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At one point I wrote to a lady who lived further out from the city and more in my general direction. I liked her reviews and although she was massage only, no full service, I found her intriguing. She was older, a "mature" lady, with very large natural breasts. When I wrote her to see if she owned any boots she responded that she didn’t but had been considering getting some. This led to a rather extensive email exchange of getting acquainted, and we also chatted quite a bit on google during the day and evening. During this time, we began planning a shopping trip to Woodfield Mall (near where she lived) to find her some boots, my treat of course. At one point during our conversations she mentioned a leather mini-skirt she owned and that it was "fun". I remarked to her that it was probably a little much for a day time shopping trip and she concurred but said while that was off the menu stockings and no panties quite likely were.Finally the day arrived, and I drove to her apt to pick. “Ohh fuck yeah,” he said as he continued to push it deeper, and deeper. I was feeling uncomfortable, never before had I been fucked with anything so big, and I really didn’t want to end up seriously hurt. The dildo was in as far as it would go and it started to hurt me as it pushed against my cervix and he showed no sign of stopping. “No more please” I cried out, and he almost withdrew it completely before plunging it back into me, causing me to cry out. Faster and faster, he went now. The friction from the dildo driving me wild as it rubbed against every wall inside me. I wailed like a tortured animal as waves of pleasure began shooting through me, muscles needing to contract but having no space to do so. My juices needing to gush yet having no exit. I came with huge intensity and tears of shame, rolled down my cheeks before the pleasure had even drifted. I felt renewed warmth and looked down, as he was pumping hot cum onto my tummy. “I’ll fuck you later,” he said and winked. Simon.
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