At least he knew one good thing that would be happening today. Each time an Apprentice began his quest, he was allowed to take the cherry and fuck one of the girls in any way they wanted, no matter how sick, twisted or dirty it was. It symbolized the loss of virginity and becoming a true man.Apprentice Nick Harris quickly made his way into the dining hall, where the other Apprentices beginning their quests were waiting. The Guildmaster stood in the front, looking over them sternly."Now that we are all here," the Guildmaster said, five minutes later, when everyone had settled in. "Let us begin the Challenge of Virginity."Most of the men (all of them were at least eighteen-years old), grinned, and the ones that didn't had quite impure thoughts racing through their minds.After another five minutes, Nick Harris heard his name being called.Stepping up to the platform, Nick bowed, his sword resting at his side, ready to be pulled out at a moments' notice."At ease, Apprentice," the. The only time I wore little boy’s clothing was when family visited or I went to school.Everyone in town knew I was a very sissy acting little boy. I was bullied a lot by other boys, shunned by the girls, pitted by the teachers and talked about by the others in the little city where we lived.Summertime was the best time as I could be totally Vanessa. Mother would be at the dinner, waitressing and I would be home alone. I was fifteen, home one rainy summer morning playing in my mother’s make up. Earlier I had slipped into one of her full length open bottom girdles and a pair of tan seemed nylons. I attached the six garters with great care making sure the dark seems were straight as arrows; as mother had taught me. My toes and nails painted bright red as they had been since school let out for the summer. Cleopatra would have been proud of my eye makeup. I had just finished painting my lips candy apple red, when I heard a man clear his throat in the bedroom door.Startled I turn.
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