OK, Cupid: The dauntless, complicated life of a webcam performer

Caleb is a young, sweet-natured 20-something with a resumé that probably doesn’t look like yours. He started web performing — or “camming” — a while back when the bills were stacking up. He was living by himself in a trailer an hour outside Oklahoma City, going to school during the day and looking to make some quick and easy money in the evenings. Unlike a weekend shift at Chili’s, Caleb wanted something that would allow him to express parts of himself he usually kept very hidden.

“I started cross-dressing when I was 5 or 6 years old. I did it in high school secretly,” Caleb said. “But it wasn’t until I started camming that I realized I had an exhibitionism aspect of my sexuality as well.”

Web performance, like many jobs in the sex industry, flips around the arc of relationships. Typically our sexual selves are the last thing we reveal to a stranger. Here, it’s the first.

First, let me claim my ignorance. Before I talked to Caleb — and Sierra, whom you’ll meet later — I had no idea what a web performer does. I think I might have seen an episode of MTV’s True Life about online sex workers back in high school, but other than that I was clueless.

Turns out, all you need to be a web performer is a webcam and a few documents that prove you are of age.

“It was strikingly easy to start doing it,” Caleb said. “You fax off a photocopy of your driver’s license and social security card, and it is all done in the span of a day.”

But that’s about the only part of it that’s simple. Cam sites are set up sort of like chat rooms. I took some time to try and find my way around one the other day — for, you know, research. I saw how difficult it would be to try to draw attention to yourself out of the hundreds of users on the site.

Success doesn’t come quickly, though many of the users might. (Pro tip from Sierra: The simple application of a Post-it note over the user viewing your show allows you to avoid watching those instant ejaculations.)

Rules of the game (or lack thereof)

A typical night for Caleb started with a red Solo cup full of whiskey and coke. He figured he would do well as a web performer, and he always knew he was an attractive person. With long hair and no facial hair, he is able to pull off an androgynous look that liquefies so many of our sexual identities into a fluid mess. But even at the height of his camming career he was barely able to pull in a few hundred dollars a week.

He defined his sexuality and gender as something that “will probably always confuse” him. At one point in our conversation he misheard the word “despise” for the word “disguise” and responded that he didn’t know exactly if he hated being a man or not.

The whole experience is incredibly casual. You work when you want to, you make some new friends, and you live out a few of your sexual identities that never get to leave your bedroom, yet stream out freely through that series of tubes we call the internet.

Sierra, a female web performer in her early 20s, was born and raised in Oklahoma and currently works two jobs while going to school. Camming is something she does at night when she has the time.

“I was falling behind on bills and I had done some nude modeling in the past,” she said. “I wanted a new experience. What I do is perform a show. Sometimes I show my body and masturbate, sometimes I have an honest conversation, sometimes I just talk about Zelda.”

Both Caleb and Sierra talked about how much time and commitment you have to put into this to see a significant cash flow. Sierra even mentioned she had seen girls who just sleep on the webcams and receive tips. I cackled when she told me this. Falling asleep in front of my laptop and people paying me is hands down what I wish I was doing with my life right now. Lord knows I got all the training I need for that career while I was in college.

Though both of them highlighted uncensored self-expression as one of the benefits of camming, it was also pretty clear that alcohol was a tool for them to fully let go of their inhibitions.

“One guy asked me to sing topless,” Sierra said. “I had to get wasted for that.”

On a small level, I get this. The closest I have gotten to web performance is sending some generously shared, R- rated snapchats after a few glasses of wine. I think that somewhere inside all of us, there is a freaky little thing that needs to get out, and if a mixed drink is the key to that lock, so be it.

Unfortunately, since we are talking about the untamed world of the internet, there are no rules here. If you are inviting one freak to come out and play, then you have to invite them all, and some of those freaks aren’t so nice.

“Some guys have certain fetishes that are too creepy,” Sierra said. “They want to be your daddy and you are the daughter. I won’t do that.”

But it is clear that the real fear is not how kinky the requests may be; it’s being discovered.

“I used to wear a ring on my left ring finger and a guy once told me he could help me,” Sierra said. “He said he knew I was just a desperate little housewife. And then he said he lived in my town, and mentioned my small town by name. I stayed away for a few weeks after that.”

Caleb is out of the game now. It was really just more of an outlet for him than anything else, but he knows the rules: What happens on the internet stays on the internet forever.

“I think about if I wanted to run for political office that it would come up,” he said. “But is it wrong to think that if it did come up, that I wouldn’t think it was a bad thing?”

Is it? The whole appeal of performing is expressing yourself in front of an audience, showing the world who you are and asking them to watch. The general public is probably not ready for a politician with a history of performing sexual acts on the web for money, but we might not be that far away.

IRL

The chat rooms are less about intimacy and more about blatancy, a fact that is hard to share with someone you are intimate with in real life. Relationships require honesty and keeping your webcam life a secret from your significant other would be a dealbreaker.

“My boyfriend was really cool with it at first,” Sierra said. “He said it sounded kind of hot. But lately he has started getting jealous and having moral issues with it. I can see why: I am making money and enjoying it.”

She asked him if he wanted to join her on a session, because couples can make more money and it might be a good way to show him what exactly she does. If she spends at least 6 to 8 hours on there every night, she can make between $200 and $300 a week. She can flip a switch and become another person, ready to please the crowd. But it gets exhausting after awhile, like all jobs do.

I had to ask if she was actually achieving an orgasm in front of strangers. Hilariously, she told me it is just like sex in real life, you often have to fake it. She requires that those who pay to “take her private,” which means they have a one-on-one chat outside of the public room, have to have their webcams on as well. She does this as a means of protection; if she can see them, she feels a little safer, with less of a chance that she is performing for her mother.

The first thing Sierra’s friends want to know when they find out she cams is if they can watch, but she never reveals her stage name to them or even what website she’s on. And if they have a problem with it, then she doesn’t want them for a friend.

“People have told me that at least I am not in strip club where people could touch me,” she said. “They seem supportive in person, and then judge you in private.”

These performances have allowed her to find what she is into, but above all it is a job. She said it was common practice for girls to not charge other girls to watch, though she doesn’t abide by this rule. If you want to see her, you are going to have to pay. And, by the way, taking off her panties will cost extra.