Conflicted Romance, Part 2 — Falling in love, and a girl’s First Time

[Previous: Conflicted Romance, Part 1.]

(Sexual content, but not graphic.)

It was several years after my unconsummated brush with RJ that I met Jim. Like RJ, Jim was a big, lovely, sweet man who enjoyed wrapping me in his arms, kissing my forehead as I nestled against his chest. The feeling of shelter and affection I experienced in Jim’s embrace is, to this day, one of my most cherished memories.

To Jim, I said ‘yes’.

After my initial round of post-transition dating, during my early 30s, I shut down for quite a while. I was unable to resolve the conflict between the need for honesty about my past, and the destructive consequences of ‘disclosure’. If I remained ‘deep stealth’* within the relationship, keeping my trans past a secret, then I faced the hideous need to misrepresent much of my history — you can’t exactly have a romantic relationship whilst not discussing the previous decades of your life, right?

On the other hand, my experience had been that disclosure of my transgender history was utterly ruinous to normal interaction with men. During the latter part of transition, once I was passing consistently as female, I had numerous encounters with this effect. In general, when women I was interacting with learnt of my trans status they would still respond to me as a woman — their essential behaviour towards me would remain unchanged, even as the inevitable confusion and flurry of questions unfolded.

But men were another matter. When they learnt of my trans status, they would literally step back to increase the physical space between us; if seated, sliding their chair away if necessary*. Even men who had known me for some time. Even liberal, open minded men. Even gay men. And even men who chose to maintain our relationship; who were so open-minded and positive toward me that they put great effort into appreciating and understanding me — even they never again responded to me as the woman they had known before disclosure. Even if they went so far as to hold me or kiss me, there was always this distinct dissonance in their action.

As I was never a man, I never had this behaviour or whatever feeling lies behind it. I have no understanding of what this is or how to counteract it. If you are a cis man, please reach out to me, I would dearly like to know what makes you step back from me, if only to know if you are aware that you do this.

Unable to resolve the conflict between honesty, disclosure, and my need to be accepted as the woman I am, I pushed all thoughts of romance from my mind and my life. When men would approach me, as continued to happen, I rebuffed them. I stopped wearing makeup and began to dress dowdy so as to discourage attention. I gained weight. Inevitably all this had an effect on my perception of myself as a woman. I stopped being the lovely creature I had worked so hard to become, and began to transform into a sexless shadow of myself, hiding myself from the Male Gaze and, in a way, from my own.

After a couple years of this downward slide I improved other aspects of my life, to where I was more comfortable. I lost the weight and regained most of my former attractiveness and self-esteem as a woman. Still single and now age 39, I started to get that now-or-never feeling. With the disclosure issue still unresolved, I resumed dating. After a number of thoroughly unsatisfactory forays, I lucked onto Jim and fell into his arms.

A few dates on, snuggled up together on a bench, watching the sun set after another lovely, romantic dinner, I was once again faced with the need to disclose. I had a real shot with Jim. The physical, intellectual and emotional chemistry were all there. We both wanted this to go somewhere. I had dodged around my personal story as best I could, but that process was inevitably moving toward the realm of outright falsehood, from which I’d soon be unable to extract an authentic love affair.

As so often happens, for me at least, the moment got in the way of the plan. That evening, I took Jim home.

Put yourself in my place. Not wanting to spoil our sunset intimacy, I delay the difficult discussion. Jim drives me home. He opens the car door for me, gathers me into his arms and walks me to my door. We kiss. Long kiss. I open the door and draw him in after me. Jim loves tawny port; somehow I just happen to have an unopened bottle of a rather good tawny port, which he opens and pours for us.

We’re on the sofa, cozied-up, sipping port. I know this is disclosure now-or-never. I’m desperately trying to gather my courage. I really need this to work. But some buttons get undone. A shoulder strap slips off. His whiskers tickle my neck. My nipples are hard. He smells so good. I feel a little dizzy, a little flushed, I feel…opened-up.

Do you seriously think I’m going to screw this up now? I don’t think so. I’m a thirty-nine year old virgin, and this is happening. Right now.

Clothing is shed; we are in my bedroom, we are in my bed. This is the first time I’ve allowed things to go this far, and…we are naked, we are intertwined, and I’m allowing everything.

A girl’s First Time is such an unknown until it’s happening, even if that girl is pushing 40. You can guess, you can imagine, but there is no way to know until you’re there, in the centre of it, and it’s all happening, now.

And if you’re lucky, if the man is loving, if he is attentive and practiced, and you are relaxed and ready, then this is when you discover something astonishing. This is when you discover an experience like no other. This is when you discover that, not only has the plumbing been fixed, but the electricity is most definitely on.*

At its best, the female orgasm is an astonishing thing. It begins tentatively, shyly, requires concentration, needs focus. It begins in your pelvis and your chest, in your belly, your neck, your thighs; starts to build, tenuously, recedes, must be coaxed forth again, builds again… After a few cycles, if you can maintain focus, then this cascade starts to happen: there is a sense of this…liquid rush…which forms across your pelvis and torso and chest and then, with gathering momentum, condenses rapidly into your lower belly, into your vulva, into a tight ball which then explodes outward until it consumes every part of your body — your hands clench, your toes curl up tight, your mouth opens, your back and neck arch, and every inch of your skin is more alive than you ever thought possible. Sometimes this illuminated state can linger for quite some time. Sometimes there will be a second condensation and a second explosion, and more lingering. Sometimes your toes cramp.

The sun is up. You awake in his arms. You bring him coffee. You make breakfast together.

And what about disclosure, now?

Along with feelings of duplicity and guilt there is an intense, overpowering sense of validation.

For a trans woman like me, making love with a heterosexual cis man, without disclosing, is the absolute gold standard of passing. It is a culmination of feminine validation unlike any other. I am not proud of this, and this may be awfully trite, perhaps even sexist, but that morning I felt utterly complete in my womanhood.

I fell in love with Jim.

And, for a time, we were truly wonderful together.

As time went on, as we grew closer and came to know each other, the reconstructed story of my past became increasingly difficult to maintain. I feel certain that he sensed that I was withholding. He began to withdraw, became more distant. Visited less often. Was unavailable more often. Stopped calling. And, eventually, he stopped returning my calls.

We lasted for almost a year. The worst part was that I felt relieved. I would no longer have to lie to the man I loved.

Jim, if you see this, I’m sorry. You were the best.

Previous: Conflicted Romance, Part 2 — Falling in love, and a girl’s First Time.
Read about the first time I slept with a man in Seventeen: Sex and the Trans Girl.

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