Why Would You Want To Wear Heels?

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.

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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Shannon FoxKaryn LobeliaAlejandra SalernoKeri Councilnayomi2438 Recent comment authors
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Shannon Fox
Member

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

Karyn Lobelia
Member

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 »

Alejandra Salerno
Guest
Alejandra Salerno

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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.

Keri Council
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Keri Council

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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.

nayomi2438
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nayomi2438

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 »

Debbie
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Debbie

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 »

Susan Veronica
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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… Read more »

Susan Veronica
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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

Susan Veronica
Guest
Susan Veronica

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… Read more »

Denise Carolina
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Denise Carolina

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.

Jay
Guest
Jay

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!

terri donavon
Guest
terri donavon

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

rogina garter
Guest
rogina garter

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!!

Vicki
Guest
Vicki

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

Lynn Jones
Guest
Lynn Jones

They don’t call them killer heels for nothing. smile 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. smile

Petra Bellejambes
Guest
Petra Bellejambes

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… Read more »