If there was some magical recipe, I'd give it to. But sometimes the answer is simply to go out and do it!

The first day can be terrifying. The first week not much better. But after a month or so, you're probably going to feel like you fit right in to the world you want for yourself. Little things will happen that will boost your confidence and each one will tell you that you're doing it--you're succeeding at living your dream. After a couple months, you might even have that magical moment when you're out and about, and you completely forget that you're trans. You'll just be a woman like any other woman, albeit with a "special" history.
It really is a jump, but with your looks, I know that you're going to be in for a soft landing.

One morning, get up, say you're going to do it, get dressed, and go somewhere that you can't get back home easily or immediately. I wouldn't recommend going to work (like I did) unless you can get away with it (like I did) but perhaps to a mall. You don't even have to go into a store! Walk in, buy something at the food court, sit in the eating space, and just be around people. Once you see the world from your new eyes and the worlds accepts you for who you are, this cycle becomes self-strengthening. Before you know it, you'll wonder what you so afraid of in the first place.