I guess I'll just keep this thread going, in that case! Sorry if it's a bit long, but letting this stuff out that's mostly been in my own head feels nice.
So, my current progression started about eight months ago (but I'll get to that).
When I was in my late teens, I had a fair number of times of trying on my mother's things. Skirts and dresses mostly, occasionally a swimsuit. I had a lot of fun with it, and even had a few fun sessions with a camera, but it was all very furtive, in the few times I could get time at home (I'm guessing this all sounds fairly familiar to a lot of you).
When I moved out of home (and in with my first real girlfriend), I mostly stopped. Happy with being in a hetero cis/cis relationship, etc etc, but also just less opportunity. But, I was still interested in that sort of thing.
Fast forward a few years, and my honeymoon with the same wonderful lady. We were discussing various interests of a sexual nature, and I brought up the idea of cross-dressing. At the time, I was mostly interested in it in a sexual context, as something naughty for me to do with her, or underwear underneath male clothes. She put me in a cute lace and satin pair of her undies, and we had a great night.
After that, I started getting my own girly underwear, since my hips aren't girly enough to share hers, and what started as an occasional treat got to be a regular thing (up to now, where I basically alternate fun vs boring undies).
After a few months of wearing fun undies, I got myself a few skirts (the cutest of which I'm wearing now), just for wearing around the house, but talking to my best friends, we somehow reached the arrangement that I could wear girly things out to our weekly roleplaying stuff.
The more I've worn girly things, the more it's felt like just the right thing to be doing, and the more that being male has felt less definite. I dread the thought that my build isn't the sort that lends itself to passing*, at all, but with help, I'm leaning towards trying, at least in private.
In the future... My birthday is in five months, and we're having a trip to my best friend's (whom I love as a sister) family coat house. I'm going to have the whole time I'm indoors en femme. As for the outside stuff... depends on how well I visually pass, I guess. On one hand, it's far from running into anyone I know, on the other hand, it's a small country town... feels risky...
*in Aussie clothing size terms, I've got size 14 hips, 18 waist, 22 chest, and about size 26 across the shoulders
