Here’s a conundrum most guys don’t have to deal with: you’ve got yourself a pretty sweet girlfriend, you’ve been dating for awhile, and then she hits you with the news that she could really only get serious about dating a cross-dresser. (If only, right?) So whaddya do? Well, the hero of this tale, despite never having cross-dressed in his life, swears up and down that he is in fact a cross-dresser—and then has to put up or shut up (and lose the girl). Of course, it turns out that he’s really really good at it (if only, right?) and events develop from there much as one would expect (or not; you’ll have to read it to find out for sure). Enjoy!
I don’t recall writing anything with this premise before, so I’ll just refer you to the first story that springs to mind (for whatever reason): “The Game“, from 2014.