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She was three years older than me, 22 to my 19, and I'd caught her glancing at me one day in class and figured that I'd take a chance. We went out to dinner a few nights later, I drove and she walked from her apartment. I dressed up, she didn't. I tried to apologize but she stopped me with a kiss. "As long as you're comfortable, I don't give a fuck what you wear." I appreciated the honesty. I went back to my car, took off my suit coat and tie and threw them on top of the overnight bag with my clothes, toothbrush and deodorant... wishful thinking. Dinner was fairly ordinary. She drank, I didn't, she ate a lot and I tried to be good. All in all, we got on all right. I knew, though, after three margaritas, that I had to escort this girl home. I paid the bill- $35 for her, $15 for me and $5 for a tip, and droe her back to her place, four or five blocks away.I had only fucked one girl up to this point and it had taken a lot more than picking up a thirty-five dollar tab. She put a record. I swung Claire around to the side of the bed, so that I could stand on the floor. Claire had a fairly high bed that was an ideal height for me to fuck either a pussy or an ass from the floor. I positioned Claire with her butt at the edge of the bed and her legs up over my shoulders. I could look down and see the fleshy pink lips of Claire's pussy, all open and glistening with her juices. I also had an unobstructed view of Claire's once virgin ass, stretched around my cock. I've always liked the impropriety of so clearly seeing my cock working in and out the wrong hole with the proper hole so close by, empty and unused. I like to lean forward while I drive my cock deep into a girl's ass and feel her wet pussy on my stomach. When I would do this to Claire her eyes that were closed in a sensual reverie would pop open with vivid intensity. The pleasurable pressure of my pelvis on her pussy (say that five times fast), no doubt helping to re-associate the twinge of pain that Claire would.
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