Yes, I agree with Paula. The first two issues are serious negative topics that should be dealt with by themselves individually or maybe lumped together depending how the conversation goes. I would guess that he is aware that you have suffered because of his behavior, but maybe or maybe not the behavior of his friend. That being said, he probably does not realize the extent to which he has hurt you and your life for all these years. Those could be some very serious and heavy discussions, or may be better than you think.

I would definitely handle the CD side later after you get through or almost through, the first two. It could also be a good positive opportunity to re-bond and strengthen your relationship with your dad. If you see your father regularly, you may have some follow on conversations with him about the first two issues as both of you grow into this new open and honest communication mode. Once you and hopefully your dad are in a better situation about those first two issues, that could maybe be a good time to bring up the other one and complete your personal task of confronting past issues.

If you stay around here long enough and read enough posts about how many members here struggle with their transgender nature, you will begin to learn that there are some very serious issues and impacts on their personalities from shame, frustration, insecurity, and a lot of others. Now, when we use transgender" around here it generally means, but is not totally accepted, that the term is an umbrella term covering crossdressers (CD's)to full on transsexuals (TS's) who are the opposite gender to what their physical attributes and organs are. All of this over a great big spectrum from a little bit to a whole lot. So, who knows where dad is along that spectrum and how well, or not so well, he has been able to deal with that side of himself? He may not even know.

You say that you are in a program to help you deal with your PTSD. Is there someone running that program who has the professional qualifications to share all this with and offer you some one on one advice? Our opinions here will vary all over the place and are based on each one of our individual experiences and points of view. This is not a bad source to get an idea about this side of the human population, but we are far from qualified to really give you good sound advice based on what little you can write here. I.e. professional counseling is recommended before you start these serious conversations with your dad and both of your pasts, presents and futures. Good luck and thanks for loving your dad.