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.