I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started to get more and more people with us until we had a fairly large group. At about 2am, the friend I had originally came to hang out with decided that it was time to call it a night and I went with him. When we got to his place he crawled into his bed and closed the door and I slept on the couch. I didn’t get to sleep very much because I kept on thinking that the roommate could be home any second and would wake me up anyway, however she never came home that night. 8am came around and I was awake and by the look of it my friend wasn’t going to wake up even if a car honked it’s horn inches away from his bedroom window. I sat up and let myself wake up a little and to see if I was sober. Three of the moreinnocent pupils were scheduled each to receive a classic caning of six strokes.She thought this would be a suitable occasion for her fateful move, since shedid not want to make herself immediately vulnerable to the excitement thatshe often recognized in the Headmaster when he had finished a more severe caning. The three pupils were called into the study together, where the Headmasterbriefly lectured them, having previously done so at greater length, and toldthem that they were each going to receive six with the cane, the one who wasless culpable six good strokes and the other two six of the best. The lattertwo were then sent to wait outside the study door, which was carefully leftajar, and the first miscreant, remaining on that critical spot in the centerof the study, was told to turn to her right, bend over with her feet together,and touch her toes. The Headmaster than folded her skirt up, pulled her knickersdown to her knees, and administered six very smart.
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