Jack was breaking the rules of our arrangement the first time he told me he loved me. I was twenty-four years old, and I was his sugar baby. The guidelines we’d agreed on had come nine months earlier via an iMessage that Jack had typed completely in Baby Boomer innuendos: I would like to get to first base, second base and third base, but the more often we do home runs, the more gifts you will get. J
Gifts was ‘sugar lingo’ for things like shoes and jewelry. I learned this from the internet after I’d met Jack at a club, where he’d slipped me four hundred dollars, his business card and a proposition to have dinner with him. Paid, cash. I googled sugar baby, only to find that the most respectable literature about this kind of arrangement was tucked away in a Reddit thread: New to the sugar bowl, what do I need to know? This prompted me to search the term ‘sugar bowl’ which at first only pulled up a lot of dessert recipes, but, as it turned out, the sugar bowl was a term that embodied the whole world of sugaring, sort of like the wizardly world of Harry Potter.
Gingerbaby96 posted: Sex is required, and The price will be decided by you and your sugar daddy (often abbreviated as SD).
Newbabe wrote: The sex could be good or bad, depending on how eager your SD is to please you.
Sugarsugar knew a lot about the financial aspect. She said: Start buying things with cash, don’t put your money in a bank, and if you must, never, ever make a transaction more than $10,000 or the bank must report it to the IRS.
Jack’s love declaration came about in the fall semester of my final year of college.
The FAFSA awards had just been offered, and I logged into my university account, hitting “decline” for the first time in my life. My college journey had been long and inconsistent: two-time drop out and twice returned.
All prior semesters had been paid for via a blend of subsidized and unsubsidized loans. Had I logged into my Sallie Mae account, I would’ve seen an ever-expanding figure reaching upwards of $35,000. Bold and awaiting payback. With ‘moderate’ interest rates between 4-7%.
I’d paid for the semester’s tuition out of my own pocket, with money I’d earned from giving blow jobs to Jack.
I clicked the mousepad with all the might my finger possessed—it was a click stronger than all the accumulated Accept clicks of the past. Good for me, I thought, for being so responsible with my money.
It was bigger than the fact I’d saved and allocated $3,656 for my education, but I understood that I’d just dodged a decade of accumulated interest on a loan I no longer had to take out. Had there been a bottle of champagne nearby, I would’ve popped that baby open and chugged it straight from the lip.
“Whoopity-do,” I cried out to my laptop screen. “Thank you, Jack!”
Wanting to share my accomplishment. I decided to ring my dad.
My father was my best friend. While we’d always been close growing up, his second divorce ran parallel to a recent break up of my own. We bonded over nightly phone calls where we’d recount our daily dramas. Sharing our pain made us feel less alone, less miserable, like it was almost funny.
I’d first told him about Jack while he and I were sitting in our local mall’s food court. I was only one week into my sugaring arrangement. My dad and I shared a lemonade and a footlong corndog from Hot Dog on a Stick. My sister was there, too.
He asked me if there was a difference between sugar babying and prostitution. “Sort of,” I explained. Sure, I was being paid for sex, but with sugar babying there were specific rules that Jack and I had agreed upon. I was making $1,200 a week, to spend one hour with Jack in La Quinta Inns. According to a 2018 stat from seekingarrangement.net, that was nearly double the national average, which the site claimed had been $2,800 a month per baby.
“Well, Shell,” he slurped the straw. “It’s not great, but as long as no one’s getting hurt. Who am I to judge?”
I nodded in agreement. My whole family seemed to agree that the arrangement was a lifeboat—come to save me from the sinking ship of my broke ass life—but what I didn’t know then was that after the sessions, when Jack would clean himself in the shower, I’d be putting my head in my hands and repeating to myself: I can’t do this. I can’t do this. I would never tell anyone the dark turn it would take, not wanting my family to know that I thought I might be getting hurt. Not in the physical way, but the invisible kind of damage. The kind that would make me wonder if I had gone bankrupt inside. The kind that would make me question what kind of person I was.
In the weeks between that conversation at the mall and declining the loans, when I left the hotel rooms with Jack—when I would feel sorry for myself—I’d think about my dad and the labor of his own body. How as a child he’d spent several months out of every school year living on migrant farms in Idaho, harvesting potatoes with his family. Sugaring—the tasks of the job—were hard on me in one way, sure, but so easy in another. Wasn’t I lucky? I would ask myself, as I counted out the money: always given to me in white bank envelopes after the fact. Stacks of hundred-dollar bills. Yes, I’d think. Just like I’d won the lottery.
After I declined the FAFSA loans, I called my dad with my good news, thinking he would best understand how much money I had just saved my future self.
“You just lost yourself a vacation to Mahi-Mahi,” he said.
“Isn’t Mahi-Mahi a fish?” I asked.
My dad assured me that the location wasn’t the important forfeiture here, but the trip.
“You should be using the money to live your life, Shell. You think for a second student loans are going to matter in the apocalypse?” He quickly pivoted the conversation into something he found much more interesting: a survival lesson. “You want to make a good investment?” he asked me. “Buy a gun.”
Given that my father was convinced the world was on the verge of total collapse, his advice scattered between clinically insane and financially astute. And while my mother was more well-rounded in some areas, she was drowning in debt accrued mostly from charging too many hamburgers and sweet teas from McDonalds. My father had found her credit card statements and asked how it was possible for someone to owe so much without anything aside from a few spare pounds to show for it. The answer was simple: consistency and only making minimum payments for over a decade.
“I think it was a good investment,” I said. Aside from sharing my student loan joy, there was one other matter I needed advice on. Jack had recently offered me a ‘gift’: buying my school books for the semester. “What do you think I should do?” I asked my dad.
“You know what I think,” he said. “Take it. Cha-ching!”
A few weeks earlier, after declining another one of Jack’s gift offers—a new iPhone—my father talked me off what he referred to as a “stupidity cliff.” This time we were eating lunch inside Taco Bell’s “cantina.”
I’d always prided myself on saying no to Jack’s gift offers, thinking it was the most responsible thing to do. In terms of sugar daddies, he was already being pretty generous, paying me over a grand a week for an hour of my time and moderate access to my body. Back when Jack had first made the arrangement offer, penetration had been agreed upon, but as it would turn out, Jack would lose his erection whenever the condom came out. While my duties decreased from sex to blow jobs, the original figure still stood. This made me feel like I’d gotten a pretty stupendous deal.
So why take Jack up on gifts when I didn’t actually need them? What I wanted was to get out of debt so I could get my real life started. Had he proposed making student loan payments for me, I would’ve said HELL YES, and even provided him the login credentials, entrusting him with my social security number and address—so he could make payments from the comfort of his own home.
“Anything, and I mean anything Jack offers you, you should take,” my dad told me. He saw this simply as good business. To him, any gift was just the opportunity to own something nice.
I wanted to tell my dad that it was complicated to receive. I worried if I took Jack up on these little side offers, he would think I was getting too much for what I was giving him. I didn’t want to encourage Jack to look for a sugar baby that required less. Like, unprotected sex. Seekingarrangement.net advertises to men on their homepage, “Four babies per sugar daddy—the odds are in your favor!” I needed to be as low-maintenance as possible; I thought of this as job security.
I spared my dad the details and just said, “I don’t think that’s a good idea. He’s not even offering me things that I want.”
“Oh my god,” my dad said. He was using a plastic spork to scrape clean the boat his Nacho Supreme had been served in—no bean or chip crumb that he’d paid for would be wasted. “I thought I raised you better than that.” My father shook his head at me, truly disappointed, and then lifted his spork to his lips. What went into his mouth appeared to be a full tablespoon of sour cream. “Next time he offers you something you don’t want, you say, ‘Yes, thank you, Jack,’ and then you give it to one of us.”
“You don’t even know what an iPhone is,” I said.
“Nope, but I know what free is.”
This is essentially where my dad, and my larger family, got things wrong with Jack. At the time, I was living with my mom in a compact two-bedroom apartment in Aurora, a suburb outside of Denver. My sister and my seven-year-old nephew also lived there. Our number one rule to a cohesive environment was a complete lack of boundaries, seeing as it would’ve been impossible to respect any of them anyway. Given that I disappeared for one hour a week, only to return home with an envelope of cash, and, often times, bags of takeout, they had all started to see sugar daddy as a synonym for magic genie. A mythical creature on whose chubby little belly I simply had to rub my palm around, as I made countless wishes, and then PLOP! He would shit out iPhones and chocolate lava cakes and stacks of hundred-dollar bills. But this was what being poor was like: wealth to my mom and dad was as foreign and enticing as a genie. And the sudden wealth I had just seemingly stumbled into was as mystifying as a magic wish: appearing, it seemed, out of thin air.
I did not ask my family to think of what these gifts cost me, and so they viewed sugaring through the lens of money and what it showed up as, things like food, dental work, my mom’s overdue hospital bills, and paying for college semesters out of pocket—all the things that made sex work seem like a really good opportunity for me, for all of us. I understood how the iPhone seemed to my father like the prize of some raffle ticket giveaway. I saw how he could think I was being silly by not saying yes to everything I was offered.
Even though I knew everything sugar daddies gave came at a cost, the conversation with my dad inspired me to take Jack up on his ‘gift.’ I texted him after hanging up the phone to my dad: Hello! J Hope you’re having a wonderful day! Can’t wait to see you tomorrow! Do you remember when you told me you’d buy my school books? I’m buying them all today, and I was just wondering if the offer still stands J
His response was quick. It almost always was: Yes! I’ll reimburse you for them. Just let me know the price J You’re so smart and sexy. I like to make your life easy.
I opted to buy all of my books off used websites, so my semester total came to a mere $200, but I looked on Amazon for the prices I’d give Jack. “Come on, baby,” I said to my laptop. “I want full price items and I want those shipping and handling costs.” A fiction anthology I bought was a lousy $.01 cents on Valore.com but could also be purchased brand new for $45. After shipping, that would be $41 dollars for me.
The total of all my books, plus $100 for the hassle of my research, came to $493.
I texted Jack the number and he promised he wouldn’t forget to bring it the next night to our weekly pleasure session. It really was that easy. He was always that easy.
“Like stealing candy from a daddy,” I said, feeling like I had gotten away with something.
When I pulled up to the motel the following evening, Jack was already in the parking lot, leaning against the trunk of his shiny BMW.
As usual, Jack was wearing a white polo and khaki pants. Such a common outfit for him that it took on the effect of a uniform. He was so consistent. Unabashedly his same old self every time. I would have found Jack boring if I loved him, but as a sugar baby there was so much safety in his lack of change. There was no surprise. No mystery. I was grateful for that.
Once inside the room, we sat on the bed side by side, the lengths of our outer thighs pressed into one another. We shared a complimentary package of cookies the motel chain left inside the rooms. This night it was peanut butter.
Jack had requested that at the start of every pleasure session we ‘share’ at least five minutes of conversation. On a few occasions, not knowing what else to say, Jack had asked me, “So, um, what kind of vegetables do you like?” I quickly learned to take the reins.
“How was your day?” I asked him.
Jack’s face was long, tired. The bags under his eyes were puffy. I listened to him gripe about his boss. Something about the task being too large, the timeframe being too short, and therefore impossible.
I nodded my head, agreeing with him. “That sounds so unfair,” I said. “You work so hard, you deserve to feel appreciated.” I chose my words wisely. These were the right things to say. I’d learned this from the Reddit thread, too. I was there to listen. Never to offer suggestions. Never to engage in a real conversation. Just to let him unload.
“Thank you, sweetie,” he said. “You’re so nice to me.”
He really meant it.
It was in moments like this one, that Jack’s loneliness radiated off of him like something toxic. As I ran my hand up along his back and tickled him with my fingers, I understood that he was paying me as much to sit next to him and ask about his day and rub his neck, as he was for the sex stuff. That’s how I tried to convince myself that, of the two of us, I was getting the better end of the deal.
Sure, Jack had cash and I needed it, but money was not exclusive to him. If I wanted to quit sugaring, I could go elsewhere and work and make money. Granted, I would earn substantially less, but it would be no different than the currency he slid into those bank envelopes. A dollar I earned from sugar babying was no more valuable than a dollar I could’ve earned working at a grocery store.
The things I gave Jack—what any sugar baby could’ve given him—were different, in as much that they were not genuine. What Jack wanted on an emotional level—to be desired, to be listened to, to be cared for—were not things one could simply buy. I was easily replaceable, I knew this, but no matter what woman Jack hired to touch him, the desire he would purchase from her would be counterfeit. The intimacy at the other end of a dollar dissipated the moment the motel doors shut behind him.
Sometimes I felt bad for him.
Twenty-five minutes later—while I was giving him a blow job—Jack said, “I love you.”
Jack had never tried to push the rules before. Surely, I thought, I had heard him wrong. But, then he said it again: “I love you, Michelley. I really love you.”
My whole body went cold as I looped the question: how could Jack possibly think he loved me? He did not really know me. How much can be known in a just few minutes of obligatory conversation? This brought about a new anxiety: if Jack didn’t really know me, then I didn’t really know him. Time slowed to a crawl. My skin tingled as my capillaries expanded to their maximum width. I was a sex worker in a motel, which matched the victim profiles of about 110% of the Law and Order SVU episodes I’d seen. What if Jack was one of those men, who, after he’d decided he loved me, wanted me to love him back, and when that didn’t happen, and it would never happen, he would kill me, and skin me and turn me into a lamp? My circulatory system sent a message to my brain, through a 1/3 blood, 2/3 adrenaline cocktail: You have gotten yourself into real a mess.
I handled the situation by ignoring it. I had to hold on to the faith that Jack’s uttering of the words “I love you” was more so for himself than to be shared with me. Maybe words of affirmation outbursts were a symptom of his chronic loneliness. Maybe he just wanted to hear it out loud. And yet: I was frightened. My body, all at once, felt valuable and valueless.
In a better world, I could pretend the rules of the arrangement were always ours. That Jack and I had met in those rooms each week with our expectations at eye level, which was how sugar babying was supposed to work. But, in the real world, Jack had the money, and therefore it was he who called the shots.
Maybe it seems insignificant, but I was already giving Jack my body, something I deemed separate from my true essence. In order to survive selling sex, I prided myself on my ability to keep the real me—the one that I was convinced really mattered—out of the deal. My body was one thing and it sat inside a box, but, to me, love was much bigger, and encompassed the whole world outside of that box. I didn’t want Jack to have it, nor did I want him to think he could buy it.
If I had been braver; if I had seen myself as Jack’s equal and not at his disposal, I think I would’ve stopped him. I think I would’ve ruined the pleasure session. I think I would’ve killed the mood, because then I wouldn’t have been afraid of what sat on the other side of my speaking up.
I often think about the cultural image of good sex workers and how they stay empowered. Think Julia Roberts and her mantra in Pretty Woman: “We say who, we say when, we say how much.” But this is where any power I want to believe I had slips away from me: I could not stand up to Jack—to say that I had not agreed to using the words “I love you”—without losing my job. If I did not play along with Jack’s rules then he could find someone else who would. Jack says who, Jack says what, Jack says how much. The odds were in his favor.
The truth, when I write it, does not feel empowering. I was a pawn.
As the minutes passed inside the motel room, Jack moaned into the air, and the fear that had pooled into my belly hardened into a concrete fist. I felt dirty in a brand-new way. I wondered if I had inadvertently given Jack permission to take more by accepting the textbooks. I was a sugar baby after all. Nothing he gave me ever came from the kindness of his heart, no matter how much either of us wanted to pretend it was so.
I worked hard to make the blow job end faster, and when Jack came into a stiff bleached washcloth, he did so with one final, “I love you!” It sounded like a sneeze. I sat up my on my knees, relieved that I was nearly free to go to my car and leave the night behind. My heart beat pulsed inside my ears as I looked down at Jack’s face. His head was pressed into the medium soft pillow. His eyes were shut. A grin crept across his lips. Jack was pleased with himself. Happy. In love?
When I spoke to my dad later that night, I told him Jack paid for the textbooks, that I had finally “accepted a gift.”
“Good job, Shell,” he said.
Good job. I had done right.
“Hopefully in the spring he offers to pay for the whole semester.”
Just imagine, I thought, He’d end up calling me his wife.
Image: “Touch thigh” by M.A. Pena, licensed under CC 2.0