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I started buying my own lingerie and had several hiding places in the attic and basement for all of my sissy clothing. I would actually purge some of my things every now and then to keep my collection from getting out of control. Back when Craigslist had a personal ads section for casual encounters, I started posting ads to have anonymous meetings with other men. Simple discreet meetings where they would come to my house, find me blindfolded on all fours in the front room dressed in skimpy lingerie and heels. They would feel me up, shoot their cum on my ass, jack me off then leave. I did this for about three years a couple times a month. Sounds silly and risky, but I would get so excited and turned on being exposed to a complete stranger and used in that way.One gentleman that jacked off on me several times, expressed an interest in wanting to grope me on his way to work. By this time I was divorced and lived alone. He wanted to do this face to face. I had never seen any of the men. After begging her to let us stop at Subway for a veggie salad, we wereoff again to find a cute handbag for me to wear around the office. I letit slip that I had always had a thing for those trendy seat belt purses,so Jenn steered us right to a place that sold Harvey's bags!I left with a medium sized black purse that would match the majority ofmy new shoes. And of course I talked to her into getting me a multi-colorlarge tote as well for my lunch and any books or files I might need tocarry with me for class or meetings.When it came to makeup, I was totally clueless. So I let Ms. Jenniferwalk me down the cosmetics aisle at Target (my favorite store!) and pickup everything I needed. It didn't even occur to me that I would have towear women's deodorant and everything.By now the both of us were super tired, and I was ready for bed. Insteadof heading back to my dorm, Jennifer let me crash at her place, a cutelittle three bedroom Cape Cod near the university and The Women's Place.I really.
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