I am sure this topic has been addressed... but since I've come out to myself, crossdressing has entered my dream time - often they've been situations where I've been caught out and left struggling to deal with the awkwardness that ensues.
Most recently, I dreamed I was to attend a wedding, ostensibly invited to act as a mature settling influence among many youngsters. It seems trouble was expected from bystanders who might feel the ceremony should not take place.
(read into any of this what you will)
Unexpectedly, I find I've arrived at the wedding not in drab but 'dressed. Quickly I remove myself from the awkward looks and find a bathroom to hide away. I look in the mirror and sure enough, I'm well dressed in a red suit- skirt and jacket, with my face well made up but I've a mustache that is totally blowing my look/cover.
I look by the sink and find what I perceive to be a razor and start to shave. Actually, in retrospect I recognize it was a variation on an epilady; one of those hair plucking coil spring apparatus'. Watching in the mirror, I use this to 'shave' with.
Once done, I return to the gathering but it's obvious from the looks I'm getting that my actions to remove the offending facial hair were much too little too late.
The dream ended there with me feeling awful that I'd put myself in such a situation.
In retrospect, I relish how nice I did look and how I enjoyed the outfit, that it was such a shame I couldn't have enjoyed the gathering as I was dressed.
I of course also still feel the inner pain of the rejecting looks from the others around me.
This story is just a vignette but is most recent and quite vivid. At one point in the dream I'm walking up a spiral stair to the bathroom and my perspective is well outside myself and I can see how nice the outfit looks, and can in fact see my feminine self which is many ways so unlike my true, physical male self.
I could just dwell on the embarrassment and pain that go with the entirety of it, but again there are flashes in there that I take as all together positive - visions of how I really see or feel rather than the 'truth' the mirrors in my world reveal.
Again, it's just a dream but it was so vivid, the memories left are rich and detailed. I wanted to share this, perhaps to generate some discussion. Mostly, it was unpleasant in theme but as in many things I'm finding positives to cling to as well.