From Business Owner to Prostitute

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From respectable to destroyed.
1.3k words
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How things have changed. From respected business owner to insatiable street prostitute.

For a long time I ran a very successful business in London employing 14 staff and loving my work. I worked six days a week and on Sunday I did the paperwork, wages and stock checks. I had no time for social life, I was working for a successful future and in the evenings I just flaked out.

One night I was on my computer and came across a crossdressing/transvestite site. Browsing through I was fascinated and instantly aroused by the beautiful "girls" and their outfits.

Over the next few weeks I seemed to spend every evening browsing and learning more and more about the Cd/Tv lifestyle. I even went to a couple of clubs in London and was intoxicated by the atmosphere and the happy relaxed attitudes of the girls and the men they chatted and danced with.

Eventually I ordered some items from the internet and trying them on one evening it was the most excited I had felt for a long long time. I found my mind wondering at work and couldn't wait to get home to see what had arrived in the post. I spent my evenings in all sorts of outfits, dreaming of going to the clubs I has visited but never thinking it would happen. I researched places to go and specialist shops then one day told my staff I was having a week off to go on holiday. They were shocked as they didn't believe I had a life outside work.

So now I had a week to indulge myself in my passion. Building up my courage, I booked a session at a make over salon in West London. I booked a two hour appointment and left there fully and beautifully made up with my long wig on and dark glasses. I got home and changed into my sexiest outfit, put my long coat on and made off to one of the clubs I had visited. OMG I had the time of my life, was chatted up by loads of men, danced, kissed and had my bum pinched at least a dozen times. When I got home I was so happy, I couldn't sleep going over and over my evening. I continued going to that and other clubs every week but trying very hard to maintain my professional standing during the day. I was losing interest in my working life which was something I never ever thought would happen. I was just living for the evenings.

One night at the club I was talking to an older man who invited me to a party saying I would be the most stunning girl there and would make him really proud. Flattered, I accepted and arranged to meet him on the Saturday. He asked me to dress sexy and laughed so I said yes.

On the Saturday I had booked a make up girl come to my house and was thrilled with the result, worth every penny. I put the shortest mini I had with 5" heels and a little biker jacket on. I felt very horny and practised my pouting and flashing my eyes and remembering the girls at the clubs how they flirted.

When we got to his house he showed me in to a fabulous room full of large leather sofas and huge mirrors. Offering me a drink, champagne, I drunk it quickly and was instantly given another. Then I began to feel dizzy but noticed more people coming into the room but only men not women. After that I didn't remember a thing until I was back home and lying on my bed very very sore and disheveled.

Waking up next morning with a really bad headache and still in my girly clothes, I struggled to the bathroom, stripped, showered and crawled back to my bed. I stayed there all day and made it to work on the Monday pretending all was fine and hoping no one noticed my tiredness.

A few days later an envelope arrived at work addressed to me. Opening it my knees went to jelly. I checked the contents closed the envelope and took it to my car locking it in.

When I got home my knees were knocking I was shaking all over. I opened the package and laid the photos out on the dining table. Tears running down my face I was looking at a tartily dressed "girl" being raped and abused by a group of men all smiling at the "victim". She had a big cock in her mouth, one in her arse and one in each hand, lying there in panties stockings and heels covered in cum. As I stared at her face I thought OMG she looks like she is actually enjoying it ...and it was me. Reading the note attached it thanked me for a wonderful evening, hope I enjoyed it and looking forward to doing it again. If I didn't agree to that then the pics would be put on the net, sent to my staff and to my family. He would be in touch.

Over the next two months I attended two more "parties" but this time without the additive in my drink. More photos were taken and by now I was terrified of discovery. The man told me he was now my Pimp and I would be expected to "perform" as and when he told me to. I couldn't concentrate and had no choice but to sell my business and telling my staff and family I was going on a long holiday. After a couple of months I had a buyer and gave up my flat to move into a smaller place in Earls Court, London. My Pimp had taken all my male clothes away and insisted I always dressed as a Street whore. I had no choice, the thought of being exposed was too much for me to risk. It would have destroyed my family and I could never look anyone in the eye again. I entertained many men in my flat and he always came to collect the money waving photos in front of me. He told me it was all on film and soon we were going to make an even better one to sell. I was totally at his mercy and couldn't see a way out.

Over the next few months I appeared in three films which went to America but I didn't see any money. With some money from my business sale, I had breast enlargement, waist reduction, lip fillers, hair extensions and permanent eye make up. My hair was now long so no need for a wig. I must admit I loved my look and even got to enjoy my work as I got so many compliments.

One night he picked me up telling me to dress as slutty as I could and then in the middle of Soho he just said "Get out of the car slut and earn me some money on the streets and don't call me to collect you until you have earned at least £500."

I was out for hours and had to please dirty smelly drunken men in their cars until I had the £500. When I called him he said he would be half an hour so get back out there and earn me more. He was pleased with the money and from then on I have been on the streets four nights a week since. I am now a Transvestite prostitute pleasing any man who is prepared to pay for me. I do anything you want and have a reputation as the best sissy slut in town and am in demand every night I work. I look after my body, keep fit and actually enjoy my work. I get high on compliments and funnily enough I am happy. It is a long way from my business life that earned me a lot of money but now I realise I was not happy just over ambitious. I know this life won't last forever but when it ends I will move abroad and live a life in the sun hopefully with a rich sugar daddy!!

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2 Comments
zazrix9zazrix9over 4 years ago
OMG

What a hot fantasy, luv to live it for a couple of years

DianeRedfernDianeRedfernover 4 years ago
Fast Fantasy

Imaginative and enjoyable quickie.

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