This is a slightly longer version of an article that was originally published at Role/Reboot. It also appears in my new collection, The S&M Feminist: Best Of Clarisse Thorn, which you can buy for Amazon Kindle here or other ebook formats here or in paperback here.

* * *

Previously on Role/Reboot, we ran an interview with my friend Olivia, a 25-year-old graduate student who had just started having sex for money through a “sugar baby” website called SeekingArrangement.com. In the interview, Olivia covered a lot of topics. She mentioned that she usually feels powerful in her relationships with her clients. As she put it, “When I show up, I don’t feel like — here is this rich, powerful person who is about to bestow wealth upon me. I feel like — here is this person who is a bit sad and lonely, and maybe I can make their day better.” Olivia also noted that her negotiations can be delicate, because some men are quite squeamish while discussing money. And she explained that she’s married — but it was already an open relationship, and she doesn’t see having sex for money as different from the other kinds of sex that she and her husband were already having with other people. To deal with it, they’re sure to communicate clearly. As Olivia said, “We just have to talk about it.”

In the months since that interview, Olivia and I have hung out occasionally to talk about her experience with sex work. She’s traveled across the city to meet me, and often bought me coffee; non-judgmental social support for sex workers can be rare, and I’ve seen more of her since she started the job. Although she really enjoyed the work at first, there were tough times too, especially after the novelty wore off. Recently, Olivia decided to stop seeing clients. We talked it through and she gave me permission to write about it. (She also reviewed this article pre-publication.)

Obviously, there were logistical complexities from the beginning. Taxes were a nightmare. Olivia wanted to pay them, but it’s not the easiest proposition. Then there was the question of paying off her debts. Some were simple enough, but then there were loans co-signed by her parents, and there was no way she could make any headway on those loans without talking to her parents… so Olivia had to maintain the fiction that she couldn’t pay.

That was nothing compared to the complexities of feelings and communication, though. I’ve already shown you how hard it was, sometimes, for Olivia to talk about money with her clients. There are other, subtler problems that are hard to handle with empathy: for example, creating the Girlfriend Experience persona.

I’ve talked to sex workers who enjoy creating a “sexy dreamgirl shell” on behalf of their clients. One of them said to me: “I create that persona for my boyfriends anyway. It’s nice to be paid for it.” But as a feminist sex writer who’s spent years working to understand my own sexual authenticity, this freaks me out a bit. I think it would feel terribly toxic and inauthentic for me.

It often felt inauthentic to Olivia, for sure, and that got harder and harder. “These men are very invested in believing that I’m super into this,” she told me once. “I have to keep up the front, and make them feel like I’m interested all the time. It’s literally my job to do that. When they tell me how happy I am, or when they inform me that I’m enjoying myself, I can’t really contradict them, even if it’s not true. Some of them use words like ‘magical’ to describe me, but the person they’re describing is not really me. Sometimes I think these guys pay me because in a non-professional relationship, a woman might push back when he says those things. She might contradict his idea of her too much.”

In fairness, Olivia naturally fits one glam stereotype of the middle-class sex worker: the sexually adventurous young student. It’s such a widely-promoted stereotype that experienced sex worker activists speak derisively about it, and some escorts lie and say that they fit the profile when they don’t. Presumably, clients enjoy believing that a girl is a sexually adventurous college student because it capitalizes on images of “sexy coeds” — and convinces the client that she’s not being emotionally harmed by the work. (I’ve often thought that it’s way past time for “fair trade prostitution,” where sex trade ethics are made into a competitive advantage. I’ve also thought that the most feminist thing I could ever do would be to open a brothel where all the sex workers are treated well. Too bad it’s illegal.)

Of course, SeekingArrangement.com actively encourages the idea that a “real relationship” can emerge from these arrangements. (In our previous interview, Olivia pointed out the SeekingArrangement blog post “Sugar Baby & Sugar Daddy: The Modern Day Princess & Prince?” Another interesting one is called “Sugar Babies Do Fall In Love.”) While some guys on the site really do just want to pay for straight-up sex, some become emotionally invested in the women whose company they buy. And we can tell from Olivia’s experiences negotiating payment that a lot of guys don’t like thinking about how they’re paying for it.

Bottom line: more than one of Olivia’s clients were into her for real, and she felt more and more uncomfortable about it as time passed. One man took a surreptitious photo of her and hung it on the center of his otherwise-bare refrigerator. Another client made faux-offhand wistful comments such as, “If you weren’t already married, haha….”

Olivia asked my advice on one of these guys, who was clearly falling in love with her from the start. She mentioned that she’d already talked to another sex worker about it. The other worker’s reaction was, essentially, “What problem?” As Olivia put it: “She told me that the guy is basically a locked-in regular now, so what am I so bothered about?” But after a while, Olivia couldn’t take how guilty and anxious she felt around this guy, what with the feelings she couldn’t return. She stopped responding to his messages, but didn’t tell him clearly that it was over because trying to phrase the email felt so awful.

“I was so unprofessional about it,” she said. “In the end, he sent me this incredibly sweet note asking what he’d done to hurt me so badly. So my husband helped me write a ‘it’s not you, it’s me’ breakup email. I still feel bad.”

Another facet of emotional difficulty arose when Olivia’s husband started taking a medication that decreased his libido. This put the couple in the odd position of Olivia having sex with other men, but not her husband — with her husband’s full knowledge and consent. Although her husband tried to reassure her, she began feeling less secure and stable at home. And sex work is stressful enough that home security can really, really matter. Indeed, at one point Olivia mentioned: “One of my friends is tempted to get into sex work. But she says she doesn’t think she can deal with it, emotionally, unless she has a partner at home who loves her and will back her up. So I’m not supposed to let her have sex for money until she’s in a good solid relationship.”

Finally, as Olivia fielded other life stresses, she flatly realized that she couldn’t have anything extra going on. What with all the above conversations, we saw signs that the change was coming, but when it arrived it was both sudden and intense. “One day I just knew I had to stop,” she told me. “It’s bad, because we’re behind on rent now, but I had to stop. My husband pointed out, gently, that we need the money. But of course he accepted it when I said I was done. Anyway, I managed to line up a good temp job, so we’re okay for now.”

I tried to show in the original interview that Olivia is very privileged compared to most sex workers. She’s got race privilege for her whiteness, class privilege from her background; she’s pretty and young and “valuable,” and has tons of education to boot. She doesn’t have a drug habit or some other truly debilitating issue. Although she’s under some financial stress, she’s not desperate.

And that leads me to this question:

If even a woman like Olivia — who was well-treated and made a lot of money and didn’t feel trapped; whose life sounded like the glam fantasy of today’s high-end call girl — if even a woman like Olivia eventually needed a break from sex for money, then what could this imply about the experience of less privileged women? I’ve got a bunch of sex worker friends, and I would never say that a woman can’t be a 100% consenting adult sex worker who enjoys her job. But what I’m trying to get at, here, is that even on the “high end,” sex work can be incredibly demanding. Even when sex work is as pleasant as it possibly can be, it’s often very hard.

I’d like to see more conversations that acknowledge the reality of sex work as emotionally intense and challenging, a job that can be bad for many people at many times in their lives — without letting go of the fact that some people can and do freely consent to the job. (The sex worker Mistress Matisse has written more on sex work and emotional labor here and here. And male sex workers don’t always have an easy time; the porn star Tyler Knight has written about some of his more difficult moments, too.)

The point is not “sex work is bad and should be banned” — but nor is it “sex work is glamorous and fun!” The point is, sex work is often hard work, even for people who are not mistreated or abused. As such, it deserves both respect (from outsiders) and open-eyed caution (from those who consider taking it up).

Olivia’s not sure she’s done with sex work for good. “The door is still open for future involvement,” she told me, last time we met for coffee. “If I do go back, I think I may try for straight-up escorting, but I’m not really sure….” Presumably, working as an escort rather than being a “sugar baby” might evade some of these confusing, strangely-negotiated situations. Would it evade all of them? It’s hard to say.

Regardless, I wish her luck.

* * *

The image at the top of this post is a panel from “Ramadan,” my favorite episode in Neil Gaiman’s legendary Sandman series of graphic novels. “Ramadan” was illustrated by P. Craig Russell and published in Fables and Reflections, the sixth Sandman collection.

* * *