I'm sure many of you have gone through this process - during my early years of trying to appear more feminine, the focus was all about the clothes - feeling good in "pretty" clothes and enjoying the experience of dressing female was a tremendous buzz. Many of my earlier attempts to look more feminine were quite disappointing. These days it's all about feeling comfortable and enjoying the experience of being out and about as a woman. My wife has been a tremendous help in this journey as she tells me what works and what (definitely) doesn't, and she is incredibly supportive when I want to get out and about! The first image is from about 20 years ago, experimenting with different fabrics and looks, while the second image is from a recent trip to the UK meeting up with some girls in Birmingham.
I'm still crazy about lingerie, but I like the more conservative external look when out and about.
Deb