Born to be Beta (UPDATED)

 A Cassandra Vignette of Stern Dominance 

By Priscilla Bouffant

My trust fund was frozen. I was in enough legal trouble to be sentenced to two years at the county detention facility. Pretty boys like me did not remain boys for long at such an institution. Three years probation as my older sister’s personal maid and Lady’s Companion was the alternative.

Chapter I: Lunch Will be Served Madame

     I minced very daintily along the tiled floors of the mansion. The clicking of my tall high heels echoed through the halls. I carried a tray with the energy drink, which my older sister Caitlin, had for lunch every day. Unless, of course, she was dining out with one of her “Sisterhood” lady friends or her new live-in boyfriend, Master Phillip. 

    I wanted to broach the subject of Master Phillip with Caitlin, if she would allow me. I found her in the library, looking over some papers. I curtseyed at the doorway, and I whispered softly, “Madame?”

   She looked up from her reading and then stood, extending her hand.

    “Ah yes. My lunch. You may enter, Andrea Maria. You will also wait for me to drink the beverage. Then you can return both the glass and the tray to the kitchen,” Caitlin said, as she began to sip her energy drink.

    This was Caitlin’s way of staying imperially slim and svelte. I didn’t dare to call her Caitlin. She was “Madame” these days. And I was no longer Andrew. I was now Andrea Maria. In many European nations I had been told, Andrea was often used as a boy’s name. As was Maria used, semi-frequently, as a boy’s middle name. Andrea was pronounced, “On-Dray-Uh,” with a definitive Eastern European accent. 

    Of course, I fully realized the combination of the two traditionally feminine names were designed to shame me. As Caitlin sipped, she relaxed and closed her eyes. I was nearly frightened to interrupt her. But I did.

    “Madame. May I speak to you on a matter of concern, please?” I asked.

    “Andrea. Can’t you see I’m in contemplation as I imbibe in my refreshment? Must you be such a mindless twit? Wait until I’ve completed my beverage, please?” Caitlin fussed.

    It was several moments before she finally took the last sip, opened her eyes and handed me the glass. I stood waiting. She glared at me.

    “What on earth are you waiting for boy? They’ll expect you back in the kitchen soon. Won’t they? Is there something you want Andrea?” Madame asked.

    “Yes, Mum. I had asked you, if I may speak to you on a matter of concern, ma’am?” I fumbled.

    “Of concern to who, Andrea? Should I be concerned about something? Is this of concern to you?” Caitlin asked.

    “Yes Mum. It’s a concern I have, Mum,” I dithered.

    “Well out with it boy. What is it?” Caitlin asked.

    “Well ma’am, I wondered if Master Phillip realized I was not a real girl ma’am?” I asked.

    “Do you mean does my Phillip know you are an effeminate sissy? Of course he does. Even if I hadn’t told him, he’d be able to tell from your nearly flat bosom. But don’t let your bosom trouble you, dear Andrea. The hormones we give you can be increased in dosage, and will allow you to have a very attractive bosom, my darling male sissy-maid,” Madame smiled.

    “If not, we can consider giving you surgical implants. Would you enjoy that dear? Now tell me. What if my Phillip does know you are a sissy? What does that have to do with anything? Why is that a concern of yours? Now. Out with it boy. Are you tongue tied?” Caitlin asked impatiently, as she tapped her foot.

    “Oh. No ma’am. Well, you see ma’am. And I don’t want to carry tales ma’am. You see, Master Phillip has touched me very familiarly on my hips ma’am. And he’s made a number of sexual innuendos. And though I don’t think he’ll make any advances towards me, I’m just concerned ma’am,” I stammered.

    Caitlin laughed and covered her mouth. “Oh my. I see. Come over here Andrea Maria. Get out of the doorway. We don’t want any of your fellow servants to hear this conversation,” Caitlin tittered.

    She began speaking concisely, just above the level of a whisper. “You see Andrea. There are certain sexual acts, which a grand lady, of my elevated station, would find loathsome. For one, I perish, at the very thought of a man’s penis entering any female’s mouth. That is absolutely contemptible. I never intend for it to happen to me. Even more horrifying, and it borders on the most nightmarish of occurrences, would be the sexual organ of a male entering the rectal passage of any woman,” Caitlin gasped.

    “However, Andrea, men continue to desire these most disgusting of demonic transgressions, to be performed for their prurient pleasures. And that is where male sissy-maids come into the picture. So, should Master Phillip, at any juncture, desire the ministrations of oral sex to be performed, I have told him you would be more than happy to accommodate him, Andrea,” Caitlin explained as if I were a dimwitted scullery girl.

    “Similarly, should Master Phillip, call upon you, because he desires anal sex with you, I would expect you to also satisfy him. Now should you prefer to take him to your femininely appointed boudoir, to engage to be pegged by him, or to fluff him, I would hope you’d prettify yourself with a bit more makeup than you are now wearing?” Caitlin requested with raised eyebrows.

    “I’d also suggest that you put on some pretty panties and one of those, very nice nighties I’ve purchased for you. And it wouldn’t hurt to let your hair down from that plain bun, you wear it in, and maybe add some curl to it? Do you have any further concerns Andrea?” Caitlin asked.

    “Oh, no Madame. Not at this time,” I said, stunned by her obliviousness to my plight. 

    “Are you certain Andrea? And don’t be discouraged that Master Phillip’s tool, might be too large for your anus. You do realize, my dear, that the rectal plug the Head Housekeeper inserted for you, isn’t just there to see to it that you walk with a pretty wiggle while in high heels. You do know that the plug is to assure that you’re wide enough should any man desire to take you anally. Don’t you Andrea?” Madame smiled.

    “No, I didn’t realize that ma’am, but it makes sense. Any man Madame?” I asked.

    “Well of course. But all the male employees left our employ once Mother gave over the house to me and moved to Europe with her handsome Spanish Count. So Phillip is the only male here, unless of course, we decide to have male guests that might desire you,” Caitlin opined.

    “Andrea. Please, pay attention to me. Please don’t doubt or hide your innate femininity. There is a sissy within you and that sissy needs to emerge. You can be very pretty, if you take the time and effort to beautify your self. I could have my hairdresser assist you, the next time she’s here to give me a makeover. I don’t mind at all. She won’t either,” Caitlin added.

    “Yes ma’am. That would be very nice of both of you,” I said.

    “Well wonderful Andrea. I’ll send for you the next time my coiffeuse is present here at the mansion. Run along now. The head housekeeper will be looking for you,” Caitlin said.

    I could scarcely believe what my ears had just heard. My older sister was more than willing to have me used as her lecherous boyfriend’s, sissy-slut. Or to serve as a slut for her male guests. I was now no more to her, than an effeminate cum-dump. She’d been so very callous and casual as she’d explained these matters to me. And to what end? To keep herself from partaking in the very same sex acts she expected me to perform willingly.

    And she did it with the same aplomb she might employ when discussing how much starch she preferred in one of her tennis skirts. Now that I knew what Master Phillip’s advances were about, I knew I couldn’t afford to be alone in the same part of the mansion with him.

    But for how long could I possibly manage to do that? Oh, what was the use? In my situation I was fairly destined to play the role of my older sister’s sexual surrogate or the casual sexual fancy of her male visitors. I knew how all of this had managed to happen and realized it was mostly my doing. Though, I had also been deceived to a certain extent.

    My journey into emasculation had likely had its beginnings, when, at age eighteen, at the University, I had begun to spend my trust fund frivolously and fancied myself to be a Lothario. My elderly father had passed away. My mother, Tabitha, who was so much younger than my very, elderly father, had met a Spanish Count, not much older than my sister Caitlin, who was then twenty-three. 

    The young Count was fabulously wealthy, somewhat immature, and adored my mother. They were married, and mother planned on moving to Spain to live with him. She intended to give the house jointly to my sister Caitlin and me. My sister apparently objected. Though I was never privy to the actual conversation, it has since been recounted to me, nearly in its entirety.  

    “Mother, I’d prefer not to share ownership of the house with Andrew. Not until he’s old enough, mature enough and properly wed to a female whom I approve of,” Caitlin demanded.

    “Well, those aren’t terrible terms to abide by. We could take care of all that in the conditions of deed transfer. Is there anything else, Caitlin?” Mother asked my sister.

    Caitlin has admitted to me she was surprised at how easily mother agreed to her terms, so she went a step or two further.

    “Well mother. Now that you bring it up, yes there is. I also want to control the purse strings to his inheritance as well as his trust fund. Only, of course, in the interest of protecting him, from his very own profligate spendthrift ways. Here are my suggested terms,” Caitlin dictated.

    “Andrew must be at least twenty-three years of age and married to a female of whom I fully approve, prior to him being able to assume joint ownership of the Warrington Estate. The identical terms shall further apply to Andrew ever gaining any control whatsoever over his trust and inheritance,” smiled Caitlin.

    “You are a very, wise woman Caitlin. I’ll have to contact the solicitor that handled your father’s will,” mother added.

    “Oh, please don’t trouble yourself, Mummy. I have a dear, dear friend that I trust impeccably to handle this. She’s a member of the feminist society I recently joined. Her name is Hester Byrne, and she’s been practicing Estate and Trust law exclusively for five years now,” Caitlin explained.

    “Don’t be concerned mother. Hester is a legal genius at thirty-two,  and mature, well beyond her years. Frankly, she’s just the type of lady I’d choose to be my younger brother’s marriage partner,” Caitlin surmised.

    “Hmm? Fourteen years older? Truthfully, boys mature so very slowly. That’s likely the perfect age spread. Look at Count Juan Carlos and I, for that matter? He’s twenty-six and I’m nineteen years his senior. My dear, Juan Carlos, does prefer to be mothered though, and that’s such an enjoyable switch after your father’s dominance,” my mother intoned.

    “I’ll gather the papers for you and your friend Hester. I’d prefer you take care of this, so that I can be off to Spain to a life of luxury at Juan Carlos’s villa outside of Madrid. We’re madly in love, Caitlin,” my mother chirped.

    To say that I was furious, simply over my trust being frozen to a trickle, would be an understatement. But when Caitlin explained to me her terms, as well as her present full ownership of the estate, and control of my inheritance I exploded into a rage. Of course, Caitlin ended the conversation.

    Then I foolishly called her back, leaving empty, but vicious threats on her voicemail. I also doubled down with bullying text messages. At my first opportunity I left the University and drove to the estate where I found all the locks had been changed.

    From an upstairs window, Caitlin warned me to go away before she notified her security staff and the local police. I sneered. I then found myself being restrained by private security and finally being arrested by the county police. I was charged with assault. 

    At my hearing, in front of a female justice, the text messages, voicemails and my verbiage, witnessed by the security staff were entered as evidence. The county prosecutor was also a female, as well as my Public Defender, Hester Byrne. I couldn’t afford my own private solicitor.

    Though I was sentenced to two years in the County Detention Center, the Prosecutor offered probation.

    “Your honor, the state will extend the option of probation to the accused,” the prosecutor added.

    “I see. And what are the terms the state offers to the accused, Ms. Phelps?” Judge Carstairs asked the prosecutor, Edna Phelps. 

    “Three years probation supervised by the state and the accused’s sister, Caitlin Warrington. Andrew Martin Warrington will serve as his sister’s Sissy Maid and Sissified Lady’s Companion for the term of three years,” Edna announced.

    The hearing was private, so the only audible gasp was mine. I wanted to shout. However, the Bull-Dyke serving as the bailiff glared at me.

    “Will the accused approach the bench?” Judge Carstairs said.

    I froze. Behind me, Hester Byrne pushed her right hand firmly into my shoulder blades.

    “Move, you stupid little bitch. Are you deaf? Walk to the Judge and get close enough to touch the bench. Now, you dimwit?” Hester hissed, barely speaking above a whisper.

    I did as I was told. Hester walked along with me, her hand still snugly against my back.

    “Yes, your honor. You wanted to see me?” I asked, trembling. 

    At this point, I want to extend a warning to anyone reading this. Do not ever cross or threaten a member of the Cassandra Sisterhood. Additionally, don’t ever put your trust in any member of this mysterious society if you have violated the sensibilities of one of their members.

    These ladies, as a group, have an unbreakable bond between themselves. And they work together for the betterment of each other. As well, they assist one another to achieve their preferred goals. I have discovered this in a way that I don’t ultimately regret. However, my experiences with the Sisterhood, have changed my life immeasurably. 

    The Judge spoke, “Yes, come closer Andrew so I don’t have to raise my voice.”

    Hester, my public defender, shoved me so that my chest was flush against the Judge’s bench. Her firm hand and arm held me there.

    “Andrew. Do you realize what happens to pretty, slim, Caucasian boys such as you, at the County Detention Center? Well, you see? Soon after you arrive, a strong, muscular, weight-lifter sort of hulk, will claim you as his sissy or girlfriend. By that evening you’’ll be having sex with him just as any girl might,” the Judge implied.

    “I recommend that you discuss this with your attorney and see if Ms. Byrne doesn’t recommend that you accept the probation as your sister’s sissy maid,” the Judge advised.

    I turned to Hester questioningly. She signaled to the bailiff that she wanted to consult with me off to the side of the courtroom.

    “I strongly advise that you take the probation Andrew. You won’t last thirty days at the Detention Center before your Bull begins passing you around to be raped,” Hester warned me.

    “Raped? But as a sissy maid won’t I have to wear female attire?” I asked.

    “Of course you will. Possibly, only sometimes, though. However, there is some very pretty androgynous attire you might be dressed in for public display. I wouldn’t be surprised if you aren’t wearing makeup and having your hair properly curled also. But you won’t be passed around as if you were a streetwalking slattern either,” Hester replied.

    I nodded my agreement.

    “My client prefers the three-year probation as a Lady’s Sissy Maid your honor, and thanks the court for their leniency,” Hester advised the Judge.

    Prior to leaving the courtroom, I observed my sister hug the Judge, the Prosecutor and Hester. They all referred to each other as “Sister.” The bailiff put me in handcuffs and my sister Caitlin made me wear the handcuffs until we arrived at the mansion. There I was turned over to the smirking Head of Housekeeping. 

    Even though the Housekeeper, Marta, had the key to my handcuffs she didn’t unlock them immediately. Instead, she shoved me down the hallway towards my new room in the servants quarters.

    “Oh, you’ll never know how much I adore making you sissy-maids look pretty. And I can tell simply by looking at you, Miss Andrew, that you’re going to be a real jewel. Oh. How thoughtless of me. You’re now Andrea Maria. Those were the Mistress’s instructions,” Marta laughed.

    “Let’s get you stripped down and denuded of all that ugly body hair. I’ll take those cuffs off now, dear. Now don’t ever hesitate to obey my commands, or try and get fresh, shan’t we? Those Bull-Daggers the Mistress hired for security, play very roughly. Now you don’t have much body hair do you?” Marta remarked.

    “You even have less hair to remove than most sissies. But you do have a gorgeous head of hair, don’t you? I’ll have to give you a home permanent soon, so you won’t have to fuss with it all the time. I told The Mistress that the girls and I will just love giving the new sissy a home perm,” Marta explained.

    I watched what little body hair I did have, wash down the shower drain. I was toweling off when both Ms. Marta and the head maid, Elspeth came into my room. Ms. Marta held a bottle of moisturizer and Ms. Elspeth had a container of body powder. I quickly covered my penis with the fluffy pink towel I held.

    “Oh don’t be a modest little sissy Andrea. You don’t have anything we haven’t seen before," laughed Elspeth as she pulled the towel from me laughing.

    If that wasn’t humiliating enough, both women covered their mouths and burst into laughter at the sight of my family jewels.

    “Well I thought I’d seen it all, Elspeth, but that’s the tiniest penis I’ve ever hoped to witness, on any, nearly nineteen year old boy,” sniggered Marta.

    “Indeed Marta. It looks something like a penis, only much, much, smaller. More like what you might think you’d see on an eight-year-old. And if you clipped the sissy’s nuts, I don’t think sissy would miss them one bit?” Elspeth screeched.

    “Now hold still sissy. And stop being a prude. We’ve got some nice scented lotion, and prissy, smelling powder we’re going to put on you. Mistress said the new sissy maid is to smell as flowery as a Parisian  homosexual,” Marta added.

    Marta got very familiar with me, as she applied the body lotion. After Elspeth powdered me with the large puff, she rubbed some warm, perfumed  oil into my tresses and wrapped my hair with a bright-pink scarf.

    “Slip into this garter belt and slide on that panty brief. Then put your feet into those fluffy pink slippers. Now, just waltz over to the new fitting room, which The Mistress recently had constructed. It was renovated, especially for you, Andrea. Then walk your skinny, dainty ass to the top of that lacing pedestal. Your to be corseted quite snugly for obvious disciplinary reasons,” announced Ms. Marta.

    Having a bone-crushing, waist-tightening, figure training corset, wrapped around my slender frame, and snugged to the tiniest of dimensions, caused me to nearly faint. While I was still hanging from the lacing bar by my manacled wrists, Elspeth slipped dark hosiery over my sleek, lotion-scented legs.

    Then Marta slid a pair of kitten-heeled, “Princess” footwear onto my feet. The Princess shoes had what amounted to two-inch heels, with a modest wedge-type arch. At least these weren’t a set of those  horrid “spikes.” Yet, I still struggled to walk “effeminately perfect,” according to both Ms. Marta and Ms. Elspeth.

    “It’s as if we’re trying to educate a cowboy-boot wearing Bull-Dyke to be Cinderella, Elspeth. If the sissy doesn’t improve soon enough I dare say we’ll be wearing sissy’s ass out with Ms. Caitlin’s sorority paddle,” warned Ms. Marta.

    I tried my very best to improve and about thirty minutes later Ms. Marta said, “That will have to do for now. Let’s get Sissy Andrea dressed the rest of the way, and familiarize the fop with his manly duties. Prissy boy had better behave when we cleanse him and put his plug in at bedtime,” Marta remarked.

    I was dressed in a plain, gray, daytime work dress. I already had a modest bosom from the fatty-tissue the corset had plumped-up in my pectoral region. I’d felt very shameful when they’d squeezed my “new tits” and fitted me for a white, training bra.

    I was put to work scrubbing toilets, tubs and bathroom floors. When I wasn’t working I was made to practice my hair and makeup skills with Elspeth. She removed the scarf over my hair, which she said she had “Hot-oiled.” Then she rinsed the oil out and showed me how to use a setting lotion and curlers to set my hair.

    “We can become good friends if you obey me, Andrea. I don’t mind this sort of tutoring. It’s easier work than house cleaning or cooking. You’re to eventually have the position of waiting on the Mistress and her guests. We servants refer to the position of Lady’s Sissy maid as a ‘Cake’ job. It’s very cushy, even if you will need to grovel obsequiously. ” Elspeth explained.

    I was told I’d be wearing my hair curlers while I slept. It was at bedtime that I gasped when I saw Marta wheeling in an enema bag, with a hose and lubricated nozzle, on a stand. I was told to pull up my nightgown and lay sideways on the bed, scrunched up in a fetal position.

    I was whimpering and begging to the giggling Marta and Elspeth, to please not  hurt me. They were very gentle with the nozzle and even allowed the warm, soapy solution to flow slowly into me. But still, as my stomach filled I thought I would explode.

    After expelling the mixture I was given a floral, scented, rectal douche. Then they began to insert the lubricated anal plug. They insisted it was the smallest size possible. I didn’t believe them.

    “What on earth is this for ladies? What does this do? Oh my goodness!” I exclaimed.

    “You’ll be just fine Andrea. This plug will make you walk so very pretty. With a tall pair of heels and a hobble skirt, your hips will just shimmy and wiggle as you mince about?” Elspeth promised me. 

    “Now off to bed with you sissy. Elspeth will wake you in the morning. Once she’s got you properly prettied, she’ll take you to The Mistress to show you off,” Marta said.

    “The Mistress,” of course, was my older sister Caitlin, whom I would be serving, as a feminized male, sissy-maid for the next three years. However, I still had no doubt, anything would be better than being the “bitch” of some “Bull” at the detention center.

Chapter Two: Madame’s Sissy

    It was Elspeth, who would convince me that doing my makeup and hair more prettily would endear me to Madame. So, following her lead, I decided to once again, set my hair at bedtime, and apply my cosmetics more vividly, just prior to serving breakfast in bed.

    As I served breakfast-in-bed to Madame, my tousled curls framed my face and my wet lipstick shone brightly, encircling my mouth. Madame had the dreamy look of a woman properly sated from last evening’s, or even this morning’s, frolics. 

    Philip on the other had, had the smug, arrogant look of any wealthy prig in his social class. The way he leered at me was most frightening. I thought he might have even drooled at the sight of my wiggling, plugged buttocks?

    “Well Andrea, I see you look a bit more like a proper sissy maid this morning. Doesn’t he Phillip?” Madame Caitlin asked of her boyfriend who had obviously spent the evening with her.

    “Yes, I find the sissy very attractive. Yes, very much so,” Phillip the Lecher added.

    “I’ll have a group of ladies here, riding with Phillip and I, today at 10 A.M. Andrea Maria. We’ll return from the ride at 1 P.M. and I’ll expect a luncheon at that time on the South veranda. Is that clear Andrea?” Madame asked.

    “Yes, mum. As you wish. A luncheon for how many ma’am?” I asked.

    “Oh gracious. What a bright sissy. There will be six of us. Besides me there will be Phillip, Hester, Judge Carstairs, Edna Phelps and Judge Carstairs’ niece, Rebecca. I’m certain Hester, Edna and the Judge will be interested in viewing how much you have progressed,” Madame Caitlin opined.

    Interesting? Every female in the courtroom on the very day I was sentenced to be a sissy maid, would be at the Warrington Estate. I was relieved to know Phillip would be riding with them. The last thing, I wanted, as Ms. Marta, Ms. Elspeth and I set-up the luncheon, was to have Phillip lurking around ready to pounce upon me.

    However, even with him off riding my worst fears were to be realized. The buffet luncheon was very near set. I’d just lit the gas warmers underneath the stainless steel trays.

    I was taking a short reprise. I’d just touched up my makeup and tousled my tresses. I then heard the sound of riding boots echoing in the halls.

   I looked up and there was that cad Phillip, a little worse for wear, but walking straight towards me. I’d later found out, that he’d made some flimsy excuse about his horse, “Throwing a shoe,” to leave the riding party about an hour before they were due to return. He laid his hands upon me and pulled me to him, trying to kiss me.

    “Please stop Master Phillip? This is hardly a private place, nor is it the best time to engage in whatever dalliances you are considering. Please? Someone could come along any moment,” I said, trying to push him away.

    Before I could say another word, and just as Master Phillip began to laugh lecherously, I heard a stern, strong, female voice.

    “Oh please Phillip. You surely can do better than a sissy, can’t you? You’ll soon likely be engaged to my dear, dear, Society Sister, Caitlin. And you are about to Peg, her Sissy-maid? Really Phillip?” Hester Byrne asked.

    “What are you doing here so soon Hester? And what business is this of your’s?” Phillip asked.

    “Unlike you Phillip, my horse actually did throw a shoe. But when I handed my ride to the stable Groomsman and asked about you, he said the horse you had ridden was just fine. So, I thought I’d check just to see what you were up to,” Hester said, with her eyes set harshly upon Phillip.

    “It’s my business because my dear Sister Caitlin is a very close friend,” Madame Hester said sternly.

    “I’ll have you know that Caitlin has given me permission to Bugger this sissy as well as have him fluff me,” Phillip laughed.

    “That’s very likely. Just as I, Caitlin detests those sorts of frivolities. However I don’t think she meant for you to enjoy that sort of ghastly entertainment when she has a house full of guests. Nor when she and those guests are just moments away from arriving,” Hester added.

    “Those sorts of pleasures are preferably to be enjoyed, only when The Mistress is away for a lengthy period of time. Now, let go of the sissy Phillip. He’s not for you,” Hester insisted.

    “And if I don’t?” Phillip asked.

    Hester took two steps towards Phillip. She wore very stylish, mannish riding garb, with tall boots. She was without a helmet. Her long, Swedish Blonde Henna shaded hair was swept back and wound into an intricate Nordic braid. The braid ended just below her shoulders. The Henna ombre gave her tresses an almost rose blush tint.

    She idly, yet menacingly, tapped a riding crop, against the boot-top of her right leg. She glared at Phillip with her deep, dark-hazel eyes. She pursed her lips and then spoke.

    “If you don’t release that sissy boy now, Phillip, I will slap you silly, with this riding crop. Your head will spin Phillip. I’ll knock you senseless,” Hester threatened.

    “You wouldn’t dare?” Phillip gasped.

    “Just try me Phillip. Go ahead. Unbutton the little fairy’s blouse, right now. See what I do. Your move Phillip,” Hester dared.

    Phillip looked at my chest, as if he was considering unbuttoning my white, satin blouse. Then he released me from his sweaty grasp and raised his hands in the air in a gesture of surrender.

    “There, enough. I’ll not touch the little fruit. Are you satisfied Hester?” Phillip asked.

    “Good boy Phillip. Nicely done. You’ve saved yourself a terrible beating. Now go and join your future fiancée and her guests. I’ll be down shortly. And remember. Leave this pretty boy alone. He isn’t for you, Phillip,” Hester said dismissively.

    I was just fine with Phillip taking his hands off of me. But I was certainly shamed by the recent happenstance. I’d just been “rescued” like a “Damsel in Distress” by this mature, female solicitor. I looked up and Madame Hester walked straight towards me.

    She tucked the crop under her arm very gallantly and put her hands on my shoulders. “Are you all right, Andrea Maria?” Hester asked.

    “Yes ma’am,” I whispered, my eyes embarrassingly downcast.

    “Are you certain, Andrea?” Hester replied, tilting my head up with her fingers underneath my chin. She looked down into my eyes.

    Her dark-hazel orbs penetrated deeply inside of me. They appeared like emerald jewels. Her prominent Nordic braid looked like a regal crown. It gave her the appearance of a Viking, warrior princess. Please, don’t think for a moment that Hester could ever possibly be confused with any ravishing beauty.

    Some might even say she has a mannish countenance. Yes, and she has a trim, slightly muscular, well-defined frame. Though she also has an adequate, firm bosom, a slender waist and ladylike hips. Her plump lips and her magical, fiery eyes, are undoubtedly her very best facial features. However, at that moment, though she was not, “My Knight in Shining Armor,” she was certainly my “Norse Shield Maiden.”

    She’d rescued me from certain sexual humiliation. Hester again repeated, “Andrea, I asked you if you were certain you were okay. Answer me, now.”

    “Yes ma’am. I am. I am now,” I smiled as I breathed a girlish sigh of relief.

    “Well good. Andrea you really are a very pretty boy. But that is no reason for Phillip to accost you in the way he just did. I will speak to your Mistress about this, at length,” Hester promised.

    “Andrea, I hope you don’t mind me saying this, but you have obviously made some great strides in makeup application and hairstyling since I last saw you,” Hester said, proudly.

    “Thank you Madame Hester. Ms. Elspeth has been a wonderful cosmetic and hair care tutor,” I said.

    “You also look more healthy. You appeared pale the last time I laid eyes upon you?” Hester asked.

    “Yes ma’am. Madame’s GYN doctor, now has me on numerous vitamins and supplements which I take daily. I also get a monthly B-1 injection. It’s noticeable is it?” I asked.

    “Well yes dear. Especially in the way your skirt and blouse fit you. So nice and snug in the bosom and the hips. Very tasteful,” Hester smiled.

    “I really have to be going, Andrea. Caitlin and the rest of the Sister ladies will be looking for me. And I would imagine you need to be ready to serve the brunch? Come here and allow me to give you a kiss, dear,” said Hester, as she squeezed my cheeks softly, and pulled my face towards her.

    I close my eyes and puckered my mouth. Hester planted her lips upon mine. I wanted to swoon. I honestly felt as if I’d totally lost all control of my emotions. I felt so effeminate, especially after Hester had so majestically swept in and rescued me. Her tongue ever so briefly titillated my lips before she ended the kiss.

    “Very nice Andrea. I’ll see you at the brunch, dear,” Hester said.

    At the brunch I attempted to stay away from Phillip, which was difficult as he was often near my Madame. At one juncture though, I saw something that surprised me. Hester was engaged in a conversation with Madame Caitlin. I noted that Madame, had her face in a contorted sneer. They both glanced up in my direction. I made myself scarce and busy.

    Shortly afterward, I saw Madame, engage Master Phillip in an animated discourse. Master Phillip was obviously distraught. He looked angrily at Madame Hester, who only smiled back at him and waved. Would this possibly spell the end of any issues I’d have with Master Phillip? 

    I dearly hoped so. I was cleaning up after the brunch, with the Head Maid, Ms. Elspeth. The Head Housekeeper, Ms. Marta took us both aside to speak to us.

    “Andrea, Madame Hester will be dining with Madame Caitlin and Master Phillip this evening. She will also be staying in the East Wing, Guest Boudoir & Bath for the entire weekend. There has been a change of assignments based on the Mistress’s preferences,” Ms. Marta paused.

    “You Elspeth, shall attend the Mistress and Master while Madame Hester is present. Andrea Maria, shall be at the beck and call of Madame Hester for the duration of her stay with us. Andrea, things will be no different than when you are responsible for the Mistress’s needs,” Marta explained.

    “Just abide by all of Madame Hester’s requests and everything will go smoothly. Madame Hester and her things should now be in the East Guest Boudoir. I suggest you see to her this instant, Andrea,” Ms. Marta instructed me. 

    I minced to the East side, and arrived at the guest boudoir and bath. I knocked lightly on the partially opened boudoir door and was told to enter by Hester.

    “Yes ma’am. Ms. Marta told me to see to your needs Madame,” I said with a smart curtsey.

    “Well. How nice of Ms. Marta to be so thoughtful,” said Hester, smiling, with her eyes opened wide.

    “Right now, Andrea, you could assist me with hanging a few things in the closets and sorting out my lingerie and cosmetics. Later, after dinner, I’d like you to give me a bath. You’ve bathed your sister, haven’t you? Oh excuse me. You’ve bathed Madame Caitlin?” Hester corrected herself.

    “Yes, I have ma’am. Yes. I have been instructed in how to bathe her, dress her, as well as brush her hair ma’am. At present I’m being taught to give manicures and pedicures Madame Hester,” I added.

    “Oh how nice. Well. You’ll make a very talented ladies’ sissy maid one day Andrea,” Madame Hester complimented me.

    Throughout the luncheon earlier, and later throughout dinner, it was quite easy to ascertain that Madame Hester was very charming as well as well-liked by everyone. During the luncheon her lady friends were most pleased to engage her in conversation.

    Madame Hester kept them all very interested in her discourse and was both pleasant and knowledgeable. During dinner she was also very much the same. Even Phillip, whom she had threatened to throttle earlier seemed interested in what she had to say.

    After the dinner cleanup I met her in the boudoir she was occupying. I was dressed in my evening maid’s attire with an apron covering, for the giving of her bath. I ran the water and added the oils and the salts. Madame Hester removed her own clothing. She stood in the doorway between the boudoir and bath observing me checking the bathwater temperature. 

    She wore a satiny robe. She’d let her braids down and her reddish blond hair fell to her shoulders. I glanced up at her and was struck by how majestic she appeared. I checked the water temp one last time and turned off the faucets.

    “Madame Hester. Will I be shampooing your hair? Or shall I tie it up upon your head to keep it from becoming wet?” I asked.

    “Oh gracious me, Andrea. How clever you are. I’d forgotten. You may tie it up, out of the way,” she said.

    “Might you sit at the vanity ma’am. I can fix it in an upsweep if you prefer,” I said.

    “Oh thank you Andrea. That would be nice. Such a versatile ladies, sissy maid you are. Later this evening I’ll have you brush my hair. Once you’ve bathed me, toweled me dry and powdered me, you may go to your room and change. Then you may return in your night-clothes, brush my hair and put me to bed,” Madame Hester smiled.

    To be in attendance, to such a mature lady as Madame Hester, was very exciting to me. I knew she was likely ten years my senior, though I didn’t realize that at nearly thirty-three years of age she was 14 years older. I also had not realized the influence she had on my sister. My sister Caitlin was now in full agreement that Phillip’s attempt at sexual indiscretion with me, had been fully out-of-bounds, considering Caitlin’s and her guest’s proximity to the estate at the time.

    Apparently at this moment, Caitlin was dressing Phillip down by saying, “Any sexual escapades with Andrea shall be taken up when I am far from the mansion. And in no way should you accost the pretty boy, unless I won’t be returning for several hours. And I don’t want to hear about what you do with your little Toy-boy, either. If you can’t control yourself Phillip, I will have self-control taught to you,” Caitlin clearly admonished him.

    I combed and brushed Madame Hester’s hair into a chignon, fastened at the nape of her neck. I asked her in regards to her statement instructing me in the wearing of nightclothes to brush her hair.

    “Do you want me to return in my robe and slippers ma’am to attend to the brushing of your tresses?” I asked.

    “A pretty nightgown and peignoir set would be preferable for that, Andrea. With some nice high-heeled slippers?” Madame Hester proposed.

    “Yes ma’am. I received such items for my nineteenth birthday ma’am. Why don’t we get you into the tub, Madame?” I asked.

    “Very well,” she said, standing and removing her robe, to show herself to me in all of her beautiful, womanly glory. 

    Hester stood there naked, except for a pair of Marabou slippers. She had her hands held up limply in an uncharacteristically, dainty manner, for her. Her nakedness revealed to me her taut, athletic frame, perfectly formed breasts, delightfully rounded hips, well-turned legs and luscious, opulent thighs.

    “Come along Andrea. We don’t want the water to cool off. Take my hand,” Hester said as she led me into the bathroom. 

    She checked the water temperature with her nicely manicured nails. She didn’t have the lengthy nails of a French-manicured debutante. Her nails were neat, clean and painted. But Hester’s nails were the nails of an active female that rode horses and and played tennis. She was just as likely to play tennis in shorts as in a skirt.

    She lowered herself into the tub smiling and handed me a loofah. 

    “Wash my breasts dear. I’ll do my face with this washcloth. Then do my stomach. After that, you can wash my legs, feet and my personal places,” Hester smiled.

    I was becoming aroused, though it was not like a normal boy’s arousal any longer. The “Vitamins and Supplements” I’d been taking and the “B1 injections” I’d been given had taken their toll on my boyishness. But for now, some sort of arousal was possible. I’d noted the girlish growth in my hips and breasts but what was I to do or say?

    Did I really want to risk argument, and be returned to the courthouse for reevaluation and possibly be sent to the County Detention Facility? Or, was it also possible that some sort of “School for Sissies” existed? I’d overheard both Ms. Marta and Ms. Elspeth discuss such an institution of higher learning.

    I didn’t want to wind up there either, if what they’d said was true. I’d read about HRT and it appeared that the effects were reversible. So I was much better off under the auspices of my sister and her associates. 

    I soaped and rinsed Madame Hester’s bosom. I moved to her flat stomach. Her eye were closed and she was resting her head on the quarry-tiled wall. She’d washed her face. Her skin was pink and so vibrant. She gleamed in the glow of the bathroom lighting. 

    As I soaped her tummy she sighed delightfully. How was I so fortunate to be bathing this virtual goddess? Even in my emasculated captivity, I thought of myself as being charmed. As I passed the loofah  down to her legs, she raised her knees to make herself more accessible to my ministrations. 

   She said not a word. She didn’t have to. I was both smitten and awed. When I bent to do her feet, she anticipated my actions. Hester then sat up straighter and lifted her legs to expose her feet. She rested her feet upon the front edging of the bathtub, to make them easier to wash.

    Of course this exposed her majestic pudenda and its perfectly trimmed and waxed bush. As she sighed once again, she stroked her pussy lips inadvertently with her right hand. As she did so, she emitted a pleasurable sound from her lips. Once I’d done her feet I hesitated. She wouldn’t allow that at all.

    She lowered her feet back into the water, arched her back and took my hand that held the loofa. 

    “You must wash me here, darling Andrea. Remember? We are just like two girls here and you are giving your Mistress’s dear friend a bath. Wash my pussy, my little Toy-boy. Don’t be afraid. It won’t bite. Though I may bite you,” she laughed.

    Toweling her off was no less arousing or painstaking. She had me dry every nook and cranny of her luscious body, including her bush and pussy lips. Then she had me moisturize her entire form. Afterwards I unpinned her hair and applied a conditioner. At last I powdered her with a puff.

    “Now run along and dress in your nicest negligee, heels and peignoir. Then return and you may brush the tangles from my hair, Andrea,” Hester ordered.

    I was changing in my boudoir when Ms. Marta knocked.

    “Oh, you’re done attending to Madame Hester?” Marta asked.

    “No Mum. She told me to change and return to brush her hair. She stated she wanted me wearing my nicest sleepwear,” I said.

    “Hmm? Well I see you are. Did she say anything about freshening your lipstick, sissy?” Ms. Marta inquired.

    “No ma’am,” I added as I departed from my boudoir to return to Ms. Hester. 

    When I arrived to Ms. Hester’s boudoir I mentioned quizzically about what Ms. Marta had said about fresh lipstick.

    “Oh, what a wonderful idea. Kneel at the side of my vanity bench. You have darker hair. You’re easily a medium brunette. Hmm? We’ll use a Sienna shade. Pucker up darling. There. Now purse your lips for Hester. Such a pretty boy. So sweet,” Hester remarked.

    “Now, comb the conditioner through my hair first. Speaking of hair. Have you thought of changing the color of your tresses? Most kept sissies do so, by the age of nineteen. We should speak to Caitlin. Her stylist could do it the next time she’s here,” Hester intoned.

    Combing and brushing the hair of this absolute Queen was delicious. I reveled in the shine of her tresses and the perfumed scent of the conditioning treatment. As I carefully undid her tangles I looked into the mirror. I saw two girls. Two pretty girls.

    Actually, what I really saw, was one beautiful woman and one effeminate sissy boy. It was how I now saw myself. I was dressed in a nightgown and matching peignoir robe. I wore high heeled slippers and fresh Sienna lipstick. My hair touched my shoulders in soft curls. I wondered how I would look with a hair color similar to Madame Hester’s hair? I thought I’d ask, as I continued to brush her beautiful locks.

    “Madame Hester. What hair color would look good on me? If you were to decide, would you have the beautician lighten or darken my hair?” I asked.

    “Would you want me to decide your hair color for you Andrea or would you prefer to make that decision?” Madame Hester asked.

    “I’d prefer you decide ma’am. I think you’d be more knowledgeable in such matters. After all. Your hair color is so delightfully stunning ma’am,” I said, nervously. 

    “Oh how sweet of you to say so Andrea. I’ll tell you a little secret. Madame Caitlin and I use the same Colorist, my dear little toy-boy. The colorist chose my coloring for me. I am a light blonde, but she made me a Swedish blonde with a Henna Hombre. I love it now,” she smiled.

    “I’d have your’s lightened if it were left up to me. I’ll discuss it with Caitlin. She’s your Mistress at present. Generally the Mistress will decide for her kept sissy. She wants all her servants to look a certain way. A sissy should blend in, as well as complement the real girls,” Hester opined.

    “Looking at you, however, you would make a very pretty redhead, I think. Yes, a very pretty redhead. You’re a very pretty boy, Andrea. Well, you’ve brushed my hair close to 100 strokes. And it’s time for bed,” Hester said as she stood up.

    Hester turned towards me and took the hairbrush from my hands. She sat it down on the vanity. Her eyes twinkled. I looked up at her. She must have been six feet tall without heels. I’m 5 feet nine inches and I had to look up slightly. She leaned down and kissed me softly on the lips.

    “Why don’t you sleep with me this evening Andrea Maria? The bed is so huge. We can snuggle and chat. Would you enjoy that Andrea?” Hester asked.

    “Yes ma’am, Ms. Hester, I would cherish that,” I stammered as she took me by the hand and led me to the King-sized bed. 

    Once we were both under the sheets and blanket, Hester surrounded me with her embrace. She nestled my head between her shoulder and bosom. Then she kissed me. This time it was a romantic, sensuous kiss. My lithe, emasculated body was soon filled with quivering chills.

    This forceful, assertive woman, was captivating me with her aggressiveness and strength. I’d been with girls. But, I’d certainly never been with a real woman and a complete Tigress such as Hester. I’d become so effeminate, that as much as her assertiveness aroused me, it also frightened me. She wouldn’t hurt me, would she?

    My question was answered when she took the initiative to separate from the startling kiss and move my head in the direction of her pudenda.

    “You must be trained to service me in an intimate, submissive way if you are to be mine, Andrea Maria. I don’t necessarily see you as a womanly dressed sissy-maid, though. You could be more useful, as well as more interesting, and a delightful curiosity, if I developed you into, a very pretty and effeminate, sissy-boyfriend and toy-boy. In any event, you will need to know how to eat pussy,” Hester stated plainly.

    “I will show you. Well, I’ll be explaining the proper techniques to you. You’ll learn as you go along. This is all about using your lips, tongue, mouth and fingers to stimulate my clitoris and bring me to a climatic spasm,” Hester explained.

    As she narrated thoroughly, each and every portion of the technique, I carefully performed what she so carefully and skillfully, described. I’d licked girl’s pussies prior to this, but never so carefully and lovingly as Madame Hester insisted that I care for her’s. 

    “As a sissy, you should cherish and worship the care you take, with your Mistress’s pussy darling. You should demonstrate the same intricate approach any subservient, femme Lesbian does to satisfy her domineering, Lady-in-Charge. That’s what I am to you Andrea Maria. I am your Lady-in-Charge. You shan’t ever forget that,” Hester cautioned me.

    As I lavished my oral attentions onto Hester, she idly played with my hair. She cooed and sighed as I varied the pressure and sucking ministrations upon her vulva, and clitoral region. As her passions increased I could sense her pleasure and her impending climax.

    Indeed, Hester’s climax was significant and I was proud that she pulled me to her, to assure me, “You’re going to make a darling, sweet and pretty, Toy-Boy for me. I knew it when I saw you. I can hardly wait to have you groomed and attired to my tastes, Andrea.”

   I snuggled into Hester’s protective arms, not caring an iota that my sexual needs were unrequited. I was simply satisfied to have made Hester’s evening most pleasant. We were laying blissfully together, and drifting into a slumber, when the unpleasant sounds of raised voices filtered into our wing of the mansion.

    I sat up in wonderment. Hester pushed me back down to the bed, gently.

    “I’ll handle this my pet. It’s hardly any affair of your’s, my delicate little sylph. Put the unpleasant noises out of your prettily coiffed head dear, and sleep,” Hester assured me.

    Whatever was in progress involved at least Ms. Marta and Elspeth, if not my sister. After Hester departed from the room we’d been sleeping in, I still listened. The voices grew louder initially and then faded. I managed to obediently return to my slumber, until I heard the distinct hum of a motor vehicle engine outside, and then more voices somewhere from below the boudoir window.

    I dared to get up, leave the bed and tiptoe to the window to peak out, by opening the billowed lace curtains. Parked near the main entranceway, to the ancestral mansion, now solely owned by my sister Caitlin, was a family-sized minivan. The uniformed female driver and two other uniformed females had alighted from the van.

    The headlights were still on and the van’s engine remained running. The three women were wearing uniforms similar to those worn by the security staff my sister now employed. They were soon joined by three members of my sister’s newly employed security team. In between two of Caitlin’s security staff was a struggling figure!

    The two security staffers, holding the wriggling body, had thrown a bag or hood over the struggling person’s head. The person’s arm’s were bound at their sides and they were soon lifted helplessly, feet kicking wildly, into the back of the van, by two of the van’s staff.

    As the rear door of the van was closed, my sister Caitlin and Hester walked outside together. Hester had one of her arms around my sister and was obviously comforting her. Caitlin was handed some papers by the van’s driver and Hester appeared to be showing her where to sign. 

    There was a small lamp I had turned on in the boudoir when I’d gotten up. It must have cast either some illumination or my shadow though the window down to the surface near the van. The very observant Hester looked up, back over her left shoulder to the window, where I was viewing the scene in front of the entranceway.

    I ducked back and released the curtains! Had I been seen? I scurried back into bed, shaking. Hester had instructed me to stay in bed. Had she seen me and would she be cross with me? I’d soon find out. I attempted to appear to be sleeping. But when Hester entered the boudoir she wasn’t buying it.

    “Deceit doesn’t set well with me, Andrea Maria. Nor does disobedience. Please don’t insult me by attempting to mislead me? I want you to get out of bed and kneel there on the carpet,” Hester said. She’d turned on a bright overhead light and was pointing to a spot near the vanity bench.

    I was squinting my eyes from the brightness of the light. Hester held a glass of bright-red liquid out to me. 

    “Drink this. You are to forget anything you saw while you were peaking from the window, Andrea. I’m in no mood to discipline you for this offense. I warn you though, my pet. I won’t be so kind upon the next occasion when you should defy my wishes. Should you ever relate what you might have witnessed tonight, to anyone, you will be the very next passenger taking a trip in that van. How do you feel right now?” Hester asked, as she took the empty glass from me, that had contained the bitter-sweet, syrupy liquid I’d just drank.

    I stared blankly at Hester, my eyes blinking. She smiled. I felt confused and when I spoke I babbled incoherently. Hester placed her hands upon each side of my head. She began an incantation, as she tilted my head downward, so that I was then staring at the suddenly swirling, colorful pattern, in the now brilliant woven carpeting.

    “Hecate, Goddess of Magic. Erase the recent memory of tonight’s activity from the consciousness of this delicate sissy. May this darling, effeminate boy, become all mine. Consume his spirit with obedience, subservience, effeminacy and supplication, for me, and for all of Cassandra Womanhood. May your all-consuming, otherworldly spell, now be cast,” Hester hissed.

    It was as if I was being sucked into the spiraling maze of churning colors that had once been a woven carpeted floor. Hester released the grip she had on my head. I screamed girlishly as I perceived myself falling into an abyss. 

    Then, it was as if I ceased falling. I was on my back looking up at the radiant apparition of Hester. Her hands and arms were moving in mystical, flowing patterns. I could hear her melodious voice. The words she was saying were unintelligible. It sounded as if she were speaking an ancient foreign tongue.

    Her emerald eyes appeared to have glowing specks of red within them. Then I awoke. Hester and I were in bed. We were in the very same guest boudoir, from the prior evening. The sun was barely rising and I was nestled comfortably, and peacefully, in what I perceived to be Hester’s totally, loving, protective arms. Hester smiled and spoke.

    “Good morning Andrea Maria. You are mine now, aren’t you my kitten?” Hester asked.

    “Yes, Madame. I am your’s always. I belong to you,” I agreed.

Chapter III: Sissy Feminique 

    “The Feminique Academy of Beauty, Dance and Modeling is an all-encompassing, non-boarding, educational and training facility for genetic females, transgender ladies and sissies, as well. Students attend day classes only. It is not a boarding school. The Cassandra Sisterhood had signed a Joint Marketing Agreement with the Alpha Ladies’ Guild, of Pankhurst, Massachusetts. “The Guild” as they like to be called, originated the Feminique Academy.”

    Thus read the article in “Aphrodite’s Swans” the monthly publication of the Cassandra Sisterhood.

    A Cassandra member visiting a lady friend in Pankhurst, had been wonderfully impressed with the Feminique facility. Through their new agreement with the Alpha Ladies Guild, the Cassandra Sisterhood was now jointly assisting “The Guild” with the Franchise Marketing of the Feminique Academy, Feminique apparel, Feminique beauty products and the Feminique name.

    I was now a Feminique Academy student. Some Feminique students specialized only in Beauty classes so they would eventually  become cosmetologists who would be employees in full-service Feminique salons. Others might strictly concentrate as Modeling students, in order to appear in Feminique fashion shows. At these events they modeled the dazzling Feminique Fashions, and would also appear in the Feminique Catalog. 

    Most of the modeling students take dance, primarily ballet, in order to develop the delicate, dainty gracefulness, expected from any Feminique sissy. In my case, Madame Hester insisted I enroll in all three programs, to become, in her words, “A well-rounded, excessively effeminate, perfectly dainty, sissy-boy.”

    I was to learn cosmetology to be able to do Madame’s beautiful  hair. As well, I would learn to groom her nails, apply her makeup, and perform massages and facials for her. I’d also be expected to employ the same services for her friends, associates and guests. Besides learning to walk and act like a proper, effeminate sissy-boy, I was to take modeling in order to be able to participate in Cassandra Charity Fashion Shows, as a sissy model, in order to help raise money for Women’s causes.

    In other words, I was being groomed to be an asset for both Madame Hester as well as the Cassandra Sisterhood. I was educated with the knowledge that a sissy walked, moved and spoke effeminately, but with a different sort of dainty “panache,” as opposed to the feline grace and true femininity of a real female.

    As for dance? Well, what “Lady-in-Charge” doesn’t prefer a graceful, demure sissy, or enjoy having her sissy perform an at-home ballet recital, to amuse her Cassandra Sisters? As such, I was attending the Feminique Academy three days a week. When not attending, I kept myself pretty and sissified for my Madame Hester and performed the duties of her obedient, Toy-Boy homemaker.

    As Madame Hester had told me, she hadn’t ever seen me becoming  a fully-feminized sissy-girl, should she one day own me. She preferred her sissy boy to look and act like a sissy. She expected me to be delightfully effeminate. However, she felt people should realize that I wasn’t a girl. 

    “Andrea Maria. Let’s not be silly. People are not supposed to think you are a real girl. It is true, someone might look at you and be puzzled and wonder if you are a real female. But as they look closer they will realize that you are a very effeminate, pretty, sissy boy. Because, Andrea, you are a sissy boy. You are, of course, my sissy boy, Andrea Maria. And you should be pleased that you are a sissy,” Madame Hester intoned.

    “I know that at times it is difficult and shameful for you. People will of course look at you strangely, and will be very amused by your appearance. But that is because I have you so sweetly attired, in the most fussy, and effeminate of apparel. But that, my dear sissy, is often times what it is like being an effeminate sissy,” Madame Hester explained.

    “There will be dressy occasions when I will put you in a pretty skirt and blouse or a lovely dress, plus high heels. But with your nearly flat bosom, most people will still realize you are a boy that is being made to dress girlishly,” Madame smiled condescendingly. 

    Of course my hair has never been girlishly long since I have belonged to Madame Hester. She’s had her hairdresser keep it cut primarily, in a darling, shaped, pixie style. The longest she’s ever allowed it to grow was a pixie-bob. I was permitted to wear my hair in a slightly longer Pixie-Bob styling so I could get a “Top-curled” spot perm, when I was the flower-boy at my Sister Caitlin’s wedding to her brand new sissy-wife, Philippa Belle. 

    Philippa is a very strikingly feminized beauty, who took quite well to thorough emasculation and submission. At the behest of my Sister Caitlin, Philippa attended a long-term, sissy, boarding and finishing school, The Winthrop Institute. The Winthrop Institute is an educational facility, sponsored, owned and operated by the Cassandra Sisterhood.

    “The Institute” as the “Sisters” affectionally refer to it, produces some of the most alluring examples of male to female transformations known to Modern Feminism. Ownership of a “Trophy Sissy,” trained at the “Institute,” is a prestigious bauble any Cassandra Sister would love to show-off at the opera, ballet or the Country Club.

    I attend classes at Feminique, on Monday (Cosmetology), Tuesday (Modeling), and Wednesday (Ballet). Thursday and Friday I am a Homemaker for Madame. On Weekends, my duties are contingent upon Madame’s needs and desires.

    A typical Thursday or Friday, when I am not attending classes at Feminique, will begin with preparing Madame Hester’s breakfast and seeing her off to the legal offices where she is employed. For my daytime housekeeping duties I am attired in black or red ballet flats, matching socks, dark Capri slacks and a peasant blouse. I wear girl’s cotton panties and a training bra. 

    The outfit isn’t showy at all, but just right for the daytime housekeeping outfit of any kept, sissy homemaker. I’m permitted to apply, light lipstick and eye makeup, with a touch of blush. If my duties for that day include grocery shopping, or attending to Madame Hester’s dry cleaning, I may use an automobile provided to me by Madame Hester, for such responsibilities. 

    I have a driver’s license with my now legal name of Andrea Maria Warrington. The document describes me as 5 feet 8 inches tall and weighing a svelte, 125 pounds. It also lists my sex as Male. In the photo taken I am wearing makeup on my lips, cheeks and eyes. 

    For shopping expeditions I’m expected to “dress-up” and “doll-up.” That doesn’t mean I’m supposed to appear to be a female. No, not at all. I’m simply expected to present myself as a more attractive, more effeminate, well-dressed sissy. Should anyone who might know Madame Hester see me, I’m to look my very best.

    This will require wearing more “dressy” or “showy” attire. I’ll usually change into something such as a pink camisole top, with a pair of white, stretch, bell-bottom slacks. I have a lovely, pink, brocade trumpet-sleeve, side tie jacket to wear for such outings. With a hand-held matching bag and some kitten heels, my attire gives me a very “smart” look for shopping. 

    Shopping also provides me with the luxury of using a little more makeup and putting enough gel in my tousled, pixie-bobbed tresses to give them a delightful shine. Fortunately, the same outfit, usually sans the jacket, is perfect for greeting Madame Hester as she returns from a day of legal work. Hester works for a very well-known, “K” street, Feminist law firm, where she is already a junior partner. 

    Therefore, the home we live in, though relatively modest, compared to Caitlin’s estate, is opulent by any standards. Hester’s younger sister, Ms. Delilah, attends law school in Virginia and resides with us on weekends and when classes are not in session. 

    So, I’m quite fortunate to have not one, but two females to keep me focused on my appearance as well as my duties. Once dinner and cleanup are completed I’ll attend to Madame Hester in her study. I’ll bring her a relaxing beverage, her favorite being, Apricot Brandy. She may have me massage her feet with Chamomile oil.

   I love to hear her say, “I’d like to see you in my boudoir this evening. Why don’t you change and await me there?”

    “What shall I wear?” I’ll ask.

    “Just surprise me, but make it very special,” she will smile.

    In an absolute dither, I then mince to my boudoir and look through the closets and dressers for just the right thing. On a recent occasion, not long after my sister Caitlin and her sissy-wife Philippa Belle, were wed, Madame Hester sent me mincing off, after dinner, with the suggestive, heady promise of an evening’s lovemaking in her boudoir.

    Gloriously ecstatic, I scurried to my boudoir and in my lingerie dresser, found a pair of striking cream-colored satin pajamas. They were so beautifully scented from the coconut-oil sachets I’d placed in the drawer. With the lavender body lotion I’d used after my afternoon shower, I knew Hester would adore the effeminate fragrance of my  body. 

    I put the pajamas on, and looked at my nails. I’d done them prior to going to the dry cleaners. The lady behind the counter had complimented me upon my delightful pearl-white polish. I decided to match my lips to my long nails, with a pearl-white frost lipstick. Lastly I used a styling pomade to give a “lift” to my recently, spot-permed curls. 

    Next, I used a strawberry-scented hairspray to keep my “do” controlled. Sitting atop Hester’s bed in her boudoir with my legs and feet curled under me, I noted my genitalia to be fully aroused. This was a change that had occurred after Hester had taken over “ownership” of me from my Sister Caitlin.

    In the first six months the courts had assigned me to Caitlin’s control, I’d been effectively, chemically and emotionally neutered, with Estrogen. Caitlin’s future plans included my surgical neutering also. I was to be gelded, given a large, implanted, womanly bosom along with matching hips. Caitlin then planned to sell me to the highest bidder among her Cassandra Sisters.

    Effectively, my inheritance, my trust fund and the Warrington Estate would become Caitlin’s. Fortunately for me, when Caitlin found herself inconvenienced with the emasculation and transformation of Phillip, into “Philippa Belle,” I became of a secondary concern to her. Hester found me attractive, and used her obvious influence with Caitlin. Hester took over both my probation with the court system, as well as my ownership documents filed with the Cassandra Sisterhood. 

    Upon the occasion of my first full day in Hester’s home and under her very strict charge, Hester relieved me of my Estrogen tablets. 

    “You can hand those tablets over to me now, Andrea Maria. You’ll no longer be needing these nor the Estrogen boosters you receive from the GYN. In fact you won’t be seeing the GYN any longer. I have proven techniques of controlling sissies such as you, as well as my own methods of redesigning your figure,” Hester smiled.

    “I also have normal female sexual needs. What you do with your lips and tongue is quite nice. However I enjoy an erection now and then. Over time, with the removal of the Estrogen from your system you’ll begin to have erections, once again. However, there are rules you must follow, Andrea. First, you shall never masturbate,” Hester cautioned me.

    “You must always inform me when you do have an erection or if you have a nocturnal emission. And never, when you are sexually aroused shall you ever initiate sexual contact with me. You may flirt with me in a sweet manner. For instance you might possibly swing your hips in an alluring manner. You might also coquettishly move your shoulders prissily. But never touch me intimately to attract me. I shall initiate all sexual contact in this relationship,” Hester ordered.

    Hester indeed had ways to control me and alter my figure without hormones. Hester Byrne was descended from a Coven of Wiccans that had come to the United States with the early settlers in Plymouth, Massachusetts. She had been schooled in, and had the access to, Herbs, potions, remedies, incantations and spells.

    As the effects of the Estrogen wore off, my body was treated with herbal packs to give me a modest, pubescent bosom and slightly pear-shaped hips. My waist was reduced through strict dietary and exercise requirements. This included the taking of ballet. To give my shape yet more definition I was subjected to further, restrictive waist-cinching measures. 

    Part of the mental and emotional aspect, of my devoted subservience to the female sex, was reinforced by my three day per week attendance at the Feminique Academy. True genetic females and numerous Transgender women took classes at Feminique. Many of the women in the cosmetology classes were studying to be salon and spa managers or certifying on the use of Feminique products.

    Feminique marketed not only beauty products for females and sissies, but their clothing line was geared to upscale females as well as the sissies they controlled. Quite a few of the models were professionals sharpening their runway skills and becoming familiar with the designers and nuances of a Feminique Fashion show.

    The same held true for the dance classes. Most of the students were studying to become dance instructors or simply professional models taking a dance class to stay in perfect shape. Because I was a part-time student, and I wasn’t really attempting to receive a certification of any sort, Hester used this to her advantage.

    Hester had quite a bit of pull in the Sisterhood. She arranged with the faculty at Feminique, to enroll me in predominantly all-female classes. There I was made to wear the same uniforms the female cosmetology students wore, as well as model alongside professional models.

    Wearing the same ballet slippers, as well as the tights and tutus, that the females in my dance class wore, truly reinforced my effeminacy. To show her control over me, every evening after dinner, Hester would have me describe the activities I took part in during class. Then she would smile and applaud. 

    However I was thrilled that my ability to perform sexually as a somewhat normal twenty-year old boy had been restored. I sat on Hester’s bed awaiting her. I looked at the pretty, cream colored ballet slippers upon my feet. I knew I looked pretty to her when she walked into her boudoir. 

    She sat on the edge of the bed, unbuttoning her blouse. 

    “Remove my high-heels Andrea. I have slacks on, so I only wore footsies. That’s it honey, slide off my slacks and panties. Now, unsnap my bra. Doesn’t my pussy look nice baby? What about Mummy’s tits? Where do you want to start my sweet boy? Mummy’s pussy? Well good. Oh, now that is so nice!” Hester crooned as I knelt and licked her puss.

    She shifted her body, and laid upon the bed, pulling my lithe frame, with her. 

    “There sweetie. Did Mummy make things more comfortable for you? Well, wonderful. That’s really very nice what you’re doing with Mummy’s pussy, so keep that up, precious,” Hester gasped as she laid her head upon a pillow and closed her eyes.

    Hester’s hips moved in a slow, pulsing, circular motion. To be licking Hester’s pudenda and vulva, knowing I could only enter her vagina with her expressed permission was all part of my innate subservience. On occasion, Hester will insist, that I was “Born to be a Beta Boy.” I’ve always believed her.

    I also know that it will be a rare treat, whenever Hester will allow my penis to touch her lips. I know she would prefer to lick the puss of one of her “Sister’s,” rather than the head of my cock. To me however, it is a gift that she’d allow me to touch her at all. I feel she could have any person, male or female, that she chose as a lover. Yet, she’s chosen me.

    As Hester’s ample bosom rose and fell, I could sense her impending climactic moment was not far off. I looked up and watched her stomach flutter as her breathing surged. Then she whinnied and sighed. “Oh!” Hester shouted.

    “Oh my! Oh my heavens, Andrea! Just so good!” Hester exclaimed as I felt her entire body shudder. Then she screamed loudly as her dam broke.

    “By the Goddess Hecate! Andrea Maria your tongue is magical!” Hester bellowed.

   I hugged her thighs and slowly licked my way up her body as she laughed so beautifully and hugged me.

   “Oh my Andrea. I can’t believe I own you for two more years. What will I do without you? I think at your next hearings, I’ll make up some offenses you have committed and get your sentence extended,” Hester laughed.

    “Darling, at the moment I am so tired from a long workday. I don’t have the energy to mount you. However, if you’ll get the lubricant for me and kneel on all fours beside me, Mummy will masturbate her darling boy. Oh, and you’re such a good boy, Andrea Maria. And so very pretty too. I love what you did with your hair and makeup tonight to entice me. That is why I love to doll you up when we go out together. Especially around my Cassandra Sisters,” she sighed.

    “You are by far the prettiest and most well-behaved sissy-boy of our clique. It’s true that Philippa Belle, your sister’s sissy-wife, is easily the most stunning, but she looks just like a real girl and practically is,” Hester conceded as she slid my pajama bottoms down to my thighs, and carefully stroked my cock. 

    I was kneeling on all fours and had closed my eyes. But, Hester insisted I look at her. 

    “Look at me, Andrea. Drink of my beauty with your eyes, my pet. Focus on me, Andrea Maria. Focus. Focus upon me and not on what I am doing with your cock, my love,” Hester demanded. 

    “Look at you. Look how I can control you, simply by grabbing your love muscle. That’s it. Stare into my eyes. Look at the beauty in my face. Take in the loveliness of my womanly bosom. You are such an easily controlled sissy. That’s it my pretty one,” Hester commanded. 

    She squeezed my balls with one hand and manipulated my cock with the other. I was floating upon air. Her hands were magical. As I looked deeply into her Hazel eyes it was as if there were red beads sparkling around her emerald irises. It was so haunting. As she brought me closer and closer to sexual nirvana, she sniggered with a throaty, husky laugh.

    “Now my prissy one, you must climax for Mummy. Come along. Do as I say. Spurt ever so prissily for me darling. I knew it. You couldn’t hold out any longer,” Hester laughed gutturally as my penis creamed fluidly and freely into the palms of her hands. 

    She appeared to expertly catch all of my seminal fluid as she permitted me to collapse onto my back. As I lay there fulfilled, Hester held her hands over my face and said, “Open you mouth sissy. Mummy wants to feed her baby bird.”

    She then allowed my sperm to drip into my mouth from her cupped hands. “Swallow,” Hester commanded.

    Then she said, “Lick,” as I cleaned the rest of my gooey salty discharged off of her fingers and the palms of her hands. 

    It didn’t matter to me. I understood that this was what I did to enjoy being in the glow of my Mistress, Madame Hester Byrne. And only Hester could remove that privilege from me. 

Chapter IV: Philippa Belle, Model Sissy

    It was a very busy weekend in the world of the Cassandra Sisterhood. It had begun with a dedication ceremony at the Temple of Hecate, Goddess of Magic. All the new Sissy Castrates that had been gelded over the summer, would be dedicated to Hecate for the Autumn Equinox. 

    Fortunately I wasn’t one of those. Neither would Philippa Belle, my sister’s new sissy-wife be included. I could see, as Hester and I sat at the same table with Philippa and my Sister Caitlin, that Philippa had already been gelded. In her upswept crimson tresses, Philippa wore the bright pink bow, with a Black Rose emblazoned upon it, that signified a Castrated Sissy-Wife at one of these ceremonies.

    Additionally, dangling from her pierced ears were Black Onyx earrings. The dark jewels in her earrings, were actually her surgically removed testicles, melded into a crystalline mixture with the Onyx. Philippa’s Mistress, my own Sister Caitlin, also wore a matching Black Onyx Rose, pinkie ring, that identified her as the “Owner” of a neutered, sissy-spouse.

    Caitlin had turned to Hester. “I’ve grown to love these ceremonies. Haven’t you, Hester? The new Castrates are dressed just so beautifully. And it’s so amusing to watch how excited the chosen Castrato Princess becomes when the High Priestess selects her. Have you ever considered having Andrea Maria gelded, Hester?” Caitlin asked to my absolute horror.

    “No. Not at all, Caitlin. Andrea behaves perfectly well, and I’m very comfortable with the way Andrea looks and with our amorous adventures together,” Hester said to my relief.

    “I know my Philippa Belle is simply thrilled that she has been neutered. Aren’t you darling?” Caitlin asked, smiling at Philippa, with a questioning, raised eyebrow.

    “Yes Madame. It has been an amazing benefit. I’m so calm and at ease now. No longer do I doubt who and what I am. Being a gelding has made an astonishing improvement in my life,” Philippa agreed.
“Philippa, I’m so glad you feel that way. I recall the day that you were neutered at the Winthrop school. You remember of course. I know you did faint, but you have to admit you didn’t feel a thing,” Hester remarked.

    “Caitlin, I clearly recall you didn’t want to witness it, so I volunteered to observe to make certain it was done properly. I held Philippa’s hand as they wheeled her into the surgery. I vividly recall that they had Philippa strapped down tightly and mildly sedated, so she didn’t move during the procedure. They don’t want to cut off too much. They were so nice. They had a mirror positioned so that Philippa could view the entire procedure but she chose to close her pretty brown eyes. Didn’t you honey?’ Hester asked. 

    No one else was saying a word other than Hester at this juncture. So Hester continued on.

    “Philippa was grimacing with her eyes closed. And the female surgeon, a true expert, administers the local anesthetic so perfectly. The lady surgeon admitted she’d done several thousand neuterings since she’d worked for Winthrop at various school around the nation. Philippa, now tell everyone. Admit it. Did you feel anything?” Hester demanded to know.

    “No Madame Hester. I felt barely a little pinch,” Philippa sighed.

    “I knew it. Then the surgeon slices open the ball sac, snips off Philippa’s useless testicles, sutures everything, and I tell Philippa the good news. Philippa honey, it’s all over. No more nasty testosterone will any longer be screwing your system up,” Hester recalled.

    “Then I realized the poor girl had fainted from the excitement. The nurse revived her and told me that it happened quite frequently,” Hester surmised.

Of course I knew exactly who Philippa Belle was, and who Philippa Belle had once been. Very likely, there had been but one incantation and spell, which Hester had applied to me, that had not succeeded fully. 

    That would be the chant she’d done, upon the evening, when I’d been ordered to forget what I’d seen from the bedroom window. As I’d been told, I’d never discussed the events of that night with a living soul. Though, I’d never been able to forget the sight of the struggling, bound and hooded figure being abducted into the minivan. 

    It is likely, however, my ability to recall that evening’s events, was spurred by the whispered discussions between Elspeth and Marta, upon the following day. Throughout that next workday, Elspeth and Marta gossiped effusively about the alarming discourse between “Master Phillip” and “Mistress Caitlin.”

    From what I’d overheard, I’d been able to piece together a reasonable visualization of what might have transpired that evening. It appears that my Sister Caitlin had sternly castigated Phillip for his indiscretions with me. She’d told him never to touch me unless she and any visitors were far from the estate.

    Phillip had gotten angry and menacing. He’d also made insulting remarks and threats to Caitlin concerning Hester, and the rest of Caitlin’s, Cassandra Sisterhood companions. My Sister Caitlin was having none of that and soundly slapped Phillip’s face. This is where things got out of hand. In a most ungentlemanly fashion, Phillip pushed Caitlin down, onto the bed.

    Struggling ensued, with more slaps and screaming. When Elspeth and Marta arrived, Caitlin screamed for them to contact security. Security soon had Phillip restrained with handcuffs as Hester comforted a sobbing Caitlin. Hester treated Caitlin as an older sister would treat a much younger sibling.

    “You’ll never have a satisfactory relationship with that cad, Caitlin. He wants you for your money. You should prosecute him for Domestic Abuse and be rid of him, My Sister,” Hester advised.

    “No Hester. Phillip can actually be a very loving, gentle, almost feminine soul when I an able to dominate him. I simply lost control of him, as well as myself, this evening,” Caitlin counseled.

    “Really? So you do enjoy his feminine side? Well, there is a way to be assured that, Phillip’s feminine persona, will always be around,” Hester surmised.

    It was actually Hester that convinced my sister to send Phillip to the Winthrop Academy for “Permanent Feminization with Partial Sexual Adjustments.” Phillip was further restrained with ropes and a ball-gag. His head was then covered with a sack. He was given an injection of a  mild sedative, so he would still be able to walk.

    What I witnessed out the window was Phillip being abducted by a security team from the Winthrop Institute. The very next time I would see “Phillip” he would be a dazzling female named Philippa Belle. Philippa would be dressed in a floral frock and tall heels with hair in an upsweep.

    She was so elegantly splendid, slender, dainty and delectable. The occasion would be the initial practice for the Cassandra Wedding Ceremony, to be held at the Warrington Estate. Philippa and Caitlin were to be married a few weeks later, with Hester as Caitlin’s Best Woman. I would take my place dutifully, as the prettily and effeminately attired “Flower Boy.”

    It would be a lovely wedding in the usual Matriarchal, Cassandra Sisterhood Tradition. From that time on, upon each and every occasion I was to see Philippa Belle, she would appear yet more demure, dainty, feminine and even considerably more, girlishly flirtatious. Femininity suited her perfectly well, and she had really taken to it most glamorously. 

    “Hester? Will Andrea Maria be modeling at tomorrow’s fashion show?” Caitlin asked. 

    We were dining, after the “Procession of the Castrates” had been completed and this season’s “Castrato Princess” had been chosen.

    “No. The fashions being modeled Saturday will be far too womanly for Andrea’s delicate, sylphlike frame. Though I did volunteer Andrea for Hairdressing and Cosmetic services throughout the event. Andrea did quite well in the Cosmetology classes he took at Feminique over the summer. I’m quite delighted with his progress in that Genre? Aren’t I baby?” Hester asked as she gently patted my newly bobbed, bowl-cut, tresses.

    “Yes Madame. Though I couldn’t have possibly done it without your continual discipline and attention to detail,” I admitted. 

    As Hester and I left the ceremony, with me clinging to Hester’s arm, Madame Hester asked Caitlin if she and Philippa would enjoy spending the weekend with us at our newly remodeled home.

    “That is so gracious of you Hester! We were thinking of a hotel nearby as the estate is just so far from this weekend’s events. What a wonderful idea. Your home is just perfectly located,” Caitlin surmised.

    Philippa, very sweetly insisted on assisting me with breakfast the following morning. I was impressed with the cooking skills she’d obtained at the Winthrop Institute. Our Mistresses decided they would engage in a luncheon with some “Sister’, that were in, from out of town.”

    “Andrea? Why don’t you do Philippa’s hair for this evening’s fashion show? You could put it up in curlers and comb her out backstage before the show? What will you be modeling this evening, Philippa?” Hester asked.

    “Mostly lingerie and formal gowns Madame. Along with a few “Ladies Who Lunch” suit sets,” Philippa giggled coquettishly. 

    “Very nice. Well there’s no need for dinner this evening, Andrea. We’ll be lunching with our lady friends and there will be scrumptious fare, prior to, during and after the fashion show. Well, you sissies play nicely while we’re noshing with our Sisters. Tootle-do,” added Hester.

    “Why don’t I change into a comfy robe for having my hair done, Andrea?” Philippa asked.

    One of the remodeled features of the home Hester and I resided in, was a Home Beauty Salon, patterned after the one my mother had designed at the Warrington Estate House. I was getting things ready to shampoo Philippa’s hair when Philippa sashayed into the home salon, on stilted Marabou slippers, wearing a shorty, satin, pastel, floral print robe.

    She smiled, as she tossed her curls back seductively. She reached out her right hand and playfully touched my arm.

    “Darling? Could we chat? I’ve discussed this with both my Mistress Caitlin and your Mistress Hester. I need to apologize to you dear, for the terrible transgressions I committed over a year ago. Can you forgive me Andrea? I’m a completely different person now. But of course you can see that. Can’t you darling?” Philippa smiled, her left hand upon her hip.

    “Well of course Philippa. Of course I forgive you. And yes it’s obvious you’re a totally different person now,” I said, nearly choking up, and hugging her tightly to me.

    We separated from the hug, however, Philippa rested both her hands on my shoulders, batting her eyes and still smiling enticingly. 

    “Thank you darling. Just you saying that makes me feel so much better. You know what would really mean a lot to me? If you found me attractive. Do you? Do you find me attractive, Andrea?” Philippa asked, her eyes sensuously dripping with lust.

    “Well yes Philippa. Of course I find you attractive. Very attractive, actually. I mean you turned out to be an extremely stunning beauty,” I added.

    “Really? Well then, do you like what you see, now? I know with my balls sliced off, I might look a little different. But how about my breasts and hips?” Philippa asked, as she opened her robe to expose her tits, ass and her very effeminate genitalia. 

    I was startled. She had such a lovely, womanly figure. Though, of course, I’d never seen anyone missing their testicles. However, testicles on such a feminine person as Philippa would appear terribly out of place. Plus, her tiny penis was virtually non-existent. 

    I was truly wowed by her lovely shape. Philippa, just like any sissy, who had been subjected to, accelerated hormone therapy, breast implants, as well as severe corseting and foundation garment training, had developed an hourglass figure, such as was once popularized in the late, 19th century. 

    “Am I upsetting you by showing you my shapely body, Andrea? You do realize I’m flirting with you, don’t you darling? There’s nothing wrong with that is there, Andrea Maria? We are two very pretty, flirtatious sissies. Even if your Mistress does dress you up so Butch,” Philippa teased.

    “Hester does not dress me butch. Frequently people ask if I’m a girl or a sissy. Just the other day, a young girl, while in line at Merle Norman Cosmetics, asked her mother if I was a girl. It was just after, Hester and I had makeovers last Saturday,” I explained.

    “The lady didn’t know, so she asked Hester, if I was a girl or a sissy. Hester laughed and told her that of course I was a sissy. Not only that, but that I was Hester’s sissy,” I explained.

    “That’s so nice, Andrea. Andrea if you don’t kiss me soon, I’m going to kiss you,” Philippa threatened.

    I thought I could give Philippa a kiss, tell her how pretty she was and all that flirting would be over with. Then I could get on with doing Philippa’s hair. But I was wrong. When I walked up to Philippa and faced her, she pulled me to her with her arms around my waist. I felt trapped.

    When I leaned over to kiss her on her lips, her really wet, crimson lipstick, mingled with the soft, sissy-pink on my lips. It was a truly, breathtaking kiss. More so lately, I’d come to find providing beauty services to females and sissies alike to be very stimulating and erotic.

    Brushing Hester’s hair or painting her toenails made me want to have sex with her. Setting and styling the tresses of the professional models that frequented the Feminique Academy salon could be sexually arousing.

    The Salon at the Feminique Academy was an ultra-feminine, chic-chic, princess palace, so to speak. It was the type of salon that could be especially intimidating to any new sissy, making one of his or her, first visits to a salon. The Professional hairdressers that tutored at the salon were also somewhat menacing in nature, when dealing with sissies.

    So to take part in assisting one of these haughty instructors, in wrapping a perm, or applying permanent wave solution, to the tresses of any reluctant, sobbing, unnerved sissy, could be especially empowering. 

    So, when I kissed the nearly naked Philippa, prior to doing her hair, and ran my arms inside her opened, satin, floral-print robe, it became difficult to resist her amorous intentions. Her ample bosom pressed against my nearly flat, boyish chest. 

    I was wearing my Feminique Beauty School uniform of white two-inch Kitten heel pumps, a white blouse with a neck-bow, a pair of pink, ankle socks and black slacks, cropped at my calves. My penis was pressing against my panty brief.

    “Andrea Maria? Darling, I’ve never had a real boy’s penis inside of me. It would mean so much to me Andrea, if you would insert your penis into my rectum. I feel it would make me more of a female. At the Winthrop Institute there were no men, of course. The female instructors dig peg me with large, faux penises, but I never experienced the real thing,” Philippa mewled, gasping.

    “Even on our wedding night, Caitlin used a silicone-plastic dildo on me. Though she’s threatened to have me buggered by a real male, she never has. I wouldn’t mind that either. I know I can hardly consider you a true male Andrea. After all, you are a sissy-boy at best. But I know you can achieve an erection,” Philippa sighed.

    “Please, my dear Andrea Maria? Allow me to take your penis out and touch it?” Philippa begged as she pulled and clawed at my slacks and tugged at the side zipper.

    “I’ll take my slacks and panties off for you Philippa. But we must be careful. We don’t know how our Mistresses might react but I can’t believe it would be good. Help me off with my heels and socks,” I asked as I undid the girly side zip on my cropped slacks. 

    The sexually hungry Philippa helped me slide my scalloped panty brief off and then grabbed and held my penis within both of her soft, French-manicured hands. I didn’t bother removing my blouse. Compared to Philippa’s bosom, there wasn’t much to see, with my herbal induced tits.

    “Oh your panties are so pretty, Andrea. But this is cock is a lovely sight, isn’t it? I hope you don’t mind, but I’m going to kneel and suck on this little prize?” Philippa giggled as she knelt and took me into her crimson mouth.

    For never having a penis in her mouth, nor ever handling one besides her own, Philippa showed amazing skills. I had to pause to wonder if she had not been given classes at Winthrop, were she was made to suck rubber cocks? I didn’t have time to wonder very long though.

    My cock was hard as a rock and Philippa had momentarily stopped giving me a blow job, in order to tear off her satin, floral-print robe.

    “Come this way Andrea. We’ll use this massage table. I’ll bend over it, and you can fuck my bum all you desire to. I’m ready. I removed my anal-plug and lubed my rectum when I changed into my robe. Yes. I know what you’re thinking. I began planning this encounter since Caitlin suggested shopping and a luncheon,” Philippa said as she pulled me along by my penis.

    She’d taken a tube of lubricant from one of the pockets of her shorty robe, and she now slathered it all over my erect dick. She then kissed me forcefully. 

    “My goodness you’re so pretty Andrea. I know Caitlin didn’t mention shopping, but she will. She never goes anywhere, especially with lady friends, and doesn’t shop. Our Mistresses will be away for at least a few hours,” Philippa said as she bent submissively over the massage table and offered me her ass.

    “I’m all yours, Andrea Maria my love. Take me. Please take me and make me a woman. I’m so ready, Andrea,” Philippa begged as she guided my penis along, as far as she could.

    “Does that hurt Philippa? Is it uncomfortable for you?” I asked as I slowly pushed against her rectal rosebud.

    “No it doesn’t Andrea. For goodness sakes. You’re such a sissy. Push harder. Rape me. I don’t care. If the roles were reversed I’d be raping you. Oh, now that’s it,” Philippa groaned as I pushed into her rectum and slid almost half of my penis within her.

    “Very nice. You’re almost all the way in my pet. That’s even better. Oh, you’ve made it. Please Andrea. Slowly, slide in and out. I’ll get into rhythm with you darling. Put your ams around me Andrea. Oh yes, that feels so sexy. So, will you be my sexy, sissy boyfriend Andrea? Oh yum, this will be our secret,” Philippa sighed as my cock went in and out, and back and forth, within her snug rectum.

    I now squeezed her tits and she gasped sexily and groaned. She was a hot little minx. Her breasts were simply so beautiful and so plump and full. Her hips felt just wonderfully against my thighs as my penis nestled within her rectum. I’d never dreamed that anyone who had once been born a boy could turn out so womanly.

    But that was the apparent magic of the Cassandra Sisterhood  and their Academy of Feminization, the Winthrop Institute. As I rutted against Philippa’s ass-pussy, I didn’t care that what I was doing was very likely adulterous, when I considered Philippa’s marriage to my Sister Caitlin and Hester’s “Ownership” of me.

    As I could now sense my passion reaching it’s height, I gripped tightly to Philippa’s breasts and ground my groin into her plump buttocks. That was all it took. The mystery of fucking this voluptuous sissy-girl, and the exciting, prurient nature of the act, combined to cause my sperm ducts to erupt. I began to wildly spurt my hot semen well up into Philippa’s waiting anal canal. My shaking and quaking little sissy miss screamed loudly.

    Thankfully, no one could hear her. With our Mistresses gone to luncheon, Ms. Delilah, Hester’s sister, just returned to Virginia for law school, and our neighbors nowhere within hearing distance, my passionate groans and Philippa’s girlish screams were heard by our ears only.

    When I’d pumped out the last of my seed, Philippa laid over sexually exhausted upon the massage table. My penis receded from her rectum. I leaned over and kissed her neck.

    “You were wonderful Andrea. Please tell me we can do this once again? I must shower. I’ll shampoo and condition in the shower to saw you that chore. Then, my sexy, sissy boyfriend, you can do my hair. I mustn’t be too excited. I don’t want to tell any of the snobby fashion models at the show about my sissy, hairdresser boyfriend,” Philippa gurgled sexily.

    “No, please don’t Philippa. We don’t need news of this spreading among the Sisterhood,” I cautioned her, as I wiped my genitalia clean and put my panty-brief back on. 

    Crazily enough I considered showering with Philippa. However I realized I’d better shower alone. Philippa returned from the bath, smelling and looking fresh and pretty. I wasn’t yet that skilled at cutting tresses, so I simply began to roll Philippa’s hair onto curlers, using setting gel.

    As I’d been taught, I rolled the curlers tightly against her head before pinning them in place, in order to get a proper curl. Then, I used an extra-hold, Aqua-net lacquer to make certain that the wet, roller set took. After that, I covered the sprayed and jelled tresses, tightly, with a hair net.

    “What color dress or outfit are you wearing to the Fashion Show, Philippa? I want the scarf I’m using to cover your curlers and hairnet to match,” I asked prissily. 

    “Just a little black dress,” Philippa answered.

    Along the drive to the Fashion Show, in Caitlin’s Mercedes, Hester, seated in the front passenger seat, contacted the Cassandra Mater, overseeing the hairdressers and the models at the fashion show.

    “Hello? Mater Portia? This is Hester Byrne. I’m doing very well Mater. Yes we are in route to the show. We wouldn’t miss it for the world, Mater. Mater Portia, I have a request. Is it at all possible for my sissy-boy Andrea Maria to be the personal cosmetologist and wardrobe assistant, for Sister Caitlin Warrington’s sissy-wife, Philippa?” Hester asked.

    “Only of course if it would not interfere with your carefully planned script of the event Mater. Oh, that’s so kind of you Mater. Yes, some of the sissy-girls have a hairdresser that they prefer. Exactly Mater. Thank you again. Well Philippa and Andrea, you have the expressed permission of Mater Portia,” Hester stated.

    “Now you two hold hands walking into the convention hall, until you are backstage. Make sure you snack on whatever they are serving so you don’t get faint. We’ll be watching for both of you on-stage. We are at table 6. So be certain to join us for the after show banquet,” Caitlin added.

    When we reached backstage, we were shown to where Philippa would be dressing. Mater Portia, who also instructed at the Feminique  Academy spoke to me. 

    “You look very dressy this evening Andrea Maria. I assume Madame Hester chose your apparel?” Mater Portia asked.

    “Yes Ma’am, she did. I’ll let her know you complimented me,” I said.

    “I love the dark-gray flared slacks against the striking crimson cashmere top. The dark-gray bolero shrug sets everything off nicely. Even though three-inch heels aren’t ideal for dressing hair or applying cosmetics, those are the correct footwear for such a sophisticated occasion, Andrea,” Mater Portia complimented.

    Philippa was enthused about modeling. She enjoyed being in the spotlight. She told me that the sound of her name”Philippa Barrington, wife of Sister Caitlin Barrington,” filled her with excitement as she sashayed across the stage.

    It was her sensuous remarks as I attended to her hair, face and wardrobe changes that disquieted me. Apparently, Philippa had only recently had her Estrogen booster and she was still filled with sexual anxiousness. I’d had thought that after our sexual encounter over the massage table, her carnal hunger would have been quieted? It seemed though, that the opposite had occurred. 

    She was being casually flirty with some of the other models and hairdressers. When, however, we were together privately, she would subtly whisper endearing seductive insinuations towards me.

    “I’ll just bet every model here would just love a little piece of my sexy, sissy, hairdresser boyfriend? Why you’re so cute Andrea, even the Mater-in-Charge singled you out for a compliment. I have to imagine Mater Portia wants to get her hands on you?” Philippa hissed.

    “You know Andrea, what just went on in Hester’s home hair salon, is not the end of you and I sexually. You do know that, don’t you? Our relationship is barely in it’s infancy honey. I’m going to have my mouth on your cock and your penis up in my ass as often as I possibly can, sweetheart,” Philippa cooed.

    “Philippa? Please? This is not the time or the place to be discussing this. I can’t imagine a group more gossipy than a gathering of fashion models and cosmetologists. We can talk about this later. Let’s concentrate on the Fashion show. Please, Philippa?” I whispered desperately. 

    “If you say so Andrea. But don’t think for a minute that what transpired between us today, was just some sort of casual fling. Do you understand me Andrea?” Philippa asked.

    “Yes Philippa. I agree. I really did enjoy our tryst in the salon. So, if you promise to remain completely silent about our tryst, I will assure you we’ll be getting together once again at our earliest convenience,” I promised, against my better judgement. 

    “Oh Andrea, that is just so wonderful to hear. So you enjoyed me Andrea? Oh I just love our little secret,” Philippa giggled.

    “Yes Philippa. You are very enjoyable. And yes, it is our little secret. And, we must kept it the way Philippa,” I added, hopefully.

    “Yes Andrea. I agree. My lips are sealed, except where your cock is concerned,” Philippa whispered, cunningly.

    “Very well. You are on again very soon Philippa. We must get you into the  nightie and peignoir,” I added.

    For the remainder of the program, Philippa was all business, though  she did subtly rub her breasts or hips against me, seductively, from time to time. But from my experience, that really wasn’t all that unusual for a model to do with her hairdresser or makeup person during a show.

    Fashion models can be very sexual, seductive creatures. And seeing that most of the hairdressers and male makeup artists are gay, the models find it to be relatively harmless flirting. By the time the show was over with, Philippa and I couldn’t wait to dine with Caitlin and Hester.

    We found our way to table number 6, which was a quiet table for four, in front of the stage slightly to the left of center. We both picked up our purses and I grabbed my hair and makeup valise. When we were finally seated and looking at the menu, Hester was the first to speak.

    “Philippa. You were amazing on the runway tonight. Your figure and your stunning looks did so much for the apparel you modeled. We could feel your energy level from the stage darling. I’m certain everyone else could. You looked and acted like a professional model this evening,” Hester effused.

    “Well Andrea made me look and feel so very pretty and girlish,” Philippa added.

    “Andrea, when they called the support team to the stage, you were certainly one of the more beautifully dressed cosmetologists there. Hester always dresses you so prettily,” Caitlin said.

    “Why thank you Caitlin,” I smiled.

    “Do you think so Caitlin? You know I want to do something different with this hair. I’m uncertain what to do, though?” Hester added, as she played with my fluffy bangs.

    On the drive to our home, Hester changed places with Philippa, who was now seated in the front passenger seat. Caitlin had soft Jazz playing on her MP3 player. Hester pulled me closer to her in the darkened, rear seat of Caitlin’s Mercedes sedan. I snuggled submissively against her. She turned and kissed me on my cheek and then again softly, from the side, upon my lips.

    “You’re such a sweet, pretty boy. I’m taking you home and you’ll be spending the evening until the early morning light in my boudoir. I’ll be bedding you this evening, Andrea Maria. Do you think you’ll enjoy that?” Hester whispered. 

    “Oh yes, Madame. I would be so delighted to serve you in your boudoir this evening,” I gushed back to Hester in a whisper. 

    Caitlin and Philippa would also be spending the evening. Then they would travel back to the Warrington Estate in the morning. We stayed up chatting until Caitlin decided to retire for the evening and Philippa followed her to the boudoir as a trained poodle would loyally follow her owner.

    Hester pulled me to her side on the sofa. She snuggled me to her wonderful bosom before kissing me forcefully.

    “Such a darling boy. You looked lovely this evening. I’m so proud of you and the way you so obediently wear what I want you to wear. I also love that you do your hair and makeup the way I prefer it. And if people think you look far too girly or sissyish, well, I happen to prefer you that way,” Hester shrugged.

    “Come along my pet. I’m taking you to my boudoir. Don’t concern yourself with stopping by your room for sleepwear. If I want you to wear anything while you are in my bed, I’ll put you into something of my liking from my own closet. Don’t worry about removing your makeup. We can shower together in the morning,” Hester explained.

    I disrobed in Hester’s room standing to one side of the bed as she stood on the other. She reached into a dresser and came up with two nighties. One was pink and one was powder blue. She laughingly tossed me the pink nightie for me to wear. 

    As we both slipped quietly into bed, she turned out all but one small night light. As was Hester’s custom she pulled me to her and held me in her arms. Then she touched my penis which was already swelling. I’d been kept modestly aroused throughout the fashion show.

    Between Philippa’s sexual banter, and the hot looking professional models, it hadn’t been difficult to become sexually charged. For me, as a natural submissive, Hester’s commanding, domineering attitude did the rest. While Hester fondled my cock, I suckled at her breasts. 

    “You were such a good boy during our last lovemaking session, I’m going to give you a treat this evening, Andrea,” Hester promised me. 

    As soon as my cock grew to maximum proportions, Hester lubed it generously and mounted me. As she slowly lowered herself down onto my penis, she said to me, “When I am ready, I will tell you to slip your fingers in between our genitals and play with my clit. In the meantime I will screw you to the mattress,” she laughed.

    She pinned my hands back on either side of the pillow my head was laying on. Then she began an aggressive fucking motion up and down upon my cock. She was so strong and forceful that I knew no effort upon my part would be possible, for me to free my wrists from her iron-like grip. 

    “You are mine tonight and for good, Andrea Maria,” Hester grinned.

    Her movements with her pelvis and pudenda were extra stimulating. Being held down tightly by her was exciting. We were both deeply into our sexual passion. Hester released her tight grip upon my wrists. Then Hester commanded me.

    “Manipulate my clitoris with your fingers love. That’s it. Oh this will be glorious,” Hester sighed. 

    We were both very, sexually high. My ball sac and penis were at the exploding point. Hester’s breathing now came more rapidly. It wasn’t a perfect explosion but it was very close. Hester climaxed initially, gasping and sobbing. Shortly after, I had a shuddering orgasm and exploded into her pussy.

    She had always told me she used pregnancy protection and that I did not need to concern myself with spurting inside her pussy.

    “When I desire your child within my womb I will advise you as such,” Hester said in her courtroom demeanor. 

    At long last our climaxes subsided and we hugged and kissed in coital bliss. 

    “We both did that very well Andrea. Now we should sleep well,” Hester said. 

    “Thank you Madame. I always desire to do well when we make love,” I agreed.

    “Oh, you do well. If you did not, you can be assured I would tell you so,” Hester smiled.

    “Thank you Madame. Your pleasure is of utmost importance to me,” I added.

    “Sleep well, my pretty boy,” Hester said as she kissed me softly, turned away, and snugged her back and hips into my torso.

    I slept peacefully with my arms around her.

Chapter V: All in “Do” Time

    It had been a mild winter and Spring was in full bloom. Hester and I were going out for an evening together at the Country Club she had joined, since she had become a full partner at the “K” Street law firm. Unusually enough we were dating without another couple coming along with us.

    Usually we double-dated with Caitlin and Philipp, or one of the Lesbian couples from her law firm. But tonight we were solo and on our own. Hester was resplendent in a white, sequined, low-cut, mini-dress. On some occasions, such as tonight, she would really celebrate her femininity. 

    Her hair was down, just touching her shoulders, in a long, symmetrical bob haircut. She’d recently had it dyed a shimmering, reddish-blond. Her French-manicured nails were unusually girlish. I hadn’t seen her quite this femininely enchanting, except upon a handful of occasions during the three years we’d lived together.

    Of course, she’d made certain that I was sophisticatedly “chic-chic,” and dazzlingly effeminate in my own attire, coiffure and cosmetic application. Any time Hester told me to wear three-inch heels I knew the occasion was special. 

    I also knew I was going to appear, to be as girly, as any sissy possibly could  look, and still pass as a sissy-boy to most people. Besides the three-inch black pumps, I wore black, crepe, ladies’ dressy, stretch slacks and matching slip-up, knee-high hose. My “top’ was a lovely, fuzzy, form-fitting, antique-white, high-neck, cashmere sweater, with a beaded bust-line.

    At the tall collar of my pretty sweater, I wore smart, pink, neck-scarf, tied prettily to the side. The sweater was so form-fitting that it couldn’t help but show off my herbal-induced, pubescent bumps, underneath my scalloped training bra. The outline of the brassiere I wore was clearly visible. 

    However, it was my hair and prettily painted face that emphasized my effeminate subservience to my date for the evening. Over the past several months, Hester and her hairdresser had been growing, coloring and shaping my tresses, until they had reached a point where they were both very satisfied with the “look” they were attempting to achieve. The stylist was keeping the sides and back, “Pixie-short” and tapered, with a shaved nape. 

    The top and front, including my “bangs” were being allowed to grow long and thick. Then Vivienne, Hester’s cosmetologist had dyed the shortened sides and back of my tresses, to a dark brunette. However, she’d conversely lightened, the much longer and thicker hair at the top and front of my locks, to a brilliant white-blonde.

    The “two-tone” effect, of both the length and the coloring, was both striking and eye-catching, to say the least. It was very easy for me, to now be the “Center-of-Attention,” wherever we went. Finally, a few months after my twenty-second birthday, Hester took me the salon and Jessica gave me a belated, “Birthday perm.”

    In actuality, what I’d been given, was a loose, body wave. But it really didn’t matter. That evening at the country club, the hair at the top and front of my strikingly contrasted “Do” had been jelled up at the top and my lengthy, thick “bangs” fell wavily, down the side of my face, across my sharply arched, plucked and penciled-in, eyebrows.

    With a charm bracelet on my right wrist, a small hoop in each ear, a white-frost French-hombre manicure, on my lengthy fingernails, and matching white-frost lipgloss upon my lips, I was just as pretty as a picture, as I hung demurely upon Madame Hester’s left arm. Although I was blushing ear to ear, the light-pink blusher on my cheekbones, might have belied that fact.

    My lidded, downcast eyes, showed dark-gray mascara and pink shadow. I had just a touch of “White-Shoulders,” Hester’s favorite perfume, behind each ear. In my left hand I held a silver, beaded clutch.

    “You and your date look lovely this evening, Ms. Byrne. I have your favorite table reserved ma’am. Just step this way, please?” Mariska, the hostess said. 

    The tapping of my high-heels upon the oaken flooring, sounded ear-splitting to me, of course. I had not felt so self-conscious since my day in the courtroom when Hester had represented me. My probation was now over, and I knew Hester’s only real hold upon me, was her token “ownership” of me, through paperwork filed with the Cassandra Sisterhood.

    In reality, I knew those papers had no legal standing in any public court. However, her mystical aura was what now bound me to her in a relationship based upon her natural, firm dominance, over my emotional needs, as well as my dire subservience towards her. As was her want, Hester asked for one menu and ordered both my fare and her’s for the evening.

    Hester looked amazingly beautiful and was so congenial and romantic towards me. Her sentiment was truly heartfelt. It was during tea and dessert that she’d dipped into her handbag and reached across the table for my left hand. All in one motion she slipped a diamond upon my ring finger.

    “I have decided that we are to be married at the end of this summer, Andrea Maria. Just prior to your 23rd birthday. You are to become Andrea Maria Byrne. Your mother Tabitha will be coming from Spain with Count Juan Carlos. Tabitha will give you away to me,” Hester stated.

    “The wedding will be held at the Warrington Family Estate. Caitlin will stand up for me. If you prefer, Philippa may be your groom’s-maid. I’ll be wearing a simple gown and you’ll be in a tux or something similar. Your mother and I haven’t quite decided just yet. You and I will talk over where to honeymoon at a later date. Are you happy, my Andrea Maria?” Hester asked.

    I was speechless, staring down at the gorgeous, diamond engagement ring. I tossed my wavy bangs away from my eyes.

   Breathlessly, with my left hand held in the light and my right hand near my boyish bosom, I managed to say, “Yes. Yes of course I’m happy Hester. I am ecstatic. I could not be more thrilled. Oh Hester, might I hold you and kiss you?” 

    “Oh course you can, Andrea,” said Hester standing.

    I minced around to her side of the table for two. The three-inch heels, which I only wore occasionally, caused my hips to jiggle girlishly. Hester extended her arms with her lips pursed. I was batting my eyes happily. This was such a dreamy, magical moment. It was as if all of my subservient obedience had culminated, and came together, for this proposal to occur.

    In reality, of course, this wasn’t a normal marriage proposal. Hester hadn’t asked me a thing. She had told me we were to be married. Then she had added in, the where, when, who would be there, and every other fine detail down to what I’d be attired in, if anything at all. But that didn’t matter. I wanted this. I wanted Hester to pronounce her complete ownership of me down, to my last name being changed to her’s.

    I pressed my body into Hester’s. Our lips met in a warm, moist, sensual French-kiss. Her arms surrounded my slim waist. My hands gently rested upon her shoulders. When we separated from the kiss, I knew my eyes were moist and watering. The occurrence had caused such an emotional effect upon me.

    Hester now looked over my shoulder smiling. “Oh excuse us Lisette. I really should have introduced my date this evening. How thoughtless of me. Lisette, this is Andrea Maria Warrington, my live-in boyfriend of the past three years. I just proposed marriage to him and he has most gladly accepted,” Hester said, turning me around to face our waitress.

    Apparently, “Lisette” had been standing behind us as we kissed. She was also smiling, and obviously holding our dinner check.

    “Oh Ms. Byrne. How exciting. Well you won’t be getting this check Madame. I’ll be giving this to the hostess and she’ll take care of it through management. Tonight you and your very pretty and quite lucky fiancé will be dining on the country club,” Lisette smiled.

    “Oh Lisette. You don’t have to do that, for us,” Hester protested.

    “Oh, no ma’am, Ms. Byrne. It’s a standard procedure here, for such 

momentous occasions. Congratulations to both of you,” smiled Lisette.

    From that day, until the moment upon which I stated, “I do,” preparations for the wedding took precedence over just about anything else. Caitlin, Philippa and Caitlin’s household staff took care of everything and anything to do with the caterer, music, arrangements for tents, and the ceremony.

    Caitlin, Philippa and Hester decided matters such as their own hair and attire. The head partner at Hester’s law firm gave us the use of her private beach home on Jekyll Island in Georgia, for our week long honeymoon. 

    I was relieved to find out that the ceremony would not be in the mystical tradition of the Cassandra Sisterhood. A number of the wedding guests from Hester’s law firm, as well as guests from Caitlin’s Wellesley sorority weren’t members of the mysterious Sisterhood. 

    Therefore, I would not be considered the “Bride,” nor would I kneel, bare-assed, to be spanked. However, Hester would still be reserving her rights to paddle me and bugger me, during our first honeymoon evening of lovemaking. My mother and Count Juan Carlos would be flying in to Reagan Airport a full ten days prior to the wedding. They would be residing with Hester and me. 

    Mother, of course would be assisting Hester with the choosing of my “wedding trousseau” as well as my hairstyle and makeup. Up to that juncture, as we drove to the airport, I felt safe, in assuming that mother’s choices would hardly be anywhere near as effeminate as Hester’s or Caitlin’s. How wrong I was about that.

    Hester parked her Lexus SUV, in airport, short-term parking. Then we walked to the concourse where mother and Count Juan Carlos would be deplaning. I became trepidatious when I heard their flight number being announced as an incoming flight. Both mother and Count Juan Carlos had seen me dressed as an effeminate sissy “Flower Boy” at Caitlin’s wedding.

    Mother had thought my “Flower-boy” attire to be so “Chic-Chic.” In fact, she’d been thrilled to know that Caitlin was marrying a nearly, totally emasculated sissy. It was Count Juan Carlos that concerned me. I’d always felt nervous dressing so effeminately and looking so effeminate in the presence of such a masculine male.

    Whether or not a masculine man said anything to me, I always felt that they looked down upon me, and thought of me very critically. Their flight was a large International flight. However they deplaned early, as they were in of course, First Class. I saw mother, but couldn’t see Count Juan Carlos.

    Then Hester said, “There they are Andrea Maria. Don’t they both look so lovely?”

    “Where Hester? I do see mother, but where is the Count?” I asked.

    “Tabitha, your mother, has her arm around Juanita’s waist. Juanita looks sensational. They did such amazingly lovely work upon her, at the clinic in Malaga. Your mother was correct. Contessa Juanita Carlotta has been feminized just so beautifully,” Hester said mysteriously.

    Then I saw “Juanita” and she was stunning. “Wait. Who is Juanita, Hester? Is that the Count’s sister? She does look like him. I didn’t know the Count’s sister was traveling with them? I’ll need to prepare another guest boudoir and bath,” I added.

    “Goodness Andrea. Please stop being so silly? Contessa Juanita Carlotta is your Mother Tabitha’s new bride and former male spouse. Your mother found the sight of both you and Philippa Belle to be so intriguing, that she decided to feminize her own marriage partner. Welcome to the magical world of the Cassandra Sisterhood darling. Another sissy-femme has been added to our sweet, little familial clique of sissies,” Hester added, as she waved to the lovely couple, that I now knew to be my mother and the very beautiful, feminine version of the Count, turned Contessa.

    I thought now, that I would swoon? I felt myself becoming moderately dizzy. Hester must have noticed.

    “Darling are you feeling faint? You look pale,” Hester asked.

    “No dear. I’m well,” I answered, lying.

    I felt far from well. It was as if I were in shock. I’d originally been concerned that I would look like such a Beta Sissy, in the presence of Count Juan Carlos. Now I needed to be even more anxious, as to just how feminine my own mother would expect me to appear at the wedding. 

    Mother gave Hester and I such wonderfully firm hugs. As Contessa Juanita Carlotta hugged me, I could tell that she was drenched in expensive perfume. Juanita was indeed a curvaceous, stunning beauty. She bore a very slender waist, an ample bosom and well-rounded hips. The Count, of course, had been a handsome, slender male.

    Mother chose to ride in the rear seat of Hester’s SUV on the drive to our home. I’d given her the choice of the front passenger seat. On the journey home, I did note there were certain positive changes between the personalities of the Count and the Contessa. Juan Carlos had been moderately immature.

    And though he appeared to be a handsome virile man, I’d also seen him as being shy and self-conscious at times. Especially for someone who was so wealthy, as well as titled. None of this seemed true of the Contessa. Contessa Juanita was certainly more outgoing and confident.

    Although, the Contessa’s worldly knowledge, did seem to center around, beauty, fashion and entertainment gossip. What did concern me, is that Juanita Carlotta insisted to mother that she be permitted to accompany us shopping, to help choose my wedding outfit as well as my coiffure.

    “But I don’t want Andrea to outshine me at the wedding, Tabitha. Didn’t you tell me I could be your bridesmaid Hester?” Juanita chirped teasingly. 

    Mother and Juanita Carlotta, had flown into Reagan, during the middle of the week. So with Hester working weekdays, it wouldn’t  be until Saturday, before we’d all be hitting the various “specialty” shops for my “Trousseau.” 

    When Saturday did arrive, both mother and Juanita were much too excited for my tastes. Hester was her usual calm, collected self, but was gleefully smiling at my apprehensive attitude. 

    “Darling, you only get married once. Leastways you and I will only be married a single time. Once I own you, my precious doll, I’ll not be relinquishing my proprietorship of you. So relax. You won’t be looking more feminine than me, at the wedding. Maybe afterwards on our honeymoon, I may see to it that you are dolled up nice and girly. But certainly not at the nuptials. Though you might look prettier, than me?” Hester smiled.

    Every shop we entered was owned and operated by a Cassandra Sister or regularly catered to Cassandra members. So, fortunately for me, three women, choosing a wedding outfit for an already effeminately attired male, wasn’t at all that unusual. We were in “Celine’s Classical Collection’s,” when I easily overheard both mother and Juanita gasp in unison.

    “Oh my stars, Hester. There it is. That will look simply perfect upon Andrea. Especially if he’s wearing the correct hairdo,” my mother said excitedly.

    “Yes! Oh yes! It’s to die for, Tabitha. I can wait to see Andrea dressed in it,” agreed Juanita.

    Hester placed her arm around my waist and said, agreeably, “They’re correct darling. You’ll look no less than stunning in that outfit.”

    The mannequin was wearing a pair of heavily ruffled slacks. The ruffles began at her waist and fell in a triple-tiered, mock-skirt. Then the ruffles continued, tier-like and individually, five tiers each, down both pant-legs. At the waist, the slacks tied prettily to the left side,  with a bandeau-like bow.

    There was a matching bolero shrug that came with the outfit. The mannequin also wore tall, three-inch heels, a jaunty neck-scarf and a camisole top. Celine the owner, heard both mother and Juanita’s feminine squeals, and came mincing around the corner smiling.

    “Celine, do you have the slacks, the heels and the shrug in a cream shade, along with some matching, knee-high slip-up hose? What do you think ladies? What about the scarf and the cami-top in a turquoise blend, with a matching beaded clutch?” Mother Tabitha asked.

    “Perfect,” Hester and Juanita agreed simultaneously.

    “Oh, I’m certain we have that color combination. Andre is about a size 10 or 12? Let’s add a waist cinch, shall we?” Celine surmised.

    Not only did Celine’s sales girl bring along a waist cinch, but when I shamefully removed my top, Celine sent her girl scurrying off for a size “A-Cup” training brassiere. The young lady helped me on with the bra. Thankfully I wore a panty-brief, albeit a ruffled one, as I became slightly aroused.

    When the cinch was determined to be “snug” enough around my waistline, I was assisted into the remainder of the outfit. When I looked at myself, fully dressed in a full-length mirror I knew I just might not be the most femininely dressed person at the wedding.

    However, I felt I might be the most fussily dressed. It looked as if I was wearing a three-tiered mini-skirt with ruffled slacks underneath. And when I walked, the ruffled tiers on the mock-skirt, swayed along with my hips. I was going to need to spend the next ten days practicing in three-inch heels, just to be able to keep from wiggling my hips as I sashayed. 

    When I whispered to Hester, in the dressing room, about needing some high-heel practice, she mockingly added, “Don’t forget darling. I’m going to be staking my claim to you during the honeymoon. In the grand tradition of the Cassandra Sisterhood, I’ll be pegging you with a double-end dildo. So along with high heel practice you’ll need to get used to wearing an anal plug.”

    It sounded as if my hips would be jiggling as I minced down the aisle anyway. Which, might not be as bad, were I going to be dressed, coiffured and made-up to pass as a real female. But that was not the plan. It would be obvious to everyone, that I was a sissified male, effeminately dressed in delicate ladies-wear. 

    In any event, after I had modeled the outfit to everyone’s approval, the discussion of my hairstyle became the new topic of importance.

    “Might I say something ladies? I honestly think that Andrea Maria’s tresses looked sensational with that outfit. The coloring and the style appeared very compatible to me. All I would do, would be to sweep back the hair on top with some gel. Then I’d spray the long, wavy bangs in place, so that they fall across the forehead, to the right,” chimed in Celine, the dress-shop owner. 

    Everyone appeared to agree. Mother decided to chime right in.    “Hester? You could have Andrea sleep in rollers the night prior to the nuptials and have someone comb him out at the estate, just before the wedding. You know? Set the long hair on top with medium-large rollers for a smooth look. Then the bangs could be set in smaller curlers, for a windswept, wavy appearance,” mother suggested.

    That evening Hester gave me a Fleet’s enema, to flush me out and then she inserted a sizable butt plug in my rectum. It wasn’t the first plug I’d ever worn there, naturally. Mother assured Hester she would have me practice in tall heels during the week while Hester was at the office.

    Andrea will sashay beautifully down the aisle for you Hester,” mother promised. 

    By the week’s end I was doing quite well in four-inch spike heels. So walking in three-inch pumps on Saturday at the wedding, hopefully, would be a breeze. Contessa Juanita Carlotta, would watch carefully as I practiced in my heels to make suggestions on the swaying of my hips.

    The night prior to the wedding, Hester insisted I spend the evening with her in her boudoir. 

    “But darling, my hair will be full of curlers and my face with be covered in cold cream?” I protested.

    “It doesn’t matter. I didn’t say we’d be making love. I simply want to hold my future spouse possessively within my arms,,” Hester explained.

    They say girls dream of being married and often dream of their wedding day. I’m not sure what type visions they have? Of course, I never dreamed of marriage that I know of? But if I had, I would be certain, that as a male, I’d never dream of laying in the arms of my betrothed, with my hair in curlers, covered in a hairnet and scarf, and my face slathered with cold cream? 

    Nor, would I think that my curlers, hairnet and scarf, would be still in place on the drive to the site of the wedding the following day. Nor would I be awaiting for my tresses to be carefully combed out by my fiancées hairdresser. Upon arrival at my ancestral, Warrington Estate, Hester and I were separated momentarily.

    I was escorted by my “Groom’s-maid,” Philippa, to the area where I would be dressed, coiffed and made-up. Shortly after, Mother Tabitha, The Contessa Juanita Carlotta, and Vivienne, Hester’s beautician arrived.

    “Let’s get Andrea Maria properly attired while Ms. Vivienne gets her things together for hair and makeup. Juanita, Philippa, open that bath doorway so Andrea can hold onto something while we cinch him up. Andrea, please undress down to your panty-brief and cooperate for us dear?” Mother asked.

   The sisterly bonding between Contessa Juanita and Philippa was something to behold. Their maleness had been thoroughly erased, but they didn’t appear to give it a second thought. They just giggled happily, and simpered, obeying every instruction my mother gave them.

   As I exposed my herbal-induced, plump, pubescent breasts, it was embarrassing to undress to my panty, in anyone’s presence including their’s. Then when my mother fondled one of my breasts and rolled it’s nipple between her fingers I thought I might faint in embarrassment. 

    “These have grown quite prettily darling. Hmm? It’s hard to believe Hester could achieve such growth with your boyish shape, without the use of Estrogen? They’ll look lovely in this turquoise, scalloped brassiere we have for you to wear. Won’t they girls?” Mother Tabitha asked, as both Juanita and Philippa agreed.

    “It’s a shame Hester doesn’t want you to be as big-bosomed as both Philippa and Juanita, because I think you’d make such a beautiful girl. But, if she wants you to remain as a sissy-boi, well, she’s the boss in this marriage isn’t she, now? What do you think about all that, Andrea Maria?” Mother Tabitha enquired.

    “Mother, whatever Hester desires has always been the final word in our relationship. She knows better than me about such things,” I admitted. 

    Before the girls put me into the scalloped, turquoise bra, they slid the cream, patterned, knee-high, slip-up hosiery onto my shaven and waxed legs. The hosiery would only be visible at my ankles where my slacks ended and my heels began. However, Hester would see them when she undressed me for lovemaking.

    Then I stood in kitten heel evening slippers and held onto the top of the bath doorway, while mother, Juanita and Philippa all took turns tightening the stays of the turquoise, waist-slimming cinch.

    “Are you ladies still pulling on the stays? I think it’s much too tight, already?” I gasped.

    “Nonsense Andrea. You’re being wed today. You don’t want to look like some sort of fatty, standing next to your beautiful Mistress Hester. Please allow us to make these decisions for you Andrea?” Mother Tabitha scolded me.

    Finally the laces of the waist-cinch were snug enough for me to be dressed in my bra. The cinch had pushed up enough flesh to make it appear that my breasts were now slightly larger.

    “It’s a good thing I ordered this bra in an A+ cup,” my mother said.

    “Girl’s let’s get Andrea into his lovely slacks, top, heels and other accessories,” mother added. 

    Next came my cream-colored, billowy, multi-tired slacks and my turquoise, camisole top. I now stepped into the three-inch, cream high-heel pumps. The cream, Bolero shrug was fitted upon my shoulders and a turquoise scarf was tied at my neck. I was handed a turquoise clutch-bag and told to sit for hair and makeup.

    The real surprises came when mother gave me some of her own jewelry to wear and Vivienne finished off my hairstyle and makeup. Vivienne removed all the rollers of both sizes. She swept back all the hair upon the top of my head, jelled it, and pinned it in back with a diamond and pearl studded brooch. Then she swept my waved bang across my forehead to the right, and sprayed it into place.

    “Vivienne? My hair looks as if it is in an updo,” I whispered.

    “Yes, it does, Andrea Maria. I told Vivienne to do it that way. Males wear their hair in buns now. There’s nothing wrong with an updo for a wedding hairstyle. In fact that is my brooch she pinned into your hair. And here are the diamond and pearl dangle earrings that match the brooch,” Mother Tabitha added, as she handed the feminine earrings to Vivienne and removed my small gold hoops. 

    Lastly, Mother Tabitha directed Vivienne on how she wanted my makeup applied. Just listening to her told me my face was going to be much too pretty and feminine. Before I could protest though, my beautiful Mistress-Bride, Hester walked into the dressing area, gorgeously resplendent in her own upswept “do,” and her perfectly fitted, classically simplistic, but radiant wedding gown. 

 Her gorgeous mini-dress gown, showed off her stunning legs to distraction. The “updo” and her makeup highlighted her regal cheekbones and her mystical emerald eyes. She indeed looked like a Nordic Queen. I was spellbound.

    “Hester, you look so majestically lustrous,” I gasped. 

    “Well I had hoped you would notice Andrea,” she smiled.

    “Hester, do you think Andrea’s makeup is too heavy, right now?” Mother Tabitha asked.

    “Oh, I don’t know? I’m wearing a bit more makeup than I would usually put on. Even for a special evening date occasion. A little bit too much makeup can’t hurt for such a festive occasion as this. Can it?” Hester opined.

    I was doomed. I’d been hoping for just a touch of pearl-white or pink gloss. Instead, Vivienne used a darker shade of strawberry upon my lips. My eyes were highlighted with Sienna mascara and my cheeks were done in a peach blush. When I stood up and swayed to the full-length mirror, the diamond and pearl teardrop earrings tickled my neck.

    Between the plug in my rectum and my three-inch heels, it was difficult not to jiggle and sway down the aisle. The tiered slacks rustled fussily as I walked. I felt so very self conscious standing there in front of everyone waiting for Hester to arrive at the altar.

    The Wedding “Chapel” was in an outdoor tent, separate from the tent where the reception would be held. Philippa, standing next to me, leaned over and whispered as Hester made her entrance to the oohs and aah’s of the people assembled in the chapel. 

    “She’s so lovely Andrea. You’re pretty also. But don’t be concerned. Today she looks even more feminine than you do,” Philippa assured me.

    The only concessions to the Cassandra Sisterhood in the ceremony, occurred when the Justice of the Peace, a Cassandra member, said, “I now pronounce you wife and partner. Hester, you may kiss your spouse.”

    Hester was also given the plain wedding band by Caitlin. Though Hester slipped a diamond encrusted band, upon my finger. At the reception I was quite popular and a curiosity among the ladies present. Not all the women who worked at the “K” Street law firm with Hester were Cassandra Members. Though they all were feminists.

    Some simply had househusbands or boyfriends at home taking care of the house while they did legal work. Others, like Hester had sissy-spouses and the rest had sissy-wives. Even those with simple Househusband’s at home came up to me to chat.

    “Well Hester did tell me she had a living doll at home Andrea, but I had no idea. Well, I’ll be paying for a dance with you, honey,” one woman said.

    In fact, several female co-workers paid Hester whatever the going fee was, to dance with me. The normal men present at the wedding, however, shunned me and either looked at me suspiciously or with contempt. I was used to that by now.

    I had originally thought that we would be flying to Savannah, Georgia in the morning, and renting a car to drive to Saint Simons Island. But there was a change of plans that I found out about at the last minute.

    “We’ll be leaving the reception around 4 P.M. Andrea. Regina, the senior partner, is allowing us the use of the Corporate Jet to fly from Dulles to Savannah. There will be a corporate luxury sedan waiting for us there. We’ll even have private baggage handlers. Everything will be taken care of. We should be at Regina’s beach home by 9 P.M.” Hester explained.

    “We’ll just sleep in our underthings and unpack in the A.M.” Hester added.

    Indeed it was a hectic few hours from the estate, to Dulles, to Savannah, and then to Saint Simons. We left our luggage in the living room, showered, and were in bed by 11 P.M. It was around 5 A.M. that I felt Hester’s hand on my penis.

    “Are you awake dear?” Hester asked.

    “Yes, that feels very nice,” I sighed.

    “Well let me know when you are truly awake. Because I need to perform the Cassandra Consummation Ritual darling,” Hester replied.

    “The what?” I asked.

    “Darling, I have obligations to the Sisterhood. I took an oath you know? I cannot let my Sister’s down, nor tell them I performed the Consummation when I did not. You are to be paddled to my satisfaction. Then your rectum is to be pegged until you climax,” Hester added, turning on the bedroom lights.

    “Oh please Hester, couldn’t we wait?” I asked.

    “There is no time like the present, Cupcake,” Hester said, as she tied my wrists together, snugly, with a scarf. Then she pulled me to the headboard of the bed. She then fastened the scarf holding my wrists, to the top of a post, at the center of the headboard.

    “Your paddling will be done first,” Hester announced.

    “This has to be done. Don’t fret about any screaming or crying you might do. This home is surrounded on all sides by tress and shrubbery. Plus the surf is just so noisy from the morning breezes. In fact, I expect you to scream and cry,” Hester commented.

    “Between this paddling, and a proper rectal pegging, you’ll fully understand that you belong to me as well as the Sisterhood. Not that you already don’t realize the truth of that, Andrea,” she said as the first strike of the paddle sounded upon my naked ass.

    Indeed I did scream. I pulled frantically at the scarf tightly tied to my wrists to try and free myself. I twisted and turned and wiggled my butt in a futile attempt to avoid the accurate strikes of the laughing Hester’s paddle.

    “My goodness, you’re kicking and screaming just like a girl would. I sort of find that to be so cute,” mocked Hester.

    “Oh please, please, Mistress Hester. I’ll always behave. I’ll always honor you ma’am. I’ll always dress and act as you prefer me to act ma’am. Please my dear Hester. This is so painful!” I cried out as she finally stopped.

    “Well lets hope you have kept that butt plug in place as much as possible? I put that  inside of you to keep you nice and open for this occasion. I hope you enjoy this as much as I am going to enjoy it? Again, I don’t mind you squealing like a girl at all. I think it’s cute,” Hester laughed as she removed the butt plug and lubricated me liberally. 

    When I tried turning around to see what she was doing with the double end dildo she hissed at me.

     “Don’t you dare look. Keep your eyes straight ahead. I’ll screw you nice and slow and easy to begin with. Then we’ll pick up the pace. Nice deep breath honey. In and out. In and out. Good boy!” Hester exclaimed. 

    As she entered me, she moved in closer and reached around and fondled the cute, plump, little bumps on my chest. She was quite happy of the progress I’d made, from the herbal-pack treatments I received from the female, Asian Herbalist, Ms. Jasmine Ling. Hester enjoyed the slight, feminizing touch given to me, by having me grow small, but obvious tits for her sexual enjoyment.

    My boobs were boyish enough to keep people guessing, but girlish enough to make me feel very effeminate. “Effective effeminacy” was how Hester referred to my small boobs. As she moved in and out of my ass with her dildo, and rubbed my tits, I whimpered prissily. 

    Hester should her appreciation of my simpering with gurgling laughter. “What a sweet, effeminate sissy I’ve married. It makes me so happy. You’ll be so easy for Mummy to control. Won’t you precious?” Hester asked.

    “Yes Hester. I’ll always submit to you,” I mewled.

    The feeling of her screwing me, fondling my little tits, and occasionally tapping my prostate and playing with my cock, really stimulated me. Soon the friction against my prostate and Hester’s manipulation of my cock, increased. The depth of Hester’s breathing was also increasing.****

    Her end of the double-end dildo had small asperities built into it, to stimulate her clitoris. My prostate as well as my penis were being stimulated masterfully by Hester. I could hear Hester moaning and finally heard her gasp as she pumped faster into my anus. Next I could feel my penis flex.

    I spurted wildly and simpered tearfully. It was such an emotional release for me. I realized how much of my masculinity I’d given to this woman and wondered how much more she would take. I also knew I wouldn’t try to stop her. Less than 24 hours ago I’d traipsed down the aisle for her, in high-heels and hose.

    I recall that I wore ladies’ slacks, a female top and a dainty bolero. My face was painted and my hair “done.” Now, after barely a night’s sleep, I’d been tied and restrained at our honeymoon bed’s headboard. Then I’d been paddled and buggered as only a sissy would permit. As I sobbed, Hester finally untied me.

    Hester had me lay beside her and lick my sperm off of her fingers. Then she hugged me and allowed me to suckle at her womanly bosom. I “nursed” as if she were my “Mummy.”

    “There, there sweetie. Now the consummation is all over, baby. Now you’ll really get to prove your loyalty to me,” Hester said, mysteriously.

    Today, I can only imagine that the “Proof of Loyalty” Hester alluded to, included the wearing of the the “Honeymoon Trousseau” she, or more likely my Mother Tabitha, had packed for me to wear at Saint Simon’s Island?

    After I had showered, I put on a frilly ladies’ robe and checked the refrigerator. It was well stocked, as was the pantry. Hester had predicted that. 

    “Regina does everything first class. If you check the liquor cabinet I’m certain you’ll find nothing but top-shelf brands,” Hester added as I prepared our breakfast.

    “I’ll shower now. You can bathe me this evening prior to our making love. I intend to put you through your paces this week Andrea,” Hester stated as she sashayed into the large, Master Bath.

    It was when I opened our luggage, to unpack our things, that I realized that the suitcases belonging to me were packed with attire that was even more sissyish than what Hester would normally have me wear. I slipped into a panty brief and realized I’d likely need a bra.

    The growth in my breasts, from the herbal treatments, now appeared to have maximized in the past month preceding the wedding. While in panties and bra, I hung in the closets what belonged there, and put the remainder of the clothing in dresser drawers. Cosmetics I placed on the vanity.

    “Having trouble finding something to wear, precious?” Hester asked.

    “Hester. Please forgive me. I’m not complaining. However there really are only tight short-shorts, ruffled summer blouses, crop tops, beach wraps and a few rompers for me to wear,” I said.

    “Did you expect slacks and blazers? It’s still summer. Especially this far south. You’ll notice there are also one-piece swimsuits in your suitcase. Your tits have become too prominent for you to go to the beach in male swimwear. Get used to it honey,” Hester said.

    “Wear that mixed print romper with some kitten-heel, strap beach sandals. Carry that cute, seagrass tote. These sunglasses are from the Jessica Simpson collection. Your mother gave them to me to give to you,” Hester said.

    “Look, if you’re uncomfortable being outed as a sissy, well, we’ll go easy on you. After all, it is our honeymoon, sweetie. You can pass. Your voice is soft and dulcet enough. You’ve been heading that way anyway. We’ll just be two girls together, having fun,” Hester added.

    “I can do that Hester. But I’m concerned. There might be two guys out having fun and I don’t want to be hit on. Could we be two girls, together, as a couple, on their honeymoon? Or at least act that way?” I asked, nervously.

    “Oh. That’s so sweet. You want to pass as a couple of sexy, lipstick lesbians, don’t you? Why not? This is the US South, but this is a hip vacation area. Maybe we can find a gay club or two? Okay, but I’m the dominant one,” Hester insisted. 

    Not that I could play the role of anything but a submissive. Walking thru town wasn’t bad. I moved my hips a little more than I would, and I pursed my lips more prissily. Hester told me it would be wise to fix my lipstick when we stopped to eat. As usual, Hester ordered my food.

    Hester also reached across the table and put her hands affectionately over mine. In fact she did that whenever we ate out during our honeymoon. It wasn’t that much different pretending we were a gay couple, versus our normal “Mistress/Sissy” relationship. 

    Our first day at the beach was trying but memorable. After breakfast as we got ready, I balked at wearing the one-piece, beige, ladies’ swimsuit she laid out for me.

    “Now stop being silly, Andrea. I know what’s bothering you and that is why I brought this. Your mother gave me this to give you to wear with a swimsuit. It’s an elastic brief. It will hide your genitalia sufficiently, so you can put on that swimwear. We can even chill your genitalia and stuff things up inside you, if you so desire?” Hester asked.

    “Can we try it without being chilled?” I asked.

    “Of course. You’re not all that big anyway,” Hester remarked.

    “Now put the suit on. There. Wear those beach sandals and the wrap. Carry that beach bag and you’ll be all set. I expect you to put lotion on my skin at the beach, just like any sweet, sexy Lesbian would, Andrea,” Hester smiled. 

    The walk to the beach from Regina’s beachfront cottage was very brief. Hester and I picked a secluded but sunny spot. We set the blanket and the chairs down. Then Hester had me put suntan lotion all over her. I removed my beach wrap and Hester coated me.

    Next, while Hester laid back on the beach lounger, she had me paint her fingers and toes. Then she allowed me to lay on my lounger. While I was laying down, she knelt next to my lounger and kissed me softly on the lips.

    “Such a sexy, Lesbian girlfriend you are, Andrea. I love girls that like to paint my toes. Now remember. If we go into the water, we wade out, and only get wet up to our mid-thighs. Sexy chicks never get their suits or their hair wet. Only swimsuit models do that,” Hester reminded me. 

    After the beach, we took a walk to a shopping area and then had lunch. We still had on our beach sandals, wide-brimmed sun hats, swimsuits, sunglasses, and beach wraps. When we walked into a restaurant, Hester spoke to the young lady hostessing. 

    “Can we come in wearing our swimsuits, Miss?” Hester asked.

    “With those pretty beach wraps on? Of course. A couple of pretty ladies like you two will probably bring plenty of boys in off the streets,” the Hostess teased.

    “Probably not, when they find out we’re here on our honeymoon,” Hester added.

    “Oh really? That’s so cool. My oldest sister is married to a female designer in New York. I think that is just so special. Well congratulations girls,” the waitress smiled.

    After a nap and before dinner, Hester told me I was going to be giving her a bath. Once I’d drawn her bath, and she’d slid sexily into the foamy bubbles, she spoke to me.

    “When you are done bathing me, drying me and powdering me, you may drain some of the water, reheat it and bathe in the same water I bathed in. Do you recall the first bath you ever gave me, my Andrea Maria? Did you ever wonder about the circumstances of all of that?” Hester asked.

    “Yes, I do recall Madame. Yes. I remember that evening. I don’t exactly know what you mean by circumstances though?” I said.

    “Of course not. I’ll be clearer. That day in court. The day I represented you. I knew you were scared. I saw how very pretty you were and you still are very pretty. Right then, I decided you were to be mine. It was all set up that you were to become Caitlin’s sissy maid of course,” Hester added.

    “But I planned on making you all mine as soon as I could. Philippa’s poor judgement just happened to play into my hands. When I requested you to be my maid while I stayed at the estate, I think Caitlin knew what I had in mind. I don’t know how soon she would have cooperated with me though?” Hester paused.

    “In spite of my incantation, I don’t think you’ve ever forgotten the events of that night, have you, Andrea?” Hester asked, suspiciously.

    “No Madame. I have not. But I’ve never told a soul,” I added.

    “I believe you. Again, when Philippa erred and so terribly frightened Caitlin, I took advantage of that situation, also. I asked Caitlin if she really wanted two sissies on her hands that needed to be fully-feminized?” Hester remarked.

    “Whether you realize this or not, I will tell you. My actions have saved, on your behalf, your trust fund, your inheritance investment portfolio, and your co-ownership of the Warrington Estate. We’ll discuss that later. However, when you turn twenty-three, all of that will be your’s, Andrea Maria,” Hester explained.

    “I won’t know what to do with all of that Madame. I’m uneducated and highly dependent upon you, my love. I dearly desire to serve you, my Mistress,” I told Hester.

    “And you have served me and continue to serve me well, my dear. And you are educated. You’ve had classes in cosmetology, fashion modeling, and ballet lessons. Did you know that the Feminique Academy will soon open a Secretarial Studies tutorship?” Hester asked

     Possibly you could enroll and further serve me in that capacity one day, Andrea?” Hester smiled as I continued to bathe her in the most intimate of spots.

    “Hmm? I think you should dry me, powder me and put body lotion on my skin. Then I’ll relax in our honeymoon bed, and you can join me after you have bathed and are smelling beautifully. Don’t forget to put on fresh lipstick. Remember, we are Lipstick Lesbians this week,” Hester teased.

    I did remember. When I arrived in the boudoir Hester had the pinkest nighty I’d ever seen, laid out for me. I was wearing the reddest lipstick I could find and it pleased Hester. I slipped into bed and as always, Hester’s arms surrounded me.

    “Good girl. Sissy lesbians, wearing bright-red lipstick should always lick their Madame’s pussy,” Hester said as she directed my head between her legs.

    I loved having my mouth between Hester’s legs. Especially when her pussy was newly out of the bathtub and had been freshly, powdered, scented with lotion and perfumed. I licked her thighs and moved to her pudenda, labia and her clitoris. As I tickled her “love-button” with my tongue I could feel her tense-up.

    Then she easily calmed, as I nibbled her clit. I used my fingers carefully to keep her pussy-lips parted. I knew I had her warmed up when she grabbed my hair and pulled me to her puss more tightly. Then when she got really passionate, she pushed me away and turned me onto my back.

    “I was thinking of having you get me off with your mouth. Then I was going to have you kneel on all fours. And while I masturbated you, I was going to move my middle finger in and out of your ass, and make you climax that way. Now, I’m just going to fuck you until you can’t stand it,” Hester laughed. 

    She had me on my back. Then she mounted my erect penis. She moved rapidly up and down on my cock. Hester was really inspired. She has always been a strong, forceful female. She really took charge that night.

    “Get your fingers in between us sissy. That’s a good girl. I think it’s cute that you’re being a sissy, lesbian girl, for me this week,” Hester said.

    When Hester was ready she shouted, “Harder, faster!”

    I rubbed her clit forcefully after wetting my fingers with spittle and pussy juice. Hester began to shake and quiver. Just the feeling of her pussy muscles snapping and squeezing on my cock, set me off. I began to ejaculate forcefully into her cunt.

    My cock spasmed wildly. Hester felt me pumping and she grimaced with pleasure. Very soon we were laying in each other’s arms kissing in coital bliss. I awoke about an hour later, chilled some wine and began to make dinner. For the rest of the vacation we play-acted as two lesbians on our honeymoon. 

    The evening prior to leaving, Hester asked me, “Would you like to drive to Savannah and meet the corporate jet as two girls? Nobody will say a thing. I mean the head partner at the firm, Regina is a Lesbian, married to a much younger female partner. It’s up to you honey.”

    I decided I would do that. We left the island around 10 AM and the jet took off by 1 PM. We landed at Dulles by four in the afternoon and were home by 6. I wore a skirt, blouse and heels the entire trip. 

    With our honeymoon over and Hester back to work, I went back to being Hester’s sissy, toy-boy. As my 23rd birthday approached, Hester told me we would be going to visit Caitlin and Philippa for a little celebration, on the following Saturday, two days after my birthday.

    Hester took her briefcase along, with quite a few papers, folders and binders inside. After cake and ice cream and a “Happy Birthday” sing-along, Caitlin instructed Philippa on what to do.

    “Honey, you can take care of this mess. Our birthday boy here will be serving tea to Hester and I while we look over some papers. After you’ve cleaned up you can pick up where you left off on the ironing yesterday,” Caitlin ordered.

    I served the tea and was told by Hester to wait as Caitlin looked over some legal papers.

    “Okay Hester. Tell me what the hell I’m looking at?” Caitlin asked.

    “That is simply a document stating that we all agree that the person formerly named Andrew Martin Warrington is now named Andrea Maria Byrne. You can sign right here under your printed name. Next is a paper saying that we all agree that Andrea Maria Byrne is now twenty-three years-of-age and is now married to someone you approve of,” Hester replied.

    “Well yes. I agree to that. I strongly approve of the marriage,” Caitlin said.

    “Well then, once these papers are notarized and filed, Andrea will regain control of his Trust Fund, Inheritance Investment Portfolio and co-ownership of this estate,” Hester explained.

    “Okay? Is that it? Now, do you and Andrea intend to move in with Philippa and me?” Caitlin asked.

    “Heavens no. The upkeep on this place, even without the servants is astronomical. Do you realize the money you’d save buying a more modern, scaled down estate with smaller gardens and some stables? You’re also paying taxes on forests and fields that have lain fallow for decades and run-down out-buildings, Caitlin,” Hester shrugged.

    “And if I bought a place such as you describe, what would I do with this estate?” Caitlin asked.

    “Sell it to the Winthrop Foundation. They would turn it into a Feminization Academy. The mansion, gardens and forests would remain intact, and be maintained. Of course the mansion would then serve as the main offices and the Headmistress’s Living space,” Hester explained.

    “Between the space occupied by the old outbuildings and the fields that haven’t been farmed for over 40 years, there would be enough space for classroom buildings and dorms. The gardens would remain as they are and the forests would have the proper thinning and upkeep,” Hester added.

    “Okay Hester. What have you been up to? What’s all this about the Winthrop Foundation and a Sissy Academy?” Caitlin asked.

    “I’ve been in communication with the Foundation. I even have an offer that comes with the full blessing of the Winthrop sisters, Lilith and Matilda. Would you like to see it?” Hester asked.

    “Please?” Caitlin said, with her left hand held out.

    Hester handed her a page from a folder. Caitlin’s eyes grew wide.

    “Gracious. Are they serious?” Caitlin asked.

    “Very much so. They are so certain you and Andrea would accept they’ve asked me to hire an architect and have an artist’s conception done. I have that,” Hester explained as she put the drawing in front of Caitlin.

    “It’s beautiful. Hmm. Why would they need two salons and two dining areas?” Caitlin asked.

    “One of each for the staff and students,” I would guess.

    “Have you seen this offer Andrea Maria?” Caitlin asked.

    “Yes I have. Last night,” I admitted.

    “And what do you think? Tell me,” Caitlin insisted. I was surprised she’d care what I thought.

    “If Hester thinks it is a good idea and a good offer, than it must be,” I said.

    “Spoken just like a well-trained puppy dog. But, as things stand right now, I agree. I’ll have to let the servants and the security team go, though,” Caitlin admitted.

    “The Winthrop Foundation will employ your servants and security detail at the Academy, if they prefer that. After all, they have 100% female staffing,” Hester smiled.

    I’m so very proud to be married to Hester. She thinks of everything.

    Hester and I were at the dedication of the facility along with Caitlin and Philippa. It wasn’t yet completed. The dedication ceremony date had been set to be compatible with the busy schedules of the Winthrop Sisters, Lilith and Matilda. They were younger than I had thought.

    Lilith looked to be in her late 30’s and Matilda must have been a few years younger at least. Matilda spoke at the dedication. As the dedication wound down and the construction workers went back on the job, a woman walked up to Hester and I.

    “Hello. I asked who Hester Byrne was and I was told that you were her, ma’am. I’m Lilith Winthrop, President and CEO of the foundation. My sister Matilda who spoke, is the VP and CFO. We’re both the Great-Great-Granddaughters of Cassandra Winthrop, the founder of the Sisterhood and the Foundation,” Lilith remarked.

    “I’m thrilled we could finally meet. We’ve spoken several times over the phone. We’re all thrilled over the work you’ve done to put this together,” Lilith added.

    “It was my pleasure Ms. Winthrop. This is my loyal spouse, Andrea Maria. He was one of two heirs to the property. He and his sister Caitlin signed the papers that finalized the sale,” Hester replied.

    “Wonderful and he’s very cute. Actually he’s pretty,” Lilith teased.

    “There is at least one office, inside the Estate mansion, that is completed. I was told we could use it. I’d like to make an offer to you Ms. Byrne,” Lilith nodded.

    Hester agreed and we walked inside. We sat at a roundtable. When the construction foreman left the room and the door locked behind him, Lilith Winthrop spoke.

    “Ms. Byrne. My sister, myself, plus numerous high-placed members of the Foundation and of the Sisterhood were very impressed with how smoothly you put this deal together. Now, of course you know we had you checked out throughly. We realize we likely cannot match your law-firm salary, though we’ll try. Still, we all agree we’d love for you to become Headmistress of The Winthrop Institute at Warrington Gardens. We hope you’ll at least consider it?” Lilith Winthrop stated.

    “Truthfully, I would like to think about it, Ms. Winthrop. I’m actually planning on having my spouse enroll in a Secretarial Studies Curriculum. Should I accept, would it be possible for Andrea Maria to accompany me as my Administrative Assistant?” Hester asked to my surprise. 

    “Anything you’d like Ms. Byrne. Although, there can be no males at a Winthrop Academy. Thusly, Andrea Maria would have be attired fully as a female. Your spouse would also need to be known as your wife. This would include while on campus or at any school function,” Ms. Winthrop explained.

    “Very well then. That will be no problem. Will it Andrea? When do you need an answer Ms. Winthrop?” Hester asked.

    “We’re in no rush. We’re in the finish stages of construction and that must be perfect. I’ll continue to interview in case you turn my offer down. This booklet is a complete job description, including  the offered salary and perks. Is 30 days enough time to make a decision? Lilith asked.

    “Ten days is more than enough. I should be back with you in a week’s time, Ms. Winthrop.

    “Thank you, and call me Lilith,” Ms. Winthrop added.

    “And you may call me Hester, Lilith,” Hester smiled.

    We were nearly home when I finally asked Hester, “Would you really give up your law career darling? To be the Headmistress at a Winthrop School?”

    “I might. Especially if it meant we’d have to keep you in skirts and dresses at work, Andrea,” Hester shrugged.

The Denouement: The Gardens

    I still did not believe that Hester had put her Legal career on hold, to become the Headmistress of an Academy, that existed solely for the training and further feminization of sissies. My former, ancestral home was now called, “The Winthrop Institute at Warrington Gardens.” During the school year, Monday thru Friday, Hester and I would reside there. 

    In the rear of the Old Ancestral Warrington Mansion, was a 3000 plus, square foot residence, where Hester and I would live, much of the time, when classes were in session. I would work as Hester’s Admin, play the role of her wife, and dress, as well as act the part of a submissive, devoted female. Leastways, I would do that, whenever we were on campus. I would even be referred to as “Miss Andrea Maria” by the students as well as the staff.

    Regina Chalmers, the head partner at Hester’s law firm, was thrilled that Hester took the Headmistress position. Regina was an ardent feminist and a 3rd generation Cassandra Member. On the firm’s letterhead, Hester was now listed as “Hester Byrne, Partner in Abstentia, Chief Legal Consultant. Currently Headmistress of Winthrop Academy at Warrington Gardens.” 

    Regina believed this would endear the Firm to any and all, wealthy, powerful feminists and likeminded Cassandra members as well. 

    Regina’s firm also began to represent the Winthrop Foundation regionally, once Hester became Headmistress. From the day Hester accepted the position, my life began to change immeasurably.

    “Darling, it would behoove you to begin a very steady, concentrated effort to transition into a thorough feminine manner of dress, coiffure and lifestyle. You are to appear to be a loyal, devoted subservient wife, who’s only concern is the advancement of her spouse’s career,” Hester demanded.

    “Your first efforts of course, will be a new, distinct manner of dress. I’ll expect you in heels at all times. You should begin to grow your tresses much longer or at least to your shoulders. Your voice modulation and mannerisms should reflect extraordinary femininity,” Hester intoned me.

    And so, I strove for perfection in my quest to become, Miss Andrea Maria Byrne, dutiful wife and secretary of Winthrop Academy Headmistress, Madame Hester Byrne. Did I have any other choices? I think not. 

    One of my first, unofficial “duties,” which Hester expected me to perform, was having my hair “done,” along with a full makeover, at the Winthrop Academy Staff Salon. With my hair nearly to my shoulders, Hester decreed I should subject myself to a distinct style and coloring.

    “A blonde-frost color would look perfect on you Andrea. You’re hair is also at the correct length for a sharply angled inverted bob. At a later date I’d recommend a stacked perm or some similar type of body wave,” Hester explained. 

    The stylist was effusive in her greeting of me.

    “Oh, good morning Miss Andrea. We’re all so very, very thrilled to see you. I am Kathleen and I’ll be your cosmetologist today. You can’t imagine just how excited everyone at the school is, to have Madame Hester, as our very first Headmistress here at Warrington Gardens,” Kathleen said excitedly.    

    “I spoke with our salon manager, Celeste Holmes, just prior to your arrival, Miss Andrea. You’re in for a cut, shaping and coloring. You’ll be a lovely, Frosted Blonde, with a delightful, long, inverted bob and a shaved nape, when I’m done with you dear,” Kathleen said chirpily.

    “Within the next two weeks, prior to the start of classes, we also have you coming in for a full, bikini, leg and brow waxing. Then a facial and mani/pedi. It appears Ms. Hester will be keeping you pretty and glamorous,” Kathleen smiled.

    “I love what you’re wearing Miss Andrea. You really do look the part of the Headmistress’s wife,” Kathleen said, nicely.

    “Why thank you Kathleen,” I said.

    I was wearing tall, pink, three-and-a-half-inch heels with an white A-line, swing skirt, and a matching, white, high-collar white blouse with lacy cuffs. 

    “After your shampoo I want to take the time to have you set with a hot-oil conditioning treatment before we frost your hair. You’re already close to the light-blond Madame Hester desires for you, Miss Andrea. The color I have mixed will look just great on you,” Kathleen promised. 

    Kathleen did a fantastic job shaping my inverted bob and frosting my hair, especially the tips. I also loved the way she shaved my nape.

    “Kathleen I love this. I can’t wait for Hester to see this!” I exclaimed.

    “Why not join her for lunch? The staff cafe is opened now,” Kathleen added.

    I didn’t see Hester there in the Cafe but I did see Mallory Hampton, the Assistant Headmistress Hester had just hired. I took my tray of green tea, celery and carrot sticks over to her table.

    “Ms. Hampton? Could I join you?” I asked.

    “Of course Andrea. I’m not going to snub my boss’s wife, my first day on the job,” Mallory joked.

    “You know? Maybe I should tell you that Madame Hester just finished her lunch and went back to her office. She said you were likely still at the salon having your hair done. It looks fantastic, by the way. I think I’ll make an appointment for later in the week,” Mallory said.

    “Thank you Ms. Mallory. I hope Hester likes it?” I said.

    “I believe she will, princess,” Mallory teased.

    Once I was done with my lunch, I returned my tray, and Mallory and I walked back together. Her office was on the second floor. I walked past my desk to Hester’s office and knocked.

    “Come in please. Oh my. Andrea darling. Please do come in. Wait,” Hester said, taking a small, “Do not disturb” sign with her. Hester placed the sign on the outside door handle and locked the door from the inside. Smiling, she returned, and sat on the top of her desk.

    “Darling, come here to me. You look absolutely lovely, my dear,” Hester said, taking me into her arms and kissing me.

    “Hester! Well thank you. I guess I should go to the beauty parlor more frequently?” I gasped.

    “Yes. Maybe so. And you will be going darling. Stay here close to me, lover girl. Yum. This is so nice. My sexy little secretary. Did you wonder why I locked the door princess? Because I’m going to bend you over my desk and screw you honey,” Hester smiled.

    “Hester, stop teasing me. I’ve actually got some paperwork to do that you gave me to complete,” I laughed.

    “It can wait doll. Your sexy boss wants some sissy ass, honey-bun. Your sexy boss that saved you from being a little jail-whore over four years ago, wants to bang your ass-pussy,” Hester said, holding tightly to my wrists.

    “Hester. Were you drinking at lunch? Ouch! Hester, you’re hurting my wrists,” I gasped.

    “Oh, I’m so sorry. Mummy doesn’t want to hurt her sissy-girl. You don’t remember what I told you that day, when you and I walked off to the side while the judge deliberated your fate? How the big jail stud, would turn you out among his friends?” Hester asked.

    “Yes, I recall that. Hester why are you bringing this up?” I asked, futilely struggling against her.

    “Kneel down honey. I want to treat you like my sexy secretary. You’re going to suck my cock, before I screw you,” Hester demanded.

    Hester slid off her slacks and panties before she took a double-end dildo from her desk, lubed it and slid it slowly into her pussy.

    “This is what it’s like being the secretary of a big, stud, boss. Get my cock nice and wet before I stick it in your ass, sissy,” Hester demanded.

    “Yes Hester, I will. I would love to Hester,” I said, kneeling and licking the end of her big silicone cock.

    I licked her cock and fondled the plastic balls. Hester ran her fingers thru my newly colored and shaped bob. She tickled me under my throat while I licked her plastic cock.

    “Okay honey. Now I’m nice and slick and wet. Get those panties down and lean over my desk. That’s a girl. Get that fat ass up in the air for Mummy’s big cock. Oh good girl. Here’s some greasy lube for Mummy’s big girl, honey,” Hester said.

    “Just think of how often we can do this baby? Now that you’re Mummy’s big girl secretary. Sexy secretaries have been getting to do this in the workplace for ages. Now you get to do it with your sexy boss honey. But this is much better than having to do it for an entire cell-block of big, muscular studs. Isn’t it girl?” Hester asked.

    “Yes ma’am, Madame Hester, it is better. Much better. And I’m so thankful you thought I was so pretty, that day in court, that I could one day be your girlfriend. Oh that’s so good Madame. Please fuck me more?” I begged as she shoved her silicone cock deep into my tight rectum.

    “And now you’re my wife. What a lucky girl you are, aren’t you, Andrea Maria?” Hester asked.

    “Yes ma’am. I am  a lucky girl. I’m ever so, very lucky,” I again gasped loudly. 

    Here I was, in my once ancestral home, where I was, at one time, destined to be the Lord of the Manor. I wasn’t much more than one-story below the very same bedroom, where I once took a sexy, little maid to bed with me. But instead of now being the predator, I was the preyed upon. I was bent over a desk. My face was painted, flamboyantly and girlishly. My hair was in the most feminine of hair designs and colored in a decidedly feminine shade.

    The woman I was married to, had a plastic cock up my ass. She was fucking me. I now worked for her as her sexy, sissy, secretary. The entire picture consumed me and the thought of just how subservient I was, overwhelmed me, to the point that I burst into a shuddering climax. 

    As my cock gushed and spurted, my domineering spouse gripped my penis with both of her strong hands. At last, I nearly passed out upon the desk from the most powerful of ejaculations. Hester kept pumping her faux, double-ended cock in and out of my ass until she also climaxed.

    As she gasped in ecstasy, she placed, her gooey, sperm covered fingers, of both of her hands into my mouth. “Lick these clean for me, would you, girly, girl?” Hester requested.

    I licked her fingers clean, until she was satisfied. She pulled her faux-penis from my ass and turned me around. “You were wonderful, sissy-girl. Such a good girl I have,” she said as she hugged me against her nicely formed bosom.

    “Thank you Madame. I’ll always be your good girl if you want me to be.” I stated.

    “Yes. Yes Andrea Maria. I think that is best for everyone. When we visit your mother and her Contessa in Spain, this coming Spring, you’ll travel as my wife. Regina’s law firm is putting together the paperwork as we stand here. It is no longer necessary for you to hide the girl inside of you. She may now surface, in all her lavish, subservient beauty,” Hester regaled. 

    “Oh thank you Madame Hester, I love you so for this,” I gushed, girlishly.

    “When I was a young girl, I knew I was different. I wanted a wife. A pretty wife. A pretty wife, just like you, Andrea Maria. And now I have you. You are all mine,” Hester stated.

    “Yes, Madame Hester. I am all your’s. You own me Madame,” I admitted happily.

    “Yes Andrea Maria, it is true. I do own you. For now and for good,” Hester nodded.

                                                         The End

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