The Prodigal Son - Part 7 - Maid to Please

After his experiences of the previous day, Ray did not feel like going into work and so he phoned in sick. 'Men's troubles' was the reason given for his absence. His friends on the admin team used it all of the time.

He lay in his silken and lace bed, feeling miserable.

His sister, Heather, came to visit him. Heather was wearing a pair of slacks, an open shirt and a red pullover. She was going to play golf with some of her friends, but, as a medical student she had a interest in medical problems.

She took Ray's pulse, felt his forehead and even produced her stethoscope and used it to listen to Ray's breathing.

"There's nothing obviously wrong with you" she announced "You're depressed and agitated. A good day's sleep should help".

After Heather had left, Ray leapt out of bed. He showered, perfumed his hairless body and dressed up in a satin gold blouse, a matching red skirt and jacket set and red high heels. Underneath, he wore lace topped black stockings, a lace boy-bra and white, lace-trimmed french knickers. Ray made up his face and picked up his handbag and went out.

An hour later, he nervously entered the Duck & Ferret public house in one of the poorer districts of the city where his mate and partner in crime, Doug was waiting for him.

Ray was hoping to persuade his friend to abandon their plan to rob his mother's company. Ray had initially been up for the robbery, even though it had meant that he had had to eschew traditional masculine clothing in favour of what he now had to wear. But, weeks of having to live in feminine clothes and living a feminine life, had altered him. He was losing the masculine instincts that had made him strong, assertive and confident and was instead adopting the more feminine qualities of timidity, lack of confidence, submissiveness and even a liking for pretty, frivilous things.

He was no longer up for doing the robbery. In fact, he was scared out of his wits at the thought of being involved in crime.

He went to the bar and bought himself a glass of white wine and a pint of beer for Doug.

Doug smiled at him appreciatively "Thanks". He looked Ray up and down "Bloody hell, you look like a posh bird. If you have to dress up like a bird, wear a mini-skirt. You've got cracking legs!"

Ray went red "I didn't dress up for you! I did it for me". It was true.

Doug sneered "You actually enjoying dressing up as a woman, don't you? I can't believe it. The great Ray McBain, heir apparent of his father's criminal empire, has become Miss Moneypenny and is loving every moment of it!"

"Doug, never mind that. We have to abandon the plan to raid Al La Mode", he said in a whisper.

"What?"

"We aren't ready! We have less than two weeks before I have to away to college".

"What do you mean, we're not ready. I'm ready! As soon as you do your part. Seems to me, you're the one who isn't ready!"

Ray looked down at the tips of his high heels, unable to contradict him, for he was right.

Doug took one of his manicured hands, gently, like a lover, and then squeezed it tightly. Ray gasped in pain. Doug leant over as if to give him a kiss and whispered in his ear "Listen to me, you stupid bitch, I'm in serious trouble! I need that money like yesterday, so why don't you stop playing at house or whatever is going on inside your head, and get us the combination to the safe! The sooner you get the combination, the sooner we do the robbery and then you can become Miss World for all I care!"

The Miss World competition had been abolished seven years earlier, as a result of feminist agitation and the ascendancy of women. Doug was the one who was out of touch with the real world.

"You're hurting me! Ray protested. Doug released his hand. "Get that combination. Soon". He whispered. "Now, get out of here. I'm sick of drinking with bloody trannies!"

Shaken and in pain, Ray gulped down the rest of his wine, picked up his handbag, and stumbled out of the pub, on the verge of tears. His attempt to avert the robbery had been a complete failure. Not only that, but as a result of him having to wear skirts, Doug had lost all respect for him. He was just a "stupid bitch" to him now and he had treated him like one.

Ray couldn't face going home. If he went home, he would merely wind up in his boudoir, all sulky and miserable in silk, satin and lace.

He jumped on the tram. On the way, a drunk businesswoman in a tailored suit had tried to chat him up and she had roughly tried to paw and fondle him. Normally, Ray would have given her short shrift, but his natural feminine instincts seemed to override everything else, and he endured the woman's attentions.

He was saved by the intervention of a group of teenage boys. They were all in tight fitting, short-skirted dresses, heavily perfumed and made up and teetering on high heels. They were on a boy's night out, hoping working girls would notice them and ask them out.

They had seen Ray protesting mildly at his treatment as his suitor tried to slide one of her hands underneath his skirt and the brash, aggressive woman had found herself surrounded by a gang of handbag wielding boys.

The woman had tried to assert herself, but came under attack from a rain of blows from the boys' handbags and was forced to beat a hasty retreat down the carriage, shouting obscenities in their direction. The boys helped Ray to his feet and he thanked them sincerely.

"No need for thanks, brother" the leader of the boys said "We boys need to take care of each other". The boys resumed their seats.

Ray was impressed by the apparent solidarity of the boys towards members of their own gender.

He got out at the next stop and walked towards his next destination. Along the way, he had to walk past a building site. In the old days, before women became dominant, the workforce would have been predominantly male. However, since men had been forced to wear skirts and high heels, the workforce was now predominantly female.

The female workers had muscles, hairy arms and tattoos. When they saw Ray, the wolf whistles began, accompanied by comments like "Flash yer knickers for us, love!", "Lookat that arse!" and "Come and sit on my lap, Dollface!"

Ray was mortified and had never felt so vulnerable in his life. His head down and blushing, He had to force himself to keep moving. His high heels meant that his progress was slow, at best,but at last he was beyond the building site.

So, he thought, this is what it means to be the member of the weaker sex! To have women pawing you, wolf-whistling you and making you feel vulnerable. Still, when he had still been a member of the dominant sex, he had never considered how woman felt about some of the things he had said and done in his time, he reflected.

At last, he arrived at his destination and rang the buzzer. When he confirmed who he was, he was admitted into the building.

Debs and Charlie were waiting for him. They had been pestering him with texts and voice messages to drop around their place for some fun. He had tried to resist, until the girls had pointed out that they had helped him out after an attack by some knife wielding girls had left him semi-dressed and helpless. He had felt obliged to go around, even though he didn't want to.

He stood in front of them, clutching his handbag. The girls did not look happy. "Charlie and I are very upset with you, Ray! After all we've done for you, after all of the attention and time we've given to you, you ignore our calls and texts".

Head down, Ray mumbled an apology.

"What was that? I didn't hear much of an apology there! Did you, Charlie?"

"Nope" said the other girl.

"I'm really, really sorry" said Ray, in a louder voice.

"That's better. Now, for being a very naughty and ill-mannered boy, we've decided on your punishment". Debs produced a French Maid's outfit "Get changed into this and be quick about it!"

Ray took the shiny black uniform with its frilled apron and cap and changed into it in one of the bedroom. The uniform clung to his body and the lacy skirt fell only to his upper thigh. The slightest movement would reveal the frilly knickers he had to wear underneath his skirt.

The girls clearly intended to inflict maximum humilation on him.

He wobbled into the living room, perched on his stiletto heels.

"Very nice!" chorused the girls. Debs handed him a feather duster "Now, pretty maid, we want this flat so clean we could eat our dinner off the floor. Get to work!"

Ray spent the next two hours cleaning and dusting. It was clear that the girls didn't bother with housework at all judging from the thick layers of dust and grime and he was exhausted by the time he had finished.

The girls watched him work, amused. Occasionally, one of them would flip his skirt up as she passed him or give him a firm slap on the rump.

Ray knew that this was all part of their game to reverse the traditional gender roles to make themselves the "guys" and Ray the "girl". It was deeply humiliating all the same to have to be a cross between a housewife and a girlfriend.

But the girls hadn't finished with him yet. He was pushed onto their bed, face down and had to endure their large, penetrating dildos. Through the painful and shameful experience of being used by two girls, he was aware that this was not sex but a demonstration that, in this new woman's world, that they had the power and he had none at all.