The author's listing on a sugar dating website. Screenshot courtesy of the author

My Life as an Ivy League Sugar Baby

After graduating from Princeton, I traded sex for money. But don't we all trade love for something?

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Jun 14 2015, 4:20am

The author's listing on a sugar dating website. Screenshot courtesy of the author

True or false? When seeking the perfect job, focus on those things that you enjoy doing for free.

I answered "true" to that statement during my last semester at Princeton when I began hunting for the perfect career. It informed my choices distinctively. Everyone around me was planning to move to Hollywood to try their hand at acting or preparing for grueling interviews with investment banks and consulting companies in New York City. At a school like Princeton, everyone speaks loudly about their ambitions and accomplishments, while our struggles and insecurities are barely whispered, even to ourselves. I was about to be released from Princeton, after being molded into the proper Ivy League renaissance woman ready for gainful employment. At least, that was the expectation. However, my professional future turned out to be more unorthodox than even I anticipated.

My decision to start dating men for money was a surprisingly easy one to make. I'd always been fascinated by stories of escorts and sex workers and had seen them as kindred spirits in the realm of libertinism and debauchery. I dimly understood that sex unlocked parts of us that we keep hidden, and I saw sex work as a foray into therapy. Since I was graduating with a psychology degree and had a reputation as an aggressively sex-positive slut, sex work seemed an obvious choice.

"Sugar dating" isn't completely distinct from any other kind of sex work. Prostitute, escort, stripper, sugar baby—in the end, men are paying you for an emotional and physical experience. Differences in names have more to do with the person doing the labeling than the professions themselves. Personally, I dislike the terms "sugar daddy" and "sugar baby." I don't like the dynamic they imply. These men are not my father and I am certainly not a child. I prefer to consider myself a "sugar cunt" and my clients "sugar dicks."

When you have an ongoing relationship with someone, as many sugar cunts do, certain familiar dynamics do develop. But in terms of the job description, that's one of the most attractive parts of sex work: you make your job into what you want it to be.

In the beginning, my peers were mostly amused at my declarations to be a sugar cunt, probably because they didn't take me seriously, though several of them expressed concerns for my emotional and physical well-being. Although, I bit my tongue when it came to my own concerns about their career plans, because who am I to judge?

As it happens, some of my favorite clients held down the exact jobs my classmates would take on. Usually it's finance or law, with entrepreneurship coming in as a close third. I feel lucky not to experience their stresses: maintaining their lifestyle, working hard enough, carving out pockets of time for their actual lives. I prefer the uncertainty of where I'll sleep tomorrow night over the tyranny of a company motto.

The trajectory of my sugar cunt career closely mirrored that of most entry-to-boss travails that my friends were undergoing. After we graduated, I lived with a friend in my hometown in Florida. While she struggled over which job offer made the most sense for her, I was scheming about how to hustle money. My beginner's luck was strong and I attracted three potentials when I signed up on Seeking Arrangement—the most famous sugar dating website, boasting "thousands of members" and "dating on your terms." I went through with two of the dates; one guy stood me up at a bar.


The trailer for Daddies Date Babies, the upcoming documentary featuring Tess Woods. Directed by Parinda Wanitwat

My focus, at the start, was to get as much money for as little work as possible. Paradoxically, this led to underpayment for overwork. I spent much more time and emotional energy than I wanted with the initial men I met. One guy was a short, doughy bunny with sandy hair who ran a company that wrote essays for college students. He also carried a chip on his shoulder that was larger than he was, and the weight of his baggage exhausted me. The other was a married lawyer, perfectly courteous and sweet, who just wanted some sexual attention after his wife had stopped providing it. My sugar dicks were cliché as they come. I didn't realize that I would be giving more than sex to these men, that they weren't really paying for my body, but my attention. My validation. The light in my eyes that recognized the light in theirs.

It was enough to make me take three years off sugar dating and try my hand at service and desk jobs. I moved in with a guy I'd met at school and spent two years with him in Chicago, letting him pay for rent and food as I worked as a bartender and temped just enough to cover my weed habit. It's funny how the relationship I had that could be most accurately categorized as sugar dating is one where we both were desperately in love. We didn't realize we were trading attention for validation from each other. I helped him feel human in certain ways, and he helped me feel human in others. The aftermath of our breakup opened my eyes to the transactional way that most of the people around me seemed to treat their relationships. My boyfriend and I had fallen into a symbiosis, where we each needed each other's support—otherwise, we fell apart.

I priced myself pretty cheap—$500 per meeting put me in the sweet spot of men who were willing to pay but were too shy to be demanding.

At the same time, as I ascended from entry-level to moderately experienced at being a sugar cunt, I came to understand a bit more about why sugar dating had been so attractive to me in the first place: Done right, you get all the perks of running your own business without the need for startup capital or marketing.

We always discussed money at our preliminary "get to know you" date. I priced myself pretty cheap, both because the idea of asking for $1,000 per meeting seemed absurd to me and because I found $500 per meeting got me into a bit of a sweet spot: Men who were able and willing to pay immediately but who were too shy or new or kind to be demanding. I got messages from some men promising thousands of dollars per meeting, but their personalities usually scared me off. My income stream has been steady, and my rate hasn't changed much since I started, but I've never been coy about asking for the money. I rarely had to ask for it once a price had been agreed upon. My experience with sugar dicks is they're either trying to scam you, which you know right away and avoid, or they're anxious to pay right away. Many of them truly believe that they are doing me a favor, and maybe they're also convincing themselves that this isn't really a transaction, but an exchange within mutual attraction and regard. I don't care what they think. If they can't be honest with themselves about the nature of the game, that's their problem—although it often becomes my problem too, when they break it off because they have too many feelings.

Photos courtesy of the author

I get a lot of questions about the nitty gritty of the business. This rabid curiosity often betrays the storybook sense of mystery and charm that other people see in my line of work. The money discussion between a buyer and seller takes place between a sugar dick and sugar cunt the same way any freelancer gets up the nerve to price their work. Business is business, and it feels that way no matter how sexual the business is. After the first time you ask for money, it seems natural.

Looking back on my heyday as a sugar cunt, I think I wanted to simplify my life enough so that I felt in control of all the moving pieces. If even my closest and dearest relationships operated on the same power dynamics that I saw in the office, it seemed logical to unify them under one hub. I hadn't been in my lovely marketing job at a lovely company with lovely people for a year before it all became too comfortable to bear. The monolithic schedule dictating my life grated savagely on me, and my mind turned again to thoughts of the hustle. Maybe I just hadn't been going big enough—north Florida was a small pond, after all—so I cast about in Chicago for potential clients. I expected to make money easily. I felt that I was armed with some experience of life, relationships, money, sugar dating, as well as alt-Barbie looks. My OKCupid profile became so popular, I had to turn off notifications to preserve my battery life. I thought I was about to take the Chicago sugar dicks by storm, turn their world upside down, and shake their money into my purse.


But I didn't meet a single man who paid me in Chicago. The well was rather dry. I don't know if the desolation of winter had anything to do with the lack of interest, but my intuition and literature studies tell me it was hubris. Instead of a worshipful sugar dick who gave me whatever I wanted in exchange for very little, I wound up quaking in a taxi, wondering how close I'd come to death.

One of the men I met up with was the personification of all my friends' worst fears. He lied about his job, his apartment, and his name while interrogating me about my birthday and background, to see if I qualified to be pinned to his board. He took me back to his apartment against my better judgment, where we role-played abusive father and obedient-but-scared daughter as he bathed me with baby soap and powdered my ass. He clapped his hand over my mouth and told me, "There is much love in abuse." Over his shoulder, I read the title of his manuscript-in-progress, The Baby Doll Murders, as he told me his elaborate plans of starting a harem with women of all backgrounds and specific zodiac signs. "I'll give you a little sister to play with," he said. "You can do to her all the things I'm going to do to you." He asked me to stay the night but I demurred, and he texted me as I left, "I want you to do this because you love me, not for money." I answered, "Yes, daddy," and ignored his other messages.

After that, I gave up on the sugar dating scene in Chicago. I met and started working with a guy in New York as a dating coach, parlaying my experience with attracting and interacting with men into advice for their social lives. Eventually I moved to the city to go into business properly with my partner, whom I'd also begun dating. Unfortunately, our relationship and the new plans for the company ended abruptly at the same time. With $25 in my pocket and my entire life in three suitcases, I stood in the rain by a subway entrance and refused to let the tears burning my eyes escape. I needed every drop of that fire to keep going.

The summer I spent in the city was a transformative experience for me. I tried to get on my sugar dating hustle, but I was hesitant to meet anymore. I realized that I couldn't trust my internal rudder to steer me towards anything healthy or safe. Based on my past, I was attracted to people who made me miserable. Because I was so cautious, I only met one sugar dick in New York. He was a decent companion: fairly interesting, courteous, kind, and generally nice as hell. Canadian, of course. I've never met a Canadian I didn't like. The only problem was that his payments were smaller than I needed and took longer than they should, so I wasn't sad to say goodbye when he finally paid me out.

They were emotional parasites, eating my orgasms to feed their ego.

Since New York was not lucrative for me, I jumped at an opportunity to move to Southern California. When I got there, I swore off the hustle, but after six months I needed cash and place to write. I crashed with my friend in San Francisco and logged onto my Seeking Arrangement profile again. It felt different, this time. The freedom, flexibility, and speculative nature of sugar dating still attracted me, and I was confident that I could play the game to my advantage.

In San Francisco, I've had my pick, more or less, of the type of man I want to date. My sugar dating life this spring was been more interesting and rewarding than ever before. I've answered messages and bookmarked profiles I liked with my morning coffee, and then met whoever I was seeing that day for lunch or drinks in the afternoon.

Although, I've finally mastered being a sugar cunt, I wouldn't say that the life is glamorous by any stretch of the imagination. The money's been good, but the pretty jewelry has becomes less enticing the more I realize that it's really a ball and chain. None of the sugar dicks I've dated have stuck, either because they felt too strongly about me and couldn't reconcile the payment with their emotions, or because I felt like they were emotional parasites, eating my orgasms to feed their ego.

Their fadeout has corresponded with my waning interest in the business of sugar dating. I've learned that a job is a job is a job, and I'm just sick of working for other people. I got into this hustle to stay out of lines of work where I would feel trapped, stuck in an office, exhausting myself on a corporate hamster wheel. I never wanted to feel controlled by my work, whatever work it was. Someone is always happy to be your boss, if you let them. I feel like it's time I stepped into those shoes.

Follow Tess on Twitter and check out her website.

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