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I gently worked her panties over her ass and down her legs until I was able to get them off of her. She moved around a bit until she was sort of on her side with one leg drawn up a little bit. I grabbed the KY from her night stand and gave my cock a good lubing up. Then I climbed back on the bed and moved behind her. Her new position was perfect for me. All I had to do was straddle her one leg and use my hand to lift her cheek up and expose her pussy from behind. I guided my cock to her lips and rubbed it back and forth just a little and then I just pushed into her. She was a little snug on this position and had to move my hips and then push the rest of the way in. When I pushed in the second time I heard her suck in a huge breath and groan, her hand came down and grabbed my wrist. I told her that I had been waiting to fuck her for 3 days and that she better hang on and started to stroke her with nice long strokes giving it a little sharp jab as I hit bottom. She would grunt and moan. " I took what she had and went to the bathroom, and after tossing things onto the sink i realized what clothes she gave me. Jan had given me a pair of sexy stockings, a thong, a sexy black dress, bra, wig, and stuffing for the bra. I sat there a second looking at everything thinking... "she wants me to crossdress for her?" I had never worn or thought of wearing women's clothes before but i thought this might be a once in a lifetime chance so i decided, why not try it out you never know i could like it.. After putting on all the clothes i called Jan and she came in telling me how good i looked and that i should think about putting on sexy clothes more often. I was a lil on edge feeling not so comfortable in girls clothes around really good friends of my family... but decided to go with the flow. Jan open a drawer and pulled out some makeup and said, "now im gonna get your finer girly details" and she painted me up in makeup. I was amazed how good i looked afterwards. i couldn't even.
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