It was late on a Sunday night, and wickedly cold outside (minus 30), but as we began to 'text' back and forth, she made it clear she was up for some company. I told her I was great at giving massages (an exaggeration) and, when asked, told me she was wearing silk panties.I was a little nervous about being set up, but my horniness prevailed, but when Dierdre (made-up name) gave me her address and invited me over, I threw all caution to the wind. About half an hour later, I was at her front door, wondering if I should knock. Once again, horniness prevailed, I knocked, and she opened the door,Dierdre had a room-mate, but he was gone for the evening. She wasn't especially attractive. A bit dumpy, in her 30's, with shoulder-length black hair. She was wearing blue jeans and a red t-shirt, She invited me into her cluttered living room. I sat on the couch, and she at a table with a computer. We made small talk for a few minutes, then, gesturing with my hands, offered the massage. Dierdre. I looked at itand noticed how small the skirt was and the thought of me wearing it wastoo frightful to contemplate. But then this voice in my head told me Ididn't have any choice.I started to wonder about those statements Pete made during our argumentof me having such an easy road to wealth and happiness. Was he right? Wasmy Stepmother going to help me marry into a super rich family? And then Irealized it would be humiliating at first to wear the mini-skirt aroundthe house but I figured she'd get bored with it, and when cold weatherarrived in the fall she would understand why I was back in my maleclothing. This whole crossdressing thing would blow over if I used theright strategy.The next morning I shaved my legs and if it wasn't for my optimistic viewthat I had a handle on the situation I would have looked at what I wasdoing and thought I had gone insane. After shaving my legs and putting onthe mini-skirt, I walked downstairs with the knowledge that I was facingmy Stepmother for the.
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