Yes, as it says on the tin, I’m going to tell my friend that I’m a crossdresser. Because both of our work schedules are bugger all, it has to be that weekend after this coming one [September 3], which is great, as it gives me two weeks to stew and fret. The purpose for our meeting is really to talk about our road trip to New England this October, but my crossdressing is supposed to be a significant part of it. One of the reasons for the trip [of which there are around thirteen] is to boost my self-confidence, to break me out of my shell of self-loathing and cynicism, and my wearing women’s clothing is a crucial part of that to me.
I just have no idea how to play it out. Do I say it outright or kind of ease into it [no, I don’t know what I mean by that]? Do I talk about the trip while writing it out for him to see [which seems kind of stupid, but that was Plan A]? I was hoping someone might have some kind of suggestion or advice.
I’m not really worried about his perception of my bisexuality; that rumor was in circulation during Senior year of high school. That fact that he still talks to me is answer enough that he wouldn’t care about that, and that he’s decently open-minded. It’s just the crossdressing I’m not sure about, whether I should just leave it for when we get to our destination.