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Jackie’s eyes opened wide as she realized what I wanted, and she spread her legs as wide as she could. I stuck a couple of fingers in her sopping cu...t and ran them around her asshole, lubing it a bit, then gently pried her buttcheeks apart. I grabbed my cockhead and slipped it into her asshole and waited for her discomfort to ease.Jackie enjoys assfucking, but it does have to be done carefully. I have a natural advantage for this. I’ve got a sizable cock, but a slim one. I’m eight inches long,. Sometimes it might be necessary, like if you’re defending your family from an attacker, or defending your country from an invasion, but it’s still sad.”“Like your girlfriend from back in eighth grade.”“Yes,” I said.We lay together for a couple of hours, kissing occasionally but mostly just cuddling. When it was time for Penny to go home, I walked her to the door and watched her as she walked slowly home, stopping several times to look back at me. I waved as she went inside. My being hurt really. We found each other online. Neither of us was looking for something intimate or deep or meaningful, just some friendly conversation, maybe, but more typically, a quick romp of a sexual cyberspace encounter for some relief and release before going on with our respective lives. Simple. Casual. Meaningless. It was her fault, really. She started things out by actually talking to me, because she made it seem like she wasn’t really interested in sex at all. It wasn’t my M.O., to go into that kind of. This gave him an excellent view of my pussy still, and my asshole I think.This is when the night turned weird for a little while. He started interviewing me, asking me questions about who I am, and about my life, avoiding anything sexual along the way. It'd be like if I was getting to know a friend. Of course, it doesn't feel natrual to get to know a friend naked and exposing your most intimate areas. This interview went on for about 45 minutes before he suddenly said, "You are a very pretty.
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