Twenty-minute Sugar Daddy

The most money I ever made in one week was seven thousand dollars - seven thousand delicious dollars, and I didn’t have to do a Goddamn thing for it. Well, not really. 

I was getting ready to travel abroad to Chile to do a six-month stint as a volunteer English teacher, so I needed to figure out a way to make some extra scratch to support myself while down there making no pesos. As per my whole adult life, I had had no savings, no real job, and no marketable skills except for being able to find very creative ways to earn money, usually involving nudity. 

The first three thousand was easy. I had accumulated some hail damage on my car the year I bought it six years earlier and had never filed an insurance claim for the repair. The damage wasn’t that noticeable and filing insurance claims is about as fun as standing in line at the DMV, so I put it off. However, there was damage - little dents all over the hood and roof of my sea-foam green Subaru, like my car had once had cystic acne. 

I figured I would get maybe a thousand dollars, give or take. The assessor came to my house and appraised the damage at three thousand dollars! I had never received a check that big in my life, and I promptly put it into my South America savings account. Fuck fixing my car. But I wanted more, at least ten grand in cash before my travels. 

The only time I had ever been able to accrue that much money within a few months was when I was a stripper, and at the time I was no longer dancing. I was, however, working as a massage therapist and entertained offering happy endings as a way to amass more money. My male clients were always asking me if I would do it anyway. But that idea quickly dissipated as soon as I visualized the number of wet wipes I would have to tote along with me for cleanup, not to mention it was illegal, not to mention even more, it was kind of gross. I had already spent years in adult entertainment reluctantly humoring men’s encumbered boners during lap dances. I had hoped I was done with all of that. But getting naked for men had been the only way I was ever able to make decent money, and aside from doing porn, I had pretty much exhausted most naked options for earning a buck or two.

Then one afternoon, I was having lunch with a massage therapist friend of mine, Mindy, lamenting my inability to achieve my financial goals before I left, which was still a few months away.

“Have you ever thought of getting a sugar daddy?” she said. I had heard about women with sugar daddies before but never knew anyone who had one. I thought those relationships were saved for Playboy playmate-types who lived in LA or New York City. Did Denver, Colorado have sugar daddies?

“No,” I said. “I wouldn’t even know how to go about finding one.”

“I had one, and it was awesome. He gave me a monthly allowance, bought me a car, clothes, presents. But he moved away,” she said.

“How did you meet him?” I asked.

“There is a site called It’s free. That’s how I met mine. You should try it.”

“Yeah, but would I have to have sex with him?” I asked.

“Well,” said Mindy, “most of the time it's like that, but my sugar daddy and I didn’t have sex. I told him I wouldn’t do that, and he was cool with it. He just wanted a pretty girl to go to business dinners with and to take on trips and stuff.” I had my doubts that Mindy didn’t have sex with her sugar daddy. Rumor had it that she did give happy endings, but I kept that to myself. 

As soon as I got home, I made a profile on and waited. Almost immediately I started getting messages from a bunch of wrinkly, old, saggy men, most of whom lived in the deep South. As I filtered through the influx of septuagenarians in the Confederacy promising to rock my world, I received a message from a man who lived but a few miles away from me. Could it be? A sugar daddy in my zip code? I opened his profile. His name was Gary. He used his real name (I assumed) instead of the campy, pedestrian handles like SugarDaddy4U or SouthernGent most men on the site used. He only had a few photos posted - a headshot, a photo of him standing next to a single-engine airplane, and another standing with some friends. He was very tall. I guessed over six feet four with dark skin, a mane of black hair that fell to his shoulders, a mustache, and a somewhat wrinkled face sprinkled with post cystic acne pockmarks reminiscent of the hood of my hail-damaged car. He looked to be of Native American heritage. His message read:

“Hi, gorgeous! You seem really fun! I am looking to spoil a beautiful woman. My sugar baby of four years recently moved to Europe for work and I am looking for another one. I am a compassionate, laid-back, fun-loving gentleman just looking for the right woman to treat like a princess!”

Sounded good to me. I wrote back, and one of the first things I asked him was if he expected sex. He told me that although he didn’t expect it per se, he and his last sugar baby did form a sexual relationship after a while. He said he wanted someone to go on business trips with him, attend dinners, go to events, and that if I chose to accept the mission, would get a monthly allowance with which I could use any way I wanted. I asked how much the allowance was and he said three thousand dollars. That was way more than I was making at the time doing massage, probably even more than if I were giving happy endings. It was more than I had made in years, and although it gave me great pause to feign romance and desire for a man old enough to be my father, I figured, hell, if I did it with the guys at the strip club in the private dance booths for over a year, I could do it with this guy for a few months.

We set up a time and place to meet - Starbucks - Tuesday - noon. I got all dolled up before the meeting to make a good impression in hopes of beating out whatever competition I had. I had done a lot of shady things in my life for money, but this felt different - like I was interviewing for a very sleazy job, which I essentially was. 

I arrived at Starbucks before him and chose a seat in the corner and waited. A few minutes passed and then out the window in front of me, I saw a big black truck pull up, and a big brown man exit the vehicle. Gary, I presumed. Oh, dear God. What did I get myself into? He looked exactly like his photo. My heart began to race and I could feel my armpits moisten with nervous sweat. He walked up to me. He was taller than I expected, maybe six-five or even six-six, a behemoth, reminiscent of Chief in One Flew Over the Cuckoo’s Nest. He wore his thinning long hair in a ponytail and was dressed in jeans and a black leather jacket. He looked more like a Hell’s Angel than what I expected a sugar daddy to look like - debonaire, well-dressed, maybe using a cane, a Thurston Howell the Third type.

“Aimee?” He asked.

“Hi!” I said with a little too much falsetto. He sat down at the little table looking like a giant at a child’s tea party.

“Well, you are just as beautiful as your profile,” he said. I wished I could have told him the same. Why couldn’t he have been a handsome, sexy older man like Robert Redford or Ed Harris? I supposed men who looked like that didn’t need to pay women to hang out with them. 

“Thanks,” I said.

We chatted for a few minutes. He told me he worked as an economist, flew airplanes, raced cars, and lived in a house in the foothills just outside of town. Then he told me he had been married, but his wife came out as a lesbian a few years prior and divorced him, which he seemed very bitter about. He kept referring to her as “the dyke." Perhaps this was why he chose to form money-based relationships with women instead of sincere, emotional ones lest one of them be a clandestine lesbian. I told him about my endeavors to go to South America to teach English, which he seemed genuinely supportive of. He then said he had some business trips coming up and would like the pleasure of me accompanying him. 

I didn’t want to just jump right in and talk about money even though that was the impetus for this whole rendezvous. I was using the same nonsensical protocol as with job interviews - never bring up salary until they do, focus on your skills for the job. But this job required no skills, except for being pretty and well, greedy. Check. My questions were burning though. Was he going to pay me for the trips? Would we stay in the same hotel room? Would I have full reign of the minibar?

“Uh, yeah. That sounds good,” I said. “So, does this mean that you want me to be your sugar baby?”

“Yes. I think you’re very cool, and I’m super laid back so we’ll get along great.” He had already mentioned being laid back several times in this conversation, had it written on his profile, and had also mentioned it in our email chats. In my experience, people who claim to be laid back, usually aren’t. 

Then he slowly reached into his breast pocket as if he were about to draw a gun from his concealed holster. But it wasn’t a gun. It was his checkbook.“Well, I like to start by giving my sugar babies a sort of sign-on bonus.” In all my hundreds of jobs, I had never gotten a sign-on bonus, unless you consider the one free tanning session the dancers got at the last strip club where I worked. But entering that old janky standup tanning booth didn’t feel like so much of a bonus as it did a way to burn my nipples right off. He scribbled on the check, peeled it out of the book, and handed it to me. 

Two zeros… no… three zeros! Four thousand dollars! A shock of adrenaline shot through my body. Now, this became the biggest check I had ever received. Two in the same week! It’s amazing what the sight of money does to your body, a high equivalent to cocaine without the shits or teeth grinding.

“Really?” I asked.

“Yeah,” he said. “I just want you to know that I’m serious about it.” My immediate instinct was to yell, “Fuck yeah!” and do a victory lap around Starbucks, shoving my four thousand dollar check in front of people’s faces as they sipped their Mocha Frappuccinos shouting, “in your faces Mother Fuckers!” I don’t know why I wanted to call innocent strangers Mother Fuckers, but it seemed à propos in my head.

“Wow! Thank you!”

“You’re quite welcome,” he said. Then there was an awkward pause between us. I felt like I should at least flash him my tits or something.

“So, what’s next?” I asked.

“Well, as I said, I have some business trips coming up in a few weeks, so we can talk about plans and things like that, but I have to go now. Work. You know?”

“Ok, well, thank you so much! I’m excited!” I said, even though the only aspect of this deal I was excited about was the money. It was going to take a lot of alcohol to get through this venture. I should hope that any and all minibars would be included. This was insane. What kind of person gives four thousand dollars to a perfect stranger? Someone hiring a hitman, I suppose, a cheap hitman. I could have taken the money and run and never talked to him again. He didn’t know where I lived nor my last name. He knew nothing about me. But that was not my plan. I truly intended to follow up with him and see how this sugar baby deal panned out.

We both stood up, and he engulfed me in an embrace. I only came up to his mid-chest which smelled of leather and sweet, pungent old man cologne. We walked out together. I got into my car, drove straight to my bank, and deposited the check. I should have just cashed the damn thing. Instead, I waited a few days until I saw it had cleared and was now in my account. Was this some sort of scam? But a scam is when someone promises you something and then you foolishly hand over wads of money only to never reap the rewards. I should know. I scammed plenty of guys at the strip clubs, overcharging their drinks, not following through with the “you can suck my tits” promise in the private dance booth, and then pocketing the money anyway. But this was the complete opposite of a scam, like, an un-scam.

I called my bank and explained that I had received a rather large check and was wondering if something had gone amiss or if it was a fake. The clerk confirmed the deposit, that my account was indeed four thousand dollars richer.

Over the next few days, I waited for Gary to call me or email me to start making plans for this business trip he had mentioned, but I never heard back from him… ever again. 

I know he didn’t die because I looked him up online and according to the data I saw he was alive and kicking. I didn’t bother trying to contact him. I was relieved that nothing came of our short meeting except for a coffee with soy milk and a big fat check in my hand. But the question remained. Over and over I asked myself, as well as my friends, why would he have given me this money and then disappear into the ether?

I kept waiting for the other shoe to drop, or just the first shoe, for the FBI to come knocking at my door asking if I had come in contact with a large Native American escaped mental patient posing as a sugar daddy. But no one came, and life continued. I briefly went back on hoping to find another anomaly like Gary, but I knew it would never happen again.

I’ll never know the reason for Gary’s generosity and subsequent disappearance. That afternoon at Starbucks still goes down as one of the most fantastical events that has ever happened to me and having worked in adult entertainment, I have seen and done a lot of weird shit.

Every once in a while when I’m with my friends, the sugar daddy topic comes up. Someone had read about Hugh Hefner or watched The Real Housewives of wherever, and the conversation usually goes like this:

“Eww. I would never do that, have sex with an old guy just for money.”

“I don’t know. I might if he was cute enough."

“Yeah, but isn't that like prostitution?”

Then I chime in. “I had a sugar daddy once,” and my friends perk up with interest.


“How much did he give you?”

“What did he look like?”

“What did you have to do?”

“For how long?”

And my thoughts travel back to that ridiculous yet wondrous day at Starbucks with Gary, and I answer,


“Four thousand dollars.”

“Chief from One Flew Over the Cuckoo’s Nest.

“Drink coffee.”

And the final response, which always gets the biggest reaction;

“About twenty, twenty-five minutes.”

Turns out, I was the one who finally got a happy ending. No wet wipes required.