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"I've had two sex changes!"

Ladies’ man Charles Kane never fails to charm women – the sporty millionaire property developer, who owns a luxury home and a yacht, seems to tick all the right boxes. However, his secret past means he’s struggling to find true love.

Charles was born a man but underwent sex change surgery to become a woman. Incredibly, seven years later, he realised he’d made a mistake – and now, after spending over £100,000 on gruelling operations, Charles has made history by becoming the first person in the UK to have two sex changes and lives as a man again.

But, speaking exclusively to Closer, he reveals he still hasn’t found happiness and is desperate to settle down with a woman.

'My past puts women off'

“When I tell women about my past, it puts them off,” admits Charles, 48. “I’d make the perfect boyfriend because I can really understand women – I used to be one – but I struggle with relationships.”

Born Sam Hashimi, Charles – who lives in London – married in 1985. He and his wife had two children together, but she left him for another man 12 years later. Feeling lonely, Charles – who’d experimented with his sexuality before he married – began visiting gay clubs. He says: “Despite kissing a man in my teens, I fancied women and felt I was straight, but after my divorce I decided to experiment.”

'I was obsessed by the perfect body'

Charles also became fascinated by transvestites and began cross-dressing. He recalls: “I bought a dress and spent hours on my make-up. I loved it and felt confident.

“I started sleeping with men and realised I wanted to become a woman full-time.”

Before surgeons would operate on Charles, he had to live as a woman and undergo counselling. In 1997, he embarked on an exhausting list of operations to become “Samantha.” It took two years and £60,000 – Charles’ Adam’s apple was removed and his vocal chords tightened to make him sound feminine, and he had a nose job, 34D breast implants and genital surgery to create a vagina.

“I wasn’t scared as I was obsessed with having a perfect body,” he says. “I loved my breasts and got attention from men and women – I even had several lesbian encounters. Sex as Samantha was very different to sex as Sam.

“I preferred sex as a man because it was easier to orgasm. But I had a clitoris created from the tip of my penis, so it was possible.”

Charles dated four men as Samantha, but admits having many more casual liaisons with both sexes. He didn’t tell any of the men he slept with that he used to be a man, but often admitted it to girlfriends.

He says: “I didn’t think the men would be able to deal with it, but some women had issues with being gay and felt better when I said I’d been a man.”

'I realised I'd made a mistake'

However, in 2003, Charles began to regret the sex change. He says: “I realised I had made a mistake – I was depressed, having trouble sleeping and was always in tears. I’d stopped enjoying sex and felt trapped.”

Charles began strapping his boobs down and dressing in men’s clothes again. After counselling, he begged for another sex change and the NHS agreed to fund it due to his depression, though he paid £40,000 for after-care and some additional surgery.

In October 2004, Charles had his breast implants removed, leaving him with scars. Two months later, after a year living as a man, Charles endured the first of three operations to reconstruct his penis.

He says: “They took skin grafts from my tummy to make a new penis, but it left me heavily scarred and it was very painful.”
Charles can’t get a natural erection now and has to inflate and deflate his new penis with a concealed pump. He’s also taking the male sex hormone testosterone and has started growing chest and facial hair again.

He says: “I wish I could say it’s a relief to be a man again but it’s not – I’ll never be the same man I was. And I haven’t seen my children for over 10 years  – they’re now 22 and 23, but don’t want to know me.”

Although he still fancies men, Charles – who chose his new name as he thought it was masculine – would love to marry. He has had several relationships with women since becoming a man again, but admits they end when his past is exposed. He says: “I keep my sex changes a secret at the start. I say the scarring on my genitals is due to a penis enlargement and I go into another room to inflate it.”

He managed to hide his history from one girlfriend for two months. He says: “One day she found out when she went on the internet and saw details of a TV documentary I once featured in.

“She dumped me and it’s not the first time – even though women don’t say why they’re leaving, I always know it’s because of the sex changes. All I want to do is find a woman to settle down with and love.” 

Words by Lisa Woollard