Why on earth would you want to wear high heels?

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.

En Femme Style

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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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14 years ago

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… Read more »

9 years ago

I know this is an old article but just in case someone stumbles upon it . . . From my perspective I find it difficult to believe that any self-respecting cross dresser would not be addicted to heels! I can’t pass a shoe store, boutique, or web page without taking a long look at the shoes. Personally I have 47 pair at last count. Some are more comfortable than others and I agree depending on the heel height and overall comfort of the toe, it can get a little strenuous on the feet. I find the more I wear them… Read more »

Keri Council
Keri Council
8 years ago

People are selecting the stick characters thatt best represent each
individual in their family and are. You will gain more
respect when people can understand you. Sharky is lovely, and
there is nothing more that hhe loves than being cool and
hasnging round the pool with his chicks.

Alejandra Salerno
Alejandra Salerno
8 years ago

Whenn we laugh, we breathe deeper, our heart rate can increase, and most people move a bbit while laughing.
Even if you’re not a comedian, don’t have a humorous
bone iin your body, or can’t get a laugh out of
a cat, you can try some of these simple tips and techniques to capture some side-splitting,
humorous photos. Both of us wre apparently exhausted from work and defaulted to our ‘I’m tired’ behavior: I couldn’t stop talking about myself
and Brien was completely shut down, offering only monosyllabic responses.

Karyn Lobelia
Karyn Lobelia
8 years ago

I love wearing high heels , but mine vary from 2 to 3 inches because I feel I love the effect of wearing heels without being absurd about the height . I love walking in heels in public and at parties , because I am honest enough to admit I am vain about how much attention I get . I spend a lot of time on makeup , hair styles , and clothes coordinated with my Jewerly , heels accentuate the effort I make to look gorgeous . I love being able to transform myself from the makeup table to… Read more »

Shannon Fox
6 years ago

I asboulty love heels still not the best walking in them but am getting better also I have small feet there a uk size 6 so I can find heels my size which is a good thing for me

Jennifer Friendly
Active Member
1 year ago

OMG, I agree, high heels are like cross dressing crack. There’s just something uniquely woman about high heels. I’m sure I’m not the only one to notice, but you ever been with a few guys around the office break room, the sound of a flock of ducks comes down the hallway, nobody even looks. The clicking sound of high heels, every one of them will look. There’s just something magical about the sound of heels, like the sound of a Harley, distinct, unique, attention getting. I love them, wear 3″ most of the time. Even my slippers are 3″ fuzzy… Read more »

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