Hi Arch,
I'm not sure if my story will help but it seems to me that I have a few things in common with you on this topic, given what I've heard so far. I'll share a bit that I think may be relevant.
I have 3 "Dads." The one in concern is the one I met when I was age 13. He was by far the best Dad out of the 3 of them, thankfully. But things didn't start out too great for him and I. I called him "Dad" for more than 20 years.
My mom was what she thought was a devout Roman Catholic. I was raised as Catholic without choice until I was 15 years old, when I started making my own choices. My past, before transition is very complicated.
My Dad past away in 2005. He knew that I had a some sexual experiences with boys/men before but I never talked about dating men to my family. It was only acceptable for me to date women. When my relationship with him grew somewhat close toward the end of the time we spent together, he seemed to be on my side more than ever. Or at least as "unbiased" as he could be. We had more of a "don't ask, don't tell" relationship when it came to what I did and didn't do, and who I did it with when I was going out clubbing and spending the night or weekend with whoever I was dating at the time.
I didn't think my Mom would accept me as trans*, let alone bisexual. After reaching my teens, I studied (and sometimes practiced) every religion I could learn about "but" hers—a sore spot for her. She knew I was "different" when I was a toddler and definitely by the time I was 8. She knew I was different in gender and sexuality than the boy she thought I was. But I was not permitted to behave in any manner other than that of a good, Christian, cissexual, "straight" male.
I was made out to be the black sheep of the family. My Mom abandoned me to state custody when I was 15. She made an example out of me to my younger brother and sister. An "example" which has left scars between us all, that have lasted to this day.
Despite the past, I lived relatively close to my family until the year 2000, with only a few spaces where I spent a year or two away from everyone. The last year that I got to spend with my Dad, I think he had really started to warm up to me. We talked about things we had never talked about before. And he seemed genuinely interested when he would ask me questions about where I was going to "hang out" on the weekends, "Oh, what kind of club do you go to? What do you do there? Do you work there?"
I wore make-up, mostly goth at that time. Leather choker/bracelets/belt and knee high black boots. Fishnet covering my forearms and waist. I had more piercings than everyone else in my family combined.
I don't mean to focus on this, to create some image of myself, but this is my memory of the last private conversation that he and I had. He was concerned and interested in what I was doing. Why I was packing a backpack full of skirts and both male and female clothes on the weekends when I went out. Did he know I had all the make-up and female clothes in my backpack? He already knew I shaved my entire body except the hair on top of my head. Actually, my whole family knew that... I did it once for swim team when I was 16 and never stopped (well, not until HRT anyway). I started feeling terribly "unclean" when the hair grew back. So I just kept up with it.
I don't know, maybe he wasn't "genuinely" interested. But he put up a good "front" in the last couple years, if he wasn't. He was "Chief of Police" when I met him. He'd been in every branch of the military except Navy and was still in the National Guard part time when I last seen him. Except he wasn't a policeman anymore—he was a Fire Chief and Paramedic of Sun City West in Phoenix, where he served the Phoenix community until he passed away from cancer.
When he asked about what was in my backpack, we were out in the garage at my parents house (I still lived with them at the time, except for the weekends that I most often spent escaping from them). It was already dark out. There was this small, quiet voice inside me that wanted to talk to my Dad. I wanted to run into his arms and burst into tears. I wanted to tell him of numerous things I was ashamed of. I wanted admit to him that I still didn't know who I was, that I didn't understand how I fit into this world yet, that there are still a lot things that don't make sense to me.
I wanted to say all of this without him being dismissive and thinking I just being foolish or illogical. I know he would have listened to me. He would have stayed up just to talk to me even though he had to be up for a 24 hour shift in less than 6 hours. I don't know if he would have understood. Honestly, I wouldn't have been able to tell him that I was a transsexual at that time. I didn't have any words or understanding of trans issues until he passed away.
I regret not telling him. Oh, how I regret not telling him. I didn't know "how" to tell him. But I wanted to try. Of all the things that I've been ashamed to tell my dad, I would not have been ashamed to tell him who I really was. I would have been very afraid, yes. But ashamed, no. It was the truth. My truth. And he never got to hear it. He never got to understand me. He never had the chance to be proud of me because he never knew who I was.
Yeah, he had said a few times in my life that he was proud of me. But it all seemed like a dream, it wasn't really me he was proud of. He was proud of this empty shell, this bruised and lost person I had become. I learned how to get by, to survive, to get the job done, to do and say what society expected of me. But I never learned how to be me. That little girl was burned, beaten, and abused mentally, physically and sexually. She was told how worthless she was, how stupid, how stubborn, how evil. She was reprogrammed. She learned to not be herself. It was safer that way anyway, less work, and much less painful and confusing.
I didn't break this programming, this "code" until I was in my 30's, until I went through 3 fathers, losing every one of them. Yes, I am sure I saved my father some pain, some tears, some shame, some fear and disappointment, maybe even some anger; by not telling him I am transsexual.
There is only one thing I remember my Dad pulling me aside and talking to me in private about, to confide in me. It was one of the very few times I had ever seen tears in his eyes. He looked at, he was frustrated for me yet hopeful at the same time. He wanted what was best for me and he said something like, "don't live your life trying to meet the expectations of someone else." I didn't understand exactly what he meant, and even less did understand who he was referring to, but then he said: "don't spend your life trying to live for my approval... for anyone's approval!"
He "was" talking about me. But he was referring to his past. He never got his fathers approval from what I understand. And I would guess that he never did. My Dad's father was still alive when my Dad past away.
When my father passed away, my family was torn into miserable pieces. I drank more alcohol than I can remember, I almost committed suicide, my brother was on drugs, my sister got a divorce shortly after, my Mom... I don't even know what to tell you about my Mom. That's a whole 'nother story.
I came out to my friends, family, work, ...the whole world in 2008. I have turned my life around and I can't imagine anyone who knows me not being proud of who I have become in respect to where I came from.
Unfortunately, my family still doesn't know me. I tried to bring them back into my life when I started my transition. But it's too late. They haven't broken all ties with me but they may as well have because I have a phone number, email, and mailing address that they never use. My own Mom. Aside from her giving birth to me and saving my life (literally) a couple times, I have nothing good to say about her at this point. And that has weighed heavily on me for the past few years... but at this point, all I can do is move on and wish that she would have opened up to me when I opened up to her.
If my Dad was here, I can't promise you that my Mom and I would have a good relationship once again, I can't even promise you that my Mom and I would be talking. But I know without doubt that my Dad would not have gone to his grave without trying to get my Mom and I back together, to explain to her that she has a daughter and NOT a son who she made herself and everyone else believe all of this time.
He would have told me that he was proud me, I am sure of it, if he knew everything that I have gone through in the past decade. I seen the tears in his eyes from the pain of not having his father's approval. And though he and I have had more than a few disagreements, because of that glimpse into his heart I know he would approve of the woman I have become, I know that he would be proud of me for who I am now.
It would be selfish of me to wish he was still here just to help me work some things out with my family. But if he were still here, or had I told him when I had the chance, things might have been quite a bit different between me and my family.
I will never know.
My apologies for running this post so long, I didn't plan on becoming this long winded or emotional.