Art Man

Save an Uber, Ride a Cowboy is a column exploring queer millennial sex culture. The stories presented here are based on true events. Identities have been changed to protect the privacy and reputations of those involved.


She met him on a Tuesday night — back when she could afford to eat a full meal only once a day — thanks to a “dating” app called Seeking Arrangement which you can no longer find in the App Store (I wonder why). Like every other [unsuccessful] conversation she’d had through said app, Amy was having a very straight-forward conversation, this time with a man named Andreas. She was a 20-year-old bisexual Latina who had just moved to Manhattan, and he was a 43-year-old man asking if she would go over to his house that same night for $400. Although the word “sex” was never mentioned, it was implied, and she didn’t really mind. So she took the 4 train to Barclays Center at 10:00 P.M.

It wasn’t a date. She’d been on exactly two dates in the city — once in Central Park with a dream-girl who always referred to her as Miss Yellow (since yellow was Amy’s favorite color) and once over dinner with a man she met spontaneously at Union Square. If only millennial dating culture wasn’t so nonchalant, Amy really thought Dream Girl and Mr. Union Square would’ve been perfect candidates for future lonely nights… then again, Mr. Andreas, who pays $400 a visit, a 34-year-old millionaire living in Uptown Manhattan, and a 42-year-old cop willing to pay $300 for a kiss, were also pretty good candidates (though, for different reasons).

These last three men were all Sugar Daddies, or men willing to pay young women hundreds (sometimes thousands) of dollars for either sex or just company. These men have so much money that they don’t mind “sponsoring” or “mentoring” girls like Amy.

She liked older men; she liked sex, and she obviously liked money. Getting paid by older men for doing anything related to sex seemed like the perfect part-time job.

At the time, Amy was crashing at her best friend’s apartment, who was currently vacationing in Puerto Rico along with Amy’s only other friend in the city. She was all alone in Manhattan, so in an effort to prepare herself for the worst case scenario, she texted her closest friends where she was going, even though they were a thousand miles away.

On her way over to Mr. Andreas’ apartment, as she was smoking her habitual calm-down cigarette, she passed a Police Precinct (and a shocking amount of drunk people). She thought to herself, Well, my friends are out of town, but there’s police and drunken witnesses. If anything goes wrong… at least I have that. She felt surprisingly calm. Soon enough, she was standing in front of one of those frosted glass doors, the shadow of a man approaching her from the opposite side.

Mr. Andreas was a little bigger than she had expected; he wasn’t ugly but he wasn’t incredibly handsome either — he was just fine. He had a beard and hair that reached his shoulders, with tattoos covering his arms almost completely. He looked like a wannabe rockstar turned family man. “Watch out for that bicycle,” he said as Amy made her way up the stairs and into his home.

And it was huge. I mean, reader, keep in mind how expensive rent can be in a city like New York, this man’s “apartment” consisted of three whole floors, each of which were bigger than the apartment Amy was living in. And every single wall was covered in artwork: paintings, a mural covering one wall from the top of the high ceiling to the hardwood floor, old musical instruments, DVDs, CDs… he was an Art Man, and as a fellow art lover, Amy was impressed.

Once inside, Amy sat down next to him on the sofa, and as they were “watching” some TV show about some comedian, they started talking about their lives. He was kind, respectful, and although perhaps he was anxious to get her into his bed — patient. After all, he knew this was, in a way, a “first time” for Amy. But then the wait was over, and he asked Amy if she’d like to go upstairs to his bedroom. She said okay, because what else was she meant to say?

Suddenly, she wasn’t so calm anymore. As Amy walked up the stairs, eventually sitting down on his bed, she realized she was actually expected to have sex with a man who was more than twice her age for money. The thought of actually going through with it made her feel dirty… Correction: she felt like she was supposed to feel dirty, and for a good reason. To this day, the [sexist] society we live in depicts sex workers like strippers, prostitutes, and Sugar Babies as a group of troubled, desperate women, who have sex with disgusting men for a miserable amount of money.

But he wasn’t disgusting, and she wasn’t troubled. Desperate for money? Only a little bit, but he was also desperate for something. And so Amy came clean, told Andreas about her newfound insecurities, to which he replied, “You don’t have to do anything you don’t want to do. I would hate for you to feel uncomfortable.”

“I did crazy things for money when I was your age, too,” he continued, in an effort to help Amy wrap her head around her thoughts. That’s when it hit her: this is just a grown man who wanted to feel the warm touch of a younger woman, and was willing to pay for it. Amy just happened to be the younger woman. Once again, he let her know, “You’re free to go if you don’t want to do this,” and she was…

And so she stayed. She stayed because she wanted to, because she liked him; Andreas was interesting and smart and pretty sympathetic. Laying in bed, they started talking about other things; Amy noticed some drawings, hanging on his bedroom wall, that looked like they had been painted by little kids — that’s when he confessed he had children.

“I have a nine year-old and a thirteen year-old,” and that was the last piece of information he gave about his private life. After that they decided, without words, to take things slow. 

Andreas started by massaging her legs, her feet, eventually massaging her whole body. What he didn’t know was that a good massage was Amy’s biggest weakness. So she let him kiss her, and he wasn’t bad at it, which lead to…

In an episode of Sex and the City, Samantha Jones said, “… money is power. Sex is power. Therefore, getting money for sex is simply an exchange of power.” And she’s right. When you’re a sex worker (whether you’re sleeping with your client or not), you know you have power. If the client offers you one thing, but you think you deserve something more, you can speak up. Just because they’re paying for sexual services doesn’t make it okay for them to abuse of their power. Sex is power. Money is power. Getting money for sex should be an exchange of power, not an abuse of it.

Suddenly, it was 11:40 P.M. and Amy was dressed again. She didn’t feel gross or bad about herself afterwards. She hadn’t been forced to do anything — she knew she had done what she wanted to do for money, not what she had to do.

Once finished, they went back downstairs and Amy played with his cats and started tuning the ukulele he had lying around.

“You play the ukulele?”

“Yes,” she replied.

With that, she realized the strange thing about an exchange of power: you might spend hours talking, but you never really know each other. The things she let him know about her life were not the same as the ones she would reveal to a person on a regular date (and vice versa). Let’s bring back Mr. Union Square and Dream Girl from the second paragraph for a quick comparison. Amy’s dates with these two individuals were actual dates meant to get to know each other better. The purpose behind a date with a Sugar Daddy, essentially, is not that. It’s just an equally beneficial business deal disguised as a date.

And so she got on a Lyft (which he paid for) and went back home, $400 richer, looking for a place where she could do her nails the following day.