Because when it happens, especially the last, when you're dressed like a woman and when you squirt with her cock buried deep inside you, when cum dribbles out of your chastity caged penis, she'll know, however much you deny it, you LOVE to be fucked dressed and fucked a woman.
It's a defining moment because she will understand that NEVER again will she have to allow you inside her, NEVER again will you be allowed to fuck her, NEVER again will you cum without her cock deep in you.
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