Sleeping with the Enemy

It was the shock I needed. I decided to clean up my act and got clear of the drugs and managed to get myself off the streets. I began to see a therapist, and it was she who helped me to understand that unless I took control of my life I could not move on. It was then I decided that I wanted to live full time as a woman and began hormone therapy with a view to a full transition.

It was at the beginning of my transition but I was already dressing full time when I first met Charlie. I was working in the beauty hall of a well known London store - the one with the bright yellow bags if you want to know - and still moonlighting with some escort work at night. The store wanted an edgy feel to it and they liked the idea of having someone with an 'alternative lifestyle' working there.

Dressed in tight hot pants and sparkly top, it wasn't the greatest job in the world, but it paid the rent and essentials. One incredibly tedious day I spotted this good looking, middle aged man walking through the hall - think George Clooney - so I grabbed his arm and spritzed him with perfume. He turned angrily towards me and I prepared myself for a shouting match when his eyes locked with mine and he stopped dead in his tracks. I saw the flash in his eyes as he made me, but he calmly brought his wrist up to his face and smelt the perfume. All without breaking eye contact with me.

He smiled and said, 'Very nice, how much is it?'

I mumbled the price to him, and he said, 'If I buy a bottle, will you deliver?'

I smiled. 'Yes, of course sir, the store will deliver to whatever address you wish.' I paused and took a big chance, 'But if you buy two bottles, I'll bring them round personally.'

He cocked his head to one side, looked me straight in the eye and I could see him making up his mind.

'Yes, yes, that would be very nice,' he peered closely at my name badge, 'Cindy. Yes, that would be most acceptable.' He handed me his credit card and what looked like a business card.

'Cindy, if you could make the delivery after 7 tonight, that would be lovely.'

I was quivering inside by this time at what I had done, but my bluff had been called and I really liked the look of him. I took his credit card and palmed the business card. I completed the transaction and brought back his credit card.

'Now don't forget Cindy, after 7 tonight, I'm looking forward to it.'

As I passed him his card and the receipt he smiled, tilted his head in a goodbye gesture and disappeared into the crowd.

Clarice, the girl I was working with that day, punched me on the arm and said, 'Are you mad, girl? That could get you into some serious shit. You're not going to do it are you?'

'Dunno, Clarice, but he is gorgeous, isn't he?' I said as I tried to catch sight of him again.

Clarice shook her head and declared, 'You is one dumb tranny bitch.'

Looking back now Clarice was probably right and I should have been sensible and stayed at home that evening. However, back then I was a million miles from sensible, and the wild child in me won out nearly every time I got myself into a scrape. Even though I had cleaned up my act I'm not too sure I was sparking on all plugs back in those days.

The business card announced George Clooney was in reality Charles Williams, with an address somewhere in Knightsbridge. I nearly backed out of going several times before I left my shared flat, several times on the way there and several times on the pavement outside the block of flats where Charles Williams appeared to live. In the end I summoned up my courage and walked into the entrance.

A uniformed doorman blocked my way. He looked me up and down and evidently decided he didn't like what he saw. I had put on my best outfit, my only outfit to be truthful, which was a black mini dress, dangerously low at the neck and tottering high heels. I had my hair in a high ponytail and my makeup was good but a bit outrageous. One of the store makeup girls had done it for me as a favour and I loved it.

'You can't come in here.' A real charmer this one.

'Why not?'

'These are private apartments.'

'I have a delivery for one of the apartments. Mr Charles Williams.' I showed him the big yellow bag I was carrying.

'Oh?' His eyebrows nearly met the peak of the fancy cap he was wearing. 'If you leave it with me I will make sure he receives it.'

'Sorry, Mr Williams was most insistent I delivered it personally.'

His eyebrows climbed even higher.

'In that case I will call him. Can I ask you name, Miss?'

'Just tell him it's Cindy.'

'Of course it is.'

This guy was now seriously jerking my chain. He dialled a number which was answered immediately.

'Mr Williams, I have a person here who says her name is Cindy, she says she has a personal delivery for you...'

The doorman was desperately hoping he would be able to tell me to shove off back where I had come from but his face changed as he listened to the answer.

'Yes Mr Williams, certainly Mr Williams, I will make sure Miss Cindy goes straight up.'

His manner changed instantly, and he came over all smiley and friendly.

'OK Miss Cindy, the lift is over here, let me carry your bag for you and I'll send you up in the lift to Mr William's floor.'

He nearly fell over in his haste to help me. Whatever had been said to him had certainly made a difference.

He showed me into the lift and pressed the button for the top floor and placing my bag on the floor..

'Good evening Miss Cindy.'

I was too surprised to say anything but as the doors closed I saw his face change to a scowl. He was not a happy bunny at all.

I had forgotten to ask which flat Charles Williams lived in but I thought his name would be on a door or something. The lift stopped, and the doors opened silently into what looked like a hallway with a big sofa to one side and a long low table on the other side. A lamp on the table cast a low light in the room. I took a step out of the lift but I could see only one door. As I stood there wondering what the hell to do next, the door opened and Charles Williams walked through.

He smiled as he said, 'Hello Cindy, it's nice to see you and so kind of you to bring my purchases personally.'

'Oh Mr Williams it's no problem, I wasn't sure which was your flat though.'

He smiled and gestured behind him, 'They all are, actually. Well, to be accurate it's all one flat but let's not worry about details. Would you like to come through? Oh by the way, please call me Charlie, everybody does.'

He reached out and took the bag from my fingers and took my arm and gently led me through the door. My mouth dropped open as I took in the room. It was vast, taking up what looked like the whole of the front aspect of the building. It was obvious that several rooms had been knocked into one and the windows had been replaced with floor to ceiling glass panels. The view was breathtaking; it was dark by this time but you could still see the glittering lights of London at night spread out before me. I had stopped dead and I'm sure my mouth was still open as Charlie said, 'It always gets me too. London is the most wonderful city don't you think?'

I nodded and finally remembered to close my mouth. 'It's beautiful. Oh my God, it's so beautiful.'

I glanced round at Charlie and he was grinning broadly, I suspect he loved to see people's reaction when they first saw the view. I smiled at the look of almost childish pleasure on his face as he showed off his creation. He took me by the elbow and gently took me over to the window.

'Can you see the Albert Hall over there and the Albert Memorial beyond? I always think it looks like a spaceship ready to lift off. Hyde Park is beyond that, and there's the Wellington Barracks and Buckingham Palace is round to the right.'

I nodded and said, 'This is all really yours?'

He smiled and nodded, 'Yes, the block is mine and I took over this floor and had it gutted and renovated.'

I whistled quietly at the thought of what that must have cost.

'Can't people see in?'

'The glass is self darkening according to the light levels. No-one can see in. I'm sorry, I'm forgetting my manners. Cindy, would you like a drink? You will stay won't you?'

I looked round at him and he seemed genuine but I was still trying to work out why he had asked me here and whether I should simply cut and run.

He read the uncertainty on my face. 'Don't worry Cindy, I don't mean any harm. You will be perfectly safe with me.'

Yeah, I thought, I bet that's what every serial killer says.

'I can offer you wine, beer, whatever spirits you would like...?'

'A white wine would be nice.' I thought that would be safe enough.

'On its way, Cindy.' he said and walked over to a cupboard built into one side of the room. He pressed a button, and a door slid silently back to reveal a bar with a built in wine chiller and he pulled out a bottle together with two glasses. He uncorked the bottle and the door slid closed again. I was impressed, the wine I drank mostly came in tetra paks.

'Please sit, Cindy, it will be more comfortable.' he gestured towards a massive L shaped sofa with a stunning view through the windows. He allowed me to sit first and then took a seat on the shorter arm of the L shape so that he could look at me more easily. He passed me a glass and took a sip from his own. I raised the glass to my lips and took a quick sip. It was without doubt the best white wine I had ever tasted, chilled and dry, it made me think of the sea and the seaside for some strange reason.

'Mmm, that's nice,' I said, 'thank you Charlie.'

'Cindy, you're very welcome, cheers and welcome to my home.'

We clinked glasses.

'Charlie, can I ask you something?'

'Of course, Cindy.'

'Why did you ask me to deliver the perfume tonight?'

He smiled as if he knew this was what I would ask.

'Well, to be totally accurate, it was you who suggested that you would deliver it, if I remember correctly.'

Smartarse, I thought, 'OK why did you accept my offer to deliver?'

'I will tell you after you tell me why you made the offer?'

Ok, in for a penny in for a pound.

'To be honest, you reminded me of George Clooney.'

'Ah,' he said, as if that explained everything. He grinned and said, 'George has actually sat where you are sitting now, and I don't think he would be flattered at such a comparison with me. However, I would be extremely flattered.'

My mouth dropped open again. A habit I know I should really break.

'You know George Clooney?'

Charlie nodded, and I sank back in the sofa, totally floored by that.

'Wow, and wow again.'

A few seconds went by and I took another sip of the wine.

'Your turn, Charlie. Why did you take me up on the offer?'

He didn't pause as he replied. 'You impressed me with your chutzpah. Spraying me with that perfume you took a risk. I was about to explode and then I saw how scared you were by how I might react and then I saw how pretty you are. When I smelled the perfume I liked it and I liked you. When you made the offer I thought why not? It might be fun if you decided to follow through.'

Uh? He thought I was pretty and he liked me? Is he the biggest BS artist in the world or what?

'Charlie, now you're having me on. You think I'm pretty? You do know what I am, don't you?'

'Oh yes, Cindy, I know, and yes, I do think you're pretty.'

Wow, I thought I had to be dreaming. I will wake up in a minute back in my shared flat with the smell of curry from the Indian restaurant next door.

Charlie didn't say anything, just let the silence hang there.

'Oh,' I said, as if this happened to me everyday.

I sipped the wine again and realised it was going straight to my head. I hadn't eaten anything since a sandwich at lunch. My stomach rumbled and Charlie laughed.

'Will you stay for something to eat?'

I didn't quite suppress a giggle and Charlie said, 'Sorry, did I say something wrong?'

'No, not all Charlie, I'm only wondering when the guys with hidden cameras will jump out and shout Surprise, you've been framed!'

'Cindy, it's nothing like that I can assure you. I honestly do think you're pretty and I wanted to spend some time with you. I'm separated from my wife and there are many, many women who would give their right arm to be sitting where you are. The truth is they are all gold diggers and would drive me mad very quickly. I have always had a flexible approach to my sexuality, one reason why my wife and I are separated.'

Seeing the look on my face he added quickly, 'Nothing kinky or bizarre I can assure you, it's that I have found myself attracted to women with let's say, a little something extra. I have never done something quite like I did with you this morning, but there was something so vulnerable about you, so I decided to take a risk. I don't normally do risk, I have spent my whole life assessing and minimizing risk.' He waved his arm around the room, 'And all this is the reward for managing risk. So when I met you I thought I would break the habit of a lifetime and take a risk.'

He paused, took another sip of the wine.

'Does that answer your question, Cindy?'

Oh brother, did it ever. In my escort work I had been picked up by some very posh guys who were into the down and dirty stuff and I knew they would scurry back to their wives in Surrey or Kent and believe they were still the pillars of society. Charlie was very different to them, he seemed open and honest. He appeared to be the perfect gentleman, and he hadn't once tried to jump my bones.

I nodded, and he said, 'OK, fancy some food? The staff have the night off, but they have laid out something in the dining room if you could stay.'

Staff? Oh my God, this is how the other half live.

He put out his hand and helped me stand. I was feeling the effect of the wine now and I wobbled on my heels.

'Please feel free to take off your shoes if it makes you more comfortable, Cindy.'

I gratefully slid off my heels and my feet cried out in thanks. The thing I loved most about dressing as a woman were the heels, and they caused the most pain of all.

Charlie smiled and led the way through a door into what was one of the most stylish dining rooms I have ever seen. It had a table big enough to have sat twenty people and was all Scandinavian chic with blond wood, muted colours and modern art everywhere. He led me over to the corner of the table where two places had been set. The window in here faced west and you could see the landing lights of the planes on their way to land at Heathrow airport.

Charlie held my chair for me as I sat down and I almost pinched myself to check this was really happening.

He moved over to a covered trolley and brought over some bowls of food. It's a salad if that's alright? I'm a buffoon in the kitchen and I thought it would be better to have something nice cold rather than you suffer my cooking.'

He poured me some more wine, and we settled down to eat.

'Cindy, I don't know anything about you, do you mind if I ask you to tell me something about yourself?'

I shook my head, 'There's nothing much to tell, Charlie.'

'Everybody has a story to tell.'

'OK, but I warn you, it's not all pretty.'

'Cindy, the best stories never are.'

For some reason I felt so comfortable with Charlie that once I started my story I found I couldn't stop. He got the full monty: from childhood, getting caught dressing by my parents, school and the dark days which followed. Apart from occasionally topping up my wine glass Charlie simply listened, never seeming to take his eyes away from my face.

I finally stopped and looked up at Charlie to see how horrified he was at my story. Instead I saw only his level gaze, a small frown on his forehead.

'You've been through some very bad times, Cindy. It must have taken real courage to deal with some of what you've been through. By the way, is Cindy your real name? You don't have to tell me if you don't want to.'

'No I don't mind. Cindy is my work name if you like, I was born Oliver but I always liked Olivia as my femme name, but there aren't too many escorts called Olivia.'

'Olivia, yes that's perfect for you. Olivia Hussey in Romeo and Juliet was one of my crushes growing up. Would you mind if I called you Olivia?'

Had I slipped into a parallel universe? Where men like this existed?

I wanted to say you can call me whatever you want, but I said, 'Sure Charlie, you can call me Olivia.'

The wine and telling my story had worn me out and I yawned.

'Oh God, I'm sorry Charlie, I think I had better get going.'

'Olivia, that's fine, I understand. Can I say I've had a wonderful evening and would you mind if I asked you if we could do it again?'

Now that's conclusive, I have fallen into a parallel universe.

'Charlie, are you sure?'

'Olivia, I'm positive. Give me your mobile number and I'll be in touch.'

I gave him my number and thought well that's the last I'll see of him but it was good while it lasted.

'Charlie, can you do me one favour and call a taxi? I'm too tired to take the tube.'

'Oh I think I can do better than that, I'll get my driver to take you back.'

Nope, not a parallel universe, I've died and gone to heaven.

Charlie escorted me to the lift door and said. 'John will be waiting in the lobby, just tell him where you want to go and he'll take you there.'

With that Charlie leant forward and kissed me on the cheek, 'See you next time, Olivia.'

True to his word, John, his driver was waiting and escorted me out to where a big black Mercedes was waiting, its engine running. He held open the back door for me and in a flash we were heading out into London's night time traffic. I asked John to drop me round the corner from my shared flat as I did not want to cope with any flatmates who might have seen me getting out of a massive merc.

As I got back into the flat my phone buzzed, 'John says he dropped you OK. Thanks again for a lovely night. Charlie'

'I loved it 2 Thank u ur a gent XOXO Olivia'

I fell asleep with a big smile on my face.

Of course, next day Clarice was all over me.

'What happened girl? Did you go see George Clooney?'

'I took the stuff round but nothing happened, honestly.'

'Oh yea, so who are these from then? Brad Pitt?'

She pulled a large bunch of flowers from beneath the counter where she had hidden them.

For the first time in many a long year I blushed scarlet and tried to grab the flowers. Clarice danced out of the way and laughed, 'You be one big tranny liar. So tell me again nothing happened.'

I finally got the flowers from her and opened the card, 'Olivia thank you for a lovely evening Charlie'

'Who the fuck is Olivia?' said Clarice reading over my shoulder.

A couple of uneventful days passed and the memory of the visit to Charlie's place began to fade. On the third day my phone buzzed with a message from Charlie.

'Olivia if you are free tonight. I would love you to join me'

So sweet of him. If I'm free tonight? In case I may have something better to do, like a date with Bradley Cooper.

'Wld love to join u. at flat?'

'John will pick you up. Is 7 good?'

It was, and I hurried home after work to get ready. I had my eye on a lovely dress, backless stretch ivory satin with a vee front with thin straps and a pleated skirt which fitted where it touched. I could just about afford it with staff discount as well as a new pair of heels. I had my makeup done in the beauty hall, a little more sophisticatedly this time, and put my hair up for the occasion. Even my very cynical flatmates thought I looked good.

Promptly at 7 John sent a message saying he was outside, and we were soon pulling up at Charlie's apartment block. Mr Snotty Doorman was a lot nicer to me this time although I could tell he still wasn't happy about it. Charlie met me at the lift and gave me a kiss on the cheek. He took a step back and said, 'Olivia, you look positively lovely tonight. I love the dress and your hair. Come through.'