When Man becomes Woman

“When Man becomes Woman: The remarkable journey of Harold Jones” (Reporter: Lauren Kerslake, Big Planet/Small World Inc). Tuesday 25 July 2013.

With some trepidation I steer my car towards the sterile box shaped building. The large sign outside proclaims my destination as “HMWP Douglas”. A burly female prison guard, who has the build of a male rugby player and a no nonsense attitude, puts out a meaty hand to instruct me to stop. The guard, whose badge betrays her identity as Prison Officer Primrose Flowers, orders me to turn off my engine and step out of my sporty mini.

Thoroughly intimidated by the sheer size of the woman warder, who could flatten a slenderly built five foot two girl like me like a gnat without even breaking sweat, I hasten to obey. Two female colleagues inspect my car, opening the boot, glove compartment and even the hood, whilst Ms Flowers lightly frisks me. She demands my visiting order, which I present to her. For what seems like forever, the warder studies the document intently before handing it back to me.

I am marched to Flowers’ booth and made to sign a visitors’ book and a long disclaimer stating that I was aware of the risks of entering part of the prison population and of the punishments to be meted out for trying to smuggle something into the prison or helping a prisoner to escape.

Then, with an air of extreme reluctance, Prison Officer Flowers allows me to climb back into my car and she opens the gate for me. I drive into the labrinyth, with another female officer riding shotgun as my escort.

HMWP Douglas, situated on the Isle of Man, was one of many women’s prisons in the UK. But this one was the only one in the whole country, if not the world, where there was one male inmate and it was for this prisoner that I had travelled hundreds of miles and endured being pawed by the likes of Prison Officer Flowers.

I am relieved of my briefcase, laptop and belt. Had I bothered with any jewellery, I would have had to relinquish those as well but few modern girls nowadays bother with such fripperies and I am a very modern girl. I am also the newest staff reporter on my paper, promoted over the heads of more experienced hacks who doubtless resented being passed over for a girl fresh from university, and I had a lot to prove.

Satisfied that I am not wearing or carrying anything that a prisoner might use as a weapon against other prisoners, guards or maybe themselves, my unsmiling, silent escort leads me to the isolation wing, where my quarry has been a permanent resident since he was admitted into the prison system ten years earlier. I pass a large area where female prisoners are doing weight training, using running machines, playing pool or just standing around talking. The voices drop to almost a whisper at the sight of my escort’s prison uniform and the female inmates look at me and the guard stonily. I note that the women, like their warders, are more masculine than feminine.

My escort crosses to the over side of me, acting as a shield in the case the worst should happen and one of the prisoners decides to attack me. Such incidents are not uncommon. Female prisoners are every bit as aggressive and tough as the males. Maybe even tougher. We are soon past the onlookers without incident.

My escort unlocks a gate and ushers me through into a cold, white corridor, before locking the gate behind us. She then turns the handle of the nearest door, an innocuous brown wooden one, and gestures for me to enter. For the only time, my escort speaks, telling me she will just be outside. Then, she gives me the lightest of shoves and locks the door behind me.

I find suddenly find myself in an environment that could hardly be more different than the cold corridors, steel gates and masculinised guards and prisoners. A lady’s drawing room. It was still a prison cell, of course. There was a steel bunk bed. The top bunk had no mattress or sheets as only one inmate occupied this cell in spite of prison overcrowding. There was also a sink and toilet. But the rest of it, a good two thirds of the available space, had a plush cream white carpet that my flat shoes seemed to sink into even though I weighed next to nothing (I worked out five hours a day, every day) on the floor.

Even disconcerted by the thought of possibly sinking up to my waist, or higher, in the soft carpeting, my natural eye for detail took in a pink chaise longe, a small delicate table on which porcelain cups and saucers rested on a silver tray, a small chair with flowered patterns and a pink and white cupboard on which sat a vase of freshly cut flowers. On the walls were pictures of flowers, cats or elegantly dressed Victorian ladies. It reminded me uncomfortably of my great grandmother’s room when I had been a very small girl. It reeked overpoweringly of traditional femininity.

But even the room seemed less odd than its occupant. A small figure, only barely taller than myself, in a flowery frock, stockings and high heels, got up from the shocking pink chasie longe and tottered towards me. I could see that the long flowing hair had been dyed auburn and that the face was expertly made up. The hand that was extended towards me had painted pink nails and delicate bracelets on the wrist.

This was the inmate I had come to see. The only male in the whole prison and he was more feminine and ladylike than any real woman here. Myself included.

The inmate’s name was Harold Smith. For the first forty five years of his life he had lived a typical male, middle class existence. Then, due to circumstances, Harold Smith suddenly disappeared and was presumed dead. Some years later, it was discovered that Harold had faked his own death in order to claim on a life insurance policy and other monetary payouts with the sole beneficiary being his sister, Isobel, and that Harold had become Isobel and was living as a woman in Antigua. He had even “married” another man. Had it not been for a persistent detective, Harold might have got away with it indefinitely, but he was found out, extradited back to blighty and banged up for fraud.

This is his story………..

I was born on 4 October 1949 to a middle class couple. I was naturally good with maths and figures from an early age and so I became an accountant. I was a good accountant and rose rapidly, becoming a partner at the age of twenty-eight, the youngest partner ever and a record that has yet to be broken or even equalled. For the next fifteen years, I lived a good life. I owned my own house by the time I was forty, bought a new car each year and became respected within my profession.

Then I discovered casinos and that was when my life changed forever. I got into the habit of working a full day and then racing round to the Roulette Casino. At first, it seemed like good fun but gradually I became addicted and began gambling more and more. I got myself into an awful mess. Outwardly affluent, my house and car belonged to the bank, I had a huge overdraft and I owed money all over the place. Going over my finances one night, I realized that I would be bankrupt and homeless before long. I could see no way out, other than stealing money from my clients and even I was not daft enough to do that.

The only assets left to me were a life insurance policy for a million pounds and my pensions, none of which I could access. I was worth more dead than alive I realized. Then it hit me that the only solution was for me to die. Not literally of course. Life was still good, even with the problems I had made for myself. I intended to live. But Harold would have to go and I would have to become someone else.

Faking my own death would be absurdly easy. I would leave a pile of my clothes on a beach and everyone would assume that I had drowned whilst swimming and that the sea had taken my body.

The more taxing problem was who I would become. Becoming my “long lost” twin brother or other male relative wouldn’t work, I realized. I would have to become someone totally different. For this to stand any chance of working, I would have to become female. It was a brilliant plan.

I didn’t even have to invent my female identity as I had had a sister, Isobel. She had her own birth certificate, national insurance number and even passport. But Isobel also had a death certificate for she had died at the age of two. My poor mother had never got over it.

Armed with the documents, over the next few weeks I updated these with the aid of a fellow gambling addict who was adept at forgery and with computers. My mother was still alive, but in a nursing home. I went to see her about once a month. Most of her clothes were still in the house but even I could tell that they were dated. No woman today would wear them and I would look even more outlandish if I wore them on top of impersonating a woman!

Getting hold of female clothes and accessories (for this was 1997 and women at that time still wore skirts, high heels, make up etc) would not be easy. The solution was the internet. Using my fake identity of Isobel, I signed up to the few websites around at that time that catered for ladies fashion, make up, jewellery, shoes and handbags. I ordered a load of stuff in different sizes. The dresses, blouses, skirts, underwear and shoes would come and I would try them on. Whatever didn’t fit or I didn’t like was returned. In a short time, I had a complete wardrobe for my new persona.

By the time I had amassed my new clothes, including a long black wig, my financial situation was reaching critical mass. The bank were sending me letters about my mortgage payments, or lack of them, and I was getting red letters from other creditors. I would have to become Isobel soon.

First, I paid one last visit to my mother. My mother, once a strong minded, competent woman, had in her twilight years descended into senility and no longer recognized me. It was a heartbreaking visit as I knew, due to my own stupidity, that I would never see her again.

The next day, I phoned in sick. I felt a pang as I spoke to Wendy, my devoted and loyal secretary of more than twenty years standing, and knew that I would never see or speak to her again either. Then, I put my suitcase in my car and drove off to the coast.

I found a quiet area of beach. Making sure no one else was around, I quickly changed out of my suit and lay it on the beach, along with my brogues, a set of underpants, my wallet and car keys. I had already shaved my legs, arms and chest and wore a lacy bra, matching knickers, a suspender belt and black stockings. I felt utterly ridiculous but had to make the changeover very quickly. My plan would be ruined if anyone saw me.

I inserted my breast forms into my bra, donned a white silk blouse, black pencil skirt and matching jacket, and stepped into a pair of black high heels. I put on my wig and applied a light make up to my face. I put on a ladies watch and some bangles and applied press on red nails to my fingers. I retrieved my suitcase and handbag from the boot and then turned on my high heels and left Harold Jones behind forever. I was now Isobel Jones, sister and sole heiress of the deceased.

I felt bloody foolish at first. Here I was, all dressed up as a woman in the middle of nowhere. It was humiliating to have to wear feminine clothes and the heels hurt like hell after only a short distance. I stumbled along the road to find a bus stop to get me to the airport. Once I was out of the country and all my policies and pensions were transferred to Isobel’s account, I could empty it and go where I liked and do what I liked.

I walked about half a mile. Luckily my case had wheels but it was odd to be dressed this way and to have to carry a handbag, a definite symbol of womanhood. A car stopped. It was a Aston Martin and it was being driven by a girl. She asked if I wanted a lift. I felt like refusing. I couldn’t risk her discovering I was not a real woman but on the other hand my feet hurt and I was desperate to get to civilization so I put on my best falsetto voice and accepted.

I climbed into the car as best I could whilst wearing a tight skirt and high heels. The girl put her foot down as soon as I was inside and my wigged head hit the headrest with the acceleration. The girl asked me what I was doing and I told her untruthfully that my car had broken down and I had had to abandon it to catch my flight.

The girl was dressed in a T-shirt, jeans and plimsolls. I was dressed in a ladies’ business suit. The juxtaposition was not lost on me.

The girl was chatty and spoke a lot about herself. Thankfully I had to do little more than nod or make an affirmative noise. I was greatly relieved when the car pulled up outside the airport. The girl helped my unload my case, wished me a good flight and then sped off. I took a pair of sunglasses from my handbag and put them on. It would be best if my eyes were hidden, I decided.

I presented my passport and boarding pass with seeming reticence even though I was trembling inside. My plan could still go hideously wrong at any point until I got off the plane in Antigua. The girl at the flight desk glanced at my credentials and handed them back to me without a word. Still struggling with the high heels, I tottered onto the plane and was grateful when the plane took off.

So far, so good.

I found my seat and found that I was sat next to a man of about my own age. I instinctively took a dislike to him. He had that odd aura about him. He looked at me, his eyes taking in my rather slender, stockinged, hairless legs (I did have very good legs), the small feet made dainty by the high heeled shoes, my bottom which was accentuated by the tight skirt I wore, my protruding breasts and my feminized, prettified features covered by a veneer of cosmetics.

Once I sat down, I instinctively pulled my skirt in a futile attempt to hide as much of my legs as possible.

My fellow passenger couldn’t take his eyes off me and I felt like prey. His eyes seemed to study me in every detail. I now had some idea what it was like to be a woman, all vulnerable and on show, subject to the predatory glance of the dominant male. I was about to tell him to look elsewhere, but dared not risk speaking. So I sat in silence while his eyes roamed all over my body.

Finally, the plane landed in Antigua and I was able to escape the predatory eyes. I retrieved my suitcase, got a taxi and checked into the hotel. My home for a few weeks until Harold’s estate was sorted out and I became rich.

It felt very strange to unpack an entirely feminine wardrobe. I had been tempted to wear men’s pants rather than the frilly things women had to wear but I had to convince the hotel staff that I was a woman so it would be knickers going into the laundry basket. There could be no trace of my former masculinity.

I was exhausted and so after a bath I changed into my nightdress, a mass of pink and lace satin, and went to bed. Over the next few days, I stayed in my room as much as possible. The less exposure to other people the better, but I still had to go downstairs, dressed as Isobel in a flowery frock or blouse and skirt ensemble, for meals. It was becoming tiresome having to shave my legs and use make up every day but appearances had to be maintained.

Just over a week later, the local police arrived to see me. The pair, a man and a woman, advised me to sit down as they had some bad news for me. When they told me Harold was missing, I of course acted shocked and upset and asked all the usual questions about how he had died. The woman officer put a comforting arm around me and said that they weren’t sure Harold was dead. He could still be alive, somewhere.

They in turn asked me about when I had last seen Harold (when I looked in the mirror, the mischevious part of me wanted to answer) and how he had been. I told them I had not seen my brother for years. They seemed satisfied and left.

More time passed. By now, I was getting bored of just sitting in my room, so put on a frock and some make up and ventured into the bar area. To my consternation, my fellow passenger from the plane was propping up the bar and his eyes immediately switched from the other barfly he was talking to in a loud voice to my skirted bottom. Clearly plastered, he made some lewd comments about my legs and rear and what he would like to do with me in his hotel room.

I had no idea what to do. A real woman would know. I just stood there, frozen, fearful and appalled. A real damsel in distress.

My white knight was a woman, dressed in a similar way to myself, named Emily, who took me by the arm and steered me towards a group of women. She gave my persecutor a baleful look. Emily introduced me to the other ladies and I had to introduce myself. When they heard of the recent disappearance of my brother, they were sympathetic and comforting.

From that day, I became part of that little sorority. I ate and socialized with these women and they seemed to accept me as one of their own. We went on a shopping trip and entered a ladies’ fashion boutique. Emily spotted a fuschia coloured dress that she thought would be ideal for me and urged me to try it on. I tried to demur, saying my funds were limited until my brother’s estate was settled but Emily bought the dress for me and insisted that I wear it tonight. So, that evening, I had to parade about in that rather gaudy dress. The girls applauded as I gave them a twirl as instructed. I felt hideously embarrassed to be treated like a female model.

Sympathetic to my poverty, the girls lavished other gifts on me of jewellery, perfume and expensive lingerie (which I was thankfully not required to model in public). Before long, I had a complete wardrobe of expensive clothes and lingerie. I felt shame when I had to put on a babydoll and pink silk dressing gown and other frilly, lacy things but had no choice. I had to remain Isobel for a while longer.

Meantime, I was phoning my brother’s solicitor daily, putting on my best female voice to find out when I could expect my money. There were complications, they told me. Since there was no body found, they could not declare Harold dead so the life insurance company were not going to pay out until they found a body and neither was the pension company.

I was in despair as my funds were almost exhausted. The girls rallied round and said they would help but I needed a more permanent solution. The answer was obvious. Like any woman in need of money, I would have to marry!

There was an old man in the hotel, Charlie Farbrook. He was in his eighties and dessicated. But he was rich and he had taken a liking to me and bought me drinks.

I could hardly believe what I was going to have to do. I would have to seduce him. I tarted myself up. I shaved my legs (a seemingly endless chore), sprayed myself with perfume, put on my best lace bra and knickers, that fuschia frock that I hated but which Charlie seemed to like seeing me in. I had my long hair styled, my ears pierced and a pair of crystal earrings inserted (which hurt like hell), made up my face and put on a necklace. A pair of killer heels and a diamond studded handbag finished off the look.

I had to admit that I looked stunning. Living as a woman for several weeks, I had learned many of the tricks of the trade of the seductress. But I was filled with shame at being a man forced to dress up as a woman, perfume his body and even getting his ears pierced in order to get another man to marry him.

Charlie was a pushover. As soon as he saw me, he drooled and within a fortnight he had proposed to me. My finances were so parlous that I had no choice but to accept or face destitution. The girls were thrilled but I suddenly realized that this meant that I would have to get married. As a bride. And then become a wife!

The girls insisted on dragging me to bridal boutiques and I had to try on dress after dress. I had to get in and out of confections of satin, silk and lace with endless flounces, ribbons and petticoats. The girls chose my dress for me and I had to go along with it. It was a white ivory gown, with a lace neck to enhance and show off my breasts, lots of embroidered flowers and bows, masses of petticoats and a delicate lace veil. That was humiliating enough for one born as a man but worse than that even was my bridal lingerie.

I would have to wear a whalebone corset. It was the only way to shoehorn me into the dress. It was the most uncomfortable garment I ever had to wear and I could not bend over in it at all. I also wore white stockings with deep lace tops and for the grande finale my much vaunted pudenda was covered only by a lace thong. The thong was the most painful thing I had to wear, since my most private areas were not built to accommodate it but even worse than the pain was the shame at having to wear such a feminine bit of fluff to please an old man.

On the wedding day, I could hardly believe that, fully attired as a bride, I was struggling down the aisle, holding my skirts up and trying to see where I was going through the lace veil. It was a deeply humiliating experience for a man to be married off as a bride. The ceremony went off alright though and I reflected that at least my money troubles were over. As Mrs Farbrook, I could spend what I liked.

Charlie was far too old for any amorous adventures with me but he appreciated seeing me in my wedding finery. He was besotted with me and gave whatever I liked. I was soon the best dressed lady in town. All of my clothes and jewellery were the envy of other women.

But gradually I realized I was trapped. I was Mrs Farbrook, a kept woman. I had to attend balls and parties with Charlie in evening gowns and high heels and play the woman. This was not what I wanted. To make matters worse, the girls were still around. I couldn’t seem to get away from them. They got me have things done. Electrolysis on my legs and body, hair extensions and finally and most shamefully, breast augmentation. I ended up with a pair of knockers bigger than any woman I had ever met. They were so big, I couldn’t see my lower body or feet and my whole sense of balance had changed.

I was now more like a woman than a man and months and then years of having to play the female turned me into one psychologically. From hating my clothes and underwear, I became addicted to them. I had to have the best dresses, the most exquisite lingerie and designer shoes and handbags. I liked pretty things and had adopted a soft, feminine tone to my voice.

My time as Mrs Farbrook lasted for almost five years. For five years, I was a wife and society hostess.

But it didn’t last. Back in England, a resourceful young detective, Detective Inspector Lucy Briggs, was looking into Harold’s unsolved “death”. Briggs, eager, youthful and determined to make a name for herself, questioned my secretary and other colleagues who had known Harold for years. Briggs checked the records and discovered that Isobel Jones had died as a child many years ago. She found amongst correspondence that had accrued since I left the UK, letters from womens’ clothing companies addressed to Isobel. Briggs also found out about my debts. Putting all this together, the determined DI Briggs worked out what must have happened.

My existence as Mrs Briggs was dramatically ended when the young woman appeared in Antigua and filed charges against Harold Jones for attempted fraud and put in a request for my extradition back to the UK to face trial. The wheels of justice and bureaucracy turn slowly, but they do turn and eventually Briggs had everything in place.

Whilst I was dining with my husband and girlfriends, the police, led by Briggs, descended upon me and arrested me. I tried to insist that it was all a mistake, but to no avail. At the local police station, I was stripped of my feminine finery and my true gender and identity were conclusively confirmed. Not surprisingly, my “husband” and former girlfriends spurned me and cursed me for my deceit.

I was flown back to the UK and convicted. The shame I had felt at impersonating a woman was nothing to the shame I felt when the verdict was handed down. Added to that, my mother had since died, so my shame was magnified. I knew I would never survive in a male prison, so my brief managed to get me incarcerated in a woman’s prison on the grounds that I had been living as a woman for several years and intended to seek gender reassignment.

And I had to go through with the gender reassignment or else be transferred to a man’s prison where a small man with large breasts wouldn’t last long. So, in addition to my boobs, I had to submit to having my most intimate bits converted into the female equivalent so that I became a woman complete. I also changed my name to Isobel to fit my new gender.

My sentence ends in a couple of years and when I leave I will leave as a woman and live out my life as a woman as I am no longer anatomically male and in truth have come so used to femininity that I'm comfortable with it. I have no money of my own, but my devoted secretary, who has visited me in prison every month, has said she will take me in. She told me that she had loved me for years and wanted to marry me, regardless of my gender. Who knows, perhaps I will be a bride again but at least this time I won’t be fooling anyone.

The beginning.