A few years ago I would have answered the following question with a definite no. Shit, even finding a home for this story would have proved difficult, if not impossible. For something as open minded and progressive as skateboarding it surprises people that this subject still remains taboo in so much of it.

Welcome Hillary Thompson.

It was pouring when I pulled up to the strip mall to meet Hillary for lunch. We had talked for about year on Facebook. A few messages back and forth about things and a handful of, “shoulds,” until one day I put a date out there. She obliged and well, there we were. Meeting.

Hillary was born September 10th in Raleigh, NC, the middle child of 3. Raleigh if you haven’t been, is a mid-sized liberal city located in a southern conservative state. It was there where two life-changing things happened when she was around 4 or 5 years old.

First, she started skating. Her first board was a single kicktail with big plastic wheels and it was love at first sight. The cool kids at the end of the block were doing it, only they had wide boards, 80’s style and they could do ollie’s and kickflips. Naturally, she wanted to be cool too. “They were like, 13-14, which was old compared to me so they would go off and do cool teen stuff and I would kinda just skate around the block. But I wanted to be like them,” Hillary says, describing her eagerness to skate. Her younger brother started to skate with her shortly after.

The second big event happened around the same time and this is where society’s imposed ideas of sex, gender and sexuality started to cause some issues for Hillary. Although society defines gender by one’s anatomy at birth, some people physically born boys or girls, don’t always feel like them. “I was naive then and I just assumed, well, yeah, of course I’m just gonna grow up and be a woman, that’s how it works. That’s who I am.”

Hillary’s assigned male gender at birth was in conflict with her gender identity. This resulted in gender dysphoria, or persistent anxiety to someone who feels there’s an internal mismatch between their assigned gender and their internal gender identity.

“I started to get really distressed about it. I didn’t want to tell anyone because I knew that… there is a stigma attached to being gender non-conforming. I knew the consequences of exhibiting feminine behavior as a male could be dire.”

So she did what many people in her position have done, she hid it away. Crying herself to sleep many nights, she prayed that finally one morning she’d just wake up a new person. She hoped she’d wake up the woman she’d always dreamed she would be.

The running away temporarily worked for a few years, until she was about 18 and realized that she was having trouble escaping everything. Depressed, she was skipping school and starting to shut down, and her parents couldn’t figure out why. She stopped everything else but skating at this point and had isolated herself from her friends. Her parents sent her to a psychiatrist and she eventually confided in him her secret. It was finally out… sort of.

”I just assumed, well, yeah, of course I’m just gonna grow up and be a woman, that’s how it works. That’s who I am.”

Instead of helping with the actual problem, the psychiatrist just told her she was depressed, gave her a prescription for some pills and sent her on her way. Obviously, she was depressed but knew that medicine wasn’t the answer. So she turned to the next best option: the internet.

“It’s great that I was able to look online. Older people I’ve known haven’t had the resource and I just know that’s been such a huge thing for me. I basically looked up, ‘How do I transition?’ At this point I knew it was possible, so I found a way to order hormones off the Internet from Canada,” which was the beginning of the end for her secret.

Hillary’s mother intercepted the package suspecting it might be drugs or maybe even hormones. This was the moment she’d feared her entire life. “I figured if I were to tell them or if they were to find out, I might not ever talk to them again, it might be the end of our relationship completely.” Her fears of being disowned slowly subsided as they sat down to talk. While they might have been shocked and confused or upset, they weren’t going to disown her. “It was a struggle for them and still is at times, but they have still been accepting and they really try, it’s unconditional love.”

“There’s a process friends and family have to go through…it varies from person to person. You have to be prepared with people needing time to deal with that kind of change.” Although it was not always an easy process with many rough patches her parents were mostly supportive.

Although the entire process has obviously been very difficult, Hillary spoke of it modestly and was very conscious of not over-dramatizing the coming out process. She asked me not to paint her as a martyr and it was shocking to hear how humbly she’d speak of transitioning. Hillary and her story is possibly one of the greater things to happen in skateboarding in a long, long time, and here she hasn’t a clue how special she really is.

The first breakthrough with her parents happened when her mom saw Hillary was still suffering and helped her find a therapist specializing in gender and gender issues. It was there she was able to finally speak freely with someone about it and knew they wouldn’t just want to, “fix her.” Thus began the transitioning process to become the woman she always wanted to be.

In addition, she decided to move to Atlanta for a fresh start. At the time she was making decent money playing poker online, so she got a nice apartment in Buckhead and started her new life. “I felt comfortable enough being in a new place to just, start presenting myself as myself, as female. I started hormones there and it was rough because I had not been socialized that way [as a woman], but, I wouldn’t have felt as comfortable doing that where I grew up.” She started leaving the house as Hillary, dressing the way she wanted to, acting the way she wanted to.

Many times, when people transition they feel the need to shed previous gender habits. Some people do it for survival and some out of societal pressures but Hillary’s desire to skate helped her ignore all of this and she picked up her board again. Alone, she would skate a flatbar in a tennis court or a skatepark nearby. “I didn’t go out and skate much with people because I didn’t know anyone and I was still scared to meet people as Hillary. I was definitely had anxiety to get back into skateboarding. I didn’t think that people would accept it.”

After a year or so in Atlanta, things had changed. Exchanging money with online poker dealers became illegal in America. So while you could still play, there were no longer legal ways to gamble, and to make money. She’d also grown as Hillary over the past year. “I was skating some but, I don’t know, maybe I felt like I had just become comfortable enough with myself to move back and face up to everything I had been so afraid of. You know? I’m still dealing with it, but, I think I’ve overcome something big.”

So she left Atlanta and headed back home to face up to her parents, her old friends and old fears.

Moving back, there were not only some social issues but there are a slew of legal issues that she, as a transgendered person had to deal with.

In many states, including North Carolina, you cannot change your gender without having gender re-assignment surgery. “In North Carolina, to legally change your gender on documents such as a driver’s license or a birth certificate, you must first undergo genital reassignment surgery which can cost tens of thousands of dollars and is not always desired by the transitioning individual,” Hillary explained, annoyed.

So why is this a big deal?

Well, simply put, it’s hard to make a full transition when you can’t legally change your name and gender. It also puts a lot of stress on people who are transitioning to get reassignment surgery, which is not just a small reversible decision. “Anytime I have to present an ID at the store or at school, I have to expose myself and it puts me in a shitty position.” As a result Hillary could be mistreated or discriminated against if someone were trans-phobic. “So if you do not want to undergo genital surgery, you are stuck with identification documents that don’t match your appearance and can face discrimination or be put into dangerous situations because of them,” Hillary explained.

Furthermore, no matter where you live, you must abide by the laws of your birth state. If your born in North Carolina, for example, you can’t simply move to California and follow their possibly more liberal laws. Your birth certificate will always be from that state and follow those rules so unfortunately for Hillary, there’s nothing she can do except hope one day North Carolina will let her legally live the life she’s always wanted to live.

Throughout the trip, Hillary had been a bit apprehensive about me constantly pointing a camera at her. After all, she’d spent most of her life avoiding looking at herself, so, I’m sure all this attention on how she looks now was nerve-racking, if not annoying. She’s confident, but still working on it.

I asked if I could set up some lights and take a portrait of her. She agreed, but first wanted to head to Bobbi Brown at the mall to get some makeup done. Which brought up something I’d never thought of before. How does one transitioning learn how to look like the person they want to be?

“For me, everything is really hard. I’m not good at that stuff, so yeah, figuring out how to get the look and the process between no make up and make up on perfectly, it’s hard to fill in the blanks.” She speaks about it light heartedly, rather than being embarrassed. These sorts of problems aren’t unique to transgendered people but are rather universal. “I mean, it can be frustrating for me, but even birth assigned females have trouble with makeup. It’s a learning process.”

Additionally, for Hillary or anyone who is transitioning, makeup is more than just personal fulfillment – It also can serve as protection. Because during the transition process, those who don’t blend well can often be at risk for violence or discrimination.

As it stands now, Hillary is well on her way towards a healthier and more accepting relationship with herself, her parents, and her friends — but where does she stand in the skateboard world?

For the most part, surprisingly well. “It’s hard to say. You’d have to ask them because like, for me, I thought everyone was just disgusted with me when they saw me so I would just skate by myself. But, I didn’t get a ton of flack from anyone.”

So is the skate world growing up?

That’s not to say there hadn’t been a few isolated incidents. She told me of a few ignorant things people have done, but instead of calling out certain people in this story, she asked to do the opposite. It’s not a story of the bad things that have happened, but of the good things that have and are yet to come.

”I thought everyone was just disgusted with me when they saw me so I would just skate by myself.”

She speaks about skateboarding with the excitement of someone who just discovered how awesome it is, again. “Well I like it more now than I ever have, because before there were always boundaries I wouldn’t cross because I was living in fear. There was the transitional period when I just skated by myself, which I didn’t like because for me skating is a really social thing. Skating alone is really depressing. Now I have friends to skate with and I’ve lost those barriers and boundaries. I can be myself.” She’s been skating almost everyday, going to school full time and working on developing relationships she’s neglected in the past. She seems, dare I say, happy. I think skateboarding is not only ready for Hillary, but it’s very excited for her.

Words & Photography: Sam Mcguire
For more of Sam’s work check out his site & work here
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