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Tim avoided jail to opt for house arrest, but the woman in his new life is determined to turn him into a woman. On female hormones as part of his sentence and under the control of his benefactress, her daughter and the female staff, they slowly feminize him. As much as he hates it all, he is just so turned on by his clothes and his new life, that there seems to be no escape.
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    ...Janice was the expert in getting me to make big changes in little increments so I didn't even realize how much I had changed, how much I was acting as a girl would by the end of it until it was over and too late.

    And then of course I had to talk with Janice in front of Cookie like we did at the beach, like I was another girl. And then as Cookie continued to join in, I had to stay in my girlish mode. And then finally Janice told me, that I needed to drop my mannish mannerisms all together around Cookie, that there was no reason to act macho. At that point Janice just expected me to act as feminine as I did on the beach or she would have me wearing my lipstick in the kitchen as a reminder. And so the soft mannerisms, not so much feminine at that time that I had adopted when with Janice at the beach became my general manor of carrying myself when in the kitchen.