. 

He only let me dress properly about an hour before the first of the household arrived home. During the weekend, I’d been banged in the rear and my mouth so much that I wore the silly smile of an air headed bimbo, and walked with the pleasure-ridden gait of a sluttish streetwalker.

Everyone noticed it. Though father did not remark he spoke to me very infrequently over the next few days. In contrast to father’s silence, Brent, Phyllis, Nicole and Ginny all had their fun with me. I didn’t dare turn down a date with Antonio after that for fear of offending him and my efforts of that weekend going for naught.

Usually after dinner, dancing a movie etc. we’d wind up at his house or a hotel. No matter where we would up, he wound up with his penis in my butt and mouth. I had become his whore, his concubine. 

Rhonda wearing the collar.

On an afternoon before another date with Antonio, Nicole and the rest of the sisterhood had a small ceremony where an expensive pink jewel dog collar was locked around my neck with the Black Rose emblem of the Cassandra Sisterhood and the word "Sissy" below.


Behind the tag it read "Antonio," it was The Cassandra Sisterhood's way to remind me that I was their submissive property and Antonio's "Trophy." No matter what I wore, whether sexy or demure the collar stayed on me though, Antonio thought my family and the sisterhood would't mind seeing a symbol that alluded I had been conquered by him. 

When it came time to see Dr. Bordeaux for my monthly check ups at her clinic, she was happy to see that I was adjusting well in my new feminine role. 

"I can see you are having a healthy relationship with you boyfriend Rhonda," she said smiling while she moved her latex finger inside my rectum. 

Finally, as the months grew cold into winter, I asked when we could make our break. “Soon my sweet girl, soon,” he would say.

Rhonda having submissive sex with Antonio.

I finally pinned him down to a weekend trip. We told my parents we’d be going to his vacation house. They agreed. He picked me up on a Friday afternoon. Everyone was gone for the day. We’d drive until after dark and actually stay at the house, which was about 3 hours away. Never having been there I had no idea where we were until we arrived.

I’d packed a weekend’s worth of girly clothes and stuff, though I planned on wearing none of it ever again. Antonio had brought male clothing for me. I couldn’t wait to get out of the hated stuff I was wearing and put on normal clothing again. After resting for the night we’d continue on to my real mother’s house.

We got out of the car, took some luggage form the trunk and made our way to the door. It was very dark. Once inside I set my luggage down. Antonio shut the door and turned on the lights. The shout of “Surprise!” reverberated throughout the house. Behind me Antonio squeezed my arms together and as I struggled he managed to bind them with a scarf and hold me still.

In the room were Nicole, Ginny, Anna, Nanette, Phyllis, Natasha, Doctor Bordeaux, and my real mother, Paulette! They moved towards me. As I whimpered they took hold of me, Giselle Bordeaux preparing a syringe, which she injected into my arm. My crying stopped as I swooned into their collective arms.

I awoke strapped to a table surrounded by these same ladies though now Dr. Bordeaux and a few others were actually dressed for what would appear to be surgery. Oh my goodness, my surgery! Nicole was going to carry out her threat of several months ago. I was going to protest but when I did, I found my mouth was taped shut.

Instead, Nicole spoke out. “Rhonda, that was a nice try, but thanks to Antonio’s loyalty and his good sense, we found out in time to foil you. Antonio knew better then to cross the Sisterhood. He realized he’d lose a little more then his job with Nanette. Also dear, your offer paled in comparison to the reward he got from the Sisterhood for turning you in.

She and the other ladies laughed as Nicole added; “ Now it’s time for you to pay the piper Rhonda. I believe the preset penalty was the loss of one testicle. Prepare to become half an eunuch dear.” I squealed like a stuck pig as Giselle approached me with a shiny scalpel in her hand. I squealed louder when the doctor told Anna to prepare a “local” anesthetic.

Thankfully, at the last minute, Nicole asked everyone to leave the room. She cautioned me to speak civilly as she prepared to remove the tape from my mouth. As soon as she zipped it off I begged her to spare me and promised to do anything. “Really?” She asked. “That’s perfect. You see your father plead your case several days ago when Antonio tipped us off. I approached the council and they agreed to forego the 50% castration as long as I’d come up with appropriate punishments,” she stated.

“So, for the next two years you will not live in our household and I’ve come up with three choices for you. After your chosen sentence is up you may have your trust fund and your identity as Ron. Choose wisely my dear, as your future is at stake,” she said as she gave me my three choices.

Eleven: Maid in Head 

I finish up my nails just in time. As I look at the clock I see that my lover will be home in less then an hour. I put on a frilly apron and check the roast in the oven. Interested in my three choices? Want to know which one I picked? I thought so. My first choice was to continue on to my real mother’s.

Considering that my mother, Paulette, is a plastic surgeon, part of that deal included a boob job and having my nose bobbed. With my red hair, I’d be a button nosed bimbo, with a small waist. I’d appear to be, more or less a latter day Anne Margaret. One of my duties would be servicing mother’s new boyfriend a 25-year-old landscape architect named Cody. It seems mother doesn’t like oral or and Cody does.

 I decided to pass on that one. Second choice was becoming a whore’s maid in a bordello. It seems a local madam wanted a sissy maid to wait on her girls and be handy for customers with weird tastes. It was getting scary but again I passed. I came real close to losing one of my balls.

My last choice was being part of Antonio’s reward. As much as I despised him for betraying me and using me, I felt comfortable with him. Besides, I was ready to use him also to aid my mistake. So for the time being I’m Antonio’s whore.

I cook his meals and clean his house. I wait on his friends wearing the skimpiest of outfits. I sleep with him when he wants me to and wait on him and his many lovers if he brings someone home.

He keeps me in sheer and shows me off to everyone. Once a week I doll up and accompany him to Salon Demure where I work as his assistant. You name it; I do it if he tells me to do it. I’m his complete slave.

What will I do when my time with him is up? I’ll be Ron again. No problem, right?

The End?

Hoped everyone found pleasure in this literature classic. I will be (like all stories featured on this blog) adding art to this tale soon. If you enjoyed this story please take a moment to leave comments below. We would love to read your thoughts
-Annabelle B