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IT WAS HARD to envision its enormity.

At the Web’s inception, few outside the tech world realized it would be seen as one of the signal events in computer science. Or that it would ignite an information revolution. Or that it would make it possible for an individual or a group or a government to communicate with billions.

Even fewer foresaw that the Web would become the largest wank-off machine in creation. Though there were inklings.

People browsing for sexual content, like those searching for illicit love, guarded their anonymity and frequented hard-to-find addresses, often at night. Like those caught up in affairs, they could become obsessive, protective of their time in the zone. Like those donning drag, they assumed new names and created parallel identities. The tech writer (and self-described nethead) J. C. Herz would make the point in her 1995 book Surfing on the Internet that the wired universe offered “gender options that don’t physically exist. For instance, the LambdaMOO virtual world gives users a choice of male, female, neutral, neither, royal (the royal ‘we’), and the natty, insouciant ‘splat’ (*) option.” Women and men would assume cross identities: a member of one sex, disguised as another, would engage in cybersex with Net partners of either gender, or both, depending on the mood and circumstance. This elasticity unleashed a new freedom to experiment, fantasize, and role-play.

As the digital age bloomed, sexual variety reigned. In the late ’80s and early ’90s, cybersex had a limited connotation: virtual-reality kink. VR sex, theoretically, involved people in proximity or in distant locations donning special suits and/or cybergloves and/or headgear, festooned with wires, and then remotely diddling their partners and sharing a simulated sexual experience, sometimes accompanied by SFX audiovisuals. (CGI—computer-generated imagery—was a huge gaming and cinematic breakthrough in the 1990s.) Cybersex was sim stim. For a time it went by the cringe-worthy name “teledildonics.” And at the time, it was pure hokum. (In 1997, Mike Myers, with a debt to Wilhelm Reich—and to films such as Barbarella, Putney Swope, Sleeper, and Liquid Sky—introduced “fembots” to explore the concept of robo-shagging in his Swinging Sixties spoof Austin Powers: International Man of Mystery. But for a species that now got its babies from test tubes, why shouldn’t a geek try to get his ya-yas out by way of Alpha Centauri?)

Back then, it was called cybersex. Or virtual sex. Or netsex. And much of it was emerging from Usenet and newsgroups. In the fantasy forums called MUDs, it was sometimes called TinySex, as Sherry Turkle would note in her 1995 book Life on the Screen: Identity in the Age of the Internet, discussing early “computer-mediated screen communications for sexual encounters. An Internet list of ‘Frequently Asked Questions’ describes the latter activity . . . as people typing messages with erotic content to each other, ‘sometimes with one hand on the keyset, sometimes with two.’ ”

Along came CD-ROMs and DVDs—interactive discs that could be slipped into a disk drive or game console—which allowed users to issue simple commands and choose various options or outcomes in their sexual entertainment. There were Internet forums where people could post erotic stories (or add to others’ stories)—many of which would evolve into multipart series—that would attract tremendous followings. There were hatchling websites that stole printed porn pictures and posted them as their own; sites that featured virtual strip blackjack; sites where online models popped up in tiny matchbook-size peep-holes, responding to keyboard commands (“How about removing those fish-nets?”). The Internet began to micropander to every type of sexual connoisseur.

According to Forbes, by the end of the ’90s there were half a million sex sites, with one hundred fresh ones popping up each week, many of them very profitable very quickly due to the sales of ads, products, and links to spicier paywall-protected areas. Come 2000, the porn industry’s total yearly take was some $2 billion in Web business alone.

The Web, by definition, offered virtual sex. Much of it was literally autoerotic. The solitary online sexual encounter, for many men and women, came to be regarded as noncommittal, less emotionally taxing, and less trouble. Why deal with the challenges or rewards of another’s needs, when one could satisfy one’s own—and so efficiently? For many online users, the synthetic actually replaced the actual: online sex became not an expression of mutual connection but of selfish release. But this was only half the picture.

For millions of others, the earliest forms of cybersex brought the promise of genuine engagement, not alienation. Strangers typing words to one another—digitally stimulating a partner by writing on a keyboard—could experience real-time interaction on an entirely new plane. Online sex brought InstaGrat. It boosted the ego. It offered a number and variety of potential partners that were theoretically limitless. It allowed for a semisanctioned embrace of new taboos, which was arousing in and of itself. Its virtual nature made “online cheating” arguably more acceptable to one’s real-life partner or one’s conscience. Its attendant anonymity could be exhilarating and often emancipating. Its seamless utility (from the comfort of one’s home) was liberating. Its relative safety, to many users, beat its real-world equivalent hands down, because electronic transmission came with zero risk of STDs.

Enter the Con Man

One of the earliest Net-sex horror stories involved an online skeeve who turned out to be a con artist. Susie Bright remembers it vividly. One of the West Coast leaders of sex-positive feminism, Bright in the early 1990s had left her job editing On Our Backs. Bright recalls that she had first gone online because she’d heard that on a computer bulletin board called The WELL a community of people was engaged in a discussion thread labeled “Why I Love Susie Bright.”

Bright now says, in a series of interviews and emails, “The WELL was like the shiny new toy that everyone in the media was fascinated with. Soon, of course, came the con man. The first time there was a sex hoax on the Internet—at least that I am aware of—it happened at The WELL. There was a private women’s conference that only [female] members could be part of. There were quite a lot of women on The WELL—for an Internet group, it was a shocking number. That was part of what made The WELL so cool. It didn’t even occur to me that computers were supposed to be a guy-only space. [As part of ] this private women’s conference—it was more gossipy and talking about our private lives and things you didn’t necessarily want everyone else to see in public—someone started a topic called ‘That Son-of-a-Bitch.’ ” She laughs. “Sounds promising, right?

“This woman told a story about how she’d met this wonderful man on The WELL and it just all seemed so incredibly touching and poignant and like a match made in heaven. It’s hard to capture how innocent we all were. So we were ‘listening’ to her describe how sexy it was. By the end of the story, as you can imagine, he turned out to be a con artist. He [had seemed] really, sincerely interested in her—‘We’re going to have dates and so on’—and then he had these emergencies where she had to send him money. That was when the worm turned. But by then she was so in love with him, so infatuated with their virtual affair: they’d had phone sex; they’d done so much [online]. So when he started extorting money from her, she didn’t even see it [coming].”

Bright remembers that one of the other WELL participants chimed in. “The woman stopped her and said, ‘This same thing is happening to me and I haven’t told anyone because I’m so embarrassed and ashamed and I’m starting to feel like a chump. And here we are, we’re both these ultra-smarty-pants, computer-genius women—how can this be happening to us?’ They compared notes—and it was the same man.” When they floated his name to the wider community of The WELL, Bright recalls, “there was complete pandemonium. They outed him. And he had been doing this with so many other chicks, it was just [crazy].”

Bright recalls her reaction: “I’m sitting there at my keyboard and I just dropped my cup of coffee, because I had just fucked this guy in New York City a couple of weeks earlier. In real life. And I felt really embarrassed because, unlike the others, I had not given him money. I had merely had sex with him. I wasn’t that attracted to him. I was on a book tour. It was proximity. Yes, he had been a big fanboy and told me how much he just loved-loved-loved the idea of seeing me and he would do anything for me when I came to New York. Then I said, ‘Well, we can meet.’ He was based in New Jersey. This guy has all these super-brainy women dangling on a string. [He] was, as far as I knew, the first Internet cad.”

More Freedom

There were downsides, there were upsides. My friend Stephen Mayes, a respected photo editor and champion of photojournalists, insists that the Web had a largely salutary effect on the sex lives and love lives of many gay men. “I had had an incredible disability in the gay world of never having picked up a man in a bar,” Mayes confides over drinks at a speakeasy in Manhattan’s East Village. “What the Internet did was give me a new awareness of myself. Previously, the gay bar scene revolved around a body fascism: a prescriptive sense of muscles, tight abs, shoulders that you had to have. And I am less of a physical specimen in that way. So in a bar, my eyes had always been filled with fear—the fear of rejection. Along comes the Web, and I dropped into this world in which I believed my body would be accepted. The Internet released me from all that fear. It suddenly gave me a freedom to meet with men in a way that I’d never experienced before.”

Mayes believes that when it came to the stereotypical sexual aesthetic of the gay man, the digital realm had much to recommend it. “The gay world seems to lend itself to this idea of sharing stuff,” he insists. “It’s open-source, like the Web. It has that reputation: open relationships, sharing partners, etcetera. It has, historically, a sense of being furtive—pushed into the underground for centuries—but once outside social constraints, it was a lot freer within a private, underground context.” In many ways, these were also the hallmarks of the early digital space: a private, members-only society with its own language and codes and libertine ethos that existed under the radar.

At the same time, Mayes recalls, the digital photography revolution of the 1990s served to enhance the sex lives of those who were drawn to the visual, to exchanging private pictures, and to creating homespun erotica that might invite and satisfy the fellow male gaze. In previous decades, many gay men, he says, had relied on Polaroids (which required no processing) since they were concerned about bringing their undeveloped film to the corner drugstore or one-hour photo shop. “There was a social stigma,” says Mayes, “and, more importantly, legal issues in taking your film to the lab. Sodomy was illegal in places like Texas until the 2000s. So the digital camera freed up people.” And those intimate digital photos could be easily traded electronically. In the early days of the Web, Mayes notes, “the digital sexual image is very private—you take it, put it up on your computer, share it just with the people you want to see it. No lab technician! In the late ’90s this changed. If you wanted to, you could place an explicit photo online to attract partners, and you felt it was private. You had to register under a screen name. You were addressing members like yourself. But it was a misguided belief that you were addressing a private club. In fact, anyone could register and, more than that, you could download the image—and suddenly your own photo [would be] feral, animal, developing a life of its own. For all the benefits that these websites brought us—gay and straight and otherwise—little did we know the extent to which our personal images would become public commodities that had the potential to spin out of control.”

Online Dating

The Internet, for many, was a virtual singles bar. On the largest dating sites, chemistry (both sexual and interpersonal) would be replaced by algebra. Algorithms that had been designed to sift through a voluminous database of attributes listed in members’ profiles would sort and rank potential partners’ likelihood of attraction and relationship longevity. Individual subscribers would then be presented with a slate of possible dates who, in time, might be possible mates.

Matchmaking services, of course, had been around for decades. But the Web brought a new level of respectability to such artificially induced interaction. Little by little, the fix-up began to lose its total-loser stigma. In the digital age, the unattached, no matter what age, came to see e-dating as socially acceptable, safe, and efficient. In fact, the algorithms and the screening process conferred a certain authority. (At the time, columnist Michael Wolff would describe online dating as a new and rather vanilla way of mating: “a perfectly decent, unremarkable, squaresville thing to do.”) By comparison, the singles scene, the bar scene began to be regarded as crass.

Dating sites took off. And this ’90s phenomenon so revolutionized the way urbanites coupled up and settled down that today, according to the New Yorker’s Nick Paumgarten, “fee-based dating Web sites” take in more than a billion dollars annually and have become “the third most common way for people to meet. (The most common are ‘through work/school’ and ‘through friends/family.’)” As the dating dot-coms grew, so did a new set of online meeting places that turned one’s wider net of contacts into their own raison d’être. These were the start-up social networks. And in terms of the wider culture they would become far more influential than the dating sites. Social media would not only help define one’s persona and sexual expressiveness (shaping one’s real-world reputation and online demeanor in the eyes of potential suitors, friends, strangers, and even potential employers), but would also have long-term effects on social interaction, free speech, and political change. Services like TheGlobe.com and SixDegrees.com (well before Friendster or LinkedIn, before MySpace or Facebook) were the online hubs where communities of users gathered to converse and exchange information about shared interests, pastimes, or backgrounds.

Sex, of course, was central to the origin story of social media. “We often forget that social networking, early on, was really all about sexual stereotyping,” says my friend Rachel Winter, the film producer. “Facebook was founded as a way of rating women’s looks. From that nucleus—devised by male students at Harvard—came everything that followed, including the trolling and shaming. At this stage I would say: let’s all take a breather and ban social media for five years. We’d all be better off.”

[“Source-wired”]