I instantly turned red but was really interested, Jan is a gorgeous fit, toned, and tan mid 40's housewife, and I wanted to play along and have fun. When i said okay Jan smiled at me very sweetly and got up and said "ill be right back, don't get cold feet" and walked out of the room. When Jan came back she had a handful of things and camera. I was a little nervous when i saw the camera, and what she had in her hands. Jan walked over to me after she had changed into something ridiculously sexy and hand took what she had in her hands and gave it to me and said, "now go put that on for me and call me when your dressed." I took what she had and went to the bathroom, and after tossing things onto the sink i realized what clothes she gave me. Jan had given me a pair of sexy stockings, a thong, a sexy black dress, bra, wig, and stuffing for the bra. I sat there a second looking at everything thinking... "she wants me to crossdress for her?" I had never worn or thought of wearing women's. ”, I replied. “Brian, I have given this quite a bit of thought. There is absolutely no way we could live together as man and woman. This town would go crazy, I am sure I would lose my job at school. People would think that something had been going on between us for years. I just can’t take that chance.”, she said softly. “So we move Ashley, no big deal. If I get drafted next month, I am leaving anyway. Come with me, no one knows us or our past. You can teach anywhere, you’re certified.”, I answered. “It’s not that simple Brian. I like it here, I have tenure at the school. I’m not sure I want to leave here.”, she told me. I was getting frustrated and I was getting there fast. I didn’t want to get upset, I didn’t want to come across as a child to Ashley, in fact that’s the exact thing I was trying to avoid. I wanted her to see me as a man, one who loved her as a woman. “Ash, I have to be honest, I’m not sure I can continue to live this way.”, I said, sincerely.“I don’t quite know how.
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