Gender-Hacking on OkCupid
I had just graduated from college in 2010 and was trying to navigate dating in the real world. So, like everyone else in my age bracket, I went on OkCupid.
Here’s the thing about OkCupid—before you can even fill out a profile, you’re asked for your gender and what gender you’re interested in. Which, yeah, makes total sense for a dating website, sure. But at the time, this wasn’t simple for me—I wasn’t really sure what gender I fit into. In college I had always identified as a butch lesbian, but I had recently started coming to terms with the fact that I might be a dude in a woman’s body.
I didn’t want to let this confusion limit my dating opportunities. So I came up with the following solution: I set up two essentially identical profiles—one as a woman looking for women, one as a man looking for men. I had always identified myself as queer, so it seemed logical to stick with what I knew. Both profiles included the same picture and the same answers to all the questions (more or less). Neither mentioned anything about my gender; I let people figure that one out on their own, just as I was trying to figure it out on my own.
Looking back now, this was the first time I had ever confidently presented myself to the world as male without apologizing or explaining or worrying what people would think. So when I went to check the activity on OkCupid a few days later, I was delighted to see I had roughly the same number of messages in the inboxes of both accounts. And not a single one of them said anything about my gender; they just accepted me for whatever I’d said I was. Man, it felt great.
—H. TUCKER ROSEBROCK
Total Web Cam
I worked in a house of domination in 2008. Men (and a few women) who had seen my videos (I’ve been working in porn since 2000) would call the house to make an appointment, booking hour-long sessions for just under $200 a pop.
My clients came from every socioeconomic class and had a wide variety of desires. In the dungeon, I made my money like a diner waitress (which I’d also been)—get them in, get them out. Some got straight to the point, like the construction worker who showed up once a week on his lunch break to touch my bare feet and jerk off.
But most of my clients wanted more—they wanted to understand. A regular once asked me, “How do you know if love is real?” I thought, “Lord, where do I begin?”
Once, a man booked a session with me and then claimed he was a Broadway producer—he said he’d flown into town because he was a longtime fan and wanted to meet me. I said, “Sure you are, now get on your knees.” For the entire hour he insisted, saying, “Look me up, I have a Tony.” Usually when a client left I’d close the front door quickly, but this time I watched him walk to the curb, where a uniformed driver ushered him into a limousine. Later I found his face in The New York Times.
That was when I started to realize I was not maximizing my earning potential. In the seven years since, the Internet has revolutionized virtual one-on-one encounters. For a number of reasons—faster home Internet connections and a rise in video content piracy, to name two—webcam shows have skyrocketed. In 2013, my coworker Maitresse Madeline combined the webcam with the Internet auction. She invited me to auction off a single hour-long webcam session. I was excited by the prospect of reach—the winner of the auction could be anyone, anywhere.
The week of the auction, we posted a video of me challenging my fans to make a bid. We watched the numbers rise to $2,000, then $5,000, then $10,000. I didn’t dare believe it was for real. Every good sex worker knows: Don’t count the money until it’s in your bra (or G-string or boot).
The final bid came from an Australian man. A few weeks later, he sent the payment: $42,000. He had paid the same amount for an hour with Madeline months before. (He still has not booked the shows.) To celebrate, Madeline and I scheduled a photo shoot, throwing all $84,000 in cash on the studio floor, dressing up in latex, and rolling in it.
—LORELEI LEE