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Jim then told me to pull my panties down to my knees. I turned a bright red as he told me to spread my ass cheeks and let him see the hole he was going to fuck.He positioned himself behind me getting ready to enter my ass. I told him that I had lube in my purse and begged Jim to use it. He laughed and told me that if I wanted to use lube to go ahead, he would love to watch me finger my "pussy."I took the tube from my pocket book and squeezed some onto the fingers of my right hand. I reached behind me and started working one then two fingers in and out of my ass. I was still laying face down over the desk when I felt Jim grab my right wrist and bend it behind my back. he grabbed my left writs and put it behind my back also. Jim held my wrists behind my back with one hand pushing me flat against the desk. With his other hand he positioned his cock against my anal opening.I knew what was coming and I tried to relax and take a deep breath. Jim was not going to wait for me to get ready as. On the way back, Jim and I talked about how close we might have come to getting lucky. For my part, I had only been with one woman, ever, and certainly was anxious to be with one again. It had now been over a year since Laura, my first true love, and I had broken up as we went off to college. Despite the confidence that my sexually adventurous relationship with Laura should have imbued in me, Freshman year had been a total loss in the love department. Now in my second year, I was hoping that my losing streak with women might finally end tonight, with Monica. But it hadn't.The only thing that saved me from total loss in the sex department last year had been when my roommate's friend Eric accidentally discovered me trying to suck myself in my dorm room. He admitted he did the same, and I soon learned his extra-long cock meant he got more out of it than I did. I ended up convincing him we should suck each other, but he got post-orgasm regret and it ended poorly. So I wasn't feeling.
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