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A prison pillow is an annoying and [extremely] [effeminate] gay man. Often the man in prison who is used to vent other inmates sexual needs and they often do it willingly. Generally the [stereotypical] kind you see with the inverted shirt-bra and calling other men their "Boo" and acting catty to other gay men. The kinda gay where they forget how to throw a punch and instead scream and try and scratch you with fake and awful glued on nails. The Pillow is used due to the reference "If you are feeling hot you just flip it over."
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