Halfway House for the Wayward Sissy: Tricked by Wife into Transitioning

By Jessica Cockburn

After years of suppressing his true self, Dan embraces his feminine identity as Daniele. With the support of his wife, Elaine, Daniele delves into a world of cross-dressing conventions, romantic dinners, and intimate discoveries. But as their relationship evolves and boundaries are pushed, Daniele must navigate the complexities of love, trust, and self-discovery.

• Language: English
• Publisher: Jessica Cockburn
• Release date: Sep 27, 2023
• ISBN: 9798215760772

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Halfway House for the Wayward Sissy

Tricked by Wife Into Transitioning

Copyright 2023 Jessica Cockburn

Published by Jessica Cockburn at Smashwords.com

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Table of Contents

Prologue

Chapter One

Chapter Two

Chapter Three

About the Author

Connect with Jessica Cockburn

Prologue

Author's note: All characters depicted in this work of fiction are 18 years of age or older.

On a Sunday, I returned home after a week away. It was the longest time my wife and I had been apart, and it was also the longest I had ever spent fully embracing my feminine identity. The excitement of it all still lingered as I pulled into the garage, leaving my luggage in the trunk before making my way directly into the house.

Being discreet around the neighbors was crucial. Since it was still daylight, I didn't want them to notice that my perfectly styled curls from last night's Farewell Ball were still intact. They looked so lovely that morning that I didn't have the heart to comb them out, and since I wouldn't encounter anyone who knew me, I decided to keep them as they were. Some fellow passengers gave me puzzled or amused looks on the plane, while others seemed intrigued before losing interest. There was even a middle-aged woman who scowled at me as if I posed a threat to all middle-aged women. However, a flight attendant complimented my hairstyle and admired my courage, wishing her boyfriend would do the same. Her words melted my heart, and I couldn't show enough gratitude whenever she handed me packets of pretzels for the rest of the trip.

I didn't see Elaine anywhere upon my arrival. In the past, this might have worried me, but not now. This was the new normal for us. I regularly attended cross dressers' conventions, and I wanted Elaine to see them just like any other business trip- a temporary separation that allowed us to appreciate each other more upon reunion. It gave us both the opportunity to be grateful for the occasional stresses in our relationship and reminded us that we are still happily married.

The kitchen appeared unchanged. The stove and counters were impeccably clean, suggesting that either the cleaning lady had just been or Elaine had been dining out frequently, possibly near her office where she often worked late. I knew she would be secluded in our study or perhaps the room beyond it, meticulously planning strategies and preparing for her court cases for the week ahead- a routine she followed every weekend. Part of me wanted to shout out Honey, I'm home! just to make sure she knew I had returned, but I caught myself and grinned. How domesticated we had become!

Of course, she knew. She must have heard the garage door's distinctive grind and growl when I entered. Despite the walls lined with books, filing cabinets, and our professional belongings, the sound reverberated even into the closed room beyond, where I dressed, worked, and kept my personal things, indulging in my fantasy life.

Elaine had stopped referring to it as your girly room and now called it our girly room or simply the reading room. I had decorated it in pink and cream chiffon, with delicate hangings, pastel sketches, and plump pillows on the overstuffed divan. A French Provincial bureau held my belongings, and a large mirrored vanity table was home to my makeup supplies. It served as my sanctuary to embrace my femininity. Initially, Elaine had resented it as an indulgence, but over time she grew to appreciate its distinct feminine ambiance. She found solace there when she needed a break from the harshness of her work, as we often sat together after dinner, engaging in our own activities like girlfriends rather than as a snug married couple. If anyone were to peek in, which was highly unlikely, they would witness two women enjoying each other's company- the tall one primly typing away at her keyboard, often dressed elegantly as if preparing to go out (though she never did), and the shorter one casually attired in tight jeans and a t-shirt, sprawled across the floor while jotting down notes on legal papers. I always appeared as the proper lady of the house, while Elaine resembled my adorable younger sister pretending to do her homework.

Elaine did take care to dress appropriately at work or social events associated with her job, donning expensive black dresses, power suits, or beaded cocktail gowns to maintain her professional image. I envied her extensive wardrobe, although I did own a few similarly elaborate and stylish dresses. However, she had the freedom to wear them whenever she pleased, whereas I was limited to donning them only during out-of-town gender meetings.

To Elaine, clothes were not a significant concern. As soon as she arrived home, she would change into shorts or sweatpants, hop onto the treadmill and stairmaster in our future baby's room, sweat out the day's frustrations, take a quick shower, and emerge fresh and natural, without a trace of makeup. Her soft, curvaceous figure barely contained in her jeans and t-shirt. Then she would peer into my feminine reading room, give me a kiss, inquire about my day, discuss dinner plans, and if she felt a little frisky, she would sit on my lap and slowly unbutton my blouse.

Before, we had both worked in town for the same large law firm. While Elaine handled litigation, I specialized in industrial matters regarding patent and trademark strategies. Now as a private consultant, I carried out the same work from home, communicating through phone, fax, or computer. I was an engineer at heart, not a lawyer, but I had retained many of the firm's former clients as my own. I had the technical expertise to solve their problems and the interpersonal skills to persuade them to follow my guidance. The firm went to great lengths to try and keep me, offering double my salary, executive privileges, anything they could think of. However, my wife eventually told them it was futile, they would never win me over with money and perks. She vowed to find another way someday. Money and privilege held no importance to me. What I wore was what truly mattered.

As an engineer, wearing corporate suits and ties was never my favorite thing. However, at home, I could dress in a way that pleased me - a more demanding feminine dress code. I would wear heels, skirts, style my hair meticulously, and ensure my makeup was impeccable, along with tasteful jewelry. This was my way of doing my job, in an office that I created for myself.

When Elle came home, I often didn't feel like changing into something more casual or removing my makeup for a trip to a restaurant. So, I ended up cooking for the both of us. It was a relaxing way to unwind after a day of solving complex problems, and I genuinely enjoyed engaging in traditional womanly activities. Most of the time, when Elle finished showering, I would already be dressed in something pretty and romantic for her, and sometimes I would have already set up an elaborate candlelight dinner for the two of us, complete with different wines for each course. I did all of this out of love for her, hoping that she would reciprocate that love and accept me entirely.

Fortunately, my devotion seemed to have an impact on her. Although she initially had reservations about my transvestism, as she developed her own sense of femininity, she grew more accepting of mine and even began to enjoy it. She started sitting at my makeup table, asking for advice on eye liner and lipstick - something she had never paid much attention to before. Her use of makeup had always been functional rather than creative, only using it to maintain a professional appearance during dates or formal events. However, as fashion trends changed and women in powerful positions embraced their femininity as a form of expression, Elle felt compelled to do the same. I had previously told her that a confident woman dressed in high style and perfectly made up could have an intimidating effect on men, especially in a courtroom. She took that advice to heart and tested it, first on me and then on opposing counsel. It always proved to be successful - her poised beauty left them speechless, and a flirtatious sway of her hips could easily throw them off balance.

Perhaps this is why she began taking more care with her daily makeup routine. One morning, after struggling with blending different shades of eye shadow, she asked for my help, which delighted me. From then on, I became the one who made up her face each morning, and sometimes in the evenings when she had late meetings or client appointments. I loved enhancing her appearance as if it were my own. She began teasing me about these feminine concerns, referring to me as Mr. Daniele as if I were a fancy hairdresser. She would often talk about her amazing personal beautician, not revealing who or where they worked. Eventually, she would simply call me Daniele, praising me endlessly.

Daniele had become her casual name for me, even when we weren't discussing anything particularly feminine. I was no longer Dan in her eyes. This remained true even when we were intimate. She would tell me how wonderful it was, calling me Daniele with a tight embrace before falling asleep. It seemed that she enjoyed my feminine side during our lovemaking. Oral sex was just as enjoyable for her as genital sex, and when she saw me as Daniele, she would guide my head towards her more often. I loved it all.

In recent months, she began encouraging my femininity in small ways. Contrary to her initial fears that it might affect our sexual compatibility, it actually enhanced it. She noticed that when I was dressed as Daniele, I was more gentle and considerate, more affectionate during foreplay and after. She realized that Daniele was more willing to serve as her lover and engage in lesbian activities. She would jokingly refer to my genitals as a cute little dildo, suggesting that she might use one on me someday.

As Daniele, I didn't feel the urge to penetrate her with my own genitals and on days when she was feeling sensitive from her menstrual cycle, she appreciated it. Sometimes, she would reach a trance-like state as I pleased her orally, gripping my face and urging me to go deeper. It was a moment of intense pleasure for her, and I savored the taste of her as her arousal increased, especially when she released her juices into my mouth. Afterward, when she was ready to sleep, she would kiss the tip of my nose, thanking me and mentioning how much she loved it when I ate her out. It was a mutual delight. Sometimes, she would make contented sounds as I gently suckled her breasts.

If I had known how to style hair professionally, I would have gladly become her personal hairdresser. I yearned to try new things with her gorgeous long blonde locks, but my own straight, shoulder-length hair limited what I could do. Occasionally, I would experiment with curlers and a blow dryer, but I always had to maintain a more masculine appearance when going out. We agreed that the real woman should look her best whenever she stepped outside, and the other should remain at home, not dressed or made up as a woman.

Over the past six months, Elle had