As always ladies, I appreciate your support and experiences to help my with this journey.
We are all different and very much the same. My background is from a long time military and suburban conservative family and background that attacked my desire to be different at a young age (7ish) with the core response; "you are what you are and not what you think". It is fair to say I did dress privately in my sisters things moving forward. Then puberty hit and it was terrible and for the most part that time my memory is limited in what I remember because I worked so hard to block the misery out. This was the second lap of counseling that suggested (as the 70's so nicely represented) that you are a man because you are in a man's body so adapt and become the man you are becoming. Being that age in that sociological time I either had to sell out or kill myself. I love myself too much for the latter.
It was hard but not impossible because I would rather have relations and relationships with women, than men. There is nothing much I like about the male gender or myself in a male body, particularly the alpha male; so I worked very hard to become the alpha male persona I detested and own it, at least outwardly and I was good at it. It was lifetime theater.
In high school I worked so hard to be appearing athletic and it took great work to develop skills to pass that way (accomplished tennis player), and even played football senior year. Never went to prom because I felt that I would hate wearing a tux vs. a dream dress, although having women at my beck and call. I will repeat, I love relations with women.
College, fooled myself too much and basically had a miserable four years, despite having a cache of clothing and decent relationships. Again late 70's, early 80's and society mandated I play the role.
Early adult life struggled while building a huge career and ultimately finding a woman I would like to spend my life with. Settled into the life with kids, community leader, dad, husband, career, money and found myriad ways to succumb to my secret desire and needs to become complete with outside diversions. Now, that the kids are out of college and in their lives, so much of the family have passed (grandparents, aunts, uncles etc), my social circle being weaned down as I don't need to gun my network to provide for my livelihood, and a transitioning marriage after 25 years (kids grown and out, dog passed, different life, but good) I feel as though it may not be too late, 53, to make the move to finally merge the physical with the meta-physical for the future. I so dream of my feminine self, the journey over the next couple of years, the mind change, body change) I really can no longer work to lie to myself and society.
But again, I like my therapist but would kill for the ability for a mentor of like women (mid-50's start in transition) to get answers or direction. Like I said early on it was my ego that kept me from killing myself and my ego to own the alpha male persona outwardly to become successful in business and the community. This ego will also mandate that I become the same outwardly beautiful woman as I am on the inside. I do not want to be a haggard old woman and fear the early and mid-transition because of this. I understand there is a means to the end, but I don't want to get stuck in the middle. Obviously I fear the unknown.
Thoughts?