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She said, “I do have an English schoolgirl outfit.”“What does that look like?”“You probably do know. They wore neckties, jackets, straw hats, that kind of thing.”“Knee socks too?”“They did, white or black or maybe gray. Plus, regulation knickers.”I didn’t know what that meant, so she explained it for me. “In each school, all the girls had to wear identical underpants. They would be green or blue or white or whatever. And if they were caught with something else on, the headmistress would introduce them to the cane.”That seemed intriguing, so I asked, “Would you wear this outfit for me?”“Of course, and maybe I’ll be naughty and wear non-standard knickers.”I tried to imagine what she would come up with. Then I said, “But I’m, you know, male.”“We can stretch it a bit and say that as a teacher you could discipline wayward girls.” I knew Tiffany would have the equipment needed for this scene.I suggested we go for lunch and coffee in Manhattan. When we got there, I wanted to ask her more. As time went on, our relationship heated up. We did almost everything but fuck. On occasion we got very close. One time she was straddling me on a kitchen chair. Her skirt was pulled to her waist and she didn’t have panties on. I was in my underwear, my cock sticking through the opening. As we kissed, she lifted up and let my cock slip behind her until it was rubbing between her ass cheeks. I was close to climaxing already. When she realized that, she lifted up again and let my cock head slipped between the lips of her pussy. I heard her whimper. Her hips jerked like she was starting to climax. When the slick and swollen lips wrapped around the head of my cock, I couldn’t control myself. I shot off like a cannon, my sperm squirting just inside her lips and running back down my cock. She began to climax with me. It was a Saturday night when the inevitable happened. I had taken Cindy out to a nice dinner for her birthday… spending almost a week’s pay. She had on a tight black dress.
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