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. I was pressing her boobs over her clothes and she was breathing heavily and asked if we can go into your room? ’cause everyone is asleep and no one is gonna know.I took her in my arms and kissed her then we headed towards my room and I softly made her lie in bed and locked my door then we started to smooch and started to remove our clothes one by one then I asked her wait for 2 mins. Then I opened my cupboard and went to the kitchen to get some ice cubes! Then I came back in and she was looking. More

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