The why do you want to cross dress conversation.

[Leelou]

When my wife and I had "The Talk" back in the early 1980's the "Why?" question arose. After some bullshit answers I told her "I do not know why I do what I do!" I also told her I wish I did not do what I do. Frankly, life would have been a lot simpler if I was not driven to wear women's attire. My recommendation for any man trying to explain himself is to avoid saying something to a woman akin to "getting in touch with your feminine side." If my wife and I were to have a conversation I could tell her how wearing women's attire makes me feel which does not answer the question of why I may have chosen wearing women's attire in the first place.

Ladyjade's wife asked a valid question. If a guy finds a dress more comfortable than "X" why does he strap on a bra with false boobs, makeup and a wig? My granddaughter raided my closet and took several of my flannel shirts to wear with her young men's jeans which fit her better than women's jeans. She has long hair; currently blue. She does not apply false facial hair. She does not roll up a sock and stick it in her pants.

I really cannot explain why I am wearing a long white nylon nightgown as I bang away on the keyboard.

That's an interesting take that you don't think that's a good idea. For me personally, I've used a variation of that to explain why I like to crossdress. I don't use the somewhat cliche "getting in touch with my feminine side". Rather I express what my best understanding of what and who I am. I say that I feel that I fall on the Transgender spectrum. There are aspects of my personality and identity that do fall on the feminine side. Wearing women's clothes helps me express that feminine side of myself.

So for me, I find the question pretty easy to answer.