Sascha Bailey has opened up for the first time about the words his girlfriend Lucy said that made him realise that transitioning into a woman was ‘madness’.
The former model, who is the son of renowned photographer David Bailey and his model ex-wife Catherine, had been suffering with depression and felt so desperately low that he contemplated taking his own life.
Yet he soon found himself convinced that his unhappiness was caused by gender dysphoria and that by transitioning he would live life happily.
Emboldened by advice from internet chatrooms, he visited a private doctor, who – after a 10-minute consultation – confirmed he was transgender and wrote him a prescription for female hormones.
Yet ahead of undergoing life-changing gender affirmation surgery Sascha was brought back from the brink by his father and his new girlfriend Lucy Brown – with whom he’s now expecting his first child.
Sascha recalled how one night things changed when his girlfriend Lucy came over and they spoke about his plans and she mirrored what he was saying back to him.
He revealed how one seven word question altered everything: ‘What will happen when you start HRT?’
In an extract serialised by MailOnline from his new book, Try to Hit the Pool, Sascha reveals in his own words what made him change his mind about transitioning…
Sascha Bailey has opened up for the first time about the words his girlfriend Lucy said that made him realise that transitioning into a woman was ‘madness’
The former model, who is the son of renowned photographer David Bailey and his model ex-wife Catherine, had been suffering with depression and at one point felt so desperately low that he contemplated taking his own life
Sascha had been living in Tokyo, Japan, where he had become set on the idea of transitioning into a woman after struggling with depression and being stuck in what he describes as a ‘submissive’ marriage.
He was married to Japanese lawyer Mimi Nishikawa, a decade his senior, for 10 years, before ‘fleeing’ Japan in October 2022.
Recalling the events the followed, he says: ‘When I got back to the UK, I still fully planned to transition. But slowly, over time—and thanks to meeting a few very important people—the idea left me.
‘I had escaped a situation where I simply couldn’t exist as a man.
‘And with time, my mind, body, and soul returned to me.
‘Of course, it helped that, as the saying goes, I found “the love of a good woman.”
‘My now-girlfriend and partner in life, Lucy, helped me see things clearly.
‘She helped me understand that what I was doing was madness. She laughed at the idea that I would grow breasts and become infertile, and that laughter—her sheer disbelief—helped me step outside of myself.
Yet ahead of undergoing life-changing gender affirmation surgery Sascha was brought back from the brink by his father and his new girlfriend Lucy Brown – with whom he’s now expecting his first child (pictured in 2023)
‘It made me see just how ridiculous the situation had been.
‘After I first got back to the UK I was still on a mission to transition.
‘A few weeks in I went out with my sister and mother to buy clothes as I really didn’t have any other than a few shirts and the suit I had worn back along with a couple of dresses.
‘I picked all female clothing preparing for my soon-to-be new life as a girl. During this time I was in a kind of strange state of euphoria at the thought of all the things I would be moving towards as a girl and the new aspects of life that I would have to explore: clothing, makeup, heels, and gel nails, which is a skill I got fairly good at (the main excitement about these things for me was the aspect of learning new skills, new distractions).
‘A lot of the things around becoming trans are learning new things. The gaining of new skills is something I have a kind of addiction to.
‘For me, learning gel nails or makeup wasn’t all that different to learning to use in-design or photoshop, it was just a new skill I had yet to master.
‘I had a box of makeup which I would practice with along with doing my nails and I was slowly getting better at it. I met with a few friends and told them I would soon be transitioning.
‘I was very much on my way. Along with this I attempted to set up an appointment with the doctor to speak about getting more HRT, which thankfully never materialized.
In an extract serialised by MailOnline from his new book, Try to Hit the Pool, Sascha reveals in his own words what made him change his mind about transitioning (pictured in 2023)
Sascha and his partner attended the VIP launch of Osteria del Mare restaurant in London on Thursday night
‘A few weeks would pass and I would message my now-partner Lucy. In an exchange of Instagram voice chats I told her I was planning to transition.
‘After a few back and forths she said hold on I need to call you. We spoke for a bit on the phone and made arrangements to meet the following week. This was when the first bits of doubt sprung up in my mind.
‘Along with my plans to transition had actually come a fairly healthy lifestyle. I didn’t really drink much nor smoke but as the feeling of wanting to be trans started to fade these habits came back.
‘Towards the night, Lucy came over everything changed. We spoke for a while about my plans and she mirrored what I was saying back to me.
‘What will happen when you start HRT?’
‘Well within a few months, I’ll start to grow breasts, my fat will redistribute and I’ll become infertile.’
‘She started repeating my points back to me and I started laughing. In those moments the feeling of certainty about transition left completely and I was again thrown into a mindset of not really knowing who or what I was.
‘That night after this I would for the first time in a very long time feel what it meant to be a man again. Without going into grotesque detail, in my marriage I was always made to be in the submissive role. I’m not sure, as I was in it for so long, that I really wanted that.
Sascha and his famous photographer father David (pictured in 2018)
‘I felt a rush of what being a man was on mine and Lucy’s first night together, a feeling I had lost, a feeling of dominance and aggression, one I had not felt since before I was married, one that used to give me a level of shame but now that feeling of shame was gone.
‘It changed me a lot and from there onwards, while still not sure of exactly what I wanted to do next. The seeds of change had been planted and I felt the joy of being male, for the first time in a very long while and maybe the first time I had felt it without any shame ever.
‘If I had to sum up what really pulled me out of the wanting-to-transition mindset it was enjoying my masculinity and being free to do so in a way that had been repressed.
‘Both in a sexual way but also in a day-to-day way of making choices, in my life travelling, going places, making my own decisions in life.
‘That and laughing at myself about what I was thinking about doing, which on its own made it impossible to carry on with anything towards transitioning as it had become extremely funny to me now.
‘The idea that young men are choosing to transition before even understanding what being a man is and having the freedom to experience the world and truly make your own decisions is, to me, insane.’
Support helpline for anyone identifying as trans, non-binary, gender variant, and their families, friends, colleagues and carers. Their phone line is open Mondays and Fridays, 8pm to midnight. Ring 0300 330 5468.
