(Originally appeared in Radar on Oct. 21, 2008)

In the past week, I have seen hundreds of vaginas—shaven and hirsute, flowering out like Georgia O’Keeffe paintings and demure as habited nuns; scores of aggressively turgid, rhizomatically veined penises; breasts of varying degrees of authenticity, proportion, and symmetry; and an emotionally scarring amount of anuses.

For I have entered the seamy world of Adult FriendFinder, the closest thing on the web to an amalgam of Studio 54 and Times Square circa-‘77.

AdultFriendFinder.com (there are spinoff FriendFinders for different ethnicities and religions, seniors, and the PG-rated FriendFinder.com) is currently the 25th most-visited website in the U.S. and the 43rd in the world; no other stand-alone dating site has cracked the top 100 for either. The casual-sex mediator boasts over 30 million members and maintains that only half are heterosexual men (a figure not borne out by either informal studies or a quick glance in one of its chat rooms, where the male-to-female ratio is 30:1 or greater). It advertises widely on the web to snare the curious and susceptible, usually with small pictures of women and text indicating that these nubile women in your town all want to have sex—with you.

In other words, it’s sort of like Ladies’ Night at the sleaziest club in the world.

I scoured the Internet for attractive amateur nude photos and signed up as a straight male (with an interest in transgenders/transvestites/transsexuals) named Clientele9, a bisexual female (LovelyRita1985), and a gay male (JohnQHolmes1983).  The site’s company, Various, Inc., was sold last December for $500 million to Penthouse Media Group, which also owns online-dating behemoth Spring Street Networks, so the interface for AFF is reassuringly conventional.  Filling out a profile, though, is a bit different.  In lieu of expressing a desire for, say, short- or long-term relationships, the AFF user can check off interests in “1-on-1 sex, Bondage & Discipline, Cross-Dressing, Discreet Relationship, Erotic Chat/Email/Phone Fantasies, Exhibitionism & Voyeurism, Group sex (3 or more), Miscellaneous Fetishes, Other ‘Alternative’ Activities, Sadism & Masochism.”  More nuanced optional questions include “What STDs are you comfortable with your partner having?,” “What bondage type gear do you enjoy using during sex play?,” and the deathless “What are your thoughts on anal sex?”

The profiles run the gamut from the subliterate (most of the men) to the cleverly crafted (a few of the women).  About two-thirds of the men put their phalluses front and center in their photos, while the females occasionally aim for the faintly artistic, with spread-eagled and -cheeked shots predominating.  A few exhibitionists upload their amateur sex videos, some of which get upwards of half a million views.  Many of the more attractive photos—especially of women—are clearly as fake and plucked from Google Image searches as mine, but the majority look genuine and are supported by additional photos.  Nearly all the males unabashedly state their goal of casual sex, though a few indicate that they would be amenable to a relationship with the right person; more of the women take this tack of looking for love in, quite possibly, the wrongest place of all time. Transgenders/transvestites and swingers have healthy representation as well.

The site is also used for social networking. Joining another member’s network entitles one to view private photo albums and write bawdy testimonials such as “The blowjobs are still the best ever, her pussy is delicious, she is beautiful, the outfits are breath-taking, the sex is passionate and hot and sweaty and unbelievable!”  Several members told me they had made some good friends in addition to finding sex partners.  Blogging is popular, as is contributing “articles” to AFF’s online magazine; it is doubtful that any prose will be anthologized in forthcoming erotica collections.

For Clientele9, I received a few messages (from transgender women) but was unable to open them, or view anyone’s profile, without first purchasing a membership (starting at $19.95 a month). With Rita, however, I had full access to others’ profiles and messages sent to me. (I could not read messages intended for John, until, without warning, the system allowed me.) AFF has caught flak for baiting men into buying memberships with decoy users in chat rooms, but this seemed like a much more insidious tactic: not many men who sign up for such a site could resist paying to see what that supposed 24-year-old female wrote to them.  (As for obvious-from-the-get-go phony profiles that requested suitors visit a porn website to contact them, I ran across just a few; the subtler method is to lure a man into sending a message, then getting his real email address to add to a mailing list.)

For skinflint men, chat rooms are the alternative to ponying up a twenty.  These are the meat markets of AFF—as Rita, I was barraged every few seconds via pickup lines no more poetic than “hi sexy”—with some webcams that display women typing in regular or skimpy outfits and men, invariably, masturbating in their desk chairs.  I spent ten minutes I’ll never get back watching a 28-year-old transvestite in Grand Rapids, Michigan, change in and out of women’s clothes.

In my first 24 hours on the site as Rita, almost 40 men wrote to me.  Most scrawled ungrammatical and misspelled one-liners addressing me as “sexy,” “beautiful,” or “baby,” complimenting my body, explaining what they would like to do with me, and attaching more pictures of—you guessed it—their erections.  Some e-Cyranos were more prolix: “IT TAKES A THIEF, TO CATCH A THIEF AND IT TAKES A WARRIOR LOVER OR A THONG HUNGER [sic] PIRATE TO CAPTURE THE CHERRIES OF ANY SWEET MAIDEN LACED IN GOLD JUICES FROM HER BOX OF EXCTASY [sic]. I AM ONE OF THOSE WARRIOR LOVERS AND THONG HUNGER [sic] PIRATES ALL ROLLED INTO ONE.”

The most heartbreaking, though, was a 52-year-old who apologized for being too old for me and for his average looks, describing himself as “a down to earth type of person, a little on the shy side, but once I get to know you; you would never believe me being shy. I have a very good sense of humor so I am told. I have been known to play practical jokes on people at work…I like children and animals, with the exception of rodents and fleas.”

Conversely, I sent out almost 50 boilerplate messages to women in my first hour as Clientele9 (depicted as a ruggedly handsome Russian solder), with just three interested responses—and two had near-identical short profiles (“Most of my friends would say I have a easy-going personality”), suggesting fraudulence.  John received a couple of messages per day from gay men that were generally equivalent in erudition to those for Rita.

Most men confessed that they had either not yet encountered anyone on the site, or had met one or two women with experiences ranging from disappointing to sexually fulfilling. It wasn’t too hard to figure out why a guy would trawl—even against steep odds—for no-strings-attached sex, but what kind of single woman uses Adult FriendFinder?

Quite a few, it turns out, many of whom could easily snag a partner in a bar if they so desired.  I chatted with a voluptuous 36-year-old Southern Californian blonde with the username sinsualdream who has been a member for almost two years.  While she estimates she has met around 30 men and women (and had sexual contact with two-thirds of them), she is currently looking for a monogamous relationship, and her profile justifies her choice of AFF: “I’m an EXTREMELY sexual woman. I love sex. I love hot, sweaty, screaming, multi-orgasmic, dual oral, fucking insane sex. I love being kinky and dangerous and pushing my limits. I want to find a man who is the same.” Besides finding like-minded kinksters, she prefers the site’s convenience: She works long hours as an advertising director, disdains the bar scene (an opinion echoed by other women), and is attracted only to black men (she’s also registered on a couple of black dating sites), so AFF helps her screen potential mates.  She receives 50 or so messages a week and responds to perhaps three, and needs to establish a rapport over phone and Instant Messenger before any encounters for coffee or dinner. Five men became short-term monogamous boyfriends, and she says she fell in love with two others. She doesn’t fear having her profile or photos exposed to acquaintances or colleagues—“my life is my life…too short to worry about those kinds of things”—and has had frank discussions about her sexuality with her 18- and 19-year-old sons. Indeed, very few users issue a standard disclaimer warning others against reproducing any of their profile or pictures elsewhere (the women pictured in this article consented as long as their faces were blurred).

The site also appeals to women getting out of sexually defunct relationships or eager to explore their sexuality.  Lynntlb69, a 38-year-old from Massachusetts, had had one prior sexual partner when she married fifteen years ago. With their relationship already on the rocks, she and her husband joined in May so she could engage in a threesome with him. It didn’t work out, they separated, and since August she estimates she has had sex with over twenty men and couples. Adult FriendFinder, she wrote, has given her “the strength to believe in myself that I was pretty enough” to attract men.  She’s embracing her newfound freedom and is not looking for anything serious: “Once in a while I meet a guy who wants more, and it really sucks when they say that I have let them down. This is a great way to come into my own sexually. I have had a great deal of wonderful sexual experiences, and I am just getting started.” Next on her to-do list? A gangbang.

A 30-year-old transgender New Yorker told me she has met four men in a year on the site, but that she’s picky and turned off by most males’ lack of courtliness: “A lot of guys here and on other sites seem to think they can send an email with a cock pic and a brief message like ‘Let’s do it,’ and I’m supposed to fall in line for them.” She also meets men through her work and in her neighborhood, but, like the Californian, enjoys the site’s filtering process. I asked if the online buffer emboldened the curiosity of straight males. “I’ve never had a problem attracting ‘straight’ men in the ‘real’ world—although it has to be said that how straight they are is always a question,” she wrote.  “In many cases, guys like TGs like me because they want to suck a cock without feeling gay.”

Despite the ease with which she pulls in partners, she’s “not here looking for instant NSA sex,” a sentiment shared by a number of women and even some men.  While it certainly has its share of randy members angling for one-night stands, the site’s name is apposite: It’s filled with a lot of adults who are, in the end, searching for a friend, lubricated or not.  As the lovelorn 52-year-old wrote to me, “The sad thing about happiness is not having someone to share it with.”  The same could be said, of course, about a raging hard-on.