I have heard of womanless beauty pageants but have never heard of one in my area so obviously, I have never participated in one.
My thought on this would be the same as my thought on dressing as a woman for Halloween; This is a case where if you do too good a job, people will suspect that you do this more than once a year. No "normal" male has a $300 set of breast forms, a $200 set of padded panties, a $100 wig and a pair of women's shoes his size.
Many, many years ago, I did a show dressed as a woman, but that was a case where it was obviously a joke. I didn't have my female stuff then.
