Magic Dress - Denise

CHAPTER 1

We were twin brothers but far from identical. I am Derek. The older he got, the more Clive resembled the photos of Dad, and the young photos of Grandad D (Dad's dad), chunky and square. It was a shame Dad was not around to see it, but Grandma D (Dad's mum) was and doted on him, though she was always kind to me.

I was more slender and oval faced and looked a bit like Mum. Grandma M (Mum's mum) said I was a bit like a cousin of hers who had died young. So we were the same but different.

We were an unexpected late addition to the family, which was hard for Mum, so big sister Kate helped quite a lot. Mum went back to work full-time as soon as she could, so Kate collected us from nursery and later primary school after she finished at secondary school. I loved my Mum but I worshipped Kate. She was kind, she was beautiful, the perfect girl, the perfect woman, the perfect human being. I was sorry that I would not be allowed to marry her when I grew up.

In a family with no male role model, Clive was enough of a boy to count more than double, and I followed along. He was the one with the naughty ideas, who got us dirty and into scrapes, but we were loved too much to be punished properly.

When we were about seven or eight years old, we were alone in the house and started messing around in Mum's room, even looking in her drawers. There was a thing that buzzed when you twisted the bottom and felt funny on your hand or arm. There were some photographs right at the bottom, face down of Mum with someone we didn't know, quite a slim man, not at all like Dad.

The game lurched around. We wrapped scarves around our heads to be an Indian Rajah. Clive found a hat and put it on and said he was a cowboy. He put on a sort of belt but with things dangling down with sort of clips as his gunbelt. He used the buzzing thing to point at me as a gun, then said I should put on some war paint. I wasn't sure how to do this, but put some lipstick on my mouth and some blue eyeshadow on my cheeks. Something with feathers I pretended was a headdress.

Then Mum came in. We were only kids, but it must have been quite a mess and quite a shock. She misunderstood. Grabbing the buzzing thing and the photographs she pushed them into the drawer and closed it quickly.

"Putting on makeup and dressing up as girls? Let's do it properly!" she said quite angrily. And I now think she was trying to distract us from the things in the drawer.

She sat us down, got some wipes and removed my makeup, then started applying some to both of us.

"Like actors in films!" said Clive happily.

Then she got a couple of Kate's dresses from when she was younger and put them on us. We could hardly stop giggling. When we saw ourselves in the mirror it was the funniest thing ever, and Mum forgot to be angry.

"Look at me, I'm a girl!" said Clive, moving around in what he supposed was a girl way.

I had a rare opportunity to be one up on him. "Look at me, I'm Kate! I'm so pretty!" I said, and walked around trying to be as beautiful as her.

We thought for a moment that Mum was ill, but she was helpless with laughter. Kate came home and joined in, then rushed and got her camera. In our teenage years that photograph was used as the ultimate blackmail threat!

CHAPTER 2

Clive and I were visiting our big sister, although I was now bigger than her except when she wore heels. She had been wonderful big sister, and we had been naughty little brothers, but really we had fun. Now she was 30 and we were 22.

"Do me a favour, will you?" she asked. "You've got a car. Take this box and bags to the charity shop."

I looked and was surprised. "Your Amy Tan books! You're not throwing them out, surely? And these as well?"

"Yes, I'm having a de-clutter. They were good, but realistically I'm never going to read them again, so someone else can enjoy them. Now tell the shop this orange bag is all new clothes, unworn, most with tags. The grey bag is worn, but only a bit, and washed."

I was puzzled. "Why are you throwing out new clothes?"

"I bought too many. It's the latest advice. If you haven't worn it in two years, then you probably never will. Some of this stuff is five years old, and I've never put it on. There's even some sexy undies still in sealed packs!"

"OK," I said. "I'll put them in the car. I imagine you mean Mum's favourite charity?"

"Of course," she said. "And obviously help yourself to anything you want first."

We got back to the flat that I shared with Clive, and I got the things out of the boot.

"Leave them in the boot," said Clive "and one of us will drop them off at the shop when we happen by."

"No," I argued. "I'm going to put them in my room, and sort out what books I want and maybe add a few of my own. Clothes as well. Then I'll take it all together and make sure they understand about the clothes."

He shrugged. "Suit yourself, though I'll be amazed if you give up any of your books."

We shared a flat, we shared a car. Most of all we shared a life as we had always done. I worked in an office at a university, he worked in a factory. While he played rugby on Saturday, I did the weekly clean-up and clothes wash. I did most of the cooking to save us from an endless diet of takeaways.

I decided I was not going to keep any of Kate's books. I would read what I wanted and then take them to the shop. I would definitely add some of mine to declutter. However, it would not be good for the clothes to stay bundled up in bags, so I made space and hung them up in the wardrobe. Our flat had been a family one, and I had the parents' bedroom with a big fitted wardrobe, mostly filled with boxes. I pulled out a lot of the boxes and thought we could do a declutter, and began sorting them into keep, junk and charity. Which was quite satisfying. I put a box of our toys in the junk section, but Clive seized it and put them on display on the shelves in his bedroom, which had once been the children's one.

CHAPTER 3

I was visiting Mum on my own for once, and asked her about Dad. Did he die or what?

"No," she said. "He just went away when you were little."

I asked if he had run off with another woman.

"No," she said, with catch in her voice, "it was another man. That's why Grandma D only talks about him as a boy and Grandma M won't speak of him at all. I may as well tell you the whole story."

"There were two boys I loved. They weren't brothers, but they could as well have been, they were as close as you two. I had a close friend as well, Pamela, and we used to double date. Both of us went with both of them, and that includes going to bed. Just a minute, I'll get a picture."

She showed me some photos. Two girls together, two boys together, boys and girls. She looked quite a bit like Kate then. The one boy was Clyde, the father I had never known, who looked very much like Clive. We only ever said 'Dad' so I had forgotten or perhaps never knew he was called Clyde. The other boy looked, well, like me.

She had tears in her eyes as she continued, and her voice was unsteady.

"I was such a silly girl. I went to bed with Clyde and he said we should do some heavy petting but not have sex until we were married. He proposed to me and I accepted. He was big, he was handsome, he was charming. I thought I had got the better one, but really I loved Dennis more."

She stopped to blow her nose.

"Of course, I didn't know he was gay till much later."

It took a little while for her to continue.

"I knew I was making a mistake, but I didn't have the courage to pull out. I had to convert to Catholicism, though I have never practised since then. There was such a fuss with both families being so happy and telling us we were the perfect couple, and it was a grand Catholic wedding."

"Dennis came to see me in the weeks before and tried to persuade me to call it off, but I couldn't do it. He also made love to me several times. But I still didn't have the courage to disappoint all those people, and went through with it."

"On our wedding night Clyde made a real effort and managed to come in me. But that was it. Nothing on the honeymoon. However, that meant the marriage had been consummated. If he had not been able to manage at all, it could have been annulled. And I soon found I was pregnant."

"For Clyde, it was the perfect cover. As a gay Catholic man, to be married with a child proved he was not. My only comfort was that I did want children and I was convinced that Dennis was Kate's father. I didn't have sex but I had a lovely daughter, so I was fairly happy."

"After about five years I began seeing Dennis again. He was married to Pamela, but it had gone off the boil. We used contraceptives of course."

"I really wanted another child, so I eventually persuaded Clyde to try again. And to give him his due, he really made an effort. I expect he was thinking about his boyfriend, and I had to get him almost ready, but he did manage to come in me a few times. Meanwhile I was having as much unprotected sex with Dennis as we could get. When I got pregnant, of course Clyde stopped, but I was able to continue with Dennis for a while in what we called our honeymoon."

"I was really hoping the child would be Dennis's, but would not mind if it was Clyde's. I just wanted another baby. I was delighted when I got two. I don't know if it's possible, but I always said to myself that we got both. Clive for Clyde, and Derek for Dennis, hence the names. So I think that Kate is your full sister, but Clive is your half-brother, if that means anything to you."

"Clyde was of course proud to be the Catholic father again, and both grandmas were delighted, but that was enough. You were three when he left to live with his boyfriend. There was no divorce, but he sent me some money for a while, then stopped because he said that I had been unfaithful."

"So now you know, and I hope you won't think too badly of me." And she cried and cried.

I hugged her and told her what a wonderful mother she had been and how she had had three children who loved her.

CHAPTER 4

Clive and I were talking about Kate: some of the naughty tricks we had played and how wonderful and loving she had been.

"I was going to marry her," he said suddenly. "I was really disappointed when Mum said it was not allowed because she was my sister."

"Me too!" I said. "I would have had to fight you for her! I thought it was because we were Catholics and it was really unfair." We then had a play fight, which of course he won.

And I began thinking about the clothes in the wardrobe. And Kate.

Not having sex with her.

Being her.

While Clive was out playing rugby, I looked at the clothes and knew what I had to do. I shaved, cleaned my teeth again and showered. I opened the pack of sexy undies: a lacy bra and panties. The bra was really difficult. How the hell did women manage? After struggling for a while and failing, I took it off and looked at it carefully. It was actually adjustable. By lengthening the straps and some trial and error, I managed it, stuffing some socks into the cups. Looking at myself in the mirror I got a real thrill.

I remembered that when Clive and I looked at porn together I had always liked the pictures in underwear while he preferred them naked. We both liked them in dresses with the bum or boobs peeking out. How great it was to be in such a picture!

Strangely, although I was excited, I did not get stiff. It was something else.

Then the moment I had been waiting for. There was a green dress which Kate had worn just once.

There are men who want to be women, but I wanted something better. I was going to be Kate!

Putting on that dress and looking at myself in the mirror was the most perfect moment of my life. Later I would have makeup and a wig and look more like a woman, but this first time was ecstasy. I walked around the flat, humming to myself, tidying up Clive's mess. Then I put on a CD and danced a bit. I was happy. The makeup didn't matter. I was in Kate's dress. I was Kate, the perfect human being.

After about an hour I took the dress off and hung it up reverently. I tried some of the other garments. I could not manage them all, but enough to know that I would be doing it again.

I bought some tights in the supermarket - easy enough to add it to some food shopping. The sexy underwear came with a suspender belt, so I would have liked stockings, but didn't dare to go to women's clothing places.

Whenever I could, I spent time dressed as a woman. I wanted to tell Clive. I wanted to tell Kate. I wanted to share my happiness. But I could not. I was just not that brave.

Eventually I was found out (which deep down I had been hoping for, really.) Clive knocked on my bedroom door and came in before I could say anything. There I was in a flowery top and plain skirt, with tights, reading an Amy Tan book. He looked astonished, then laughed.

"So this is what you get up to! Dressing up in women's clothes and having a good wank! Let me know next time - I'd love to see it."

I was red with embarrassment, and sat up, putting my feet on the floor and pulling my skirt down. What could I say?

"I'm sorry." Of course, I said I'm sorry! "I just found I like it. And I don't wank actually."

"No need to be sorry, little brother." (He was born a few minutes before me.) "Or should that be little sister? You're welcome and I won't make fun of you, I promise. Just keep out of the way when I bring a girl home."

He thought a moment. "What shall I call you when you're in drag? Derek doesn't seem right, and I can't have two sisters called Kate or we would get confused."

I thought of my real dad and answered "Call me Denise." So I acquired a name. And things were much easier, now I did not have to hide.

I told him how I wanted stockings and he just went and bought them without embarrassment. "They're obviously a present for my girlfriend," he explained. He is so much more daring than me.

"Actually, my live-in girlfriend, now I think about it. You know you would brighten up the place if you wore some makeup. It wouldn't be the first time would it?"

I agreed I would like to try some makeup but didn't know where to start.

"Obviously Kate," he said. "She would understand, and she loves us."

"No!" I said. "For pity's sake don't tell her. I just could not face it."

"OK, I won't," he said. But he was lying.

A couple of days later the doorbell rang, and I hurried to hide in my bedroom, saying "I'm not in."

"Yoohoo, Derek!" came Kate's voice which would have pleased me at any other time. "Apparently you say you're not in. Come on, don't be a mardy girl, come out and give your big sister a kiss!"

Shamefaced I crept out.

"Oh," she said. "That green dress. It looks so nice; I don't know why I didn't wear it more. It was funny, it did not seem quite right on me. I'm glad someone else gets to enjoy it."

And she kissed me and hugged me and kissed me and hugged me some more. I loved her.

Clive went off to make some tea.

"Well, it will be nice to have a sister after all this time. Please let me help you. You were so unbelievably cute when you did your dressing up. I've never showed the picture to anyone but Mum, but I have looked at it so much. I might throw some more clothes in your direction."

We talked and then she put some makeup on me. Then I got the most important lesson: how to take it off at night. She said she would come by after work when she could to make me up for the evening, and maybe we could have some sessions discussing clothes at weekends.

Next day she brought me my own set of cosmetics including a different shade of lipstick, a wig she had had for many years, two nightdresses that she never wore and some panties.

People at work asked why I was so cheerful. When I say people, I actually mean the specific sort of people called women. I am the only man in a departmental office at the university, doing a job that would formerly have been called a secretary, but now is clerical staff. Nothing remarkable really. The head of department is a female professor and has a male secretary, called a Personal Assistant these days.

I was now looking at them in a different way, thinking how their clothes might look on me, observing their hair and makeup. I hope they did not misunderstand. Or perhaps I hoped they would understand even more.

On the weekend, Kate brought me a handbag, and some flat heeled shoes.

I got some extra help from an unexpected quarter - the rugby club. Clive knew one of the players was a cross-dresser and told him he had a friend looking for advice. He had made contact, and the wife of another cross-dresser had offered to visit for discreet help.

It was a woman called Betty who worked in the women's clothing floor of a department store. She turned up and told me to take my clothes off. All but my panties. She then measured me in a lot of places, got me to put my bra on, and measured me again. She made some adjustments, which felt better.

"A lot of people in your situation rather like bras," she said, "and buy a lot of them. It is of course much better to have ones that fit. Now I have your measurements, you can come into my department at any time and I will tell you if a particular model is suitable. Just make sure you only speak to me and of course say you are looking for a present for your girlfriend. If there are any other garments such as dresses you fancy, tell me the model and I will check if it is likely to fit, and your sister can collect it."

She then got me to dress up in the clothes I had, and made notes.

"The green dress is particularly nice, but the elastic on the waist is stretched to the limit. You really could do with losing an inch or two. Reducing the waist will give you a lot more choice and make you look more feminine. Quick diets just empty your guts, which is OK as a temporary fix for a special occasion, but you know what to do. There is also an exercise sometimes used by body builders to suck in their waist. I'll give you details."

"Lots of people in your situation simply enjoy wearing a dress, and a bra is enough. If that suits you, there are plenty of less shaped garments for women. You might look at suppliers who make clothes cut to fit a male body. However, a bra is only one sort of what we call foundation garments, and you might want to try to get a more female shape at some point."

"An easy one is pants with padding for your bum and hips, just the equivalent of a bra, really. A little can make quite a difference, and I think you should consider it at some time."

"Women commonly wear control garments which pull them in a little without being as restrictive as a corset. This can give you a bit more waist. Let me know if you ever want advice on this. For now, try to lose a little tummy and think about bras."

"There are things called breast forms which give quite realistic look and feel in bras. Don't buy them without asking me."

"We can also show you how to hide your cock and balls away, but that is for the future if you want it."

It was a lot to take in, but I was excited by the possibilities.

In due course I lost some weight and got foundation garments which really helped to give me a more womanly shape. Not an hourglass, but convincing enough. Kate was delighted.

"Since you were 8 years old and first put on my old dress, I've been wishing you were my sister and thinking about how I would help you with clothes. As you grew up I was thinking of what a girl of your age could be wearing. In my mind you have had so many outfits for school and parties! Still, better late than never!"

With her experience and love we found some really flattering outfits for Denise. And we both loved the realistic breasts that Betty suggested.

I did not always do it, but I quite liked tucking my genitals out of the way so that I had a flat front, using special pants and a technique I was taught.