Everyone has already given some really wonderful responses.

First, based on your pictures, I'd say you're already well on your way--and I'm not saying this just to be nice. You look a lot like my aunt Martha, who has a very active social life.

Second, I would definitely see a gender therapist ASAP! They will help you work through all these issues.

Finally, I am 49 and had a lot of the same concerns you have--and still do. What am I doing? Is it too late for this when my better years have passed? Then I stumble across several quotes that helped me:

-- Someone told me that when I'm 60, I'll still be sixty whether I transition or not so why not go ahead and transition if I'll be happier?
-- Joseph Campbell always said "Follow your bliss." If you're not familiar with the whole passage, you can google it. I reprinted one paragraph below.
-- George Elliot (see tagline) "It's never too late to be who you might have been."

I've also met several late transitioners in person who all tell me the same thing: they are much happier than before. To me, that means a lot.

Jane

"If you do follow your bliss you put yourself on a kind of track that has been there all the while, waiting for you, and the life that you ought to be living is the one you are living. Follow your bliss and don't be afraid, and doors will open where you didn't know they were going to be."

Ahhhh Quotes.  I nearly forgot the seminal one told to me by a very special angel in my group

Argue for your limitations and sure enough they are yours - Richard Bach from Illusions

I sit to breakfast every morning with that framed right in front of me on the table where it can't be missed

Hi Cathy,
In actuality that was my first question when I came to Susan's... Am I to old??? The responses I got were overwhelming to say the least. It was then I realized I wasn't the only one and there were many just like me... (Well almost, I'm an original... LOL) I think that was my biggest fear was transitioning at age 57. All I can say is the last few months have been a wonderful adventure. I am learning to love the real me and not stuff this girl in the back of my mind. It is truly liberating to say the least. I am working with a great therapist who is helping me to see the true me, and believe me I was a total train wreck trying to be a man. Bottom line though it is your choice.... Myself I chose life and happiness.

Quote from: CathyAnderson on April 26, 2014, 10:07:23 AM
As I've crossdressed on and off for years, I've often thought about this.  My conclusion is that what matters is not so much passing as to present an amiable, pleasant appearance, and generally to be a positive experience for other people.  In other words, I'm quite fine if someone walks away thinking, "Obviously that is not a genetic female, but he/she was very friendly and thoughtful."  What I mean is that the more my focus is on benefiting other people, the less is any concern about passing.  Hopefully we are approaching the day when people *respect* transexuals in view of their complex life journey.

An old photo from 2001 when I used to frequent the Queen Mary club in Los Angeles:

You have a very healthy mentality.  With that mindset and the feeling that transitioning would offer you a happier life, I think you are in good shape.  That matters much more than age does.  Good luck with everything and keep us posted.