Take a Letter, Jenny Part One
By David Brennan
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John knelt before her, with the first signs of tears welling in his eyes. He'd never been so humiliated before, but he knew it would be impossible to resist her. "Please mistress, please let me wear my pretty new clothes. I want to wear my dress and high heels and stockings and apron. Please mistress... I just want to serve you and be your maid."
She seemed pleased and allowed him to stand. The humiliation of having his naked body paraded before her was overwhelming, especially as she watched him with a cool, appraising look. She handed him a pair of black, delicately laced panties with a tiny red rosebud motif. He shivered slightly as he lifted his legs into them and pulled them on.
He suddenly felt very embarrassed, but she handed him a jet black corset and indicated that he put it on. He kneaded it over his rather slim body and breathed in as it settled into place. Suddenly, she grabbed the laces at the back and pulled hard, until John felt all his remaining breath escaping from his lungs. He gave out a sudden little scream. She fastened the corset and he realised that his breasts filled the cup and completed the girlish outline of his body. He also felt more trapped than ever, as if the corset was locked around his body.
Her eyes gleamed as she handed him the sheer, black silk stockings. They felt so soft and delicate that John was almost afraid to feel them in case he laddered them - and incurred the displeasure of his mistress again. He put them on very gently, which heightened the sensation as they glided over his shaved legs. He knew something was happening which could never be revoked, and the feeling of helplessness and vulnerability was growing with every item of clothing she forced him to wear.
Next came the shoes. They were shiny black court shoes with a stiletto heel and a pretty little bow at the back. He forced them onto his feet and silently cried as he stood up and the pain became intense.
"Now, walk over to the mirror, Jenny," she mocked. He staggered over to the full-length mirror and immediately understood why she had chosen this particular punishment for him - he looked so feminine, with his calves stretched into shape by the high heels to give the impression of a leggy girl's body. This impression was helped by the slimming effect of the corset, which not only pulled in his waist but also gave his hips and bust a much fuller, feminine appearance. John began to almost enjoy the transformation!
"Now then, Jenny, I think you should wear this."
He picked up the elaborately-frilled and laced petticoat and, raising his arms in the air, let it rustle down his body. He watched, fascinated, as it settled into place around his waist, reaching just above his knees. He played with the delicately trimmed edges and wanted to cry. This wasn't right... and yet it felt right to him.
The jet-black cire dress cam next. It hugged his body as far down as the waist and then flared out with the petticoat. He teased it into shape to produce the best effect, and was suddenly conscious of her staring intently at his every move.
"Enjoying yourself... Jenny?"
He realised then that his humiliation was complete - he was standing before her with a man's features and a girl's body. He wanted to hide, to avoid her mocking glance. He knew how ridiculous he looked.
"W-w-would you make me up, please mistress?" he pleaded. He knew it would be the only way to look even vaguely normal, and yet he understood that if this was to go any further, he would rather be mistaken for a girl than be seen to be a transvested man. All the same, he hated to ask her to complete his humiliation - it seemed like a final admission of defeat.
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