You have asked so many questions! We have a quite complete wiki here and many of your questions are answered there. Also if you look through some of the forum threads you'll find the stories of people who have had similar experiences.
Just to answer one of your questions, though, if you have male to female gender reassignment surgery, you will have to use a dilator (it's not a dildo) pretty much for the rest of your life. And no, you do not, actually cannot, walk around with it in. *there are a number of forum threads dealing with the dilation regimen*
As far as personal stories go, what do you want to know? If you go to my blog, listed in my sig, and here, you'll find many personal stories about my transition from male to female. There are other blogs here that have many stories.
And how about you? We are interested in all our members and their struggles. Take a bit and tell us about yourself in our introduction thread.
-Sandy