Passing on a Date: A Crossdressing Adventure - Paperback

by Alan Barrie (Author)

He was 25 and had been doing it since childhood. But after his widowed mother had died when he was 22, and, in the three years following, living alone in the house in which he was raised, it had become progressively more important to him.So important that he practiced and practiced endlessly, almost every evening after getting home from work, almost every weekend. "Cassie" practiced at dressing as a woman and eventually became successful at being a woman in the world ... occasionally. Shapewear, clothes, makeup, voice practice, movement practice, searching the internet for guidance incessantly, studying the women around him compulsively: slowly she got to be incredibly good at it.First, it was just in the house. Then it was walks in the evening in her little town in southern Indiana, but always in a quiet neighborhood far from her own. Eventually, he would travel to cities around the state so Cassie would have the opportunity to leave hotel rooms for hours at a time: shopping in malls, having lunches in restaurants, drinks at hotel bars, trying on dresses in department store fitting rooms, attending meetups of like-minded girls.Without anyone detecting her secret, she could talk to salesgirls and waitresses and bartenders. She could have conversations with the other women at the hotel bars and even fleeting, flirty ones with men. At some point, she came to know that others found her pretty in a small town, midwestern kind of way.But never before had Cassie been Cassie for more than a few hours at a time.But then, after planning it for months, Cassie left her house as Cassie, headed to the train station, headed to a three-day weekend in Chicago. In her purse, Cassie had credit cards and ID in her full name, Cheryl Ann Sanders. She had a reservation in a fancy hotel in that name also. She had girl's clothes, and only girl's clothes, in her suitcase.She expected three days of shopping and of museums, of dining out and of theater, of long walks and quiet times as a girl, as a young woman in the world.What she didn't expect was that she would meet a man on that train. What she didn't expect was that she would find him as attractive as she did. What she didn't expect was all the time that they would spend together that weekend.What she didn't expect was romance. What she didn't expect was passion.What she didn't expect were the astounding things that were to happen to her that weekend.