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Sissy (transgender) - wikipedia, the free encyclopedia, In "sissy role play" a sissy is a person (typically a man) who adopts hyper-feminine behaviors, and engages in stereotypical "feminine" activities (e.g., housekeeping. It's sissy boy saturday! via petticoat discipline, It's sissy boy saturday! via petticoat discipline quarterly plus jane's story via jane. M missy’s series of book - the sissy maid missy series, Interesting, entertaining and arousing… experience a distinctly satisfying literary adventure through m missy’s books! delve into more than 20 books from four.