This is part of a recurring column about modern romance, dating, and more.
I never intended to be a prostitute. Or a hooker. Or a sex worker. That certainly wasn’t what I was planning, but somehow I wound up towing the line.
“You’re going to be a goddamn prostitute! I can’t believe we’re even having this conversation. You know how you’re always worried about making your parents proud? This makes every other bad decision you’ve made look like you were a choir girl.”
And just like that a friend of mine, called it like she saw it and a friendship of 12 years went on a two-day hiatus.
I’m a writer, I live in Chicago, and I am poor. There is privilege here, sure, but I am also poor. When your phone gets disconnected, when your internet turned off after a 60 hour work week, and when you have ramen for dinner everyday, it’s hard not to feel like you’re empty.
A week before I logged into seekingarrangements.com, I had made a budget to try to figure out why I was so strapped every day/week/month. When the tallies were made, only accounting for credit card bills, electricity, water, rent, and some prescriptions here and there, even with the absence of ever going out to dinner or for drinks, I would be $4,000 short every year. That is a problem. So I came up with a solution, a new part-time job, if you will. I would become a Sugar Baby. A Sugar Baby is a “companion” for a presumably wealthy man, who helps his Baby out with bills and gifts and whatever he would like to treat her with. She provides more companionship than just sex; sometimes sex is involved, but not necessarily and not always.
A friend of mine and I had joked about it years ago, and I had never had the nerve to even Google how to do this. It was a silly idea. I’d never go through with it, right? And then I searched and realized how easy it is. I read a few Thought Catalog blogs about experiences girls had had, and heeded their advice about setting up the profile. Not too much information, not too little. Classy photos, not just selfies. Always smiling, always with a full face of make.
First I change my age to 27, because 30 is probably too old to be a Sugar Baby. And then I dumb down and shorten my About Me section. “I like wine, whiskey and writing. Great conversation and laughing!” I posted recent pictures featuring my assets: big boobs, big ass, big smile, and long luscious dark hair. Selfies have taught me how to feature myself. I waited for the offers to come in while I avoided thinking about my friend’s comment. How quickly I can be considered a prostitute for trying to find a solution to my current problem that doesn’t involve declaring bankruptcy at age 30. I’ve made bad decisions in the past, sure, we all have. But this isn’t one of them. This is an opportunity for me to use the tools I have available, namely my stunning personality and curves, to assist with my needs.
Finally the wealthy benefactors began to contact me and I see a way out! The first man wants to pay off my credit cards! How kind! I don’t have to do anything except give him the numbers! Wait…that seems fishy. So I delete his inquiry and block him.
Next a nice looking married man asks me if he can pay me $225 to come over and cum on my face. I’m really broke, I mentioned this right? So after a bottle of wine I consider this but then choose ultimately not to.
Man after married man contacts me to ask what I like, what makes me happy, and when can I meet for coffee/dinner/drinks. We flirt via messages and I remain perky and carefree, telling them vague details and asking about them, their lives.
I receive more requests and continue discussing with these men what they’re looking for and what I’m looking for, yet I can’t get my best friend’s words out of my mind: You’re a goddamn prostitute! The thing is, most of these men weren’t looking for sex, or at least not just sex. They wanted camaraderie. They wanted to know about me, what makes me happy, what makes me smile, and they mostly wanted to tell me how great they were and why they were doing this. Time after time, they each told me they just felt like something was missing, the old “spark”, as they say. They’re busy men and most purchase what they want, when they want it, and companionship is no different.
My friend went on to tell me that no matter how I shined it up, it was prostitution. You know the old adage, call a spade a spade. So while I disagree, wholeheartedly that this lifestyle is prostitution, I’m coming to terms with calling it that because I believe in calling a spade a spade, it doesn’t matter to me what you call it.
I did more research, I talked to more friends and mentors about what they thought of the idea. Spoiler alert: most people think it’s a horrible idea. Most friends couldn’t believe I would ruin another woman’s marriage. Still others advised I’d have no normal career prospects if anyone finds out. Then it occurs to me that my reservations aren’t my own, they’re the reflection of what I think everyone else will think or does think. I’ve always been a reflection of being who I thought I should be, who someone else wanted me to be. But I’m 30 now. This is my life. These are my bills. These are my morals. I decided then not to spend anymore time asking for opinions or worrying about them. The confidence breaking away from expectations, led me to actually follow through. Make the move. Meet the Daddy.
The first Sugar Daddy I met was Peter. Our first date was a four-hour phone conversation the day of the eclipse. We talked and laughed for hours. It was nice. I quickly realized my need to reflect what others want is a strength when you’re a Sugar Baby. I could be whomever they needed. I can fill the role that they’re looking for, and they can fill my monetary needs. Peter is 36, married with one child. He needed someone to make him feel attractive, like he’s the only one in the room. He said he used to be fat and had recently lost weight and now he finally felt like he could talk to any girl in the room! He said when he got married 10 years ago, he settled because he didn’t think he could do any better. But now, look at him! We talked about his wife and his marriage and how he justified going outside the bounds of the relationship. (More to come future columns on Peter and all the ways that men describe these excuses, these reasonings.) I practiced the empathy and understanding that I was being paid for. He needed a confidence boost. The last Sugar Baby that he had was 19 years old. The one after me, 22. I was not like the others, which is likely why it didn’t work out, but I didn’t know that at first.
I played the part, I was his laughing, silly, smiling Southern girl, hanging on every word he said. This wasn’t hard because he was actually funny and interesting, but I use it to illustrate that the first lesson I learned about being a Sugar Baby is to be a reflection.
Becky is your friend, girlfriend, wife, and mistress. She plays and writes in Chicago. You may have seen her in The Establishment, Vol 1: Brooklyn, The Washington Post and others. She gets around.