The Self-Flagellation of My Eternal Sugar Daddy Hunt

It’s not a coincidence that a rather large percentage of female artists today are current or former sex workers. Here, art perv Maidenfed documents her search for the human lottery ticket known as the “sugar daddy.” Main image of Maidenfed by Ian Reid.

Note: I think it’s important to make it clear that I do not intend any of my writing — especially about sex work — to be construed as representative of any “typical” lived experience or attitude. I am aware of my many privileges, and I hope that writing about my individual experiences and feelings does not suggest that I am any sort of spokesperson or authority, because I do not consider or assert myself as such.

I already am debating whether or not I should even publish this, as I doubt it will help me land the benefactor I am always hoping for, but here I fucking go… 

Since college, I’ve been an on-again, off-again (but usually on) member of several sites facilitating the establishment of “arrangements” — aka sugar daddies aka predominantly self-important whorephobic tricks. I have only ever had a longish-term SD once and — since I was an addict at the time — I think of it as part of a past life, when I wasn’t really me. 

Maybe it’s just pure laziness that creates — and pursues, though any effort would contradict it being sheer sloth — the fantasy of finding what is essentially a human lottery ticket who will take away the vast majority of my woes. I’d prefer to think that it’s somewhat less straightforward and unflattering than that. 

Besides, it seems more unusual these days to find a woman who hasn’t at least tried some form of sex work (and any insistence that “arrangements” don’t fall under that umbrella is misguided and likely straight-up delusional), especially in cities with a cost of living as high as NYC. Despite the carefully curated luxury and euphoria of social media, most people are underemployed and just scraping by; as such, I don’t think it’s irrational to romanticize the metaphorical — or literal — briefcase full of cash stacks.

And it’s certainly not a coincidence that there’s a rather large percentage of female artists who are current or former sex workers, whether they dabbled or made it their full-time vocation. I don’t think it’s an exclusively artsy-fartsy, special-snowflake thing to find the idea of a regular full-time job somewhere between uncomfortable and unbearable — especially when there’s been a taste of the immediate gratification of making [comparatively] a lot of money in a short period of time. However, when your main passion is something unlikely to make you enough money to survive, let alone prosper — like mine, and, sadly, most other creative endeavors — it’s ideal to find a lucrative-enough hustle that leaves you with enough time and energy to continue that [probably dead-end, financially speaking] pursuit.

But one of the difficulties I’ve found navigating the sugar daddy terrain is the infection of anti-sex worker sentiment. Many SDs include “no pros” in their profiles, and that’s the nicest iteration; there are also those who spew misogynistic rants about the manipulative shrews who are just in it “for the money.” I guess the absolute dream for the potential sugar baby is to find someone who will fund their entire existence; for the man on the other side of it, the miracle would be to find a woman—usually less than half his age — who genuinely wants a relationship, and the “pampering” and “spoiling” offered is merely a bonus. The omnipresence of disclaimers like “I don’t want this to feel transactional” and “don’t treat me like an ATM”—along with the almost comical overuse of the word “chemistry,” as though it’s an incantation—belie the primary motivations for most women who sign up for these sites in the first place. 

It’s all well and good to prefer an arrangement that doesn’t feel like a business relationship, but just about every woman I know who has experience in this realm wants to pay her fucking bills. She wants to have some financial comfort. The [extremely hypothetical, and usually never-realized] fancy dinners and tropical vacations and lingerie shopping sprees might enrapture an already well-off woman who is happy with embellishments and bucket list experiences; but for the majority, it is not the end game. Neither is the supposed “mentorship” many of these dudes proffer. At the end of the day: cash is king. And if you’re struggling to afford rent on a monthly basis, the dangling carrot of professional tutelage seems a bit ridiculous and irrelevant. The freedom of having money to use right now as one deems appropriate is — speaking for myself — of far greater significance than a buttery steak or a buttery leather boot (or a pair of them, even!). 

To be clear: I am not suggesting that 100% of the men who populate these sites fit into the aforementioned archetype. I have met plenty who, although a sugar daddy/sugar baby dynamic did not develop, were open-minded, talented, interesting, and highly knowledgeable. There are many dudes who are simply lonely, have been out of the dating pool for years (if not decades), and think that an “arrangement” is a desirable alternative to or placeholder for an exclusive, marriage-on-the-horizon relationship. He may favor the theoretical transparency that such a dalliance embodies; but those waters of clarity can get muddied by a cognizant or subconscious aversion to the concept of exchanging money for intimacy. 


I keep hoping that I will sooner or later — and, let’s be real, sooner would be just peachy — attract a multimillionaire who will be speechlessly dazzled by my non-generic approach to this shit (I seem to endlessly fuck myself over by actually being myself at all times [which my therapist has dubbed “radical genuineness”], despite the knowledge that they really want a fantasy, even if they insist they want the “real you”). And then said tycoon will fund everything I’ve ever dreamed of doing and having. Is this because I feel I deserve it? Not really. I don’t think I deserve much of anything. Is it because I am especially proficient at “mutually beneficial” relationships? Not at all, or I wouldn’t even be writing this. Rather, I have very little confidence in my ability to ever successfully figure out how to become fully self-sufficient. This is predicated on the discouraging belief that I missed too many life-skills checkpoints while I was escaping reality via isolation and substance abuse, and have no chance of “catching up.” 

And although I absolutely do not subscribe to the mentality that sex work is inherently damaging to its practitioners, I am aware that I have developed a somewhat skewed perspective on what I feel I need to do to “get ahead.” Out of both a comfort level with presenting myself in a sensual manner and an often-paralyzing anxiety that I lack the requisite knowledge and qualifications, I convince myself that unless I astonish someone with my charm/wit and/or blow/fuck that someone, I will never get anywhere in life. It’s hard to tell how much of this is actual truth and how much is my own warped outlook. After all, the trope of the woman “sleeping her way to the top” is obviously not wholly fictitious; which isn’t to say it’s “better” or “worse” than any other route. 

I frequently think to myself, not in a particularly kindly or forgiving manner: “Jackie, hun (jk I’d never say that, to myself or anyone else), you know, if you put half the effort into just about anything else in the universe as you do into this persistently fruitless quest for The Dude Who Will Fix It All, you could be rather successful at that other thing and possibly would no longer be convinced you need aforementioned Dude.” And as I learn and grow — and my sobriety progresses — I do develop interests and goals that elucidate the fact that I do not want a life in which I consume 100x more than I produce (I mean art; not, like, agriculture) and laze about on island beaches with Chanel sunglasses and Gucci sandals and an IBM bikini, or whatever the hot swimwear brand is currently sorry I’m out of the loop. The “seeking” in “seeking arrangement” for me signifies the quest for a means of some form of stability so that I can then eventually realize these projects and ideas. Because when it comes down to it, it’s very difficult to have any sort of propulsion towards a fulfilling life without at least some monetary momentum. 

So, in closing: if you’re a well-to-do entrepreneur who was enthralled by this piece, my Square Cash is$Maidenfed

Maidenfed (Jackie) is a New York-dwelling 25-year-old spinster who collages because she can’t paint and writes because she can’t rap. She is in a perpetual battle against relying on social media for external validation.



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