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Jennifer checked her watch and noted he was ten minutes late. She smiled as she noted, that she had done much to make his life better too…mostly in ...he bedroom. Their first two meeting had been chaste evenings …dinner at two of the finer restaurants in town…Jen could see the lust in his eyes but soon realized he didn’t really know how to even broach the subject of sex…with a woman. He was a widower who lost his wife over a year ago…not really a player. After their second dinner and his. James began to contemplate again what it would be like to have something inside it. He decided to try it, just one finger. It can't hurt, and he could stop if he wasn't enjoying it. His hand moved away from his balls and cock and began to gently rub his hole, making it moist with sweat. He took his middle finger and tried to slide the tip in. It hurt, it stung, but the tingles went all the way into his balls and he loved the feeling it left deep in the pit of them. He wanted more. He had to. More

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