Disaster Hookups, Sexy Misadventures and being the Awkward Trans Girl in the Room.

Wanna do something dumb tonight? And when say "something dumb" I mean "me".

Lovers, I’ll gladly give you one cringe anecdote if you’re a free subscriber… but if you want more, you know what to do. X

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When it comes to hook-ups, I think the technical term for what I am is “a trash fire”?

It’s not always my fault! I swear, sometimes it’s completely out of my power. Sometimes the clock of post-hookup glow is ticking down, and your “night-time visitor” just wants to pack their things and leave but you cannot find the sex toy they brought with them. The minutes stretch out while you turn the room upside down cause of course they can’t leave it behind. You’re so baffled by its disappearance you even start to wonder “is it still *in* them? Is it still *in* me?!?” No, that would be ridiculous. You KNOW that’s ridiculous cause you didn’t even use the damn thing… but there’s no reason for this clearly expensive piece of equipment to have just vanished and as you’ve searched every other possible hidey-hole in the room you get to thinking why not check there too?

And then you remember that the item in question is rubber.

A particularly robust rubber that’s also used in the fabrication of chew toys for dogs.

I don’t have the words to describe the feeling in my chest of washing my dog’s saliva from another person’s sex toy. Seeing my beloved pup’s little teeth marks where they have worried at it. You make that pained face and apologise. You offer to replace it, but you know that no matter how understanding your visitor is you’ll forever be “the trans woman with the dog”.

Sex with me isn’t always terrible, I promise! Sometimes it’s good! Honestly!

Sometimes it’s wonderful and life-affirming, gender-affirming, prowess-affirming but goddamn there have been some clangers. The sort of encounters that are burned into your brain and you can’t help but internally scream and wish to erase yourself from history lest anybody find out about how awkward, cringe and pathetic you are.

Yeah, so I’m just gonna tell you some of them.

There’s that Hemingway quote “All you have to do is write one true sentence” that regularly jumps into my mind. I’m not in the habit of lionizing abusers so I attribute that quote to someone else. More than a decade ago a friend, a talented and published writer in her own right, gave me a sticker with that quote on it. I affixed to my cheap, chocolate-brown IKEA cube shelves. It sat there for years and always made me think of her. So, fuck you Hemingway ya gaslighting prick! I’m invoking “death of the author” and now attributing the quote to her. Yes, I will do as she’s instructed, I will write something honest. I will lay myself down on the altar of dignity and be truthful about the shambolic shit-show that is my sex life.

Okay so here goes… Christ I’m cringing already… Sometimes I hook up with couples.

One-on-ones have a lovely “meeting in the middle” vibe (pun intended), where you both discover each other’s bodies simultaneously. But the dynamic of a couple? Oh boy, you better recognize you’re being parachuted into an entrenched sexual dynamic that you have next to zero reconnaissance on. You gotta find the vibe and your place in it real quick or else you’re just the strange trans girl, awkwardly hanging out in a room while two people fuck.

Mostly it’s easy, you just start kissing someone and let the urges take over.

Sometimes though the nature of the sex a couple has been engaging in is so outside your expectation you’re left wondering “how the hell do I interact with this?” One such couple explained to me that they discovered the joys of hotel luggage racks. You know the ones? The light aluminium frame, the broad straps with wide gaps? Perfect for holding the weight of a heavy suitcase. But also, it seems, perfect for holding the weight of someone seated. Perfect for their partner to comfortably lay underneath. Perfect for positioning said partners face directly under the exposed genitals of the seated party. And yes, perfect for the person laying on the ground to service said genitals with their mouth and tongue without any of the necessary body strength if they were doing it on a bed.

I can’t stay in hotels now without thinking of this couple.

They were delighted to demonstrate. Her seated, her sex exposed between the webbing. Him on the ground underneath, mouth at the ready. And me… just fucking standing there wondering what the fuck I’m supposed to do now.

It started out weird, but I eventually figured it out. It was a fun night.

Thinking about all these “disaster hook-ups”, these “sexy misadventures” I need to keep reminding myself that more often than not this is the outcome. Fun. Reminding myself that despite me being a “trash fire” the awkward cringe of hook-up missteps are more likely to create connection than break it. You’d be amazed at how strong the “now fuck me senseless” vibes can be after seemingly unsalvageable dates.

One of the most memorable and beloved sexual encounters I’ve had came after my sweet, disabled dog, who had a laundry list of health problems, shat himself in my dates lap. Maybe it had something to do with the gentle connection my date and I forged by sitting on the bathroom floor, us both bathing a trembling pup and soothing his distress that later made my date fuck me with such fervour as to leave bruises on my pelvic bone and fingernail gouges up my legs.

Maybe the enthusiasm of another date, when they brought me to their black velvet and silk boudoir, came from the way we navigated the awkwardness of me revealing that they’d known me years earlier when I was still living as a man. And not like… casually knowing me… but having been neighbours for years. The awkwardness of watching the dawning realisation that I wasn’t some random hook-up but that we’d spent long nights talking across the gap between our apartment balconies. The discomfort of reminding them that for years our bedrooms shared a wall, and I’d lost count of the number of times I could hear them moving around in the night, either in sleepless or in the throe of lovemaking with their girlfriend.

Or the uproarious warmth resulting in from the awkwardness of explaining to someone that in your haste to book a shitty motel room, to hide away from the world with them for a few days, you’d gone and found the shittiest motel possible? No bathroom. Communal toilets and shower. It’s a hell of a way to find your lower limits. There’s nothing left to do but joke about how it’s going to make all that shower sex you’d planned weird for everyone else staying in what you strongly suspect is a converted half-way house.

You could ask why I’d keep putting myself (and others) through this ego-destroying shit-show? Yes, I could say I was doing it “for the plot”, or the joy de vie of it all. Yes, part of it is an attempt at some devil-may-care affect. An attempt to forge the emotional shield of ensuring that no one on earth could make me feel as pathetic as I make myself, but there is a greater truth.

The truth is I keep doing it because it feels honest.

Sex is messy. It’s awkward. It rarely looks how we think it will look.

Despite the cringe, those instances when the maw of embarrassment yawns open and draws you down into the cold earth, you still tumble into bed. Despite the gnawing fear that they must think you pathetic, you still fall to your knees at the altar of “them” and worship as a good lover should. Despite all the “bad”, still it’s rapturous.

Perhaps this isn’t universal but simply testament to the sort of people I attract.

I’m open to the argument that the people who would look upon this body, this face, this life and instead of seeing the ways in which it’s inadequately attempting to “be”, they instead see the ways it “is”. Perhaps it gives them a greater capacity for compassion, for understanding in the face of disaster. Perhaps these traits are inexorably linked to being interested in the mundane marvel that is this body like mine?

In all my time snatching intimacy from the jaws of disaster in this shambolic farce of a sex-life I’ve learned that it more than just feels good, but that it also makes me feel better about the world. I’ve learned that there’s a huge amount of kindness for incurable fuckups like me.

Oh, and that I should probably keep my dog away from my dates.

–S