More than 20 years ago, a man went to Philadelphia and, after a lifelong struggle, “lost… More than 20 years ago, a man went to Philadelphia and, after a lifelong struggle, “lost it.” He shaved his beard, put on makeup, cross-dressed and went shopping.

Later came the hormones, the name change and the surgeries.

Now, Wendi Miller scratches her layered, sandy-colored hair as she muses on the fact that the last two decades of her life — after her decision to become a woman — have been fascinating.

Like many others, Miller identifies as part of the trans community — in her case, as a biological man who became a woman. She is the president of the PTSG, the Pittsburgh Transsexual Support Group, which has more than 40 members.

Biology does not view gender as fluid, said Irene Frieze, a Pitt psychology professor. She said that in the sciences, gender is set, and she believes biology and hormone baths in the womb shape not just genitals, but gender identity.

“It’s what’s going on in your mind versus what you feel free to express in terms of your own behavior,” she said, acknowledging that there are cultural roles men and women are expected to take on.

Sociologists tend to think that our culture shapes our views of masculinity and femininity. “People expect men and women to interact in specific ways…for the most part,” said Emilia Lombardi, a Pitt professor and transgender researcher. For example, a man might be harrassed for wearing a dress, while a woman might receive a negative reaction for shaving her head, she said.

Miller offered a similar view and broke gender and sex matters down into three categories. There is an assignment a doctor gives a baby based on genitals — sex. Then, there’s the social role that that child plays based on those characteristics — gender. Finally, there is how someone feels in terms of his or her own gender — gender identity.

A new life

Perched on a stool in Miller Frame, the Pittsburgh shop she’s owned since graduating from Carnegie Mellon in 1972, Miller explained that not understanding the difference between sexuality, sex and gender led to her 40-year confusion.

“[I was] finding myself attracted to the girls, wanting to be one of the girls, and once I reached my physical adolescence … also physically attracted to them too … it confused me horribly,” Miller said.

In college, when her name was William Miller, she once experimented with homosexuality, but she realized she wasn’t gay. Eventually, she married a woman and they had a son named Cooper.

Miller, now 64, made a point of differentiating between sexuality and gender, explaining that “trans” has nothing to do with whom you’re attracted to.

“There just seems to be no way to make [sex, gender and gender identity] all line up, except changing the physical and the [gender] role,” she said.

But altering biology is a long and often painful process.

A man becoming a woman must take what Miller jokingly called “lethal” amounts of hormones. Then there’s surgery — breast implants, castration and vaginoplasty — and electrolysis, which Miller jests “separates the girls from the guys.” Miller had all of these procedures performed.

Then there are the issues of documentation and legal identification.

The state of Pennsylvania allowed Miller to change her sex on all forms after having her surgeries. During the transition, she chose to use “W. Miller” on credit cards and documents to avoid confusion, but the preliminary measure meant eventually picking a “W” women’s name.

“There’s about five ‘W’ female names. You can count them on one hand. It’s Willow … Wendi, Wilma — I really can’t stand Wilma … — Whitney, which is like Whitney Houston, that’s too over-the-top. So there was really just no choice, it was going to be Wendi … It was almost by default,” she said.

In addition to physical pain and legal logistics, there are other difficulties, particularly with family.

Miller had been in marriage counseling with her wife before going to Philadelphia for business. Upon returning home to Pittsburgh, she confided in her counselor that she wanted to become a woman. The counselor advised her not to tell her wife, but she did and soon found herself divorced and acting as her own lawyer in a custody battle.

During the divorce process, Miller had to come out to Cooper, who was 9 at the time. Cooper said, “It was different … and it was somewhat strange because I didn’t have any context to understand it, but when you’re a certain age, the world throws a whole bunch of stuff at you, and you don’t understand it and you’re in a state of more acceptance.”

At 13, Cooper chose to live with Wendi.

“I think a lot of transsexuals shut out their family … and Wendi very intentionally chose not to — which I think is probably the best thing she could have done,” he said.

Most kids go through a time of being at odds with a parent, but Cooper said he felt that with his mother more than with Wendi. His mother encouraged him to keep mum about his father — perhaps to protect him from bullies — making him feel as though he should be ashamed.

But he wasn’t, and living with Wendi gave him support in unique ways.

“I went through puberty the same time my father did basically … It was a different father/son relationship because it was more complex. Both of us were going through physiological changes specific to the genders we were going into,” he said.

Though Wendi and Cooper were comfortable with their situation, they were still hestitant to share their experiences with people outside their immediate family. Cooper said Wendi pondered every step of coming out and found support online.

“Without the anonymity, they were too afraid to talk about what they really felt … PTSG started online. It’s a fascinating thing, too, because it shows that society and technology are developing in tandem,” he said.

This isn’t unusual, said Lombardi, the transgender researcher. She noted that the Internet and particularly features like AOL chat rooms have been vital tools in helping trans people find acceptance.

With college comes a new gender

Many years after Wendi Miller began using AOL chat rooms as a forum for trans discussion, Dylan Drobish explored his own struggles on the Internet.

The Pitt student, who once identified as a bisexual woman, was exposed to the idea of trans lifestyles through Rainbow Alliance, an advocacy group for homosexual, bisexual, transgender and queer students and their allies.

He’d known for a long time that he wasn’t comfortable as a woman.

Now 22, he recalls growing up in the very small town of Larksville, Pa., about 35 minutes outside of Scranton. There, he attended Catholic school. His name was Elise.

“Those skirts were fun,” he said sarcastically. “I remember the exact day in third grade I just started wearing shorts underneath up until I graduated high school … just because it was so uncomfortable for me.”

This is particularly obvious in pictures of himself in a dress, he said, where he can see the pained expression that passed over his face while wearing feminine garments.

“I didn’t know how to be graceful either,” he said.

As he sits, shoulders forward and arms extended, he explains that there came a point at which he realized his gestures and activities were much more characteristically male.

“The way I talk, the way I sit … and the way I am in a room full of people ­— it’s just, I guess I’m a bit rowdier in a lot of ways,” he said.

After meeting several trans people, he became “obsessed” with reading books and watching YouTube videos in which people chronicled their changes. He realized he might be interested in becoming a man. Eventually, he decided to document his own transition in the form of YouTube videos.

Drobish had dabbled in masculine dress all his life with Halloween costumes like the blue Power Ranger, Link the elf, and Angus Young of AC/DC. The first time he performed drag at the 2009 drag show, he brought out school-boy shorts like the ones he used when portraying Young.

He now performs drag in his group Hot Metal Hardware, considering himself a drag king because he is satirizing different types of masculinity. It was while performing in these shows that he realized he’d like to be a man.

“This is not just something I want to pretend to do,” he remembered thinking. “It’s the way I feel, the way I made myself. There’s a confidence here that I can’t find anywhere else. It didn’t feel like pretending.”

Drobish can recall the various points of his transition very clearly.

On Jan. 29, 2010, he had his first meeting at PERSAD, a support group for gay, lesbian, bisexual and transgender people. On March 10, 2010, he received his first shot of testosterone. After, he and his friend celebrated with an “It’s a boy” cake.

Drobish explained that becoming a man can, in some ways, be physically easier than becoming a woman. Biology makes women a natural “blank slate” so that testosterone has powerful effects, he said. In just the last year, his shoulders have widened, his voice has deepened and he’s gained 20 pounds.

“It really is [like puberty], it’s exactly the same thing. Your voice starts squeaking and cracking,” he said, adding that there’s also more hair growth and an increased sex drive.

After the hormones, some people also opt to get surgery. While Drobish would like to have the expensive upper-body surgery to remove his breasts, he’s not interested in the far-from-perfected surgery that either fashions a penis or cuts the clitoris to act as one. Drobish said he must wait because, as a college student, he doesn’t currently enough money for the procedure.

Income aside, he’s found that college is a very accepting setting and that the autonomy allows many people to feel freer.

“Obviously, a lot of people do find out in college because you’re not doing anything for anybody else anymore and you’re like ‘well what if I do this?’” he said.

Though friends have mostly been accepting, some have not taken the transition as well. Drobish sites difficulties primarily with older generations he encounters.

Often the discrepancy between his appearance and his legal name — as he hasn’t had the ability to change it from Elise to Dylan — forces Drobish to explain himself immediately when a professor takes attendance for the first time in a class.

“I do enjoy being a voice and being out there for everybody, but I want it to be on my terms … like if I’m going to tell somebody I’m going to tell them,” he said.

One situation in which his story comes out rather quickly is dating. Drobish has been in relationships since his transition.

He identifies as queer, citing that he used to identify as bisexual, but felt that the term implied there are only two genders. As a transgender man, he feels that isn’t the case.

Still, there are always many factors to consider, such as the mechanics that go along with dating a transgender man. Drobish knows all about this.

“People have come up to me and said, ‘Well, when you get a dick…’”

But there have also been positive reactions. Some people have told him that he’s changed their mind about trans guys. And being trans has obviously had an effect on Drobish, making him consider the multitude of people he could connect with.

“It depends on the person and the whole package, so it’s not really about what you’ve got between your legs,” he said.

Drobish has seen an increase in this kind of thinking. In the past year, five or six people he knows have come out as transgender. In total, he knows about 15 trans people, most of them being female to male.

Frieze, the Pitt psychology professor, on the other hand, says she knows more male to female trans individuals than vice versa.

“My theory about that is women have so much more freedom — women do masculine jobs these days, they can wear really masculine clothing and nobody cares about it … but men have a lot of trouble,” she said, using the idea of a man wearing a skirt as an example.

That’s not how Drobish sees it. Having lived it, he agrees that women can get away with a lot, but that doesn’t necessarily equate with the kind of freedom he was looking for.

“I thought about this too. I look at it in a different way … You can take on a masculine appearance and that sets on a different role for you in society. It’s not like it’s any less restricted than what people see,” he said.

Instead, he presented the idea that having only two genders is a big part of what makes the trans community small and complex. People often feel they must choose one or the other. This is where the idea of gender queer comes in.

Being gender queer means that you might not comfortably conform to male or female societal standards.

Drobish thinks that if people recognized the kind of freedom of expression they could have by experimenting with the boundaries of gender, there would be a lot more trans people.

“If more people were aware of terminology of things, of ‘this is what it means to be transgender,’ regardless of whether you pursue hormones, how many people would identify that way? If there weren’t this stigma, how many people would say, ‘I don’t fit into one of these two categories’?”