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. With a steady, firm and continuous push Doug entered my now well lubed anal cavity once again. My butt hole was so tender that the pain was of such intensity that I could only managed to open my mouth and gasp in very short burst, for breath. Doug continued to slowly enter my anus, pushing three quarters of his steel hard cock into my rectum. Than slower than he entered, Doug pulled most of his cock from my anus and re-entered, this time sinking balls deep into my rectum. I gripped. More

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