Magic Dress - Jady Pt. 01

GRANNY

It was Granny who put on my first makeup for the dance. It was always Granny for the fun things. Grandpa tried hard, and I loved him, but I did not like the same things as him. He took me to football matches until I could persuade him and Mum and Dad that I did not like hanging around for nearly two hours in the cold. He was the one who took us all to the Railway Museum. Mum tried to point out how interesting it was, but it wasn't.

It was Granny who took me to the pantomime each year, where we had a good laugh. Mum and Dad went once, but Dad left at the interval to go to the bar, and Mum said it made her a bit uncomfortable, with men dressed as women and women pretending to be men but showing off their bodies. Granny and me thought it was funny, and laughed and sang along.

Now for the sixth-form fancy dress dance, the costume had been Granny's suggestion. It was the eyeliner which really made it, and I thought I looked great.

Captain Jack Sparrow, the dashing pirate! Folks said I looked good, particularly some girls I liked.

She was my Mum's Mum and a widow. She had become a mother quite young so was not that old now. Dad's Dad was divorced so I only had the one Granny and Grandpa, but I was always Granny's special boy.

It was Granny who took on the duty of spoiling me with extra sweets and pocket money. She took me to fairs (which the others didn't like), and we laughed, bashing each other on the dodgems and pretending to be scared in the ghost train.

She also took me to the theatre: just the local amateur dramatic society; I loved it so I joined DramSoc when I went to university.

I learnt a lot in the first year. When I came home for the summer, it was Granny I told the most important thing.

I was gay.

Partly it was some lectures by the Student Union and a couple of boys in DramSoc who kissed and held hands openly. I also liked the dressing up and makeup, though I wasn't a very good actor. I began to realise that I liked girls a lot but I did not really desire them. My attempts to get girlfriends had really been a sort of acting.

On the other hand, there were some boys I had as friends, and I had got a stiff cock sometimes just chatting with them. I had dismissed this, as unwelcome erections were just a curse of teenage boys. They seem to arise any time it would be embarrassing. I wasn't sure if I fancied the boys or not.

I never got the courage to do anything, or even tell someone before Granny.

In those days gays and lesbians were only just beginning to come out, and there was none of the understanding or help there is today. I really knew nothing apart from feelings which did not seem to fit in with the world of Mum and Dad.

"You know," said Granny, "I've been thinking. I don't think you're exactly gay."

"Of course I am!" I said. "What else could I be?"

"Well," she said, "I've known some gay men, but I reckon you're not like them. I think you're a girl."

It was a shock, but strangely not exactly a surprise.

"How do you mean?" I asked, somewhat timidly.

"Well," she said, thoughtfully. "I had a boy and a girl, and they were quite different."

"There was your Mum and her brother Bob. Bob's your uncle, of course, but he went to Australia, so you won't know him."

"Your Mum was a proper little girl with her dresses and dollies, while Bob was a proper boy, always shooting things and playing football. They were both a lot of fun in different ways, so I've got a rough idea about these things."

"Anyway, you were also a lot of fun, but very much like your mother: like a girl really. I remember you once asked for a doll at Christmas, but you got a train set, which your Dad enjoyed at least. As you grew up you reminded me so much of your mother, especially the way you enjoyed dressing up and being made up for the fancy dress. I think your Mum could see it, but was always trying to deny it. She would have loved a daughter, I know, and was perhaps afraid to treat you like you both wanted."

It was a bit much to accept, but I could feel there was something in it.

SUMMER

Unfortunately for the summer, my parents had booked a family holiday in Spain: a package with Thomas Cook. Even worse (just by coincidence, if you can believe that) my Uncle (Dad's brother) and Aunt were staying at the same hotel with their daughter, my cousin Sandra. (Actually, she was my Aunt's daughter from her first marriage, so not really a cousin, I suppose, and I had hardly ever met her before: perhaps once or twice when we were much younger.) Hence two slightly disgruntled young people were told to "go off and have fun". This was before the days of internet and mobile phones, so there was only one implication.

Dad had secretly given me some condoms, saying "Don't tell your Mum, just be careful". Mum had done the same with a similar warning!

Sandra made her position clear.

"Don't call me Sandy."

"All right, if you don't call me Jerry."

"So it's Jeremy, then?"

"Jerry's OK if you didn't have a bully at school called Tom. If I'd had a middle name, I might have used it."

"I know, I'll call you J. D.: just your initials. How does that sound? I think it's quite cool."

I said I rather liked it. She went on.

"But still don't think you're going to get anywhere with me because you're not my type."

"I don't fancy you either," I said and rather regretted it.

"That's all right then," she replied, jutting out her lower lip. Then I did something right.

"Though you are rather pretty," I added. Which was true. She must have known it, but looked puzzled.

"Because I'm gay," I added, blushing. "I haven't told Mum and Dad, yet."

She stood open-mouthed for a second, then laughed.

"Fuck me! Or rather don't fuck me! You haven't told them, so they're trying to be matchmakers? Maybe this holiday is not such a washout, after all. Perhaps we can pick up a couple of handsome Spanish waiters, one for you, one for me!"

I realised I could be in trouble.

"No, no, please don't do anything like that. Let me tell them when I think it's right, but you do whatever you want. You don't have to hang around with me."

"I don't know. A gay boyfriend's quite cute. Every girl should have one. You can still be my strong protector until I pick out my victim."

It rains, even in Spain. My parents and Sandra's parents had gone off on some kind of coach trip, smiling as they left us "to entertain ourselves". We ended up in Sandra's room, since she had determined I was completely safe. My parents had booked a family room for us with two bedrooms, but Sandra had a room to herself.

We had a laugh when she told me that her Mum had also given her some condoms.

"Well," she said suddenly, "why don't we use a couple?"

"What," I said, falling for it, "you don't mean?"

"Don't I?" she said in a husky voice, getting one out of its packet with some difficulty.

She put it to her lips, said "Eurgh!" took it away, then put it back to her mouth and started blowing it up.

I did the same with one of mine and we made two balloons which we sort of patted around in the air. It was childish, but actually the most fun I had had so far.

We had some wine, and got rather silly. I told her what Granny had said to me.

It was then she decided to put makeup on me, and I was tipsy enough to agree.

My one and only rebellion had been not to cut my hair at university. Seeing the cool kids with long hair or the adventurous ones with weird hairstyles, the one I chose was the one which involved not actually doing something (and saving money). Coming home at Christmas and Easter, I had resisted suggestions, and had actually managed to resist before going on holiday.

So the first thing she actually did was to comb and brush my hair, which was actually rather nice, sort of friendly. Then the makeup, which took longer because we were giggling, and I didn't know how to hold still while she was doing my eyelashes.

When we were done, I looked at myself in the mirror, and we both laughed. But not much, because it wasn't as funny as we were pretending.

"I know!" she said," and went to the wardrobe, where she got out a green dress.

"Mum and Dad got it as a surprise for the holiday. I wish they wouldn't do that. It's a bit large for me, as you can't always tell from the sizes. This manufacturer is a bit generous. Come on, get your jeans and T-shirt off, and let's see you."

I slightly protested, but not enough. Over my head it went. It was sleeveless, so there was no struggle, and it was on. Later I realised how simple it had been compared with pulling up trousers and doing up the flies and belt. Just one go.

We stood silent for a moment.

"Oh," she said. The silence continued.

"You look better than I expected, J. D."

But I was lost. I was just looking at the girl in the mirror. Me. And I knew it was what I had always wanted. What I had always been. A girl.

I was happy in a way I had never felt before, and just wanted this moment to go on. It was so exciting to be a girl at last!

Exciting. Yes. And my boy's body knew exactly what to do. What would cause the maximum embarrassment.

I could feel a deep blush on my face as the stiffness began. And the more aware I was, the harder it became. I was mesmerized seeing the bulge starting to push my skirt.

And Sandra fell on the bed laughing as I tried to hide it.

"Oh my God! You fancy yourself!" And she started singing a bit of that song from West Side Story.

"See that pretty girl in the mirror there. Who can that attractive girl be? Such a pretty face, such a pretty dress, such a pretty smile, such a pretty me!"

She had tears of laughter in her eyes, and was gasping a little as she said "Just go to the bathroom and have a wank! You may as well try to enjoy it as much as I am!"

Cheeks still burning with shame, I slunk off. In the bathroom I pulled down my underpants and gazed at the offending organ. It was demanding, but I didn't feel like it. I saw a rather angry and sad girl in the mirror, holding a big stiff cock.

Sandra came in.

"It's all right, I'll do it. I owe you that at least. Get your knickers right off, and point it into the bath."

She got some body lotion and sat on the toilet lid.

Obediently I stood there, holding my skirt up. She was no longer laughing: she was being kind.

I had never been wanked by someone else, so it was a new and rather pleasant experience. I guessed she had done it before, as she certainly got on with it as if it was routine.

"You've got a rather nice one," she remarked, and I started to come!

"Oh, well done! And more! Oh yes!" she said encouragingly.

It was the best one I had ever had, and I felt so good afterwards.

"Keep your skirt up, and I'll clean you off," she said in a matter-of-fact way. I thought for a second she was going to suck me, but she got a wet flannel with a little soap, and washed me into the bath, also clearing away the spunk, and drying my shrinking cock.

"Put your knickers on, and come back to the bedroom," she said.

There she produced a green bra.

"It's supposed to go with the dress," she said, "So let's try it."

Off came the dress, and she put it on, which took a bit of fiddling with the straps. It was a bit tight though. She told me to take off my socks and we put them in the bra cups. The dress looked much better. And I felt better. And I needed a pee.

"Sit down, and wipe yourself properly," she said as I went to the bathroom. "We're not finished yet."

I tucked my cock downwards and brought my thighs together instead of holding it. And pissed like a girl! I was quite proud of myself. I used several sheets of paper to dab myself dry.

"And leave your pants off!" she called from the bedroom.

There were some frilly panties to go with the bra.

We had some coffee and talked.

Suddenly she said "Of course!" and I asked what.

"Your name: you should have a girl name, and I've been wondering what to call you. Then I realised you've already got one."

"Jeremy?"

"No, Jade! Jade is a green stone, and Jade is a girl's name, so when I called you J.D., I was saying Jade: J-A-D-E. It can be our secret!"

She looked at me and frowned. "If you want, that is. I mean, this is just messing about. We don't have to do anything again, if you're just humouring me."

I took a moment to think about it.

"No, I like it. At least on this holiday, please teach me to be a girl!"

She hugged and kissed me, like one girl to another.

"It'll be a pleasure. I always wanted a little sister."

The next bit of fun was showing me how to walk.

"This is how a man walks," she said, leaning forward with her chin stuck out and arms dangling like a knuckle-dragging caveman, then sort of evolving into macho man swinging his arms. Then she showed me how a lady walks, very upright, tummy in, elbows in, legs never quite straight. Then how a model walks, like on a tightrope, and finally how a girl on the pull walks, waving her hips. I tried to copy and we laughed so much!

She peeked out of the room, and we even walked up and down the corridor a bit until the lift went ding! and we scuttled back to her room before people came out.

It was nearly time for the old folks to come, and she had thought of something.

"Listen, Jady," she said. [Although I was supposed to be Jade, it tended to be Jady.] "These are your clothes now. I'll take them in my suitcase, of course, until we can work out a way of you having them at university. You can take the knickers home, though. If your mum and dad should see them, they'll think it's a souvenir of your sexual conquest."

"Now let's go shopping tomorrow, or at least window shopping. You could at least have some brighter man clothes, even if you don't wear dresses all the time."

I cleaned off the makeup and dressed as Jeremy again before the old folks came back from their trip. There was then an embarrassing family dinner followed by drinks in the lounge. I only had cola, having had enough wine for now. We were told about some historic buildings and fascinating facts rather muddled up.

Sandra said she'd like to go shopping tomorrow, and her Mum said "Oh good" and how nice it would be together, but she made it clear that it would be shopping just with me.

"Never mind, son," said Dad. "Better get used to trailing behind a woman."

Next morning it was sunny so our parents were heading for the beach. I went to Sandra's room, where she had a plan.

On went the dress, and up went my cock, and she wanked me off which was just as nice as before. Once cleaned up, I put on the pretty panties.

"Listen," she instructed me. "Girls don't wear dresses all the time, so if you are wearing nice feminine underclothes, that makes you a girl. You are now Jade, so you can go into shops just like any other girl, without embarrassment, because we are going to find some clothes for you. Don't worry, we won't spend much, it's the actual shopping that's the thing, with all the nice clothes that we can think about wearing."

I was thus introduced to a fascinating world. One that had been there all the time, but I was afraid to enter. Ostensibly she was looking for clothes for herself, but we were really looking for me. (Though quite often she fancied things for herself, and I was pleased to comment how I thought they would suit her.)

We stopped for cold drinks and occasional snacks rather than any formal meals, usually at pavement cafés where Sandra would comment on the girls going by, which was also fun. It was interesting that she praised some older women who she thought had style if not youthful figures. She had done O level Spanish at school and got a top grade so could talk with the locals a bit more than most.

I had to go to the Men's toilets of course, but sat down to pee, wiped myself and admired my panties.

We bought (and I paid for) another bra and panty set with a slightly larger band size, and a baby doll nightdress, again a bit larger than Sandra's size.

"Won't that be lovely to wear each night at university?" she said, holding it up against herself. I had to agree. In our minds we were designing a basic wardrobe for me as a girl at university, not just dresses of course. Some more feminine tops to go with jeans. Perhaps something that might be just a casual man's things, but definitely something more colourful. However, not bought at this time.

At last we bought a floral short-sleeved shirt. The sort of thing a tourist might wear on holiday. Or a gay man. Mum and Dad looked wide-eyed. Mum said it was very colourful. Next day I wore it not tucked into my shorts, which was cooler, but also a tiny bit like a dress, or at least a girl's top.

There was one more thing she bought (with her money): a necklace with a jade pendant which she put around my neck. My first jewellery, which did not show under a shirt or T-shirt, but I knew it was there. I bought another and gave it to her. That was nearly the last of my holiday cash.

We went to the obligatory discos and danced together, which I had not done before and rather enjoyed, though I would have loved to do so in a dress.

"One day you will!" Sandra promised me.

Sandy (as her mother called her) had to go shopping with the two mothers while the three men had a day together. I did my best and they did their best but it was pretty boring. However, I was glad to agree that I got on well with Sandra. This allowed my uncle to say how much he loved his stepdaughter, and how proud he was of her, and also remark what I fine young man I had grown into, and how his brother had always been so proud of me.

But the best thing was the times I managed to spend with Sandra, though I felt a bit down that I had stopped her from having a holiday romance. Particularly during the second week she pointed out boys she thought were particularly dishy, and I began to see them from her point of view a little. Or as a gay man perhaps. I had no practice in thinking that way, of course. I supposed it would come.

Then the holiday was over. Sandra and I kissed in front of our parents before going to our different flights. My thanks to her were sincere.

The dress and nightie and bras had gone. I was really worried about the panties and necklace in my case, but customs did not search it, and I was able to get them away and hide them before Mum took the washing.

Sandra knew what to do. She contacted Granny, who took charge of my limited girlie wardrobe. She said I could dress up whenever I came to visit her. Unfortunately I could only do this at weekends as I had a summer job to earn some money.

But they were wonderful weekends, wearing makeup and nice clothes and sleeping in a nightdress. Granny bought me some more knickers in different designs, and another dress and some tights. On the final weekend she actually persuaded me to go outside with her.

"Nobody knows you here," she said. "Let's just have a walk, me and my granddaughter."

It was such a lovely idea I could not resist. I was just walking about, a girl with her granny in a nice dress in the sunshine, and so happy. I told her about my new name, and she said "I think Jady sounds nicer." Of course, she was right, and that's what I became. Like Jerry or Sandy, I suppose.

She gave me a final gift of a soft bra with almost no cups that she said wouldn't show under clothes if I was careful. I took it and the new knickers, but left the dresses and nightdress and other bras with her for safekeeping.