Monday, 28 February 2011

The Prodigal Son - 2028 - Part 3 - His First Dress

Ray and his father stood in the dock, each dressed in shabby suits. Ray McCrae Snr had just been found guilty of twenty one counts of money laundering, extortion and threats with menaces.

The judge turned her wigged head in the direction of the foreman of the jury "Foreman of the jury, how do you find the defendant, Raymond Philip McCrae, junior? Guilty or Not Guilty?"

The female foreman of the jury answered immediately "Guilty, your honour".

A gasp went up from the galleries. Ray's mother broke down in tears and had to be comforted by her relatives.

It had been Ray's last sight of his mother, as he and his father were led away to the cells.

He had never felt so ashamed and humiliated in his life.

But, ten years later, what was happening to Ray McCrae junior at this exact moment in time was, for him, a hundred times worse!

"Give me a twirl!" his baby sister, Heather, ordered.

Ray obediently turned around slowly, feeling very foolish.

"What do you think, Cass?" Heather asked Cass Golde, one of her university pals that she had brought along.

Cass gave Ray an appraising and critical look and finally said "He looks adorable! You'd better take care of him, Heather, cos the women are going to eat him alive dressed like that!"

The two girls giggled.

Ray's face went a deep shade of red. What on earth had made him agree to this humiliation.

He had been offered an admin assistant's job at Al La Mode, a male clothing company owned by his mother. He had initially turned it down for two reasons. Firstly, he intended to resume the criminal activities he had gone to prison for, only this time he would make sure that he wasn't caught! Second, it had been a condition of the job that he wore a skirt, blouse and high heels, just like all of the other males who worked at Al La Mode.

He had been encouraged to re-consider his decision by his mate of long-standing, Doug, who owed money to a man who was known to break limbs even for trivial debts. Doug's idea for getting their hands on some instant cash had been for Ray to infiltrate Al La Mode for as short a time as possible, obtain all the information needed about the security of the place and then rob the safe. Doug could repay his debts and Ray would get a wedge of money to start over somewhere else.

Reluctantly, Ray had sought out his little sister, Emma, who had offered him the job, and told her he had changed his mind. He spun her a load of nonsense about trying to go straight and help the family and all that tosh and Emma had bought it.

But then Ray had to fulfil his part of the deal. He would have to wear a skirt and everything else to work at Al La Mode. This meant a shopping trip to Jessica's, the city's biggest department store. Emma was busy with work, so she drafted Heather (who drafted Cass) to accompany Ray to buy himself a new wardrobe.

And that was why Ray McCrae, aged twenty eight and a former hoodlum, was standing in the menswear department wearing a flowery frock that clung to the contours of his body to show off his bottom and his hips to best advantage.

He also wore a pair of black stockings on his slender legs and a pair of white high heels that he could barely walk in without threatening to topple over into an untidy heap.

Ray didn't even want to think about what he wore under the frock. He was actually wearing a bra! Not a woman's one stuffed with falsies, but a boy-bra. This consisted of a thin strip of lace with, straps, hooks and adhesives to hold it in place on Ray's upper torso, to preserve his modesty.

The point of the boy-bra, Ray quickly discovered, was not to make him appear to be a woman, but to make it obvious that he was a man who was undergoing the process of being feminised.

Ray also wore a thong with a pink heart shaped front panel and much glitter. Wearing it hurt like hell!

Ray groaned when he saw a store assistant wheeling up a rack of dresses.

"So, Cass. My brother has his first dress!" cooed Heather "Isn't that so sweet?"

Cass took another dress off the rack and held it up to Ray, whose head was bowed in shame "Oh, yes! Let's see what he looks like in this one!".

The girls made him try on about a dozen dresses before deciding on the two they would buy. Ray also had to try on shoes, skirts, blouses and tops. At the end of it, he was too exhausted to even feel the humiliation as keenly as he had two hours before. Heather and Cass were of course loving every moment.

Ray lumbered into the cubicle, eager to resume his normal, masculine garb.

His clothes were gone!

"Heather! Where are my clothes?" he demanded.

"You're wearing them!"

"I'm not wearing these outside! I want my old clothes. The ones I came in wearing!"

"You'll have to go out in the buff then. Those....rags you were wearing...I won't dignify them by calling them clothes....have been taken away to be burnt!"

Ray couldn't believe how stupid he had been. Whilst he had been trying on dresses, his sister had got one over on him and got rid of the only masculine clothes he had.

"Heather" he pleaded "I can't go outside in a dress! You have to get those clothes back!"

"Too late, I'm afraid" Heather said, without much regret or sincerity "Look, bro, you have a body that was just made to wear a dress!"

Later, whilst the girls went off to pay for Ray's purchases with Mum's platinum store card, Ray sat quietly with his head in his hands. Having to wear dresses! He felt utterly ridiculous and emasculated.

Nearby, he could hear two women having a conversation. One women, clothed in a tailored suit, was examining an evening gown.

"This one will do!" she exclaimed, taking it from the rack "Stephen will look quite ravishing in this little number!"

Her companion, also in a tailored suit, said "I quite agree with you, Cynthia! It will show off his figure to perfection".

Cynthia sniggered "He's going to hate this dress! Stephen's never come to terms with having to wear dresses! He really resents it!"

The two women laughed together "I can't wait to get home and see his face when I show him his new dress! His face crumples and he looks like he's about to burst into tears! He looks so pathetic and helpless"

Alix spoke next "My Geoffrey is very different from your husband. I can't get over the change in him. He used to be such a masculine man. Played football and cricket. But put him into a dress and he becomes all pliant and submissive! He keeps house for me beautifully, simply adores his frills and positively loves it when I order him around and chastise him. He is the perfect little wifey!"

The two women laughed. "We're so cruel to them, aren't we?". The two women moved out of earshot.

Ray felt rage against the two women and sadness for his gender. Men being put into dresses for the amusement of women! What had things come to?

Then he remembered that he was now in the same predicament. When Heather and Cass returned, they would take him home and show him off in all his feminine finery to his other female relatives.

In less than a generation, women had so dominated men that it was the men who now had to look pretty for and be submissive towards women.

Ray felt great shame.

Ray had to suffer the ordeal of leaving the store dressed as he was. He could barely walk in his heels and the girls had to help him down stairs and escalators. He had to expose himself, dressed in a flowery frock and stockings, to others. He was surprised and relieved to find that his appearance hardly raised an eyebrow.

Heather drove them home. Ray's purchases were taken to his room. Ray, his head down, went into dine with his mother, sisters and Aunt, in his frock. The women applauded him politely and offered him compliments.

Embarressed beyond endurance, Ray ate quickly and retreated to his room.

There was a surprise, for Ray's brother, Eddie called to see him. Ray had not been close to his younger brother. Eddie had lacked the street smarts and lack of morality needed to be part of their father's operation and so he had been left out.

Eddie had got a regular job, he had married and he had children. Last Ray had heard, he worked as a waiter in a local restaurant. Eddie was a loser in Ray's eyes.

Ray was stunned by his brother's appearance. He was dressed as a waitress, in a very short skirt, stockings and high heels and a frilled apron. His hair was long and had been coloured and styled in a very feminine way. Eddie was fully made up and had french manicured nails.

Eddie was short and slim and had delicate features. He would have made a perfect woman, Ray thought.

But then, dressed as he was now, Ray could hardly talk.

For a while, the brothers exchanged news. Ray had little, but Eddie went on about how well his daughters were doing, how his wife had earned yet another promotion at work and gushing praise upon his mother and sisters.

Then Eddie noticed the bags from Jessica's and pulled out a lacy thong. Ray blushed at the thought of having to wear the little strip of femininity.

Eddie twanged the thong playfully "Nice underwear, bro!" Then he looked at Ray "Heather tells me this is your first time in a dress, right?"

Ray reluctantly nodded. He felt so embarressed and ashamed.

"You'll feel shame now. I did when my Jennifer bought me my first dress and told me to wear it for her. But, I got used to it and you will too! Hell, someday you'll look back and wonder what all the fuss was about".

Ray didn't think he'd ever get used to having to dress like a woman. It went against all of his instincts.

Eddie left him. Ray looked around his boudoir, at his new high heeled shoes, lingerie and clothes, and at his dress. Everywhere he looked, he was reminded of his feminine existence and his status as a member of the weaker sex. Flowers, frills, ribbons, lace seemed to be everywhere, suffocating him, sapping his natural masculinity.

Ray put on his new silk nightdress, with its lace trimmings and pink ribbons. A part of him, a very small part, admired its prettiness, but his masculine core felt nothing but shame.


  1. Great story line
    I sitting here in a dress with heels and stockings drooling

  2. His first dress and the last trousers. ;)

  3. nice story

    sittin here in slip panties and cami

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