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Initially, Deb was all business when we spoke but I would throw some innocent flirts with my text, such as telling her how great she looked, just to test the waters. Now being a pretty shy asian 19 year old k**, normally I would have never been so bold with such a woman out of my league, but talking over my text I figured I had nothing to lose. As our working relationship grew, Deb would start to open up to me more and tell me about more then just work. I learned Deb married young and had a 18 year old daughter that had just given birth to a daughter of her own. Now only was Deb my teacher sex fantasy, she also became my milf, gilf, and married woman fantasy rolled in one. Deb also became more receptive to my more elaborate flirts as I began to tell her how much guys, including myself, fantasized about her.The day of the concert it was snowing pretty hard so our shuttle job became as important as ever. Though simple enough in idea, we came up with the logistics to really make these. A buzz sounds and the door pops open, i walk inside.The hallway is dark, a curtain separates the vestibule from the rest of the flat. A red light perpetrates round the edges, clearly showing me where i am. I large sign on the wall displays my instructions. It says "Strip Naked then proceed".I remove my clothes and hang them up. Despite knowing what is coming, my penis is getting hard, very hard. I move the curtain aside. My mistress stands before me. She wears a long black leather skirt, with a long slit up the side, i can clearly see her boots and stocking tops. She wears a white blouse, clearly displaying her black corset underneath. Her long brown hair is in a french pleat. She wears a collar and long black silk gloves. Oh such a heavenly sight.She points to the first room, which i enter. Its a medical setup, gynacological examination chair sits in the middle, i'm told to get on, but i hesitate. I feel a sharp pain across my ass, then again and again, i cry out in pain and leap.
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