I've only been out dressed as a woman a few times. The main reasons why I haven't done it for six months was because I was too fat and didn't look right. But I am addressing that now with my diet.

 

Another reason was I wear my court shoes round the house but as soon as I walk outside, my shoes come off. I cannot keep them on my feet. The heels are only 2 and a half inches.

 

The shoes fit nicely when I am wearing them round the house but outside they come off. I tried tighter shoes. They stayed on but they were killing me.

 

Any tips?

Do you only wear heels?

I've been wearing heels exclusively for years when crossdressing, but recently I discovered the virtues of flats!

Speaking for myself, I came to the conclusion that I can wear awesome looking heels OR I can walk around. I consider heels to be shoes for display and not for real walking.

When the going gets tough and I want to walk on SERIOUS TERRAIN (like an outdoors wooded area) I have to "bite the bullet" and wear the clunky boy boots.

Years ago, when I visited Denver, I noticed the office girls on their lunch breaks walking around. I could tell that they worked the offices because they wore their pretty "traditional" pretty dress and skirt outfits but they were also wearing tennis shoes for heavy long-distance walking.

 

This may not be the answer that you would want to hear, but I'm saying what I would do.

 

And btw, I recently found a pair of "mary jane" flats that I think are pretty cute!

Im very very lucky, i have size 5 feet!! im also only 5ft 5inch and a size 10/12, so finding shoes and clothes that fit me have never been an issue.

 

I know you didnt want to read that, but heres my advice. have you tried heel grips? i used to run a very successful shoe shop, and that was the solution to many ladies who loved shoes but they didnt quite fit properly? The are only a few pounds, not sure in other countries but they arnt expensive.

 

Hope this helps.

 

Ayla xx

Kitty...

I have to admit, Ayla is right. Heel grips! I should've thought of that.

Never mind what I said. Ayla's response is much better than mine.

Dianne Cassandra said:

Do you only wear heels?

I've been wearing heels exclusively for years when crossdressing, but recently I discovered the virtues of flats!

Speaking for myself, I came to the conclusion that I can wear awesome looking heels OR I can walk around. I consider heels to be shoes for display and not for real walking.

When the going gets tough and I want to walk on SERIOUS TERRAIN (like an outdoors wooded area) I have to "bite the bullet" and wear the clunky boy boots.

Years ago, when I visited Denver, I noticed the office girls on their lunch breaks walking around. I could tell that they worked the offices because they wore their pretty "traditional" pretty dress and skirt outfits but they were also wearing tennis shoes for heavy long-distance walking.

 

This may not be the answer that you would want to hear, but I'm saying what I would do.

 

And btw, I recently found a pair of "mary jane" flats that I think are pretty cute!

 

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Hi, I tried wearing flats but they do me no favours. For me personally it's like wearing man's shoes. That's just me. I like to feel my feet in heels. They don't have to be big heels, just a good heel. Makes me feel more feminine. Also, when I go out I always wear skirts.

 

Skirts with flat shoes do not go. That's just my view.

This post was edited by Kitty Koil at May 31, 2013 8:10 PM BST

I've heard of heel grips. Never tried, so I'll have a look now. Thanks.

Glad I could help hun, let us know how you get on xx

Have you tried shoes with straps at all, such as mary janes for example.