When Man becomes Woman: An Update

“When Man becomes Woman: The remarkable journey of Harold Jones. An Update” (Reporter: Lauren Kerslake, Big Planet/Small World Inc). Wednesday 17 October 2016

Back in the summer of 2013, I wrote an article about Harold Jones, a man who, due to an attempt to get himself out of a hole, ended up living as a woman for several years and even went as far as to become a bride!

Three years on, I decided to follow up this story. Since the original article, Harold (or Isobel as he is now officially known) has been released from prison as he had served his sentence for attempted fraud. He is now living with the woman who was for years his secretary and who loves him even though Isobel has had gender reassignment surgery and lives full time as a female.

I went to visit Wendy and Isobel at their home. Home is a modest semi-detached house in surburbia with a garage and a small garden. The door is answered by the lady of the house. Isobel, formerly Harold. Isobel looks every inch the sophisticated older woman and wears a blouse and skirt with a frilled apron. She is even wearing marigolds. I find it astonishing to believe that this woman was once a man and lived as one for most of his life. Isobel is shy, so Wendy takes command.

Wendy is physically bigger than her “wife” and dressed much as I was in the trouser suit favoured by most women today. Wendy invites me in and asks “little wifey” to make tea. Isobel seems relieved to be told what to do and disappears into the kitchen.

Wendy and I sit down and chat. Presently, Isobel produces tea on a salver. Wendy tells Isobel to come and sit beside her, which Isobel does and Wendy takes one of her small hands in her own. The affection and sense of protectiveness she feels for her more delicate and shy spouse is apparent.

Beaming, Wendy tells me that she and Isobel are very happy together in their new life. Once Isobel left prison, they were married a month later and Wendy shows me the wedding pictures. Isobel, fittingly, is the bride in a gorgeous gown whilst Wendy wears a variation of her current outfit. Now they are both retired. Since Isobel (as Harold) got himself into debt and tried to defraud various financial institutions, she has lost all her assets and pensions, but luckily Wendy has a generous pension that is sufficient for them both and now that Wendy is in control of the finances Isobel is only allowed enough money for housekeeping and a very small allowance.

It is clear that Wendy is the “husband” and Isobel the “wife”. At times, Isobel seems uncomfortable with the loss of her old gender and status says Wendy but is coming to terms with it.

Wendy then tells me her story……..

I was born in the same town as Harold and about a month after he was born. My parents weren’t as well off as his and so in addition to the handicap of being born a girl in the middle of the last century my prospects were always limited.

I attended the girls’ school and Harold of course went to the boys. As the schools were right next to each other, I saw Harold often. He was small, weedy boy and hopeless at games and the other boys ragged him mercilessly for this. But he was bright, especially with numbers. I instantly felt affection for him. But I had to look upon him from afar since boys and girls simply did not mix in those days.

Suddenly, school was over and I did not see Harold for a while as he went on to college and then university to become an accountant. It was a lonely time for me. My own career prospects were far more limited than those of Harold. Only a very few bright girls went on to further education in those days and I was not destined to be one of them.

Girls in my position had few choices. Get married or get a job in a shop, factory or office on low wages. Lower than the men certainly. One of my teachers had taken an interest in me and steered me towards a secretarial college. Being a secretary seemed better than serving in a shop or working in a factory and there was really nothing else for a girl with no means in those days.
The secretarial college course was easy and I finished top of the intake. I then got a job with a firm of accountants, initially working in the typing pool but after six months I was promoted to work as secretary to a new accountant.

It was Harold. I was over the moon to see him again. I did all I could to please him and make him notice me.

I was never a girly girl. I resented being put into frocks and skirts as a girl and being made to look pretty. As a secretary, I had to wear the “uniform” of silk blouse, black skirt and stockings and high heels. My hair, make up and nails had to be immaculate, day in and day out.

I secretly hated this but for Harold I went all out. I had my ears pierced and fitted with earrings and even spent all my savings on expensive perfume and clothes. For him, I would conform to the feminine ideal.

Harold noticed all this. He appreciated my dressing up for him and wearing perfume. He asked questions about my clothes and I wondered if he was a secret transvestite as it was unusual for men to show too much interest in ladies’ things.

He would have made a fine woman with his small build and slender legs but back then it would have horrified me if he had come to work in a blouse and skirt, or if he had shown the smallest tendency to be feminine. I wanted him as a man and expected him to be one.

I yearned for Harold to make some sort of sign that he was interested in me for more than dictation and shorthand. But no sign came. Harold moved up in status and my own status and pay were likewise enhanced. I was proud when he was made a partner and I became a partner’s secretary.

Harold was clever and he was a good accountant. Hard working and considerate. I had absolutely no idea that he would finish work and then gamble away his money at that casino. Had I known of it, I might have been able to help him.

Harold phoned in sick one day. It was the only sick day he had ever taken and it surprised me. Then days passed and there was no sign of Harold. I tried to call him at home but there was no answer. Finally, two grim-faced bobbies showed up and said that they had found Harold’s clothes and car on a beach. It looked like he had drowned. I broke down in tears.

Weeks and then months passed and I lived through them in a kind of daze. Eventually, I resigned my job. If I couldn’t work with Harold there was no point. I owned my own semi and the pension I had built up over the years was ample for my needs.

Since Harold had disappeared/died and his mother couldn’t even remember her own name, I took on the business of sorting out Harold’s affairs. I was shocked to learn that he had been heavily in debt. His estate had been left to his sister, Isobel. Harold had made out his will only a few days before he died and had got me to witness it, I recalled.

There was something odd about all of this, I thought. There was a nagging doubt in my mind. I tried to recall fragments of conversation with Harold. Something about his family he had talked to me about years ago but came up blank.

The police came to talk to me. An old Chief Inspector, Barker, who seemed disinterested, and his younger Detective Constable, a girl called Lucy Briggs. She looked like his granddaughter than a colleague but at least she had a spark of initiative and energy that was lacking in her superior. I told them what I could.

The bank took back Harold’s house and I went to clear it out. House clearance had removed all of the furniture so all that was left was post and a few knick knacks. For sentimental reasons, I took a tie pin that I had given Harold as birthday present in happier times. The rest of the knick knacks was junk and so I binned it.

I looked at the post, which had built up quite a bit since Harold had disappeared. Most of it was final demands and threatening letters. I ignored these as the solicitor would have to deal with them. The rest of it was bewildering.

“Angel Fashions: Clothes for the Modern Woman”

“Eve Lingerie: Sexy, feminine lingerie to bring out the inner woman”

And there was more. Letters from several similar companies. All addressed to this Isobel. All demanding payment for goods delivered.

Time was short. The representative from the bank would be along in a minute to formally take possession of the house as Harold had failed to keep up mortgage repayments. I took the post with me, gave the bank rep the keys and left him to it.

That evening, I laid out all of the statements. This Isobel had ordered an entire wardrobe of womans’ clothes, shoes and accessories. The bills came to more than five thousand pounds.
I smelt a rat. I had been to Harold’s house many times over the last few months to deal with his affairs and apart from his mother’s room, there was absolutely no evidence that a woman had been living there. No beauty products, no toiletries, not as much as a woman’s hankerchief.
What the hell was going on here?

The answer came when I went to see Harold’s mother. She had no-one now, poor thing, and her senility was getting worse. It took me half an hour to convince her of who I was. I tried to talk to her about Harold but all she wanted to talk about was her little girl, her dear little girl, Isobel. Where was her little Isobel? She rambled on in the same vein for another hour. It was hopeless. I went tell the nurse I was leaving. I mentioned the patient’s distress.

“Isobel again. That poor woman. She doesn’t even remember that her little girl died more than forty years ago”.

“Isobel’s dead?” I was stunned.

“Yes. I have a copy of the death certificate on Mrs Jones’s file.

I asked the nurse to show me the certificate and she did so. There is was in black and white. Isobel Mary Jones. Born 21 December 1950. Died 11 January 1953”.

There was no Isobel. So who was the Isobel who had been receiving all those clothes?

My brain gave me the answer. Harold. Harold had assumed the identity of his long dead sister to escape from his debts. It was the only answer that made sense.

I had an incongruous image of Harold dressed as a girl secretary and had to stifle the urge to laugh. This was not funny. This was serious.

And, if I was right, it meant that Harold must be alive! My heart leaped for joy.

But I had no way of finding him. I kept the correspondence for a few years and hoped that one day Harold would return.

I spent the next few years in happy retirement. This was interrupted by Lucy Briggs, now a Detective Inspector. She was re-opening the Harold Jones case.

I showed her the correspondence and a copy of Isobel’s death certificate and my theory.

Nobody else knew Harold as I did so it was no surprise that the police had drawn blanks to date.
Lucy took the evidence away with her after giving me a stinging rebuke for not coming forward sooner. She even threatened to report me to the DPP for withholding vital evidence and wasting police time but I shrugged it all off. This resourceful young officer would find Harold. I was sure of it.

And so it came to pass. A few months later, Harold was in a woman’s prison. I immediately went to visit him. He was completely dressed as a woman now and even had breasts. But it was him and that was all that was mattered.

I wore a trouser suit. I had thrown out all of my dresses and skirts after I retired. Harold met me dressed in a pretty white blouse, suede skirt and high heels. He wore make up, earrings and he had long hair that he had styled. He looked very womanly, but he was very embaressed.
He had had to remain dressed like this and to affect womanly behaviour, he had told me, in order to convince the authorities to keep him here. He would die if he ended up in a men’s prison. Especially with those breasts. I told him he made a quite lovely woman.

I eventually prised out of him his misadventures in Antigua. I burst out laughing when I heard he had had to become a bride!

I visited him every month and we became closer. Harold needed someone right now and I was there. His mother had meantime died, which had upset him. In addition, he was coming under pressure from the authorities to accelerate his gender reassignment surgery.

Years ago, I would have been horrified to see Harold dressed as a woman, let alone becoming one full time but now my view was different. The truth was that I was stronger and more masculine than Harold. He made a great looking woman and was adjusting to the feminine role. He would make a lovely wife, I thought.

I convinced Harold to go ahead with the surgery. I would love him regardless. So, he had it done and the authorities were satisfied.

When Isobel was released, she moved in with me. As I had the house and money, I was the master and she (formerly a he) was the mistress and housewife. Isobel was not entirely comfortable with it at first but has come to accept that I am the masculine element and she is the feminine element.

We married as soon as possible. Isobel made a lovely bride. I think she hoped I would be the bride, but I was determined not to wear a dress or assume a feminine role again. That was henceforth Isobel’s position, even though she had once been male. Isobel became the bride and became a little tearful and threw a tantrum but my will prevailed.

We are now husband and wife. Isobel knows that I love her but that her role is as the wife and to obey me as I know best. Isobel is adapting to her new life and is becoming pleasingly meek, shy and submissive. She must conform to the feminine role, as I once had to.

She is, and will remain, my little wifey.