What Being a Phone Sex Operator Taught Me About Lonely Men

My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your “first time” is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that’s how sex stays fun, right?

This week, we’re talking to Angelica Whyte of chat line 1800-PHONE-SEX about her first time working on a phone sex line. You can catch My First Time on Acast, Google Play, Apple Podcasts, Stitcher, or wherever you get your podcasts.

There’s a reason I’m good at phone sex. It’s because I’m pretty straightforward. I try to sound real.

I got into phone sex when I was working as a makeup artist in a strip club. One of the dancers there told me about how much money she was making, working from home, and that kind of sold it for me.

I was 20 when I started, and I’m 24 years old now, so I’ve been doing it for four years. Thinking back to when I started, I had no expectations of it. It took me a few weeks to understand it and start making money.

The first time I ever had phone sex, the guy said, “are you open-minded? Will you do anything for me?” I replied, “of course.” Then he asked me: “I want you to blow dry my ass.” He got on all fours, and I grabbed my hairdryer and turned it on. All the while, he wanted me to talk dirty to him.

Afterwards, I was disgusted and confused. I wasn’t expecting anything like that. But then I thought, they’re calling a fantasy service for a reason. These guys can’t tell anyone about their fantasies in real life, not even their partner, because they’ll get the reaction like—what is wrong with you? Then I started to understand it a lot more. When I first started doing phone sex, I was quite timid and closed-up, to be honest with you. Now I’m not just a phone sex operator: I’m literally a therapist. These guys open up to me about everything.

Guys don’t just call in for phone sex. They’ll open up about their wives cheating on them; or how they got fired; or how they never see their kids after their divorce. They have nowhere else to go to express how they feel. Sometimes they admit their faults, and other times they just blame other people. I always just listen and am sympathetic. I say, “I’m so sorry you’re going through this, but there’s always a light at the end of the tunnel. You’re not going to be alone. You’ll find the perfect person for you.”

When a guy calls the service I work for, they pick a different call tag based on their fantasy. It might be “Barely Legal,” or “Anything Goes.” And you base your character upon the tag they’ve selected. Say a guy calls and it’s the “Barely Legal” call tag, the first thing he always asks is how old you are.

So I say something like, “Can I be honest with you? I just turned 18 literally two days ago. My parents are on vacation and I’m a spoiled brat. My friends call this service sometimes and they always tell me about how amazing it is. They get to talk to so many mature guys! So I decided to call in and have some fun. I really don’t know what I’m doing right now, but I hope you don’t mind.”

Some of the guys I talk to are aggressive. They downgrade you. They’ll say, “You’re a slut, you’re a bitch, you’re nothing, you’re just a woman.” But there will also be these callers who are incredibly sweet, and will tell you how amazing and sexy you are.

You have to adapt to their fantasies, and you can’t give up. It’s the same as any job. Most calls are just normal phone sex, but sometimes guys get really creative with their fantasies. Like Jim: he wants you to have his babies. He wants to describe, in detail, how he’s going to get you pregnant. It doesn’t matter if you’re 18, 35, 60, or 80. He wants to get you pregnant. He wants to spread his seed in every woman. He wants 500 kids. Or there’s Tiny Tim. He wants to be humiliated. He wants me to tell him how small his penis is. I have to say, “That’s disgusting. How are you going to satisfy me with a one-inch penis?”

The most important thing is to think on your feet, expect the unexpected, and not get stuck. For example: I had one caller who wanted me to pretend I was a fat squirrel, jumping from tree to tree. I thought, what on earth does a fat squirrel sound like? So I said, “Throw me a nut. Feed me. I’m always in your backyard, looking from tree to tree to jump to, because you feed me.” That got him off for 45 minutes.

You have to separate fantasy and reality. Twenty percent of the time, I get into the call and do enjoy it. You can get really sexy guys on the phone who want to pamper you with words and pleasure you. But the other percentage, it’s just fake orgasm. If there’s an 80-year-old on the phone you can barely understand, you can’t get into that. So I pretend.

I make between $1200 and $1400 a week. You need to set yourself a structure and routine. If you don’t, you’ll get distracted. It’s all about trying to hold them on the phone for as long as possible. Milk every call. The longer you hold them on the phone, the more money you make.

Experiencing all the different types of personalities you meet through phone sex does really affect you. At the beginning it bothered me a lot. I’d be at the grocery store and I’d start profiling the men I saw. I’d think, is this the guy who thinks about having sex with someone underage? Is this the guy who wants to rape women? Is this the executive who fantasizes about being penetrated with a dildo in his office?

After a while, I realized that these guys probably didn’t want those things in real life. It’s just talk; a fantasy. I stopped over-analyzing things and judging these guys, and started opening up more. My personal life got better, too. I became more comfortable with my sexuality, and kinkier. I’m more open-minded now.

Doing phone sex made me realize that we’re all just playing characters that are suppressed inside of us. I feel like I’m doing a service for society. Because I’d rather these guys came on the phone and acted characters for me, then they had nowhere to go, and they suppressed it, and it boiled up. At least this way, they release the steam.

I’m playing a character too. But the difference is, I’m just doing it for the money. They’re paying. I play along with the fantasies they come up with in their head. I’d rather they opened up to me, then did some of this stuff in real life. So I say, “talk to me.”