Chaye Unfolding: Empowering My Transition From Male To Female

By Chaye Hartwell

Imagine a little girl trapped inside the body of a boy. This little girl has dreams of becoming a fashion model one day, but instead, life forces her to learn the art and craft of living as a male. She attends an all-boys boarding school, plays dominant male sports, and eventually crafts herself into the societal ideal of a young man.

This little girl is me, and for twenty-five years, she remained living her life in secret. Appearing in short bursts in the dark of night through a laptop screen or my imagination, her need for existence was my greatest shame and fear. Eventually, the pain of not sharing her with the world grew too intense, and regardless of how established my male life was, she needed to come out.

Chaye Unfolding is the story of my journey towards self-acceptance and self-love. It explores my search for identity as a female, the bewilderment I felt as a child by the worlds and environments around me, and my continual struggles to eventually discover who I am.

• Language: English
• Publisher: Tablo Publishing
• Release date: May 19, 2021
• ISBN: 9781649697455

Book preview

One

New Year’s Eve heralding the start of 2018 should have been a celebration for Sabrina and me. However, it was far from this. We spent the night watching the fireworks display at Circular Quay, near Sydney Harbour, but were still both exhausted having spent the last few days with my mum and extended family in her Bowral home over Christmas.

On New Year’s Eve we got some ice cream and idly watched The Simpsons on my phone as we waited for the show to start. We weren’t drinking, so our energy levels and excitement weren’t on a par with most of the people around us. As the show started, it was clear we weren’t having fun. I hadn’t planned anything for New Year’s Eve, beyond going to The Rocks and watching the display. It’s all I wanted to do with the little money we had. We had no food with us, nowhere to sit down, and were continuously moving on our feet. It certainly wasn’t an ideal situation for us, especially Sabrina, with her eight ankle surgeries due to professional dancing.

After the display ended at around 12:30 am, we made our way through the rest of the thousands of people towards our apartment, which was on the other side of town. With all the road closures we didn’t get home until 1:30 am. We were both tired. Despite this, we routinely managed to have sex. By this point in our sex life I honestly believed that I was doing a good job, that she enjoyed it and that I enjoyed it. There was no other possible narrative I could tell myself. We were engaged, after all, and had lived with each other for almost two years. We were both independently working and living in one of the most incredible cities in the world. Our apartment was modern, near the water, and in the heart of everything. Why would I think anything was wrong?

Sex with each other had been rocky at the outset of our relationship but improved with time as we worked out what worked best for each of us. At least this story is what I wanted to believe. I still had a very dark secret that would surface in my mind 90% of the time during our lovemaking. To ejaculate, I needed to imagine myself as a woman. I was still turned on by her and more than happy to pleasure her in different ways, but to get myself to cum was a different story. And whenever she gave me blowjobs I found it even more difficult. There was a part of me that, despite all appearances, felt like it was in the wrong body. Increasingly I would imagine myself as Sabrina during sex, not myself. I attempted to bury my dark secret in the back of my mind and convince myself I was remaining faithful to her. I managed to delude myself into thinking this led me to a deeper, more spiritual and intangible connection with her – to feel into what she was feeling as a woman. I was lying to myself.

Something about that night on New Year’s Eve was different. Perhaps it was the growing distance between us intimately that made me question things more, or the symbolic start of the new year. We each have pivotal moments in life that force us to change course, and for me, this was one of those nights.

As we were having sex, I felt increasingly separate from her and found myself becoming anxious. I wanted to be her, not be on top trying to fuck her. I didn’t want to continue living this lie any longer. I was tired of not being me. Sabrina, of course, didn’t know this was all going on inside me, which made me feel even worse. Not only did I have to live with the shame of this secret, but I was dragging someone else’s life down with it. She believed that I was a twenty-five-year-old man who had ambitions as an entrepreneur in the start-up industry. She had no idea that in less than eighteen months, that man would undergo a gender reassignment operation to become female. To be fair, neither did I.

After we fucked we went to our separate beds (we both found it easier to sleep well alone). Sabrina’s was in the bedroom, and mine in the living room. Mine wasn’t even a proper bed as we had just moved in. Instead, I was sleeping on a Pilates mat with a blanket and doona. I had this notion that roughing it with only a few possessions was a ‘woke’ and ‘manly’ thing to do. I lay there on my mat and reached for my laptop.

As I had done so many times before I typed into Google, ‘how to feminise the male body’. I read articles, looked at pictures, and watched videos on YouTube. Eventually, I came across an article about someone who transitioned from male to female in their mid-30’s while they were working in the corporate finance world. It was one of the few stories I’d ever read where I felt the person was similar to me in terms of upbringing and their role in society. I never did identify with transgender stories of girls who were hyper-feminine, or even stories where the person was openly gay before transitioning. I didn’t consider myself a drag queen or even a crossdresser. I didn’t have a stash of women’s clothes in secret, nor did I know how to apply makeup. The closest I came to crossdressing was with my mum’s clothes in secret, before I grew out of them at seventeen. My only connection to this part of myself was through research online and in my sexual fantasies.

I thought my ‘research’ and fantasies were forms of sexual addiction, or just fetishes. I needed them for arousal and to reach moments of climax. When I was having sex with Sabrina, I needed to imagine myself as a woman to cum. When I was by myself, in my bed, or the shower, I needed to do the same. Since the age of fifteen, anytime I needed sexual release, I had to imagine myself in this way. I was never with anyone else in my fantasy. Just me, my body, alone, with feminine curves, and wearing female clothes. No one knew this about me.

In the early hours of the first day of the new year I completed a self-diagnosis test to determine whether or not I was transgender. The assessment was lengthy. I had come across it several times in my ten years of ‘research’. Each time I answered the questions, I tried to become more honest with myself. On this particular occasion, my results indicated that I had an 80% likelihood of being transgender.

It asked questions like: do you wear clothes of the opposite sex in private? Do you like the gender you are currently? Would you prefer to live as the opposite sex? I don’t think these questions were scientifically validated, yet they forced me to address my secret more fully that morning. When I took the test this time, I wanted to be as honest with myself as possible. In the past, I had always answered falsely just a little bit, wanting to hide from my identity — well, not this time. Now I wanted answers, no matter how confronting or challenging. And there it was. 80%. Scared for what was to come, I fell asleep anxious and exhausted.

I woke on January 1st 2018 feeling sick to my core. Around 10 am Sabrina came out of her bedroom and into the living room where I was lying. I got up and attempted to go about my day pretending nothing had happened. We chattered, ate breakfast, and listened to music. I was still tired, so told her I needed to have more of a lie-down.

I went into her bedroom and collapsed, exhausted, on the bed. I tried to sleep, but my mind was racing. My heartbeat was fast and unsteady. I closed my eyes and tried to forget, willing myself to ignore the article, the test result, and that I might indeed be a woman trapped in a man’s body. I started to sweat and began what felt like hyperventilating. I was having a panic attack. I couldn’t breathe. Eventually, practising some mindfulness techniques I had picked up over the years, I managed to breathe calmly. I tried to sleep again, but nothing. My mind was racing. What if I was transgender? What if this is who I am? What will Sabrina think? Will she stop loving me? Will she kick me out? Can I ever be happy again? Maybe I should just end my life now? Would anyone even care?

These are the questions you ask yourself when you are terrified of how someone you love is going to react to life-changing news that is irreversible once told. After two hours of tossing and turning I took some deep breaths and went out into the living room. My palms were sweaty as I pushed the door open. My whole body felt uneasy, and my vision became blurred. It felt surreal. Sabrina was on the couch with her computer, and when she saw my ghostly-pale face she asked, Are you sick?

No.

What is wrong?

I don’t know, but something is.

Come and sit next to me, she said. She was concerned and a little angry at my evasive answers. I was scaring her, and I was scaring myself. My expression probably suggested two things in her mind: either a family member had passed away or I was breaking up with her.

We’d had emotional conversations in the past, but never like this. Open and honest communication had been the bedrock of our relationship, we felt we could tell each other anything and everything – this secret was the only thing I’d never spoken of because I didn’t even want it to be real. It felt like an addiction or disease that had infected my body and wouldn’t leave me alone.

I was scared, anxious, with no idea how to start. I looked into Sabrina’s eyes, then closed mine. I breathed slowly and began to speak. Do you remember how I told you that when I was a teenager I wore my mum’s clothes sometimes?

Umm, yes… she said, feeling even more nervous about where this conversation was going.

And do you remember how a few months into our relationship you found the ‘sissysecrets.com’ website open on my phone?

Yes, she said slowly, becoming angrier.

Well, I paused and took a deep breath. Tears welled in my eyes. Sheepishly I continued, I’ve been looking into transgender things lately... and I don’t know what it means... but I need to do something about it.

She was silent, staring in disbelief at the man she loved telling her that he might be transgender. Wait! So you want to be a woman? Is that it? She exclaimed.

No, no, I back tracked to appease her. I was terrified of how my news would impact her. I loved her deeply, but could no longer go on living this lie. I just need to explore my feminine side more, like maybe I could shave my legs and body hair. And perhaps we could change the sexual dynamic in bed?

We spoke for another two hours in tears, exchanging our disappointment, shame, fear, and anger. Once the emotion had settled down we discussed the possibility that I might be transgender, but probably wasn’t. Sabrina was open to the idea of us exploring different sexual kinks, including her penetrating me, and she was even open to the idea of me wearing female lingerie during those scenes should I wish. She wasn’t, however, open to the idea of me taking hormones, changing my name, and starting a gender-transition. For now, things would have to remain as a sexual fetish and nothing more. In both our eyes at this time, I was still very much a straight man. I was in denial.

Later that afternoon she finger-fucked me anally for the first time. I had never allowed anyone to do that before. I had experimented on myself since I was sixteen, but never with someone else, or even had the thought of someone else. In that moment with Sabrina, for the first time in my life, I allowed myself to surrender fully sexually. My body started to shake and quiver as I got closer to orgasm. I had never felt a sensation like it. My entire being was vibrating and pulsating, coming alive. I came without fear of what I wanted to feel, and loved it. Never had I experienced intercourse like that. I wanted more, and my body needed it.

I had been so sexually wound up that I needed to experience a massive wave of sexual release just to keep moving forward. Over the next few weeks, we would continue to have sex like this, sporadically intermixed with our usual form of play where I was dominant and penetrated Sabrina. We found that after she fucked me, I had more energy to fuck her. I thought it would be enough to feel at balance once again with my feminine and masculine selves. However, more and more, it became evident that this wasn’t the case.

By removing the taboo of wanting to explore my feminine side, I started to feel more comfortable making slight changes to how I presented myself. I started shaving my leg hair, and then arm hair. I removed my beard, ate less red meat, ate smaller meal portions, and began doing yoga more consistently at home. The week leading up to me fully accepting my trans-identity I started wearing one of Sabrina’s maxi skirts around the house, with her consent. I began to research gender non-binary and what that meant. Perhaps I was like Jayden Smith, who wore feminine style clothes in public sometimes, yet was still very masculine as well. We even had the idea of creating a skirt company for men, as Sabrina was more and more interested in fashion. I thought this would be enough, but it wasn’t.

Soon my behaviour in the bedroom began to turn Sabrina off. I was more interested in her fucking me than I was in fucking her. On numerous occasions I also