That was the beginning of my journey into Crossdressing.I think I was about 8 and the school I went to was having a Halloween fair the evening of Hall...ween and I wanted to go. I went home and told my mom and she asked what I was going to go as and I said I am going as a cowboy. She smiled and then she took my face her hands and looked at me and said I think you would be a much prettier girl than a cowboy. I was thrilled but scared and said I would not do it but in my heart and wanted to do. Here was this cute brunette about a third my age coming on to me. After dessert and coffee, I found her sitting outside on a truck tailgate by herself and strolled up to her. She said, "You are the nicest man here. You have been so very nice to me and made me feel very much a part of the family." I told her she was a beautiful girl but it was hard to see much of her with the long denim skirt and heavy sweater. She pulled me close and kissed me softly. It was kind of like a thank-you kiss. I. More

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