"How Can You Wear Those Heels?"
"How Can You Wear Those Heels?"
While I was out and about on Saturday, I had a woman walk up to me and ask how I could stand in the four inch heels I was wearing. In all the years I've been publicly wearing women's clothing (close to twenty and counting), that's THE one question I've been asked most, especially by women who look perplexed, even awed at my accomplishment, as if what I did defied the laws of physics. My answer to her consisted of just one word: "Practice".
Being asked that question always makes me chuckle because it seems so silly to me. That leads me to suspect women believe men are inherently incapable of standing, much less walking in high heels, in THEIR shoes, and when they see men like me pulling off that feat, they have trouble accepting that reality. For me, it's no impossible task, I've been wearing heels since I was thirteen when I wore a pair of my mother's shoes to satisfy my curiosity over how she could walk in them. Once I discovered it wasn't all that hard (after some practice), it became great fun, and I've been strutting around in heels like in the picture below ever since.
Perhaps women who pose that question think men lack some genetic ability to master the feat of wearing heels, the simple truth isn't earth shattering: it's not that hard. Really. If women can do it, so can men. Plain and simple. That's the answer.
Being asked that question always makes me chuckle because it seems so silly to me. That leads me to suspect women believe men are inherently incapable of standing, much less walking in high heels, in THEIR shoes, and when they see men like me pulling off that feat, they have trouble accepting that reality. For me, it's no impossible task, I've been wearing heels since I was thirteen when I wore a pair of my mother's shoes to satisfy my curiosity over how she could walk in them. Once I discovered it wasn't all that hard (after some practice), it became great fun, and I've been strutting around in heels like in the picture below ever since.
Perhaps women who pose that question think men lack some genetic ability to master the feat of wearing heels, the simple truth isn't earth shattering: it's not that hard. Really. If women can do it, so can men. Plain and simple. That's the answer.
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I don't want to LOOK like a woman, I just want to DRESS like a woman.
Re: "How Can You Wear Those Heels?"
I concur, wear a fantastic skirt and some heels, people will notice the heels first and comment on them, way before getting to the skirt. I was on a platform in full latex, skirt and all, and the question asked was "how can you walk in those heels?" I used the same response as you "practice" and like you have been absorbed in trying feels from a small boy.

I still admire women who can walk well in heels and wonder why more women do not get good at them. I know having heels on your feet, makes running away harder, I feel that when I am in tough areas. But for getting attention, heels do that in spades.
I once had a long conversation with a couple of women in Tesco's who were marveling at my heels and me walking in them. One woman came out with the line, "I could never wear a pair of heels like that, it would kill my husband!!!" I responded that she should try a pair and I was sure that he would lover her for it.

I still admire women who can walk well in heels and wonder why more women do not get good at them. I know having heels on your feet, makes running away harder, I feel that when I am in tough areas. But for getting attention, heels do that in spades.
I once had a long conversation with a couple of women in Tesco's who were marveling at my heels and me walking in them. One woman came out with the line, "I could never wear a pair of heels like that, it would kill my husband!!!" I responded that she should try a pair and I was sure that he would lover her for it.
Last edited by Uncle Al on Mon Mar 30, 2026 7:42 pm, edited 1 time in total.
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Daily, a happy man in a skirt...