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IMO, it is just fine for a little boy to ask for a dress, for someone to give him one, and for him to play in it as he likes. But we've now reached a place where such a thing is like quick feet or "piano fingers," a hook for neurotic, over-invested parents to hang a heavy hat.
The hard Qs I think you're pointing at trouble me. A kid can decide (as a function of his own interests + peer group, etc, to degrees impossible to tease out) that he'd like to try drag. Should he be stopped, knowing that *other* adults will exploit him to signal their own stuff?
What *I think* is clear is that the moment a little boy performs publicly in drag, the perception others have of him, the language and feedback that surrounds him, and the amount of attention he draws will dramatically transform in ways that are *very* sticky, for better or worse
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