Forced To Be Their Sissy!: They’re Making Me Dress Like A Woman!

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The only assets left to me were a life insurance policy for a million pounds and my pensions, none of which I could access. I was worth more dead than alive I realized. Then it hit me that the only solution was for me to die. Not literally of course. Life was still good, even with the problems I had made for myself. I intended to live. But Harold would have to go and I would have to become someone else. They both sat in the car as his mother put on a head scarf – she did not want the hotel receptionist to notice that she’d dyed her hair blonde when she went to settle the bill. I live in the flat underneath. My name’s Polly and I wondered if you would like to come down ad play. What’s your name?”

A cruel smile appeared on her face. "Look at him, Sarah. He's crying, just like a bride on her wedding day. Why he's…she's becoming emotional." Then Mrs. Jennings voice became harsh again. "If you think crying is going to get you out of this you're wrong young lady. This is your fantasy, and I'm going to complete it for you. Now keep your hands up."The girl was chatty and spoke a lot about herself. Thankfully I had to do little more than nod or make an affirmative noise. I was greatly relieved when the car pulled up outside the airport. The girl helped my unload my case, wished me a good flight and then sped off. I took a pair of sunglasses from my handbag and put them on. It would be best if my eyes were hidden, I decided.

I climbed into the car as best I could whilst wearing a tight skirt and high heels. The girl put her foot down as soon as I was inside and my wigged head hit the headrest with the acceleration. The girl asked me what I was doing and I told her untruthfully that my car had broken down and I had had to abandon it to catch my flight. I took to wearing increasingly androgynous clothes, jewellery, nail varnish and a little subtle makeup – being careful not to embarrass my boys at school parents’ evenings – and began opening up about my transvestism to friends and employers. I don't know, I kind of like you. I'm not in love with you or anything, but I always thought you were a nice, sensitive guy. Now I understand why." She paused for a moment. "Despite what my mom might be feeling, I've found dressing you up kind of fun. Maybe next time I'll dress you as my little sister." Charlie was far too old for any amorous adventures with me but he appreciated seeing me in my wedding finery. He was besotted with me and gave whatever I liked. I was soon the best dressed lady in town. All of my clothes and jewellery were the envy of other women. An evil smile crossed Mrs. Jennings lips. "You'll find out soon enough my dear. Take our hands." Sarah stood on one side and Mrs. Jennings on the other. Together they held my hands and on the count of three lifted me out of the chair. It was my first pair of high heels, and I found myself wobbling as I stood.I am marched to Flowers’ booth and made to sign a visitors’ book and a long disclaimer stating that I was aware of the risks of entering part of the prison population and of the punishments to be meted out for trying to smuggle something into the prison or helping a prisoner to escape. He can also start to dress in some women’s clothes and experiment with feminine fashion. If he isn’t quite comfortable with that, he can try to wear more feminine colors instead. You committed the worse sin," Sarah explained softly after her mother left the room. "My mother can't stand it when anyone uses her things without her permission. She gets mad at me if I borrow something of hers without asking. Then again, I was a little peeved when I discovered you had been through my things."

Where do you think you're going?" she hissed. "You wanted to be me…and now you're going to get your chance!" Well, as long as my mother isn't around it doesn't have to," she winked. "I'll think about it. Now, if I were you I would do everything my mother tells you to do to the letter. Once she calms down then she'll let you go. She's been waiting for this moment for weeks."

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This went on for hours. I stood in front of the windows as hundreds of people drove and walked by. A couple of ladies stood there for so long that Mrs. Jennings invited them inside for a closer look. I sashayed nervously around the room so they could observe the flow of the dress. The ladies kept saying how pretty I looked, and then Mrs. Jennings told them that the bride to be was really her nephew who was being punished for going through her things. The ladies laughed with evil delight, and chastise me for being such a 'naughty girl'. Mrs. Jennings smiled and told them she didn't think there would be any more problems from me after this. Each of them posed with me for a picture, and rubbed their hands up and down my silky dress laughing and commenting about how 'pretty' and 'feminine' I looked. I felt total humiliated. The next day Roger was left in the flat on his own while his mother went to see her old friend. He was wearing a little blue skirt and a white frilly blouse that had taken his mother’s fancy in Debenham’s earlier in the week. First, I paid one last visit to my mother. My mother, once a strong minded, competent woman, had in her twilight years descended into senility and no longer recognized me. It was a heartbreaking visit as I knew, due to my own stupidity, that I would never see her again.