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I am sitting with my dick snuggled in her thighs and she keeps rubbing making me stay hard as a rock. Portland reach behind her with both hands and pulls her cheeks wide apart and tells me to quit teasing her and put something in her, so I slowly insert a well lubed finger in to her ring. She pushes back and moans with delight. After a couple of moments of this I insert a second finger. Portland just keeps moving in time with my strokes. By this time I’m getting pretty excited and know its time. I put lube on my dick with my free hand and continue to stroke with the other hand. Portland has already moved her hand to her pussy and is fanning herself rapidly. I move up to her ass with my dick and place it at the ass ring where my two fingers are still at work. I us the two fingers to guide my dick into the ring and exchange places. Oh how good it feels. Warm, tight, textured yet soft. And I haven’t even gotten past the gate yet. Portland couldn’t wait though, she pushes her ass up and. He'd mentioned that he was doing well with the girls out there, and so I was looking forward to seeing what kind of damage I could do in a new city. After I dropped my bag off at his new apartment, we immediately went out to hit the bars. We drank hard and settled in to have a great time.As the night went on, I found myself on a barstool off to one end of the bar, enjoying a flirty conversation with a very sexy woman named Jane. At thirty years old, she was about eight years older than Adam and me and still as sexy as ever. She had all of the requisite curves and good looks, yet she also had a level of confidence and self-awareness that I hadn't seen in the college-aged girls I was used to picking up. Adam sat a few people down the bar from us, chatting it up with a younger girl named Lauren. She looked smoking hot, was still in college, and was enamored with Adam. So far things were looking perfect for my first night in Chicago.Unfortunately, Lauren seemed a little too into Adam. He.
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