Notes from a Working Girl

We fear what we don’t know. But I believe enough fear exists already, meaning we as a society need more understanding, more knowledge of each other.

In this series of interviews, entitled Wholesome People, we’ll explore perspectives not often heard in mainstream conversation. The hope is to find commonality between people who may at first appear wholly different, in the interest of bringing us all closer together.

Now, please open your mind . . . and enjoy.

It feels fitting to start this journey with a woman who works in the oldest profession, as they say: sex work. I met her through a friend of a friend. We talked over chips and salsa at a popular Mexican restaurant in downtown Boulder, Colorado. For obvious reasons, I’ll keep her identity anonymous, and be warned that this interview contains adult themes. Beyond that, let’s have her tell her own story . . .

I met a guy on Tinder who paid me to kick him in the balls. That was a fun thing, I guess. And it just grew from there. I’ve always been a very hypersexual person. Nobody was shocked when I told them, which was weird . . .

I’ve always struggled with that. I generally say that I have sugar daddies because I am more in that sector of sex work. Compared to, like, escorting, having sugar daddies is a lot more about creating a relationship with these guys beyond the sex. It feels like we’re dating, but then I leave and we don’t talk and they get the perks of dating someone without having to take care of a relationship or caring about another person’s life too much. You get a girlfriend when you want it, which I think is very nice for people.

Like I said, I think some people want that connection with someone without having to maintain a relationship. A lot of people work from home nowadays and that makes it hard to meet people. I can be there. Other people are really socially awkward and might find this easier than dating. And then some people are just really busy. That’s a common thing. Sometimes this kind of thing can just work well for people in their life.

It depends on the dynamics. Some people just want to hang out, watch a movie, or get dinner and go on dates and it feels more like fulfilling that crave for real connection. When I first started, I was more escorty than sugary and that was always just about the sex. We would meet in a hotel room, have sex for an hour, and then go our separate ways and just meet up again whenever. With sugar dating, I think it is more about the emotional connection than just the sex, but the sex is also a big part of it.

Okay, so I used to work at Dutch Bros. Coffee and a big thing they always talked about was, like, your job is to brighten someone’s day, be the bright spot of someone’s day. So I would really connect with these people who I would see for two minutes every day. I got really good at building connections that felt really deep for the other person. But I also have a certain level of just, like, love for people. I really do care about people a lot.

Totally, big people pleaser. It is genuine, but not so much that I’m bent out of shape if we stop seeing each other tomorrow.

From stories I’ve heard, it’s very common for guys to fall in love, you know, because you’re basically pretending to be in love. Like that’s the dynamic. But I like to think that I’m pretty good about setting those boundaries early on, and maintaining them, and being set in what I actually want.

At the beginning I really wanted to have sex with older guys, so I’ve been with people in their late 60s and even their early 80s, but generally I’d say people are in their 40s. Most of the men I see are married or in a relationship of some sort. I think the biggest reason people come to me is because they’re unhappy in their marriage and not getting any intimacy, but still want to stay for whatever reason. And I think it can be good for these guys because someone like me isn’t really going to be in their life—I guess I’m the safest person to cheat with.

Then some people I see just don’t really know much about sex at all, like how to do it or what to do, because they haven’t had much experience. So I’ve definitely had people learn through our interactions. I try to create a very open space for people. Like, I don’t react too much when people tell me things, because I want them to be able to just keep talking and not feel like I’m judging them.

I just try to create a safe space, a comfortable space, and fill the role that they’re looking for. And I think that comes from when we talk initially, because that’s the purpose of the interaction. Then creating a space where they feel loved and making sure they feel cared about afterwards and don’t feel like I’m judging them for anything, because there is definitely space to judge, you know?

For sure. As much as it sucks, I think that’s a big part of sex work. If you are wanting to get into it, you have to know that’s a risk. Because when you’re around men in their most primal—sometimes their worst setting—they aren’t always viewing you as much of a person, you know? And you can definitely be put into some pretty uncomfortable or even dangerous situations.

But I have enough people who I talk to frequently throughout the day that I feel like it would be noticeable if something happened. So I’m careful. People have my location and I’ll text them when I’m safely there, and then as soon as I get to my car. And if I don’t then there’s something wrong. And I heavily check people out online. It’s so easy to find out a lot about people.

Yeah, when someone’s just regular weird or, like, too weird, I feel like I can gauge that. But sometimes you think people are going to be really weird and then they’re so sweet, just a little strange. I feel like the weirdest people I’ve met are the ones who seem the most normal at first.

Yeah. It has been for a while.

I’ve heard of people making up to $10,000 per month.

Yeah, I’ve gone a ton of places. Iceland and London, Italy, and Amsterdam . . . Vegas a couple times. New York a couple times. LA a couple times. It’s been awesome. But most of that travel was with someone who I was seeing consistently.

I’m really struggling with this question, because I always thought I had a good handle on it. I’ve always tried to focus on the positives, but I recently had a negative experience that has made me reconsider my ability to balance it all. I apologize for this story, but a couple of months ago I went on a trip with someone who I trusted, who I’d been seeing for around a year and half, and while on this trip he totally took advantage of me. I completely shut down when I got home and just the thought of sex repulsed me. I had always been a very sexual person and now I’m not. This sort of work can be life changing and glamorous but sometimes that’s not enough to balance the negatives and the risks that come along with it. At least I don’t know if I can balance them anymore.

I would tell her to be careful, to not get swooned by the quick money. You can definitely get stuck in this kind of work and it’s important to be cautious that you don’t. I think it’s important to know the risks, and the impact this sort of work will likely have on your view on relationships and people in general.

I’ve seen so much cheating and, unfortunately, been a part of it so many times that the concept of marriage and having one partner forever seems impossible to me now. Which, maybe it always did, but this work definitely confirmed it. The money is charming but it doesn’t always feel worth it.

I’ve always viewed sex work as a good thing, for the most part. Because people need connection and I think you can’t really hate on how someone’s going to find it. Everyone deserves to feel cared for, and I can provide that. It’s just a service, like any other service, you know?

If you’re anything like me, some of these ideas are challenging to consider. But I’ve long thought that the beauty of hearing things which challenge current belief comes from the possibility that: one, you discover ways to expand your perspective, or, two, you find even more strength in your own convictions. Either way, it seems beneficial.

So, I hope you find either new perspective or deeper conviction in these words.

Until next time . . .

Martin

If you are interested in reading more of my work, I recently published a book of essays about staying human in the algorithmic age. You can buy it HERE.