Sascha Bailey – son of iconic photographer David

At the peak of his unhappiness, Sascha Bailey was so desperately low that he contemplated taking his own life.

But internet chatrooms convinced him there was another way out of his despair: he could transition into a woman.

Sascha’s vision was to become ‘like a real-life Barbie’, with pneumatic curves and long blonde hair.

Had the 29-year-old son of the renowned photographer David Bailey and his model fourth wife Catherine spent a lifetime believing he was trapped in the wrong body?

He insists not. Instead, thoughts of becoming a woman began to emerge as the art curator endured a volatile and difficult marriage, becoming so profoundly depressed that he was barely able to get out of bed.

‘Transitioning was a way of killing myself without dying, because I was so unhappy with my life,’ he says, talking exclusively to the Mail. ‘I thought that if I could do this one thing it could change everything, I could reinvent myself as an entirely new person.’ 

So convinced was Sascha that this was the right course of action, and so anxious to hasten the process, he saw a private doctor who confirmed he was transgender and wrote him a prescription for female hormones as a prelude to gender affirmation surgery.

Yet 15 months on, Sascha sits before me, not as a woman but as the handsome young man he has always been. Nurtured by his family and the love of a new partner, 32-year-old photographer Lucy Brown, he has been pulled back from the brink of a life-changing and — he now believes — potentially ruinous decision.

To say he is deeply grateful is an understatement. Indeed, his enormous relief is the reason that, with extraordinary candour, he is opening up about this deeply personal subject, determined to use his experience for what he believes is the wider good.

He is easy company, with a disarming smile, but you can still sense his vulnerability.

‘I feel there’s a huge problem with over-diagnosis of gender dysphoria,’ Sascha says. ‘Obviously it is very real for some, but I think there are a lot of people who, like me, aren’t actually trans, they’re just incredibly unhappy and transitioning is a way of making themselves into a new person which they believe will fix everything.

‘This new person won’t have the old problems or the old societal expectations. But of course that’s not really true.’

Sascha knows that by speaking out so boldly he may be a target for trolls. ‘But no one can say it’s not my lived experience,’ he says. ‘I am only speaking from the heart about something I know.’

All of this, of course, feels a very far cry from an upbringing steeped in glamour.

Sascha’s father David, now 86, counts famed beauties Catherine Deneuve and Marie Helvin among his ex-wives, and he has a portfolio of extraordinary fashion and celebrity portraiture. Sascha’s mother Catherine — to whom David remains married today — is also a celebrated model.

Together with his older siblings Fenton and Paloma, Sascha grew up in bohemian privilege between London and the Bailey country estate in Devon. The family are close.

‘Growing up with my parents was fantastic — they were both inspirational people,’ he says, recalling a household which was no stranger to A-listers. ‘I remember Ronnie Wood told me to tie people’s shoelaces together at some event, and the shoe designer Manolo Blahnik kicking me, which was well deserved, as I had pulled someone to the floor as a result,’ he smiles.

Dyslexic, Sascha was educated privately at a specialist London school, leaving at 16. Within a year, having inherited his mother’s fine bone structure and brunette colouring, he’d been signed by renowned model agency Storm.

By then he was already living with an older girlfriend. ‘I was going through a rebellious phase, and just wanted to get out there and do my own thing,’ he says.

Then, aged 19, having returned from several months of modelling in Japan, he met lawyer Mimi Nishikawa through a mutual friend. She was 20 years his senior, but this was no bar to an instant attraction.

‘She was magnetic and charming, and we just bonded,’ he says. ‘I think we were both a bit lonely, too, and I guess we found each other.’

Of the age gap, he says: ‘It did raise a few eyebrows, but honestly that part of it was never an issue for me, and still isn’t.’

In any case, the relationship unfolded with astonishing speed: within three months the couple married at Camden register office with just two witnesses — Sascha’s best friend and Mimi’s roommate — despite the misgivings of friends and family.

‘Loads of people told me it was a bad idea, but when you are in that sort of zone, you have blinkers on,’ he says. ‘I know people were worried, although my dad laughed and said: ‘Do whatever you want.’ He was married at around the same age, so what could he say?’

The marriage was happy enough at first, with the couple settling in Whitechapel, East London.

Over time, however, it became increasingly toxic.

‘It got to the point where it was pretty terrible,’ he says. ‘There were a multitude of issues, and on top of that she was also just not very nice.’

Increasingly unhappy and isolated, he was unable to confide in family and friends. ‘You put yourself in a metaphorical cage when you’re in a situation like this because you start coming up with all these reasons why you can’t leave,’ he says. ‘In a way you enslave yourself.’

By the end of 2019, Sascha suggested the couple move to Japan for a fresh start. They settled on the outskirts of Tokyo, but things continued to deteriorate.

Shockingly, by September 2022 he confides he was so unhappy that he considered taking his own life.

‘I wrote a note,’ he reveals. ‘I still have it on my phone.’ He changed his mind at the last minute. ‘After that, I just couldn’t get out of bed for ages,’ he says.

It was at this point that the notion of changing gender started to crystallise. ‘I’d already been thinking about it and it’s an idea that just grew and grew,’ he says. ‘It became this way of not having to kill myself, but to become someone new.’

An escape, if you like. This possible ‘solution’ was reinforced on the internet chatrooms that Sascha had been frequenting, where changing gender was talked about as a ticket to a new life.

‘It’s the ultimate way to solve your problems because you’re being told everything about you boils down to this one thing that is wrong, and if you can fix this one thing everything will be perfect,’ as Sascha puts it.

Having made the decision to transition towards the end of September 2022, he felt liberated.

‘When I decided I was trans, I felt great because I felt I was moving towards a goal, towards something achievable. If I followed this path — took the hormones, did the surgery — then I would end up in the place I needed to be. When you are so lost, this is game-changing.’

After meeting a psychiatrist at a private clinic in Japan — with whom he communicated through an internet translation forum — Sascha was ‘diagnosed’ as transgender.

‘It took ten minutes,’ he says. ‘He referred me to a surgeon and I was given a box of HRT (hormone replacement therapy) patches and sent on my way.

‘I’m never someone to do anything by halves, and my plan was to go quite hard on the surgery,’ he says.

He envisioned becoming a statuesque blonde. ‘The full Barbie cliche,’ as he puts it now, adding: ‘There’s an irony really; you’re not allowed to adhere to stereotypes unless you are trans.’

It is no small irony that the fact things abruptly came to a head in his marriage was what prevented him going farther down this road: within a couple of days of visiting the clinic, Sascha fled to London.

‘I genuinely felt that if I didn’t leave, something disastrous was going to happen,’ he says. ‘So I just got myself out of there. I had a ‘go bag’ in a cupboard that Mimi didn’t know about, and the next morning I just grabbed the bag, went straight to the airport and paid for a plane ticket to London at the terminal.’

He sought refuge with his parents, and says that they, along with everyone he knew, were ‘unbelievably supportive’ when he revealed his plans to change gender: ‘They were supportive to a fault.’

‘My mum was a bit confused, but definitely supportive, as was my brother, and my sister was super supportive,’ he says.

‘That’s wonderful on one level but I feel like that’s another issue — it’s almost like society has a gun to its head, because if they’re not supportive of it, the only choice is to be cancelled. You are either for it, or you’re transphobic; there is no middle ground.’

In fact, Sascha’s plans had to be put on pause because, anxious not to start hormone therapy until he could be sure that he had a second month’s supply from the NHS, he struggled to get an appointment.

‘So I guess you could say that the slowness of the NHS helped to save me,’ he says with a smile. Back home, and with space to think, Sascha says he came to a realisation that changing his external identity was not going to resolve the complex feelings he had inside. He has been diagnosed with PTSD as a consequence of experiences within his marriage.

He says he realised two things: ‘One, there was no actual way I can know what it feels like to be a woman because I’d never been one, so the idea of me saying ‘Oh, I feel like a woman’ was absurd.

‘And the second thing I came to realise was that I didn’t actually need to change my outside because of how I felt on the inside. I just needed to come to terms with it.’

None of this has been easy: having been suffused with what Sascha calls ‘gender euphoria’ — a sense of having a ‘solution’ to his unhappiness — he now had to face the real world. ‘It meant I actually had to face my problems, and it floored me,’ he says.

It’s fair to say that process is ongoing; while Sascha is in a ‘much better’ place, he confides to still feeling rather lost.

‘Going through any traumatic experience takes time,’ he says. ‘I’m also having to confront the fact that ten years have gone, I’ve lost my home, we’d built up an art company together and that’s gone too.’

But family and friends are giving him time to lick his wounds.

‘I live with my parents at the moment, and they’ve been really understanding,’ he says.

So has his new partner Lucy, whom he credits with providing loving, non-judgmental support. ‘Lucy has saved my life in many ways,’ he says. ‘She’s such a fantastic person.’ They are shortly to move into a place of their own, and he plans to curate another art exhibition soon.

More than anything, he is glad that he did not take those first few tempting steps down the road to becoming a woman.

‘Thank God I didn’t do the hormones, because within a few months you’re risking infertility and the thought that I could not have children is devastating,’ he says.

‘But it also shines a light on the uncomfortable reality, which is that we are asking kids aged 15 and 16 to make the choice about whether or not they will want children themselves and that just isn’t right.’

He acknowledges that his experience was at the extreme end in a society where, if you have money, you can pay to realise your dream without too many probing questions. Nonetheless, he believes his journey has huge resonance in the UK, where mounting numbers of young people are being diagnosed as transgender. ‘I wish everyone could just take a breath,’ he says.

‘I think we’re going to look back on this time and be shocked at how quickly we ran away with all this stuff. We need to allow people space and time to talk and explore their feelings before we rush them down the medical route.’

He also hopes that his story can be one of optimism to anyone who is struggling. ‘I still have some work to do,’ he says. ‘But after everything I’ve been through I’m so happy to be rebuilding my life.’

For confidential support, call the Samaritans on 116 123.