While I'm sure his desire to live as a woman is sincere, this could also be a ploy to get a transfer to a cushier federal pen. If I was an Army lawyer or general, I'd be worried about getting involved in a precedent setting court case that ultimately allowed Manning to start his journey while serving his sentence in a military prison.
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I think she's hot, hot, hot and that gives her vagina tattoo bonus points. The cat-nose-and-whiskers, though, makes me wonder. That doesn't seem like a smart tattoo at all.

-- Rear Admiral