Drama LGBTQ+ Transgender

This story contains themes or mentions of suicide or self harm.

The number 2 bus finally came to a screeching halt at Jack Healy’s stop. “Thanks, driver!” he shouted, and the driver lazily put up his left arm. Now came the dreaded hill. He already had a full workout at the gym, and his legs felt like jelly. Why even bother going to the gym with these Wellington hills? Finally, out of breath and sweat dripping down his back, he reached his house, and stopped to get the mail from his mailbox. He looked through them as he took the steps to his front door. A postcard from his sister, who is on holiday in Bali, junk mail from a realtor who wants to sell his house (which he doesn’t own), a statement of account from the bank (even though he’s ticked the box to go green multiple times), and a letter addressed to someone else. 

He switched the kettle on, and read the postcard as he waited for the water to boil.

Hey Jack, 

Sending you a warm hug from Ubud. Hope you’re feeling better! Remember, I’m always here for you and I’ll be back soon. 

Lots of love! 🖤


Was he feeling any better? Some days were better than others. The medication was definitely helping, and the scar was not as visible anymore. But even just the memories of what happened were enough to make him shudder. How could he be sure he wouldn’t try again? Would he ever be able to live without those meds? He still had a few days off work remaining, but was already dreading going back. The loud hum of the boiling kettle dragged him out of his reverie, prompting him to pour the water over the patiently waiting tea bag. 

He then proceeded to throw the realtor’s brochure in the recycle bin, discarded the bank’s communication, and picked up the other letter. It was addressed to a Stephen Harris. The address was the same as Jack’s, so either the sender wrote the wrong address, or this Stephen lived here before him. The address was written in a fancy cursive handwriting and there was a heart on the envelope, which piqued Jack’s interest. Who still writes love letters these days? He knew he shouldn’t open it… it’s illegal after all. But what was the worst that could happen? Nobody will know and he deserved at least some joy in his life. 

So he proceeded to carefully open the envelope. He took out the letter, which was written in the same beautiful handwriting, and started to read as he took a first sip of his tea. 

My dearest Stephen, 

Oh, how hollow are the days without you! I wish I could be in your arms again. Though the scenery here is beautiful, I find myself yearning for the comfort of our shared world. I’ve questioned my decision to come on this trip with Jess more times than I can count. It’s as if a part of me is missing without you by my side. Although it’s definitely been good to spend some quality time with my sister! 

One of the absolute highlights so far has been a small Turkish restaurant that we stumbled upon  – the food and the atmosphere were just amazing! You know how I adore Turkish cuisine. I couldn’t help but imagine you by my side, savouring each bite with that infectious grin of yours.

Another highlight has been a day trip we took to a hidden waterfall. The hike there was arduous, but the prize at the end? Totally worth it! I wish you could have seen it. Well, you probably saw my Instagram posts, but still – in person it’s totally different! This trip is really allowing me to hone my photography skills. 

Oh, and we went shopping of course! I found the most beautiful green dress with matching shoes – I can’t wait to show you when I get back. I think I look pretty damn adorable in it ;)

But, it hasn’t all been fun and games… As you know, I’ve continued working remotely part-time on the trip. It’s not so bad though, Sarah has been very supportive of the time difference and my odd hours. It’s such a blessing to have her as my manager! She’s so much better than that idiot Rick. I actually enjoy being a developer again and I remember why I went into the industry in the first place. 

I have to go now. My sister is shouting something about urgently wanting to walk to a very old tree. Haha, it’s not like it’s going to go anywhere! Please send me news about you soon. I know you think this letter-writing business is silly and that we can just use WhatsApp, but I do think it’s so terribly romantic! 

All my love xxx


After reading the letter, an uneasiness settled within Jack. Part of it stemmed from the intimate nature of the love letter; its personal words seemed to touch a chord deep within him. Yet, it was more than that. The sender, Jackie, was describing a life that appeared to eerily mirror his own in many ways. Their commonalities spanned a shared occupation, the vexatious presence of an moronic manager named Rick (although, in Jackie’s case, it was her former boss while Jack was unfortunately still under his thumb), shared interests, and even the presence of a sister named Jess. And then of course there was the similarity in their names, separated by a mere two letters. The resemblance was uncanny, evoking in Jack a mixture of intrigue and discomfort.

He wondered what he should do now, if anything. He felt bad for both Stephen and Jackie, but he had no idea how to get the letter to Stephen. There was a return address though. He could write back and explain. His counsellor did say he needed some new hobbies to occupy his mind… this counts, right? 

He seemed to have convinced himself. He went into his study and sat down to write. He couldn’t remember the last time he wrote an actual letter with pen and paper, and felt a surge of childlike excitement. He took out the best pen from his drawer and started. 

Dear Jackie, 

This is not Stephen, it’s Jack. Your letter was delivered to me and I opened it by accident – please forgive the intrusion. I wanted to write to you so that you’re aware your letter didn’t reach the intended recipient. If you can send me the correct address, I’d be happy to get it to Stephen. 

Again, I’m sorry for having read your letter, but after starting I just couldn’t stop. I noticed so many similarities between us. I’m also a developer and my current boss is named Rick – a major pain in the neck! And I have a sister named Jess too. What’s more, I also love Turkish cuisine, photography, and…

Jack paused, wondering how upfront he should be. It wasn’t like she knew him or that they’ll ever meet, so he might as well. A flutter went through his stomach as he continued writing. 

…and I have a soft spot for green dresses and high heels! Well, not exclusively green dresses, but it’s my favourite colour, and it looks darn good on me! I’ve never admitted that to anyone. Not even my sister, and we’re pretty close. Are you close with your sister? 

Anyway, I’m sorry for invading your privacy and wasting your time. If you send me Stephen’s correct address, I will get your letter to him promptly! 



An audible sigh of relief escaped Jack’s lips as a weight he hadn’t realised he was carrying slowly lifted. He hasn’t confided his love of the more feminine things to anyone, though he has considered it. He put the letter in the envelope and put it in his backpack, ready to post it the next time he ventured out. 

In the following weeks, as he waited for Jackie’s response, not sure it would come at all, his mind couldn’t help but drift to the origin of his depression – what ultimately led him to hurt himself: he has never felt like he could truly be himself. He carried the weight of societal expectations as a constant burden, like a stone pressing down on his chest. 

He thought back to his childhood, and how he always preferred to play with Jess’s dolls and was particularly drawn to her dresses. One particular memory stood out. He was around 10, and he dared to try one of them on, a beautiful pink one, and added some of his mom’s make-up as well. Then suddenly his moment of exhilaration was instantly squashed – his dad walked in, disappointment and disgust painted clearly on his face. “What the hell do you think you’re doing?” he bellowed, each word a blow. “Take off that damn dress! If I ever see you behaving like this again, I will hit you so hard you won’t be able to sit for weeks. Fucking fruitcake!” 

Later that night, his sister, sensing his turmoil, reached out with a tenderness that touched his heart. Her concern was palpable, her innocent inquiry an opportunity to confide in someone who felt safe. A war waged within him – longing for acceptance, yet gripped by fear. The words danced on the tip of his tongue, but the scars of his father’s rebuke were too fresh, the fear of rejection and ridicule too great. He hesitated, the words left unspoken, a shield forged from self-preservation guarding his true self.

Jack had almost given up on Jackie’s response when one day, finally, a letter arrived in the beautiful handwriting he immediately recognised. This time it was addressed to him. 

Dear Jack, 

Thank you for your offer of getting my letter to Stephen. That is very kind of you, although I have to admit I was a bit upset that you had read my intimate words – but no matter. His (hopefully correct this time!) address is written on the reverse side. 

To answer your question, yes I am close with my sister. In fact, I would say that she’s my best friend. She’s six years older than me, and has always been my protector. The thing is, I was born a boy, but I never was one, not really. I always felt out of place in my own skin. Once, when I was 10, I put my sister’s old dress and my mother’s make-up on. John was furious. (He’s technically my father, though I don’t like calling him that. I don’t have any contact with him anymore.) Later that day, Jess asked what was wrong, and I decided to confide in her – I explained to her exactly how I felt, as best I could. She listened patiently and didn’t judge me. In the next few years, as I navigated this maze and started transitioning, she was always there to support me. It wasn’t always easy (an understatement!), but it was the right choice for me for sure – Jack, I can finally be my authentic self! 

From your letter it sounds like you may be having some similar thoughts, though later in life. Although I don’t know you, and everyone’s experience is unique, I would really encourage you to confide in someone – perhaps your sister? 

Be brave, Jack – it’s worth it! :)


Jackie Healy

P.S. – Please don’t forget to post Stephen’s letter! 

Jack’s pulse had quickened as he read the letter, and now, as he contemplated its contents, a subtle tremor coursed through his hands, which had grown slightly damp. Everything Jackie described mirror his own life. With the exception that he decided not to confide in his sister. Because he was afraid that she would also be disgusted in him and no longer love him. Instead, he pushed it down, which eventually caused his anxiety and depression. Was this some alternate universe, how his life would have turned out had he confided in Jess, had he been braver? Jack realised how silly this sounded, but it all was just too much of a coincidence. Their lives were like reflections in a vast cosmic mirror, each choice, each action branching out into its own reality. It seemed to Jack that the similarities were more than just coincidences – they were echoes of the same soul resonating across the boundaries of existence.

Heeding Jackie’s advice, Jack resolved to take the first step by broaching some of his unspoken feelings about gender expression in his upcoming therapy session. That morning, he donned a shirt that he had not yet been brave enough to wear outside – it was pink with delicate green flowers. He painted his nails a matching shade of green, and added a subtle touch of make-up. As he took a seat on the bus, he overheard some young boys at the back making derogatory remarks in his direction. Jack shifted uneasily in his seat, trying his best to ignore them. 

In the walk from the bus stop to his counsellor’s office, Jack glanced at his Fitbit and noticed that his heart rate had increased to 160. His fingers were tapping an anxious rhythm against his thigh. The city buzzed around him, a symphony of hurried footsteps in his ears. His gaze darted around, drawn to his reflection in storefront windows – a subtle reassurance that the shirt he chose was indeed a visible statement. 

Mary’s warm smile welcomed him into the room. Sunlight filtered through the window, casting delicate patterns of light and shadow on the walls. Her eyes lingered on him for a moment, and her voice held a gentle curiosity as she asked, “How are you feeling today, Jack? You look… different.”  

Jack seized the opening, cautiously testing the waters as he responded, “Yes, I… just wanted to try something different?”  

“That’s wonderful!” she exclaimed encouragingly. “Tell me more. Do you like it?” 

The pen on the table before him beckoned to Jack’s fingers, an inviting distraction from the thoughts that swirled in his mind. His thumb clicked the pen open and shut in a rhythm that mirrored his racing heartbeat. The rhythmic sound filled the room, a palpable manifestation of his inner turmoil. After a brief pause, he offered his thoughts. “I’m not sure. I mean, if no one cared or judged me, I would feel more comfortable openly expressing my feminine side in the way I want to. But… people make it difficult. And sometimes, it seems easier to just… hide who I am and blend in. Does that make sense?”

Mary nodded in understanding. “It does make sense, Jack. Have you felt this way for a long time?”

Mary’s soothing presence encouraged him to delve deeper into the recesses of his mind, where buried emotions whispered their truths. He found himself gnawing on his left thumb nail, a habit he had developed to cope with the anxieties that bubbled within him.

“It’s been there for a while,” Jack finally admitted, his voice catching. “Suppressing these feelings felt safer somehow, but now it’s like trying to hold back the tide.”

Mary’s gentle gaze provided a lifeline as Jack’s words poured forth. “I can’t even pinpoint when it started exactly. Maybe it was when I was a kid, drawn to things my family and society deemed ‘not for boys’. I’ve spent years grappling with this battle between my authenticity and what’s expected of me.”

His words, a cascade of truths that had long been imprisoned, tumbled out. “And now, I’m at a crossroads. I don’t want to keep denying myself the chance to express who I am. But the fear, the judgement, it’s overwhelming. And I don’t even know exactly what it is that I want. I feel like I’ve been hiding for too long. Maybe it’s too late? But I don’t want to hurt myself again. Can you help me?”

“That’s what I’m here for. We can navigate this maze together. I do want to mention that this isn’t my primary area of expertise, so I might need to refer you to someone else eventually. But we’ll cross that bridge when we get there.” 

As the session with Mary continued, Jack found himself delving into the depths of his past. Memories from childhood resurfaced, each one a piece of the puzzle that shaped his present. With each recollection, he unravelled the complexities of his struggle to express his true identity. The weight of suppressed feelings, the moments of anxiety, and the overwhelming despair all found their voice within the safety of Mary’s couch. There was still a long way to go, and there was a lot that he didn’t yet understand, but he felt better now that he’d finally taken the first crucial step. 

Jack emerged from the therapist’s office, his steps faltering as he crossed the threshold into the bustling street. His eyes squinted against the sudden burst of light. Emotions churned within him, a turbulent sea threatening to overflow its boundaries. Amidst the chaos, a small flame of happiness flickered, fuelled by the realisation of a new path he had embarked upon.

His thoughts were interrupted when his gaze collided with another pair of eyes. The intensity of the connection startled him, momentarily diverting his attention from his internal tempest, a spark that seemed to bridge the gap between them. The surrounding pedestrians manoeuvred around them, becoming part of the background as they stood still. The stranger extended a hand, an infectious grin on his face. “Hey, I’m Stephen,” he introduced himself. 

Jack couldn’t help but laugh. Confusion flickered across Stephen’s face, his outstretched hand hesitating awkwardly in the air, when at last it was seized with enthusiasm. 

“It’s nice to meet you, Stephen. I’m Jackie.”

August 25, 2023 23:30

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John Rutherford
09:15 Jan 30, 2024

I like the subject and the mature style of your mature writing.


19:32 Jan 30, 2024

Thanks John, much appreciated!


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