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It hurt so bad and we still hadn’t begun the actual fucking. He pulled all but an inch of his dick out slowly. I could feel my ass muscle gripping Jimmy’s cock for dear life - the exact opposite of what it should have been doing. I put my face in my hands and cried and he pushed his dick back into my ass. He was way too long and thick for this, I told myself, yet didn’t mutter anything other than cries and gasps. Then, as if a switch was flipped, my anus relaxed. The muscle loosened and Jimmy could feel it. He began to pump, his dick stretching my ass. My stretched ass now welcomed it. The lube was doing its job as he smoothly slid in and out of my ass. It still hurt, but it was transitioning to a pain/pleasure dynamic, if there is such a thing. He pumped harder and harder as I reached between my legs and rubbed my clit. I could feel a wave coming within the depths of my body and it crashed with what I’d call the most intense orgasm I had experienced. I was crying -. . make some kind of play. Quietly, I got up and went over and sat down next to her. "What are you reading?" I asked."It's nothing really, just a romance story," she said. "See" as she showed me the cover. Looking, I could see a white corset sitting on a love seat and the title, The Plantation Owner's Daughter. "From what I could see as I walked by, you looked to be enjoying the read." I said. "Yes! I like it a lot" she responded. "Anyway," I said "my name is Paul. What's yours?" "Anna," she told me."So," I grunted "where are you headed? And all by your lonesome I might add." "Oh, San Diego and yeah, all by my lonesome. I got divorced about two years ago and have been playing the singles game ever since. That's okay though, I'm loving it!" she said "what's your story?" I'm off to San Diego too, although I never made it to being married. Always been more of a spontaneous singles guy myself." I said as I boldly reached over and put my hand on her thigh. When she made no move to remove.
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