There’s an ache that I have not yet told you about On Here. It throbs beneath the surface of my every other need. I have no idea if it’s something I’m legitimately allowed to feel, or if publicly acknowledging it is silly and self-defeating. It isn’t something I can actively chase, and it will definitely scare a few men. But let’s have a go anyway: what I ache for is decades of sex. With the same person. I am up for being open, being polyamorous, whatever relationship structure best fits my own needs and his. But fundamentally, powerfully, deeply, I yearn for long-term intimacy. As my life marches on, I find myself growing colder and colder at the thought of sex with total strangers. These days I dream of a man who I can fuck for decades.

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I’m delighted to welcome Emory Oakley to the guest slot today! Emory is a queer trans man who writes fantastic educational content about gender and sexuality over on his blog. He got in touch with a pitch about dating while trans, specifically about how getting hit on by a gay man validated his trans identity. I’m really honoured that he’s up for sharing his story here, and if you’d like to find out more do click the links to some of the other fantastic pieces he’s written elsewhere on all the details of his journey in learning about how own identity.

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Note: this piece tackles some stuff about femininity, womanhood, and ‘worth’. I do not believe that any of the things I say about ‘good girl points’ are true and I don’t encourage you to believe or internalise them. But as with all weird notions, sometimes you have to state it to slate it, so I’m allowing myself to be a bit more open about the dark beliefs that power a lot of my decisions, especially in light of some Twitter discussion I’ve seen about why you shouldn’t just keep trying to be ‘good’ and ‘liked’ all the time. Rest assured I’m working on these things.

The other day, at about 11pm, a guy offered to walk me to the train station. We’d been having a lovely evening together – eating dinner that he’d cooked for me because he knows it’s one of my favourites, watching a weird film that we’d chosen together because he cares about my opinion, then enjoying a teasing blow job because when we started getting horny I specifically requested that he let me be ‘playful’ for a bit. It was fabulous. I felt very content. Very… what’s the word? Very heard. Valued. Appreciated. But when it came time for me to head home, he offered to walk me to the station, and this objectively kind gesture made me deeply uncomfortable.

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Earlier this week, my best mate asked me if I’d tried using ChatGPT to see if it could accurately do my job. I am fascinated by machines that can learn, because I enjoy exploring the philosophical implications of computers that can genuinely think: the same thing that drew me to sex robots a few years ago now has me salivating over the possibility that a chat bot might one day achieve personhood. But in today’s world we are less worried about AI ‘achieving personhood’ than ‘stealing our jobs’. So… is ChatGPT good enough that one day it might take my job? Can robots write sex blogs? I thought I’d test it out to see whether I was in trouble.

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I could count on the fingers of one hand the number of times someone’s removed my bra with dexterity and skill. It just doesn’t happen very often. There’s a reason for this: bra hooks are pretty tricky to handle! When I was younger I think I bought in to the propaganda that a guy who was ‘good in bed’ would be able to magically unhook my bra one-handed while we were making out, without any fumbling whatsoever. But that’s bollocks. Nowadays, I think that the hottest way to remove a bra isn’t to fumble with it, or even dispense a little quick-fingered wizardry. The sexiest and most efficient way to remove my bra is to just tell me to take it off.

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