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Who is going to know who in the heck you are. Or if I were to pair the pic with your name on Tumblr… which is crawled by google and thus if someone were to Google your name for whatever reason, they could easily come across your nude pic. From the description, it seems that the forced transformation blackmail contract goes a step further then the forced feminization contract.
You start it similarly, bring him and yourself to the edge of an orgasm, and you throw a coin, if you win you lock him back in without cumming, and finish yourself off (or him finish you off), and if he wins, you pull your sexy panties back on, and finish him off.