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We proceeded to the bedroom and I got the Strap-On from the one of the drawers under the bed. She put it on without hesitation and I'm going to admit at this point I became very nervous. Luckily, the missis saw the funny side and we had a laugh, she was wearing it and laughing because she had a willy. This was a first for us both, new territory and she really put me at ease. She then grabbed the lube and asked me to get on all fours, which I did. She then lowered to me and started to rub lube around my hole, she then started fingering me and after a few minutes she said "Let's begin". She started to move the dick up and down over my hole and every other stroke she would push the tip in slightly but each time it she would put it in a bit more. Finally it was in, at first it was weird and the great thing is it didn't hurt and I started to enjoy it. We had to stop a few minutes in for more lube and she said "Let me know if you want me to slow down or go harder" so I asked her to go. "It's not like that," Josie protested. "I mean, my whole family has known Preston for... well, for years. He and my dad still play golf together! My dad has Preston's law firm on retainer. It's just a family thing, Freddie." So how did it happen, that you two broke up?" He dumped me, actually," Josie said. She tried to make the statement flat and neutral, but I thought she came off sounding a little wistful. "I mean, on the surface we made this mutual decision to call it all off, but it was really Preston's doing, when you get right down to it." Just like that?... One of those 'I think we ought to start seeing other people' things?" It was more than that," she said. "We were engaged. We were going to be married in the spring." Jesus Christ!... How come you never said anything to me about that?"Josie, clearly, was becoming uncomfortable. "It's ancient history," she said. "Why would I assume you wanted to hear about my old boyfriends? Maybe you and I will talk to each other about old.
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