would your father be proud of you
not only no but hell no. When i was 10yrs old and got caught by my folks wearing my mothers skirt, my father said that real men don't wear skirts,and he also said that i was sick in the head. He thought that i was sick in the head until he died about 5yr ago.
Add me to the "Nope" list
My dad was a pretty conservative, hard-working, hard-playing man who didn't approve of my look during my "hippy" years. He didn't realize that when he left my mother, he removed the best male role model around. Mom became the one that I followed and emulated. She wasn't too happy when she found out I'd been trying on her clothes and sent a 13-year-old me to stay with Dad for the summer. I don't think he knew why I was there. We never talked about it. Based on everything I knew about him (he's been dead for 15 years or so), he may have been proud of my education, career and my ability to build things or play ball, but not crossdressing. His may have been the "greatest generation", but it wasn't the most understanding one.
Whatever floats your boat...
probably would have been my father's response. We had a pretty good relationship after I graduated from college - enjoyed similar literature and were interested in the same issues. He tended to speak in generalities and I to speak in specific examples. We traded books regularly. I visited him every 4 - 6 weeks until he died, not quite 2 years ago (I still think I should take a new book to him).
As far as I know, he had no clue about my cross-dressing, but we had enough mutual respect by the time I would have been ready to discuss CD'ing with him (the last year, roughly), that I think his response would have been this email's subject. He might have had some questions, so it could have led to another interesting discussion... I miss those...
Lee