I was trying to think yesterday whether I've ever read a story where the usual teen-age (give or take) male dweeb -- shy, introverted, socially clueless -- after finding it necessary or desirable to live as a girl or young woman for a time, discovers that having done so allows him to fit in more confidently as his male self, able to be more assertive, recognize social cues and better understand other people's reactions and behavior.
(FWIW, the hero starts off as inept, not cretinous; Aunt Jane and other petticoat punishment or humiliation scenarios don't count.)
I was surprised that I wasn't coming up with anything off the top of my head that solidly fit that pattern. I can think of a couple on StorySite, Emmie Dee's Forgetful Frankie and Hebe Dotson's Round Trip, that are in the ballpark, so to speak, but Frankie's a preteen who hasn't reached the potential relationship stage and Dotson's Bob doesn't have social difficulties to overcome.
I feel as though there's an author or series that I'm completely overlooking here. Anyone know?
Well, the OBVIOUS one
would be Tuck, in my opinion, since much of what you talk about here applies to that story, at least for the time being.
I've seen quite a few stories where crossdressing led to a boy becoming more socially adept and attractive, but it was usually as an interim phase before an eventual transition to female.
Melanie E.
I Wasn't Considering Tuck...
...though as you say it does meet the conditions I ended up with above. And Tuck may be the reason I thought it was a more frequent/iconic story device than it's turning out to be.
Trouble with Tuck in this context is that it seems clear that his situation remains a temporary one. As much as he'd prefer to avoid a decision and stick with the status quo as long as he can, his body is on a timetable of its own and staying in between doesn't seem to be one of the choices it (or medical intervention) is offering.
Eric
back and forth
How about Camp Kumoni by Anistasia Allread. It's long, and unfinished, but at the last parts, he, no she, no he was a successful male. And a good read
Princess and the Jock
I liked the saga too.
It's hard to say, though, whether A.A. was really taking the story in that direction, since two plots -- one male five years later, and one female in Erika's present -- were being overlaid on each other, with the strong implication that they weren't both true. But in any case, we'd pretty much stopped getting the male version about halfway through the existing six chapters of book three.
The problem I had with that ending was that we'd spent about 100 story parts trying to figure out whether Eric was choosing his Erika side because his life as "the Plague" had been so horrible or because he really felt female inside. Having finally answered that question, to throw it back open (even though the story had found a way to explain it, which I'll omit here because it's something of a spoiler) seemed a little annoying to me.
Eric