I can relate to the shopping anxiety (guess most males can to a degree), but as any anxiety, it will get better with exposure and practice. I've sometimes chosen and then regreted the easier way of bringing company when shopping for clothes (especially female clothes) and it often turned out to be counterproductive: it helped me to relax and get to it but after that I'd prefer to be alone without the other's suggestions or criticism.
As for the shoes, you guys&gals and your petite feet
I've got 45/46 so the shoes have always been at the utter end of to-do list. And heels? Impossibility, I would be scraping thy sky!
In fact I've walked in heels only once and it was a powerful experience. I and my ex were on a trip, descending a steep hill, a terrain ill-fitted for the heeled sandals she was wearing. She suggested swapping our shoes. Hers had an open tip so, to my amazement, I could walk in it quite comfortably. And oh, how I felt... delicate, precious, fragile, so very feminine...
It was absolutely unprecedented and unexpected. We got down to the village and I strolled the street slowly and silently for a moment, to and fro, totally lost in it, even loathing the fact that there is no audience of villagers to give embarassed looks to
When she saw what it's doing to me (and, maybe, how I look being dressed quite androgynously), she lost her good humour and coldly demanded it back...
It's strange to realize that this happened about a month ago and since then I practically supressed the memory... Bad subconscious, bad!
And as to the restrictive society... well, half of the thrill of the ride would be lost without it, wouldn't it? We can imagine ourselves as torchbearers
. Whether it's a torch of freedom or a torch of decadence, I'm still not sure...