She went into her closet and rummaged around for a while. Finally she came back with a number of garments. Her old gear, she explained. First she started wrapping a bra around me, changing the straps until they seemed right to her. Then she showed me two breast forms that she slid in the cups. I felt the weight suddenly on my chest with my shoulders providing some relief. Next was a corset and she tied it very tight but in the mirror I could see what it did to my shape. Then I had to step in what I first thought were panties but when she pulled it up she moved my dick inside it until it was fully pulled back with no chance of moving back due to the tight material. At first glance it looked like I had a pussy. Next she pulled stockings up my legs. It didn't look great because of the hair on my legs but it had to do. The stockings were dark enough to hide the hair a bit. She connected the top of the stockings to the corset and finally had me step into real panties.

In the mirror I could see my body looking more female, all it needed was the dress now. I was right and although I had not believed it, it fit around me and she zipped me up.
I don't know, if you're reading this, then maybe you have more experience in this than I, but for years I have carried this fantasy, without acting on it really, other than making it harder in the dating scene. To be honest, I never really expected this to ever happen, and now that it did I was stunned. It felt so right that it scared me, was I really gay? I just sucked a guy's cock for crying out loud, technically. But already I was wondering when I could do this again and what dress would I love to try next.

Iona looked at me and it seemed like she knew what was going on in my head. "Isn't it funny", she said, "it's just a piece of fabric right, but doesn't it feel like how your life will never be the same?"
I nodded and she continued, "Listen, when I look at you and see your reaction, I see me just a few years ago. We're so alike, we love the same stuff, and all you needed was someone to push you over the edge. I had Evelyn a few years ago and she's still my best friend. I think you're on a similar path now and I hope in a few years we will be best friends as well. Or is there more you think?"

"You are the woman I've been searching for all my life", I blurted out, "we'll be lovers as well. The idea of being a woman has always attracted me, but it scared me because I thought I would automatically have to date men. Maybe taking hormones would change my mind on that but it kept scaring me so I never acted on the desire. But you are just perfect for me."

She laughed. "The hormones are weird, they mess with your body and mind indeed. I became more girly, more feminine if you like, right away. As I said, my dick simply stopped working while I started growing breasts. But look at nine out of ten transgender sexual images and they have huge dicks as well as huge breasts. Maybe it's all photoshopped but can they do that with videos too? I don't know. But I am attracted to other transgenders, not so much to men with a similar sized dick. You said the right things to me tonight and that's why you're here, but now I think you may well be what I've been looking for as well."

I did not know what to say, but I pulled her into a hug, I embraced her with all I had, mind and body, and that seemed to me what we both needed. Finally I said, "You need to finish me, I'm still a guy in drag." And with that she got the wig she had found and she spent an hour on my makeup. But by then Pierre was gone and she asked me what my name would be, for the rest of my life.

"I'm Rowena." I said. It had always been there in the back of my mind. There was a girl in school by that name and I never understood why I was jealous of her name. Now I knew.
"Nice!" Iona said, "that's a strong name, I like it. Welcome in my life, Rowena."

She put me in heels, not too much but enough to make me stumble around. I had to practice and practice and felt the movement of the dress around me, the weight of my breasts, a little wiggle in my step. At some point she decided I'd look better without the hair on my arms and legs so she worked on me with a razor and it made wearing the stockings so much better. I don't remember how much time but it was already getting light again before we finally went back to bed. I kept on most of the gear, as she called it, so I would experience sleeping with breasts. I could sleep with the makeup she had applied although normally you would take that off before bed. But it would give me a wonderful experience, she said, waking up as a woman. We were both wearing sexy nighties but so tired we fell asleep in an embrace immediately.