Debbie Prologue

John had finally made it through high school and escaped from the confines of his hometown. And now he had made it to the big city. OK, he had no real friends and no family, but at least he wasn't harassed as much any more. Back home in high school he was always picked on for being too small and too weak. It didn't help that he looked slightly feminine or that he had been caught checking out the butt of the star quarterback. He had instantly been branded a "fucking sissy homo asswipe". He had tried to protest his innocence, told everybody that he had been checking out the ass of the cheerleader standing next to the quarterback, but it had been in vain. He was branded. And he had to admit there was some truth to it; even though he had never had sexual relations with anyone but himself, he was attracted to both sexes.

So the rest of high school had been hell. And there was a thing about his sexuality. He was attracted to both sexes; in fact he had fantasized about both the cheerleader and the quarterback. But it went a little further than that. He was also secretly in love with women's clothing. He dreamt about dressing up in a pretty dress and putting on a pair of high-heeled shoes. He dreamt about being pretty. When he was sure that his uncle was away, he would dress up in women's clothes he had bought in the next town. He would pose in front of the mirror and dream about being taken by large and strong hands. Held by his assailant and being dominated until he gave in to his attacker and performed some humiliating and highly arousing service. There were endless variations, but they all ended with him masturbating frantically. Afterwards he was always shameful that he couldn't be more normal, couldn't be more like everybody else. He would remove the panties, the bra, the dress and the high-heeled shoes vowing never to put them on again. But it never worked. He didn't dare throw them out, and sometimes he used them only a few hours later. For all his lust he was still a virgin. It had all remained in his fantasies.