By EJ Dickson on October 5th, 2014


I only have vague memories about the first time I had sex. (I was 15, and it was the intermission of my camp's production of A Midsummer Night's Dream; I was Helena, he was Lysander, and that's all you need to know.) I do, however, have a very clear memory of the first time I had cybersex. I was 10.

His AIM handle was FrankZappy, and I believe he claimed to be a married man from Queens. I was Dana, a name I had lifted from a character on my favorite Purple Moon CD-ROM. Dana was 19, an aspiring veterinarian, and everyone told her she looked like Britney Spears. We met in an AOL chatroom in the "Friends" category, bonding over a shared interest in baseball and the inspiration for his screenname; I'd impressed him by referencing the lyrics to "Don't Eat the Yellow Snow."

Every day (except Monday and Wednesday, when I had Hebrew school), between 3:30pm and 5:30pm, I'd grab the Compaq laptop from my parents' room, zip past my babysitter watching General Hospital, and log onto AOL to see if FrankZappy was on my buddy list. I don't remember the specifics, but I remember we talked about classic rock and which colleges he thought Dana should apply to.

It was easier to be anonymous on the Internet back then, to flirt and wink and experiment behind purposefully misspelled, sexually charged screennames like seksikittee69 and bigboi17 that weren't tethered to a public Facebook account. While technology like group video conferencing existed, it was painfully slow and not readily available. This veil of anonymity let an entire generation of young women like myself experience their sexual initiations in AIM chatrooms.

It was easier to be anonymous on the Internet back then, to flirt and wink and experiment behind purposefully misspelled, sexually charged screennames like seksikittee69 and bigboi17.

For the first few weeks or so, my relationship with FrankZappy skirted the lines of PG-13 respectability. Then one day, he started telling me what he wanted to do to me if he met me, and I, picking up on his cues, told him what I (or "Dana") wanted to do to him. Of course, I had no idea what I was saying; much of what I said was based on what I had seen on General Hospital and read in Jackie Collins paperbacks. And to be honest, I don't think he knew what he was saying either. He wasn't particularly imaginative, or even literate. (For the next few years, I thought "cum" was a synonym for "penis," in large part due to FrankZappy's sloppy syntax.)

I don't remember being sexually aroused by my relationship with FrankZappy, so much as I was just fascinated by anything vaguely related to sex at the time. I probably got a similar thrill from watching my Sims family make woo-hoo. There wasn't anything particularly special about FrankZappy, who would later become one of a string of anonymous strangers I would cyber with online.

He was just the first man online who gave me the most attention, and as a knotty-haired, awkward 10-year-old who desperately craved male attention, that was good enough reason to be excited whenever the AIM chime symbol sounded, signaling that he'd signed on. It was invigorating to have an older man express interest in me and my life; it didn't matter that that life wasn't mine, but Dana's, or that he was supposedly old, potentially married, and borderline illiterate.

For me, cybersex with FrankZappy was nothing short of a full-blown sexual awakening.



For years, I didn't tell a soul about my relationship with FrankZappy, assuming they would think he was a pedophile and I a snaggle-toothed sex maniac. But I later discovered that I was not the only pre-adolescent haunting the AOL adult chatrooms. Most teens of the early AOL chatroom era, or the mid-to-late-1990s, experimented with cybersex or had their sexual initiations online, in chatrooms with names like "Bored housewives over 30" or "Naughty wellhung surfer boys 18+."

In 1996, AOL had 5 million subscribers; by 2002, it had 25 million and was the biggest dial-up service in the country. Chat had never been more expedient or accessible, so it was only a matter of time before people started using it for sex. Rob Weiss, an expert on porn and cybersex addiction, attributes the cybersex boom of the mid-'90s to what he referred to as the three A's: "accessibility, affordability, and anonymity."

First and foremost, cybersex allowed people to get off without the effort required to obtain pornographic material or find a new partner IRL (in real life), especially if you were taken to begin with.

"It was incredibly powerful for people to be able to go into chat and talk about sex and be sexual without risking their marriages, or their relationships," noted Weiss, who estimates this practice started exploding around 1996, when AOL was first gaining steam. "This was a way to have a brand new sexual experience without having to take the same risks you took in a real meeting."

Unlike phone sex or late nights in bars, meeting someone in an AOL chatroom for a little at-work afternoon delight was essentially free, or at least the price of a dial-up Internet connection. And for those who were too nervous to put themselves out there in real life, cybersex was a conduit for experiencing the pulse-racing high of anonymous sex.

If you secretly wanted to be spanked, for instance, but were worried your partner wouldn't be receptive to the idea, it was easy to find someone who would be in one of the hundreds of BDSM-themed chatrooms. The fact that you had no idea what the person you were typing with even looked like in some ways heightened the thrill.

"Emotional arousal and fantasy are incredibly powerful instruments," Weiss said. "The idea that you could play out your kinky fantasies and ideas with these strangers across the country who you'd never met, and have them be excited and responsive and engaged, was incredibly exciting to people."

When I surveyed my friends to see if they had had cybersex in AOL chatrooms, nearly all of them remembered having similar experiences, usually with friends.

"My cousins and I would huddle together in front of one of their slim-for-the-time Dell monitors 'playing' online checkers (or something) and engaging with people who were probably (but maybe not?) a lot older than us," recalled Jenny Kutner, an assistant editor who writes about sex and dating for Salon.

For me, cybersex with FrankZappy was nothing short of a full-blown sexual awakening.

"I do remember someone once telling me he wanted me to shove marshmallows up by butt while I touched myself," she told me in a follow-up email, "and I felt a little bit confused about whether this was 'normal' or not."

Eventually, though, curiosity would take hold, and those who had started venturing into chatrooms playfully started ducking in in earnest—and alone.

"I know everyone talks about how they did that with their friends and lol it was so funny, but like, I was kind of turned on by it," Amy*, a freelance writer who was 12 years old when she first started going into AOL chatrooms, told me. "I feel like everyone who talks about it now and is like, 'Oh me and my friends would do that all the time' are covering up that they were probs kind of turned on too."

Like many relationships that start online, these interactions were marked by a patented, often outrageous dishonesty. "I lied about my age, my location, my gender," one of my coworkers told me. "I think I probably was truthful about my species, but beyond that I just fed everyone lies."

More often than not, these lies would backfire in absurd, hilarious ways: One of my best friends, for instance, once sent an image of Mandy Moore from her desktop when she was asked for a photo by a chatroom paramour, at which point he "politely informed me there was a copyright notice at the bottom of the photo."

Without Skype, Facebook, or any identity verification system to speak of, the adult AOL chatrooms made up a universe that was almost completely void of accountability. Even if someone didn't believe that you were, say, Stone Cold Steve Austin or Mandy Moore, it almost didn't matter; you might have been lying, and your partner likely knew you were lying, but because he or she was probably lying too, no one seemed to care.

For people my age, who knew little about sex or relationships but were thirsty for more information, cybersex wasn't just an opportunity for exploration or self-reinvention—it was also educational.

My former colleague Maya*, for instance, used her cybersex misadventures as an opportunity to find out what penises and vaginas actually looked like by soliciting naked photos from people in the adult AOL chatrooms. "I clearly had some adolescent voyeurism tendencies," she told me. "So I would pretend to be both genders and then send people the pictures that other people had sent me earlier."

Of course, it's not surprising that curious adolescents would use the Internet as a conduit for their early sexual education. But it's also not a coincidence that the majority of the people I spoke to for this piece all had their sexual initiations in AOL chatrooms. (I did speak with some men who had early cybersex experiences, also with friends, but women were far and away more likely to report doing it in isolation.)

In his practice, Weiss says, women tend to be "much more involved" with text-based, sexually charged chats, while men are more likely to report compulsively watching porn.

"Chats involve an emotional context and a narrative. You can get a sense online if you have a connection with your partner," he said. Because he says men are more visually oriented, "they might have dabbled in the chatrooms, because that's all that was available at the time, but for the most part they were looking for porn any way they could get it."

Regardless of whether you agree with Weiss's contention about the roots of male and female desire, early cybersex allowed young women to explore their early sexual identities and desires without the fear of guilt, judgment, or censure that would usually accompany such efforts at school or elsewhere. Even still, for many of the people I spoke with, feelings of guilt and shame were part and parcel with the cybersex experience, especially considering how young and ignorant of our sexuality we truly were. Maya, for instance, stopped soliciting naked pictures from her cybersex partners because she was ashamed of her voyeuristic tendencies. "I was convinced my dead grandpa knew what I was doing," she recalled.

And Amy, who credits cybersex with helping her discover early twinges of erotic feelings, says she stopped because she felt too guilty about lying to her partners. At one point, while posing as a "22-year-old blonde who wanted to bang," she started chatting with a firefighter who sent him photos of his daughters.

"This was a way to have a brand new sexual experience without having to take the same risks you took in a real meeting." —Rob Weiss

"He just seemed like this nice, kind of lonely guy somewhere in the Midwest who really loved his kids, enough to talk about them to a stranger on the Internet who was trying to seduce him via ASL mentions," Amy said, referring to the Internet shorthand for "age, sex, location." She remembers feeling guilty about what would have happened to him had he (or anyone else, for that matter) discovered how old she was: "Would it have been his fault, if I had presented as a 23-year-old consenting adult?"

(Short answer: Yes. In 2012, for instance, one St. Paul man was found guilty of having cybersex with a 15-year-old boy, an offense punishable by up to three years in prison, despite the fact that the boy in question told him he was 16—the legal age of consent in his state.)

It was these feelings of guilt that led me to ultimately break off my relationship with FrankZappy. It ended in much the same way other online relationships do: He wanted to meet up, and I freaked out. At one point, I thought about telling him the truth—that I was actually a very precocious, very sexually curious, very strange 10-year-old girl—but I ended up only revealing a version of it.

I sent him an email saying I was actually 15, and I had to stop our relationship because I "didn't want to let down my folks." (I vividly remember typing that exact phrase, because now it seems like such a blatant approximation of how a 10-year-old would think a 15-year-old would talk.) Then I apologized and wished him the best.

I never heard from him again.



It's been nearly 20 years since the dawn of dial-up, and 15 since I took my first giggling, tentative steps into the murky waters of sex on the Internet. Now, I write about it professionally, and I regularly comes across news stories about children doing exactly what I did—of learning about the dangers of sexuality too fast and too soon, of leaping headfirst into the red-light districts of Craigslist, Snapchat, Tinder, Facebook and Skype.

There's the 16-year-old girl who posted a photo of herself giving a blow job on Instagram, only to become the laughing stock of her small Michigan town. There's the group of Montreal 13-year-olds who became embroiled in a child porn scandal when their friends encouraged them to take nude selfies on Snapchat. And when I went to high school in New York City, there was the eighth-grade girl from a neighboring school who was known throughout the tri-state area as "Swiffs," because she once emailed a video of herself masturbating with a Swiffer WetJet to a boy she was interested in. The stories are endless, and endlessly depressing.

When I read these stories about underage girls sexting on Snapchat, or being assaulted by older men they met on Facebook, I think about how lucky I was to have had my sexual awakening at a time when technology was limited, when there was only one digital platform available for a young girl to be exploited, rather than dozens.

Without Skype, Facebook, or any identity verification system to speak of, the adult AOL chatrooms made up a universe that was almost completely void of accountability.

It's never been easier for a lonely, Web-savvy, preteen girl to learn about sex from a FrankZappy type. But considering how far technology has advanced since the mid-'90s, how much that veil of anonymity has been lifted, and how easy it is now to see someone's face or body, that kind of relationship would now have real-world, potentially dangerous ramifications. And now, with the proliferation of webcams, Google, and social media, it's no longer possible to be truly anonymous—at least for novices—or to go into a chatroom and claim to be a 19-year-old veterinary student. There are too many tools at our disposal to verify or refute such claims.

When I look back on my time cruising for cyberpeen in AOL chatrooms, I don't think so much of the people like FrankZappy that I met, because honestly, what was there to know about them? I think about what would have happened to me had I done the same thing today. I think about Amanda Todd, the 15-year-old Canadian girl who committed suicide following years of blackmail and cyberbullying after flashing a stranger online when she was 12. The stranger had been a "capper," a group of men who haunt the darkest corners of the Internet, looking for underage girls to bully into performing acts on-camera.

Had webcams and capper culture existed back then, I like to think I would have had the wisdom and moral fortitude to withstand such pressure. But if I'm being honest about who I was then—bookish, lonely, patiently waiting at a computer screen for a man I did not know to ask me how my day was going or what kind of music I liked or what color panties I was wearing—I am not so sure.



A few weeks ago, I decided to see if the AOL chatrooms were still around, to see if I could recapture that high of typing naughty words to anonymous strangers. What I found were a few text-based, fairly unsophisticated chat platforms, like 321chats or 99chats, where a handful of people with screennames like "Texasboy529" or "sexykitty328" were asking the same questions—"asl?" "anyone wanna cyber?"—that filled AOL chatrooms two decades ago. The only difference was, there were fewer of them.

Most everyone seems to have migrated to Grindr, Tinder, and AdultFriendFinder, services that offer real sex with real people revealing the truth about themselves—or at least, some version of the truth. But the appeal of anonymous, text-based chatting still lingers, even in the era of Tinder hookups and instant gratification.

It's never been easier for a lonely, Web-savvy, preteen girl to learn about sex from a FrankZappy type.

"Everything on the Internet has changed," Weiss said. "It's faster, it's more immediate, and there's more of it. But what happened in these chatrooms and what we're experiencing now [with Grindr, Tinder, etc.] is not about the devices. It's about people. We've always had the same desires, the same needs. It's been in humanity since we climbed out of the sea."

To the knotty-haired, snaggle-toothed, awkward girls out there, staring into the lights of their screens and hoping to make a connection with someone, anyone: I hope, for your own safety, that you will be smarter than I was at navigating these treacherous waters. And to FrankZappy, wherever you are, whoever you are, I would like to thank you, and leave you with one final admonition: Watch out where the huskies go. Don't you eat that yellow snow.


* Editor's note: Names in this story have been changed where noted.

Illustration by Max Fleishman