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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. Top tips for sissy maids | crossdressing tips, Ing: 0.0px;”> to that end i invite all sissy maids out their to send in your “top tips for sissy maids”. it could be about something that you do that is going.