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Billy’s parents were planning to go to Clemson, SC to attend an alumni cocktail party and dinner. Although they would leave on Saturday morning and return late Sunday, they asked that we keep an eye on Billy until they returned. Alice Wilson had prepared a casserole meal for Saturday night and Billy was instructed to prepare his own breakfast the following morning. Even though he was a teenager and fully capable of caring for himself, they said that they would feel better with the neighboring adult couple in charge. The afternoon they left, I sat chatting with Billy on our deck until I felt the time was right to initiate the plan that I had developed. We eventually got around to talking about girls and the ones he dated. I carefully directed the discussion to whether he had any sexual experiences with them. Somewhat embarrassed, he said that he hadn’t done much other than getting inside their bras and feeling their breasts and occasionally rubbing a pussy through. ‘Why?’ she said. ‘Well, if you don’t enjoy the first time he has your bottom then you won’t want to do it again, at least not as often as if you do. Don’t you see. It’s in his interest to make sure you enjoy your first time with him. That’s where he’s so different from Steve. He wouldn’t make you have anal sex with him if you didn’t enjoy it. So, on the whole and if you want to, it would be nice to wear that for him. He would certainly appreciate it, I know I will and I’m only watching.’ ‘Won’t you do anything?’ ‘Oh, I might help him now and again but you know I don’t like him inside me down there during my period. I might suck him at the start if you don’t mind, but most of the time I’ll just watch and enjoy. Do you mind me watching.’ ‘No, not really. It’ll be quite exciting knowing you’re watching everything we do. Anyway he’ll need someone to talk to when I pass out,’ she said laughing. ‘If it’s anything like Wednesday I’m going to need time to recover.’ ‘So,’ I said, ‘will you.
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