Priest, 20, has been on and off the streets since he was 15. These days, it's the streets of Lakeview, and he's bracing for his first Chicago winter.

As autumn creeps into the neighborhood, he starts to shiver. He pulls his arms deeper into the sleeves of his sweater. He needs some warmer clothes, he says.

Priest was emancipated from his family in St. Augustine, Florida five years ago. He struck off on his own because his mother was struggling to support him and his siblings, and he wanted to ease the financial burden (his father died when he was 12).

"I sat there and talked to my mom for a really long time about it, and she finally agreed to it," he said.

He recalls the places he hitchhiked and train-hopped through since he left.

"Florida, Georgia, South Carolina, North Carolina, Alabama, Tennessee, Indiana, Chicago, Missouri, South Dakota, Iowa…"

Texas and Arkansas also make the list, which totals 19 states.

On a return visit home when he was 18, Priest pulled his mother away from making dinner and sat her down.

"Mom, I like men and women," he remembers telling her. "She basically told me, 'It's okay son, I already knew.' I was like, 'How the hell did you know?' She said, 'What kid wears six inch stilettos when he's three?'"

Two years later, Priest has made his home in Chicago's official gay neighborhood, Boystown. Chicago captured his heart when he visited last spring. In July, he returned to Lakeview to stay.

"I love the big city," he said. "I love the crowd, and there's always something to do."

He chose Lakeview because he liked the neighborhood's gay culture, atmosphere and social services.

"I would describe this neighborhood as a place where you can be yourself, don't have to worry about anybody bothering you about who you are or what you're into," he said.

Lakeview's street youth know Priest well, so well that some still forget and call him by his birth name, which he no longer uses.

But despite having a large community in the neighborhood, he prefers to keep to himself. It's easier to evade trouble that way, he says. When you let people in, you never know what can happen, especially on the street. If you're on your own, it's easier to trust the company you keep.

On warm days, Priest might go out toward the lake to sleep, or he might go to one of his "spots" to sleep and stash clothes. He usually has three spots around the neighborhood, secret nooks where he can store clothing and doze during the day.

In August, one was tucked into the architecture of the Inter-American school on Addison. A few paces past the school's jungle gym, up a couple stairs, over a storage shed and onto the roof, and Priest had his own space below an overhanging tree. But he must move quickly, so as not draw attention from the police station on the other side of the playground.

That spot was compromised months ago, however, when someone saw him and called police. That day, Priest woke up to a female officer standing above him. He joked to her that he might just be having a good dream.

Priest spends a lot of time being bored, he said. Despite the neighborhood's excitement, there are times when there is just nothing to do. He regularly applies for jobs using a resume he built at the Broadway Youth Center, but so far that hasn't worked out. He is honest about the fact that he's homeless, and it usually counts as a strike against him.

"It gets very frustrating… you get interviews but then all of the sudden they come back around and say, 'We have somebody else that is more experienced than you,'" he said. "Or they just blatantly say, 'We don't want you.' So it gets your hopes up a bit, but then it gets crashing back down."

Priest changes his look regularly. One day, he and friend got a hold of army fatigues, and they walked around the neighborhood confusing passersby. When asked, Priest told them he was part of the anarchy militia. Another time, he got novelty contact lenses that made it look like he had lizard eyes.

But despite the playful atmosphere of the world he sometimes inhabits, being homeless is difficult he says.

"For someone who is rich and has never been homeless, they wouldn't really comprehend what we go through on a daily basis," he said. "You can't sit down wherever you want. You can't rest wherever you want. You can only do things at certain times. You can only sleep at certain times."

The first time he became homeless, he said, it was hard to handle. He couldn't sleep because he was used to having a bed. Now, after sleeping on cardboard and concrete, he isn't sure how he would deal with having a bed.

Next week's issue will feature a Priest photo essay, plus an exclusive video tour of Boystown.

Next week in Generation Halsted, an in-depth look at the Broadway United Methodist Church's innovative Youth Lounge. Photo essay: Overnight in Boystown. Watch what really happens.

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