Sydney and Leah say they started dating pretty much as soon as they met in 1995, though neither of them really realized it. After they finally acknowledged their relationship, they were married within a year. But their bond was tested 17 years later, when Sydney blurted out, "I'm transgender," one day in the car. Now, post-transition and a few years behind them, they spoke to Cosmopolitan.com about how Sydney's transition impacted their lives.

What was your relationship like in the beginning?

Sydney: We just enjoyed each other's company and we were always hanging out with each other. It was girl time, almost.

Leah: Although I didn't see it as girl time at that point. Sydney is very tall and at that time, was a very masculine-presenting person, so I thought I just had a very sensitive and fantastic male friend. So even though it was kind of girl time for Sydney, it didn't feel like girl time to me. My experience up until then had been with guys who didn't think women were smart or to be listened to, so it was really nice to finally meet someone who was good-looking and smart. And sweet and thoughtful. I thought I found the perfect man! And in many ways, for 20 or so years, I had that in my mind. It's been a very interesting set of changes for me to go through and looking back on it, it feels weird because I have become acclimated to the difference now.

Leah, had you always dated men and women?

Leah: No, I only was attracted to men up until my late 30s and had only a very slight attraction to women. And actually, when I realized I was attracted to women, I didn't understand what was going on. I went to see a therapist and she basically said that it was not a big deal. And this was before Sydney decided to transition. I had never really dated any women except for Sydney, so it was a big change.

Sydney, when did you reach a point where you realized you were a woman and wanted to transition?

Sydney: Well, I knew that I was different as a child. My father was very strict and wanted a son really, really badly because he was the only son in his family. He also tried to beat out any form of femininity in me and still to this day doesn't really accept that I'm a woman. For a long time, I didn't really understand being transgender because in the late '80s, no one really talked about it. Even when I was with Leah, I just kept brushing it off until I started to identify as gender fluid around 2008, and then later, genderqueer. Even though I still was perceived as male, I started letting my hair grow a little longer instead of cutting it, and I started painting my toenails and shaving my arms. Those changes happened because I'd recently stopped working with my family business and dealing with a lot of personal challenges that caused me to put my personal life aside.

Leah: From my perspective, it seemed like the more people around her who expected her to be a certain way, the less free she felt. And when she left the company to work with me, she started to relax a little bit more and I think that caused the shift.

Sydney: After a while, the dysphoria started hitting me harder. Then one day we flew to Portland for a conference and I was still presenting as a male, but my hair was long, and a woman addressed me as ma'am and I was kind of shocked. I went up to Leah and was like, "Did she just call me ma'am?" and she was goes "Yeah, she did.'" That was the first time that had ever happened to me. It felt nice to me, to be female. And that was huge for me. I'd been thinking about transitioning for a long time but I kept brushing it off and that summer, I realized I really wanted to. Then I started reading more in the media about transgender people and started to think it might be possible for me. Then one day when I was driving in the car with Leah, I just said, "Honey, I'm transgender," and she was shocked, so I told her again. Then she said, "Pull over the car now!"

Leah: I remember that day so clearly. We pulled over into the parking lot of this little brick pizza place, and we sat there and looked at each other for a few minutes and then she started talking. I think it was an avalanche that started very slowly, and I believe we'd made a really safe space for each other to communicate. We'd also gotten really into the kink community, which was a very no-judgment space, so we were very open people with each other.

Sydney, how involved was Leah in shaping the woman you wanted to be?

Sydney: In the beginning, I was kind of taking on her personal style a bit, so I had to find my own. I'm also more femme than she is and she wears very little makeup, so I had to reach out to other people to help me figure out how to do my makeup the way I wanted to do it.

Did you ever have doubts that you'd be able to stay together after Sydney transitioned?

Sydney: We'd made a pact a long time ago that if either one of us was ever unhappy in the relationship, we'd end it, so I was worried that if I told her, she'd be unhappy and want to leave. Still, even though I was nervous when I told her, deep down inside I knew that I had to be myself and tell her, no matter how she reacted. I figured if it cost us our marriage then well, that would be the price of being myself. I couldn't continue living a lie and pretending to be something I am not. I would rather her be happy without me than miserable with me.

Leah: I struggled a lot with the transition because I had to let go of a lot. I had to release any expectations I had about how Sydney would be physically. I didn't know what was going to happen during the transition. It was also letting go of being in a heterosexual relationship. When Sydney would tell me how worried she was about losing me, I tried to be very careful not to say, "No, stay straight and don't become a woman because I need to have a heterosexual marriage," even though a big part of me enjoyed that aspect of our relationship. I didn't really want to let go of all of it, but I also remember not wanting to be selfish. I also thought about how the first person she came out to was her biological father and he was very cruel to her and told her that if she came out, her business would fail and her marriage would fail and she would lose everyone. So even though I was scared, I wanted to try to be there for her so that didn't happen.

How did people around you react?

Leah: I had never discussed any feelings of bisexuality with my family, so it was a tough conversation to have with them because I kind of had to come out. I just told them, "I've had these feelings before," but they actually thought that Sydney was forcing me to become a lesbian. I just said, "You guys raised me to be an independent thinker. Do you really think that someone could force me to be anything that I didn't want to be?" And they said, "Well, we know how much you love Sydney and you would do anything to be with her."

Sydney: We've been very lucky because people have been really supportive and just want us to be happy. The only thing that is strange is being viewed as a lesbian couple versus a straight couple when we're out in public. Where we live in the Northeast, they are more accepting of gay marriage, but Leah's father lives in the South and we have to be more careful about holding hands in public. You don't know how people are going to act.

How did the dynamic of your relationship change over the course of Sydney's transition?

Sydney: We never had real gender roles, so not much changed in that way.

Leah: I was raised in a household where there really were no gender roles enforced on us. The women were expected be able to cook in the kitchen and clean and also go outside in the garage and do what had to be done. My dad always told me, "You're not a person who does anything that a girl would do or that a boy would do, you are a person who would do what a person would do."

Leah, how was it for you to have a partner with a different body than she had before?

Leah: She looks very soft now. Her cheekbones are softer and more feminine, but there was a point in time when she was in between looking like who she was then and who she is now. It was very interesting to watch. Some changes were rapid and some changes weren't. I actually cried a lot because it was like the person that I married was gone but also still there. It kind of felt like my partner was dying in front of me, but also she wasn't going anywhere because she was becoming a new person.

How did your sex life change over the course of Sydney's transition?

Leah: It changed tremendously once she started taking hormones because there are some sexual acts we can't do anymore in the same ways. I love penetrated sex. It's my favorite thing and even though we can still have it in a different way, it's still not exactly the same. Having that emotional closeness isn't as easy with a dildo and missing that closeness doesn't really ever go away for me. She also doesn't expect me to be as dominant any more, which was a big part of our sex play.

Looking back, how has Sydney's transition affected your relationship overall?

Sydney: Once I came out as a woman, we really had no idea what was going to happen to our marriage, so we put everything on pause and even opened things up so if we wanted to date other people, we could. We never chose to though. Instead, we just kinda started dating again. And then once we'd been dating again for a while, we just realized, "This is working. We should be together."

Leah: We've become stronger. Our relationship really boils down to everyday human stuff. Our sexuality and gender and the way we present ourselves to the world doesn't really make a difference.

Correction: A previous version of this article stated that Sydney had gender reassignment surgery, but she has not.

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Lane Moore Sex & Relationships Editor I'm Lane Moore, sex & relationships editor at Cosmopolitan.com.

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