It was the start of my senior year in high school in Laurel, Maryland. New from the barren wastes of Idaho, I was still a little awkward, but got alon... with the geeks and the theater types. I was even a supporting lead in the fall musical the year I turned 18. My girlfriend at the time was named Cara, a tall, dark-haired volleyball player at my high school. She was one of those gorgeous, athletic types who should have been strutting around with the popular crowd, ignoring all beneath their. ... something.” she replied.With the caning now over I allowed my hand to explore the now rugged terrain of Michelle’s well-striped buttocks before slipping my fingers between her sumptuous thighs feeling the dripping warmth around her luscious cunt lips. With my thumb pressed against her throbbing arsehole I teased my fingers into her wetness as my eyes feasted on the beauty of her well caned buttocks, my free hand gently kneading and squeezing her tender flesh as I did so. Michelle moaned. Then you hear the bathroom door open and someone comes in to wash their hands. You let out a little moan as the plug has already stretched your ass slightly. You can sense that what you are doing is wrong and is slightly painful, but it is pleasurable in a strange way as well. The other person leaves the bathroom and you think of me out there waiting for you, so as quickly as you can you wiggle the rest of the plug into your ass. Taking a deep breath steadying yourself after the invasion, you. I didn't think about it atthe time, but talking about boys when I'm dressed as a girl was a wholelot different than when I'm in 'boy' mode. She asked me if I felt like Iwas attracted to them. I'd never thought about it before, but standing infront of Mother in my leotard and wrap-around skirt, I told her I feltlike I'd like it if one of my friends saw me like this and thought I waspretty. Mother said that when I wear fancy underpants, and a boy happensto see them, that's like teasing the boy.
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