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BOY was I wrong!If I didn't already mention, I worked with Alex at a popular hotel chain and the more I worked with her, the more I wanted to see more of her. We started hanging out outside of work, getting dinner, drinks, etc, and I started to grow to like her. Really like her. Things weren't serious at first, but all good things come to an end. They either get better or they come to an end. Well my situation got better and Alexandra got more aggressive in her chase and my crush developed.Alex and I were out at a bar with other colleagues and because we were a couple years younger than the rest of our co-workers, we sat away from the rest of the group."So how many partners do you think you've had roughly? And be truthful, I can't stand a liar..." she asked.I thought for a second and then thwarted her question with another. "I would be inclined to ask a beautiful girl of your caliber the same question." ha ha," she giggled. "Nice try, don't answer my question with a question and then. She put her head down on the floor, raising her ass up high, offering me her virgin asshole."I'll be gentle Sherri. Tell me to stop and I will if it hurts you," I spoke softly. I ran my dick down between her legs, letting her pussy wet my cock, coating it with her juice, before moving the tip of my cock to her back door. With gentle motions, is pressed it with the tip, letting her get used to the feeling of the tip on the very outskirts of her ass. My tip was barely being inserted in her and I felt her tense up, and watched her anus clamp shut. I slowly moved it up and down, caressing her pussy with the tip of it, then sliding it back upwards to the forbidden hole, letting the tip get more slickened, her ass relaxed after a few times, and the she soon moaned in pleasure, as my tip pressed into her. I did not push it in, I merely kept still, letting her get used to it being there. I could feel her muscles clamping down on my tip, squeezing it and then releasing it. I started jerking.
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