Wednesday, November 18, 2020

Up and Down and Up Again in High Heels

By Gina V

Perhaps the most quintessential part of a woman’s wardrobe is at the bottom, where her shoes live – especially if they are the high-heeled variety. I read somewhere that said items were invented by the vertically-challenged Catherine the Great to lord it over taller court rivals*. But whatever their origin, I am pretty sure they were not designed for comfort. Yet millions of women still don them at times in preference to something more practical (nowadays without eyebrows being raised as a result), for it is fairly likely they know it is a quick-fix means of looking elegant and feeling gloriously ladylike. 

Despite the trial presented, many appear able to strut about in them the way a duck takes to water. Yet even the most agile can (metaphorically and physically) get too close to the sun when they reach for the sky. With the result that they look in dire need of the nearest toilets!

Many things have come easily to me in life (and if not, then I made it someone else’s problem), one being able to wear high heels without effort when I came out the closet in my late 30’s. I could pose in imposing ones for a drag revue I produced plus spend all night on the local transvestite scene in them with no problem. I once even walked several miles home afterwards in some. 

Despite that, I eventually realized said scene wasn’t meeting my aspirations (that’s another story). So I “retired” for several years and put on several stone. I then relocated to a place of my own, and shifted a fair bit of blubber in the process. So took advantage of that to try out my old femme gear again. Fortunately the more-forgiving garments didn’t make me look like a sack of potatoes, but every pair of shoes gave both my feet and Achilles tendons a hard time.

Regardless, overall results were encouraging enough to rejoin the scene as the next step in my rehabilitation process. So I wore a different pair of approximately 3-inch heels whenever I went out in the expectation I would get used to them as the evening wore on. I realized I was rusty as well as older and heavier, but saw it akin to “riding a bike.” However, it soon became clear the natural ability I once possessed had now deserted me. 

So I then took several pairs out with me and when those I wore became insufferable, I would kick them off with great relief before stepping into a more comfortable pair. Yet despite that, I would still end up in stockinged feet thanks to the discomfort. The final straw was doing a gig while dressed and having to keep perching on a stool to give my complaining calves some much-needed relief.

Therefore, I realized that something else had to be done to reach the dizzy heights of yore. Initially, I solved the problem by acquiring some shoes with a 1½-inch kitten heel. They were manageable, but I felt that I was not only cheating, but envious of my peers prancing about in ones at least twice as high. So I finally bit the bullet and realized that for once in my life, I would have to put in some hard work.

When Olympic champion Jessica Ennis came back to athletics after a break, I read things were not going according to plan due to similar problems. However, that she managed to overcome them to win the world title gave me encouragement in my own battle to triumph against the odds. I also noted that actor Sean Bean prepared for the role of a transvestite by walking around his house in heels on a regular basis. Not an ideal way for an actual crossdresser to tackle the problem, as the thrill might be diminished or even lost in the process. All the same, it was still something to think about. For if one could no longer walk the walk, one would need to take a more down-to-earth approach in order to be less down-to-earth.

So I reluctantly resorted to Mr. Bean's method (Sean’s, that is, not THE Mr Bean!) in the hope that I could overcome my physical and psychological issues. Unlike many, I could wear heels in my home at my leisure, thus, I did so (trying out ever-more daunting ones as time went on) when the mood took me, which was usually while relaxing with a glass of wine or three. Once I got into that habit, I decided to wear some even when not feeling particularly inclined. In that regard, I kept in mind the following experience I had a few years back.

While attending a wedding, I enviously took note of a couple of female peers dancing at the reception in high heels they probably didn't wear any more regularly than I did formal male attire nowadays. I then overheard one say to the other, “My shoes are killing me now!” To which the other responded, “So are mine! But you can’t take them off, can you?” To which they both giggled before carrying on boogieing without apparent concern, as I watched on in my own “shackles” of suit and tie even more wistfully.

So I have kept that regime up for a while now and as a result, have come to view the higher heels in my collection as at least acquaintances, if not friends, as opposed to the intimidating strangers they were before. Sadly, these troubled times dictate that at present, the only convenient place available to test my endeavors in public is my local precinct. Which I have no immediate plans to visit en femme anyway – coronavirus or not!

* I believe that is why court shoes are so-called!

Wearing Boston Proper
Wearing Boston Proper

Rob Lowe and Paul McCrane femulating as nurses in the 1984 film The Hotel New Hampshire
Rob Lowe and Paul McCrane femulating as nurses in the 1984 film The Hotel New Hampshire
You can view the film’s trailer on YouTube.


  1. Love Wearing Boston Proper

  2. I conducted my own experiments with heel height last year. I discovered that I am comfortable with 2.5" - 3" heels, but when I tried 3.5" . . . woof! I could tolerate them for about 15 minutes, and then had to change them out. On the plus side, after that trial, the 3" heels actually felt comfy! Go figure.

  3. Thanks, Gina. In sad response, I agree about the importance of heels and was sent to the edge of depression when my right foot went to hell. Major foot surgery has left my foot fused and I can only wear short clunky heels -- and not for all that long. My personal opinion is this is the worst thing that could have happened to this long-time crossdresser! So I'm sadly supporting your point of view. And I was buzzing around in 4-5" heels before this happened!

    I suspect high heels preceded Catherine the Great. I've seen a number of pictures of French kings wearing some mighty high heeled shoes -- clunky, not stiletto. I wonder if Napoleon wore high heels???

  4. Also, HOTEL NEW HAMPSHIRE is my favorite John Irving Film Adaptation. (WORLD ACCORDING TO GARP is a close second.)

  5. For me wearing heels seemed to come easily - a bit like a duck to water. My only challenge was finding heels in the right larger sizes. Fortunately I have finally found a factory outlet (Diana Ferrari)which stocks a great range of heels up to EU 45. I did have a glitch a couple of years ago, when sciatica caused my left leg to lose all stability, resulting me having to wear flats for an eternity. Perhaps I exaggerate. The physio gave me an exercise regime which meant I was back tottering around in less than 3 months. He was surprised how quickly his exercises has cured me. Most of his patients aren't as motivated as I was.

  6. As a femulator only in the privacy of home, living alone and working from home these months during Covid has allowed me to dress enfemme for many more hours than ever before. And I've been pleasantly surprised to be able to spend the day comfortable and confident in my 4" heels. Although, I must admit, my feet are quite happy when I slip them off when the work day ends:)

    Ciao! Elise

  7. mary:i actually walk &feel at ease in my medium high slingback pumps ..than in man shoes...i am a born sissy