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Milwaukee's Daily Magazine for Wednesday, July 30, 2014

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Unlock your imagination.

Getting down to it with a phone sex operator


When you think about the sex industry you might immediately think of the billions of videos and the billions and billions of images that populate the web. But what about phone sex? In a world where porn is easier and easier to find, is there still pleasure in the imagination?

During a casual night out with friends we started a conversation with a couple of strangers. Everything was very typically friendly until one fuel-filled sentence sparked an exciting interview.

"My friend just likes to blurt things out about other people to inspire conversation," said Jessica Stuart, who, during a lull in the conversation, was outed as a one-time phone sex operator a few years ago. Stuart asked her name be changed for the story. "She does that at parties a lot. Then she'll leave and let the other person tell the story."

Wow. My mind reeled. After an initial, fascinated barrage of questions we decided to move it to a quieter place a few days later. Under these circumstances it was easier to hear Stuart's sweet and confident voice. The conversation was strictly business, but it's not hard to imagine that she was probably good at her job.

OnMilwaukee.com: How long ago did you stop dialing in to work?

Jessica Stuart: What was it: four or five years ago?

OMC: How big is the phone sex industry?

JS: You know, I don't even know. There are books and stuff out about it, but I don't know any statistics. That's a good question, though. I've never really even thought about it.

OMC: It didn't seem like something to ask when you started?

JS: No.

OMC: OK, so with the Internet … phone sex is still a thing?

JS: It is! I don't remember the numbers, but there were several larger companies you could work for. The owner of my company, she had been doing it for 20 years. She was very successful. I don't even know how many people worked for my company, because we all worked from home. Every once in a while I'd talk to (another co-worker) on the phone, if somebody wanted to talk to two girls or whatever. Other guys every once in a while.

OMC: Was your service advertised late at night on TV?

JS: There was a chat-line number and there were a bunch of different lines that were in the back of magazines and porn site ads.

OMC: So you have no idea how the industry is holding up without you?

JS: I imagine it's doing fine. I was really surprised by how many people there were and how busy it would be for me sometimes, because there's internet and the internet is free. But people would just call to talk. They wouldn't even be talking about sex necessarily. Some people were just lonely. But it works differently than the internet because you have someone to talk to and to create the story with you.

OMC: It seems like it would be more interactive. More imaginative.

JS: Yeah, because with a lot of people I wouldn't even necessarily need to talk. They would just tell me a story.

OMC: So how did you get into becoming a phone sex operator?

JS: Well, I was on a message board of maybe 30 people or so. We used to have people come on who had an interesting life and we could ask them a bunch of questions. We talked to a monk and a LARPer and different people like that. One girl came on and we got to ask her a bunch of questions about phone sex. I wasn't working at the time so I thought, "I'm gonna try it."

OMC: So you just heard this and thought, "This is a good idea."

JS: Yeah, and the guy who ran the forum told me it would be cool to write about. He was trying to get a collection of different sites where writers would write about whatever they wanted. He was always trying to get me to write. He said, "You can get this job, make some money, write for this website." So I kinda got talked into it. But I wasn't working and I did think it would be interesting to try.

OMC: Is this part of your personality? Are you an adventurous person?

JS: No, no, no. Not at all. I've always been a goodie-two-shoes. I don't like to take risks. I'm very straight and narrow. And that was part of it, too. I've never done anything like this before, but it was anonymous enough that I thought that I could do it without worrying about it too much.

OMC: How bad was money for you at that time?

JS: Very. My mom was helping me pay my rent. It was really bad.

OMC: Did you make any friends on the job?

JS: No. There wasn't really anyone who I wanted to talk to and get to know in real life. People were calling from all over the place and we weren't allowed to do any of that even if there was.

OMC: No co-workers either?

JS: No, you know I never really got to know my co-workers. There were the secretaries that I would talk to when they were setting up a call. I don't even think they used their real names, so everything was pretty anonymous. Even if we did a team phone call I never really knew that person's real name. Because they would be like "You're going to be on a call with Diane" but then I would think, "Wait, I thought you were Brenda."

OMC: So what was it like the first time you told you mom, "Oh, you don't have to pay my rent this month?"

JS: I lied and told her I got a job in a call center. After my first day she called and was asking all these questions, like how many people I work with, what my boss was like. I couldn't answer because I'm not a very good liar, so I started crying, "I've been lying to you this whole time!"

But she laughed really hard. So if my mom was okay with it, and my brother already knew about it, it was fine. My stepdad just said, "Just keep in mind you're only talking to a small percentage of the male population." And that was pretty much all they said about it.

OMC: Nobody tried to talk you out of it?

JS: Most of my friends thought it would be interesting, but there were a couple of guys who said I shouldn't do it. "It's going to mess up your head, it's going to screw up how you interact with people, it's going to interfere with your personal sex life." My stepdad asked if it was going to make me feel bad about myself. All of the guys were worried I would listen to something that would be so terrible that I would be scarred for life.

OMC: I kinda want to ask those guys, "So ... what are you into?"

JS: (Laughs) Yeah!

I was also single at that time, and people who I would be interested in dating wouldn't want to talk to me. It was a weird jealousy thing.

OMC: Do you have any advice for anyone?

JS: You start to see patterns, like the code words people would use. If they were into something taboo they wouldn't feel comfortable coming out and saying it. There would be certain indicators. They would ask for a "motherly type" or if you were older they might start asking about your kids. They became indicators of where it was where it was going.

If they wanted to talk to me, they would ask about my measurements or ask what I looked like. If they didn't ask about me then these codes would lead me into the direction they wanted. We couldn't talk about any kind of underage activity ... unless the caller was an adult baby.

But I swear half the guys I talked to wanted to talk about d*cks.

OMC: Uh ... explain?

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