Courting Disaster is an advice column on matters of the heart (and loins) coming to you directly from the revolving door boudoir of international queen of hearts, Morgan M Page. A long-time notorious dater from sea to shining sea, Morgan is a trans girl on a mission to solve all problems big and small in your feminist, queer, and trans situationships. Not just any old Carrie Bradshaw, Morgan is the creator of Brazen: The Trans Women’s Safer Sex Guide, and will put her near-decade of experience as a sex educator at your disposal.
Dear Courting Disaster,
I am a non-binary faggy sort of bi trans woman who tends to be mostly into other trans women and men (cis or trans). For better or for worse, I effortlessly pass as a cis woman despite that never being the goal for my own transition.
I’ve hit a problem where years on hormones have transformed how my genitals work such that I have become an arcane puzzle-box that bewilders all of my sexual partners until they give up.
Since hormones, I have not been brought to orgasm by a sexual partner even once. Everyone who has slept with me has been a cis str8 man, also far from intentional (they only got past my “I don’t want to be seen by straight people” filter by marking themselves heteroflexible). In my experience, str8 men are generally bad at sex anyway. When I was cruising as a gay man, I was usually able to teach str8 men what to do to me to make me finish. Unfortunately, I now have no clue myself what exactly they should do. It doesn’t respond like a dick anymore, nor like a clitoris. I’ve been able to do it to myself but when others do the same things it doesn’t seem to feel like anything.
I’m not sure if this is just because the str8 men I’ve slept with aren’t very good at sex, or because I’m really that much of a challenge now. Inevitably all sexual partners get dejected and give up and many ghost on me after their second or third time failing – after getting me to reassure them post-coital that it’s ok and it’s not that they’re bad at sex. Every time I have to “nah that’s not working” it tends to kill the mood. I worry that to partners I have become a confidence-killing undesirable freak, and even that this may have led to my last relationship ending.
How do I find people who know how to sleep with trans women without resorting to attracting chasers (who tend to have no clue what they’re doing anyway) or fetishizing other trans women myself? How do I teach partners how to touch me without killing their confidence and ruining the mood? Touching someone on their body how I want them to touch me doesn’t work so well when your bodies aren’t the same.
Frustrated Fag in Massachusetts
It is a truth universally acknowledged that str8 men are bad at sex. However worldly or experienced such a man think himself to be, this truth is so well fixed that even the #NotAllMen-iest of bros must inevitably admit to it. This plain fact is the driving force behind most media aimed at str8 cis women, exemplified in Lily Allen’s Dolly Parton-inspired music video Not Fair. Lily sings, “There’s just one thing that’s getting in the way / when we go up to bed you’re just no good, it’s such a shame / I look into your eyes, I want to get to know you / and then you make this noise and it’s apparent it’s all over!”
Who among us—excluding the “Gold Star” lesbians—have not been subjected to the inept sexual fumblings of cis str8 men at one point or another? This semi-ethical slut has spread her legs from sea to shining sea, for all the legions of str8 trade who have tried to give it to me, and I can count on one hand the number who’ve managed to bring me to the Big O all on their own.
In your situation, many of these str8 men are being forced to confront their own ineptitude usually covered up by other women’s faked orgasms, and as a result they’re ghosting you rather than doing the (honest to god minor) work required to give the good D. So my advice to you starts with: don’t take it too personally that these men are failing at getting you off. They are almost definitely also failing at getting everyone else they sleep with off. It is a peculiar function of patriarchy that women (and other feminized subjects) are made to internalize the failures of str8 men. Have a feminist second wave about it by resisting this drive to assume it’s the fault of your body rather than their lack of ability.
For the str8 men who are reading this and perhaps feeling insecure— do the work before you @ me.
Now that we have that business out of the way, I would like to say that I feel a spiritual connection with you and your Samantha Brick-ian ability to complain about your life while also casually reminding us that you are beautiful and passable. I’m not dragging you—this is a gendered performance I am 100% here for! I, too, know how hard it is to be so beautiful that people are too intimidated to want to fuck you.
Onto the more serious matters: relearning how to have sex after hormones is a real journey for a lot of trans women. Estrogen and anti-androgens change the size and function of our genitals, as well as our orgasmic ability and sexual drive. Some of us suddenly lose all interest in sex, others (such as myself) find ourselves set to a constant simmer of arousal. What we might have found erotically compelling before may hold no allure now, and things we were previously unmoved by can become the bedrock of our new sexuality. Cis psychiatrists, with their harebrained theories, have sufficiently confused the discussion of trans women’s sexualities that it’s hard for us to ever have open and real conversations about it, even with each other.
That’s why it’s a breath of fresh air when someone like Torrey Peters writes a whole novella about it. In Glamour Boutique, which you can buy or read for free on her website, Torrey tells the story of trans girl Amy through vivid snapshots of her morphing sexuality over the course of her transition. Amy has, like many trans women, learned over time to completely dissociate while having sex and is overwhelmed by the discovery that poppers make her terrifyingly present for it.
I think this character’s situation may help us get at some of what is going on for you. You write that you’re able to get yourself off when you’re alone but directing partners to do the same to you fizzles out. This takes us directly into the realm of the psychological! As we all know, sex is as much about what is going on inside your head as it is about physical sensation. My question to you is: what is different about your headspace when alone vs. with a partner? Solving that one is key to unlocking your puzzle-box. Ask yourself: what situations and sensations do you need to be able to get into the right headspace with a partner, and how can you orchestrate that where possible?
As for communicating what you want from your partners, there are really two approaches. One: be direct. This is probably the best method, but if your own sexual persona is structured around being a submissive bottom it may kill a bit of the mood. So that takes us to number two: be indirect. While this way can uphold the tenuous sexual fantasy you and some VGL dom top are constructing, subtly maneuvering your partner into doing what you want but thinking it was their idea all along requires serious skill learned only through trial and error.
I advise a middle road: keep your direction minimal and your praise maximal. Instead of saying in the negative “that’s not working,” go with a positive “more like this.” Unobtrusive directions should be followed by much enthusiastic praise if even a small improvement is achieved. After a few sessions, the clumsiest and most insecure of heterosexual men will be getting you off like naturals.
Finally, I would recommend the obvious: fuck other trans women for a while until you get the handle on what works best for you. It will be especially helpful if you can find a trans woman a bit further along than you, as she’ll probably have some tips and tricks up her sleeve (one of my old tricks is fingering a trans girl’s taint during a beej—getting off that phantom-sensation pussy always works for some reason). It is not a mistake that trans women often sleep with other trans women—sometimes we’re the only ones who can help each other navigate the changing physical and psychological pathways to getting off. Sisters are doing it ourselves, etc etc.
If all else fails, huff some poppers about it (just try not to start crying with your girlfriend’s dick in your mouth, like Amy does in Glamour Boutique—very gauche).
Send your feminist, queer, and/or trans dating problems to Courting Disaster at firstname.lastname@example.org with the subject line “Courting Disaster.”