Head cheerleader and Prom Queen in high school, I bet." Thanks for the compliments." I felt the heat of a blush on my cheeks. I'd never felt comfortable accepting compliments for things I'd been born with. After all, how much credit can you take for being the recipient of a lucky arrangement of bits and pieces of genetic code? "But you lost your bet. Cheerleader, yes, but not the head cheerleader and I got enough votes to be a member of the Queen's Court but not the Prom Queen." If I lost, then you won. I've got a job offer for you. You see, ten years ago I was sitting in a chair much like the one you are sitting in now and looking across a desk very much like this one. I was being offered the same opportunity I'm offering to you. Different office, different city, of course, but the offer was the same." And in just ten years you worked your way up to being the boss? Or CEO, or whatever your job title is? You must have been very hard working." I was. You could say I worked my ass. I was enjoying being submissive. It's like the pressure's off. Someone else will put a dick in you when they want to. They tell you what to do and when to cum. This switch really turned me on, even though I was still apprehensive about someone fucking me in the ass. The ambivalence actually seemed to add to this sensual encounter. The pressure of the dildo head against my asshole brought all of these emotions to the fore. My conscious apprehension was shown to be a lie by my ever-hardening cock. It had been quite awhile since my cock was so fully engorged. I could feel my cock stretching to its max when I felt the dildo pressing painfully on my sphincter. Judy pushed slowly and I could feel every bit of the head as it entered, and then suddenly the pressure was off and the pain subsided as the head was fully inserted. "How do you like that, Jed?"I was still too breathless to say everything was just fine, and I wasn't sure if this was going to start feeling good. I just grunted an.
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