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This is normally when Cindy would roll onto her back and have me mount her missionary style.Instead, she worked the head of my cock up and down between her firm ass cheeks. She was teasing me for sure. In the ten years we’ve been together, Cindy had not been receptive to trying anal intercourse. We did have some ass play a few times, but nothing more than a little external stimulation and digital penetration on each other.My pre-cum was plentiful and, conveniently, a good lube. Cindy continued to stroke my cock while rubbing my head up and down between her ass cheeks. She started working it in a circular motion, eventually settling on her tight little pucker. She arched her back, pushing her ass back against me. I pushed back and felt the tip of my cock slip partially in. Cindy gasped softly and let go of my cock. I pulled her hips back toward me and I felt the head of my cock clear the tight ring of her sphincter muscle. She gasped again, so I pulled out. This made Cindy quiver,. She’ll be gone when he gets back from work this afternoon. If not, he’ll fuck her again and then send her on her way.He dresses quickly and is out the door in record time. Stopping off for coffee, he heads into the office to get some paperwork done. Alan isn’t in his office for more than thirty minutes when Judy steps in. “Can I help you with something, Judy?” he asks, looking up from the paperwork on his desk.The secretary is hesitant for a moment. “I ... I have been thinking about how I broke my rules...”Immediately fear begins to well up inside Alan as he starts thinking the worst. Did I push too far? Is she going to quit because of it? Should I have just left things how they were and let her initiate it? He just doesn’t know where to start or what to say. Judy is the perfect woman, what dreams are made of. So he does the next best thing—he doesn’t say a word.“It’s not your fault, it’s mine,” she continues. “Victoria has no idea what we did, and I don’t want her to. She knows I.
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