Maybe I would. I do love wearing a bra with forms, but I often just don't bother for comfort reasons if I'm simply relaxing at home and not dressing completely and wearing a wig and makeup. I've wondered about trying a "flat chested bra" just to have that bra "hug" without the discomfort of my usual sturdy bras needed to support realistic forms. Does that make sense? Other than that, the draw of wearing women's clothes is wearing women's clothes. You won't catch me in "men's" panties or pantyhose with a sheath. And, I don't like fetish wear at all... I want to wear clothes a normal woman wears, not strip-club attire.