I can understand why a man would want to wear women's shoes and boots. I don't crossdress, but I do have my own women's footwear that I wear while masturbating.
I've been wearing women's shoes since the age of 6. My mom never wore high heels but I was lucky enough to have access to my aunts' closets from an early age. They even seemed to encourage it.
I even tried sex with a long-ago girlfriend while wearing thigh boots. For some reason neither of us enjoyed it very much although I still think it was a worthwhile experiment.
Another failed experiment was wearing pantyhose and garter belts. It seemed to actually prevent me from getting hard! On the other hand I get extremely powerful orgasms when I beat myself off while wearing long leather gloves. My cum almost hits the ceiling!
Would I have shoe sex with a crossdresser? I definitely would have, if the opportunity had presented itself when I was still single.
My wife pretty much tolerates my hobby. When she goes on a business trip, she tells me "This week you can sleep with your boots on".
That's pretty much the story of my life, constantly on the lookout for new and different ways to get my rocks off.