Conflicted Romance, Part 1 — Dating after Transition
I kind of fell for this guy, in the first year after transition. I was highly feminised and ‘passing’ as female by then; in fact, truth be told, I was really freaking cute, in a big-hair high-heel Euro-chic 1990 kind of way. Thirty-three years old going on twenty (oestrogen!), very slim, with long red hair and perfect legs. I had a great wardrobe, an absurd number of shoes, nice jewellery, professionally maintained nails, and excellent makeup.
I had left the job in which I had transitioned into womanhood oh-so publicly — the ‘fish bowl’, I called it — my body and my life had been on constant display, with everyone treating me as a titillating conversation piece. Now I had a new position, many cities away, where no one had the least notion of my history. I had walked away from my old life and was now undisclosed and in the woodwork. Perfect.
For the first time ever, I was solid in my life, in possession of every aspect of the womanhood I’d dreamt of — I had a body which not only had all the right bits, but was pretty much the cultural ideal of ‘hot’; I had youth and good looks, a professional career that paid well, a whole new set of personal and cultural skills which were clicking along like I’d always owned them…and did I mention my awesome wardrobe?
I had every aspect of womanhood I’d ever dreamt of — almost.
So I started dating this guy I met at the gym. He was gentlemanly, kind, generous, complimentary, affectionate, a good listener, always went out of his way to treat me as a lady, had an amazing body, and — wow — was I thrilled. He also thought we should have sex. Really soon. Like second-date soon.
But — and there’s always a ‘but’ — transgender people face this thing called ‘passing’. Passing is being seen as your proper gender, the gender you are presenting to the world, who you are. Passing is what most cisgender people do every minute of every day without even knowing they’re passing. Passing, for a trans person, can mean comfort, safety, being able to pee or hold a job or go on a date.
Passing is difficult, especially for women, whose bodies and behaviours are constantly scrutinised. ‘Passing privilege’, as we call it, depends on a hundred different factors, only some of which are in one’s control. Even years after one is successfully passing, that anxiety can be present.
Because the thing about passing is that you can never really be sure you’re passing. You can think you’re passing, but maybe people are just being kind. Or maybe you are passing — it’s not like you’re going to ask, right? And there’s no point in asking the people who ‘know’, because they know and can’t really tell you if you’re passing or not, because they know. Passing is a bitch, either way.
So was I passing? With him, I mean? I knew for certain I was cute: men made that abundantly clear. But cute and passing aren’t necessarily the same thing. And it’s not like I was going to check this with him. (‘Hey, am I convincing as a woman?’ Right.) I had no intention of disclosing the awkward past I had worked so hard to leave behind. Honestly, worrying about passing is hopeless tail-chasing, and anyway — look at the picture — seriously girl? But that’s what we do to ourselves. We treat passing as life-and-death. Which it kind of is, for some of us.
Anyway, he seemed to be really into me, wanted to know all about me (ha!), couldn’t keep his hands off of me; and boy, was I loving this.
But — another ‘but’ — there’s this other thing: Some call them ‘trans-attracted men’; we call them ‘chasers’ — hetero guys who use trans women to satisfy a particular fetish. Even though they’re straight, they’re looking to hook-up with pre-op trans women, and it’s a common enough thing that there’s a whole ‘shemale’ chicks-with-dicks porn industry built around them. Good money if you’ve got the body and can stomach it. Post-transition I no longer had that body (thank god), and wouldn’t it be ironic to get into bed with a straight man (without disclosing) and have him freak out when he found out you had a vagina?
So I could never really be certain if I was passing and he was just really into me (probably), or if I wasn’t, and he was a chaser (possibly), without disclosing (out of the question). I worried that maybe he was a chaser — he was so very clear that he thought we should have sex really, really soon — but then, you know, maybe men are just like that? (Probably.)
I never did say ‘yes’ to him, poor guy. For one thing, this was less than a year after, you know, getting ‘fixed’ — that’s a lot of cutting, and it takes a year or two for things to settle ‘down there’. I wasn’t ready yet, and eventually he gave up, so I’m guessing it wasn’t my brilliant mind and colourful personality that were his main focus. Poor guy.
I was really skittish after that, with the whole passing/disclosure/chaser thing. At that time I’d only been passing for a year or so, and I’d only been woodworked (living undisclosed, ‘in stealth’) for maybe half that. With so much newness and insecurity, I decided to give dating a rest until I’d sorted out how to handle all this.
Then there was RJ... This was a year or so later, I was far more confident, and I knew for certain he read me as female. Oh, very much so.
RJ worked in the same office as I. Big guy. I’m six-foot/1m85 in heels, and even then RJ was half a head taller and could wrap me up like a blanket; which he did as his standard greeting. Oh, yes, he was into me. Only problem was — married.
There came a time when things weren’t going so well for RJ at home. We went out for drinks after work one day and had somewhat too many, which ended up in a major make-out session in a booth at the back of the restaurant. We’d just decided to go home to my place…when we decided not to. Well, truthfully, he decided not to. I’m not proud of this, but I found the obvious struggle he went through thoroughly validating.
So we had to be satisfied with a long, luscious, lingering goodbye in the car park. Oh yes, I did want him. Now I was ready, but —
And there’s always a ‘but’.
The next morning, at work, RJ greeted me with a smile, but no hug this time; we tacitly agreed that it was for the best. I have mourned the missed opportunity. I had a real hot-spot for RJ — in my memory I still do, and wonder ‘what if?’ To this day I look back with fondness, and a certain regret.
Next: Conflicted Romance, Part 2 — Falling in love, and a girl’s First Time
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