By Priscilla Bouffant
I found that both my Fiancee, as well as my mother and sister, had no issues whatsoever with me appearing in their offices Androgynously, or even A La Femme, in spite of me not feeling very comfortable at all with that.
Chapter I: Ms. Martine
I’d met Adriella Martine when my mother, Eileen Greystone, the CEO of Greystone Import/Exports Ltd, had recommended me to Adriella as a manicurist when I was working at the La Belle Femme Beauty Spa.
Adriella was an up and coming Junior Exec with an MBA, who the Greystone HR department had just hired. Myself, I was living at home, milking the fact that I was an heir to a fortune. Unlike my older sister, Tabitha, who was now the CFO of Greystone.
Both mother and Tabitha knew very well that I was dressing En Femme at home, quite frequently as a matter of fact, when they were at the office working late. All they asked of me was that I purchased my very own “Pretties” and didn’t wear their Things.
I also dressed quite Androgynously at the Beauty Spa and always wore girl’s underthings. Although I’d completed two years at a Community College and had an Associates Degree in Business Administration, I didn’t like the idea of office work, especially considering the late hours which mother and Tabitha would expect from me as an Admin at the family business.
When I did at last do Adriella’s nails, we hit it off wonderfully. Within the week she’d called me for a Saturday Evening dinner date. As we discussed the timing and the Logistics, I brought up my attire.
“Adriella, you’ve seen how I dress, coif and look at the Beauty Spa. I even wear light cosmetics and nail polish. Would that be too much for our dinner date?” I asked.
“Oh, of course not Nico. Be yourself honey. You know, you really do ‘Rock’ that Femme-Boi look, Doll. And I wouldn’t be asking you out if I did not find it very attractive. In fact, you might just be wearing too little makeup for a Beauty Spa, you know. On our date feel free to wear a bit extra lipstick as well as perfume if you’d enjoy that. I know that I would,” Adriella opined.
Wow! What a dream-lady Adriella was. I’d been named Nicholas Brent Greystone. My very elderly father had passed away when I was barely a year old. I’d been sort of a “Surprise” baby, when my busy Mother’s birth control pill cycle was more or less out of sync. My sister Tabitha was 8 years older than me. Mother was 30 when I was born.
By then, Mother was up to speed on running the business. Because of my more or less Inherent Femininity, by the time I was 18, I’d insisted on being called “Nico” as I was trying to put on this facade of being a cool, aloof, sort of “Butch” Femme-Boi, which was of course a total contradiction within itself.
Deep down inside of my spirit, I knew that I was a Sissy. And that truth was getting yet more and more, very, very, difficult to conceal.
It would not be long before the least feminine name which Adriella would be calling me was likely Nikki. Dinner that evening was wonderful. After our meal, as Adriella opened the passenger door of her Lexus Sedan in front of the restaurant, she took me aggressively into her arms, kissed me, and said, “I do dearly hope you don’t mind Nico darling, but you’re coming home with me this evening and I’ll be taking you to bed.”
Adriella really took charge once we were in her Boudoir. After having me strip off everything, including the cute lingerie I wore beneath my leather Capri’s, and my billowing Sateen blouse with the high ruffled collar and the Bishop sleeves, she placed me on my back as she kissed all over my smooth, hairless, scented body.
“Oh my, you are just so very Girly, my dearest Nico. Your perfume is intoxicating. Is that Arpege by Jeanne Lanvin? Just so classically feminine. And I love the curls in your brassy blonde tresses. Is that a perm? No? You slept in curlers to look pretty for me? How very, very sweet of you darling,” Adriella concluded.
“Yes, Adriella. The ladies at La Belle Femme have wanted to perm my hair for some time. But there is just so much more that can be done with curlers, rollers and Bobby pins,” I offered.
“Really? Are you a licensed Cosmetologist in addition to being a Nail Tech?” Adriella asked.
“I just did finally get all my credits and I take the Cosmetology exam next week. I had to put beauty school on hold though, when Mummy and my sister Tabitha, held up my monthly stipends from my trust fund, until I completed my Associate’s Studies Degree in Business Administration,” I explained.
“Oh, my poor, dear, sweet little Nico. It does sound as if your Mummy Eileen and your big sister Tabitha, just Baby you sweetheart. Well, I can baby my Nico also, and you are going to adore it. Aren’t you Doll?” Adriella cooed.
“Adriella. What you are doing to my body is phenomenal. I’d love to eat your Pussy if you’d like?” I said.
“There will be more than enough time for that later, my Princess. At this instant I want to mount your stiff little Pee Pee and screw you to the mattress. Obviously neither Mummy Eileen nor your Big sister Tabitha, have put you on Estradiol just yet,” Adriella stated casually.
As Adriella lowered her wet Puss onto my penis, which was already dribbling pre-cum, I gasped enormously. I could feel my cock inside of her and it was as if the suction of her Vagina had swallowed my Dick in it’s totality.
The palms of Adriella’s hands were pressed against my shoulders, and it was as if she were doing push-ups, as the up and down motion of her hips bounced her pussy in a rhythmic pulsation, upon my stiff, male member.
“If you do prefer to titillate my Clitoris, dear Nico, you could slide one or even both of your very lovely manicured hands between our crotches, Love. Yes, that’s it Baby. You’ve found my G-Spot now sweetie. Oh yes. Keep that up honey,” Adriella insisted.
I’d had sex with a few women. Primarily Clients at the La Belle Femme beauty spa. Mostly, Forty and Fifty “Something” Divorcees, looking for a Boy-Toy to easily manipulate. But never had any of them dominated me in the manner which Adriella Martine would begin to Subjugate me that evening.
As her strokes became more intense I could feel she was nearing some sort of Apex. I myself was getting fairly close to my peak. As her breathing increased in intensity she gasped, “Now don’t you dare ejaculate before I climax, you little Fairy Queen. If you do, I can assure you that you will regret it.”
I couldn’t help but subserviently respond to her. My mother and sister assuredly had trained me well. “Oh yes ma’am, Ms. Adriella. I’ll do as you say, ma’am,” I pleaded.
“Oh you bet you will, Dolly Boi,” Adriella replied.
I could almost instinctively sense her intense orgasm was imminent. And then her floodgates really did open. “Oh my gracious this is so very awesome. What a sweet obedient Fuck you are sweetie. I’ll bet later on you do a really nice job eating me out. Oh wow, this is so, so very nice,” Adriella nearly shouted as her body quivered and then I let loose.
I could not hold back any longer and I knew she’d climaxed substantially. The cream flowed from my cock in what seemed to be a very steady stream. I could feel it dripping from her puss onto my thighs. Adriella kissed me full on the mouth laughing.
“I dearly hope I didn’t scare you too very much concerning having a Climax before I did. Honestly I wouldn’t have done much more than spanked your ass with my great-grandmother’s glass-backed, antique hairbrush. And then maybe I’d have wiped your sperm from my puss with my panties and then stuffed those very same pretty panties into your mouth,” Adriella laughed.
As wild as that comment was, I did believe that she meant it, and I know you are wondering why I didn’t run right then and there? However, she already had me within her clutches and I hadn’t a clue. And she was as insatiable as she was irresistible, once she’d had an orgasm. It is said that a lady of 30 years old is at her sexual peak and Adriella certainly was.
By 5 AM, she’d have another climax as I sucked her pussy with her sitting upon my face. She’d also used what she told me was her “Smallest Strap-on” to penetrate my rectum.
“Oh my. You really are a tight little bitch aren't you Nikki honey? We’re going to need to get you stretched out with some butt plugs. You don’t mind me calling you Nikki do you sweetheart? Nico is just a bit too Buff for you. Don’t you think so, Pretty-Boi?” Adriella asked and of course I readily agreed.
Adriella was in tip-top shape from running, playing tennis, horseback riding and even some golfing and racquetball. She “Allowed” me to sleep in until ten that morning, even though she was up by six.
“Well, we’ve missed the fabulous Sunday Brunch at O’Brien’s. We can do lunch at Rafferty’s around two. Let’s shower together Precious,” she added as she took me by the hand and drug me into the bath attached to her boudoir.
In short order I was naked and kneeling at Adriella’s feet with my head between her thighs. As the warm shower water splashed all over me, my lips, tongue and painted fingertips stimulated Adriella’s clitoris as Adriella shampooed and conditioned my hair. Her hips rotated her pudenda as I pleasured her.
Just as Adriella was using the portable shower head to rinse the last of the conditioning treatment from my tresses, her thighs locked against my ears, and her hands pressed against my tresses, as she orgasmed wildly. “Oh what a good sweet boi you are. Yum, you are just so very precious. Let’s make ourselves pretty. I don’t want you wearing anything you wore on our date last night Nikki. Let’s see what I have that should be able to fit you, darling,” Adriella said.
I balked when Adriella laid a swing skirt on her bed along with a pair of 4 inch heels at the bedside.
“What’s the matter Princess?” Adriella asked.
“I’ve never worn a skirt or a dress,” I lied.
The truth was I’d never worn a skirt or dress publicly. But in the privacy of the home where I lived in with Mummy and Tabitha I’d certainly worn numerous skirts and dresses.
“Are the heels too tall? Weren’t those three inch heels you wore on our date?” she asked.
“No ma’am. Those were 2 and a half inch Kittens,” I admitted.
“You are such a Sissy, aren't you? Well, at the very least try on these three inch heels. I do really want you in something Fab and Femme for lunch. Here we are. Wear these High Waisted, Sicilian, Lemon Tile Palazzo Pants, with this Crop Top, Lantern sleeved, Turquoise blouse. And for goodness sake Nikki. Stop your mewling. I have plenty for you to wear, including panties and Silicone Gel Tit Inserts,” Adriella said with a hiss.
Once I was dressed, Adriella had already heated up a set of small hot rollers for me to do my hair.
“I intend to do your makeup and I want you to use plenty of gel products in your hair. I want it shiny and glistening. We’re just a couple of ladies out having lunch together on a Sunday. Use your softest voice and click your tongue and smack your lips on occasion when you speak. Plus use a certain amount of flighty hand gestures. I know you’re likely cautious about being around men, so leave it to me if we need to appear to be Lesbian girlfriends,” Adriella commented.
It would be a first for me to wear my hair “Up” in a curly upsweep, outside the house, which is how Adriella decided it should look. My makeup was a little heavy for lunch and I know she was attempting to make me look sluttish. She added a couple of bracelets to my wrists and removed one set of studs from my pierced ears, to hang a set of dangling turquoise fobs to match my blouse.
She handed me a pink “Clutch” to carry my “Touch up” cosmetics, and with our heels clicking on the pavement we made our way to her BMW sedan. Everyone who worked at “Rafferty’s” seemed to know Adriella, and she asked for a “Quiet table in the rear sun room.”
The hostess who seated us smiled and said, “You ladies follow me. I’ll seat you where you can speak to each other both very privately, as well as intimately.”
“Just one menu Gwen. I’ll be ordering for Nicole,” Adriella said to the Hostess.
Once we’d received our meal, Adriella asked me, “Have you ever thought of severing the Apron strings from Mummy and Tabitha, Nikki? You know, were you to move in with me, you’d have your very own, very private, personal, Boudoir and Bath Suite. You don’t need to decide this very minute. Just think it over. You’d still be very close to the nail salon where you work, and I simply have to think that both Eileen and Tabitha would approve.”
Before I could say anything, Adriella added, “I have an excellent professional as well as personal relationship with both your mother and sister. In fact, your sister and I go out to lunch together and well, at times, it’s as if we were sisters. As for your mother, she has referred to me as her Protege on a number of occasions.”
“Adriella, I’m truly honored you’d consider me to be your roommate. Of course I’ll think it over and discuss it with mother and Tabitha. Truthfully, my very first impulse would be to say that I’d love to move in with you,” I stated.
“Nikki. We’d be much more than just roommates. If it becomes solely up to me, we’ll be lovers, and more,” Adriella said in a truly, sultry tone.
I believe that she already knew, then and there, at that very moment in time, that everything I’d soon be doing, once I moved into her home, would be solely up to her.
As much as I desired to stay the evening, with me having to be at work at 9AM the following morning, I opted to return to the home I more or less shared with mother and Tabitha. I’d hoped I’d be able to sneak in and go right to my Bed and Bath suite but both Mummy and Tabitha were waiting for me in the parlor.
“So there you are. We wondered if Adriella would be keeping you? You must have had a fabulous time?” Mummy said.
“Yes. We insist that you sit down with us and tell us all about it, Little Brother,” Tabitha added.
“Of course. In fact I’ve been on the go and I’d love to sit and relax. We had dinner last night at O’Brien’s. Then lunch today at Rafferty’s,” I began.
“And you spent the evening with Adriella, of course?” Tabitha smiled.
“Yes. That’s true. And this afternoon at lunch, Adriella brought up the subject of she and I becoming roommates,” I stated.
After mother and Tabitha stole glances at each other, Tabitha opined, “That would be simply just a fabulous idea. Don’t you think, mother? Personally Nico, I believe that it would really assist you with gaining some emotional growth as well as a new focus in life.”
“Tabitha is correct Nico. I’m all for it. Adriella is a fabulous woman. She’d be an excellent influence upon you,” my mother agreed.
“I must admit that I truly had such a wonderful weekend. I don’t want to get ahead of myself, but I really do think I’m, in love,” I simpered, nearly bursting into tears. As I wiped my eyes, my smiling mother stood up.
“Come here darling. This is all so very special and wonderful. Give both Mummy and Big Sister a hug and a kiss. We are both so very, very thrilled with this and we are truly happy for you,” Mother stated as I began to sob. I really had become such a Sissy.
Chapter II: A New Regime
“I simply just cannot believe you did this to me Nikki? You not only hid things from me, you lied to me, right to my face. When I asked you to wear a swing skirt to lunch at Rafferty’s you told me you had never worn a skirt or dress. And as it turns out, you have an entire closet full of dresses and skirts. And right here in my home,” Adriella glared.
When I’d moved in with Adriella I knew I had to eventually reveal to her that I “Closet Crossdressed” on a regular basis in my most intimate of moments. But, I hadn’t said a word to her concerning that. In fact, the day I moved in with her, I’d left my Femme Wardrobe in the closet of my bedroom at Mummy’s. I’d waited until Tabitha took Adriella on a business trip to Miami to sneak my Girly things into the closets and dressers of my Boudoir and Bath suite at Adriella’s.
The closets were perfect for hiding such a wardrobe. They were very deep and had two rows of hanger racks per closet. The dressers were sumptuous and it was very easy to obscure most of my intimates. Besides, Adriella wasn’t one to “Peak” into someone’s belongings.
I knew that Adriella had a camera security system but I had no clue that she was in the habit of putting it into 24/7 mode when she went out of town. Initially I had no idea that she would review it when she returned to Westchester after her Miami trip with my sister.
She’d just completed viewing it when I’d returned from a drive to the drugstore, where she had sent me to purchase Strawberry Flavored Douche, Tampons and Sanitary Pads for her. She was seated in the living room and waved to me saying, “Come in here sweetheart. I just mixed us both a whiskey sour. Watch this movie with me. You’ll just love it. In fact you are the star, Princess Nicole.”
I sat down nervously, as she ran an edited film, just of me, dressed to the nines and “Flitting” about the house in high heels, full makeup and perfectly styled tresses. Each and every time I stood up or tried to interject something she’d say, “Sit down and shut up you Prissy little Bitch and watch what I’ve just viewed. And yes you are in very big trouble, girl.”
When the movie was over and she had dressed me down, I began to sob. “Oh, is the Little Sissy’s heart broken? Listen to me you selfish little Pansy. I’ve known about this all along. Your Sister told me about your cute little habit. I’ve waited and waited for you to reveal it to me but no. You decided to keep your little Sissy secret all to yourself. Well Girl, you’ll need to pay for that. Strip down and go into my boudoir. On my vanity you’ll find my Great-Grandmother’s Glass Back Hairbrush. I fully intend to blister your ass with it, and then some.
I returned to the Parlor, as naked as the day I was born, still whimpering and holding the hairbrush.
“Well. Hand it to me and get over my lap you Prissy Fairy. This nice little ass of your’s is going to be so hot and pink when I’m done with it. And please darling. Do not feel too timid to kick and wiggle your legs like a damsel in distress and sob hysterically,” Adriella teased.
“Ouch. Oh please Adriella. Please forgive me. I’ll never lie or hide things from you ever again. Ouch!” I shrieked.
“Oh you can bet your sore little ass you won’t lie or hide anything from me again,” Adriella promised.
I was indeed sobbing hysterically and wiggling my legs like a Sissy Girl when she was finished spanking me. But, she wasn’t done. She very unceremoniously pushed me off of her lap and down onto the living room carpet. As I whimpered she said, “My Pussy just gets so very Fucking wet when I spank a lying little Bitch like you. Here baby. I have a present for you. Stand up. And open that mouth nice and wide.”
When I did, Adriella’s slacks were off and I could see her Pussy Bush. In her hands were her panties which I now knew she’d rubbed into her Vagina. She stuffed the wet panties into my mouth, grabbed me by the ear and walked me to a corner of the living room.
“Now just keep your nose in that corner until I decide what else I need to do to shame you into realizing just who the Freaking Boss is in this home,” Adriella stated.
I could hear her walking around, happily humming a tune when she finally said, “Get into your Boudoir Sissy. And keep those panties in your mouth until I say you can remove them.”
When I arrived into my room there was a rubber sheet on top of the bedspread. “Face down girl. I’m giving you an enema. Then I’m going to fit you with your very first butt plug. It’s for your own good you know. That way, eventually, I can stop using my Baby Strap-on every time I want to rail your asshole.”
As the warm, soapy water flowed into me, Adriella pulled the panties from my mouth and let me know I could hand wash them in my sink once I was finally wearing my very first, of a steadily increasing size, of butt plugs. When I thought I was actually going to burst, Adriella stopped the flow of the enema and told me to hold it in, until she gave me permission to finally relieve myself.
Honestly, receiving that enema was one of the most undignified things I’d ever done. What a relief it was to finally “release” the contents into the toilet bowl.
“Now for the fun part. You wiped yourself nice and clean, correct? Great. Now, once again, lay face down while I get you all nice and lubed up, Princess. Here comes your very first plug. Relax. I’m very skilled at inserting these,” she said as she rotated the plug into my rectum. When it was finally all the way in I gasped in relief.
Then Adriella had me put on a panty brief and sit at my vanity while she instructed me on exactly how she wanted me to do my makeup. Next she had me brush my hair “Up” into a “Do” and pin a white ribbon into it.
“Now, put on some high heels, go into the kitchen and I’ll put you into a nice pink apron and you can make me lunch,” Adriella said.
I next minced around the kitchen in my heels, panty and apron. My ass was sore from the enema, the butt plug and the spanking. I noted between the heels and the plug, my ass really swayed prettily and girlishly. As Adriella dined on her lunch and sipped her beverage I cleaned up around the sink. Once Adriella was done eating, I completed the cleanup.
Just as I put away the dishes and cup she’d used, Adriella came up behind me and kissed my neck. It felt so good, having her show me affection. As she ran her fingers through my sprayed hair, she kissed the side of my face and nibbled my ear. She turned me around and kissed me on the mouth, and as I closed my eyes girlishly, it felt so very good.
“I have the feeling that someone is going to be my good girl from now on, and never lie to me or hide anything from ever again. Isn’t that true, Nicole?” Adriella asked.
“Oh yes Adriella. Never again will I ever deceive you. Oh, I love you Adriella. Oh, please kiss me again,” I begged as she did.
“I’m going to be taking you to bed soon. You can eat my puss, and then I’ll put you on your back and screw you. First though, I want to tell you that there are going to be some changes around here. And you may not enjoy them. And if you want, you are free to leave honey. The doors here swing both ways girl,” Adriella cautioned me.
“Oh no Adriella. I’ll never leave. I want you. I adore you. I’ll do whatever you want me to do. I’ll wear whatever you want me to wear. I’ll look and act however you desire me to. I just always want to be with you Adriella,” I cooed.
“Well then. Let’s go into my boudoir sweetie,” Adriella stated.
Adriella laid on her back and I placed my head between her thighs. Her Puss tasted so wonderfully, and the scent of her vagina was just heavenly. Just an incredible miasma of powders, lotions, perfumes and moisturizers all mingling to excite and stimulate my senses.
Adriella was simply just an amazing sexual partner. She could go from being in a very relaxed, almost meditative state as I begin licking her clit, to a wildly, Tigress-like huntress as she climbed atop my smooth, hairless body to either mount my penis with her cunt or enter my rectum with her strap-on.
That afternoon, she breathed deeply and sighed as I sucked at her clitoris. I could tell I’d aroused her from the way She’d grabbed my head and wound her perfectly manicured fingers into my tight, springy curls. As she did so, her well-formed, shapely thighs pressed against my cheeks.
“Oh yes, my darling Nicole. Your pink lips and magical tongue have aroused my button. I won’t allow you to stop, but I know you won’t try to stop, will you? You exist to pleasure me darling,” Adriella spoke huskily.
Her arousal excited me and I redoubled my efforts. Soon I felt my Mistress’s body tense. Then she arched her back and began to thrust her pelvis snugly against my mouth as her juices smeared my lipstick and oozed onto my heavily, made up face.
“Yes! Oh yes!” Adriella screeched.
Her thighs were so very tight against my ears, and when the tension finally did relax, I realized the denouement of her climax was in progress. Her arched back returned to the mattress as she released a passionate sigh. “Oh what a good, good, Girlfriend you are Nicole. And honey you are Nicole now, you know that I hope, my dearest. Any hot little bitch that can doll up as well as you just needs to be a girl. I’ll come up with a sexy middle name for you very, very soon,” Adriella promised.
I sincerely did not realize how soon it would be, prior to the day that I would officially become Nicole.
“I cannot believe this but I am far too spent to screw you with my Pussy. Reach into the drawer of the Lamp-stand table on the right side of my bed and remove a tube of lubricant and the Curved vibrator. Yes that one. Good girl. And now, get that small pack of tissues from my Vanity, right next to the atomizer of Opium Parfum. Excellent,” Adriella added.
“Now stand close to me as I slide out your butt plug. There. Wrap that in some tissue and place it on the Lamp table. Now kneel on the bed, on all fours, my sexy little Sissy. I’ll lube up your butt, smear a touch of lube on your cock, and now Voila!” Adriella laughed as she began to masturbate me and move the pulsing vibrator in and out of my anus.
Adriella stood beside the bed in order to have full control of what she was about to do to me. As the vibrator slid in and out of my rectum, the curved end began to contact my prostate and send tingling sensations throughout my body. My penis was fully extended and Adriella hummed, oohed, and sniggered as I sighed and gasped in maddening pleasure.
I would one day discover that I could be tied down upon a vanity bench, and my prostate could be “Milked” without Adriella ever so much as lightly touching what would one day be my shrinking cock. That day, however, my penis was swollen to its maximum proportions.
At the very moment that I could have imagined my testicle sack literally bursting, my cock jerked and spasmed, emitting a stream of thick, gooey ejaculate onto the bedspread. The noisier my gasps became the louder Adriella’s laughter was. I was noisily screeching when I at last collapsed upon the bed.
I was in dizzying ecstasy as Adriella kissed the back of my neck. We both laid there exhausted until the often businesslike Adriella stated, “I intend to call out and have dinner delivered. I’ll order for you. I want you plumping up in certain places but I’ll be the controlling factor in that.”
After we ate, I obediently cleaned up. Then Adriella remarked, “You’ll be giving me a bath, prior to taking a bath of your own. You already know how to do it, so I insist that you set your hair and sleep in curlers, as well as with moisturizer on your face this evening. Make certain you make the roller set snug by using a hair band as a wrap. Of course cover everything with a hairnet.”
“Really Nicole, setting your hair at night and using moisturizer on your face regularly, is an excellent form of Discipline for you. And truly, it is in perfect harmony with the plans I have for you, which we’ll discuss after breakfast in my home office tomorrow. And I’m not like some sort of male, who doesn’t enjoy sleeping with their girlfriend, Fiancee or wife, with they have their hair rolled up and face cream on. I want you in my bed tonight, Nicole,” Adriella insisted.
When I awoke to prepare breakfast Adriella instructed me not to remove my hairs curlers until she gave me permission to. Once I’d cleaned things up after breakfast I went to her home office and sat down across from her in front of her large Mahogany desk.
“Nicole, I want you to understand that everything I’ve decided for your future is in your best interests, as well in Concert with the wishes of your Mother Eileen and you sister Tabitha, who only want the very best in life for you,” Adriella began.
“Very soon I will be needing you to fill in at the office for my Admin Kellie, who is going out on extended Maternity Leave. So, when you go into La Belle Femme tomorrow, you’ll need to give them two weeks notice. Shortly after you’ll be coming into the office to ‘Shadow’ Kellie and train as her temporary replacement. I do hope you are okay with all of that, Nicole?” Adriella asked.
“Well yes. May I ask if I’ll be expected to dress femininely?” I said.
“Yes. And your mother already has our legal department working on getting you a State of New York official I.D. denoting you as a Trans-Female. That includes a driver’s license. You have been trending in that direction since your mid-teen years, Nicole. You cannot deny that,” Adriella added.
“I guess I have. It’s just that this all seems so sudden,” I mused.
“Truthfully, in your case, Nicole, sooner is better than later. You must admit Nicole, with an older sister wrapped up in her education, a mother who had to suddenly take over a corporation after your father’s death, and no father in your life, you lacked a strong disciplinarian to guide you. I fully intend to be that strict disciplinarian Nicole, and give you the guidance and direction you have for so very long, desperately need,” Adriella insisted.
I was suddenly filled with emotion and began to sob. Nicole came from behind her desk, put her arms around me and lifted me to my feet. She hugged me to her shoulder and kissed me upon my cheek.
“You’ve needed someone such as me in your life, for far too long my dearest Nicole. You’ve hidden behind the facade of Nico forever. Haven’t you, dear? You can now be who you were meant to be, darling. Now, I want you to get dressed. We are going to go on a Sunday outing together. I’ll explain everything very shortly,” Adriella said.
As Adriella attired herself she assisted me with dressing. As she padded the brassiere I’d be wearing, with Silicone inserts she remarked, “A light dosage of Estradiol and some figure training foundation garments could give you some permanence to the shapeliness a girl should have.”
When I was finally attired in a skirt, blouse and heels, perfumed, and wearing makeup, nail polish and jewelry, Adriella informed me, “We won’t be doing your hair sweetie.”
“I can’t go out wearing curlers, can I?” I asked.
“Of course you can. We’re just a couple of women doing some light grocery shopping. A young lady with her hair up in curlers, wearing a hairnet and a fashionable head scarf, just might have a date with her stud that evening and simply wants her tresses to look perfectly coiffured. Besides, grocery stores aren’t crowded at all on Sunday. The next time we leave the house together your hair will look great and it won’t be up in rollers. It will very likely be in a curly Bob,” Adriella smiled.
It was my first real time out in public in a skirt and blouse. With my hair in curlers it was a good test of my female poise and bearing. I was very selective in my speech, mannerisms and movements. Of course the butt plug and high heels really did assist me in taking mincing steps and sashaying my hips properly.
I removed the curlers after we returned with the groceries, however I’d sleep in a hairdo bonnet until just prior to putting on my makeup Monday morning. Shortly after arriving at La Belle Femme, I let the owner, Marcella, know I’d be leaving in two weeks. She and all the girls were thrilled that I’d eventually be working as an Admin for my girlfriend Adriella.
“It really is about time you put your Associates Degree in Business to use, Nico,” Marcella agreed.
Though none of the girls yet knew about “Nicole” they would soon find out. They gave me a “Going Away” party and invited Mother, Tabitha and Adriella, who had no trouble letting everyone know of my impending transformation into Nicole.
“Well then, you and Adriella will have to come in and have a Girly Spa Day together as soon as you can,” Marcella insisted.
Adriella wasted no time seeing to it that I began my Estradiol Hormone Replacement Therapy. The following Saturday we drove to a GYN clinic that specialized in working with Transgender Therapies. They were open to the public Tuesday through Fridays to meet the regular GYN needs of Genetic Females. However Saturdays they had special Weekend hours for Transgender Females.
I’d first need to see the GYN, Doctor Jennifer Tyler. “Nicole. Is that correct? You are now using the name Nicole at present? Great. In speaking to your family members, which is important, though it doesn’t always occur, you have presented En Femme, though primarily Androgynously, since your mid teens. Agreed?” Doctor Tyler asked.
“Yes ma’am,” I said.
“Now you will still have to see our Psychologist as well as the Endocrinologist. My job is to tell you everything concerning the physical affects, Nicole. Naturally your bosom and hips will grow and round out. Your nipples will first begin to itch and feel a little sore. We’ll be giving you some cream to apply to help with that. Your body hair will grow very sparsely if at all, and the hair on your head will become thicker and fuller,” Doctor Tyler began.
“You’re quite young, so the Estradiol is likely to not affect your ability to attain and maintain an erection too very much. At least not at the dosages we’ll be prescribing. Now I want to send you to our Psychologist Doctor Melanie Peel to discuss the emotional changes you’ll undergo. Adriella has been speaking with her. While you’re with Doctor Peel I’ll be going over things with Adriella,” Doctor Tyler said.
“Hello Nicole. I’m Doctor Peel. Nice to meet you. Now that you know the physical changes you’ll undergo, allow me to fill you in on the emotional changes. First off. Do you cry very much, Nicole?” Doctor Peel asked.
“Yes somewhat,” I admitted.
“Well the Estradiol is known to cause emotional outbursts, frequently over silly things. If you and your girlfriend have a spat you may become upset and begin to get overtly emotional meaning you will start to blubber like a baby. It’s possible you may become upset when you break a fingernail, or get a run in one of your stockings. A romantic ‘Chick-Flick’ just might send you into an absolute tizzy. Are you following me?” Doctor Peel asked.
"Umm.. yes."
“However there are some very positive aspects of Estradiol treatments. You will become far more obedient and compliant than you have ever been. This of course will endear you to your girlfriend as well as your immediate family and co-workers. Which in your case is just perfect as I understand you’ll soon be employed as a Administrative Assistant,” the doctor added.
My injections began that day and once we picked up my prescriptions at the pharmacy we headed off in a direction away from Adriella’s home.
“We’re are we going, Adriella?” I asked.
“It’s a surprise. Do not ask me to ruin it. Okay?” Adriella said.
When we pulled into the parking lot of La Belle Femme where I had worked, I asked, “Why are we stopping here?”
“Now why else would we be stopping here? The day of your going away party I purchased a Girly Spa Day for two. We’ll even have some champagne and a light lunch. Let’s relax, my girlfriend and lover,” Adriella added.
I’ve had my hair “Done” before, of course. And my nails and makeup. But Adriella had paid for the works, including a facial and complete full body zip-wax and massage. I adored the Ice-Blonde coloring she had them put in my hair, and the Pixie Cut and French Manicure were To Die For.
However, the thorough Full Body Zip-Waxing, especially on my Pubic Patch and my Butt-Crack were a bit much. But the very best part besides the massage, was setting there with Adriella right after our makeup and manicures were done and we were waiting for the nail polish to dry.
“Melanie already told me that you got an erection during the massage she gave you, Nicole,” Adriella whispered.
“Oh no. I didn’t think she noticed. I feel terrible Adriella,” I whimpered.
“Hmm. I’ll likely forgive you, by the time we get home. At least you didn’t ask her to jerk you off,” Adriella purred.
“Oh no. I’d never do that,” I gulped.
“Oh really? Never? Am I supposed to really believe that? Anyway, just the idea made me wet. And seeing they waxed your ass-crack, I’ve decided to use the next size up from my ‘Little Boy’ dildo to fuck you when we get home. Simply to let you know who the Boss Lady is in this relationship. Don’t fret. I’ll use plenty of lube. Oh. And bye the way Sissy. You look very pretty,” Adriella whispered.
Chapter III: “Ms. Martine’s Office, Nicole Speaking”
It had been six months since my visit to the GYN’s offices. I had developed a presentable, Post-pubescent sized, 34 A+ set of “Girls” and my ass had rounded out to a shapely, 34” sized bubble, due to the Estradiol injections, plus the tablets, lotions and creams which I’d been taught to use. From the strict low carb, “White” protein only diet, that Adriella insisted upon, my 5’9” frame was a svelte 123 pounds with a 25” un-corseted waistline.
Due to my strict figure training I really only needed a waistline “Cinch” to promote a shapely 22 inch waist. I’d been into La Belle Femme for 3 lip-plumping treatments, each a month apart from the next.
My “Pretty” mouth had that pouty, Bee-Stung look. Or as Adriella frequently would remark, I had a gorgeous set of Plump, “Cocksucker” lips. I was becoming so enamored with the way I looked that I’d went so far as to having my hair, face and even nails, “Done” for my new driver’s license photo. I’d had my hair color changed from the “Icy” blonde they had put in my tresses during the “Girly Spa Day” I’d had with Adriella, to a deep, rich, “Chocolaty” Brunette.
I’d went with plenty of Deep Crimson shades for that photo including my lips, earrings, nail polish and blouse. I was now legally a Trans-Female named Nicole Brianna Greystone. I hoped to one day be Mrs. Nicole Brianna Martine, but as of then, nothing of that sort had yet to be mentioned.
The good news was that I had been promoted. I was no longer Adriella’s Administrative Assistant. Due to Adriella’s promotion from Junior Exec to Individual Accounts Executive, I was now a Personal Executive Assistant. I answered all of “Ms. Martine’s” calls, and either routed them directly to her, took a message down, or sent the call to her voice mail.
The greatest benefit of the position was traveling on business trips with Adriella. Especially if we journeyed without any other employees present on the excursion. There is just something so very terribly romantic, about checking into a luxury hotel suite with your stunning girlfriend and very sexy, domineering, lady boss, knowing you’ll be catering to her every wish and whim, without exception, for the next several days.
Even prior to being pumped full of female hormones I was putty in Adriella’s hands. One I’d begun HRT, however, I had morphed into an absolutely obsequious, groveling, Milquetoast, who was willing to bow and scrape to serve Adriella, as a Lady-in-Waiting might serve her Queen.
Much to Adriella’s pleasure, through the use of a “Kit” of Vaginal Dilators (Butt-Plugs) she’d given me, my rectum was now “Right-Sized” which was the terminology Adriella had used. I could now take her largest Strap-on into my anus. It was a very special one she’d proudly purchased in Paris, France which she referred to as “Madame DeParis”.
This particular strap-on fit perfectly against her Vagina, and was designed with a “Pinky” finger sized rubber “Nub” which contacted Adriella’s Clitoris. So as she screwed me, she would also stimulate her Clit.
We were traveling to Atlanta to do a presentation at Clarington Industries, a Privately owned, Family company that imported Mega Yacht’s throughout the Deep South and Southeast. When we arrived at their offices we were led into Arthur Clarington’s Executive Assistant’s office. He and his son Dirk Clarington and two attorney’s would be present at our sales pitch.
“Will you need one of our young female admins for the coffee and pastry service, Ms. Martine?” Gladys Elspeth, Arthur Clarington’s Personal Secretary asked.
“No we won’t. Just as long as the coffee is brewed and the pastries are there, my Girl Nicole will take care of that Ms. Elspeth. Won’t you Nicole?” Adriella winked.
I was certainly dressed, coiffed and “painted” to kill. I wore this satiny, turquoise, long sleeved Pussy Bow blouse, with a snug, black leather mini-skirt. My dark, seamless hosiery were held up by garter straps. My newly dyed, very dark brunette tresses had recently been permed for the first time and beautifully shaped and stylized.
I had to admit though, that sitting through the girlish ritual of being permed, was nearly as feminizing an experience as being “Fitted” for my very first Custom Contoured brassiere. My fingernails were extra elongated and curved, as well as painted a dreamy Coral Pink. As instructed by Adriella I wore four-inch, strappy heels.
The blush and eyeshadow I wore were quite vivid and in a nearly burgundy shade. My lipstick as it often was, had been done in a double coat of wet-look Guerlain Vermillion.
As I knocked lightly at the door, and then proceeded into the Clarington Industries Conference room we had been assigned, I did a prim curtsey and introduced myself.
“Good morning gentleman. I’m Nicole, Ms. Martine’s Personal Secretary. How would you like your coffee. Mister Clarington Senior, sir?”
After I’d served everyone’s coffee I said, “There are some lovely pastries here gentleman. Various Danishes and Strudels. Anyone? Enjoy. I’ll return to continue serving while Ms. Martine gives her presentation.”
Adriella, as she usually managed to, had all four of the men eating out of her hand. It was agreed that we’d return in the morning to negotiate further. When we returned to our hotel I was looking forward to either a late lunch or early dinner when Adriella received a call.
“Hello, Mister Clarington. Adriella Martine. Well yes. I can call you Dirk. And feel free to refer to me as Adriella,” she said, as she walked away into the bedroom we had shared the evening prior.
When she walked out of the bedroom smiling, she said, “Well it looks as if you’ll be sealing this deal for Greystone, Nicole. Won’t your mother and sister be proud of you.”
“Dirk Clarington, like most wealthy, Sons of the South, is married to a well-to-do, but empty-headed, Southern Belle, that has no earthly clue just what Dirk does, on any given day, when he is out of her range of vision. In any event, he keeps a Rooftop Suite at the Atlanta Omni where he has sexual trysts with any number of females,” Adriella began.
“I just got off the phone with Dirk and he told me he liked very much what he saw of you at the meeting. Now I explained to him that you were not yet, completely a girl, and that you did have a moderately functioning male appendage, but that you would just love to pleasure him in any way that he desired,” Adriella went on.
“You told him what?” I gasped.
“Relax. By the way, you can’t really go prancing into the Omni under the guise of being Mr. Clarington’s Massage Therapist dressed the way you are. You look like a Call Girl. Change into that pair of light brown leather slacks and the Burgundy top we got you at Filene’s when we went on that Boston trip. Your hair an makeup are fine. Wear some dangly earrings and some kitten heels,” Adriella added.
“What do you expect me to do with him?” I asked, nearly in a panic.
“Settle down Princess. This is just business. It’s a one afternoon stand. He’s already married, you know. It’s not even a date. I expect you to do whatever he wants you to do. Probably no more than a Blow-job and a Butt-Fuck. I don’t know that he’s kinky, but even if he is, he might just want to tie you up and maybe spank you?” Adriella surmised.
“So. Get changed. And save yourself some time. Remove your butt plug now. Then I’ll call you an Uber. When you get to the Omni go to the front desk and say you are Mr. Dirk Clarington’s Masseuse and he’s expecting you in his Rooftop Suite, 510. Once you get there, act flirty and do whatever he wants you to do. When you leave his suite, call me and I’ll have an Uber sent to the front of the hotel,” Adriella shrugged.
“This deal is huge for Greystone. We’ll be the Northeast Rep for Clarington’s Mega Yacht Sales and Chandlery in Newport, Cape Cod, Hyannis, The Hamptons, and anywhere up thru Maine. Your mother will be over the moon when I return to Westchester with that signed contract. Okay. You look great. Now lets see. Perfect. Hadji is your Uber driver,” Adriella said as she led me into the hallway outside of our suite.
Dirk Clarington was indeed a very handsome, manly Alpha Stud. He greeted me at the door, saying, “Nicole, you look just as phenomenal as you looked at the office earlier. Please come in. What would you like to drink? How about some Grand Marnier Cordon Rouge?”
He then took me by the hand and and sat me down on a plush sofa. He began discussing what he liked about Adriella’s presentation. As I sipped the ample glass of Cognac, it went right to my head and relaxed me. Before I knew it, Dirk had his arm around me and was kissing me on my wet lips. I opened my mouth so our tongues could link and I leaned into his muscular chest.
It dawned on me later that between the hormones and the Grand Marnier, I was just about as compliant as I could have possibly been. I even began contemplating how romantic it was, to be with this married man in his plush, private roof top suite, overlooking the city.
“Nicole. I think you know what I want. I’m going to stand up. Why don’t you kneel at my feet and get me ready to screw you,” Dirk said as he stood up.
I very obediently got on my knees and leaned my head against his chest. As his fingers ran thru my curled hair, and he held my head in his hands, I massaged his cock thru his slacks and then began to unzip his pants and loosen his belt. His pants dropped to his ankles and when I lowered his underwear, I took the moist end of his hardened cock in between my lips.
It seemed as if I had not been sucking his hard cock and playing with his testicles too very long when Dirk said, “Why don’t we both strip from the waist down and you may go lay on your back in the bedroom?”
Dirk stepped out of his shoes and socks as well as his slacks and underwear. Then, as an afterthought he took off his tie and jacket. After removing my slacks, heels and panties, I put my Kitten Heels back on. I was still wearing my garter belt and hose and I wanted to protect my stockings. Dirk had me lay upon my back, and Then slide my ass to the edge of the bed.
He lubricated my asshole liberally, prior to smearing the same Jelly onto his cock. Then, he took hold of my nicely shaped, smooth, hairless legs, by the lower calves, and rested my ankles upon his shoulders. He was practically lifting me up. At last he began to slide his cock into my rectum.
He worked his penis in and out of my ass slowly, as I gasped. I really felt completely helpless as he slid the entirety of his penis up inside of me and began to pump his hard cock in and out. I could really do very little, other than wiggle my butt crazily, as I gasped and cooed.
I had become Dirk’s dangling, bouncing, Rag Doll, Fuck Toy. Honestly, Adriella had screwed me many times with her strap-ons. But the very manly, Alpha, Dirk Clarington, was fucking me as if he owned me.
By the time Dirk was ready to climax into my rectum, I was screeching, sobbing and whimpering in utter, shivering helplessness. However, my total helplessness was simply so very excitingly erotic. As Dirk’s semen flooded deep into my anus, there was a flow of cream from my cock that would not seem to cease.
As Dirk’s cock pulsed and spasmed, my penis streamed white Gooey ejaculate endlessly. It dribbled down my abdomen as Dirk filled my anus to overflowing. Then, I truly knew what it was to be fucked by a real man.
Once I had cleaned up, I contacted Adriella to send an Uber. I was just getting back to our hotel as Adriella was getting off the phone with Dirk.
“Oh baby, you did fabulous. We can drop by Clarington’s tomorrow at 9AM and pick up a signed contract, and be on our 2 PM flight back to Kennedy. Give me a hug. How do you feel Doll? That look in your eyes tells me that you really enjoyed being Butt-Fucked with a real cock. You need to get into a hot bath tub and relax. Your mother and sister are going to adore you for this,” Adriella said as she ran the water into the tub and added the salts and oils.
As I bathed, Adriella asked me, “Is your butt sore Princess? Was he really big, Sweet-thing?”
“Yes, I’m a little sore there, and he was about the same size as Madame DeParis, your favorite strap-on. And please don’t be cross with me Adriella. But I enjoyed it. You might even say that I loved being Buggered. And I’d do it again with any man that was as handsome, masculine and a true Alpha such as Dirk Clarington is,” I admitted.
“And why would I be cross with you Nicole? I’m thrilled for you baby. You know what being a girl is all about now. And honey, I’d have you do it again, if it would close any deal that I’d been working on for six months,” Adriella admitted.
I stood nervously the following morning as the papers were signed. Just prior to us leaving, Dirk Clarington took me aside and said, “I hope I can see you again, Nicole, if either you come to Atlanta or I make it to New York. I enjoyed every minute of the time we had together,” Dirk said as he kissed me on the lips.
After a brief gasp I added, “It was lovely for me Dirk. I’d really enjoy it if we could be together once again.”
On the way to the airport I repeated for Adriella what had passed between Dirk and I after the deal was signed.
“Honey. I’m very proud of you. It’s not every Sissy that impresses a male that much the very first time she screws one. I cannot wait to tell Eileen and Tabitha,” Adriella added.
We arrived at Kennedy far too late on a Friday evening for even my mother and sister to be at the offices. However we were there bright and early Monday morning, and before even Adriella had time to get to my mother’s office, Mother was tapping on the glass door to enter my outer office.
“Good morning Mummy. Adriella was just going to bring the signed contract to your desk,” I said.
“I’ll bet she was. She texted me just before the two of you boarded the plane that the deal was in,” mother added just as Tabitha entered the office.
“Why don’t you both go in and see Adriella. I’ll bring in coffee for three,” I said as I got up and minced to the coffee maker. As I put three cups of coffee the way they enjoyed it, as well as three pastries, all on a tray, I could hear chatter and then laughter coming from Adriella’s office.
By the time I walked thru the doorway with the refreshments, Mummy, Adriella and Tabitha were all laughing hysterically.
“Well there She is. Our secret weapon. There should be a nice bonus in your next check for the way that you took one for the Greystone Corporation, Nicole. And congratulations on no longer being both an oral or anal virgin honey,” my sister Tabitha said, as she wiped tears of laughter from her eyes.
I know I was blushing through my makeup. “Well thank you Tabitha. The bonus will be appreciated,” I said as I served the coffee and pastries.
“And Adriella stated that you enjoyed your Tryst with Dirk Clarington. So much so that the two of you made a tentative date to see each other again,” my mother added.
“Truthfully, Dirk Clarington was an absolute hunk and he knew exactly what to do with a girl. Most girls just are not lucky enough to have a man such as him, upon their first time, when their butt is finally pinned to a mattress. However, I was just so very, very fortunate,” I admitted, happily, practically cooing.
It would happen to occur, on the occasion of Adriella and I celebrating my very first bonus as an employee of Greystone, that Adriella would decide to thrill me beyond my wildest dreams. We were having dinner at O’Brien’s, where we’d went for our very 1st date. After the meal while we had coffee and cheesecake for dessert, Adriella said, “Now close your eyes darling, and give me your left hand.”
I felt so very sexy that evening. My hair was “Up.” I was wearing a cream colored pencil skirt with a color matching Pussy-Bow blouse and pink, three inch heeled pumps. My makeup was luxuriant and vivid, with an extra coat of Coral lipstick. My nails were pointy, curved and French Manicured.
I held my left hand out, my wrist was limp and dangly. Then I felt it. I gasped. I had not opened my eyes, but I knew what it was. I could feel the band encircle my ring finger.
“You may open your eyes now, my Princess,” Adriella said, huskily.
“Oh my heavens. Oh Adriella my love. It’s just so very stunningly gorgeous. Do you mean?” I asked as my voice trailed off. The most beautiful diamond engagement ring was nestled around my finger.
“Yes my darling. We are to be married. You are to become my wife,” Adriella said.
I was very near to blubbering and I knew my eyes were tearing up. Just as any Mistress would, Adriella did not propose marriage. She simply told me we were to marry. That evening in Adriella’s bed, the lovemaking was beyond incredible.
I melted into her arms. As always Adriella would take the lead. I was her puppet upon a string. Initially she had me lay upon my back while she mounted me with her dripping wet puss. As she slid my cock inside of her I whimpered girlishly. I knew by them I was no longer any sort of a boy at all, and certainly not a “Straight” one.
As I once have read in a teasing, Capped Photo, “Honey, Straight Boys don’t get wet panties when they put on lipstick.”
Adriella pumped her Vagina up and down upon my penis, cautioning me, “Do not dare to ejaculate you Sissy Bitch.”
Then she pulled her pussy back off my cock and got her favorite strap-on, “Madame DeParis,” out of her panty drawer, and lubed up my asshole as well as her dildo. As she slid the dildo into my rectum, she pulled up, on my legs, and rested my ankles on her shoulders. It startled me that she was so fit and strong, compared to how slender, dainty and Sylphlike that I’d become.
As she railed my ass, she passionately said, “Oh, how I love the way that the nub on this Faux Cock fingers my clit.”
When Adriella did come, she very vigorously pounded my rectum, and stimulated my Love-Button Prostate, to the point that I screeched like a Harpy until I collapsed into a simpering whimper, once again unable to control my deepest emotions. Any longer I became a dithering pansy as far as my sensitive outbursts were concerned.
“Oh my what a melodramatic Girly-girl I now have on my hands. Everything will be just wonderful Princess. Mum-mum is taking care of everything from here on. Including her Best Girl,” Adriella assured me.
It took me so long to shower that evening. I simply just laid there in the combination of our passionate sweat, sperm and Pussy Juice, so very contented with the fact that I was to be Adriella’s wife. That I would be, Nicole Brianna Martine. Isn’t that just what every Little Sissy dreams of?
Chapter IV: An Open Marriage
Our wedding took place at our family estate. If I had not mentioned it just yet, yes, my mother, sister, as well as Adriella and her mother, were all members of the Cassandra Coterie. I would be expected to meet with Adriella’s mother, the High Priestess, Myla, prior to the ceremony, to fully understand what she excepted of me as her “Sissy-in-Law.”
As Madame Myla was to conduct the marriage ceremony, she had dressed in a tux. With me in my Bridal gown, full makeup, stylized tresses, plumped lips, and tall heels, I felt incredibly girlish, ineffectual and quite vulnerable.
“I must say, Nicole, that your mother and sister did an incredible job with you. I realize my daughter merely added the finishing touches to what I find to be an amazing Sissification. In the ways of our Coterie I see you as a work of our art. A creation of our female dominance and a statement of our full power and control. I don’t see my daughter having any trouble at all in having the full and complete say in what will obviously be a Female Led Relationship,” Madame Myla smirked.
“Your mother will be paddling you?” Myla asked.
“Yes High Priestess. Mistress Adriella is having her use your Sorority paddle from Wellesley,” I said humbly.
“Oh how very wonderful. That paddle has heated up more than a few Sissies’ asses,” Myla said proudly.
As I minced, no tottered, into the Grand Room of our estate, no organ played “Here comes the Bride.” Instead, the Eerie musical strains, of ballads played by Celtic Shield Maidens, as they went into battle, filled the rafters. High Priestess Myla stood at the podium alongside my sister Tabitha, and my future Spouse, Adriella. Tabitha was Adriella’s “Best Woman.”
Tabitha and Adriella both wore tuxes. Tabitha’s was white and Adriella’s was in Burgundy. My mother walked beside me, guiding me to my right, also in a White Tux, as the “Grand Mater” of honor, as was customary for a Coterie wedding with a Sissy Bride. Her left hand was firmly placed in the small of my back at my very slender, snugged in waist.
As we neared the Ceremonial platform, though my eyes were lowered self-consciously, I could just barely see the spanking paddle in my sister Tabitha’s right hand. As we reached the lowest step of the platform my mother maneuvered me into a kneeling position and used her left hand to lower my forehead to the next step.
I was now, in effect, bowing to my Mistress/Spouse and the Sisterhood as a whole. I held my bouquet of pansies tightly as my hands were actually tied together with a pink ribbon. The music stopped and the High Priestess Myla began her Soliloquy.
“Dearest Grand Maters, Maters, Sisters and Friends. We are here today to witness, finalize and sanctify, in the eyes of our Goddesses, and our Sisterhood, the Marriage of my only daughter, Adriella Martine, to a Sissy who she has found to be worthy to serve her. Adriella, do you vow to take this Sissy in marriage as your maid, slave and concubine, and to care for her, discipline her and protect her as if she were a child?” High Priestess Myla asked.
“Yes, High Priestess I do,” Adriella agreed.
“Sissy Nicole. Do you vow to love, honor, worship and obey Adriella, to take her last name, to cater to her whims and wishes, and remain always beautiful and girlish?” Priestess Myla asked.
“Yes, High Priestess Myla, I do solemnly vow,” I agreed. I was nearly shaking with my forehead pressed to the carpeting on the second step of the platform.
“Who holds the paddle to discipline the Sissy?” Myla asked.
“I do Priestess Myla,” Tabitha said.
“And I will paddle her,” my mother stated.
“Is it possible to raise her gown?” Myla asked.
“Yes. And as she is caged and plugged, I see no issue with lowering her panty brief. Only if it pleases the Priestess, I would enjoy paddling her on her bare bottom, Madame Priestess,” Mummy said.
“It would please me very much, Sister Eileen,” Myla agreed.
I could feel Mummy raising my gown and laying the hem on the small of my back. Next she slipped the waistband of my panty brief to the middle of my thighs.
“You may begin her paddling, Sister,” Myla stated.
“Gasp!” The first of three paddle strokes fell solidly upon by butt.
“Hail Cassandra!” Resounded thru the Grand room.
“Oh my, ouch!” I screeched.
“All hail Aphrodite!” Roared the Sisterhood members.
“Oh wow! My poor butt!” I murmured.
“All hail the Sisterhood!” Echoed throughout the Grand room.
I was sobbing as Mummy restored my Panty and lowered my gown. Then she stood me up and gently wiped the tears from my eyes with a hanky.
“The best is yet to come my gorgeous, Sissy Daughter. Let us proceed up the steps to meet your Spouse,” Mummy said.
Mummy led me to the top step where Adriella awaited me. I kept my head bowed. I was not to be permitted to raise my head or eyes to look at Adriella until she lifted my head by raising it with her fingers beneath my chin.
Mummy handed me to Adriella and then walked back down the steps. Tabitha remained. Adriella turned me to face her by taking me by both my arms. Then she lifted my head and looked into my eyes.
“Kiss me, my Princess Bride,” she smiled, as she took me into her arms and kissed me forcefully, taking my breath away.
She untied my wrists, to symbolize I could now touch her. She handed my pansies to Tabitha. Then she removed my Diamond engagement ring and placed it on the ring finger of my right hand. Finally she took the wedding ring from Tabitha.
“With this ring, I claim you as my property and my wife, and I dedicate you as a Bride of Cassandra. Kneel and kiss the toes of my high heels,” Adriella declared as I dropped to my knees.
After I kissed the very toes of her shiny, black heels, she pulled me to my feet and turned me towards the wedding audience and said, as they cheered, “Tonight I will bed this Trollop in my marriage bed!”
****************
We honeymooned on Barbados. I just loved it on the sandy beaches in the hot sun when Adriella and I would cover each other in suntan lotion. And the lovemaking in our hotel Rooftop suite was amazing.
However, as a Sissy Wife I wanted to have the most amazing figure and always look extra girly, and the Estrogen finally did take its toll on my “Boy” parts. I could of course still pleasure Adriella with my mouth, lips, fingers and tongue. And I could use a vibrator on her puss. But, as she would later tell me it just wasn’t the same.
“Please darling Nicole, do not be upset with me. Your figure is too die for, my love. I’m so very proud of you when we go out, or when you strut around the office and everyone there knows that you belong to me. But it’s just been so, so, long, since I’ve had a cock inside of me. I really do miss it,” Adriella practically pleaded, which wasn’t quite like her.
I began to sob. I acted like such a Sissy. Which of course, I really am.
“Oh for goodness sake Nicole. Let me finish. I am not selfish and I am not greedy. I want to share with you. And I want you to have the very same experience with a man which I desire, so that you will not only enjoy what I am missing, but you’ll also realize what it means to me to have a man inside of me,” Adriella intoned.
I paused, slightly confused, but I did stop whimpering. “Hmm? Explain further please?” I asked.
“Of course, Baby Doll. I want us both to have boyfriends. And I know just the two men for us. You know that your mother and sister are big investors with Hamilton Funds in Boston. And they’re so very important that both Lance and Edward Hamilton, the sons of the owner and his heirs, come down to New York once a month just to take Eileen and Tabitha to lunch and go over their investments with them. And they usually stay a few days after,” Adriella began.
“Well I was talking to the younger brother Edward, and I know he’s attracted to me, and he also told me his brother Lance has a real thing for Femmes like you, and they’d both be really interested in a night out with us. What do you think? I mean Lance, the older brother is a stud just like Dirk Clarington, don’t you think?”
“I don’t know Adriella. I mean we’re married. And you want us to date a couple of guys and have sex with them?” I asked.
“You’re just being a Silly Sissy Nicole. We won’t be living with them. It would be a couple of days a month. We’d still be married and have sex with each other. Why not do this? We’ll just give it a try next month. They’ll come down on Friday, they’ll take your mother and sister to lunch, and we’ll meet them for dinner,” Adriella insisted.
Whatever Adriella wanted, Adriella would always get. A few weeks later we met Lance and Edward Hamilton for dinner at Adriella’s favorite restaurant, O’Brien’s. I decided that if I was going to meet a man for dinner and eventually have sex with him, I was going to look very appealing.
I’d done my dark brunette hair in a real “Teased,” fluffed out “Do,” with a white, pinned bow on the left side. I wore a very snug, cream-colored, cable knit, mini, sweater dress, with sheer hose, beige four-inch heeled pumps, and I was dripping in both jewelry and perfume.
My nail polish and makeup were lush, vibrant and full. At the restaurant I limply extended my hand to Lance Hamilton. I loved what I saw. The older of the two Hamilton brothers was an absolute manly, Alpha hunk. As he took my hand, he leaned over and gave me a “Peck” upon my heavily blushed cheek.
I ordered light fare, though I imbibed generously in two cocktails. Lance and Edward had rented a car. When we departed from the restaurant Adriella insisted that she drive her vehicle with Edward as the passenger, and that I ride along with Lance, to give him directions to our residence.
On the drive from the restaurant I took it upon myself to reach over and massage Lance’s crotch. After another cocktail at the house, Lance and I were ready for hot sex. We both undressed ourselves as soon as we were in my boudoir, and shortly after, we were both in bed French Kissing.
Lance paid me a lovely compliment when he said, “Every time I saw you at your Mother's office, I could never believe that you were not a genetic female. And you have the most amazing set of breasts and the most gorgeous ass I’ve ever seen on any woman.”
“Such an adorable thing to say, Lance. Well then, let me suck your cock, and I’ll give you the most fabulous Blow-Job you’ve ever had,” I answered taking his penis into my hands and then encircling it within my wet, plump, crimson, “Cocksucker” lips.
His dick grew quickly in my mouth and was soon rock hard. “It’s up to you my lover. You’re the male. Tell me what you want. I can suck you until you shoot your load and I’ll swallow every last drop. Or you can screw my Sissy Ass, in any fashion you prefer,” I offered.
“There will be plenty of time later for you to drink my ejaculate. I’d enjoy taking you Doggie-Style,” Lance said.
“That’s fabulous. Your wish is my command, my Master. Allow me to lubricate you and then I’ll coat my asshole with the same Jelly,” I stated.
I then knelt on all fours as Lance slowly and masterfully entered my rectum with his stiffened cock. It felt just so very amazing. Visions of Dirk Clarington fucking me wildly came rushing back. Adriella was simply, just so definitely correct, when she’d said there was nothing to compare to being Fucked by a real man.
To this very day, I just thoroughly crave a man’s penis inside of me. And so does Adriella for that matter. As Lance drove his hardened shaft in and out of my butt, I responded to every manly stroke with a wiggle and a bump of my plump, girly ass. I could feel his cock swelling to what seemed to be its maximum proportions.
My Sissy Clit was partially erect. Not really enough to penetrate a female or a Sissy of course, but enough to give me some spurting cream, once I climaxed. Before Lance eventually ejaculated, I felt my penis spasm and I spurted semen all over the comforter.
When Lance eventually blew his load, I could feel my asshole filling up, prior to the overflow of semen eventually leaking out of my rectum. We both collapsed to the bed with me very needfully snuggling into Lance’s well-muscled chest.
Later that evening I began to warm up Lance’s cock by playing with it. Very soon he was “Tit-Fucking” me while my head bobbed and I sucked his cock. When he finally orgasmed some of the sperm splattered all over my face and hair. However I did swallow a good portion of it.
Our new boyfriends stayed the entire weekend, and after they drove off, I hugged Adriella very passionately. “Oh Adriella you were so correct. What a fabulous weekend. We have to do that once again,” I pleaded.
“Oh but we will, my dear sweet Sissy Wife. I talked Edward into the men coming down every other weekend. We’ll pick them up at the airport on the alternate weekends when they aren’t doing business with Eileen and Tabitha,” Adriella promised.
Having these two men in our lives brought Adriella and I even closer. Just not in the way one might think.
The Denouement
The bathtub was draining. My hair was up in curlers. My Tanning Salon, tanned skin, was fully coated in scented moisturizer. My makeup was Vampishly done and I was dressed in a Coral Pink Peignoir set with Crimson Marabou Heels. It was a Saturday and Lance was at the Golf Course with his father and brother.
My plan as always was to meet Lance in the foyer, with my hair and nails “Done” and me on my knees with my head bowed. I had always wanted to be the consummate, 1950’s Stepford Style Wife.
Adriella and I still love each other. Just not as Mistress and Sissy wife. We’re more like sisters or BFF’s. It just happened. Our divorce was amicable and based on “Irreconcilable Circumstances.”
I had decided to move in with Lance. I became his Concubine. Adriella stated that she wanted to once again play the field.
When Lance arrived home from the course, he of course found me kneeling and ready to serve him in any way possible. “Why not suck my cock while I sip on a Scotch and Water, Nicole?” Lance asked.
I could barely wait for the Ejaculate to coat my throat and mouth. I always did like just a dribble on my heavily painted lips.
Ended and Postscript to Follow.
Priscilla did a few interviews for various Mags, with Adriella, Mummy and Myself. I’ll show the cover pics, and in the future expect the interviews to eventually be posted.
****My most Gracious Thanks, to the very Amazing, Miss Nicky8787 at Deviant Art for granting me the artistic license to do a story based on her talented art work, and the ideas contained in her captioned photos as well as her Magazine covers. Kisses Nicky Girl.**** Priscilla Gay Bouffant
Email: priscillagaybouffant@gmail.com









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