Hi VS Fan, I'm right where you are now: I want to tell my best friend, (a woman), and have even posted here that I'm telling here "this week", etc, but still haven't found the nerve.
Reading your post made me think about "why" I want to tell her, so thank you for that.
I also dress like you do, and while driving. I don't own a wig though yet.

I liked in your second post you said that maybe that you're really hoping for her to find it "fun", and maybe expand your relationship to something like what TheHiddenMe has?
In your case, what are you wanting to get from admitting you crossdress? Simply validation and acceptance? You'll always find that here of course. Or, per your second post,
you're really hoping for an accepting friend who you can dress in front of, show you
how to do make-up, wear your wig, etc. (You kind of admit that in your third post)

So it really comes down to this specific person: your massage therapist/pedicurist. You want to share more with her, have her as a friend, etc. She's a professional: most likely she's going to take any revelations professionally, like you said, I don't think you have to worry too much about that, and like others said: in her field she's almost definitely heard similar stories. Like others said too, if that's something that bothers her, and you can tell, there's other fish in the sea in case the "real connection" seems to dissipate, it's just simple fear of rejection of course. You'll never have that
particular friend you seek unless you try. So it's not really a CD issue if you think about it.

Expanding on your connection first to blossom to a real friendship (before revealing more to her) would be a normal course your could take, but approaching a married woman for friendship is very tricky. It may actually be a benefit to be "femme" in a case like that. You might just go slow, tell her you enjoy your time with her as it allows you to feel, in your words: "open and honest", or "real", and talk more about your nails, or color, etc., or talk about her clothes, etc. She's going to figure it out if she hasn't already.

Friends are valuable; accepting friends are a treasure. Seek the first and hope for the second.