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Coming Out To My Exes As A Gay Trans Man

Here’s how the men in my life reacted to the news that I'm not the straight girl they thought I was.

I'm one of those people who has managed to stay close with my exes. I also have a tendency to sleep with my friends. (At least I know we'll have something in common at brunch the next day.) As a result, there are a lot of guys in my pool of friends and acquaintances that I have, at one time or another, had sex with.

This is probably not much of a problem for anyone who hasn’t transitioned from being a straight girl to a gay boy.

That one sentence makes the whole process sound easier than it actually was. In reality, my transition involved years of internal struggle, capped off by another two years of living half my life as one person and half as someone else. When I was finally ready to step outside all the time as the real me, I had to tell these guys that the person they'd been screwing (up until quite recently, for a few of them) wasn’t exactly who they thought she was.

I worried about coming out to straight guys in particular, since they’re notorious for taking hits to their masculinity very badly. I was afraid I would lose friends, have people spread horrible rumors about me, or even face physical violence. I agonized over telling these guys, wondering if it would be simpler and easier just to cut them out of my life all together.

That would have been relatively difficult. I'm from a small city in New Zealand where even if someone doesn’t know you, they know your classmate, once dated your sister, or do yoga with your mum — avoiding these guys entirely may have involved wearing elaborate disguises or possibly fleeing the country. Since I didn't have the money to run away to Argentina, and glasses paired with a fake mustache probably weren't going to fool many people, I realized I was going to have to put on my big boy pants and get ready for a whole load of awkward conversations.

No one reacts to this kind of news in exactly the same way, but a lot of the guys I came out to reacted so similarly I have been able to boil them down to their essence and present them to you here in their respective categories. All guys’ names have been shortened to their initials to protect the innocent, the guilty, and the terminally clueless.

When I had a farewell shag with S at the end of the summer before my last year at university, I was still trying very hard to be a girl. I made my first steps on the road to manhood while I was away at school that year. When I came home with a haircut, a new wardrobe, and a hilariously ineffective attempt to sound butch, S chose the prospect of having sex over noticing that anything about me had changed.

We were pretty much friends with benefits, one of the benefits being a shared interest in drinking cider and talking bollocks. When we met at a bar, I thought he might notice my shirt, pants, and significantly flatter chest and have an epiphany all on his own — thus saving me the trouble of actually coming out to him. (I pretty quickly realized that this was a completely useless coming-out strategy, and I would actually have to use my words.)

At this point in my transition, using my words was not my forte. I braced myself repeatedly to tell S what was up and completely failed. Six hours and far too many ciders later, the night progressed pretty much the same way as it always had in the past. S stripped off my binder with nary a puzzled look. I went with it — the sex was pretty good, though I didn't know any better then.

So it continued. Where strangers now stumbled over my pronouns, with S I was resolutely "she." Where my friends were getting used to calling me my chosen name, S didn't shift from the one on my birth certificate. And even after I finally had the courage to come out to him properly — using actual words and everything — my transition only seemed to fully penetrate his skull once I stopped having sex with him.

When I told him it was the end of booty calls for us, we were sitting in a booth at our usual haunt, because difficult conversations are always best had while drunk. He squinted as I finished speaking, somewhere after the fifth pint of cider.

"But...why not?"

"Because," I said slowly — mostly so he would understand, but partly because I was also five ciders deep — "Because you're straight. And I'm a guy."

“Yeah, but…not where it counts."

I dropped my forehead onto the table rather harder than I meant to.

M recognized me on the street a couple of months after I had properly started my social transition. We'd been friends in high school, but not such good friends that I'd added him to my new Facebook account. Really the only thing we'd done of note was fuck, once, in our first year of uni while we were on a sports exchange. (And when I say of note, well, it wasn't a very long note.)

But still, he smiled and greeted me by my girl name.

By then, I had a little script for just this situation.

"Hey M, sup? I'm [boy name] now, just for future reference."'

His face creased up. "But why?"

"Because I'm a guy now. Well, I was always a guy, but now I'm living as one."

"You're a guy? But... we... I'm not gay!"

I had no idea how he’d reached that conclusion. He was turning an alarming shade of red.

"Woah, woah," I said, trying to reduce the volume at which he was losing his mind. "Why would you even think that?"

"Because I had sex with someone who is now a guy!"

"Well, you didn't know. I didn't even really know. Me transitioning doesn't retroactively mean we had gay sex."

I managed not to add, “Because if we had, I would have had more fun.'”

"Oh, OK.” He still looked stressed, but he at least stopped talking for a moment. Then, once more: "You sure I'm not going to become gay?"

Look, I know you are all judging me right now for sleeping with him. In my defense, it was just the once, and he is very pretty.

R and I became mates from the moment we met at a house party. He's good people, and we had a friendship marked by obnoxious levels of flirting and occasional sex when when neither of us was in a relationship. I came out to him early on, because I figured I could gauge how other people would react by testing it out on him first.

Not quite.

We were in the pub in the middle of the afternoon, with only old smokers and a bored bartender for company. I mean it when I say the only time to have awkward discussions is while drinking. R listened to my speech, then nodded and said, "You'll make a hot guy. I'd still hook up with you."

My mind boggled as I made the necessary links. "You're into guys?"

"Well, not all of them, but yeah." He then proceeded to list a few mutual male friends he had gotten to various stages of intimacy with.

"Well, I'm glad I meet your exacting standards."

"You should be. Wait...does this mean you're having your boobs removed?"

"Hopefully soon, yeah."

"But they're such nice boobs!"

"I don't care, I want them gone."

"Can I throw a farewell boobs party?"


"Well can I at least cop one last feel of them?"

"Oh my GOD, no!"

He sighed, and pronounced my chosen name with weary disappointment. "Gotta say, you are no fun anymore."

For the record: I've since had chest surgery, there was no party, and R still flirts with me so hard I fear he'll hurt himself.

At first, A seemed to have the perfect reaction to my transition — he said OK, and tried to use my name and pronouns right. I really thought I had lucked out. Then, one night after a few beers, A made a confession.

"I think I'm bi. Only don't tell anyone; I'll say when I'm ready."

That was perfectly reasonable, so I agreed. And with that revelation, of course, A wanted to resume the benefits which had once been part of our friendship.

But as we did so, I noticed several things: A showed me no affection in public; he was still way into my boobs, even when I said they were a no-go area; and he seemed really uncomfortable around my cock (and not just because, being a sex toy newbie, I had accidentally bought one in a lurid shade of purple).

I'm sure there are really good conversations to have while wearing nothing but a binder and a nylon harness, but the one I had with A wasn't it.

"Hey, do you really like guys? Because you only seem to be interested in my...girl parts."

He mumbled something about this all being new to him.

"Have you ever been attracted to a guy who wasn't me?"

He went red and muttered something that sounded suspiciously like no.

I sighed and started gathering my clothes.

I don't want anyone to think my life is entirely full of cartoon characters. Most guys who knew me before my transition — ones I'd kissed or crushed on, ones I dated in high school, ones who had professed their interest and I hadn't reciprocated — most reacted the appropriate way: by saying OK, and freaking out in their own time.

Some I didn't say much to; they just avoided using names and pronouns for a while until they figured what everyone else thought. A couple smiled and said they weren't surprised. Another wanted to hang out more, picking me, wrongly, as the ultimate wingman.

A special mention must go to C, who put up with me when I was wearing waistcoats every time I went out of the house (a fashion tragedy many trans men go through); and to P, who was inviting me on boys’ weekends when most people were still tripping over pronouns.

When I asked them both for this essay what they’d actually thought when I came out and how they’d dealt with it so well, P told me: “I just figured it would be less weird for both of us if I started treating you like my other guy friends as soon as possible, because you did still look kind of girly, and I needed to make sure I didn’t start fancying you again. No offense.”

C had what was probably a more typical response: “I didn’t really know what you were talking about. So I kind of nodded and smiled and may have googled some things.”

I did not ask what C had googled, because the internet is a big and scary place and I do not need to know what type of porn he found.

Even most of the guys who I've cobbled together for these demonstrations have gotten their shit together and we remain, if not BFFs, then at least drinking buddies.

Now I'm past the stage of coming out to everyone from my past that I want to have in my future. The anxiety I felt seems as ridiculous as some of the reactions. But you never finish coming out, not really — on a recent trip home, I had to come out to the owner of the local newsagents, who has been selling me lollies since I was old enough to spend pocket money. And I now undergo the dilemma of wondering when to tell the actual gay men I date — and when not to.

But there are upsides. Being trans requires a broad sense of humor to deal with how crap the world can be. And to my fellow gay trans men who may be facing the same struggle, I have this advice:

Make it easy on yourself. Flee the country.