Magic Dress - Sam Pt. 01

CHAPTER 1

It started with the makeup, especially the eyelashes. The dresses came later.

It was a special wedding anniversary, and we had holiday in Bangkok. The children were now grown up and almost out of the house. Our daughter was well away and our son had a promising girlfriend at university, so we had high hopes of losing him too. The main thing was we could go on holiday ourselves, and even afford it (just).

My darling wife Marie had always wanted to visit Thailand, and I am glad to say it did not disappoint. We stayed in a lovely hotel. The staff were so friendly and eager to help, the food was fabulous, and our trips out were great. I even had a suit made to measure at quite a low price, delivered and adjusted in a few days.

Best of all, there was a little office in the lobby with a sort of travel agent: a little woman who seemed about 100 years old, but was utterly charming. We discovered her recommendations were really good and avoided some of the rip-offs. We went on sight-seeing trips until we had seen enough temples to last a lifetime, but all beautiful. A boat trip to a floating markets. Even to see tigers close-up! But her suggestion for a ladyboys show made us hesitant.

"Is nice," she said. "Nothing rude." She looked at us questioningly. "You want rude show? I can fix." We shook our heads.

"Thought so. Is just cabaret, sometimes funny. Nice music, dance. Lovely costumes. And girls so pretty you not believe!"

"Many married couples like, go again."

We decided to risk it and were glad we did. The trip included transport door to door, dinner and some drinks.

"Enjoy," she said as we left.

We both agreed the show was fabulous. It was everything she said. There was nothing indecent, but they were a little rude, in sort of mocking sex shows and themselves. Yes, very glamorous and sometimes funny. You could tell that some of them were men, but only just. However, they were all pretty and some unbelievably beautiful in their glamorous dresses and sometimes leotards or bikinis.

"They didn't seem to have a cock between them," Marie said in amazement.

I was slightly embarrassed by the way my cock had made itself known quite often during the show. I was not at all embarrassed by the way it performed afterwards. We were both desperately turned on, and screwed passionately as soon as we could get most of our clothes off.

We were cleaning up and making ready for bed for sleeping, when she said "Do you love me?"

"I just proved it," I said and we laughed. "Why?"

"Would you let me put some makeup on you? I really want to see how you would look."

How could I refuse?

I have to confess I have always liked women in nice makeup, which is good because Marie likes to wear it. She said she would sooner be seen naked in public than without makeup. I said seeing her naked with or without makeup was always good for me.

Of course, I had seen how it changed her. Don't get me wrong, I love her and like her without it. Her explanation is that she is a wife all the time, a woman without her makeup, and a lady with it. Oh yes, and with a bra. While she is often without a bra for comfort at home, she will not answer the door unless she is wearing one under her clothes. Obviously I like her a lot without a bra, but appreciate the way she always looks smart. A proper lady.

I shaved, of course, and discovered that there was a lot more to the process than I had realised. There was an element of shading with the cream and powders. Lipstick of course made a big difference as I was not used to seeing it on my face.

She trimmed some stray hairs from my eyebrows and nose with nail scissors, then marked the eyebrows, which definitely made me more of a woman. But the eyeliner and most of all the mascara on my eyelashes made me surprisingly feminine. Eyeshadow made me glamorous.

"There!" she said in triumph. "Sam is now a ladyboy!"

We had bought her a Thai silk dressing gown, which she went and got. It was a little small for me, but I got it on, and tied the belt. She put a silk scarf on my head and we looked together in the mirror in amazement.

"My God!" she said. "You're so pretty! Flutter those eyelashes for me!" So I did.

We both said nothing for a while.

"Do you like yourself like this?"

I hesitated before saying "Er, it's interesting."

Next day she bought a larger size of dressing gown. In the afternoon we went to see a different ladyboy show, and came back to the hotel, but did not have sex straight away. Instead she made me up again. I was also fitted with one of her bras. I say fitted because she had arranged something at the back to allow for my chest being larger. The cups were stuffed with some knickers, and I was put into tights before the new dressing gown. She did the belt quite tightly, and put the scarf on my hair before being satisfied.

"Yes," she said. "Makeup and a bra! You really are a proper lady now. Walk about. Show yourself off and admire yourself!"

Which I did. It was funny, but exciting and impressive how good I looked.

"Do you know what your best feature is?" she asked.

"My eyelashes?" I guessed.

"They are really good," she admitted. "But I was thinking of that stiff cock trying to escape from your tights. I think you should let it free!"

In makeup, with a bra and in what was virtually a silk dress (and tights still on one leg) I gave my wife a very satisfactory fuck!

"I'm glad we still have a cock between us!" she remarked afterwards.

For the remaining three nights I was made into a lady and fucked her. It was a great holiday!

Back home it became a tradition on Friday night for me to have makeup and the dressing gown and bra while we enjoyed a Chinese takeaway (the nearest to Thai food). She said somehow the ladyboys had been hot, and we always had great sex that evening.

She said she liked me in makeup, mentioning Johnny Depp, of course! I got used to it and I think quite liked it - appreciating a little what it did for her and her confidence as a woman. I was still me, but, fancier. The eyebrows and eyelashes especially. And of course, lipstick. My eyebrows were trimmed regularly - not removed, just shaped a little.

I don't know - did we play up the lady bit? From what happened later, I think we may have. Sometimes I would walk around, putting on a higher voice with hand on hip etc, and she would call me Samantha, but I thought it was just fun, nothing serious. I put on her nightdress a couple of times, with some frilly knickers. Just silly games.

CHAPTER 2

A year later we had an anniversary holiday, but I did not know the details. I guessed and hoped it was going to be a concert with Jenny Lind, a singer I rather fancied. I liked her singing too.

We stayed in a very nice hotel and in the morning took a taxi to a discreet door. Inside there was a waiting room with a man sitting there, looking clean and smart.

"Hello," he said. "I'm Deidre." I obviously looked puzzled.

"Because I'm Ken the rest of the time. Ken and Deidre. In Corrie?"

We still looked blank, but he had his hand out, so I shook it.

(This is a reference to a couple in a long-running British TV soap opera Coronation Street. Their TV wedding had a bigger audience than that of Prince Charles and Diana Spencer. But obviously Sam and his wife are not fans.)

"I'm Sam," I said, "and..."

"Samantha?" he interrupted.

"No," I said, "Samuel."

"Fine," he said in a resigned way. "Forget it. This must be your lovely wife. You're a lucky man!"

She smiled and shook his hand.

"I wish my wife was here. She tolerates my dressing, but doesn't support me. God, I envy you!"

I was no wiser, but my wife looked as if she was trying not to laugh.

Just then a very smart and good-looking woman came in. Quite tall, with a figure like a catwalk model, slender but nicely shaped, in a short skirt but very proper.

"Oh, hello, Deirdre. Nice to see you again. And you must be Sam, is that right? And of course your lovely wife, Marie. My name is Joy. Let me welcome you both and hope you enjoy the day."

"Now Deidre knows the score, but just for Sam. We will do our best to transform you into the lovely ladies you really want to be. There will first of all be a glamour shoot, then a party dress, and finally a walking outfit, and we will have a nice stroll outside, all girls together."

"What the fuck!" I exclaimed, and everyone looked at me.

"Please," Joy said sternly. "Remember there are only ladies here today, please act like one in every way!"

Marie was covering her mouth and unsuccessfully trying not to laugh.

"Oh," said Joy. "You didn't know! I'm sorry. Your wife said you liked dressing up and makeup, so thought you might like to try being a girl for a day. She has been a bit naughty in not warning you. You don't have to. You can leave if you want, or wait to see what we do with Deidre, but I don't think I can give a refund."

"Go on," urged Marie. "Just try it for me. We're here now, and no-one will know." She turned to Joy.

"It's not been much. I told you on the phone how it started. But we've just done a bit occasionally, with makeup and a silk dressing gown with a bra underneath. We both like it and he looks really good, so I really wondered how he would look as a woman, and thought he deserved to try it."

She turned to me. "Sorry, darling. I knew you would never agree if I just put it to you. If you insist, we'll just leave, but what is there to lose?" And she kissed me.

It had only been a few times, I thought, and only to please her. I saw how she had been laughing at the practical joke. I dreaded to think what it had cost.

"What sort of people are you?" I asked rather rudely. "And what is this business?"

Joy was obviously offended, tightening her lips, but put on the smiling face of a professional receptionist or something similar.

"This is not a business," she said. "It's a hobby. My sister and I are makeup artists, working with photographers, and the film industry. When we have time, we try to help men who like being women. Most of them just like dressing up, but we have some transgender ones we have helped. I am transgender myself..."

The surprise must have shown in my face as she paused.

"... but my sister is not, so we have a good range of experience of being a woman and becoming a woman. We charge a reasonable fee for the time and use of materials and clothes, but it is mainly because we like helping people. We also have social events for which there is no charge, just for safe time in all-female company."

"Sorry, I didn't mean to offend," I said.

"It's all right," she answered. "I'll take Deirdre and make a start. Have a think. Sybil will come round in a bit to see what you've decided."

As they were leaving the room, Ken/Deirdre turned and said "Give it a go, mate, or at least stay so that you can see me. I really like you and you will be amazed what these girls can do. He smiled appealingly.

"OK," I said. "I'll give it a try."

CHAPTER 3

About five minutes later Sybil came in, a small woman with bright red hair and a bouncy personality, wearing a sort of apron with lots of pockets and things in them. She was, of course, perfectly made up, and pretty.

"Now," she said. "This is our reluctant princess, is it? Don't worry. Just relax. It's only a bit of fun."

And actually it was, but only because she was so clever. She kept up a constant chatter, simultaneously explaining things to Marie for future reference, and telling tales of experiences with the film industry and photographers.

Behind a screen, Marie helped me on with some lacy silk-feel knickers shaped to include my man bits and a sort of bra and breasts combined to give me a cleavage. I then put on a wrap-around smock and sat in a chair like at the barbers. Sybil then shaved me and put a sort of cover on my hair, then applied God knows how many layers and false eyelashes. Finally I was given a wig, and invited to admire myself in the mirror.

"That's amazing!" said Marie. "You look fantastic!" and Sybil beamed.

I looked at myself: a tanned cover model, over made-up. And didn't like it.

"Very nice," I said.

We sat and had a cup of tea, as Sybil said "for me to get used to it". I didn't get used to it. I looked silly.

Then there was some work taking the fake tan makeup down my neck and blending it in with my fake tits. I was instructed to go to the toilet, which I did.

Coming back, I put on patterned tights, and a wrap-around dark red satin dress was put on me. Again I was invited to admire myself in the mirror, while the two women commented favourably.

"Amazing!" I said as enthusiastically as I could, while definitely not admiring myself.

I was then draped on a chaise-longue wearing shoes with ridiculous high heels. There were fixed lights and flashes, and Sybil had quite a big camera, all very professional. She posed me with false cleavage showing and one leg raised a little so there was a lot showing out of the dress. She flashed and poked me and moved me and flashed some more, telling me to look up, down, pout, smile and so on for ages. She kept looking at the screen of the camera and sometimes showing it to Marie, who seemed pleased.

When she was satisfied, off came the dress, the fake tits, the makeup and wig. We had coffee and biscuits.

"Right," she said. "That was the glamour shoot, now let's get you dressed for a party!"

I was given a padded bra with no cleavage, different makeup and wig, and put into a pink dress with a higher neckline, short puffed sleeves and a short skirt with lots of lace underneath. I had tights and pink shoes with low heels.

Looking in the mirror I felt a proper twerp, but the two women enthused on how pretty I looked. More photographs were taken with me posing as instructed and smiling as well as I could. Holding my skirt or putting a finger to my chin was really silly. I did not like it.

I was then taken to see Deirdre.

Ken was a bigger man than me with a square chin, dressed as a bride in white. My prejudices were getting ready to be confirmed.

But he was radiant. He was so happy, I could not begrudge him the feeling, and in a sort of way I understood. It might be hard to persuade people he was a real woman, but in himself he was as feminine as could be, and I wished him every happiness. Maybe my outfit was not so bad, after all.

We praised each other, and were praised by the women. I was no longer grumpy. Not feminine, but OK with being dressed up for fun.

CHAPTER 4

We were wisely given frilly aprons to wear while we had a stand-up buffet lunch. (Quite a light one.) I was asked several times if my shoes were still OK during our pretend party. Joy talked to me, and asked me about my work and interests, while instructing me how to speak. Just in the upper region of my comfortable range, and a little soft. She reminded me to be a lady if I started to go off when I got enthusiastic. She also adjusted the way I was standing, and began to get me to take steps more on the balls of my foot. Deirdre was being kept walking around by Sybil, while Marie chatted to her.

We then parted for a toilet break and to change for the final session.

I was in the makeup chair again scrubbed clean, and Sybil was looking at me thoughtfully, when Marie said "Do you mind if I try something?"

She put on makeup in the way she had always done it on me since Bangkok, and Sybil inspected it minutely. They then had a technical discussion about eyeshadow, and agreed a different shade. With a new wig, in the mirror I looked the best I had looked that day, or ever.

I felt OK about the makeup, but was less happy about the promised finale, where apparently I would be taken outside for a quick walk, not more than ten minutes. For this, an everyday outfit was required: smart but not drawing too much attention.

Sybil had put together a selection in my size, and asked me which I would like. Two women looked at me expectantly.

"Whatever you like," I said, and shrugged. "You choose."

I was just thinking how glad I would be when the day was over. It had been a crazy idea by Marie, and sort of interesting in a way. But never again. She could put makeup on me if it amused her, and look at the pictures of me in costume, but I was not going further. In a sense it had been useful. I was not going to be a crossdresser like Ken, though good luck to him.

They held up dresses and suits to me, when Marie said "What about that one over there?"

It was a green dress. I didn't notice anything else about it, I was just resigned.

"Maybe," said Sybil. "Actually, we've had it for ages and no-one has chosen it. It's still got the price tag on it." She cut off the tag, and they put the dress on me.

You know how in films sometimes they change the scene by moving a line down, and sometimes it shows someone dressed in one way, then another. It was weirdly something like that. As the dress was raised above my head, I was Samuel. It came down and in the mirror was Samantha!

There was a sensation of calm and prettiness and being right and proper. Femininity.

This must be what Deirdre and thousands like him (or her) must feel. It was not the artificial appearance of the glamour shoot or the forced femininity of the party dress, just the everyday naturalness of it. It was almost shocking how easy it had been.

There was just one thing wrong.

"Not this wig," I said. We all agreed and put on another one. What a relief!

I had new tights and shoes, dark ones with heels of about two inches. Sybil got me to practise walking under her direction, and I was eager to learn. I was clumsy, but in a strange way it seemed as if it was something I had done before and was getting back to, after an accident or long illness.

Some more photographs were taken. This time I did not need much encouragement to smile, and Marie was beaming as she stood beside me for some.

Deirdre joined us and said I was amazing. I said the same of her. She came closer to whisper in my ear.

"I'm terrified, mate." It was Ken talking. "I so much want to go out as a woman, but I've never been able to manage it. Could I hold your hand?"

I was given a green cardigan. Deirdre had a jacket over her blouse and skirt. Holding hands, we went out.

Deirdre had been practising walking at home, so was better than me. After about a hundred yards, she let go of my hand and turned with a smile to say "Thank you so much, Samantha dear," in quite a feminine voice, and I felt good.

Joy took us, while Sybil stayed to deal with the photographs. She kept pointing out things - a bit of architecture, a cat washing itself, some birds in the trees - just to keep us from wondering what others were thinking. In a while it was just a pleasant stroll around a nearby park, and the ten-minute walk became a thirty-minute one. Just a group of women chatting.

Back inside it was Ken who said "Whoo hoo! Nailed it!" before becoming Deirdre again, and thanking us all. He insisted on giving us his contact details and we felt obliged to do the same.

Joy who asked me how I had enjoyed the experience.

"Wouldn't have missed it for worlds," I said sincerely. "Can I buy this dress?"

"If you like," she said. "Sybil told me you liked it, and we have the price tag. Just give us that. Take it off and I'll put it in a carrier."

"Wait a minute," I said. "How about the wig? Can I buy that as well?"

She hesitated.

"Well, it's a good quality one. I am sure you can get one much cheaper that will do. If I sold it, I would have to ask the cost of replacement."

"Fine," I said immediately. "And the shoes too. In fact, everything I'm wearing. Don't cheat yourself. I want the lot."

"I'm so pleased the experience has been worthwhile," she said with a big smile. "I hope we'll see you and your friend Deirdre at one of our social times. They're free. I'll let you know when."