David Bailey’s son Sascha says he practically transitioned to be a girl

Sascha Bailey, the son of celebrated photographer David, 86, has revealed he almost transitioned into a woman after he fell into the ‘transmaxxing’ scene during the break up his marriage . 

Former model David, 29, said he had a ten-minute interview in a specialist gender clinic in Nagoya where he was immediately prescribed hormone replacement medicine as he believed he was ‘born in the wrong body.’ 

Sascha told the Times that at this time he was reeling from the end of his marriage to Japanese lawyer Mimi Nishikawa and was planning to return to the UK where he would live as ‘Sacha without the s.’

Sascha, who is now identifying as a man once more and in a new relationship with photographer Lucy Brown, who previously worked as an assistant to Tommy Robinson, told the paper that historic sexual abuse as well as a suicide attempt led him to question his identity. 

He explained: ‘I often found it hard growing up to identify with males and male characters. I used to love Ripley [Played by Sigourney Weaver in Alien] because she was strong and she didn’t represent the person who had hurt me – she looked sufficiently different.’

Certain in his mind, Sascha told his then wife Nishikawa, who he claims was supportive with certain conditions. 

He explained: ‘She tried to make me sign a contract where I agreed that I would give her most of my money while I was transitioning and she could be with anyone she wanted, but I had to stick around and pretend not to be trans for a long time.’ 

Sascha says his journey down the trans pathway came when he stumbled across internet forums on ‘transmaxxing’, a sub culture of men who believe their life will be easier if they transition into women. 

He recalled: ‘It’s a form of problem solving. When you think about [transmaxxers] you have to take away all the feelings and the internal stuff because what they’re trying to do is make themselves right for the situation.’ 

After returning to England, Sascha says he was ready to begin the ‘project’ of transitioning and had his HRT medicine ready to go but delays in securing his second month’s prescription from the NHS ultimately gave him time to reconsider. 

He said: ‘I wasn’t going to start because the worst thing you can do is to stop and start.’ 

He then says he met Lucy Brown who he also told of his plans, however her response was slightly different. 

He says: ‘She repeated back my reasoning to me and I just started laughing. It all unravelled from that point.’ 

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.’