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Tony was married to Carrie’s grandmother for a long timeso they had already become good friends. She knew he wasintelligent, non-judgmental, imaginative, and open-minded. He was basically aware of her marital historyand multi-boyfriend lifestyle. Now that there was anintimate physical relationship, their trust and opennessgreatly increased just as it had with me. He became amentor as well as a lover. Carrie’s grandmother had enjoyed sex but only wanted thebasics. Now Tony had an opportunity to try all theinteresting activities he had only fantasized aboutearlier in his life, sort of like a second childhood.Carrie always got lots of pleasure helping guysexperience, for the first time, stuff that she had donemany times. It kind of made it new to her again. Oneafternoon when she visited him I was asked to accompanyher. It was great to meet this man who was so importantto Carrie. After visiting a while she excused them and they went tothe bedroom for about 20 minutes. I could. “Well, I can’t actually be sure of that. I’ve never done it by choice, but I think it may have happened one night. I was at a college party and got really drunk. I ended up in one of the rooms having sex with some guy I met. All I can remember is I made sure he was wearing a condom when we started, but I passed out at some point and woke up with my bottom a bit sore. There was no cum anywhere, and he was gone, but I think he may have finished in my ass.”“You understand that as his pet, Master will take your ass when he wishes to,” she asked. “He’ll be gentle if you’ve never done it before, but it will happen. The plug is to help keep you ready for him when he wants you.”“I’m not against the idea, I’ve just never let any man I was with have that,” I explained. “I’ve had fingers and tongues in my ass more than a few times with female lovers. It’s just that most of my male lovers were casual flings that I didn’t trust enough to try anal sex with.”“Then we’ll start with the second.
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