Operators reveal all to photographer Phillip Toledano about the needs and desires of their customers—and why eating a peach mimics cunnilingus.

“Just last night I received possibly the most disturbing phone sex call I’d had in a long time. A caller shot himself with me on the phone,” a middle-aged phone sex operator, who lives her life in an electric wheelchair, revealed to artist and photographer Phillip Toledano.

Her experience is recounted in Toledano’s book Phonesex, which captures more than two dozen men and women who live their daily lives as phone sex operators.
“The unmistakable sounds of a gunshot,” she continued, “followed by the heavy and wet sound of a body falling with a thud to the floor. Things like this always scare me.”

It’s not a story you’d immediately expect from a phone sex operator, especially since the occupation allows callers to play out their wildest sexual fantasies without fear or judgment.

You’d assume a comfortable escape from the stress and pressure of everyday life; a thing of pleasure rather than a moment to take one’s life.

But at that point, the woman’s track record stood at three suicides. She’d also experienced a “confession of incestuous sexual abuse.”

The suicides are by far the darkest confession in Phonesex, though others detail bizarre accounts of callers wanting women with super strength, fantasies of becoming the size of a tampon, and desires of being emotionally dominated.

A brunette who seems to be in her mid-twenties recounts in the book how a client, Gary, was watching a “World’s Strongest Woman” show when he called in.

To play into his fantasy, she casually suggested that she could easily pick up a motorcycle.

He begged her to lift his girlfriend’s car, a Mazda Miata, with her inside. He became “breathless,” playing into every word she said. “A part of me may miss getting paid for this when I move on,” she’s quoted as saying.

Other guys prefer a female operator who is more emotionally dominant and in control.

A young woman with pale skin, jet black hair and bright red lips talks about how her callers want “total denial of release.”

“Some want to be forced to be in chastity,” she’s quoted in the book. “Others get off hearing a bossy (and sometimes bitchy) woman tell them they are pond scum.”

“Some call it odd. They call it kink. I find that most of my regular callers form some sort of bond with me—almost an addiction. I am the one they come to for punishment if they feel the urge. The one they come to for discipline, instruction, and permission. I am their drug.”

I feel like I teach them how to please themselves, by telling them where to put their hands, and how to stroke themselves. It still gets me horny.”
The most sickening of all the stories was from a guy who wanted the male phone sex operator to sleep with his girlfriend.

Not only that, but he wanted him to “cum on the baby,” the operator is quoted saying in the book, then “cum on his girlfriend’s tits so the baby could eat it,” he added. “Usually these guys get off on being told what a loser they are. Not this guy.”

The operators do it for its monetary value—to help out family members in need or to escape abusive relationships. Some love acquiring the mental strength it takes to adapt to each new fantasy, while others find empowerment in finding their own sexuality.

“To be a phone sex operator, you’ve got to be incredibly smart and have such an incredible, vivid imagination,” Toledano told The Daily Beast, admitting his own surprise at seeing the people face-to-face after creating an image in his head based on their phone conversation.

“You have to be extremely mentally elastic so, when someone calls, you can hear what they are and are not asking for. Then, you have to create this very believable world within minutes. It takes incredible interpersonal skills to do that. And you’ve got to be very intuitive and empathetic.”

It’s a set of skills the artist saw a vague familiarity in.

After his mother suddenly passed away in 2006, he was left to care for his 95-year-old father who suffered from dementia and had no short-term memory.

Multiple times a day Toledano’s father would forget that his wife had passed and constantly re-lived the pain and suffering a death can bring. So Toledano was forced to create an illusionary world.
“I decided that it was my job as his son to make his life and our life together as full of joy and have as little pain as possible,” Toledano said. “So I created this fiction between my father and I that my mother had gone to Paris to take care of her sick brother.”

This idea of an agreed or complicit illusion between people really stuck with Toledano and led to the formation of Phonesex, which touches on the relationship between “two people who call each other up and agree to participate in an illusion together for a certain amount of time,” Toledano believes.

So, he put an ad on Craigslist and was thrust into the tight-knit community of sex phone operators. Not only was he seeking to know about them and why they did it, but he also wanted to capture the profession before it eventually gave way to more sophisticated technology like webcams.

“Once I got into it, it became utterly fascinating,” Toledano said. “Every kind of person did it: there were NYU students, mothers, women who were saving up to escape abusive relationships. And one of the most surprising things to me was that there were men.”

Toledano found that roughly a quarter of the operators who reached out to him, or he was introduced to, were men. And, in retrospect, he realized: “why wouldn’t women want to call up and have the same experience?”

But there seemed to be a big difference between how the two sexes viewed their positions.

“For the most part, there was kind of a sense of power with the men,” Toledano said. “It was more like a sense of accomplishment,” while the women find empowerment for themselves.

For instance, a pale-skinned Latin man who holds his pet Chihuahua boasts: “They want me… They want me to talk to them and to take them to another world. I’m good at it. I’m a pro. A ladies man… They want me to meet up and have my way with them, but I keep it only to phone conversations.”

Another guy brags, “I share myself with individuals who’re not getting what they need at home. I feel like I teach them how to please themselves, by telling them where to put their hands, and how to stroke themselves. It still gets me horny.”

He’s also perfected the art of sound manipulation. Knocking a chair against a table resembles a bed rocking. Tapping two fingers against the mouthpiece mocks “the sound of your dick slapping against the phone,” and eating a peach mimics cunnilingus.

One guy, who has been working as an operator on and off since he was 19, crows that “most callers are impressed with the way my tongue can balance their hot cocks, mind, and soul. They don’t expect it, yet they embrace it.”

Women, on the other hand, seem to focus more on how the job has helped them grow and become more comfortable in their own skin.

A woman who poses shirtless, reveals how being a phone sex operator has increased her “self-esteem so much, knowing guys are looking at my pics and wanting to talk to me. Wanting me to take them to a whole other place, filling their fantasies… painting that picture in their minds for them.”

Another discusses how she discovered herself and her sexuality through the job.

One of Toledano’s subjects has earned enough money to escape an abusive relationship.

She had “no way in the foreseeable future of getting out,” the book details. “Then a regular customer of mine sent me a very NICE tip and along with my income tax refund, I put it all together and was able to relocate and terminate that abusive relationship.”

“If I didn’t work this job… I could have been killed by that man,” she reveals. “I’m getting paid to talk to all kinds of people and deal with their fantasies, as well as delving into my own. And you get tips and gifts.”

“Everyone has assumptions about life,” Toledano said. “I went into this not knowing what to expect and I certainly did not expect what I got. I found it really gratifying to know how smart and skillful these women had to be to do what they did.”