Great story, Carica – you found something more powerful and compelling than the urge to dress!
I don’t think wanting to pass is a generational thing – it’s just one aspect of the craft.
On one level, cross dressing is an art – Drag Queens are an extreme expression of that art, and some create exquisitely beautiful looks, while some create parodies or even deliberately horrifying versions of female appearance.
“Passing” is on that level – it takes artistic skills to create a look that transforms a male face into one that is convincingly female – and attention to detail on the figure, voice, fashion and accessories.
But that’s not the entirety of cross dressing – many are happy to just wear a dress, underdress, wear makeup or nail polish, and it’s all part of the lifestyle – it only has to be art if that’s how you want it – you don’t even need to label it cross dressing if you don’t want to – fashion is marketed, and we can choose to follow or lead, or do our own thing – and I believe that’s how it’s always been.