GameTheory: Drew isn't genuinely trans and has been manipulated by Hunter.
We see in what if 7 that Hunter both likes to have someone manage his girls and doesn't mind sharing with said manager so long as they don't knock up the girls.
We know from chapter 11's bad end that Hunter is capable of manipulating someone into believing they are trans.
We know that Drew has been Hunter's sidekick since Hunter's exile and helping him take over families. Only transitioned during this time, conveniently keeping his hog but removing his baby makers.
We know that Hunter believes it's his destiny to be "
Dio del Sesso" and hates that he was robbed of it. Making it clear that he's not interested in being passed over by Sterling and therefore we can assume he felt the same way about Drew.
We know that Hunter is willing to lie and manipulate Drew, even going as far to kill her if she gets in the way.
I believe Drew got canon bad ended in the past without even realizing it. The clues are all there.
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