I am happy to be a skirt-wearer, & am proud of what I have been able to achieve.
I wear a skirt for two reasons: The first is that I genuinely feel more comfortable in a skirt than in trousers. The second is that I feel I should make the most of the opportunity to expand my wardrobe, & make choices beyond what is currently accepted for men. So, in a nutshell: I'm pushing boundaries, because I want to & because I can!
Essentially, I am a bloke in a skirt, not a cross-dresser. I do not have the physique to pass as a woman, no matter how hard I might try. Nor am I interested in the hair, makeup & other feminine attributes.
What I do have is, though, is the confidence to allow myself to be seen in public in a skirt, without worrying unnecessarily what people think. There is a time & a place for wearing a skirt, & I expect to maximise the opportunity as best I can, but presenting as male, not female.
Somebody asked me recently what I thought this might lead me to. So I said that, for me, this is a journey, not a destination. And I think that sums it up quite nicely.