I may have touched on this subject before (really?), but this is could be described as a cautionary tale about a cross-dresser whose unfettered desire to emulate a woman gets him into a wee spot of trouble. This, in a nutshell, is the difficulty cross-dressers have: our aspirations to womanhood are undeniable and intensely pursued, but for most of us are almost impossible to realize. Frustration, thy name is cross-dresser! So when, as in this little tale, someone comes along with the full intention of making us live up to our own hopes—to walk the walk, as it were—it can be a shock to the system to find oneself in strappy heels and a slinky gown, about to make that fateful step out into the world. Enjoy!
Oddly enough, I wrote this caption back in May and then forgot about it. I wasn’t quite happy with title or the wording at the time and it got lost in a folder with about three hundred files vying for my attention. The stuff I’m actively working on usually gets moved up a level to make it easier to find, but for some reason this one didn’t make the jump. When I stumbled across it again yesterday, I was able to finalize it with only a few minor edits.
This caption is reminiscent of any number of others, so I’ll just mention “Like Never Before” from 2016. Oh, and “Disbelief” from 2015, because I haven’t mentioned it in quite awhile. There are lots of other examples.
P.S. This is a very large caption, so here’s the JPG file for your collection (assuming anyone out there saves these things). Click on the above icon for the PDF version.