Updated! Saucy Sylvia

Coerced into emasculation by my Ex-Girlfriend and her new lovers, I found myself deeply immersed into overt femininity where and a new world awaited me as "Sylvia."

Chapter I: Cosmetic Sissy

    I could hardly have been any more upset. I was very near to tears as I prepared dinner. When Kathryn arrived home from her Gynecological clinic, she took one look at me and asked, “Okay Sylvie. What gives with the Pouty, little face?”

    She and most all of her friends, especially her new boyfriends, no longer called me Sylvan, my birth name. It was simply Sylvie. It was the same at work. Most people teased me and said I was no longer enough of a male to be deserving of a a masculine name such as Sylvan.

    “Well, because of all this, I no longer work at Bennington’s, dressing the mannequins,” I said, pointing to the feminine leaning, Androgynous apparel I was wearing, as well as my dyed, styled hair, and the cosmetics adorning my cheeks, lips and eyes.

    “When you say ‘All This’ you are of course referring to your attire, coiffure, makeup and pierced ears? Yet, you are still dressed as you were when you went to work. And if nothing else, it appears you have touched up your makeup. I can definitely detect that you freshened your lipstick,” Katie smirked.

    “Of course I did. You said dinner for three. And all of your boyfriends prefer me to look as if I’m not a threat, as to you and I getting together again. Especially Carlos. This was all your idea as well as his,” I said, shaking.

    “Maybe his, but it was not my idea. I was merely supportive as to him being the Man of the House. Besides, just because Carlos mentioned he preferred you looking more girlish, as did Connor, Dylan and William, you didn’t have to become more skillful than most women are, at applying makeup. That was your doing. You do realize, Sylvie, that you have even gone so far as to do my makeup for my dates? So you lost your job? Well, you can do a greater share of the housework, to make up for that towards your rent,” Katie shrugged. 

    “No, I did not lose my job. In fact I received a raise and now I even earn commissions on top of my salary. I was transferred to Ladies’s cosmetics and Perfume. I now work for Judith Leonard, the Lipstick Lesbian, who manages both the Cosmetic and Perfume counters, as well as the Beauty Salon at Bennington’s,” I explained.

    “Now wait just a moment Sylvie. You received a raise, with commissions, and you’re pouting? Well, if you haven’t become the epitome of a whiny, little bitch,” Katie sneered and shook her head.

    “I didn’t tell you everything Katie, I mean Ms. Kathryn. Judith, my new boss, wants me to go even more femme, towards presenting myself as a girl. She thinks it will be a fabulous marketing idea, if the word gets around, that a Transitioning, Transgender girl, is doing makeovers and selling cosmetics and perfume at her department in Bennington’s,” I shuddered.

    “She even made up a name tag for me that reads, ‘Sylvia’ on it. She wants me to go by Sylvia at work and if possible all of the time. Can you believe that?” I asked.

    “I mean why not? You’ve really went quite far with this entire Sissy thing, Sylvie. Or should I say Sylvia? Of course I should. You are heretofore Sylvia, in this household honey. I can’t wait to tell Carlos this evening. No I’ll let you tell him,” Katie laughed.

    “You can also inform the rest of the men I am dating by texts, with some cute, new pics, when we get you attired properly. In fact, it’s about time you began wearing a few more of the things Carlos has bought for you, Sylvia. You know whenever a man buys me something really pretty, I wear it as soon as I can,” Katie added, taking a hold on my arm and escorting me to my femininely appointed guest bedroom.

    “Carlos has been so very patient with you. I hope that you do recall that you initiated all of this? When I informed you that we were no longer compatible, and that you just were not able to satisfy me sexually, and I wanted to break off the relationship, you became practically hysterical,” Ms. Kathryn, insisted.

    “You nearly begged me on your knees to allow you to continue to stay here. You promised you’d do anything for the privilege. That included taking on much of the housework and cooking, as well as staying out of the way of my relationships with my lovers. Beginning with Carlos, my new boyfriends have all insisted that you adopt a more girlish persona, so that you did not appear, at all, whatsoever, as any sort of competition for my affections,” Kathryn reminded me.

    “I’ll be the first to admit that Carlos was the most aggressive where that was concerned. He stood very firm on having you learn to apply your own makeup as well as rid your wardrobe of any clothing that we determined was far too boyish for you to be wearing. He even had me give you Cosmetic application lessons as well as buy you books, mags and videos on the topic,” Kathryn added.

    “You have come very far Sylvia, and your new position at Bennington’s Department store proves that. Obviously, Judith Leonard, your new Superior, saw in you, someone who really wanted to be Fab and Femme. Carlos will be very proud of you. However, he’s told me he is a little bit annoyed that you have yet to wear any of the pretty blouses, slacks, shoes, skirts or dresses he’s purchased for you,” Kathryn frowned. 

    “Not to mention, the lingerie. And I think, you recall what he does to you, when he isn’t pleased with you?” Kathryn said.

    “Yes. I know, ma’am. He’ll eventually spank me,” I shuddered.

    “Yes. And he spanks you in front of me, with one of my grandmother’s hardback, antique hairbrushes. That must be so very shameful for you, Sylvia? Being spanked by one of my new boyfriends, while I watch?” Kathryn asked.

    “Yes, it is, Ms. Kathryn,” I sniffled.

    “Then why don’t we get you dressed and prettied up, prior to Carlos arriving here? I mean really dolled up! And then, we’ll discuss doing something really nice for Carlos, that will truly endear you, to him, and make up for all of the clothing he’s purchased for you that you have never put on?” Kathryn smiled, clapping her hands together. 

    Kathryn really outdid herself in getting me looking very femme, for her man. She had me take a dip in a scented tub and made me shave my legs and pubic patch. Next she had me wash my hair prior to moisturizing, perfuming, and powdering my entire body.

    “Carlos is spending  the night with me in my bed. He’ll leave early to play golf. I expect you to be up by 9 AM and I’ll show you how to use a depilatory on the rest of your body and shower off your body hair. Then I am taking you to Sophia’s salon to have your ears pierced again, along with a pedicure, a manicure with extenders, and I’ll have her wax your eyebrows,” Kathryn stated.

    Sophia was Carlos’s sister and owned a number of Salons. She was the lady who had dyed my hair a Light-Auburn, with Ginger-Blonde Highlights, and cut it into a Just-Off-the-Shoulder-Length Bob. Kathryn had me apply my makeup really heavily as she set my hair. She had me dress in a Powder Blue, satiny blouse, with a Pussy-Bow, and billowy sleeves, along with a pair of white Capri slacks, matching anklet socks and my very first pair of 3 inch high heels.

    The blouse matched my panties and training bra. Carlos had purchased all the items for me, though Kathryn had picked them out. Up until now I’d only worn heels as high as a 2 inch, kitten heeled shoe. Kathryn insisted on styling my hair after I took out the rollers.

    Using a lot of styling pomade, a teasing comb, “Back-Brushing”, and copious amounts of spray-net lacquer, she stylized my tresses into a dramatic, Beehive Bouffant. On the right side there was a lock of bangs, that would fall to the side of my face, near my right eye. Every now and then, I’d have to brush it back away, from out of my eye, with my hand, as I did a Hair Flip.

    It was a very feminine, girly gesture and confirmed my “New” dedication to being as girlish as I possibly could. My makeup was dramatic, with dark eyeliner, Mascara “Wings,” at the outside corners of each of my eyes, and Coral-Pink, eye-shadow. My lipstick was Cherry Red, with Smoky, Burgundy blush.

    Kathryn had me “Pose” and “Twirl” for her, as she took photos for each of her other three, new boyfriends, for me to send to them, introducing myself as Sylvia. Next, she led me, by the hand into the “Sitting-Room” that was part of her large Boudoir Suite. She had me sit, and then pulled a plastic Penis, complete with testicles out of a desk drawer.

    To my shock and horror, she held up the lifelike Man’s Cock, and said, “It is time for a lesson in how to give a blow-job, Sylvia. Because I want you to begin giving all my lovers, Blow-Jobs, girl. They will like you much more and feel better about you being around. Plus, I really don’t enjoy sucking cocks, so why not have you do it for me?”

    “I can’t, and I won’t do that, Ms. Kathryn. I’m not Gay,” I protested.

    “Of course you aren’t Gay, Sylvia. And as long as you are wearing pretty, feminine clothes and shoes, and have makeup on your face, and your hair in a Lady’s hairstyle, it won’t be Gay. You’ll just be a pretty girl, sucking a man’s dick. Now listen to me, Sylvia. If I have to tell Carlos that you refused my request, to suck him off, I cannot guarantee he won’t discipline you,” Kathryn cautioned me.

    “And it might not just be a spanking. He may tie you up and use the Rattan Cane I keep in my closet for severe indiscretions, or even the Riding Crop I use when I go riding with the women in my Ladies’s Horse-club. You had better behave Sissy Sylvia or you could find yourself without a place to live,” Kathryn warned.

    “Please Ms. Kathryn, don’t say that? Please? I have just never done anything like sucking a man’s penis,” I mewled.

    “Yes honey, I know. I know Baby. But for every girl, there is always a first time. But once you get that first time, out of the way, you’ll grow to really enjoy it, sweetie. And that’s why I’m going to show you how to do it. You’ve had a few blow jobs from girls, correct? Well good. Then you know what you enjoy. Now pay attention, girl,” Ms. Kathryn ordered.

    “Always take the penis in one hand, and the testicles in the other, to begin. Touch them lovingly. Then lick the Balls, especially in that hard to get to spot, way in the back, not far from the crack in your lover’s ass. Make everything nice and wet. Next, take the cock in your mouth and lick and suck as you caress the balls, with great care,” Ms. Kathryn said as she looked at me very seriously.

    “By now the cock is getting hard or may even be really, very, stiff and firm. Listen carefully, Sylvia, honey. This next part is very important. As you move your mouth and lips back and forth on your man’s penis, and fondle his testicles, make very certain, that you look up at him, adoringly, and wide-eyed, like his worshipful puppy-dog,” Ms. Kathryn sighed.

    “That groveling look on your face, will tell him that nothing is more important to you than the pleasure you are giving him. And always ask him if he wants you to swallow his sperm, or if he prefers to ejaculate all over your face and hair. Who knows? He just might prefer to do a combination of each?” Ms. Kathryn shrugged. 

    “Lastly, once you and your lover are both comfortable with each other, there will be a time, when you are just fluffing him, to prepare him to screw you. It’s very important then, that you get his cock, really, very sloppy wet, so that it goes into you butt-hole more easily. And always ask him how he wants you to present your Sissy-Ass-Pussy to him,” Ms. Kathryn added.

    Ms. Kathryn had me practice for a while on the Faux-Penis. Then she had me rehearse what to say to “Master” Carlos when I greeted him at the door. Ms. Kathryn added a Pink, Heart-Shaped, apron, tied at my waist so that I’d have something to hold onto when I curtsied to Master Carlos. 

    I nervously minced to the door as I heard the bell ring. Ms. Kathryn told me she’d be finishing up the dinner preparations. When I opened the door to greet Master Carlos he just stared at me questioningly.

    “Hello Master Carlos. Won’t you come in sir?” I said, in a practiced girlish voice, as I dipped into a curtsey.

    “What the fuck? Is that you Sylvie?” Carlos asked.

    “Yes sir, Master Carlos, but from now on, Ms. Kathryn stated that I should be referred to as Sylvia,” I nearly lisped, I was so shaken and scared.

    “Well that fits. You actually look really nice Sissy-Girl, Sylvia. And I see you are wearing some of the things, Katie and I bought for you. Nice,” Carlos said, as he closed the door and I dropped to my knees in front of him. 

    Shaking, I said to him, “Master Carlos, would you mind at all Sir, if I sucked your cock and gave you a Before Dinner, Blow job, Sir?”

    Carlos, once again looked at me in surprise, but then smiled. 

    “That would be no problem at all Miss Sylvia Girl. No problem at all. I’ll even lower my pants and underwear for you,” Carlos said.

    “Thank you so much sir. As this is my very first time sucking a cock, I must ask you to spank me, if I displease you at all sir,” I said, with tears in my eyes.

    “If you screw up this blow job, Sissy, I won’t just spank you. I’ll bend you over a chair, tie your hands and ankles to the legs of that chair, and I’ll blister your Sissy-Ass red-raw, with the belt that holds up my pants. You can begin sucking me off girl,” Carlos grinned. 

    I began the blow job in the manner that Ms. Kathryn had instructed me. Very soon, I had a very erect, hard penis between my heavily glossed, red lips. I’d taken nearly the entirety of Master Carlos’s thick, above-average-sized penis into my drooling, slobbering, wet, mouth. By now, I was looking up lovingly, into his eyes and his smirking face, as he held tightly to my slim, shoulder blades with his strong manly hands. 

    I moved my lips and mouth, eagerly, greedily and hungrily, back and forth, as his hardened cock seemed to grow yet bigger in my mouth. He moved one hand to hold tightly behind my slender neck. For the very first time, in my twenty-three year life, a man’s erect penis, jumped and spasmed in my mouth as Carlos jettisoned gobs of thick, rich, gooey, salty, manly ejaculate into my throat.

    My gulping and gagging reflex worked very well, as I frantically attempted to gobble up all the creamy, masculine sperm that I could possibly swallow. Carlos let out a very mannish grunt, and then exclaimed, gasping, “Oh, you hot, little bitch. Wow, can you ever suck a cock!”

    “Yes, she did wonderfully, didn’t she Carlos? Oh my stars, Sylvia, that was fabulous,” I heard Kathryn say, as she clapped her hands, from behind me and to my right.

    With just a little drop of sperm, still at the edge of my mouth, I looked in the direction of her voice, and saw Ms. Kathryn, sitting on a settee, legs crossed and smiling. I hung my head and closed my eyes, covering them in humiliation. My ex-girlfriend had just watched me suck off one of her new boyfriends. 

    “Oh no. You were watching? Oh my. I thought you were staying in the kitchen and dining room to tie up some loose ends for dinner?” I asked, shamefully.

    “Oh no, sweetie. I just didn’t want you to be nervous over giving  your very first blow-job. Carlos, I truly believe our girl, Sylvia, is going to become a fantastic cocksucker don’t you? Doesn’t she still have a little glob of cum just at the edge of her mouth? Yes right there. Sylvia, lick Carlos’s finger clean where he just dabbed that sperm from your mouth. Good girl, honey,” Ms. Kathryn said as I lapped my tongue over Carlos’s index finger. 

    I served Surf and Turf to Carlos and just the Lobster to Kathryn as Ms. Kathryn passed on the steak. I was now on a diet with “Zero” red-meat and very low in Carbs. I was not quite 5 feet 9 inches tall and only weighed 140 pounds. However “Doctor” Kathryn insisted I needed to lose 15 pounds. 

    For dinner I had a veggie stir fry with slices of Chicken Breast. The “Lovers” imbibed in the dining room. I dined at the Breakfast bar in the kitchen, within ear-shot, should Ms. Kathryn ring the “Maid’s” bell for service.

    I heard the bell ring and Ms. Kathryn say, “Sissy Maid Sylvia, more Chablis, darling.”

    As I was pouring the Chablis, Ms. Kathryn said, “Sylvia, darling, from now on I would suggest that calling me, Doctor Kathryn or Doctor Bradford would be more appropriate, don’t you agree, princess? And Carlos would prefer you call him Daddy Carlos or simply Daddy.”

    “Yes, of course, Doctor Bradford. I agree. I am mostly a servant,” I added.

    “And you will become a new clinic client as well, Miss Sylvia. We’ll begin your Estrogen Therapy tomorrow sweetie,” Doctor Kathryn added.

    “Though Carlos thinks it to be very sexy, being called Daddy, I of course refuse to do that. I am not a little girl. You will also become Carlos’s outlet for anal and oral sex, for the foreseeable future. Therefore I’ll also be providing you with a set of Vaginal dilators for you to wear in your rectum to make it comfortably accessible to a male’s penis,” Doctor Bradford, stated, very professionally. 

    “Once you’ve cleaned things up after dinner, I’ve laid out some lingerie for you to wear to bed. I’ve also spritzed your pillow with perfume for the night. Most of my Transitioning girls, whom I adore treating, find that being immersed in femininity really aids them in their journey,” Doctor Kathryn explained. 

    “Once you’ve cleaned off your makeup and put moisturizing cold cream on your face, freshen your lipstick and come to the sitting room of my boudoir to serve Carlos and me a glass of Cognac, and say goodnight. And don’t forget to wear a sleep-net to protect your Beehive Bouffant,” Doctor Kathryn added as she left the dinner table.

    Kathryn was an amazingly “Liberated” female. She was a top gynecological surgeon, with her own private practice, at a clinic which she owned.  When anyone dared to mention her “Playing the field” and having four boyfriends, whom  she kept on a string, she’d counter with, “Tell me. Don’t single, Male doctors bang every nurse, technician, and radiologist within their reach? And what about married male doctors that cheat on their wives? Does any of that disturb  you, nearly as much as a single, professional female, with multiple male suitors?”

    By 9 AM Saturday, I was out of bed, naked, and standing outside my shower, wearing a protective, “Big-Hair” shower cap. Climbing into the shower, I watched as the warm water, washed the remainder of my body hair, along with the depilatory, down the drain.

    “From now on, whenever you need it, we’ll have Sofia give you a leg, bikini and eyebrow wax. Don’t wear stockings to the salon. You’re getting a pedicure today. Maybe some anklets or even no socks at all, with open-toed sandals? Those Gold, Extreme-Harem-styled, Palazzo pants with the floral pattern would look nice, with that white blouse with the fussy furbelow,” Doctor Kathryn stated.

    “Let’s brush out your Bouffant Beehive. I am certain Sofia will want to inspect the color and highlighting job she just did on you,” Kathryn suggested.

    Indeed, as one of Sofia’s girls began my Pedi and another girl did my French Manicure with nail extenders, Sofia examined the color and highlights which she’d personally put into my thick locks.

    “Her hair is so full and vibrant Katie. I’d love to do a body perm on her at a latter date. It would give her so much more volume and wave. And Lip Fillers would not be a bad idea either, along with some extra piercings, in locations, besides the new ones in her ears,” Sofia stated. 

    Then Sofia initiated my double-ear-piercing. She began by removal of the studs in my lower lobes, and replacing those with seriously Oversized, Gypsy hoops. Monday, when I started my new position as on of the “Girls” at the Perfume and Cosmetic Counter, those hoops were certainly going to garner plenty of attention. 

    “I’ll put these pink, pearl studs in the piercings which I will be doing at the top of her lobes. In the holes I’ll be placing at Mid-Lobe, a nice set of Dangling Pendants will look fabulous once the initial studs are removed,” Sofia added. 

    On the drive to Doctor Kathryn’s GYN office and Clinic, I looked down at my Burgundy shaded toenails, visible thru the “Peep-Toe” pumps I was wearing. I also gazed at the two-tone (Pearl-tipped and Burgundy) nails and extenders on my fingers. I was continually touching my new set of very large, Gypsy hoops as they tickled my neck. I waited in the car as Doctor Kathryn returned with a briefcase.

    Upon arriving back at Kathryn’s opulent home I assisted her with placing a plastic covering over the comforter on my bed.

    “The first thing we are going to do is give you a nice, one-quart, colon, cleansing enema, just chocked full of warm soapy water. You’ll need to remove your Palazzo’s and panties for that, Princess,” Doctor Kathryn explained.

    I sighed as Kathryn placed two lubed fingers in my rectal opening. The nozzle seemed cool, and long, as it entered my anus. It was the release of the warm soapy fluid that made me nervous as it began to flow into my tummy, and cause it to swell. When I began to whinny, just a little, Doctor Kathryn smacked my butt and said, “Stop being such a big, baby, Sylvia. You need to take the entire quart in, as you need to be perfectly cleansed for the initial placement of the new Vaginal dilator you’ll be wearing, very regularly, within your rectum.”

    After being permitted to evacuate my bowels, I was given a second rinse with clear, warm water. Then I went thru the indignity of having a lubed, vaginal dilator slowly worked into my rectal cavity.

    “May I inquire as to what the purpose of the dilator is, Doctor Kathryn,” I asked, very politely. 

    “Of course you may Princess. It’s actually two-fold. The dilator will add a very cute, very feminine wiggle to your manner of walking. Your butt will sway and jiggle, very prettily. There is also an added benefit, once you find a real man. The very same man you will desire to eventually Bed you, of course. The dilators, as we introduce you to yet larger sizes, will widen your anal entryway and passage, so that you’ll have much less discomfort when a male’s penis penetrates you,” my lovely Doctor stated.

    “The only occasion on which you should really need to remove that dilator, honey, is when you have to do Poops. Or of course, if a man really wants to put his cock inside of you. Either way, be certain to clean and lube yourself, as well as the dilator, prior to inserting it back into your anus,” Kathryn instructed me. 

    “Now, stay just where you are. I’m going to inject you with your very first, Estrogen Booster. The Estrogen will cause you to be calmer and more relaxed, though you could have an occasional mood swing. On a truly positive note you’ll have the desire to be more compliant, obedient and submissive. Your physical characteristics will change of course,” Kathryn commented.

    “Your skin will be softer and you’ll have a pretty glow. You’ll grow small tits, and you’ll be far more shapely, especially if we introduce you to the proper figure training accessories,” Doctor Kathryn explained as she injected me in my butt. 

    Once I put my panties and Palazzos back on, Kathryn handed me a bottle of prescription pills.

    “One right now and one each morning with breakfast. Most of my Trans Girls, call these their Pretty Pills,” Kathryn smiled.

    “Princess, I will be going out this evening with my girlfriends. After all the changes you’ve went thru, of late, I really don’t want you feeling so very lonely and alone. I’ll likely not be home this evening. So, I’ve asked my boyfriend Connor to come over and keep you company, for the evening,” Kathryn explained. 

    “Now, I know that Blow-Job practice isn’t the easiest thing to do. However, you really need to keep it up. You just never know when you’ll finally meet that very special man, that you truly desire, and you   decide to have him Fuck you into Sissy Nirvana,” Kathryn paused.

    “Now I want you to greet Connor the very same way that you greeted Carlos yesterday evening. That is correct. You should greet him on your knees, honey. And once he agrees that he’d like you to perform orally, I want you to ask for Spankies, if he is displeased with the way you sucked his cock. And Sylvia honey, I will definitely ask him about everything, the next time I talk with him,” Kathryn warned me.

    “Once you two get better acquainted, ask him if he wants to watch a movie and find out what you can get him to drink and what he’d like you to make him to eat. Of course ask him if he’d enjoy spending the night, and if he’d prefer sleeping with you or in one of the guest rooms?” Kathryn went on.

    “If he wants to get in bed with you, well, make yourself sexy and pretty and you know what to do from there. If he wants anal, explain that you’ve never done that, and that you’ve just began to stretch  yourself out with a dilator. If he really wants anal though, well, the good news is, that Connor has an averaged sized Penis, so you are in luck there. Just use plenty of this lube,” Kathryn said, handing me a tube.

    “It has a numbing agent mixed in with it, that will negate, as much as possible, any discomfort experienced, by the extreme tightness, which a snug butt-hole, clamping down over a rock-hard penis, might cause. Now why don’t you assist me with getting pretty for my night out with the girls, sweetie,” Kathryn asked.

   Chapter II: Sex and the Single Sissy

    Connor arrived not too very long after Doctor Kathryn departed to go “Clubbing” with her professional lady friends. I greeted him effusively and so very girlishly at the doorway, daintily taking hold of the billowy pleats of my girlish Palazzo pants and dipping into a pert, demure curtsey.

    “Oh, please do come in, Master Connor! It is so very, very sweet of you to agree to keep me company this evening, Sir,” I cooed.

    “Wow, Sylvia, you look even hotter in person, than those modeling pics you sent me, letting me know about your new name. By the way, doll face. You can call me Connor darling, or Connor my love. It’s way more sexy,” Connor stated.

    “Oh of course, Connor, darling. I’d love to give you a special treat this evening, for coming by to take care of me. So, Connor my love, would you enjoy it, if I gave you a nice blow job as a way of saying thank you? And because this will only be the 2nd time I’ve sucked a cock, please do feel free to spank my Sissy ass if you are displeased with me,” I added, as I fell to my knees in front of him.

    “Sylvia, that’s an excellent idea. Especially when I look at those wet, red lips of yours. Don’t fret the spanking though, unless of course that’s a special Kink of yours.” Connor said, lowering his slacks and underwear. 

    “If getting spanked is a game you enjoy playing, then just let me know that you’ve been a bad girl, and ask Daddy to spank you. By the way, if this is your second blowjob, who’s cock did you suck first, I might ask?” Connor added.

    “It was Daddy Carlos’s penis that I gave my first blow job to,” I responded as I carefully took Connor’s cock and testicles into my soft, girlishly, moisturized hands. 

    I allowed my brand new, acrylic nail extenders to brush against Connor’s, growing erection and swelling balls. First, I licked all around the head of Connor’s nearly, fully erect penis, prior to licking and sucking on his testicle sack. Connor held my head in one of his hands and he had his other hand behind my neck. 

    I next took the head of his penis in between my Carmine lips, as I began to bob my head up and down the entire length of this sweet man’s lovely erection. If what I had in my mouth at that time was an “Average” sized cock, then my penis was most assuredly “Well-Below-Average” in size.

    It dawned on me that it was no wonder that Doctor Kathryn had relegated me to the status of “House-Sissy” and had made up her mind to seek sexual activity elsewhere. I became certain that Connor’s cock was as erect as humanly possible and I added little flicks of my tongue, around the head, as my mouth moved back and forth on his hardened boner. 

    As I felt Connor’s fingers twisting and intertwining themselves in my  bobbed tresses, I could sense he was getting really close to spurting his manly seed into my sopping wet mouth.

    “Would you like me to swallow all of your Cum, my lover?” I asked, pausing, and then continuing my sucking, as I looked up at him, Doe-Eyed and worshipful.

    “Oh yes! You are fantastic girl. What a sweet cocksucker you are, you hot bitch,” Connor gasped.

    I felt his body jerk, prior to feeling his cock swell and spasm, as I tasted the salty jets of sperm enter my mouth. I gulped and gobbled reflexively, to swallow every last drop of his very manly, Baby Batter. As I swallowed, Connor held tightly to my thick, Bobbed locks. I grabbed his butt cheeks to savor the magic moment of our sexual coupling. 

     Connor pulled me to my feet, as my mouth separated from his cock. He held me to him, saying, “Oh Sylvia, you can suck me off any time. That was fabulous girl.”

    “Thank you Connor, darling. Can I make you something to eat?” I asked.

    “No, nothing. I would like to watch some sports on TV. How about some chips and a beer?” Connor asked. 

    “Yes, of course. Come this way. Well, by now you know where the Television is,” I giggled.

    After serving Connor, I asked if he wanted me to sit with him.

    “You can, unless you have some duties to perform that Katie assigned to you,” he said, focused solely on the Game that was on TV.

    “Well, I do have some ironing to do. Call me if you need more beer and chips, Connor,” I said, as I minced off to the room where I did my sewing and ironing.

    I served Connor another beer and some pretzels, prior to asking, “Connor, would you like to stay the evening? You may sleep in one of the guest rooms or you can sleep in my bed with me.” 

    “Actually Sylvia, if you won’t be lonely sleeping alone, I was going to leave when this game is over, if that’s okay?” Connor asked. 

    “Oh yes, that’s fine. In that case, I am going to clean off my makeup, shower, wash my hair and put it up in curlers for the night. I’ll also put some cold cream on my face, and wear some fresh lipstick to kiss you goodnight,” I said, batting my eyes.

    “Wow. You’ve seriously have the Girly thing going on, don’t you Sylvia?” Connor laughed. 

    He was correct. It took me some time. However, I eventually minced back into the TV room, wearing a pink nightgown, high-heeled mules, with a sleep-net covering my rolled up hair. My lips were done in a “Wet-Look” Burgundy and my face was shiny from a heavy application of Pond’s Cold Cream. 

    As Connor was still avidly concentrating upon the game he was watching, I sat on a Settee, catty-corner to the Easy-Chair he was seated in. As the game ended, he stood up. 

    “Well, I’ll be going now Doll-Face, do you want me to put the leftover Chips away, and toss the empty beer can?” Connor asked.

    “No honey. I’ll get those. Can I give you a kiss goodnight? Don’t fret. I brushed my teeth and gargled with mouthwash,” I smiled.

    Connor laughed and held out his arms, as I walked towards him. He pulled me into his chest as I encircled his body with my slim arms. My freshly painted lips met his. His tongue probed my mouth and my tongue encircled his thick tongue. It was an awesome kiss, my first truly, romantic kiss with a male. 

    I could feel my cock stiffening. I mean it was really hard. At that moment I seriously wished Connor was staying the evening with me in my bed. At that juncture in time, I simply could not explain my giddy, girly, feelings, even to myself. As we broke from the kiss, I whispered, “Wow, that was really very nice.”

    “Sylvia, I hope you get to suck me off again,” Connor smiled.

    “Oh, I think I will. According, to Doctor Kathryn, I’ll be sucking off all of her men, as well as performing anal sex with them, should they desire either service,” I stated.

    “You know I am amazed, at how you have embraced this entire, Sissy, Girly thing, Sylvia,” Connor added.

    “Truthfully Connor, this is what Doctor Kathryn wants from me. And I’ll do anything I possibly can to make Doctor Kathryn happy with me. She’s who I live for Connor,” I simpered. 

    Once Connor departed, I minced off to bed. I was still partly erect when I slipped under the bedsheets. I really needed to masturbate, as well as hide any evidence of my masturbation. Kathryn had, as of yet, not mentioned locking my cock and balls up in any sort of Chastity Cage. However I knew it was a distinct possibility.

    When I’d initially agreed to being Sissified, in order to remain in Kathryn’s household, I’d searched the internet for more info on what it actually meant to be subject to Sissification. I found out that what I actually was, was a Sissy-Cuck. And most of the Sissy-Cucks that I read about were in chastity, as well as chemically or surgically gelded. 

    A number of these “Cucks” had been subject to one or more of these procedures due to being chronic masturbators. I didn’t want anything like that to befall me, so I knew I’d have to keep my masturbation very private and hide any evidence of it. That evening however, Connor had made me so horny, I desperately needed to jerk-off. 

    I took a jar of cold cream and plenty of Kleenex to bed with me. I lavished the cold-cream all over my my cock and balls. I laid sideways, with my head on my perfume scented pillow. One of my hands was stimulating my penis, as the other hand was massaging my testes.

    I began to fantasize that I was in bed with Connor. However, visions of Carlos continually appeared in my fantasizing mind. At last, I succumbed to the images of Carlos making love to me. As we kissed I felt so pretty and femininely vibrant.

    My makeup was done to absolute perfection. I had a pert bosom with excited, swollen nipples. My hair was bobbed shorter and cuter, with a shaved nape. I was giggling as Carlos touched my face gently, along with the tip of my nose. I cooed as he used his fingers to flick my oversized Gypsy hoops, along with the glamorous pendants, dangling from my pixieish ears. I felt so very ravishing! 

    His cock was quite wet, hard and ready in my hands, so I asked Carlos, “Would Daddy enjoy it if Sissy laid on her back and Daddy put himself inside of me?”

    He smiled and nodded as I turned and readied myself, looking up at him as I raised my ass for his cock to enter. As he slid his penis into me I wrapped my svelte, waxed legs around his torso and practically begged, “Oh please Fuck my ass silly, Daddy. Make your Sissy girl whimper and cry?” 

    As his cock went in and out of my ass, I strained to rise up to meet his manly thrusts. However when I next looked at him, it was not Carlos that was screwing me. Oh yes, the face was familiar, but I couldn’t affix a name to it. 

    The “Stud’s” body was more slender than Carlos, and definitely more athletically trim and taut. He was younger and even far more handsome in a partly “Pretty” but strikingly Boyish manner. Whoever he was, I wanted him as my man.

    “Make me your’s darling. Take me away and make me your girl,” I gushed passionately. 

    As his manly seed, spurted wildly into my rectum, I also exploded and I felt totally fulfilled. It was the Orgasm that I’d never, ever had, the climax of a lifetime. As soon as the fantasy faded, I came to, holding a wad of cum-soaked Kleenex. 

    I felt puzzled and thought out loud, “Who did I just imagine that I was with?” 

    I was shaken as I disposed of the Kleenex down the Bidet, as I flushed it. When I finally laid back down under my satin sheets, I sighed and went right off to sleep. In a dream, I saw “My man” once again, flirting with me, as I sat at a desk, smiling, prettily, in a truly, girly-girl satin blouse with a pencil skirt. 

    When the morning sun peeked thru my ruffled curtains, though, reality set in. I felt relaxed as I went thru my usual Sunday morning duties. I was dressed in a Kimono robe, with panties and satin, bedroom, mules, with my hair still up in curlers, covered with a sleep net. Soon enough, Doctor Kathryn retuned from her evening out with the girls.

    “I sincerely hope that you did not take Connor to bed with you, with your hair up in rollers, Sylvia?” Kathryn asked.

    “Oh no ma’am. And welcome home from your evening out, Doctor Bradford. No, Connor did not stay the evening. Though I did greet him with a blow job and he declined to spank me ma’am. Would you like coffee Doctor Kathryn?” I asked.

    “Yes. With just a splash of cream. Then sit with me at the Breakfast Bar for a chat. I have some news for you, dear,” the Doctor added.

    “Thank you. Aah, the coffee is perfect, my Maid. Well, I never mentioned it, a professional courtesy I would guess, but I’ve known your new Boss, Judith Leonard, as a Client, for some time now. Coincidentally, she waltzed into the same night-club which the girls and I attended last evening. Her and her group sat very near us,” the Doctor began. 

    “There happened to be ladies in each group that knew each other socially, as well as professionally. So we put the tables together and became even better acquainted. Of course I couldn’t help but speak to Judith concerning you. Both between the bond of her being a Patient, as well as both of us knowing you, well, we really hit it off personally,” Doctor Kathryn explained. 

    “So much so that I went home with Judith, to her gorgeous residence. We stayed up quite late and I spent the evening there. Then this morning over breakfast we had another chat and we both came up with some important decisions concerning you, Sylvia,” Kathryn went on.

    As I looked at her questionably she added, “We want to legally change your name, only for your own good and protection, Sylvia. So what was your Mummy’s maiden name?” Kathryn asked. 

    “Mummy’s name prior to marriage was Conte. Please explain to me how a legal name change would be for my own good, and protect me?’ I responded. 

    “Well, just imagine if you will, driving into Bennington’s one morning  to work at the Cosmetic and Perfume counter, and a police officer stops you for a taillight being burned out. The driver’s license you present to him states that you are Sylvan Marple, a male. However, you are in a full face of glam makeup, wearing a pencil skirt, heels, heavily perfumed, with your hair in a Chignon. Would that not be embarrassing?” Kathryn asked.

    “Yes. I would imagine so? Isn’t there another way around this circumstance, though?” I asked.

    “I’m afraid not, Sylvia. Both Judith and I caucused for quite some time and the only thing we could come up with is an official change of legal name. We came up with a lovely middle name for you, however. It was Cerise, darling. Sylvia Cerise Conte. It simply sounds so sexy, doesn’t it? Hmm? Why don’t you stay in curlers until your morning comb-out, Monday?” Kathryn asked. 

    “If we go anywhere today, you can wear a scarf or a turban. Now, until your legal name change comes thru, I will be driving you into Bennington’s and either Judith or her Admin, Allison will be taking you home,” Doctor Kathryn proceeded to tell me. 

    As it was, we didn’t go anywhere for the rest of the day. Kathryn had me practice doing my own makeup and painting my nails, as well as giving her a makeover and a manicure, as practice for giving ladies makeovers at the Perfume and Cosmetic counter at Bennington’s. 

    When I arrived at work Monday morning I went straight to Judith Leonard’s office as instructed. There, I was met by Allison, Ms. Leonard’s very attractive Admin. Ms. Leonard looked me over smiling. I wore the alluring cosmetic application that any girl would be expected to achieve if working in the position I was to be employed in.

    My hair was “Up” and pulled back, to show off my earrings and vividly applied makeup. I had on a silver, satiny blouse with a fussily knotted Pussy-Bow. My high-waisted, wide-legged slacks were in a shocking-pink shade. On my feet were Peep-Toed, silver pumps. I held a pink, “Clutch” with my compact and lipstick.

    “Welcome to Bennington’s Sylvia. You look very nice today. I understand from Doctor Bradford that she expects you to be wearing a skirt and blouse or a dress, with stockings or hose by next week some time? That’s sensational, for a young girl just Transitioning,” Ms. Leonard complimented me. 

    “Keep your clutch close by you. I expect all of my girls working in Perfume and Cosmetics, to regularly sample a spritz of perfume, on their wrists, as well as touch up their lips and powder their nose and cheeks. It attracts more customers as they feel you girls are very fastidious about your appearances, and they want to feel the same way. Now let’s introduce you to the rest of the ladies at the counter as well as the salon,” Judith added. 

    Both the ladies at the counter where I’d be working, and the girls in the salon were very welcoming. Apparently each had been told that I was in the midst of a “Boy-to-Girl” transition. 

    “This Bennington’s location in White Plains, is our ‘Flagship’ Department Store in the Tri-State, New York, New Jersey, Connecticut, region. It is the newest and most modern of all the Bennington’s stores. The corporate offices are located on the top, three floors,” Ms. Judith explained.

   “At times, the salon becomes so very busy that we have you girls from makeup come into the salon to do cosmetic applications,” Judith informed me. 

    My 1st day there, I did several makeovers. All were enjoyed by the customers. I sold quite a bit of cosmetics and perfume. On the drive to Doctor Kathryn’s home, Ms. Judith was exceedingly friendly. In fact she’d been that way all day long, touching me whenever she possibly could and giving me a hug nearly every opportunity she had.

    “You know, Bennington’s has a very expansive web-site as does each location. I took the opportunity to announce your transition publicly, both at the regional and local sites. Each department has a section where we do a brief bio of the individual employees,” Judith began.

    “When we took your official employee photo, this morning, I gave myself the liberty of posting it, along with the information that you were born a boy, but had decided a year or so ago that you were meant to be a girl,” Judith smiled.

    “And truthfully darling, from the evidence of you being a complete Girly-Girl, nature truly made a very huge mistake. I am certain you were never ever meant to be very much of a boy, Miss Sylvia,” Judith smiled.

    “You should have no reservations whatsoever about anything, my dear, dear girl. Bennington’s is so very, very, LBGTQ friendly darling. We afford all Gays and Transsexuals every single governmental and workplace protection that the law will provide. You will be fully shielded from any bullying or harassment my dearest Pet,” Ms. Judith assured me.

    As Judith drove her automobile up the long drive to Doctor Kathryn’s opulent home in a private neighborhood, she placed the  absolutely gorgeously manicured fingers of her right hand upon my left thigh and lightly massaged my leg. Turning to me with her lips pursed she asked, “You do know I am a lesbian don’t you my sweet Sylvia?

    “Yes, my darling, girl. Ms. Judith is a lesbian Cougar and from the moment I laid my hungry eyes upon you, dressing the mannequins in the front window in our latest ladies’s fashions, I was determined to get you into my department,” she said, stopping the car in front of Kathryn’s residence. 

    She leaned over and pulled me to her, demanding, “Now give Mummy Judith a nice kiss goodnight Princess. I won’t take no for an answer, sweet-lips.”

    “Oh yum. Let’s try some tongue, Little Girly,” she added as she French-Kissed me very forcefully. 

    It had been so very long since I’d been kissed by a female that I couldn’t help myself. I surrendered willingly to her aggressiveness, and fully immersed myself in the moment. When we both came up for air, I sighed and smiled at this handsomely attractive, older lady.

    “I do hope you enjoyed that as much as I did, Sylvia?” Judith asked.

    “Yes I did, Ms. Judith,” I answered. 

    “Sylvia honey. Ms. Judith or Ms. Leonard or ma’am, is perfect for the workplace setting. However, for intimate moments like this, and I am certain we’ll have yet more cozy encounters, calling me Judith or Mummy, will do just fine, Princess,” Judith insisted.

    “Yes of course Judith. Mummy? Could we kiss goodnight,” I asked, babyishly.

    “Yes of course, darling. Mummy would love to kiss her good girl,” Judith added, embracing me once again and French-Kissing me aggressively. Though confused at that moment, I still wondered how I would now balance my undying loyalty to Kathryn, versus my new sexual attraction to Judith? 

    I did have sexual needs at that juncture and of course I still do. From that point onward, Judith volunteered to not only provide my transportation home from Bennington’s, but to additionally pick me up every morning and take me in to the workplace. Even after I posed, smiling prettily, for my new, New York State driver’s license, Judith and I took every opportunity to car-pool to our place of employment. 

    One Friday morning, during the 1st week of September of the following year, as I did my morning preparation for my day selling cosmetics and perfume, Kathryn spoke to me as I was seated at my vanity. 

    "Sylvia honey, I took the time to pack a couple of suitcases for you. William is coming over for the Holiday weekend and he requested complete privacy, sweetheart. You’ll be staying with Judith for the next four evenings or so. It was a last minute thing and I didn’t have time to tell you,” Kathryn explained.

    “I am certain you two girls will have fun together,” Kathryn smiled.

    I paused and then said, “Of course we will. Are my bags in the foyer?” I asked. 

    I was mildly excited on the drive to Bennington’s with Judith. I was also uncertain as to what exactly lay in store for me.  

Chapter III: Seasons of Change

    Judith showed me to the guest bedroom I’d be spending the next few evenings in. It was just absolutely so gorgeously girly. Then she took me in her arms and squeezed me to her firm bosom. 

    “You’ll never dare dream as to how long I have yearned for this moment, my darling Sylvia,” Judith gushed as she smothered me with kisses.

    “Please dear? Take your clothes off. You don’t even need to slip into anything sexy if you don’t want to my love. Just come to my boudoir and get into bed with me,” she insisted. 

    Climbing into bed with a female was something that had not occurred for me in at least a year and a half. The hormones I’d been taking for the past year had given me an A+ to B- sized set of tits. My ass was more well rounded. From dieting and the “Figure-Training” garments Judith had put me into, I’d developed a cute, 34-26-34 figure. 

    My skin was soft and silky, and my entire body was mostly hairless. I’d not only changed physically, but in addition, I had evolved more femininely in an emotional sense. I was increasingly subservient as well as compliant and obedient in both my personal home life as well as in my workplace. I lived to make both Kathryn as well as her lovers, pleased and satisfied with my behavior.

    I readily agreed to suck off, or “Fluff,” Carlos, Dylan and Connor whenever Kathryn even implied that I should. Carlos especially enjoyed these services as well as having me provide myself to him by presenting my “Sissy-Boi-Pussy” for anal sex pleasuring. 

    “You may leave the dinner dishes and kitchen mess to be cleaned up later, Sylvia. I want you in my boudoir in two minutes to prepare Carlos for me by Fluffing him,” Kathryn instructed me one evening. 

    I entered Kathryn’s boudoir. She was on the bed in sexy lingerie reading a medical magazine. Carlos was sitting on the edge of the bed naked. I went to my knees, smiling, and took his cock into my mouth. I looked up at him adoringly as I fondled his large testicles. He was just so very manly.

    “Tell me Sissy. Your Boi-Pussy should be ready by now for deflowering, isn’t it? I should come to your bed one evening and finally shred away the very last pieces of your non-existent  boyishness. Don’t you think, girl?” Carlos asked.

    “Why not take her this evening, darling? After we’ve had sex and I’m in a deep slumber? She’s worn that Butt-Plug far long enough. Now be careful Sissy. Don’t suck him dry. Remember slut. You are preparing him to please me. You look hard and ready my lover. Go stand over there by the window Miss Sylvia and observe how a real male Fucks his women,” Kathryn instructed me.

    I don’t know exactly what was more shameful actually. Kathryn once had me give Carlos a “Thank You” blow job on his birthday. Prior to sucking him off she had me thank him for Fucking her in a way that I never could. But somehow, watching him screw her, the lady I once bedded, brought tears to my eyes.

    Kathryn was older than me. Nine years older. I met her thru my mother. Kathryn was the daughter of one of my mother’s instructors when Mummy had attended Wellesley. Kathryn had been a student there prior to going to medical school.

    I was 20 at the time. She was 29. I don’t know what the attraction was for her, unless it was the way she could completely control me? In any event, the attraction was over for her in less that two years. It was then I agreed to sleep in one of the guest rooms and become her housekeeper, in order to continue living in her home. 

    As Carlos continued to masterfully screw Kathryn, she emitted squeals and screams that I never heard when we had sex. Even when I pleasured her clitoris with my lips, mouth and tongue. After they had both climaxed and they lay there, totally sated, Katherine gutturally moaned out, “Come over here Sissy and lick my lover’s penis until its squeaky clean. Then you can suck his gooey sperm from my dripping pussy.”

    As I sashayed away from the cuddling lovers, I could hear Kathryn throatily whisper, “I insist you fuck her silly this evening, Carlos. Wait until I’m sound asleep. Then you can give me a full description come the morning.”

    And Carlos did come into my boudoir later that evening. As he crawled into bed, I moved towards him, needfully and kissed his hairy chest. He strongly French kissed me prior to rolling me over onto my stomach, saying, “If you have lubricant, you little cunt, you should use it.”

    I was prepared. I’d removed my plug and had a tube of lube by the bedside. I greased up my ass, and his dick. Then wiggling my butt, while kneeling Doggy style I begged, “Please fuck me and make me your girl, Daddy?”

    “Next time you’ll be on your back just as any real girl would be. This time though, you are on all fours, just like the Sissy-Faggot that you are, bitch. And you’re taking it up your Sissy-Ass,” he laughed.

    I can still totally recall, how I felt that evening, as a man’s seed squirted violently into my rectum. I knew right then, that I would never, ever again, consider that any part of me, even my shrinking genitalia, could ever make me, emotionally or mentally, believe that I was a boy.

    Things continued in that vein, not only with Carlos, but also with Dylan and Connor. Though, William never considered having me provide him with any pleasure sexually. 

    At Bennington’s my submissiveness spoke volumes. I followed any edict set down by Ms. Judith as well as her admin, Allison. Any suggestion they made about my attire, makeup and tresses, I followed to a T. 

    Which brings me to the evening that I so very willingly went to Judith’s bed without question. As she had told me, I stripped to the buff, though I minced to her boudoir still wearing three-inch High Heels. The arches of my feet had been so strictly trained, that I could barely wear a set of two-inch kitten heels without some sort of discomfort. From the change in the angle of my arches, and the continual wearing of heels 4 inches tall and higher, my legs were as shapely as any Hollywood Starlet. 

    As I slipped underneath Judith’s cool satin sheets I kicked of my heels expertly in one fluid motion. Judith’s loving, experienced hands reached for me and as she’d done earlier, she pulled me to her warm bosom. That she was old enough to be my Mummy hardly mattered.

    In fact, as I was then, already a Full-Blown Sissy, Judith’s age likely made things far better for me. I really felt safe as our lipstick coated mouths met and the creamy tastes and scents of the lipsticks melded so perfectly. That will always be something that will be impossible for me to forget. 

    I sucked upon one of her nipples as I carefully tweaked the other. I wanted all of her. I doubted she would allow me to enter her, as much as I realized that my penis probably wouldn’t become hard or erect enough to accomplish that sort of thing. 

    We explored each other’s bodies so very wonderfully just as any loving Lesbians would. Though I was not aware at the time that I was falling deeply in love with Judith. Had I forgotten Kathryn? Heavens no. However I was obsessed with Kathryn. 

    I was totally charmed by Judith. Plus, she was now in the process of rapidly becoming my comforter and protector, as I would soon be placed in a precarious position of vulnerability. Judith took hold of my shoulders as she kissed me. She was turning me so that my head would soon be aligned with her pudenda. 

    “Now darling Sylvia, I want you to give my pussy some loving care and attention by using your oral skills,” Judith cooed as I opened my mouth to place my tongue upon her vagina. I’d frequently had oral sex with Kathryn early in our relationship. Mainly when I would fail to sustain an erection. 

    So as I licked, sucked, kissed and fingered Judith’s labia and clit, I recognized the lovely sighs of pleasure that she soon released. Judith’s thighs were firm and taut, from the exercise dancing she performed at the gym she attended. I could feel those strong thighs snug against my head. Judith was straining against my face as I licked her.

    All at once her body stiffened and she let out a womanly screech. She arched her back and pulled on my heavily sprayed and scented hair, gasping, “Oh don’t stop! Don’t you even dare stop. Oh keep that up. Please, rub my tummy, oh yes. Oh you are amazing girl.”

    I kept up what I was doing until she took hold of my shoulders, once again gasping, “Oh, okay, that’s enough. Oh please honey. Come and kiss Mummy, my sweet Sylvia. Oh good girl. That’s it. Kiss my face. Oh yum. Kiss mum-mum’s lips darling.” 

    I sucked on her neck and licked her face until she pulled me close to her. Wiping her hand on her vagina to get some pussy juices on her fingers, she then took hold of my genitals and began to manipulate my cock and balls. 

    “I need to stimulate my girlfriend’s clitoris for her. Mummy will always take care of her girl, sweetie,” Judith said, as she reached for a tube of lubricant at her bedside.

    “I’d be embarrassed to tell you how long it has been since I had a sweet young lady such as you, to lick my cunt, darling,” Judith added as she increased the pressure on my penis and testicles. 

    I was pleasantly surprised as to how firm my erection was at that moment. No, it wasn’t as hard as a rock, however I was hardly disappointed. My passion grew with Judith’s increasingly fervent ministrations. I found myself gasping, and twisting my body from the chilling, electric waves of excitement coursing thru my lithe, svelte frame.

    “I want you on all fours honey. Mummy well knows that a Sissy-Girl’s Love Button is in her rectum,” Judith teased.

    I knelt and then leaned over to place my hands upon the bed. My head drooped from sexual exhaustion and my hair fell into my eyes. As Judith masturbated me with her left hand, she took two well-lubed fingers and slid them into my anus. She used the combination of moving her fingers in both an “In-and-out” as well as a circular motion.

    As Judith twisted her fingers within my “Sissy-Puss,” she would lightly massage my prostate, and increase the pressure on my “Girly Love Button” to raise the level of my sexual intensity. I was panting and whinnying by this time and my emotions were reaching an uncontrollable state. 

    The combined stimulation of my genitals as well as my innermost rectum was driving me to total distraction. I simply could no longer control myself. I eventually completely lost any self-restraint that I may have had, and and began to blubber and drool exorbitantly.

    “Oh my heavens, Mummy Judith, I think I am about to faint!” I screeched so very femininely.

    “Oh dear me, my girl, but you are in a tizzy, aren’t you? Hold on my Sissy Angel, you are beginning to spurt. Mummy has this for her Sissy-baby. Spray your Sissy Cream all you wish Girly. Oh what a good, good, Girly-Girl Mummy’s Sissy is. Oh that’s better. Oops, I think my Sissy Girl has passed out?” Judith laughed.

    I wasn’t completely out, but I had collapsed upon the bed and was shaking, with my body spasming, as I sobbed and dithered as if I were a ravaged Damsel. 

    Judith laid by my side and pulled me to her bosom and said, “Suck and Nurse on Mummy’s Boobies, sweetheart. Oh, now doesn’t Mummy’s tits taste so good to her girl. Oh, you sweet, sweet Angel,” Judith cooed.

    I couldn’t help myself. I had lost all restraint and self-control. I whimpered and sucked on Judith’s bosom until I fell off into some sort of inexplicable trance. I never dreamed I could possibly experience a sexual climax of such epic intensity. 

    I came to, upon my back, with Judith playing with my hair, and kissing my eyelids, as she hummed, so very prettily. She smiled and kissed my lips firmly and said, “We can do that all over again all this weekend Precious. It’s just the two of us alone, for at least four days, Darling.”

    We sat in our lingerie, at the breakfast bar in the kitchen. Our hair was mussed, our makeup was smeared. We drank red wine and gazed at each other smiling. Judith took a hold of my hand and led  me to a very large, comfy couch.

    “Sit with me, and let me hold you. Here, allow me to pour you another glass of wine. We need to talk. Or I need to talk and you need to listen. Now drink your wine and relax,” Judith paused.

    “Kathryn wanted to be alone with William for the weekend as she suspected he was going to pop the Marriage question to her,” Judith informed me to my surprise.

    “And she told me that if he did, she believed she would accept his proposal. And you do not have to speak with her concerning any of this, my Angel. I have told her to contact me with any news. I’ll relate the information to you, darling. I dearly want to shield you from having your heart broken as much as I can possibly protect you,” Judith explained. 

    “Thank you Judith”, I whispered as I leaned my head into her bosom.

    “Why don’t we watch a romantic movie and drink our wine and maybe nibble on some finger food? Wait. Why don’t you shower first and shampoo your hair. I’ll give you a hot oil treatment and then set your tresses on rollers,” Judith offered.

    “I want to take you shopping for some increasingly restrictive figure training items tomorrow. And possibly some hobble skirts. I want you to have the most prim, proper and prissy posture as well as the daintiest of mincing gaits. You may wear the curlers while we shop, covered with a scarf. In the evening we can go out to a Lesbian club. We can comb out your hair for our date at the club,” Judith suggested.

    Later, Judith sat on the couch, with me dressed in a fluffy, white robe, sitting on the carpet, laying back, between her thighs, while she rolled my hair onto medium sized plastic curlers. The “Chick-Flick” we watched, could not have been more appropriate. 

    On her Amazon Prime account’s “Favorite’s List” Judith had dozens of Lesbian Romance Movies from around the world. Many were in languages besides English, with subtitles. That particular evening, we watched one made in England, about a Mature, Thirty-something war widow and her Late-teen’s Lady’s companion, falling in love.

    The older of the two Lesbians did remind me of Judith, as she was tallish and athletically trim, with her hair in a shortish, Salt and Pepper, Pixieish Bob. When Judith completed my roller set, she patted the cushion next to her and said, “Sit here with me darling.” 

    I couldn’t help but snuggle and cuddle romantically with her, placing my hands in her lap as she hugged me, and we kissed intermittently as we watched the film. The morning light found me with my back and butt, cradled against her, with Judith’s left arm holding me tightly. We were wrapped in her silken sheets and covered with a down comforter. It had been an absolutely beautiful night’s sleep.

    Our first shopping stop, mid-morning, was Greta’s Foundation Wear. It was my very first time, in public, with curlers in my hair. Judith had wrapped my curler-infused tresses with the most gorgeous, colorfully designed satiny scarf. Prior to wrapping my curled hair into the scarf, she sprayed me very liberally, with a Spray-Net Lacquer.

    I was wearing, a Pink, “Rah-Rah” skirt, with a slenderizing, white tube top and a Pink, bolero jacket, with tall, 4 inch, white, high-heel stilettos. 

    Greta Stern, the proprietor of the boutique met us and looked me up and down, and said to Judith, “Well Judith, it’s refreshing these days, to see a young lady with her hair up in a scarf and curlers, obviously for an evening outing? Is she your niece I presume?” 

    “My niece? Well, something like that Greta. Greta, this is Sylvia Conte. She’s an employee in my department at Bennington’s. Yes, we’ll be dining and dancing at Aphrodite’s this evening. Sylvia, meet Madame Greta Stern, the proprietress of this lovely establishment,” Judith added.

    “Greta, Sylvia is a Transgender girl in Transition. I want to put her in a more restrictive corset as well as taller stilettos and much snugger pencil skirts. I prefer her to have the posture and the prissy mince of a 1950’s Debutante,” Judith stated.

    “Oh my. Well we simply adore young ladies who are transitioning,  here at my boutique. My girls love working with them. I’ll appraise her posture and her gait, in the “Preening” suite. Who knows? She just might need a posture collar along with everything else,” Greta said smugly. 

    I didn’t exactly know where or what a Preening Suite was, however I was soon in a very spacious dressing area, naked to the waist and being fitted for a new, uplift brassiere. While Judith went off with a sales lady to choose dresses, skirts and blouses for me to model, Madame Greta and three female attendants, fondled, probed and measured my “Girls” prior to fitting me for an underwired, uplift bra.

    “She’s a full B Cup ma’am and a 36. If we pull her waist in 2 inches she’ll be a perfect, 36 and 24,” one of the young females cooed.

    “Measure her hips, please. 34? Very nice. It’s her posture I’m concerned with. Sylvia, stand as straight as you possibly can. Your right foot should be slightly in front of your left. That’s much better girl. Now look straight ahead at that red triangle painted upon the far wall, please. Very nice. Hmm? She’ll be needing a posture collar, straight away girls. Let’s get her fitted with a number three initially,” Madame Greta spoke with authority. 

    “Leslie, continue with her brassiere. Colleen, we’ll try a waist cinch to snug her in. Renee, you know where the posture collars are kept. I’ll contact Cynthia, to bring a panty girdle when she returns with Ms. Judith and the items she’s picked out,” Greta said, commandingly.

    I’ll readily admit, these ladies worked as an efficient team. Unfortunately for me, I was very soon marched to a “Lacing Pedestal,” above which a Corset Lacing Bar hung. When I reached the top of pedestal, the widest of the three steps, I was told to hold tightly to the lacing bar as Colleen fastened my wrists to the bar with manacles. 

    Judith had yet to return. In the meantime, Leslie who would soon put me into my new, Brassiere, Removed my High Heels, Panty-Hose and my Panty-Brief, exposing my “Not-So-Very-Big” Penis and Testicles. She then slipped my Heels back on my feet along with a pair of peds. 

    “That will assist you with your balance Miss, as Colleen corsets you,” Leslie explained. 

    Just then, Judith entered the room, accompanied by Cynthia who was pushing a rack with a vast array of Ladies’s attire hanging upon it.

    Madame Greta was viewing my Genitals when Judith entered the room and remarked, “Gracious Judith, you don’t have her in chastity just yet.”

    “No, she’s not yet truly mine. In any event though, she isn’t really very big, is She?” Judith asked.

    “That’s true. In fact she is borderline tiny, if you ask me,” Greta smirked, as her four female employees giggled. 

    “As we have the panty girdle here, Cynthia, with panties and hose, why not dress her lower half prior to corseting her? Do you have a preference as to girdle, panties and hose, Judith?” Greta asked.

    “Oh my, those skimpy very lacy panties, with sheer hose, as well as the paneled girdle with the garter straps,” Judith said.

    “Very well ma’am. I’ll dress her,” said Cynthia as she removed my peds and heels and attired me in the panties, the girdle with the garter straps and sheer hosiery, prior to slipping my heels back onto my feet.

    I was looking into a full-length mirror, aligned with the lacing pedestal as Colleen approached me from behind and said to Leslie,    “Why not hang up her bra, and assist me with putting her in this waist-cincher, Leslie. We’re taking her in two full inches. That won’t be easy as she doesn’t have much body fat.”

    “Now girls. If you need to, just place one knee in the small of her back to get enough leverage to snug her all the way in,” Greta scolded her employees.

    I felt the two girls pulling the laces. My corsets would be pre-laced and I would put them on by using the snaps and catches in the front of the Cinches. I’d only need lacing if they became loose from my waist becoming tinier. 

    I could have sworn I was going to faint away as the lacing became more snug. Renee, the girl who’d went off and returned with my “Posture Collar” placed a tape measure around my waist and said, “Less than a quarter inch to go Ladies. There we are, she’s at 24 inches. Her butt is a 34. Nearly a perfect figure.”

    “The Estrogen will assist with her derriere Judith. She’ll have a lovely figure. While she’s still on the pedestal, why not put her in her new Bra, Leslie?” Madame Greta asked. 

    My bra fit so very snug, as the waist-Cinch had pushed a tad more flesh into the area around my bosom. The hideous Posture Collar came next. Besides shaping my figure, the secondary feature of the foundation garments and my tall heels, was to keep my carriage, supremely erect.

    The posture collar would see to it that my head and neck were wonderfully and perfectly positioned to give me a prim, proper, dainty and demure countenance to my overall appearance and gait. Once the collar was fastened in place, I could barely move my head and neck a few inches without my entire carriage following along. 

    I was then dressed, the remainder of the way, in the attire I’d be wearing that evening. Removing my heels momentarily, I daintily slipped into a gray, pencil skirt, that tied snugly at the left side of my waist with a delightful, sash bow. After stepping back into my heels, I was put into a baby blue, back buttoned, satin blouse with full Bishop sleeves, an Elizabethan collar and a fussy, ruffled furbelow that went from the collar to my waist line. 

    “Judith, if you give my girls the keys to your Lexus SUV, they will gladly pack all of your purchases into your vehicle. Ladies. Box and bag anything that needs to be, as well as placing anything on a hanger into a garment bag,” Greta announced.

    “Sylvia? Young lady, I want you to walk towards the mirror that takes up the far wall. Then stop and turn to the right, and walk along the mirror, with your head turned to the left, and staring at yourself. That’s it. Mince and sashay darling. Prance and preen. Walk pretty for us,” Greta said, clapping her hands as she continued to instruct me on modeling my new outfit.

    On the drive to Judith’s I turned to her and asked, “Is everything you purchased just for me? You did buy yourself something, didn’t you? You must have spent a fortune,” I asked, incredulously.

    “Don’t be silly. You are worth it, Sylvia. I’m very well off. I’m a Trust Fund Baby, and my inheritance is very well-invested. I don’t really have to work. I enjoy it though,” Judith explained. 

    We had arrived at Judith’s and put all the purchases away in the dressers and closets. Judith had just spoken of combing out my hair for the evening date at Aphrodite’s, when her cell phone rang. She moved nearer the kitchen door to take the call. As she listened, as well as spoke, she had a serious look on her face.

    Once she had ended the conversation she walked into the kitchen and returned with a bottle of Peach Brandy and two glasses, saying, “Come to the settee and have a drink of Brandy with me, Sylvia. There is something I must tell you. Take a nice large swig on your glass. Very good honey.”

    “Come here and cuddle with me and continue to sip and listen. That was Kathryn. Yesterday evening William proposed marriage and Kathryn accepted. They have done a lot of talking and made numerous decisions since then. Kathryn will be selling her home and most of the furnishings,” Judith stated.

    “She will be moving in with William. Unfortunately, William refuses to employ a Sissy Maid. You and I will be collecting your belongings, which are already boxed, after 2, tomorrow afternoon. I am so very sorry to tell you this dear, but you do know you have a place in this home with me darling,” Judith said hugging me to her bosom.

    “Yes, I know. I feel like crying, but I won’t. Could we cancel the dinner date, this evening? I just feel as if I want to spend the night alone with you Judith. Please, take me to bed and make love with me Judith?” I asked.

    “Oh honey, you can bet on that. Still, a nice girly cry will be good for you, baby. I’ll have to warn you sweetie, that I am going to do things to you that very likely, no woman has ever done to you. I’ll make that call to Aphrodite’s now, lover. Get into my boudoir and strip off your heels, stockings, panties and girdle. I’ll be right in,” Judith smiled.

Chapter IV: Sexy Salon Beauty

 

        Judith entered her boudoir with the Brandy and both of our glasses. I stood by the bed, naked from the waist down. She went behind me and unbuttoned my satin blouse. Then she removed my bra and posture collar. She left the corset in place. My hair was still up in curlers and covered with a scarf. 

    I’d just freshened my lipstick. I’d become extra fastidious concerning my makeup. Judith led me to her bed and said, “Let’s snuggle and sip some Brandy. We have all evening. Follow my every lead. You’ll see that it will be more than worth it.” 

    Judith stripped to the buff and laid beside me. We hadn’t even turned the bedsheets down. We were resting against her big, fluffy pillows sipping the Brandy when Judith reached into a bedside lamp-table and came out with a Fat Joint of what she said was Hawaiian Weed. She lit it and took a firm long pull and handed it to me. 

    I loved the way the warm smoke mixed with the cool Brandy-on-the-Rocks. Judith took the scarf off of my curlers and removed a couple of the rollers, saying, “We’ll still comb you out tonight, after I ravage you the first time, Honey Pot. You are in for a long night of hot sex, my little Sissy-Girl. I’m impressed with the way you are handling this sweetie.”

    I took a long pull on the joint, sipped some Brandy and said, “I’m sort of glad that it is all over. I’d be ashamed to tell you some of the things I did sexually when I lived with Kathryn and she had her boyfriends coming over.”

    “Oh no, girl. No secrets. Secrets cam be very painful. Coming out is good for your soul. You can tell me anything. I would never judge you. I adore you Sylvia,” Judith said, kissing me on the lips.

    “Well, I fluffed her boyfriends' cocks, to get them ready for sex with her. All but for William. William was very bland. He never touched me. Though he never minded that I presented myself very femininely. I also cleaned them off, as well as Kathryn, after they had sex. Kathryn often had me watch them screw,” I said, whimpering slightly. 

    “Oh you sweet, sweet thing. I’ll care for you Sylvia. I want you here with me,” Judith whispered.

    “I also performed oral sex upon her new men, while she sometimes watched, and I usually swallowed their sperm. Of course, they also came to my bed at night and screwed me just as if I were another girl in the house,” I added as I began to sob.

    “Oh that’s it baby. Let it all out. See just how healing it is to share your secrets with someone who cares for you? Oh baby, let me love you and keep you here with me? We’ve come this far. I’ll take such wonderful care of you. I promise you, Doll,” Judith added.

    “I’ve become very fond of you Judith. Yes, I’ll live with you if you so desire,” I cooed sexily.

    “I want you as Sylvia, honey. You’ll always have to be Sylvia for me. It’s Sylvia I’ve fallen in love with,” Judith said. 

    “Of course. I understand. I’ll be your girl Sylvia, Judith,” I promised as we both set our drinks down.

    I stubbed the Joint out and we embraced and French kissed. Judith  got on top of me and then crawled to put her head at my crotch. She licked my penis and balls.

    “I’m going to lick my girl’s clit and labia. You will always call this thing between your legs a clitoris. Never call it anything else. If you don’t do as I’ve just said, I’ll never lick it again or take it in my mouth. Do you understand, Sylvia?” Judith asked.

    “Yes Judith. You are touching my clitoris,” I agreed.

    “Good. In fact, to make you feel as more of a girl, I’m going to make you have a ‘Period.’ You’re to have a time of the month which we’ll mark on a calendar, and you will wear a Pad to cover your clit and a tampon is your Ass-Pussy. Agreed?” Judith added.

    “Yes, of course. Anything. I’ll do anything for you. Oh gracious, but that feels so divinely wonderful, Ms. Judith,” I mewled.

    I was surprised at how erect I could still become. It wasn’t the gigantic boner that I remembered Carlos placing between my Carmine coated lips, but it was still firm and could possibly enter a vagina. Not that I actually cared any longer. As I got further along into sexual excitement, Judith said, “One moment, young lady, I have to get my cock lubed and ready for you.”

    I was mildly startled, when Judith produced an average sized Faux-Penis which she strapped to her hips and smiling, said, “I’ve used this on a few, sweet young lesbians and a few my age. Now to make certain. You regularly wear a butt plug and you’ve already been plowed?”

    “Yes. That’s all true. I’ll need to remove my plug though,” I gasped.

    “Put it in my bathroom sink and get back in here so that I can lube you up, girl,” Judith demanded. 

    Judith had me stand with my back to her as she applied copious amounts of lube to my rectum. She also massage my “Clit” to keep it modestly stiff. Then she turned me to face her and asked, “How would you liked to be Pegged, my lover? Do you have a favorite position?”

    “For tonight. Could I sit upon your lap, facing you? So we could hug, and kiss, as well as bite each other’s necks and play with each other’s Tits,” I asked.

    “Of course Princess. That sounds just so very, very lovely. Climb up on Mummy’s well-oiled cock, Baby,” Judith said in a sexy voice, as I sat facing her and locked my legs around her waist as I lowered myself slowly down upon the dildo. 

    I’d become so very fashionably svelte and sylph-like, from very strict, girly dieting. I likely only weighed about 120 pounds and was not quite, Five-Feet-Nine. Judith was nearly six-feet tall, and weighed a very well-toned 160 pounds. She looked so very stylish in her silver and brunette, Pixie-Bob. 

    I looked directly into Judith’s smiling eyes as the very last inch of her rubber cock went deep within my asshole. As I sighed in gratification, I threw my arms around her and sucked on her neck. Then we French-Kissed for some time as I slowly and very carefully went up and down on her Faux-Cock. 

    Anyone would find it incredible that even with two curlers taken down from my roller set, my curlered tresses stayed totally intact. Even after the passionate sex, that Judith and I would engage in. That was just how well Judith would put up my hair when she did it in rollers. Each and every curler was perfectly positioned and exceedingly, tightly wound and well-pinned. The application of spray-net lacquer was profuse and thorough. 

    I then began to bounce up and down crazily upon Judith’s well-formed rubber cock. The cock had several soft, small nubs where it came in contact with Judith’s vagina, which would titillate her labia and clit. As I bounced, squealed and gasped, Judith increased her pumping action and further aroused my sensitive prostate.

    I was near exploding and I knew Judith was quite aroused. I began to whimper, and then the stress of the entire day compounded and I began to squeal and sob as I ejaculated wildly all over Judith’s flat tummy. I was shaking, nearly feverishly. All I continued to say was, “Oh Mummy. Oh Mummy. Please hold me and love me Mummy. Please?”

    Judith stood me up so that the Faux-Cock slid out of my ass. Then she pulled me to the bed saying, “Come to Mummy, my Princess. Mummy will take perfect loving care of her Precious Angel.”

    I don’t know how long I laid there, sobbing in her embrace. I had never felt so absolutely sated and fulfilled in my entire lifetime. I looked deeply into Judith’s eyes and told her, “You mean everything in the world to me at this moment. What may I do to please you the most, my Beautiful Queen?” 

    “Crawl between my legs as I remove this plastic cock. There now. Position your face inside of my thighs, and care for my clitoris until I pass out, please” Judith sighed.

    I took the greatest of care to give Judith the loving attention she’d just given me. In no way shape or form could I possible envision her having the massive climax I had just been given. I wanted dearly however, to please her sexually the best I humanly could. 

    I tongued her twat softly at first. Then I increased the pressure as my lips sucked her clit. I kept her labia spread wide with my fingers to maximize the area I was stimulating. By now, Judith held my head snugly between her thighs and the heels of her feet pushed against my upper ribs. 

    Judith moaned so seductively as I kept her clit wet with my tongue and lips. I massaged her clitoris with my fingers. Her gasps and coos, became more frequent and the pace of her breaths increased. As her strong, shapely thighs clamped tightly upon my roller set tresses, I could hear her let out a soft gasp and a long moan, followed by a satisfying screech.

    Her body spasmed, and she reached to grip my slender shoulders as she exuded her damp juices all over my face. She pulled me to her and told me, “Kiss my eyes darling and rub my tummy. Oh so nice. Such a sweet, sweet girl!”

    We lay there for a long moment, facing and holding each other, our eyes taking in the perfection of the other’s soft, adorable face. Then we kissed and Judith laughed.

    “I need to do something with your hair. I simply must take it down out of the rollers and style it. You can’t be sleeping in those curlers again this evening. You can wear a sleep net. We can take in a nice restaurant Sunday after we collect your things at Doctor Bradford’s,” Judith announced.

    “I am just so sorry we couldn’t go to Aphrodite’s this evening,” I cooed.

    “Oh no. Don’t fret over that. I can always show you off to my Lesbian Coterie on another occasion. It’s far too special making love with you, to pass on such a lovely opportunity. You have such sweet, pussy-kissing lips, you know. Which reminds me. I want to make an appointment for you this next Saturday to begin a Collagen, Lip-Plumping process,” Judith said.

    “I want you to have those lips fattened, and give you a more ‘Shampoo and Style’ type Do. Hmm? Maybe a Body-Perm and a shorter cut, and reshaping,” Judith winked.

    That evening Judith dressed me in a new, Rose colored negligee she’d just purchased for me and put my hair into a Prissy, Ballerina, Updo and Top-Knot. Then we watched a series of Transgender Beauty Pageants. It was during a “Miss Gay Venezuela” Pageant that we viewed a stunning young contestant, named Sandra Primera.

    Sandra was stunningly gorgeous and must have easily won the First Place Crown. She also had a hair stylization that Judith loved. Judith insisted that  she would have the girls at Bennington’s salon give me the same hairstyle. The following Saturday I found myself at the Salon at Bennington’s wrapped in a Pink cape and seated in a salon, makeover seat, in front of a Three mirrored, wraparound styling vanity.  

    My tresses were still quite wet, from a shampoo and creme rinse. Lydia, the stylist was reshaping my hair, based on a video of Miss Gay Venezuela, 2022, Sandra Primera, having her hair done, by her boyfriend Carlos. They appeared to be a very sensuous couple.

    Sandra did seem very Prissy as she spoke to Carlos about how she wanted to look after her hair was done. As Lydia trimmed and shaped my locks, Donna, the skin care specialist carefully injected my lips with the “Plumping” chemical product. 

    While my hair and lips were being done, Judith had departed for a special meeting in the Bennington Corporate Offices on either the 11th or 12th floor. I would have thought that it was very unusual for anyone to even be present in those offices on a weekend, let alone having a meeting there?

    When Judith returned, she was smiling, and when she spoke to Renee, the Salon manager, Renee hugged and kissed her and became very excited. At the same time, Lydia was finishing my Cutting and Shaping. I noted She had left quite a bit of length and volume on the top, tapered the sides, and clipped the back with an Electric trimmer to undercut my nape. Even so, she’d still left the hair on the sides and back thicker where it met the top. 

    By the time Lydia began to wrap my hair on the larger body-perm rods, Donna had completed the first in my series of Lip-Fattening injections, saying, “I’ll see you in four weeks Princess. Then a month after that we’ll finish things up. Afterwards, you should come in every nine months to keep your pretty Bouche, plump and pouty.”

    As Lydia continued to roll my hair on the perm rods, Judith took one phone call on her cell and made another. Each time she used her cell, she would glance over at me, smile, wink, and give me a really cute, Girly finger wave. As Lydia completed putting all the rods in my hair she took time to explain the process of a Body-Perm.

    “We use larger rods and a looser wrap to give a more relaxed curl and wave, then you’d get with a curly perm or a poodle perm. Even more relaxed than a spiral perm. Your hair will be similar to a Beach wave. You’ll rarely need to set it and it will take a styling and keep it’s shape,  with just some Pomade and a little teasing and spray,” Lydia explained. 

    It was the application of the perm solution I wan’t quite prepared for. I would find out why my lovely sister Elaine would always roll her eyes, once she was 16 years old, whenever my mother might suggest that she go to a salon to have a Permanent wave put in. Elaine, like Mummy Vivian, had such thick, Dark Auburn hair. 

    My natural color was medium Auburn, though I’d had it lightened and then had Ginger highlighting added, when my Sissification had began. Once all my wave rods were in Lydia pulled the rods tightly by placing a cotton gauze wrapping around my hairline. She also tucked a towel over my shoulders prior to tying the towel tightly at my neck.

    “The towel and the gauzy wrap are to keep any waving solution from dripping down your face and neck, darling. However, hold this wet washcloth to wipe away any perm lotion that does find it’s way past the cotton gauze, dear,” Lydia added. 

    As Lydia cut the tip of the bottle of Perm Solution, she began to squeeze the bottle and carefully distribute the pungent smelling lotion all over each section of hair wrapped around a perm rod. It was very obvious to me why my sister would reject the idea of going thru such a process.

    However, in spite of the odorous scent, there was something about getting a perm, that as a Sissy, excited me. As feminizing as being fitted for a bra had been, somehow having a permanent wave done, even a loose body perm, was stimulating and exciting in a sensuous, sissifying manner.

    To see myself in a wraparound mirror, my head full of colorful wave rods, with the towel around my neck, wearing a pink, plastic salon cape, as well as the cotton gauze, really put me in touch with the fact that my fading boyishness had alarmingly melted and evaporated far away, and would never ever return.

    Just thinking about how weak, pathetic, subservient and girlishly  feminine I now was, actually aroused me. Fortunately, for me, Ms. Judith had decided that on this particular Saturday, my four day, “Menstrual Cycle” for this month, would begin.

    I not only had a Tampon inserted in my anus, but I had a Maxi-Pad placed in between my “Clitoris” and my Satiny panties. So when my “Clit” leaked some Sissy-Cream, the pad did soak it up to keep me from staining my pretty panties. I felt fortunate in some ways, to have had the Tampon inserted into my rectum, rather than the usual butt-plug.

    Additionally I was also expected to change both the pad and the tampon upon each trip to the Ladies Room, as well as drink a minimum, of a gallon of water each day to experience the bloating involved with a Period. In any event, once my tresses were saturated with the Body Wave lotion, a plastic cap was placed over my permed tresses, and I was escorted to a Dome Hair Dryer and the heat setting was placed on warm.

    As the dryer whirred and the warm air wafted over my head and shoulders,  the perm rods tightened slightly and the acrid scent of the lotion filled my nostrils. I was given a copy of my favorite Beauty and Fashion Magazine, Les Femme Tres Chic. 

     However I didn’t get to read much of the article on the Lady who started Runway Rogue Cosmetics, as Ms. Lydia checked the intensity of my curl every few minutes, prior to turning the dryer off and taking me to a sink for a rinse. Then the neutralizer was added prior to a second rinse. 

   Next I was taken back to the styling vanity to have the rods removed prior to stylization and makeup. As the rods were plucked from my tresses, Ms. Judith used her phone to snap photos of me during my comb-out, styling and makeup application. Lydia tilted the chair back so that she could basically use my face as if it were and Artist’s Palette.

    I was in the usual position of a fashion model having her face done prior to a runway show or a photo shoot. Lydia turned to Judith to ask, “How do you want her face done, Judith?” 

    You’ve seen her dolled up at the cosmetic and perfume counter. I’d say go with a really glammed-up look. Especially considering the ‘Do’ you’ll be giving her,” Judith winked.

    “Besides, with my new promotion, to Tri-State VP, for Ladies’ Beauty Products, Hair and Fashion, I’ll want my new receptionist to be a stunning piece of Eye-Candy,” Judith commented. 

    “Oh my! You’ve been promoted to Corporate? I’m going to be your receptionist?” I gushed.

    “Hush Princess. Ms. Lydia is doing your face and hair. We can talk about all this and more, later today at luncheon,” Judith said sternly. 

    Lydia went with a decorative enhancement of my natural colorings. She used bold Burgundies and Sienna’s around my eyes, with splashes of Coral, along with a blend of Beige upon my cheeks. For my recently injected lips, she went with a striking, Plum Lipgloss with a crimson outline. As she lifted the chair to an upright position, I could see that my permed locks were still slightly damp, and a crazy mass of curlicue ringlets and soft waves. 

    I also noted that Lydia had done a simply extravagant makeup application to go with my Soon-to-be, new hairstyling. After snapping yet another photo, Judith set out the three sets of earrings she wanted me to wear, once my hair was styled. Lydia promptly began my stylization.

    She worked a water-soluble styling pomade into my freshly body-permed locks. Judith told me, “I generally prefer Styling Pomade over gels and mousses, as it gives a stronger hold and your tresses will simply shimmer and shine. With a generous application of spray-net lacquering, your ‘Do’ will hold in place well into the evening with just an occasional touch up with a comb and some hair-spray.”

    “When you come back in for your next treatment of Lip-Fillers, I’ll redo your Ginger Highlights and touch up your Light-auburn color. Oh. And I have some splendid, new, Cosmetic Setting Spray just out by Rula Habib Cosmetics. It will seal your makeup for the rest of the afternoon. All you may need to do is powder your nose and freshen your lips,” Lydia stated.

    “Oh my, but Sylvia does love using her compact. Even more so than most girls her age enjoy using their cell-phones. The ladies at the cosmetic and perfume counter tell me she pouts into her compact mirror and paints her lips more frequently than anyone else in that department. Not to mention spritzing her wrists with perfume,” my Partner, and Lesbian Lover, Judith remarked.

    “Oh Judith, under your strict tutelage she’s simply become the consummate Girly-Girl. We should both be exceptionally proud of her, darling,” Lydia effused. 

    I observed, in rapt fascination, as Lydia did her magic, and while using comb, brush and spray, she designed and fashioned an absolute tonsorial masterpiece with my delightfully waved locks. As she teased my hair Lydia created a daring, sleek, shiny, stylish, swept back, high lift Pompadour with a trendy, Duck-Tail just above my shaved nape. 

    When she had completed my makeover and removed my cape, Lydia pinned a black bow just above my Duck-Tail. Judith hung a pair of huge, circular, silver, Gypsy Hoops in the lowest portion of my earlobes. At about the lobes’ center, Judith attached a set of Coral Pendants. Lastly she pinned a duo of diamond, Starburst studs, at the upper portion of my ears. 

    When I stood, and Judith turned me toward a full-length mirror, I could see for myself that I appeared as if I were a movie-star or a model. Besides my delightful, new fashionable “Do,” my dramatically painted lips and face, my extravagant ear decor, I wore the absolutely most gorgeous Floral Jacquard, Lantern Sleeved, Tie Neck, Silver, Satin Blouse, with a slenderizing, high-fashion, Lavender, pencil skirt, and Mauve, four-inch pumps.

    With Judith’s hand in the small of my back, and my Taupe, Doctor Style Purse in the crook of my arm, I sashayed to the lobby, where Judith removed her New Corporate credit card, to pay for my beauty services, explaining, “As my receptionist you’ll be the Eye Candy the visitors to my office will first see. This is money well-spent by Bennington’s.”

    “All you’ll need to do is smile, mince prettily, sway your hips, twirl seductively and only speak if spoken to, Sylvia,” Judith added.

    Once in her new Mercedes Sedan, on the way to Sardi’s in White Plains, Judith explained the Logistics of both her promotion and our move to the Corporate floors. Then she told me we’d be changing Gynecologists. 

    “I have nothing against Kathryn and neither should you, dearest. It’s simply, for the best, for all of us, for the time being. There is a GYN in my Lesbian Coterie that does fabulous work with Transitioning Girls. She can take you in first thing a week from now. 8 AM, for consultation, injection and exam,” Judith added.

    Then she dropped a real bomb, when she added, “You’ve been a naughty girl, haven’t you Sylvia? I spoke to your Mummy Vivian today. You haven’t spoken to her or your Sister Elaine in over a year.”

    “You spoke to Mummy?” I asked.

    “Yes. And I told her you will contact her this evening. And sooner than not later, we will have her, Elaine and Elaine’s partner, Jasmine over for a nice visit and dinner. That still reside in Chappaqua. She contacted me thru the Corporate phone directory at the Bennington Web Site,” Judith explained.

    “A close family friend saw your Bio at Bennington’s online. She mentioned to your mother that there was a Sylvia Conte listed there. Your mother looked you up and not only did the similarity in names convince her, but she could still see the resemblance of her little Mummy’s Boy in Sylvia’s photo.

    After a lovely lunch, at Sardi’s, we returned to the residence where I now lived permanently as Judith’s partner. I called Mummy and we had a lovely conversation. That evening as Judith and I hugged and kissed on the love seat in the den, Judith insisted, “We’re going to pay quite a lot once those lips are fully plumped. I’d better take you to bed and do a preliminary test to see how well they perform.”

    “Oh yes darling. And I’m guessing you want my lips kissing your Pussy?” I panted lustfully. 

Chapter V: High-Fashion Girly Mode 

    I was at the Cosmetic Counter, fixing my lips, powdering my nose and spritzing my wrists and neck with perfume. I was thinking about the new six-month time release capsule of Girly Hormones that our new, GYN Doctor Jessica Trent, had inserted into my butt, right behind my hip, a few days ago. I’d no longer need to ingest my “Pretty Pills” and would only need a Booster every two months. 

   It was as if I could sense the Estrogen streaming thru my girlish body, and in every second of time I was becoming increasingly more feminine and womanly. It had been a surprise, when I was strapped into the exam stirrups and the Doctor had explained that I’d need to give a sperm sample. 

    Of course, I wondered if I’d be given the privacy to masturbate, or possibly one of Doctor Trent’s pretty Nurses or Techs would be masturbating me? As soon as I’d signed the papers for the exam, injection, bloodwork and sperm sample, the Doctor smiled and said to Nurse Sofia, “Why not get our newest, Tech Trainee, Bambi, to extract the sperm sample, Sofia?”

    “Bambi” entered the exam room, mincing prettily, her heavily painted mouth shimmering with Hot Pink Lipstick and a nearly matching Coral shadow upon her eyelids. “Bambi” was an Asian, limp-wrist, fairy pansy, who was quite eager to extract some sperm from me. She walked with a thoroughly exaggerated swivel to her hips. 

    Yes. I know that I have hardly ever been a keen example of even mild boyishness. It’s just that Bambi was the epitome of a lisping, giggling, Sissy-Femme.

    Her entire outfit was done in Sissy-Pink. That included both her scrub top and her slacks, which were pegged similar to a pair of Capri pants. Her four-inch pink heels were a bit much for a GYN clinic, however that added to her allure.

    Bambi took one look at my penis, bent over the exam table and licked all around the tip of my cock, to the amusement of the medical staff. She used the moisture from her mouth and took hold of the end of my dick, and massaged it with her fingertips. As my penis expanded she winked at me and took it into her mouth.

    She was going to suck me off, in front of the GYN, my lover Judith, the nurse Sofia, and a medical tech. The Tech giggled and reminded Bambi, “Honey, now don’t forget. Some of the sperm needs to fill the sample bottle. So please don’t swallow all of it, Doll?” 

    Doctor Trent turned to Judith and added, “She’s just so very eager to help out with these Sperm samplings that I simply feel so compelled to allow her to get involved.” 

    “I find her absolutely delightful. I love the Pixie-Cut. It’s just simply so Sissified,” Judith agreed. 

    “Imagine some of these Sissies, who are scheduled for Castration, and Bambi is giving them their very last Ejaculation?” the nurse remarked, smirking.

    I closed my eyes, to avoid looking at anyone during those moments while Bambi was giving me a blow-job. She licked all around my cock and gently handled my testes. The erection I experienced was the stiffest and most erect my cock had been in several years. Of course, my penis was then inside of the mouth, and between the puckered, painted lips, of a Gay-Sissy-Faggot, who was just as much of a Panty-Wearing, Dick-Licking, Anal Fairy, as I was. 

    I wondered if Judith had noted the hardness of my penis and compared it to the stiffness I managed to achieve when I was with her? As my penis swelled, Sofia the nurse, set the sampling container very close to Bambi, who nodded her wide-eyed assent, as her head bobbed up and down upon my cock. My ankles were securely fastened in the examination stirrups and at this point, the Nursing Technician held my wrists snugly above my head.

    I was more or less forced to gyrate my pelvis and pump my cock into Bambi’s mouth. I began to breathe heavier and whinny. Tears began to form in my eyes. I looked down at Bambi who was looking up at me. As I released my ejaculate, Bambi gulped and swallowed the initial gush of semen.

    Next she placed the sample bottle at my cock and watched it fill. In one simultaneous motion she handed the sperm sample to the Nursing Tech, who corked the bottle, as Bambi placed her lips back around my penis and sucked the last vestiges of my ejaculation dry. 

    I nearly passed out. Bambi then stood up and walked to stand next to me. As she leaned over she whispered, “I hope that was as special to you as it was to me Princess?”

    “Yes it was. It was very, very special to me,” I admitted as Bambi planted a kiss upon my cheek. 

    Next, Doctor Trent examined my rectum with a sterile glove coated with KY Jelly. She excited my prostate just enough to force me to gasp and sigh.

    Doctor Trent, then remarked,“Oh, I think she enjoyed that, Ladies?”

    She then felt my boobs. After she examined my penis and testicles she spoke to me.

    “Your Two Girls are coming in very nicely Sylvia. Your penis and testicles appear to be shrinking just so very, very, beautifully. A lot of my Sissies consider, larger implants, castration, as well as SRS. You should sit down and discuss all of these procedures that we offer here, with your partner Judith. I’ll see you in two months for another booster,” Doctor Trent added.

    On the drive to the residence where I now lived with Judith, Judith asked, “Would you enjoy having a Play-Date with Bambi, Sylvia? You really don’t have any Sissy friends, or companions, you know? Bambi works part time at the Clinic. She is actually Doctor Trent’s housekeeper and Lady’s Companion. So I do have her personal cellphone number as well as Jessica Trent’s.”  

    “Let me know if you are interested in developing a relationship, with Bambi, honey. Okay?” Judith added.

    I’d been thinking of all this as well as the move next week into Judith’s new office, when a sultry voice spoke nearby me, “Well you must be the advert for the Makeover services here? As every girl would want to look as fabulous as you do, Princess.”

    I turned towards the voice and viewed a stunning, Arabic female.

    “Well I don’t think my makeup skills could possibly make you appear to be any more stunning than you already are? Where have I  seen you before? You look very familiar,” I stated.

    “Possibly in a Fashion magazine or on TV? I’m Rula Habib. I once modeled for a living. Those days are mostly behind me. I now have my own agency, as well as my very own Ladies Fashion line, along with both a Perfume and Cosmetic brand,” Rula introduced herself.

    “Yes. I recall you being at Televised tennis matches. Doesn’t your brother play? And I’ve used your perfume. It’s lovely,” I added.

    “Thank you. Yes. My brother Elijah is currently number 1 in the world. May I ask if you’ve done any modeling, dancing, or acting?” Ms. Habib asked.

    “No, nothing like that, I’m afraid,” I blushed.

    “Well you should. I can picture you doing cosmetic and perfume commercials at the very least. And you have the figure to walk a runway, certainly. Please? Take my business card and allow me to keep a copy of your’s? Thank you,” Rula smiled and we exchanged business cards.

    “Sylvia C Conte? What does the C stand for?” Rula asked.

    “Cerise,” I answered.

    “That’s beautiful. So very glad to meet you Sylvia Cerise. I’ll be back in touch,” Rula promised.

    I am guessing I next saw Rula, a month later, at least. The excitement around the office was infectious. Rula Habib and her brother Elijah, were coming to discuss a deal to have Bennington’s exclusively represent all of her products in the New York, Jersey and Connecticut region. Her attorney’s were already caucusing with Bennington’s Lawyers, in the conference room. 

    I had been mincing and sashaying about, serving food and beverages, smiling profusely and only speaking when someone spoke to me. I had been told to be a pretty face, as well as a sexy body, swiveling my hips for all of the men within the room. As for speaking? Well? I was to have an empty head and closed, pouty, Bee-Stung lips. 

    Judith walked over to me and advised, “The Habib’s have just entered the private, Exec elevator. I need for you to meet them and escort them here Sylvia.” 

    I sashayed to the elevator. The door opened as Rula and Elijah Habib, stepped into the hall. I hadn’t bothered to pull up any photos of Elijah Habib. I must have watched him at least once, or twice, when he played tennis on a sports program? I’d also seen his handsome face in a sexual fantasy.

    Yes it was him. It was assuredly him. My mind wandered to an evening at Kathryn’s home when I had sucked Connor’s cock. Prior to Connor leaving for the night, we had kissed and I’d became quite sexually aroused. I needed to masturbate. 

    As I lay in bed, with my eyes closed, with my lubed fingers upon my penis, I attempted to picture Connor, entering my rectum with his firm cock. However, try, as I might, to conjure up Connor in my fantasy, the masculine face and body of Carlos, intervened for a time, only to be replaced by a male with a handsome swarthy face, and a very well-toned athletic body, not to mention a firm, meaty cock.

    That “Mystery” man, now appeared next to Rula Habib in the person of her brother, Tennis Pro, Elijah Habib. And I could still recall the orgasm I received when he fucked me in my fantasy. 

    As I smiled at Rula and extended my hand, she threw her arms around me and bussed me with a Sisterly kiss upon my cheek. I immediately returned that lovely greeting.

    “Sylvia it is so very exciting to see you again. Ms. Leonard told me you were now her receptionist. I mentioned you the last time I spoke to her. Sylvia this is my brother, Elijah,” Rula added, stepping back.

    As Elijah kissed my extended hand as I limped my wrist, Rula added, “Elijah, this is Sylvia Cerise Conte. This is the girl I want as the ‘Fresh Face’ to represent our products as Spokesmodel.”

    “Yes and a lovely face at that, my brilliant sister. In fact she is every bit of Stunning, in my opinion,” Elijah winked. 

    Between the wink and the kissing of my hand I was weak in the knees. Startled, I said, “Please, follow me to the conference room. We have food and refreshments.”

    Once again I was lost in the chatter of the lawyers and the principals. I took the Habib’s food and drink order and delivered it with a very proper curtsey. Then Rula asked, “Ms. Leonard, have you discussed with Sylvia, the possibility of her being our spokesmodel?”

    “No. I have not Ms. Habib. I didn’t think the deal would be completed today. I’ve really been procrastinating on that front,” Judith apologized. 

    “Which I can understand, Judith. Based upon the closeness of your relationship with Sylvia. I think the deal can be closed by tomorrow, Friday, however. Would it be possible to discuss it this evening? The logistics would involve Sylvia living at my Manhattan Condo so that she could be closer to the Charm, Modeling, Acting and Ballet Instructors,” Rula explained.

    “I believe it would be at most, a six-month window prior to her being able to do Perfume and Makeup Commercials and model my fashion line. You could visit any time, as well as her family. Later, I’d expect her to open a few fashion shows for me. Possibly in New York, Paris, and maybe Tokyo?” Rula went on.

    “After that, I’d only need her for TV spots or Magazine interviews,” Rula shrugged. 

    “How do you feel about it honey?” Judith inquired of me.

    “It is overwhelming, yet very exciting, all at once,” I answered.

    That evening, while Judith held me in her arms in bed, in my boudoir, we discussed, what to me was an intoxicating future. 

    “I have my fears and doubts, especially being away from you. Yet, the challenges and the possibilities are exhilarating,” I agreed. 

    “Then, I am all for you giving it your very best, darling,” Judith said as she kissed me upon the lips.

    “Oh Judith, I love you so very dearly,” I cooed, as we began to consummate our love for each other. 

    The deal was signed, my bags were packed, and I was on my way to Manhattan in a chauffeured limo with Rula, 3 days later. Elijah had already boarded a plane for a Tournament in Europe. 

    The “Acting” classes I would be subject to, would prepare me for doing the Perfume and Makeup commercials. The “Charm” lessons were designed to prep me for public appearances, such as talk shows, televised interviews, and awards banquets.

    Rula Habib desired to portray me as a Prissy Debutante that would properly smooth my skirt when sitting, paint my lips after dining, and spread my fingers, as if I’d just painted my nails, whenever I minced about daintily. Of course the “Model” training would ready me to walk the runway or catwalk during a fashion show. It was the Ballet practice that Rula considered most important.

    “As you study Ballet Dancing Sylvia, you’ll learn gracefulness and poise. You will gain confidence that you are indeed, truly feminine. Madame Bouchard, your Dance Mistress, will not be training you to become a professional Ballerina. She will be teaching you to feel exceedingly feminine throughout your daily life,” Rula explained.     

    “Prior to any release of a Perfume or Cosmetic commercial, I plan on introducing you as our Spokesmodel thru a combined article, interview and photoshoot, in the Monthly Fashion and Beauty Publication, Les Femmes Tres Chic. As a backdrop I want you comfortably ensconced at the home were you reside with your lover and partner, Judith Leonard,” Rula stated.

    “We’ll also use this as an opportunity to introduce your family, as well as allow everyone to realize that you are Transgender. I’ve spoken to both your mother and sister, and they are completely on board with this approach. I understand you only recently admitted to them that you dressed in their attire as a young boy?” Rula asked.

    “Yes. That’s true. I also hid makeup in my room, and used their curlers and other hair care products. And once Kathryn told me I had to present femininely in order to not appear to be a threat to her new boyfriends and lovers, I feigned recalcitrance. I also did the same when Judith insisted I appear more girly, in order to work for her in Perfume and Cosmetics. However, I was in actuality, a very cooperative participant in my own, seemingly enforced, emasculation,” I admitted.

    “I plan on the interview taking place when your mother, sister and your sister’s partner visit you and Judith during the last, long weekend at the end of Summer,” Rula stated.

    After several weeks of Acting Classes, Modeling Practice, Ballet Lessons and Charm Tutoring, I went through the grueling procedure of filming my very first Perfume commercial. Once the director and Rula felt that the final “Take” was “Perfect.” I sat with Rula at her headquarters to Preview what the Television audience would be seeing. 

    In the commercial, I was seated primly at a Very Elegant, Lighted, Mirrored vanity, “Touching up” my hair and makeup. When, in reality, the professional stylists and cosmeticians had actually just spent an inordinate  amount of time, beautifying me. Indeed, I appeared absolutely stunning. I was tightly corseted and girdled, and wearing Ultra-High, six-inch stilettos, as well as a shimmering, silver-lame, ankle-length, fish-tail evening gown. 

    My tresses were in a swirled, “Updo” and the golden choker at my neck and the high Elizabethan neck-line of the Gown, easily obscured my posture stabilizing collar. With the restrictive attire I wore, as well as my ever-present, intrusive rectal dilator, I was limited to little more than a very tiny, mincing, wiggling gait. 

    My makeup was absolutely flawless, along with my elegant, lengthy, painted, fingernails. As I looked into the mirror and feigned a critique of my face, nails and hair, a doorbell rang in the background. I then acted as if I was going to stand, but I then looked down at the vanity top and smiled.

    I picked up a spritz bottle of perfume and sprayed a small amount of the perfume upon my wrists and gave each side of my neck a spritz. Then I rubbed the sprayed areas gently and smiled. I minced thru what appeared to be the parlor of an elegant penthouse suite.

    I next opened the door, that led to the hall, and said “Oh Raoul. Please come in darling? It’s been far too long my love.”

    The handsome, Latino male embraced me and we kissed. Smiling, I then hurriedly led him away, as we held hands. The camera then panned back to the boudoir vanity to show the bottle of perfume. A Sultry female voice than said, “Every girl wants some Seduction in her life, when that special man visits. Seduction. A Boutique Perfume by Rula Habib.”

    For the first cosmetic commercial, I was to advertise “Merlot Magic” which by then had become my favorite lipstick. The skit began in a similar way with me at a vanity. Though, my hair was in a “Swept-Back” styling, and I was wearing an Off-the-Shoulder, Lilac colored taffeta dress, with Bouffant Petticoats and a darling, pink, Bolero Jacket.

    In the scene I was portrayed as if being in a backstage dressing room. A beautician had just finished styling my hair, and I said, “Thank you, Maurice. You’re a Jewel, darling.”

    I looked at myself as if something was missing. A girl with a clipboard stood behind me and said, “Miss Conte, you are on in five minutes, ma’am.”

    “Thank you Janice. Tell them I am on my way,” I added

    At the very last second, I smiled, picked up the tube of lipstick and carefully coated my mouth, with the shimmering Merlot Magic. I confidently stood up and sashayed towards the wing of the stage, with a seductive woman’s voice adding, “Every girl wants some Magic with her, when she’s entertaining her adoring public. Merlot Magic. A distinctive lipstick for discriminating ladies, by Rula Habib.”   

     After the weeks of classes and training, doing commercials, and feeling as if I always had to be somewhere, it was just so wonderful to be home with Judith. I was looking forward to the upcoming visitation from mother, my sister Elaine and her Partner Jasmine. Even the interview with the writer from “Les Femme Tres Chic” would be an opportunity to Bare my Soul. 

    I did however have something on my mind that I absolutely needed to share with my lover, Judith. During the weeks I had spent living with Rula Habib, her brother Elijah had been in Manhattan about half of that time. Though not a frequent visitor to his sister’s condo, the very masculine and handsome Elijah was present often enough that I realized there was a definitive, sexual chemistry, that was building  between us. 

    Often enough when we were together, the manly Elijah would take liberties as to hugging me and touching me in a manner that could only be described as Intimate. Soon enough, the hugs led to him fondling my buttocks, and the Pecks to my cheeks, then became soft gentle kisses upon my lips. 

    The thing was, as much as I was committed to my loving relationship with Judith, a sexual encounter with a sensuous male such as Elijah Habib was much more than tempting. But how would I possibly be able to explain all of this to Judith? My thoughts were primarily surrounded by this as the chauffeured limo, provided by Rula Habib Fashions, arrived at the very opulent home where Judith Leonard and I resided.

    It was mid-morning, on a Thursday, and I’d planned it that way. I’d woken early to shower and set my hair. My tresses were still up in rollers and a scarf, as I minced to the front door to unlock it. The driver carried my bags inside as I held onto my cosmetic case and purse. 

    “Could you please carry my bags to my boudoir, Carlton?” I asked.

    When I tried to hand him a tip, the driver said, “No ma’am Miss Conte. Ms. Habib has already taken care of that.”

    Judith was already at her Executive office Suite, as it was 9 AM. I decided to text her. “I’m home, Lover,” I wrote, adding a few heart emojis. 

    “I can’t get away until early afternoon, darling. See you at 2 PM? That’s when my four-day weekend begins. I’m taking tomorrow off.” Judith wrote.

    “Perfect my love. I’ll be ready and waiting with your surprise,” I added.

    “Now aren’t you just Mummy’s Good Little Girl?” Judith teased.

    We had a big, busy, holiday weekend ahead of us. My Mother,  Vivian, my sister Elaine, and her lovely Asian Partner, Jasmine, would be arriving, Mid-Morning on the morrow, Friday. On Saturday, Rula Habib would drop by with the writer, Photographer and the makeup and hair people from Les Femmes Tres Chic.

    Sunday would be the busiest day as we’d do the photo shoot and the interview for my favorite Fashion and Beauty Monthly Mag. Monday was the last holiday of the summer and my family would be using that as their getaway day for the very brief return trip to Chappaqua. 

    So, I wanted to make today very special for Judith and me. I began by putting together a tossed salad and a Peeled, Shellfish, casserole. I chilled a couple of bottles of white wine, rolled a joint of Hawaiian Marijuana and got out two Brandy glasses, along with a bottle of Peach Brandy. 

    As it got closer to 2 PM, I took the curlers from my hair, and put my tresses in a swirled upsweep, prior to doing my makeup. I pinned a pink bow in the back, to match as closely as possible, my pink and white, Baby-Doll, Bridal nightie. I set a Red, Floral Kimono by an easy chair in the living room.

    When I heard Judith’s car pulling up, around two-ish, I minced and sashayed to the door and opened it as I stepped back. Judith had her briefcase and handbag in her hands. I closed the door and took those from her smiling. Then I posed for her.

    “Oh my. Mummy is going to send her good girl out of town more frequently if this is how she meets Mummy when she gets back,” Judith insisted as she embraced me and French-Kissed me aggressively.

    “Wow, that was nice. Would you like me to undress you and have you sit in that easy chair and sip some Brandy and Smoke some Hawaiian weed?” I asked.

    “You do look amazingly Fuck-able right now honey. First, take my blouse and bra off, would you please? You know they call our Menstrual Cycles the Curse? Well, I think the real curse happened when some Swishy Clothes Designer invented the Brassiere,” Judith laughed.

    As Judith got ready to sit, I held the Red, Floral Kimono open for her. 

    “Where did you get this? It’s lovely,” Judith opined.

    “It’s a gift for you from Rula Habib. It’s from her collection,” I explained.

    “I’ve never seen that Baby Doll. I assume that’s from Rula?” Judith asked.

    “Could we possibly hold off on dinner? I really do want to take you, my love, this Brandy and this Weed, to my boudoir, where I want to screw your Sissy-Ass, completely Silly, girl,” Judith smiled.

    I laid on her bed, with my head tucked into her bosom, while we both sipped Brandy and toked on the weed. I knew when Judith stubbed out the joint and took my glass from me, that she was ready to fuck me.

    As we kissed and fondled each other’s tits, Judith teased me by saying, “You know, if you’d just screw up now and then, and be a bad girl for Mummy, I really could enjoy giving you a spanking. I want to Fuck your ass, Doggie style and hear you yip and yap occasionally. Just as if you are Mummy’s Pet, Sissy French Poodle.” 

    Judith had me kneel, on all fours. I’d already removed my rectal dilator. She took plenty of time lubricating me and her Strap-on, Faux Penis. As she slid the rubber cock into my ass, she said, “Once I start to screw you, I want you to bark like a little Sissy Doggy, Sylvia.”

    The rubberized cock felt so good in my ass, especially when it contacted my prostate. I could feel my own cock swelling slightly as Judith pumped into me and I pumped back at her. As I’d already been told, I began to let out little, sissified barks just as any tiny, Toy-Poodle might do. The shame and indignity of me acting as if I were Judith’s Little-Bitch-Dog actually turned me on even more than usual. 

    Just thinking about her “Threat” of spanking me if I was ever a “Bad-Girl” was strangely erotic to me. All at once, I could feel my “Clit” which had not spurted in quite some time, begin to spasm uncontrollably. My little barks turned to screams, as my passion went completely Over the Moon. 

    It was phenomenal. In the aftermath of my climax, as Judith held me, I was shaking and sobbing. When I finally stopped whimpering, Judith said, “Why don’t we just lay here and enjoy how we both feel? Then we can have a bite to eat. After that, we came come back her to my boudoir, and you can suck my pussy. Does that sound good to you Princess? Because I love the idea.”

    By then, I knew very well, that I would do whatever Judith suggested. I was her Good Girl. Even if I did want her to spank me and blister my ass pink.  

 Chapter VI: A Model Life

    I’d become quite jaded. As thrilled as my mother, sister and my sister’s partner were, about the photo shoot and the prospect of being primped and pampered, I truly took for granted being fussed over by hairdressers and cosmeticians. Mummy Vivian, My sister Elaine, and Elaine’s lover Jasmine, had arrived at 10 AM on a Friday morning, in time for the Brunch that I’d so very carefully prepared.

    “Judith, I’m just so very thrilled to meet you. And I’m simply ecstatic that my Little Girl Sylvia has found such a Strong, Well-Educated, Assertive, female Partner to look after her,” my mother, Vivian effused. 

    “Thank you Vivian. It has been a joy to be so deeply involved in cultivating your daughter’s, burgeoning femininity,” Judith added.

    “You know Sylvia. Had you come to Mummy and me, or had we discovered your desire to be a girl, we would have loved to assist you in that endeavor,” Elaine said, kissing me on both cheeks.

    “I just feel so fortunate that both of my daughters have found loving female partners. It comforts me knowing that neither of you will ever become involved with a Jackass such as your father,” my mother laughed. 

    Elaine’s partner Jasmine was just so very intriguing. She was a very Petite Eurasian, with a sleek and shiny, chin length Bob. She still spoke with a very slight, sexy accent. She had a sensuous way of curling up on Elaine’s lap, making it obvious as to who was the Domme Butch in their relationship. 

    On Saturday, Rula Habib arrived with the writer and interviewer from Les Femmes Tres Chic. Along with her were the photographers, the lighting crew and the Cosmeticians. Rula, along with the writer and the head photographer discussed the angles they would be looking for. 

    Sunday, after breakfast, the interview began with me sprawled out on a Divan, attired somewhat casually, wearing a Romper and Sandal-Strap heels, with my hair still up in rollers. In fact, Kaitlin, the writer asked the photographer to take a “Casual” shot or two, of me, with my hair still in curlers.

    “What is it like, being new to all of this? To be the Face, as well as the Focus, of Rula Habib Beauty and Fashion productions?” Kaitlin asked.

    “Oh wow. At the very start it was all just totally overwhelming,” I said.

    “Really? That isn’t what I see when I watch the Cosmetic and Perfume commercials. I don’t think the public sees that either? In fact I don’t pick up at that right now. You appear to be completely at ease with everything,” Kaitlin countered.

    “Well I took two Valium an hour ago. No, I’m just kidding. Honestly. With moving to Manhattan. Living with Ms. Habib. Taking lessons in Charm, Acting, Ballet and Public speaking. And then, prepping for the commercials, I was simply beside myself,” I explained.

    “But that was then. Now, I’ve adjusted. Truthfully I’ve began to enjoy it. I adore all of the attention. I love being the center of what’s going on,” I smiled.

    “Really? What do you enjoy the most?” Kaitlin asked, smiling and warming to my honesty and enthusiasm. 

    “Hmm? Food for thought. Isn’t it? Honestly, I’m just Over the Moon about the Primping and Pampering. At heart, I’m a real Prissy Missy. There are times when I can look into my compact and simply be obsessive over fixing my lipstick,” I said.

    “So I can’t help but adore being pampered by the makeup artists, the manicurists, the wardrobe people and the hairdressers. I just love it. At one juncture, I became so used to it, I’d get up in the morning and I’d look around for Damian my favorite hairstylist,” I laughed. 

    “I do hope we can cover this with you? I realize how personal this must be? You are a Transgender Spokesmodel. There are a number of Trans models in the fashion industry currently. There are also Trans Actresses in Hollywood as well as Trans Singers and Dancers in the entertainment industry,” Kaitlin paused. 

    “However, and I have researched this through several avenues, you are the very first Spokesmodel from the LGBTQ community. You are the Face, as well as the Voice of a major Beauty and Fashion Venture. Is their any pressure there, with you being such a groundbreaker?” Kaitlin asked.

    “No, not really? Should there be? Just as you said, there are plenty of other Trans-Ladies in Modeling, Acting and Entertainment. They really paved the way for me. On the other hand, Rula Habib is the person that took the real risk by looking around for a ‘Fresh Face’ and choosing me, to be that person,” I added.

    “Think about it. She’s launching a new company. A new brand. And she finds a Transitioning Female working behind a Perfume and Cosmetic counter and she rolls the dice and casts me as her Spokesperson. Rula is an amazing Lady and I truly look up to her and admire her,” I gushed.

    “In concert with your transition. How young were you when you decided you wanted to become a female?” Kaitlin asked.

    “Oh gosh. I struggled with it, fought it and hid it away for so, very  long. It wasn’t until my Partner, Judith took me under her wing, a little over two years ago that I began to Flower and Bloom. I’m twenty-five now, but I don’t regret my struggles with Gender Dysphoria. I’m glad things turned out the way they did. I cannot imagine what my life would be like, without Judith’s Love, Care and Encouragement,” I sighed.

    “Sylvia. That was perfect. I’m going to end things right there with that beautiful Soliloquy. Dear readers, meet Sylvia Cerise Conte,” Kaitlin closed.

    The remainder of the afternoon was taken up with various photos of me, hugging my sister and sitting in my mother’s lap. There were several staged poses with Judith. One with her taking the curlers out of my hair. The following morning my mother, sister and Jasmine drove back to Chappaqua. Prior to Rula departing, she gave me the dates for our European tour with three scheduled Fashion shows and a side trip to watch Elijah play tennis in London.

    The European tour would begin in less than a month, and I knew that now was the time to reveal to Judith my concerns over Elijah Habib’s flirtations towards me, as well as my sexual attraction to him.

    We were seated on the living room sofa when I began with, “Judith. I need to speak to you about something troubling, that I’ve been harboring within me.”

    “Well then Kitten. You need to lay your head in Mummy’s lap and tell  me everything. It’s our secrets that are the most dangerous to our emotional well-being. Oh, you have such pretty hair. Can Mummy play with your hair, Baby?” Judith asked in such a comforting manner.

    The entire time that I poured my heart and soul out to Judith, she smiled at me and played with my tresses. Whenever I closed my eyes, she’d whisper, “Look at Mummy, my pretty Princess. Mummy loves you.”

    When I was through with my entire discourse, or “Confession” as I then thought of it, Judith paused in thought.

    “Well, as interesting as that was, I see no problem with Elijah’s flirting, or your suppressed sexual sexual desires towards him,” Judith shrugged.

    “You don’t? I asked, perplexed.

    “No, of course not. Elijah is simply acting as a normal male, who has an attraction for a very gorgeous young lady. You are a girl Sylvia. And you? You have the normal heterosexual urges any female would have for any handsome, charming, masculine male. I mean I’ve taken a good look at Elijah Habib myself. And honey, I’m a dyed-in-the-wool Lesbian. But, I think he’s a Hunky Stud, girlfriend,” Judith exuded.

    “I love you Sylvia. And a portion of loving someone means that I should be willing to allow that person their freedom. I don’t want you suppressing your urges. I desire that you explore your sexuality, Baby. I realize you’ll be crossing paths with Elijah in London. If indeed, he makes his move, go with your urges. I know your heart belongs with me,” Judith said, confidently.

    “I’m simply flabbergasted Judith,” I sighed.

    “See what happens when you share your innermost self with someone who cares for you and loves you?” Judith asked.

    “You can discuss something like we just spoke about with a close friend such as my Admin, Allison,” Judith counseled me.

    “And more truthfully as to the point, Sylvia, you have never experienced a loving, healthy, sexual encounter with any male, have you? Of course you haven’t. When you pleasured Kathryn’s men, you were used as a Cum Receptacle, weren’t you? Then I would think it would be very apropos for you as to exploring that option? Don’t you think, dear?” Judith inquired.

    “And now, I believe I need to spank you. If for no other reason than to teach you to reach out when you are troubled. Just think about it. You’ve done this all of your life. You suppressed your femininity inside of you from both your mother and sister. And from Kathryn. Elaine and Vivian both said they’d have supported you,” Judith insisted.

   “Now go to your boudoir and return with a sturdy hairbrush and a bottle of Aloe Vera Gel. Now girl,” Judith said with a wave of her hand.

    When I returned she had me remove my slingback pumps, and my panties. Then she told me to kneel, bow my head and present her with the hairbrush held with both of my hands, as I said, “Mummy, please spank me. I need to be cleansed.”

    Judith lifted the hem of my romper and one of her hands roamed lovingly over my ass, as she said, “You know, girl, you have the most gorgeous ass. I love it and I love you so very much, I think from here on, you should receive a monthly maintenance spanking to keep you purged of any sort of harmful secrets.”

    “I’ll be giving you one dozen spanks with this hairbrush. Count each and every one. Then say, Thank you Mummy for making me so very self-aware,” Judith ordered. 

    By the 5th spank, I was screeching, and confusedly blubbering out my Mantra. At the very end I was shaking and slobbering. Then Judith put down the paddle and used some cooling Aloe Vera Gel to soothe my reddened ass. 

    "There, there now, Mummy’s Little Princess. Doesn’t my Sweet, Sissy Girly feel so much better now?” Judith asked. 

    “Oh yes Mummy, Ooh! Oh Mummy. Oh my!” I said as she rolled me onto my side and oiled-up my Clit. 

    I couldn’t restrain myself. I turned and sat up, wrapping my arms around Judith. I next began to kiss and lick her neck. I had not realized how slender and Sylph-Like I had become. Nor how sturdy a woman Judith truly was. Judith lifted me and had me wrap my slender, waxed legs around her waist. She then carried me bodily into her Boudoir and easily deposited my upon her bed. 

    “Keep those well-turned legs spread apart little girl. I want to rail your ass with my favorite strap-on,” Judith announced as she attached her faux penis to her body. 

    She used her fingers to lubricate my anus, with the Aloe Vera, Vitamin E Gel. Then she coated the Strap-on penis with the same type of lube. Judith slid me towards her, practically dragging me to the foot of the bed, to finally sit my thighs upon her hips. As she slid her rubber cock slowly inside of me, she said, “Now scissor your ankles together behind me.”

    We both began an in and out rocking motion. The faux penis was long but slender and easily slipped inside of me, unlike the fat cocks of both Carlos and Dylan. The length was virtually perfect for contacting my Prostate. Judith had very special, French Designed Strap-Ons, which included small, rubber nubs that came in contact with her clit to stimulate her, as her lover’s fingers might.

    So, as she buggered my anus, her faux cock would titillate her love  button. My prostate became sufficiently excited and I began to leak Sissy-Cream from my Sissy-clitoris. As Judith and I pumped more fervently into each other, Judith leaned over and pulled me to her and our breasts rubbed together.

    I was now hanging onto Judith, with my arms around her shoulders and panting like an excited puppy-dog. As my clit began to expel fluid,   I heard Judith gasp and shriek. 

    “More. More, pump harder. That’s it! Oh yes. Oh heavens, this is fabulous!” Judith screamed.

     She lowered me to the bed, as she pulled her rubber cock from my ass-pussy. She then laid beside me and kissed my face as I licked around her eyes and cheeks. I was sobbing right along with her as we embraced. 

    It was a fabulous way to consummate our love, and we would continue to satiate our sexual appetites until the morning that the Limo arrived to take me to LaGuardia to meet Rula for our flight to Paris. All I needed to take with me was a tiny carry-on, as all my clothing, shoes, cosmetics, hair care products jewelry, handbags and accessories would be packed and provided by Rula Habib Beauty and Fashion. 

    The day of the Fashion show I’d have a limited role as far as being a model was concerned. I sat comfortably back-stage as Damian readied me for my appearance. I’d be wearing a silver, off-the-shoulder, pencil gown, with tall heels, full evening makeup and a high-fashion updo. I was dripping with earrings, bracelets and a museum-piece necklace. 

    I stood in the wings of the stage holing Rula’s Hand, Damian looking me up and down, and confirming, “You look Sensational, Miss Conte.”

    A voice over the Public Address system announced, “Ladies and Gents, Miss Sylvia Conte.” 

    As I sashayed across the stage to the podium I was smiling with my hips swaying. I stood at the podium as the polite applause died down. Smiling once again, I spoke into the microphone. Behind me a large TV screen telecast in French, what I was saying. I looked to the teleprompter to recite my practiced speech.

    “Thank you everyone. As the announcer said, my name is Sylvia Conte. Some of you may know me as the Face or Spokesmodel for Rula Habib Cosmetics and Perfumes. Many of you are probably wondering, who in the world is she? That doesn’t matter,” I shrugged.

    “What does matter is that we have a fabulous show for you today introducing our Fall Fashions. Those fashions will be shown by a fabulous group of world class models. So please, sit back, relax, enjoy yourselves and also enjoy the world view of Ms. Rula Habib and her top designers as to where Ladies’ Fashions are going today. Once again, thank you for joining us,” I closed as I minced off the stage. 

    It was much the same in Rome, however there I also closed the show, by being the very last Model to walk the runway. In London it was very much the same. That evening, prior to dinner, Rula reminded me, “My brother is looking forward to seeing you after the tennis finals tomorrow.”

    “Well, of course I’ll be excited to see Elijah once again,” I agreed. 

    “He’d like us with him as soon after the matches as possible. He’d enjoy introducing us to the press,” Rula relented.

    “Of course, that would be great, Rula,” I again agreed.

    “And of course you’ll join us for dinner and a late night-cap,” Rula asked.

    “Yes. Of course I will. I’d love that,” I consented.

     I’d looked at my airline ticket and we wouldn’t be leaving until the middle of the week. I just might be testing the waters of my sexual attraction to Elijah Habib? 

    Elijah’s finals match was grueling. However he won out. There was the awards ceremony, where we sat directly behind the singles and doubles winners. After Elijah had showered, we met him where the press mobbed him.

    “Please. Please? Guys, girls, allow my Sister, Rula and her beautiful Spokesmodel, Sylvia to join me? Ladies, come on thru. Let the ladies thru guys. Sylvia you look fabulous as always. Oh Rula, always so lovely and my good-luck charm. Okay folks. Fire away. Fifteen minutes and we’re out of here for dinner,” Elijah announced.

    It was at Dinner, in a private dining room at our Luxurious London hotel that I realized that our suite of rooms, adjoined with Elijah’s. Was that on purpose, I’d wondered? 

    Throughout dinner, Rula, ever the adoring sister, praised Elijah’s tennis play during the finals match.

    The ever polite and modest Elijah agreed with her that it was a tough match and praised his opponent. Then turning and looking at me, Elijah asked Rula, “And how did our lovely Lady Sylvia perform during her first, real, public appearances?”

    “Oh Elijah she was fabulous. She was just so incredibly poised and graceful,” Rula stated.

    It was then that Elijah began his very obvious flirtations. He leaned over, placed his hand on my shoulder and kissed me on my face, very near to my pouty lips, saying, “I’m so very proud of you Sylvia.”

    Prior to dinner ever being over, Rula informed us, “I don’t know about anyone else, but I’m going to turn in soon.”

    “I’m still pumped from the match. Sylvia would you join me for a nightcap and some talk? Maybe we could listen to some Jazz?” Elijah asked.

    I quickly looked to Rula, who smiled coyly and nodded her head. 

    “Yes, I’d enjoy that Elijah. And I’m certainly not adverse to Jazz,” I consented.

    Elijah escorted me to his hotel suite, with his arm around my slim waist and his hand cupping my very pert, round ass. I enjoyed the way that made me feel, and I seductively leaned into his shoulder, and looked up into his eyes, adoringly as I  licked my Plum colored lips. 

    When we reached his hotel suite I stood primly with my clutch purse held in two hands in  front of me, at the level of my snugged, genitalia. My “Clit” and my two minuscule “Peanuts” in my testes sac where now so very tiny, that it only took a sanitary pad between my panties and my “Teeny-Peewee” to obscure the last physical vestiges of my boyishness. 

    “Why don’t you sit on that Mauve Sofa, Sylvia? What can I get you to drink, Love?” Elijah asked.

    “These suites are fully stocked. I thought I saw a flask of Courvoisier in our bar,” I said.

    “On the rocks, or neat? Neat? A Lady with perfect tastes,” smiled Elijah. 

    As he sat down next to me he handed me my drink. As he sipped his drink, he put his arm around me. This was no time for me to play coy, and I leaned over towards him and snuggled against him seductively and sighed sexily. 

    He held me even tighter and said, “I’ve thought about, and looked forward to, an intimate moment such as this, with you, ever since you stayed with Rula in Manhattan.”

    “As I have also Elijah. I think we should seal this moment with a kiss, don’t you darling?” I teased. 

    That’s all I needed to say, as he took my drink from me, set both drinks down and kissed me passionately. I was so very moved and excited. It was like a dream come true. He easily unbuttoned my Back-Button blouse and expertly unsnapped my brassiere. He was kissing and fondling my pert bosom and I was in 7th Heaven. I felt so honored and special.

    This sexy man, was an International Tennis Sensation. He was handsome, wealthy and athletic. His sister was a world famous model and business woman. She also had wealth along with her influence. Besides everything Elijah had going for himself, women also threw themselves at him, hoping he might influence his sister on their behalf.

     Elijah was a world class Playboy, sought out by aspiring models, actresses, singers. Ingenues and dancers. Among his conquests there was rumored to be Royalty. And here I was, in his arms, with my breasts bared, and ready to be bedded by him.

    “Elijah. I’d like to taste your penis, and feel it inside of me,” I panted as we came up for air.

    He literally lifted me like a bride being carried across the threshold, as he carried me into the bedroom. I easily divested myself of my bra and blouse. I unsnapped my slingback sandal pumps and slipped out of my confining pencil skirt. As soon as Elijah was nude, I slid off the bed and knelt at his feet.

    I very carefully licked all around his groin, his testes and his cock, prior to taking his lovely, rock hard penis into my mouth. I lovingly savored the manly taste of his erect member. When I thought he was ready I said, “Do you have any lubricant? If not, I’m still eager to feel your cock within me.”

    From a dresser drawer he removed a bottle of Aloe Vera, Vitamin E Gel. How so very wonderful and thoughtful of him. As he lubed my rectum and then his cock, I remained kneeling obediently on the bed, positioned “Doggy” style upon all fours. It was then Elijah told me how he would prefer me to position myself. 

    “Sylvia. Why don’t I sit on the bed, with you on my lap, facing away. You have such a lovely bosom. I’d enjoy playing with your ‘Girls’ while I screw you?” Elijah requested.

    “Oh of course darling. When we are like this, so intimately, my body belongs to you. Always,” I said, panting and breathless. I slowly lowered myself down, upon Elijah’s gorgeous cock. It fit so very well in my anus. It was as if I’d always been meant to fuck this man.

    And it was a lovely fuck. The excitement was infectious. I acted like such a slut as Elijah squeezed my tits and rammed his cock up my rectum. I began squealing as I bounced up and down, frenetically upon his blood engorged penis. As Elijah’s “Man-Meat” exploded with a fountain of ejaculate into my anal canal, I squeezed his member with my rectal muscles as if I had a Pussy.

    As I felt his erection subside and his Baby Batter leaked down my leg, I sobbed as would a Rescued Damsel. Elijah massaged my tits and kissed my neck. I finally stood up giggling, and reached out for him to hold me. As he took me into his arms, it was all I could do to take him to the bed, as my body had become so sylph-like and girlish. It was then I licked his face, his lips, and firmly kissed him as I extended my tongue deep within his mouth.

    We then laid side by side as we drifted off to sleep, deep within a carnal bliss. Before the sun even rose, I slowly came awake. I rolled over and held his sleeping body. Then I reached for his penis. It was erect. I then crawled under the covers and sucked him awake. I listened to his groans and sighs as I gave him a blowjob. And when he at last ejaculated his gobs of gooey sperm I swallowed every bit of it.

    He held me in his arms as I kissed all over his chest, and he said, “Last night. That was very special. When you said, your body belonged to me, whenever we engaged in any intimate moment.”

    “Yes I meant that. What I helpdback saying, as I wanted to live in that moment, was that my heart, wherever I am and no matter what I am doing, will always belong to Judith,” I paused.

    “I can accept that. Even as much as I know, if that were not true, I’d give anything to take you as my wife,” Elijah admitted.

    “Oh Elijah, I wish that were possible. But, you must have dozens of women that would give anything to be with you in a marriage?” I said.

    “Oh I don’t know if it is in the dozens? There are a few. But you were the very first I ever considered. I simply met you too late. Will you stay with me until your plane leaves for Manhattan?” he asked.

    “I’d love to. What will Rula think, though?” I asked.

    “At this moment, my sister could not be more thrilled,” Elijah said.

    “Well then, lets spend the day touring London like two lovers, and then we can spend the evening screwing,” I suggested. 

Denouement 

    The double wedding was small, intimate and unusual, to say the very least. Judith had prepared me for the ritualistic intricacies of a “Cassandra Coterie” wedding. I of course would be marrying Judith. My sister Elaine would be marrying her Eurasian Princess, Jasmine. Mummy Vivian and Allison, Judith’s Secretary, were to be the witnesses. 

    The only other person present would be the High Priestess Elena. The wedding was to take place at her estate in Chappaqua, in her ample Conservatory. The High Priestess would be conducting the ceremony.  When the festivities began, Jasmine and I were kneeling at the feet of Priestess Elena. Our heads were bowed. Our hands were clasped together, demurely. 

   Jasmine and I were dressed identically, wearing pink Cami dresses, with matching pink brassieres, three inch strappy high heels and pink, ruffled panties. Jasmine’s Tresses were fixed in a very short, severely undercut, cheek-length Bob. My inverted bob was styled in an asymmetrical pattern, with the increased length over the left side of my face.

    To my right stood my soon-to-be spouse, Judith. She was dressed gorgeously in a white linen suit with matching three-inch pumps. Her hair, just as my Sister Elaine’s, was done up in a high-fashion, swirled Updo. My sister Elaine was to Jasmine’s left, attired identically as Judith was.

    The Priestess stood in front of us, in her majestic robes. Mummy Vivian was behind me holding a birch, spanking paddle. Allison was behind Jasmine with a similar implement of punishment. The Priestess Elena began speaking.

    “Do you, Jasmine and Sylvia, vow to adore, honor and obey Elaine and Judith? Do you promise to devote your lives slavishly to them, as well as give them ownership of your very bodies?” Elena asked.

    “Yes we do, Honored Cassandra Priestess,” we said in unison. 

    “Very well. We’ll see won’t we girls?” Esteemed Sisters, Judith and Elaine. Do you intend to protect and guide both Jasmine and Sylvia, as if they were children? And do you you believe it is your duty to Discipline them promptly and severely for any and all infractions?” Elena again asked. 

    “Yes we do Madame Priestess,” Judith and Elaine answered.

    “Excellent. Then with the power vested in me, by the State of New York, and the Cassandra Sisterhood and Coterie, I pronounce the four of you, Owners and Wives. Will the attendants provide the Owners with the birch paddles? You girls, should lower your heads and place your faces in the pillows provided,” Elena announced.

    “Ladies, raise the hems of their dresses, and lower their panties. At my signal begin spanking your girls. Give them six strokes on each of their ass cheeks. Hail Cassandra, Hail Aphrodite, Hail the Sisterhood!,” Elena exclaimed. 

    By the third stroke of the paddle, I heard Jasmine begin to whimper.  By number six, we were both sobbing. By number 12, I was shaking, and I was certain that Jasmine was also. As soon as the spanking subsided, Elena spoke. 

    “Girls, compose yourselves. You may rise young ladies. Very good. Sisters, you may embrace and kiss your brides,” Elena announced.

    Judith held my shaking and shivering body in her arms. She licked the tears from my face and then kissed me passionately. As she held me at an arms length, smiling, I could see my sister attempting to calm the very frightened Miss Jasmine. 

    Later, we followed Madame Elena into her Great Room, where her effeminate Sissy Maid, Candace, helped serve a lovely brunch. Also present was Madame Elena’s Young, Boy-Toy, Stud, Mario. I am certain Elena enjoyed some real bedtime fun with Mario.

    However, considering Elena was older than Mummy, I had to believe that Mario also was forced to plant his seeds in the rectum of Candace to keep himself occupied.

    It was on the drive back to White Plains that I asked, Judith, “Darling, would it be within the scope of our marriage for me to ask, what the Cassandra Coterie is?” 

   “Certainly Princess. Now that we are married you can. It’s a very special and select group of ladies in the Cassandra Sisterhood. The Sisterhood was founded around 1890 by Cassandra Winthrop and a group of her Sorority Sisters at a College in England. Cassandra won a court case against a male who had left her at the altar. He was sentence to become her Sissy Maid for two years,” Judith began. 

    “At the end of the two years, Cassandra agreed to marry the Sissy Maid, but only if the Sissy would become her effeminate housewife. They had three children. All Girls. 30 years later, the oldest daughter, Camille, decided that the Sisterhood, needed to draw up a charter. It wasn’t yet worldwide but had spread from England to France, Canada and the US,” Judith went on. 

    “Camille was so driven to increase the influence of the Sisterhood, that she successfully organized a Census of the entire Sisterhood over those four countries. Upon the 100th anniversary of the formation of the Sisterhood, the financial arm, named the Winthrop  Foundation, decided to use that Charter and Census to give special membership to the descendants of the Charter members, and the Cassandra Coterie was born,” Judith explained. 

    “My great-grandmother, Lavinia Leonard was a charter member. I was a Junior at Wellesley when I was notified of my membership in the Coterie,” Judith said proudly.

    “Wait. You went to Wellesley, just as Kathryn, my mother and Kathryn’s mother did?” I asked.

    “Why yes? I never told you that, Princess? I thought you knew?” Judith remarked.

    “No I didn’t. Then did you know my mother?” I asked.

    “Not very well,” Judith shrugged.

    “Is she a member of the Sisterhood? And what about my Sister Elaine?” I asked.

    “Your mother joined, after her divorce, she told me. Elaine only joined recently. I’ve been a member since my Freshman year at Wellesley,” Judith smiled.

    When we arrived home, Judith patted my ass and asked me,” Do you still sting from your paddling, Sissy?”

    “Yes,” I said.

     “That’s too bad as there are things I must discuss with you. You know, it’s getting near the time that you should be having those little peanuts that are between your legs, clipped off,’ Judith surmised.

    “You want me to become a Gelding?” I asked.

    “Only until you become a girl,” Judith added.

    “We’re married now, and you knew when we did marry, I’d be calling the shots. Let me know when you want me to make the appointment with Jessica Trent. Did you know that they offer a pre-op final ejaculation, with every procedure?” Judith asked. 

    “That’s very thoughtful of them. Can you make it two weeks from today?” I asked 

    “Of course I can, Precious,” Judith winked.

    I took a valium on the drive to the clinic. I was in pre-op, with a drip feed of Anesthesia attached to an IV when Doctor Trent came in smiling. 

    “Hello, Sylvia. You’ll be out cold when we snip you. I’ll be freezing your little testes as Judith wants those made into a set of teardrop shaped earrings for you. I’ll be leaving just as soon as my Tech, Bambi gets here to do your ejaculation procedure. Here she is. Don’t you look lovely today Bambi? Well, I’ll leave you two alone, so as you can become much better reacquainted,” said Doctor Trent, closing the curtain for privacy. 

    Bambi looked absolutely glamorous. She wore her Jet-Black hair in a chin-length, curled, wavy bob, and her lips were coated with really bold, crimson lipstick. In her ears were one set of Large, gypsy hoops and another of dangling, zirconium pendants. Her tall, high heels clicked on the tiled floor, and she wiggled seductively in her beige, form-fitting, sweater dress. 

    “Hello darling, it’s always awesome to see you girl. So, we’re getting ourselves fixed, today are we? Honey, I had this done over three years ago. Doctor Trent did it for me. I’m her housekeeper you know? I’ve never felt better, sweetheart. You know, too very much testosterone makes girls like us just go simply crazy,” Bambi lisped. As she flopped both her wrists dramatically, for emphasis.

    “Now where is that tiny little thing? Here it is. Mine was small like this about the time I had my nuts sliced off. Don’t tell anyone but my new boyfriend, Emilio has the largest cock I have ever seen, girlfriend.  And he tells me all of the time that I give the best blowjobs he’s ever experienced,” Bambi giggled as she took my penis into her mouth.

    Even with the valium and the dope that was dripping into my veins, Bambi’s wet, painted lips surrounding my cock, felt so warm and special. Almost like a Pussy. Dreamily I closed my eyes. I was going to have my very own Pussy in a few months, I was thinking. Then, I got this little, cool rush and my body tingled as my sissy-cream seeped from my tiny cock. It was all over that fast. My final ejaculation.

    “Yum. You tasted so good Sylvia. You’re going to love being an Eunuch honey. I do so very much hope you decide to join the club and become one of us girls, soon, sweetie,” I heard Bambi whisper as I drifted off. Shortly after, they came and wheeled me into the surgery to snip away my tiny balls.

    Bambi was correct. I did enjoy the fact that my “T” level was now minimal. My thoughts seemed far more dreamy and less convoluted. I felt so much more femme and relaxed. A few months later, when Judith told me we needed to visit Doctor Trent to discuss my Gender Affirming Surgery, I just smiled and said, “Oh, thanks for making that appointment for me, Judith darling.”

    I took a couple of Valium the morning I checked in at the hospital. Judith was right there, holding my hand when I came too. She leaned over and whispered into my ear, “Jessica tells me she gave you just  the most delicious looking Pussy honey. Mummy can’t wait to lick it.”

    Throughout my recovery I made certain that I used the kit of larger and larger vaginal dilators as frequently as I could, to exercise and stretch my Brand New Pussy. 

    I was back to work as Judith’s receptionist at Bennington’s in about six weeks. It was shortly after my 1st weekend back to work that I received a call from Rula Habib. 

    “Hi Doll. I’ve spoken to Jessica Trent and she tells me you are cleared for travel, darling. Well, you know the Spring fashion lines will be ready to show soon. So, we’ll be doing a three week tour of shows throughout Europe and a few in the states. And I want you to do a some new commercials in Europe for perfumes and makeup, also,” Rula cooed.

    “Once again, you need not pack a thing. Everything you’ll wear will be from my collection. Now, Judith tells me she wants to come along this time. I can’t blame her one bit sweetie. You’ve had a lot of work done, baby. I have to go now. We’ll see you in New York at LaGuardia,” Rula closed. 

    I was excited about another European tour, especially when I realized it would be a sort of Honeymoon for Judith and me. We met Rula Habib at the concourse in LaGuardia. As we got closer I saw him. He was standing right next to Rula. It was Elijah Habib. 

    “Is Elijah coming to Europe with us? I asked.

    “Yes. Of course. Didn’t Rula mention that?” Judith asked.

    “No. Not a word,” I remarked.

    “I guess I should have told you. But I know how you just adore surprises. I’m doing this for Rula also. Just as much as I’m doing this for you, darling. Rula tells me it’s just so lonely for her on these tours. Being the CEO of a Beauty and Fashion house and sleeping all alone, not wanting the public to know she’s a Lesbian,” Judith began.

    “So I’m going along and playing the role of her social secretary and I’ll be keeping her company, sleeping with her in the same bed, every evening. Which means you and Elijah can share a bed in the other suite of rooms should you so choose to do so. Isn’t that nice Sylvia dear?” Judith asked as we arrived and Rula handed us our airline tickets.

    I gave Rula a hug and a kiss. Then I turned, half smiling towards Elijah. He pulled me to him and kissed me right on the lips. On the flight over, I relaxed. I was seated on the aisle in first class, next to Elijah. Across the aisle from us were Judith and Rula, chatting happily away. 

    At Heathrow, we took separate Taxis to the hotel. At the reception desk, the Concierge said, “Hello Mister Habib. It is always nice to see you sir. Let’s see. Suite 363. And this lovely lady must be your traveling companion, Ms. Sylvia Leonard? So nice to meet you ma’am. Your luggage is already in the room.”

    By this time, Elijah had one arm around me, with his hand resting on my ass cheek, wherever we went. As we walked into the room I offered, “Why not take a seat Elijah? I know where the bar is. I’m having a Peach Brandy. And you? The same, darling? Lovely.”

    As I sat next to Elijah on the sofa, I took a small drink from my glass, set it down and turned to him, asking, “So where’s my kiss before we jump into bed, lover?”

    “Oh yum-yum. Oh you big handsome hunk of man. You fucking kiss so wonderfully, don’t you? Wow, three weeks or more of sucking and fucking with you? I know by then my new pussy will be nicely broken in for Judith’s strap-on. Won’t it darling? I guess she planned it that way, didn’t she? The bitch.” I smiled.

    I took one more unladylike slug of Brandy, prior to getting on my knees, unzipping Elijah’s slacks, and putting his growing cock between my lips, saying, “Let the games begin, Big Boy.”

   “Remember now. My body is always yours, just as long as my heart belongs to Judith,” I whispered, as I took his hardened man-meat deep within my cheeks. It was like medium rare, Filet Mignon.....

     The End