New! Barista to Rich Man’s Bitch

By Priscilla Bouffant

Once again I’m on the road for Urban Boi Wives, as well as the very popular, Alpha Male publication, VIP Culture. This time I’ll be interviewing an Alpha Money Manager that found that a Boi Bride would make the best Wife ever for him. 

     My flight to San Francisco went smoothly, and my rental vehicle was ready.  The 1 hour and a half drive to the Escondido Winery at St. Helena in the Napa Valley took place without a hitch. 

     The sprawling winery takes up 13 acres and the primary residence is an unreal 12,000 square foot Mansion. It is the domicile of a  Diamond Fund Manager of the Equity Index 500 offering, William Carstairs, and his Femme Boi Wife, Cerise Vivienne Carstairs. Cerise, looking very Glam, answered the door.

     She was attired in a white A-Line dress, with Pink Polka Dots. She wore a matching white ribbon, intertwined in her Champagne Blonde Tresses which were styled in a chin length, Flipped-Bob. She walked beautifully in her strappy, 5 inch high heeled sandal style stilettos. Her cosmetic application was simply perfect. It looked to be professionally done.

     She wore a jeweled collar. The nail polish on her lengthy nails matched her pink frost lipstick  and she had multiple ear piercings for her diamond earrings, dangling pendants and gold hoops.

     “Please do come in Ms. Bouffant. William is in the Parlor. Follow me please,” Cerise said softly, adding a pert curtsey. 

     “William darling, Ms. Bouffant is here from the magazine,” Cerise announced, once gain curtseying. 

     Mr. Carstairs greeted me warmly then gestured to his wife.

     “What type of beverage would you prefer Ms. Bouffant? If it isn’t too early for you, I could offer you a glass of any of our vintage wines,” Cerise offered as she went down an extensive list of the wines she could serve. 

     I chose a Chablis. Then she asked, “And you, William, darling?”

     “I’ll have what Ms. Bouffant is drinking,” William said.

     Once Cerise poured us both a glass each, and set the bottle on the coffee table she said, “I’ll be in the home salon darling, painting my nails. Should you need anything, please Buzz me.”

     “Cerise won’t be in the interview?” I asked as she minced away. 

     “No. If you really want to ask her anything after you interview me, I’ll need to be there. She really won’t say anything, unless she checks with me initially,” William stated.

Priscilla: Okay then, let’s begin. You received your MBA from Stanford. You also played baseball there. Though you were scouted by MLB teams you publicly announced you had no desire to play professionally. Your junior and senior years you Interned at Diamond Financial. You developed a great working relationship with Veronica Diamond, the Boss’s daughter. You went to work for them once you completed your Masters. In less than two years you were managing their Equity Index 500 Fund when the former manager retired. Good so far?

William Carstairs: Yes. You’ve done your homework.

Priscilla: Next. Your personal life. Married at 26. Divorced 3 years later. Married again, in two years. Divorced 2 years later. Then you stayed single for ten years. Once you met Cerise, you were married in a little more than a year. And now you are two years into the marriage and everything seems perfect. In fact I believe you met Cerise right after you bought this Winery. Tell me. What is the difference between Cerise and your two Ex wives?

William: First, I bought the winery only after the management team said they would stay on. I wanted the property and the winery was highly successful, but I knew nothing about running it. Everything about Cerise is 180 degrees different from my two Exes. 

Priscilla: I see, would you mind telling us how is that so? 

William Carstairs: I would be happy to or I’ll spell it out. After a year or so of marriage to each of those women, they changed radically. Sex became extra bland if we had any sex at all. I’d be lucky to get a blow job on my Birthday. They went from sleeping in Negligees and Baby Doll’s to wearing flannel nightgowns or ugly pajamas with cartoon prints on them. 

They stopped wearing high heels and tight skirts and out came the Tenner Shoes and Jeans. They might wear light makeup when we went out, but the dressiest they ever got was a pant suit. They’d rarely actually get their hair “Done.” Usually they  just had it trimmed. Rarely ever had it colored. Just boring. You did see how Cerise was dressed, coiffured and Made up. That was not because we had company. That is because I want her looking like that. I know it sounds blunt, but I know what I want in a woman. 

Priscilla: Its fine that’s the purpose of this interview to get to know William Carstairs, sooo how did you two meet?

William Carstairs: First let me begin by saying, I saw several articles in consecutive months in the VIP Culture Magazine, about men my age. Especially divorced men, who were disillusioned with today’s ‘Liberated’ Women. These men had discovered the advantages of having a Femme Boi Sissy Wife. I began to ask around, made some phone calls to sort of get an idea of how to find a Sissified Male. Then I lucked into Cerise. Who at the time was named Cyril. I had studied how each and every one of these Alpha Execs had emasculated and feminized their sissies.

There is a Radical Feminist Group that began in England that has an available Plethora of Resources to Enhance Feminization. Essentially they are Alpha Women Emasculating Beta Males and they have no problem at all with aiding Alpha Men who want to accomplish the same task.

Priscilla: You are speaking of the Cassandra Sisterhood.

William: Yes, exactly. So I began lining up a hormone doctor, and a  cosmetologist that was an accomplished transformation specialist. It was just that Cyril, soon to become Cerise made it so much easier. The key to the entire Emasculation thing, is to disconnect the Sissy Candidate from their old life and make them totally dependent on their Master or Daddy. 

Priscilla: So where did you meet Cyril/Cerise?

William: Right here in St. Helena. Cyril was working at the local coffee shop where I’d stop prior to driving into the ‘Frisco office. In the literature I received from the Winthrop Foundation, they listed ‘Signs’ that might give away a possible Aspiring Sissy. Cyril, was almost ‘Sweet’ in his everyday personality. And when I looked close enough it appeared that he just might have been wearing makeup and not cleaned it completely off. And even though he wore one set of earrings, he had piercing holes for three sets. What happened next was total ‘Fate’ not just coincidence. 

Priscilla: Now that’s certainly intriguing.

William: I work out regularly. In fact I have a gym here that I had built when I began to renovate the mansion. And during later renovations, I had a Home Beauty Salon put in for Cerise.

Priscilla: Well that was very sweet of you.

William: It was more for convenience than anything. You see, I do not permit Cerise to drive a car. Ever. I drive her, our chauffeur drives her unless it’s on his day off, and it’s the same with our Social Secretary/ Household Manager.  So, if I decide that Cerise needs a makeover and there is no way to get her to the hairdresser, I simply pay the Cosmetologist to come here.

Priscilla: Well you do look in fabulous condition. Shall we get back to the “Fate” that brought you and Cerise together?

William: Of course. Every Friday I would work out, shower and put on casual clothing at the Diamond Financial office gym in Frisco, and go out on the town. It occurred to me that I might meet a Twink to feminize at a Frisco Drag Night Club. I wasn’t in the club 30 minutes when Cyril/Cerise walked in and it turned out that the Sissy was one of the Entertainers there. He did impersonations of both Taylor Swift and Christine Aguilera. I took pictures of him as Cyril. I got more pictures of him in drag. I even got photos of him in Drag, kissing with a male in the audience. At that time  Cyril/Cerise lived over in Deer Park, worked at the coffee shop in St. Helena and nobody knew where he went on weekends. 

Priscilla: So as many Sissies do, Cyril/Cerise was hiding his Crossdressing Hobby.

William: Precisely. The following Tuesday, when he brought me my coffee at the Coffee shop, I pointed to the seat next to me at my table and said to him, “We need to talk.” I then let him know I knew all about his female alter ego and his possible ‘Trysts’ with male customers. I made him understand that I expected him at my Estate at 730 PM that night. He arrived right on time. I sat him down, gave him a glass of Pink Chablis and told him exactly how things were going to be from then on. He began sobbing. I put my arm around his shoulder and I told him I was going to be taking good care of him. I promised that from then on I would be the Sissy’s protector. He had nothing to worry over.

Priscilla: He…err I mean, she sounds as if they were broken already. 

William: Quite alright, you see right away I had Cyril quit his job at the Drag Club. I wanted him home with me on the weekends and at the house all day Monday, his other day off at the coffee shop. I wanted him doing housekeeping in panties, high heels a training bra and an apron, wearing full makeup. I insisted that he style his longish hair femininely. I began the hormones with the lady Doctor I had found through my transformation resources. And the hairdresser I had located that did Private, Male to Female Transformations at her home, began to stop by to give “Cerise” Charm Lessons. 

Priscilla: I see you didn’t waste any time. 

William: No. I then met with his landlady at his condo and explained that I was his uncle, and wanted to help him go back to college. I asked what we could do about his lease so that “Cyril” could move in with me. She told me that he rented by the month. So by the end of the next month he was residing at my estate. The condo he lived in was furnished so all he really had was his male apparel. I allowed him to keep any feminine things that belonged to him. Such as cosmetics, unisex, female and androgyne style attire. I then donated everything else of his to charity. I’d also begun to purchase a female wardrobe for him. I took his car keys away, sold his car and put the money into a joint account with me. The last thing I did to seal my Ownership of Cyril/Cerise, was have him quit his job at the Coffee shop, after that…. he was now all mine.    

Priscilla: You are quite the Alpha.

William: Thank you Priscilla. I sense you have experience or appreciate Alpha Men like myself?

Priscilla: Umm… yes- I mean-you were saying at that point Cerise quit working. 

William: (*snickers) Right, the the feminization really took off. Between the hormone dosages, the foundation garments and the figure training exercises, Cerise’s body really took on a truly feminine shape. With  her Charm Lessons she walked, talked and acted so very girlish. And slowly, even though I still saw some resistance, Cerise began to see me as her total Master and Daddy. Just a few months in, after her hairdresser had come to the Mansion, given her a makeover, dressed her gorgeously and continued her Charm Training, I came home from the office at about 5 PM on a Friday. Cerise had heard my car pull up and was waiting at the front door. She looked sensational. Her Champagne Blonde hair was curled and in an upsweep. Her makeup was heavy and flawless. She was wearing a pink, Pussy-Bow blouse and a white Pencil skirt with really tall sandal style high heels. Her bare legs were shiny and moisturized. Three sets of earrings dangled from her ears. Incredibly enough she reached out her arms and pleaded, “William Darling, I so desperately need you to make love to me. I simply just need your cock up inside of me. Hold me please and take me to your bed.”

I really didn’t need any more prompting than that. I’d given her, her very own really girly boudoir, but she wanted to be screwed in my bed. 

Priscilla: Oh my! She sounds as if she had become totally dependent upon you.

William: Yes. And she still is. Dependent as well as fully devoted. She’s told me, that without me in her life, she doesn’t really feel whole at all, and is simply a very needy, helpless and totally overtly-emotional female. And she craves my masculine strength, guidance and loving dominance. By the way. For this interview and article, how descriptive, if at all, is it acceptable to speak openly concerning the lovemaking?

Priscilla: Oh honey. The Editors at both Boi Wives and VIP Culture who will be doing the Spreads, each requested a complete tell-all. Go for it doll. I’m all ears. 

William: I see. I undressed her fully. I have a really “Thing” when it comes to unbuttoning or buttoning up, one of her dresses or blouses with the buttons in the back of the item. It just makes me feel so very much in control of her as well as the situation. I undressed and then stood in front of her and fondled her Sissy Clit-cage prior to unlocking it. She sighed and hugged me, saying, “Oh thank you Daddy,” when I freed her prick and testes. Next, I sat on the side of the bed, with my feet on the floor and told her to kneel between my legs and suck my cock. She then told me she had already took out the butt plug I make her wear, to be ready for me to Rail her asshole.      

Priscilla: Ahhh…. So she wears a butt-plug and she’s locked in Chastity?

William: These days she wears a vibrating butt-plug. I place it on the very lowest setting when I require her presence. As for a Chastity cage. Well not any longer. I mean the Estradiol and the T-Blockers have rendered her genitalia so completely useless, she just may as well be Castrated or have a Pussy. It would really be superfluous. 

Once she began to suck me off, I realized everything I’d been told concerning Sissy Cocksucker Wives, by their Masters, was completely true. Beyond a doubt, Sissies give the most phenomenal Blow Jobs possible. They are just naturals and they love to suck cock. I believe it’s in their nature to please their Masters. I’ve never had any blow job from a spoiled genetic female that was done with such great passion. I wanted terribly to shoot my seed right between her Blushed cheeks, but I saved that for another time. At this point I could not wait any longer to screw her butt. 

Priscilla: Wow. Allow me to guess. You took her with Cerise facing you, on her back, with her legs wrapped around your waist? (typical Alpha Male behavior) 

William: Very close Miss Priscilla. Her legs were in the air. I held them against my shoulders. It just might be the very most helpless position a Beta can possibly be placed in while being fucked. To me this is all about helplessness, dependency and neediness, on Cerise’s part, and Power and Dominance from me. And I really screwed her to the mattress. I plowed my oily cock into her lubed up Sissy-Pussy hole. She was screeching and panting and begging me to fuck her harder and faster. As I pumped my seed into her rectum, her Sissy-Clit oozed her juices all over her thighs. 

Priscilla: Wow…..Oh my….umm- please don’t get me too excited. 

William: It was not my intention, but I am pleased you are enjoying me reliving my experience. By the way, Miss Bouffant can I say, you are very attractive for a reporter yourself. If you get too excited let me know. I’m not exactly a One-Sissy man. 

Priscilla: Oh my… Mr. Carstairs.What about the wedding?

William: I didn’t really ask her to marry me. I just let her know we were going to be married, here at the Winery. I’d given a substantial financial donation to the Winthrop Foundation for all of the information, literature, videos and contacts they’d given me, to assist with Cerise’s Feminization. I wanted us to be married by a Cassandra High Priestess and they provided me a contact with one here in California. Locally, most people had wondered where Cyril had disappeared to, so it was a little too soon to reveal my new wife. Plus, we didn’t yet have a complete backstory for Cerise, just yet. The only people I planned on inviting to the wedding were people involved in her transformation, such as the staff at the GYN clinic, the hormone doctor, her hairdresser. Then of course key members of my household staff, and I wanted Cerise’s parents to meet their ‘new daughter.’ 

Priscilla: Wow. How did you plan on doing that?

William: Oh. I almost forget. I also intended to invite other men I’d contacted who had Sissy Wives, and of course their Sissies also. As for Cerise’s parents, I insisted she call them, admit she’d been a Crossdresser since even prior to when she reached puberty, and that she’d finally met a man who had helped her realize her lifelong dream of living as a female. Later on, I planned on letting people at work know I’d met a girl while nightclubbing in Frisco on the weekends, and that we’d had a quiet wedding at my Estate. 

Priscilla: How did Cerise’s parents react? And which key members of your household staff? 

William: Her mother, from the start was very understanding. In fact she wasn’t at all that surprised. Her father, who is my age wasn’t exactly thrilled about his only son becoming a woman, but with his wife’s help and encouragement, he came around. As for household or I should likely say, Estate Employees, my two most important are the Winery Manager as well as our SocialSecretary/Household Manager. The guy who runs the winery, does all the hiring, sees to the landscaping and even oversees renovations at the mansion. 

By the time the Home Salon was being done, Cerise was quite feminine and girlish, and he had no idea she’s been born a male. On the other hand,  the woman who manages the household and is also the social secretary, was there to witness Cerises transformation as was my driver/bodyguard. But they’re both very open minded and understand why I wanted a Sissy for a Wife.

Priscilla: Is there any way I could ask Cerise some questions?

William: Of course. But she will look at me for consent if she’s unsure about answering. I’ll buzz her.

     Cerise minced into the Parlor, smiling sweetly, holding up her freshly done fingernails for us to see. “Yes William Darling. You require my presence?” Cerise asked.

     It also appeared that she’d touched up her hair and makeup. She did a twirl on her tall, high heels as if she were Ginger Rodgers. 

     “Yes. Priscilla would enjoy asking you some questions, Princess,” William said.

Priscilla: You and William, like other couples where the wife was once an effeminate male, just seem to have an amazing marriage.

Cerise: Yes. Exactly. Our relationship is amazing, and my life is amazing as it has totally changed, and my wonderful husband is totally responsible for that. I’d been attempting to fool myself and everyone else into believing that I was a normal male, when truthfully I was a female hiding within a male body. I recall how I began sobbing after I arrived at William’s estate upon what would prove to be a fateful evening, and William informed me that he had planned for me to reside with him as his Live-in Girlfriend. Though I sobbed due to the mysteriousness of it all, I was sobbing in relief. I would now have the opportunity to be forced to confront my thorough failings as a male. 

 Priscilla: Wow. That just seems so profound. 

Cerise: I’d found someone who was willing to support me throughout my Feminine Journey. That he found me pretty enough to make love to me, was just awesome. And when we finally were married it was total Blissfulness. 

 Priscilla: How did you feel at the wedding?

Cerise: It was simply just so very magical, Miss Priscilla. I felt as if I were a Fairy Tail, Storybook Princess. I wore this lovely, Fishtail, Mermaid gown with my hair in this tall, upswept, curly Updo. My heels were so high and with the snug gown I had to take the most babyish of steps. And I just knew that everyone was looking at me. And when William lifted my veil to kiss my wet-look, Crimson lips, I just swooned into his strong, protective masculine arms, and I knew I wanted those arms around my Girly body forever. We honeymooned in Barbados at a Private compound, and William made love to me on a blanket in a cove at the beach. Our oily bodies coated in suntan lotion in the warm sun. 

Priscilla: That does sound very special. What are things like today? Are you a housewife of sorts? Do you cook?

Cerise: Ms. Hilton, our Head Housekeeper and Social Secretary has taught me to make some very fancy meals for William and I. I do very little cleaning though. Just dusting now and then. Ms. Hilton has a cleaning service come in once a week. Usually towards the weekend. If we have a get together with friends, or people from William’s office, Ms. Hilton hires a caterer. I’m totally just the hostess and the Lady of the house. At both Christmas and Halloween we open the Mansion to the Local Children. I just love having children around. We’re hoping to adopt a boy and a girl in the future.

Priscilla: Your parents were at the wedding.

Cerise: Yes. I was so very excited. Of course they’d come to the estate a few months prior, to meet William and also meet their new daughter. It was incredible. When Ms. Bianca, my hairdresser and charm coach, began my Transformation, when I’d moved in with William, she’d promised me that, One day my own mother would not recognize me, and she wasn’t kidding. I just love who I am today and how I look. I simply just love going to the Salon, the Boutiques, and Jewelry stores. I’m a total Girly-Girl and I adore being that. 

Priscilla: I’m happy to know that Cerise. Allow me to get some photos of both of you for my personal collection. If you both prefer, I can stay through tomorrow when the Magazine Photographers will be here. 

Cerise: That would be fabulous!

Priscilla: Umm…do you mind, if I use your washroom.

Cerise: Certianly, its-

William: I can show Miss Priscilla where it is myself darling.

Priscilla: Mr. Carstairs I think I can manage-

William: No, please I insist. This home is very large and one can get easily lost, besides for a lady such as yourself its very private.

***************

Priscilla: This home is rather large, thank you for walking me- ahh (*gasps )Mr. Carstairs why is your hand on my ass? 

William: The restroom is right this way, darling.

Priscilla: Sir, I don’t think Cerise would approve.

William: Shh…. I'm going to give you an exclusive, now inside.

(door shuts closed and locked)

***************

Priscilla’s note: I did stay the evening after an interesting detour.... The photos were taken for both Magazines I had done the interview for. I’ll post photos from the VIP Culture Mag, just above. Doesn’t Cerise look simply amazing and just totally in love with her man?