This article was the recipient of a Lisagor Award in Non-Deadline Reporting, Non-Daily Newspaper or Magazine, Circulation Above 20,000.

On a warm evening in early June, patrons in summer khakis filled the restaurant patios of Boystown, the north-side gay bastion marked by rainbow pylons and suggestively named bars. Just up the block from Whole Foods, Nikki Taylor Donahoe, 19, sat atop some firewood bundles stacked in front of the Circle K convenience store at Addison and Halsted. The store parking lot is familiar terrain; Donahoe and her friends have been congregating there nearly every afternoon for a while now. Donahoe has a moon-shaped face and a strong, broad torso. Her dramatic makeup creates deep shadows around her cheekbones. Her gaze is at once piercing and sunken. Dressed in a tight tank top and a pair of hoop earrings embellished with the word Barbie, she surveyed the passing scene like a queen holding court. "It's a cycle here," she said. "Boystown doesn't change. Same shit happens every day: getting high, getting drunk, making money."

Like any teenager, Donahoe is prone to complain about her brittle hair, her weight, and her lack of cash. But youthful vanity is the least of her worries. That night she was trying to figure out how she was going to pay for the motel room she'd been using since she'd lost her apartment several weeks earlier. She needed the room not only for sleeping but for her work as a prostitute.

Donahoe says she didn't have a childhood. The irony that she's not old enough to get into most clubs (at least when she's not holding a fake ID) irritates her, "because I feel old as hell."

She grew up as Troy, a white, middle-class boy, in Urbana, a town of about 12,000 in western Ohio. Home life was always difficult. "Troy's birth mother would take him to bars, leave him in public places," says Donahoe's adoptive mother, Kathy. "So he was put into foster care when he was 18 months old. We adopted him through foster care when he was almost three."

Kathy recalls Donahoe taking an interest in women's clothing from an early age. "He'd play dress-up at his grandmother's house when he was a kid. I didn't think anything of it." As the years passed, Kathy says, Donahoe ran away several times. She turned to medical professionals for help: "One doctor said that Troy has 'reactive attachment disorder,' since he never formed a bond with his birth mother."

Donahoe came out to Kathy in 2009, at age 16, and she responded by forbidding the teenager to date. "I never expected my son to tell me that. Processing it was such a thing. It took me a while to get used it."

The family had just moved to Naperville, about 50 miles west of Chicago. Donahoe found the website for the Boystown-based LGBTQ-focused service organization the Center on Halsted and struck up a correspondence with an employee there. The employee advised that if Donahoe ever made it to Chicago, it would be a good idea to stop by the center. "I decided, 'Fuck it, I'm gone," Donahoe says.

In February 2009 Donahoe took a Metra train from Naperville to Union Station and, with little money, walked the five miles from the Loop to the Center on Halsted. "I got to Belmont and it was like a fantasy land," Donahoe recalls. "I'd never seen a place where guys were holding hands and there were trans[gender] people everywhere. Everyone seemed to be happy in their own skin. The place grabbed hold of me."

Boystown has been a destination for LGBTQ youth since 1970, when neighborhood residents marched in Chicago's first gay pride parade (which this year attracted an estimated 850,000 people). For many of those kids—especially the ones who've been rejected by their families—the neighborhood offers a new start. Or at least the hope of one.

But it can also be a dangerous and rejecting place where young people find themselves living on the streets, doing sex work or committing petty crimes to get by, and attracting the wrath of established residents—pariahs amid the rainbow.

"These kids are superheroes of survival," says Jake Bradley, youth outreach manager for the nonprofit, nondenominational Night Ministry. "They're incredibly resilient and have really powerful ways of understanding who they are."

Late last year Chicago Public Schools reported 15,580 homeless students age 14 to 21, 10,684 of whom were living on their own, without a legal guardian. Those statistics aren't comprehensive, though, since many students don't report their homelessness. Nor do the stats include all of the kids who, like Donahoe, migrated to Chicago. According to the Chicago Coalition for the Homeless, the number of homeless youth has increased by 24 percent over the last two years—yet there were only 209 beds available for them in the city's centers and shelters during 2011. And a 2007 study by the National Gay and Lesbian Task Force states that 40 percent of Chicago's homeless adolescents identify as LGBTQ.

Homelessness, however, can trump such distinctions as sexual preference. Prostitution is often among the fastest ways for homeless youth to secure food, find shelter, and build community—however precarious. As a result, sexual orientation takes a backseat to fulfilling basic needs.

For all its perils, homelessness can be monotonous. Many of those afflicted by it find themselves stuck in a daily pattern. "Every night I try and get into the Crib at 8:30," says 23-year-old Apollo Jones. There are only 20 beds at the Crib, a queer-friendly emergency shelter run by the Night Ministry, and those who don't get one have few options. They might call friends, ride CTA trains, visit a bathhouse, head to "Ho Stroll" (a sex strip near Belmont and Sheffield where they can make quick cash), or just walk around until a drop-in center opens in the morning.

Homeless on and off since 2007, Jones usually doesn't check on the availability of beds at adult shelters, where LGBTQ youth are often targets of violence and sexual abuse. "If I don't get in [to the Crib]," he says, "I find a Starbucks or Dunkin' Donuts, and hopefully I have some money to buy something so they don't bother me. I wait until the morning when the Center on Halsted opens for breakfast club at 9 AM." Jones visits the drop-in program at the Broadway Youth Center (run by the Howard Brown Health Center) on Monday, Wednesday, and Friday afternoons, and attends its Wednesday community meetings. On Tuesdays and Thursdays he goes back to the Center on Halsted to talk with social workers and use the computers to search for jobs.

click to enlarge Temara Jazmyn became homeless last fall and spent six months on the street.

Todd Diederich

Jones keeps most of his worldly possessions (hygiene products, a change of clothes, notebooks full of poetry and song lyrics) in a single backpack, which he either carries with him or stores for days on end in Dumpsters around the city. "It's really hard" when his backpack gets stolen, he says. "I just have to start again."

Jones tries to appear put together and says the same is true of most of his friends. Good grooming makes them harder to pick out as homeless, as does the vitality they exude by virtue of being young. The Boystown residents and workers I talked with were often unaware of any problem with homeless youth in particular, tending to fixate on the older street people instead.

But if Jones and his friends aren't identifiably homeless, they're unmistakably present. On any given summer afternoon, bus stops, storefronts, and parking lots along Broadway between Belmont and Addison are crowded with flamboyant teens and twentysomethings wearing everything from oversize T-shirts to wigs and four-inch heels. They gather in public spaces, yet seem to exist in a parallel universe.

Walking along Broadway, Donahoe points out several shops where she does business. "The manager here is one of my clients," she says, pointing to a by-the-slice joint. "I can always get free pizza from there." Donahoe says she sees some johns several times a month and builds a rapport with them. A few even bring her breakfast.

Donahoe started doing sex work because it was the quickest way into the Boystown LGBTQ community. "One of the girls gave me a wig, put some makeup on me, and I became passable. You work your way up, too. At first I could barely make 100 bucks a night. I didn't know my worth." She notes that her white skin is an advantage. "I'm not racist—it's just how it is. I was blessed in that way." She figures that now she can easily earn $600 on a weekend night. And she uses the cash to fund her ongoing sex change. "I'm two years into my transition, and I've paid for all of it through street work," she says with pride. To hear her tell it, Donahoe's story isn't about being forced into sexual slavery but about choosing a destiny.

She claims that achieving that destiny involves servicing a regular rotation of Chicago police officers. She says it started last year when she was approached by a cop in uniform. "I thought I was about to get arrested," she says. "Instead, he told he had a 30-minute break and asked me to meet him in the Dunkin' Donuts parking lot." Donahoe claims she now sees him about twice a month, and that her roster of customers includes a few other officers as well. She says she doesn't view the relationship as an abuse of power but as a silent, protective contract. "Having police clients benefits me on the street. They need you to keep your mouth shut." She's not alone in her allegations. The police-as-johns narrative is ubiquitous among homeless kids in Boystown.

The Chicago Police Department did not comment on the allegations.

"Street-based young people are the ones who experience the worst police misconduct, leaving them with very little protection," says the Night Ministry's Bradley. "Things are set up so that a police officer can have sex with a minor, pay them or not, and decide whether to arrest them or not . . . It's completely common."

Despite her swagger, Donahoe faces innumerable hazards. A study published in 2006 by the National Gay and Lesbian Task Force shows that all street-based youth, and primarily those who identify as LGBTQ, are severely affected by mental-health problems, substance abuse, risky sexual behavior, and abuse and violence.

In May 2011, Donahoe says, she was raped while working on the west side. She adds that she'd suffered two prior rapes, but describes the latest incident as the most violent. "It was really hard to work through that," Donahoe recalls, stopping every so often to get her breath. "I had to get stitches that time. On the other two occasions it was like I kind of said no, but you let them get away with it because you know they're going to anyway." Now, Donahoe always carries two cans of Mace and at least one knife in her purse. "I'm more cautious now. The things that happened, they've made me stronger and they've made me wiser."

One important survival mechanism among homeless youth is tribing up. Let down by the civic authorities and their own families (when they have them), street kids start ersatz families of their own, usually including a father, mother, siblings, and even more distant relatives. These fictive families ignore the conventional niceties of age and gender: a son may be older than his mama, an auntie may identify as a male. But they're formalized in other ways and feed into a larger street-youth network.

"The most important thing for a homeless individual is their circle," says Jones. "It's easy to get bogged down by the stress of being homeless. You need friends who will help keep you mentally, emotionally, and physically healthy. It's also how you stay safe." Jones describes the small group he spends most of his days with as a simple alliance built on trust.

In contrast, Donahoe's affiliations are expansive and multifarious. She puts her greatest trust in her closest friend and "sister," Chloe. "We watch out for each other," Donahoe says. "We sleep in the same place, spend our days together, eat together."

click to enlarge "I'm not comfortable in men's shelters, and the women don't want me in theirs." —Temara Jazmyn

Todd Diederich

Donahoe also has day and night families. The nighttime kin are the Mattel family, organized according to the model of a "ballroom house"—a kind of underground fraternity that mentors black and Latino gay men through classes and voguing competitions. Each ballroom house is run by at least one "mother" who looks after any number of "children." The Mattel family has three main mothers, all of whom are black transgender prostitutes. "I don't know all my Mattel family,' says Donahoe, "but we all have a stamp—it's a tattoo." The tattoo consists of a hexagon about the size of a dollar coin, with the word Mattel at its center. Donahoe's is on her lower back. "I have upper rank in the family," Donahoe adds. "I'm the only daughter of Mimi Mattel."

The Mattel family may be structured like a ballroom house, but it operates more like an old-school street clique. "If one of your clients robs you, these girls have your back," Donahoe says. "You can't find anything like the Mattels anywhere else."

Donahoe usually uses the term "girls" when referring to her fellow family members. She says they're known for their violent behavior, and even suggests that the Mattel family is responsible for the increased violence in the neighborhood. According to the Chicago Police Department, the crime rate for District 23, which includes Boystown, hit a ten-year high in 2011. And the number of reported robberies for the first five months of 2012 is up over the same period last year. In the first two weeks of June, the Chicago Police Department's online crime map showed 18 armed robberies, two sexual assaults, and two aggravated batteries.

“I don’t want this life. I don’t want to worry about getting enough cash to pay for my hotel room—which I can’t even reserve because I’m not 21. I want to work in the day and sleep at night. I just want a normal life.” —Nikki Taylor Donahoe

Although unfamiliar with the Mattel family, associate professor Lance Williams, who studies Chicago gang and youth cultures at Northeastern Illinois University, notes that over the last 30 years many major Chicago gangs have decentralized, allowing smaller, niche cliques to emerge. Queer kids who migrate to places like Boystown from the south and west sides, hoping to escape the homophobia at home, may bring learned street behavior with them. "A street mentality usually consists of a range of antisocial behaviors, like fighting, petty crime, gang-related activities, as well as participation in the street economy," Williams says.

The new neighborhood is open territory—and where there's no competition, violence can escalate quickly. "It reminds me of the flash mobbing downtown," Williams says. "There's a lot of stuff you can get away with."

The activist organization Take Back Boystown was started after a series of robberies and stabbings last summer, one of which was caught on a video that went viral. The group was supposed to be a platform for neighborhood residents to air their grievances and suggest solutions for the rising crime rate, but the very phrase "take back" suggests an unwanted foreign presence and raises the question of who does and doesn't belong in an area where the resident population is about 80 percent white and the median income in 2009 was $65,340.

The Take Back Boystown Facebook page ignited with contentious conversation after a young black man from Bronzeville attacked a civilian and injured a cop in the early hours of June 25. The incident came in the wake of the Pride parade and was one of at least 18 crimes reported that night, eight of which were violent. Such numbers seem minuscule when you consider the hundreds of thousands of people at the parade, but they still attract a fearful response.

A contributor to the TBB page posted a photo of a large group of black kids loitering in the middle of Halsted Street at around 3 AM. It elicited 127 responses in its first week. "Something has changed and it's not the residents or the businesses, but rather the influx of people coming in from outside the neighborhood with the intent to cause trouble," wrote one respondent, echoing a common sentiment among those who weighed in. Still, some urged a more sympathetic reaction, and one commenter charged that "this whole thread is draped in racism disguised as 'concern.' If the majority of the photo faces weren't black this wouldn't even be posted!" The concern about race and class in Boystown isn't just a matter of online venting—it permeates the neighborhood.

And it's triggered a backlash from some queer kids there. "I fucking hate the Take Back Boystown people," declares Temara Jazmyn, 24, who grew up religious in a "crappy little hick town in Missouri" and, like Donahoe, is currently in the midst of her gender transition. "I don't identify with the upscale faggotry of the neighborhood, I don't identify with the yuppie ignorance here. I hate this neighborhood. I wish it would burn to the ground. Ninety percent of the people in this neighborhood are garbage to me. I have no tolerance for misogyny, racism, or classism, and that's all that there is in this neighborhood."

Black and slender, with delicately feminine features, Jazmyn says neighborhood people immediately tag her as a prostitute because she's young, trans, and, well, there. She insists that's far from the truth. "Sometimes I steal food because I'm hungry, but I'd sooner sleep outside than submit my body to the disgusting class system."

Her confrontational language stems, at least in part, from trauma. Last fall Jazmyn became homeless and spent six months on the streets. Although she had a few short-term jobs, she found it nearly impossible to save money. "You're eating out every day, and if you're working and don't get into a shelter, you're going to want to get a hotel. And you're paying for hormones." Jazmyn found herself in Boystown by default. "I ended up here because it was difficult for me to find a shelter. I'm not comfortable in men's shelters, and women don't want me in theirs." She says her first experience in Boystown was living with a man who promised to show her the ropes but instead solicited her for sex. The Crib provided an alternative.

click to enlarge Apollo Jones, 23, has been homeless off and on for the past five years. "It's hard enough just being young and LGBTQ," he says.

Todd Diederich

"When terrible things happen to someone, it can arrest their development," notes the Night Ministry's Bradley. "Many people we work with might be three, five, 12, and 53 [years old], all at the same time and in different ways. The developmental age brackets change."

To Jones, one of the hardest parts about being homeless "is still having to deal with everything everyone else deals with."

"You still have romantic relationships, you're still encountering people sexually and dealing with them. It's hard enough just being young and LGBTQ." The absence of parents and guardians easily leads street-based kids to unhealthy adulthoods. And while, as Bradley observes, many of them have powerful ways of understanding their own identity, they're still young adults.

"Adolescence is a really complicated time regardless," says Joe Hollendoner, senior vice president of programs at the AIDS Foundation of Chicago and founding director of the Broadway Youth Center. "Imagine the complications that homelessness adds to that. It's unfortunate that we as an LGBTQ community haven't come together around that problem. Instead you see the community galvanizing to get the youth out of the neighborhood. And the fact that these youth are developing and surviving really underscores their brilliance."

Even so, some might be willing to exchange brilliance for a little normality. "I've pictured where I'd be if I'd never come to Boystown," Jones remarks. "I'd have a small apartment because I'd be working. I wouldn't have a 'background.' I'd have my coffee in my hand, my trench coat on, and I'd go to work with a smile on my face."

"The streets really change you," Donahoe says. "It feels like I've already led myself down a path, and I can't turn around. My kindergarten teachers used to ask me what I wanted to be when I grew up, and I told them a music teacher. Never in a million fucking years would I have thought, 'Oh, I want to be a transsexual prostitute!'"

Last December Donahoe returned home, for Christmas, for the first time since leaving in 2009. "It was the best Christmas I've ever had," says her adoptive mother, Kathy. "I feel terrible about some of the things Troy has done and experienced. Maybe if things had been different from the start, maybe if I'd been more accepting when I first found out." She trails off. "I don't know. I'm worried he'll do something wrong. I just want him to have a good life."

Donahoe believes that Boystown "gets you trapped." For her as for many LGBTQ kids, the neighborhood that started out representing freedom finished by feeling as constricting as the place she'd fled. "I don't want this life. I don't want to worry about getting enough cash to pay for my hotel room—which I can't even reserve because I'm not 21. I want to work in the day and sleep at night. I just want a normal life."

As Donahoe finishes that thought, her phone buzzes. She thinks it might be a text message from somebody responding to a couples ad she posted online earlier that day. She takes a look, closes her phone, and says, "It's still about survival."