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…
Eyes are the mirror to the soul. But I agree; What’s the point of not wearing high heels and pumps when your female inside demands. Is natural for feminity to go hand in hand with high heels, slips, make-up, lipstick and nylons in stockings and pantyhoses. I love them all.
It also helps with walking like a female and teaching us walk with the grace of a woman. One is more careful stepping in high heels compared to flats when knowing that something sexy like a slip and a skirt confines the thighs.
I am not ashamed, I am fortunate to have a female side and work with it. I wish I could find a job, especially one I can work as a female and a good girl who likes creatures like us.
Susan Veronica
Come on girls!
Wear high heels who’re a fit for you and your feet.
Wear them at home, at social conventions and for the amount of time they Will Not Cause blisters.
Do not use them for walking up or down the incline or long walks. Just use common sense.
Susan Veronica
Good common sense tips for shoes.
High heels are for special events where beauty is to be enhanced. As my grandmother use to say; Don’t wear Sunday’s best at work.
Use them for the time you feel comfortable in them Only.
Do not let your feminine side push you to extremes. As beginners goes, we all tend to go all the way out and loose sight. Start small and do little at the time in all from make-up to shoes and attire. Do Not Go for the 6+ inches in high heels because of the advertising. Use a two to three inches, enough of heels or pumps in a combo enough of a flat and high heel shoe, as in a hybrid.
The big heels will only attract attention to you and that will be a problem if not confident enough in your self.
As soon as your feet says; I’m tired, change in flats right a way. Listen to your feet.
Use them for walking on flat, non-slippery surfaces only.
When at the desk, take them off to give your feet a break.
Have a pair of flats handy to change in when the feet is tired or you have to walk for a long distance or on inconvenient terrain.
I have one pair of high heels with three inch heels… of good quality… designed for a dancer. There a saddle style and black so they go with most everything. They are very special because they are my very first pair of feminine footwear.
With a tight pencil skirt they I practice walking in small steps… and more feminine movements. But my feet only want short stints in these ‘female torture devises’… but I love the look and their click as I walk.
I can relate to the walking down hill for a long distance and have your feet killing you. I did this on a backpack trip with proper broken in boots designed for this type of walking… for all sexes. I’ve walked long distances before with no problems and in these hiking boots. But just going down hill which sounds easy was very painful in the end.
So if you see women who commute on the bus in comfortable walking shoes and then change into heels at work… they know something by experience. We should listen to our experienced sisters… and take a hint… or stand out with our tortured feet.
I’m not saying to not wear heels… but be smart about where you walk… and what shoes you wear. You need to keep your feet in shape… and ready to go dancing. *wink*