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I did go out crossdressed once in Edinburgh with a former 'understanding' girlfriend - just for the experience and, I suppose, the thrill of doing it.
One problem was that I was over 6ft in small heels and she was about 5ft 3" - so a bit like little and large in every respect.
Worse still we chose a 'football' day when Hearts (the local football side) were playing and the street seemed awash with 'male' crowds. So lesson one: Pick you day and your place.
We carried on - I had a good wig and a long coat to cover up with. We soon hit the shops to do some womanly shopping.
The first stop was into real woman's territory - a big store with blouses, skirts, underwear and what should have been heaven.
The strangest thing was that it wasn't heavenly. Had I been there as a man, which I frequently am in many women's shops, I don't feel at all embarrased. I feel through the racks, look for what I want and buy.
Here I felt like a 'pervert' with the eyes of other women shoppers on me while I looked through 'their' clothes. It made me very uneasy and I didn't buy.
We left and went on to another shop and passed a group of children, who I heard snigger and say 'he's a man dressed up'. I couldn't take any more and after another brief shopping call we turned around and headed back to the hotel. Since then... well that's tomorrow's little story.