The first time I posted an ad seeking a sugar daddy, I still lived with my parents. I had just landed back in my sleepy Central Coast hometown after six months on the road as a merch girl with goth-indie-pop darling Amanda Palmer. While living out of a tour van and making out with bass players were things that truly fulfilled me in the way that a career should, they just didn't pay the bills.
I had student loans to pay, and I really didn't want to live with my parents for any longer than absolutely necessary. I had a job, but it paid just $15 an hour, which meant that in order to save enough money to move to San Francisco, I was going to be stuck living in the toolshed-turned-guest room in the backyard of my parents' house for way longer than was mentally feasible for me.
I'm not sure when “sugar baby” first entered my vernacular, but the idea that an older, well-off gentleman would drop some serious cash for the privilege of being my boyfriend didn't sound that impossible. I knew there were scores of wealthy, lonely men in this world, some just a few miles from me.
I pictured a Pretty Woman fantasy where I made $10,000 a weekend to go to the opera and the Kentucky Derby, or shop for dresses on Rodeo Drive. I knew there would most likely be sex involved, but I also assumed that he'd look like Richard Gere.
I knew that posting internet ads for sexual arrangements in one's hometown is ill-advised, but I did it anyway and crossed my fingers that I wouldn't end up on a date with an old teacher or one of my mom's friends.
The first stranger I consented to meet in person looked like a straight Freddie Mercury, had he lived to be 55, who claimed to be a cosmetics tycoon with an infirm wife. We met in a safari-themed basement bar of a weird hotel that my mom liked to go to for lunch. Best salad bar in town. He smelled nice, and when he gave me money, my attraction to him was able to surface and bloom into something that felt real enough.
He wore expensive linen pants with no underwear. I didn't dislike hanging out with him, and he brought me expensive bottles of wine (I was really into wine then) every time we got together. The last time I saw him, which was also the first time I let him fuck me, I sat naked in the toolshed after he left, sipping the jammy Bordeaux he had brought me. It was too sweet, cloying, like it had gotten too old sitting in his fancy wine cellar in his big house by the ocean. I didn't like it.
Later, I got an email from him informing me that I was too chubby for our arrangement to continue.
“Nothing personal,” he assured me. “I just prefer girls who look borderline anorexic.”
So I decided to take a break from the whole sugar situation. I got a waitressing job and started dating a girl I had gone to high school with. I didn't tell her about my forays into the world of transactional romance. I knew she'd freak out if she knew, even though my waitressing job made me feel cheaper than drinking expensive wine in a toolshed. Eventually I managed to hustle enough cash to finally make my way to the Bay Area.
But once I was stable, with a wage-slave position at a stationery store, I got antsy again. I could pay my rent, but I couldn't afford much more, and I yearned to experience the incredible parts of San Francisco that seemed so out of reach — killer seats at AT&T Park, fine dining, opera. …
Again, my imagination turned to the fairy tale of being someone's sugar baby, so I posted an ad on a website called Seeking Arrangement, hoping to find my Richard Gere lookalike this time. I had far more confidence in the wealthy men of San Francisco. At the very least, there would be more to choose from, and there would be far less of a possibility that they knew my parents. …
Come back next week for the rest of Siouxsie Q's thrilling origin story.