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Plus I always thought she was just so darn cute, even as the nerdy girl from high school. I was at her office a couple weeks ago, going over the insurance on our new car, when it hit me again how she lovely she was. She was wearing a conservative gray skirt and blazer, with her silky orangish redhair modestly tied back, but still radiated a certain sexuality. Maybe it was her quiet demeanor and lovely innocent smile, or maybe it was her beautiful toned legs that were highlighted even more so by her short skirt. Or just maybe it was the plunging neckline that was a surprising contrast to her unassuming gray suit. I was staring at her cleavage, wondering if this reserved woman had a boob job or actually had big natural breasts. I don’t remember her being that busty back in school. She caught me looking and just smiled at me while sucking on her pen as she was reading through our policy. She repositioned herself to give me a better view, and I swear she had nothing on beneath the gray. ” I was scared and as he felt on my ass he said, “This time, really try to relax, especially when I am in you."Nodding my head, he told me to put my head down on the pillow again. As I did, he again fingered my ass with KY, and then immediately tried to push his cock in my ass. Again, it hurt and I tried to have him take it out, but he refused. It hurt so much and when I tried to pull away, he held me by my hips keeping his cock in me. It was painful, I couldn't do it, I quickly pulled away again, which pissed him off.In a frustrated voice he said, "Come on, what's wrong now."I again told him that it hurt, and in a huff he said, “You have got to try to relax.”I hoped he might give up trying but when he again said, “Let me know when it stops hurting,” I realized he wasn't going to stop trying until he got to fuck me. The pain had subsided, and moving closer, he told me again to relax. I had to relax so he could fuck me but as he again pushed his cock in me, it started to hurt the.
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