Pillow Talk is a series that deciphers our mixed signals about sex—who’s actually having it, who isn’t, and why—one interview at a time. Get in touch to suggest a subject.
This week, we meet Devon, a tall, bearded, and silver-haired 54-year-old media professional in the Southwest who, despite what you’d expect from a man his age, makes a small killing as a sugar baby. In fact, he often runs circles around his younger competitors. This interview has been edited and condensed for clarity.
Slate: How did you get into sugaring?
Devon: I started when I was 17, long before the term “sugar baby” or “rent boy” even existed. I was at university, and I had a scholarship for my education, but I had no housing or food. I was 3,000 miles away from my family in an unfamiliar city. I had no resources to lean on. I found myself really struggling.
I had a work-study job as part of my financial aid package. One day, my boss, who was a married 46-year-old woman, took me to lunch. She asked me how I was doing, and I told her I’d been having a hard time paying for rent and food. I was shocked at the solution she proposed.
She wanted to pay my rent in exchange for us having a relationship. In hindsight, it was rather predatory. But I was desperate, and not exactly innocent when it came to sex. I had friends and family who were sex workers, and they were some of the best people I knew. I’d also been exposed to porn and professional sex at a very young age through a friend’s dad, who would now probably be categorized as a “porn addict.” So, sex work wasn’t a foreign concept. It all just sort of clicked.
When we started seeing each other, it felt like a huge weight off my shoulders. I didn’t find her unattractive—she was smart, very hungry sexually, and a marathon runner. At first, she was kind and easygoing, and it was exciting to be a teenage boy having sex with a much older woman. It lasted about two years, and then things really went downhill. She started to become deeply possessive, and stopped respecting my needs and boundaries. She’d show up whenever she wanted at my house, and question me about who I’d been with. She saw me as her property. A lot of it felt violating, so I ended it.
Did you keep sugaring after that?
I did—I had to find some other way to pay my rent. One way I figured out how to do that was playing poker. I was pretty good, and could occasionally scrape by on my winnings. One day, a male professor who’d been watching me play approached me. He was like, “You’re really good at this,” to which I replied, “Yeah, I gotta pay my rent with it, so I’d better be.” Then he made me a proposition—he’d be my stakehorse if I’d be his companion (“rent boy” is more accurate). Like my first sugar relationship, he just sort of fell into my lap.
Were you interested in men at the time?
Yes and no. My sexuality has always been experimental and fluid and I had both boyfriends and girlfriends in high school, but my homosexual relationships were fewer and more chaste. My first sugar daddy was my first experience as a bottom, though. I was ill-prepared for that.
That said, he was actually extremely kind to me, and I enjoyed a lot of our time together. It was because of him that I got to go to Vegas and play poker and stay in the high-roller suites, which also helped me make money. He only taught classes for half the year at his university, and the other half of the year, he spent with his husband in another city. So I had his place to myself a lot of the time, and I paid my rent with sex.
How was the sex?
I found it distasteful because I wasn’t really attracted to him. At the same time, we were building a mutually beneficial relationship. He was great at taking care of me in certain ways—and we had really good conversations—so I developed certain feelings of intimacy with him that made the sex tolerable. It’s not that big of a jump to see how you could have sex with a person who is truly kind to you, who you appreciate, and who is improving your life—even when they’re not physically attractive to you. Sugaring is about building a relationship. Sex is just one part of it.
Isn’t that relationship mostly fake, though?
Not always. Sometimes we really do feel for our clients. Spending time with someone creates intimacy, and you’re enriching each other’s lives in pretty clear and important ways. It’s more than just the money, too. Clients often bring a lot of novelty and excitement to your life, in addition to stability and security. You get exposure to new places, cuisines, people, ideas, and ways of living you’d never ordinarily have access to. Sometimes, clients are intolerable and you’re acting the whole time. Other times, you learn to appreciate, and even care for them.
How did all this affect you as a young man? You had multiple random and fortuitous relationships with people much older than you, at a time when you were still developing.
My frontal lobe was definitely still forming at the time, but I learned a lot about relationships—specifically the kinds you want to be in versus the kinds you need to be in. Sugaring also made me far more conservative about who I spent my personal time with, because my clients took up so much of my energy. I really had to be into someone to see them non-professionally.
Also, because I was used to being the much younger person, it really set the tone for a lot of future dynamics. As I’ve aged, I’ve become the person with the normal, stable, well-paying job, benefits, and vacation time. And so all my personal relationships tend to be with people who are like the person I was when I started sugaring—younger creatives, artists, and thinkers. I’m drawn to these people because they bring a lot of adventure, novelty, and enrichment to my life. They’re drawn to me because I provide some stability and financial support. Both parties are equal providers to the relationship—no one needs to think too hard about it.
So you’ve been on the client side of this, too?
Yeah, numerous times. These sorts of relationships just make sense to me.
But you kept sugaring at the same time you were playing the daddy role?
Sometimes, yes. Most of my sex work career has been PPM (pay-per-meet), not sugaring, which allowed for some flexibility in the roles I played. I was mostly escorting and pro-Domming into my 40s, with some sugaring thrown in every now and then. I would have one, maybe two sugar relationships a year between when I started in 1992 and when I left sugaring for an extended period in 2015.
One of the more notable ones was with a high-end gallery owner in NYC. I was in my 40s, and she was a few years younger. It lasted just shy of two years. She had no space for dating or lack of clarity in her life, so a sugar dynamic is what she preferred. Like a lot of my clients, she wanted someone she could actually have a conversation with, go to events with, and be seen with in a way that didn’t seem suspicious. In part because of my age, what I offered wasn’t simply sexual ease and reliability, but being at a gala or an event with her and nobody questioning if I should be there. My diction, knowledge, and appearance fit the environment, and her.
Ah, I see the appeal of an older baby now.
Right. With younger babies, it’s often just sex and shopping. That’s one way to go about this, but when you’re my age, shopping is the last thing on your mind. You generally have a lot more to offer than just dick—you’ve sort of matured to a point where you’re curating an experience that someone can take with them, whether it’s at a restaurant, on a vacation, or at an event. A lot of clients feel they can trust people their age to be mature, hold a conversation, speak up for themselves, be present, and stay up on current affairs—which are all things that can create intimacy and intrigue in a relationship. In my case, I look the part, I speak the part, and I can support myself—so clients feel like I’m not just for behind closed doors. I’m not that far off from the type of person it would be acceptable for them to date or be seen with, so they feel less like they’re hiring a sex worker and more like they’re “getting to know” a peer. Also, when you’re 40 and 50, you can likely support yourself more than you could in your 20s. So you seem less desperate. It gives clients the illusion you’re with them because you want to be, not because you have to be.
What sorts of clients seek you out? What are they looking for?
Mostly men and women around my age who want someone on their level. They’re looking for a person who can match them, not just rely on them. Interestingly, the male clients I had were mostly in relationships with women. They had a clear idea of their needs, and they didn’t hide it from their spouses. These were guys who were happily married, but also needed to be with men. They wanted to talk to men and spend time with them, not just have sex with them for an evening. It’s more than just “Where are the poppers?” I also had a lot of male couples who wanted a third, and didn’t want it to be complicated.
Do you ever get younger people who are interested in you?
As a sugar daddy, Dom, or escort, yes. As a sugar baby, rarely. There’s a very small market for younger clients seeking older male sugar babies. One of my female clients was in her 20s when we were seeing each other.
Where do clients find you?
Seeking Arrangement. The rest of the sites are weird.
And you do pretty well there?
I do, particularly in the Northeast. When I was living up there, I had rent and expenses mostly covered, and there was a good bit of travel, too, which helped because when you’re traveling, the client pays for everything. People are more generous up there. Other regions are different. Where I live now, I could barely cover food and gas by sugaring. Men also make way less money in this business than women, and there’s a far bigger market for female babies. But in certain areas, it’s not that hard to be a man in this space. In the Northeast, Mid-Atlantic, and Florida, the gay sex work market is active and visible. That does mean more competition, though, so you either have something unique to offer or accept a lower wage.
For color, I used to date an escort. We were demographically the same in terms of all the sociological and educational strata and what we offered clients, but there was a stark contrast in how much we brought in. She could charge $800 to $1,000 an hour and would have to turn away clientele, and she had two sugar daddies that gave her $10,000 a month each for two overnights and one dinner/play meet. Meanwhile I topped out at $700 an hour and was getting $4,000 to $5,000 a month for one overnight a week.
You said you live in the Southwest, which, to me, is a surprising place to flourish as a male sugar baby. Maybe I shouldn’t be so surprised?
Let’s just say that where I live, there is a very large military base. There is also a lot of industry, particularly chemical industry, so there are a lot of really wealthy people—people who need to present a certain way in public but really want to live another way behind closed doors. This is the kind of town where a 17-year-old dropout can become a stripper and buy a house, and where second-tier income is made up of a huge amount of sex work. It’s all very hush-hush. But again, that’s the benefit of being older in this space—you wouldn’t look at me and expect me to be doing what I’m doing. I can fly under the radar because I blend in.
Was there ever a point where you thought, “I’m too old for this”?
It’s part of why I stepped away from sex work in 2015. I stopped having patience with having to play a role, and with needing the kind of rest that followed. I struggled to keep up the act like I could when I was younger, and that made the job hard to do.
Is that why you gave up sugaring? And are you done for good?
I actually only sugared for like eight months in my 50s. I had a financial goal, I met it, and that was that. But broadly, what made me stop was some combination of the 2016 election, SESTA-FOSTA, and the destruction of all the methods sex workers used to keep themselves safe, like Backpage. Not being able to communicate with other sex workers and share stories and find out whether clients are safe was a huge breaking point for me. The safety net was gone, so it really came down to like, what am I willing to sell?
This was the most apparent with one client, a Republican rancher woman who found me on Seeking Arrangement. She was the classic spend-all-your-money-on-fitness-and-plastic-surgery type, so when the time came for sex, it wasn’t that hard to do, but I absolutely could not handle the role I had to play for her. She actually expected me to agree with her views. Usually, when clients got all MAGA, I’d just keep quiet and let them rant (a lot of them just want validation, and they see your silence as validating). But she wanted more than silent nodding, so I hit a breaking point. I realized I was still willing to sell my body, but could no longer sell my beliefs.
A few years ago, I moved from the Northeast to the Southwest and rapidly got into motorcycles. I found myself needing some money to support that, so I got back on Seeking. And absolutely every single person I came across was a struggle to even get past the introduction with. There was just too much political divide. If it was just about sex, I guess I could get past the MAGA thing, but it’s not. Sugaring is about intimacy. And I can’t fake that with them.