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We agreed to have dinner at her place after some small talk. I went with one intention. It was quite obvious in my attire. I showed up in black pants and a black tank top with a bottle of Jameson. Her place was decorated in a retro chic Austin Powers type of way. It was quite flattering. She had a white piano as well. She smoked way too many cigarettes and her place smelled like she was in denial of that fact. I wasn't. She flirted and asked why I bothered with dinner with her with myself looking so fine. I honestly wanted some mature pussy and we'd hit it off enough via chat. I could tell that some BBC would get her week along just right. Gertrude cooked shrimp over rice. It was mediocre but I appreciated the effort for sure. I could tell she was sweet beneath her business executive exterior. After dinner we sipped whisky and talked. As we came to a brief silence she propositioned me, "so what'll it be? Bedroom or dessert?" I quickly chose Bedroom in my tipsy yet focused resolve. We. When he asked me again I said that I did it almost everyday when I was alone. He asked me what I did and I told him. I even told him that I had my panties on then. What he said next surprised the hell out of me. He asked me if I would like to wear Girls clothes in front of somebody other than a girl. I was thinking about it when he said he had some of his daughter’s clothes at his house for when she comes and visits him. He said I could wear them if I liked. I decided I would love to. So I went to the room he showed me and got dressed in a little school girl outfit. I had a plaid skirt (pink and white) a white blouse with pink bra and pink thong panties. I felt like I was a real girl. More than I did when I left the house this morning for work that morning. When I came out of the room John had just stared straight at me and told me I was beautiful. I felt very beautiful standing in front of a boy. John had me lay down on his bed while he kissed my body all over. I.
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