Hi Amber,
Welcome to Susan's. My sympathy to you about losing your wife.
I really recommend spending time reading posts in the many different forums, if you haven't been doing that already. There is much information here. I've CDd my whole life, but didn't go out until I was in my 20s and living on my own. When I did it involved skulking around in the dark safety of the night, mostly driving around. I only did that a few times, and I spent years in circumstances that prevented the opportunity to dress or even have much to dress in. Also, being seen at a distance dressed wasn't a big thrill. I know who I was, I didn't have enough need to being seen and miscatagorized at a distance.
You will find many brave friends here like Jillieann; I never have had the courage to venture out to the mall! It will also be obvious how brave they are in the way they are dealing with their gender issues. I'm in awe of them, and have been helped just by reading their stories.
Susan K (not the Susan of Susan's)