A bet?

I'm not really a fan of this fetish in particular, but i'll chime in an idea.

if you work out the **** angle, maybe either a mother, or a sister, maybe an aunt, ends up daring the male lead to wear womans clothes for a while, or maybe a bet that he loses and has to wear lingerie. If you wanted to, you could incorporate some BDSM and femdom to it as well. The only thing that would really turn me off from it though is if they all have strapons and use it on the guy. Other than that, I don't really have much of a problem with it.