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…
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Vanessa is a happily married 30 year old transgendered woman from Seattle. It's been a long road to acceptance for her, despite the fact that she has been crossdressing for more than 25 years. Sometimes, when she looks in the mirror she longs to see the girl that lives
within her. 
9 Comments
Dear, dear Vanessa
Never, ever waiver. You know you love the heels. Some things just do not, never have and never will require a “why”.
Heels are top of that list.
2 thoughts. No, lets make that 3:
1. Setting appropriate shoes. Low wedgies make a nice casual walking shoe that stresses out the legs less. But truly, heels are not really made for inclines. Downhill is harder on the feet in all footwear, but magnified by elevation.
2. Quality + Fit count. This is a part of the wardrobe to overinvest in.
3. Practice. Not that this is a chore. Spend an hour a day at least around the house.
Courage my dear, and do let us know how the boots hold up to same walk when you inevitably, unavoidably, listen to them call your name and ask you out to play ….
They don’t call them killer heels for nothing.
I’m afraid that a certain amount of discomfort must be embraced if you want to wear fancy shoes.
While some heels (Mary Janes with a strap?) can be comfy – because they’re not too tight – other designs are not so kind to your tootsies.
I think it’s a case of finding what’s right for you – and what’s right for the terrain.
Haha, Lynn that made me laugh. Killer heels indeed! I’m willing to embrace some discomfort to look fabulous. Blistering my feet so that I can barely walk is pushing the limits – the heels would have to be absolutely divine for me to sacrifice that
Petra, so true! We’ve gone through so much as crossdressers to get where we are, we can’t let a bit of physical pain dissuade us now!
Darling Vanessa
Why not?
I could list a number of Good reasons, but I guess, beyond why not… it’s a woman’s prerogative.
Maybe we’ll tiptoe into each other somewhere on the slopes above LW, though the streets where I live, tend to have some mighty elevation and very few sidewalks. Just getting to the Burke Gilman trail in my 5″ boots would be a challenge. I can barely handle it in my running shoes.
Til Later
Vicki
PS You have been posting the darn cutest little pictures with your posts recently.
Ciao for now
I love heels and am entirely comfortable in all my pairs,however,some are better for going the distance.You can still be girly in running shoes if you wear them right and look the part.Cork wedgies are a good in between shoe and can go the distance.My feet belong in heels…even my wife admits that!!
Rogina – I need to try some woman’s running shoes. It’s been a while since I owned a pair. That would definitely help with the longer trips
But yes, even walking around the hills in Seattle can be quite daunting 
Vicki, hehe – now walk the length of the Burke Gilman trail in 5″ boots and I’ll give you an award
I guess I’m lucky, heels dont hurt my feet, of course I never wear them for more than 3-4 hours, by the way, Ihave a pair of 4inche heels and they are the most comfortable I have. Also, I only dress a couple of times a week, so I could missing out on the real pain
heels can be fine if and when this is what you would really like to be wearing as for me i do perfer flats and littile girls shoes t straps and mary janes theses do not alwasy ahve heels so can vbe much more comfortable but need them in large sizes please!
Someone said once: the feet are the mirror of you soul. If our inner female feelings are socialy repressed inside a male body, the heels can be the “door” to let express ourselves in a very convenient and pratical way. Feminine high heel shoes and sandals are the most favourite acessories of ggs.