polarbearx8,
Welcome to the site. I think, like Dena said that the person you have to ask and work with is yourself. Not trying to be mystic or elusive. It is a decision and a journey you have to make on your own. This is a very supportive site and full of people with a lot of information. I am sure there are many here who can give you similar or dissimilar stories to your own and that may encourage you to transition, it is still up to you.
That being said, you can ask for advice and I highly recommend therapy. Many people find a good gender therapist invaluable. Sometimes a general therapist is helpful in guiding you through the maze of decisions you have to make. Are you currently in therapy?
The term transgender is an umbrella term that covers a lot of spots along a spectrum. Some are fine with dressing as the other gender or mixing to an androgynous level; some find under dressing helps and maybe eliminating (or growing) body hair helps; others go the path of HRT; still others go through all the surgeries. You have to find what works for you.
I won't really respond to the pictures. I find that while HRT is great to help mental dysphoria, it can become a path some follow just looking for physical femininization. The trick is, it effects everyone a little differently. Some start to question if it is working because they don't seem to be changing fast enough. While it would be nice to look like an attractive cis woman, it comes down to does it ease some symptoms. That's just my opinion.
I wanted to post some threads that we like to pass along to our new members. If you have not had a chance to read them, please take a moment:
(As I was proof reading my post, Dena already posted them.)
Welcome to Susan's. Look around, continue to ask questions and join in. I hope you find what you are looking for.
With warmth,
Joanna