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Bob: Debby. Bill is rude and crude. What’s your last name?Debby: Uh, do I have to say?Bill: Afraid your mom is listening in?Bob: Or your boyfriend?D...bby: Yeah, I guess so.Bill: Which, mom or boyfriend?Debby: I don’t have a boyfriend, I’m married. (Laughing) (Holy shit! It was Debby! But was she naked? I pulled off into a mall parking lot to listen.)Bob: Now Debby, Bill was correct earlier. There were two parts to this contest. You not only had to be the first woman to come in... Bill: Yeah, you. As I gingerly inserted a finger in his tight anus I felt his cock stiffening in me and him start to move his fingers in my ass. Whether it was the cream I had lavished on my rear or the fact that he had totally relaxed me it felt Ok and when he murmured "Eileen, I really would like to have your ass -- do you think you're up for it?"I said "Mmmm , Alan really hurt me but if you're gentle I'll try."As I started to turn over Alan butted in " Hey honey, I'm the senior partner here I want a bit more. (As a man, I can only empathize with the poor guy. My confidence would be shattered if that ever happened.)That first night was terrible, mostly because she was nervous and scared. Her pussy was really tight and I made sure to slowly work my cock into her. She had her eyes closed in pain the whole time and I stopped, telling her that we'll work on the physical side more but that I didn't want to push anything and make her feel bad.Over the next several weeks, there was virtually no improvement. " Do you trust me?"A few more well chosen words and she agreed to meet me at the motel. For some reason (probably her parents, or more likely, her mother) she wouldn't let me pick her up. She insisted on taking a taxi there. I gave her plenty of time and made sure I got there well ahead of her, registered and was waiting when she arrived.She tried the motel door, found it unlocked and pushed her way in from the rain. Her hair was a mess and her coat tucked around her jaw and lips. I stood.
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