Room and Board
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James, a college grad student takes a job as a housekeeper for an older, very attractive woman, who pays him a salary, plus room and board. He discovers that his employer is unlike any woman he's ever met and, as he later learns, prefers her young men in panties. She slowly feminizes him and helps him discover that he is a sissy.
Things are complicated when he meets and falls in love with a young woman his own age, Lisa, as he is torn between his infatuation with his employer, who knows he is a sissy, and his love for Lisa.