Cross dressing by a man who is not genderqueer (that is, someone who does not feel a dissonance between his subconcious sex and his physical body) has two possible political meanings
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I just finished reading a young adult novel called 'Parrotfish' in which Angie, a 14-year-old girl comes out as a transgender boy named Grady in a slightly left-of-center upper middle classish suburban high school. One scene discusses in depth the issue of cross-dressing - it's a few weeks after Grady has officially come out as transgender, and his peers decide to deal with their homophobia by putting on a display at the pep rally where footballers and cheerleaders switch clothes and stuff shirts and pants with gelatin-filled balloons and rolled-up socks. Grady goes through a similar internal discussion (pretty sophisticated for YA lit I'd have to say) about how their performance reinforces male cisgender privilege rather than displays a position of alliance with Grady
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