A story of romance by Miss Priscilla Gay BouffantI was so fortunate to land such an exciting and high paying job for a famous Latina star. I had no idea how much it would change my romantic life and personal life. She knew what what she wanted to do to me.
Chapter I: Ms. Montenegro’s Office. Francois Speaking
However those events were usually blockbusters, such as the Super Bowl or a huge 4th of July special. She still could command starring female leading lady roles in films, as well. Plus her sensational figure, her glamorous looks and her voluminously curled and dyed, reddish blonde hair, belied the fact that she had a tall, handsome, twenty-seven year old son.
Her singing voice was still smooth and fabulous. Plus, this Half-Latina, Half-Anglo beauty could dance as well as most girls half her age. I’d always been a huge fan and I could barely contain my excitement.
“Francois Maurice Bronte? When I first saw your name I thought you were from France, but I see now you are French-Canadian from Quebec. Do you prefer to be called, Francois, Maurice, or something else?” Isabella asked.
“Francois is perfect, ma’am,” I answered.
“What really impresses me about your resume is that it appears you worked your way through Junior College and got your Associates in Business Administration while being employed as a hairdresser. That not only shows me you are not afraid of challenges, or work, it also makes it obvious you can be an added asset to me,” Isabella smiled.
“You see. I do have my own personal hairdresser, but it isn’t like she’s at my beck and call every moment. She has other important clients. So, should I need a touch up for a meeting, or an outing, you wouldn’t mind performing as my hair stylist also, would you?” Isabella asked.
“No, not at all ma’am. I’d be honored,” I nearly stammered.
“How about my makeup or manicures and pedicures? You’d enjoy helping me there?” Isabella asked.
“Oh yes ma’am. Absolutely,” I agreed.
“Well, you already know the salary and approximate hours. I’ll pay you well for any extra hours, above that. What I didn’t tell you is that the position comes with a Condo near my Laurel Canyon residence. You’ll be trained by my current Personal Assistant, Brianna, who is being promoted to become my Chief of Staff,” Isabella explained.
“Brianna has already moved from the condo to a guest house on my estate. I’d like to have you over for dinner soon, to meet my lovely, young, partner, Elaine Kaufman. I want you to feel like you are part of the family, Francois. If you don’t mind, of course? My son Alistair works here and still lives with me,” Isabella smiled.
“You’ll meet him today. Of course you’ll meet Brianna shortly. They will also be with us at dinner. It’s just something I do, to have everyone get to know each other better, away from the office. Oh, and you’ll be meeting my lovely Lady’s maid, Sondra. She’ll serve dinner of course. She’s from England. You’ll love her accent,” Isabella added, smiling.
Brianna, who I’d be replacing seemed very nice and efficient. Alistair Montenegro looked more like his divorced father, Primo Montenegro, a music producer, than he did his mother. Though I also saw the resemblance to Isabella. In any event Alistair was extremely fit, very masculine and quite handsome.
I truly felt like a Beta male in Alistair’s Alpha male presence. I bore a slender, runner’s frame, had nearly, shoulder length hair, and was just less than 5 feet, ten inches in height. That, coupled with very cute, girlish facial features, had sometimes prompted women to refer to me as “pretty.”
When we returned to Isabella’s office she said, “I told you I had a female partner. She really is a lovely, young, striking Jewess from New York. I consider myself bi-sexual, though I have preferred females as sexual partners for some time now. Are you gay, Francois?” Isabella asked, to my surprise.
“No ma’am,” I said quickly.
“It wouldn’t matter darling. By any chance do you crossdress? That wouldn’t matter either, of course. It’s just that you have a slightly effeminate bearing about you. As a dominant Lesbian, I find that sort of demeanor especially attractive in pretty, young males such as you are. Well, I want to offer you the job. It also comes with a grooming allowance for clothing and trips to the beauty salon. So, would you like to work for me?” Isabella asked.
“Yes, I would love to work for you, Ms. Montenegro,” I answered, smiling.
“Wonderful. I want to get you moved into the condo. If you have any sort of long term lease I’ll have my attorneys care for that. If you need to give a job notice anywhere I’ll understand. But if not, can you begin next Monday?” Isabella asked.
“Yes I can Ms. Montenegro,” I replied.
“Wonderful. Then how about dinner and drinks at six in the evening this coming Saturday? Business casual is fine. We can spend the rest of this week getting you into the condo. Oh, by the way Francois. Naturally my son calls me mother, but everyone else at the business refers to me as Isabella or at the very most, Ms. Isabella. Please, no more Ms. Montenegro if possible, Francois,” Isabella added.
The condo was unreal. So roomy and wonderfully furnished. Though, I would guess, from Brianna, very femininely appointed. I was surprised when Brianna coordinated with me the hours and dates I’d be moving, and she, Alistair and Sondra, the maid, showed up at my former apartment with a van to assist me with the move.
Brianna was very attractive. As I said, Alistair was quite handsome. But the English maid, Sondra was no less than stunning. The ladies took care of much of the light stuff. I’m certainly no weakling and still do a lot of running and swimming. However, whenever I went to lift something with Alistair, he appeared to act condescending about my strength compared to his.
I might also have been self-conscious by being in the shadow of his Alpha-male persona. Plus there was Isabella’s comments about my “effeminate bearing” to concern me. Then there was her inference that I might be gay or a crossdresser.
You see, I’d been raised since I was about ten in a household with four, domineering females. My father had absconded to Sweden with his bimbo, European girlfriend. When I’d reached my teens and began to act too much like a boy, my mother, aunt, grandmother and later my older sister had stepped in to “petticoat” me and “rein in my boyish spirits.”
The excuse was that they didn’t want me becoming like my father, of course. But I’d spent many evenings, weekends, holidays and even parts of several summers, dressed as a female and being taught to act like and emulate a girl. Not only had there been charm lessons, makeup tutorials and high-heel walking exercises, but many trips to the beauty salon, as well as occasional spankings and paddling’s when they thought I had been a “naughty girl.”
I was taught that bad boys and naughty girls were punished. Conversely, I was instructed that well-behaved young ladies were fawned over and treated like princesses. So, these days my clothing tended to be very masculine and rebellious.
I kept myself in shape, but could never seem to build muscle or gain weight. I kept my thick hair, long, to give myself a “devil-may-care” appearance. But I couldn’t seem to shake my naturally, “pretty” facial features. Though Alistair Montenegro didn’t treat me like one of the girls, he did often check to see if something was “too heavy” for me.
My aversion to being controlled by the women in my family led me to put myself thru two-years of business administration school at community college. During my “Petticoat Discipline” years I had intentionally been sent to beauty school. It was my Mother and Grandmother’s way of controlling me.
They believed, that with the average income of a hairdresser I’d always be somewhat, financially dependent upon them. So I intentionally enrolled in college, paid my own way, finally moved away, and refused any financial assistance from them, unless it was an absolute emergency. Even then, I insisted on paying them back.
Moving to the West Coast of the US and filing for citizenship was my attempt to break the apron strings. At twenty-three years old I’d been working as either an Administrative Assistant or Personal assistant, for nearly four years, at the time I went to work for Isabella Montenegro.
At the new condo, once I was moved in, Brianna suggested a shopping and grooming trip after my first week of work.
“Sondra, you’ll have to come with Francois and I to shop at Millicent’s Unisex shop and get Francois a complete, very hip chic-chic wardrobe. Plus he’ll need a makeover at Christine’s. You do know that Isabella gives all of us a very generous grooming and clothing allowance, don’t you, Francois?” Brianna asked.
“Yes, thank you. Does she prefer Millicent’s for clothing and Christine’s for hair?” I asked.
“Well she has accounts there, as well as other retailers, but yes, she’s fond of Millicent’s trendy androgynous apparel and loves the way Christine’s does makeovers to go with the attire,” Brianna added.
Before I could actually say I was a little leery over the terms, “makeover,” “unisex,” and “androgynous,” Alistair spoke up.
“Yes, mother would be very pleased if you became a regular at both those places, Francois. Brianna, why don’t I accompany you, also? I could give a more masculine perspective on what would look attractive on Francois. I could also help in making some suggestions on hairstyling and nails,” Alistair smiled, as he put a strong arm around my shoulder and hugged me playfully against him.
So, it was settled. Dinner at the Montenegro’s this Saturday evening. Then, after my first work week, a Saturday trip for a new wardrobe. Plus a complete “makeover” at a Beverly Hills beauty salon. I tried to look my manly best at dinner. I wanted to impress everyone, but especially the hot, English maid, Sondra.
Maybe Sondra and I could become an item? It was early autumn and still mild. I wore a white, linen shirt, a cream-colored, light, sports-coat, a tan pair of Dockers and a fawn colored pair of moccasin style shoes. My shirt was opened at the neck. My hair was tied back in a ponytail.
I was glad that the Macho-looking, Alpha-male, Alistair Montenegro also wore his hair long. I didn’t feel so insecurely effeminate and Beta around him. My heart skipped a beat when Sondra answered the door and led me to the Sun-deck for drinks.
I immediately said “Yes” to a glass of pink-chablis which Sondra also served to Isabella, Brianna and Elaine. Elaine was Ms. Isabella’s stunning, dark-haired, lesbian lover. Elaine made things very obvious, snuggling against Isabella on a chaise-lounge. Alistair walked in as I was being introduced to Elaine.
Then, the raven-haired Jewess, Elaine, remarked, “Oh my Isabella. You did picked a really pretty one to put on display as eye-candy this time didn’t you?”
“Elaine, you’re making the poor boy blush. Alistair, let Sondra know what you want to drink. Sondra, take Alistair’s drink order, please?” Isabella asked.
“Thank you mother. Sondra knows what I like. Don’t you kitten?” Alistair winked as he sat down across from the four of us who were sipping Pink Chablis.
“Yes sir I do Master Alistair. Your usual. Two fingers of Chivas Regal neat?” Sondra smiled coyly.
Oh no. Alistair had ordered a double, top-shelf, manly, Scotch Whiskey, while I sat with the ladies sipping a half-flute of Pink Chablis. Again, it was as if I was destined to be the eternal Beta-boy, basking in the manly glow of this masculine, Latino hunk.
Dinner was lovely and I made certain to ask for my steak, medium rare, with a glass of Glenlivet Scotch instead of California Red wine. It may have been a mistake when I did have a glass of red wine. Then, again, after dinner, I may have erred, when I drank a B&B. I was now tipsy and unable to drive.
Everyone insisted I stay overnight. When I protested that I didn’t bring any sleepwear, Isabella insisted that Sondra find me something to wear.
“Well I doubt he’ll fit into anything belonging to the very muscular Master Alistair. I should have something that isn’t too, too, extremely girly for him to wear, though,” pronounced Sondra.
“Come along Francois. I’ll also draw you a bath and mix up something to help your stomach in the morning and your head this evening. You can get out of those clothes and into the bath first. I’ll launder your clothing for you to wear home by tomorrow afternoon,” the bossy Sondra stated.
I watched as she walked in front of me, her sexy ass swaying, as she minced on tall heels. She wore, what to me, was the traditional fantasy costume of a French Maid. Her Sandy-blonde hair was pulled back away from her face and fastened behind her head with a butterfly barrette, pinned at the crown.
The remainder of her elaborately curled and sprayed hair bounced at her shoulders. I sat naked, on a chair, in the bath as the tub filled, before she handed me a woman’s, red velour robe. “Put it on sweetie,” she winked as I hesitated.
Then when the tub was full she helped me remove the robe and assisted me into the foamy bubbles, and began bathing me. She also had me drink something that she said would relax my stomach and fix any hangover.
“Don’t fret. The Mistress enjoys a party. By the Mistress, I am referring to Mistress Isabella, of course. She wants her employees to enjoy them selves. Getting a little tipsy is no big deal to her. She had a few herself,” Sondra assured me.
I became aroused as she bathed me but she paid no attention to my erect penis. Even as she toweled me off and put sandalwood bath powder on me she said nothing about my engorged cock. I wanted so badly to kiss her. But I had enough of my wits still about me, to realize that making a pass at her, might not be the best idea.
But when she sat me on the guest-bed and handed me a set of silvery, filmy, Harem Girl Pajamas, I balked. “I cannot wear those. These are much too feminine. Don’t you have anything in cotton or flannel?” I begged off.
“Don’t be ridiculous. Do I look like that sort of girl? Do you think I’m some kind of Butch-Lesbian? I would not be caught dead in cotton or flannel. I’m a girly girl,” Sondra insisted.
“In fact, The Mistress, Ms. Elaine, nor Ms. Brianna would ever think of wearing cotton or flannel sleepwear. And Master Alistair has nothing to fit you. You’re much too svelte and sylph-like. You’d look as ridiculous in his clothing as I would. Maybe even more so. Now put those on,” she ordered.
“So, you are going to make me entice you into wearing my things, girly-boy?” Sondra teased.
“I’m not a girly-boy,” I protested, having been called both a “girly boy” and “sissy boy” a number of times, especially by my older sister, Muriel.
“Oh no? We’ll see about that,” threatened Sondra, licking the tips of her fingers and encircling my swollen cock with her wet, right hand.
This sexily dressed, gorgeous, English maid began to stroke my erection and coo to me. “Well now. Is pretty Miss Francois going to behave for her ladies maid, and be a sexy Harem Girl for her? Maybe do a sexy dance for me?”
“Oh, Sondra that feels so nice,” I whimpered.
“Then you’d better put on the pretty pajamas for me, love. That is, if you want me to continue,” Sondra threatened.
“Oh gosh. Of course I will. That just feels wonderful and you are so beautiful, Sondra,” I gasped, slipping into the wide-legged bottoms and pulling the flouncy top over my wet hair.
“I thought I could change your mind. And you’ll wear these to breakfast along with your velour robe? As well as anything else I give you to wear until the clothes you removed are either brushed, washed, dried and pressed? Do you promise, Missy Francois?” Sondra asked as she climbed into bed with me.
“Yes. Yes of course Sondra. Anything for you. Oh I can’t believe you’re in bed with me. You are the hottest girl I’ve ever been with,” I gasped.
“How sweet of you to say so, Miss Francois. Now, let’s make love, shall we, my very pretty, sexy thing?” Sondra growled as she took me in her arms and brazenly French-Kissed me.
As we kissed, and I held her, she worked her hands into my pajama bottoms and fondled my cock and balls. Her kisses were taking my breath away. She smelled so lovely. Her lipstick was so wet. She was still fully dressed, but I could feel her lovely bosom pushing against me.
She’d kicked off her heels and clasped her legs around my waist. Visions of me entering her pussy with my penis, filled my head. Then she released her hold on my waist, stopped kissing me and pushed me onto my back. She pulled the pajama bottoms down to my knees.
Smiling she said, “We need to finish you off and put you to bed angel. I’m going to do my girly magic and suck you off, my sweet.”
Sondra then went down on me. She took my penis very easily and very skillfully into her mouth. Like nearly all, Beta-boy sissies I was never very large, even when erect. As Sondra sucked my cock she made noises to show that the act was very pleasurable to her.
I was enjoying it immensely and when she did break away to suck my balls intermittently I knew for certain I was not going to hold out for very long. With very efficient, if not professional guile, she gave me the most wonderful oral sex I could have imagined. As she blew me she looked up towards me with the most dreamy devilish look in her eyes.
Before I knew it I lost complete control and spurted wildly into her mouth. My ejaculation felt like a geyser exploding. Sondra appeared to gobble my sperm as I collapsed backward in ecstasy. Then she crawled on top of me, dry humping me wildly. She nuzzled against my face. Then as she kissed me I realized her mouth was still filled with my gooey load.
I tried to turn my head but she held me steadily while she dumped my messy discharge into my mouth. “It’s only fair, sissy-boy. I swallowed half. You must swallow the other half,” she insisted as she massaged my throat, forcing me to gulp down my own ejaculate. I was surprised it was only half. It seemed like it had to be all of it.
Then, she got up from the bed. “I must be going to bathe. I’ll be preparing and serving breakfast. Plus I have your laundry to do, as well as tennis dresses for the Mistress, Ms. Elaine and Ms. Brianna,” Sondra explained.
At breakfast I was happy to see that everyone was dressed very casually in sleepwear and robes. Of course, Alistair’s pajama’s were navy blue and far more manly than my girly Harem Pajamas. Not to mention his robe being more masculine that my red velour confection.
I nearly fainted when I returned to the guest bedroom to see the apparel Sondra had laid out for me to wear. “Is something troubling you, Miss Francois? I do hope you’re not going to tell me that the lovely things I laid out for you are too effeminate? Especially after you promised to wear what I would loan you? As I recall I sucked your cock to assure your cooperation,” Sondra said, entering the room from behind me.
“But the Capri slacks are pink. You don’t have any other color? And a crop top?” I asked.
“You ungrateful twit. No, I don’t have anything else. It’s Sunday, darling. I’m up to my ass in laundry from the work week. Now damn it. Unless you prefer that I tell the Mistress that you forced me to have oral sex with you, you’ll damn-well wear whatever it is I lay out for you. Do you hear me? Even if I hand you a fucking form-fitting, cocktail dress, you will wear what I say to wear. Now put those things on,” Sondra hissed in her charming, English accent.
I pulled the filmy satin panties up my hips. Then I slipped into the hot-pink, very snug Capri slacks. The white crop-top, with the very fussy, attached, furbelow shoulder-shrug came next. After I slipped on the ruffled anklet socks, I stepped into the patent leather, slip-on pumps with inch and a half kites heels.
“Very nicely done, Miss Francois. Would you like some lipstick?” Sondra teased as she kissed my mouth with her very wet, creamy, freshly applied, pink frost lipstick. I knew some transferred to my lips. She used her finger and laughingly redistributed it. Then she sent me downstairs.
I asked her to stop calling me “Miss” but she waved me off. Naturally, I would run into Alistair who was looking especially hunky in a muscle-shirt and wearing casual workout shorts.
“Well, hello Francois. Whoa. I really like the way those slacks fit you. Hold still. Oh yes. My goodness. With the right chemicals and proper workouts, you could have as nice an ass as Sondra does,” Alistair remarked flirtatiously.
I say flirtatiously, as while he said this, I stood stock still and he ran both his hands around my thighs, hips and butt cheeks, sensuously, in the same manner that any man would as he appraised his girlfriend’s figure. What bothered me the most was that I subconsciously felt flattered, and additionally experienced arousal in my groin.
When he ceased to rub my ass he turned me around smiling to face him and charmingly added, “You really look very nice this morning Francois. Let’s join the ladies, shall we?”
He looked down at me, deeply into my eyes. He must have stood about six feet, two inches in height. Even in the kitten heels I was at least three inches shorter. It was then I first noticed, the absolutely gorgeous and really dreamy, deep blue eyes he has. Those must have come from his mother’s Anglo side of the family.
Those eyes are really striking against his swarthy complexion and his thick, long, dark hair. He easily turned me back around and escorted me, with the palm of his hand pressed against the small of my back. He then complimented me on my “Very slim, trim, waistline,” as we walked together onto the vary large, garden patio at the south side of the Montenegro mansion.
Isabella Montenegro was seated at a patio table facing us and Elaine was lovingly massaging Isabella’s shoulders. Brianna was seated to Isabella’s right. When Brianna saw Alistair and I, she smiled knowingly with Isabella as they exchanged glances.
“Oh, what do we have here? Alistair, I must say that Francois looks absolutely lovely in the outfit that Sondra chose for him,” Elaine said, gushingly.
“Yes. Francois is assuredly a striking beauty,” Alistair added, smoothing my ponytail, which Sondra had tied atop my head. She’d brushed my hair after I’d dressed and she’d knotted the ponytail much higher upon my head than I’d ever normally wear it.
As Alistair ran his hand along my tresses, he stroked my back slowly, down my spine, sending shivers through me.
“Well, the two of you make a cute couple”, Brianna said smiling.
This was all very confusing to me, but I played along, also half-smiling. I nervously looked back at Alistair as I sat down. Before I could sit though, he held the chair for me. He was really treating me like a girl. His girl. Mentally, I was trying to shrug all of this off.
For a moment I told myself I was making too much of nothing. I was just being self-conscious around this very close-knit group of people who were simply trying to be very nice to me and welcome me to their home, their family, and their business.
I do know I was very glad when Sondra showed up to inform me my clothes were ready. I excused myself explaining I was going to be running along as I wanted to do some things around the new condo and prepare for my first day of work the following day. Alistair escorted me to the door.
“I really do believe it’s going to be very interesting working with you, Francois. I’m truly excited about this and looking forward to it,” Alistair said.
The following work week went along very smoothly, even when things got busy. “Isabella Production Management” not only took care of everything concerning Ms. Montenegro’s career, but also the careers of many up-and-coming entertainers she managed and produced. There seemed to be a common thread or two, with the acts she had in her stable.
They were all young females. They were also, already “out” or rumored to be members of the LBGT community. Apparently since Isabella had “come out” herself, she’d gotten involved in helping other lesbians and bi-sexual women.
It wasn’t until Friday that Brianna reminded me of our clothes shopping expedition and my salon makeover appointment scheduled for Saturday.
“You’ll need to meet us at Ms. Isabella’s residence at 8:30 AM sharp, Francois. We should be at Millicent’s for shopping by nine and will likely be there for two hours. We’ll get you fitted, purchase a week to ten days of apparel with outfit changes, and then proceed to the salon by noon for your makeover. There they will serve you lunch,” Brianna informed me.
“While you’re being dolled up we’ll be at your condo, boxing up your present wardrobe and putting your new items away in your closets and dressers. Let me explain something, carefully. If there is one thing Ms. Isabella is a stickler for, it’s having you wear the clothing we’ll purchase for you, when you are at the office. She won’t like seeing you attired in anything else,” Brianna explained.
“And that also goes for social occasions with her, as well. So it’s best for you to disregard your current wardrobe completely, for the time being. Another thing is the salon treatments. Whenever she has me schedule you for work to be done at the salon, you are to undergo any and all of the treatments she has me order for you. Understood, Francois?” Brianna asked.
“Oh yes. Of course, Ms. Brianna,” I answered politely.
“Once we box your present wardrobe we’ll store it in the condo attic,” Brianna explained.
As we traveled to Millicent’s Unisex Boutique, Brianna drove, with the very attractive, talkative maid, Sondra in the passenger seat. Alistair and I sat in the rear seat. During the week, Alistair had been pleasant and businesslike at the office. I was now relaxing more about the perceived, affectionate flirtations he’d made towards me.
I was certain now I’d self-consciously imagined he’d been coming on to me. Possibly that had been due to me having doubts about my own maleness due to the petticoat discipline I’d undergone in my teen years. If I had any doubts about being too effeminate, those perceptions would return at Millicent’s Unisex Boutique.
There didn’t seem to be anything very “Unisex” about Millicent’s shop. I could not imagine Alistair or any straight male shopping there. We walked past a large section of very feminine clothing that both Brianna and Sondra “completely adored” on our way to the “Androgyne” apparel.
Everything we passed was as fluttery and feminine as it could have possibly been. Though the “Unisex” clothing we were now viewing wasn’t quite as flouncy, it certainly didn’t appear to be anything I’d normally purchase. However, according to Brianna, Millicent, Sondra and even Alistair, what we were now looking at was “all the rage” for any Chic-Chic, “Personal Assistant” in the entertainment industry,
Especially a Personal Assistant for a Queenly Fashionista such as Isabella Montenegro. Friday, Brianna had gone over my hours with me for what she was sending to payroll. It would be another week before I’d be getting my first two-weeks pay, direct deposited.
When I looked at the money numbers, and thought of my rent-free condo and my other benefits, I realized I wasn’t going to find too many positions like this one. Thus, I now decided I might have to make a few allowances, adjustments and exceptions as to my wardrobe and possibly my grooming.
As Millicent and one of her girls took me to a fitting room, and had me strip to my underwear, Brianna, Sondra and even Alistair began to choose my new clothing line. Immediately, Millicent’s employee, an Australian girl name Matilda, pronounced my underwear “horridly drab.”
“Could someone possibly find Francois some colorful, satiny briefs please? Please hold still darling. Very nice. Only a 28-inch waist? Lovely. She has, I mean, he has a twenty-eight-inch waist,” she called out loudly, to no one in particular thru the fitting room’s curtained entrance.
Once I was dressed in an “outfit” it was time for me to “model” for the entire group. Matilda would parade me out to an area where everyone would be seated. I’d walk to the center of the group and then promenade back and forth in front of them.
Next, I’d be expected to mount a pedestal for further appraising. Comments would be made as to how the outfit “hung” and how well it fit me. After that, I’d descend the pedestal steps and be marched back to the fitting room. It was exhausting and I began to look forward to relaxing at the beauty salon. I had no idea then, how much of a girlish reaction that was. The clothing they picked out was all in bold colors and designs, as well as bright pastels.
Nearly everything fit snugly to my hips and buttocks. The “tops” were mostly all roomy and flowing. Though some tops were sleek, snug and form fitting. The pumps and half boots all had a heel of sorts. At least there weren’t any skirts or dresses. Not as of yet, anyway. But there were some Palazzo pants and suit “sets” that came with both slacks as well as matching shorts. None of the socks were what I considered “normal” length.
They were either anklets or “hosiery” that came to my knees. I wanted to draw the line with the Camisole tops that went with the suit-sets but then I thought of the concessions I’d decided to make for this very, lucrative position. Besides, none of these items were anywhere as terribly emasculating as the things I’d been made to wear as a teen, during my sissified “Petticoat” period.
One of the last outfits I tried on caused Alistair to make a real fuss over me. It was a suit set, done in a dark turquoise with a yellow camisole top. The slacks had a flared cuff. Underneath I wore a pair of white satiny underwear and some smoky gray, knee-high hose.
On my feet was a pair of cream-colored, leather half boots with narrow, Cuban heels. Brianna had undone the scrunchy holding my ponytail. Using a brush and some hairspray she had fashioned a hairstyle where the ends of my hair had been brushed forward to just touch my shoulders.
Matilda had accented the dark turquoise slacks with a beige, sash belt tied in a casual, uneven bow off to the right of the center, at my waist. Looking in the mirror all I could think of was how girly I really did look. I truly did feel self-conscious as I readied myself to model the outfit for Millicent, Brianna, Sondra and especially Alistair.
As Matilda propelled me from the fitting room, with her hand pressed against my ass-cheeks it was as if I went into a sort of time warp. I was again, at my Grandmother’s estate outside of Quebec. I was with my older sister, Muriel. We were leaving her bedroom where she’d just been drilling me in “skirt management” and high-heel walking.
My sister Muriel was now going to show me off to mother, grandmother and auntie. I was again, “Francine” and I wanted to save myself the indignity of a spanking and mince prettily so that the ladies would be pleased. As much as I’d would have liked to be taking normal strides from the fitting room into the space where Millicent, Brianna, Sondra and Alistair were seated, I could not.
As Sondra came into focus I came out of my momentary trance. However the steps I took were still precise, measured, and very nearly, dainty and mincing. The Cuban heels were slightly over two-inches high and a narrower more ladylike heel. So of course, I walked as carefully as I possibly could.
When my eyes locked with Alistair’s deep blue eyes, I blushed and looked downward shyly. It was about as girlish a thing as I could have possibly done. I felt pretty. I now realized, as I turned to walk to the pedestal and mount it, that I was holding my arms at my sides with my hands extended and my fingers spread.
It was the exact sort of delicate hand and arm position a young girl would assume while attempting to carefully and daintily balance herself when walking in her first pair of real high-heels. When I stepped to the top of the pedestal and “displayed” for everyone, I could hear Sondra say, in her most proper English accent, “So absolutely, lovely. Don’t you think, everyone?”
Millicent added, “You look perfect darling.”
“Sensational,” Brianna agreed.
“Francois, you have the bearing and the countenance of a runway fashion model. Please, you must wear that outfit to the salon,” Alistair added.
Alistair beckoned me to him and hugged me. He escorted me to a seat in the viewing area.
“Please sit with the rest of the ladies, Francois. Millicent, you know the correct sizes. Why don’t I pick out some more things that you can have delivered, while Francois rests. Now keep that outfit on and we’ll get to the salon shortly,” Alistair insisted.
While Alistair chose some more outfits for me, Sondra slid over and snuggled with me in the viewing area of Millicent’s clothing salon. She gave me a soft peck on my lips adding, “You’re such a lovely boy Francois. We need to get together soon and explore each other. Don’t you think love?"
Quite soon, I was at the beauty salon, and in the capable hands of Christine’s staff. Alistair, Brianna and Sondra had departed for my condo to put away my clothing purchases. They would also have lunch. At this point, I found out that I’d been scheduled for a leg, bikini, eyebrow and chest waxing, among the vast number of beauty treatments I was about to undergo.
Once I’d been waxed I was given a massage, manicure and pedicure. Thankfully a clear gloss polish was put on my nails. When I next looked in the mirror though, I saw that the arch of my brows gave me a “wide-eyed” almost surprised look. I was now fully dressed and ready for my cut, color, highlights and styling.
As Christine herself began my haircut her colorist was mixing my new shade. I hoped things wouldn’t turn out too, terribly, girly, but by now you would have thought I’d suspect otherwise. My worst fears were realized when Christine not only shaved my nape, but tapered my tresses into a really pronounced, inverted bob.
She combed my wet hair out to show me the style, but then assured me it would “Look, a lot prettier,” when it was colored, highlighted, set, styled, dried and sprayed. When the colorist began to paint in the dark brunette mixture, she let me know I would be served lunch once she foil wrapped me for highlighting. When she asked me, what type of wine I’d prefer, I automatically asked for Pink Chablis.
After the coloring was dry she foil wrapped me and they brought my seafood salad and wine. Once I’d eaten and had a second glass of Chablis my burgundy highlights were painted in and the infra-red color accelerator was turned on to dry my hair.
The two glasses of Chablis had relaxed me, and I had decided that as long as they didn’t make me too girly, and Sondra liked the way I looked, I would go with the flow. The experience at Millicent’s had passed and I felt that Alistair was just being nice and trying to make me feel good about myself when he fawned over me about the outfit I now wore.
Shortly after my color dried, Christine began to set my hair on large hot rollers. I sat in front of the vanity styling mirror looking like a fashion model being groomed, sans cosmetics of course. I felt a hand on my shoulder and realized it was Sondra.
“You look so cute with curlers in your hair,” Sondra smiled. She bussed my cheek and this time kissed my lips more firmly and with more promise.
“I’ve gotten a little extra time off today. I’ll be going back to your condo with you. We won’t be able to do everything as I’m in the midst of my Lady Moon. But you know how talented I can be. Plus I have a few real surprises for you, starting with, when I remove my skirt,” Sondra smiled.
It sounded to me as if Sondra was having her period and I wouldn’t be screwing her pussy, but I knew there was more we could do together. I could hardly wait. Christine then busied herself removing the hot rollers. With a teasing comb, brush and plenty of mousse and hairspray she gave me this truly voluminous pouffy “do” that made my inverted bob look like something a James Bond girl from the 1960’s might wear.
I’d worked or attended classes in salons from the time I was 15 until I received my Associates degree at 19. I was familiar with all the sights, sounds and scents concerned with beauty parlors. But I had not had my own hair colored or highlighted since I attended beauty school. I’d completely forgotten what it was like to leave the salon with the perfumed scent of hair coloring wafting around me.
The total girlishness of it was a bit much for me, but if Sondra “adored” it as she said, I was thrilled. Both Alistair and Brianna commented that my new “do” was lovely. Sondra was all over me in the rear seat of Brianna’s car on the way to the Montenegro estate. As she and I got into my new sports car, Sondra called out to Alistair.
“Master Alistair, sir. Please tell the Mistress that I’ll return this evening and I’m already well-prepared for the brunch she and Miss Elaine are having from 10 to 2, Sunday, sir,” Sondra added as Alistair bid us both adieu.
When we arrived at my condo the bossy Sondra insisted that I fix each of us a glass of Chablis. When I told her I’d pass as I already had two full glasses of Chablis at the salon, she said to me, “You’ll need another glass darling. Now do as I say, please?”
As we both casually sipped our wine, Sondra began to disrobe right there in the living room. She encouraged me to do the same. She removed her blouse and brassiere to reveal two, very nice, pointed, plump breasts. When she slid out of her skirt she revealed she was wearing a panty girdle.
Her stockings were attached to the girdle. She had kept her heels on. Then she turned and said, “Well here is your first surprise, lover.”
Her panty girdle obviously surrounded her crotch and her thighs. But in the rear it only covered half of her butt cheeks, fully exposing her rectum and making it very accessible.
“Miss Sondra is wearing the perfect panty girdle for a girl having her period. It holds her sanitary napkin firmly in place, but allows her sexy boyfriend full access to her ass-pussy,” Sondra teased as she wiggled her ass and shook her tits.
My mouth fell wide open.
“Oh for goodness sakes. Please don’t tell me you’ve never screwed a girl in the ass, before? Well, Dolly Boy, there’s always a first time. Come to my new boudoir please? Oh you didn’t think I had a boudoir here? Well I do. I spoke to the Mistress. When I have time off, I plan on coming here and being your housekeeper. Come along, I’ll show you,” Sondra added, further surprising me.
“Just another little surprise love. I’ve moved some clothing in. The Mistress gave me the gift of an old vanity she had. Here are my cosmetics. Now, if you expect to have any sort of sex with me, anal or otherwise, you’ll doll up for me, won’t you dear?” Sondra asked.
She wasn’t exaggerating. The dressers and closets in the spare bedroom were brimming with her skirts, dresses, lingerie, tall high-heels and blouses. The ornate, antique vanity was further stocked with stockings, cosmetics, hair care products, creams, lotions and scents. Nervously I fully disrobed while she handed me panties and a negligee.
Even while I dressed, stepping into some Marabou slippers, I intended to tell her of my aversion to being dressed in girly things. She pointed to the vanity bench. “Would you like to do your own makeup or shall I? I ask you as you did work as a cosmetologist, didn’t you?” Sondra asked.
I sat at the vanity facing the bed with my back to the vanity mirror. “Sondra. I have to tell you something. Could we slow down just a moment? Please?” I asked with seriousness.
“Well, of course, pet. Hmm? You seemed concerned. Please, proceed, my dear,” Sandra added, seating herself on the edge of the bed.
It took me several minutes. However, I gave her a synopsis of my teen years when I was raised under the strict, emasculating regimen of Petticoat Discipline. I sat quietly looking at her and then she smiled.
“Darling, you’re preaching to the choir. England, the country I was born in, very likely invented Petticoat Discipline. Though I know it’s practiced everywhere these days, to rein in unruly boys and errant spouses. You shouldn’t let it bother you though dear. It’s definitely not a stigma,” Sondra explained.
“Why, look at you. You’ve done quite well, haven’t you? You’re a very sweet, polite, well-behaved boy. You have a wonderful job. And there is nothing wrong with role-playing sexually, is there, darling? Now be a dear, and relax. Let Sondra prettify your face and we can make love. How does that sound angel,” Sondra asked.
“You mustn’t let something that happened a number of years ago, disturb you and keep you from having fun, my love. Agreed?” Sondra asked, opening a tube of foundation.
“I guess not? I’ve let it bother me since I was thirteen. I’ve made much too big a deal out of very little, haven’t I, Sondra?” I asked.
“Yes you have love. No hold very still darling, and let Sondra make you into a beauty. You’re going to make such a lovely girl, Francois. I knew it from the time I first laid eyes on you. What did they call you dear? When the ladies dressed you so pretty, I mean?” Sondra asked.
“Francine. They called me Francine,” I answered.
“No. That’s dull.You’re just so very exotic love. You are definitely a Francesca. With your dark eyes and that new, dark hair-color you could be Italian or Hispanic. It has to be Francesca. When I dress you as my girl, you are Francesca. Do you like that?” Sandra asked as she worked on my cheeks.
“Yes. It’s pretty. Yes, call me Francesca,” I agreed as she enhanced my brown eyes.
To this day, even after my hair is finally, “done,” I’m still thoroughly mesmerized by the magical qualities which are inherent in cosmetics. Yes, of course, there is still nothing like a dramatic, heavily-sprayed, “do” to make this pretty girl’s heart flutter. But with a dainty femme-girl, such as me, there is a certain excitement concerned with a well-done makeup application. To view the completion of my very own feminizing makeover can be so absolutely spell-binding.
The foundation and powder set the tone. The excitement of the blending of the blush and then the fulfillment of brilliant, vibrant, eye-makeup captivates me. And then to see the absolute sorcery of a lip-wand along with a tube of scented, moist lip-cream, makes me certain that shimmering, wet lipstick was the true gift from the Goddesses to all members of the female sex and to demure sissies as well.
The last thing Sondra did, prior to bedding me, was to affix a feminizing, white, girlish, hair-bow, to the top of my slightly bouffant “do” to complete my very, emasculating look. Sondra then, took me by one of my shaking hands and laid me upon the bed in the boudoir she’d recently laid claimed to.
The blending of our tasty, mingling lipsticks gave me a quietly, emasculating fulfillment, that I’d never dreamed I could possibly experience. It was as if, she and I, could kiss infinitely. Then as her hand went to my engorged penis, my prettified lips encircled one of her swelling nipples. She emitted the prettiest, most pleasant cooing sounds from deep within her.
As our erotic passions increased Sondra moistened her fingers to make my cock even wetter. Then, she gasped. “I want you inside my rectum, darling Francesca. I have some lube there on the vanity top. Excellent. Give that to me,” Sondra ordered.
She fixed my penis with plenty of lubricant. Then she put the applicator head of the lubricant tube up her anus and squeezed. Sondra had my lay on my back and then positioned herself over my penis. She slowly lowered her ass down over my cock. Soon, my penis was entering her rectum.
My genitalia is not exactly huge. However I was still very surprised at how easily my cock went sliding up inside Sondra’s rectum. She squealed as it slid home and then gasping, began to hump up and down as she encouraged me to screw her.
“Oh, so very good my lovely Francesca. Give me that hot cock. Shove it into my ass and fuck me honey. Oh, fuck me so good, precious,” she moaned.
Sondra was just so smoking hot. I was going to enjoy her coming in to keep house for me. I couldn’t wait to get a piece of her hot pussy. For now her ass was just perfect. I humped and pumped her until I couldn’t take it any longer. Then, emitting a whimper, I announced, “Oh Sondra, I’m going to climax!”
“Good, my little sissy-bitch. Get it all out. Fill-up my asshole with your seed, angel!” Sondra exclaimed.
I pumped out all of my sperm until I could no longer expel any. It was easily the strongest explosion I’d ever had. Sondra and I lay there, with me shaking, quivering and mewling in her arms. I’m not certain how long we did enjoy that post-coital bliss but it couldn’t last forever.
“Francesca my pet. I’m going to shower. You should do the same. Then you must transport me to the Montenegro estate,” Sondra explained.
On the way there, she gave me specific instructions on our relationship going forward. “I expect you to try on my things and practice with my makeup. Be a girl in private. I enjoy you that way. For me, as a committed bi-sexual, it’s really the only way I want to experience sex with a pretty boy such as you,” she explained.
That evening, I felt it wouldn’t hurt at all, if I took her up on her invitation and spent the night in one of her baby doll sets. I even touched up my recently waxed legs with a razor. I used a depilatory and moisturizer on the rest of my body.
After putting on some fresh lipstick I tucked myself into bed. I slept quite well. Just before the morning came, I awoke, sweating, from a dream. It was a very vivid apparition. I’d been at the Montenegro home. A very festive noisy party was in progress. I realized I was one of the guests of honor.
But, I didn’t look like me. No, I didn’t look at all like Francois. I wore a white, form fitting dress with a very snug, tight, hobbling hemline. I had on sheer hose. My nails were beautifully done in a crimson shade with white, French-manicured tips. They were elongated and very girlish. My white dress was decorated with pink polka-dots.
I stood daintily and prettily on tall, spike-heels. I was laughing and giggling excitedly with a group of other pretty females, and holding something upper them to gasp at. My haircut was a cute bob and even shorter than the recent bob I’d just been given. It was tightly permed and curled on top and the ends of the bob curled under.
My makeup was vivid and wonderfully enhancing. Creamy, Guerlain Plum, enhanced my lips. Then I realized I was holding a ring daintily in the air for my girlfriends to see. It was a diamond engagement ring, on the slender ring finger of my well-manicured left hand!
Walking towards me were Isabella Montenegro and her son, Alistair. As Isabella stood in front of me she grabbed both of my hands and hugged me to her. Then she released me from her embrace and held my hands delicately observing me smilingly at arms length.
“Oh Francesca my darling girl, I just know you’ll make the most perfectly obedient and subservient daughter-in-law for me, and a darlingly demure, submissive wife for my handsome son Alistair. Won’t you my angel?” Isabella asked.
“Oh yes, Mother Isabella. I’ll always do as both you and Alistair instruct me to,” I cloyed.
“ Well, I’ll leave you two lovebirds to yourselves,” laughed Isabella.
Alistair then took me into his strong arms and kissed my wet lips. His smoldering blue eyes drank of my captivating beauty as he smiled. He then put his head beside mine and whispered to me.
“Francesca my love. This evening, after everyone departs us, I will take you to my bed. There, you will take me into your mouth and moisten me. Then I will enter you and fill you with my hot ejaculate and make you my woman forever,” he promised.
“Oh yes Alistair. I want to be your woman always my love. Just tell me what you want of me and I will do it without question, my manly stud,” I gushed.
I awoke with a start from this unusually bizarre and inexplicable fantasy. I felt obviously disturbed and rightfully so. Shortly, I realized the baby-doll bottoms I’d worn to bed were stuck to me and soaked with the nocturnal emission from the wet dream I’d just awoken from.
On the drive to work I managed to suppress the memory of those haunting images. But by the time I’d returned home, those memories had returned. I just couldn’t dismiss from my mind the pictures of me as a giddy, fluttering, glamorously dressed and coiffed female, joyously celebrating her wedding engagement to her bosses son.
Of course I’d blamed it on the clothing I’d worn at bedtime and my my recent sexual escapade, while crossdressed with Sondra. But instead of ceasing my dress-up games, I immersed myself every evening in the further wearing of Sondra’s attire.
As Sondra could not presently find the time to drop by, we’d talk in the evenings, on our cell-phones, with me in full, feminine regalia, including girlishly coiffed tresses and make-up. I’d masturbate as she whispered sexual fantasies to me.
Then, at the office the next day, I’d again take on the role of Ms. Isabella’s personal assistant, hoping that soon my sex-life with Sondra would again resume. I wouldn’t have to wait very long for my sex-life to begin again.
Chapter II: Yes Master. Anything You Desire My Love
Approximately two weeks had gone by since my very unusual but stimulating dream. It was a Friday, after lunch. Ms. Isabella called me into her office. She was smiling.
“Sit down and relax Francois. I have a small favor to ask of you. Actually my son Alistair does, but he doesn’t want to impose on your free time for the weekend. You see he’s looking at some houses. He wants to purchase his own home,” Isabella explained.
“But he wants someone to go with him to offer a second opinion. I told him I would go, but what twenty-seven year old wants to house hunt with his mother? He really does value your opinion Francois. Would you have the time to accompany him, this Saturday, to view houses?” Isabella asked.
I was surprised, but I was also flattered. “Why of course I would,” I answered.
“Wonderful. One moment,” Isabella said as she speed-dialed her cell phone.
“Alistair, come into my office please,” she smiled.
When Alistair entered, Isabella said, “Alistair, Francois said he has the time to house hunt with you on Saturday and it’s no imposition on your part for him.”
“Oh thank you Francois. You’re certain it would not put a cramp in your schedule? Well wonderful. I’ll treat you to lunch. Is 9 AM too early to pick you up at your condo? Well great. It’s a date then. See you Saturday, Francois,” said Alistair excitedly.
When I dressed Saturday morning, I found myself subconsciously putting on the Turquoise suit-set that Alistair had found so attractive. Everything was identical to the way I was dressed at Millicent’s, right down to the cream-colored half boots, and the beige, belted sash at my waist. I even slept in curlers to give my hair a slight “lift.”
The smile on Alistair's face, as he surprised me, by holding the passenger side door of his Lexus, for me to be seated, told me I’d picked the right clothing. Alistair surprised me further as he leaned across me to fasten my seat belt. As he did so, he inadvertently brushed his cheek against mine.
He told me there were five houses to look at and we’d be meeting the realtor at the first home.
“I’m saving the best for last. It was Jasmine Laurent’s first purchase after her big film debut. From the photos it’s quite femininely appointed but it’s a gorgeous home and it can always be redecorated,” Alistair explained.
He was correct. When we finally arrived at the residence, it was easily the most impressive. It was also gaudily feminine, dripping in pastels, lace curtains, four poster bed-frames and plush, white carpeting. However, I liked it the most.
As we turned a corner, on our way to the fitness room and the indoor pool, Alistair stopped suddenly.
“Ah, here it is. When I saw the photos of this I thought of you Francois. Francois was a professional hairdresser, prior to becoming my mother’s personal assistant,” Alistair explained to Marta, the realtor.
“Francois. What do you think of this home salon? Isn’t it fantastic? I want your opinion as a professional as well as someone that appeared to enjoy their last pampering,” Alistair asked, coyly.
“I’m told Jasmine Laurent and her clique of lady friends used this space very liberally for Saturday morning coffee klatches,” Marta, the realtor explained.
The “space” was phenomenal. I could have gone into business with a very nice, small shop, considering the number of mirrored styling vanities, domed hair dryers and shampoo sinks available for use.
“Well, considering how glam, Jasmine Laurent usually appears, this isn’t a surprise. Yes, the layout is perfect, the decor is exciting, and the equipment as well as the furnishings are stylish and top shelf. It would be a lovely and very relaxing venue for a makeover,” I agreed.
“Yes, you’d have your own at home beauty retreat, wouldn’t you Francois?” Megan, the realtor agreed.
“Oh, excuse me. Am I being presumptuous? Are the two of you looking at the home together, as a couple, or is it just you that will be living here, Alistair?” Megan asked.
“At the moment it’s just me. However, I truly value Francois’s opinion. Yet, I’m not certain I’ll be comfortable in such a vast residence alone? So, if I were to consider a housemate, Francois would be first on my list,” Alistair explained, with a raised eyebrow, as he looked towards me.
As we drove to lunch, Alistair spoke to me about the possibility of us being housemates.
“Would you consider it, Francois? You wouldn’t just have your own room. We’d share the entire home together. And it would be no different than the arrangement you now have at the condo. It would be rent free,” Alistair said.
“I wouldn’t be imposing, would I?” I asked, considering the option. Though I wasn’t really keen on it. Not with arrangement I now had with Sondra.
“No, not at all. You’d be helping me. I’ve never lived by myself in such a huge house,” Alistair added.
As we walked into the restaurant, I told Alistair I would need time to think about it. What I didn’t tell him was that I now realized I’d have no place to play dress-up and be “Francesca” for Sondra.
Lunch was wonderful and Alistair encouraged me to have two glasses of wine instead of just one. He was holding off on a Scotch as he was driving. “I’ll wait until I return home,” he said.
When we pulled up in front of my condo he asked if I’d mind if he came in.
“Personally, what I’d love to do Francois, is discuss with you, in great detail, each of the homes we just toured. I want you to be open and honest, just as if you’d be living in each, and what you liked or didn’t like. It would really mean a lot to me Francois. Please?” Alistair asked.
“Well of course, Alistair. Again, I’m very flattered,” I said.
“Would you mind if I got some Scotch? And I want you to try some of this Cherry Brandy that Brianna left behind,” Alistair said, walking to the stocked liquor cabinet which I rarely used.
We sat at each end of the living room sofa. I noted the large snifter of Brandy was very flavorful, but seemed to have a real kick. It went right to my head. Before Alistair could say anything I interjected my opinion.
“Alistair, right now, of those five homes, the Jasmine Laurent residence is far and away the very best. I honestly wouldn’t consider buying any of the first four if it were me making the purchase. If the Laurent home isn’t what you are looking for then I’d say, look further,” I added.
“Really? You were that impressed? Interesting. Tell me more, if you care to?” Alistair said.
The two glasses of wine and now the Brandy had really loosened my tongue. I went into a detailed soliloquy detailing my full impression of Jasmine’s former home. I couldn’t restrain myself or hold back my excitement about the home hair salon either. I’d finished the first, sizable, snifter of Brandy which Alistair had poured for me. Without asking me, he poured me another, which I began to gulp instantly.
Alistair stared at me intently taking in every word I said. When I felt I’d exhausted my opinion of the home, I stopped speaking. It was then that Alistair set down his glass of Scotch. He stood up and walked to my end of the couch. He then took the glass of Brandy from my hand and set it down.
Taking me by the tips of my fingers he easily raised me to my feet. Then, wrapping his arms around me he kissed me deeply. It was not, a strong, forceful kiss. However, it was a sensuous, nearly smothering kiss that left me breathless. I will never say that I did not enjoy my first kiss with Alistair Montenegro. However, at the time, I felt it was wrong.
I thought it wrong to be kissing a man. I believed it was wrong that kissing this handsome man gave me chills. It was even further strange that I was becoming aroused by his kisses and his touch. I subtly broke away, holding him at arms length.
“Alistair. Why are you kissing me? I’m not gay, nor am I a female. Please Alistair. I don’t know what’s going on?” I shuddered.
“I’m kissing you, because I find you very sweet and pretty. I’m attracted to you. You don’t have to be gay or a female to enjoy that. This tells me there is something about me kissing you that you enjoy, Francois,” Alistair said, as he stroked his hand across my crotch. Through my slacks he touched my growing erection.
He kissed me again, very passionately. This time I reached my hands up to grab his shoulders and push him away from me. Instead, I placed my hands lightly and daintily upon his broad shoulders, as a girl would, who was fully enchanted with her man. He continued to kiss me and I was definitely returning the kiss.
As his tongue entered my mouth, my tongue met his and we intertwined. He was holding me at the waist. Then he disengaged the kiss once again and looked at me. He brushed the hair back away from my forehead.
“Alistair, I don’t know what to say, and I don’t know what is going on?” I explained.
“Then why don’t we go into your boudoir, take our clothes off and lay on the bed and explore?” Alistair asked as he propelled me toward the bedrooms. As we entered Sondra’s room, I told him we were in the wrong bedroom.
“No we are not. This is your room. It’s Francesca’s room. This was never intended to be anyone’s room but your’s, Francesca. These aren’t Sondra’s cosmetics nor are they her clothes. I purchased that clothing for you, at Millicent’s while you sat with the other ladies after you modeled.
“Brianna bought the cosmetics at Christine’s while you were being body-waxed. The ornate vanity belonged to my mother when she was a teenager. I’ve intended for you to be my girlfriend, Francesca, ever since the day I saw your profile photo at LinkedIn,” Alistair said to my amazement.
“You’ve tried on the attire haven’t you? Didn’t everything fit well? Sondra’s derriere is much plumper than your’s. Those skirts would look to be painted onto her ass. Though we could take care of plumping up your hips. Let me undress you Francesca?” Alistair said.
“No. I don’t want to be undressed by you. I don’t want to be your girl. This was all a ruse wasn’t it? Stop this, this instance,” I blubbered, still being held by Alistair and sobbing into his chest, my arms now around his waist.
I was so inebriated, emotional and very confused. On one hand I was smitten with this handsome man’s romantic intentions. On the other side of it, I feared the amorous feelings I had for him.
“I never, ever wanted to be a girl,” I protested futilely, as Alistair sat me on the bed, and began undressing me. Once I was naked and he was divested of his clothing, he used a Kleenex to wipe away my tears. Then he laid down beside me and put some lubricant on his fingers and touched my penis lovingly.
Then he kissed me again. By then, he’d lubed my fingers and pushed my hand towards his penis. At first I pulled my hand away. But as he fondled my cock, kissed me, and my organ became erect, I began to stimulate him and kiss him back more fervently.
When we were both rock hard, he took my penis in his mouth and began to suck me. As I became more aroused, he maneuvered us into a “sixty-nine” position. At first I hesitated, but finally I took his cock into my mouth and sucked it willingly.
“I think it would be too soon to enter your rectum with my cock, Francesca, my love. You would need to be properly stretched for that,” he explained.
Since those moments I’ve never stopped enjoying him, calling me “Francesca”. When he sensed that we were both nearing an orgasm, he then positioned himself so that we were once again face to face and lovingly engaged in the mutual masturbation of each other.
It was just so perfect, to alternate between looking into his eyes and kissing him romantically. We masturbated each other, until we finally both reached a near simultaneous climax. It was a shuddering ejaculation. I was shaken to the roots of my recently colored tresses.
Spurt after spurt squirted from my penis. When Alistair, who was softly kissing my lips, smiled at me saying, “Oh my pretty Francesca,” I received chills to my toes. Once our climaxes were complete, I couldn’t believe the way I felt. I sensed closure, somehow.
I had experienced completeness, as well as satisfaction. Something was different. I traced circles on Alistair’s face as he played with my hair. I finally spoke to him.
“Do you really want me for a girlfriend? Do you really think I’m pretty enough to be a girl?” I asked.
“Oh yes. You are lovely. With lessons and practice, you can be no less than stunningly beautiful,” he answered.
“Would you want me to dress up as your girlfriend all of the time?” I inquired further.
“Yes I would love that, Francesca. That would be ideal. I desire for you to move in with me, live with me, and appear even publicly, as a female. If you want it, the Jasmine Laurent mansion is yours. It will be ours. I will take you places as Francesca. To dinner. To my country club. I will introduce you as my date, as my girlfriend,” he intoned.
“You will be Miss Francesca Monet Bronte,” Alistair added.
“Francesca Monet? You already have a middle name for me? You’ve thought this out well, haven’t you?” I asked, wide-eyed.
“Well yes. Do you like the name?” he asked, blushing.
“Well yes, it is a pretty name. It’s also very sexy and it stays with my same initials. But you’ve put some thought into this and made some effort. Even though I should be somewhat disturbed over the obvious ploy and the stratagem. I’m actually flattered that you would take such pains to see to it that I was immersed in this,” I laughed.
“It’s all so cute,” I said teasingly and girlishly as I kissed him.
“What if I don’t want to be your girlfriend full time or I can’t pull it off?” I asked.
"I’ll take whatever you’ll give me of yourself. I’m very smitten with you. However, have no fear of pulling it off. You are a sensational beauty and you’re soft and delicate. We’ll hire you the best possible female acting coach on the West Coast to tutor you. She’s worked to fine-tune, numerous Transgender Actresses and Models,” Alistair explained.
“She’ll teach you everything there is to know about being a glamorous female down to the nuances of a sultry voice. Your own family wouldn’t recognize you after she’s schooled you,” Alistair declared.
“We’ll also go at as slow a pace as you prefer. You’ll have at your disposal the finest clothiers, the best cosmetologists and anything else you desire or require. Please say yes? Say yes for me, for you, for us. I adore you so much Francesca,” Alistair declared.
“By ‘we’ I am assuming you also mean your mother? Possibly Brianna and obviously Sondra? I also believe the Modiste and the Salon would be involved. I would guess Elaine would know?” I asked.
“Yes. Everyone you’ve mentioned,” Alistair agreed.
“You cannot imagine how intrigued I am. To think that, from one, on-line, profile photo for a Personal assistant or Administrative aide, that something like this grew? It’s taken on a life all its own. I’m truly complimented Alistair,” I agreed.
“Yes, it began with the photo, but the more I have been around you and gotten to know you, my attraction for you has grown, darling. You cannot imagine,” Alistair added.
“I have no issue with posing as a female on a 24/7 basis. But at present I’m not comfortable with taking any figure changing medication. As for any permanent change, I have a true aversion to anything, such as that,” I stated.
“I would never dream of you doing anything you did not want to do, Francesca. And going slowly is preferable to anything else to me,” Alistair said sincerely.
“One last thing. You said, for me to be able to experience being penetrated rectally by you, I would have to be stretched? Is that how you put it?” I asked.
“Well yes. That’s correct. For you to enjoy it, and for it to be comfortable, there is a method used by females as well as males, that gradually expands that opening. Sondra will be a much bigger asset to you for that,” Alistair said.
“Yes, Sondra. And why, pray tell would she be any sort of expert there, Alistair?” I asked.
“Because she is a transgendered female,” Alistair explained.
Now that floored me! Sondra? I could not imagine that?
“Sondra is not a true female? Impossible! Why she’s one of the most attractive females I’ve ever met. And you tell me she’s a boy?” I asked, alarmed.
“Yes, it’s true. When I met Sondra, I didn’t believe it either. But now you can see the possibilities. Of course Sondra has had her breasts done. But between her thighs she’s nearly as male as you, Francesca,” Alistair informed me.
“I do hope you’re not too angry with me, Francesca. I’ll understand, though, if you are,” Alistair again spoke, sincerely.
“I should be, but I’m not, really. It’s somehow comforting that someone so charming and so manly, finds me attractive from a feminine standpoint. It’s actually a relief. I’ve struggled with my masculinity for so long,” I explained.
“Maybe I’ve needed to come out and couldn’t come to grips with it? Well, I will give it an effort, love,” I said as I kissed him.
I looked deeply into those striking blue orbs and asked, “But why you darling? You, of all people? You’re so very affluent and so strikingly handsome and mannish. Alistair, you could have any true female you desire. I’ve seen photos and news clips of you with some of the most striking beauties anywhere?” I said, with intrigue.
“It would be too lengthy to explain, though it’s as simple as stating, that someone like you is who I prefer. I don’t like the gold-diggers. I don’t like the spoiled, pampered bitches. I want someone who appreciates being spoiled and pampered without coveting it,” Alistair tried to explain.
“What’s next darling?” I asked. We were now standing and I put my arms around him and rubbed my naked frame against his. What turned out to be next, was more lovemaking. This time I requested he at least attempt to enter me from behind. It had seemed so easy when I entered Sondra?
With much lubrication and effort, we managed to work about a third of his erect penis into my anus.
“I don’t want to force this, love. When we do it I want it to be as smooth and enjoyable as possible for you. I don’t want to force anything,” Alistair said, compassionately.
By the time he’d departed, we’d both showered. I’d then dressed in some pretty slacks, a tube top and kitten heels. I’d put on makeup and brushed my hair. Sondra called me prior to bedtime to make a date to drop by Sunday morning to assist me further with my impending transformation. Brianna would be calling me every evening prior to a workday with instructions on apparel and appearance at the office.
My “transition” was to be accomplished at a reasonable but evident pace. When I spoke to Sondra, she immediately asked, “Are you upset with me, Francesca?”
“No, but I certainly should be. You do have some explaining to do, though. You know that, don’t you?” I asked.
When Sondra arrived Sunday morning, she gave me a warm hug and a very sexy kiss. That did go a very long way to smoothing things over. Then we sat. She had black coffee and I sipped Chamomile tea. Yes, it did dawn on me, as to how much of a sissyish thing, drinking Chamomile tea was.
“I do understand that you’re likely upset. I know that the entire time we were having sex, you thought I was a woman sucking your cock as well as taking the same cock into my ass. But please understand Francesca, that as I am another sissy, just as you are a sissy, I am also very attracted to you. I was’t faking my sexual and amorous feelings for you,” Sondra stated.
“Yes. But you do it so well. Being a girl, I mean. I still cannot believe it. How long have you been Sondra?” I asked incredulously.
“It’s been over four years, full-time as a female. Somewhat more since I began crossdressing part-time. Which only should tell you, that with your background and your feminine bearing and countenance, you will be strikingly beautiful and delightfully girlish, even before you are a finished project,” Sondra added complimenting me.
“I was married to Elaine. We met in New York at acting classes. Her parents were holding back her trust fund because she wasn’t married and they suspected she was a lesbian. It was a marriage of convenience. The pre-nuptial stated I would get a nice chunk of money in case of a divorce,” Sondra explained.
“That was my payment for marrying her and helping her to get her hands on her inheritance and trust fund. Almost right away Elaine told me that the only way she could have sex with me, was if I dressed and acted as a female. You’ve seen Elaine. She’s a striking beauty. I couldn’t help myself. We were house-sitting in Scarsdale. The house belonged to rich friends of her’s that were summering in Europe,” Sondra went on.
“She gave me the name Sondra from a former lover that had moved on. Her parents thought we’d bought the house. It got so that the only time I wasn’t Sondra was when I was out of the house or when her parents visited,” Sondra smiled.
“Two weeks prior to her friend’s return from Europe, we packed our things into Elaine’s SUV and drove to Southern California. Elaine is very resourceful. She already had a house rented and a plan. She would continue to pursue her career as an actress. If I wanted to stay in the relationship, I would need to be Sondra 24/7.” Sondra shrugged.
“By then I had no problem with that. I still adore Elaine. She got some bit parts and some as an extra. She took time to school me in femininity. Then she got the chance to read for a minor part in a film with Isabella Montenegro as the leading lady,” Sondra said, with excitement.
“Elaine’s agent was a long-time friend of Mistress Isabella’s. She knew very well of Elaine’s sexuality. She also knew of Mistress Isabella’s burgeoning Lesbianism since her divorce. The agent had a lunch date with Isabella prior to the reading,” Sondra explained.
“She told the Mistress all about Elaine and even showed her photos. Elaine got the part. She and Isabella Montenegro walked the red carpet arm-in-arm at the premiere. Once they began to live together I was heartsick. When Elaine asked for a divorce I begged her to let me live with them as their maid. Mistress Isabella actually thought that having their very own sissy maid would be ‘cute’ according to Elaine,” shrugged Sondra.
“The Mistress insisted I play the role perfectly and arranged tutoring with Helena Ferraro. Helena has schooled nearly every big name transgender female in modeling, stage and screen. She really did polish me. I had no idea what it really took to be a female,” Sondra added.
“She may be the woman Alistair mentioned hiring as my tutor?” I replied.
“You can bet she is. Mistress Isabella will want her son’s paramour to be feminine perfection personified. Only the very best for the Mistress. Well, I am supposed to teach you about rectal dilators this morning,” Sondra replied.
“Yes. I also have some questions on hormones and implants. Just in case, of course,” I smiled.
“Yes, of course. Just in case. Well, let’s get you an enema, a rinse, and a douche. Everything we need is in your new boudoir. The Francesca Monet boudoir,” Sondra said as she led the way.
Sondra showed me how to give myself an enema. She hooked the one-quart bag to one of the bed-posts. She’d filled the bag with warm soapy water. She showed me how to insert the lubricated nozzle in my anus. Next I was taught how to slowly release the fluid by using the hose clamp.
I thought I would burst as the contents of the enema entered me. I was doubled over gasping for several minutes when Sondra finally allowed me to use the bidet to purge myself of the soapy contents. I felt so helpless and submissive.
After a similar but less lengthy experience with a fresh water rinse, I was shown how to give myself a scented, flavored, refreshing, rectal douche.
“Are you serious. Scented and flavored?” I asked.
“Just in case, I guess. It isn’t like I expect Alistair to sniff or to lick your ass, but you never know? I know he never did that with me,” Sondra said, before she realized she’d mentioned the wrong thing.
“Excuse me?” I asked. I was already acting like a jealous girlfriend but I couldn’t help myself.
“Please. Don’t become envious, Francesca. It was nothing. Alistair has always had a penchant for demure sissy-boy/girls. Our outright subservience and neediness, intrigues him. When I first moved in, to become the sissy-maid, he had a thing for me. And he has had other sissies. But I can tell from the way he acts about you, that you are it for him,” Sondra said, as I pouted.
“I mean that, girl. You are who he’s been looking for, for a long time. He’s very excited about you. You’ll be seeing that soon enough. Now that you are clean why don’t we fit you for the smallest size plug. Up on the bed with your ass up in the air. Just as if Alistair was going to screw you,” Sondra ordered.
“There are other ways for us to get screwed but this is the most common. I’m certain Alistair will begin to experiment with you as soon as we get you loosened up. Now, put this gel applicator up inside you and give it a squeeze. Then coat the plug. This is a size-one plug. There are six in this kit. Each is progressively larger and longer,” Sondra explained.
“Some women use these after a surgery that tightens up their pussy. Trans-girls that have surgically constructed pussies also use these. In most of these cases they exercise their pussies for minutes at a time. We sissies keep these in our ass for as long as we can stand it during the day, so we can stay sufficiently stretched for anal sex,” Sondra explained.
“Now that you are lubed and the dilator is lubed, we slowly work it inside,” Sondra added.
It took her some time but Sondra finally got it all the way inside me. I was breathing heavily but I finally relaxed.
“Oh my goodness. Is this all worth it?” I asked.
“You’ll know it’s worth it when Alistair finally makes you his woman. Especially when his hard cock taps your prostate. Our prostate is like a real woman’s clit. It’s our love-button. You’ll coo like a dove when he gets his penis that far into you,” Sondra promised.
“And wait until you really get nice and open, and you can sit on his lap, face him and kiss him while you fuck. Well, then you’ll know it was well worth it. Wear it as long as you can during the day. Once you hardly notice it, it’s time to move up to the next size,” Sondra added.
“There is an added benefit you may already know about? It really helps us walk really pretty. It adds a wiggle and sway to our hips. The men really like watching our asses when we have one of these up our butt. There are sissy training schools around the country where the Comportment Mistresses make the sissies wear a butt plug for the entire school day until after dinner. That’s a real test,” Sondra explained.
“They have schools where they train sissies?” I asked.
“Yes. All over the country as well as worldwide. The training of male to female sissy transgenders is a big business. They train maids, secretaries, hairdressers, Ladies’s companions, concubines, kept mistresses and even wives,” Sondra added.
“Can we take a break for lunch and then tell me a little about hormones and implants,” I asked.
After I made us lunch and served it, we relaxed and imbibed. I needed some Cherry Brandy to relax. Then we sat on each end of the same sofa where Alistair has first kissed me and Sondra filled me in further.
“Female hormones of course will feminize your body as well as your emotions. With the right amount of Estrogen you should be able to grow up to an A-cup set of tits. Alistair isn’t a big ‘boob’ man, so that would likely be sufficient. He’s more into legs, asses, and a real hot, runway model look,” Sondra said knowledgeably.
“He likes his girls slim, and slightly curvy, with glam makeup and fashionable clothing and hair. This evening, Brianna will be calling to fill you in on your outfit for tomorrow. Make sure you follow her dictions to a “T,” Sondra intoned.
I took a nap and then had dinner. Sondra had to return to the Montenegro estate to perform her duties. I was watching a movie when Brianna phoned.
“If you haven’t showered as of yet, make sure when you do, to shampoo and condition your hair, make sure your body is hairless and moisturize extensively. We are going to see to it that your look, your total appearance, will become increasingly feminine, each and every day from now on, Francesca,” Brianna said, firmly.
“Of course until such a time as you can easily pass as Francesca, we’ll refer to you as Francois. Of course, we all might want to think of your name in the feminine form, of Francoise, with an ‘e’ at the end,” Brianna added, simply.
“I’d like you to pin your hair up in a top-curl type of set, with small curlers or Bobbie-pins. Have you ever slept in curlers Francoise? Oh? Well good. I also want you to put on a very light coating of makeup. Let’s say some waxy-white lip-gloss? Next, a soft beige foundation with just a touch of pale-rose blush. Use a red-tinted mascara and pencil. Also a beige eye-shadow. You’ll be fine,” Brianna assured me.
“Use lots of hair spray to hold your top curls in place. Let the rest of your bob fall naturally. Wear some Palazzo slacks, with your tallest kitten-heel, open toe pumps, and panty-hose. I recall we got you a pair of white Palazzos with a dark-grey pattern. Wear those with a form fitting, black, scoop-neckline top. You’ll look great,” Brianna reassured me.
“Over the next several days we’ll add jewelry, some perfume, nail polish, maybe even a bow in your hair? Speaking of jewelry. After lunch, you and I will be going to get you a couple of piercings in each ear. That will be fun, won’t it?” Brianna asked, without waiting for an answer.
“If you want, I can pick you up for work, if you’d like me to accompany you into the office?” Brianna went on.
“Oh, could you, Ms. Brianna? That would be so special for a few days. Oh thank you,” I said, elated.
“No problem honey. That’s what I’m here for. That’s what we are all here for. We want to make this transition for you, for Alistair and for us, as smooth as we possibly can, darling. I’ll see you between 8:15 to 8:30 A.M. darling. Don’t forget to moisturize, Francoise with an ‘e’,” teased Brianna.
I felt so much better that Brianna would be going into the office with me. After my bath I made certain my body was hairless including my bush. Then I decided to paint my toenails pink as they would be hidden by my pantyhose. Then I moisturized before setting my hair. I slipped into a negligee before laying down in bed.
To calm myself I felt for my penis and began to massage it. Then I turned on the bedside lamp to find some Kleenex and lubricant. I laid on my back once again and began to masturbate sincerely. I first thought of being with Sondra in a sexual situation. My mind wandered to Brianna, who now appeared to be my mentor, who would be conducting the nuances of my “Transition” and feminization.
But, I couldn’t put out of my mind, the obvious person without whom, this transformation would not be in progress. I couldn’t forget the very handsome Alistair. Even if I pictured myself chatting with Sondra while we did our nails, or doing my own hair and makeup with Sondra supervising, Alistair was in the picture.
So I close my eyes and pictured myself in a form fitting cocktail dress with my hair piled atop my head in a high-fashion updo. I was fixing my lipstick and inviting Alistair to dance with me. He took me in his arms and swept me across the dance floor. From the dance floor we twirled into an adjoining room where he laid me upon the bed.
When our clothes were finally off I was struck by the picture in my mind. I had large tits and a pussy! My penis was gone! Was this a premonition? It didn’t matter. Alistair licked my pussy and then he entered me. I could no longer hold back. I arched my back and took his cock well inside of me.
He covered my face and mouth with kisses. As I fantasized more, I stroked my cock, faster and stronger. I was building to a crescendo. As I climaxed I imagined Alistair pumping his seed into my vagina. That felt so rewarding and nurturing. In real time as a climaxed I called out his name loudly, “Oh, my handsome Alistair, I adore you my sumptuous man.”
I slept well that evening, and awakened to the world of a new me. I was no longer Francois. I was now Francoise, transitioning to Francesca Monet. I hoped it would not be too trying?
Chapter III: The Glamorous World of Girlishness
My first week at the office as Francoise, was exciting, for no other reasons, than the changes in wardrobe and coiffure that I was beginning to experience. Ms. Isabella welcomed me with a new name tag and nameplate for my desk identifying me as “Francoise Bronte.”
At the end of the first week, Alistair, who had been pleasant but very busy during the week, came to my desk, outside his mother’s office sometime in mid-afternoon.
“I purchased some earrings for you, to go with your new piercings Francoise. I hope you like them?” Alistair asked.
“Alistair these are lovely! I’ll wear them as soon as these piercings are ready. Thank you!” I said as I stood to give him a kiss. It felt natural. A man had just given his girlfriend some new jewelry and she had kissed him excitedly as her way of thanking him. Regardless whether I were a girl as of yet, or a sissy, I felt like I was Alistair’s girl or sissy.
Alistair now took the opportunity to hold me in his arms and ask me, “Would you do me the honor of brunch at mother’s tomorrow at ten? I’ll pick you up thirty minutes prior. You may dress as Francesca if you prefer?”
“Of course. Yes, I think I’d like to try out my Francesca look, if everyone would be in approval,” I smiled.
“Yes of course. By the way, mother asked me, if you would mind meeting your transitional tutor, Helena Ferraro, at the brunch?” Alistair asked.
“No. Not at all. I’ve heard so much about her, and I know she’s very familiar with working with girls that are like me. She did a fantastic job with Sondra,” I agreed, cheerily.
I’d be driving to work the following week, without Brianna escorting me for support. Still, I’d be Francoise, of course. I now had about a dozen sets of earrings for my newly pierced ears. Between Alistair, his mother and Brianna, I not only had numerous earrings, but new bracelets, necklaces, brooches and pins.
For the Saturday brunch I planned on a skirt and blouse, taller heels, full makeup, perfume and a daring hairstyle. Maybe an updo? I would also wear a pair of A-cup, ersatz breasts that Brianna had given me. She’d actually given me three sets of false boobs.
The fake boobs were in A, B and C-cups. I needed to use a light, suction-type adhesive, to keep them in place underneath my new brassieres. In keeping with the early stages of my transition I’d stay with the more modest A-cup.
I set my long, inverted bob with mid-size curlers at bedtime. I didn’t know exactly which way I’d be going with my hairstyle for the brunch. I awoke extra early to prepare. As I sipped my girly, Chamomile tea, I planned my outfit.
I wanted to make a good impression on everyone. But I especially wanted to impress Alistair, his mother Isabella, and Helena, my, soon-to-be, new tutor. I decided to go with some white, ruffled-seat, sissy-panties, over a garter belt and sheer hose. I would wear my size-one butt-plug.
The sissy-panties had a built-in, cache-panel, where I could safely tuck my penis, should it become erect. I went with a pale-blue, bubble flip, mini-skirt, and a navy-blue, puff-sleeved, chiffon, pullover blouse, with a swan neckline. I wore a chain-linked, sterling silver, slave-necklace, given to me by Isabella. The snug fitting bust-line of the pullover, accentuated my modest, false bosom nicely.
I’d been practicing in the evening, all week in three-inch high heels. However I still was not perfectly confident in those. So I stepped down to a pair of two-and-a-half inch, open-toe navy pumps with a matching, small shoulder-bag. In the shoulder bag I placed my make-up for touch-ups and some lubricant. A girl can’t be too prepared.
I checked my cell-phone and saw that I had plenty of time remaining for my hairstyle and make-up, prior to Alistair’s arrival, to collect me, to take me to the brunch. I’d had plenty of practice doing my hair and makeup as a teen.
Plus, I’d spent several years between beauty school and being employed as a hairdresser to have styled the hair and done the makeup of numerous females. For my own purposes, I love fashioning a hairstyle first, before doing a cosmetic application to go with a “do” and the outfit being worn.
It’s really no different whether it’s me as the subject or another female. Every girl wants to look her best especially when her man is escorting her somewhere. I also wanted to look my finest for a fashionable beauty such as Alistair’s mother, as well as a stylish fashionista as well known as Helena Ferraro.
I began by unpinning the curlers I’d slept in. I looked at myself with the medium sized curls which the rollers had left behind in my hair. I decided on a sort of cross between an updo and a tousled, flirty styling. I began to smooth the top curls into a teased “Bouffant” look. Then I took the curls on the right side and lifted those, before pinning the curls in place with a tortoiseshell brooch.
I left the curls on the left side to bounce and sway. After I sprayed everything in place, I picked up a tube of foundation and gave my face a bronzed, smooth, highly polished appearance. After some plum blush, I used a smoky kohl mascara, rose shadow and a dark pencil to enhance my eyes.
To me, my lips had always been one of my best facial features, even when I’d foolishly wasted my time, attempting to appear to be a boy. They always had a certain plump, girlish, puffiness about them. And that was even prior to Ms. Isabella and Ms. Helena’s plans for me to obtain collagen treatments. My mother had instilled in me a preference for Guerlain lipstick. I almost always used it for makeovers at the salon where I was employed during college.
I took a lip wand of Cherry to outline my mouth before filling in with a tube of Mango. I finally dabbed just a touch of Jolie Femme, by Faberge behind my ears, with a slight touch just above my false breasts. I blotted my lipstick slightly, just prior to Alistair’s arrival.
I’d done my nails in a similar shade of Mango the evening prior. I felt good about the way I looked. It felt natural being dressed as Francesca. I wondered how long it would take me to feel comfortable as Francesca publicly?
All the time I took to get ready was worth it, just to see the way Alistair looked at me, when he arrived to pick me up. He took my hand to walk me to his Ferrari. I slid into the front seat gracefully as he held open the door. On the drive to his house he rested his hand gently upon my hands which were folded in my lap.
When we walked, hand-in-hand into the dining area where the brunch was set up, a smiling Sondra winked at me. Brianna bussed my cheek and said, “You look perfect, Francesca.”
Isabella was even more gracious. “You’re no less than stunning, my child. I can’t wait for Helena to see you. She’s using the Little Girl’s room, right now.”
Before I’d be introduced to Helena, I overheard Isabella, admonishing a very pouty petulant, Elaine. “Darling, must you always be the center of attention? After all, this is Francesca’s moment. And I might add she will have numerous moments as she comes out further. Now enjoy yourself Elaine. Be nice.”
Isabella took me off by myself to finally introduce me to my soon-to-be tutor, Helena Ferraro. Helena was about Isabella’s age and just as perfectly “well-preserved” as Isabella.
“Helena, this is Francesca Monet Bronte, who I’ve told you so much about. She’s my son, Alistair’s, girlfriend. She also works as my personal assistant,” Isabella smiled.
“Oh yes. Let me look at you dear. And she’s to be my new student, isn’t she? Hmm. Very lovely and you were so correct as always, Isabella. Francesca has given us so much to work with, hasn’t she? So. You are transitioning, Francesca? And beautifully, I might add,” Helena said.
“Yes. I’m still in slacks at the office and being called Francoise. The girly version of Francoise,” I added, smiling.
“Yes, of course. But not for long. Not with me as a tutor you won’t be,” Helena promised.
“If you work all week long, it might only be possible for us to have classes on Saturdays and/or Sundays? Is that correct, Isabella?” Helena asked.
“I’ve thought of that Helena. It might be possible, for me, right now, to give Francesca Wednesdays off. I’ve presently found the need to keep my Elaine occupied with something other than looking beautiful,” Isabella added, conspiratorially, with raised eyebrows.
“So why not Wednesday’s and Saturday’s. Other than a Wednesday when Francesca might need to visit my GYN or a Saturday when she’ll be busy at my Hairdresser’s? I can begin breaking-in Elaine as a personal assistant, part-time, for whenever my son’s lovely girlfriend needs some time off,” smiled Isabella.
The brunch was over at noon. Helena confirmed that my first class would begin next Wednesday at 10 A.M. A very pouty Elaine, went to her boudoir with an equally perturbed Isabella, closely behind her. Brianna returned to the guest house and Sondra did what maids always do after a brunch. She cleaned.
That left Alistair and I to wander out to the South Patio. He snuggled with me on a divan and kissed me. I became quickly aroused and massaged his chest lovingly.
Looking at me he asked, “Could I take you to my room? It’s on the other side of the mansion from anyone else’s boudoir. We can have privacy there. Maybe we can discuss the purchase of the Jasmine Laurent mansion?” Alistair asked.
“Maybe we could? Or maybe we could think of something else to do?” I said, squeezing his growing erection, through his slacks.
It didn’t take any more than that, to get Alistair to pull me to my feet and escort me very quickly to his masculinely appointed bedroom. I didn’t waste any time.
“Alistair. Might I use the bath to remove a few things? Specifically my inserts and my plug? I want you to be able to bite my real nipples and to enter me, my love,” I explained.
“By all means, my precious lover. Yes. Biting your nipples and entering you sounds very exciting,” Alistair agreed.
I returned, wearing only heels, garter belt, hose and panties. I’d set my purse on the nightstand. I’d divested myself of my skirt and blouse. My hair was unpinned and fluffed. My lipstick was freshened. Alistair was naked, laying upon the bed with the sheet and blanket turned down.
“But first,” I said, kneeling on the bed, and positioning Alistair’s back against the headboard. Then I knelt over him and took his gorgeous cock in my hands. I licked its entire length before I took it into my mouth. Sucking it briefly I released it and sucked his balls.
He stiffened and I giggled. Then I returned to the business of giving him a blow job. I did my best to take nearly the entire length of his cock into my mouth. I slurped and sucked to excite him. My wet, lipstick covered mouth surrounded his penis.
I loved every inch of his engorged manhood as much as I adored this lovely man. His stark masculinity so complimented, as well as contrasted, my delicate, girlish effeminacy. Right now I wished terribly that I could have orb-like tits for him to suckle. His cock had grown to its full proportions when he bade me to lay next to him.
I did as he prompted me. As I daintily laid my slim body next to his muscular frame, he pulled me to him. I automatically and delicately fingered his cock as he took one of my boyish nipples into his mouth. How sweet of him to treat me as he would a female. I shivered with delight.
“Oh darling I just found myself wishing I had womanly breasts for you to lick and to suck. I don’t yet feel as a female should. I feel more like a dainty sissy than I do a girl, with my flat, boyish, sissified chest,” I whimpered.
“That is just fine my very sweet, prim, prissy, creampuff. I delight in your effeminate, sissyish, cherubic, body. You are my pretty sissy, my pet. No one can ever take that away from you. You look just so delightful with makeup on and curled hair. And your body is as delicate, smooth and femme as any female I have been with,” Alistair promised.
“Oh thank you, my handsome man for saying such sweet things to your worshipful sissy femme. You are such a wise, kind Master, to your little sissy-slave,” I tittered.
As he nipped at my flat chest I fondled his cock more thoroughly.
“Alistair my love. I would like once again, to try for you to enter me. I want to feel as one with you as your woman. Please, darling? Could we try?” I begged.
“Of course my Petit Chou. Did you bring lubricant? Oh yes, wonderful my pet. You did,” Alistair said, pleased.
I removed my panties and at last I kicked off my heels. I lubricated both of us and knelt. I bent over on the bed, my ass up in the air to welcome his strong, manly cock. Alistair gently and lovingly probed my entryway.
As he pushed gently into me I breathed deeply and arched my back to push my ass against his penis. I wanted so badly for him to fill me up. I wanted terribly to finally feel as his woman should. Slowly his oiled cock entered my lubed anus. I tired not to struggle and I let it all happen.
At last I felt it slip deeper within my rectum and I tried not to tense. I let out a deep sigh of relief as his prick lightly contacted my prostate. I felt cool chills. Now I cried out, “Oh yes, Alistair. Please fuck me Master?”
“Yes darling. We will fuck very slowly. Let us enjoy this to the maximum. Yes my love. This feels very nice,” Alistair agreed as we began a steady back and forth, rocking motion.
I was so deeply enthralled with the lustful feeling of being screwed so beautifully by this well-muscled man. I felt so, very, very horny. I began to pick up the pace. Alistair’s cock was magnificent and he could use it so well.
My penis had swelled to its max proportions. I had never, ever dreamed that being screwed in my anus by a big, strong, masculine man could be so exciting. Then of course, I could still get a very nice erection. I was reaching a point where I was certain I was going to spurt.
“Oh Alistair I am getting so close. Do I have your permission to climax?” I asked inadvertently.
“Not just yet, my pet. You must wait for me. Do your best to control yourself, my love,” Alistair ordered.
“Yes, of course Alistair I will. Whatever you wish my dearest,” I feebly complied.
Shortly I heard Alistair gasping out mannishly. He began to pump harder and harder. I loved it! Then he cried out.
“Now. Now you may now cum my princess. I’m about to fill your ass with my man-seed,” Alistair said as I felt his cock swell and begin pumping his hot, gooey sperm into my rectum. Oh, it was so fantastic!
At the same time I began to shoot my load. Squirt after squirt of my spunk, gushed out of my cock, onto Alistair’s bedsheets. Alistair squeezed me around my waist gasping as he completed his strong climax. I fell to the bed completely spent and Alistair collapsed on top of me.
We kissed in glorious blissful love. I could not believe that being with a man, especially a really strong, confident, man like Alistair, could have ever been so rewarding. He was everything I could never, ever be. I reached for some Kleenex and cleaned him.
Then I cleaned myself. I looked to the bed and saw the large puddle of sperm I had spent onto the sheets. Alistair excused himself.
“I’m going to thoroughly clean my cock, darling. Thank you for wiping me, however,” he smiled.
“Oh Alistair you were so fantastic. Darling, what should I do with this puddle of sperm on the bed?” I asked.
Alistair paused, looking puzzled. Then he answered. “Why not do your best to lick it up, my love? After all, you’ve never tasted sperm have you? And sooner, rather than later, you are very likely to be swallowing my load when I shoot into your mouth during a bow job?” Correct?” Alistair answered.
“Lick it up, dear? Oh yes. Of course. You’re correct. I don’t know what it tastes like,” I answered as I knelt on the bed to lick up my own sperm.
“Francesca, darling. I have a spare toothbrush here at the sink that you may use to brush your teeth,” Alistair added.
I licked and sucked up as much of my salty sperm as I possibly could. When I told Alistair there was still a wet spot evident, he walked from the bath with a washcloth.
“I’ll take care of the rest, princess. Please brush your teeth now?” Alistair directed me.
When I returned from brushing and gargling, Alistair was standing by the bed. I was still so filled with post-coital joy, that I threw my arms around him and kissed him. As we kissed passionately I reached for his cock and felt it stirring. He was already getting hard once again!
“Oh my gracious Alistair! You already are getting another erection. You are just so manly aren’t you? What am I going to do with you, my lover?” I asked.
He placed his hands upon my shoulders and spoke, as he pushed downward, “Well, seeing that you ask, my love, you may kneel if you care to, and suck my hard cock for me, my lovely Francesca. That’s it darling. Be a dear and get on your knees. That’s it, take me in your pretty, red, mouth,” Alistair sighed.
As I knelt and licked both his cock and balls, I eventually again, took the entirety of his cock into my painted mouth. He assured me he wouldn’t muss my makeup anymore that he already had.
“I know you’ll want to take great care to prettify and beautify your face and tresses prior to me taking you home, darling. So I won’t give you a sperm facial or get any ejaculate in your hair. Just swallow my seed my pet. As you now know, how it tastes,” Alistair explained.
“Yes, darling, I can’t help but want to swallow your discharge my love. And thank you so much for being so understanding as to my appearance,” I gushed.
I now knew, while on my knees, what type of relationship I could expect with Alistair. He would always be a good lover and good provider. He would fully appreciate that I’d keep myself pretty and slim for him. I’d live a luxurious life, as he’d shower me with gifts and I’d be pampered endlessly. But sexually, I’d always be Alistair’s hot, sexy, acquiescent, sissy-bitch.
I knew I could live with that. For most men, that is the attraction with sissies. We are ultra-femme. We live to outdo real girls. We are dithering, cloying, maidens. Especially where subservient behavior comes into play. If Alistair wanted me to drink a Champagne glass full of his sperm I would.
And I intended to prove that to him, in his bedroom, that Saturday afternoon after the brunch. I sucked his cock until he took the hands he had upon my shoulders and intertwined his fingers into my curled, brunette locks. As he pumped his cream into my throat, I sucked down every last drop.
I emptied his ball sac until it was dry. I wanted it to be the very best blow job he’d ever been given. As he fell back upon the bed, I sat next to him.
“Is everything okay dear? Are you all right? Did you enjoy the blow job I just gave you, lover? If you don’t need anything else, I’m going to brush my teeth and rinse. Then I’m going to get pretty for the drive to my condo. Unless you’d like me to hold you dear? Well I will hold you then,” I replied and snuggled with him.
Once we were both dressed, and ready to depart we walked through the Montenegro residence to the front doorway. The house was quiet and appeared empty. When I mentioned the possibly that his mother might be out shopping with Elaine, Alistair shook his head.
“I don’t think so. Please don’t repeat this, of course. However, I would guess that mother is performing a private disciplinary session upon Elaine. She’s become perturbed with Elaine’s petulant behavior of late. Mother describes this sort of discipline, as an ‘Attitude Adjustment’. To further shame Elaine, mother will frequently have Sondra assist her with the chastisement,” Alistair quietly explained, to my surprise.
I didn’t say any more about Elaine’s possible disciplinary session, during the drive to my condo. Though I suspected what Alistair might be referring to. From my own previous chastisements as a teenager, I knew discipline could be very shaming. Alistair walked me to my door and gave me a very nice kiss goodbye.
“You looked fabulous today and you were no less than fantastic in bed my love. Getting together with you in the near future should be very exciting,” Alistair stated.
“Yes. I’m looking forward to it, myself. Oh Alistair, just hold me. Please? Oh yes. That’s just so right. I love you Alistair,” I said, and gave him a long, promising kiss right at my front door.
I couldn’t help but touch myself thinking of Alistair, in the days that followed. Nearly every evening I masturbated myself thinking of Alistair at bed time. During the weekdays, I wore to work exactly what Brianna prescribed every evening prior to the next workday. She had me add jewelry, mostly, to my outfits.
It was my tutoring sessions with Helena Ferraro, that were most rewarding and interesting. For the first session, Helena arrived promptly, just prior to 10 AM on the Wednesday following the brunch where I had met her.
I was dressed as girlishly as possible for Helena. I had tea ready for the both of us. She had me stand and appraised me, as she sipped her tea. Then she made me walk back and forth across my living room as she critiqued me.
I was mildly apprehensive about my lessons with Helena, as Sondra had warned me she could be a strict disciplinarian and quite the martinet when displeased. I’d experienced my share of spankings, paddling sessions, as well as chastisements. Often, I’d been made to stand with my nose in the the corner of a room, by my mother, auntie, grandmother or sister, during my Petticoat Discipline years in Quebec.
Helena did tell me that it wasn’t beneath her to “warm up a girl’s butt” if she was displeased.
“However I don’t expect to need to do that with you, Francesca. You have had previous training sessions and you are likely quite used to being under the strict control of feminine authority. Aren’t you dear?” Helena asked.
“Yes ma’am, Ms. Helena, I am experienced with female rule. I only recently began to realize that I might need more of that. I know I really do enjoy pleasing, my Alistair, as well as Ms. Brianna and especially Ms. Isabella. I realize Master Alistair could hardly be described as feminine though,” I laughed.
“What I mean is, I have begun to realize that my need to please him in a very feminine way, is quite important in my life,” I agreed.
“That is how it should be dear. The more feminine you are, the easier that will be to accomplish, also. Now, I never force my girls to do anything. Well I might do that, were I sissifying a nephew for my sister, or emasculating my niece’s boyfriend. However I do encourage all of my girls, at the very least, to begin Female hormone replacement therapy,” Ms. Helena explained.
“Hormones not only feminize your body, but they aide you in grasping the world around you from a female perspective. Your entire personality changes to that of a girl. The more physically and psychologically feminine you feel, the easier it becomes to look and act feminine,’ Helena added.
“Now let me listen to your voice and examine your posture, your mannerisms and your body language. Read this magazine description from a fashion and beauty editor, describing the experience she had getting a complete makeover at one of Miami’s most exclusive beauty spas,” Helena said, handing me a fashion and beauty magazine.
“The writer is a true Latina Fashionista, much like your new boyfriend’s mother. I want you to read the article as expressively as you possibly can. I want it to be as if you are sharing it with me, and I’ve never heard or read the story before. You want me to be as impressed as the writer was with the salon,” Helena explained.
“I insist you use your body language, hand gestures, and voice inflections, to make the article as exciting and girlishly interesting as possible. I want you to act as if you are very impressed with what the writer says about the salon. So much so, that you want the both of us to make an appointment at this salon very soon. Do you think you can do that for me, Francesca?” Helena asked.
“Yes. Yes I do think I can Ms. Helena. Could I read it through silently to plan my presentation? I asked.
“Of course you can, Francesca. You are an actress wanting to perfect your craft. You want to impress me and act as girlishly as you possibly can. I’ll finish sipping my tea while you read it over,” Helena agreed.
I began to read the article to myself. Indeed, the full-service salon and spa sounded very elegant and top-shelf. Over the years, my impression and opinion of salons and salon visits had changed. In my teen years, when I was under a very strict regimen of Petticoat Discipline, I had dreaded going to the salon.
I had great trepidation about any sort of salon appointment. The ladies at the salon all knew I was a weak, effeminate, sissy-boy who was under the strict control of feminine authority. Therefore they would tease me with mocking comments as to how girly I was going to look when they were finally finished with my hair, face and nails.
I would cringe listening to the gay peals of laughter and subtle remarks directed my way, as my new, very femme, “do” would take shape. Once I entered beauty school, it wasn’t unusual for the Headmistress and owner, to allow the instructors to use me as a “Hairdo Model” for the other trainees. The Headmistress, Marta Lang, knew my Aunt Cerise.
Marta was keenly aware that I was being trained as an effeminate sissy-girl, and would have the female salon students color and curl my hair in girlish styles and shades. A day at beauty school was a day immersed in feminizing emasculation.
It wasn’t until I received my beautician’s license, moved away, achieved my high-school equivalency and enrolled in business college, that my life attained a semblance of boyish “normalcy.” If, of course, one could describe it as such?
Working at a nice salon while attending a two-year business college had it’s benefits. Even if I was often gently teased about my “pretty,” “girlish” looks. A few girls in college dated me because I didn’t mind doing their hair and makeup before a date.
And if these same girls requested I wear one of their sequined pullover blouses on a date, I would eventually relent, to make them happy. I did, from time to time, get playfully chaffed by the female salon employees about how “cute” I might look with curls in my hair, or wearing some makeup.
However, they would often flirt with me, and at least treat me like a pretty boy, that they might consider dating. A few of the salon girls did go out on dates with me. From Helena, I knew I might soon find that I’d be in attendance as a client at Isabella’s favorite salon, in order to please Isabella, Helena, or even my handsome man Alistair.
Of course I had never dreamed that a thorough beauty makeover would become a welcome and glamorous diversion from a mundane day at the office. Nor did I believe I’d ever prefer a day at the salon, to staying at home, in an apron, polishing the silverware, awaiting my husband’s return from a morning at the Country Club golf course.
But, there are changes in a girl’s life, aren’t there? I now finally felt comfortable enough to read the full article on the fashion editor’s beauty makeover for Helena’s critique. I began reading expressively, making sure to engage in eye contact with Helena. I was careful to use dainty hand gestures and light, tittering laughter, to emphasize what a fun day it would be, to have our hair, nails, faces and bodies pampered at this salon and spa.
Helena appeared satisfied when I’d completed the reading. She went over a few things which she thought I could improve upon, and assigned me homework to practice these skills and re-read the piece the following Saturday. She then moved on further, to walking, sitting and standing exercises, as well as more extensive tutoring on my speaking voice.
Prior to leaving, she once again discussed hormones with me, as well as figure training. She emphasized both these “phases” of transformation as critical to my successful transition.
“Isabella’s GYN is the same lady that Sondra has seen for Hormone Replacement. I will also make an upcoming appointment for you at the Modiste, of a corsetiere, I frequently employ with my girls. Figure training is essential for girls such as you. It’s important for disciplinary motivation and it builds self-esteem. You look good, as well as feel good, when a shapely figure presents itself in a full-length mirror,” Helena emphasized.
The following day at the office, right after my lunch break, I spoke with Isabella. “Madame, I was wondering if I could make an appointment with the same lady whom Sondra sees for Hormone treatments?” I asked.
“Why of course you can, Francesca. We’ll skip Francoise during private moments like this. We may be moving directly to Francesca anyway. Once, of course, you decide to begin Hormone therapy, we’ll be left with little choice,” Isabella added.
“I’ll make an appointment with Glynis de Laurier, my GYN, for next Wednesday. I’ll let Helena know you might need some time off from your Wednesday lessons,” Isabella added.
Saturday, when Helena arrived for my Saturday tutoring, she informed me that instead of classes, we had an appointment for a fitting with her corsetiere. On the drive there, she filled me in on the process.
“Alicia will be snugging you into what will eventually amount to pre-laced foundation wear, and shape wear. Isabella informed me that you are considering Estrogen injections. The garments you’ll be trying on at Alicia’s, will insure that once the hormones kick in, your chemically feminized body, will be adjusted to conform to the proper contours of a womanly figure,” Helena explained.
“Between the physiological enhancements of the chemicals and the psychological effects from the reshaping of your body, you’ll see yourself in an ever-increasing positive light. Your confidence in being beautifully feminine will soar, Francesca. Mark my words, you’ll adore being who you are,” Helena promised.
Standing in tall heels, upon a lacing pedestal to be “garmented” and “girdled” initially made me feel very self-conscious. I was surrounded by mirrors and Alicia’s various female assistants kept coming in and out of the fitting room, carrying numerous changes of lingerie, undergarments and foundation wear for me to try on, and for Alicia and Helena to critique.
“Don’t worry honey. Just put yourself in our hands and relax. All of my girls end up craving what we eventually achieve. What with the constant attention we pay to their bodies, and the lovely enhancements we make to their figures, all my girls become striking beauties,” Alicia promised.
“Between Glynis de Laurier’s expertise and my establishment’s methods, you girls just keep returning, because you look better everyday, and you feel progressively better about who you really are. Not to mention, who you were always intended to be,” Alicia intoned.
“Do you have a husband or boyfriend, precious? Because when Glynis and I are through with you, he won’t be able to keep his hands off of you. We’ll have you looking like a centerfold model, before we’re even completely done molding you,” Alicia promised.
“We’ll use some padding early on. But, you won’t need an ounce of padding once you fill out in all the right places and we eventually re-shape and re-mold your contours,” Alicia added.
When we had completed all of our purchases, one of Alicia’s assistants instructed me on using the snaps and catches on the front panel of my “pre-laced” corsets and cinches. She helped me fasten the pre-laced items into place, around either my entire torso or simply my waist, depending on the garment.
“As your waist narrows and your hips and bosom fill out, you’ll need to come back in, and we’ll re-adjust everything to properly contour your foundation lingerie to your new dimensions,” the girl explained.
I was slightly apprehensive concerning my Wednesday visit to the GYN, with my boyfriend’s mother, Isabella. However, Doctor Glynis de Laurier was tops in her field. Not only was she an amazing GYN, but, also a gynecological surgeon, and a well-known advocate of Transgender females. On the staff of her clinic she had also employed a renowned bust-enhancement surgeon.
Before she did my exam or bloodwork, she asked me to discuss my background as a transgender, with her. Just so she could assess my actual interest and potential as a candidate to transition as a female.
“Francesca, you do have a definite lengthy and somewhat extensive experience as a transgender. You also appear to have a real interest in tossing aside your life as a male and experiencing life from a feminine standpoint,” Glynis agreed.
“There are a few, very positive things I see that you might currently view as not so positive, Miss Francesca. For example. Your experiences, that began when you were thirteen. When your mother and the rest of the females in the household dressed you as a girl. Tell me this Francesca. Did you ever, even once, attempt to resist, complain, or refuse to cooperate in your transformation?” Doctor Glynis asked.
“No ma’am, Doctor. I did not,” I said, shamefully.
“I thought that might be the case. You see, Francesca. What I think, is that they knew, what they were doing, was best for you. They saw a timid, weak, girlish boy, trying to break out of his shell and act out as some sort of hooligan. They desired to protect you and not allow you to become like your father,” Doctor Glynis intoned.
“They also knew you were going to have a difficult time making it in a world filled with Alpha males. They realized you were a Beta-boy. Your full compliance in surrendering to those feelings of effeminate submission and dependency tells me you realized it also,” the doctor said.
“You enjoyed the protection which being emasculated provided to you. You hid timidly behind the skirts, blouses, dresses and makeup. It was the same at beauty school, Francesca. Did you ever tell the girls in hair design classes, to stop when they colored or permed your hair? Or protest when they painted your face with cosmetics,” Doctor Glynis asked.
“No ma’am Doctor Glynis. No, I did not,” I said, looking away from her, thoroughly ashamed.
“That’s exactly what I suspected honey. You really weren’t much of a boy, were you? I realize that being sent to hairdressing school limited your job selection options. You practically had no choice but to work as a beautician throughout college. But look at the courses you took in college,” Doctor Glynis explained.
“You enrolled in a curriculum that would put you on a career path towards a very stereotypical female job. However, nothing at all is wrong with any of this, Francesca. Those choices as well as the path you’ve taken, makes you a perfect candidate for transition to a life as a female,” the doctor smiled.
“Everything about your life thus far, are all pluses when it comes to being a transgender girl. I totally would approve of you beginning Hormone Therapy today if you so desire to. And should you come to me and ask to be gelded or even go so far as ask me for a sex-change, I wouldn’t hesitate to agree, Francesca,” the doctor added.
“Why don’t we get you into a pretty robe and up on the exam table? Nurse, assist her with changing and prepare for a blood draw. Now honey, it will be your choice if you want to begin Estrogen treatments today,” the doctor explained.
I looked at Isabella who had been silent but listening. My glance to her was questioning.
“I think you should honey. I think it’s what you want. I’m sure it’s what Alistair would agree to,” Isabella said.
“Yes, Doctor Glynis. Let’s begin the medications today,” I said.
Shortly, I was up on the exam table with my feet in the stirrups. After the nurse had drawn blood and before the doctor began my injections, Doctor Glynis surprised me by saying she was going to masturbate me.
“It’s nothing really. Just a little test to keep track of your sperm count, is all. Shall we begin? Nurse, you’ll need to catch the ejaculate in a measuring tube and transfer it into a test tube. I’ll need to lubricate your rectum also Francesca, as your prostate needs to be examined,” the doctor assured me.
One of the doctor’s gloved, lubricated fingers slowly worked its way into my rectum, while she fingered my penis with her other gloved, lubricated hand. I gasped girlishly, as she, the nurse and Isabella all smiled.
“Does this feel stimulating, Francesca?” Glynis asked, almost teasingly.
“Oh yes, Doctor Glynis. It feels very nice,” I tittered as she moved her right hand up and down upon my growing cock.
If this was going to be a part of my monthly visits to Glynis de Laurier’s office, I was really going to enjoy it. It was a little embarrassing with Isabella and the nurse in the room. But having a pretty young doctor like Glynis de Laurier masturbating me was very stimulating.
Little did I know or even suspect, at that moment, how much the Estrogen was going to inhibit my ability to get erections in the future. At the time however, it was very enjoyable. I laid my head back and closed my eyes, and focused on being with Alistair.
Fantasizing about being in Alistair’s arms and having his penis inside of me, accelerated my climax. At the moment that I began to breathe heavily, Doctor Glynis’s finger probed my rectum further and massaged my prostate. That alone would have been enough to send me over the edge.
Along with my dreamy fantasizing about Alistair and the doctor’s stimulation of my penis, I arched my back and practically screamed, as I held tightly to Isabella’s extended hand. I gutturally expelled a groan, as my sperm exploded into the tube held out by the nurse.
Once I’d given the sperm sample, I was cleaned up and given four injections. Two in each hip and two under each arm, near to my pecs. After dressing, and fixing my face and hair, I sat in the doctor’s office, next to her desk and she discussed the hormone injections and hormones in general, with me.
“I want you to take one of these tablets every day, Francesca. I also want you to massage this cream onto your aureoles and all over your buttocks and thighs, every evening. One pump for each application. One moment Francesca. Isabella? Just as we did with Sondra, we should begin referring to our girl, exclusively as Francesca from here on. Plus, she should dress and live as Francesca 24/7 at this juncture,” Glynis explained.
“Now, Francesca. I’ve given you some new, accelerated acting hormones, that have been getting marvelous results. We can likely achieve an A-Cup bosom for you. You’ll begin to feel some itching around your aureoles before you actually see growth in you bosom, hips, thighs and buttocks,” Glynis said.
“You’ll also begin to notice a change in your mood, your emotions, your thought process and your personality. You might get some silly emotion swings. You’ll pay much more attention to how you look. You’ll definitely take more care to redo your makeup and touch up your lipstick. Your sexual urges will certainly change,” Glynis remarked.
“For instance. Do you have a boyfriend?” Glynis asked.
“Yes she does. Francesca and my son, Alistair, are dating,” Isabella smiled.
“Oh how nice! Well. Shortly after your second or third series of Estrogen shots, you are very likely to begin thinking about getting really intimate with Alistair, in a very urgent way. Don’t let it trouble you, Francesca. It’s normal. Most girls have the same urges. The best action to take is to go with the way you are feeling,” Glynis advised.
“I’m certain Alistair will be flattered by your attention to him. You may contact me easily by messaging me through your patient portal through our clinic’s website. Don’t hesitate. Make an appointment for one month from now on your way out. See you then, Francesca,” the doctor added.
On the drive back to the office, Isabella asked if I would like her to have her attorneys begin the paperwork to have my identity and identification changed to Francesca Monet Bronte.
“I really believe that would be best, Ms. Isabella,” I agreed.
“One other thing, Francesca. You are practically part of the family, you know? You work for me. We have a close relationship. You date my son. The two of you have a budding relationship. Would it be too much for me to ask, to have you refer to me as Mother Isabella during our more private, personal moments,” Isabella asked.
“Really? Oh that’s so nice of you. I’m flattered. It would still be Ms. Isabella at work and publicly, correct? Of course, Mother Isabella. I’m just overwhelmed that you would permit me that honor,” I added.
I felt so comfortable since I’d left Glynis de Laurier’s office. I slept well that evening. I arrived at work with Brianna. I was nervous about driving into the office for my first full day attired fully as Francesca. But once I arrived at the office and saw my new name tag and the plate on my desk identifying me as Francesca Bronte, I really felt secure.
Was I ready for all the changes that were about to come about in my life, though? Time would tell, wouldn’t it?
Chapter IV: Is This Love or is it Lust?
I stopped more frequently to view myself in mirrors. And when it dawned on me, I’d take my compact out, and touch up my cheeks or paint my lips. Plus, after the second full month’s injections, the doctor’s prediction concerning my impending increased sexual urges came to fruition. I noticed it almost immediately when I arrived back at the office after leaving Glynis’s clinic.
The hormones which had just been injected into me were coursing through my body. I saw Alistair pass by my desk and I became flushed as he smiled at me, waved and said, “My, don’t you look lovely this afternoon, Francesca?”
I knew at the time that I felt very lovely and desirable. And I wanted to be with Alistair, intimately. I waited about thirty minutes. And then I minced, jiggling, my now fattening ass seductively, into his office. Then I tapped lightly on the open door. “May I come in?” I cooed prettily.
I paused, leaning over the front of his desk, showing off my new modest cleavage, and then asked Alistair, “Would you like to drop by my condo on your way home from work today? You know. Maybe we could have a drink, some chit-chat and I could make you dinner? Only if you’re hungry, of course,” I said.
Alistair paused. “I’d like that very much, Francesca. I’ll let mother know, so that Sondra will only cook for mother and Elaine. I’ll head right over to your condo as soon as I leave the office,” Alistair added.
About an hour prior to when I normally would leave the office, Isabella came out of her private office and stood at the side of my desk, smiling.
“Why don’t you leave early today, Francesca. Alistair told me he’s having dinner with you. You’ll need time to freshen up and prepare everything, won’t you? Things are slow here today. Why don’t you leave right now. I want the two of you to have fun. Tell Alistair I’m not going to wait up for him,” Isabella teased.
I rushed home. I now had a driver’s license identifying me as Francesca Monet Bronte, Transgender female. So, I wasn’t as concerned about receiving a ticket any longer as Francois, while dressed up in girly drag. I wasn’t so much in a hurry to get dinner ready as I was about getting “Me” ready for my man.
I wanted to look as smoking hot for Alistair as I possibly could when I greeted him at my front door. I couldn’t get into the shower fast enough. Once I toweled dry, I scented myself in moisturizer and powder. I nipped-in my waist with a cinch. I squeezed the new bumps on my chest and put my budding “girls” into a training brassiere.
I wanted to be accessible, especially in the rear, so I put my filmiest panties on. I’d removed my butt-plug. I was now up to the largest plug and couldn’t wait to fit Alistair’s engorged manhood into my ass. I passed on wearing any garter or hose. I simply slipped into a velvet, crimson, shorty robe.
I set my hair quickly onto hot rollers and began to lavish cosmetics onto my face. I’d recently had my dark, brunette colored hair, done over with a vivid, wine red hombre. I’d also had it cut shorter, with a chin length “bob.” It was tapered in back with a striking shaved nape. The style and color were eye catching enough without the curled, “high-lift,” wet-look, which I now gave it, as I sprayed my hair into place.
The makeup “look” which I gave myself was borderline “overdone,” with dark, “come hither” eyes and really dripping wet, glossy lips. When everything was complete I gave myself a few dabs of French perfume and I again spritzed my tresses. My ears sported a set of large Gypsy hoops and some dangling, jeweled pendants.
I felt good enough about my looks to “stop traffic.” Luring Alistair into my “den” was my next move. When he knocked on my front door, I sashayed to the foyer in a pair of tall, five-inch, ankle-strap, spike heels. I had a glass of his favorite Scotch in my right hand.
“Please come-in darling? Take this Scotch and let me remove your jacket and tie, honey. There. And now lets unbutton that collar, shall we? Very nice. Why now sit in the parlor and relax. I could take your shoes off and rub your feet, for you. Hmm? Would you like that?” I asked, taking his hand and leading him to a nice, comfortable easy chair.
“This Scotch tastes wonderful and you look marvelous, Francesca. If I didn’t know better I’d suspect I was being seduced,” Alistair smiled.
“Oh you are being persuaded sexually, my lover. When I saw you earlier this afternoon I couldn’t help but think that I needed to be alone with you. Now, I haven’t begun dinner yet. But I have a few ideas I wanted to run by you,” I said.
I was sitting on the floor with my legs curled under me. I laid my head on his thigh and began to unbuckle his belt.
“Let’s call out for something later, Francesca. Please get a glass of wine and sit on my lap?” Alistair asked.
“Of course I will,” I said.
I got up. I went to the bar and poured a glass of Cherry Brandy. Then I seated myself in Alistair’s lap. He immediately encircled me in his strong arms. I rested my thick, perfumed, titian, teased tresses upon his chest and sipped my Brandy.
He’d set his glass of Scotch on the lamp table next to the easy chair. He took my Brandy from me and sat it there also. Then he smothered me with a very, manly kiss. This was just what I needed and wanted. My loins were really stirring. Just as Doctor Glynis had predicted, I felt all “juicy” inside my panties.
I put my hands on Alistair’s big shoulders and really enjoyed our French kiss. My tongue snaked around his tongue and I began to suck his lips hungrily. I was grinding my ass into his crotch and moaning. I’d become one, very horny, sissy-bitch.
Alistair certainly noted it. “Should we move this into your boudoir, my princess?” Alistair asked.
“Yes, please, darling. I’d love that. I want you in my mouth and then up inside of me so badly Alistair. I can scarcely believe I’d have ever wanted a man as badly as I want you in this instant, my hunky, stud,” I gasped.
I’d really been watching my waistline, and this majestic brute carried me to my bed, easily. Just as any strong, masculine man, would carry his virgin bride across a threshold. Depositing me upon the bed, he began to undress. I looked up at him, crazy-in-love and craving his cock, deeply inside of me.
I slid my panties down, as I dangled my heels, to drop my shoes to the floor. I opened my robe to reveal my brassiere, which held my new, growing girls. A naked Alistair turned me over to unfasten my bra. Then with me on my back, he licked my newly formed, pubescent tits.
I shivered with delight as he bit my nipples. “They look so lovely on you, my precious angel,” Alistair spoke.
“Oh thank you, my love. They’ll grow bigger with the Estrogen. I’m hoping for a nice, firm, A-cup,” I whispered as he took me into his strong arms.
His kisses, as always, were full of lust and promise. I wasn’t going to allow this magical moment to pass us by. With his strong masculine body pressed against mine, and our lips meshed together, I grabbed Alistair’s hard cock and fondled it.
Then I told him I wanted to suck on his penis.
“Yes, of course, but not for too long. I want to be inside of you badly,” Alistair said.
“Oh yes, my Master. I want that also,” I agreed as I began to blow him.
I could taste the small amount of pre-cum in my mouth, that most men dribble when they are strongly erect. I knew by now, from taking female hormones for a couple of months, that the day would come where I might never again attain or maintain a sturdy erection.
I had something like an erection at present but nothing compared to the massive boner that Alistair sported at the moment. I couldn’t hold back any longer on having Alistair inside of me. I reached to the nightstand for some lubricant to put on his penis.
“How would you like to take me, my Masterful Prince?” I giggled in a guttural, sultry manner.
“Why don’t I sit upon the side of the bed with my feet planted upon the carpet? Then you can mount me while you face me? That’s a girl. You put some lube inside your pussy didn’t you? Oh, you’re sliding down my pole nicely, aren’t you angel?” Alistair smiled.
“Oh, good girl, Francesca. Now lock your legs around me, princess. Oh that’s nice,” Alistair added as his penis went fully inside of me. I placed my arms around his shoulders with his arms around my back.
Then, I laid my face against his. Between kissing him hungrily and and moving up and down upon his cock, I began a steady rhythm of pleasure for both of us. I never dreamed I could feel so girly and so crazy-in-love while being with any man?
At this point I’d been with Alistair in coitus enough times to know when he was nearing a climax. I knew I’d begun to dribble between my own legs. And the action of his hard penis against my prostate was filling me with much pleasure. I knew I couldn’t hold out much longer when I heard his breathing increasing rapidly.
As I could sense his his moment of passion peak, I shrieked wildly. Then I started to gyrate crazily upon his rock-hard organ. When Alistair did finally begin to ejaculate I could feel his hot semen filling my anal canal. It seemed like it was pumping out in such a large quantity that my rectum could not hold all of it.
My own sperm squirted and dribbled down between my legs. I was sobbing hysterically between kissing Alistair’s face and his lips. I was so emotionally and girlishly drained. At long last I stayed seated upon Alistair’s cock as his erection slowly subsided.
“Oh Alistair, I just adore being with you my lover. Hold me tightly please, and don’t let me go. I simply love you up inside of me you big, manly stud. I don’t know how I can ever be without you Alistair?” I sobbed at long last.
Later, as we munched on some carry-out from a Spanish Deli, I asked him to stay the night.
“Of course I will. You know we’ve never woken up with each other? I thought of that, the other day. I’d like to wake up with you more frequently Francesca. Why don’t you and I put in an offer on the Jasmine Laurent mansion? We can afford it. My mother has decided to have her attorneys finalize the paperwork to make me a full partner in the business,” Alistair informed me.
“The Laurent mansion? It’s gorgeous. You know we’re going to have to masculinize some of the decorating? There are so many pretty rooms. Even my Grandmother’s estate in Quebec didn’t have that much space,” I said.
“Yes, I know. Jasmine is such a fluttery female. The decor is so fussily feminine. I know I’d like to redecorate the game room, the home theater and the workout room. Plus, I’d want my very own Man-Cave and of course I’d prefer my bedroom be manly,” Alistair opined.
“We’d have separate bedrooms?” I asked, coyly.
“Yes. In our social class, even unmarried lovers and newlyweds have separate bedrooms. It’s more for privacy, the storing of separate wardrobes and of course to have private baths. For sex, we’d pick whatever bedroom we wanted to make love in, whenever the mood struck us,” Alistair winked.
“Well I hope the mood would strike us frequently. Like right now I feel like sucking your big cock,” I whispered.
“Oh my, Francesca. What has gotten into you?” Alistair asked, laughingly.
“It’s the hormones. Glynis told me that sooner, rather than later, shortly after I get my monthly boosters, I’d begin to want to have you intimately in a big way. So you’ve got this to look forward to at least once a month,” I said, with my hand on my hip.
“So, do you want that big cock sucked, my Master, sir?” I asked.
“Well yes. But right here? In the dining room?” Alistair asked.
“Why not? Finish your Gazpacho. I’ll just crawl underneath the table. And while I blow you, imagine that I’m sucking you off, in your locked office, underneath your desk at work. Just in case you decide to hire your own personal assistant after you sign the partnership paperwork with your mother? Just think of me, as if I’m submitting my resume right now,” I said as I took Alistair’s cock in my mouth.
You can bet I got the job, too. ;)
Denouement: Laurel Canyon Lady
I’ve always just loved to have a salon cape over my shoulders and be able to look into the wraparound vanity mirror of my very own home beauty salon on a Saturday morning. It’s also been truly comforting to have my very supportive, and often very affectionate Mother-in-Law, Isabella Montenegro, having her hair, nails and face done along with me.
On Saturdays, Alistair has come to enjoy golfing at the Country Club his father belongs to. As if Alistair didn’t have enough to do, his father wants him to take an interest in his Music Production business. Alistair is working on merging the family businesses.
But, back to my home salon. Not every Saturday, but most Saturdays, Isabella and I have come to meet at the home Alistair and I purchased from Jasmine Laurent. We have coffee and bagels, along with wine and makeovers. Christine, who owns our favorite salon, will send over two of her best girls to make us over. “Mother” Isabella and I have become very, very close.
As Francesca, Isabella has been the only real mother I’ve ever had, actually. She was an amazing help counseling me and caring for me after I had my boobs enhanced to a “D” cup brassiere size. She was equally astonishing when at long last, I had my testicles removed, along with having a beautiful, new pussy surgically constructed.
A week after Alistair and I moved into our new home, Alistair proposed marriage, after I’d given him one of my bewildering blow jobs. I insisted on having Mother Isabella announce our engagement at our housewarming party. I also asked that it be Mother Isabella that would give me away at our wedding.
So, when Elaine and Isabella had a falling out and Elaine moved back to New York, the very least I could possibly do was be there for Isabella, with a warm hug, kind words and a daughterly kiss or two to comfort her.
And so, whenever Alistair and his father decide to play 18 holes of golf, we get together and we have Christine’s girls make us beautiful. As a rule Carlotta does me and Pamela takes care of Isabella. We get our hair washed and conditioned. Then we decide if we want to get trims, full haircuts, coloring or even perms.
We laugh a lot and we sip wine. We coo and tease each other as we get mani/pedis. Every once in a while after the stylists have left and we pose in front of full-length mirrors in fresh makeup and sexy outfits, my cell-phone might ring.
“Honey, this is Alistair. Look, babe. Dad wants to go to his offices and have me look over some papers for him. It's a new production contract he hasn’t signed just yet. Then he asked me if I’d have dinner with him and a few drinks. Will you be okay with that? I might not be home until around 8 PM,” Alistair might say.
“Of course my love. Though I’ll miss you. Don’t worry though. I understand you are a busy, entertainment executive. And, I’ll be waiting here patiently with my new makeover ready to greet you when you arrive home,” I say, winking at a pouting Isabella.
When the conversation has ended, I will sashay over to Isabella. She will put an arm around me and kiss me warmly. The first time Isabella ever kissed me was shortly after Elaine moved out, and I went over to her Laurel Canyon mansion to comfort her. Even then, I thought the taste of our lipsticks mingling was just so sensuously perfect.
On this occasion and most others, it will be no different. Our lipsticks are always wet and fresh. Why wouldn’t they be? The beauticians have just done our makeup. Our hair will look stunning. And our hairspray and perfume smell so lovely.
After a lengthy French kiss, I might take Isabella by the hand. We’re going to mess up each other’s makeovers, but I’ll have plenty of time to fix myself up before Alistair sees me. We then fall into bed and I pull my cool satin sheets over us.
“You were always very pretty Francesca. But when you got those big tits and a new pussy, you began to look stunningly beautiful to me. I always thought Elaine could tell that I thought of you lustfully whenever I looked at you. I wonder if she was jealous?” Isabella once asked.
“Come to me my angelic pet. Am I a bad mother for wanting to screw her son’s wife? Speaking of screwing you, I don’t have my strap-on with me. But I can suck your twat and finger fuck you,” Isabella will say as I giggle.
I will then move my body to position my head over Isabella’s pussy. I want to lick Isabella’s clit. Isabella loves it when I suck her puss. Her body will stiffen as soon as I make contact with her clit. She sometimes get’s so aroused she laments in Spanish, which I sometimes don’t quite understand.
But eventually, she squeezes my head between her legs and screams. I know then she’s having a climax.
“Oh Cara Mia. Come to me my heavenly angel. I must suck your big tits and finger your pussy,” she adds, and I giggle and relax in her arms.
What would Alistair say if he knew? Sometimes I think he does know. I recall him sniffing me in bed and asking me if I was wearing the same perfume Isabella wears. I do know that Alistair does love both his mother and I very much. He really wants both of us to be very happy.
What I really think, knowing my man the way I do, is that he would be happy I was comforting his mother after she lost her lover. Until he does say something though, I’ll enjoy my bisexual lifestyle, and my elegant life. And as long as I take care of Alistair sexually, the way I usually do, I doubt he’ll investigate too much.
The End
PS: Look for my next stories. I’m working on two. Born to be Beta and Sissy-in-Law. In Born to be Beta, a brother becomes his sister’s sissy maid. In Sissy-in-Law a divorced sissy becomes his ex-in-laws housekeeper and sexual play thing.
Loving the new storues. Just wondering if finishing some of the older stories is planned?
ReplyDeleteThank you! The question about completing some of the unfinished stories has been asked in the past. I am guessing those would be Sorority Sissy, Makeover at the Mansion, A Concubine for Doctor Rochelle and Intermission? I have honestly attempted to get interested in those stories again to complete them, but there are times when I get writers block and they just go nowhere. I can't force it or it shows and the story ends up being a dud. So no. Unless of course something magically comes to me in the way of creativity. Thank you for inquiring though. I appreciate the concern.
DeleteIn the tale of two sissies we have another interesting story from a talented writer with some neat twists (always a must have ) how underhand of Madame Isabella to use subterfuge to ensnare her son's unbeknown to the hero love,very cleverly written with Ms Isabella's staff acting in concert to gradually draw into their web poor Francois he being focused on the lovely Sondra the Housemaid and the plot twists were extremely well done too,All in all a very good story.
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