In the weeks after, I brought groceries and cooked in her kitchen. And by then, with my own cleaning supplies as well, her kitchen was as shiny as my own. I had gone through a similar transformation, with make-up on my face, a wig on my head, breastforms now filling my bra cups, and finally in the heels she wanted me in. Actually enjoying the things she had picked for me, I had slowly gotten rid of my body hair, and I almost looked as feminine as Kayla.
By now she'd given me a female name as well, although I made it clear I didn't want to be Ronda or Ronalda, so we settled on Rihanna, as we both were big fans. One night we had finished a bottle of wine together, and since then I had stayed overnight. We were actually looking forward to our first full weekend together. And although neither of us had spoken about it, it was clear we were really liking each other's company.
It was probably what drove me to look as female as possible for her. I practiced walking in heels every night in my own place. As well as practicing make-up, working out way more and doing yoga. I had my own skirts now and couldn't wait to feel the weight of my breastforms in my own bra, as soon as I came home from work. And that's how I slept as well, in one of the nighties Kayla had given me.
She was teaching me how to control my voice, my mannerisms, and she shared a bunch of books and videos with me, stuff she had used herself during her transition. And apart from realizing we were falling in love by now, I was clearly on a path to becoming a woman as well.
Our first full weekend together would start Friday after lunch, and include Monday as well, and Kayla had made it clear we'd be going out in public. I'd be Rihanna during all of it. We had agreed already that I no longer would wear the same outfit each week, but whatever she would give me.
The first thing happening that Friday afternoon, was that she glued the breastforms to my chest. It was a very intimate moment, as I was naked, looking like a woman. I was happy to get a bra on though, to spread the heaviness on my chest. She had one more thing for me, although she was a bit shy about it.
It was a chastity device, not metal, not plastic, but a rubbery material, which would be very comfortable she promised. It had a very symbolic value though, as I would be a true girl for the weekend. My dick would not take part in any sexual act.
I thought about how quickly our sex life had settled already in a rhythm. I could no longer deny that I was hooked to sucking Kayla's dick, it had been my choice from day one. And as much as I had liked her blowing me, I could not wait for her to take me in my rear. But I always would cum from my dick, and that's what she was trying to change. Wearing this device, would my body switch to coming anally?
So I had her put it on me, and although there was no visible lock, something clicked and she had a tiny key in her hand, which she hung from the necklace I had given her the week before. Somehow my dick was now curved down between my legs, leaving a small bulge under my panties, that could easily be regarded as a woman's vagina.
For my first time as a woman in public she had me wearing a nice summer dress, and low heels, which I could easily manage. We spent hours in a salon, where my wig was replaced by hair extensions and my make-up was done professionally. Diamond studs in my now pierced earlobes. Matching nails on my fingers and toes taught me another thing about women. How the heck would I operate my phone?
They also used a machine on me to permanently remove my body hair, and although it hurt like hell, Kayla promised me it was worth it. I truly appreciated the cooling massage afterwards, thinking that women really knew better how to please our bodies.
Renewed, after we were done, I got a better look at Kayla. She was beautiful, and two things at once made me gasp. The realization that I had really fallen in love with her, and the effect the chastity device had on me, as I knew I would have grown rock hard. She smiled, apparently aware of my discomfort, then moved me in front of a full size mirror, and I gasped again.
I had gotten used the past so many weeks, on what I looked like dressed as a woman. It had not prepared me for what I saw now in the mirror. A cute, sexy girl, and now I twitched, from the sight of myself. Kayla joined me, her hand on my hip, a beautiful couple in the mirror, and she leaned into me, not helping my urgent desires down in my crotch.
Things didn't get better when we shopped for party wear in an adult store. Kayla wanted leather for both of us, and the dress she found for me was stunning. It would show off my boobs and the skirt, just above my knees, was roomy enough to dance in. She picked a catsuit for herself and I wondered how she managed her own dick out of sight, because she had to be hard by now as well. She had stiletto thigh high boots, whereas my own boots were more heels with straps that snaked up my legs.
I had seen a latex dress as well that I fell in love with. I don't have OCD, but I love cleaning, it simply gives me a good feeling. I have always liked long rubber gloves, to protect my skin from the harsh fluids. The dress had matching gloves, way over the elbows. Likewise it came with matching stockings and a bandana to wrap around my hair. So it would essentially fully cover me in latex, and allow me to take a shower afterwards, while dressed, to get all the grime off me. Unfortunately it was too expensive, as the leather outfit was not cheap either.
But Kayla said she'd pay for the party outfits, so I got and paid for the red maid's dress, as it was called. When I told her however that I would clean and cook, but I did not intend being her maid, she laughed and hugged me. The look in her eyes told me that she was probably more than in love with me as well.
We took an Uber to the dancing and although we both were very sexy, it was clear that I was the girl in our relationship, and she a powerful alpha, just the way she towered over me. She was very protective of me as well, given all the beautiful people in the club, many of them ogling me, both men and women. I heard her tell someone we were an exclusive couple, and it gave me a pleasant buzz. Likewise, when I finished a dance with a polite gentleman, and he asked me to join him for a bit in one of the backrooms, I declined, telling him I was taken.
I did end up in one of the rooms though, as Kayla could no longer control her urges, and I learned how a smartly positioned zipper let her monster out, without having to take the suit off. She took me from behind, my skirt giving easy access, and she made me her woman. Obviously, it wasn't the first time I was fucked like this, but it was the first time I came as a woman, my own dick out of the equation.
It was then as well that she asked me to move in with her, she did not want to live any longer without me. I said yes, before I thought about the consequences, but sometimes you just have to follow your heart, and my heart told me I loved her. I was in love with her.
When we met up with her friends again, she called it an engagement and we celebrated with champagne. I had a slight worry how that would work, but everybody was so happy for us, I just soaked it up. It's funny, just a few months earlier I had wondered how to meet a trans woman, and here in the club there were so many, including some of her friends. And although I didn't think I was transgender myself, I was surprised how easy it was to talk with them about serious issues, including our sex lives. They didn't care if I was a CIS girl, a cross dresser, or a trans girl, I was one of them and they loved me for what I was, and what I meant to Kayla.
I won't bother you too much with how the rest of the weekend went. Believe me, there was a lot of sex, non of it included my male part, which stayed locked up. But we did go to my apartment and moved over all my stuff. I spent a full day in my maid's dress, cleaning my new house, enjoying it even more thanks to the layers of latex. Three times Kayla tackled me, and we fucked like rabbits.
But come Monday, we had to sit down and discuss our future. I needed to know what she thought my future looked like. The cross dresser that I had become by now? Or was the chastity device that I was still wearing an indication she wanted me to progress into a trans woman, like herself? Or different perhaps, as my dick was no longer in use, and hers was still very much.
Apart from that, I had no clue myself what I wanted. The last so many weeks have been so amazing and after Friday I couldn't see myself anything other than a girl. Her girl. I was truly happy, moved in with her without a second thought. I could even see us being married already, and we were sort of engaged.
But on Tuesday I had to go back to work, so I had to become Ronald again. That meant my hair had to go back to normal, my breasts had to come off, and what about the thing on my dick? Would Kayla still want me in her bed? Do I go back to wigs again, and become Ron each morning before I leave for work?
It became clear real quickly that Kayla wanted me to stay a girl, and perhaps started a physical transformation as well. Why couldn't I go to work as Rihanna? Would they fire me? And if so, she herself had a well paying job, plus quite some money from an inheritance. We didn't need a second income, which would give me time to find a new job. As a woman.
So it was my decision in the end. And I did what I normally do to sort out my thoughts, I took a piece of paper and started writing all the reasons for and against:
I wanted a trans girlfriend
I found Kayla
I love her and she loves me.
I like dressing up.
I am her girl.
They will probably freak out at my work.
Or will they think I'm a freak?
Or will they laugh behind my back?
Is it worth losing my job over it?
I love sex with Kayla!
I like her friends.
I never felt so alive.
I want real breasts!
I stopped there for a second, looking at my last line. Anytime Kayla fucks me from behind, she grabs my breasts. But I don't really feel it. I want to feel that sensation...
And so I added:
Am I trans too?
Do I dare?
Do I need my dick to be happy?
Or do I want a pussy?
The way my body reacted told me the truth. But will she still love me if I'm a complete girl? Wouldn't she want a man, once she's fully transitioned herself? Or will we be lesbians?
"Honey?" I asked her, "would you still love me, if I'm a complete girl? With pussy and all?"
Suddenly I was in a tight hug, and her tongue deep in my mouth. When she pulled away finally, she said, "we'll be married for life. You'll make a wonderful bride. I have the perfect dress for you!"
It was clear that she was happy. When we discussed it further, she actually wasn't sure if she'd ever let go of her own dick, given the fact we both enjoyed our current sex life, where I took her in either oral or anally. Adding a pussy on me would simply improve it even more. And I started fantasizing on that.
So a decision was made, and all worries had left my body and mind. I had scheduled a meeting with Human Resources at the start of the business day on Tuesday, and Kayla helped me getting ready. She had a business suit for me, undeniably female. With killer heels and some classic accessories. She helped me with my makeup and I looked like an executive.
In my car I realized I was out in public as a woman, by myself for the first time. No Kayla to guide me or back me up. Or drive me, as I realized how hard it was to drive with these heels. But I got used to it, all of it, and by the time I reached the office, I had my self confidence back.
When I knocked on Mrs Swift's door she called me inside right away. The astonished look on her face was quickly replaced by an understanding. "Ronald?" She asked. I nodded, and said, "Yes, but I go by Rihanna now." I was actually surprised how quickly she had guessed.
I was even more surprised how quickly she took control over the situation, like she was seeing male employees in female attire every day. She wanted to know how long this had been going on, and how serious I was. Then she asked if I wouldn't feel better to slowly transform, little by little every day, so colleagues could adapt. But I told her that my last weekend had opened my eyes, and I had no desire to get back being a man.
She accepted the explanation without further questioning and moved to more practical details. She suggested I take two more vacation days this week, and she would give me two, giving her time to prepare my colleagues for the change and some new rules, starting next week Monday. For one, she wanted me to change my legal name, and suggested Rihanna was probably not the best, but I could be Riha Anna, which would leave my initials the same as Ronald Andrew. I didn't have a problem with that, as my new friends last weekend had already called me Riri or Ria.
She also made it clear that my dress style would have to be pure female. Nothing unisex or remotely male. And of course, like that I could no longer use the men's bathrooms, but she needed a security to protect worried female employees, if I used their bathroom. She suggested I wear a chastity device at all time in the office. That was again no problem for me, as I was wearing one already. She nodded, but still warned that any violation would result in a warning and two warnings would be reason to terminate my employment. As harsh as that sounded, I still had the feeling she was rooting for me, her whole demeanor was warm towards me.
She asked if I was on HRT and I told her I had an appointment later in the week. She warned me the therapy could cause mood swings, but she expected me to remain professional in the office no matter what.
Then she suddenly picked up her phone and she summoned Ms Johnson. Desirae? I wondered why she needed to come. She was in Customer Relations and we were friendly, having gone for lunch together a few times, and chatting around the coffee machine. She had also been clear that she didn't want to date anyone in the office.
Desirae was always impeccably dressed, and today was no exception. I suddenly realized I have always admired her actually for her choice of clothes. She looked surprised at me, apparently not expecting another woman in the HR office, apart from Mrs Swift.
Mrs Swift introduced us, with a smile asking Desirae if she recognized me. It took her a moment, then she said, "Ron?"
I smiled as well, nodding but still not clear why she was here. Mrs Swift told her how I had decided to come out as a transgender woman, and she asked her to take me for a very early lunch, or maybe coffee first, while she did some paperwork that I was to sign after we came back.