So I thought I liked where this was going. So I went out and bought a skin tight red leather dress that you could just see the bottom of my ass in and some red high heels to give me some height because I am only 4'11". The night of the party came so I had to sneak out of my house so i didnt get caught. I had to walk 2 blocks from my house where Jake picked me up. He was in shock by my clothes that he couldnt stop starring at my chest and legs when I climbed in his car. On our way to the party all we could talk about was how drunk we were going to get and how much fun we were going to have. Then out of no where he layed his hand upon the top of my thigh and slowly caressed it gliding across my nice, smooth skin slowly working his big hand to my inner thigh. I couldnt help but get an urge. I looked up at him and he turned his head and smiled and I grinned back. My pussy started to get damp as he moved closer to it and then as soon as his fingers touched my clit I was dripping. I stopped every now and then for various reasons, but the urge from deep inside me always calls me back. It is late 2017 when I start crossdressing again and this time it was very different. I was watching a porn video of this beautiful crossdresser being fucked and I felt this feeling like none other before. I realized that I would love to let a man have his way with me. I have been fucking myself with dildos for years and I now was intrigued about having the real thing. One evening I put together some sexy photos and posted them on Craigslist….( I miss that site ). Basically, I wanted to find a date for new years eve and bring in the new year as a woman. I received many replies but only a few stood out. Of the few there was one that made a great impression on me. He was single, 48, 6’1” and had a body type that I was looking for.Over the next few weeks we flirted and as the new year drew closer I began to get excited that this was really going to happen……. fast forward to new years.
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