My 2 cents worth
Most of us hide our crossdressing because we don't know how our family,friends would react if they knew.Most of us would love to be free of that worry.I'm sure your father kept it a secret because he is worried you would reject him if you knew.I only dress in front of my wife but all my children and two of our grandchildren know about Michelle but that's as far as it goes but it was a huge relief when they found out about her( by accident,long story) and still accept me as a dad and grandfather.I think if your ok with him dressing it would be a huge relief for him to know that.How to go about that is not for me to say.You'll know.