I see lots of postings asking for advice, so I figured I'd throw my hat into the ring. Here's a set of photos showing where I'm at now:
https://goo.gl/photos/63eDC4ZzoJEUE7MW9As you can see, I'm an older man (58), and I'm never going to win any beauty contests, but my appearance as a woman is better than I would have expected. I'm still a relative novice when it comes to cross-dressing, but I learn quickly. As I mentioned in my other post, I have long experience with cosplay and I can make just about anything from corsets to ball gowns to prosthetics.
I am seriously considering HRT, FFS and possibly more.
I have several advantages in this process: first, I live in a part of the world which is very open to sexual diversity; the vast majority of my friends are either poly, pagan, or kink, and there are already several trans / genderqueer folks in my social circles. So I'm not too worried about all my friends abandoning me. Family is not an issue, since I've lived alone for the last 20 years, never married, no children, parents deceased and none of my siblings are close. So I am beholden to no one. (Why this is is a longer story which I may relate at a later time...)
Second, due to my being an eight-year veteran of Google, and success in investments, I'm financially secure and can afford whatever is needed to affect a transition.
Thirdly, I now work in a small startup that is 50% women (it's an animation studio), and as the lead engineer in the company there is virtually no chance of me being discriminated against in any kind of official way. Whether I get discriminated against in unofficial ways remains to be seen, but the folks there are pretty enlightened so I am hopeful.
My plan is to take this really slowly, to experiment with ramping up my femininity over the next, say, 2-4 years.
BTW in the photo you'll notice my hairline. I got 2500 neografts from Dr. Beck a year ago - my opinion now is that 2500 was not enough, as the hair is still very thin just above the temples. Fortunately my MBP never touched the crown of my head.
I realize that I'm never going to pass (for one thing, my head is too large), but I'd like to come as close as I can. Fortunately, living in Silicon Valley means that my not completely conforming to gender stereotypes is more likely to be accepted here than it would be in some other parts of the world, so I'm willing to settle for less than perfection.
I've been inspired by many who have gone before me, but in particular I am thinking of Danielle Bunten Berry (
https://en.wikipedia.org/wiki/Danielle_Bunten_Berry) the creator of the classic computer game M.U.L.E., who I met at GDC both before and after her transition. A remarkable person who died all too soon.
Anyway, I'm looking for advice / criticism / ideas from folks out there who are more experienced in this.