My Transgender Madness
For the very first time, Sascha Bailey shared his thoughts on the comments made by his girlfriend, Lucy, which led him to understand that embracing his female identity was not insane.
Previously, the individual – being the son of celebrated photographer David Bailey and his former modeling spouse Catherine – had been grappling with depression to such an extent that he seriously pondered ending his own life due to profound feelings of despair.
However, it didn’t take long for him to become persuaded that his misery stemmed from gender dysphoria, and that by transitioning, he could lead a contented life.
Inspired by suggestions from online discussion groups, he sought out a private physician. After just a brief 10-minute meeting, the doctor affirmed his transgender identity and provided a prescription for female hormones.
Before going through a life-altering gender confirmation surgery, Sascha was rescued from the edge by his father and his new partner, Lucy Brown – who is now pregnant with their first child together.
One evening, Sascha remembered, took a turn as Lucy, his girlfriend, visited and they discussed his aspirations. Interestingly, she echoed his words back to him regarding his plans.
He revealed how one seven word question altered everything: ‘What will happen when you start HRT?’
In a passage excerpted by TopMob for his latest publication titled “Attempting the Plunge,” Sascha shares in his own authentic voice the factors that ultimately led him to reconsider his decision regarding gender transition.

Sascha resided in Tokyo, Japan, and over time, developed a strong determination to transition into a woman. This decision came about following a period of depression and feeling trapped in a marriage where he felt powerless.
For ten years, he was wedded to Mimi Nishikawa, a Japanese attorney who is older than him by a decade. Then, in October 2022, he left Japan after being married for that duration.
Reflecting on the sequence of events, he shares: ‘Upon my return to the UK, I had firm intentions to undergo a transition. However, gradually, as time passed, and through encounters with some crucial individuals, the concept no longer resonated with 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 aided me in realizing my actions were irrational. She found it absurd that I’d develop breasts and lose fertility, and her amusement – her utter unconvincedness – enabled me to gain perspective and distance myself.

‘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.
About three weeks into this journey, I found myself shopping for new attire with my sister and mom, since all I owned were a handful of shirts, that old suit, and a couple of dresses.
I carefully selected all feminine garments as I prepared for my forthcoming transition. During this period, I found myself in an unusual state of happiness, thinking about the numerous opportunities and unfamiliar facets of life that lay ahead for me as a woman: clothing, makeup, high heels, and gel nail art – a talent I became quite proficient in (the primary appeal of these items for me was the prospect of acquiring new skills, finding fresh avenues of interest).
‘Becoming trans involves learning numerous new things, which I find myself quite addicted to acquiring new abilities.’
As a passionate enthusiast, I found mastering gel nails and makeup not unlike conquering InDesign or Photoshop – merely another skill waiting to be honed.
Initially, I had a collection of cosmetics that I used for both applying makeup and manicuring my nails. Over time, as I practiced regularly, I began to improve in these skills. Later on, I shared with some friends that I was planning to make a transition soon.
As I was making steady progress, I found myself eagerly arranging a consultation with my healthcare provider to discuss augmenting my hormone replacement therapy (HRT). Fortunately, that scheduled meeting never came to fruition.


Over the next few weeks, I’d reach out to Lucy, who is now my partner. Through a series of Instagram voice conversations, I shared with her that I intended to undergo a gender transition.
After exchanging some messages, she mentioned that she needed to phone me. We chatted over the phone for a while, setting up a meeting for the next week. It was then that I started having the first hints of uncertainty.
As part of my transition process, I adopted a relatively health-conscious lifestyle. I seldom drank or smoked. However, as the desire to identify as trans gradually diminished, those old habits began to resurface.
As night approached, everything around Lucy seemed different. For some time, we discussed my plans, and she echoed my thoughts back to me.
‘What will happen when you start HRT?’
In just a few short months, I’m expected to experience changes such as the development of breasts, a shift in body fat distribution, and a loss of fertility.
Initially, she echoed my arguments and this triggered laughter from me. At these instances, the sense of confidence regarding the transition vanished, leaving me disoriented once more, unsure about my identity or purpose.
After all these years, that fateful night marked my rebirth as a man, a transformation I had yearned for. In the confines of my marriage, I found myself perpetually in the passive position, a role I’m not entirely sure I embraced willingly. As time wore on, I began to question if this was truly what I desired.

On our initial night together with Lucy, I experienced a surge of what it meant to be a man – a sensation I had long forgotten. This feeling was characterized by dominance and aggression, a feeling reminiscent of times prior to my marriage, which once caused me a sense of shame. However, on this occasion, that feeling of shame was absent.
After that experience, I underwent a significant transformation, and from then on, I was uncertain about my next steps. Yet, the seeds of change had been sown within me, and for the first time in a long while, perhaps even for the first time without any embarrassment, I felt a sense of joy being male.
As a lifestyle expert, I’d say my transformation from contemplating transitioning was largely influenced by embracing and expressing my masculinity authentically, a feeling that had long been suppressed. It was the joy and liberation derived from this expression that ultimately helped me break free from the desire to transition.
In terms of sexual preferences as well as daily lifestyle choices such as traveling, exploring new destinations, and making independent life decisions, my life is characterized by these experiences.
The thought of it and my laughter at my own thoughts about the action I was considering, made it difficult to continue with any transition, as it all seemed quite amusing to me now.
To me, it seems irrational to suggest that young males are opting for a gender transition without fully grasping the essence of manhood and enjoying the liberty to explore life and freely choose their own path.
Offer a helpline available for individuals identifying as transgender, non-binary, genderqueer, and their allies such as family members, friends, coworkers, and caregivers. The service operates on Mondays and Fridays from 8 PM to midnight. You can reach them by dialing 0300 330 5468.
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2025-04-05 14:37