A woman in a gray suit, her legs clad in Wolford tights, sits alone at a round marble table in a dimly lit bar, holding a glass of red wine—a quiet evening reminiscent of nights at Pink Punters.

Meet Katherine: A Boomer Sissy on Acting the Role, Cousin Fantasies and Sixty Years of Self-Discovery

Katherine is a Boomer sissy from the US who’s been quietly figuring herself out since the 1960s. Her answers are reflective, a little philosophical, and wonderfully candid about the lifelong relationship she has with her own femininity. Here’s her story, lightly edited from her 2025 Crossdresser Survey responses into a Q and A.

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