My wife, Daphne’s, lifelong girlfriend, Lisette, a Psychiatrist, was uncomfortable with my crossdressing, and encouraged Daphne to go into “Couples Therapy” with me. I was convinced it was not necessary. I mean, after all, it wasn’t as if I were Bisexual or Gay!.... Correct?? I have to secretly admit, Lisette's younger innocent brother Stefan is very cute and delicious. That means nothing about my sexuality.... right?
*Note from Priscilla: “This is semi-autobiographical, as well as filled with fantasy. Sometimes we don’t explore an avenue that we later on wish that we had traversed. My Darling Estefania might have been within my grasp? Not that I regret my current life’s situation. But it’s fun dreaming what it might have been like with a Sweet, Sissy, Girlfriend for a lover.”
Chapter I: Les Bellas Fashionistas
We were at a Costume party at Lisette’s when I met Lisette’s brother, Stefan. He was beyond gorgeous. He was svelte, and nearly Sylph-like, similar to a fashion model. He had thick, dark, wavy locks just like his Half-Latina, Half French, Sister, Lisette. He was pretty enough to eat. As a Sissy Crossdresser, it was the first time that I thought I could possibly be bisexual? But never Gay, of course.
I tried my best to hide my attraction for him. I made casual conversation and did my very best not to stare. He was one of the Prettiest young boys I’d ever seen. I simply had to find out more about him. I especially needed to know if he was old enough to be fucked. I was that hot for him.
On the drive home I couldn’t help myself. I asked, “There must be at least a few years between Lisette and her brother, isn’t there Daphne?”
“Yes. I believe so, Blair. Oh excuse me. Your using your Sabrina voice, aren’t you, darling.? Yes, Sabrina. Lisette is my age, at 32. I recall her saying that Stefan just turned 19,” Daphne said.
“It sounded as if he’s been living with Lisette?” I asked.
“Yes he is. Lisette is trying to help him. He isn’t in college and he doesn’t have a job. He’s had a few delinquency issues and a little drug use. He’s easily influenced by his peer group. His mother sent him to live with Lisette to get him away from his old friends,” Daphne explained.
“I could easily employ him at the salon. I’m looking for someone to answer the phone, do appointments and occasionally do shampoos and conditioning treatments. But, most young boys his age really don’t want to tell anyone they work at a beauty parlor,” I shrugged.
“Hmm? I don’t know? I’ll ask Lisette. What would the pay be?” Daphne asked.
“Because he’s your best friend’s brother, and he really needs a job, I could match Amazon’s, $20.00 dollars an hour. Plus he’d get tips doing the shampoos and conditions,” I agreed.
“Oh Blair. That’s just so very sweet of you. I’ll tell Lisette. For that sort of compensation, for any 19 year old male, even the embarrassment of saying he worked at a Beauty Parlor would be far outweighed,” Daphne readily agreed.
At 25 years old, I was seven years younger than Daphne. We’d met 3 years after she’d left grad studies, at Columbia School of business. I was 19 then, and she was 26. I’d done her hair for an awards ceremony, that took place where she worked. It was a whirlwind courtship, mostly upon her part. Three years later she wanted to help me get started in owning my own salon. We’d already been living together all that time.
But I got cold feet on ownership, even joint ownership of the salon, saying, “I truly don’t know if I’m ready for that, Daphne. Why don’t I attempt managing it, and you take on the ownership” I asked, and she agreed.
Above the salon was a very nice two bedroom apartment with a bath and a half, that Daphne decided to have remodeled and used as a rental property.
It was shortly after we closed on the salon property, that we were married. We hadn’t been dating very long when I told her all about my Femme, alter-ego, Sabrina. At that time she thought it was cute. We experimented with “Sabrina” for a year or so sexually, before I actually began to become “Sabrina” around the house, and even when we went out for an evening.
Of course anytime there was a costume event I became Sabrina. Lisette, who had a Psychiatric practice, and was a childhood friend of Daphne’s was one of the first people to actually openly speak negatively concerning me being a Crossdresser. So, it actually did surprise me when Lisette called me concerning my potential hiring of her brother.
“Hello, Blair? I truly want to thank you for offering Stefan a job. And he will take it, if indeed the offer is still open? Right now I need to tell you that the apparel he wears isn’t quite what would be suitable for a Full-Service Salon and Spa such a your’s. So I’ll be loaning him some of my less feminine outfits until we can get his wardrobe up to speed,” Lisette said.
“You and Stefan are more than welcome Lisette. Have him let me know when he wants to come in to fill out the paperwork. And he need not concern himself with how he dresses on that day. But yes, we do have a certain dress code at ‘The Sophisticated Lady’ Salon and Day Spa,” I agreed.
“As for transportation, Stefan can commute with me and work the same hours that I work,” I offered.
“Oh that would be fantastic Blair, and so very kind of you. I have seen how you and the girls at your salon dress, so I’ll see to it that Stefan is properly attired. He has that thick, long wavy hair. What should I do about that, to keep it from getting in the way, of the services he may perform?” Lisette asked.
“Oh, you could put it up in a bun, or he could wear it in a ponytail. I’d gel it heavily to keep it in place,” I said.
“You know Blair, he’s spoken of wearing it shorter,” Lisette added.
“Oh no. Those locks are far too lovely to cut very much at all. I’d suggest a trim to clean up the splits. And then I’d put in a perm, or a body wave. The curl would shorten his tresses enough to make his hair look more shapely and manageable. I would do it for him at no charge,” I offered.
“Oh. You are just such a sweetheart, Blair. I know we’ve had issues, and I really think I’ve misjudged you?” Lisette admitted.
“No harm and no foul Lisette. Bring Stefan by this Saturday for the paperwork and a little walk thru and introduction. Don’t fret over what he wears Saturday. I’ll pick him up on Monday for work. I’ll see you Saturday, Lisette,” I said.
Monday, I was really very impressed and surprised with the way Lisette had dressed her brother for his first day at the salon. If she had been concerned over me ever Crossdressing, she certainly didn’t characterize “Androgyny” as any form of Transvestism. Head to toes, Stefan epitomized the picture of an effeminate, Swishy, Sissy Hairdresser.
Not that I didn’t frequently take on that same type of appearance. Though I was impressed with the lengths Lisette had went to, in assuring her brother, “Fit-in” properly in the atmosphere of a salon.
Stefan was wearing a pair of Cordovan Ballet flats, with what appeared to be, dark nylon hosiery.
As he already did have a somewhat, svelte, girlish frame, Lisette’s grey, pant suit combo, with a Burgundy, Camisole top, fit the young male perfectly. It turned me on, just thinking about him wearing panties, and then allowing me to put some lipstick and eye makeup on him. My burgeoning Bisexuality was in full bloom.
It was his hair that really presented a darling, Girly “Look” for me, though. Lisette frequently depended upon me, as to showing her how to “Affix” her tresses, for the very professional look of a “Doctor,” which she required, when she saw clients in her Psychiatry office. Even my wife Daphne would request me to aid her with her workplace presentation as an Executive Money Manager.
And apparently Lisette had never done a “Man-Bun” for anyone, including her brother? As it turned out that morning, Stefan’s hair was in more of a “French” Roll, than anything else. For me, it was perfect and I didn’t say a thing. He’d had his ears pierced as young males his age did, and two pert, pearl studs graced each of his ear lobes.
Along with the French Roll, he really looked cute. When we arrived at the salon, I turned Stefan over to Deidre, my Assistant Manager for training. She immediately took him to the reception desk and got him started on the appointment book. I had clients all day long, and really didn’t have time to track Stefan as the salon was very busy.
I was doing the hair of a Chevy Chase Matron, Beverly Hayden, when Bev remarked cattily, “Well, I love the new Shampoo girl, Blair. It’s about time you hired another effeminate male like yourself.”
“Beverly? I know your speaking of Stefan. But neither of us are hardly effeminate,” I protested.
‘Oh stop it Blair. I’ve seen you dolled up at Charity events with your wife Daphne. Nobody looks as good as you do, when you dress as a female. Unless of course, they work at it. Little Stefan isn’t your new boyfriend is he?” Beverly asked.
“Beverly, now you are implying that both Stefan and I are either Gay or Bi-Sexual. You’re being naughty Bev,” I teased.
“Well. He and you dress quite alike. Does his girlfriend dress him for the salon, the same way Daphne dresses you every morning?” Bev said, teasingly.
It was true, in a way. When Daphne assisted me with actually managing the salon, she insisted that women did feel more comfortable with male stylists that attired themselves in a more androgyne fashion.
“If you’re going to dress femininely on occasion Blair, there is nothing wrong with you Coming Out a little at the salon. There is really no sense in you hiding that side of you, publicly,” Daphne had chided me.
Truthfully, I really had plans for Stefan. On the drive home, I asked him how he enjoyed his first day.
“Things went well. It really is going to be different, working around and with, so many ladies, though. It’s a little embarrassing to admit it, but I am really very shy and withdrawn in the company of Women and young girls. Especially young girls. I really don’t have a lot of experience with dating,” Stefan admitted.
To me, Stefan really sounded, effeminately vulnerable. And that truly excited me, ever so, terribly. I’d denied being “Bi” or even “Gay” for so long. However, I’d just never been in the position to be mentoring such a beautifully lovely young male, such as Stefan was.
I bided my time, until Lisette and my wife, Daphne, took an entire “Girl’s Only” week at a North Carolina, Island, Beach house, with some of their Sorority Sisters from College. I’d have Stefan all to myself and I knew I’d be recruiting him for some kissing, fondling and hopefully more.
I just wasn’t certain how far either of us were willing to go? It was going to be a real adventure. I hatched my plan towards the end of the work week when the girls would be launching their stay in Carolina.
“Are you still considering a Perm or Body Wave, Stefan? With Daphne away, I’d have plenty of time and space to do your hair in our home salon, which Daphne had a contractor put in, after we purchased the house,” I said.
“Hmm? Yes, Lisette has mentioned that salon. I think she said you had done her hair there a few times? It just might be more comfortable for me to have a perm put in at your home salon, than at The Sophisticated Lady? You know, the girls at the salon, sometimes tease me about being some sort of Femme,” Stefan blushed,
We were standing at my Lexus, getting ready to climb in and make the drive to where Stefan lived with his sister, Lisette, when he added, “They also sometimes tease me about being your boyfriend or even your girlfriend. There’s no telling how much they would mock me if you gave me a perm at the salon?” Stefan continued.
“Oh you poor young boy,” I said, throwing my arms around him, squeezing him to my chest, and patting his back consolingly. Just being in that sort of close, intimate contact with him gave me an erection, which I hoped he couldn’t feel against his thigh?
I actually really wanted to kiss his neck and then his cheek. But I restrained myself.
“Hopefully they don’t tease me when I turn up next Monday with a perm in my hair?” Stefan added.
“Let’s plan on it around 10 AM at my house. Can you use Lisette’s vehicle while she’s gone? I know they are taking Daphne’s SUV to the beach. They’ll leave around 5 AM I think?” I opined.
Everything was set. Daphne departed our place at around 4:30 AM. I gave her 20 or 30 minutes to get away, and then I began my preparation to greet Stefan, with me dressed and dolled up as Sabrina. I began with a scented bath and shaved my legs. I pretty much always kept my body as free of hair as possible with weekly depilatory applications.
Next I got into a steamy tub of water, with plenty of scented girly oils and perfumed bath salts. I shampooed and conditioned my hair and even added a creme rinse. Once I’d toweled dry, I moisturized head to toe, and used a powder puff to smell even prettier. I was going all out. I then slipped into a pair of high-heeled bedroom slippers and put on a satiny kimono.
Then I sat at a vanity in “Sabrina’s” Boudoir and began to set my hair on medium-small plastic curlers. I’d just had my hair colored in a soft, Champagne blonde, and then cut and styled into in a Bobbed Pixie. The “Bixie” was parted on the left side and fell to the tips of my ear lobes.
It was a really sexy, cute styling and color, and I decided to “Spice” it up even more, for Stefan, with a roller set. Besides. Sitting under a hair dryer, doing my nails, with my hair up in curlers, was such a “Girly” thing to do. I decided to go with medium-small, plastic rollers and setting gel, to give it a firm hold. I was really looking forward to some heavy action in bed later on, that just might “Muss” it up a little.
I was just really taking so much care with my “look” that I really hoped Stefan would appreciate it. As the salon-style hair dryer whirred, I chose a really striking Lilac color for my nail polish. I’d always made it a “Must” that my nail shade matched my lips. I dearly hoped that Stefan could fall in love with Sabrina.
When my hair was at last dry enough for styling, and prior to actually plucking out the rollers, I decided to dress. I had some very nice “Pre-Laced” waist cinches that I’d been encouraged to purchase by Daphne. We’d picked those up at a cute shop in Fort Lauderdale, owned and operated by a Crossdresser and “Her” Mistress/Spouse.
These were laced very tightly with the back-lacing, and could be removed and then worn later, with the hooks and snaps in the front. In reality, Daphne had “Tired” of lacing my into a corset, and with these, unless there was a weight loss/weight gain adjustment to be made, I could dress myself as “Sabrina” with only a little bit more than a normal effort.
With the corselet on, I even had a little bit of a “Boob” formed from the fatty tissue of the flesh at my pecs, being squeezed upwards and outward. I decided to go with a lightly padded training bra, a garter belt, sheer hose and regular panties, along with a form-fitting dress. I wanted to make certain my penis was very accessible.
The dress was in a Beige-Colored shade, with a scoop neckline. I then went with the identical shade of three-inch pumps. I was then ready to apply my cosmetics do my hair and dab on some seductive perfume.
There is something about sitting on a vanity bench in front of a large mirror, and seeing one’s self with a head full of curlers, while applying makeup, that is ultimately so very feminizing. As I painted my face I took great pains to enhance my Lilac Tinted lips, and to contour my eyes seductively. I wanted no doubts in Stefan’s (Estefania’s) mind that I was available for sex.
With a second shiny coat of coloring applied to my mouth, I next set out the three sets of earrings and one set of bracelets I’d be wearing. Then I plucked the rollers from my hair. I deftly styled my Pixie-Bob, into a curly fondue of waves and tendrils. I sprayed everything into place and then sat, within earshot of the doorway, reading the latest issue of Marie Claire.
When the doorbell chimed, I checked my dainty wristwatch and minced to the door. It simply had to be “Estefania” and it was! I smiled cheerily and welcomed my guest in. He acted surprised at my appearance and asked, “Blair, is that really you?”
“Yes silly. Come in. But it isn’t Blair today, it’s Sabrina, Doll. Didn’t I mention I was going to Femme-up when I did your hair, sweetie? Oh, maybe I forgot then? But, what do you think? Aren’t you going to tell me how pretty I look?” I simpered.
“Well? Uh? Yes. Of course. I’ve always thought you looked very pretty as Sabrina, you know. In fact, I’ve always wondered what it must be like to doll up like you do?” Stefan said.
“Well, there’s one way to find out, you know? Just try it yourself. You know what? You could try it today after your perm. I guarantee you’d look fabulous. You could even wear what you have on right now. Just add some makeup and wear your permed hair up, or something?” I suggested.
“Hmm? Maybe but I don’t know?” Stefan added.
I looked him over as I had him sit so I could wrap and tape the soft, protective paper around his swan-like, girlish neck. Then I made the future “Miss Estefania” stand while I put “Her” into a bright, pink cape, that I’d set aside just for my new girlfriend.
Stefan was wearing ballet flats, which he’d now gotten used to as footwear. He had on a pair of Girl’s, Baby Blue, embroidered “Skinny” jeans, with a white Camisole top. He was nice and ripe for plucking, I thought.
I put some “Girly” pop music on the home audio, that included Taylor Swift, Miley Cyrus, and Beyonce, as I shampooed and conditioned Stefan’s hair, with the most fruity-scented products I could find. Then I began to lightly trim his absolutely gorgeous locks. I’d already set out the Perm Kit and the wave rods in plain sight. Just so he was fully aware that he was getting a permanent wave.
Thought the entire procedure, from Shampoo, to cutting his hair, along with the perm and comb-out process, I took every opportunity possible to touch, pet, and rub my body up against Stefan. I wanted to make him feel comfortable with our bodies touching and later being intimately in contact.
I’d decided on giving him a Stacked, Spiral Perm, which would really come out Extra-Girly. He’d eventually have the most deliciously, delightful, and darling, corkscrews, tendrils and curlicues, gracing his lovely tresses. I couldn’t wait for him to view his styling in the vanity mirror.
In the meantime I wrapped his perm very carefully. I wanted him to get the full effect and I planned on using as many different colored rods as I could, so Stefan could not help but feel ultra-feminine as he saw his perm develop. I’d be observing his response very carefully.
It took some time to wind his perm. Then I very slowly and precisely wrapped the cotton gauze, around the circumference of the perm rods, and pulled and knotted it together nice and snugly. I cued into the look on Stefan’s face and it was apparent that this gentle, mostly effeminate boy was mesmerized by his present appearance in the mirror.
“Take one of these gauzes in each hand, sweetie, and dab at any perm solution that might drip. Here. Let me put this plastic trough around the back of your neck to keep any of the lotion away from your collar,” I gently whispered.
As I applied the perm solution I could see his cute, little button nose, wiggle from the odorous scent. Once I had emptied the entire bottle I wiped around Stefan’s forehead and cheeks, prior to having him stand for the walk to the hair dryer.
Prior to placing him underneath the dryer, I placed a plastic cap over the wave rods. His eyes appeared to be watering slightly. I leaned over and asked, “Is everything okay, Stefan?”
“Yes. I just didn’t know the smell of a perm was so strong,” he said.
“Mummy never gave Lisette a home perm?” I asked.
“She may have, but we are about 12 years apart in age. Did you say you wanted me to read this Marie Claire magazine to learn more about ladies’s tastes in hair, fashion and makeup?” Stefan asked.
“Yes I would Doll,” I added, gently touching him on his upper arm with the tips of my fingers as I called him Doll.
Once I tested the intensity of a few of Stefan’s curls, while he was under the dryer, I decided to do a rinse and then add the neutralizer. He was going to have a simply adorable, head full of very feminine spirals. After the neutralizer had taken I gave my new, Sweet Thing, another rinse, prior to toweling off his very, prissy tresses, and taking him back to my styling vanity.
As I removed the waving rods, Stefan could not keep his eyes from viewing himself in the mirror. He was astonishingly mesmerized by the pretty, bouncy curls that had formed atop his head. Once the wave rods were all removed, I used a lilac tinted towel to scrunch some of the slight dampness from Stefan’s curls.
Then I used a little styling pomade on the tips of my fingers to begin Stefan’s stylization. He looked simply gorgeous. With a warm blow dryer, some finger and comb styling, along with a deft brush, I outdid myself shaping his bunches of corkscrews and curls into a lovely hair styling. Stefan sighed as he peered at himself.
“I think it’s time we played with some makeup sweetie, don’t you?” I cooed almost lustfully.
“Well yes, if you must Sabrina darling,” Stefan answered.
I couldn’t wait. I spun his moveable chair away from the mirror to face me. Then I tilted the chair back slightly as I gazed into his pretty dark-brown eyes. His entire face was my palette now and I planned on beautifying it wonderfully. As his shiny locks were dark brunette I’d stay with very vivid crimson’s and coppery tones.
I wanted his lips and cheeks to light up and his eyes to really pop. Stefan looked up at me with his eyes wide and occasionally closed them as I put on his foundation. I thinned his brows slightly, though I really wanted to wax those, but I thought I’d save that for another time.
“Now. Once I pretty you up, we can’t keep calling you Stefan. I’m Sabrina right now so it isn’t fair that I have a pretty girl’s name and you have a boy’s appellation. Let’s see, you will be Estefania, a hot Chica Latina,” I teased.
“Oh, I like that. I’d adore being a sexy Latina for you. Just so very, very hot and very sexy,” Stefan giggled. If he wasn’t already Gay or Bisexual, he would be very soon.
I finally finished Estefania’s makeover with a brilliant coat of Deep, Cherry Red, by Runway Rogue. Then I had “Her” stand up as I brushed and pinned her hair into an upsweep. Then I walked her towards a full length mirror and posed her, seductively, with her hand on her hip.
“Whoa. Unreal. Both Mummy and Lisette would tease me about me being pretty enough to be a girl. Well, I guess I really am, aren’t I Sabrina? Thank you so very much, Sabrina,” Estefania said, turning towards me and placing her hands on my shoulders.
That’s all I needed. “Please Estefania. Just a little kiss, please? You’ve really never kissed, until you’ve kissed a girl who is wearing lipstick and you’re wearing lipstick too, you know? Oh the taste of lipsticks melding is so exciting. Daphne and I have done it,” I pleaded.
“Yes. Of course. I think that would be delightful Sabrina. Why not? We’ve come this far, haven’t we?” Estefania said as our lips met and we melted into each other’s arms.
The kiss was long, investigative and passionate, as most “First” kisses usually are. Our tongues intertwined as we explored each other’s mouths. Estefania’s hands roamed over my back and shoulders, as mine squeezed and probed her butt.
This just wasn’t the first kiss that Estefania and I had between us. I know for me, it was the first time I’d kissed any person that was not a true, genetic female. I was certain it was the same for Estefania.
“Estefania honey. Why don’t we go and lay down together, Princess? Let’s really get to know each other,” I whispered.
“Yes, off course, Miss Sabrina. And why not? I think that would be very lovely,” my new, Girly-Boy tittered, femininely.
With my hand in the small of her back and resting on her ass, I directed Estefania to the very same boudoir that Daphne and I usually made love in. We both stripped down slowly, kissing each other intermittently and rubbing each other’s bodies until we became comfortable laying side by side, in bed.
We looked lovingly into each other’s eyes, as my hand took hold of Estefania’s hardened penis. I knew instantly what I was going to do with that Rock-Hard piece of meat.
“Let me suck you darling?” I asked.
Chapter II: Suburban Domestication
“Of course, my love. Please do? I think that would be so, very much amazing,” Estefania whispered.
I maneuvered myself in the “69” position with my lover. I was giving Estefania, the option to enjoy me sucking her as she relaxed. Or she could play with or suck my penis if she so desired. Initially as I took her cock into my mouth, she sighed and enjoyed what I was doing to her.
“Oh Sabrina darling. This is so much more than amazing. I’ve never experienced anything like this,” my Sissy Girl sighed as I licked her balls, sucked lightly on them, and then I swallowed her gorgeous penis up to the hilt, suctioning it between my painted lips and my beautifully blushed cheeks.
The tip of her cock nearly touched my throat but I didn’t care as long as it wasn’t gagging me. I sucked and licked her erection hungrily as I fondled her testicles. Then Estefania began to play with my cock. Wow! That was so very wonderful. I wondered how far we’d go from this point? And then I imagined how amazing it was that we would have an entire week together to really get to know the limits of our eroticism.
When at last my darling Estefania finally took me into her mouth, it gave my body shivering chills, from my painted toes, through my spine, to the hair-spray scented tips of my my curled, Champagne-Blonde tresses. I felt as if I were crazily in love. I began to realize then, and I do know now, that I’d never experienced that sort of sexual thrill or sensuous union with anyone, including Daphne.
But then, that mattered very little to me. If indeed, It was to be my fate, to become involved in a “Lipstick Lesbian" affair, with another Sissy, then so be it. As far as I was concerned, whether I was the “Butch” or the “Femme” in the coupling, it was very safe to say, that I then felt far more passionate about Estefania than anyone else in my lifetime.
Estefania was doing a fabulous job of sucking my dick. Though, she was so excited that she was literally “Humping” my mouth as I sucked her. I adored her enthusiasm. I could feel that she was closing in on a climax. I was fabulously aroused also. The closer that Estefania progressed towards a climax, the more intense her efforts became, to give me a fabulous blow job.
She was now sucking and slurping so vigorously that I wondered if I would not be the one to orgasm first? However, I could feel her cock expanding in my mouth. Though that was an unfamiliar sensation for me, I still realized that it was the sign of an imminent ejaculation about to occur.
Then, Estefania “Came” in a gusher of thick, creamy, warm, gooey sperm. The virtual geyser which “She” pumped out, filled my mouth and throat until I wondered if I could possibly swallow all of it. Indeed a few drops did drip from my lips to my chin. On her part, Estefania elicited a number of muffled, girly screeches, as she still held my penis between her crimson lips.
I could barely contain myself and at long last I erupted in a climactic surge that resulted in my cock spasming and my back arching, and a loud squeal emitting from within me. Instead of swallowing my milky seed, though, Estefania pulled my cock from her mouth. As she held my penis tightly in both of her soft, elegant hands, she allowed my “Cum” to spray all over her face and hair as she laughed giddily from the spectacle.
For a few moments we both laid upon the bed, breathing heavily and touching one another’s bodies lightly. Then Estefania appealed to me.
“Please, Sabrina my darling. Come here please? Come to me and hug me to your body, please dear? Oh yes, that’s it girl. Oh how I love having you close to me. Oh, that’s so nice,” she added, with my sperm still dripping from her beautiful hair, and droplets of ejaculate at the corners of her mouth and the tip of her chin.
“Oh that was so wonderful. When I arrived here, I knew this was to be a very special day, when I saw you so exotically made up as Sabrina. This was something that was a long time in coming, and a real eventuality. A suppressed dream come true, my dearest Sabrina,” Estefania revealed.
“Oh you don’t know how long I have held these girlish emotions within myself. When I was younger, before Daddy returned to Colombia and left Mummy, Lisette and me to fend for ourselves, I would watch Mummy do her hair and makeup and wish it were me. I’d even pose, looking into her vanity mirror and wonder if I were pretty,” Estefania admitted.
“Those were my secrets. Later, once Daddy had gone, I’d do the same, peering into Lisette’s room as she prepared for her dates with boys. And, of course I believed these secrets of mine to be so very shameful. Real boys did not want to fix their hair or wear makeup. And a real boy would never, ever wonder if he were pretty,” Estefania sighed.
“These past weeks, going into the salon with you, and seeing how chill and mellow the atmosphere was, that existed in a Beauty Parlor, among the ladies, changed all of that. I wanted to fully immerse myself into everything associated with the Salon Experience. And now, you’ve made that and more possible, my lovely Sabrina,” Estefania giggled.
She laid her sperm soaked hair against my face and then kissed me, depositing my own gooey sperm upon my face. I reached to her penis and felt it hardening once again. I squeezed it and she cooed, as she touched my cock.
“Oh my. You are hardening once again my Princess. Would you enjoy finding out, what it feels like to put your penis inside of my rectum?” I asked.
“Oh my. That sounds just so very delicious, darling. But, won’t that cause you any discomfort?” Estefania asked.
“No. Not too much. I’ve been trained and widened. You see, Daphne has had me wear Butt-Plugs, which are really vaginal dilators. Women use them after having surgery in the region of their vagina. Transexuals will also widen their pussies after SRS. Daphne wanted me to experience what getting fucked as a female was like. She has used Strap-on dildos when we have had sex,” I explained.
“Let me lubricate you, as well as my anus. Then I’ll kneel on the bed, doggy style. Next, we’ll slowly work your cock into my rectum,” I added.
It did not take very long to have Estefania’s lubed cock sliding in and out of my well-oiled ass. It was just so very wonderful. I had just recently sucked my first cock. And now for the very first time, I had a real penis inside of my anus. Having Daphne bang me with a rubber strap-on dildo was one thing.
It was an entirely different thing all together though, having a real flesh, blood and bone cock humping inside of my asshole. I used all of my supple leg, arm and torso muscles to push up and off the mattress, and thrusted my asscheeks back into Estefania’s pelvis until her balls slapped repeatedly against my taut butt.
I knew then that I needed to prepare Estefania to be taken anally as soon as possible, so that I would be able to butt-fuck her by the coming weekend. We really began to get into a lover’s rhythm. I was using a rocking motion to set the pace. My sweet Estefania followed along wonderfully. She was panting excitedly and enjoying herself immensely.
As I continued to alternate between squeezing my ass cheeks around her cock, and then releasing the tension, I was getting her very near to the ejaculation point. I then felt her hands grip my buttocks firmly and she shouted, “Oh my Heavens, I’m coming! Oh wow! Oh I’m coming!”
It was such an absolute joy to feel her cock and balls, release a warm stream of Ejaculate into my rectum. The moment was both thrilling and so very fulfilling for me. As Estefania screeched and cooed, she gripped my nipples and pinched them. As her cock receded from my ass she pulled me down to the bed and licked my face.
She giggled as she covered my face in kisses. It was Sunday morning after breakfast, when I took her into the bath and had her lay on her side on a soft, fluffy, bath rug, while I filled her colon with a warm, soapy enema fluid. Once she had evacuated, I gave her a warm water rinse, prior to a scented, Massengill, rectal douche. Then I inserted, her very first, lubed Butt-Plug.
She very well knew that I was getting her ready to take my cock inside of her in a few days. Throughout the following week, whether at the salon, out on the town, or at home, we were like lovebirds on a honeymoon. We both wore makeup and nail polish during our workday at the beauty parlor.
All of the girls at the salon loved Estefania’s new perm. We both also wore “Campy” effeminate attire. It was obvious to even our salon clients that something was going on between us. At home, whether we were cooking, eating or housecleaning, we’d give each other soft kisses on the lips, or little pats on the butt or genitals.
We were living in a fantasy world and we knew it would all end when my wife Daphne and Estefania’s sister Lisette returned from Oak Island, North Carolina. The problem was, that they returned all too soon ahead of time, and discovered us sleeping intertwined in bed, dressed in Chiffon nightgowns.
The evening prior, just before we’d fell off to sleep, in a sated, peaceful slumber, I had at long last buggered my lovely Estefania, and filled her rectum with my creamy, white seed. It would be the last time we’d ever make love together again.
As it occurred, the girls ended up leaving the Island later in the evening on Saturday, rather than their original plan of departing in the early afternoon on Sunday. Apparently a storm was moving in and the County authorities suggested an evacuation. We were completely oblivious to anything outside our little fantasy dreamworld.
Neither Daphne or Lisette saw any reason to contact us, as we might become worried or overly concerned. Sometime around 4 AM on Sunday morning, Daphne and Lisette arrived at Lisette’s home. Almost immediately Lisette noted her spare vehicle was missing. Neither wanted to believe the worst.
However, they immediately drove to the home where Daphne and I resided. When they entered the boudoir where Estefania and I were laying in each other’s arms, things became frantic, very quickly. Daphne was the first to speak as she turned the bedroom lights on.
“Oh my goodness, they’re sleeping together! Lisette. Look at them. They’re wearing negligees. Blair. You had sex with a 19 year old boy in our marriage bed? You disgusting pervert!” Daphne spat out.
There was real confusion as Estefania and I got out of bed, our make-believe world completely shattered. Lisette spoke next.
“Oh Blair. You twisted pansy. You recruited my baby-brother for your sick, fairy-like purposes, didn’t you? What did you do with his hair? Is that a Perm? Really? You won’t be going into that salon any longer Stefan. Get dressed as if you were a boy, please. I’m taking you home,” Lisette insisted.
“Lisette. You won’t have to worry about Stefan working at the salon around Blair, any longer. That won’t be a concern. I own the salon. Blair feared the responsibility of proprietorship. He was only the manager. I said he was the manager, because he’s now fired. I won’t have my employees being sexually harassed by their supervisors,” Daphne stated.
“I’ll be promoting the assistant manager Cynthia and I’ll allow her to personally pick her own assistant. Please let Stefan learn a vocation, Lisette. From what some of the salon clients and the employees have told me, Stefan will become a wonderful hairdresser,” Daphne insisted.
“Would you enjoy that Stefan? Would you like to become a cosmetologist?” Lisette asked.
“Yes. I think it would be fun. I believe I’d enjoy making ladies pretty,” Stefan agreed.
I was glad that Stefan was being given a free pass as to us having a sexual relationship. I already knew that any chance of us having any sort of illicit affair was over with. For the time being, I was banished by Daphne to “Sabrina’s” room. It wasn’t until Monday afternoon, when Daphne retuned from work that she handed me a phone number.
“I want you to clear out your office at the salon. I’ll be giving you some boxes to pack up your male things. Put Sabrina’s attire and your Androgynous apparel into the suitcases I’ll be providing for you. I spoke to your mother, Roxanne. She doesn’t want to speak to you or see you. However, her very close friend, Vivian Rothschild, says you can stay with her,” Daphne added.
“Roxanne said Vivian always thought you were cute and would she have enjoyed a fling with you. So good luck. Call her. I want you out of this house by the end of next week. I’ll take care of your male clothing. According to Vivian you won’t be needing it while you’re living in her home,” Daphne shrugged.
I called Vivian that evening and left a message. She returned my call the following day around 10 AM. I’d already went to the salon and packed my belongings from my office.
“Well hello Blair. Or is it Sabrina, these days? Don’t worry. I’ll be renaming you when you move in with me. And by the way, honey. I’m to be referred to as Ms. Vivian, by you,” Vivian laughed.
“Thank you Ms. Vivian. Thank you so much for helping me out,” I replied.
“Don’t worry sweet-thing. You’ll earn it. This is a big place and you’ll be my housekeeper in between the visits by the housekeeping service I employ. Plus, I’m going to have you waiting tables at the new coffee bar and food service, that I’ve added to my bookstore,” Vivian replied.
“You know dear, I once thought we’d make a cute couple. Of course that was prior to me discovering that you were Gay,” Vivian stated.
“I’m not Gay, Ms. Vivian,” I politely added.
“Oh really? You’re not Gay? Excuse me, but didn’t your wife just catch you in bed with a Barely Legal, 19 year old teen male?” Ms. Vivian asked.
“Well yes, but….” I said as I trailed off and Ms. Vivian cut in.
“So, did you suck this young male’s cock?” Ms. Vivian asked.
“Yes, but I…” once again I tried to add a caveat, but, Ms. Vivian stopped me.
“Now tell me, something, Sissy. After you sucked him off, did he ever stick his cock up your ass?” Ms. Vivian added.
“Uh, yes he did, Ms. Vivian,” I agreed.
“So you gave him a blow job, and he fucked you? I’d say you were Gay, Princess,” Ms. Vivian went on.
“But I still like Ladies, Ms. Vivian,” I added.
“Honey, I also like Gay men. You will be meeting some of those Pansies, by the way. But I’m not having sex with any Fag, that has had sex with another man. You may think you’re bisexual and not a Homo. But please don’t tell the next girl that you date, that you enjoy sucking cocks and taking it up the ass. I can almost guarantee, that she won’t be giving you any Pussy that evening, once you describe your sexual preferences,” Vivian stated.
“I’ll see you at 9 AM this Saturday. We’ll get you moved in. Remember this Sissy. It’s my house and you’ll live by, obey my rules. If Daphne hasn’t already told you, don’t bring any Boy clothes with you. While you’re with me, here at the house or in public, you’ll wear female attire or Androgynous, Unisex apparel,” Vivian informed me.
“Yes ma’am, Ms. Vivian,” I agreed.
“Good Girl, Coco. I’ll see you at nine, Saturday morning. Oh, in case you wondered, your new name just popped into my creative mind. You are now Coco. Coco Colette to be exact. But we’ll rarely use your middle name unless you are dressed, full-on Femme. So sleep well until I see you, Coco,” Ms. Vivian said, as she terminated our phone call.
The following Saturday evening as I was tying up any loose ends before my move, Daphne informed me, “Vivian wants you dolled up fully as Coco Collette when you arrive at her home in the morning. She suggests you set your hair at bedtime and be in full makeup when you pull into her drive.”
“You need to be there at 9 AM? I suggest you retire very early to get ready in the morning,” Daphne said as she closed the door to my boudoir.
I had my car packed, my “Outfit” picked out, and my makeup travel bag ready for use on the boudoir vanity. I did waken early. I’d showered the evening prior, moisturized and set my hair at bed time. I wanted to be extra careful with my appearance. I’d be going through a monitored security checkpoint, as Vivian lived in a private, gated community. I didn’t wanted to be “Made” as a male.
I put a pre-laced cinch around my waist and fastened it snugly with the clasps in front. I used a panty brief to keep me modest as I didn’t think Vivian would care for it, if I got an erection around her. I used a garter belt and sheer hose, as I was wearing a beige sweater dress with matching three-inch heels.
I’d yet to take hormones then. So I went with a lightly padded bra. I wanted just enough cleavage to pass as a female. I’d painted my nails at bedtime. I was careful with my makeup. I didn’t want to overdo it and look like a drag queen. Nor did I want anyone to realize I was a feminized male.
It was as if I was going for an early morning job interview, so I kept my “Look” to a daytime makeover, with soft, nude, pink matte lipstick. Once I fluffed and sprayed my hair I went out to my Minivan and drove to Vivian’s. Daphne had told me not to bother to wake her as she really didn’t plan on any tearful goodbye’s.
At the gate to Vivian’s neighborhood there was a female security guard. I hoped she couldn’t “Out” me.
“Yes, I’m here to see Ms. Vivian Rothschild,” I said.
“Oh yes. She let us know. She said she’d hired a live-in housekeeper. You must be her? Miss Coco Danvers? Could you sign here, Miss Danvers?” The Guard asked.
That threw me for a loop. My mother’s maiden name was Danvers. Luckily I caught on. Typical of Mummy’s “Bestie” to assign me a last name also.
“Yes. Of course Ma’am,” I agreed as I used a really flowery script to sign, Coco C Danvers. The “C” being for Colette.
I continued on to Vivian’s address. As I was removing my luggage from the minivan, Vivian made her way towards me.
“Let me get a good look at my new housekeeper, Coco. Very cute. I like the pert Pixie bob, but we’ll need to redo the color. You look a bit too fashionable for a cleaning girl and a coffee shop waitress. The Champagne Blonde needs to go. You strike me as more of a Medium Shading, coppery tinted, auburn redhead,” said Vivian, a dyed strawberry blonde.
“And we just might consider trimming up the Pixie just a bit, to make it appear a tad more boyish and Elfin? Let me snap a photo and I’ll text it to my hairdresser, Sandy,” Vivian opined.
Vivian showed me to my boudoir and en-suite bath. It was as suitably “Girly” as I had expected. She even assisted me with putting my “Things” away. Vivian insisted that I carefully separate the “Girly” outerwear, from my “Sissy-Boy” Androgyne attire.
“The underthings, and the Lingerie are for the most part, all-purpose. However, I feel that I’d prefer you to ‘Present’ at least, 75% of the time as an effeminate, swishy, sissified, Toy-Boy. The remainder of the time I’ll permit you some latitude, to look as girlish as you appear at this moment,” Vivian stated.
“Of course I’ll always expect you to wear cosmetics to some degree and have femininely styled and colored hair. I have a very active social life, as does your mother, Roxanne, and Linda, who is part of the ‘Triumvirate’ your mummy and I belong too. On occasion Roxanne will bring Brenda, your Mother-in-Law, with her,” Vivian explained to my chagrin.
“I enjoy attending Gay bars, Transgender Clubs, Lesbian Taverns and even Drag Shows. So be prepared for me to begin showing you off as someone who happens to be ‘New’ to the Scene. If you understand what I’m getting at? In any event you’ll be seeing my GYN on Monday, for a dosage of Estrogen. Just a series of injections and some daily tablets. I’ll not have you horny all of the time and making a pest of yourself, while you are here,” Vivian insisted.
“The Estradiol will Chill you out, as well as make you extra cooperative and exceptionally obedient. Oh here we go. Sandy has already made a 9 AM appointment for you on next Saturday for a cut, coloring and curl. He’d also enjoy having you come in for a body wave in three weeks. There now. I’ll confirm that appointment also,” Vivian added boldly.
“You’ll like Sandy. He is as Gay as a Lilly, but really nice looking. You two should really hit it off very well. He also mentioned in his text that we just might consider some lip-fillers for you? And why not? Okay Sweet-Cheeks. Let’s get you out of that girly outfit and into something a touch more Swishy. I want to introduce you to some of the girls at my Bookstore and Coffee bar,” Vivian announced as she propelled me towards my new, femininely appointed, Boudoir.
After I removed my Sweater dress and heels, Vivian told me to dispense with the bra. She had me leave my Corselet and panty brief in place but wanted me to remove my garter belt and hosiery. She then went to the closet furthest from the bed and returned with several shopping bags.
From the logo on the bags, I realized they were from Linda’s upscale boutique at the Town Center Village shopping center nearby.
Vivian looked at me and said, “Go fetch the rest of the bags from the closet, Coco. I took the liberty of getting your sizes from Daphne. Then I went a size less when I made these purchases. I want everything to fit you nice and tight, to show off your dainty frame and your shapely figure.”
“We’ll sort thru these. Oh there it is. Here’s the outfit I want you to wear. Hopefully you’ll have footwear to match. If not, I just may. I didn’t dare purchase shoes for you. I want you present for that sort of fitting,” Vivian explained as she pulled a pink, Cami-top from the bag.
“We’ll put all of these items away for you, once we return from the Cafe. Try that Camisole top on. Oh it’s gorgeous on you. And there’s a little room for cleavage. Wonderful. The stretch slacks and the hip-length Cardigan match also. Aren’t they divine? Do you have a pair of nude or beige heels?” Vivian asked.
“I think I have a pair of kitten heels in Beige?” I replied.
And I did. Once I was dressed, Vivian looked me up and down. Then she posed me in the mirror. With my makeup, styled hair and flat chest, I looked the part of a slender, delicate, pretty, boyishly-shaped female. I’d certainly be a Lesbian’s Delight, if there were any such ladies at Vivian’s Bookstore and Cafe.
As Vivian’s Literary selections favored Women’s issues, I didn’t doubt that there might be a few Feminists in attendance. Vivian drove to the shopping area. In fact she’d taken my car keys and locked them in her safe, telling me, “You will need to request my permission to go anywhere without me or a chaperone approved by me, accompanying you, Coco.”
Vivian and I were off to a wonderful beginning. Strangely enough, her sheer dominance, excited me. Plus, I didn’t dare rebel. Ever.
Chapter III: An Orderly, Supervised Lifestyle
I sat obediently on the exam table at the GYN office. I wore a pair of Billowy, white Palazzo pants with multi-tiered cuffs and a tasseled drawstring that knotted at my abdomen. I had on a Beige, back-button blouse, with a Standing Collar and a frothy lace furbelow that fell to my midsection. I wore pink, round toe, kitten heel pumps with a bow-knot ankle strap and white, ruffle, anklet socks.
My Pixie Bob had been jelled and swept-back into a heavily-lacquered pompadour. The GYN and her Charge nurse were discussing hormones and “Blockers” with Vivian. Vivian decided to just have the Estrogen administered. We were now waiting for the “Tech” who would administer 1/2 of the dose.
Then Vivian would give me the other half. The idea was to allow Vivian to administer the injection at her home.
“Shari, show Ms. Rothschild how to load up the syringe. Now that’s half of the dose Viv. The prescription I’ll give you will be good for 5 months, and ten injections. It will include the syringes and correct sized needle,” the doctor explained.
“Coco. Stand facing the table. You may grip the exam table top and then take your weight off the right leg. That’s it. Point your toe downward. Now watch, Ms. Rothschild,” the Charge nurse added.
“Reverse your feet Coco and take the weight off of the other leg. Now you inject Coco, Vivian. Very nicely done,” the Doctor added.
Two day’s prior I had “Waitressed” at the Coffee, donut, bagel and sandwich bar at Vivian’s Bookseller location. I was wearing my beige Kitten Heel pumps, and my Pink Camisole, with matching stretch slacks and hip-length Cardigan. The three-piece outfit was all designed in a soft, fluffy Cashmere.
When I arrived at the shop, Vivian had fitted me with a floral-print apron. The apron came complete with ruffled shoulder straps, a snug waistline, that tied with a large bow in back, and a flared, petticoat hem. I couldn’t help but blush as I minced from table to table taking and serving orders.
There were more than a few “Domme” females and Lesbian’s present having lunch, working on their laptops and discussing the Stock Market as Vivian worked the room. At around 5PM, a tall slender male with bleached blonde hair wearing jeans, sneakers and a Chambray shirt entered.
I went over to take his order. He looked me up and down and smiled. Then he asked, “Are you Coco? The Sissy that Vivian hired as a cleaning girl and kitchen bitch? You’re a cute one aren’t you, girly? My name is Sandy. I’m Vivian’s hairdresser. I took off today and I’m slumming. But I wanted to look you over. I’ll be doing your hair next Saturday and I thought we should get to know each other better.”
The way Sandy was leering at me made me feel naked. To top it off, he was only one of a number of Gay men that Vivian planned on introducing me to. Throughout the week Vivian kept me very busy cleaning her home and preparing meals. Even though she could sleep-in most any morning, Vivian had me up early to prepare her breakfast.
She preferred eggs over easy, veggie bacon, tea and fresh fruit. After the clean up she’d have me do the bed making, vacuum the living area, and the boudoirs, as well as clean the tubs, sinks and toilets. She’d shower prior to going into the bookstore for lunch, and then have me blow-dry and style her hair.
The plan going forward was for me to “Wait” tables for the lunch hours at the Bookstore, and leave in time with Vivian to prepare her evening meal. Whenever I was cleaning, I was permitted to wear Ballet flats. However, whenever Vivian was “Showing” me off, such as when I waited tables, or “Entertaining” I was to be in heels.
The Saturday following the Monday GYN visit, Vivian and I headed for Sandy’s salon. She was also having her hair done for a date that same evening with a “Gentleman” College Professor she’d met at her bookstore. On the way to Sandy’s salon she explained to me what she expected of me for the weekend.
“You are to meet, Edward, the professor I’ll be dating, when he comes to my home. Greet him properly with a curtsey and offer him a drink. I’ve already informed him you were Gay, so you may act as much like a Pansy as you possibly can. Whatever you do, do not act manly, which shouldn’t be too difficult for you,” Vivian stated.
“If you do attempt to act Butch, I’ll spank your ass beet red right in front of Edward. I expect you to serve us Breakfast in bed Sunday morning. I also expect you to act sweet and interested in Sandy while he does your hair. Do not disappoint me, Coco,” Vivian insisted.
Sandy greeted us both effusively. He was dressed far more trendy for a workday at the salon, in shined, black, dress loafers, and a matching gray slacks and blazer combo, with a white shirt opened to just above his pecs. He handed Vivian off to a “Butch” looking female named Grace.
Vivian was sort of a “Legend” among the local LGBTQ community, for her fundraising and activism on behalf of their cause. Sandy escorted me to the shampoo sink. He placed a Salon Cape over my shoulders. As he did so, he put the cape on me from behind. He took an inordinate amount of time fastening the clasps at my collar.
His hands roamed over my back, shoulders and neck. He pushed up against me and his pelvis contacted my buttocks. As his body pressed against mine I could feel his already hardening penis pushing against my ass-cheeks. It was easy to both sense and feel that he already had designs upon me, and that he was making a play for my affections.
Strangely enough, I’d just experienced my first few sexual encounters with another male. And now, through Vivian’s “Trans” network, I was already being sought out by a Gay man. As Sandy shampooed my hair, he soothingly and carefully massaged my scalp and the back of my neck.
I’ll admit, his attention towards me was very flattering. After he conditioned my hair he kept me at the sink with my head and neck still resting in a position where he would be able to begin my hair coloring process.
Sandy lathered in a bleaching creme mixture in order to strip my hair of it’s present Champagne Blonde color. After a rinse, he sat me at the vanity mirror so that I could view my present, Bright, Brassy Blonde color.
“Don’t fret, my little Princess. I will be making you a lovely, Coppery, Medium Auburn Redhead very soon. And once I’ve trimmed you and curled you up, you’ll be a real stunner for our date this evening,” Sandy smiled.
“We have a date tonight?” I asked.
“Why yes, of course we have a date, Sweet-Lips. Speaking of lips. I’ll be giving you the first of three Plumping treatments today. You see, Coco, while Vivian is out with her man Edward, you’ll be at home with me, enjoying some private quality time with Your man,” Sandy added boldly, as he foil-wrapped my hair and painted on the Medium Auburn tinting.
During the coloring process, Sandy had one of his girls manicure my nails and paint them with a shimmery, frosted, Rose-Gold shade. As my nails dried, Sandy removed the foil wrap and gave my tresses a final creme rinse prior to cutting and styling my hair. I watched while he clipped, trimmed, cut, set and stylized my Pixie-Bob into a cute, curl-topped Pixie.
Though the cut was certainly shorter, with the color, as well as the new styling, it was far more Girly, as well as totally Sissyish. Sandy sprayed my hair heavily prior to painting my face is a sexy, alluring manner.
Prior to my leaving the salon with Vivian, Sandy kissed me fully on my wet, crimson lips saying, “You are an absolute doll, my gorgeous Coco. We’ll have such a fabulous time this evening. Won’t we Doll? In a few weeks we’ll perm or body wave your Pixie and you’ll be my sexy hot, girl.”
On the drive to Vivian’s Mansion I asked, “Do I really have to be subjected to a ‘Date’ with Sandy this evening?”
“Yes you do, girl. Is there a problem with that? Listen to me Coco. Understand this. Your Heterosexual life, if that ever really, truly existed, is over and gone. Finished. Don’t you get that? You are now primarily either Bisexual, or in reality a homosexual. Because I truly doubt any female is ever going to date a Pansy such as you are,” Vivian boldly stated.
“If you don’t care for me matchmaking you with my Gay male friends, then you can leave today and find your own place to live. But you are incapable of doing that, Coco. We all are aware of that, aren’t we dear? I mean you never had your own place, did you, now? No. Of course not. Why, we all know, that you very well ran right from your Mummy’s apron strings, into the Motherly arms of Daphne,” Vivian said.
“When Daphne bought the new house, all you did was show up at closing and sign papers. When she bought the salon and the upstairs apartment you were afraid of joint ownership. You really only managed it in name alone. She made all too he real decisions. You are like Mummy’s Little Boy. or really, in your case, Mummy’s Little Sissy Girl. Aren’t you Coco?” Vivian teased.
I blushed, shamefully as Vivian continued with her scathing discourse of me.
“You do know you were played don’t you? I mean Lisette played you like a Toy Fiddle, Coco. Lisette never really cared for you at all you know? She loved Daphne far too much. In a Sisterly way, of course. She and Daphne were childhood playmates. She always believed that Daphne deserved far better than you as a Spouse. That’s because Lisette, a Head-Shrink, analyzes people. And Daphne a Master CPA analyzes numbers,” Vivian went on.
“Lisette saw the attraction you had for her brother and continually dressed Stefan effeminately, every day that she sent him to work at the salon. You never wondered why Lisette, who found your Crossdressing to be distasteful, would attire her brother as a Mincing Swishy Pansy, did you Coco?” Vivian asked.
The reality of what Vivian was saying hit me and I began to sob and whimper. Stefan and I had fallen for each other, fallen into each other’s arms, and fell into bed together. And I had fallen for the trap his Sister Lisette set for me.
“Have good cry Sissy. Your marriage is over. I have spoken to both your mother, Roxanne and your Mother-in-Law Brenda. You mother is very disenchanted with you, more so due to you hiding your true sexuality. Brenda of course, is glad her daughter will be rid of you. You are Fag-Bait now Coco. So be nice to the Homosexual men I set you up with, and enjoy your new lifestyle and make the most of it. Be sweet to your lovers. I’ll see to it that they all have plenty of money to spend on you and that they are very generous towards you,” Vivian promised.
“Remember this Sissy. Crying will cleanse you and wash away your fears. Don’t fret over your makeup. I’ll help you fix it later,” Vivian added as we reached the security gate to her community.
I was so upset that I ran, mincing rapidly, my high-heels clicking on the parquet flooring, on the way to my boudoir. I threw myself down upon my bed and sobbed, nearly hysterically. As I blubbered into one of my fluffy, perfume scented pillows, Vivian came into my room and lovingly massaged my back, neck and shoulders. It took a matter of time, but I finally quieted down.
I then sat up and hugged Vivian in a “Daughter to Mummy” manner. Vivian kissed one of my cheeks softly and reminded me, “We have our dates coming to the house. We should get ready soon, darling. Edward will be here at 6:30 PM. We should leave for Dinner by Seven. We won’t return until after Mid-Night.”
“Sandy won’t arrive until 7:30 PM. He will stay until around 11:30. You need not wait up for Edward and me. I’ll expect Brunch in bed by 10 AM. You know how I expect you to greet Edward. Now, understand that Sandy is both physically, emotionally and sexually more mature than you are Coco. He’s very likely a Dozen years older. I believe he’s about Thirty-eight,” Vivian said.
“However, he enjoys the sort of Mentor to Ingenue relationship that the two of you should have together. He’ll relish ‘Bringing you Along’ so to speak. And it’s possible that, his type of mentoring might involve some discipline and he’s a notorious disciplinarian among our social set. Now I do realize that spanking and paddling are both sexually stimulating for many, but not all Sissies,” Vivian paused to note my reaction.
“And of course, privately and especially publicly, that sort of display can be very shaming and humiliating. Though there is still some sensuous excitement with that type of socially embarrassing incident. So, my advice to you Coco dear, would to be on your very best behavior. Be extra dainty and delicate. Attempt to appear demure, sweet and very submissive,” Vivian went on.
“And try your very best to dote upon Sandy and be as cute and giggly as you possibly can. Now let’s pick out what you’ll be wearing before we fix your hair and makeup,” Vivian announced.
When Vivian’s man, Professor Edward, arrived, I was walking on two and one half inch, high heeled pumps in a “Nude” shade. My feet and shaven legs were encased in white knee-high hose held in place with silicone “Stay-up” lace tops, along with matching white-lace panties.
Vivian had handed me a gorgeous pair of cream-colored, billowing, Palazzo pants, with a floral pattern of tiny Rosettes. I had on a Beige, Spaghetti-Strap, Camisole top, with no brassiere. With my Gamin Pixie hair and my beautifully contoured makeup I looked as effeminate as I could possibly ever be.
Vivian was still doing her makeup when Edward rang the doorbell. I answered the door with a flourish, just as Vivian had expected me to.
“Please do come in Mister Edward sir. May I pour you a drink Sir?” I asked with a demure curtsey.
“Yes. Please do. You must be Coco? Vivian said that she had hired a Pansy to keep house for her, as well as dress her hair, and do her makeup and nails. Bourbon on the rocks, one finger only, will suffice, Coco,” Edward stated as he took a seat in the living room.
Shortly after serving Master Edward his drink, I sashayed into Ms. Vivian’s boudoir to affix her hair, prior to escorting her out to Master Edward.
Just prior to their leaving on their date, Ms. Vivian instructed me, “You have my permission to leave the house with Master Sandy should he desire to take you out to a club to show you off to his friends. But you must return prior to midnight and get into bed. You’ll need to be up and out of bed, by 8 AM to prettify yourself and prepare our brunch for ten o’clock, Coco.”
Ms. Vivian also cautioned me to dab some perfume on my wrists and my neck to be as “Alluring” as possible for my Date. Master Sandy arrived slightly early. As I greeted him, smiling at the door, he took hold of me and kissed me strongly on the lips, pushing his tongue into my mouth.
I was very surprised at how quickly he took charge of the situation. His arms were around me so snugly, and his mouth had smothered mine. I nearly swooned. What an amazing kiss it was! I tried to relax and go with it. I entangled my tongue with his, and squeezed his ass with my fingers.
I knew that my lipstick was smeared. Even so, I was glad he hadn’t yet mussed my hair. I’d spent so much time on my hair and face. I sincerely thought the kiss was going to take my breath away when Sandy slowly released me from his grasp.
“You are one, really hot looking sexy, Sissy-Boi tonight. Aren’t you sweetie? I don’t know where to start. Should I take you right here on the floor or drag you into your bedroom? Sandy asked.
“I do have permission to leave the house with you, if you’d like to take me to a club. I love Latin dancing. Especially in high-heels,” I stated.
That must have been far too tempting for Sandy. We took his Sports Car and he drove to a Gay Club in the Front Street District. The club was jumping as it was a Saturday evening. Every time we got up to dance, Sandy would tip the DJ and ask for something along the lines of a Ricky Martin number.
I loved the way he twirled me on my heels as he threw me across the floor, with my billowy Palazzo’s flowing. I also simply adored the manner in which Sandy embraced me into his chest and rubbed his groin into mine. The feeling of his hardened penis against my own penis was so very overstimulating.
To say that I felt so very “Gay” at those moments would be quite the understatement. I had sprayed my curled Pixie so stiffly that not a hair was out of place by the time we departed from the club.
Of course the sexy dancing had stimulated Sandy considerably, and I now knew that I was in for an “Exciting” evening of sex. We’d only been at the club for around two hours, so we had a few hours before “Miss” and her date would be returning and would need to be in bed.
As we entered the Mansion, I reached into my Michael Kors, Light-Pink, leather, “Hobo” bag for some lube and a Tampon. The Panty-Liner I had worn to the Gay Club was already wet from me “Dripping” from sexual excitation. As of yet, the Estradiol dosages I’d been given, hadn’t truly began to fully effect me Mentally, Physically or Emotionally, to the degree that they eventually would, in time.
I’d been allowed to wear panties by Ms. Vivian instead of the usual panty brief. “Miss” cared very little whether or not anyone at the Gay Club saw me with an erection poking thru my Palazzos. It would be far different should I be in the company of her friends from her Ladies’s Coterie.
Sandy wasted no time in taking me into his arms and pulling me down onto one of the soft, comfy, living room sofas. His kisses were so very sensual, and I would sigh deeply when he’d permit me to come up for air. Our tongues twirled together and our lips meshed wonderfully. I reached for Sandy’s groin and felt the hardness of his cock.
“We need to do something about that. Don’t you think? I could kneel right here and use my mouth and lips. Or I could get on all fours and you could bugger me from behind. What do you think?” I asked.
“Your mouth. It’s so pretty. Could you freshen your lipstick first?” Sandy asked.
“Of course love,” I agreed.
I then reached, once again for my Michael Kors “Hobo” purse, and took hold of a tube of Runway Rogue “Strut,”a truly, Vibrant Violet Lipstick.
I put on a fresh application of lipstick, smacked my lips, and added a second, exotically shimmering top-coat. I was now ready to suck the cock of the second male I’d ever been with in a romantic situation.
I do realize now, and even then, I was somewhat cognizant of the fact, that the timely manner in which I took to a homosexual lifestyle, only proved that I’d been destined for that manner of living, from the dawn of puberty.
I thought back to that afternoon in bed, with the lovely Estefania, when she’d described “Herself” peering at her mother and sister, as they prettied themselves in front of their vanities. That discussion with Estefania had brought back, suppressed, “Stuffed” subconscious memories for me.
I also had watched Mummy, and Big Sister “Doll-Up” in their boudoirs. I would also wish it were me making myself pretty. And I would also shudder in shame, thinking of how my father, a Consummate, “Man’s Man” would react if he knew what a Sissy-Pansy I was.
Now? None of that truly mattered any longer. I’d been liberated. I fondled Sandy’s balls and licked the end of his cock. Then I licked his testicles prior to finally placing his cock between my lips and then surrounding it with my entire mouth. I began to suck, lick and slurp, while kneeling slavishly on the Living room carpeting, groveling worshipfully at Sandy’s feet.
HIs slacks were at his ankles. My head was bobbing back and forth bringing him pleasure as I sucked his penis in the way that only a very effeminate Gay lover would pleasure their man. My lips were locked tightly around his cock, awaiting the forceful discharge of his warm, sticky semen. My penis was bursting for relief.
I heard my handsome lover Sandy sigh and then grunt. Next his pelvis bucked and his dick swelled as Sandy erupted into my mouth. I gladly swallowed his semen, sucking him dry. I held his deflating penis lovingly in my hands and licked all around it.
Sandy patted me on the head and said, “Good girl, now get on all fours. I won’t be able to fuck you with my cock tonight. We’ll save that for our next date, Coco. But I can finger fuck you while I jerk you off. Where did you put that lube you took from your purse?”
“There, on the end table, Sandy Darling,” I practically lisped, as I waved my hand, wiggling my fingers daintily with a limp wrist, in the direction of the lube.
I untied the belted sash that held my Palazzo pants in place. Along with my panties, I slid my slacks to my thighs, exposing my rectum. Sandy lubricated both his hands thoroughly and took a gob of the KY-Jelly and coated the inside of my anus completely.
Then, as two fingers of his right hand entered my asshole, he squeezed my cock with his left hand and began to carefully masturbate me. The pleasure was so intensely erotic that I began to quietly whimper and sob, before simpering, very prissily, “Oh Sandy darling, that simply feels so very, very lovely, dear. Oh my, I don’t know how long I can take that before I climax.”
Sandy increased the intensity of his ministrations of me, until my body began to quake, and my dam just simply burst. Waves of pleasure washed over me, and as I ejaculated, I broke into tears, blubbering, “Oh, I feel as if I could faint dead away, this is just so glorious! Oh my gracious, I could just swoon!”
I collapsed to the carpet with Sandy’s fingers still up my rectum. As my simpering subsided, Sandy rubbed my lower back and bare ass. He then whispered in my ear, “I need to get going and you need to get to bed, as per Vivian’s instructions.”
“Oh yes, Darling. Let me put myself together and see you to the door, Love,” I said as I pulled up my Palazzos and panties and walked Sandy outside. We kissed fervently before he got into his sports car and drove away.
I showered and even washed and set my hair prior to slipping into a pair of Harem pajamas and falling off into a deep, blissful sleep. I really wished I’d been fucked by Sandy’s cock, but being finger-fucked would have to do. I woke early and before I even put my makeup on Ms. Vivian sent me a text.
“If you are up, I need for you to come to my boudoir and do something for me,” the text read.
I tapped lightly at her door and was told to come in. Mr. Edward was nowhere to be seen and Ms. Vivian was sitting on the side of the bed.
“Oh there you are. Come over here to me Coco and kneel down. Don’t worry. Edward just got into the shower and he spends quite a bit of time showering. Coco, Edward just fucked me completely dizzy and he left a bucket of Cum inside of me. I want you to begin licking and sucking my Pussy to clean all of Edward’s sperm out of me,” Vivian said, as if she were telling me to Fluff her pillows.
“What are you waiting for? I thought you’d be thankful? How many women are ever going to ask you, a Fruity, Pansy such as your are, to Eat their Pussy? Now get to work, Sissy,” Vivian said, pulling on my curlers to force my head into her crotch.
She held my head snugly against her pelvis, and I began to do her bidding. I tongued her pussy lips and tasted Edward’s salty seed. Next I began to suck her, with my lips and tongue. She had both her hands firmly on neck.
“Ahh. That feels nice. You do this very well Sissy. Daphne taught you to eat cunt, didn’t she? That’s a good girl, now. Suck Mummy’s Twat. Do you enjoy how Edward tastes?” Vivian asked.
I don’t really recall how long I sucked her until she released me.
“All right Sissy. You may go and comb out your wet-set, get dressed and paint your pretty face. We’ll see you at 10 AM,” Vivian added as she pushed me away, with her hands against my shoulders.
I wasn’t crying as I brushed my teeth. However I could feel the deep, humiliating shame that came with being Vivian’s Sissy-Servant. I knew as long as I depended on Vivian for a place to live, I should be prepared to exist with some sort of occasional degradation.
Of course, if I were prepared to grow up and act like an adult, and take care of myself, I could find somewhere to live as well as a position as a hairdresser to support myself. Mummy had found me the Stylist’s job I had when I met Daphne. Daphne had helped me open my very own checking and savings accounts. So I did have money.
But it was just so much easier to depend upon someone else. Why bother? “I can live with a certain amount of embarrassment. Everyone does. Why should I be any different?” I thought to myself as I removed the curlers from my hair and began doing my makeup.
Chapter IV: Mummy’s Sissy Boy
Ms. Vivian’s hair was up in curlers. Ms. Linda’s hair was wet and ready for setting, when the doorbell rang.
“That should be your mother, Coco. Please answer the door, sweetie,” Ms. Vivian said.
Indeed it was Mummy. “Hello Mummy. Won’t you please come in? Oh Mummy, your hair looks so nice. I thought I’d be doing your hair, before we all went out to the party?” I asked sweetly.
“No thank you Coco. I did my own hair for this evening. Is that what you call yourself these days? Coco? And what shade of lipstick is that which you are wearing?” Mummy asked me.
“It’s called Marvelous Creme. It’s a Muted Raspberry, Satin Shimmer by Runway Rogue,” I informed Mummy.
“Hello girls. Linda, Vivian. Always lovely to see you both. You know Coco, I thank the Heavenly Stars that your father did not live to see you wearing Lipstick, High-heels, Stirrup Pants and a Camisole top. With all of that, along with your hair up in a permed, Auburn shaded Pixie, I don’t think he could have taken it?” Mummy said.
“My late husband was a real Man’s-Man, Linda. And he was a wild animal in bed. I never, ever, had a man make love to me as fervently as he did, before or after I met him,” Mummy said, as I began to roll up Ms. Linda’s hair.
“Now, all of the men at the party tonight, won’t be Fags, will they?” Mummy Roxanne asked.
“No of course not Roxie. William, the host, is Gay. He’s a big time K-Street Attorney. It will be a mix of numerous people from his firm and other K-Street businesses,” Vivian explained.
“Great. Because I feel like having a man’s cock inside of me this evening,” Mummy Roxanne added as I continued to set Ms. Linda’s tresses and I checked the dampness of Ms. Vivian’s roller set.
“Will Sandy be there Ms. Vivian?” I asked.
“No Darling. Sandy isn’t quite in the same league as the K-Street crowd,” Vivian said.
“And who is Sandy, if I dare ask?” Mummy Roxanne added.
“Sandy is Coco’s boyfriend. He owns the Ms. Fabulous Salon and Day Spa. He cut, colored and permed Coco’s hair,” Ms. Vivian announced.
“Oh how wonderful. A hair stylist? Well. Could it possibly become any more Gay than that? I mean two hairdressers crazy in love,” Mummy Roxanne replied.
“Coco when you get Ms. Linda’s hair rolled up, I want you to change into the outfit I laid out for you on your bed, Sweetie,” Ms. Vivian instructed me.
“Oh, she’s still not Mummy’s Big Girl is She? Auntie Vivian still picks out her clothes for her,” my Mummy Roxanne laughed.
Ms. Vivian did have sensational taste. Especially since she was walking the tightrope between having me “Present” as a Limp-Wristed, Fairy-Pansy or a Hip-Wiggling, Painted-Up, Girly, Plaything. Of late, she’d occasionally had me wearing Shapely, Body-Con, Ankle-Length, Fishtail Dresses, or Form-Fitting, Mermaid Skirts.
It did appear that for the party with the K-Street crowd, I’d be dressed more Effeminately and Swishy. As I looked over the clothing laid out on my canopied, four-post bed, I couldn’t help but think of the last few times that Sandy had made love with me, either at his residence or there in my boudoir.
Sandy was not terribly masculine. In fact he could be a true “Sassy” Bitch-Boy. Nevertheless, he was the “Butch” and I was the “Lipstick Femme” in our relationship. And Sandy enjoyed taking me to task and spanking or paddling me whenever he thought it to be necessary. “The last time that he spanked me, he also Fucked me,” I thought to myself.
Just thinking about that day made me wet. I’d went to Sandy’s salon, to have a “Spot” Perm done to my Pixie Cut. During the entire process, from being shampooed to having my Perm stylized, Sandy had been all over me. Every chance he had, he was touching my ass, rubbing his crotch against me, or giving me soft little kisses and licks to my lips and cheeks.
Finally, just before he did my makeup, I’d said, “Please Sandy, could you possibly wait until we have departed the salon and maybe we are at your place or in my boudoir before you get intimate with me?”
He didn’t say much as he painted my face. He just sort of went, “Humph.”
I didn’t realize it, but he didn’t like, what he later would refer to as, me being “Prissy.”
He’d just finished applying my lipstick when he pulled me to my feet and removed the salon cape from over my shoulders. I was posing in the mirror fluffing my still slightly damp “Top” curls when he took me by the hand.
“Come with me Little Missy Prissy, we need to talk. Into my office please,” he said as he pulled me along thru his office door prior to shutting it and turning the lock.
‘What’s the idea? You don’t like me fawning over you, and showing you lots of affection? Sort of Prissy, aren’t we Coco?” Sandy asked.
“Well, I don’t know. But you can kiss me now if you like. We have plenty of privacy,” I purred.
“It is very private. I think it’s private enough for you to suck my cock. Kneel down Coco,” Sandy said, pushing me down to my knees.
Sandy what are you doing? Can’t we kiss first?” I asked.
“Yes. You may kiss my Dick, Coco,” Sandy said, unzipping his pants, taking his already swelling cock, and wiping the wet, Pre-Cum across my mouth.
“Sandy please,” I said as he put the tip of his cock between my open lips.
“Suck, Coco,” he told me as he pushed his cock deeper into my mouth.
He looked very serious. I shyly blushed as I opened my mouth to receive his Penis. I began to suck as he held my neck and shoulders snugly.
“Ah. Now this is nice. And don’t concern yourself about someone coming in here. The door is locked and I have the Privacy Please sign hanging on the knob. Oh Coco, you have the sweetest set of lips. Nice and sexy-plump. And I put on an extra coat of Passion Plum by Revlon when I did your makeup,” Sandy explained.
“Ah. Now, that I’m wet, and nice and hard, It’s time to butt Fuck you my sweet Fairy Bitch. That’s it, stand up and come over here and bend over this end table. Good girl. Hold onto the legs while I tie up your hands,” Sandy said.
“Sandy please. Is tying me up necessary. Ouch!” I squealed as he whacked my ass with an opened hand.
“You are being naughty Coco. And naughty pansies get spanked you know. Let’s get these slacks and panties down around your ankles so you are ready to be spanked as well as fucked. Do you want the paddle or the hairbrush Coco?” Sandy asked.
“Couldn’t I just have your cock?” I pleaded.
“Ow!” I squealed as he hit me again with an open palm.
“Paddle or Hairbrush? You Prissy bitch,” Sandy asked again.
“The hairbrush Sandy. Please Sandy. Whack my bare ass with a hairbrush please. Wow! Oh Sandy, that hurt!” I yelled, pretty loudly.
“Now you are being far too noisy, Sissy. I’m going to have to gag you,” Sandy said as he got a Ball-Gag from a vanity drawer.
“Oh please no Sandy. No, please?” I wailed, as he shoved the ball into my mouth and fastened the leather strap tightly behind my neck.
I was now going to suffer, very silently. The ten swats with the hairbrush he gave me, brought tears to my eyes as well as spittle from my gagged mouth. Then Sandy began to lube up my rectum, and I knew I was about to be butt-fucked.
As he began to push his well-oiled cock into my anus, I attempted to beg him to remove my gag.
But my efforts were futile. I simply made gurgling sounds as his cock rocked back and forth inside my asshole. Then I just closed my eyes, began to breathe deeply and evenly, and decided to enjoy being buggered by my lover.
When he fucked me from behind, Sandy knew just how to push my buttons. Gag or no gag, he would squeeze my tiny tits or fondle my testicles and penis. He could drive me completely wild. Sandy was 10-12 years older than I was and far more experienced sexually. Especially as far as Gay Male sex was concerned.
As I stood there, bent over a table, gagged, with my wrists tied to the table legs, I was totally helpless while Sandy buggered me silly. His cock went in and out of my ass, as he “Railed” me wildly. He had turned me into a defenseless slut who he could do with as he wished. My ass reflexively moved back and forth in time with the strokes of his cock.
I mewled and slobbered into the snugly fitted ball gag. Though I‘d easily lost most all of my self-respect as I performed as Sandy’s sexual plaything, I relished every single moment of being Sandy’s Carnal Captive. I was his, I belonged solely to him, and I reveled in that role. I was his Common Tramp, his Bitch, his Fuck-Toy.
My “Boy-Parts” were as excited as the current hormone dosages would allow them to be. I wasn’t rock-hard, but I was “Stiff” enough. I knew that very soon, sperm would ultimately flow from the head of my penis. As I began to dribble, I felt Sandy pause in his thrusting, and then release a low moan, prior to emitting a long sigh. Then Sandy’s body jerked.
I felt his cock expand dramatically as he spasmodically pumped a large quantity of sperm up inside of me. The feeling of the warm goo being ejected within me permeated thru my entire body in a series of hot flashes. I held tightly to the legs of the end table as both my body and Sandy’s jerked simultaneously.
My penis was no longer dribbling, it was spurting as Sandy’s right hand pumped up and down my sticky shaft. As Sandy’s cock relaxed in my anus and then slowly slipped out, I rested my torso down flat upon the table top. As Sandy panted he removed my ball gag and pulled up his pants.
Before I realized it, he had produced a Tampon and was plugging my anus with it, sealing his spurted seed inside of me.
“Let’s get you untied, your slacks and panties back on, and we can lay on the settee together, Coco,” Sandy said.
“Oh Sandy, that was so very, very Fabulous my darling lover. Oh, just so amazing,” I said as he walked me to the settee.
I laid my head back on his chest and enjoyed the aftermath of our climax. So, as I was dressing for the party in my boudoir at Vivian’s Mini-Mansion, I revisited that past seduction of me, in Sandy’s Salon. My Sani-Pad was dripping wet by then and I knew I had to change it soon.
Vivian had left out a pink training bra for me to wear. I carefully fitted it over my small but growing tits. Over the bra I put on a red lace, V-Neck blouse. I wiped myself well, prior to changing my Sani pad and my pink, tummy-paneled, control, panty-brief. I slipped on a pair of sheer knee-high hose with lacy, elastic hold-ups.
From a hanger I took a pair of white linen slacks and a matching double-breasted jacket. I stepped into a pair of beige 2 inch pumps, and sat at my vanity to touch up my makeup and use some styling pomade to “Plump-up” the top curls and side waves of my Permed Pixie.
Once I’d completed doing Vivian and Linda’s hair and makeup, we made our way to Vivian’s Lexus SUV. Vivian drove and Mummy sat in the front passenger seat. We traveled a moderately impressive distance to the edges of Montgomery County, near to Virginia.
We made our way off of the interstate and ultimately to a Private road that led to an Estate that had obviously been well maintained over the years. Several cars were parked in the large arched drive. Once inside the home I was impressed with the opulence of the setting.
Small groups of people were chatting, and Vivian was greeted effusively by the handsome host, William. He had a slight, British accent. Vivian introduced Mummy, Linda and me to William. I was introduced as Vivian’s “Live-in Housekeeper, Hairdresser and Lady’s Companion, Coco.”
Mummy added, smiling, “Yes, She’s my son.”
William took it all in stride. As he escorted us to an area of the home where we could chat and meet other people, William placed his hand on the small of my back, just above my butt to guide me. I made absolutely no attempt to discourage the handsome Englishman from touching me in a familiar manner.
Vivian spotted a few other people she knew, and as she began to introduce Mummy and Linda, William directed me into the Large, modern kitchen and asked, “Would you enjoy a tour of the house Coco, as well as the grounds as long as it remains light out?”
“Why yes, of course, Mister William. That sounds so very interesting,” I said so very sweet and softly.
“So. You are a hairdresser? Where do you work?” William asked.
“I work for Vivian right now. My partner and I are in the process of a separation. I did work at a salon which my partner owned. It is called The Sophisticated Lady,” I said.
“Yes. I see. I must admit that Vivian has told me quite a bit about you. All good of course. I must admit that I was impressed and delighted with what I heard from her, concerning you, Coco,” William added.
“We’ll, that’s good to hear. Oh, I’m sorry if I might have been too familiar,” I added as I inadvertently touched William on his bicep as I spoke.
“No, not at all. I don’t mind at all that you chose to touch me. And I wouldn’t care one bit if you were to become very familiar with me,” William smiled and winked.
“Oh. Well thank you so very much, Mister William. I’ll keep that in mind,” I said.
William then gave me a very thorough tour beginning with the outdoor gardens and stables. From there we went to the wine cellar and the remainder of the home that were not occupied by the guests at the party. He had apparently paid cash to have the entire estate refurbished after he’d purchased it.
The tour ended at a lovely, very feminine boudoir that his younger sister had once, temporarily occupied.
“She and her partner, an airline stewardess, recently purchased a home near Dulles which is very near both of their places of employment. She left some very nice items of apparel that she says she no longer wears. She told me to donate all of it to charity. I just haven’t gotten around to packing it up,” William stated.
“You know she’s very near your size, I believe? If indeed you’d care to look everything over? Well, I think it’s time we return to the party. They just might send out a search party for us. Coco? I’d like to ask a very personal question if you don’t mind? Have we known each other long enough to experiment with an Introductory kiss?” William asked.
“I think we might be able to do that,” I said, as I raised my head to look up at him, and extended my nicely manicured hands towards him.
He leaned down to me and as our lips met, my hands lightly touched his biceps and he gripped me lightly at my upper torso. Our tongues touched very softly in a mildly probing manner. My eyes were closed, dreamily. I thought to myself that the kiss held much promise.
“Well that was very nice. Thank you William,” I whispered softly as we ended the kiss, prematurely, I thought.
William, like Sandy was older and far more experienced in romance than I was. I thought him to be in his early 40’s, which, it turned out, he was. For the remainder of the afternoon and into the early evening, we went just about everywhere together, throughout the party. Even holding hands at times.
As the party was winding to a close, William spoke to Vivian and surprised me when he asked, “I’d like to borrow Coco, for some housekeeping for the remainder of the weekend Vivian. Could I return Coco to you, say, this coming Monday evening?”
“You may keep Coco as long as you care to William. In fact, I packed a suitcase and a makeup bag for Coco in the luggage area of my SUV. Coco. Here are my keys. Why don’t you take William to my Lexus and the two of you very discreetly bring your things into his residence,” Vivian stated.
“Coco, let me grab a key to a very private entrance to the home. We can take your things to my sister’s boudoir suite,” William said.
Neither my mother or Linda seemed very surprised that I’d be staying at William’s for a day or so. As they departed, my mother kissed me on the cheek and said, “Have fun dear. He’s very handsome, and quite Continental, I think.”
The party had been catered. As the caterer’s employees cleaned up, William and I began to watch a British Spy Thriller. I turned to William and said, “I saw a Pink Negligee in the closet that I’d love to wear. Could I try it on as well as a matching pair of heels I noticed?
“Yes. Of course,” he said.
By the time I returned from getting changed the caterers had departed. I sat very close to William, touching his knee with a “Feigned” attempt at catching my balance. I didn’t want to appear too, very forward. However I hoped he’d make a pass. He did make his move very shortly.
William put one arm around me, and placed his face very close to mine. I looked at him to my left, with a quizzical glance. He then asked, “Isn’t it about time that we continued that kiss from earlier in the day?”
“Yes, I would think that it is. I was hoping that you’d bring that up,” I said.
This time, when our lips met, sparks flew. We were completely alone, in William’s large, palatial home. There would be no concerns whatsoever on our part that someone might view us in our moment of unbridled passion. Our mouths opened to permit our tongues to intertwine. My aggressiveness truly surprised me.
I was hungrily sucking on William’s lips and tongue and really didn’t want to let go. My hands roamed from his hips, to the back of his shoulders, squeezing and kneading his body. My unabashed need to have him carnally came to the fore as my fingers grabbed greedily at his belt to unfasten his pants.
With that task completed, I pulled at, and unzipped his fly. Tugging at his slacks and underwear, I exposed his penis and took hold of it in one hand. As we separated from our passionate kiss, I blurted out, “Please allow me to pleasure you with my mouth?”
“Of course. Let’s go to my room where we can be more comfortable upon the bed. I really don’t want you kneeling on the living room floor,” William said.
I could barely get there quickly enough. Though I maintained as much of my composure as possible. I assisted William with undressing. Myself, I wore no panties, so most all of me was accessible with the open-front negligee which I wore.
As I began to suck William off, I announced, “You may ejaculate into my mouth should you so desire. Or, you may enter me anally with your hardness, if you feel the urge to do so.”
“Are you equipped to handle my penis rectally, Coco?” William asked.
“Yes I am. I’ve worn plugs regularly. I’ve also had both Faux and real Cocks in my rectum,” I said as I slipped William’s “Dick” from my mouth long enough to reply to him.
Of course I fully realized William was Gay. He wasn’t a Swishy Gay Male such as my “Boyfriend” Sandy, though. William did have a mannishness about him. I, on there other hand, was rapidly developing into an absolute overtly Effeminate, Fairy “Queen.”
I wondered of course if William had even been with any females as I had? I did believe that should we progress in our relationship, we’d likely discuss all of that.
William relaxed, laying on his side as I manipulated his cock and balls, with my mouth, fingers and tongue. He did, however, suck in a quick intake of breath as I took his testicles into my mouth. His cock, of course was far less sensitive and he was able to close his eyes as I sucked him and gently massaged his balls.
He wasn’t touching my penis just yet. Though I imagined he would, just as soon as he began to “Peg” me rectally. His cock was fat and juicy, and coated with my spittle, when he informed me he was ready to copulate with me. As I knelt and then positioned myself on “All Fours” upon the mattress, William reached into a bedside lamp table drawer for a bottle of Lubricant.
HIs fingers felt so wonderful as he coated my anal passage with the creamy, oily substance. His lubed cock felt yet even more amazing, as he slowly slid it into place, to begin “Railing” me. He began to slowly pump his penis in and out of me, and I soon got into a wonderful rhythm with his steady, tempered pace.
As relaxed as William’s ministrations were, I craved far more. I had grown to enjoy my sexual activities to be “Rough” and Turbulent. So I then increased the intensity of my backward thrusts as well as the “Squeezing” action of my ass-cheeks upon William’s cock. As I would shove my ass back towards William’s pelvis I would emit a, "Screech” and expel my breath.
Conversely as I would pull away from William, I would clamp my ass-cheeks around his cock, and let-out a gasp as I would inhale. At that juncture our “Fucking” took on a frenetic, passionate, rhythm. I expected that neither of us would possibly be capable of sustaining that sort of tempo without ejaculating in short order.
My estimation was accurate. William climaxed initially. The action of him pumping his warm seed inside of me caused me to screech and then burst forth with my very own, stream of sperm. I struggled to stay up on all fours and somehow managed to remain upright until William’s cock shrank and slid from my ass. At that point I finally laid on my side, upon the bed and pulled William’s warm body to me.
“I need something to plug my ass with, to keep your seed inside of me,” I sighed, femininely.
“Wait. Here, use this,” William said.
He’d reached into the drawer of the same lamp table where he’d gotten the Lubricant, and handed me a Tampon.
“Oh? I see that I might not be the only Sissy you’ve had in bed with you here,” I said.
“No, but you certainly are the prettiest, by far the most effeminate, and absolutely more Doll-Like, than any Sissy I have ever seen,” William commented.
“Oh? Well I’m very flattered,” I admitted as I plugged my rectum with the Tampon.
“William. Have you ever been with a real female?” I asked.
“No I haven’t. I knew at a very young age that I was fond of girlish males. I never even attempted a relationship with a female,” he admitted.
“Vivian has told me of your marriage and the occurrences that broke it up. She also tells me that you can appear as an absolutely stunning woman,” William added.
“Well. If you’d like. I can do that for you. Though, I’ve become very fond of presenting as a truly, effeminate Sissy,” I replied.
“We’ll have to think about and consider that, going forward. I do love how you looked today, when we met,” William admitted.
It was later on, in the early morning hours, when I turned my body over, and snuggled against William’s warm, firm, muscled frame, that I knew I never wanted to leave this man’s side. I reached over his hips and held his cock in my right hand. I attempted to turn him over, towards me.
He awoke slightly, and smiled, pulling me into his chest. I said to him, “I want to suck you off and have you shoot into my mouth.”
“You do? How nice. Do you want me on my back like this?” William asked.
“Yes please. Just like that. That is so very perfect. Relax, and lay still. Close your eyes and enjoy what I do. Let me take care of everything, for you. You took amazing care of me last night,” I whispered, as I licked the end of his penis and began to feel it grow in my soft, smooth hands.
I lovingly cupped William’s balls as I took more of his cock into my mouth and really began to suck on it whole-heartedly. I listened to his steady breathing as I increased the action of my mouth, tongue and lips upon his penis. I knew from my prior experiences with both Estefania and Sandy, that I could give an amazingly proficient blow-job.
Such a wonderful method for two lovers to begin a day. I looked up at William from between his legs and I could both see and feel his body tensing. His breathing became more intense. His eyes opened as he pushed with his hands down upon the bed. It was then I sensed and felt that wonderful moment when a penis swells, and ejects sperm.
I was prepared. I am always prepared to do my lover’s bidding when he ejaculates. Unless I am told otherwise, I swallow every spent drop of sperm that I possibly can. Of course there are times that my lover prefers to spew his sperm upon my face, into my hair, all over my tits or any combination of the three.
In any or all of those cases I acquiesce perfectly. I’m well trained, well behaved and perfectly disciplined. As I gulped down William’s seed I then realized I had his sperm in both my rectum and tummy. What a lovely thought that was. I wanted to always be able to make love to this man. I hoped our union was to continue.
Chapter V: Vivian’s Creation
“Mummy? Are you most certain you don’t desire to give me away?” I asked.
“I am positive dear. Vivian should be the one to give you to William. It was Vivian that brought you to the place that you are at today. Vivian saw to it that you would find your true sexuality. She introduced you to both numerous Gay men, as well as the Gay lifestyle. She even made it possible for you to meet William,” my mother insisted.
“I’ll be perfectly happy to be the Mother of the Bride. You are going to be the Bride? Aren’t you dear?” Mother asked.
“Oh yes Mummy. But not in the truly conventional sense of the word. I won’t be wearing a gown. I’ll be wearing heels of course and I’ll carry a bouquet. And my hair will be ‘Done’ Up. But William wants me to be dressed is a white linen slacks and jacket set, with a lacy pink blouse, similar to what I wore when we met,” I explained.
“I see. But the person officiating the ceremony will pronounce you and William, man and wife?” Mother asked.
“Yes. Of course. The head partner at the Mendoza Law Firm, where William is employed, will officiate. That would be Carlotta Mendoza. She applied for and received one of those ‘On-line’ Minister’s Licenses,” I explained.
“Yes, I’ll be William’s wife in the sense of being a Gay, Sissy-Wife,” I agreed.
Neither Daphne, Lisette, or Brenda would be present. I’d been invited to Daphne’s wedding. However I had declined. Later on, Daphne and I had discussed things and agreed we’d eventually get together with our new husbands at one of our homes for dinner. However, Estefania would be present to assist Cynthia, the new manager at “Sophisticated Lady,” with my hair and makeup.
Estefania and I had a lot of catching up to do. She also had a new “Man” in her life. He enjoyed her fully as a female named Estefania. On the other hand, William, primarily enjoyed me “Presenting” as “Coco” an Effeminate Sissy. Which was how I’d look for him at our wedding.
Then, there were those occasions when I’d “Doll-up,” as a girl, named “Coco.” I’d grown a nice set of “A+” sized tits and could nearly fill a “B” cup brassiere at that point. My full legal name was now, Coco Colette Breckinridge, as I’d already taken William’s last name, even prior to our marriage.
There were, of course, times, when William would have me dress as a glamorous female. Those would generally be events such as attending the theater, or something work related, where we would dine at the home of one of the other “Partners” in the law firm.
The Mendoza Law Firm was very “Progressive.” At these dinners I would be accepted and treated no differently than any other wife, fiancee or girlfriend, of any Male Partner in William’s office.
I’d never really returned to live with Vivian after the lengthy “Weekend” when she’d “Loaned” me to William to do some “Housekeeping” for him. I truly don’t yet recall how long I had been living with William and “Playing House,” when he’d said to me, one evening, “If you’d like to stay and live here Coco, I’ll arrange with Vivian for you to move in with me.”
That was it. The following Saturday afternoon, we drove to Vivian’s to pack up my “Things” and drop off Vivian’s house key. From that day forward, I have never spent another evening in anyone’s bed, other than William’s.
William was very well connected. A few months prior to our wedding, and after we were officially engaged, he asked me if I missed working as a hairdresser.
“Understand that I desire for you to be happy, Coco. And if you prefer to be my stay-at-home wife, you may do that,” William added.
“Well there isn’t a lot of housekeeping to do with the cleaning service you employ. I do enjoy cooking for you from time to time though, even if we do eat out quite a bit. Hmm? Doing hair part-time might be a good way to begin, and get a good feel for just what I want to do?” I opined.
“Consider it done. I’ll arrange an interview for you with Emilio at Salon Bellissimo near McPherson Square. It isn’t very far from our offices at Mendoza Law,” William explained.
Emilio, who was very obviously Gay, was really very nice. Even if I did feel as if he was picturing me naked and undressing me with his eyes, the very day I went in for the interview. He looked me over, as well as up and down, prior to having me sit across from him at his desk. Then he read over my resume.
“William did some legal work for me when I purchased the salon. I feel that I am indebted to him as to what little he did bill me. By hiring his future wife I feel I can make things right between us. You are very attractive, Coco. Many of our wealthier Clients are very forward with the stylists. Of course if you are working three days per week, you should experience less of that,” Emilio shrugged.
“I can handle it. I’ll let them know I’m happily engaged and in love with a wonderful man,” I explained.
“Ah yes. Very well said, Coco. I have another question. We are open on Mondays, but only for Private Appointments of a very personal and exclusive nature. William didn’t tell me every personal detail concerning you, of course. Only the highlights. So, I must ask this. When you were younger, were you ever Petticoat Disciplined by your mother, or possibly an Aunt?” Emilio inquired.
“No, but I sincerely wish that I had been. It might have made the journey I have been on a little smoother. I’ve hid for years behind the ridiculous facade of pretending to be someone that I truly wasn’t,” I explained.
“I understand. You see, these private appointments I spoke of, concern Feminization and Emasculation. In some cases, the transformations are being mildly Enforced by a dominant partner, employer or even a parent. Though none of the feminized subjects are minors. Would you find it objectionable to be a participant?” Emilio asked.
“No, I don’t think so. In fact, in the earliest days of my current transformation, I wasn’t exactly a totally eager candidate myself,” I said.
“I’ll keep that in mind, as I believe you would be an asset during one of these carefully guided Makeovers,” Emilio added, smiling.
The day of the wedding, I was terribly excited. Besides it being the day I would marry William, I’d also be seeing Estefania for the very first time since the day we’d been discovered in bed together by Lisette and Daphne.
Both Ms. Linda and “Auntie” Vivian, helped me both prepare and dress for the ceremony. Though William was planning on having a spare bath remodeled into a Home Salon for me, the construction was only in the planning and bidding stages. Thus, Vivian shampooed my hair with me kneeling over my bathtub.
The two “Matrons” escorted me to my boudoir where I saw my clothing for the festivities laid out upon my bed. Along with my slacks, top, jacket and undies was a waist cinch.
“Am I going to be corseted today, Auntie Viv, Miss Linda?’ I asked.
“No dear. That’s a waist-pincher darling. Not a corset. We just want to give your Svelte figure a bit more definition,” Linda, the dark haired, brunette beauty commented.
“Sweetie. Everyone coming to this wedding knows you are a Gay, Sissy-Boi. So, to contrast your effeminate prettiness, with a striking, feminine shapeliness, will only serve to exaggerate and overstate your breathtaking Androgyny,” Aunt Viv explained.
“Were is Mummy?” I asked.
“She’s here, Princess. She’s with Cynthia and Estefania in a guest boudoir. She’s already dressed and having her hair makeup and nails done,” Ms. Linda informed me.
“Estefania has already arrived?” I nearly gasped.
“Yes Darling. You’ll see her very shortly. As soon as we have you dressed. We know the two of you want some private, quality time together,” Vivian added as she wrapped a fluffy, pink towel around my wet locks.
Linda had me hold tightly onto one of the four bedposts of my canopied bed. I was about to be snugly encased within the figure shaping, waist-cinch. As the ladies wrapped the cinch around my torso and began to tighten the lacing, I thought back to that day in Sandy’s salon when Sandy bent me over a Vanity end table, tied my wrists to the legs, plugged my mouth with a ball-gag, and fucked me senseless.
In most all respects, my future husband William was everything Sandy was not. He had a masculine exterior, though he was Gay. He was fabulous to go clothes shopping with, as he knew just what looked really good on me.
Oh, but I did miss the manner in which Sandy “Played Rough” with me when we had sex. I was in the process of convincing William that he could always take punitive measures with me whenever I was a naughty, Sissy-Wife.
As William’s Boi-Bride, I needed strict discipline in order to perform all of my wifely duties to perfection. William was sometimes puzzled by my desire to be a reprimanded subservient. However I believed I was making progress with respect to that.
Once Vivian approved of my waistline, she and Linda continued dressing me. The Waist-Pincher as always had pushed some flesh up into my bosom area, giving me a solid, “B” cup. Vivian fitted me with a pink uplift brassiere before Linda slipped a matching panty-brief up my legs. I would also wear pink, knee-high hose with lacy, elastic stay- ups.
Next I was helped into my ruffled, back-buttoned, red, lace blouse with a Fussy Furbelow in front and Frothy, Lacy cuffs. Next came my matching Cream colored linen slacks and jacket, with four-inch heeled beige pumps. My heart skipped a beat as I could hear voices coming down the hallway to my boudoir.
I knew that one voice was that of my former lover, Estefania. When Estefania entered my boudoir with Cynthia, I was speechless. She looked so very stunning. We both just stared at each other. Cynthia broke the silence.
“I still have to do Coco’s mother, Roxanne’s, nails ladies. Why don’t we leave Estefania and Coco alone, to reacquaint themselves? You girls still have to change and do your hair and makeup, don’t you?” Cynthia asked.
Once Estefania and I were alone, I stood and hugged her, “You look amazing, girl. Allow me to at least kiss your cheek. We’re both taken now, aren’t we?”
“Oh yes we are love. You will be married today and I have such a wonderful man in my life, in my boyfriend, Carlos,” Estefania replied.
“Now relax and sit down sweetie. Vivian told me exactly what she wants me to do with your hair and makeup. We’re going to backcomb and tease your Pixie into an Updo. It looks as if your spot perm grew out, so you do have a little more length to work with,” Estefania opined.
“And your Auntie Viv wants your makeup to be vivid, striking and very dramatic, and I simply adore that idea,” Estefania gushed.
That was so very much Vivian. She wanted me to stand out as emphatically and as showy as possible. I didn’t mind. What bride doesn’t want to be noticed at the wedding? Estefania began to set my hair on large hot rollers with a gooey setting pomade. As she did so she “Gushed” concerning her love life and how much she enjoyed hairstyling.
“If it weren’t for you, Coco, I don’t think I’d be this happy about my lifestyle. I mean it was you that brought me to the place I am at today. You truly made me take an amazing look at who I was, and what I really wanted to be. I do so simply love being a hairdresser and working at a Beauty Parlor,” Estefania emoted.
“And I’m so very crazy in love with Carlos. I never dreamed I could possibly adore any man the way that I am smitten with him. And it was you that introduced me to the Girl inside of me, that I am today. I cannot thank you nearly enough Coco. Oh, I see you did your nails, recently. Last night?” Estefania asked.
“Yes. Estefania, I am so very thrilled that you are so completely happy. The week we spent together as lovers eventually led to me learning who I really was, also. It’s just so amazing honey,” I agreed.
With my hair “Done” and swept atop my head, and my makeup shimmering brilliantly upon my face, I made my way to the gardens of William’s estate. I kissed Mummy, Linda, Cynthia and Estefania, prior to taking a deep breath and smiling at “Aunt” Vivian as I held my bouquet.
Two large tents had been set up in the middle of the gardens. One for the wedding and the other for the reception. Vivian took my left arm as we entered the tent. Some sort of Celtic music was playing over the sound system. William was standing at the stage, with his best man, who was another Partner in the law firm.
Over the sound system, the music was interrupted as Carlotta Mendoza announced through a microphone, “Ladies and Gentleman, the bride and the bride’s escort have entered the tent and are making their way to the stage.”
Everyone stood and turned. All eyes were upon Vivian and me. When we reached the location where William stood with his best man, we stopped. I turned to look at William.
“Ladies and Gentleman, family and friends, we are here today to witness the Marriage of William and Coco. Together, and along with me, they have written out this brief ceremony. So, who gives away Coco to William?” Carlotta asked.
“I do,” said Vivian as she took hold of me and slowly posed me so that I was directly facing my future husband.
“Very well. So. William, do you promise to care for, protect, discipline and instruct Coco as if she were a helpless child?” Carlotta asked.
“Yes I do,” William said.
“Very well. And you Coco, do you vow to love, honor, adore and obey William? Do you also promise to keep yourself, pretty, slender, sylphlike and sexy as long as you are married to him?” Carlotta asked.
“Yes I do,” I answered.
“That’s just so very wonderful. Vivian, do you have the rings? Place William’s band on the ring finger of his left hand. And give him Coco’s diamond. Very good. Now William, please place Coco’s diamond on the ring finger of the bride’s left hand. Perfect. I now pronounce you man and wife. William, you may now kiss your, Boi Bride,” Carlotta stated as everyone clapped and cheered.
William and I had kissed so frequently ever since we’d met. But that kiss just seemed so very different and so amazingly special. We went from the marriage ceremony tent, to the tent where the reception was held. As the sun set, nearly everyone had left the reception. We said our goodbyes to those that remained.
The caterers would be cleaning everything and taking the tents with them. It was Saturday evening. We wouldn’t be leaving for Aruba and our honeymoon until Monday morning. I’d forgotten to place a Sani-Pad in my panty brief and I was already dripping and making a mess of my panty.
As we kissed in William’s bedroom I said, “Please. This evening. Please make me your whore? Treat me like a slut. Please?”
“I will, my little Fairy, Boi-Bride. I promise to make you feel as if you are a cheap whore and a real slut. I promise that and more to you upon this, our wedding night.
Hearing that from William truly surprised me. We stripped to the buff in silence. Then William pointed to the bed and said, “Lay face down Coco. I’ll prop up your ass and torso with some pillows. Scoot ahead as close as you possibly can to the headboard. I’ll be tying your hands and wrists to the headboard center piece.”
My cock twinged in excitement once I heard William say that. I knelt on all fours and gripped the headboard centerpiece to make it much easier for William to fasten my wrists so very snugly. He used some old neckties which he was ready to donate to a charity.
Once my wrists were snugly secured, William slapped my ass with an open hand and ordered me firmly, “Now lay down quietly upon those soft pillows I’ve provided my Little Sissy Boi.”
“Yes Daddy,” I replied as I also complied quickly to his instructions.
“Now Coco. I’ve spoken at length these past few days, with your Mummy Roxanne, your Auntie Vivian, and even your Ex, Ms. Daphne. And they all say the same thing. Prior to you coming under my watchful eyes, you were a sneaky, whorish, cheating little Bitch-Boi, weren’t you Sissy?” William asked as he slapped my ass with a leather belt.
“Ouch!” I whimpered, as I had not seen this coming.
“Well were you? Now answer me Sissy,” William spoke as he slapped my ass once again with the belt.
“Oh wow! Ouch! Yes. Oh that stung, Daddy. Yes Daddy. I was a real slut. I did not keep my marriage vows. I was a very naughty, nasty whore,” I agreed.
“I thought so. Yes. Now Mummy Roxanne, Aunt Vivian, as well as Ms. Daphne have all encouraged me to purge you of all of these simply vile behavioral tendencies with a firm whipping, and then a good, vigorous Ass-Fucking,” William stated in his proper British manner of speaking.
“Yes. They are correct. I need to be punished for my horrid transgressions, Master Daddy William, Sir. Please do. Both whip me and fuck your silly, naughty Bitch-Whore senseless My Master,” I said, while shaking and whimpering.
“Well then you shall get a Dozen of the very best. Three each on each ass cheek and thigh, in random order. Shall I ever have to do this once again, I will add three each to the soles of your feet, Bastinado style. I’ll not be married to a cheating Sissy-Slut for even another moment,” William pronounced.
“Count each stripe, and thank me. Prepare to be cleansed, my darling Little, Bitch-Boi Bride,” William added as he struck me upon my right ass cheek, with his leather belt.
“Oh my! Oh yes, number one. Thank you Daddy Dearest for my correction,” I gasped.
The next eleven Stripes came so rapidly that I soon became a blubbering, slobbering mess, by just futilely attempting to both, keep count, and thank my Daddy for disciplining me.
“There now my Prissy, Baby, Boi-Bride. Let Daddy soothe your hot, plump, pink ass, with some cold cream and Aloe Vera Gel. There, there, my Little Pansy. Why don’t I rub a small amount on your tiny, shrinking cock?” William asked.
As he soothed my butt, and massaged my Nub and my tiny Peanuts, I began to pant. I was being driven to distraction. Then I felt William’s well-oiled fingers enter my anus and I fully realized I was about to be screwed right into the mattress.
The excitement had my body vibrating. I realized William wasn’t about to Domme me every single time that we screwed. But I would readily accept whatever he could allow to me. It was like a wedding present that I’d wanted, but didn’t expect. My asshole was really opened up from the sensuousness of it all. His penis slid nicely into my anal opening. His male fervor as he “Banged” me was far more zealous than usual. My penis was leaking all over the bed sheets. I was so hot from being spanked as well as being thoroughly, verbally chastised.
His cock slid in and out of me rapidly. I held tightly to the place where my wrists were bound snugly, at the headboard centerpiece. I used this fulcrum as a lever to thrust my ass back and forth in time with the back and forth motions of William’s pelvis. My heavy breathing had turned to squeals and shrieks.
I was already dribbling, when my Nub began to squirt semen from my tiny shriveled ball-sac. Then William let loose with a gusher of ejaculate which filled up my lonely, lubed rectum. That felt so amazingly wondrous that I screamed. In the aftermath, as I laid in William’s arms and kissed his pecs, I let him know how amazing our coupling had been.
“Oh thank you my dearest darling for such a memorable wedding night. You are my Prince forever, Master William,” I sighed.
“I rather enjoyed the excitement of our foreplay and also the copulation that followed, my sweet Pansy. To see you so Supercharged from being soundly castigated is very arousing. You have such a deep need and desire to be derided as well as subservient to your lover. I find that aspect of your effeminate psyche to be amazingly erotic,” William added.
“Will you grant me two wishes upon our honeymoon, my Master? First, fuck me in the early moonlight on the beach? Then, allow me to suck you dry at sunrise on our veranda, after I have served you your morning coffee? Please?” I practically begged.
“Yes. Of course my Darling Boi-Bride,” William agreed.
“Thank you. And for that, you are no longer my Prince. You are my King,” I said as I kissed and licked, his sperm-coated cock.
I carefully plugged my rectum with a tampon to hold William’s seed within me overnight. Then I slipped into a negligee and laid beside him as we both basked in the glow of our post-coital bliss. Until that evening, I don’t imagine that I’d ever dreamt that I could ever feel so very sexy and fulfilled as I did at that moment.
Little did I ever dream, that my journey as William’s sexy Boi-Bride was then only in its infancy.
Denouement
We were shopping for me at Cecily’s Sissies, a boutique that advertised “Ladies Attire and Uni-Wear for the Very Discriminating Style Queen.” It was located just off of Dupont Circle near one of the Mid-Eastern Embassies. A wealthy dowager, Elaine, who regularly brought her adult son “Mimi” into Salon Bellissimo, for a “Private” Monday appointment, had recommended “Cecily’s” to me.
I had just exited one of the dressing rooms, to model a very “Chi-Chi” outfit for William. The ensemble consisted of a pair of Pink Capris, with a sash belt, along with a matching Bolero Jacket, over a white Cami-Top. With it I wore white 3 inch pumps and matching anklets.
My hair was now in a very stylish, heavily jelled and sprayed, Titian Pompadour, with a severe undercut, at both the sides and the back. My makeup was daring, though flawless. My nails were elegantly lengthy and French-Manicured in Lilac and Pearl. Baubles hung from my ears and dangled from my slender, limp wrists. My entire appearance loudly exclaimed, “I’m a Flamboyant, Gay, Pansy Queen!”
William was rather comfortable showing me off, even to the top partners at the Law Firm. Of course, Mendoza Law was very notable for their strong support of LGBTQ issues. It was quite well known that Carlotta Mendoza, the head of the firm, lived openly with her female “Partner.”
As I pranced from the dressing room, hands on my hips to “Show-Off” my new attire to William, I heard a female voice ask, “Blair, is that you?”
I paused and stopped. Then, looking in the direction of the voice, I saw Jessica Habersham with a puzzling look, yet a smile on her face. Jessica had been a client of mine at the “Sophisticated Lady.”
“Yes. Oh hello Ms. Habersham. Yes. It’s me. But these days my new, legal name is Coco,” I stated.
“Oh yes. I think I heard that from your old flame, Estefania. But now, that I see you for myself, the name Coco fits you perfectly dear,” Jessica Habersham agreed.
“Thank you Ms. Jessica. Oh. How very rude of me. Ms. Habersham? This is my husband, William Breckenridge. William. Jessica Habersham. She was a regular with me at the Sophisticated Lady,” I added.
Jessica and William shook hands and exchanged greetings. Then Jessica turned back towards me.
“Yes, I heard you and Daphne had split up. Now I realize why,” Jessica added.
It was then that William excused himself to use the men’s room.
“So, you are now the wife of a very handsome man. And he’s English also. Isn’t he? Interesting. Coco. We were always very honest and up front with each other, weren’t we?” Jessica asked, and I agreed.
“Then tell me something. When you make love to your husband, do you pleasure him with your mouth Coco?” Jessica asked, her voice barely above a whisper.
“Yes ma’am, that’s true,” I agreed.
“I don’t enjoy doing that at all, and my husband loves it. And then, when you copulate. Does William enter your rectum?” Jessica inquired.
“Well yes ma’am, he does,” I nodded.
“I could never do that. It must be very painful, isn’t it?” Jessica went on.
“It might have been at first? However, I regularly used vaginal dilators to widen my passage. And there are all sorts of amazing lubricants, these days. Some even have numbing agents. I do know the numbing feature allows the Husband to last longer,” I admitted.
“Oh I would hate that too. I want it to be over as soon as possible. The quicker the better,” Jessica admitted.
By the time William returned from the Men’s room, Jessica had departed.
“So, do you like this outfit on me, dear Master” I asked, after adding a dainty, pink neck-scarf tied off to the side.
“It’s lovely. I really enjoy the way the Capris hug your nicely shaped hips,” William stated.
I wore the very same outfit the very next Monday to the salon. I wanted to show Elaine what I’d purchased. She and her Sissy, Adult son, Mimi, were coming in to have Mimi’s hair, nails and makeup done. “Mimi” had been “Mummy’s” Lady’s Maid for the past several years.
Mimi had experienced some issues at a Private High School where he’d boarded, and had to be home schooled until “Mimi” entered college. It was while Mimi was home schooled, that his governess had initially introduced Mimi to Petticoat Discipline and the results had impressed Elaine.
When Mimi had once again ran into legal problems due to drug use, gambling and sexual assault while in College, “Mummy” hired an even stricter governess to “Tame” Mimi’s “Boyish” ways. Mimi was kept in Petticoats, dresses and high heels right into adulthood. Elaine also had a very tight legal hold upon Mimi’s trust fund.
One stipulation that Mimi’s late father had insisted upon, was that Mimi must be at least 25 years old and married, prior to ever being allowed to manage the trust fund on his own. Elaine realized if she kept Mimi in dresses, heels, makeup and styled hair, he may never, ever become married. Unless of course, Mimi’s Spouse, turned out to be a very strict Mistress or Master, in their own right.
“Mimi” was now 23. “She” was an attractive, Ash-Blonde. The outfit she wore to the salon was to Die For. She has on a puffed-sleeve, Flared-hem, Nipped-Waist, White dress, with red Polka-Dots and organza petticoats. Her white gloves were wrist-length, and she had a pink, Michael Kors Pouchette which she carried adorably, “French” style in the crook of her left arm.
Her white pumps had 4 inch heels. I was so excited by her fabulous outfit that I used a knee-length salon cape to protect her apparel. I then asked Ms. Elaine, “So what are we doing today, Madame Elaine?”
“Mimi has a date. Actually she’s spending the long, holiday weekend with a dear friend of mine that just gave a talk on Antique Curios to our ladies’ club. He’s an absolute expert on various Estate items in this region,” Elaine said proudly.
“His name is Edward and he’s a few years older than me, and I believe he’s just what Mimi needs in Her life. He’s a stern disciplinarian and he won’t hesitate even a moment to give a insubordinate Sissy Girl an over-the-knee paddling,” smiled Elaine.
“Well then. Are we planning on a trim, along with a wash and set, with full evening makeup?” I asked.
“Oh yes. That would be perfect, Coco,” Elaine agreed.
While I shampooed and conditioned Mimi’s blonde locks, Elaine looked over various styles in a folder I presented to her. I only trimmed away Mimi’s spilt ends. I then turned to Elaine who said, “This Bouffant Flip will be perfect, Coco.”
I agreed and began to roll up Mimi’s hair onto large, plastic curlers. After I put Mimi under the dryer with a “Cosmo” to read, I sat with Ms. Elaine and we chatted.
“You know Ms. Elaine, I sometimes envy girls such a s Mimi and my old flame, Estefania as they ‘Present’ daily as Girly Girls. Then I realize that isn’t who William wants me to be. And my sole objective in life, is to make certain William is thoroughly happy. And William prefers me to appear as a Showy, Effeminate, Limp-Wrist, Pansy,” I stated.
“And that is what any subservient wife strives for Coco. Even an Ultra-Effeminate Boi-Wife such as you. You husband must be happy and contended 24/7. That is you job, honey. And honestly Coco, you pull-off the entire ‘Gay’ thing, wonderfully, Princess. I tell everyone I know, all about you, sweetie,” Elaine effused.
“Oh thank you. And you know what, Ms. Elaine? Dressing and presenting as I do, here at the salon, at home, and among our friends, family, and publicly, makes those occasions when William expresses the desire for me to be his Girly-Girl, all the more exciting,” I admitted.
“Most of those instances are very special anyway. You know. He’ll have me really Femme-up when we attend the Opera, or the Theater. Or possibly there might be an evening or afternoon event put on by a Member of the Law Firm, or even a romantic dinner at the Country Club,” I said giddily.
“And obeying him fully, is what makes your relationship work, Coco. William remains the Master, and you admit that you are his lowly servant, simply by showing your absolute obedience.” Elaine added.
“Yes, it’s wonderful. Now let me check on Mimi,” I said.
Until William provided me with an SUV for transportation, he’d take me into the salon 3 days a week, and should William work late, Emilio would transport me home. Once he gave me the SUV for my birthday though, I had more freedom as to work and shopping. Mimi had been my last “Private” client of the day, so I made it home in time to prepare William’s dinner. I became very excited when I heard William’s Maserati pull into the drive.
I minced to the foyer wearing the very same outfit I’d worn to the salon. “Welcome to your castle my wonderful, Master. Let me have your laptop and briefcase. Relax here in the Parlor and I’ll bring you a Scotch on the Rocks,” I tittered.
As William sipped his drink I knelt at his feet and removed his shoes and socks. Then, like a Lap-Dog, I rested my beautifully manicured fingers upon his knees. He looked down at me smiling.
“I have a surprise for next weekend. Carlotta Mendoza and her Partner, Deborah, are having a Saturday afternoon and possibly into the evening, Soiree. And you, my adorable Fairy, Boy-Bride, have been such a sweet Princess lately, that I believe it would be a wonderful day for you to appear as my Girly-Girl,” William winked.
“I think something very ‘Stepford-Like’ would be perfect for your appearance,” William stated.
“Oh William, that will be so very exciting and wonderful, darling. I know what I want to wear, too. Oh yummy. That long, hip-hugging, white, fishtail skirt, with a matching, midriff length, tube top. With tall, pink heels of course. And enough jewelry to make me look as if I’m some sort of Sultan’s slave girl,” I giggled.
“I’ll use a curling iron on my Pixie, now that’s it’s grown out enough, and I’ll really look showy. I adore being your girly girl, William, you know that, don’t you darling? Do you want your steak right now? I’ve made the salad, marinated the meat, chilled the wine and I’ll need to put a little heat on the baked potatoes. I just feel so sexy right now,” I said, dreamily, looking up at William.
“You’ve had such a long day, and it’s the middle of the work week. Why don’t I suck you off prior to dinner?” I asked.
“You’re amazing, Coco. I don’t think any man I know has a wife with the sex drive that you have. Of course you can suck me. Let me take off my slacks and underwear,” William said.
Within a few moments, I had a big, hard cock between my painted lips. He’d paid me such a marvelous compliment, comparing me to the wives of the men he knew and worked with. I wondered how much he had ever told them? As I sucked his cock and it grew fatter, longer and harder, I closed my eyes. My life had become such an astonishing dream.
Of course I recalled my past. However that person I was had disappeared. That person had vanished into thin air, never again to ever exist. I felt as if I’d always been Coco. And I knew I’d been destined to be the Boi-Wife of William Breckenridge. He took such wonderful care of me.
He shielded me from any sort of real decision making. I simply was not cut out for that sort of thing. And he loved me for just who I was. There was almost nothing like having William’s cock in my mouth. Truly, the only thing better was having William’s cock in my rectum. I almost wanted to stay kneeling, turn around and offer him my asshole for his pleasure.
It was far too late for that however. I could feel his penis expanding within my mouth, and immediately a jet-stream of sperm splashed against the back end of my tongue. I gulped and swallowed that, plus the next gusher of ejaculate that spurted from William’s cock. The taste of his Cum, was so wonderful.
I could have drank a full glass of it, as if it were chocolate milk. I swallowed down every last drop and then licked up and down William’s genitalia, from the tip of his penis to the underside of his balls. Then I laid my head in his lap and sighed, “Oh I love you darling.”
“Stay there as long as you need to my Angel. Dinner can wait,” he added as he ran his fingers through my hair.
My life had become an undeniable magical fantasy. And I wanted to caress that moment as long as I possibly could.
The End
*Thanks for reading. You may email me at priscillagaybouffant@gmail.com
I hope everyone enjoyed reading this as much as I enjoyed writing it.
ReplyDeleteThank you for posting this fabulous tale. Loved the conversation with your client Beverly. She really has your number.
DeleteDonna
Thank you Donna! Oh yes. The conversation when Coco is modeling a new outfit in a Sissy Boutique for William?
DeleteVivian is a very controlling mentor. I loved when she informed Coco that her marriage was over. She made it clear that Coco will only be dating gay men from now on. Most men love redheads with curls. Coco looks very sexy.
DeleteDetails make any story more interesting. Having Coco wearing Palazzo pants and carry a MK hobo purse on her date with Sandy leaves no doubt who the "girl" in that relationship is. The oral sex scene was terrific!
Donna
Oh? Beverly. Yes. In the salon at the very start of the story. I just re-read that. I forgot. You read in small "Bites" so to speak.
DeleteYes. Vivian was and still is a fabulous mentor to Coco. She is responsible for Coco's new lifestyle as well as her marriage to William.
DeleteThank you Donna! Yes, Vivian was, and still is, the most fabulously, supportive, domineering Mentor that any Aspiring, young homosexual could possibly wish for. Coco began as most Crossdressers do, starting out as a "Straight" male. Then, as Sabrina, Coco had sex with a gorgeous Hispanic boy, and realized "She" might be bisexual. But when exposed to a fully Gay lifestyle by the very Pushy, Vivian, Coco melted and eventually fell head over heels in love with William. What Gay Sissy Boy wouldn't relish life in the fast lane with a handsome, British, K-Street Attorney? And Coco owes it all to Vivian for her relentless insistence that Coco was then and now no more than "Gay-Bait" to put it very bluntly. I really tried to put it all out there with this story, Donna. Thanks for reading it so very carefully. Priscilla
DeleteLovely story Priscilla and many thanks for posting.
ReplyDeleteDenise Bouffant
Thank you Denise, Sweetie!
DeleteComments are being deleted by Blogger again. One of Donna's plus my response did not make it.
ReplyDelete