This is an unusual story in that the cross-dresser is not the viewpoint character. I’ve probably done this before (I’ll refrain from trolling through my archives to find examples), but it definitely isn’t the norm. But as you’ll see, the theme of this story makes it necessary to tell the tale from the point of view of a young man who isn’t quite sure whether his date for the evening is male or female. But there are times, in the service of other goals, when maybe it doesn’t matter and it really is better not to know—even though he’s pretty damn sure she isn’t. Female, that is. (You knew that, of course.) Enjoy!
This story actually hearkens back to a vignette I wrote nine years ago: “Empty Nest” from 2009 (near the bottom of the list). It was (very) loosely based on a personal experience, which thankfully (or sadly, depending) did not result in my discovery and being forced into feminine garb. You can think of this vignette as a sort-of follow-up to the 2009 vignette, wherein events are taken to their logical conclusion.