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?

JS: They wanted to handle them or they wanted to compete with them. Sometimes they wanted penetration or forced feminization. Dress them up all slutty and take them out somewhere. Or have my male friend over. But yeah, there were a surprising number of guys into penises.

Some of my friends wondered why they didn’t just talk to a dude; there are male phone sex operators. I don’t know if it’s just easier to deal with that situation if you’re talking to a woman.

OMC: Maybe if they had the balls to talk to a dude they probably wouldn’t need to call in the first place.

JS: Yeah. And maybe they don’t really want to be with the guy. They just want the penis. Plus porn is just so fixated on giant penises. I don’t know if that’s part of it, too.

OMC: I could see that. Porn is so exaggerated most of the time.

JS: That’s the only thing I could figure out. If they ask me how many guys I’ve been with I know we’re not talking about me. "What’s the biggest d*ck you’ve been with?" OK, maybe we’re going to put you in a dress and we’ll see where it goes. Of course the d*cks all needed to be enormous and most of the time they had to be black.

OMC: Wow, so you’re dealing with a whole lot of issues there. I wonder if there is a way to unlock these issues and use them to create a more accepting environment. Use phone sex to fight homophobia and racism.

JS: Do you think of it as racism?

OMC: I don’t know. Maybe that’s too strong a word?

JS: I guess it could be. I mean, fetishizing another race is pretty racist. I’ve been propositioned by guys in my daily life before who say "I’ve never been with a black girl before." Then I know they don’t want to get to know me. They just think "She’s brown. I’m gonna go hit on her."

I had an Asian friend and she could tell who liked her just because she was Asian. It’s kinda creepy to be fetishized in that way. And the people who say that think that it’s somehow a compliment. "I’ve always really liked black women." OK? That’s a really strange thing to say to someone.

But it just became a joke to me. As soon as I would find out he wants to talk about a d*ck, I’m gonna mention a black d*ck and that’s where we’re going. Or sometimes they would confess. Something like, "I went to this truck stop, and ..." And then I’d start asking all the same questions.

It took a long time to figure out those hints they would give, cuz my training was a 20 minute phone call with another woman who had done it for a long time. She was at that stage where she was really angry, so all the guys were "jerks calling in here." She was very hostile and angry about it, so the training was like, "Well, you'll figure it out." She told me to get stuff to make sound effects and practice my accents.

OMC: Oh yeah, accents. I hadn't thought about that.

JS: Yeah, I'm really bad at that, so I got hung up on a lot. "You don't sound Asian." If they called for an Asian girl I’d just say I was adopted. (Laughs)

Then usually they’d be OK with that. Sometimes they’d hang up. I would have made a lot more money if I could do accents.

OMC: Is there anything else you couldn't or wouldn't do?

JS: I had a hard time with the "N-word." Racial degradation. Everything else would be fine. We could talk about bestiality, I'll pretend to be your mom, but you can't call me that word for 35 cents a minute. I got into a really big fight on the phone with a guy because he wanted me to say it and I wouldn't. We ended up getting into this argument while he was doing whatever he was doing on the other end of the line.

I was like, "You'd never be able to have sex with a black girl in real life!" (Laughs) I was super pissed off so I said no! He said, "I'm paying you, you have to do it!" and I said, "No I don't. I'm not gonna." So that was kind of fun.

OMC: Could he get his money back?

JS: He could have hung up and they would have given him someone different, but he didn't, so he must've been enjoying it on some level.

I got into an argument with someone else who didn’t think I was really black. "You don’t sound black."

I said, "We don’t all talk like that, you know." He said, "No, no no, I know you don’t. I’m just sayin’."

But what gets to me is that I understand. It’s part of the whole thing. If you want to be with a transvestite you don’t want one with a three-inch penis. If you want a chick with big boobs she’s gotta have unrealistically big boobs. I get it. But it’s still awkward.

I was also really bad at being a mean dominatrix and making fun of people and their small penises. As women we're taught to be like, "No, it's fine." You don't want to make fun of that, so it was really hard to break out of that. I had to get together with a bunch of friends and tell them, "Okay, we have to come up with a bunch of small penis insults."

OMC: I feel like that could have some real world applications.

JS: Yes! I can insult people a lot better and I don't feel quite so bad about it anymore.

But a lot of times when people wanted something that was weird and fetish-y, it wasn't really that bad. There were always people who wanted something that was relatively harmless but they would be super ashamed of it. They wanted to wear panties or something and would apologize at the end of the call. Really, it's not that bad, but I think about how difficult it is for that person to express that to someone they care about.

There was a guy who had a haircut fetish. He wanted to get his head shave and wanted his girlfriend to get her head shaved and had all these stories built around going to the salon and getting cut. And he told me he really wanted to do this but he just could not tell his girlfriend. He was so worried that it was so weird that she just wouldn't be able to deal with it.

OMC: Because you offered this sort of safe haven, did anyone ever get too attached to their imagination?

JS: There started to be guys who would call all the time and have personal feelings for these characters I had developed. Since I'm not great at lying and deceiving people I felt bad about it. They were all different characters and they all had a backstory with elements that would inform their personalities. This guy would call every Sunday and he was really nice and he eventually started saying he wanted to spend time with me off the phone.

But a friend reassured me that those people know that they're paying and they know it's a game and that it's not real so you have to separate the real you from your character. You can't feel bad for these people because they know what they're doing. You called a 900 number and gave someone your credit card information and said "I want to talk to this kind of girl," so everyone knows what's going on.

But you got paid more if you got regular customers. I had a journal so that I could keep notes so if a customer called back I could pretend that I remembered them. I had six characters and I’d put the guy’s name and when they called and what we talked about. Most things were pretty much the same, but if there was something different I could take notes and remember it.

OMC: Do you still have the notebook?

JS: No! I had a bed bug invasion and had to throw all that stuff away. Now I think, "Why didn’t I save the notebook?" It would be fun to go back and read some of that. I’ll go back and read my blog and remember things I hadn’t thought about in a while. If I had kept it I could put it in a spreadsheet and find out how many guys wanted to talk about penises.

OMC: Where are you from originally?

JS: I was born in Italy but I grew up here. My mom was Italian and my dad was in the army.

OMC: How long have you been in Milwaukee?

JS: Pretty much most of my life. 30 years or more.

OMC: Do you speak Italian?

JS: Yeah. My mom came here and she didn't speak any English and she also wanted us to know how to speak Italian. It was my first language, actually.

OMC: Do you speak it with an accent now?

JS: Yeah. My grandma always yells at me about it, but I guess my mom also speaks with an accent, too.

OMC: How was it growing up in Milwaukee?

JS: It was fine. When I was growing up there weren't a lot of bi-racial kids. Now it's not unusual to see a white person with brown babies. When I was a kid that wasn't the case so it was kind of weird trying to figure out where you fit in. Then I went to high school in the suburbs. That was totally different. All these super rich people. But I like it here.

OMC: So what makes you more tolerant and free compared to the rest of America?

JS: It's hard for me to separate what's real or what's culturally induced. But I've always been more sexually open or curious than a girl is supposed to be. I'm not ashamed of it, but there have been a few people who think I should be. Somebody on the phone asked "What's wrong with you that you have this job?" I just asked them, "Well, what’s wrong with you that you’re calling this number?" Then he hung up on me.

OMC: Were you religious as a child?

JS: No. I’m sure that helps. I mean, my mom would never talk to me about sex, but she was exploring a religion when we were growing up. When she lived in Italy she grew up super Catholic. Then she started to lose her faith, so we would go to alternative book stores and she would let me read whatever I wanted to about religion. She didn’t impose anything, just whatever I was curious about. Any time I had a question she encouraged me to read about it. Be curious about it. So I couldn’t necessarily talk to her about sex until recently, but she was open about everything else.

OMC: So it’s gotten better recently?

JS: Yeah, she’s a lot more open minded about things. But I think the phone sex was part of it. She would ask, "Really, you’re okay talking about that stuff?" So now she’s trying to be more open.

Now I don’t necessarily have the religious guilt part of it, but it’s more about how women should not behave this way. A woman should not think those things or say those things, so that part of it is hard to fight against. The first person I was in a relationship with was very prudish, saying something is wrong with me. I thought maybe there was something wrong with me. But then I went the opposite way. "No there’s not! And I refused to be ashamed of it."

I really wish we didn’t have these sexual hang-ups. I’m pretty vanilla as far as things go in my personal life but having talked to so many people who are not it made me feel bad because I’m thinking about all of these unhappy and unfulfilled people running around who have to pay to tell someone that they like to get their head shaved. It’s so unnecessary. It’s really sad.

As long as you’re not hurting anyone who doesn’t want to be hurt, do it. I talked to someone who lived in the south. He was black and he was into these slave re-creation scenes. He would get together once a month with these people and re-enact a slave trade and put him up on a stand. It was horrible. I punched out and I cried but that’s what he likes and that’s what he wants to do. And just because I think it’s awful doesn’t mean he shouldn’t be able to do that. He’s in a safe environment with people he trusts. If that’s what he wants to do he should have the freedom to enjoy that.

OMC: Was there a dress code on the job?

JS: (Laughs) When I first started I was like, "I’m going to get up and take a shower and I’m going to get dressed like I’m going to work. Turn off the TV." But eventually I wouldn’t even get out of bed. I’d just put the phone next to me. It didn’t really matter. But eventually I’d just have to leave. Just go outside. The job was usually fun and funny, but there were things that were difficult to deal with. It was nice to be able to write about it and have people to talk to about it, vent and get it off my chest.

OMC: Do you miss the job?

I think about doing it again because it was fun. That was one job that I felt good about because I felt like I was doing something good. I knew that I was making people happy. I had proof! But it just paid really poorly. I was able to do it around work and school, so that was nice, but some days you’d have to punch in and just be on call for six hours and not get any phone calls.

OMC: Does your past experience inform your current on the job abilities?

JS: Yeah. A lot of the jobs I've gotten after that my bosses have commented, "You're really good on the phone." It always makes me laugh.

You can read further about Stuart’s exploits on her blog, Tasting Caterpillars.