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I positioned the head of my penis against the pucker of her rectum as she continued to hold herself open for me. I asked her "Diane, are you sure you want to do this?" Yes, Mike, I'm sure. But thanks for asking.", she answered, pleased by my question.Holding myself in place with one hand, I put the other on her hip to steady myself as I gently pressed forward. I could see it as my efforts pushed the ring of her anus inward, but it wasn't enough to get me THROUGH - I was simply too reluctant to risk actually hurting her. I eased up for a moment, then tried again, with a little more pressure; still without success.Diane, recognizing the problem, told me "Mike, it's okay. I want you to do this. If it starts to hurt or anything, I promise I'll tell you."Reassured that she really did want it to happen, I realized that I could do what I'd done the first time I'd deflowered her: simply scan her, continuously, so that I'd know if/when I was hurting her. With that in mind, I took a deep. He is the guy she found obnoxious and arrogant! I wondered what she would do if she liked the guy? He had only been with the company a couple weeks if my memory was correct. He was a fast worker!"I told her you were the same age as her mother and weighed 220 pounds," laughed her boss. "When she sees you, I'll have to fire you anyway!" Then he added, "I told her I was house hunting this week. Now it looks like I won't be getting too far from the hotel for a couple days."Emily returned to the room and laughed. She looked great and Mr. Boss, (Was his name Joe?) grabbed her and gave her a slow, wet kiss. I was tempted to grab an umbrella off the shelf and shove it up his ass!"Why don't you plan on spending tomorrow night with me, right here. We can go to dinner and be in by 8 PM. You may get lucky when we get back and you will be looking at a house, after you have your way with the owner," offered Emily. "If you're 'up to it', you can have me in every room! Would you like that tour?".
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