I love high heels! So much so that I own over a 100 pairs.
The second piece of woman's apparel I ever wore were my mother's high heels (after I slipped on a pair of her nylons). Since that initial crossdressing experience, I almost always wear high heels when I present as a woman. Occasionally I joke that this whole transgender thing is just an excuse to wear high heels.
Without a doubt, wearing high heels is the most difficult thing about presenting as a woman.
Walking gracefully in high heels is an art.
And then there is the pain! Wearing a girdle, waist cincher or clip-on earrings can be painful at times, but you can almost always count on wearing high heels becoming a painful experience sooner or later.
Despite the drawbacks, I'll give up my Louboutins when you pry them from my cold, dead hands.
Abby of Vivian Lou fame feels the same way and she offers some tips in her blog to make your high heel experience as painless as possible.
How to stop feet from slipping forward in high heels.
How to walk up and down stairs in high heels.
Why not to wear the same pair of high heels every day.
As Abby says, "Here's to high heels without the hurt!"