Sex & Relationships

Sex in Exchange for Gifts and Cash? What It's Like to Sleep With Wealthy Older Men for Financial Support

A 25 year old woman's experience on a "Sugar Daddy" site raises a host of class, race, and gender issues.

The following piece first appeared inRole/Reboot. 

Sex work is a controversial and polarized topic, and there are many perspectives on it. My position is complex—but for me, when it comes to how we actually interact with sex workers, one important factor is whether or not they consent to and enjoy their jobs. I am absolutely in favor of giving better options to sex workers who do not enjoy their jobs, and I am horrified by the idea of a person being trafficked or coerced into sex that they don’t want to have. But I also know people who have sex for money 100% voluntarily, and I do not want to deny their experience.

My friend Olivia, a 25-year-old graduate student, recently started advertising her services on a “Sugar Baby” site called SeekingArrangement.com. I think it’s important for more people to understand these kinds of experiences, so I asked to interview her. Many people have pointed out that once a person starts thinking about the definition of “prostitute,” it’s a bit difficult to define what exactly a prostitute is. Some of my sex worker friends have asked the question: What exactly is the difference between a person whose partner buys her a fancy dinner after which they have sex, and a person whose partner buys sex with money? Olivia has thought at length about this, and I’m grateful to her for sharing her perspective on that question, and others.

Please note that Olivia is exceptionally privileged. What you are about to read is a portrait of what the sex industry looks like for a person who is very privileged: she comes from a white upper-middle-class background, she is not desperate, she is being paid a lot of money, she does not have a drug addiction. Many other peoples’ experiences in the sex industry are very different.

The interview went long, so we’re going to post it in two parts. Here’s part 1:
Clarisse Thorn: Hey Olivia, thanks so much for being willing to talk about this incredibly complicated topic. Could you start by defining a sugar baby site? What is it?

Olivia: I use the site SeekingArrangement.com. It’s very hard to pin down exactly what it does. I guess it connects people, usually with a big age gap, who are interested in exchanging some kind of material goods or financial resources for some form of companionship that is often sexual—but not always.

As far as I can tell, the site’s founder is very against the claim that this is prostitution. He puts out a lot of publicity claiming that this site has nothing to do with prostitution. At first I thought that he was trying to evade legal consequences, but I think he actually probably believes that. The site has a blog that he controls, and you can look at it to get a sense of what he’s thinking. One post I think is really interesting is called “Sugar Baby & Sugar Daddy: The Modern Day Princess & Prince?" which compares being a sugar baby to a kind of “happily ever after” princess fantasy.

So far, no one I’ve talked to seems remotely interested in hiring what they see as a “prostitute.” They seem to want to be having sex with someone they find very attractive who is also someone they feel like they can respect, whose intelligence they respect. For example, someone I see occasionally—the last time I saw him, he gave me money at the end and he said that he felt good about giving me the money because he knew I wouldn’t spend it on, quote, “a designer handbag.” He seems to think that I am reasonably ambitious and have my shit together, and he seems to feel more comfortable giving me money because he knows it goes towards my grad school costs and credit card debt. My ability to write with proper grammar, without overusing emoticons, appears to be my biggest sales point. Men have told me this outright.

That guy also mentioned feeling more comfortable because he thinks I’m from the same social class as he is. There are a lot of class issues coming up in these encounters, I think. Being white and from an upper-middle class background may help me get clients. My background has also given me a ton of confidence that puts me at an advantage when negotiating. I do not think I radiate “take advantage of me,” and I (nicely) tell guys who start doing that to go away.

The guy I was just talking about—he also mentioned that he feels like he doesn’t want to have sex with someone that he doesn’t feel at least a little bit connected to. There’s a distinction between meaningless sex and casual sex. I think these guys want casual sex—maybe they aren’t at the point where they want to deal with having a partner, or they’re really busy at work, or they already have another partner—they want casual sex but not meaningless sex.

In my encounters with these men, the money does two things. Firstly, it enables them to have a relationship with me that they wouldn’t otherwise be able to have. Secondly, it puts them in this position where they can give me something valuable and have that be appreciated. The guys I see really want to feel appreciated.

Clarisse Thorn: Do you feel like this has given you any new insight into gender roles?

Olivia: Hmm …. It’s made me feel more powerful. I definitely feel like I am the one with the power in this situation. 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.

A lot of the men who are on this site want to feel appreciated, so it’s important to them that the woman they’re with gives off the appearance of appreciating them. So, for example, on the website, there’s a lot of talk about sugar daddies being “mentors” or “benefactors” rather than clients. They seem to want some combination of me asking them about their day, and they also want to feel like they’re bestowing knowledge upon me about the world. One of the men I see will always talk about his opinions about money. He has complicated feelings about himself having money because he doesn’t come from money, so he’s trying to work those out. But he also keeps telling me in a very serious voice that money will not make me happy, that nothing I can buy will make me happy. I tell him that I can buy security and he says yes, that is one thing I can buy.

Other men seem to be having issues with their age. One mentioned that he’s just turned 40, and that’s really bugging him. Then he flaked out on me a couple times—I don’t think he was completely OK with his own decision to be seeing me. But anyway, often, another thing these men seem to get out of it is access to someone who has a bunch of youthful energy and optimism and just plain new ideas. A lot of them have mentioned feeling stuck, or bored, or cynical, or intellectually constrained. So in this sense, sex is only one thing I’m offering them—I’m also offering them optimism, hope, energy, and so on. Firstly, the sex is good in and of itself, as most of them aren’t getting laid otherwise. But the sex is also a symbol of them getting access to my youthful energy or whatever.

I think the archetypal image of a mistress involves a woman being “kept” so that she doesn’t have to work, so that she can be available for sex basically whenever. But I don’t think this is what the men I see want. I am more valuable to them because I have other work that I am seriously invested in, and am having sex with them anyway. Again, these men are interested in a woman who they see as more “equal” to them—in this case, defined by earnings potential—and they seem gratified by the idea that they could help me enter their income bracket someday. This is, of course, still kind of patronizing; like I said, they keep using words like “mentor.” It’s also presumptuous. But I think a lot of them being patronizing and presumptuous can probably be attributed to age and wealth, and only some of it to gender.

I think I’ve learned more about class and money than I have about gender. It turns out there are people to whom $1,000 versus $3,000 doesn’t matter that much, and I finally understand that on a visceral level—$1,000 doesn’t mean the same thing to me as it does to most of them. I knew this, but now I really know it.

Another thing I’ve been struck by is exactly how much romantic relationships are worth. I’ve had several clients tell me they don’t feel wealthy, and they feel like they worry about money a lot. I think they were sincere. Of course, my first thought was: don’t you think that your $2,000-per-month prostitute is part of the budget that could be trimmed? But I think that maybe it’s not, actually. I think they think that investing a lot of money in me is a good investment for them if it gives them a release valve so they can deal with the rest of their lives. They’re probably right.

 

Clarisse Thorn: You mentioned that you feel powerful in your relationships with these men. But there are issues of your safety, right?

Olivia: I think there are issues of safety anytime a person meets someone they don’t really know, especially if they plan to spend time in private. And especially if you’re dealing with topics as sensitive as sex or money. There may be more issues of safety with this because some people really do believe that money can buy them anything. But for the most part, when I meet people they seem very respectful.

Things I do to increase my safety are that I tell my husband and my friends where I’m going to be, I tell them exactly where I am. I’ll do things like take down a client’s license plate number and text it to my husband. I’ve been thinking maybe I should look at each client’s driver’s license too, and text the client’s name and driver’s license number to my husband. I think some clients might feel threatened by that, though.

The most important thing for my safety is that I’m willing and able to walk away from situations. I’m not desperate—I won’t starve or die if I don’t do this work. I meet all my clients in public first for a meal, and if someone sketches me out, I leave. I’m not so desperate that I’ll get into a situation that scares me.

I guess I am at risk if I meet a really crazy person who wants to chop me up and put me in a dumpster. But I could meet a person like that during a normal night at a bar, too.

The major risks that I see is that I might catch an STD—but I use protection. I might end up alone with someone who believes that the money he’s paying actually gives him the entitlement to do whatever he wants to my body, but I’ve never encountered anyone like that. The thing is, as I said before, I haven’t met anyone who I think would actually describe themselves as paying for sex. The terms on which I continue to see these men are probably less explicitly negotiated than an escort’s terms would be. I don’t have flat rates, for example.

I’ve heard escorts complaining that people who use sugar baby sites are unprofessional, and I think that from an escort’s perspective, they probably are.

Clarisse Thorn: If people are unwilling to actually talk about sex for money, it must be hard to negotiate your encounters. Do you have a set of steps for negotiation?

Olivia: I haven’t been doing this for very long. It’s varied so far. Usually, I meet them for some kind of meal, and we chat. We have a perfunctory conversation, like, “How was your day?” Then one of us will say something like, “Tell me a bit more about what you’re looking for. Why are you on the site?”

Then we’ll explain our deal to each other. Like, he might say: “I’m divorced, I’m looking for companionship.” At some point, money comes up. I am always extremely vague when I talk about money. I’ve found a good deal of variation in how squeamish people are about money.

For example, one client was saying that he wanted to get married again, but not yet. I said, “Huh, well, if you’re interested in a more emotional relationship, how do you feel about involving money?” The way he explained it to me was that people are attracted to each other for all kinds of reasons, probably including money, so why not be up front about the fact that money is attractive. He seemed almost confused about why I asked. With that guy, I ended up sleeping with him before we even talked about money, which was a huge risk, but I thought it might work, and it did. We had the money conversation immediately after we had sex—at some point when we were taking a break, I asked what he was looking for more specifically from this relationship, and he said that he wanted to see me again, maybe once a week. I think I asked him his preference for a monthly allowance as opposed to every time we meet, and he said he’d rather do something monthly. Then when we were getting dressed, he pulled out $1,000 cash and handed it to me, and said, “I’ll give you the balance next time we see each other.”

With other people, I can be more straightforward. Maybe they aren’t sure how to set up the relationship, so maybe I talk about another client, like: “I have another client I see three times per month for $3,000,” and they might say, “That sounds good.” But some guys will just negotiate it per encounter. One guy brought it up very quickly after we’d exchanged some emails. He said that he prefers to do a “per meet” of $300—he called it a “per meet”—I told him that was too low and quoted him $1,000, and he said he’d meet me in the middle. Another guy told me that he would just slip $400 into my purse when he saw me, and that’s exactly what he did.

I have one client I’ve never explicitly discussed money with at all. I had lunch with him, and we didn’t negotiate anything, though we talked a little bit about our reasons for being on the site. The next time I saw him—we were deciding where to meet, and he asked if he should get us a room. I said that I would like that, so I met him and we had sex. He knew it was my birthday soon, so as we were getting dressed, he said, “I know we haven’t talked about money, so I got you some birthday spending money,” and he handed me an envelope with $400. The next time I saw him, he asked about my plans for the evening. I said I was having dinner with a friend, and he handed me $400 in an envelope and said, “Maybe this will help pay for it.” I’m lucky that I’m willing to accept $400—it’s my lower bound, but I’m willing to accept it. Imagine if I hadn’t been willing to take $400—that would be super awkward. Probably I should have negotiated that situation more clearly, but it worked out OK .

I’ve heard about situations where unclear negotiations did not work out OK. There was a “New York Times Magazine” article about the site published in 2009. In that article, there were some examples of unclear negotiations that didn’t work out well. But it sounded like that woman didn’t really know what she wanted, and didn’t really enjoy the work. But I do. And I know other women who do, too.

I have a new client who paid me $3,000 up front to see me three times a month. But I haven’t heard from him since our first meeting. If I were his girlfriend, I’d call him, but he asked me not to call him. So I don’t really know what the deal with that one is. Maybe he’s gonna flake out on me, but he already gave me $3,000, so that would be weird.

Clarisse Thorn: So, your husband. You mentioned him briefly. How does your husband feel about this?

Olivia: He does not seem particularly threatened. We already have an open relationship. I think he sometimes feels very visceral jealousy, but that’s just like any other time one of us has sex with somebody else. We just have to talk about it.

Part of the deal here is that I’m doing this because I’m broke. My husband really wants to be able to support me financially, but he can’t right now, so I’m supporting both of us doing this. I think that’s a real blow to his ego. To the extent that he gets bothered, I think it’s because I’m allowing other men to support me and give me money; he doesn’t care about the sex. Even though I see this as work, he sees this as “here’s this rich successful guy who just gave my wife a bunch of money, and she slept with him, so probably she’s attracted to him.”

I am kind of attracted to my clients, and I kind of get off on making them happy, and I happen to think that the age difference is kind of hot. I like having sex with them; it’s not unpleasant. I like hearing about these guys’ life stories. I think it’s interesting. But these guys would never be a threat to my husband. I would never be sleeping with any of them except for the money. And I love my husband. I’m always very up front about the fact that I’m married and I love my husband. My clients accept that.

Clarisse Thorn is Role/Reboot's Sex + Relationships Editor.