A FEW BLOCKS EAST OF of the Space Needle, Seattle’s open-air sex market is going full-tilt. It’s midnight on an autumn weekend and, as usual, the men are in cars and the women are on foot. The men circle the surrounding blocks and thread through parking lots, their faces obscured by the tinted windows of luxury SUVs and the grimy windshields of tired station wagons. The women are of every size and race, conspicuous in their tight jeans and short, body-hugging dresses. A black Hummer rounds the same corner dozens of times. On one corner, “warm-up ladies” from a local ministry dispense coffee, counsel, and condoms.

Potential customers get neither come-hither glances nor bold invitations; the women stare straight ahead, silent and expressionless, as they troop up and down the sidewalks of the soliciting district known as “the track.” Only when a car slows next to one of the women will she make eye contact, then talk business through an open window before getting in. She’ll usually ask to touch the customer’s genitals to ensure he means business. A decoy cop would be far less willing to accept what’s known as “the dirty handshake” than a genuine customer.

Suddenly the thwack-thwack of high heels hitting the pavement echoes against the empty buildings. One woman, with caramel curls and a metallic copper skirt that’s a mere band around her hips, has begun to run. Minutes later, another woman does the same. Behind them follow swaggering, well-groomed young men, most of them African American. Sometimes they jeer at the women. “Bitch coming out to the track in flip-flops!” one man in an oversize rugby shirt hoots at a miniskirted Asian woman. “Hos supposed to be wearing heels!” When this sort of talk gets Mr. Rugby Shirt nowhere, he resorts to physical intimidation. First he lopes after a busty blonde, chasing her down the sidewalk. Then he blocks the path of another young woman in tight jeans until she raises an elbow to clear the way. For the most part, the women ignore the attentions.

To understand the running, the chasing, and the aloof behavior, I sought out an expert on the street-based sex scene. His explanation shows how much the world’s oldest profession is changing in Seattle’s new millennium—how popular culture has overtaken the once surreptitious skin trade, and why in the age of slick marketing and social networking, old-style streetwalking can’t compete.

Daddy Cool is a convicted pimp with an epic rap sheet. He’s now appealing a sentence for promoting prostitution and assault that’s as long as he is old—24 years. He is smart and charismatic and speaks with a soft Louisiana accent. A faint dimple below his left eye sets off a shy smile. Tall and muscular, he stays fit by running in place in his tiny cell. He says he was “born a pimp” and lived the pimp life for four of his adult years. He got his start as a junior drug dealer but soon found that “what a woman got between her legs is a gold mine.” He embarked on his career in typical fashion for pimps, with sweet talk and promises of a glamorous lifestyle made to women willing to perform sex for pay and then turn the money entirely over to him. His gift for gab served him well. With the earnings, he provided occasional gifts and a place to stay, and once there was even a “working” trip to Europe. At one point he counted 19 women on his team, all of whom were subject to his “way of life” and “expectations,” which included discipline and punishment. Ultimately those last measures led to his imprisonment.

Many of the working women busted on the street are older, homeless, or addled and prematurely aged by drugs, and can’t find safer, more lucrative venues.

The women working the street are permitted to speak only to customers, explains Daddy Cool through the visiting-booth glass at the King County Jail. So they run from “the new jacks, wannabe pimps,” men who accost the women in an attempt to “knock hos.” That’s their term for persuading women to switch their allegiance from one pimp to another. The numbers of wannabes began to swell in 2005, when pimp chic swept movies and television. Hit songs like Slim Thug’s “Everybody Loves a Pimp” and “Pimpin’ All Over the World” by Ludacris and Bobby Valentino topped the rap charts. For Daddy Cool, the wannabe invasion poses a threat to the trade of established pimps. Even now, after 16 months behind bars, he fumes at the disruption: “Nobody can make money. They’re fuckin’ the game up.”

“I used to tell my girls I’ll break your jaw if I ever see you running from a pimp,” says Daddy Cool, adding pointedly that he would never actually carry out such a threat. “I told my bitches not to run, but to grab a door handle and jump in a [customer’s] car instead, or else to call me if they have to.”

Streetwalkers and their pimps aren’t the only ones who would love to see the new jacks disappear. More and more, customers are turning to the Internet to vent their frustrations. On chat boards devoted to the subject of buying sex, they gripe that the pushy pseudo pimps have spoiled the Seattle street market. “It has turned into a full-on circus,” grumbles a poster named “Croakie,”* “with mostly clowns trying to act like wannabe pimps.” Croakie laments that he saw more of them than he did streetwalkers. “I agree, I no longer cruise [the track],” reads a reply posted by a customer named “Streeter”—even though “the girls were hot.” Other street customers recount confrontations with the pretender pimps. More often, they complain of going home unsatisfied.

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It could be worse. They could get busted. On a warm autumn evening, about 25 Shoreline and King County police officers set up a “john patrol” on Aurora Avenue North. Four female officers do their best to look the part of prostitutes, costumed in short skirts, high-heeled mules, and chandelier earrings. They saunter along a preset length of sidewalk, masking their nervousness with Tootsie pops, bubble gum, and cigarettes. Within 15 minutes, a beige sedan pulls alongside a decoy officer. She leans toward the open window. Soon she gives a predetermined signal to indicate to her colleagues that an “offer and acceptance” has taken place—an arrestable misdemeanor.

The driver is unaware that some two dozen law enforcement agents are hidden, observing the exchange. He coasts down a driveway toward a rough parking lot, expecting only one kind of encounter. Suddenly the team swarms his car and pulls the door open. “Hands up!” officers shout. “Put it in park!” They order him to lie down on the rough asphalt while he is handcuffed. As he’s led away, he looks stunned. By now the officers and plainclothes detectives are pumped up. Sergeant Diana Neff, who is overseeing tonight’s sting, says it can take 72 hours to get over the “adrenaline dump” of an operation like this. To ease the tension, several of her comrades tuck chewing tobacco beside their gums.

Over the next seven hours, one decoy officer with tiny pigtails, painted-on jeans, and a gravity-defying tube top around her prominent breasts is especially successful in reeling in johns. Once an arrest is made, she and her colleagues become all business, kicking off the high heels and typing up reports on their laptops. A small room borrowed from a storefront starts to fill with suspects of various races and occupations, all sitting handcuffed and forlorn.

A few claim it was all a big mistake. Two young sailors who’d been cruising in a Corvette insist they were just “messing around.” “Oh my God,” one mutters as he realizes he won’t be reporting for duty in the morning and may face serious military charges. Then he musters some bravado: “I hate the Navy, so I don’t care. Yeah, I’m married, and she’ll care, but she’ll understand it was a big joke.” His companion is less sanguine: “This could end my career,” he says.

Nearly half the men caught in the sting are Latino. One is a chef and another a radio disc jockey; they are expected at work first thing the next day. “Why do we get so many Mexicans?” one deputy booms. But the suspect he’s patting down is actually a 26-year-old Eritrean man, neatly dressed in white Hilfiger corduroys, who worries about his fiancée back home and his new job at a gas station. Another suspect is African American: “I did it—guilty,” he admits; his wife is out of town and his job as a foreman may be jeopardized. Later, he wets himself, apparently from sheer nervousness. Another, a cabdriver, speaks too little English to explain his situation, though he managed to communicate well enough to get arrested and have his taxi keys taken from him.

Two suspects, both Asian American, face graver charges than attempting to procure sex. One tried to race away and struck the patrol car blocking his path. A porn magazine lies on the backseat of his car. He’s sullen and touchy when asked about his job delivering newspapers. The other wears baggy pants and long cornrows and says he stays with his mother: “She always worries,” he says, looking around warily. A police dog sniffs out a bag of neatly wrapped cocaine rocks in his trunk; they look like popcorn. The police also find a stash of gift cards from major retailers; gift cards are notorious tools for fraud. “I was just doing some shopping,” he explains, and the cops chuckle.

On Tahoe Ted’s Wed site, male customers and women workers share jokes, sports opinions, and even personal problems.

Perhaps the most visibly agitated was a Caucasian man, an architect by profession, pale and sweaty and obese, trembling and breathing heavily. He says he has a heart condition. He had half an hour to kill before picking up his daughter. “I’m not big on prostitution, I just went for the bait,” he mourns. He says his arrest will be an awful shock to his wife. “I’m over 60. How am I going to get another job?” he asks.

By 1am, a dozen men have been arrested, enough to fill the jail van twice. Sergeant Neff says if the team had had more officers, it could have nabbed even more johns. Then again, if these johns had had the means, ability, and foresight to troll for sex on the Internet rather than the street, the cops might not have busted any of them.

Many of the working women busted on the street seem to have little choice but to be there. If they’re older, homeless, or addled and prematurely aged by drugs, they can’t find safer, more lucrative venues for selling their services; about all they can do is show up. They don’t pretend to enjoy the life. “I’ve never liked sex, I’ve never had an orgasm,” says a chubby, unkempt young woman named Julie, writhing handcuffed in the back of a patrol car; her latest binge on heroin and crack has left her unable to sit still. Julie’s eyes don’t quite focus and her tongue keeps sticking out. She blurts out a quick account of her life: She turned her first trick at 15. Like many women who have been at the work for years, she considers pimps exploitative and unnecessary; she prefers to go “indie,” to be a “renegade.” That’s not easy, but Julie says she has a special edge. “I’m a thief,” she gasps. “I can steal a wallet—from your console, your pocket, from over your visor.”

Another streetwalker, 22-year-old “Breanna,” likewise struck out on her own; she’d worked for a pimp and hated it. She carries two cell phones to manage her dates. She says she loves sex as well as money—“But why give it away for free?” “Breanna” grew up in Kent and though she says her parents provided well for her, she always hated school and craved cash and bling. At 15 she convinced a friend to come with her to score a trick with a rich guy. Two blocks later: Mission accomplished. “I can make a thousand dollars a day,” she crows. “Now do you see why I do what I do?” Like many other others in the trade, she admits she still hasn’t learned how to handle money. “I’ve made a million dollars, but I barely have two pennies to scratch together.”
Despite the bravado of practitioners like “Breanna” and the weekend bustle near Seattle Center, street prostitution is declining in Seattle. And the trade is not just moving to outlying strips; it’s also moving off the street altogether. Daddy Cool, from behind the glass at the King County Jail, says that the world he came up in is changing: “The street scene? It’s dying off.” He pauses to consider the sex trade as a whole. “Actually it’s just changing with the times. It’s getting elevated.”

Off the street, an explosion of highly visible sex-for-hire advertising gives the impression that society has made its peace with prostitution; that while laws against practicing and promoting it still sit on the books, a tolerance policy prevails. The back pages of Seattle Weekly and The Stranger are filled with ads for escorts and “adult services.” Some of the papers’ readers may find them objectionable, but similar ads appear under “Escort Service—Personal” in the quaint old yellow pages. “Hot Blondes & Brunettes / $100 Specials,” reads one in Qwest’s Seattle Metro Official Directory. “College Cuties Gone Wild / Call Us We Love to Have Fun…Discreet Reliable Service.”

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A common assumption is that escorts are hired to accompany visiting businessmen to banquets. M. T. Hayden, a King County detective who’s worked 10 years in vice enforcement, buries the myth. “I haven’t seen an escort yet who is just about being a companion,” he says. Sergeant John Urquhart, a spokesman for the King County Sheriff’s Office, shakes his head: “The fact that escorts advertise in the yellow pages for sexual services tells me that society has accepted this, that they say it’s okay.” For law enforcement agencies, whether to investigate the services becomes a question of priorities, says Urquhart. “Obviously we can’t go through the phone book and put every massage parlor and escort service out of business.” It usually falls to patrol officers to police the street trade, the lowest rung of the industry and the spectacle that most offends ordinary citizens and draws complaints from irate neighbors.

Some prostitutes escape the patrols by working at massage parlors, but even they offer little protection from arrest. It’s a sunny afternoon when Detective Hayden walks up to an unmarked office in a Kent business park, the premises of the American Beauties Massage Parlor. Hayden wears a work shirt, sports a ponytail, and has slipped a lump of tobacco under his lip; he could be a regular guy knocking off from work in the middle of the day. Seven of his fellow officers park their unmarked cars, positioned so they can watch him enter.

Exactly 20 minutes later, when Hayden’s “massage” should have just gotten under way, one deputy rings American Beauties’ doorbell. The woman who answers is startled to see the rest of the team all wearing “SHERIFF” emblazoned on their jackets. They frisk her, search her belongings, then lead her, handcuffed, to a patrol car. Another woman tries to hide behind the door; she too is led out in handcuffs. Both women have soft, slightly pudgy bodies, highlights in their shoulder-length hair, and wary, shocked expressions. They say nothing. The business park’s manager stands outside, fretting and horrified, anxious to change the locks.
Inside, Hayden’s comrades uncuff him; when they stormed the parlor they cuffed him too, in order to maintain his cover. He complains wryly that one of the knots in his back feels a bit better, but now lotion is sticking to his shirt. The sheriff’s team swarms the spotless, carpeted office, taking photos and hunting for evidence. In the kitchenette cabinets they find paperback novels, takeout menus, and coffee mugs. “Now what the hell are they doing with a meat thermometer?” mutters one officer. In the drawers they find receipt books and an envelope stuffed with cash. The bathroom trash can yields empty cigarette packs, frozen dinner packages—and a used condom, which they photograph. Soft music is still playing, a strong odor of air freshener wafts through, and a courtroom show jabbers at low volume on the little TV in the waiting area. Under a small table lies a pair of women’s high-heeled mules.

While Hayden and his comrades search the massage parlor, King County’s SWAT team serves a search warrant at the south end home of an American Beauties employee. The hunt turns up stolen guns, an automatic weapon, and a boyfriend’s outstanding warrant for arrest from Texas. And that is a main reason the sheriffs carry out these busts: Prostitution operations are often bases for other illegal cash-only activities, such as money laundering and human trafficking. The two women arrested at the massage parlor will be released shortly, to await hearings on charges of prostitution and conspiracy and probation violations. One of them has 45 prior convictions for prostitution.

American Beauties drew a small part of its business through the Internet. Many others in the sex trade have left the streets, massage parlors, strangers’ cars, and newspaper ads behind; the Web provides all the marketing they need. Every day under the heading “Erotic Services,” hundreds of offers for paid sex go up on Craigslist. Accompanying the ads are photographs, sometimes taken by the women themselves, sometimes lifted from other Web sites (caveat emptor). The women appear in inviting or starkly revealing poses, atop living room sofas and motel bedspreads. The text is brief and the terms of exchange are couched in transparent euphemisms: “100 roses for ½ hour!”

Thanks to the Internet, the world’s oldest profession may be experiencing the biggest boon to prostitution since the advent of reliable birth control. From a law enforcement perspective, that could be a good thing. “God bless the Internet!” says Detective Hayden. “At least it’s reduced street traffic. A lot of those guys using the Web were the same ones driving around.”

Prostitution has entered a new online era—call it Sex Web 2.0—that, in keeping with the times, is all about social networking and user—generated content. In that brave new world, Tahoe Ted may be the world’s foremost john, thanks not to any high-spending ways but to his Web site—a simple message board that’s transforming paid sex locally and perhaps farther afield. Ted guards his anonymity closely: He communicated strictly via phone and e-mail, and only after checking bona fides with my editor. “I Googled you,” he wrote. “How do I know that you’re the real L. D. Kirshenbaum?”

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Tahoe Ted describes himself as a college-educated professional in his 50s, a “law-and-order Republican” with short brown hair who lives and works on the Eastside. He says he has been a connoisseur of paid sexual services for the past 30 years, starting with an unforgettable post-college experience one night after closing time at the Bavarian Gardens, a Bellevue club owned by the notorious strip king Frank Colacurcio; Ted wound up “with two gorgeous strippers in a gorgeous condo.” One of his most fulfilling arrangements, with a woman in Bellevue, lasted 18 years, until she retired. “She still has the same phone number!” he marvels.

Ted has operated his Web site, the Review Board, commonly known as TRB, since 2001. There, as on many online sex boards, men post reviews of their experiences with “sex providers,” which is what modern, politically correct johns call the women whose services they engage. But on TRB, providers post as well. They issue invitations and offer specials, like “Luscious and Sweet Tanya Coming to Town This Weekend and Awaits Your Call!” But surprisingly, and perhaps uniquely on TRB, they join the clients’ online conversations. The male customers and women workers share jokes, sports opinions, and even personal problems. They invite members to karaoke outings, birthday parties, and baseball games. They behave like a genuine community of people who sincerely enjoy each other’s company, even outside the exchange of sex for money that brought them together.
“I love my job,” one woman, a popular provider on the site, posted. “I love my clients. I love TRB. Thanks so much for making my life full and complete. Now I’ll stop crying!!” One man wrote to say he had just been released from the hospital after triple-bypass surgery. He made sure to check in right away with his friends, male and female: “Ted, you have an awesome board…. Take care everyone.” Ted for his part waxes protective toward the women who provide sexual services. “For many this is their occupation,” he explains. “It’s their only method of supporting themselves and their children.”

Ten years ago, recalls Tahoe Ted, before the trade took to the Internet, wariness prevailed on both sides of the transaction; providers and customers alike routinely took huge risks. “There was no community,” he says. Cruising the streets or bars, “I could get shot or ripped off.” Or exposed or arrested or infected. For users, arranging sexual encounters online has eased many of those worries. A message board like TRB, where everyone seems to know everyone else, also makes it possible to screen references and check reputations. Customers can check out rates, photos, and reviews before setting up an encounter. While the risks certainly haven’t disappeared, they are hugely reduced. “Very few guys on TRB get ripped off,” Ted says proudly. He reports TRB is still growing, with over 16,000 registered members and 1.2 million hits a month. Many readers, he says, are lurkers who don’t post, some of them business and sports professionals. Some are law enforcement officers who want to stay in the loop. At least one was a pimp: Daddy Cool reports he used TRB to keep up with trends of the trade.

High-priced escorts may be "witty, charming, sexy," and usually have Web sites touting their refined manners, sophisticated literary interests and advanced degrees.

By contrast, many other Web sites for prostitution patrons, such as BigDoggie.net, are merely the Seattle pages of national and international sites. Men and women don’t chat together there as they do on TRB. These sites require a $130 credit card payment with registration, potentially threatening users’ privacy. By contrast, TRB doesn’t require real names or payment. It’s a local outfit with no fees or advertising, and it reinforces the cohesiveness of its community.

That sense of community may encourage newcomers who otherwise wouldn’t have dared to buy or sell sex. It also allows the customers and the providers to be more selective. TRB users tend to scorn the street scene; the idea of selecting a partner off the street strikes them as dangerous and distasteful. They leave all that for desperate women and “mongers,” the term for customers who seek sex on the street. TRB customers who shop on the Internet want “escorts,” not “bitches” or “hos.” They don’t consider themselves mongers, they’re “hobbyists.” And they see themselves as relatively chivalrous.

Tahoe Ted and his fellow hobbyists seek what they call the GFE, the “girlfriend experience,” which comes with a high level of service. The provider is expected to be attentive, caring, and warm. She spends time, she listens, she even kisses. She is reliable about showing up and she enjoys the sexual attention she receives—or she’s good at pretending she does. Most likely she has her own Web site with an obligatory warning directing underage surfers to stay away.

All this is very different from the interaction sought by street sex customers. Street rates are a small fraction of escort rates—a blow job in a car runs $20 to $30—so customers can hardly expect a GFE. But they still use the Internet to share their experiences. On the bigger sex boards, mongers post explicit snapshots and recount their experiences with streetwalkers. They describe the “thrill of the hunt” they get from cruising the street scene or the occasional massage parlor. “Snake” posted his motives on USASexGuide.info: “I don’t want it free… as it complicates the affair. It’s the Last Tango in Paris experiences I seek. No names, no identity. Just brief and meaningless affairs. But it requires the patience and the deliberation of a spy.”

Some johns lament their addictions to paid sex and the risk of ruin that accompanies it. Or they bemoan the wham-bam-thank-you-sir brusqueness of the women engaged via Craigslist: “Once I was through…she hopped right up and headed off to the bathroom to clean up,” one posted on TRB. “That’s why I like the ladies here on TRB,” another replied.

Like any subculture, this world has its own argot. A review might read: She was a spinner (petite woman) with a natural rack (no breast implants) and hardwood floors (completely shaved genitals), allowed DATY (dining at the Y, cunnilingus) but French lessons (fellatio) were translated (using a condom); after ½ and ½ (oral sex followed by intercourse) I spilled a second cup of coffee (ejaculated a second time).

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Ted deletes posts that delve into fetishism or homosexuality, though he tolerates discussions of threesomes that include two women. To avoid antagonizing law enforcement he forbids posts that might warn of pending busts or otherwise obstruct justice. He estimates that half the men who pay for sex are married and another 10 percent are in outwardly monogamous live-in relationships. Some are devoted to their partners but still seek to sexually experience as many women as they can. Some are just lonely. And some don’t think they can score otherwise, at least not with the nubile partners they desire: “If you’re 58 and not especially rich, you’ll never get a date with a gorgeous 22-year-old,” says Ted. Many don’t want to endanger their jobs and relationships the way mongers prowling the street do.

I used to be a $300-an-hour TRB girl,” says an escort who, for this article, asked to be known as Inara Serra. She agreed to meet at a French bistro in San Francisco, where she sometimes does business; her Seattle time is overbooked. The man at the next table can’t focus on his menu; he keeps grabbing eyefuls of Serra’s slim jeans, red high heels, dark strawberry-blonde bob with professional highlights, and -tattoos that occasionally flash on her wrists. Whether laughing, sipping red wine, or explaining how she got in the business, she is perfectly poised. Her precise words and gestures complement her good looks.

The photos on her Web site are even more well-honed: beautifully lit shots of her wearing expensive lingerie and shoes, silhouetted against antique settees in tastefully retro interiors. It’s a highly professional marketing pitch; sex sells, and in this case, sells itself. It’s how Serra made the leap to the top echelon of Seattle escorts: She charges a minimum of $1,200 for a three-hour “dinner date.” That kind of money enables her to pay for college tuition (she hopes to return for a degree in psychology), a condo in Seattle, trips to Europe, and designer leather goods. The odd jobs she used to hold just couldn’t provide the glamour she envisioned when, living on a farm at the age of 13, she first saw Julia Roberts playing a streetwalker Cinderella in the movie Pretty Woman and thought, “How cool that she’s an empowered woman.” At 32 she still hasn’t told her parents how she makes a living, though she says she had an ideal childhood and remains close to them. Nevertheless, she declares, “I’m proud of what I do. I built this life for myself.”

Serra lives and works light-years away from Daddy Cool’s track. Her peers include escorts whose fees start at $3,000 for three hours. “We are a tight-knit group,” she says. “There are some amazing women out there. Smart, funny, witty, charming, sexy.” Escorts working at this level usually have Web sites touting their refined manners, sophisticated literary interests, and advanced degrees. They may make themselves available in several cities; Las Vegas often shows up on their lists, Seattle only occasionally. The language on their sites is often arch or flowery: “I am a courtesan and companion to a handful of discerning men (and occasionally a woman or couple) around the globe,” announces one. “I aim for seduction on all levels—mind and body—and the creation of experiences which are transcendental.” The postings conclude with a disclaimer, along the lines of “The rates quoted above do not constitute an offer for prostitution. They are for time and companionship only and anything else that may transpire is simply a matter between two consenting adults of legal age.”

Such locutions give at least the illusion of immunity from the busts that dog the street and massage-parlor trades. And the Internet, with its supportive, self-reinforcing user communities, makes the whole unlawful business seem safer. “It might be safer, but it’s still an unregulated industry,” says Detective Hayden. “Just because you’re paying $300 to $400 an hour doesn’t mean you aren’t taking a chance you’ll catch syphilis, MRSA, or AIDS.” And just because you advertise on the Internet doesn’t mean you won’t ever be busted; in Lynnwood last November, police arrested seven escorts they’d approached through Craigslist.
As popular culture chips away at old taboos, commercial sex ventures into increasingly mainstream territory, particularly in the higher end of the escort market, which is populated mostly by free agents who aren’t under anyone’s control. A century ago, a woman could ruin her reputation by appearing on stage; today, soccer moms take pole-dancing lessons and farm girls make career choices based on Pretty Woman. In the next century, prostitution might even be viewed as a socially acceptable way to support a family; law officers muse on the pros and cons of legalizing it. Until then, save for a few parts of Nevada, selling sex remains against the law. Sergeant Urquhart declares, “We have a job to do.” But as Tahoe Ted says, nature doesn’t change: “Guys have to poon and ladies have to earn a living.”