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It was my smallest and I knew it would fit in easily, but I wasn’t out to be cruel to the girl. This was just the next part of her education. I still had a coating of lube over my fingers so placed them back on her anus and spread it around. I tried to work some inside, but she tightened up as I did so.“Don’t be silly, girl, try and relax. Don’t fight me, it’s going in if I say it is.”I slipped the plug between the cheeks of her arse and then played the pointed end around her hole. She was trembling as I started to press it into her and she gave a little sob which I ignored but which only made me take my time. I watched as it slowly entered her, and she expanded to take it. Millimetre by millimetre I pushed it inside her. When it was about half way I took it out and then started again going a little deeper. I kept teasing her until we were on the brink. I stopped pushing and just held it there allowing her time to adjust before I let the widest part breach her virgin anus. She. Finally we were seated and were half way through our meal, and in my case my third martini, when they walked in: Jennifer and her escort. He was at least six-five and very handsome and, I thought, at least ten years younger than Jen. All of the old feelings came back to haunt me. Sylvia noticed. She also noticed who had caused it."Someone you know?" she said."Yes, the woman. She's my ex," I said."Oh my. Are you okay? You look upset." She said."Truthfully? No, I'm not all right. The whole thing still bugs me," I said. "Would you mind if we went somewhere else?" I said."No, of course not," she said.I signaled for the waitress. I handed her a fifty and we began to make our way out, but Jennifer and mister whoever were too near the door for us not to be noticed."Harlan! I didn't see..." started Jennifer."Hi, Jen, we were just leaving; have a nice evening," I said, helping Sylvia with her coat. The man with Jennifer looked perplexed—at first—then amused. He could see something was going.
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