Funnily, although I was ready to go to bed, I checked email on my computer, even played a game for half an hour, never even took my heels off, and I basked in having made a new friend, a real friend. And when I finally went to bed, I slept in my new underwear, my manhood still safely tucked away.

The following morning I knew my waistline was slightly narrower again, my boobs more perky and I knew my buttocks would look good in yoga pants. Did I mention how much pain I had in some of my muscles? I knew I'd get used to it soon enough, with the exercise plan I had signed up for.

I took a long hot shower, which relaxed my muscles a bit, and I washed the panties Emily had given me by hand. I felt like I had to buy at least another pair, so I could wear them for every gym session, but how do you do that as a man?

When I got dressed I felt for the first time in my life that my own clothes were outdated. I had pulled my hair back in a ponytail, and I walked in my heels, but everything I owned was shapeless, and made from rough material. And soon I was online, buying more than just another pair of panties. I knew my female sizes and I didn't even bother to see if there were yoga pants for guys.

I purchased a beautiful set that looked like a one piece, with a long sleeved control top, in a light purplish color named lavender. The model that was wearing it looked amazing, and it was more or less the same material I had gotten used to. There was a tank top that went with it as well, so I added that too. When I researched about tucking my manhood, I ended up on a website specialized in male to female transformations, and although I had no desire to become a full time woman, there were a few things I liked, for when I would be with Emily.

I ended up buying a special sleeve that would pull my manhood between my legs, and would lock it through an anal plug. It took me minutes before I clicked the purchase button, not sure how I'd feel about something in my rear, but they guaranteed a smooth crotch, which is what I wanted in my leggings. And I don't know why, but I added two small breast forms, thinking they would give me a slightly better look than the padding. While checking out they offered a hair removal cream at half price, and I added that as well.

I did go to the supermarket, to buy some of the ingredients and foods on Carla's approved list. I got a few looks and I wondered if some of the makeup was still on my face. When I checked once in the car I realized I was still wearing my ponytail, and I had to laugh. I kept it in. But I had picked up lipstick and an eye pencil. More than that I didn't dare to try.

When home I texted Emily to tell her the joke on my ponytail. Then I drew a tiny slant at the side of my eye, and was quite pleased with the result. It took three tries to get the lipstick right, and then I sent her a picture of my face. She promised to give me some lessons the next day.

Although I had worn some sneakers outside, I put my heels back on once home, and I wore them again until bedtime. It was a bit compulsive I realized but I liked the extra inch or two they gave me. I attempted to cook my new food, but it was rather tasteless, but at least I felt good about it.

My new purchases were delivered Sunday morning, and I tried my lavender fit first. It felt like it was made for me, and for the first time in years I didn't feel fat. Later, when my “other” purchases arrived, I first tried the small breast forms and I was pleased with the little bit of curves they added. It took me half an hour to figure out how the sleeve worked, and then another half before I got used to the plug in my rear. But the result was indeed a flat crotch, as promised.

By then it was time to go to Emily, for our first measurements, and to get ready for the gym. I wore my lavender long sleeved suit, but just to make sure I brought my other yoga fits as well. I took my car, as I would bring a good amount of the ingredients I had bought, and I realized I drove for the first time in my life with heels on. I survived, actually quite liked it.

Emily was in awe of my new fit, and she felt my breasts before she realized what she was doing. I laughed as I explained the small falsies, but she was so embarrassed that she wanted me to feel hers in return. And although I wanted to just brush by hers, when I got my fingers around her generous breasts, I lingered way too long. I squeezed softly and a moan escaped from her lips, before I got myself under control.

I apologized profusely, but she laughed now herself and told me she clearly enjoyed it, and I could grab her anytime. So, I made her promise she could do the same to me, and to prove it, I put both her hands on my tiny breasts, hidden under the fabric of my fit. Her soft squeezing actually turned me on, and we both moaned now. Interesting…

She had bought a gaffe for me to tuck my manhood. Very similar to what I had, except it went up with a string between my buttocks to a string that was around my hips. She liked my butt plug solution better, but I kept the gaffe, knowing I'd need it at some point.

We measured each other's waist line, and we both had lost another inch or so, and we used her cell phone to upload the new information. Then she did my makeup better, and she taught me the tricks, as she did so. From now on I would go to the gym as Jackie.

Carla was pleasantly surprised with my looks and my desires to be Jackie while training with her. And somehow it was easier to get through her regime of exercises. As a girl, in my lavender fit, I felt more confident and stronger. Later, Emily bought exactly the same set, and we looked forward to going as a true couple.

Back at her home she was going to wash our gym outfits, and she asked if I wanted to try on a bra, so I could keep my falsies on. That was a whole new experience, as the bra was designed to show off more than what I had, rather than flatting it out, which happened with the gym outfits. Then she convinced me to wear a new white dress, which brought my new curves out beautifully. I knew I shouldn't, but I couldn't resist, and once more the soft material felt like a dream on my skin. A black waist cincher completed the dress and I actually felt pretty.

Emily convinced me that higher heels were needed and we found a pair that was decently comfortable, but once again I had to get used to the extra height. We both loved cooking together, and I quickly learned what I had missed the day before. It was called spices.

In my apron, to protect my dress, I looked like a housewife, and in her leather leggings she couldn't resist grabbing me from the back on my hips or around my breasts. I did my best returning the favor, and I liked the feeling of the leather on her. Once again we became more intimate, and small kisses were the result of that.

So, kissing while wearing lipstick is a different experience from kissing someone who has lipstick on. We had both, and the taste was a thrill each time. It quickly went from innocent to adding in our tongues, and we both moaned more and more. And once my apron was off, I flirted with my skirt in a very sexy way when she passed by, and she pulled me around, into her, and her kiss went deeper than before. And I realized I was the girly girl in this relationship that we slowly started forming. And I just couldn't resist that thought, that idea.

After dinner, which tasted much better than my attempt the day before, it was clear that I would stay for the evening. We watched a movie again, but it had quite some sexy scenes, and this time I was in her arms. Soon I could feel her fingers under my skirt, as she played with the plug in my rear. I don't know what she did, but soon it felt pleasurable, partly because her other hand was kneading my breast, and her tongue was deep in my mouth.

It was no longer giving and taking, as she took full control over the situation. I was Jackie, her girl, and she did everything to make me feel good. And somehow, some way with her fingers, she made me cum. Not like a man, but like the girl I was. And when she asked me if I liked it, I could only confess I did, and that sealed my future with her.

By then she was so horny and she asked me to eat her out. It was a question, but I knew it was a request that I couldn't refuse. And I went on my knees between her legs, and I tasted her pussy for the first time. It didn't help that she flooded me with her wonderful taste, as I tried to keep up with her orgasms, but the tone was set. She could make me cum, and she could make me let her cum, and I was in it for the ride. And I loved every moment of it.

We changed the rules some more. All four times in the week that we had to go to the gym, we'd have dinner together at her place, then relax afterwards, which meant cuddling and making out. She introduced more and more clothes, but always skirts and dresses, but she added stockings, garters, a corset and jewelry. And I got used to shaving my whole body while in the shower.

By Friday I stayed overnight and we had “real sex”. I say that in air-quotes, as she used a strap-on and took my anal virginity. It wasn't quite what I had expected, but there was the beginning of some stimulus. Emily did her best to make it worthwhile for me. I just enjoyed eating her afterwards, the situation clearly a turn-on for her.

The second time, after we woke up in each other's arms Saturday morning, hit the right spot inside me, and she was thrilled by my orgasm. I was staying over through Sunday night, and sex was on the menu multiple times, both planned and unplanned. But the best part was when she took me out to the spa.

I had no clue what to expect, I only knew I was becoming more and more female, and this turned out to be an exciting turn in my life, unlike what I had thought only days before. By now I was quite used to the different exercises, and my favorite machine was one in which I would hang upside down, my own weight stretching out my body and my spine, and I felt truly at peace during those moments. The shrinkwrap did its thing right away, and gravity caused the fat to go to my chest. And by the time I stood on my own feet again, that fat had no room to move back where it came from. And the least resistance was followed by pushing it into my man boobs.

By now, my man boobs were more and more pronounced, over a more narrow waist, and they looked more like female breasts. I had been using falsies to give me some extra, but right here in the spa they used a minimally invasive procedure to shape my breasts into undeniably female. Silicone inserts were used to shape them and leave ample room for more natural fat to fill it up even more in the weeks to come.

Soon I would need a bra to truly support my breasts, without a need for any breast forms, and in a way it made me feel more female than anything else that had happened to me to reach this point. More than my shrinking waistline, more than the female clothing, the dresses and heels, more than the new way of sex, and more than the lack of my manhood being used.

But wait! There was more!!

Haha, always wanted to say that…

They did some magic to my face. With a laser. Not just to remove my facial hair, but to make my skin softer and younger looking. Add my more pronounced lips, slightly thicker and colored, just like my cheeks stood out more, and the slant of my eyes became permanent, with my shaped eyebrows enhancing the effect.

My face would simply never be thought of as male again, and with highlights in my hair, and a cut that allowed my hair loose or in a ponytail, it became distinctly me, showing the gold in my pierced ears. I couldn't stop looking in the mirror afterwards, and not until I brushed my hand through my hair did I notice my bright-red “claws”. That was my male mind speaking, trying to explain the delicate extension to each of my nails.

I knew that some of that stuff could not be undone, and for a moment I worried about Monday, having to go back to work, but I killed that thought, simply because I liked the new me. And so did Emily. She herself had gone through some beauty treatments, and although people would still think of us as fat, or maybe thick, there was no denying that we looked good together. And with a standing appointment to come here once a month, our looks would only improve.

And where I bought myself a leather skirt and some matching boots, Emily was more practical and she got me a business suit that was professional, yet feminine, and it made it clear that Jack was gone at my office as well.

We went out that night and for the first time in my life I was hit on by a guy. He got a dance out of me for the effort, but I made it clear that Emily was my lover, and he took it with a smile.

It all took just about three weeks, before I moved in permanently. My coming out in the office had been anticlimactic. The first changes in my face had raised a few eyebrows, but when I came in as Jackie, it seemed like everybody was happy the fat guy was gone. And although I still had a significant size, I wasn't sloppy anymore, but dressed for success. The only person that commented was the HR guy, who told me flat out that I was not allowed in the ladies room, until I had officially been designated as a woman. Neither was I allowed in the men's room, looking the way I was now. But there was a unisex bathroom that I could use. Funnily enough he suggested I work two or three days per week from home, until my transformation was complete. Perfect, I thought.

For our relationship it was perfect as well. Being home more than Emily I started taking responsibility for dinner and the more domestic chores. Under her guidance I had become a decent cook, and I actually enjoyed making healthy food as tasty as possible. And as impractical as it was, I was always in high heels, while cooking. Easier to reach the higher shelves with spices, lol.

Our second visit to the spa, a month after my most drastic changes, was more about me than Emily. Apparently laser hair removal was planned for my complete body, not just my face. To help with the pain I had a few drinks with high alcohol content. Or perhaps something else was mixed in, but I had a pleasant buzz as they worked on me. Raquel, with a Q, did most of the work, and she was a lovely woman, who understood what I was and what I wanted to be.

What I hadn't expected was her getting to the most intimate parts of my body, but with my buzz I let her. She actually removed the sleeve that kept my manhood back, and got everything in that area first clean, then hair free. I smiled as I saw her face twitch a bit, it must have been smelly. But, as my mind slowly came back again, and her work completed, I saw worry in her face.

“Honey”, she said, “I'm doing my best to make you a beautiful woman, but when was the last time you saw a doctor that guides you through your transition?”

At my blank look at what she was asking, she continued. “Just what I thought. I have a cousin, who is a gender specialist. I made an appointment for you with her right after you're done here. You may have an issue, but I'd like her to assess that.”

I wasn't sure if I should be angry with her about meddling in my medical “issues”, but I liked her and she seemed genuinely concerned. She didn't want me to put the sleeve back on, as I dressed, and for the first time as a girl I felt awkward. I had enough room in my skirt to not show my tiny man bump, but in a way I felt naked. She handed me the sleeve and told me to show it to Dr Evans.