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First Time Out Crossdressing

Harold sat on the bench with his heart pounding in his chest. It was his first time stepping outside in broad daylight dressed as a woman. In his mind, he went over everything again to calm himself that he hadn’t forgotten anything. He had remembered to put on the red lacy bra and silicon breasts, and his cotton panties were comfortable and holding everything in place that need to be out of sight. His black pantyhose were clean and without any runs or tears in them. Beneath the soft nylon, his waxed legs were smooth and hairless. His skirt was just short enough to show some knee and thigh, but not too short to attract unwanted attention. He went over again the lengthy make-up procedure he had gone through to give himself a smooth feminine face. His wig was attached, combed, and sitting comfortably on his head.

There was no reason for anyone to think he was anything other than a young woman sitting on a bench yet he felt like everyone in the busy street was staring just at him. The walk into downtown had been terrifying, every step taking an effort to not pick up his skirt and run for safety. But with each step, he noticed how little anyone seemed to notice him. He had promised himself five minutes sitting on the bench, but when that deadline passed he forced another five minutes and then another. Men and women passed him by and he dared not look them in the eye at first. Little by little he raised his head and looked around him and was glad that no one seemed to be paying any attention at all to him. Finally, after half an hour, he got up ready to head for home. As he stood up a large burly man bumped into him as he was passing the bench. “Oh, sorry Miss,” he said smiling at Harold and then continued on his way without looking back. Harold was so relieved his knees nearly gave way but after a few moments, he gathered himself together, smiled, and walked home, his steps now much stronger and more confident than the journey out. He had done it! He had been outside during the day as a woman and now he couldn’t wait to do it again.

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