“The first time I went out, I forgot all about condoms,” remembers 22-year-old Kimberly. She’d grown up on Long Island with her mother and stepfather and began fending for herself at the age of 15. She started prostituting before even finishing high school. “I didn’t want to take any chances,” she says of those early years, “but I had a pimp and I knew he wanted his money.”

Thousands of New York City teens find themselves in Kimberly’s situation, thrown into sex work by circumstance, without the power to protect themselves. An estimated 15,000 to 20,000 adolescents are homeless in this city, and, according to a 1996 study by epidemiologist Michael Clatts, funded by the Centers for Disease Control and Prevention, at least 40 percent of them sell or exchange sex to survive. Kimberly joined their ranks in 1991 after becoming addicted to cocaine and losing the support of her family. When she first began sex work, making enough to satisfy her drug habit and her pimp and still pay for a hotel room made safer sex seem like an impossibility.

“You start by making rules for yourself,” says Kimberly, who has left drugs and prostitution and continues to test negative. “But if you’re out there and you’re not getting the money you want, you can start giving in.” Especially when some customers are willing to pay more for “raw sex,” sex without condoms. For cash-strapped young people, that can be a powerful incentive. And safer-sex negotiations become even harder in the underground economy of sex work. Frequent police sweeps cut down on the time prostitutes can spend establishing boundaries with a client. Women dressed to work are sometimes arrested simply for being in the vicinity of a stroll, a pick-up area for prostitution. “You want to get off the street as quickly as possible,” Kimberly says. “I learned how to stay out less time and still do more tricks. And, of course, I took more risks.”

Raising the stakes even further is widespread drug use at all levels of the sex industry. “Your decision-making is impaired,” says Matt Bernstein Sycamore, a 24-year-old gay man who has been working in the more exclusive -- and better paid -- escort field. “You may not be interested in the guy, but you get more interested when you’re high. And clients are conscious that they can use drugs to get whores to do things they wouldn’t otherwise do.” Over a third of the homeless youth Clatts interviewed in his 1996 study, “Youth at Risk,” used drugs, primarily cocaine. Interestingly, young women who work in a more formal commercial sex structure may be somewhat protected, forbidden by their pimps to do hard drugs -- since it decreases their marketability.

Neal Hoffman, MD, is the medical director of the Adolescent AIDS Program, a 10-year-old project at Montefiore Medical Center in the Bronx that provides primary care for adolescents with HIV and outreach to those who are most at risk. Much of the population he serves is involved in some form of sex work, which he describes as a continuum between organized prostitution, on the one hand, and “survival sex,” on the other. “We see kids who come into the city from all over,” he says. “They may even be middle-class kids, but, for whatever reason, they leave their homes, they’re sleeping on friends’ living room floors, and in order to go home with someone they’ll sleep with them. They do it out of desperation, it’s not thought out -- and those are some of the most risky situations.” He says kids with “gender atypical behavior” are often the first to get kicked out by their parents, and then, looking for a meal and a place to stay, “they quickly learn they’re a commodity.” These youth, functioning outside of an organized sex-work structure, may have very little ability to assess risk.

This desperation, Hoffman says, often springs from violence at home. “At least a half to a third of the prostitutes we see at our program talk about childhood sexual abuse,” he says. “You have to wonder how that contributes to risk behavior in the teenage years.” Certainly some sex workers attribute their entry into prostitution, at least in part, to this kind of sexual history. “If someone violates you and gets away with it, you feel like what you have to lose by prostituting is already gone,” says Kimberly, who was molested as a child. “You learn to distance yourself, to look down at what is happening to you. It’s what you have to do when you’re pulling tricks.” Prostitution allowed Kimberly to enter an alternative family structure, which offered her a more respected role. Such “family” positions shape HIV prevention among more organized sex workers.

The “bottom bitch,” Kimberly says, is usually the oldest and most trusted of the women in a pimp’s family. She manages operations on the stroll and oversees the use of condoms. “There are rules and everybody follows them,” says Kimberly, who used her position as the “bottom” to convince her pimp to follow a condom-only policy with tricks. “I only gave him fifty dollars once because I didn’t have a condom, and I didn’t want to do what the guy wanted me to do. After that he made safe sex a rule.”

Pimps realize they too are vulnerable, since they have sexual relationships with almost all of their workers. Shelley is a 19-year-old woman with legs and a wardrobe that rival RuPaul’s. “I learned about safe sex out here, from my man,” says Shelley, who walks a stroll in a working-class neighborhood in Queens. “He told me to use a condom no matter how much they offer me -- because I’m screwing him and he doesn’t want to get sick.”

The need to maintain control in their often dangerous relationships with tricks only seems to strengthen the desire of sex workers to lower physical and emotional barriers in their personal lives. Not using condoms with your pimp demonstrates that you trust both him and the system he represents. “Sometimes you think it’s the only way you can show affection,” Kimberly explains, “by taking a risk.”

Fifteen-year-old Precious works in the meatpacking district, a transgender stroll on Manhattan’s far West Side. “The tricks tell me how much they care for me, how much they need me. I’ve heard it all,” she says, pulling out a large pack of rubbers, “but I use condoms for everything.” Still, many transgender sex workers make exceptions for their pimps. Transgender prostitutes often deal with tricks who are so ambivalent about their own sexual identity that they lash out more violently -- and are perhaps less open to safer sex -- than other clients. Rosalyne Blumenstein of the Lesbian and Gay Community Services Center’s Gender Identity Project, which serves the city’s transgender community, says, “It’s scary out there on the street. This [pimp relationship] is nurturing. No matter how dysfunctional it is, they might not be getting it from any other place.”

Young male hustlers usually drift into prostitution more casually than their female counterparts, adopting an informal relationship to the work. “Things just happen,” says 19-year-old Danny, who has been working Times Square since he was 14. “Someone asks you to hang out, gives you some smoke or some beer, then asks you what you would do for what amount.” Many young men don’t even see what they do with their male tricks as sex, let alone gay sex. “I don’t have sex with guys,” insists Danny. “If they want to suck me off, or just hug or smooch or something, that’s OK.”

Ironically, their refusal to identify as gay or bisexual protects many young male sex workers from getting infected. “We don’t do it for the pleasure,” explains Fernando, a 19-year-old from Harlem who works Times Square. “We do it for the money, so it’s better to do it safe.” And the sexual activities that pose the least threat to their heterosexuality happen to be those that carry a lower risk of HIV infection, namely, getting sucked or fucking someone else. “If they want me to get fucked, I tell them ’Sorry,’” Danny says. “That’s my manhood, my pride and joy. I never want that taken away.”

Many of these males do sex work on a part-time basis, going out a few nights a week for extra income. “Our jobs really don’t pay,” says 19-year-old Alex, Fernando’s cousin, who works by day in a midtown shopping arcade. “It’s enough for yourself, but not enough to go out and chill with your girl.” If they don’t depend on sex work for survival, it puts them in a better bargaining position with the tricks. “You gotta let them know what’s the deal,” Fernando says, “tell them what you will or won’t do. They’ve picked up a lot of men before you, and you don’t know if they did it safe.”

Of course, their girlfriends don’t know whether their hustler boyfriends do it safe, either, but putting female partners at risk doesn’t seem to be a major concern. “We used condoms the first few times,” says Alex of his relationship with his 20-year-old girlfriend. “But then I got to know her better.” Nor does Fernando use condoms with his 18-year-old girlfriend. “I know she’s not going to do nothing,” he says.

This “me-first” approach is also reflected in the attitudes many male sex workers have toward their tricks -- attitudes that may make them vectors for infection. “Christian” is a gay-identified 21-year-old who worked as a “girl” until the recent closing of Sally’s Hideaway (Times Square’s only drag club) forced him to go back to hustling as a boy. “When they suck me, I don’t care if they use a condom,” he says, “because I know I don’t have anything. But when I suck them I always use one.”

Matt Bernstein Sycamore, the escort, started doing sex work in San Francisco at age 19. He says he has observed a one-sided approach to prevention among many gay and bisexual male prostitutes over the years, which he attributes in part to gay self-hatred. “Gay men don’t feel responsible for each other’s health,” he says. "The message is, ’Keep yourself safe.’“ Sycamore says that the outcome- -- exposing partners to risk -- is common even when sex workers have intimate relationships with each other. ”In my personal life, I was having unsafe sex with a person who I thought cared about me,“ remembers Kimberly, ”but he was a prostitute too, with gay men. I didn’t put it together that I could get something from him. He cared about me and didn’t look at me as a hooker. I felt I didn’t have to use a condom because that felt so good."

According to Tracy Brown, planning and resources coordinator at the Empire State Coalition of Youth and Family Services, there are over half a dozen groups providing HIV prevention outreach and a range of services to street youth and young sex workers in New York City. Young people who are reached by such programs are “significantly more likely” to change their HIV risk behaviors, says epidemiologist Clatts. One of the more established programs, Victim Services’ Street Work Project, located a quick walk north from Manhattan’s West Side piers, might reach up to 300 different kids a week. Yet, according to Clatts’ “Youth at Risk” study, only one out of five homeless youth have any contact with street outreach programs in a given year. For sex workers, finding ways to protect themselves both at work and in private is a challenge many still have to face alone.

Kimberly, whose feelings about sex work are entangled with those about her past relationships and drug use, chose to leave the profession entirely. Today she waitresses and lives in the Bronx with a “square,” with whom she has an 18-month-old son. She’s been clean for nearly two years and hasn’t prostituted for three. One way she confronts her past is by doing peer outreach to adolescents at risk through midtown’s New York Peer AIDS Education Coalition, one of several organizations in the city that use former and current sex workers to distribute condoms and safer-sex information to other youth at risk. But memories of the chances she took linger on. “Even today,” she says, “I go for an AIDS test, get the needle stuck in my arm, and the face of every trick flashes before my eyes.”

Sycamore is looking for a healthy way to continue doing commercial sex. He has been reflecting on his experiences as a prostitute by editing a forthcoming book, Tricks and Treats, in which male, female and transgender sex workers speak out about their clients. He’s given up recreational drugs, one of the largest risk factors for male sex workers. And he has redoubled his efforts to come up with a work ethic that protects his clients, his lovers and himself. “I won’t do anything that’s unsafe for them,” he says. “I know that they can find someone else to do it, but I don’t want to be that person.”