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We had eaten on the main balcony a few times with each of us taking turns with the food and wine. I took a bottle of my better wine and headed over after a shower and change of cloths.She had the food just about ready so I asked if she wanted me to open the wine, She said it would probably be best since she was already on her second Scotch and water. I told her I like to let the wine breath for a little while so she offered me a Scotch on the rocks. She asked how my gf was and I told her she had moved about 5 weeks before to Boston. We didn't believe in long distance relationships so we parted as good friends with occasional benefits.Gail thought that was funny and then I explained we both were retired Navy. I retired shortly after turning 38 and she had retired in the last year. We had known each other for several years while in the Navy but did not date since she was a Commander and I was a Master Chief. I recommended her for a software development position in a company that I. ‘Janet, being an escort would be great. Imagine you would be paid to date out of town business men, or maybe women, on occasion. I would have fun buying you dresses and shoes, but the only condition would be that I would chose the styles and the sizes,’ I started telling her. She did not reply, but I could well imagine the images in her head. I have a wicked sense of fashion and when I feel like dressing a friend in a sexy way, I can go trashy. Janet has been a very willing model for my nasty urges. I always felt the shoes were so great, it gave her the courage to wear my selection of dresses in public. Receiving pictures of Janet in bars, restaurants or other public places as proof of her obedience was my reward. ‘So Janet, can you picture yourself, letting me choose the outfit and the shoes, sending you to get your hair and make-up done?’ I asked. Of course, I knew the answer. She had very crisp images of herself in her mind. Janet is a mature woman, a short brunette, plump like I.
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