The next week she was serving my table, I was glad she got the job. We chatted a bit and I learned her name was Stella. She noticed I stared again at her bottom, this time covered by a leather skirt. You like leather, she suddenly asked, and without thinking I nodded and replied, I have a leather fetish. I shut my mouth once I realized what I just said, that's not something I've ever shared with anyone. And in the Midwest it's not a common thing, boots yes and maybe a coat but not skirts or dresses. She said nothing as someone at another table motioned for her, but when she walked there she brushed her skirt against my hand, clearly not by accident. Later on I got an opportunity to lay my hand on her behind and I cherished the feeling and so did she it seemed. As usual I payed with my card but I also slipped a twenty in her hand.

This went on for a few weeks and we both got more intimate in our touching and talking. She was thrilled to have found someone with a similar fetish and I gave her extra cash towards a new outfit that she was saving up for. One day she simply wrote her number on the bill with the message "Text me". And so I did, it was fun and sexy and eventually she texted me a picture of herself in what I considered my favorite skirt on her, a leather skater skirt. That night I confessed to her that I had gotten myself off on her picture and she laughed, asking if I wanted a nude picture as well. I declined, saying that I wanted more leather on her, not less. She fully agreed. She only asked me to text her each time before I would masturbate, just because she got a kick out of it. It was a simple promise but in the days after I had to confess it to her two or three times a day. I was getting hooked on her and the fact that she sent me more pictures of her didn't help to slow me down.

The next week she invited me over to her apartment as she had finally been able to purchase the dress she wanted so bad. I could easily stop by as she lived on the road towards my work. Early morning was fine with her as she worked from lunchtime to midnight. When she opened the door she had a bathrobe on but as soon as I was inside she dropped the robe and I was stunned. The dress she revealed was smooth and shiny showing her perfect curves. For the first time I got a good look at her gorgeous set of breasts as well, covered perfectly under the leather but with an amazing cleavage. She pulled my hands onto her, one on her butt and one on a breast. There was no hiding of my excitement and that's where Stella's hands went. She pulled my monster out of my pants and before I could protest she took me all into her mouth. I've never had a partner who liked to give blowjobs and I was literally blown away. I lasted only seconds before she expertly drained my balls. When she got up she pulled me into her and she kissed me deeply. With my arms around her, my hands covering her hips and our lips locked I got a taste of myself. I was disgusted for a moment until I realized that the taste of her lipstick and the toothpaste that she apparently had used just minutes before mixed nicely with both our saliva. Our tongues twisted around and slowly we worked away my load. I don't remember ever experiencing such a sexy encounter.

I was getting ready to return the favor but she held me back and said, not yet, I'll let you know when it's time for that. Why don't you make some pictures? She posed sexily and I got a quick set of her beauty. I have only one favor to ask, she said. Anything, I replied. Next time you jerk off on me, I don't want you to waste your cum. Catch it in your hand and then suck your hand clean, I want you to think of our kiss when you slowly swallow it. I was a bit repulsed by that idea but I nodded. Promise? And I promised. The idea clearly turned her on so it was the least I could do.

That night I went through all the pictures I had of her. I could not find one on which she didn't look perfect but one particularly that I made that morning was such a sexy pose, showing so much tight leather, it really stood out. I texted it to her and only a minute later I had a handful of cum and one more minute and I had it in my mouth. It wasn't great but not too bad either and thinking of our kiss I actually started enjoying it. I made a picture of my mouth full of cum and texted that to her as well and she clearly got a kick out of that.

We got in some sort of a rhythm, each morning I would stop at her place for a blowjob, and our kisses getting more spectacular. At night I would wank off and she confessed that she was stimulating herself at the same time, getting very horny herself. After another week or so she came up with something new. After the blowjob and kiss she showed me a device that I had seen in porn pictures but never in real life. It was a metal cage that could easily fit my now soft dick. She looked at me with excitement in her eyes and I just nodded, anything to keep her happy. It took her a bit but when I looked down the cage was guiding my member down in a curve between my legs. I could hardly see it but it didn't feel uncomfortable. When she pulled my pants over it I no longer saw my familiar bulge. But she couldn't keep her hands away from it.

I would still be able to cum, she said, but I would have to find different ways to stimulate it, less physical and more mental. She would just let me out in the mornings for the usual blowjob. Sitting was a bit weird but it wasn't uncomfortable. That night I realized the difference. I had my favorite image of her and let her know I was going to try. She was replying with very sexy messages and I got quickly hard. But instead of standing straight it was bent between my legs and it couldn't grow as big as I normally get. I started fantasizing how she would stimulate me with her fingers and I touched myself on the tip through the metal and my other hand around my anus. I concentrated more on the picture and less on my member, thinking of her fingers and tongue on me and eventually I came, less intense from my dick but more intense across my body. I managed to get most of the cum out and fed myself without another thought. Then I texted Stella how things went. She was excited and proud that I managed to cum this way.

During the next days things seemed slightly different, the blowjobs were still intense but the aftermath lasted longer, we were holding each other longer, tighter and I saw a new happiness in her face and I felt it too. Our relationship started developing more mentally and I was wondering if I had found the one for me. Then one day while my dick was in her mouth she pushed something in my anus. I tensed up but it wasn't really big and it slipped in real easily. But when it started vibrating I went nuts. I could feel myself grow in her mouth, bigger than I've ever experienced and I started cumming hard and long. Even when I was dry my orgasm kept going until finally the vibration stopped. Stella's smile was huge and stayed while she shared my enormous load with me. Afterwards she installed an app on my phone that would allow her to control that thing remotely.

I thought it was perhaps a dildo but it wasn't and I was sort of happy about that as I'm not gay. It was more like a sheath or a hose which had attached itself comfortably to my intestines allowing me to still go to the bathroom yet there was a small enlargement right where my prostate was and it would stimulate me through vibration. That week I only had to text her and she started the vibration and I would come even without touching my dick. Sometimes she would start it before I was even ready and I had to rip my pants off before I'd wet myself. Then more often she would start it a few more times and having blown my load already I started experiencing what could only be anal orgasms. It got more and more intense and affected my whole body, from tingling toes to my tongue stiffening. She even turned it on sometimes while I was sleeping and my dreams became more and more erotic.

I trusted Stella with my heart by now and I was fantasizing of our future together. She clearly had similar thoughts and one morning she explained to me that her fantasy was to see me in leather as well, in a leather skirt more precisely. By now I was wondering myself what it would feel like on the other side of the leather fabric, so rather than feeling her skin through it, how would it be as she felt me up. So I gave in and before I knew it she was fitting the skater skirt on me. With her hands on my hips and buttocks and her face under my skirt sucking on my member and just a little of vibration another piece of a new world was opening up. It was clear that I needed to lose some belly and she next added a leather corset that she would tie down more and more tight. She also started making my breakfast and lunch with healthy portions of a new diet and soon I could fit in any of her skirts and then her dresses.

The corset was pretty much 24/7, she would take it off only so I could shower, now at her place. I was arriving earlier and earlier as our sessions took longer and longer, so I could still be at work in time. I don't think that people could tell I was wearing a corset but I got a lot of compliments on my new figure and my diet that was clearly working. When I got home I'd wear my own leather skirt now and I was feeling myself up feeling both the inside and outside at the same time. My masturbation sessions were no longer wanking off, it was much more sensual now with Stella remotely stimulating my ass and I rubbing myself until I came. It wasn't perfect still though as I didn't like the hairs on my legs to show under the skirt and when I mentioned this to Stella she agreed. And she had a solution as well, as she had a home laser hair removal device that she used herself as well. 

It took a number of sessions to make me completely hairless, my complete body as well as my face. Every touch on my skin was now sensitive and erotic. And using Stella's soap and cremes had made my skin softer and softer. A new corset started accentuating my curves more, it even made it look I had some boobs now. And this seemed to be the trigger for Stella to suggest I move in with her. We finally slept together, something she had prevented until now. Reason for that, and to be honest I wasn't even surprised anymore, was a nice sized dick that she had been hiding under her skirts. I was the one now giving the blowjobs or I took her fully into my ass. I was in a bliss no matter what. It was good to taste some decent cum again as my own has diminished to almost nothing. Apparently she has been adjusting the size of my cage over time and my member looked more like an oversized clit than anything male.

She wanted to use the money that we could save now that we shared one apartment to stimulate the size of my boobs and with her sucking them all the time it really made my anal orgasms even more explosive. Or female orgasms as I started to identify more and more. So I took the pills she gave me and indeed I started showing more and more cleavage. I used a wrap when going to work so it wouldn't show but soon I found myself in my bosses office, explaining to her I was transitioning into a woman. 

She was thrilled, something I hadn't expected, but she wanted me to make it public as soon as possible, to stop all the gossiping about me that was apparently going on. So one week later I was introduced as Deanna to the whole staff, and I was trained to move into my boss's position so she could move up herself. She had delayed her own promotion because she couldn't find the right replacement within the all male staff in Engineering. I basically saved the day and she mentored me personally and we became very close friends. I also learned a lot of female secrets from her in how to deal with groups of men. That, mixed with my own male knowledge, made it easy to get everybody's respect.

A year later to the day of meeting Stella for the first time I had a surgery that made me a complete woman. I found that it was still possible for sex to be even better than what I had experienced already. From the day I became Deanna I have never worn pants again, always skirts and dresses, although I didn't wear a lot of leather to the office unfortunately. But I was the most stylish and I dare to say I stimulated a lot of female colleagues to dress better and be confident in doing so.