Whores and Pimps - Part I

As he had no idea how to dress like a woman she would have to help him. She eagerly agreed and was pleased that the normally quiet, reserved Malcolm was coming out of his shell for this event. She told him to bring along the pictures on Saturday morning and they would go shopping for everything they needed so that Malcolm would look as whore-like as possible; it would be fun!

When Saturday arrived Malcolm met his sister Angie in the city outside of a large department store. He had already figured out that he needed to behave naive when it came to world of women's clothing and makeup; but he was determined to ensure he got exactly the look he wanted; he would have to be cunning that's all.

Hi Angie, he said, and kissed her cheek when she arrived outside of Myer; one of the better stores in town.

Hi Malcolm, she responded.

Let's get you feminised then, you hussy, she laughed, and Malcolm blushed; 'If only she knew the truth,' he thought.

Come on; lingerie first, she said enthusiastically and took his hand and led him into the store.

They made their way to the lingerie section of the store and started looking around.

When you say you have to look as realistic as possible does that mean underwear too? she asked.

We can get away with some cheap foundation garments if you like; we can squeeze you into a cheap bra and you can just wear your own underwear under women's clothing if you like? she added.

Malcolm was horrified at the prospect.

No; definitely not! he enthused, If we are going to make me look like a hooker, then lets go all the way; I want to win best dressed and who knows how good some of the other guys will look; it can be quite competitive you know and it might come down to who is wearing the best knickers! he laughed, hoping he hadn't gone to far and given his real motive away.

Alright then; lets turn you into a complete slut, Angie giggled, This is going to be fun!

My boring, unadventurous, brother is really getting into the swing of things. It's about time! she added.