Yes I love the feeling I get when I wear a sexy pair of highheels and tights and a sexy dress its an absolutely grand feeling ,I don't try to pass as a women so I don't wear wigs or a lot of makeup with exception of the occasional nailpolish and lipstick ,no jewelry like earrings or bracelets,etc.
this is my favorite pair of stilettos
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Do you have a goodwill near you or some sort of consighnment shop if so you can get them really cheap just to try them as far as size ,for me I wear a men's size 9 1/2 in women's a 10M so about one size up I think you'll have to find what fits you best of course ,each of us is different