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Crossdresser high heels present the same challenges for us as they do for the women they were designed for. They hurt! In that area we share the same pain as women do which has led some of us to explore the problem in search of a solution. Its possible that crossdresser high heels are even more painful that what women experience.

The pressure of standing with your foot shoved into a 4-inch pump is different for a 100 LB woman vs. a 200 LB man. Crossdresser high heels need a little stretching to make them more wearable. There are mechanical shoe stretchers available, but I prefer a couple of different methods.

  Crossdresser high heels fix one.

crossdresser high heels

The freezing method where you insert a zip lock baggy into the toe of the shoe. With your hand inside the baggy use your finger to push the corner as far into the toe as possible. Then add enough water to fill the toe area. Make sure the zipper is at the top of the heel area when you are done or it might leak. Then put the shoes in the freezer overnight so ice will form in the toe area. The shoe stretches as the ice expands gently widening the shoe. Let them sit for a couple of minutes when you remove them from the freezer so the ice will melt enough for the baggy to slide out. Repeat several times if you need more stretching but be careful as there are limits to how much can be done.

Crossdresser high heels fix 2

crossdresser high heels

Get a leather conditioner like Cadillac Boot and Shoe Leather Lotion. Rub it in the inside area around the top and sides of the toe area where your foot will touch. Being careful not to get it on the sole of the shoe making it slippery. Let it soak in a little then put more on again allow it to soak in. Then take a hair dryer on high pointing inside the toe area for a few seconds. Be careful not to do it too long getting it too hot it’s better to do a less at first. You can increase the time and temperature if you need to. Next put the shoe on and stand putting your full weight on it allowing the shoe to mold to your foot. Do the same with the other shoe and wear them around before doing it again. Don’t repeat this process until after you have worn them out for an evening because they will stretch even more with wearing. I got carried away with the stretching and now the shoes are too loose.



  1. Personally I’ve stretched my first pair of heels 4 sizes bigger by making the leather damp, very damp and then walking in them with thick socks

  2. Excellent article!! Thank you! Just got a new pair of heels and they are definitely on the tight side. Your advice will be put to the test straight away.

  3. Dear Micki, Thank you very much for this great advise. I have some shoes that I will treat as you suggest to make them more comfortable. I am fortunate to have found one brand of shoes, though, that fits perfectly in size 8 1/2 and by now own several different pairs of this brand. Best wishes, Franzi

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