In theory it should be quite easy, once I have made the decision to tell somebody, it shouldn't be that difficult to say "I'm a cross dresser" but somehow it still is. Of course that is partly because as a statement it begs more questions than it answers. When I told S the other day I was searching my brain for another phrase but failed to come up with one. When I told P a few months ago I just phoned in advance having already said I wanted to tell her something personal I went on to say that it might be a bit of a shock, but when I'm dressed like this I prefer to be called Paula.
As I say whatever phrase or word is used it begs more questions, like "what is a cross dresser" so "you're a transvestite why not say so?" to most civilians one catch all term is quite sufficient, for us we know we are much more of a spectrum than that. I have explained that I don't like the T word because of the overtones of sexual fetish, and that trans sexual was different to trans gendered, I don't want to go into the whole sissy thing. Those of us who spend time and effort thinking, reading and researching these things find it very easy to forget that to most people we are just a bunch of blokes who like to wear dresses.
Update ~ it is now Tuesday evening and I have spent the day working with S, although neither of us spoke directly about our conversation on Sunday afternoon, S did refer to something that is a part of her life which I didn't previously know about, but that she expected me to understand following that conversation. I also made some comments about my lunch and shopping trip with P without mentioning what was wearing or what I bought, but I think it was understood. It looks to me as if all is going to be just fine, I'm glad I told her.