Do you want to be 'The Man in the Dress'

Are You ‘The Man in the Dress’?

What have I done – what have I won? What am I doing? Why am I trying on a whole collection of new clothes? Clothes so very unlike anything I have ever worn before.

I’ve put 50 stories up so far. I was aiming for the next one to be kind of special rather than just ‘ok’ !!….. but it’s not up to me to judge. If you feel like hitting the ‘kudos’ button for my stories or for anybody else – please be generous. And maybe even drop a dollar into the kitty for Erin who on our behalf has spent much more money than is sensible.

Thanks AP


I enter competitions. It’s one of the things I enjoy doing. Sometimes I win, generally I hear nothing. But I’ve won a year’s supply of dog biscuits (given quietly and anonymously to the local dog’s home); I’ve won a car which I was allowed to sell; two holidays – one to Skegness (which was nearly as dull as I expected) and one to the Edinburgh Festival with tickets for three days – wow). I’ve won quite a lot over the years. But never anything that made my life really complicated.

Until now.

I’ve won a competition which should, well, oh god, how do I describe the hole I’ve got myself into. I entered a competition for Beauty products and all that. Oh god, I really do have to go into details. The top prize was for a Lady’s Supreme Weekend. A trip to a famous underwear shop for new lingerie; then to a dress shop for three new dresses and other outfits; shoe shop for shoes to match; beauty parlour; hairdresser; to a Grand Presentation at a local hotel – and lots of minor items of less immediate importance - except the big extra : the winner would almost certainly be expected to attend suitable events in the weeks and months afterwards, for publicity and promotions.

And the prize was not transferable. Although of course I could refuse it.

And the prize could not be converted to cash.

And even though I had never even thought about anything like this. I had never pretended to dress up. Never thought about dressing up. Never wanted to dress up. Somehow, the idea of accepting the prize excited me.

What to do?

I’m a thirty-two year old single man. Five foot eight and slim-ish. Quite fit, with neck-length mouse-coloured hair. Nothing special to look at, I’d say. My social life is quite busy – after all I’ve had a number of girlfriends since I was seventeen. And I’ve been, er, active with about eight – and I’ve never had a one-nighter or actually anything less than a month with any of them.

I certainly don’t look effeminate or girly or anything like that – but where has this idea come from? And the idea is so strong. I can feel myself being readied for a plunge into ice-cold boiling water – and I’m ready. I want it. I feel absolutely certain that this is what I want to do. Even though I’ve never had any idea like this before.

I’m in a bit of a dither. Alright, I’ve flipped my lid temporarily – but this strange, burning intent keeps pushing at me. So, I call my friend Nancy.

“Nancy, I’ve been a bit of a pillock. I’ve got a problem and I think you can give me an idea what to do. I need to make a decision quite urgently – and I’m either going to be really embarrassed or very embarrassed.”

“Oh, dear me, boyo. That sounds just too exciting for words. Scamper over here. I’ll get the tea on and chill a bottle for later. Yeah?”

“You’re not going to believe this story. I’ll be there in about half an hour. Thanks.”


“You’ve done WHAT?”

“Erm. I said – I won this competition.” And I waved the leaflet at her.

There were tears in her eyes. “I wondered about entering that. I could see me having such a great time. And now it turns out that you’ve won. You plonker. Didn’t you read the conditions. The strict rule that this was only suitable for women over the age of 18. You idiot, dolt, you mere man.”

“Yeah, but I didn’t expect to win.”

“Well, you shouldn’t have entered, should you. Idiot. Again.”

“Nance, my chum. We have to deal with what is – not what we would like. I’ve got this situation – what do I do about it?”

“Why are you even thinking about NOT refusing the offer? You’ve just told me that you’ve never even thought about doing any girly type stuff. You’ve never cross-dressed, have you, you said. Have you ever worn your sister’s panties? Stolen any of mine from the laundry hamper? What have you done in the line of a dirty young man wandering through Marks and Sparks fondling the panties and looking at the bras? You’re blushing. So at least you’ve been that interested in girly stuff.”

“Well, yeah, but only because I don’t get near enough often enough to the real thing.”

“So, if a girl asked ‘do you want to get into my panties’ – you’d never think of wearing them for yourself.”

“Erm, no. Perhaps if she suggested it as some sort of sexy prank.”

“We are far far away from a ‘sexy little prank’ here, my friend. This has to be for real – if you’re going for it. And I guess you wouldn’t be here unless you were thinking that way. Am I right?”

“Erm. Dunno. Really, I don’t know. It’s just. Somehow I’ve got in into my mind that I’d like to find out.”

“Find out what?”

“What it’s like to wear pretty clothes, to be made to look beautiful. Whether it would be exciting or weird or what. Am I nuts?”

“You’re going a bit beyond the average for unusual behaviour, that’s for sure. Have you any idea why you’ve started wondering about this?”

“No idea. None. I might have been wandering the internet, like you do, but I’ve never deliberately looked at tranny stuff, the shemales, the sissies and all that.”

“You know a lot of the words for someone who’s done no wandering in that area!”

“Well, y’know. Late evenings with perhaps a drink taken.”

“You ARE a dirty young man.”

“No, really, really not. But now I think about it there was one picture that caught my attention. It was me – it really looked like me and then suddenly it was transposed, transformed into a girl. As if I was a girl. And she was really pretty.”

“Well, show me.”

“Can’t. I only saw it the once and I could never find it again. I did look because I couldn’t believe how real the girl was and how like me the boy was. And now it’s in my head. And I can’t get rid of it. Then I won the competition. I entered some weeks ago and got the news last night. I found the picture about a fortnight ago so I didn’t enter with this in mind. I couldn’t have – the timing’s all wrong.”

“But now that the picture IS in your head – you’re wondering, eh?”

“Guess so.”

“So – choices. Are you going for this or not.”

I took a deep breath. “Yes.”

“Are you going to tell them in advance that there is a problem?”

“Give me some for and againsts.”

“If they know, they can prepare to do a better job. You’ll know in advance who is willing to help and who isn’t. They might want to build a new advertising project ….. ‘if we can do this for a young man, how beautiful can we make YOU’ sort of thing. I’m sure I can think of other points.”

“Perhaps it’s the hair.”

“What d’you mean?”

“I’ve always been fascinated by long hair. And the competition promises hair extensions. I’ve always wondered what they’d feel like. The hair brushing against my neck and shoulders. I’ve always had an eye for girls with long hair.”

“NOW we’re getting to some of the nitty-gritty. That’s interesting. Just hair is it. Not makeup, lipstick, frills, or anything else.”

“Well, not until that photograph.”

“That’s really got inside your head, hasn’t it.”

“Did the girl in the photograph have a name?”

“Not that I remember. Giselle maybe.”

“Did you look up all the combinations of Giselle and transition, cross-dress, transgender and so on?”

“No, I tried to find it on the history – but without success.”

“Should we look to see if Giselle is for real?”

“I don’t know. I think if I’m going to do this, then it’s me for me, not me as a copy of anything.”

“That’s a much better attitude. Don’t be a copy of anything – be an original. Now let’s look at this leaflet and your letter. Exactly who are the companies who have signed up to this. I’d be more certain they’d be flexible if they were local rather than part of a chain. And do I get anything from any of them myself.”

There was a pause while Nancy read. I picked up a magazine and, pure fluke, found it falling open at an article on hair extensions. I was as usual instantly fascinated. I really did love long hair – and here (perhaps) was an opportunity to find what it was like for myself, on myself. I wanted it. Each time I thought about it, I wanted it more.

“How are you going to deal with work?”


“and how are you going to deal with your parents?”

“um ….”

“And what are you going to do if you like it?


“And you haven’t thought about this at all have you?”

“errghgh. No. Clearly not. I just ….”

“You just what? Got yourself into a tangle, got all excited about the hair idea dn put your brain in neutral. You’re a pillock. Even for a man, you’re being dim, stupid, unbright. Pillock.”

“Okay, yes. I didn’t think it through. But I’m still fascinated by the whole idea. I think I still want to do it.”

“You are as bonkers as custard on steak.” She did have a few amazingly colourful expressions learnt from her Jamaican grandmother.

“Help me, please.”

“You know, that one of the few times you’ve said ‘please’ to me and definitely the first time you’ve said ‘help me’ as if you meant it. You want my help, truly. You’ll do what I suggest.”

“….. Yes. Yes, I will.” I repeated it more forcefully. “I don’t know how this is going to work out but I want to have the experience.”

“First off, I really think you’re going to have to be up front and open to the organisers. You are willing to do whatever they ask but you’re doing it as a young man interested in the experiment. You’re not, as far as you know, transgender in any way. You just want to know what it feels like in a beautiful dress, with long lustrous hair out in public.”

“In public?” I squeaked.

“Did you read ANY of the competition rules. Were you pissed or something when you did it? Gawd, you’re even more off beam than I thought. Yes, In public. Several of the events you have signed up for by ‘winning’ include appearing in public and even speaking in public.”

“I think they’re going to throw me out as fast as they can.”

“Yes, but maybe no. It mostly depends on what they can see in you as a new and different advertising package. I think we need to measure you thoroughly, go to the shops and see what sort of things you would be willing to try – then talk to the organisers. When do they want a reply?”

“Probably by today, but I’m sure tomorrow would do.”

“We need to get ahead of them. Give me their details and I’ll do a bit of webbing to find a mate who can help. After all, everyone is only a few clicks away.”

“Mmmm. Okay.”

“And we’ll go to my salon too.”

“Wha, why?”

“So you can try on a few wigs and decide if they’re anything like you imagine or if they give you some idea of the feel you want.”



It didn’t take very long for Nance to find her link.

“Yvonne, it’s Nance. I’ve got a problem and an idea.”

“Cooee, that’s not the usual start to one of our chats. What about the wine, the where and the when.”

“Definitely but later. Are you able to talk freely?”

“Pretty much, wassup?”

“I have a friend who has been told they’ve won the Beauty Girl contest.”


“Wants to know the feeling of wearing a beautiful dress, long hair, all the works.”

“And …”

“30 years old, bit of a hideout, definitely inexperienced, willing to do pretty much whatever the organisers want, five foot eight, thin but not skinny.”

“And – how about some numbers, breast, waist, hip, cup, weight, you know.”

“I haven’t got all the measurements yet. But we’re on our way to get some new undies and a dress.”

“Whaat. Excuse me. What is going on here? A 30 year old and you’re going to get underwear and a dress. What is this some sort of wind-up or what? You’re not trying to swing this for some sort of freak or something? What is she, three foot tall, three foot wide? A nun? An alien with green skin?”

“Getting close, Yvie. She’s a bloke. My sometimes friend and neighbouring idiot, Martin. He entered the competition without reading the rules and conditions (he was probably a bit pissed) but weirdly and amazingly he wants to go through with it. Even though he’s never dressed up before. I’ve met some of his friends before and the girls say he’s definitely not homosexual – but he wants to do this. Full on, willing – at the moment – to agree with whatever he’s asked to do. I’m not sure I understand what this is all about – but he’s not drunk. He’s not, visibly, been smoking wacky baccy or drugs or anything like that. He’s just hit the weird-ometer bigtime. What do you think?”

“If he wants to put on a dress, there must be easier ways.”

“I haven’t asked him about that. But he has won the competition. So?”

“Yeah, ‘so’. So what do you want me to do?”

“How about sounding out the organisers. You’re an occasional journalist. Give them the story as ‘I’ve heard about this exciting new project you’ve got now that your winner turns out to be a young man …. and that he’s willing to comply with all the rules of the competition, the dresses and the appearances. I’m so excited to see how you can sell all your products with, what’s your slogan going to be? ‘If we can make a young man this beautiful, what can we do for YOU?’.”

“You have been doing some thinking about this. And Martin is really willing to go with this?”

“I think he’s planning to get at least some money out of this. It’s going to be difficult for him to stay with his company if he takes a lot of time off.”

“What does he do now?”

“He’s currently a web-designer, having been a salesman until he diversified.”

“So, what? Mid-level, earning okay but would like more?”

“Pretty much.”

“I’ll send out some feelers. Be back asap. Then a BIG drink this evening, yeah.”

“Usual place, yep. 7-ish.”

I pulled my eyebrows back down after their exhausting effort at going up and up and up as Nance’s call progressed. “So.”

“As yet, nothing changes. We gotta get moving and see what you could look like.”

So – it was into town and in and out of a variety of shops that I had never been into before. Never thought of going into before. Salons to talk about hair extensions, hair-styles, nails, makeup lessons and options that baffled me. Words that baffled me.

Then the clothes shops. First the underwear shop – where Nance insisted that I ask the girl to help me choose a bra. And insisted that I ask if the girl could check the fit for me. And then made it worse by asking about inserts and fake-boobage. I was alternately scarlet and pale.

But I did leave the shop with several bras of my own – including the one I was wearing which held a set of 36 D prosthetics. That’s what the girl said the proper word was for them. They were lightly stuck to my fortunately almost hairless skin. Nance had popped next door to get a quick razor to minimise the fluff even more. The weight of the breasts was weird, but fascinating. The new curve at the bottom of my eyeline was equally interesting. It was indeed true that it was more difficult to see my feet. That made me smile.

Then back to the dress shops to find some clothes to wear that fit my new outline and my new character.

And I still didn’t understand why the whole idea had taken off like it had. Why was I suddenly so intent on dressing up, on pretending to be a woman, even going so far as to be willing, if not eager, to parade in public as a cross-dressing man. To consider doing so as a deliberate publicity angle which would ‘out’ me as thoroughly as any cross-dresser had ever been outed in recent years.

Was I nuts?

But I left that shop with three dresses, four blouse and skirt combinations that would make ten or more outfits. A couple of cardigans and other sundries.

Then to the shoe shop – and the whole rigmarole began again. Measurement. Try-on. Try-on more. Select. Pay. Leave.

And into several accessory shops – Select, consider, change, more choices, decide, pay. I could feel my wallet whimpering with pain. But my determination to present to the organisers seemed to outweigh any potential embarrassment.

The car was full of bags by the time we left. The last stops were various second-hand and charity shops where Nance said “there’s always a chance that you’ll find something really good for just pennies. I got a beaut handbag a few weeks back.”

“How are you coping with all this, eh, Marti?”


“Whatever you might say, I aint acallin’ you ‘Martin’ dressed like that. Do ma street-cred no good at all. Not until it’s all sorted and the contest organisers want to have you out as ‘Martin, the man who won our girls-only competition’. Or whatever they decide to do.”

“Have you heard from Yvonne?”

“Not yet – but I expect she’ll be pretty quick in getting an answer. But whether that’s going to be a ‘go or a go away’ – that I haven’t got a clue about. Would you be upset about a ‘go away.?”

“I really don’t know. I don’t know quite why I’ve got so intent on this idea of dressing. It’s as if I’ve got a splinter - and I can’t rest until it’s fixed.”

“If you asked me – you’re completely bonkers. But if you really do want it then Yvie is the one who I reckon is most likely to make it happen. She’s really good at getting things to go her way – or in this case – getting them to go your way, Marti girl.”

There was a pause as we walked to the nearby coffee shop. Nance saw me watching the other people walking by.

“Tha’s good. To look at the folk and see what you like. Every time you sit and watch you’ll see several outfits that looks awful and maybe something that looks great. And sometimes you’ll think ‘now that piece with that other piece would look great on that woman’. But by golly where they are on who they’re with – it don’t work none.”

Almost as we sat down, Nance’s phone rang.

I could tell from the excitement and the voice that it was Yvie – and that the news was a ‘go’.

Nance’s eyes lit up as she listened. She nodded enthusiastically at me. As soon as she was off the phone, she said ‘we’ve gotta move. They want photos and some clothes from a couple of specific stores. And they want to see you in them asap. Move it, Marti girl.”

I moved it – even though my feet were beginning to hurt. And the heels were only 2 ½ inches high.

Was I mad? Had someone drugged me? Had I been hypnotized? What was I thinking?

Would I work out answers before or after I took this truly ludicrous idea any further. I could see that the pressure was building and that all too soon someone would be saying ‘there’s rules and so on that you’ve broken – do you want to go to court about this ….. or else.”

What did I really want to happen. Then the breeze caught the edge of my dress and I thought once more ‘that feels gorgeous. What have I been missing for so long? Perhaps I just want to break out of my cosy little hutch and do something wild?’

My mind clutched at the thought and I grabbed a pen from my pocket ‘The Man who wants to be Different’. Perhaps that was an idea I could put forward. I suddenly realized that I was really tired of being ‘just too ordinary’. Time for a change – maybe?

But was converting my whole wardrobe and lifestyle to that of ‘The Man in a Dress’ - was that going too far. I didn’t know – but I was enjoying the process so far.

The two shops which Yvie had specified weren’t too far away. It was fortunate that they both had branches in our mid-sized town of Birchester. And that they had some of the items which were listed on Nance’s phone in the right size for me.

Once we had taken a whole series of photographs and selected the 10 or so best – and emailed them to Yvie and the organisers – I thought we were done for the day. But Nance said we were meeting Yvie in an hour to talk about the possible range of options. What we might be able to push for. What we or rather I, might be pushed into doing.

Yvie liked my phrase ‘The Man who wanted to be Different’. And she had already talked with the organisers about a campaign based on ‘The Man in the Dress’.

Perhaps ……..

I just don't know what will happen next ...... who does?

If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
141 users have voted.

And please, remember to comment, too! Thanks. 
This story is 3913 words long.