He asked me to get up on all fours, doggy style, he squirted a lot of lube up into my crack and began to ease his lubed finger in and out of my hole, stretching it gently, and that was fine at first but increasingly difficult as he then placed a second, third and finally, four fingers were sliding in and out of my ass ! At times it felt okay but still difficult. He explained that he was trying to ease and stretch my hole wider so that his cock would feel a bit easier. He worked on me for ten or fifteen minutes, adding more lube, widening my hole gently and then said that he was going to try and fuck me but would stop anytime I wanted him to. I heard him open the foil on the condom he then pulled of of my ass apart guiding his big cock head towards my virgin hole. At first I felt a slight pressure against my hole but then he began to ease his cock in. I took a deep breath as I could feel the hardness of his big cock entering me, slowly he eased forward, I was began to feel some. I could hear the seconds thumbing in my head. He’d better say something soon. It was his turn to talk, and I couldn’t stand the wait. He looked me over thoughtfully, then spoke, “I’ll tell you what this is about. I’ve noticed you have been ... preoccupied lately. And your last report was, it was good, but it wasn’t Bailey good.”I felt a huge rush of relief, I couldn’t help but break out into smile, “Is that it?”“Yes, but I don’t think-”I laughed. I was worried that somehow he knew - if anyone would be psychic about something like this it’d be him, but nope, he just thought I wasn’t my usual superdork self. “Jeez, Mr. Wainwright, don’t freak me out like that. I thought you were going to say I had cancer or something.” I gathered my things and slung my bookbag over my shoulder. He kept making very reasonable very weak entreaties to my soul about whatever concerns he had and how there was help to be had, but his voice spoke more than words. It was weak, defeated, it was the words of a.
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