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Notes -
Maybe. It implies either a sincere interest in permanently abandoning their current sex, or a sincere interest in joining the other sex, but not an indifference such that changing would be no benefit, because it would follow that remaining would be no worse. But also an interest that isn't strong enough to accept the substitute of even temporarily changing gender.
It's a little like trying to think of someone who would enlist but wouldn't wear any camo that wasn't issued.
I suppose the men who want to transfer to women's prisons might qualify. I can't think of any others. Faildaughters of nobles in primogeniture jurisdictions, perhaps?
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