Jill is masculine-looking and attracted to women.Jill cross-dressed as a prepubescent and adolescent and found it sexually exciting.Jill underwent gender reassignment surgery at the age of 42.Based on the descriptions in your text,Jill is most likely

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Jill's description suggests that she is a transwoman, as she was initially masculine-looking, attracted to women, and found cross-dressing sexually exciting. Her decision to undergo gender reassignment surgery at the age of 42 supports this interpretation.

Jill Is Masculine-Looking and Attracted to Women