The woman in your life has overcome the initial shock of your crossdressing disclosure. She is satisfied that she won’t find a definitive answer as to why men crossdress. She has come to terms with seeing her man in feminine finery. Yet at the back of her mind there is still a lingering question, “I know you want to feel like a woman, but why would you want to wear heels every day?”
While pondering this she is nursing memories of bruised and blistered feet. Of evenings out in 3” heels followed by a painful hobbling to work the next day. Of dress codes that require – or social codes that expect – woman to wear heels to work. She knows that heels make her look taller, her legs look sexier and her walk seductive. Yet she can’t help but harbor some measure of hate for those instruments of torture. And continue to wonder why anyone would willingly submit themselves to similar misery.
Crossdressing With Tender Feet
Yesterday I came to fully appreciate the wisdom of such wonderings. My wife is preeminently practical, and shuns heels on all occasions except for those rare times I can convince her otherwise. She doesn’t understand why I want to wear heels, why anyone would want to wear heels. But yesterday it was my feet and my choice.
After spending the morning at the salon – and feeling suitably fabulous – the day had cooled such that I longed to walk around the neighborhood and feel the refreshing call of evening. I had worn strappy wedge sandals with a 2” heel that day, and thought nothing of taking a brief stroll wearing them.
My usual wanderings around the neighborhood take me on a mile and a half loop. Nearly halfway through there is a small hill that offers a fabulous view of Lake Washington. Taking in such a view would be a wonderful way to end the day. On this particular trip I discovered a few things.
Firstly, in 2” heels the small hill in our neighborhood might as well have been Mount Rainier, which towers almost fifteen thousand feet above the Washington landscape. Every step up was an arduous journey.
Secondly, it’s really hard to walk like a woman when you’re fighting against gravity and awkward foot positioning. I cringed inside as I clumped like a traditional African dancer.
Fortunately, at some point I realized that this adventure was a bad idea. Unfortunately this realization came at just about the half way point in my little journey. It’s here that I discovered another wonderful truth:
It’s even harder to walk downhill wearing heels.
When I finally got home I could feel the forming of blisters and my feet were burning. I spent the evening icing my feet, pondering my wife’s sage footwear advice. Truly I can appreciate woman’s distaste for high heels. So I made a pact with myself:
I will stop wearing high heels…
For at least a week while I let my blisters heal. High heels are like crossdressing crack, I’m not even sure an intervention could wean me off this addiction 
Despite my wife’s thoughts to the contrary, I’m not too crazy – I won’t ever wear those sandals when I walk around the neighborhood. Though I wonder, would such a journey be as painful in the cute pair of boots I just bought? I’ll have to try that sometime…
