*Note From Priscilla*: Hi girls. This is a story where I took some ideas from the real life of a very sexy and sweet Trans Girl named Alleta. She is a gorgeous Southern California Filipina Lady Boy Night Club Girl. Much of this is fiction of course. Thank you so much Alleta honey! I hope you enjoy this? I loved writing it girl! Priscilla.
A story of change, redemption, and coming of age, by Sissy Miss, Priscilla Gay Bouffant
Chapter I: Miss Celine
I always knew I was a sissy of sorts. But, did I really want to live as a female? I’d need a little push for that to occur.....
I was easily, and by far, the most effeminate of the four male children born to my parents. Or as my very successful, Philippine immigrant father had said to me, “You are the daughter your mother has always wanted.”
My father operated a Luxury Home Building business that constructed mansions and mini-mansions throughout the state of Florida. He was from Hispanic/Asian ancestry and born in the Philippines. My mother was a Caucasian, born in the US. They had met at the bank where she worked.
Father had become so upset when I’d told mother I wanted to attend hairdressing school, that she’d sent me to live with her older sister. My Aunt Lynette was happy to enroll me in a Vocational/Technical High School. I took Business/Secretarial classes before lunch.
After lunch I drove across town to a School of Cosmetology. Being away from my father, allowed me to be comfortable wearing unisex apparel. I was still much too self-conscious to wear female things publicly, though Aunt Lynette allowed me to experiment with girl’s things and makeup around the house.
We both had fun with it. She’d call me “Alexandra” instead of Alex. Because of my mixed, Asian, Hispanic and Caucasian looks, she added the middle name of “Jade.” So I was Alexandra Jade when I dressed more femme. No matter what, I still strongly identified with being white and privileged.
I had yet to identify really strongly with being a girl, but I knew I had a strong, feminine side to my personality. By the time I was eighteen, I was working full-time as a hairdresser at “Lady Helene’s,” a very Chic-Chic salon and spa in Miami Beach. There, I’d meet someone, who would finally begin to assist me with the cultivation of my inner, female, self.
My Aunt Lynette had used her connections to get me the job at Helene’s. However, I had also been tops in my class at Cosmetology school. After I’d been at Helene’s for six months, Helene Mural, the owner, told me she had a regular client that wanted to meet me.
“Her name is Celine, and she’s a very special friend and person. I told her how talented you were. Not only is she dying to meet you, she wants to become a client of your’s,” Helene explained.
I was very flattered. Celine was an absolutely stunning brunette, likely ten or so years younger than my aunt, and possibly that much older than I was. After a shampoo and condition, she told me how she wanted her bobbed hair, shaped. As I cut her hair, I let her lead the conversation as I did with all my clients.
“You know Alex, I’ve been wanting to met you for so long. I mean you are so very stylish in your manner of dress and coiffure. Not many boys would dare wear crop pants and a cowl neck tunic top, with patent leather ballet flats. Even to a hair salon. Do you happen to own any Palazzos or Gaucho pants?” Celine asked.
“Well thank you Celine. I guess I do dress a little effeminately. In fact I do own a couple pairs each of Gauchos as well as Palazzos,” I remarked.
“Well, very nice than. And I love the Caramel Brunette, long, inverted bob look, with the gold highlights. Again, very Chic-Chic. And your makeup is subtle, though just obvious enough. By the way, Alex. I understand from Helene you are looking around for some new digs?” Celine inquired.
“As a matter of fact, I am. My Aunt Lynette is so sweet, but I think I need to spread my wings. I do well here at the salon, but the area is so expensive. I drive and own a car, but even the Burbs are a little pricey,” I replied.
“Yes. That’s correct. It’s also another reason I wanted to speak with you. Why don’t we meet after work for a nosh? I can offer you a room that I want to rent. You’d still have full house privileges of course. We could have a quick bite and then drive out to my place. It’s on the way to your Aunt Lynette’s and a shorter drive to work for you,” Celine offered.
I agreed, and after we’d eaten I followed a Celine out to a gorgeous, privately gated community called “The Breakers,” just outside of Miami Beach. I was a little overwhelmed with the size of Celine’s luxurious home. I knew she was some sort of Executive VP with a money management firm, but this place was too much.
It was very much like the type of home my father’s company built. I took a tour of the home and she showed me the large suite I’d be occupying. It consisted of a bedroom, bath and a large sitting room. It was very femininely appointed as to the color scheme, the furnishings and the decor. Celine even referred to it as a “Boudoir Suite.”
When we sat down to discuss things, I said, “Celine, I don’t think I could afford the rent. This place is a palace.”
“Don’t be silly, Alex. I am not going to charge you a lot. I want to help you get the feeling of being on your own. Let me get to the point Alex. I have an ulterior interest in getting to know you better,” Celine smiled.
“I’ll be very honest Alex. I was once a very, feminine boy, just like you. And I had a truly difficult time finally coming out. If there is any way I could assist you and make thinks go more smoothly for you Alex, I’d love to do that,” Celine said sincerely.
Once I’d gotten over the shock that Celine had not always been a stunning female, I said, “I can’t believe you were ever a boy Celine? It just doesn’t seem possible? Yes, I know how very feminine I am, Celine. And I do struggle with the decision to go further in that direction. It is confusing.”
“Yes. Very confusing. That is were I could help you, Alex. Now maybe, becoming more feminine, isn’t in the cards for you? And by the way Alex. Though I’ve lived full-time as Celine, a Transgender female, for a few years now, I have not completely made the physical change,” Celine added.
“I have a bosom, and take hormones. However, I still retain the vestiges of my boy parts. But I am currently transitioning thru the final stages of my transformation. However if you need help deciding on your own transformation, I am here for you, dear,” Celine offered.
“Celine, I’ve already decided I want to take you up on the offer of living here. I need the space, my aunt needs her space, and I do feel I would benefit from availing myself of your experience and your counsel. I’m just so glad we met,” I added as both Celine and I stood up and hugged.
I was fully moved in with Celine in less than a month’s time and paid her in advance, the small amount of rent she was charging me. It seemed as if, almost immediately, I felt even more comfortable appearing as “Alexandra Jade” around Celine, than I had been with Aunt Lynette.
I think that was due to my belief that Celine knew that my need to be Alexandra Jade was stronger than my need to be anyone else. It was Celine that finally suggested we go “Clubbing” as a couple of “girlfriends.” I just wasn’t certain how “Girly” I could be on my “Virgin” trip.
“Honey, only be as girly as you can comfortably be. It can take time. It can be scary. I know from experience. But you’ll have the advantage of having me there and I won’t allow anything to happen that you don’t want to go through. You only have to tell me that you want to leave, or that you’d rather be doing something else,” Celine said, holding my hand and then hugging me.
As Celine had promised, “Raven’s” was a very upscale Transgender Night Club in an extremely nice area of Miami Beach. We pulled up and found parking for her elegant Mercedes sedan. I had to take a very deep breath. I was dressed, coiffured and made-up far more femininely than I’d ever been at any time in my life.
Celine had been “Schooling” me for nearly month now in our spare time. She also had me on a schedule of sorts. Whenever I returned home in the evenings after work I was to shower, inspect my body for hair, remove it, and then thoroughly moisturize my smooth, hairless skin. I had been using depilatories by then, regularly.
Then I was to dress as femininely as possible in panties, pantyhose or stockings, a skirt and blouse or a dress. I was also to wear heels of no less than two-inches. By the time Celine would arrive home I was to be in full makeup and curled hair, with dinner waiting for her. Prior to, during and after the meal I was to use a well-practiced, very feminine voice for our conversations.
I was to walk, move, sit, stand and gesture extra-femininely and go to bed wearing feminine sleepwear. Even at work, the following day, I was to look, act and speak as effeminately as possible. Weekends away from work, were even more intense, as Celine and I would take brief trips to shop, attend a movie or do something as two girls.
But, for my first evening at “Raven’s” as Alexandra Jade, I was as “Ultra-Femme” as I could possibly be. I wore a ladies’ suit and skirt set. It consisted of a Burgundy mini-skirt with dark hose, dark, three-inch heels, and a camisole top, underneath a matching Burgundy jacket. My chest was not padded and I only wore a white training bra.
I’d only recently begun a light hormone regimen. I certainly wasn’t taking the regular dosages Celine took. My fingernails were beautifully done and I’d spent the day with my hair in curlers. I’d only recently took the curlers out and had fashioned my hair into a curly updo. I was in as full a complement of makeup as I’d ever worn.
Prior to alighting from Celine’s car, I asked, “Do you really sometimes meet men here, Celine?”
“Yes, of course I do. Though, I’ve never brought a man home with me. I have, however, spent the evening at a gentleman’s house with him,” Celine smiled, patting my leg.
“You just stay with me, Alexandra. You should follow my lead. But should you feel uncomfortable just whisper in my ear that you’d like to speak privately with me,” Celine added as we stepped from her car.
Celine paid the cover and we went into the club. I felt like I stood out. I could feel everyone’s eyes upon me. We sat down and a “waitress” took our drink order.
“Let me have a Jack and Coke honey. And the sweet-thing with me wants a really girly drink. So get my girly, girlfriend a Brandy Alexander,” Celine smiled.
We were sipping our drinks when I heard Celine say, “Oh my. If it isn’t my old friend, Alain Picard? I thought he was in Europe right now? Imagine. He’s famous as an International Playboy but he’s got the hots for girls like us, honey?”
“Do you mean the handsome older man with the stylishly long, salt and pepper hair, along with the mustache. He’s accompanied by the two younger men, correct?” I asked softly.
“That’s right doll. Both those young, dashing beasts are his bodyguards. One of them is also his driver. He likely came in a Limo. I’ve spent the evening with him more than once. Oops. He’s seen me and he’s coming our way. You look sensational, so don’t worry. He’ll assume you are a Lady-Boy anyway if you’re with me,” Celine said as she patted my hand and smiled as Alain Picard strode our way.
As Alain spoke to Celine, he smiled. Both his bodyguards put their backs to the table and watched the crowd.
“You look as lovely as ever Celine. Who is the ravishing beauty seated next to you?” Alain asked with only the slightest hint of a European accent.
“So good to see you once again, Monsieur Picard. This lovely young lady seated next to me is named Alexandra Jade Villanueva. Alexandra, this is Monsieur Alain Picard. He and I are acquaintances. Say hello Alexandra,” Celine smiled.
“Hello, Monsieur Picard. I’m very pleased to meet you,” I said as I very elegantly extended the long, slender fingers of my well-manicured left hand.
I was surprised that my hand was not shaking. However, I felt calmed as Celine had rested one of her hands on my thigh, out of sight, just underneath the table. I was somewhat proud of myself at this very feminine gesture. My wrist was delicately and languidly limp at the moment. Alain reached for my hand and kissed it.
I thought I would faint and I got chills from him doing that. He was also peering at me with the most beautiful pair of grey-blue eyes that I’d ever seen on anyone, male or female. Alain’s orbs were the most gorgeous combination of a steel grey, with a bluish tint. I’d thought of attractive older men, pruriently in the past. But never in the way that Alain affected me.
With a handsome smile on his face, he asked, “Please call me Alain, Miss Alexandra? Being referred to as Monsieur Picard makes me feel my age.”
“You may call him Alain, if Monsieur Picard insists, Alexandra,” Celine teased.
“Of course, Alain. It will be my pleasure,” I somehow purred, in spite of my self-consciousness, brought on by my exaggerated feminine appearance.
“Thank you, Miss Alexandra. Goodness Celine you treat her as if she were your teenage niece. Might I sit down with you ladies?” Alain asked.
“Shall we let this man sit with us Alexandra, or shall we shoo him away from us? Yes, Alain, you may sit with us, but don’t get fresh. And yes my dear, I treat her as a child because she still is a child. She hasn’t yet turned nineteen. I have only recently taken her from her Aunt’s care, Alain. I am her mentor. She is also my housemate as well as my hairdresser, Monsieur,” Celine smiled.
“I see. Well, she isn’t yet nineteen. Such a pity. If I asked her for a date, you’d have to chaperone wouldn’t you, Celine?” Alain asked.
As the night went on, I danced with Alain twice. I’d practiced with Celine, but being in the strong arms of a very masculine man, was far different. Then Alain asked us to accompany him to a late-night, Miami Beach gathering.
“You may leave your Mercedes here, Celine and I’ll bring you both back in my Limo. Or you may drop your vehicle off at your home as it is on the way,” Alain suggested.
Celine decided to drop her Mercedes off at her residence and we drove over to the party with Alain and his two bodyguards in Alain’s limo. The event was in a lavish Penthouse suite of a Miami Beach high rise. The hostess was a gorgeous Latina, who, I would later find out, was the Mistress of a Colombian cartel head.
I stayed very close to Celine. I could feel, sense and later see the stares of numerous men and even a few women. As Celine appeared to be Alain’s date, I also was quite near Alain for much of the evening. When I did use the powder room, in order to repair my makeup, I returned to find Alain and Celine deep into what appeared to me, to be a secretive conversation.
I was glad neither Celine or I were driving, as we both had quite a bit to drink. It was nearly daybreak when Alain’s limo dropped us off at Celine’s home. Both Celine and I immediately went to our respective boudoir suites to shower. When I walked from my bath, Celine was standing in my boudoir.
Her hair was wrapped in a towel. She wore a fluffy robe.
“Let me prepare both of us a light breakfast with some hot tea. Then come lay with me in my bed. Not as lovers, but as big sister and little sister. We need to talk,” Celine winked.
Once Celine and I had eaten and we were cuddling under her covers, Celine began by saying, “I’m so very proud of you Alexandra. You were so perfectly ladylike this evening. You put your lessons into practice very well. Part of it of course, is your desire to be perceived as a female. However, it is also very easy for me to see, that you have an inherent, wonderfully feminine spirit, which is deeply imbedded within you. That girlish psyche is now rapidly forcing itself to the surface.”
“If you’d like I could put you together with the wonderful female therapist who eventually assisted me in my transition. You can also see my GYN for increased hormone replacement therapy. Now I need to discuss one other thing, my baby sister,” Celine paused.
“Alain knows you are not yet nineteen. However he spoke of dating you. I told him unless we double-dated, my answer would be no. If you do consider that, please understand that Alain is very worldly and would eventually expect from you, what any man expects from a female,” Celine cautioned, as my face flushed.
“It’s a big decision to give yourself to a man sexually, Alexandra. However, shall you consider it, there are precautions to take. One safeguard, of course, is to preemptively widen your rectal passage with vaginal dilators. I can assure you, that Alain is of an above average penile size for a man,” Celine said, frankly.
“Oh there’s just so much to consider Celine, but I do eventually want to experience it all, and for me it will all be worth it,” I sighed as I snuggled deeply into her bosom.
“Yes, I know Princess. It’s been a long night Angel. Why don’t we kiss each other good night, even though it’s already morning? And then we can get some well-earned sleep?” Celine suggested, giving me more than a “Sisterly” kiss upon my moist, collagen creamed lips.
I returned her kiss in kind, saying, “Thank you so much for everything you’ve done for me Celine. And I do need to cuddle and snuggle with someone right now,” I sighed prettily.
“Sleep well, darling. You are a very, wonderful, younger sister,” Celine added as we both drifted off dreamily, holding each other in our entwined arms.
Chapter II: Alexa Emerges
I began to see Celine’s former Transgender Transitional therapist as well as Celine’s current GYN for Hormone Replacement Therapy. A increasingly feminine Alex now appeared every day at Lady Helene’s Salon. I had nearly progressed to the point that I would need to be called Alexandra while at work. I’d also took Celine’s advice and purchased a set of vaginal dilators no different than any true female or Transgender female would use after vaginal surgery.
Though the dilator was proving to be discomforting, I had to admit that Celine was correct. Inserting the dilator within my rectum did provide me with a delightfully effeminate wiggle to my hips when walking. It was an additional, continual reminder, along with the earrings tickling my neck, that my goal was to now, presently, become increasingly feminine.
The other employees at work had taken notice. The ladies delighted in teasing me about becoming more and more like the rest of the girls. The homosexual male employees flirted voraciously with me. When I mentioned it to Celine, she just smiled and spoke in her knowing manner.
“You’re going to find all your efforts to be rewarding Alexandra. Alain Picard has a certain picture of you as both an appealing female as well a courtesan for his pleasure. He has expressed quite an interest in you and has requested I assist you, as well as him, in fulfilling his wishes concerning you,” Celine informed me.
“If you allow me to consummate Alain’s wishes where you are concerned, I believe you will be quite pleased with the results. Alain is privileged and wealthy beyond the imagination. And you will be well-served, shall you stimulate his interest in you, as well as enhance your appearance, to please his exotic, prurient tastes, where girls such as us are concerned,” Celine surmised.
I felt so challenged at that moment, as well as excited. I set out to prepare for my next encounter with Alain Picard, in a manner which I’d never focused on anything else, in my very, young life. If Alain desired a striking, colorful courtesan, I would realize that fancy upon his behalf. I’d be the Lady-Boy he desired me to be.
Why not set my sights on attaining the picture of femininity desired by a prosperous, satiated male? What could possibly be any more subserviently feminine, than transforming myself to meet the exacting standards of lustful girlishness, coveted by a very masculine man’s dreams? And in his hands, as well as the hands of my mentor, Celine, I would become putty to be molded as they saw fit?
In my estimation, nothing could have been more delightfully exciting than the possibilities in front of me. I would set out to become the pampered love object of this intoxicating man. I placed myself under his spell and the knowing custody of Celine’s able skills.
Upon a lazy, sunny, Florida, Sunday, springtime afternoon, Celine and the owner of the salon were I worked, Helene, spoke over speakerphone. I was easily within hearing distance, rubbing strawberry scented lotion over my beautifully manicured hands. I gazed idly upon my French-manicured nails.
“I’d prefer for Alexandra to arrive at the salon tomorrow dressed as girly as she could possibly dress. Why not give her the works between now and tomorrow morning? Put her in full makeup, a dress, curled hair, painted nails, tall heels and jewelry,” Helene said eagerly.
“I think that can be arranged Helene. Don’t you think so Alexandra? Wouldn’t that be fun sweetie?” Celine asked.
“Oh wow. That would be so crazy. But, okay,” I giggled.
“I know I’d love to see it and so would the rest of the girls as well as the clientele. We’ve all been waiting for it to happen girl. I’ve even got a name tag for someone named Alexandra Jade. It’s all printed up and ready to pin on her dress or blouse,” Helene stated.
My nails were already French Manicured and my ears had been double pierced. I had plenty of girly jewelry, such as earrings, necklaces and bracelets. By now my wardrobe was overflowing with dreamy outfits and sexy heels. My body was in the process of changing.
Celine had even began the paperwork for my official name and gender change with the legal department where she worked. I was a girly-girl waiting to happen. So why not go for it? I smiled at Helene, stood up and wiggled toward my boudoir.
“Tell me what to do Madame. I’m your’s for today,” I said, looking back over my shoulder at Celine.
“You can begin with shampooing and conditioning that hair, young lady. Then you need to put it up with tiny wave rods and setting gel,” Celine announced.
Later, I sat at my vanity with my hair up in small curlers, and my face covered with a green clay facial pack. Celine, who once worked as an aesthetician had recently injected my now puffy lips with collagen. She teased me saying, “We girls like to think of pretty lips like your’s and mine as Perfect Cocksucker Lips.”
I was naked with the exception of a fluffy robe and some Marabou slippers. I’d also just had a lovely bubble bath and my skin had been fully moisturized. I felt like a pretty, sexy girl, getting ready for a date, instead of just prepping to go to work en-femme the next day. I decided to tell Celine what I was thinking and she responded.
“Well, speaking of dates little girl. I’ve made a double date for both of us for next Saturday, with Alain Picard and one of his connections, Rocco Grimaldi. Alain sometimes associates with seedy types and I’ve met Rocco. He’s a sort of Mob figure. But I can control him,” Celine said.
“Oh my, that sounds so very exciting. Will we be going to Raven’s for some dancing? You know, getting dolled up like this for a date is just fine, but seriously, for a day working at the salon?” I inquired.
“Alain said he wants to go to his Country Club for dinner. We can dance a little there. Then we might hit Raven’s or possibly Dahlia’s, another Transgender hot-spot. As I recall, Rocco has a penchant for Trans-girls. We give men such as Rocco and Alain something they don’t get from Genetic Girls. We provide complete subservience,” Celine explained.
“As for getting beautiful for the salon? Honey, your job description changes when you go full-on Girly-girl. You are no longer the prissy, sissy, Gay-boy that provides amusement for Style-Queens like me. Not any longer Sugar. You are now a luscious Beauty Princess that all of your clients from 18 to 80 want to emulate,” Celine remarked.
“Besides Helene, you hot-looking girls are the Face of the salon. You are what we ladies notice when we walk inside. You gorgeous females are the reason we spend an hour under a hot, hair-dryer, just so we can look like you for our men,” Celine went on.
“When I was working at making believe I was a male, I could put on a jacket and tie, brush my teeth and head to work. Now my lipstick has to match my nail polish. My blush can’t contrast with my eye shadow, nor can my bracelets clash with my earrings. You know how often I come in for a trim and a color touch up. For us girls it’s so much different,” Celine added.
Of course I slept in curlers that evening. Celine snugged a hairnet over the tightly wound perm rods. Then she tied a brightly colored scarf over the hairnet. The wave rods were of the tiniest size and there were just so many! It was a little difficult to get comfortable with so many curlers in my hair. The scent of the Lavender infused setting lotion and the perfumed face cream I wore to bed enveloped my senses.
The soft folds of my pretty nightie soothed my lithe, girlish frame. As I snuggled against a big, fluffy pillow, I sighed. I knew I was now growing a bosom and that the definition between my hips and my waist were now changing. The following morning as I dressed, I could sense my everyday life was going to be different.
“Would you like to pad-out your boobies today, or continue to wear a training bra for now, Alexandra?” Celine asked.
“I want things to look as real as possible. I like seeing my boobs growing. I’ll stay with the trainer until my ‘Girls’ get bigger,” I decided.
“Okay, but I’d suggest a corselet or a waist-cinch to define your shape a little more,” Celine recommended. So I agreed to let her snug in my already slender waist-line a little more.
I could see what Celine was going for as she helped me choose my clothing, hairstyle and makeup application. She and my boss at the salon, Helene, were going for the “Hot Girl” look for me. The “Hot Girls” at the salon, attracted attention. We were like part of the decor and the glamorous furnishings of the salon.
Along with the “Hip” background music that was playing, we were the first things anyone noticed when they entered the salon. We looked really good, and really sexy. The “Hot Girls” wore tall high-heels and tight-fitting clothes. We chewed gum and hair-flipped. We looked like we were ready to go to a night-club and dance at any minute.
When I sashayed into the salon that morning, I received a number of second and third looks. More than one of the ladies I worked with gave me a “You go girl!” My spirally, tendrils were teased, sprayed and pinned up on the left side of my head. My makeup was full, vivid and luscious. My three-inch heels clicked on the gleaming, tiled floors.
The gypsy hoops and the set of pendants dangling from my ears, swayed with my hips. Everything about me screamed, “Look at me!” Was I a little nervous being “out” in broad daylight, and so obviously dressed as a female? Of course I was. But knowing I had the support of my mentors, my co-workers and my clients meant everything to me.
I was making that passage from Sissy to Girl. It was never going to be seamless, but it did feel smooth that morning. I was also becoming ever more ready for our double date with Alain and his friend, Rocco, who ever he was? It was fun, as I sashayed thru the salon, with an exaggerated hip-wiggle added to my walk, being complemented on my girlish appearance by clients as well as co-workers.
I was wearing a tight, wrap skirt that hugged my hips and thighs. My ruffled, off the shoulder blouse showed off my milky-white shoulders. The corselet enhanced my slim waist and pushed up the flesh around my pecs to make my tits look larger.
My dark patterned hose enhanced my long, pretty legs beautifully. My French-tipped nails added that exotic touch, every girl looks for. What a great day! By the time I returned home and put on an apron to begin preparing dinner for Celine and me, I felt just about as girly as I had ever experienced in my young life.
I couldn’t wait to see the look on Alain’s face when he saw me, so totally, smoking-hot looking for our date. When that Saturday rolled around, I had ginger highlights put into my auburn hair at the salon. It was just so nice and relaxing to lay my head back into one of the shampoo sinks at the salon where I worked, and have my boss Helene pamper me as she washed and conditioned my long, thick, auburn tresses.
As she painted on the ginger tints, she teased me about my first real date with a man. I’d brought in my own rollers and Helene set my hair and then wrapped it in a bright-red turban. I drove home with my hair in curlers. Such a sissyish thing to do, but I just loved it. As Celine helped me prepare for our double date, she cautioned me on a few things.
“No butt plug tonight lovey. Just bring along some lube though. Be ready for your man. Alain is like a lot of men. He and I have dated in the past. He doesn’t show his affections publicly, but he likes his females to be girly and sweet, showing affection towards him. It would be wise for you to make eyes at him and flirt,” Celine smiled.
“Reach out and touch him, snuggle against him, and give him light, teasing kisses. Really make all over him, and act like a little sex-kitten that is just so impressed with his overpowering manliness. Men like Alain, love that sort of effusive cooing and cloying from their girls,” Celine suggested.
“Oh I can do that. I feel like such a sissyish, daddy’s girl sometimes, when I look at handsome men. I always have been like that Celine. This is why becoming a sexy girl like this is really just so right for me. I’ve always known I was sissy and that I’d wind up with a boyfriend and not a girlfriend. I just wasn’t certain what clothes I’d be wearing,” I admitted.
“It has just relieved so much guilt for me to know that I can be accepted as Alexandra Jade by both females as well as males, Celine. It has been especially rewarding to not be ridiculed. Being rejected by my father for being such an effeminate boy was just so shaming and hurtful for me. And his angry reaction when he found out I wanted to become a hairdresser, really belittled me,” I said, with tears forming in my big, pretty, brown eyes.
“I think it is always why I’ve desired to be treated affectionately by a man, and wanted the love and attention of a strong, fatherly male such as Alain. Women such as my mother, my aunt Lynette, you and Helene always made me feel valid for being effeminate. But now, to have a handsome male that wants my company as a pretty girl is simply so rewarding, Celine. It just makes me want to cry,” I sobbed.
While I whimpered, Celine held me and comforted me saying, “It’s all okay Angel. It’s okay to be who you really are. I know how you feel. I’ve been there. That’s why I wanted to help you. Every time I saw you in the salon I saw so much potential in you as a girl. I always wanted to reach out to you. I saw myself when I was your age,” Celine said as she kissed my tear-stained eyes.
“When Helene told me you were looking for a new place to live, I knew positively that the time was right for us to become friends as well as housemates. I told her to put me on your client list. If you’re nervous I can give you a valium or two. But let’s dry those tears and take out those curlers,” Celine offered.
“Then we’ll give you a sexy ‘do’ and get you made up. We’ll put a big bow or ribbon in your hair. No, wait. I’ve got a lovely jeweled brooch we can pin into your curls. Then we’ll cinch your waist and put you in that emerald green off-the-shoulder gown we just bought you. You’ll look just like a princess,” Celine added.
When Alain’s limo arrived his driver came to the door. Celine and I minced to the limo. Alain’s other bodyguard stood by the front door of the vehicle. Alain was standing at the passenger side smiling. Rocco was at the driver’s side rear. I walked sexily towards Alain. I’d taken half a Valium and it was helping. I stopped very closely to Alain. I could hear Rocco greeting Celine. My eyes focused on Alain’s manly shoulders and his handsome face.
“You look so very exquisite this evening Miss Alexandra. Please, let me assist you into the limo?” Alain said.
“Of course Alain. And thank you. Being with you makes me feel even more lovely,” I whispered throatily, with just the slightest, nearly lisping, click of my tongue.
I extended my left hand to him. With my clutch held in my right hand, I touched the edges of my spirally tresses as I jauntily “Flipped” my hair as sexily as I possibly could. He kissed the tips of the fingers of my left hand. My French manicured nails gleamed in the early moonlight.
As he assisted me into the rear, double-seat of the limo, I brushed slightly against his manly chest. I smoothed the hem of my mid-thigh gown beneath me as I sat. I winked at Celine and smiled politely at Rocco. Alain slid into the seat, just beside me. I moved over to sit much closer to him, placing my right hand on his thigh for balance.
I laughed, girlishly as I leaned into his chest, feigning a loss of balance. Alain steadied me by holding me firmly with both of his hands.
“Thank you darling. I think I caught one of my tall heels in the carpet. Please excuse my lack of finesse?” I said softly, smiling up at Alain.
“Not at all, my dear. It was hardly a lack of anything on your part. You move very gracefully Alexandra. I’ll have the driver check the carpet. I recall this occurring once before,” Alain said so gallantly pulling me slightly towards him. I took the hint and very affectionately snuggled into his left arm and shoulder.
Alain’s country club was fantastic, including the decor, the music, the food and the atmosphere. I ate lightly, watching my waistline. After a glass of white wine Alain and I slow-danced. When he held me I melted into his strong arms. I felt so safe and secure. All the hours at the salon, dressing prettily, moisturizing, and doing my makeup seemed so worth it.
After another glass of wine and two more slow dances in Alain’s masculine embrace, Alain asked me, “Would you like to go to a club? We could go to Raven’s, Brianna’s or any club of your choosing. Alexandra? Are you okay?” Alain asked as I looked off dreamily into space and then back at Alain, with a silly, blissful smile upon my face.
“Would it be all right if you took me back with you, to your place, Monsieur Alain? Where we could get together privately, and come to know each other so much better?” I asked almost innocently and childishly.
After staring at me for a moment, Alain smiled and said, “Wait here off to the side of the dance floor while I speak to Celine and Rocco. I’ll only be a moment my beautiful one.”
When Alain returned he said, “My driver and bodyguard will take us to my estate. There Rocco will pick up his car and he and Celine will continue to Raven’s. Celine would like to speak to you in the powder room momentarily, my precious one.”
When I arrived in the powder room, Celine asked me, “Are you certain, you want to spend the evening with Alain, on your own, without me, Angel?”
“Yes. Isn’t that why we are here right now? Isn’t that why I made myself so beautifully feminine? The time is right Celine. I can feel it. And Alain is the man I want to have, to make me a woman. I feel so alive in his arms. I feel electrified when he touches me. I want to be his. Yes, I’m certain,” I said as she smiled and kissed me.
“My little girl has grown quickly, hasn’t she? Well then, I’ll see you whenever Alain brings you home to me Princess,” Celine added, as she hugged me and again kissed my lips.
I fixed my face and walked back into the dining area. Alain was signing the check. I nodded to him and he smiled. The drive to his estate was brief. We said our goodbyes to Celine and Rocco. I should add now, that I didn’t care for Rocco very much. But Celine enjoyed the company of masculine men and they seemed to get along.
When we walked into Alain’s home, we were met by his personal secretary, Ms. Miriam Featherstone. She and I were introduced.
“I’m very pleased to meet you Ms. Villanueva. Monsieur Picard if you won’t be needing me I’ll be retiring. Where and when would you like your Sunday breakfast Monsieur? I’ll inform the staff and wake you with a light knocking sir,” Miriam said.
“Hmm? Breakfast for two on the south patio at 9 A.M.? How does that sound, darling? And yes, you may wake us, Ms. Featherstone,” Alain said turning to me in question.
“Oh? It all sounds perfectly wonderful, Alain,” I answered.
On the way to his bedroom suite, I linked arms with Alain and laid my head against his bicep. I loved the sound of my four-inch-high-heels echoing against the parquet flooring. At barely nineteen I felt so grown up. I was about to go to bed with, make love to, and be taken, by a man that was old enough to be my father.
Only adventurous, big girls did things like that. Alain and I walked arm-in-arm into the large sitting room that adjoined his bed and bath. As I found myself a seat on a divan, Alain asked, “Would you care for some Brandy, Miss Alexandra? And would you mind if I changed into something more comfortable? In fact, if I’m not being too presumptuous, would you indeed care to put on something more casual?”
“Well. Decisions must be made, mustn’t they? Yes. I’d just love some Brandy. Of course you may change into anything you’d care to. After all, Alain, this is your home. And it interests me that you’d have something for me to wear that I would be able to lounge in? I don’t think one of your robes would fit me?” I teased.
“My personal secretary, Ms. Featherstone, who you just met, purchases certain items on my behalf that my female guests might enjoy wearing. If you care to, just saunter over to the guest bed and bath outside the doorway to the right. The first closet to your left, as you enter the boudoir should contain various robes and slippers in dissimilar sizes,” Alain explained.
“You may leave your own things on the bed in that boudoir, should you choose to change. The choice is completely up to you, of course. Here is your Brandy. I hope you like peach?” Alain smiled.
“Peach will be just lovely. Oh my, this is exquisite, isn’t it? Oh yummy. Well, then, let me see if the selection of robes and slippers are just as elegant as the host and the beverages he serves,” I added cutely, as I minced to the spare boudoir.
Indeed the lingerie in the closet was all lovely as well as very expensive. And the slippers all had high-heels that would show off my waxed legs. I kicked off my tall heels and slithered out of my gown. I unpinned the brooch from my hair and shook loose, my sprayed curls. I removed my bra, unhooked my corselet, and took off my panties. Lastly I removed my garter belt and hose. I slipped on a short, floral-print, pink, kimono-style robe.
Once I’d stepped into a cute pair of Marabous with kitten heels, I neatly folded my things and put everything on some shelves within the antique wardrobe. I minced back into the sitting room. Alain was also in a robe, sipping Brandy, seated on the same divan as I had been seated upon.
I can take a hint. I picked up my glass of Brandy and sat next to Alain. As I did so, I curled up next to him and snuggled comfortably into his left side. I leaned my head into his shoulder and kissed his cheek, saying, “I’m feeling very romantic. Are you Alain?”
“Yes I am, Alexandra Jade. What a beautiful name. Do you smoke any hallucinogens Alexandra? I have some fantastic Cambodian pot, rolled up with a fabulous strain of Lebanese Hashish. The joints are then dipped in a liquid strained from a very potent Afghan Opium poppy,” said Alain holding up a yet, unlit joint.
“How nice. Why not light that one up, Alain?” I asked.
Alain did so, took a long pull and handed the joint to me saying, “A friend of mine’s girlfriend claims the opium helps relax her sphincter muscle.”
“Darling, that sounds lovely. I have some lubricant in my pretty, little, clutch purse that not only desensitizes my anal passage, it prolongs erections. So, Alain, between your pot and my lube we are going to have a memorable evening my love,” I said as I took a long pull on the joint.
Alain and I proceeded to pass pot smoke back and forth by kissing. We began to cough and laugh like a couple of silly high school kids. Then I took one long, last pull, before I stubbed out the joint and took a big gulp of Brandy to cool the last of the smoke in my throat. Then I climbed up upon Alain, kissing and biting his neck.
I continued to laugh loudly and thought I might pass out. I calmed down and started to rub my crotch against one of Alain’s legs. I threw my arms around his neck and kissed him passionately.
“Oh Alain darling. Please be my Daddy? I want a Daddy to love me and screw me and be strict with me if I’m a bad girl. Could you be that kind of Daddy to me Alain?” I asked sexily.
“Of course I can be the Daddy that you want and need Alexandra. You are such a sweet girl though, I can’t imagine your Daddy ever having to spank you?” Alain teased.
“Oh no Daddy. Oh I’m being bad right now, humping your leg and thinking of all sorts of naughty things, that I want to do with you tonight. Please spank me Daddy? Please spank me and warm my ass up just a little? Pretty, please Daddy?” I begged.
“Of course honey. If you insist. Let’s pull your robe up and put you over Daddy’s lap. There. Now how my spanks should I give this bad, nearly naked girl?” Alain asked.
I so very badly wanted and needed a really hard spanking from Alain. My real Daddy never spanked me. Although he did spank my three older brothers when they were bad. He told my mother I was much too much of a fragile sissy. He told her she had to be the one to spank me.
“The sissy boy is too much like a girl. Only a woman should spank a sissy like Alex. You must spank his girly ass when he misbehaves,” my father ordered.
So I always went thru the shame of being spanked like a girl by my mother in front of my father and brothers. I was told by my father to kick my legs and scream like a sissy girly when mother spanked me.
Throughout my entire life I had wanted a big, strong, older man to spank me. The idea excited me sexually. It even excited me more as I laid over Alain’s lap, as I knew that after my spanking we would be having hot passionate sex. I couldn’t wait for Alain’s cock to penetrate my pinkish, sissy ass pussy.
“I think, that maybe you should give me ten spanks Daddy?” I said.
“Ten spanks it is going to be for bad, little Alexandra,” Alain said as the first swat of his hand struck my ass.
“Yow Daddy! Oh, ouch Daddy. Oh, ouch that hurts so much Daddy!” I began to scream as one, two, three, four and five swats him my slender, but growing ass.
“Oh please Daddy? Stop, please stop, Daddy!” I screamed louder, as the 7th swat struck my ass once again.
“Silence girl. Never interrupt me and I mean that. That was seven. And because you interfered with your spanking you will get two extra,” Alain promised.
By the time the next five hard swats had fallen, I was a sobbing, blubbering, trembling mess. I’d been kicking and screaming wildly. As Alain raised me to my feet I fell into his arms and kissed him all over his face, with my tears streaming down my cheeks. I felt just so very cleansed.
“Oh thank you Daddy. Oh I feel so much better now. Oh, I’ll be a good girl for you now Daddy. I promise,” I said, kneeling and taking his cock in my hands and kissing it.
It was already erected, but it grew still larger. When Alain’s penis had reached its full size it was already between my lips. I now knew what Celine had meant when she described Alain as being, “A better than average sized man.”
I took as much of Alain’s huge member into my mouth as I possibly could. Today, I know two things for certain. When I am looking into a mirror at a downtown Miami Beach night-spot, I am the hottest looking bitch in the entire club. It is a fantastic feeling to know that. I also know that I can suck a man’s cock better than any bitch in that club, especially the Genetic Girls that were born female.
That first evening with Alain, I still think, even though I had never sucked a real cock before, that I gave Alain the best blow job he had ever received. When I was ready for him to shove his cock up my sissy ass, he was rock hard and ready to explode.
“Oh Alain, honey? I really want you and need you inside of me. Please screw me? Please! Oh my gosh I need your cock deep, deep, within me baby,” I begged frantically.
“Of course my Princess. How would you like me to take you?” Alain asked.
“Oh geez. I don’t know. I’m a virgin, my dear Alain. No one has ever screwed my sissy-ass-pussy before,” I gasped.
“I’ll sit on the divan and then you can lower yourself onto my penis. Use your lubricant. You purse is right here darling,” Alain said, ever so nicely, as he handed my clutch to me.
I tried my very best to calmly remove the lubricant and I coated Alain’s prick. Then I handed him the tube.
“Could you put some on your fingers and do me, please? I’m nice and clean. Celine helped me to douche before we got dressed tonight,” I explained.
When I felt properly lubed, I put my ass over Alain’s lap and let him place his strong hands on my hips. I placed my hands on my thighs and slowly lowered myself onto Alain’s big dick. As Alain penetrated my anus, he instructed me to lower and raise my ass in moderate increments, as his cock steadily entered my rectum further and further upon each additional thrust.
The numbing agent in the lube really helped with the discomfort, and I knew it would assist Alain in lasting much longer, as he screwed me. I moderated my breathing and finally I took a nice deep breath and Alain’s cock went all the way up inside of me at last.
“Oh. That’s so nice. Oh I feel you Alain. Oh Daddy. That is so damn good Daddy. Oh Alain, fuck me please? Oh yes fuck me my darling man. Oh you fucking stud, screw me good,” I gasped.
My ass, and Alain’s pelvis, went up and down, as Alain’s cock went in and out of my rectum. Alain was such a fabulous lover and set a smooth, sexy pace. As I adjusted to the undulating motion, his hands moved from my hips to my small tits and my not quite as small penis and testicles.
His left hand massaged my growing left tit nipple. His right hand played with my “sissy-clit” and my balls. I knew eventually as the hormones made my bosom grow, then my genitalia would shrink. Unless I decided on implants and backing off on the Estrogen, my cock and balls were going to ultimately diminish.
But, I did love how the Estrogen made me feel so much more girly, and truly attracted to men. Especially strong, handsome, mature, assertive, rich men such as Alain. What Alain was doing to me was wonderful. I just hoped I didn’t make sissy cum too soon. I knew from what I’d been told that the desensitizing chemicals in the lubricant would make Alain’s lovemaking last much longer.
His cock felt so strong and firm in my ass, that I felt like we could last all night. I was feeling like such a woman at that moment. I was just so hot, sexy, lustful and feminine. I couldn’t have been more happy and fulfilled. Alain proceeded to pick up the pace and now had both hands kneading my tits.
“Oh Alain, I simply adore how you are touching me darling. You’re just so very sweet. I know my breasts aren’t big and womanly just yet,” I sighed.
“I love your breasts my Angel. They are just fine. They will grow, and I will grow to love and enjoy them even more so,” Alain said.
“Oh my gracious, what an adorable man and lover you are Alain. I feel so fortunate to be with you,” I gasped.
“As I am also fortunate my Princess. Let us increase the pace and make ourselves climax, darling,” Alain said.
I moved up and down upon Alain’s cock as quickly and firmly as I possibly could. The pace became nearly frantic and I loved it. I felt my sissy-clit swelling. I could sense Alain’s manly cock expanding in my rectum. We were now both much closer to ejaculating, than we had been, much earlier in our lovemaking. My breathing, as well as Alain’s, had increased demonstrably.
“Oh Alain, squeeze my tits. Please, Alain. Squeeze them. Oh that’s so nice, darling. Oh, I love you so much, Daddy! Fuck me Daddy, oh Fuck me!” I screamed as I spewed sissy cum from my sissy clit.
Shortly afterwards, Alain’s cork popped and I could feel the stream of his hot ejaculate into my rectum. He pumped his cock strongly inside of me as I gyrated wildly upon his penis. The feeling of a strong man’s semen up inside of me was just so very fulfilling. As I stood up, turned around and kissed my lover, I reached for my clutch purse.
From my pretty, beaded, girly clutch I took a Tampon which I snugged up inside of my anus. Not only did I not want to make a mess with any sperm leaking from my rectum, I also wanted to keep as much of Alain’s manly seed up inside of me as possible. I wished at that moment that I was a real female and could one day bear his child.
I laid down on the bed in Alain’s room and snuggled under the covers with him. It was such a romantic girly feeling for me. His arms were so strong as they enveloped me. His scent was so musky and manly to me. The safety and satisfaction I felt laying next to him was surreal.
“Oh Daddy. That was so wonderful. You drained me darling. I’m so sated at the this moment,” I girlishly cooed to my man.
“For one so very young, you are a sensational lover my Alexandra,” Alain complimented me.
“Oh Alain, I’ll be anything you want me to be. Just tell me, darling. I’ll do it for you and I will be it for you, my love,” I sighed as I melted into him.
I slept the secure sleep of a slave with her Master, that night. I was a concubine with her Prince, a consort with her King. I came to, slowly in the morning. Alain was still sleeping. I glanced at a digital clock by the bedside and saw from the time, that it was likely just prior to dawn.
I reached under the satin sheets and saw, as most manly men are won’t to do, that Alain had a massive, very stiff, morning boner. It looked just so very delightful to me. I couldn’t resist it. I crawled under the warm covers and wrapped my pretty, cocksucker lips around his exciting penis.
I took as much of the penis into my mouth as I possibly could have, and wet it from its tip to Alain’s balls, with the moistness within my mouth. I licked it as a child would suckle a popsicle or ice cream cone, and then proceeded to slowly bob my curly-topped head, up and down is a sensuous rhythm.
I was pleased to see Alain stir and then moan quietly. I sucked at Alain’s swollen balls before going back to his cock. I didn’t intend to slip his cock inside my ass. I wanted him to cum in my mouth that morning. Alain began to slowly roll his hips as I continued to lick and suck his penis.
At long last he began to spurt and emptied his balls into my waiting mouth. I gulped and swallowed his manly seed as quickly as I could. I wanted all of it. The fingers of Alain’s right hand were intertwined in my long, thick, lovely, auburn tresses. I loved the feeling of that. I adore it when a man touches or plays with my hair.
When Alain had at last spent all of his ejaculate, I cleaned up his cock and balls, before snuggling beside him. He let me know, that Ms. Featherstone wouldn’t be by to wake us until around 8:15 AM.
“Then I’ll just fall back to sleep snuggle in your arms, my love. Did you enjoy your morning blow-job darling?” I whispered.
“Yes, it was delightful, Princess,” Alain said.
“That makes me so very happy,” I said as I closed my eyes.
It was such a dreamy morning to catch a few more hours sleep. How nice it was to have Alain’s ejaculate inside my rectum and nurturing me, inside my flat tummy. I felt so girlishly blissful at that moment. I didn’t want it to ever go away.
Chapter III: My Jeweled Cage
Alain and I began to date regularly each weekend, frequenting his country club, and Trans Clubs around Miami Beach, such as Raven’s, Dahlia’s and Brianna’s. I felt so safe with him that Celine only came along for the fun of being with us. She no longer saw Rocco as she’d tired of his sexual shortcomings.
“He creeps me out Alexandra. He’s a good lover. But he makes too many suggestions as to threesomes with other women or me giving one of his cronies a BJ. Not on your life. I’m not into girls, nor am I into being his slut,” Celine informed me.
I was uncomfortable with Rocco also. When he looked at me lustfully, my flesh crawled. Of course being with Alain was totally different. In the aftermath of our steamy lovemaking I enjoyed the delightful Sunday morning breakfasts on the veranda outside his bedroom or on one of the several patios at his estate.
On varied occasions, Ms. Featherstone would join us. She was so delightful to be around. Though younger than my mother, she had a very motherly instinct about her, especially concerning me. In fact, as I’d just turned nineteen, and frequently referred to Alain as “Daddy” during our lovemaking, I sometimes felt so “Little-Girlish” when breakfasting with Alain and Ms. Featherstone.
They often discussed subjects such as business or politics. Those were two matters I knew very little or nothing about, at all. I was also so very clueless about sports. I liked girly things such as hair styles, makeup, nail polish and fashion. Pretty clothes excited me.
I simply loved that Ms. Featherstone had taking me shopping one Sunday afternoon, so that I could have a wardrobe to keep at Alain’s estate, along with sumptuous cosmetics and hair care products. There was a certain type of Girly Boy, Alain was looking for and Ms. Featherstone, just like Celine and Helene, was making certain I was a model of that type of Lady Boy.
At long last, the inevitable occurred. I’d been expecting it somewhat, I’ll admit. One Sunday morning at breakfast, Alain invited me to move in and become his kept mistress. I was overwhelmed, even though I’d thought about it and had anticipated the moment. Ms. Featherstone was present and also encouraged me.
“We’d both love to have you here, at the estate with us on a permanent basis, Alexandra. You are such a lovely child dear, and Monsieur Picard adores you. I could take over quite ably from Ms. Celine and continue your proper grooming and schooling. We must assure that you become an appropriate courtesan for the Monsieur,” Ms. Featherstone added, boldly.
“Your presence here, Alexandra, excites me beyond description. When you enter a room, the very sight of you, lights up everything within your proximity. You cannot imagine how being with you, affects me,” Alain added.
“I’m so very flattered. Really I am. This is all happening so very, very fast it seems. However, I really am tending to want to say yes. It will be a much longer commute to the salon for me. Possibly I could reduce the days that I go into the salon,” I replied.
“Why go in to work at all? You don’t really need to work darling. The Monsieur and I shall provide all that you could possibly want or need dear. Besides, you’ll be assisting me as you learn to run the household. I’m certain the Monsieur will provide you with an allowance or a stipend. Won’t you Alain?” Ms. Featherstone asked.
It was the first time I’d heard Ms. Featherstone refer to my Alain by his first name.
“Yes, of course. And I know how much you enjoy styling hair and making ladies very beautiful my love. And if you should miss working at a salon, we’ll secure you a position at a salon nearby,” Alain promised.
Within thirty days I was ensconced at Alain’s estate as his paramour. The girls at Helene’s gave me the most lovely going away party and I received the most wonderful gifts from them. Though Alain and I spent most evenings sleeping together and making love, I had my own separate boudoir and Alain his very own Man Cave.
I enjoyed the privacy, the extra closet space to store my pretty clothes, as well as being able to nap, undisturbed. The first evening that I spent with Alain after officially moving in was quite special. It was a Saturday. Celine and I had spent a good portion of the day getting me settled in. Celine stayed for dinner with Alain, Ms. Featherstone and I.
After Celine departed I was going to assist Ms. Featherstone and the maid, Brandy, with the cleanup. Ms. Featherstone deterred me by saying, “No darling. You’ve had such a long day. I suggest you go to your boudoir and sink into a warm bathtub full of scented oils, salts and bubbles. Then dress for a long, romantic evening with Master Alain.”
So, indeed, I did as I was told, and soon found myself luxuriating in my steaming tub, up to my swanlike neck in a fragrant bubble bath. I felt so elegant, wealthy and special. Like a spoiled little princess in her castle. When I stepped from the bathtub to dry, moisturize and put on powder, I watched thru the door to my bedchamber as Ms. Featherstone made her way around my boudoir.
She laid out sexy sleepwear and checked the cosmetics that were available on top of my vanity. Smiling, she peeked into the bath, adding, “I’ll send Brandy up to your chambers. She’ll assist you with your preparations for the evening. She’ll be following my instructions which come from Master Alain. Please defer to her.”
“Yes, Ms. Featherstone,” I replied.
I assumed I was to wear the satin, pastel, baby pink, backless, solid cami nightdress, with matching, fluffy marabous. As I completed dressing, Brandy knocked lightly on my open boudoir door.
“Might I come in Miss Alexandra? Ms. Featherstone sent me to do your hair, fix your face and adorn you for an evening with the Master,” Brandy said politely.
“Yes, of course Brandy. Please do come in. I’ve washed my hair, dressed and I’m ready to be beautified, thank you,” I said.
As Brandy plugged in the hot roller set and began to comb a conditioning setting gel thru my hair, I thought about how much I would not only enjoy this type of pampering, but it also appeared I’d be under the control and tutelage of Ms. Featherstone. Truthfully, I rather liked the possibility, at that juncture, of no longer having to think for myself.
Making my own decisions had never been my strongest suit. So having those decisions made by Ms. Featherstone and my wonderful “Daddy,” Alain was just perfect. The way I saw it, as long as I looked pretty, acted sweet, and remained obedient and subservient, everything would be just fine.
Brandy sectioned my hair and began using the already steaming, hot rollers to set my thick, beautiful tresses. Once she had my hair rolled up, she had me turn to my right and look at her as she painted my face. “I could get used to this,” I thought as she applied my foundation. I was getting a full makeover just to entertain Alain for the evening. How nice!
As Brandy worked around my eyes she spoke to me, “You are such a pretty young lady. Monsieur has not ever had a girl live with him. He must find you very special Miss Alexandra? You are very fortunate, you know? The Master is fabulously wealthy and very generous. You will be living within the lap of pampered luxury,” Brandy said, as she scrutinized her work carefully.
Brandy decided to take my hair down and style it prior to finishing off my makeup. She slowly plucked the individual hot rollers from my shiny, auburn locks. Pursing her lips she began to back-comb my tresses. When my hair is wet, it’s very shiny and lustrous like many Latinas.
Even a Latina such as me, who is mixed race, with both Asian and Caucasian ancestors. So as Brandy, brushed, combed and teased, she fingered in some styling gel, as well as spritzed my locks, with copious amounts of lacquered hair spray to make my tresses even more glistening and glossy. My maid was finally satisfied with the cute little bouffant bubble “do” she had given me.
She affixed it with a pink bow, to match my nightdress and slippers. Then she outlined my lips with a magenta lip wand before filling in with a tube of glossy lavender lipstick. Brandy then dabbed some expensive French Perfume, “Boudoir Passion” behind my ears, upon my wrists and between my pubescent breasts.
“Come, Miss Alexandra. I shall take you to the Master,” Brandy said as she took my hand.
She knocked lightly upon Alain’s open door, saying, “Monsieur, your Favored One, Alexandra is here for you, sir.”
“Very well Brandy. You may bring Alexandra in. Then, please close the door as you depart,” Alain said.
“Yes sir, here she is. You look lovely, Miss Alexandra. Good night miss,” Brandy said as she made her way out.
“You may latch the door Alexandra. You look so very special tonight. Our first night together with you residing here. Come and sit on my lap,” Alain said, lifting a glass of brandy as if he were toasting me.
I knew Alain loved to drink brandy at bedtime, especially prior to and after lovemaking. I minced daintily to him and smoothed my nightdress as I seated myself upon his lap. Alain pulled me towards him. I leaned against his chest. Looking up into his eyes, I asked, “Oh please Daddy. May I kiss you?”
“Yes, please kiss me, my sexy kitten. How lovely you look tonight my Angel. Ah. Such a sweet kiss, my Princess,” Alain said as our mouths met in passion.
He squeezed one of my breasts delightfully, sending shivers throughout my svelte body. The Brandy on his breath was so sexy and tasted so manly. His maleness was simply overpowering for a dainty, demure, sissy girl such a I’d finally become. And I’d only become more feminine as time went on.
I reached inside of Alain’s pajama bottoms. The expected large erection filled the fingers of my right hand. I loved the way Alain’s cock felt. I asked him, “Can I make this wet for you with my tongue?”
“Why not lubricate it and I’ll lube your saucy rectum? Then you can face me, wrap your legs around my waist and mount me. We can make love while we kiss and I play with your tits. Come over to the bed my Princess,” Alain said, as he picked me up and carried my lithe, dainty body to his King-sized Bed.
I couldn’t help but lick his cock before I lubricated it. Then he turned me around to face away from him as he used his fingers to distribute the lubricant up into my anus. Alain turned me back around to face him. I gleefully jumped onto his thighs as he picked my lithe body up into the air.
I was so excited, as I always was, as Alain, slowly lowered me down upon his penis. As always, whenever Alain and I made love, it would begin as a sweet, romantic encounter, and it would end with me riding Alain’s cock, as if I were a common, wanton, sluttish whore. I loved the feel of Alain’s hot cock entering my butt. And as it slid within me, my rectum seemed to swallow him up.
I could barely wait for his penis to slide all the way in so I could begin bouncing up and down upon his cock. I loved making love to him while sitting upon his dick facing him as I could lick his face and kiss and bite his lips so forcefully. I additionally loved that I could rub my tits against his chest and he could lick and bite my boobs as well.
On his lap, bouncing up and down, and facing him, just might be my favorite sexual position. Once his penis was all the way inside of my ass, I began to shimmy, crazily upon his cock. I went slowly at first, but ultimately this resulted in me moving my ass in a wild frenzy.
I always felt so desperate to feel the gushing flow of Alain’s manly seed entering and filling my rectal cavity. In my wildest fantasies he was flooding my ovaries and impregnating me with his child. Never when I was a a teen sissy had I felt ever, so effeminate, as to want to have children.
To be truthful, when Auntie Lynnette, and later my friend Celine and my boss Helene had helped transform me, I did not ever think of being a mother. But, only when I began making, passionate, tender love with Alain, did I imagine bearing a child. Of course, even with SRS, that would be a complete physical impossibility.
However, I still coveted the idea of having a little girl, that looked just like me. A little Filipina girl whose hair I could curl and whose nails I could paint, and who I could dress in darling, pretty little outfits. Oh I was just so silly in love with the idea of one day being a mother. Hoping of course that my little girl would have a Daddy, just like Alain who would love her.
As Alain’s cock grew stiff and strong within my tight ass, I became excited. I wanted his hot, creamy sperm. I pushed down upon his shoulders as if I were going to vault over him. At the same time I increased the motion of my ass. Finally he let out a manly grunt and his penis exploded, giving me what I’ve always desired. He gave me his masculine seed.
I clenched my butt cheeks around his cock because I wanted to keep all of his ejaculate within me. I screamed loudly as his sperm spurted inside of me. As his cock and balls emptied, I threw arms around him, smothering him with kisses, prior to my head collapsing upon his shoulder. As his erection subsided, I climbed off of him to plug my anus with a tampon.
“I love keeping your ejaculate within me. I make believe you have impregnated me. I wish it was possible for me to have a child with you,” I smiled.
“Come to me my Princess and let me hold you. One day we can discuss children and more,” Alain added as I lay down with him.
“I want pretty girls. Pretty Filipina girls,” I said.
“Then we will find some pretty Filipina girls for you. I’m certain there are many that need a good mother and a good home,” Alain stated.
“As well as a good Daddy,” I added.
I always slept very well after lovemaking with Alain. Especially when I slept in his arms with his sperm inside of me. Over the next month we made love constantly and I grew to adore this man. I was disappointed though, when he had business overseas in Europe and could not take me.
“It will be boring for you. When I take you to Europe with me, I do not want to be conducting business. I want us to be sightseeing, dining, shopping, lovemaking, and being together all of the time. I am having my sister Renee come here to keep you company while I am gone for that month,” Alain said.
“Ms. Featherstone will also be away during that time with her younger sister who is having a baby. I’m certain you and Renee will get along famously. She is closer to your age than either Ms. Featherstone or I,” Alain explained.
Indeed, Renee did seem quite nice during the week I got to know her, while Ms. Featherstone and Alain were still at the estate. However, I thought, that after both Alain and Ms. Featherstone departed, Renee became a little nosy over my personal affairs.
One weekend, Celine and I decided to go clubbing together, just for some fun. We hadn’t seen each other in a few months and she wanted to go to “Diva’s” Transgender Club to see if she could meet a man. Renee told me she didn’t think that was a good idea.
“You are going to a nightclub with your girlfriend, who is intent on picking up a man? Do you think that is a good idea under the circumstances?” Renee asked.
“My girlfriend Celine is looking for man, Renee. She is single. That is normal. I am simply going to accompany her there. I’m not looking for a man. I have a man that I love. His name is Alain Picard. He is your brother. Renee. Why don’t you come with us? Maybe you will meet someone? Plus, you can keep an eye on me,” I offered.
“Why Alexandra! How nice of you to invite me. I’m not sure I really want to meet someone? But I’ll accompany you anyway. But not to keep an eye on you Alexandra. I know you love Alain, and I know that he loves you, and that you have eyes for him only,” Renee said.
“That is true. Now understand Renee, that most of the men that go to Diva’s are looking for girls such as me. But plenty of genetic girls go there and find men. You are gorgeous Renee. You’ll be fighting the men off,” I smiled.
“Oh, you are too sweet Alexandra,” Renee laughed.
Of all the men that could have hit on Renee, Rocco Cabrini, who Celine and I couldn’t stand, came to our table. I couldn’t believe it. I was hoping he’d get lost, but instead, Renee encouraged him by dancing with him. If that wasn’t bad enough, she decided to bring him back to the house with her.
Renee had driven one of Alain’s numerous vehicles to the club. We had met Celine there. Celine had picked up a very handsome black man at “Diva’s” and he was following her home. I decided to drive with Renee. Rocco followed us. When we arrived back at the estate I said goodnight to Renee and Rocco and locked myself in my boudoir.
Worse yet, after an evening of lovemaking, apparently Renee and Rocco became an “Item” as it’s often called. Well, it was only going to be for a month. At least that is what I thought. I really began to get tired of Rocco flirting with me when Renee invited him over to dinner.
One evening after dinner, Renee begged me to have a drink with her and Rocco, instead of me going to my room or driving over to Celine’s.
“Just this once, Alexandra? Please?” Renee asked so nicely and sweetly.
“Of course Renee. But doesn’t it bother you that Rocco, the man you are dating, flirts with me when the three of us are together?” I asked.
“Of course not, Alexandra. He’s only playing. He doesn’t mean a thing. He’s crazy about me,” Renee shrugged.
I was right in the middle of a very large glass of Brandy, when my vision became blurred. Then the room began to spin. I stood up but could not keep my balance and fell to the floor, spilling my drink everywhere. I continued to try and stand up, but repeatedly stumbled and fell. When I tired to focus my eyes and look at either Rocco or Renee, they seemed to be smiling.
“Help me, please?” I asked.
“Of course darling, just lie there and relax,” said Renee, sitting on top of me after turning me over onto my stomach.
Renee then took both of my hands and held them behind me as Rocco cuffed them together. Then as someone slid down my panties, I felt a prick in my butt and I passed out completely. I barely remember a thing until I came to, at Rocco Cabrini’s estate on Antigua Island. I was staring at a woman who turned out to be his older sister, Brianna.
Chapter IV: Filipina Club Girl
I do not recall being clearheaded for some time. I vaguely recall being locked into the trunk of Rocco’s Lincoln Continental. I also barely remember being tied up and gagged prior to being seated in the rear of Rocco’s private jet. The flight to Antiqua was a blur. I don’t know how and when we cleared Customs but I’m certain Rocco was able to pay someone off.
I came out of my stupor to discover I was tied spread-eagle to the headboard and footboard of a truly ornate, canopied, four poster bed. I was no longer gagged so I decided to try and call for help. I was weak from the drugs though. My scream of help came out in a pitiful gasp.
Nevertheless, that was when Brianna Cabrini sashayed into the boudoir, saying, “Oh how delightful. The Princess awakens. Don’t bother to introduce yourself darling. I already know you are Miss Alexandra Jade Villenueva. It’s a pleasure to meet you Miss Alexandra,” Brianna smiled.
“In case you were wondering, I am Brianna Cabrini, Rocco’s older sister. You are now ensconced at our lovely estate on Antigua Island in the Caribbean. Rocco has admired you from afar, for so, so very long, my pretty one. He paid quite a lot of money to Renee Picard, Alain’s sister, to assist him in your kidnapping. You might say my brother now owns you Alexandra, and he intends to collect handsomely for the price he paid for you,” Brianna explained.
“Oh what the fuck? Is this some sort of joke? Did I just wake up in the middle of ‘Bad Sister Week’ or something? One little bitch sister sells me off, and now I’m in the hands of the evil sister of a greaseball gangster?” I asked as Brianna slapped my face.
“You mind your manners, you little Tranny Slut. It’s my job to make you into a hot, little, Filipina Club Girl for my brother. So are you going to cooperate or do I have to get tough?” Brianna asked.
Brianna was quite close to me. I looked at her and spat right into her face, “Fuck you and your brother, you slimy, Mafioso whore!”
“Okay you little bitch. I’ll be back and you’ll regret everything you just said and did,” Brianna promised me.
Brianna was the stereotype of an Italian, racketeer’s wife or sister. She had “Big” hair done up in a Beehive. She looked as if she did her makeup with a trowel. She wore tight spandex slacks and four-inch sandal style pumps. Her lipstick and nail polish were a hot crimson. She returned with a bleached blonde version of herself.
“Shelley. This is the mouthy little piggy I told you about. Why don’t we get started on her?” Brianna asked.
“Sure Ms. Cabrini,” Shelley said, chewing on her gum, with one hand on her hip.
They had a big gallon jug of water with them. Shelley poured out a glass. Brianna came over to me and attached a spring-loaded plastic clamp over my nose, saying, “Drink down this water honey, or your nose stays clamped shut.”
I really had no choice. In between each glass of water they gave me, they fed me plenty of black grapes. I’d eat about a dozen grapes, and then I’d drink a big glass of water. If I resisted at all, the plastic clamp went back over my nose. I don’t know how many grapes I ate, but I know I felt ready to explode as they made me drink most of the gallon of water.
I was really bloated. Then Shelley stuffed what looked like some “Chiclet’s” gum tablets into my mouth and said, “Chew it and swallow it or I’ll slap the shit out of you face, girl.”
I was now sobbing, begging them to stop. Shelley made me eat three pieces of what I thought was gum. Then they took off my high-heels, skirt and panties and slid what looked like a baby blanket under my ass, as Brianna asked me, “When was the last time you wore a diaper Allie? Because your going to need to wear a diaper tonight babe. We’re leaving you tied up. You just drank almost a gallon of water and ate about a pound of grapes. Plus to get things started, Shelley just gave you three pieces of Ex-Lax gum.”
“Let’s get her ass smelling pretty with powder and baby oil Shelley. Then put a nice heavy duty adult diaper and rubber pants on her. Make sure you give her a nice little sedative to relax those muscles,” laughed Brianna.
Shelley oiled me up, all over my butt, with baby oil, even sticking her fingers up my ass. Then she powdered me. Finally the disposable diaper went on and was taped into place, before she put the plastic pants on me. They forced two valium down my throat and told me to sleep tight, as they slid a small, plastic sheet underneath me.
“We’ll be back in the morning to change you Angel. Have a nice night Princess. Here, give Mummy and Auntie a kiss,” Brianna said as both she and Shelley forced their tongues into my mouth.
It didn’t take long for the Valium to kick in. Additionally, it was as if the Valium also reactivated the drugs I’d been given during the trip from Miami to Antigua. I began to feel as if I had to urinate. I continued to try and hold it back. But I knew I’d never hold out until the morning.
I sort of drifted off to sleep, but then the feeling of wanting to pee woke me up. Then my stomach began to groan and gurgle. The combination of all the water I drank, the fruit I had eaten and the Laxatives, were really working on my insides. Plus I knew once I gave up holding one thing back, everything would let go.
I began to urinate first. It came like a real flood. As I peed my pants I started to cry. I felt so humiliated. Then, just as I had expected, once my bladder had let go, I could no longer control my bowels and I pooped myself. The stink was awful, only making me cry all the more.
I found myself sobbing, “Oh please Alain, come and rescue me?”
I somehow managed to sleep for little while but then I peed myself and messed into the diaper all over again. I struggled against my bonds but I couldn’t do anything. I was a sobbing, smelly, nervous wreck by the time that Brianna and Shelley came into my boudoir the following morning to change my diaper. They were laughing, waving their hands and holding their noses when they entered the room.
“Oh my goodness does it ever stink in here? Shelley open a window. Did baby Allie have an accident last night? It smells like the pretty baby had a few accidents. Well, let’s change baby’s diaper and make her smell pretty again,” laughed Brianna.
“You and Rocco won’t get away with this Brianna. Alain will come for me,” I threatened.
“Alain isn’t coming for you, Princess. Not after his sister tells him that you ran off with Rocco because you were angry with Alain for not taking you to Europe. Besides, what would he do if he does get here? My brother has this place so heavily guarded,” Brianna said.
“Face it slut. My brother owns you. You may as well play along and enjoy a life as his hot, little, Nightclub Lady Boy. Or we can keep you in diapers, and feed you tropical fruit, laxatives and water for months. Shelley, let’s get Little Miss Piss Pants freshened up,” Brianna ordered.
“Then get her another gallon of water, a pound of bananas and some Ex-lax for her breakfast. How does bananas sound Alexandra?” Brianna asked.
It was bad enough spending a night peeing and crapping in my diaper. I couldn’t imagine what it would be like for an entire day? That would have to be worse than having sex with Rocco. Oh my gracious what a horrid choice that was to make.
“Please? No more. No more diapers. I’ll do whatever it is you and Rocco want me to do. Please? I’ll be a good girl. I’ll behave. I can’t take living like a baby in diapers,” I begged.
“Shelley, there has been a change of plans. Get the enema equipment. We need to get Little Miss, Stinky Pants flushed out with an enema and into a scented bubble bath. I’ll contact the hairdresser. We can’t take the chance of taking this whore to a beauty parlor just yet. She might make a scene,” Brianna added.
“Whatever you say Ms. Cabrini. It will be fun giving her an enema, anyway. Did Mummy ever give her sissy an enema, sweet, little Allie?” Shelley asked.
A few hours later I found myself seated in front of my large, ornate vanity mirror. A lovely, young, dark-skinned beautician was setting my hair. My tresses were now, very shiny, and dyed into an off-black shade. The length was still about shoulder length. My locks had not only been colored, but had been given a sexy, bobbed, fashion cut. The stylist was using plenty of pomade gel and tiny permanent wave rods.
It appeared my hairdresser was looking for a real crinkle-curl look. I didn’t care. Rocco hadn’t touched me as of yet. I’d recently had a nice, pretty-smelling, bubble bath. Prior to that I’d been flushed out with a warm soapy enema and then rinsed out with a room-temperature spring water, colonic.
I was wearing a satiny, shorty-robe and high-heeled mules. Brianna had left me and the West-Indian hair stylist all-alone. The girl was beautiful, dainty, polite and very gentle. Her name was Angela. She spoke English with a very British accent. She referred to me as “Missy” or Miss Alexandra.
“While Missy’s hair dries, would she prefer Angela to assist her in dressing?” Angela asked.
“Yes, of course. Do you know what they want me to wear, Angela?” I asked.
“Yes, Miss Alexandra. Ms. Brianna has chosen your apparel. I must put you into a waist cinch first, ma’am. Would you please hold onto the lacing bar attached to the ceiling?” Angela asked.
“Yes, I will Angela,” I replied.
For a slightly built, little native girl, Angela showed some strength as she tightened the laces of the waist cinch. She displayed no curiosity, nor had any change in her demeanor, whatsoever, when I removed my robe and she saw the penis and testicles between my legs.
In fact, once I was laced-in and she helped me with putting on my bra, she said, “You have lovely breasts, Miss Alexandra.”
I blushed at such a nice comment from a truly sweet girl. I really hoped I’d see more of the genteel Angela after dealing with the loud and very crass duo of Brianna and Shelley. Next Angela handed me a pair of panties to slip on. Just like the waist-cinch and the brassiere they were in black. I’d be wearing no hose nor any sort of brief or garter belt.
I was to be made readily accessible to Rocco. Now, Angela handed me a mini-dress. It was a ruched, satin mini-dress in a dark green brocade. The dress featured a sleeveless V-neckline with padded cups, adjustable spaghetti straps, a ruched side seam, and a mini length silhouette with an asymmetrical hem. The dress was composed of a lined, stretchy satin fabric that offered a curve-hugging fit. To complete my “look,” Angela handed me a sleek clutch and a rhinestone choker.
After stepping into a pair of black, sandal-strap, four-inch heels, I sat back down at the vanity and readied myself for a comb out and makeup. As Angela wrapped a salon cape over my shoulders I asked her about herself.
“Where do you live Angela? Do you have family here? If I’m not being rude, how old are you?” I asked.
“I rent a small studio apartment above the salon where I work. It belongs to the owner of the beauty parlor. I was born here. All of my family, mother, father, brothers and sisters moved to either England or the United States. I chose to stay here. I’m nineteen,” Angela stated.
She was a year younger than me. A local girl. I wondered aloud.
“Angela. If I were to secure a job for you here at the estate, as my attendant? Would you accept it? I’d see to it that you received room, board and salary,” I added.
I knew I was going beyond my bounds, but I wanted to see to it that if I were to be Rocco’s whore, that I was properly compensated.
“If you could arrange that Miss Alexandra, I would accept this. The estate is so lovely and I’ve always liked Ms. Brianna Cabrini,” Angela stated.
Just then Brianna knocked and entered, saying, “I don’t want to interrupt. Well, it looks as if you’ll be ready to be presented to Rocco shortly. Alexandra? I have a local GYN coming by this evening. She’s making a special visit, just for you. She has some amazing bootleg Estrogen that all the Trans-Girls at the clubs are raving about,” smiled Brianna.
“The doctor says that it’s extra-strength. Perfect for a growing young girl like you. Don’t you think dear? She’ll give you a booster and she’ll leave you with a six-month supply. She’ll also return in two-weeks for another booster. Once we can trust you we can begin going to her office downtown as well as the salon where Angela works,” Brianna explained.
“I usually only get a monthly booster. And I’d like to speak to you about Angela, if you don’t mind, Brianna?” I asked.
“Well, Rocco and I want to see some real growth in your boobs and your ass, Sweet-Thing. So you’ll be getting boosters every two weeks. Now, what about Angela?” Brianna asked.
“I’d like her to be hired as a private attendant for both of us. To do our hair, nails, makeup, help us dress, and things of that nature. Sort of as a ladies’ companion? Live-in of course. With room, board and salary, along with a clothing allowance. We’d want her to look her best when we entertained, wouldn’t we?” I said.
“I’d say it sounds as if you think you’re now the Lady of the Manor? I mean you are making employment decisions already? However, I love the idea. Consider it done. I’ll run it by my brother, but that will only be perfunctory. I make those sort of household decisions around here,” Brianna stated proudly.
“You can do that today? So she could take care of notifying her employer? And thank you Brianna. I’d really like us to get along, you know? After all, I’ll be having sex with your brother very soon,” I added.
“Yes, I’ll do it today. In fact she’s hired this instant if she wants the position. And I’ll see that she’s well-compensated. I’m not cheap. Yes, I’d like to get along with you also, Alexandra. We don’t need to have an adversarial relationship in spite of getting off to such a bad start,” Brianna stated as she warmed to me slightly.
“Incidentally. Your hair looks fabulous with those crinkle-curls. I think we should have your tresses, spiral-permed. Dressing and coifing you will be like having a baby-sister. In fact, seeing that we’ll be having our own personal hairdresser, I’m going to purchase some salon equipment,” Brianna said excitedly.
“I’ll have the vacant area near the sun-room converted into a personal, home, beauty parlor. I’ll be back soon. Will she be ready in forty-five minutes, Angela?” Brianna asked.
“Yes ma’am,” Angela stated.
As Brianna walked away, even though my hair was only half done, I motioned for Angela to allow me to follow Brianna. I minced out into the hall, with the cape still around my shoulders, half of my hair in crinkle-curls and the other half still up in tiny perm rods.
“Brianna. I need to speak to you privately. I just wanted to add that Angela is an innocent, nineteen year old village girl, if you know what I mean. And I’d like her to be hands-off. Please? Is that at all possible, Brianna?” I asked.
“Well look at you, Alexandra. So, you’re a Whore with a heart, aren’t you? Look, I know exactly what you mean. She’s a kid. Don’t worry. I know my brother and his associates are pigs. Real pigs. But you don’t know the swag I received from my father when he died. I have real influence around here Alexandra. Besides, my brother will have his hands full with his new, Filipina Lady Boy slut, won’t he?” Brianna smiled as she walked away.
Then Brianna stopped, turned around and called back to me, saying, “Don’t fret. I’ll take good care of our girl. You just keep my brother happy. You hear me, girl? I’ll even put her in the boudoir down the hall from you.”
An hour later I stood in front of Rocco as he sat relaxing in his den. He held a glass of Chivas in his right hand. He looked me over. My hair was really “done” beautifully. Off-black, shiny, crinkle-curled and heavily sprayed. My makeup was no less than lustrous. I’d never in my life worn such vivid, crimson lipstick.
I did a twirl for Rocco. He loved it. I sashayed over, much closer to him and asked, “Does Don Cabrini like what he sees?”
“Yes, very much. You are every bit the gorgeous Filipina I knew you would be. You were much too prissy and innocent as a white girl. This is what I wanted. You vamped-up nicely,” Rocco stated.
“I’m very happy that Master-Daddy is pleased. May I pull Daddy’s penis from his slacks?” I asked, kneeling down in front of Rocco.
Rocco said nothing so I unzipped his pants. I pulled his penis out and licked it. Then I unbuckled his slacks and he sighed, sipping his drink. I motioned that I’d like to take his pants off and he nodded. I began with his shoes, sliding them off. Then I slipped his pants down his legs.
I folded his pants off to the side near his shoes. Once his underwear was off, and he was naked from the waist down I took his cock fully between my wet, crimson lips. As I sucked his cock, to take my mind off of this crude, brute, I inhaled deeply. I took in the beautiful blended scent of my hairspray, cosmetics and perfume.
I knew I actually looked more lovely than ever. I hoped only, that one day Alain could see me looking this way. Prior to making my way with Brianna to Rocco’s den, Angela had posed me before a full-length mirror, standing on my tall heels. I took in the dark sheen of my lovely thick hair, my pretty red lips and the stunning, figure-hugging, brocaded mini-gown I was wearing. Dangling from my pierced ears were slutty looking, large gypsy hoops, along with elegant, jeweled, teardrop pendants.
I stared at my slim waist and my well-turned legs. I then recalled a TV show I’d seen as a young teen. My father had been proud of his Filipino heritage. However, when he’d become well-renowned as a builder of luxurious homes, he’d moved our family into an upper-middle-class, predominantly Caucasian community.
He became a member of the local chamber of commerce. My brothers all played sports on the local high-school and later college athletic teams. As a young, girly, Mummy’s boy, I assisted mother in cleaning house and cooking. I also reveled in doing my mother and aunties’ hair and nails.
One evening, as my father and brothers watch a sports program in the living room, Mummy and I watched TV in the den as I brushed her hair. Mummy had the PBS channel on and a show began on Transgenderism. The narrator warned of Adult Content. In spite of the fact that I was a young teen Mummy didn’t change the channel.
The show covered stories about Transgender males and females throughout the United States and all over the world. However when the program moved to Asian countries such as Thailand and the Philippines my interest became captivated.
I had completed brushing Mummy’s hair so I sat down next to her and snuggled in her arms. My eyes grew wide and my pulse raced at the sight of the exotic Filipina Lady Boys in the bars and nightclubs around the city of Manila. I couldn’t believe the gorgeous dresses and gowns they wore.
The tall heels and the tight clothes along with their beautifully coiffured “Big” hair, mesmerized me. Their brilliant makeup and their gaudy jewelry excited me. Mummy must have felt my heart beating faster, for she said to me, “They are so gorgeous, aren’t they Alex?”
“Yes Mummy, they are,” I gasped.
I had an erection and I told myself it was because I saw them as pretty girls I’d like to kiss. But, I know now, today, that it was because I wanted to one day look like them. Did my mother know? Yes, of course she did. She has told me so, since the time she finally met me as Alexandra.
When at last I saw myself, displayed by Angela in the full-length mirror, as a perfect vision of the Lady Boys I saw that night on the TV screen, I knew my destiny had been fulfilled. Even though I would soon be in the arms of a disgusting mobster, I knew one day, I would make love with Alain as his lovely Filipina.
As I surrounded Rocco’s cock fully with my mouth, I looked up dreamily into his eyes. He smiled as I gave him a seductive wink. Then I asked him, “Does Daddy want his girl to swallow?”
“I was thinking, that you could bend over the back of that couch, lift your dress, lower your panties and I could put my dick up your ass, honey. I’ve got some KY Jelly in my desk drawer. You won’t be the first sissy I’ve screwed in this room. But you will be the prettiest,” Rocco said.
“Lovely,” I thought to myself, as I let his cock plop out of my mouth, and I minced over to the couch and positioned myself for a screwing. Rocco’s penis was well sized but nothing like the massive organ that Alain displayed. I kept that to myself, not wanting to bruise Rocco’s ego. As manly cocks go, Alain’s is just much too impressive for words.
I wiggled my girly ass, saying, “Oh Daddy, here is your hot sissy, ass-pussy, all ready for the taking!”
I felt Rocco’s clumsy fingers lube my ass. His style just wasn’t as careful and gentle as Alain’s. I couldn’t help but compare him to Alain, though really ladies, there wasn’t even a fair comparison. As Rocco slid his lubricated cock inside of me, he pushed roughly, in a blundering, animal-like fashion.
He grunted as his dick slid all the way up inside of me. Then he began pumping. It felt good enough. What cock doesn’t feel good up a girl’s ass? Even the cock of this thuggish pig gave me some pleasure. But if I live to be a grandmother, no man’s penis or lovemaking will ever compare to Alain Picard’s.
Plus, Alain would always touch my small cock and balls, or my “sissy-clitoris” as I thought of it. He’d always gently rub me in some way to stimulate me so that I could have a “sissy-cum,” and ooze my sissy-cream from the head of my clit. On a few occasions Alain would even lick me there to stimulate me wildly beyond my imagination. But not Rocco. Never did he seem to care about my pleasure.
Only his pleasure was important as he pounded away at my pretty ass. Finally Rocco grunted loudly and thankfully expelled his semen. I was so glad. It was over. I didn’t expect any post-coital touching or snuggling and I was correct. And gladly so. I didn’t want him touching me. Nor did I attempt to keep Rocco’s seed inside of me.
I allowed his cum to drip from my ass, down my leg and onto the plush, carpeting. Thankfully Rocco did not notice. Nor did I care.
“That was nice baby. We need to do that some more. I knew you’d be a hot fuck. I knew it the first time I saw you. I’m glad you’re mine now,” Rocco smiled and the thought of me being “his” gave me the creeps. I needed to do something to make him think I’d enjoyed the sex.
“Oh Daddy, you bet that I’m your’s. I’m all your’s honey,” I said as I hugged him and kissed his lips.
The problem with Rocco, as Celine had told me was that he enjoyed threesomes and it was all about Rocco. Plus, he liked sharing his girls with his buddies. That was where my problems with Rocco really began.
Chapter V: Damsel in Distress
Having a perm put in, wasn’t tops on my list of beauty treatments, but Brianna found it to be essential. Keeping both Brianna, as well as Rocco happy, was a priority for my survival. So, of course getting a perm was what I did. I’d given dozens of perms as a hairdresser, though I never thought I needed to get one myself.
But there I sat, after a shampoo, a conditioning treatment and a light trim, with my lovely girlfriend and attendant, Angela, winding wave rods into my thick, dark hair. Brianna had insisted that my hair was to be permanently “Kink-curled” in keeping with her brother’s fascination with me emulating a stereotypical Filipina Lady Boy.
My sexual sessions with Rocco had become frequent and only recently I’d participated in a “threesome” with him and the very distasteful, Shelley. Brianna was quite happy with the home beauty salon that she’d paid a contractor to set up. It was rather elaborate, with two shampoo sinks, a massage table, two styling stations, a cosmetic station, and exotic, ornate furnishings.
She herself had made great use of the salon already, and Shelley had recently had her blonde hair dyed a shimmering, “Anne Margaret” red. As Angela wound my hair around the perm rods, I could barely get the picture of that “Flame red” haired, skank, Shelley, prancing into Rocco’s bedroom to have sex with us, out of my mind.
But I managed to forget it, and relaxed, as my beautiful girlfriend Angela completed my rollup and began wrapping my perm with the cotton gauze prior to adding the acrid smelling perm solution. As Angela did saturate my hair with the smelly perm lotion I thought about what fun it would have been to have my Mummy give me a home perm.
Not as a little sissy boy but as my Mummy’s little girl. Somehow I knew if my mother could see me as Alexandra Jade, she would adore me. I just knew it. I also knew that whenever Alain came to rescue me from this crude, crime family I wanted to see my Mummy and let her know how pretty a girl I had become.
As I sat under the hair dryer, reading a fashion mag, I thought of the fun Mummy and I would have together. And as Angela finally removed the perm rods from my hair and smilingly gave me a comb-out and final spray, I wanted Angela to take a photo of me and my “first” perm to show to Mummy.
But, for time being I’d have to somehow learn to tolerate the piggish nature of Rocco and his horrid friends, along with Rocco’s crude ideas of lovemaking. Not that I’d ever considered being in Rocco’s bed with him, any more than screwing. Upon the evening that Shelley had strolled into Rocco's bedroom I had no idea what I was in for.
Rocco insisted that Shelley and I “Eat each other out” first, as he watched and played with his own cock. I don’t know which of us found it more distasteful? Was it me, licking Shelley’s pussy, or Shelley having to suck on my shrunken, girly, penis and testicles?
I’d never really been turned on by girls. Even as a sissy Mummy’s boy, who had kissed girls, I preferred to curl a girl’s hair or paint her toenails rather than have sex with her. The first girl I’d ever been to bed with was Celine. Even then, though we had cuddled, petted and kissed, I’d never even came close to “Going all the way” with Celine, even in an oral sense.
Being in bed with Celine, was more of an affectionate, “Mother” or “Sister” thing. Of course, with Shelley, I wasn’t aware of what Rocco would do if I ever refused to have sex with him or someone else. As I licked Shelley’s twat, she really did come alive. I figured if I was going to be eating pussy on a regular basis I might as well be good at it.
Shelley wriggled her hips, the more pressure I put on her clit. She was doing a nice job of licking my little sissy bits. I could feel myself getting excited and I knew Shelley was. What would happen shortly, was hardly in keeping with what I desired in the way of lovemaking. But at the very least, I was adjusted for the time being with the threesome.
The more excited Shelley became, the harder I tried to make her orgasm. I could hear Rocco breathing heavier, and when I peeked out of the corner of my eye, I could see that the dirty pig was jerking off. I continued to lick and suck Shelley until she convulsed screeching. At the same time my tiny penis and testicles squirted out sissy cum.
Rocco masturbated himself to climax. While we were all laying there sated, there was a knock upon the door and one of Rocco’s friends, Carlo came in. He began to undress and Rocco said, “I want you girls to show Carlo a good time.”
I stood up and put my dressing gown on and walked to the door.
“No thank you Rocco. This is where I draw the line. One threesome is enough for me. This is why Celine dumped you. Someone else can show Carlo a good time,” I said as I walked into the hallway.
Rocco came out into the hall and began to become angry. When he said something threatening in a sexual way concerning Angela I began to yell threats towards him. Just then his older sister Brianna appeared out of nowhere and told us both to shut up.
“You get back to your room, Alexandra. Rocco. If you look cross-eyed at Angela, you’ll regret it. This is why Daddy left me in charge of the family business. Now both of you shut up,” said Brianna.
It was then I noted that Brianna was armed, with a machine pistol at her side. Rocco actually looked scared of her. The following evening things seemed to be forgotten as I dressed to go to Rocco’s nightclub. I actually did enjoy the club. I felt as if I was the hottest bitch there. Everybody paid attention to me as I was Rocco’s girl.
There were other Lady Boys, just like me there. But I always felt I was better looking than any of them as well as any of the genetic girls at the club. And I always believed I was the best fuck and the one who could give the best blow job in town. I looked fantastic that evening. My off-black hair shined in the club lighting.
My recently permed hair was jelled and teased to perfection. I wore this glorious masque of thick, brilliant makeup. I had been getting Collagen Lip Plumping from Angela. Brianna had decided I needed nice fat cocksucker lips. Truthfully, I loved the way my bee-stung lips looked with Creamy Lavender Lipstick.
I wore a gorgeous, shorty, wraparound floral-patterned gown, and stood prettily on five-inch pumps. I had dark, seamless patterned hose and a garter belt. I felt so fucking hot! We arrived at the club in Rocco’s limo. I waltzed into the club and took over from the hostess. I went from table to table asking people how they were enjoying themselves?
I’d ask them about their drinks, the food and the entertainment. I was always popular with the Tranny-Chicks that turned tricks at the club. We’d been there about thirty minutes when Solly, one of Rocco’s bodyguards came to see me.
“Mr. Cabrini would like to speak with you in his office, Miss Villenueva,” Solly said.
“Of course Solly. Virginia, would you take over for me and see to the customers honey?” I said to the regular hostess.
I followed Solly into the office. He held the door for me. As soon as Solly closed the door two of Rocco’s thugs grabbed me. Rocco sat at his desk smiling. I tried to pull myself free from both of Rocco’s thugs but my attempts were fruitless.
“Hi sweetie. So you didn’t want to fuck Carlo the other night? I got the message from my sister about keeping my hands off of Angela. But she didn’t say anything about you. Well tonight you’ll be servicing a few more of the club’s guests besides Carlo. Enjoy yourself, you little bitch. Boys, take her to the seat of honor,” Rocco laughed, pointing to his right.
In the middle of the office floor was a large, wide, wooden, office desk chair. At the front of the chair seat, was a built-on extension. The extension was constructed very similar to a set of “punishment stocks” that one would see in a movie about old colonial days in a place such as Plymouth, Massachusetts.
As Rocco’s two “boys” drug me over to the chair I struggled and screamed, “You bastards get your hands off of me! Rocco? What the fuck is going on?”
“You didn’t want to screw Carlo, the other night? Well tonight, once your head and arms are locked into the seat of that chair you’re going to suck a little bit of cock and eat some pussy too, and everything in between. Plus with that hot little ass being exposed you might take a little screwing, up your ass, too,” Rocco laughed.
I was fighting but those two thugs were far too strong. They locked my head into the center-piece with my neck tightly secured. Then my two arms were locked into the end pieces around my wrists. Now anybody that would sit in the seat would easily be able to insert their penis into my mouth.
“Bobby? Why not have a seat, take your prick out and let Alexandra give it a lick? That a boy. Get those pretty fingers around his cock Allie. Good girl. Give Bobby a nice blow job honey. You know? I’m going to put a tip jar next to your chair and make a little money,” Rocco teased, really enjoying himself.
Bobby decided not to have me swallow and shot his load right into my face and hair. I’d spent all afternoon on my hair, makeup and getting dressed and Rocco now had me imprisoned in his office sucking cocks and licking pussy. For much of the rest of the evening I was degraded by customers of the club and friends of Rocco that he invited into the office.
Some people came in with their drinks, just to watch. Even more humiliating were the “tips” I was given. After a blow job or a puss lick, my various male and female clients, would throw a dollar or two or sometimes a handful of “pocket change” into jar. I’d never been so humiliated in my life.
At one juncture, while I was eating a woman’s puss, her husband was screwing me from behind. I had sperm all over my face and hair, and quite a bit of ejaculate was dripping out of my ass. After a few hours of this I was a nervous, sobbing wreck. I was swearing at Rocco and becoming hysterical.
He even had one of the Tranny Hookers come in and get her cock sucked. I could tell the girl was a little nervous and felt sorry for me, so I gave her the best blowjob she’d probably ever had and swallowed every drop of her cum. Finally though, my emotions exploded.
“You dirty, filthy, greaseball cocksucker! How could you do this to me? Let me out of this. I hate you, you creep!” I yelled.
“Watch your mouth you slut. And who are you calling a cocksucker? You want out? You beg me you bitch. You tell me you learned your lesson. Are you ever going to refuse to screw one of my friends again?” Rocco asked.
I couldn’t take any more of this. I had to beg the son of a bitch. I swallowed any pride I had remaining, and began begging, “Please let me out of this? I’m sorry Rocco. You’re my Daddy. I love you. Please? I’ve learned my lesson, honey. I’ll do whatever you say,” I sobbed hysterically.
Covered in cum, with my ass sore, Rocco sent me to the bathroom to clean up.
“Take your purse with you. Fix your hair makeup. You look like shit. Then get your ass out there and schmooze the customers,” he ordered.
By the end of the evening, I was thrilled when Rocco told me we were leaving. However my degradation wasn’t quite over with. As we climbed into the limo I gasped when I saw that Carlo was seated across from us.
“Before we leave, get over there on your knees in front of Carlo and suck him off. Now, bitch!” Rocco ordered.
My entire body was shaking. I took Carlo into my mouth. But that wasn’t enough for Rocco. As I blew Carlo, Rocco got behind me and started screwing me. Carlo came in my mouth first. Soon after, Rocco shot his load into my ass. By the time we returned to Rocco’s estate, I ran from the limo into house leaving a laughing Rocco behind.
I was laying in bed sobbing, when Angela came into the room asking, “Miss Alexandra? What is wrong? Oh, you look a mess. I’m drawing you a bath, ma’am.”
My lovely Angela not only bathed me, but she spent the evening with me, holding me, running her fingers thru my hair and comforting me. Thankfully, it was only a few evenings later, that I began to hear the loud noises outside.
I was reading a fashion magazine, when I thought I heard an airplane. It was actually a helicopter. Then I heard sirens and wondered if those were from police cars, fire trucks or an ambulance? Then there was shouting and loud voices. Finally I heard the sounds of guns being shot.
I jumped out of bed and laid on the floor, scared and shaking. It seems as if I had laid on the floor forever when Brianna burst into the room, threw on the light and yelled, “Where the hell are you Princess? Oh, there you are. Get up. Now. We’re getting out of here and you’re going to be my hostage Angel. You’re my ticket out of this mess.”
She was holding a gun. She walked over to me and pulled me to my feet. Then, out of nowhere, my “Knight in shining armor,” Alain came thru the doorway, armed and wearing some sort of military uniform.
“Drop the gun now lady and move away from her,” Alain demanded.
“You drop your’s or she gets shot,” Brianna said.
That was all it took for Alain to pull the trigger. Alain’s gun only made a sort of pop. He later explained he had a silencer on it. I watched as Brianna’s body jerked. Then the gun dropped from her hand, she pitched forward, and fell to the floor. She laid there motionless, a pool of blood forming around her.
“Oh Alain, I knew you would come for me. Oh my Alain, you shot her?” I said.
“Yes. I’m sorry it took me so long. I hope they haven’t hurt you in any way, Alexandra? Yes. I had to shoot her. She threatened to shoot you. She left me no choice. Who was she?” Alain asked.
“She was Rocco’s sister, Brianna. She was a bitch. She’s dead, isn’t she Alain?” I asked.
“Yes. Now come. I have a helicopter waiting to take us to my private jet at the airport,” Alain stated.
“Can I change? I have my nightgown and marabous on?” I asked.
“We haven’t the time. You look fabulous by the way. Your hair is much darker and curlier. But I like it somehow,” Alain stated.
“We have to get Angela. She’s right down the hall,” I said.
“Who is Angela?” Alain said, following me.
“My friend. You’ll like her. We must take her to Miami with us,” I insisted.
A call came over Alain’s two-way radio, saying, “Colonel Picard, this is Captain Drummond. The residence and grounds are secure sir. Numerous arrests have been made and a number of the hostiles have been neutralized,” the voice said.
“Excellent Captain. You are now in command. I will be leaving with two passengers on the copter. There is the body of one, Brianna Cabrini, in a bedroom of the south wing,” Alain added.
I was able to get Angela to unlock her boudoir door and come with Alain and I to the copter. It wasn’t until Alain’s jet was in the air that I could relax long enough to throw my arms around Alain to kiss him passionately. We settled in for the three and one-half hour flight to Miami. We arrived at Alain’s estate at 4 AM.
On the flight, Alain explained that he had been forced to “interrogate” his sister Renee about my whereabouts as well as the truth concerning my kidnapping.
“I don’t care that she’s my sister. You are the woman that I love and she harmed you in no uncertain terms. I can have her jailed for a long time as an accessory to kidnapping. However, I will leave it to you, as the party that was wronged, to decide her fate, Alexandra,” Alain added.
“Hmm? Well, I’ll have to think about that, among other things Alain. I love you Alain. You realize that, don’t you?” I asked.
“Of course I do darling,” Alain said, as he took me in his arms and smothered me with kisses.
“Alain, I didn’t know you were some sort of soldier?” I asked when we came up for air.
“Only a reservist at this point, but I have connections. When you are wealthy, you have connections,” Alain smiled.
Chapter VI:The Princepessa and the Sissy Wives
I looked at the two, gorgeous, little, five-year-old, Filipina twins in front of me and could not believe they were mine? Mine and my husband Alain’s of course. Angela and I had just finished curling their hair, dressing them, and putting a tiny bit of makeup on each of them. We were getting the girls ready for an outing with my mother and Ms. Featherstone.
Prior to us being married, Alain had insisted that my mother, Diana, move in with us. As she was then, finally divorced from my father, she was thrilled to take us up on our offer. But before to that, of course, she needed to meet me, as Alexandra, the daughter she had yet to see.
That was a big day for both her and I. I was excited, with my hair still in curlers, as Angela dressed me in a virginal, white crepe dress and matching white heels with sheer hose. I sat at the vanity as Angela tried and succeeded in calming my nervousness.
“Your Mummy will be so happy to see her daughter Miss Alexandra. She will be so proud and happy to witness how sweet and pretty you have become and she will be thrilled that you are soon to be happily married to your handsome future husband Monsieur Picard,” Angela said.
At that moment my new maid, Betsy Ann knocked and asked permission to enter my boudoir. Betsy was so well-trained, subservient and properly attired. She was also the epitome of a perfectly drab, inconspicuous, English maid. Betsy hadn’t always been like that. In fact she’d once been haughty, arrogant, beautifully coiffed and stylishly attired.
She had once been called Renee. And before I’d asked Alain to disown her, and cut her off from all her family funds and holdings, she’d been Alain’s younger sister. The timid, unassuming, so obedient Betsy Ann was at one time the evil bitch that had plotted my kidnapping.
“Yes, Betsy, what is it? Oh my but you look so nice and prim today Betsy. You’re so much the plain wallflower aren’t you dear?” I snickered.
“Oh, thank you ma’am. You do look lovely, Madame Alexandra. Everything is prepared for luncheon ma’am. Is there anything I can do until you honored Mother and Aunt arrive, Madame?” Betsy asked so properly.
“Yes there is girl. Miss Angela just tossed several pairs of my soiled panties, dripping with my pussy juices and lubricant into one of your laundry baskets. Those panties need to be hand washed. And don’t you have a number of blouses and tennis skirts which belong to Miss Angela and I, in your laundry basket,” I asked.
“Yes ma’am, I do,” Betsy whispered.
“Well then hop to it girl. The panties come first and you should already know that. And then the blouses and skirts. You’ll be able to hear the doorbell when the guests arrive,” I answered.
By the day after our arrival back from Antigua, I knew what sort of consequences I wanted the former Renee to pay. I let my darling Alain know in no uncertain terms.
“Darling for what I was put thru in Antigua, I’d like your sister to be rendered penniless and to become totally and unequivocally dependent upon us. Her penance, as well as her prison, for her indiscretions, shall be to spend a heretofore indefinite period of time as my drably attired, colorlessly coiffed, inconspicuous, insignificant English-styled maid,” I pronounced.
“It shall be done immediately, my Princess,” Alain said, as he smiled and bowed so handsomely from the waist.
“And Ms. Featherstone, Angela and I, will see to her new coiffure, as well as her attire,” I grinned.
We could all hear the wails and the screams from the girl, once named Renee, as Alain announced her fate to her. We led the whiny bitch, to her new, tiny, plain maid’s room in the nearly empty servant’s quarters. Then we took her to the newly decorated and remodeled home beauty salon for her “Makeover” of sorts.
I must take the time, to tell you of how Renee’s tresses were once coiffured. She was always so very proud of her hair. Her locks were quite long, past her shoulders, and colored a brilliant honey blond. They fell beautifully in distinct spirally curls. The first order of business was for Ms. Featherstone, Angela and I, to securely tie and gag Renee into a beauty salon chair.
We forced her to look into the well-let, wraparound mirror and observe, as Angela began to use scissors to chop off large swaths of Renee’s cornsilk-like locks. Renee squealed futilely against her gag and struggled mightily with her bindings but her efforts were useless.
Smiling, I held up the large clumps of cutaway tresses for everyone, including our “Maid” to see. I caused Renee to squeal even louder when I asked Angela, “Darling, when you worked at the salon, did you ever shave the head of one of you female clients, completely bald?”
“No Miss Alexandra, that would be a first for me,” Angela added.
“You know ladies, instead of shaving Betsy Ann bald, why not give her a short bobbed hairstyle. One that hardly covers her ears. Then clipper and shave her nape, up quite high. After that we’ll dye it a nondescript, mousy-brown. And our new maid is to be renamed, Betsy Ann,” I announced.
We led the sobbing Betsy Ann back to her new, tiny maid’s quarters and showed her the very plain wardrobe she’s be wearing. Her long locks had been shorn. She’d been given a short bobbed “do” that barely covered her ears. Her gaudy earrings had been removed. Then her bobbed “do” had been clipped and shaved ever shorter in the back.
Her former flashy clothes were given to Angela. Her new maid’s outfits were as plain and shapeless as could be. She’d now be wearing “sensible” footwear as well as skirts and dresses in non-colorful shades such as grey, black and brown.
I told her she was not allowed to use any cosmetics with the exception of a coat of soft, pink, lipstick, a touch of rose blusher and a smidgen of mascara and eyebrow pencil. Until further notice she was forbidden to apply eye shadow.
The former Renee had never had a large bust. Certainly nothing compared to the implanted set of 36-C tits that I have today. But now, with the loose fitting unshapely attire she’d be sporting, she’d look virtually shapeless and flat-chested. Betsy Ann would look more like a boyish sissy maid than she’d look the part of a real girl.
And certainly no woman wants a glamorous maid in her household anyway. Upon the day that Mummy and Auntie were coming to visit, as Betsy Ann minced off to hand wash my panties, Angela began to style my hair. It had been Ms. Featherstone that had first contacted Auntie Lynette who had told her, that Mummy was now divorced and living with Auntie.
“She is looking for her own place to stay though. She wants me to have my privacy. So you say Alex, I mean Alexandra is now living full-time as a female? I always thought she’d be happier as a girl,” Auntie Lynette said.
“Well then, why don’t I visit you and your sister Diana, and bring along some recent photos of your lovely new niece and of course Diana’s daughter? Alexandra Jade would love for both of you to visit, see her once again, and renew the relationships,” Ms. Featherstone stated.
“She also wants you to meet her handsome, soon-to-be fiancee, Alain Picard. Would you allow me to visit Lynette? And would you consider a visit to the lovely estate where Alexandra Jade now lives?” Ms. Featherstone asked.
Ms. Featherstone’s entreaties worked and Mummy would soon be arriving. I felt like such a Fairy Princess in my white heels, white crepe dress, which dripped in lace appliqué, and my all white underthings. My dark, thick, curly hair contrasted so dramatically with my attire. I heard the doorbell ring and listened to the click-clack of Betsy Anne’s kitten heels on the tiled flooring.
I could hear the voices in the hall. The voices faded as the people moved into the parlor. Then I heard Betsy’s light knock and her soft voice saying, “Madame Alexandra. Your guests await you ma’am. Monsieur requests your presence.”
“Thank you Betsy. You may run along girl and see to our guests. Angela will escort me and announce me as well,” I stated, feeling so much the part of a Princepessa.
I followed Angela to the doorway of the parlor. Angela entered the room and introduced herself to Auntie and Mummy, saying, “Hello Ms. Diana and Ms. Lynette. I’m so pleased to meet you. I am Angela, Miss Alexandra’s Personal Assistant. Monsieur Picard, shall I have Miss Alexandra make her appearance, sir?”
“Yes, Angela. Please do. I’m certain her Aunt and Mother are most excited to see her,” Alain stated.
“Very well sir. Ladies and Gentleman, Miss Alexandra Jade Villenueva, if you please. Miss Alexandra?” Angela called out.
I minced so daintily into the parlor, balancing perfectly on my five inch spike heels. My lavish curled upsweep, glistened with all the gel and hairspray Angela had used in my stylization. I’d even inserted a butt plug so that my hips would have an exaggerated feminine wiggle.
I adored the three sets of dangling earrings I wore in each ear. My crimson nail polish perfectly matched my wet look lipstick. I was truly the glamorous Filipina that I strived to be. I stopped in the middle of the parlor and curtsied perfectly.
“Auntie Lynette and my dearest Mummy Diana, I’m so honored and thrilled you would visit today,” I said in my sweetest little girl voice.
Aunt Lynette smiled. She’d seen me dressed in the past, though never like this. But I think she’d always known I had amazing possibilities. Mummy, on the other hand, had momentarily opened her mouth and eyes, wide in shock and surprise. Then with her hand on her chest, and smiling from ear to ear she stood up and approached me.
“You were always such a pretty, effeminate child. But, Alexandra Jade, I never dreamed you’d make such an enchanting daughter?” Mummy said as she came to me and threw her arms around me.
“Lynette, look at her! Isn’t she amazing? How beautiful she is. Oh my lovely child. Oh, I love your hair. You look fantastic like this, Alexandra. Kiss me my little one, please?” Mummy said.
I kissed her all over her face and hugged her incessantly. I did the same with Auntie. They were crying. I tried my best not to cry as I dreaded ruining my makeup. I realized I’d forgotten my clutch handbag until I looked at Angela. My faithful girlfriend then winked at me, and held my clutch in the air briefly.
I was so relieved. I could fix my lipstick. I sat nearest Auntie and Mummy. As Betsy served refreshments, Mummy chattered away, talking about me as a child.
“I always felt Alexandra should have been born a girl. I know that after three rowdy sons, I prayed for a female to be conceived. She was born such a beautiful boy and became such a gentle, effeminate child. She was a joy to be with and was so very helpful around the house,” Mummy said so sweetly.
“I am very happy about you Alexandra. I am thrilled that you have discovered who you really are. And I am excited that you have found a man that you love and a man who also loves you,” Mummy added.
“Oh thank you Mummy for saying that. Alain, wasn’t there something you wanted to ask Mummy for the both of us?” I asked.
“Yes. Ms. Diana. I understand from speaking with Ms. Featherstone that you are considering looking for your very own place to live, in order to give your sister privacy. Alexandra and I would like to extend to you a place in our home. You wouldn’t just have a room, you would have an entire suite, including a kitchen,” Alain stated.
“But of course as a member of the family you could always dine with us, should you feel so inclined,” Alain continued.
“Please Mummy. Say yes. Say you’ll live with us. Alain and I will be married in the not-so-distant future. We plan to adopt. I promise you Mummy, we will adopt all girls. You will have granddaughters right with you, were you live Mummy,” I said.
“Oh that sounds wonderful. Your brothers have given me all grandsons. Yes, I’ll be more than glad to accept your kind offer, Monsieur Picard,” Mummy agreed.
“Please call me Alain, Ms. Diana,” Alain asked.
I then instructed Betsy Ann to serve the food and beverages. I was so very happy. Mother ended up moving in within the month. As I now had Angela as my Personal Assistant and Betsy Ann as my Personal Maid, I assigned Brandy, my former maid, to care for Mummy’s personal needs. Now I got down to the more serious matter of becoming a real female, or as close to a real female as physically possible.
I visited my GYN to make an appointment for surgery to have my testicles finally removed. I had it done under general anesthesia as I didn’t want to be awake. Once my nuts were clipped off, my empty ball sac would still be there. It would one day be used, along with my now useless penis, to form my vagina.
I waited a small amount of time before seeing the surgeon who would ultimately make me a female. I wanted to have a pussy for Alain to screw on our honeymoon. I also never wanted the girls I would one day adopt, to ever know that I was once a boy.
The female surgeon went over all the details with me. Now that my body no longer made testosterone, I felt more like a female. My surgeon felt that I would not need a tracheal shave, vocal cord surgery, or any work on my face.
“Your voice is perfectly girlish Alexandra, as is your throat and neck. You facial features are also decidedly feminine. Outside of the larger 36-c bosom that you desire, you vaginal reconstruction is all you really need done. Would you like to do the boob job during the same procedure?” Doctor Gladden asked.
“Yes ma’am. I would. It will only involve one recovery,” I agreed.
Indeed, as I hadn’t yet turned 21, I was young and strong enough to go thru the recovery with a minimum of pain meds. And I had the most wonderful home nursing staff of Mummy, Ms. Featherstone, and Alexandra. Of course Celine and Auntie Lynette dropped by to help.
When I felt well enough to get around, I began to plan a small intimate wedding for Alain and I. Of course mother would give me away. Aunt Lynette and Ms. Featherstone would be my Matrons of Honor. Angela and Celine would be my Maids of Honor. What I really cared about the most, was wearing a beautiful white gown, an elaborate hairdo, and amazing, wedding makeup.
After the wedding, we spent the entire month of June, touring Europe in Alain’s private jet, and screwing in each luxury hotel we stayed in. I was hardly a virgin in the truest sense of the word. But as my brand new pussy had never known a man’s cock, I was certainly virginal in that respect.
Our first stop was the Costa Del Sol, in Malaga, Spain, which had become an absolute Mecca, for Transgender Girls, the world over. I did think, however, that the Brazilian Trannies, that walked the beautiful beaches by day, and danced in the clubs at night, were truly, the most special. Our first evening in our spacious and luxurious hotel room, we began with a romantic, candlelight dinner.
I settled on Lobster with white wine. Alain looked so amazingly handsome and masculine in the candlelight. For weeks on end I’d been preparing my new pussy for this very night. I’d been softening my inner vaginal walls with Estrogen creams, Lubricating gels and Asian Herbal Lotions.
Celine had been privy to the same surgery a few months prior. She had been so very wonderful as to assist me with widening my passage with the numerous dilators given to me by my surgeon. I was ready for my man. I was being as flirty, girlish and passive as I possibly could.
As much as I wanted to throw myself at Alain, I waited ever so patiently for him to make the first move. I was intent on being the perfect, subservient wife. When the meal was over, Alain took me to the couch to share another glass of wine.
It was there on the sofa that he began to kiss me. As he kissed me he kneaded my breasts. Just touching my new, implanted breasts was all it took to excite me enough to unzip his slacks and begin to fondle his manly organ. As it grew in my hand I wanted desperately to suck it.
“Alain my love. Let us move to the bed. I’ll put on something sexy and comfortable. Then I want to wet your penis with my mouth so it may be nice and slick to slip inside of virgin pussy,” I said in a sultry manner.
Alain agreed. He was satisfied to wear not a thing. I wanted my shiny, silver-colored peignoir. Together we slid under the sheets and intertwined in a romantic kiss and embrace, before I engaged his penis with my wet, crimson lips. I could hardly stay there that long as I desperately wanted this man within my vagina. I could not hold out much longer. I just wanted to be screwed.
“Alain my love. I want your cock now. How do you want to take me?” I asked.
“On your back, with me on top of you. That is the way any man wants to have his virgin wife. I’m certain you want the same, don’t you, Alexandra?” Alain asked.
“Oh yes, Alain. Please do me?” I gasped.
He climbed on top of me. I lubricated us both very well with my favorite Asian Herbal Lotion. As he slid in I had such an anxious moment. I pushed back hungrily to get more of him inside of me. Then I smiled blissfully as I was able to receive all of him. I’d done my work well with my dilators.
Alain was now inside of my vagina and I was his. I embraced him and pulled him to me. Oh such a feeling of belonging to my man. As he fucked me I could feel nothing else but his overwhelming masculine strength. I felt so small and so very weak. I felt as if I were owned.
But in my smallness, in my weakness and in my girlishness I could feel safe, secure and protected by Alain. I needed this man. I needed for him to always be my loving Daddy. My breasts tingled and my cunt ached for him. I wanted to be all his. I gasped out, “Oh, just please keep fucking me Alain. Always fuck me, my loving Daddy!”
Alain was screwing me slowly at first, but when I cried out, “More Alain,” he picked up the pace. At this juncture I cared little about anything other than him emptying all of his seed into me. And when I finally felt his cock pulsing, I let out a wild screech. As his load shot from within his penis and balls into my cunt, I felt so much like a woman at long last.
I received all of him blissfully. Our honeymoon had truly begun. My new pussy had been taken. I was now Alain’s wife. I was fulfilled and contented.
We returned to Miami after a wonderful month of European travel. That evening Alain agreed we could begin looking for children. One afternoon when Alain returned from his Miami office he handed me a photo. It was of two lovely mixed-race, Asian infants.
“Aren’t they pretty? An Adoption Judge friend of mine sent me that. She says they are three-month old, female, Philippine twins,” smiled Alain.
I could have fainted. It could have been a much lengthier process without Alain’s connections, and we adopted the girls. I wanted them to have very Anglo names and Alain agreed to named them Winifred and Cassandra. We nicknamed them “Winnie” and “Cassie.” Mummy adored them, and as they got bigger they became very fond of “Grammy.”
And now dear reader we come back to the start of this chapter where Angela and I were preparing the girls for an outing with “Grammy,” and Ms. Featherstone.
“Oh, you girls just look so perfect. Don’t they Angela? Let me page Betsy Anne and she can find Grammy, for us,” I said.
It never takes Betsy very long to come to me.
“Betsy. Please find my mother, and let her know we have the girls ready for her. She should be in her suite in the south wing. Run along please. I have such a big day ahead of me,” I said to Betsy.
Betsy returned with mother, who remarked that my hair was in curlers.
“Yes, Mummy. I’m hosting my wives club today. In fact Angela set my hair right after breakfast. Where are you and the girls going today?” I asked.
“Ms. Featherstone and I are meeting your Aunt Lynette for lunch and shopping. I want to get the girls some outfits for the start of Kindergarten,” Mummy added.
“Well Mummy you go right ahead and spoil them. I won’t stop you. Run along with Grammy, girls,” I said as I kissed the adorable children goodbye.
Then I noted Betsy was standing there in the room as if she wanted to say something.
“Yes Betsy? Is there anything you want to ask me?” I said.
“Yes Ma’am. Might we speak privately?” Betsy asked.
“Anything you can say to me, you may say in front of Angela. Don’t dawdle Betsy. I don’t have a lot of time to spare. The girls from my wives club get here in an hour or so,” I added.
“Well yes ma’am. I wondered, how long that you and Master Picard intend to keep me as your maid?” Betsy asked.
“Why Betsy? Are you unhappy here? Did someone else offer you a maid’s job?” I asked.
“No ma’am. I was just wondering about my future,” Betsy said, shyly.
“It sounds as if you have much too much time on your hands Betsy. Maids are not supposed to have such concerns. Let me ask you a question, dear. How long have you worked for Alain and I?” I quizzed.
“It has been slightly over six years now ma’am,” Betsy said.
“Six years? Has it been that long? Let me speak to my husband. Betsy is the food and drink for my wives party ready for my guests?” I inquired.
“Yes ma’am. It is,” Betsy answered.
“Very well then. The girls will be here by 11 AM. We’ll meet in the Florida room promptly at that time. See that it’s ready,” I said.
If there is one thing I am proud of it is that Celine and I co-founded the Miami Beach Sissy Wives Club. We meet once a month. I hostess most all of the meetings because of all the room we have at the estate. We now have eight members. In fact the day that my silly maid asked me about her “future” with Alain and I, we initiated our 8th member, a Hispanic Girl named Anna Maria.
The only real requirements we have is that each girl must be a sissy, live full-time as a girl, and live with her “Daddy” or as two of our members do, live with their “Mistress.” In fact our newest member, Anna Maria has a female Husband.
I decided on having my hair down for that particular meeting. Celine arrived first. We gave each other a kiss. All of the girls in the club are very affectionate to each other and there is often a lot of sexual tension between all of us. Especially girls like Celine and I, who now have pussies.
Priscilla, who owns her own beauty salon, brought the new girl, Anna Maria, who had recently moved here from California and was a client of Priscilla’s. At the usual Sissy Wives Club meetings, we have some wine, and some snacks. Then we might talk about hair, makeup, fashion, housekeeping or sex with our Daddies or Mistresses.
Then we might pair off and paint each other’s nails, play with cosmetics, or give each other a different hairstyle. But when we are “Initiating” a new girl, well, there is a certain excitement and tension in the room. Of course, the new girl is unaware that she is about to get a spanking, if she truly wants to join our club.
As hostess, I was given the responsibility of getting things started. I began by having Betsy serve the food and beverages. Then I prompted Priscilla to introduce our new girl. We all began engaging each other in silly, girly talk. Then I asked Anna Maria to tell us a little about herself.
I continued to check the time. Today the usual hair, makeup and nails portion of our meeting would be superseded by Anna Maria’s spanking. When the time was right, I had the girls quiet down a little bit and I spoke to Anna Maria.
“Anna. I know that Priscilla has told you some things about our little club. Usually, for the next portion of our get-together, we pair off and do some hairstyling, nail painting or practice makeup techniques. But because today we are initiating you as a new member, we won’t be doing that,” I said.
“Has Priscilla mentioned to you that we put all of the names of the current members in a serving bowl, and I have my personal assistant, Angela pick a name from the bowl?” I asked.
“No, she never got that far,” Anna giggled.
“Really? Then she didn’t tell you that the winning member, whose name that Angela picks, gets to sit in that large chair over there and give you a hairbrush spanking?” I smiled.
“Seriously? I’m going to get spanked in front of the entire group?” Anna asked.
“That’s right honey. Does your Mistress ever spank you? I know my Daddy spanks me when I misbehave,” I said.
“Well yes. Charlene spanks me,” Anna Maria answered.
“Does she ever spank you in front of a group of her friends?” I replied.
“Yes. She has spanked me in front of her lady friends,” Anna nodded.
“Then there won’t be any problem when one of us spanks you and the rest of us watch?” I added.
“Oh no. I won’t mind at all,” Anna shrugged.
“Well good Anna. Girls, let’s get started then. Here’s the bowl. Here’s some paper and pens. Betsy, find Angela for us. Check her office,” I ordered.
“Angela, there you are. Pick a name for us honey, so we can get going, with Anna’s initiation spanking,” I said.
“The winner is, Miss Alexandra. Oops,” Angela giggled.
“That isn’t fair. You got to spank the last new girl, Alexandra,” Priscilla, the hairdresser laughed.
“Really, Prissy? I don’t recall. How did you remember that?” I asked.
“Because it was me that you spanked girl. I remember because I recall you saying that I had a nice, plump ass,” giggled Priscilla.
“Come over here Anna. That is such a pretty mini-skirt you are wearing. That will make it just so very easy to get at your pretty ass. Let’s flip up that skirt and pin it to your blouse. There you are honey. Oh, oh. You are wearing a panty brief. Do you still have your boy bits, Anna?” I asked.
“Yes, I do,” Anna giggled.
“What should I do ladies? Leave her panty-brief on or spank her bare butt?” I asked.
“Give her a bare butt spanking. Boy bits are always so cute to look at,” Priscilla agreed.
“Lower your panty brief, Anna Maria so we can see your boys bits and then I can spank your bare ass. Look at that girls. A nice pretty ass and those cute little boy bits?” I laughed.
“Her sissy thing is standing up too. Anna Maria you naughty girl you are excited about being spanked, Aren’t you honey?” Priscilla teased.
“Miss Alexandra. I hope I’m not being nosy? I think you should place a towel over your lap or Miss Anna Maria might squirt all over your pretty dress when you spank her. I’ll get a towel for you Ma’am,” Angela said.
“Thank you Angela. Get over my lap Anna Maria. Angela could I have my hard backed wooden hairbrush please? How many girls?” I asked.
“Ten, no twelve. At least two extra for having an erection!” The Sissy wives all screeched out in unison.
“Twelve it is. Count them Anna!” I ordered.
“Whack! One! Pow! Two!” And so it went. Then at one point around seven spanks, I felt little, dainty, Anna Maria’s, slim body quiver, and I realized she’d just did a nice sissy-squirt into the towel on my lap. I could have kissed Angela at that point.
“Oh my, Miss Alexandra. This is so embarrassing. I ejaculated while you were spanking me,” Anna whispered.
When I had completed Anna’s spanking and she got off of my lap, I handed her the towel so she could wipe her tiny penis clean. Once she was fully put back together, with her panty brief back on and her mini-skirt back down, all the girls hugged her and welcomed her to our Sissy Wives Club.
I left the clean-up to Betsy. Angela went for a run thru our neighborhood, leaving Celine and I alone.
“Oh Celine we just don’t see enough of each other girl. We need to get together and do some girly things. Let me kiss you Celine? Oh, now that was nice and sexy, wasn’t it? Celine, I don’t know what I’d have done without you?” I said.
“I wouldn’t be a girl now without your mentoring. I don’t think I would have met Alain, Celine. You mean so much to me. Let’s kiss again, please?” I asked.
“Of course honey. I love kissing you. I think you would have found your way, but thanks for all that credit. You know honey. We’re both girls now. I mean almost like G-Girls. When we kiss, the dynamic is so different. It’s like we’re a couple of bi-sexual Lesbians. Don’t you think?” Celine asked.
“I discussed this with my Daddy, Marcus and he thinks it might be sexy if you and I put on a little show for him and Alain. What do you think girl?” Celine asked.
Marcus was a truly handsome black man that Celine had married. He did some business now and then with Alain.
“I could mention it to Alain,” I said.
“You do that girl. Give me a kiss goodbye. You’ve made me horny for Marcus now,” Celine teased.
Early that evening the girls and Mummy arrived home with Ms. Featherstone. Alain arrived shortly after. He said he’d played 36 holes of golf, whatever that meant? The girl’s asked to spend the night with “Grammy” and of course I said yes.
Alain and I laid in bed together. I had two things I needed to ask him. I also badly needed his cock, after spanking Anna Maria and playing “Kiss Face” with Celine.
“Darling, are you too tired for me to ask you some things?” I asked.
“No. Of course not,” Alain said.
“First, your sister asked me, how long we intended to keep her as our maid?” I said.
“She did? A while ago, I asked a Federal Circuit Court Judge friend of mine and he told me that she could have done at least seven years in prison for accessory to kidnapping. So I think, that a seven year indenture would be proper. But what would she do after that? I’ve divested her of all her assets. She’s a pauper,” Alain explained.
“She tells me she’s been with us a little over six years,” I explained.
“Well then, after seven years, offer her a contract of employment. She can earn her way back into society. We can think about it then,” Alain stated.
“Was their something else dear?” Alain asked.
“Well yes. When Celine and I were kissing today, we got a little carried away. We talked it over and she said her Daddy, Marcus, thinks it would be sexy if she and I got together and put on a little Lesbian show for you men. It was just a thought,” I said.
“Yes, Marcus mentioned that. I think that might be fun,” Alain stated.
At this point, I reached under the covers and found his penis. He was becoming erect. Maybe he wasn’t too tired to give me some cock, after all?
“But Alain. Don’t you think it was naughty of me to be thinking of something like that? Haven’t I been a bit of a bad girl?” I asked.
“Hmm? Maybe you have? Yes. Of course you’ve been a naughty girl. Roll up your nightgown and get over my lap. You deserve a spanking. Right now girl. There now. Oh such a nice round girlish ass you have Alexandra. And I know you love the feeling of my big strong hand when I hit you like this,” Alain said.
“Whack! Oh my Daddy. Ouch that hurts. Oh ouch Daddy. You’re going to make me cry Daddy! Oh Daddy, oh I need this spanking so badly. Daddy, do you know what else I need, Daddy? I need some cock. I need some hot, hard cock Daddy. I need your cock,” I begged.
I reached beneath Alain’s legs as he smacked my ass, and I could feel his cock hardening. When he finally had reddened my ass to his satisfaction, he allowed me to kneel on the floor at the bedside and begin sucking him. I wasn’t sucking him for too long when the ache inside my pussy became unbearable.
“Oh please Daddy? Can I climb on top of your cock and ride you as if you were a big, Stud Horse?” I cried.
“Of course you can. Get up here now girl. That’s it. Ride your Daddy to your heart’s content Angel,” Alain added.
“Oh thank you Daddy. Oh I love you Daddy. Oh my gracious this just feels so good,” I gasped.
The End
Thank you my darling Alleta for your patience and input. And thank you my precious Annabelle for having this blog and for supporting me so strongly in my endeavors. I hope you both, as well as all the girls, enjoyed the story. Priscilla.
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