Chloe needed a ride home, and I was asked to do the honours. A sixty year old guy driving a thirty year old woman home was thought to be a safe bet."W...y?" she asked."You are a beautiful woman. I was mentally undressing you" I admitted knowing that I would not be seeing her after this car journey so I had nothing to lose and everything to gain. Hopefully not a slap to the face I hoped."Why me?" she asked again quite calmly. I expected her to be screaming at me, calling me a pervert or something. Her shoeswere arranged in a line on the floor by heel height and then boots. Icouldn't believe that her closet was organized like a department store.Girls certainly are neat I remarked to myself. This was my first timedressing myself as Jenny and I wanted something simple, so I decided ona skirt and blouse. There were lots of different styles, lengths andmaterials to choose from. I tried on a few just for fun. Boy's clothesdon't button and zip in back, so I struggled for a while until Ifigured. I teased her about looking at them and she blushed and denied it. After the swimming she went out to do some shopping at the nearby mall and I went online and found a male escort service that did couples. One of their escorts was a young black guy who looked like the ones we had seen at the pool. His ad indicated that he had a photographer who could take pictures during the evening for our enjoyment later. I called and arranged for him to come for about eight PM and when he called back to. I sat down on sofa and enquired about her child. She sat opposite me and enquired about my wife. I told her that she had gone to her mother’s house and would be back late in the night. After this i left her house though she offered to pack some food for me. I again masturbated after reaching my house. She was really getting on my nerves. Next day she again telephoned me at office and said that she had forgotten to give me money for medicine. I asked her not to worry now but promised to collect.
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