99protagonists | One Night In LA
One Night In LA
July 21, 2020
99protagonists | Quarantine Dreams
Quarantine Dreams
July 21, 2020
99protagonists | My Sugar Daddy Part One

My Sugar Daddies, Part I

Photo credit: Saturday Evening Post

It was half past eight when the cab skidded to a stop at 45th Street and Sixth Avenue in midtown Manhattan. Before that evening, I had only seen Butter in a couple episodes on Gossip Girl — the clear glass exterior allowed me a peek into its posh subterranean space. I threw a wad of two $10 bills at the driver, who muttered a string of profanities under his breath as I exited the vehicle knowing full well I didn’t leave enough for a tip. I’ll make up for it on my next ride, I promised to the karma gods.

I was about to meet my first sugar daddy, and I felt a thrill of anticipation at the thought of life as a sugar baby. I was a full-time grad student, with only a couple thousand left in my savings account. Although I could stretch those funds for the rest of the school year, a little extra cash never hurt. Plus, this seemed easy enough. Dress the part, play the part, right?

I straightened out the sequined sheath that added a few years to my 21, quickly glanced at my reflection on my phone’s dimmed screen, and entered the restaurant. The maître d’ greeted me with a nod.

“Table for two, Richard Smith*,” I offered, nervously. Surely she could tell that I was barely an adult? Glancing around, I spotted a melange of trendy patrons — a middle-aged couple in spirited conversation; a table of four women not much older than me, all of them dressed in variations of black; a trio of 30-somethings hunched over their phones.

But the maître d’ only said, “This way.” She promptly led me a dozen steps or so down the center of the restaurant when a chisel-jawed stranger with salt and pepper hair rose from his seat to tower an entire foot over me and block my path.

I recognized the man — it was as if he jumped off the screen of my phone. The half smile, raised eyebrows, dark features, with a birthmark just below his jawline. Then it was just us, me and my sugar daddy.

For me, sugar daddies conjured up either images of severely balding, pudgy sad men in their mid-50s who sought simple companionship or striking silver foxes with extreme BDSM fetishes. But Richard was neither.

I met him online just two weeks prior to our dinner. I was browsing prospective daddies on the dating site Seeking Arrangement when I stumbled upon an image of a suited-up gentleman with his face intentionally blurred. I clicked on the profile and discovered more photos — one of him standing in front of a silver Mercedes Coupe, another at a ritzy restaurant with city views. I was also able to see his annual income (“more than $1 million”), his height (6’4”), net worth ($15 million), education (PHD/post-doctoral), body type (athletic), and drinking habits (“social drinker”). He left his occupation and his relationship status blank.

“Wow,” he said. “You’re beautiful.”

“You, too,” I said, out of habit, and then cringed at the response. I awkwardly laughed it off.

But once we took our seats, the conversation flowed like wine — of which we had two bottles — and was as juicy as the steak for two that we shared. We skipped past the pleasantries and immediately negotiated the terms of our arrangement: He sought a date for certain “professional functions.” I wanted financial security with a monthly allowance of $1,000. He desired intimacy with an “organic” connection. I requested Givenchy bags and Chanel shoes in return. He was looking for novelty and excitement amid contentious divorce proceedings. I was after sexual escapades in unexpected —

Wait. “Divorce?” I asked, dumbfounded. We had spoken every day leading up to that dinner, and while I assumed that he had been wedded at some point, my inexperience never led me to believe he was still married.

“Yes, from my wife,” he said, as if this information had repeatedly fallen on deaf ears.

“But you’re still married?” I made a furtive glimpse at the direction of his left hand, which rested on his lap under the table and hidden from view.

“Yes,” he said again, swallowing the last of the Châteauneuf-du-Pape we had ordered just a half hour ago. “Is that going to be a problem?”

I could’ve said no. In the grand scheme of things, did it really matter? But morality took the better of me. Sure, the sugaring lifestyle seemed fun and lucrative, but at whose expense? I didn’t know his wife, but I could say with near certainty that she wouldn’t have been too thrilled to find her soon-to-be-ex-husband canoodling with a 21-year-old (if it were to come to that).

Before I could reply, he threw me another curveball: “I also have two kids — you knew that though, didn’t you?”

I shook my head before I could even spit out the words, “Absolutely not.” We stared at each other for what seemed like a full minute. “You preferred not to say you didn’t have kids on your profile,” I said, almost accusingly, “but you never suggested in any of our conversations before this that you had kids.”

That was a dick move, Dick, I thought.

Instead of addressing this, he began talking about his children. “My son is in finance, he graduated a few years ago,” he said. “My daughter is 18, in her senior year of high school.”

Senior year of high school. She couldn’t have been older than 17 or 18. I was closer in age to my companion’s daughter than my own companion.

My face must’ve betrayed my thoughts because Richard asked, “Is everything okay?”

I folded the table napkin that was sitting on my lap and excused myself to the ladies’ room. When I entered the restroom, I stared at myself in the mirror. Young and not unattractive — stop it, you’re beautiful — and, best of all, astute. I would rather stay single my whole life than be labeled a homewrecker, and I most certainly am not looking to be anyone’s trophy date. I knew at that moment that I couldn’t agree to an arrangement, but I could still milk him for all he’s worth tonight.

At the table sat a new bottle of Grenache, which he poured into fresh wine glasses when I had settled back into my chair.

“Everything okay?” He repeated.

“Of course,” I smiled — for everything was actually more than okay. After another hour of lighthearted topics and inside jokes from our online chats, I had been sent off with a free meal and $500 in cash — and no promise of another meetup. It was a win-win for me.

At the end of the night, Richard — who had taken the hint — was gentleman enough to hail me a taxi, chivalrously open its door, and instruct the driver to take me to my Upper West Side apartment. When the car stopped in front of my building an hour before midnight, I took out the envelope that held more than two dozen $20 bills and tossed four to the driver.

I liked to call my first one “Dick.”

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