I’m a Straight Man, and He’s My New Sugar Daddy

When one broke Brooklynite embarks on a new side job as an escort for hire, he finds himself swimming through a murky world of easy money, broken promises and naked truths.

I’m a Straight Man, and He’s My New Sugar Daddy

When it comes to setting up an encounter with a potential sugar daddy, there are certain precautionary steps that my sex-work mentor, an exotic dancer, model and sugar baby whom we’ll call Chelsea Dawn, always takes. Curled up with a mug of tea on the cozy end of her cloth-covered futon, she takes me through the process.

While I listen to her motherly advice and gentle admonishments for my own previous lack of caution, I’m enjoying my own cup of Moroccan mint in Dawn’s spacious Bushwick loft, the rent of which is now paid for by one of her sugar daddies. The living room is crowded with DJ equipment, hula hoops, racks of costumes and a “Scarface” chandelier hanging from the ceiling, declaring that The World Was Ours.

Sugar baby/daddy relationships are more nebulous than those between most other sex workers and their clients; compensation varies wildly, sugar babies are paid for anything from going on casual dates to accompanying sugar daddies on vacation, and sometimes sex isn’t part of the deal at all. So it’s that much more important for a sugar baby to set up clear terms from the outset. Some of Dawn’s tips are fairly common sense: she always comes to an agreement about how much she expects to be paid for her time and whether sex is on the table; meeting in a public space is a must and she almost never goes with a sugar daddy to their home.

But before all of this, if she comes across a handsome prospective sugar daddy online, she makes sure that they are using an actual, current photo of themselves. In her fast-paced, caramel-soft voice, Dawn explains that, “after they send me a couple of pictures, I will tell them to send me a picture holding up a certain number of fingers or have them write a sign that says my name on it and hold it up to the camera and take a picture of it.”

Not only does this step ensure to some degree that you don’t get Catfished, it also shows the prospective date that your trust is something to be earned.

The more hoops a sugar daddy has to jump through, the more likely it is that he is serious about the arrangement in the first place and less likely to take advantage of you. Or at least this is what Dawn, who has been on upwards of twenty sugar baby dates and held down two long-term arrangements, has found.

Nodding along, I wish I had met Dawn a few months earlier, before I tried my own hand at being a sugar baby.

Late one night last August, after taking a shower and brushing my teeth, I spent a longer-than-usual time rifling through my underwear drawer. I wanted something plain and simple that would amplify my package without being too uncomfortable. While perusing my options naked in my bedroom, I opened my laptop for one last scan for clues that I might end up headless in the Gowanus Canal the next morning.

His picture only revealed his bare torso and enough of his legs to get the idea that his briefs were packing heat. His OkCupid profile claimed that he was Italian and a ripe thirty-two years old. His messages to me said that his name was “Renato” and he lived by himself in a slightly ritzier part of Brooklyn than my own.

When I asked Renato what he was looking for, he said he is just a straight “cool dude” looking to experiment with other “cool and open-minded guys over a few beers.” He also told me he would pay for the cab both ways, all the booze I could ask for, and even the occasional meal. His mindset seemed to at least partially align with my own interests.

My goal in meeting this man was simple: I wanted to perform both a social and personal experiment.

The personal would aim to satisfy a confused mix of self-loathing and curiosity about men after experiencing a string of failed romances with women. I identify as straight, but after contracting a surprise STD from one love of my life and being routinely cheated on by the next, I felt like taking a break from women. My hope was that, in having sex with a man, I might avoid the traumatic memories of vaginas past while enjoying the same release that healthy sex had once been for me.

My social experiment would be to dip my toes in a world that has been getting a lot of media attention in New York City lately: sugar babying, a type of sex work (although sex is not always on the menu) that connects the young and broke with the rich and lonely.

The New York Post and Daily News have written a number of eye-grabbers about sugar baby/daddy social events over the last few years. In September, the Atlantic published an in-depth look at the nature of sugar baby/daddy relationships, which featured several college educated women in their mid-twenties and based in New York City. In January, one of the most popular sites for both babies and daddies, released a press kit that claimed 585 of their active users attended either Columbia or New York University. This put both schools in the national top twenty rankings of universities with the most sugar babies. The press kit was titled SBU: Sugar Baby University. For New York college students and recent graduates like myself, word is getting out that rent and student loans don’t have to be so hard to pay off after all.

Over the summer, a close friend of mine signed up on SeekingArrangement. We were both suffering financially from the mid-summer service-industry slump, and she figured it was finally time to give something new a try. After a couple of weeks, Annabel started getting offers from sugar daddies, including one who paid her fifty bucks to sit in a park and talk for half an hour. If she made that much sitting on a bench, I wondered how much I could make lying on my back.

So, with fantasies of subverting societal conventions of sexual orientation, prostitution, and the best way to afford a New York night out, I strolled onto the Internet looking for some dude to bang who would pay for my time in the form of alcohol, cab fares and bar snacks.

Renato’s pictures and messages gave me no reason to suspect he was anything but an out-of-shape-ish, horny, aggressively lonely but essentially harmless, closeted and internally conflicted, cautiously masculine and emotionally racked dude. Just another normal New York City male. But I still wrote the name he gave me, his number, the address where I was meeting him, and the time and date on a piece of notebook paper that I placed in a very obvious spot on top of my dresser.

I was unsure whom exactly I was leaving it for. Was my roommate going to stumble over this and be filled with questions, or was some Mariska Hargitay character going to find it and say, “here’s the answer to what happened to the late Mr. Miller?”

As an added precaution, I texted my sugar-baby compatriot, Annabel, that I was about to do something risky and would check in with her in an hour.

My cab honked outside and I quickly settled on a tight-fitting pair of black boxer briefs before throwing on my most elite dive-bar attire and hustling out into the damp and dirty heat of the summer night. I texted the man who would become my sugar daddy that I was “on my way, winky-face emoticon.”

We would meet five or six times over the course of the next seven months, always at either his place or a dimly-lit and sparsely-populated piano bar down the street. Our more-or-less-unspoken deal was less lucrative than I had hoped for, although he did once offer to buy me a ticket to Puerto Rico to vacation with him.

Renato would pay for my cab rides and any drinks I would get at the bar, with the expectation that I would provide sex in one form or another before heading home; not a terrible deal as long as he kept his promise to never expect anything that I wasn’t comfortable with. It took a while for me to realize that Renato would not be respectful of my boundaries when I most needed him to be, and on more than one occasion he took it too far.

One of the last nights we went out together was to Pumps, a famed down-to-earth strip club nestled between repurposed warehouses and a creek at the northeastern border of Brooklyn.

It was a slow night. Some of the dancers were sitting at the bar watching one of the two televisions that hung over the flanks of the stage, both playing an episode of S.V.U. with subtitles. As the night drudged to a sleepy close, “Creep” by Radiohead started playing on the bar stereo.

For the few blessed seconds during the melancholic opening notes of the ’90s paean to stalkers, the loudest noises in the room were the claps of the eight-inch heels on the dancers as they caressed and danced around their poles with angelic grace. I was in near silence, watching an assortment of naked beauties of my generation flutter across a stage in a dark, empty room at the edge of an industrial wasteland.

That was when Chelsea Dawn, a round-nosed redhead with smoky eyes and rapturous presence, stepped up to the stage.

Moments before, Dawn had told me offstage about her other career as a performance artist, fire dancer and model. She also told me that she works as a sugar baby. I asked her why she worked at Pumps rather than at a restaurant as a server or something similar. Her response was simple: without rich parents paying her bills, sex work had become the most efficient way for her to afford living as an artist in New York City. “As much as I love this,” she said, “it’s about the money.”

It was those troubling words that ran through my head during her routine. Pumps has a reputation for stellar pole dancing, and Dawn gave proof to the rumor. After a well-executed martini spin down the pole, she rested on all fours with her back to Renato and myself to demonstrate her twerking skills.

She was good. And judging from the alluring smile, she was having a good time demonstrating just how good she was at her job. I was reminded of the feeling I get when I pour an expensive bottle of Cabernet Sauvignon at my restaurant job without spilling a drop. Or when I chastised Renato into buying me the top-shelf whiskey before letting him give me head in the back of a bar.

Renato nudged me out of my thought process and pointed down at Dawn’s undulating backside, “do you want to have sex with her?” Yes, I did. “Ask her how much she wants to have sex with the two of us.”

For some reason, I felt that a line — one that had grown increasingly hazy since I began my relationship with Renato — had now been crossed. He wouldn’t go up to a dancer at a stage show and ask that question, just as he wouldn’t make an offer to me if I flirted with him while waiting tables at a restaurant, so he shouldn’t assume that a dancer at a strip club is looking for people to pay them for sex. I told him so.

Drunkenly, Renato made a stand for himself. His argument ran somewhere along the lines of “because she is putting herself out on a stage sexually, she is obviously open to having sex for money.” He made the analogy that she was like a painter displaying her works in a gallery, and it was his right to ask to purchase one of them.

“Was this true?” I wondered, trying my best not to stare at Dawn’s labia, which had slipped past the thin barricade of lingerie while she demonstrated her chopper spin. It seemed in incredibly poor taste to proposition a performer during their performance. I told him so and, after a quick spat, we decided to leave the dimming venue and its masters of the American dance behind.

A few days later, Dawn responded to my friend request on her Facebook dancer/model profile page. I needed to know why Renato’s proposal had felt so upsetting, and why sugar babying was so intriguing to a new group of sex workers. I needed to talk to someone about what I was doing myself. She agreed to have a conversation at her loft in Bushwick about her experience as a sugar baby.

Dawn works two to three days a week at Pumps to ensure that she can make rent in her ancient converted loft building, within spitting distance of an elevated train in Bushwick, a few miles from the club. After visiting a New York rave in 2012 where she met several artists and had her body painted for the first time, Dawn dropped out of college to move to the city, where she’s been modeling and performing ever since.

She told me all of this after a mild-but-supportive scolding for taking such a huge risk on someone who turned out to be less than trustworthy.

I had told her about the instances that made me regret not making the arrangement between Renato and myself clearer. The first time was in his apartment. After he physically overpowered and spanked me because “that’s the way you like it,” despite my pleas for him to stop, he hid my clothes behind him so that I could not leave the apartment until he let me, which would only happen if I helped him reached orgasm. It was a brutal, cold and lonely walk to the train station that night.

Another instance took place during the cab ride home the night we met Dawn at Pumps. While we were in the cab Renato drunkenly pulled my dick out of my jeans in order to coax me into letting him stay at my place. It was not a convincing routine. To avoid letting him find out where I lived, I jumped out of the cab at a busy intersection and darted around as many corners as I could, inadvertently exposing myself to the rats, garbage, and a few late-night prowlers on Flushing Avenue.

Dawn could relate. Her first sugar baby-daddy relationship began a little over a year ago, when a handsome and “pretty creepy” older man in his forties approached her at a venue while she was being painted and hinted at an “arrangement.”

At the time, Dawn had very little understanding of what a sugar daddy-baby relationship would entail. “If you look at even the naming of it, I kind of expected it to be like a daddy-daughter relationship, but with sex.”

Although Dawn dispels the idea of being completely naïve when she began working as a sugar baby, it does sound like there was a faint glimmer of romanticism about what it would be like to have a sugar daddy, “I kind of expected it to be a little more of a mentoring relationship, not just, ‘your time for my money.’”

After a year of meeting men on, Dawn holds little esteem for the pretense that having a sugar daddy is anything other than sex work, “‘I’m just here to look out for you,’” she says, mimicking what guys have said to her, “like, obviously you are here to look out for me and fuck me.”

Still, the terms that Dawn and her first sugar daddy set over the phone more than a year ago did not include guarantees of sex. For the most part they met in public at fancy day-spas where he would pay for the two of them on top of her $250 fee. Not a bad gig.

Unfortunately, Dawn had to terminate their arrangement for reasons I myself had recently become familiar with.

Her last night with that sugar daddy ended when he tried to rape her following a birthday party at his house, after she forcefully rejected his proposal to, “let me put it in your ass, I’ll give you $2,000.”

“I was in his apartment, his wife was already passed out in bed, and everybody had already left, and my friend was not very conscious, kinda going in and out,” Dawn tells me with a sudden uncharacteristic falter in her voice. “Only he and I were awake.” (Bringing her six-foot-eight, two-hundred-and-something-pound friend along had been Dawn’s precaution, but she says her sugar daddy had been very intent on getting the friend as drunk as possible that night.)

“He was very drunk and I was not drunk at all. I was scared shitless because I knew that if worse came to worse, my friend couldn’t help me, his wife wouldn’t know…If I fought I would lose, and if I ran I would be leaving my friend behind, which I would never do.”

Eventually Dawn managed to rouse her friend to the point where he could walk and the two of them made a hasty escape, never to see that man again. Since then, she has been decidedly more selective of her daddies.

She currently has two sugar daddies, one who lives in New York City and another across the country. She only sees the latter one when he invites her along on occasional business trips; she spends the days exploring new cities by herself and nights as his date. The first trip was to Charleston, South Carolina; the second will be Toronto.

It’s not only the $250, tax-free, she makes in a night that Dawn hopes to get out of her experience as a sugar baby. For her, it is also the chance to bump elbows with people who can further her other career interests, such as a new project she started in March — a line of sex toys made specifically for people in transition between gender identities.

“I will never do this without someone who is willing to mentor me,” says Dawn, speaking of what she finds to be the empowering element of sugar babying.

Her New York City daddy is a forty-two-year-old man who does something involving e-commerce (as two art-scene hipsters not versed in the goings-on of Manhattan high-rise offices, neither Dawn nor I could figure out what his actual job title was, try as we might).

He once told her that, “this money is in lieu of a commitment I can’t give you,” referring to the amount of time his work requires of him. In a sense, he sees her as his part-time girlfriend, who will plan dates and at least pretend to be interested in his career, which is something Dawn has begun to master.

“The ‘feigning interest face’ — you gotta perfect that,” she says, demonstrating with a slightly downward tilted head, folded hands and an inquisitive grin.

It is that perspective that seems to make all the difference when distinguishing sugar-babying from run-of-the-mill prostitution. The idea that this is a real relationship, one which requires those involved to at least partially enjoy the company of one another, allows educated (and even financially stable) young men and women to engage in sex work without feeling as much of the stigma.

Since a sugar baby/daddy connection is an ongoing relationship in which both people must get to know one another and provide for another (the daddy: financially, and the baby emotionally and physically), it essentially makes this type of sex work sound like old-school traditional marriage. The key difference is that this is not a legal contract, and a sugar baby, unlike brides from the not-too-distant past, has the ability to choose their partner.

After the night of our visit to Pumps, my inconsistent six-month relationship with Renato ended with me blocking and deleting his number. It just wasn’t worth it to spend my nights out feeling nervous about what might happen next. He wasn’t the last sugar daddy I reached out to online, but after a handful of other prospective men and women sent me messages via SeekingArrangment and CougarLife (a website designed to link older women to sugar babies), I began to feel disconnected and depressed. I decided to not meet up with any of them and deleted my accounts. Although I certainly got what I was initially looking for — a new experience and a few free nights out on the town — my experience with Renato has left me feeling that even if it were just a simple trade of my time for other people’s money, it would still feel like a risk with little guarantee of reward. Especially now that there is much less of an illusion of safety.