Tim finds out his long-time “innocent” childhood crush Alice has been secretly meeting with an older man. Humiliation and shame brings out the sissy in him, and Tim escapes by becoming Penny after transformative night from being dolled up by stolen make-up, clothes from various women, including Alice and Tim’s very own mother. Penny gets revenge on Alice the only way a sissy knows how, seductive revenge, and soon becomes addicted to the thrilling rush of crossdressing and the associated suspenseful, risky sissy experiences.
But Penny is soon caught, and her dirty little secret is soon out of the bag! How does she keep people quiet? How does Penny feel about herself, her identity, and her sexuality? Does Penny go crawling back home to beg forgiveness or start a new life? Will she continue on her sissy journey or go back to her miserable, boring life living as a male?
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