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Authentically asexual & trans: Winter’s LGBTQIA journey

Authentically asexual & trans: Winter’s LGBTQIA journey

Welcome to the fourth and final installment of the candid LGBTQIA+ series of stories on my blog. In this interview, I had the privilege of chatting with Winter Cayman, an extraordinary individual who identifies as asexual, transgender, and non-binary.

Shortly after moving to Sevierville, Tennessee, I met Winter and discovered the LGBTQ+ Facebook group they started. After witnessing bigotry and ignorance all around me in this area, I was craving a space that felt loving and inclusive. I joined the group as an ally before coming out as bisexual and have been so grateful for the community Winter created. I often wonder how someone as open and accepting as Dolly Parton could be from this same town, but it’s people like Winter who restore my faith in humanity and give me hope for our future.

Winter’s enlightening narrative below really captures the essence of pride and reminds us of the magic that unfolds when we open ourselves up to self-discovery and living authentically.

Tell us about your personal LGBTQIA+ journey.

I didn’t start identifying as queer until my early 20s—I’m 24 now. I was really ignorant growing up in East Tennessee. I didn’t have access to information on what it meant to be queer. When I was a teen, I knew there were gay, lesbian, and bisexual people but I thought that was it. I sympathized as an ally though. When I found out about Chick-fil-A donating to anti-LGBTQ+ causes, I thought that was horrible and started boycotting. When someone would say something bad about a gay or lesbian person, I would say they were making assumptions and that we’re all worthy of love, respect, and fair treatment. I got pushback from my family. They thought it was gross that someone could be with the same sex. But it made sense to me—just another form of love.

I went through all of middle school and high school and didn’t feel like I fit in anywhere romantically or sexually. All of my friends had crushes or went on dates. I tried going on dates, but it wasn’t appealing to me at all. I felt like I was cos-playing a straight person, so I thought, ‘okay, I must be a lesbian.’ During high school and some of college, I dated girls. That felt even more wrong and like now I was posing as a lesbian. I went on so many first dates, but never got to a second date with anyone. I figured the one would come along and sweep me off my feet like people tell you. Everyone just kept saying I didn’t meet the right guy yet, but I would, and then I would get married and have babies.

But I didn’t feel attraction to men or women, so I didn’t know how I fit in.

During my first year of college, I came across some information about asexuality. It just made so much sense to me—it was the experience I’d been having my whole life and I instantly identified with it. I came out as asexual at 21 or 22. It wasn’t overly hard to come out, but it had its challenges. When you’re gay or lesbian, people know what that is, but for me, I had to also explain asexuality because people aren’t familiar.

Some people wouldn’t believe me. They just kept saying, ‘you want attention,’ or ‘you’re not open enough to dating.’  But I simply don’t feel attraction to people.

Last year I also came out as transgender. That was really hard. When I was growing up, I looked like a stereotypical female—I wore makeup and dresses and played sports that are traditionally for girls. You never would’ve thought that I was non-binary or gender non-conforming. But I felt immensely uncomfortable with my body. Boys would show me attention because I was attractive to them, but I was completely disgusted by that.

There was a misalignment between how I looked when I looked in the mirror, how others saw me, and how I actually felt. I had gender dysphoria.

The day after I graduated from high school I cut off 13 inches of my hair. The first hairdresser I went to wouldn’t do it. Someone I didn’t know was trying to tell me that they knew better than me. But I finally found someone that would do it and it was great. I felt more myself than I ever did in my whole life. At that moment, I experienced gender euphoria. I was instantly obsessed, thinking, ‘this is right, this makes sense.’  I looked in the mirror, took pictures of myself—it was amazing!

I started wearing sports bras, doubling up on sports bras—basically DIY binding before I knew what binding was. I didn’t know anyone that was trans or non-binary. I had no language to describe what was going on so I just kept everything to myself for years. When I came out as transgender, people thought it happened overnight so they couldn’t believe it.

Last year I had two gender-affirming surgeries. I had a hysterectomy and I had my fallopian tubes and cervix removed, and then I had top surgery (mastectomy). Now I’m much more comfortable in my body and with my identity. I have language to actually describe it so it’s not as confusing or distressing anymore.

This year, I married the love of my life—me! I always pictured myself having a wedding, but could never see myself in a marriage. I saw stories of other people gathering their friends and family together and marrying themselves and I thought that sounded like so much fun! I thought, ‘why should I deprive myself of having this experience just because I’m not partnered with somebody?’

We rented a gazebo and one of my friends flew in to officiate the ceremony. It was a beautiful thing to see all of these people come together in support of this idea. I thought the weather would be nice because it was April, but it was freezing and raining—they say that’s good luck though, right?

Winter's asexual wedding

I didn’t marry myself out of self-love entirely. Self-love is very hard to attain. You have to reach an okay-ness or neutrality with yourself that I’m not sure I’ve achieved. This was more an act of just loving my life. And feeling the love of my community, friends, family, and chosen family.

You also started an LGBTQIA+ Facebook group in our area, can you talk about that?

There is an absence of affirming environments in Sevier County, Tennessee. During the pandemic in 2020, I was laid off from work, doomscrolling on my phone, and watching the news 24/7. We have these local Facebook groups here and I just found myself fighting with people on their ignorant posts. For example, there was a same sex couple getting married and asking if there were any photographers in the group, and the comments were so horrible. And I just thought, surely everyone here isn’t like this…

So I made a group for LGBTQ+ people and allies thinking that maybe me and 10 friends would join and share memes. But two days later, there were 500 people in it! There’s a queer presence in our county, we just have to keep finding each other.

In 2021 we started to plan events in person for the first time. Over a dozen people showed up and it was so cool to be in an all-queer/ally space where we could just be ourselves and no one was going to fight with us or judge us or damn us to hell. It was absolutely amazing to be in an environment like that for the first time in my life. Now we have picnics, movie nights, mini-golf, book club, Pride marches, an annual talent show, and prom.

Sevier County LGBTQ group

I didn’t think very much of it when I first made the group, but now it means so much to me and other people trying to find community in a non-affirming county. I feel a sense of responsibility to keep it going because I don’t want to see an absence again.

In 2022 I joined the Board of Directors of the non-profit, Appalachian OUTreach, and run entertainment for Sevier County. If anyone reading this is interested in joining the Facebook group, it’s called LGBTQIA2S+ & Allies Sevier Appalachian OUTreach.

How has your identity (and/or coming out) impacted your mental health?

I really struggled as a young queer person trying to figure myself out with very little understanding of queerness. If I had known about asexuality and gender non-comformity, I think I would’ve had a much easier time. Being queer in this area, I repressed it all so much just out of a need for survival because I knew people wouldn’t accept me.

I have friends who have been threatened with violence or assaulted. Lesbians who have heard ‘I’m going to show you that you’re actually straight’ and endured unthinkable acts from men. Obviously that doesn’t make people straight—that’s assault—and I didn’t want that.

I was afraid that people would want to try to cure or fix me so I put off coming out for years, especially coming out as transgender. I struggled a lot. I knew it wasn’t going to be seen as a positive thing, and for many people, it’s not a positive thing. People can sort of understand an asexual person by thinking they’re basically straight but celibate. The transgender thing does not compute.

I would never go out of my way to be in a stigmatized community. No one is seeking out violence against them. If I had any control, I would just be a heterosexual cis-gender man.

After unlearning and learning a lot of things, settling into my own skin after my surgeries, and sharing with my social circles, I’m a lot more at peace with myself now. I’m accepted by my chosen community and family and I’m not too concerned with what happens outside of that. I don’t have to live up to anyone else’s expectations. If I’m okay with who I am then that’s all that matters.

How has your identity affected your relationship with religion?

I’ve never been religious, I’m atheist. I went to a few church services when I was young and realized religion is not for me. It just didn’t make logical sense to me that there is a “sky daddy” damning us to hell for things after giving us free will. It’s all just a bunch of oxymorons and it instantly felt like a fairy-tale to me.

My parents gave me the space to figure it out on my own. They were okay with me going or not going to church. No one forced anything on me besides all the church services at my school and county meetings that begin with The Lord’s Prayer every time. But I never struggled with my faith, I just had an absence of faith.

How has your identity affected your creativity, decision-making, and relationship with others? Have you faced any unique challenges or discrimination in forming and maintaining relationships?

I grew up dancing and took ballet lessons for 12 years. I really liked it. I enjoyed the structure and discipline of it. I was always comparing myself to others though—when one of the walls is all mirrors, it’s hard not to look at yourself and compare yourself all the time.

Winter dancing

After high school I took a break from ballet. I joined a modern dance group and it opened my eyes to so many possibilities. I saw people who were different sizes and genders and transgender people all dancing together. You can be yourself and be free and you don’t need to conform and fit in this neat box. Improv, jazz, it was new and fun and I was coming into my own at the same time so I began gravitating towards the weird forms of dance art.

I tried drag for the first time in 2021. As a drag king, I thought, ‘oh my god, this is so much fun,’ and I’ve performed 4 times now for fundraisers. I feel like my identity has allowed me to really put myself out there creatively.

I feel fortunate that I haven’t been discriminated against in any significant way. I’ve seen it a lot second hand in my community and it bothers me that this area is not accepting. We’ve been trying to get Pride month (June) recognized in Sevier County, but that hasn’t happened yet. And there are the county Facebook pages I mentioned before with all the horrible comments. It doesn’t bother me much anymore because I know it would just be wasted time to engage with those people. I thought I could change their mind to recognize that we’re human, but it’s just a lost cause with some people. I have to choose inner peace over being combative with people.

I love my family to death, but we don’t relate on everything. We come from different worlds. They do make an effort to understand where I’m coming from, but we clash on things. I see them making efforts with other people’s pronouns and being respectful, but when it comes to me, I don’t get that same level of care and respect. None of them use my pronouns (they/them). I don’t feel comfortable talking about queer things in front of them. Maybe someday we’ll get there. You have to meet people where they’re at.

What are your thoughts on LGBTQ+ representation in media, society, and pop culture? Have you found role models or individuals who inspire you within the LGBTQ+ community?

We’ve come a long way but we still have so far to go. I want to see people in every form of media in all places of visibility representing all of the LGBTQIA+ community. A two-spirit individual, an asexual person, intersex people. We do see more gay and lesbian people in the media, but we don’t see the rest of the community.

I would also like to see more racial diversity in queer representation in media and positions of leadership in our local organizations. There’s a lot of whiteness in queer communities and media and I don’t think that reflects our community as a whole. We’re not going to get anywhere with LGBTQ liberation if we don’t even have racial liberation. I have privilege because I am white and I don’t have to think about my skin color because it doesn’t affect me personally. I try to confront my own biases and not center myself in spaces where I shouldn’t and amplify voices of people of color when I have the opportunity to do so.

As for role models or people who inspire me, I look to real life people and anyone that is visibly queer. Those are my heroes. When you are out and proud in public, you are giving other queer people the green light to be themselves too which is the most comforting thing. I have so much respect for people that tell others there is nothing shameful or taboo about them.

When I was younger I didn’t have queer people to look to in my own life so I would look to TV and movies. Queer Eye was one show I loved—I really like Jonathan Van Ness. I read their books and listen to every episode of their podcast because they’re so open and honest about things. Part of their identity is queer, but they’re so many other things too. Because of them, I realized you can be a queer person and also be successful, healthy, and have a fulfilling life. They showed me those things are possible.

How would you define pride?

To me pride is the opposite of shame. It’s being yourself fully and authentically when the world is telling you that who you are is shameful. Pride is not flaunting your sexuality or wanting to have a party, but being genuinely glad that you’re still alive and made it to this point.

When we celebrate pride we’re celebrating our persistence, survival, and how far we’ve come despite all the challenges we’ve had to face. We’re honoring the people who came before us and fought for our rights. They picketed, voted, had hard conversations with their families, and disrupted things. People have been killed and are still being killed for being queer. The fact that we made it this far and we’re thriving, and beautiful, and diverse, and in every profession, and have survived—that’s what pride is about.  


Thank you so much to Winter for graciously sharing this inspiring story! Their maturity and self-awareness at such a young age really blows me away—I didn’t start to feel a sense of peace with myself until I was well into my 30s. But regardless of age, I hope this makes you think about how you can do some of your own self-discovery and begin to live more authentically.

If you’re interested in more personal stories, check out the rest of this series:

Authentically gay: an interview with my Gen-Z nephew

Authentically queer: exploring my sexuality in my 30s

Authentically gay: an interview with black activist Jamal Taylor

With love,

Alison Rose

Social media: @alisonrosevintage





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