In Her Shoes - Chapter Three - One of the Girls?

"...Admit that you find the idea fascinating......" Fiona Harrington's simpering voice penetrated Leo Cavendish's brain.

Leo's brain processed the information. Fiona was proposing that he, Leo Cavendish, experience life as a woman for a month to demonstrate his own point that women had an easier time of it than their menfolk.

At first, Leo's instinctive reaction was to refuse. He could not think of anything more humiliating than wearing ladies' clothing!

Yet.....he had to admit to being curious about what it would be like. What would it be like to have to wear a bra? Or sexy lingerie? Or a skirt? Or high heels? Or make up? To have one's body soft and devoid of hair and yet to have long, styled hair.

The two women in front of him, both very attractive and feminine beings, exchanged amused glances. "Come on, Leo! I challenge you to try it!" Chloe goaded him.

"Don't tell me big, manly Leo is scared of the idea of wearing a dress! How disappointing!" exclaimed Fiona. She looked at Chloe and said in a loud voice "I guess Leo just isn't man enough to try life as a woman and to prove to us how much easier a woman's life is than a man's".

Leo felt a sudden surge of irritation and anger. It was one of his many weaknesses to rise to a challenge. It had always been the same since early childhood. If someone had dared him to do something, or had expressed doubt that he could do something, Leo would be determined to prove them wrong. He had ended up in hospital or at the receiving end of a ticking off by his parents as a result of his trying crazy things that no-one with any sense would dare do.

Before he could stop himself, he blurted out "I'm man enough to do it!" then he faltered, instantly regretting his impulsiveness, and almost whispered "...but I'll have to run it by my girlfriend first! And Ms Carruthers".

The women gave him beaming smiles and each took one of his arms "What a brave boy you are!" cooed Chloe, almost purring with pleasure. Fiona insisted on buying another bottle of wine. As he drank his wine, Leo thought to himself. I'm safe. There's no way Milly would go for it and I'm too valuable for Ms Carruthers to let her top reporter go around in drag!

He fuelled the womens' delusions, jokingly saying how he was looking forward to wearing his first dress and learning how to walk in high heels.

Fiona and Chloe had to go. Their partners would be waiting for them to come home. Leo left with them and escorted them to the tube station. He saw them onto their train before boarding one himself and travelling home to the modern, luxury flat he shared with his live in girlfriend, Milly Prescott.

Milly was some eight years younger than Leo. In many ways she was still more girl than woman. As Milly was a little over five feet tall and had a very petite build, she and her former guardsman boyfriend drew more than a few looks as they walked together. Milly owned her own hairdressing salon, which she had built up from nothing.

Milly was the latest in a long line of girlfriends. Leo kept her around for pleasure, but he had no plans to get married any time soon. A girlfriend typically lasted a little over six months before Leo's eye began to wander and he ultimately replaced her.

Milly's young and earnest face greeted him as he staggered into the flat, a little the worse for wear due to the amount of wine he had drunk. Milly watched him, amused.

"I see someone's had a good time!"

Leo laughed. Milly helped him off with his coat and shoes, fetched his slippers and put them on his feet and made him a steaming hot cup of coffee. Milly cuddled up beside him and asked him in that sweet voice of hers how his day had gone.

Leo recounted his day, almost to the smallest detail and then stopped as he came to the part when he had agreed, in principle, to become a lady for a month.

Milly sensed something was wrong. Leo was normally so exuberant, so confident, so masculine. A little too much so, she thought.

"What is it, Leo?" she asked him.

Leo reddened slightly "I made really stupid mistake today, Milly. My temper got the better of me again!"

Milly put a hand over her mouth, thinking, Oh no! What has he done? Got into a fight? Insulted someone? Lost his job? The last scared her more than anything since it was handy having a boyfriend who was loaded and who let her live, rent free, in his flat.

"These cunning females, Fiona Harrington and Chloe Bright! They know how to push my buttons! Do you know what they talked me into doing? Becoming a woman for a month for an article in the newspaper. Imagine that! Me, as a woman! I can't do it of course, for your sake!"

He looked at his girlfriend, expecting her to be stunned, horrified by the notion, but she had collapsed into a fit of giggles.

"It's not funny! It'll be bloody humiliating! Me prancing about in high heels and skirts!"

Milly laughed herself silly. Leo glared at her. The girl composed herself, suppressing the urge to giggle.

"I'll tell them I can't do it because you don't approve" Leo said.

"Oh, no you don't!" said Milly "You're not using me to wriggle out of this one! You volunteered to do it, so you should just live with it. Actually, I quite like the idea!"

Leo's mouth fell open.

As Leo walked into the office, he was sure that the Editor, Ms Carruthers, would never wear the idea of her star reporter in drag. It would make the newspaper a laughing stock. It would never be taken seriously again.

Leo hadn't even made it to his desk when Ms Carruthers' voice sang out "Leo, step into my office please!" Leo dumped his laptop onto his chair and walked into Ms Carruthers' office, a spacious, rather masculine space with a fantastic view of the River Thames.

To Leo's consternation, Fiona and Chloe were already seated. Leo had hoped to make it into the office before them and talk Ms Carruthers into vetoing the idea. But those scheming females had made it first. Leo sat down beside the two women.

"Leo, Chloe tells me that you've volunteered to be the star of her new article "In Her Shoes: When a Man lives as Woman!". Great title! Well, Leo, how do you feel about it?"

The three women looked at Leo expectantly. For once, Leo wished he was not the centre of the universe.

"To be honest, Ms Carruthers...." he began slowly "I WOULD do it. But....how would the paper cope without me? I mean, I'm the political correspondent, the most important job in this office, next to yours, naturally Ms Carruthers!"

"Chloe's thought of that" said Ms Carruthers "Haven't you, Chloe?"

Chloe gave Leo a big smile. Leo felt at that moment like a helpless prey being circled by a hungry predator "Yes, Ms Carruthers. I propose that I join the political correspondence team, on a part time basis of course as I still have my womens' section articles to write, to free you up so you can be the central character in my article! And Ms Carruthers has agreed, haven't you, Ms Carruthers?"

Ms Carruthers gave a brisk nod "Indeed I have. I think the article will be splendid for the paper! A truly original and novel idea! And you, Leo, will be the star. Another feather in your cap!"

Leo gulped. Oh my god, he thought, I'm going to have to become a woman!