Content Warning This is an interactive storytelling experiment with strong adult themes including explicit language, discussions of sexual orientation and gender, trans misogyny, queer hookup culture and more.
It is sometimes hard to share my experience with people, either because the subject matter is too heavy to bring up in casual conversation, or the questions are never really asked. There remain things I would like to share, or would at least like to give friends and family the option to learn about so that you might understand me better.
You can read them in a chronological order, or sort them by happiness score, or writing quality score, which is my personal assessment of what writings were most inspired. I don't necessarily think that chronology is as important as following curiosity and mood.
You may read however many short essays as you'd like to earn badges. Just hit the "I'm Done" button at the bottom for a conclusion.
Thank you for taking the time
Kai
p.s. The names of people have all been changed out of respect for their privacy
If you're expecting a clear cut explanation of how I have strongly identified with being a woman my whole life, you won't find it here. In my mid 30s I started coming to realize I was trans and, truthfully, I resisted believing it for a long time even as I took steps to transition to an existence that felt more authentic to me.
We are often looking for a clear cut origin story. That's not always the case. For some trans folks out there it has been this clear, but for many of us it's been far from anything easily summarized in a sentence or two. There is a pressure out there in society to have some story that justifies our existence and why it all makes sense. I've realized it overinvestigating the past for justifications at every step in life can become an exhausting task. And for what? So you can compile a little story for the skeptical that proves you are valid? No.
🌱🌱🌸🌸🌸🌱🌱
🌱🌸🌷🌹🌷🌸🌱
🌱🌱🌸🌸🌸🌱🌱
The best analogy I can think of is that the human mind is kind of like a vast garden. When we're born we have a garden full of flower buds waiting to bloom with the right nurturing. Over the course of our lives some areas of the garden are watered more than others. Society naturally waters parts of your garden, and other areas you need to manually water yourself if you want them to bloom. Society also encourages you NOT to water some areas of the garden. Sometimes this could be for a good reason, such as if those areas represent dangers like addiction. Other times rules simply exist based on arbitrary things, like what genitals we were born with.
Every mind is different and some flower buds will bloom more naturally than others from person to person. Ultimately we are all trying to maintain the best garden that we feel represents who we are and what brings us joy.
My from personal experience, I didn't water areas of my garden that were important to me until I gave myself permission to try. I didn't even fully understand how special this part of my garden was until I tried. I couldn't see that the colors of the blooming flowers were more representative of me until they had recieved a little water.
🌊 ➡️ 🌱 ➡️ 💥 ➡️ 🌺
Once upon a time I was all too familiar with regularly tolerating these questions from people, because I was closeted too. These days the word "discreet" is complete repellant. Over a period of exploration I quickly came to recognize that there was so much trouble with discretion I never really understood from the outside. I'll give a few reasons why:
When you're discreet, you're navigate a world of anonymity. The more anonymous you are, the more it seems people treat you like you are just an NPC in their adventure. The selfishness I have seen people exhibit is mind boggling. The information people deliberatly choose to omit can be shocking. The respect they have for your time is non-existent. It just leads to a much higher rate of asking yourself "Who the fuck did I just let into my home?".
There are people out there looking to prey on discretion and inexperience. It doesn't really matter how old you are, when you start exploring you are vulnerable. People can also leverage the ideas of blackmailing you with the threat of exposure. They don't even need to do it, they can just raise the idea even as a threat and cause you enough stress.
There is a strong correlation between discretion and not taking sexual health seriously. For example: A married man who is discreetly looking for queer sex is not telling his doctor about his sexual activity. He is not getting regular STI checks, he is not taking HIV prevention medication. He is discreet, and all of these things need names, identification, phone calls, paper trail etc..
If you are still in the closet you are likely wrestling with a lot of challenges around what your family, friends and workplace might say or think if they knew this about you. When you haven't overcome those problems yourself, it's really hard not to project them on others.
I don't think this is a particularly exhaustive list of all the problems with discretion, but it's enough to paint a clear picture why being out is safer for one's mental and physical health. It really didn't take a long time for me to recognize that maintaining discretion was not the path for me. It had many moments of elation but also many wrought with absolute despair. The elation came when things went well and the despair came when things went poorly. I recognized that I was not going to receive the best treatment from people as long as I hid in the shadows.
This was a really important first step to growing into my pride. Self worth is something that can really take a huge hit when exploring orientation and/or gender identity. Recognizing that I deserved better than this and that my orientation/identity were not a valid excuse for being mistreated was a profound step forward.
While I was still closeted, I tried to have a more serious relationship dynamic with a man. It started with a level of warmth, nurturing and attention I had never experienced before from anyone I had spoken to. I was quickly drawn in to what might be possible, but within a very short period of time he was attempting to completely control my life and break my will to resist.
Never in my life had I experienced anything close to a toxic relationship like this. A relationship where the masculine expects complete control over the feminine. Where any failure to behave as expected could be met with ire.
One evening, my friend Annie and I had a movie night. I told him in advance I would be spending time with her that evening and he requested that I keep in touch. So during breaks I would send a text. Apparently this was not enough. I was accused of being unfaithful and not texting him enough during the movie night. He was livid with me.
I remember one moment vividly after the movie ended. I picked up my phone to see a message from him saying I hadn't texted him enough, and Annie watched my body language completely shift into a pensive, distracted state. I told her we had to wrap this up shortly, so that I could deal with the angry boyfriend. When she left, despite my explanations, he was insistent I was unfaithful. He gaslighted me over and over in attempts to me feel like unworthy trash. He just wanted me to yield and apologize to him. I felt in that moment that if I didn't immediately end this he would quite literally break me. The really scary part to me is that I know for a moment I considered yielding, and it just reflects the state of vulnerability I was in to even consider such a thing.
I dumped him that night. Shortly after he started persuing my friends, including Annie! He trash talked a bunch about me to one friend because we had a shared an online photo together. Honestly, I don’t know how he thought shit talking a trans girl to another trans girl was going to work out in his favour, but he tried. His game was always about isolation, so telling someone else their friends aren't good for them fits the playbook.
I felt a bit terrorized by him for a little while, both at the conclusion of our short engagement as well as the subsequent weeks. It also made my next relationship a bit harder at the beginning, because I had residual anxiety from the fear of disappointing a partner and being brutally scorned.
This was one of the last people I met before I concluded I HAD to come out to family for my own safety and wellness. Predators lurk in the discreet corners of queer dating.
My friend Alex and I met through the dating site OKCupid. We had a mutual interest in making new friendships, so we set up plans one Friday evening to hang out at their place. This was one of the first times I had met a trans person and felt so comfortable and human. We had drinks, shared laughs and got theoretical about gender with one another very quickly. It was nice to meet someone a similar age, working in a similar field who understood what I was going through so well. They had navigated this journey already for many years and demonstrated such a relaxed attitude towards navigating gender identity.
What I did not expect that evening, however, was for Alex to propose that we go out to a bar together with their other friends who had already been invited. Quickly an evening that I thought was going to be a quiet meet and greet turned into the prospect of my first night out.
I was conflicted about taking that step into public for the first time. It wasn't because I was afraid of how anyone would react, so much as the fact that I still wasn't out with my family. I wanted to talk to them first before I ever left my home. I didn't want to risk getting caught and having them learn from anyone else. Simultaneously, the act of stepping out would bring a lot of clarity about things that I had on my mind, which could help me find the strength to come out. There was a bit of a chicken and egg problem at hand in terms of what would help move me forward.
I decided to join them that night because I saw an opportunity that I wasn't sure would happen again and I knew I'd feel safe with them. What might seem like a mild night at the bars was a life-changing experience for me. We walked to O'Gradys in the village, caught some drag, had a couple drinks and went home. I don't really want to oversensationalize the evening because what was monumental about it wasn't so much what was happening around me as inside of me both in that moment and thereafter.
Over the next couple weeks I hung out and chatted with Alex several more times. We talked a lot about the strong desire I had developed to start talking to my parents after stepping out in public. I wasn't really sure of what kind of labels to use and the wrong one felt like they could be a trap of expectations.
With Alex's help, we both concluded Queer was the best label for me to break the ice with. The term queer is great in the sense that it has no clear expectations around what it means. It just indicates you're a little different and capable of anything. Shortly after drawing these conclusions from our chats, I spoke with my family over a Sunday dinner. Overall reception was good and a new sense of comfort and freedom overcame me. I didn't have to hide my face any longer online or in public.
I'm so grateful to the friendship I made with Alex that got me over that hump. It's hard to explain just how important friends can be to helping you see things more clearly and finding the self worth and courage within you. I often say to people that are struggling with gender identity that making local gender non-conforming friends can be a huge boon.
The night I first went out in public with Alex was also the night I was introduced to Natalia, who I consider a first mentor. Natalia and I quickly bonded over passions for make up and fashion. I admired Natalia a lot for the confidence that she demonstrated and the fallibility she showed as she worked to improve her presentation. She was always great about giving constructive feedback if you were interested, but never pushy either.
Over many months, Natalia and I made plans to hang out in the gay village of Toronto night after night. We had a shared drive to grow and experiment with makeup and dress. She pushed me in ways that I wanted to be pushed because I didn't want to be an awkward, looking crossdresser in the back of the room. I wanted to be able to hold my head high in pride at the skills I had developed. Confidence in dress, was confidence in life.
Around the same time, I made friends with a trans woman from Dubai named Lorna. She just about stunned me the first time I met her because her makeup and dress were so well put together. She had a clear sense of taste for higher fashion and the same passion for improvement that I shared with Natalia. Lorna would visit Toronto from time to time for a few weeks or a month and when she was in town she was eager to get out and socialize. We would meet for drinks, chat over martinis and compliment each other's outfits and makeup. We would chat about navigating men and it's many challenges.
Natalia and Lorna both had reasons to leave Toronto at a similar time the following Spring and it left me feeling very empty for a while. Without them I had worried I'd have no one to get drinks and watch amateur drag with at The Well on a Wednesday night. No one to go dancing with at El Convento Rico on a Saturday. I had grown so much with them, but it was time for the training wheels to come off and find my own independence.
Very quickly after they both left, I took it into my own hands to make new friends who were interested in spending more time out. Although I had trouble finding the faith in myself at first, I realized how much of a foundation in confidence spending time with Natalia and Lorna had given me. The idea of grabbing a drink with someone wherever and whenever had become so much less daunting.
Natalia and Lorna have both had reasons to come back to Toronto recently, which makes me so happy. While I don't need to lean on them like I used to, I'm still up for a Dirty Vodka Martini and some drag and they are still some of my favorite people to do that with.
I feel very lucky that I've managed to make a lot of friends with other trans women and gender non-conforming people in Toronto. There's been a lot of positive outcomes from this that I couldn't have necessarily predicted.
After I came out to my family, I started opening my home to guests and hosting small parties for friends. Small parties grew into medium size parties, and medium size parties grew into ones about as big as I could fit in my place. New connections made one-by-one over social media, dating sites, chat groups, and other peoples connections. I've managed to form quite a network of supportive people around me and also helped my friends meet each other and grow their own networks too.
We're lucky in Toronto to be able to find each other so easily. Sometimes I think about how if I was living in the United States right now in a red state how impossible it would feel. Nonetheless, I do see many people from these places finding a way, because that's how important this is to us. No matter the constraints, if it's true to who we are, we find a way.
A few years ago I went to an event in Las Vegas for gender non-conforming folks, and I met people who had no one else to share their identity with back home. The importance of this event for them was tremendous, and they had travelled long distances and spent large amounts of money to have the opportunity to feel like part of a community that didn't judge them.
My friend and I have discussed returning to Vegas for event like this again but the cost in time and money seems a little bit high, considering all the opportunity we have at home.
After spending enough time building my own confidence in public, I felt like I had the capacity to give back to people who were in the situation I once was in. From time to time when navigating social media and dating sites you will meet folks who say they look up to you and want your help. Who would I be to deny this after such an extension of gratuity from others helped me?
I have tried on many occasions with varying levels of success to help other people come out in public. Unfortunately, I have seen many people disappear on me suddenly, come up with excuses, or simply admit they don't think they're ready when the time comes.
This can be frustrating to deal with because I will spend time warming up to someone and trying to champion for them before they deliver the news that they can't really go through with what they asked me for one way or another. It's important to remain patient through these experiences and just let people do things in their own time, but that doesn't mean that I have to wait for them to be ready or entertain their indecision on ongoing basis. I think it's fair to give them a shot and if it doesn't work out, let them know that they may have to try with someone else when ready. I will encourage them not to give up if this is important to them, even if they've just flaked on me.
One other thing that can be very challenging with navigating the closeted is that they will inevitably harbour a lot of internalized transphobia and homophobia, and that can be projected on me. This is a risk when helping people in situations like these, especially when I'm trying to find my own way too. I shouldn't be letting myself be brought down in order to try to bring them up.
I help when I can. I don't burn myself out. I come first and I still set an example for them by existing.
chaser | ˈCHāsər | noun
A cis man who can't get his shit together when it comes to his trans attraction. In the process of navigating his own bi-curiosity he contacts trans women to mostly objectify them, flop on plans made, and compartmentalize them in a space reserved for fetishes.
admirer | ədˈmī(ə)rər | noun
A term you also hear for trans-attracted men that can behave a bit more appropriately, though that doesn't necessarily mean they want to do anything other than send polite praise and encouragement from a distance.
What this adds up to is an inordinate number of trans-attracted men not showing up for us when push comes to shove i.e. keeping it to private quarters only.
I have many trans friends that date other trans women and avoid navigating cis men altogether. I get it. Even though I feel mostly attracted to men these days, I find myself frequently thinking I could deal with so much less garbage treatment, so much less trans misogyny, if I just dated other women.
I have noticed that many sapphic trans women have an extremely low opinion of chasers/admirers and minimal sympathy for their circumstances. I find myself on the other side of this though as someone frequently navigating them. I feel like finding ways to build trans-attracted men up and reduce the stigma would improve things for all trans women, because it implies a societal shift in public opinion. It would also hold men accountable to better behavior if we weren't relegating trans women to the bedroom as a society.
I can almost hear the hisses and boos from some of my friends and acquaintances as I say...
Afterall, for all the mistreatment they feed us, why would we owe them a damn thing?
Both ourselves and the chasers are living in a society that stigmatizes us for what we like and how we live. We both need that stigma to go away. Shame drives men to compartmentalize these feelings. Compartmentalizing the feelings makes them come out in weird ways. Trans women end up experiencing the results of those weird outbursts first hand on socials, dating sites, and on quiet street corners when noone else is around. It hurts our safety and our mental health.
As of writing this, I know of no events in the city of Toronto that cater specifically to making a safe social space for trans women to meet others without any implications of sexual activity. Sex clubs may hold events, and one bar on the Danforth has an event that helps sex workers meet clients in a bar enviroment. That's it. How on earth is maintaining this this status quo going to help make things better?
I have been spending a lot of time thinking about how to change this situation. One solution could be safer community spaces for interacting together run by and for trans women first. Meetups with strict codes of conduct that protect trans women against harassment and promote respectful treatment. Creating a safe space for trans women to meet each other as first priority, then letting allies and admirers in to events that welcome them, but only after trans community trust is strongly established. This is just an idea that I'm currently thinking through and will possibly try to organize in the future.
I recently ended the first relationship I’ve ever had where I fell in love with a man. Beyond that there were a lot of other firsts and I grew as a person in the 5 months we spent texting or audio/video calling every day.
Ultimately a few things brought it to the ground:
Distance. I was skeptical from the start I could handle dating someone who lived out in the Niagara Region, a little over an hour's drive from Toronto. I gave it an honest try but despite them being not that far away, it was too much like a long distance relationship.
White lies. While I don’t think my partner was a blatantly dishonest person, he withheld information a few too many times and it started to add up to major distrust. Patterns repeated that I couldn’t stay naive about any longer.
A toxic love triangle mislabelled as polyamory. My ex was extremely busy with work, a divorce and a child. Nonetheless he was intent on having 2 partners both of whom he couldn’t see enough. This other partner and I never spoke but I was blocked one day on socials without a word. I suspected it was out of jealousy that he and I went on a fancy date one night and shared photos. I can’t blame her either because I would feel jealous of her too at times. I've tried to stay open minded to different kinds of relationships beyond classical monogamy, but there's a lot of people just playing it selfish and pretending like this is the same as being authentically polyamorous. I felt at times like he was testing the limits of my patience, both trying to keep me on hold but never really having sufficient time or energy to carve out more physical space for me.
After having evening plans changed from a Thursday evening to during my work day, and our following Tuesday evening plans completely cancelled without any backup plans, I started to see a pattern emerging. My kindness was being exploited for weakness. I was getting less because I was tolerating it. For one of the first times in my life I had met someone who fulfilled so many of my validation needs as a trans woman that I was going blind to some of mistreatment and marginalization happening simultaneously.
I broke it off Tuesday morning and wept uncontrollably for hours. Collapsed in my shower and sobbed as hard as I could, cursed his name, and grieved the loss of potential. I grieved the loss of connection and not feeling fought harder for. Then another thing happened - I started breathing sighs of relief. The many stresses I’d let stay on my shoulders as I navigated the "polyamory", the distance and the lies of omission started to fade away. It became clear the relationship was worse for me than I could see clearly from the inside.
I will end this with some gratitude. I am grateful for the confidence he gave me to love myself in less makeup, without my long blonde wig on, wearing only sweats. I was never not beautiful in his eyes no matter how little I tried. I know this is something that has taught me to want more for myself and expect men to see beauty in me without a big facade of clothes and makeup.
It has been such a wonderful year so far and it’s not stopping now. Upward and onward!
In April of 2024 I finished coming out with my family. As of writing this that's actually only a few weeks ago. There was a 2 1/2 year gap between when I told my parents that I'm queer and when I told them I'm trans.
Finding the clarity of mind to finish the job was no easy task, but a lot of things that I do in my life I do by gut feeling. I wait until my gut tells me I'm ready and then I get it done. Since the winter time I had known I was approaching a state of readiness to talk to them. However, I found myself frequently choked up and overwhelmed with emotions when I started to prepare what I would say to them.
Telling my parents that I was queer was orders of magnitude easier than it felt to tell them that I was trans. For a very long time I had wished that I was just gay. Growing up in the 90s, there were not a lot of great models for gender non-conforming people in the media or public. My mind was filled with worry that if I only told my parents without showing them their minds would race to the same kinds of negative images and associations I had grown up with. I was worried that all the skeptical anti-trans journalism would shape too much of their opinion. I worried that if I showed them first without speaking to them it would come as a shock and make starting a grounded conversation difficult.
I didn't really get over those fears before calling them one Sunday. I think I just got exhausted of worrying and my gut finally told me I was ready enough champion through what I needed to say.
The news was as well recieved as one could expect from family. Telling them I was queer a few years prior had helped give them time to adjust, learn more on their own and be prepared to hear more. After the call I immediately sent them pictures of myself, just so there was no extended period of time spent wondering what they would see. We planned to meet for dinner at a restaurant 2 days later and I finished delivering all pertinent information, with time for Q&A.
It's really hard to put into words what coming out to a supportive family feels like. After finishing the job I had a moment of confusion where I almost didnt know what to do next. So much of my mind has been occupied by this problem, it was like having new free time I didn't know what to do with. In the coming days I saw what that empty space made room for though. A sense of balance, and control over my life. I felt like my parents' child again instead of a failure for not living a heteronormative life. With that feeling came a greater capacity to share love, passion, and gratitude.
After coming out there is still work ahead to grow our bond and find absolute comfort with one another, but I'm confident in time things will only get better.
Thanks for taking the time to read as much or as little of this as interested you.
Depending on how much you read, or the order you read it in, you may draw different conclusions about who I am or how I'm doing these days. The short answer is I'm doing really awesome. Life continues to improve every day. I'm grateful again for my supportive friends and family through this.
The other day someone was telling me about how I was brave. While I don't disagree that it takes steps of courage along the way to drive forward, I'm not sure I see myself as particularly brave. It has felt like something I just needed to do, because the alternatives were worse. It feels more like getting out of quicksand. Why would I be brave for escaping quicksand? That's just survival.
Despite navigating new challenges, quality of life has gone up. The brighter I shine, the easier navigating or completely avoiding the junkier side of trans journeys has become because I'm built on top of it.
Some of my friends reading this already follow me on Instagram, but many of you don't. If you want to reach out and stay more in touch with me let's connect there -- @sea_and_kai
Kai