Seventeen: Sex and the Trans Girl

We are in his room. It’s my first time.

And…I am in his room. I have butterflies like I never had on stage.

I have a fair amount of alcohol on-board, not out of control, enough to take the edge off the fear.

He looks gently expectant. We both stand awkwardly for a minute, then he reaches tentatively, with an inquiring look, undoes the top button of my blouse. I stand passively, hands at my sides, and he undoes the next. And the next.

I concentrate on not shaking. He slides my blouse back, off my shoulders; it falls off my arms to the floor. His fingers travel lightly up my neck, through my long red hair, draping it over my shoulders and down my chest; one hand touches my throat, then runs slowly down, from my collar bone to my belly, around my waist to my hip.

‘You are so…beautiful.’

I close my eyes, inhale, taking that in. This is what I am here for.

He moves in close, cradles my face in his hands, kisses me very, very gently.

Then, eye contact, deep and unwavering, as he takes my hand and leads me to his bed, sits me on the edge, and gently lays me back. This time the fingers travel upward, from my navel, up my chest, back to my throat, the weight of his hand resting there as he kisses me again, deeply this time. Very deeply, waking my entire body in a flush. My fear is forgotten, my focus now on his hand, his mouth.

But…

This was my first time, and it was on my terms. I was only seventeen — he thought I was older, of course — but I’d been on my own for a while, and I’d hardened-up. Men were already a part of my survival strategy. This might be my first time willingly* ‘going all-the-way’ with a man, but I’d already had experience managing their attention and their advances. I knew how to say ‘no’, how to get what I needed, how to escape. And how to set conditions.

For example, I knew he would want me to give him head; but I hadn’t done that before, wasn’t ready for that, and I’d told him so up-front. Later, with other men, sex would not always be on my terms, but this first time, with this first man, it would be — partly because he was just a good guy, partly because I was so obviously skittish that it was clear there was no other way this was going to happen. Following my wishes was in his interest.

So, no head.

There were other conditions — he didn’t know them yet, but he was about to find out.

You see, once again, it was complicated.

I’ve been a virgin three times. This was actually the second time; the first had been with a woman, a year or so earlier. The third and final deflowering would also be with a man, but that was still well over a decade in the future, after my transition, after hormones and surgery, when it would no longer be complicated.

And here’s another odd thing: I am not now, nor have I ever been, gay or bisexual. I have always been heterosexual — OK, a bit ‘flexible’, shall we say — but at the core neither my gender nor my sexuality has ever varied (despite appearances to the contrary and the occasional confusion of my partners).

I am now and always have been a heterosexual woman. But I appreciate that this man may have been unaware of the fact, since at the time I did have a penis. Which he liked and I didn’t. Awkward.

He unzips my jeans and runs a hand down into my panties.

‘Don’t touch that.’

The hand withdrawn, confusion. I slip out of my jeans.

‘It’s OK love, I just don’t want to be touched there. Kiss me?’

It’s hard to explain how this works, but when you’re a woman with a penis and raging gender dysphoria, sex is complicated. One craves intimacy, like any human, and all the usual urges and attractions are there…but there is a kind of mental gymnastics one must go through to convince the mind to go along with the body. Sexuality is whom you go to bed with; gender is who you go to bed as. It is wrenching to live in a body that does not align with your most basic identity, and never more so than when someone else is touching that body. Whether he realises it or not, I am a woman going to bed with a man. The mental gymnastics require holding an image of my female body intact whilst everything happens.

So, no touching that.

Kneeling on the bed, I unbutton his shirt, run my hands up under the collar and slip it off as I slide my hands over his shoulders and down his back. Kiss. He lays back and I undo his trousers, he kicks them off as I cup him, kiss his chest, his trim belly. Going lower makes me uncomfortable, so I move back up to his lips, slide down next to him, and pull him on top of me. I whisper in his ear.

‘Take me like a woman.’

There is evidently a disconnect on the meaning of the verb ‘to take’: he starts to do precisely the wrong thing.

‘No!’

He is alarmed and confused. Of course. After all, he thinks he is in bed with a man. He isn’t.

‘Sorry, no, don’t touch me there. Look, just love me as if I were a woman, OK?’

Now he’s got the idea. But there is a problem. He says,

‘Um, honey? It doesn’t really work like this, you need to roll over.’

Well, how would I know? This is my first time. Not quite the way I’d imagined it, but I’m able to hold my body image intact throughout, so things go OK.

He finds me beautiful; that’s the main thing.

So, if this is my second first time, what about that first first? And if that was with a woman, then how can I be heterosexual, and not lesbian or bi? It’s hard to explain how this works, but when you’re a woman with a penis and gender dysphoria, sex is complicated…

Not all trans women are sexually functional, but many are, and I was. And gender dysphoria — the painful, pervasive sense that one’s sexual anatomy and chemistry are at odds with the self — is not a constant; it waxes and wanes, from discomfort to agony. In my case it would lie quiescent for periods, operating at a low level of vague distress, only to rise up unexpectedly, raging and crippling every aspect of my life, until the crisis broke and I would recover, through some drastic action, back to a state of functional discomfort.

Humans are incredibly adaptable and can adjust to the most severe and outrageous conditions, even ones where the body and mind are at war. I was trapped in an intolerable condition which I learnt to tolerate. During periods of relative quiescence, between major dysphoric episodes, I learnt to function ‘as a man’. I learnt male behaviours and met society’s male expectations, and one of those expectations is that men are attracted to women.

I was attracted to women, and I took that attraction to be of the ‘normal sort’. In retrospect, it wasn’t. I was fascinated with women’s bodies, and combining that with the urges that came with the body I had, I parlayed that into a functional sexuality. I was uneasy around men and generally preferred the company of women, so during periods of dysphoric quiescence this worked.

Decades later, out of deep curiosity, I contacted a woman with whom I’d had a love affair during my teens. She remembered me as a most unusual bedfellow, unlike any man she’d been with before or since. Not only was I strangely feminine, but I seemed to be interested only in her body and not in my own. She remembered me fondly, as a most attentive lover. She was not the least surprised to learn that I’d transitioned — it answered a suspicion she’d had at the time.

I can only speak for myself, and this is speculation, but I think that a kind of vicarious identification with a female partner — a sort of psychic transposition — accounts for many transgender women being able to function in the role of heterosexual men. After transition many do carry on as lesbians, but many of us ‘flip’ — switching from female partners to male ones — including women who have not had relationships with men prior to transition. I find this fascinating.

I think it has to do with the ‘who you go to bed as’ part of the equation: we respond as heterosexual women once anatomy and hormones have been brought into alignment with the self, and — this is key — once heterosexual men respond to us as women; something that cannot occur until we ourselves are ‘right’.

So yes, prior to transition I functioned as a strangely feminine, oddly attentive, ‘heterosexual man’. Except when the dysphoria surged up and consumed me — then the red-haired green-eyed woman took over once again. This is one of those times.

He is up and dressing as I awake.

‘You’re leaving?’

‘Just going to the store, it might take a little while, don’t go anywhere, OK?’

‘OK, I’ll be here.’

I shower and dress in his absence, poke around, snooping just a bit. He’s very well-off, his flat is rather posh, appointed with nice things; I’m very poor and I feel the envy. There are banknotes and some change in a dish, but I leave them. I look through his books. He’s gone quite a long while.

He returns and takes me out to ‘brunch’ at a very nice place. He fits in, I feel way underdressed. He is very, very sweet to me. I feel seen, special, beautiful. His eyes sparkle.

Casual conversation halts and he looks searchingly into me.

‘You really do want to be a woman, don’t you?’

I am young, confused; I don’t yet understand that I am already a woman — that knowledge will come, much later.

‘Yes, I suppose so.’

He smiles, takes out a small package: he has bought me a gift.

He stands, and I can’t see what he has as he moves behind where I’m seated. Then a fine gold chain is looped around my neck as he works the clasp and sweeps my hair clear. There is a single tear-drop pearl at the base of my throat.

I tear up. He kisses my cheek.

‘I hope you get what you want, honey.’

I will see him again.

For backstory as to why I was in this man’s room, see this thread.

How it happened that this event was my entry into sex work is covered in this story in SELF Magazine.

For another episode related to sex work, four years later, see The Woman I Left in San Francisco.

* ‘…my first time willingly “going all-the-way” with a man…’
I was previously raped. That story is told in What He Did to Her.

I tell the story of the ‘third and final deflowering’ in
Conflicted Romance, Part 2 — Falling in love, and a girl’s First Time.

Metamorphosis describes my very different life, just prior to this story.

I make a spare living doing this. You can support my work and get draft previews and my frequent ‘Letters Home’ for less than the cost of a coffee.