I am sitting in my psychologist’s office. It is largely a white space save for a bevy of coloured book spines behind him. His desk is spartan – a Macbook, his trusted printer, an unused computer monitor. On the wall behind me is a collage of serene watery photos – you’re supposed to look at them and pick the photo which most resonates with your mood and focus on it, a thought clearing exercise.
My psychologist wears his regular ambvalent gaze, a kind of attentive but passive semi-smile, almost bordering on a secret grin – I can tell he has practised it so as to not give a reaction to the many private things his clients might say. It is through this secret grin that he speaks.
“You need to shove more things up your arse,” he says.
Okay. He didn’t say it quite like that.
“Are you familiar with the peritoneum?” he says.
“No, I’ve never visited France.”
We have been discussing the change in my sex drive, or lack thereof, since I started dosing myself with groovy girl-making drugs for my transition. I think it’s swell that my sex drive has all but died – it’s a damned relief from the horny carnival that comes with masculinity. But he seems… disappointed, if not worried.
“Some call it the male g-spot. Here – I’ll print you something out.”
Before I can say no, he has Googled it, and he hands me a print-out of a diagram of the male testes, prostate and general bummery area. He pulls out his highlighter.
“Are you familiar with anal play?”
I pause. It is my turn for a secret grin.
Prologue: Discovering The Hand
I am late into my twelth year, A.D. and have just started experimenting with self pleasure. My Catholic primary school had pretty much avoided the topic of sex, save for a rogue teacher who had once described orgasms as like “happy sneezes”. Beyond this, the school has taught us that the son of God was born of a virgin, and that he watches everything we do. Every. Thing. He knows when you are sleeping. He knows when you’re awake.
In year eight I transfer to Mudgee High School and suddenly there’s sex-ed classes which talk about… sex. Apparently, it wasn’t a god-crime. I know this has become important in my life because I’d had my first wet dream. In the dream I was being chased by hordes of zombies, when I ran up a tree to escape. Until one of the zombies, an unusually attractive walking dead female, climbs the tree and we… thrust… into one another, repetitively, and it’s… awesome. Like a really happy sneeze. Suddenly I am awake and I am covered in some kind of goop. It is like uninvited Clag glue.
Here’s the thing no guy will tell you about wet dreams: they’re usually not a plural. Once you have your first one and you… activate, like Captain Planet, you take over the function which makes it autonomous and your body has no need of a routine purge – you’re perfectly capable of doing it yourself. Constantly.
The first thing I banged was my bed. I did this a lot, sticking my junk between the mattress and the base. This was not a long term solution for two reasons: it was ruining the bed and it was ruining my twinkie. Both came away damaged, and worse – I felt guilty! What if I got it pregnant, I didn’t know how babies worked, and I couldn’t support a tiny mattress on my pocket money.
It wasn’t until a family holiday that I found a better way. There was no way I was banging a motel mattress, and while initially I tried using a ring from a shower curtain, eventually I discovered that I could just… use my hand. The payoff wasn’t as good as my bed back home but I didn’t come away with blisters! And I could do it… anywhere! It was like upgrading from a Nintendo Wii to a Nintendo Switch!
Of course, there was something wrong about all of this. And not just the threat to forestry which came from all the tissues I was burning through. I was a boy, mostly… sort of… but I also – wasn’t. My horny teenage orgasms were fun, but they came with shame. Was this how I was supposed to prepare for sex? What if things went inside me instead?
Part One: My Digits
The first thing anyone usually shoves up themselves – is themselves.
For me, it was my fingers. It was kinda messy. Warm maybe, and a little gooey. Not exactly the “warm apple pie” that Jim predicted in American Pie, and it felt a little like I had to – poop myself out. But it was an interesting experiment.
It’s difficult to derive much pleasure from fingering your own bumhole. Partly it has to do with reach. But predictability also plays a role. Your fingers are sensitive, your bumhole is sensitive. The two provide a feedback loop that make the experience… kind of muted. Plus, unless you’re a gymnast yoga monk, you often end up holding your breath. Both because you’re squishing your ribs and also because… you’re up your own bum. Like venturing into a haunted house, you’re always on the ready for a scream.
You also need your hand for other things throughout the day, and it’s hard to escape the image of where it’s been.
Part Two: Tampons
In my early teens I have no language for what a transgender person is. In high school in the 90’s there is only “gay” and you don’t want to be that, because anything uncool is “gay”. Like homework. Or a teacher telling you to pick up rubbish from the quad.
But there is this nagging feeling inside me that – oh man, I wish I could be a girl! Like many people who later transition, I am feasting on stories of forced feminization. Stories where unwitting school boys are kidnapped or sent to stay with strange aunties who make them wear dresses or submit them to strange scientific algo-squab-minators which turn them into girls.
The compulsion to experience a female puberty burns in me. It is as strong as the need for human companionship – but instead of wanting to be with another I desperately want to be with my true self.
This includes periods. And so, I regularly stuff my undies with sanitary pads. The rush of buying them in the store is exhilarating. I create stories, just in-case I’m interogated by a cashier – “Yeah, they’re for my… sister. Doesn’t every teenage boy buy their sister’s Libras? That’s a thing, right?” Once, I even cut my finger just so I could have some blood in my pad.
Eventually, I work up to tampons. I start with the brands I have seen in ads of the girlie magazines I have nicked from girls at school: Libra, U, Tampax. As there’s not enough holes in the front of the male crotch – well, holes big enough – the only place you can stick a tampon as a teenage boy is straight up your coight.
It is not delightful.
There’s a scene in South Park, when an alien species has hidden a radar dish inside Cartman’s anus, and it protudes from him to send signals to their home planet. When Kyle asks Cartman what it feels like when the satellite dish goes back inside him, Cartman says something like:
“You know when you take a really, really big relieving crap? Well it’s like that… backwards!”
This is kind of what it feels like to have a Tampon in your bottom. And brand matters. Some are pointy. Some have ridges. The best brand I’d ever used was Tampax Applicator Tampons – because they make insertion easier by using a little guiding shaft which looks like a nuclear launch silo.
I try to keep them in for several hours, changing them after 3-4 hours to avoid Toxic Shock Syndrome, as the little pamphlet in the tampon box says to do. But I rarely survive more than one change – making for a very short period, the envy of just about any cisgendered girl. More than anything though, I feel so ashamed. I am all different shades of wrong… I’m a teenage boy, shoving girl’s products in the wrong hole… because… why?
Plus they can really hurt when you sit down the wrong way.
Part Three: Toys
Woody: You, Are, A, Toyyyyy! You’re not the real thing. You’re an action figure!
Buzz Lightyear: You are a sad, strange little man. Farewell.
No, not those kind of toys, you weirdo. Nothing sentient.
After I turn 18, I wander into adult shops – because… I’m an adult now and I have to check off one of everything in grown-up bingo. While I’m sure a lot of guys look for fleshlights or silicone vaginas, which I hover around when I sight other consumers, I’m really there for stuff I can stick inside me.
I’ve even devised the perfect plan to avoid detection – I buy one of the gift cards they have there on the rack, because I’m really buying this stuff for… someone else. I’m pretty sure greeting cards are the margin-rich staples of sex shops, because no-one is ever buying for themself.
I’ve tried a variety of toys over the years – silicone dildos, vibrators (hard, soft, bendy, long, chunky, short, ribbed) and even products aimed to hit the peritoneum – the fabled male g-spot, the prostate gland.
Of all the products I’ve bought for “other people” the most pleasurable I’ve found were anal beads. These are beady strands which look like forsaken christmas decorations. You stick them inside you for a while until you approach orgasm, and then yank them out for a double dose of cosmic power. They’re messy… like pulling out a baby calf from a future steak, but they certainly do heighten pleasure.
Adult shops also introduced me to lube.
Lube, like pockets, are essential. If there’s one thing you take away from reading this, it’s that pockets are great. If there’s two things – lube!
Part Four: Amanda
Doesn’t everyone want their girlfriend inside them?
Being an MtF transgender girl with an MtF transgender girlfriend makes sex… interesting. On one level, I can see how people would immediately want to compare it to a male homosexual encouner. This, however, is wrong. Your self is entirely different. You are not male. She is not male. You might have guy junk still, but the way you feel about your body is different. Your sensuality has changed, the way you receive and hold others has changed. Your skin is soft, you’re not covered in hair, you have boobs, you have curves and you’re not riddled with testosterone.
But more importantly, anti-androgen drugs like Cyproterone or Spironolactone, which nuke testosterone, make erections… hard. Or rather – they don’t. It’s very rare to get an erection as a transgender girl. In an act of pure mercy, you almost never get an involuntary one. And even when you try, all it takes is the slightest side thought and your progress is… softened.
Which makes it difficult to penetrate or be penetrated.
Amanda and I talk about it a week in advance of trying. We talk about our limits, what we want from sex, what we’re keen to try – consent is critical in any encounter. But when the big night comes, we’re too tired. Meh. We just order pizza and cuddle in the glow of Netflix.
The following night, we give it a bash. I’m excited. I’ve never had anything alive inside me, and I wonder if it might be the magical gateway to making anal great again. After a good hour of cuddling and kissing, when the time comes it… doesn’t go to plan.
“I’ll just… okay, yep.”
“Climb over, I’ll go this way.”
“No, it’s easier if I… yep, stay there.”
“Really? Okay, is it… are you…”
“Hold on, I’ll just… there we go… nope. Hold on.”
“Oh, that was – no, wait, nope…”
“Okay, let me try… thiiiis…”
(Silence ensues… distantly a train is heard shooping down the Burwood line. Onboard is probably a granny carrying probably cabbage back to a probable kitchen. Maybe she has a cat.)
“This isn’t working.”
“Wanna watch Rick and Morty instead?”
There’s no wrong way to make sex. Or not.
It has taken me almost 34 years, 22 of them actively, to discover that like all experiences in life – whatever, go for it. It doesn’t matter what you shove inside yourself, or who, or where you put it, as long as it’s good for you and it makes you feel good.
For me, nothing beats a cuddle. I still have a strong desire to be penetrated, I still fantasize about having vaginal sex with a guy, or a girl. Thanks to modern medicine, I could, if I really wanted it. But it’s not a high priority for me, and its certainly not as fulfilling as the warmth of my girlfriend pressed against my back, her hands cupping my boobs as I feel her breath tussling the hairs on my neck.
And as for anal play – well, maybe one day I’ll give it another crack. But it’s a lot of effort, and frankly – it can be a bit of a pain in the bum.