I told the clerk that I needed to get my "niece" a few pairs of shoes and we spent some time on picking out a pair of flats and a pair of Mary Janes and a pair of heels with a demure one inch heel which she and I agreed was the best for a young girl to start out in. Then, we went into a department store and we picked out a selection of panties and bra's, some sox; anklets, knee highs and a couple pair of tights, stockings and a garter belt and a couple of nighties. The clerk was very nice and she helped fit Bobby's new bras, reassuring my Niece" that she would be filling out in no time. Then we wandered over to the Junior Miss department to picked out a couple of outfits. After having Bobby try on and model several, I decided on a simple school girl kind of outfit with pleated skirt, white blouse and blazer, a more casual skirt and blouse, a dress with A-line skirt. We stopped at the make up counter and I had the girl there give Bobby a make over and she was so happy to introduce. Deb had explained that she had been with couples and just women and really enjoyed the experience, especially if the other woman was new to it. I told her I would contact her as soon as I could make the arrangements. About 2 weeks later, the time was right. My wife was going away for a weekend and Ellie had arranged a “girl’s night” with her husband. Ellie knew I had something planned but did not know what. She thought this might be another one of our standard sex filled romps. She was right, but if all went well, I would be watching this time around. Ellie and I made our way to the hotel and got checked in. We decided to get cleaned up and head down for some drinks. As we drank and talked, I noticed Deb had made her way to the bar as planned. Both she and Ellie were looking very hot. I was wondering if I would be able to just watch later. Time would tell. After a few more drinks, I convinced Ellie it was time to head back upstairs for some fun. As we walked through the bar to the.
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