Cassie Brighter’s mission statement packs quite a punch: “I bring empathy and humor into conversations that lead to social change.” But who exactly is Cassie Brighter? And why should you get to know her? Cassie is a trans woman, a storyteller, an activist, a strong feminist, and an altogether delightful human being. And yes, after our conversation, I can vouch for the fact that she does indeed bring empathy and humor – as well as a tremendous amount of warmth and knowledge – into her storytelling. Take some time to get to know her as I did, as we meander our way through stories of a youth filled with questions; a few fumbling sexual encounters; some time spent first in a cult, then as a husband, and finally, time spent as the fabulous woman who now identifies as monogamish, and who speaks up against the patriarchy.

Cassie Brighter headshot smiling into camera

A Lot Less Scary When You’re Making Them Laugh 

As a trans woman, Cassie often encounters people who have never met someone like her.  So how does she handle that? You need to challenge the way they consider the world,” she tells me, “You can’t do that without humor, you can’t do that without lightheartedness. If you do that with seriousness and rigidity, then the other person is going to get defensive.”  It’s much better to challenge people’s ideas when you’re making them laugh because, “You seem a lot less scary when you’re making them laugh and I have endeavored to make myself not scary — because for some bizarre reason people find transgender people very scary.”

Cassie feels that the reason for this is a combination of things — not the least of which is that, “Many people are stuck on the idea that there’s such a thing as a man and there’s such a thing as a woman, and that the man is defined by having this little thing hanging between his legs and the woman is defined by the ability to make babies. Science has of course uncovered that gender is a spectrum, and that gender and physiology are two distinct, separate things… but folks are scared of change. It’s like you’re rearranging their furniture. Folks like things where they used to be.” 

So, then along comes somebody like Cassie who disrupts the notion that these two camps are separate, and, as the Catholic Church put it, “Destroys the concept of nature”. “I found that hilarious,” laughs Cassie. “I posted that day on Facebook: ‘I have a pretty busy day ahead of me, because I have to do some studying for my MBA, make some phone calls, then I’m going for a walk, and then I’m going to destroy the concept of nature’.  But I do hope we’re destroying something — and that ‘something’ is patriarchy. And people don’t want that messed with.”   

Cassie Brighter posed on a city bench smiling and looking like your average soccer mom.

Just Like Your Mother

Cassie says she was always aware of the fact that she was a woman, a girl. But she grew up in a chauvinistic household, in a macho society in Argentina where the dynamic was very clear: her mother was helpless, and her father was the knight in shining armor who saved her.  

“So I grew up understanding that I’m a girl, I also grew up understanding that girls are not quite as good as boys… Women are not quite as good as men. My father would often say ‘You’re just like your mother,’ in arguments.”

“There’s this word in Spanish – maricon – and it means sissy… nancy… and I was terrified of that word. I knew what it meant. It meant homelessness, it meant ridicule, it meant you’re a pariah in society… It meant getting beat up, and it meant getting raped.  I didn’t want any of those things in my life, so I had to learn how to hide really well.” 

Cassie Brighter at Pride Portland with an unknown participant kissing her cheek.

The Deliciousness of Sexuality

At the same time, concedes Cassie, there were many tells early on. Aside from more stereotypical ones such as, having a tea set or collecting shiny stickers of flowers and fairies, (which – one could argue – doesn’t make a woman) there was this one time when Cassie was eight and a boy from the neighborhood convinced her to play a type of doctor. “He got behind me, and I felt his penis touching my butthole and it just caused a very strong cascade of emotions. Basically my sexuality awakened and I was very aware of the fact that I wanted to be penetrated.  I was very aware of just the deliciousness of sexuality, but also how scary and dangerous this was because I was also very aware of the fact that this was not the way that this was supposed to turn out. This was not the desired result, so to speak. At that exact moment my father caught us, just to make it more interesting. He wasn’t awful about it… But my father made fun of me being swishy quite often, so I learned how to butch up.”  

None Of It Made A Lot Of Sense

Time went on, and Cassie eventually did lose her virginity to a boy at seventeen and then a week later to a girl. “The results were inconclusive. I really didn’t enjoy any of those experiences. I enjoyed the newness of it. I remember I didn’t climax. It’s funny, my first experience with a boy I thought, ‘I would really like to have sex with men’ and my other thought was ‘Not this one though,’ ” she says with a laugh.  

She continued having interactions with both sexes, “And none of it made a lot of sense to me in terms of enjoyment.  I realized, many years later, that – and it’s really unfortunate that it took me so many years to realize – it wasn’t my choice of partner that was the problem, it was who I was in the bedroom. Because they were reading me as a guy, and they were expecting me to do things as a guy — and none of that really pandered to my sexuality.”  

Cassie Brighter at a march for sex positivity and black lives matter

Not Something I Believed Was Available  

Because of the religious context of the time and the way that society teaches you the binary structure of gender, Cassie grew up, “With the understanding that I would have to try harder being a boy. That I just wasn’t getting it right and that I just had to apply myself more. And that hopefully things would sort themselves out over time.” She always thought in terms of, ‘I wish I was a girl, I wish I had been born a girl’.  “But the idea of living as a girl,” Cassie says, “The idea of being a girl in society was not something I believed was available to me. You just didn’t get lucky and that’s it.”

Celibate For The Next Eight Years

By the age of eighteen, Cassie was now living in New York City, exploring the dangerous peep-shows on 42nd Street and venturing into the gay sections only to find that men were having sex with men – enjoying themselves very much! – and no one was getting struck down by God. That is until…

Shortly after buying herself a very realistic looking dildo, Cassie watched as Rock Hudson died publicly of AIDS on national TV. “I became convinced that I was going to die in a hospice. That I was going to waste away with sores all over my body and my family was going to disown me. I was not afraid of that possibility, I was certain of that possibility.  So I was celibate for the next eight years. I didn’t even masturbate for the next eight years. I joined a cult… Which in retrospect was a mistake,  but it kept me alive. I am pretty certain that I would have died, because the drive that I had toward men was strong and terrifying. In the cult, they told me that I was a pervert, they told me that I was broken, they told me they were going to fix me.”  

She Was Normal And I Wasn’t

Cassie stayed involved with the cult and during all that time she lived with this idea that the real Cassie was shameful and broken. “By the time I left the cult I figured my only option was to try to live a middle class suburban life. I was going to have sex with like two hundred people and I was going to try and find myself. I was going to sleep with women and with men and I was going to try to sort myself out.”   

Things didn’t quite work out that way.

Cassie met a woman. “The nice way to say it, is I fell in love with her. The cynical way to say it, is that she ensnared me.” They dated, got engaged, and then married. “I had two children with her and stayed with her for twelve years. There were a lot of happy things about it. It felt really good to have a family, considering how grossly off the rails I felt my sexuality and my gender were.”

Something that Cassie mentions in her storytelling standup, A Pineapple Is Not A Broken Orange, when speaking about her ex-wife  is that, “She was normal and I wasn’t, but she took me anyway.”  

“From the get-go, she knew that I was ambiguous in both gender and sexuality,” says Cassie, “So during that relationship, I tried to open up the marriage.” A spin on the bisexual website BiCafe, had her carrying on a conversation with a particularly flirtatious man. “I remember asking my then-spouse permission to fly to Miami to be with this man.”

And what was the reaction?

“She didn’t give me permission,” Cassie says with a laugh. “She wasn’t horrified, she wasn’t upset at me, she just didn’t think that we could have an open marriage. She thought that would be dangerous and too risky. She was fairly right.”   

The marriage ended after twelve years, after which Cassie realized she was “Free to do as I wish”.  

He Had Taken The Death Card Off The Table

Something very awful and very out of the blue happened: her brother died in a bicycle crash in 2009. ”Of course I felt all the grief and all the loss, but I also felt something else… resentment toward him. I was trying to scratch at what that resentment was over the month that came after that, and it shocked me to realize that I resented him because he had taken the death card off the table.”  

Cassie goes on to explain what she means by this. How many people can die in a family within the same year or two? “How shitty would it be for me to take my life immediately after he’s dead?” Horrifying as it sounds, she was always thinking that if and when things got too tough in her own life, she had the option of killing herself.   

I tell Cassie that this is a dark, dark thought.  Did she realize this?

“Yeah, it’s funny because I never really thought of it as dark,” she says, “I never really confronted how morbid this all was. I had a pretty good plan of how I was going to do myself in, for me it was like ‘Well  if things ever get too insurmountable there’s always this option,’ with my brother’s death I had to confront all this, and I had to ask myself if it was healthy to be living with this kind of mindframe.”  

Cassie brighter in a rainbow pride crosswalk carrying a pride flag and a bi-sexual pride flag.

Everybody Say Hi To Cassie

It was during this point that Cassie decided that the only healthy thing to do would be to transition. “The thing I would say, that’s the most uncomfortable about transition – not about being transgender (which is a constant), but about transition (which is the active process of trying to make the two things more congruent: your identity and the way that you look), is that a butterfly gets to go into a pupa and do it all very privately, but we are forced to live through the ugly and the messy stages in a public way. And that’s terrifying.”  

The first people who helped Cassie with her transition were her roommates, who supported her as she wore women’s clothing around the house.  There was even one roommate who,  “Somewhat between convinced and forced me, to go with her to 7-Eleven to buy some cigarettes, while I was dressed as a girl. And that was an adventure… and I was scared to death. I stayed in the car, it was absolutely terrifying. But we did it. So those were the friends who started supporting me.”

It was however, moments like the one that happened in 2014 that started making an impact. “I went to orientation at Sex Positive LA and there were about sixty people in the room and they were asking everybody to say their names and their pronouns. I had never heard of this before. It was a completely new concept to me – that you could own your pronouns… That these were not imposed on you.” When they came to Cassie, she had to say her name and pronouns. “You would think that’s an easy thing to do for a human. I sat there forever and they were going to move on, and finally I said, ‘This is my birth name, but I would prefer to be called Cassie,’ and quietly kind of mumbling, I said, ‘and my pronouns are she/her’ and I literally was hoping that they would move on. Gabriella Cordova – who was leading the group – turned to the sixty people in the room and said, ‘Everybody, say Hi to Cassie and welcome her to the group.’ And I just started bawling.” 

They’ve Got Work To Do 

While Cassie is “tremendously grateful” to Sex Positive Portland and Sex Positive LA for the way they helped her along the way during her transition, she also believes such communities often stumble in their efforts to fully embrace their trans members.  

“Being in a sex positive community really, really helped me because I was able to start sorting myself out, some of them would understand me and would acknowledge me,” she insists.  

While she values SPP and SPLA, they are places where one can see efforts at inclusion – especially compared to the outright transphobia and trans-exclusion one often finds in swinger spaces… She believes that there’s still so much work to be done. In her eyes, the biggest challenge in these liberal, progressive communities is a self-congratulatory feeling. Their leadership might be thinking, “Look how inclusive we are, we have two trans women in the group.” We’ve got to recognize that these communities — Polyamory and Sex Positive communities — still have a lot of heteronormativity and cisnormativity in them, and often leave out protocols that would make trans folks safe. Events such as “Adoring the Feminine” which sound thrilling for a cis woman, can be agonizing for the trans women who can’t be sure of how they will be embraced – if at all. “It’s a complete tightwire act,” says Cassie. And while sex positive communities offer somewhat of an umbrella of safety, there is no shield from the ignorance, which can turn an evening of celebrating the feminine into something else for those who don’t tick all the boxes. 

Cassie Brighter giving her A Pineapple is Not an Orange performance on stage

They Were My First Love As Cassie 

“I had a really positive relationship for two years with a non-binary person… They cherished me, which is a word that means a lot to me. That’s a lot to ask of sex, but that’s the kind of interaction I value. If somebody is going to touch my naked body, I want them to cherish me.”  

In her storytelling show, Cassie told a story of a lover, who had finally “made her feel seen”. I asked her if this was the person she had been referring to.

“Yeah… And they’re still the love of my life. I’m tremendously sad that it had to end.  But at the same time, we knew from the moment we started dating that this wasn’t going to last forever. They were a lone wolf, they had a path in life, that they were going to pursue, and the last thing that they needed was a girlfriend. We were in a really kind of unusual situation. They were in transition themselves —they had recently come out as non-binary. Eventually we had to part ways. Essentially, they were my first love… They were my first love as Cassie. And it really feels like one of those thirteen-year-old relationships. But it was true passion. And after something like that, it’s really hard to take the crumbs.”  

The Uhura Moment

These days, Cassie is devoting herself to two different efforts: one is Empowered Trans Woman (, a trans advocacy hub;  and the other is Smart Sluts (, which promotes female sexuality and women’s empowerment. She founded Empowered Trans Woman because, “For so many decades, I felt like I was the only freak in the universe and I felt like I had no resources available to me. What I found as I began to transition, and do research is that there are millions of trans people in the world, and I found that there are a lot of resources in place, only I didn’t know any of them. That got me really angry. To see that, once I had a good framework through which to look at my life, I felt empowered and I felt legitimate. There’s a direction I can go and it’s so important for a young trans woman to have these tools, to have this in front of them.”

Cassie likens it to a moment that Oprah talks about – when she was very young and she saw Uhura – a very black and very female, communications officer on the bridge of the Starship Enterprise. Oprah, seeing that show in the sixties, ran to her mother in the kitchen to tell her there was a black woman on tv who wasn’t playing a maid. “And that kind of a presentation, starts shifting what you think might happen to you in your life.  

I kinda had that moment when I watched Wonder Woman with Linda Carter for the first time. Kind of realized that women can be powerful and can kick ass. But there was nothing like that for trans women specifically. Something for girls like me. Then I saw some stories told in the nineties about trans women, they’re all really sweet and tragic as fuck and they all end horribly.”  

“I wanted to tell a different story. One of the most important opera singers in Argentina is transgender. She learned how to sing soprano after singing tenor, which is a huge accomplishment at her level. There are women of trans experience who are politicians and doctors, and engineers. Right now we can see the Secretary of Health in the state of Pennsylvania — She is a trans woman. So, I wanted to shine a light on these experiences. I wanted to point out different options and I wanted to tell a different story so they’ll have that ‘Uhura Moment.’ ” 

My Ideal Relationship

Cassie believes that consensual non-monogamy is really important and considers herself monogamish. “If I was going to contemplate my ideal relationship in the future, it probably would have either one or two primaries, but then we would all have the freedom to go have our adventures, meander, and discover. I’m never going to be the owner and keeper of somebody else’s genitals or their human interactions, the idea’s ridiculous.”

This was not; however, an idea that was ever discussed during Cassie’s marriage.  Mainly because, “That would indicate a failure on her part, if I was to find sexual enjoyment or emotional fulfillment with somebody else. So within that framework, it was impossible because she would have had to have confessed herself a failure as a spouse. I didn’t know how to explain to her that I wanted something different. 

It was a good relationship, but the fact that I was forcing myself to be monogamous, that  felt pretty bad. It’s okay if you want to be a vegetarian and only eat vegetables, it’s okay if you want to be asexual and never have sex, it’s okay if you only want to wear yellow.  But If any of these things are imposed on you, it starts feeling like a cage. That’s a really big challenge with relationships, where one wants to be monogamous and the other one is intrinsically polyamorous… I know several relationships like that and they make it work. They just do a lot of talking.”

Cassie Brighter in her butterfly costume on the Portland Waterfront

Empowered Trans Woman and Smart Sluts

Right now Cassie is spending much of her time with the two endeavors that she founded in order to bring information and education to both trans and cis women. “Both initiatives are really close to my heart. Empowered Trans Woman is more mature and I feel like I’m getting more traction, but Smart Sluts is coming up pretty strong too.”  

“I do care a lot about the polyam trans women and I care a lot about all trans women. But really I care about women as a whole and I want to empower women in general. The reason it’s called Smart Sluts is because the word ‘slut’ makes everyone uncomfortable.  The fact that a woman could be sexually active in a way of her choosing and have sexual agency to fuck as much as she wants to, makes other people uncomfortable. I added the ‘smart’ in there because I think we need to get better. Learning about our body and our sexuality. The amount of miseducation and ignorance I find in grown-ass women is shocking.”  

Patriarchy Enslaves Too Many Of Us

If Cassie could have her one wish – what would that be?

“The greater picture is to go to a citadel and to kill the patriarchy… That’s a really ambitious goal,” she says with a laugh. “But it’s not something I need to see happen in my lifetime and it’s not something that needs to follow me. I just need to be a very, very tiny part of something much bigger. That’s what we need to realize: that this patriarchy that got set up somewhere between five and six thousand years ago, serves very, very few of us. And enslaves too many of us.”  

Thank You, Cassie

Whether she’s up on stage telling her life story, in the classroom leading a lecture, or just on the phone with me, there’s no way Cassie’s warmth doesn’t come through. She’s been through a series of challenges, but has faced them all head on with the desire to make things different – to make things right and above all, to make things Brighter.

Thank you so much, Cassie, for sharing your life with me. You are a tremendously, lovely woman, who I am grateful that I got to know. If anyone else would like to find out more about Cassie, make sure to find her YouTube storytelling show A Pineapple Is Not A Broken Orange and look for her Medium articles by going to  


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