Guest blog: My first time with a cis woman

Image by the fabulous Stuart F Taylor

Regular readers will already be familiar with Jenby’s excellent work. I’m going to keep the intro for this very short indeed, it’s just here to let you know that the following contains references to transphobia and violence, and I’m extremely grateful to her for tackling this. Here’s a piece by Jenby about her first time with a cis woman.

My first time with a cis woman

What I’m about to say may shock you.

I’ve never had sex with a cis woman.

I can count the number of cis female play partners I’ve had on one hand, and while they’ve done a lot of stuff to and with me – tranced me, diapered me, pissed on me, come while I played with their tits and another girl fingered their pussy – and I’m perfectly aware that play can also be sex (often the best kind) I don’t think any of them would necessarily class our various debauched exploits as such.

As for cis men, beyond a couple of fumbles I’ve only ever slept with cis guys for money (we don’t count the assaults lmao). I didn’t suck my first cock until I was 30 and when I did finally take up the habit it was girldick on which I cut my teeth (not literally of course, my girlfriends’ members – glorious as they are – have never been that granite-like), and prior to that I’d honed my pussy-eating skills on my enbyfriend of twelve years.

The upshot of all this is I’ve very little sexual experience with cis folk. I’m about as T4T as it’s possible to get. All seven of my partners have been transmasc or transfem, and truth be told I can’t really imagine myself, for all the respect I assuredly have for them as a community, falling in love with or marrying a cis person.


I must confess something of a guilty secret at this stage. The vast majority of porn I’ve consumed over the years has featured cisgendered women.

I find them endlessly fascinating. The strange combination of boobs and a pussy – not a neopussy, a homegrown one – on someone who IDs as female(!?) has always been a source of profound curiosity for me. I stroke to cisgenderist girls all the time. Can’t get enough.

At the heart of it I think I just love women. I love women so much that even when I’m fucking cis men for cash they occasionally ask when I first realised I was gay, despite my not having breathed a word about my sapphic inclinations. My dykery is writ so large upon me people can tell I’m a wlw even when I’m literally in the act of fucking a dude. I’m just that gay.

That said however, when it’s been your default for so long, one does tire of real women. Sorry, uh, biological women (you know, the ones who have a biological underpinning to their womanhood despite their outward sexual characteristics and who may use biology to feminise their bodies in order to affirm it. Double biology!) and at those times, inevitably, one starts craving the firm, commanding touch of a fe-shemale.

A chick with a clit.

So imagine my unbridled delight when I got an offer to shoot with a pro-domme who ticked that exact box. I was finally going to experience how it felt to do it with a cissy.

As soon as I laid eyes on her my pulse quickened. She was so wonderfully exotic. And she really looked like a woman, to boot. But a woman with a natural born vagina which she got for free!

As she stripped down to her lingerie and slipped on her strap, I marvelled at her perfectly flat, nonexistent bulge. And my girldick twitched with the knowledge that she had made a conscious choice to keep her pussy, to make herself an object of perverse desire, a walking fetish.

I couldn’t wait to have her inside me.

Then, the moment of truth.

The moment the scales fell from my eyes and I found out what I’d been missing.

And what I’d been missing is that, actually, she was just like other girls.

Other, trannier girls.

Girls like me.

Because of course she fucking was.

Because of course she fucking was.

I need a minute.


Well, that was one of the hardest things I’ve ever had to type, and I imagine whether you’re cis or trans it was just as hard for you to read.

Imagine how hard it is to hear every day at the office.

There are some parts of sex work I and my trans colleagues absolutely love, then there are the men who talk about us like the above. And these are not the exceptions. These are the rules. A constant white noise. An endless pool of molasses we have to wade through (unrelatedly, yes, I am available for WAM shoots), a tiresome, inescapable backdrop to the occasional blip of genuine pleasure, connection or joy that we find so easily when working with other SWers.

And believe me when I say it gets old.

But boring escorts out of our minds is the least of it.

Lethal violence against trans people is on the rise, most recently in a park in broad daylight just three hours from where I live. It’s not hard to see why if you’ve spent literally any time in this country over the past five years, but it is still desperately sad and entirely preventable, and it makes me angrier than I can possibly fathom.

To all you naughty boys who think you’re so kinky for loving trans girls, who think it makes you somehow special or interesting or desirable, hear this: it doesn’t. You aren’t. And you categorically do not ‘love’ us.

When you fetishise us and objectify us for things out of our control and not on our terms (yes, I’m talking about my dick! I know you love it when I do that. Well take a good look cos it’ll be gone soon), when you treat us as a kink and not as people, you other us. You make us something strange and alien. Something all too easy to hate, fear and ridicule.

Your hands may not be as bloody as those of the UK media, prominent comedy writers or children’s authors and all the other GCs actively campaigning for our genocide.

But they are not spotless.

Not by any means.

Rest up, Brianna.


  • SpaceCaptainSmith says:

    Aww. That was another really good piece. I know Jen a bit (well, we’ve met a couple of times) so will have to send my well done for this. Especially the honesty of it.

    I can only imagine how difficult it must be to make your living by relying on people who fetishise and objectify you. (I guess that’s true for SWs and porn stars in general, but clearly particularly true of trans SWs.)

  • Ava says:

    This is very powerful reading a year on from Brianna ‘s murder, too true Jen, too true – another trans individual from the UK

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