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.