“I’m a Man and I’m Going to Start Transitioning Now.” Transgender Man Comes Out To Girlfriend.

by mitch kellaway

I’m Mitch Kellaway and I’m from Waltham, Massachusetts. I came out for the first time when I was 16 years old. I came out as a lesbian. I was at a high school in Newton, Massachusetts, probably one of the most liberal areas you can probably imagine.

I came upon this book in the library and I started reading for the first time about what being transgender means. And it kind of clicked in my head at that moment, I was 17 at that point, that this word describes me. I told about two people and then I just didn’t mention it again for six years. Not until I was 23, and that’s the same year that I met Jocelyn.

We actually met online, on the site OKCupid. We had this great dynamic from the start. I was, at the time, really like butch or masculine identified woman, and she is and always has been, remains, a really feminine identified woman. It wasn’t something even when I entered the relationship that I was thinking this is something I need to tell her about me. It’s hard to explain how I had compartmentalized that part of me and just put it somewhere else and it hadn’t come to the fore for several years.

So it was about a year into our relationship, and I decided–I just knew–that it was time to tell her. So she would be the first person that I had said those words to in six years. That night I knew when we sat down next to each other in bed to talk like we usually do before we go to bed, and I thought, “This is it, this is the night I’m going to tell her that I’m going to start transitioning and I’m going to live as a man.” I didn’t think I was going to feel nervous but in that moment I did feel nervous.I started tearing up a little bit and crying, and I didn’t want to cry. So we were just sitting in bed side by side, and I said, “I have something to tell you,” and I said, “I’m a man and I am going to start transitioning now.”

And she said, “Okay.” So she comforted me, she hugged me, it was fine. And the next morning we woke up as if it was any other morning.

One of the hardest things for me to face after I came out as trans* and I had my big happy moment, was the fact that, from then on, or until I decided to stop, I’d be facing a new medical regiment, and I had, knock on wood “had”, a terrible phobia of needles. And while some trans* men use gels, I was like, “I’m going to use the needles, they’re just going to be the most effective for me.” So I went to the doctor, got my prescription, and knew that I had to face this horrible fear that I’d had since I was a little kid.

That’s where Jocelyn really showed up for me, because she was there with me at my first appointment. I had to ask her, “Will you be willing to do the injections for me?” because I knew that it would probably be prohibitive. It would make it really difficult, if not impossible, for me to use the testosterone myself because that would mean I’d have to inject it in my own thigh.

She said, “Yes, of course I’ll do that.” I think even before she realized how difficult that can be to stick a piece of metal inside the person you love every two weeks.

It wasn’t long into our relationship that I realized, this is a person I could spend my life with.

On our third anniversary, we went back to the place we first met. We had both somehow independently decided that we were going to offer each other a ring and make it official on our third anniversary, so we both decided that the photo booth inside the cafe would be the best place to do this so we could have it on camera. So we sat in the photo booth and she beat me to it. She just pulled out the ring and said, “Will you marry me?” and I said “yes.”

About four months ago, we went back to our hometown in New Haven, Connecticut and we had a beautiful, simple ceremony on the beach. It’s almost like you don’t know what you need until you need it. I needed someone who just unconditionally loved me in order to feel comfortable enough to accept myself and love myself for who I am. And that was Jocelyn.



  1. I applaud you Mitch for your bravery, but I don,t understand one point in your story.
    You came out as a lesbian at 16 and discovered at 17 you were transgender, which is fair enough. Then at 23 you met your current girlfriend Jocelyn.

    Can someone explain to me, how can Jocelyn be sexually attracted to you. If she is a lesbian and now you are becoming a heterosexual male. I don’t get it.
    Can anyone clarify, maybe I am missing an important point in the story.

    Again I mean no disrespect, best of luck to you both,
    I hope you both live a long and prosperous life.

  2. Sorry I just discovered a trans man can have many different sexual identities, but what about Jocelyn’s sexual identity to begin with.
    I need to educate myself further.

  3. Mitch has given me the impression, that his girlfriend has selected to ignore her own sexuality.
    Forgive me but I don’t believe sexuality is black and white. I am not trying to be a protagonist here. This narrative does not make sense, someone please clarify.

    Again another excellent story.

  4. WTF I am so confused so a dude was hiding from everybody he is a dude. Now he is making himself into a straight dude.

  5. Patrick – His girlfriend chose love over her identity as a lesbian. Jocelyn is, or rather was a lesbian, but Mitch stole her heart and gave her the choice to stand by HIS side or walk away. Jocelyn decided to stay and is happy.

    Derek – No. This is a story about a female transitioning into a male. It is written a little weird. But Mitch was a butch lesbian when SHE met Jocelyn on OKcupid. Mitch was a female but felt she was meant to be a man already. She finally told Jocelyn, Jocelyn decided she didn’t care and still wanted to be with her, even if SHE became a HE. So Mitch started to become a man.
    Got it?
    Born a female.
    Thought she was a lesbian.
    Realized she was transgender.
    Met Jocelyn and fell in love.
    Told Jocelyn about being transgender.
    Became a man.

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