Seeking Arrangement: On My Brief & Failed Attempt at Becoming a Sugar Baby

BY ANONYMOUS

Seeking Arrangement, a website that connects potential "sugar babies" with sugar daddies and mamas, has been around since 2006, but about once a year some enterprising reporter seems to discover it anew, thus provoking another round of incredulous blog posts and Tweets.

I signed up with Seeking Arrangement in 2010, when I was living in Brooklyn, NY and—due to rent, road trips and too many visits from the weed delivery service—somewhat cash-strapped. But more than that, I was curious. Single for more-or-less the first time since age 17, this was the same time period when I first began blushingly perusing the Craigslist casual encounters ads. I wanted adventure. I wanted money. This seemed like a good way to satisfy both needs.

So I created a seekingarrangement.com profile, carefully crafting my image as a young writer eager to rely on the kindness of strangers. And, soon enough, the messages began pouring in. What I hadn't accounted for was all the online communication necessary to weed the weirdos from anyone with potential—I can barely manage to keep in contact with the people I love, let alone find time or motivation to talk to would-be sugar daddies. I had all but declared the experiment a wash until one night in July when my house threw an afternoon party.

The afternoon party is only relevant because it involved a lot of drinking, early in the day. It also involved a lot of being around my most-recent ex, whom I was still living in the same house with. At some point, the combination of the two propelled me away from the crowd, up to my bedroom and onto Seeking Arrangement. I can't remember exactly how it happened, but I ended up agreeing to meet up with a man we'll call Dave at a bar in the Lower East Side.

Now, normally, you couldn't drag me from Brooklyn to Manhattan on a weekend if you told me there was a free Malbec, macaron and kitten party. The fact that I felt willing to do so explicitly says I was in no condition to do so. Because I knew my friends would try to stop me, I told no one. I snuck out, took that L train under the East River and considered what I knew about Dave: He was around 40. He was blond and a little stocky, according to his profile pictures. He was married (but no children). And he held some sort of job in the music industry.

This last bit was what made me settle on Dave, I think; we had exchanged messages about Arcade Fire and LCD Soundsystem, and he seemed like someone that, under other circumstances, I still might hang around. Sure enough, Dave did turn out to be easy to talk to. Conversation flowed naturally and normally, and I remember enjoying myself as we drank wine and discussed bands, life in NYC and why he was looking for a mistress. After the first round of drinks, he pulled out a wad of cash and handed it to me.

"Let me give this to you now, for your coming out to meet me," he said. "So you know I'm not bullshitting you. There will be a lot more if, you know, we decide you want to see me again."

I took the money sheepishly, without so much as glancing at how much it was, and put it in my purse. After another round or two of drinks, the entire day of drinking had really caught up with me. "I'm starting to get dizzy," I told him as we stood outside the bar smoking cigarettes together. "Let me put you in a cab," he said. "Or if you need to lay down first, my office is right around the corner."

Dave wasn't a bad-looking guy—a little chubby for me, a little short, but not bad. He looked a lot like the writer Chuck Klosterman, black-rimmed glasses and all. I'd been enjoying hanging out with him, and wanted him to like me. Plus, laying down did sound nice. "Let's go to your office," I said.

That is pretty much all I remember. If you're thinking "Oh, no, she was drugged!"—nope. I mean, I'm 99.9% certain that's a nope. I was just really drunk, way too drunk to have even left my house, let alone go somewhere alone with a stranger. Luckily, Dave did not turn out to be a rapist or a serial killer or anything else nefarious. I woke up the next morning on a couch, fully-clothed, with a blanket draped over me and a massive headache.

The first few minutes of that morning were mind-boggling. I looked around at my surroundings: A very large loft space, with one entire wall of windows. A desk toward the back of the room, separated from the couch I was on by a pool table and a pinball machine. I checked by body: Clothes in-tact, no sign of forced entry. On the table there was a note: "Liz, you passed out and I had to get back to my wife. Take care--there's vitamin water in the fridge. Talk to you soon."

At that point, Vitamin Water sounded like manna from Heaven. I made my way to the fridge, which was entirely full of nothing but Vitamin Water and Red Bull (I took two of the former and one of the latter). Then I remembered the money Dave had given me at the bar. I checked my purse: $200.

It was only about 6 a.m. at this point, a beautiful July morning. I decided to walk home across the Williamsburg Bridge, and as I did—barefoot, carrying my painful shoes, downing the grape Vitamin Water, smoking a cigarette—I'd like to tell you I was thinking about how lucky I was that nothing bad had happened. But all I remember thinking about was that this had been a strange adventure and the sun coming up over the East River made the whole world seem beautiful and full of potential.

Back home, I messaged Dave apologetically, and a few hours later he messaged back proclaiming it NBD. He'd had fun hanging out and wanted to see me again if I was into it. But I was too embarrassed by the whole thing by this point—the drunkenness, the passing out, the very fact of meeting up with a sugar daddy. It seemed somehow, suddenly, sordid. I vowed not to see Dave or use the site again.

Conviction, however, has never been my strong point. A few weeks later, I accepted a request to meetup with a youngish lawyer who wanted to go to Roberta's, a wood-fired pizza joint near where I lived. I'd frequented Roberta's when it first opened, back when it was still BYOB; but now it attracted Manhattanites who would otherwise never set foot in Bushwick, and there was always at least an hour wait on weekend nights. I don't think there was anything particularly exciting about the profile or online conversation between me and the lawyer, but he was legitimately attractive—thin, Asian, shaggy-haired—and I really liked Roberta's, so I agreed.

It didn't start off on a good note. One of the first things he said to me was "I'm not really looking for a sugar baby; I just thought this seemed like a way to meet cute girls."

This annoyed me,of course, because I wasn't looking for a boyfriend. I felt tricked, which is never a good way to start things off, and dude also turned out to be that awesomely obnoxious combination of boring and cocky. It became clear within about 10 minutes that we had absolutely no conversational chemistry. Later that night, I left him dancing in a group on the Roberta's patio, insisting he should stay and have fun and I could find my own way home, thanks.

My third and final foray into becoming a sugar baby involved a man who called himself Ralph. After the first two attempts, I decided maybe I needed to go more against type. Ralph looked to be in his 50s and his profile pic was him standing next to Dick Cheney. Bingo. He asked me to meet him in Midtown for tea, because he didn't drink.

Over tea, he told me how he lived in Connecticut but worked in the city (I want to say he lived in Greenwich, but I think that's just mis-remembering out of stereotype). He kept an apartment here for when he worked late. He hinted at belonging to either The Carlyle Group or the family that owned The Carlyle hotel, I couldn't discern which. After barely a few minutes of conversation, he wanted to get down to business: "So what kind of financial support are you expecting?"

"Ummmm .... uh ... I don't know."

"What kind of arrangement are you seeking, then?"

I didn't have a good answer here either. I am the worst sugar baby ever, I thought, and went with the ol' 'What are youuuu looking for?"

What Ralph was looking for was someone to meet him at his Midtown apartment, once or twice a week, for sex. Each time we met, he would give me $300, with bonuses for good behavior. Occasionally, he might want to go out to dinner or take me to a work event.  His directness was admirable yet off-putting. Did I want to see the apartment when I finished my tea?

I agreed, though I was pretty certain this was not going to work out. Ralph looked like an older Baby Huey, and seemed to have a high-school nerd's chip on his shoulder. Back at his apartment--which was entirely empty, save for a few kitchen goods, some clothes in the closet and a mattress on the bedroom floor--Ralph cozied up and started kissing me. He smelled awful. "Tell me about what you were like in high school," he said.

"I ... went to Catholic high school for a bit, and then switched to public," I told him. "I got good grades. I ... was a cheerleader."

"Mmmm, my little cheerleader," Ralph said. "Did you wear a short, short skirt? Did you naughty things with the boys?"

Oh, gawd, it was too much. I can abide bad x-rated talk from someone sexy, but this just would not do. Unfortunately, Ralph was much less understanding than Dave. When I tried to politely excuse myself from the situation, I was met with more pawing and a side of guilt trip. I am probably going to regret admitting this, but I gave him head because it just seemed like the easiest and quickest way out of the situation. The whole time, he talked about my cheerleading uniform and Catholic school jumpers.

Afterwards, he gave me $300 and asked when he could see me again. I told him I would be out of town for the next two weeks (true) and would get in touch when I got back. I never did.

As I took the subway back to Brooklyn, I thought about all the different 'arrangements' I'd encountered people seeking. Anyone who looks at or uses the website can attest that the desires are diverse. There really are folks looking for totally non-sexual arrangements -- people to take to events, people to provide companionship, people to take shopping because they (the men) have shoe fetishes. There are sugar daddies looking for someone to fulfill all sorts of specific fetish requests, and those looking for an old-school style mistress arrangement (some complete with housing!). There are men who simply want a girlfriend that's hotter than they may get without a little financial incentive. There are those who really want genuine companionship, and see this as a short cut. There are those who want  a girlfriend who won't make as many demands on them, whom they can essentially pay to not have hardcore needs and wants of her own.

And there are men, like Ralph, who mostly just want to pay women to meet them for sex. I guess in doing what I'd just done, I had just made myself a "whore." It didn't bother me too much, partly because I've turned down free drinks at bars from guys my whole life (part feminist principle, part misanthropy). I'd never expected or wanted dates to pay for me for anything. Meanwhile, I'd watched so many girlfriends over the years fool around with dudes they just weren't that into because they bought them jewelry, whiskey sours and concert tickets. 'Whoring' is just a matter of degrees, and I couldn't for the life of me believe this was qualitatively different than that.  But really, most importantly, I just don't think having sex for money is necessarily anything to be ashamed about. I respect sex workers and I respect sugar babies. We've all got to eat, and some of us really don't like working in retail.

Nonetheless, I never met up with anyone from Seeking Arrangement again. Avoiding awkwardness is pretty much my MO in life; and my preferred method of dating is to have enough drunken conversations with someone that we start sleeping together and sleep with each another enough that we start considering ourselves a couple. Finding a sugar daddy seemed too much like traditional dating, and that was 100% what I did not want.

I feel like I should come up with some moral to this story, but there really is none. As far as takeaways: 1) I suck at being a sugar baby and 2) sugar daddies come in all stripes. Maybe this is my moral: That there is no one type of woman or man using this site, and its silly to make blanket conclusions about them. And maybe that you shouldn't get wasted before meeting a strange man for drinks? But, meh, I can't even say that with much conviction, because it worked out just fine for me. Maybe my moral is just that there doesn't need to be a serious moral served up with stories like this. Sometimes we randomly decide to meet strangers for strange sexual arrangements, and it's really just not that big of a deal.

Editor's Note: An earlier version of this piece appeared on lunalunamag.com, our old site, in 2013.

 

Mandy's Strange Sex Questions Answered Through Literature: Spiders

In Mandy De Sandra's first advice column installation, she will answer reader's questions about their ‘kinks’ and fantasies. Of course, Mandy will share personal advice and recommend a book to further explore their fantasy or fetish. Feel free to send a question via the form below. 

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Question: Mandy I have fantasies about spiders crawling on me while I touch myself. Is this weird? Should I ever try it?    

Mandy: Spiders have a sexy strut don’t they. They are a very sexual being, they basically cum houses. These bukkake homemakers are sexy, and your fantasy is normal. I write a lot about creatures and naughty idea that are taboo, with common sense we can really fulfill our fantasies. I think a good golden rule is if I want to make the fantasy a reality and it involves another breathing being—I need to get permission.

I personally recommend the book “Arachnophile” about the lust for a spider. Through fiction and fantasy we can find ways to play out our fantasies. Books are good too cause you only need one hand. 

- Mandy.

Mandy De Sandra is a Department of Labor worker by day but an erotica writer at night. Mandy is a #BizarroFiction#Erotica author, and more work can be read in Vice, The AVClub, Jezebel.

4 Classic Books That Gorgeously Explore The Subtleties & Madness of Sexuality

BY LISA MARIE BASILE

Sex writing is often a separate conversation from that of craft. I myself have taught Poetics of Sex but have always questioned the segregation of sex writing. Most successful writing is vulnerable and authentic - qualities that often seem intangible and subjective -  so why would sex somehow fall outside those confines?

Sex is part of the human experience, and if we take time to write the human experience well, sex would be like anything else: ordinary, as a cup of tea. It's the presentation of that truth that matters. Below, we compiled four incredibly honest, very human and beautifully written excerpts we loved. They may not be comfortable, but they are true to condition of wanting, lusting, desiring and even sinning. 

Anais Nin once said she was “conscious of a difference between the masculine and feminine treatment of sexual experience," which is one way of exploring sexuality  - its dynamics, its fragility, its physical differences. 

In Playboy, Nabokov explains Lolita, perhaps the most difficult of these books to digest:

“Playboy: Speaking of the very sick, you suggested in Lolita that Humbert Humbert’s appetite for nymphets is the result of an unrequited childhood love affair; in Invitation to a Beheading you wrote about a 12-year-old girl, Emmie, who is erotically interested in a man twice her age; and in Bend Sinister, your protagonist dreams that he is “surreptitiously enjoying Mariette [his maid] while she sat, wincing a little, in his lap during the rehearsal of a play in which she was supposed to be his daughter.” Some critics, in poring over your works for clues to your personality, have pointed to this recurrent theme as evidence of an unwholesome preoccupation on your part with the subject of sexual attraction between pubescent girls and middle-aged men. Do you feel that there may be some truth in this charge?

Nabokov: I think it would be more correct to say that had I not written Lolita, readers would not have started finding nymphets in my other works and in their own households. I find it very amusing when a friendly, polite person says to me—probably just in order to be friendly and polite—“Mr. Naborkov,” or “Mr. Nabahkov,” or “Mr. Nabrov” or “Mr. Nabohkov,” depending on his linguistic abilities, “I have a little daughter who is a regular Lolita.” People tend to underestimate the power of my imagination and my capacity of evolving serial selves in my writings. And then, of course, there is that special type of critic, the ferrety, human-interest fiend, the jolly vulgarian. Someone, for instance, discovered tell-tale affinities between Humbert’s boyhood romance on the Riviera and my own recollections about little Colette, with whom I built sand castles in Biarritz when I was 10. Somber Humbert was, of course, 13 and in the throes of a pretty extravagant sexual excitement, whereas my own romance with Colette had no trace of erotic desire and indeed was perfectly commonplace and normal. And, of course, at 9 and 10 years of age, in that set, in those times, we knew nothing whatsoever about the false facts of life that are imparted nowadays to infants by progressive parents.”

— Playboy

I love what Nabakov has to say because he diminishes the critic's obsession with finding the author's sin and instead says that whatever truth is within a person is going to manifest no matter what, even if the plot changes. That, to me, is letting the honesty run through the work, and I think the below excerpts showcase this duende and unbridled exploration of desire perfectly (not necessarily healthy desire or sex, per se, as Lolita is a story of both desire and non-consent or rape, to some). 

While Nabokov's novel is slightly different in that our lead is the step-father sexually objectifies his young daughter, his writing still explores those nether-realms where the true human condition, no matter how disgusting, is written about with honesty and clarity. 

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LOLITA, VLADIMIR NABOKOV
“I recall certain moments, let us call them icebergs in paradise, when after having had my fill of her –after fabulous, insane exertions that left me limp and azure-barred–I would gather her in my arms with, at last, a mute moan of human tenderness (her skin glistening in the neon light coming from the paved court through the slits in the blind, her soot-black lashes matted, her grave gray eyes more vacant than ever–for all the world a little patient still in the confusion of a drug after a major operation)–and the tenderness would deepen to shame and despair, and I would lull and rock my lone light Lolita in my marble arms, and moan in her warm hair, and caress her at random and mutely ask her blessing, and at the peak of this human agonized selfless tenderness (with my soul actually hanging around her naked body and ready to repent), all at once, ironically, horribly, lust would swell again–and 'oh, no,' Lolita would say with a sigh to heaven, and the next moment the tenderness and the azure–all would be shattered.” 

THE LOVER, MARGUERITE DURAS
Hélène Lagonelle’s body is heavy, innocent still, her skin’s as soft as that of certain fruits, you almost can’t grasp her, she’s almost illusory, it’s too much. She makes you want to kill her, she conjures up a marvelous dream of putting her to death with your own hands. Those flour-white shapes, she bears them unknowingly, and offers them for hands to knead, for lips to eat, without holding them back, without any knowledge of them and without any knowledge of their fabulous power. I’d like to eat Hélène Lagonelle’s breasts as he eats mine in the room in the Chinese town where I go every night to increase my knowledge of God. I’d like to devour and be devoured by those flour-white breasts of hers.

I am worn out with desire for Hélène Lagonelle.

I am worn out with desire.

I want to take Hélène Lagonelle with me to where every evening, my eyes shut, I have imparted to me the pleasure that makes you cry out. I’d like to give Hélène Lagonelle to the man who does that to me, so he may do it in turn to her. I want it to happen in my presence, I want her to do it as I wish, I want her to give herself where I give myself. It’s via Hélène Lagonelle’s body, through it, that the ultimate pleasure would pass from him to me.
A pleasure unto death.” 

TROPIC OF CANCER, HENRY MILLER
“When I look down into this fucked-out cunt of a whore I feel the whole world beneath me, a world tottering and crumbling, a world used up and polished like a leper's skull. If there were a man who dared to say all that he thought of this world there would not be left him a square foot of ground to stand on. When a man appears the world bears down on him and breaks his back. There are always too many rotten pillars left standing, too much festering humanity for  man to bloom. The superstructure is a lie and the foundation is a huge quaking fear. If at intervals of centuries there does appear a man with a desperate, hungry look in his eye, a man that would turn the world upside down in order to create a new race, the love that he brings to the world is turned to bile and he becomes a scourge. If now and then we encounter pages that explode, pages that wound and sear, that wring groans and tears and curses, know that they come from a man with his back up, a man whose only defenses left are his words and his words are always stronger than the lying, crushing weight of the world, stronger than all the racks and wheels which the cowardly invent to crush out the miracle of personality. If any man ever dared to translate all that is in his heart, to put down what is really his experience, what is truly his truth, I think then the world would go to smash, that it would be blown to smithereens and no god, no accident, no will could ever again assemble the pieces, the atoms, the indestructible elements that have gone to make up the world.” 

DELTA OF VENUS, ANAIS NIN
“How do I look to him?" she asked herself. She got up and brought a long mirror towards the window. She stood it on the floor against a chair. Then she sat down in front of it on the rug and, facing it, slowly opened her legs. The sight was enchanting. The skin was flawless, the vulva, roseate and full. She thought it was like the gum plant leaf with its secret milk that the pressure of the finger could bring out, the odorous moisture that came like the moisture of the sea shells. So was Venus born of the sea with this little kernel of salty honey in her, which only caresses could bring out of the hidden recesses of her body.”