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When a naive young man gets a job offer from a well-to-do woman who owns her own company, he feels like he has hit the jackpot. Upon starting his employment, he discovers to his surprise that his new boss also desires him as a bedmate. A bigger surprise is that she wants him to dress as a woman. More specifically, she wants him to look like her and act as her daughter.

While this is unusual, as soon as he accepts her peculiar demands, he finds that he enjoys the new role he is playing. Before long, the boss lady raises the stakes by suggesting that he might enjoy actually being a woman rather than just impersonating one. Our protagonist may feel like he is on a runaway roller coaster speeding down a hill with no botton but it's a ride that he increasingly accepts as his new life. Shockingly, even with a feminized face, a fabulous figure and breasts to die for, the new girl is to discover that there's still one huge surprise awaiting her.

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    “I would like to take our fantasy one step further. I want you to don an outfit from among my things each evening upon our arrival home,” she said seriously. “I also had two wigs custom made for you to wear, both jet black to match my own hair coloring.”

    “Two wigs?”

    “Yes, for you to wear depending on the time of the evening. One is drawn tightly back into a bun and the other with the tresses falling long and free like mine when I prepare for bed.”

    “In other words,” I said, a little breathlessly and with an insight that astounded me later, “you want to be able to look upon me, while we’re intimate, as yourself twenty or thirty years ago. I’m really stunned by this, as you can imagine. I am curious though, how you can possibly hope to see in me a replica of yourself, just by having me wear your clothing and a wig?”