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The saga of the ongoing feminization of Bob continues, with even stranger turns of events than before. He is torn between his love of womanly finery and his attraction to girls. To his mind, why should the one interfere with the other, even if society deems it forbidden. Even though he adores wearing skirts, dresses, panties and bras, he doesn't enjoy being forced to do it by his female relatives.

His financial obligations mean that he is stuck in his current predicament, however. In parallel to all this, the guys Bob used to pal around with are finding his Cindy persona
very attractive. Could things possibly get more complicated? Why yes, they can and do. The prettier "Cindy" becomes, the more out of control Bob's life becomes.
He's even forced to work as a woman! What's next?

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    I knew Mme. Norman had not read me and as the luncheon progressed, Leslie mentioned that I was looking for a way to stay in New York for the winter.

    Trina Norman offered me a modeling job on the spot. I demurred, telling her I would let her know.

    Here was a daring and dramatic answer to my dilemma; perhaps too daring, too dramatic. Leslie encouraged >me to take it. I hesitated. I wasn’t sure that I was ready to take up a transgendered lifestyle.

    The Lockmans encouraged me to take it if I felt comfortable with it. That was my sole hang-up. Could I get comfortable with the sudden reality of entering a life entirely as a female? The idea both thrilled and appalled me. I didn’t discuss it with my family at all. I had decided to make my own decision. However unusual it might be, it would be mine.

    Then one evening about three weeks later, when I was not dressed, Dr. Lockman took me into his study, poured each of us a double shot of his rare Scotch single malt whiskey and talked to me like a Dutch Uncle.

    “You are a transvestite, my boy. You always have been and you always will be. Believe me, I know! In my long years of psychiatric practice, I have never met a crossdresser that wanted to be, or who could be ‘cured’. It is a condition that befalls certain of us and never goes away. I also know it runs in families."

    With this last remark, he peeled off his brocade smoking jacket, loosened his tie and unbuttoned his shirt to reveal a lace-trimmed camisole.

    I was astounded!