Cis people are known for their stupid questions.
One particular question I’ve been asked a lot since I broke up with my ex a year ago is: “Would you ever date another trans woman?”
Sometimes it’s a genuine inquiry. Sometimes it’s framed as a gotcha. How can you expect real lesbians to have sex with your penis if you won’t have sex with someone else’s? I can feel them salivating with this follow-up question. Of course I would date another trans woman, I reply. That’s when they clarify that they meant a trans woman with a penis. Of course, I say again. And then they stop talking.
The fact is dating other trans women was a major factor in opening and then ending my last relationship. Yes, I generally wanted the experience of dating for the first time as a woman and a queer person. But I also explicitly wanted to explore my sexuality with someone whose body was more like mine – and, more importantly, whose experience of gender was more like mine.
It took me a damn year.
Sometimes it feels like nothing scares trans women more than queer cis women.
Considering the physical danger, explicit transphobia, and array of other bullshit my trans women friends who date men receive, I’m always fascinated by their morbid curiosity around my dating life. But – whether fairly or unfairly – the reputation of cis lesbian community is not a positive one. And while cis straight men certainly aren’t better, there’s a specific pain of being told you aren’t a woman from other women.
I constantly remind people that TERFs on the internet are not indicative of the average cis lesbian. But the truth is in my year of dating I’ve encountered plenty of transphobia and cissexism – it just tends to be more subtle. From queer cis women – and AFAB non-binary people – I’ve been explicitly rejected due to my transness, implicitly rejected due to my transness, listened to a barrage of genital-based microaggressions, and had sex with people who – sometimes in the moment – I realized were fetishizing my trans body in a way we usually only expect from cis men.
This isn’t everyone, of course. I’d say the vast majority of AFAB people I meet in lesbian community are trans women-inclusive – even if they don’t always say the right thing or haven’t had sex with any trans women before me. But it’s still pervasive enough to make my desire to be with other trans women all the more present. And it’s still pervasive enough to scare others away and make that difficult.
Being in lesbian community was never a question for me. It was my raison d’être for transitioning. Sexuality and gender are not the same, but my sexuality is explicitly tied to my gender – if not in who I’m actually having sex with then the culture and presentation that tends to accompany it. To put it simply, I identified as a lesbian long before I identified as a woman. I didn’t know what that meant and felt guilty for those thoughts, but I always surrounded myself with queer women, dated queer women, and cared about queer women culture. My transness does not preclude me from the same coming-of-age fascinations as cis women queers.
Trans women are just as likely to be queer as cis women – in fact, more likely. But many don’t share my love of this culture opting instead to form community with each other or separate from queer community altogether. I’m certainly not the only trans woman to wade through specific lesbian world transphobia – trust me, I am like other girls – but it’s not common enough to create a vast dating pool. Within the trans women inclusive spaces I spend my time, I’m not always the only one – but I’m usually one of two or three.
This is one reason I feel so invested in trans women characters appearing on shows like The L Word: Generation Q. Lesbian community desperately needs a rebranding. These spaces actually are safe for trans women and I want people to know that.
Please. Join us. Date me.
I stopped using dating apps in November, because they were making me miserable. Before my breakup I had never used them and – while exciting the first few months – I quickly remembered why. Maybe an oversaturation of media consumption has me tied to meet-cutes or maybe it really is the limitations of a dating profile, but I’m rarely drawn to people on apps the way I am literally everywhere else.
I found myself only swiping right when I was drunk and depressed and then I’d wake up the next morning and feel dread with every match. My first year post-breakup I’d only had one good experience from a dating app. Everyone else I’d met in person. Apps are just tools and this tool wasn’t working for me so I deleted it.
But over the next three months I didn’t find myself dating organically – I didn’t date at all. Except for a long overdue hookup with a friend and one surprisingly delightful one night stand, I wasn’t even having sex.
Then something strange happened. Sober, during the day, not particularly struck with loneliness, I had the desire to redownload Tinder.
I had a message from November already waiting for me – from a trans woman.
I told her that I’d been off the app and then responded to her opening line three months late. We chatted a bit about astrology – both Capricorn suns and Taurus moons, she an Aquarius rising, me a Leo – and then she asked if I wanted to hang out. She clarified that she had no expectations beyond new friends.
I told her I would love that adding: “I do think you’re cute too for the record, but no expectations :)”
We scheduled drinks for the next day.
I walked to the bar thinking what a welcome change a trans woman Capricorn was from all my AFAB air and fire signs. I wondered if maybe it was time to abandon the pride I take in my attraction to signs astrologically worst for me – Geminis, Libras, Aquariuses, Aries, Sagittariuses – and instead connect with someone supposedly more like myself.
The date was lovely – conversation was easy and comfortable. She invited me back to her place and I said yes. When she turned on her record player and Anti was playing I knew we were going to have sex.
Afterwards I found out that she’d mistyped. She’s actually an Aquarius sun, not a Capricorn. Not just an air sign – my ex’s air sign. It made sense.
That’s as much as I can share about the experience, because it doesn’t feel like my story to tell. Earlier in the night she revealed that she’s only been out for a year and that she has no trans women friends. My first encounters with other trans women were so meaningful – I can’t even imagine how I would’ve felt if sex was involved.
It was also my first time being with another trans woman, but the night simply wasn’t about me. And that’s okay. First times don’t have to be anything other than a first time.
I may not have felt what I wanted to feel. I may not have left her house knowing whether or not I wanted to see her again. But our night together had confirmed what I’d assumed for over a year – I wanted to have sex with other trans women.
Two days later an ad popped up for a new “trans-friendly” dating app called Fiori. I immediately downloaded it.
Fiori is a mess.
The first question the app asks is for you to choose your “Gender Identity or Expression.” You can only choose one and the options are as follows: trans woman, trans man, xdresser, nonbinary, queer, woman, man.
Apparently this trans-specific app isn’t familiar with the word cis. I don’t even know where to begin with the inclusion of the word queer.
I made my profile with the same five pictures I have on my Tinder and the app said my last photo didn’t pass moderation. I’m topless lying down on my bed, but not even a nipple is showing. I found a way around it – taking a screenshot during the upload process seemed to stall their moderation – but I was still annoyed.
The interface looks similar to Grindr – you browse profiles and can send “Wows” or messages to anyone you like. There are ways to filter which identities you see, but you can’t filter from their preferences. The vast majority of trans women on this app are only looking for “men” – some looking for “trans men” as well – and you have to individually click on their profiles to see if someone might be queer.
Expecting a lot of cis men to message me I made this my bio:
I write about movies and TV shows for a lesbian website.
You wouldn’t believe how little I care about cis men.
Cap sun/Sag Venus
I immediately got a “Wow” from several cis men, and one messaged me saying, “I hope you’re someone I can always talk to and get to share my deepest feelings with.” Okay, buddy.
I found two queer trans women relatively in my area but I wasn’t into them. I had to scroll all the way down to Mexico City and Ivano-Frankivs’k, Ukraine to find people I wanted to message. Neither responded which is probably for the best – if I could afford to date trans women a plane ride away I’d just date my number one Instagram crush.
I had to scroll to Philadelphia and Utica, New York to find two cis women on the app. Utica asked, “So you’re a trans?” and Philadelphia asked me what cis meant and then said she was a “transfan” but had never dated anyone trans – she had hooked up with “a nonbinary.”
I also got a message from a nearby twenty year old cis queer woman. My age settings are 25-42 on all my apps, but that didn’t show up for her, because the other thing about Fiori is its functionality is low to say the least.
The “Wows” and messages from cis men continued rolling in and I began to write a simple negative review of this app with jokes like, “Okay you’re sort of cute, but you only have one picture, no info about yourself, and you live in fucking Long Beach.”
But then someone new joined the app and messaged me.
I’m going to call this person Van, because she lives in Van Nuys and it’s a testament to how hot she is that my Echo Park-living, no car-having self was willing to travel to her.
After complimenting each other, we slipped into easy messaging small talk – how’s your day, where are you from, what part of the city do you live in. Then she said we should grab a drink sometime and despite it being 8pm I suggested we do it now.
I’ve never met up with someone from an app like that. I’ve never gone directly to someone’s apartment either. I’m usually a very cautious Capricorn. But I have electrolysis on Wednesdays and knew I wouldn’t be able to shave most of the week. And my roommate was filming a movie in our house so it was too loud to get work done anyway. I downed two shots of tequila and ordered a car.
It wasn’t until I was in the Lyft that I realized I probably should’ve asked for her Instagram handle or some sort of confirmation of her identity. She was certainly hot enough to be a catfish. I shared my location with a couple friends and hoped for the best.
I walked into her very dark apartment complex, made my way up the stairs, and knocked on her door. My stomach tightened as I waited for the door to open and reveal a middle aged man. But no. There she was – exactly like her picture.
Van invited me into her studio and I met one of her cats and sat on her bed as she uncorked a bottle of wine. She mentioned she was an escort and then apologized for not telling me ahead of time. The thought flashed across my mind that this wasn’t actually a date and that’s the explanation for why this incredibly hot person was into me – but then I realized she was just apologizing for not telling me, because some people are really whorephobic. I told her it was obviously fine and then we chatted a bit about the clients she’d seen that day.
We started talking about astrology and added each other on Co–Star. Then this Sagittarius sun, Scorpio Venus kissed me. We kept talking and kissing and talking and kissing each as easy and pleasurable as the other.
She went to pour herself another glass of wine before saying that she shouldn’t drink too much, because another date said it made her really loud and a lot. I laughed and told her she should feel free to be loud and a lot. And she was – in the best way – and it was adorable.
We kept hooking up and she told me she was a switch but wanted me to fuck her. I told her I was also a switch, but had never done that before – never fucked someone in the ass with my penis. I don’t usually fuck people with my penis anymore in general. But with her I wanted to. She asked if I was sure and I said yes.
I didn’t quite fit and it was a bit painful for me – some sort of epic irony that cis men everywhere are desperate for an extra inch and I have a decently-sized penis I couldn’t care less about – but with enough lube we eventually got it and it started to feel good. It was also just so hot to be there with her and be inside of her and watch her feel good.
The last time I fucked someone with my penis was this summer with a cis woman. It felt fetishy and made me dysphoric. But with Van we were just two people using our bodies to give us pleasure.
Neither of us came, but everything we did made me feel present. The last year I’ve only felt that way two or three times during sex – the fading of my anxious brain. And there was something unique about that happening with another trans woman. She admired my tits like only someone else on estrogen could and then she grabbed them harder than anyone had before. It was so nice.
We naturally started to slow down and get back to just kissing and talking. And then she asked if I wanted to watch Myra Breckinridge.
I wasn’t sure I heard her correctly. Myra Breckinridge? The trans cinema classic starring Raquel Welch and Mae West based on the book by Gore Vidal? She said, yes. She loved the movie and had been meaning to rewatch it. I told her I’d owned the DVD for awhile unwatched and would love to.
You haven’t seen Myra Breckinridge until you’ve watched it cuddling with another trans woman pausing to make jokes and make out.
The most iconic scene of the movie finds Raquel Welch as trans woman Myra fucking a hunky young man with a strap-on to rid him of masculinity. It’s a wild, campy movie that deserves celebration in all its problematic glory. It’s meant to be transphobic, it’s meant to be shocking, but it’s also the only piece of media I’ve ever seen where a trans woman wears a strap-on – even if the moment is less than consensual.
The movie features a lot of cutaways to classics of Hollywood cinema and in her commentary it quickly became clear that Van was a full-on cinephile. I wasn’t looking to catch feelings on this impromptu app hook up, but when a hot woman has very strong opinions about Bette Davis movies you have to succumb.
We ordered delivery from IHOP and after finishing my waffle I felt like it was time to go. I started getting dressed and she said we should hang out again and I said definitely knowing it might not happen. She’d mentioned that she wasn’t much for commitment and was usually only into people if they were unavailable. Sagittariuses.
I gave her my number and left around 2:30 in the morning. I wasn’t sure if I’d ever see her again, but I felt happy either way.
There was always a part of me that wondered if those inquisitive cis people were right. The more time that passed the more I wondered if I couldn’t blame the scarcity in my community or my pickiness – maybe it was just internalized transphobia. I wondered if maybe I would get turned off by penises and suddenly justify all the transphobic talking points I’ve fought against. That wasn’t the case at all.
The most surprising thing about these encounters wasn’t that I felt less self-conscious around other trans bodies – it was how similar these experiences were to the sex I’ve had with cis women. The acts were different, but when sex is good you’re just a body connecting with another body, listening with words and touch – hoping for some sort of connection and pleasure.
Trans people are forced to experiment, try new approaches, work around dysphoria, push through dysphoria, check-in as certain things that used to feel good stop feeling good and certain things that didn’t suddenly do. This shouldn’t just be trans sex. This shouldn’t just be queer sex. It’s nice to know what makes you feel good and it’s nice to know what generally makes other people feel good. But every new person is a new person and every new connection is a new connection. Every new body is a new body.
Fiori is not an inclusive utopia here to solve the difficulties of dating while trans. But you might meet someone just like you might meet someone on Tinder just like you might meet someone on Instagram or Twitter or – gasp! – in person.
There’s never going to be an app that’s not transphobic until we live in a world that’s not transphobic. But we have the apps we have and we have the world we have. We have the bodies we have too. Use what you have and, if you want to, fuck.
This is such a gut punch and so utterly relatable.
The intro was kinda rude tbh as a cis woman reading this trying to figure out and better understand my trans partner of 3 years. I know not everyone is the same, but I come from a place of empathy and love and don’t want to feel attacked or have assumptions made against people of my gender identity. Like, fighting fire w fire isn’t good, and anger is not what makes the world go round. :/
I read and love everything you write Drew! This was no exception.
Holy hell Drew, that’s some good writing about good sex.
On a totally unrelated note, I found out I have a stalker recently. Dude approached me on the bus and laid out his game, which I will summarize:
He is fifty years old.
He works in doggie daycare.
he lives in his mother’s basement.
Would I want to come down there and get high?
.
.
.
He knows where I live. And he proved it by describing my house and saying that he had watched me there multiple times, and his mother’s house is just down the street from mine.
Then he followed me off the bus, through the grocery store, and past my house.
I’ve seen him on the street once since then, looking at my house.
uh but anyway! Dating apps, cool cool. Maybe I’ll get on one of those one of these days. Hopefully sans creepy guys WHO KNOW WHERE I LIVE
Ahhh I’m so sorry! That’s really scary.
I cannot promise that dating apps will be free of creepy guys… but sometimes it’s worth wading through them!
Thanks Drew. I’m still trying to figure out how to feel safe again. My ex should be moving out in, oh, another two months, so I’m looking forward to dabbling in dating again.
As a cancer sun dating a sag sun for the past 3-years, I’d say the whole commitmentphobic thing might be overblown. But perhaps it’s their scorpio rising? Or the fact we both have aquarius moons?
Anyways, thanks for sharing your thoughts and life here. I really like how you write about your dates. I still dream about that story about the person making out with you, regardless of gender. It gives me hope (besides of your recounting of it being hot!).
Haven’t used this app but have plenty of experience with OKC, Tinder, HER, Bumble. I am trans feminine and identify as a lesbian. Femme presentation.
My experience dating as a lesbian with a dick was frustrating. I met a lot of bi women who seemed to be experimenting and were
You know have me interested in trying this app, but with all the cis men on there that’s giving me pause. Also, the fuck is xdresser? If it’s your clothing then, it’s yours; fabric has no gender for fuck sake.
While certainly not my experience, I know that identity is important to some people! I’m fine with someone identifying as a cis male cross dresser as long as they’re well-versed on trans issues and don’t say anything transphobic while defending their own identity.
Haven’t used the app in question but have plenty of experience with OKC, Tinder, HER, Bumble. I am trans feminine and identify as a lesbian. Femme presentation.
I stick mainly now to Tinder and OKC. Every app I’ve tried that tries to cater to trans women or lesbians has been a trash fire of catfishing and trolls. Tinder and OKC aren’t great either.
My experience dating as a lesbian with a dick was frustrating. I did not date a cis lesbian until after GCS. Before GCS the only cis women I dated via apps were women who identified as bi, but seemed to have no experience dating women. Usually just one or two dates. After GCS things changed dramatically. Way more matches and messages on apps (reluctantly I added “post op” toy profiles despite the fact that it made me cringe. Since then everyone I’ve dated has identified as a lesbian.
I don’t want to badmouth my (lesbian) community, cause I care about it so much and feel very welcome now socially here in DC. But you can read into what I’m saying.
I also dated more than one trans woman who couldn’t handle my penis. The aversion to penis is not strictly coming from cis lesbians.
I don’t know what will make things better…. Make people who identify as lesbians more accepting of some of us other lesbians. I hope that more of us coming out and challenging gender norms helps
I think because surgery still feels far off I just sort of approach dating with a feeling that I *should* be accepted for my body and if people want to have an issue with it then that’s their problem. Of course, this is easier said than done! But it’s the attitude I’ve tried to have.
I thought over the last year I would be able come up with patterns, but any time I think I’m onto something I find exceptions. I’ve had some experiences where I felt like a stepping stone for recently out bi/pan cis women. I’ve also had great experiences with bi/pan cis women. I’ve also had experiences with bi/pan cis women who had been out for a while who were fetishy towards me or uncomfortable with me. AND then I’ve had experiences with cis lesbians that have been great! Similarly I haven’t found much consistency among AFAB nonbinary people.
Guess we’re all just people! Which is nice… but also sucks, because I’d love to be like “the secret to dating while trans is only date *blank*.”
So true. I’ve searched for that pattern and haven’t really found it. The people I’ve clicked with romantically don’t have a lot in common with each other…. Except maybe that they’re tops Lol
“The most surprising thing about these encounters […] was how similar these experiences were to the sex I’ve had with cis women.” I have noticed the exact same thing! As a cis woman I’ve slept with both cis and trans women and a trans man. Out of that list, the sex I had with my trans male ex was the different and unique experience for me as a wlw. Sex with a trans woman however fell very much under the same experiential umbrella as sex with a cis woman.
Hi Drew, thank you for this wonderful ‘personal essay’ (to quote its title)! Sometimes (often?) we disagree about television and movies, but I always enjoy reading what you have to say on a subject <3
I especially related to the part about focussing on the embodied experience of oneself and one's lover. Sometimes I'm really frustrated by many cis men's disinterest in or incapability of being vulnerable and open enough during sex to experience this.
[cis, bi, GNC woman for reference]
i loved this! also genuinely laughed at “okay buddy.” 😂 need u and van to go out more times!!!!
this was really lovely. from an AFAB nb trans person, really appreciate seeing this
I would love you to drop you cell phone number or text me or text my phone (3one4)three8four4nine8zero or my gmail
Thank you for taking the time to write this Drew! Amazing as always!
Hello this was a great essay and so is everything Drew writes!!
Drew I am always so excited when I see you have a new personal essay for me to read! They are always such incredible pieces, thank you for sharing aspects of your life.
Every time I see there is a post from you Drew I get excited for some great writing. Once again thoroughly enjoyed this piece!
This was so good, Drew! Thank you for being so vulnerable in talking about these things. Also, woof, I hadn’t heard any reviews of Fiori yet but I definitely had expected/hoped for better.
I always get so excited to see there’s a new Drew article!
Thank you for writing this, Drew. Lots of recognizable t4t emotion. Lots of pathos and joy.
Hey Drew, I feel stupid commenting on this now since you wrote it a year ago, but I just wanted to say that it’s fucking powerful and brilliant and once again your writing has took my breath away