Preface: Some folks will think I'm a terrible person after reading this, and perhaps they're right. In truth, there were several points early-on when I'd thought about breaking things off, but something always drove us together. What I've detailed below is simply the product of wonderful happenstance.
I'm a guy in my early twenties who loves to write, and as it happens, I enjoy pursuing online roleplays with other writers. As it also happens, most of the characters I'm inspired to write happen to be female. In days past, this hadn't presented a problem, right up until I met Jay.
Jay isn't his real name, of course. Like me, he's a writer who's comfortable with depicting both male and female characters. Unlike me however, he had the courage to disclose his identity from the get-go. I myself was skittish, as most of my past partners would've found it rather unsettling for a guy to depict female characters. When the topic came up, I lied and told him I was a girl.
Meanwhile our characters interacted, fell in love, and eventually even proposed to one another. The story's all but fallen by the wayside, but I'm entirely certain our actual friendship was the chief reason it occurred.
On that note, Jay happens to be bi just like me, and even had a husband till he passed away in tragic circumstances. I only mention this as it might make him more accepting of the real me.
After a brief lull to finish university, I started talking to Jay again in January of this year. From the start, we'd both known that real life would be a purely platonic affair between us, yet by some turn of luck we've grown incredibly close to one another. I've even told him I love him, albeit explicitly as a friend. He's served as a lodestar in those terrifying weeks after I was diagnosed with chronic pain, and I've helped him through some of the worst days of his own life. In fact, aside from a pseudonym and a fake ethnicity, every aspect of my interaction with him has been completely genuine.
On some level, I'd honestly like to believe he already knows. Our conversations usually segue into economics and military history, two rather uncommon pursuits for the fairer sex. And though neither of us has ever asked for photos, insofar I've drawn the line at interacting with him outside of the IM app we use. He never even knew my (fake) first name till a few months back, and only since I mentioned it offhand.
Why I'm Afraid
Ever since another of my internet-friends confessed to me about wanting to transition, the thought of coming clean has weighed heavily on my mind. When Jay asked me if I could play video games yesterday, I found myself awash with guilt and grief for the better part of ten minutes. I want to tell him - a great part of me needs to - but I'm deathly afraid he'll react poorly. Even if he doesn't immediately distrust me, I fear the magic would be gone. Jay would soon take his leave, and my world would become just the slightest bit colder.
I've already made it my mind to tell him who I am. The question is, How can I approach letting him know my gender in a way that's more likely to end with us remaining close friends?