When you’re 23 and getting divorced after 5 years of staying home, the only logical thing to do is to look for a sugar daddy, no? It made perfect sense to me; I wasn’t interested in a serious relationship, but being taken out on nice dates and having help with the bills seemed like a win-win situation. I truly believed there were these handsome 30- and 40-something year old men who were just happily fluttering $100 bills in pretty girl’s faces; that they deemed it their responsibility to financially support young women. My career in sex work started this naively.
Those illusions clashed with the reality of being a sugar baby as soon as I met “Jim,” who convinced me that he was a generous sponsor after a dinner at Beni Hana and an offer of a winter coat. I spent our dates high out of my mind, so my perception of things was undoubtedly flawed, and my memories of him confuse me to this day. But as I recall, we would go to his house where we had Thai delivered every time I came over. He was in such a rush to get upstairs that he would hurry me through dinner. His “son’s room” was like no child’s room I have ever seen – it looked to be straight out of a Pottery Barn catalogue with not one thing out of place. At the time, I didn’t think he really had a son, and looking back it makes me wonder what else he could have been lying about.
Each time we saw each other he gave me a couple hundred dollars, except for once. The last time we spent together, he slapped me across the face while we were in the middle of sex and began what he believed was dirty talk. “You like that, don’t you? You like being my dirty little whore?” I was so shocked I didn’t respond at all, and when he dropped me off, he gave me $60 “for gas money this week.” Based on the agreement that he would give my girlfriend $40 each time for babysitting, this meant I ended up with $20 for being smacked around. I could discuss how much my sitter needed to be paid, but talking about my own compensation, for whatever reason, was too uncomfortable. For the first and last time, I had wrongly assumed that a man “just knew” what the magic number was.
“Samuel” picked me up in his 300Z and we went to Montana Grill where he spent the evening asking me “deep” questions, wanting to discuss in detail his exhaustively descriptive emails about books he’d read, articles he wanted me to read and share my opinion on, and lifelong dreams he wanted us to share in hopes of finding the all-elusive connection. His longing for an emotional connection was apparent. After that first dinner, he drove me back home and handed me $300, not asking for anything else from me. YES! I thought, this is more like it! When we got together again, he took me to his house in a suburb west of Denver. Turned out he lived with his parents, whom I was introduced to when I arrived. (It was the first of several times in my career I’d be introduced to parents.) I listened as he showed off all of his autographed porn star memorabilia. We spent some time in the bedroom before he took me back home, again giving me $300. Sam was looking for more of a girlfriend, and he wanted to have unprotected sex, which I was not comfortable with. Sam’s last relationship had been with an escort who eventually passed away from a drug addiction. He seemed deeply wounded, and was searching for an exact replacement.
Since it was evident it wasn’t going to work between Sam and I, he suggested that I try escorting. It was with him that I first encountered the notion of a “hobbyist,” and he told me he would be happy to write a review for me. It was with Sam that I realized not all sugar daddies are new, gullible, hesitant men who are reluctant to plunge into the escorting world; rather, they’re often hobbyists who are in search of less boundaries, cheaper “deals,” and more of a connection than is usually found at the standard hourly rate. We wished each other well, and a few months down the road when I decided to try actual escorting, he did write my first review.
But before I took that plunge outright, I branched out from specific sugar daddy sites to try my luck on Craigslist, coincidentally in the year the adult personal section was shut down. “Dave” —the first man I met from CL—was overly anxious and so we skipped the initial meet-and-greet dinner date that was standard protocol. I needed the cash, and less time spent bullshitting was fine by me. So he picked me up in his Jeep and took me downtown near the Capitol. He handed me the cash in an envelope and suggested I excuse myself to the bathroom to count it: all $350 was there.
He told me he’d created an “online story” about the two of us and was going to write our experience down like a journal entry. He also offered to be my manager and suggested that if I didn’t want to do official escorting regularly, I could just be a high-end courtesan and he could design a website for me. He reminded me of an overweight Gene Simmons, and he talked endlessly about his band and recreational drug use. He was the only 50-year-old I knew with a MySpace page. Dave whined half-heartedly that I insisted on a condom for everything, but didn’t resist.
It was a year later when I was working for an agency that a photographer made a comment about a particular hobbyist’s handle on a review board. I perked up remembering this was Dave’s email and MySpace page handle. His favorite pastime was apparently writing elaborate reviews of naïve girls just getting into the business, and what bareback services he was able to coax out of them before they “learned otherwise.”
When I first began dabbling in the sugar daddy world, I really had no intention of doing any consistent or long-term. It was simply to bring in a little additional money when I needed it, and have a date with some rich guy who enjoyed arm candy. But then the child support payments dried up and my full-time job was only covering half of my monthly expenses. Being in a huge city essentially by myself with two young children, my options felt limited at the time. I was already meeting with strange men and accepting their money, so the step from the Craigslist personals section to the Backpage escort section was no large leap. After a particularly upsetting conversation with my ex-husband, I angrily posted my first ad on Backpage. I will never be dependent on someone else to support my children, I said to myself. And 5 years later, I still haven’t regretted that decision.
I met a few more men from these websites, but eventually abandoned the notion because I realized there was faster and better money to be made as a full-fledged escort. I enjoyed the business-like aspect of escorting much more than long drawn out emails and phone conversations. If a client was interested, they contacted me and we simply scheduled a time. The boundaries are so much more established, whereas being a sugar baby leaves so much gray area, at least in my eyes. My personality is very orderly and professional, and that clashes with trying to be the wide-eyed, affectionate baby doll sugar daddies seem to prefer.
My early days as an attempted sugar baby paved the way for me to escort and many of the things I learned — how to stay anonymous, sober, etc. — were as, if not more, important in the escort world. I also realized that by having a sugar daddy (or two,) most of my time was consumed with maintaining the illusion of an intimate connection with them, and my finances were, yet again, dependent on one person who could simply back out of the agreement at any point in time without warning or recourse. For my situation, and my personality, escorting made sense; I was able to remain in control of my own time and finances without the dread of a dysfunctional/delusional relationship distracting me.
While one might hope (or assume) that sugar daddies have far more discretionary income than the average escort client, it seems from my experiences to be the exact opposite. I’ve met both great and shitty men in both situations, and while my patience levels led me to focus on escorting exclusively; I also see the benefit of marketing to both pools. The unashamed ability to seamlessly push a relationship beyond the hourly commitment of escorting and into the SD/SB realm is an art, a skill that is developed over time, and it’s not for everyone. In the sugar daddy realm, I was never able to make it work in a way that was a profitable as I wanted. However, over the few years that I have been escorting, I have developed several on-going relationships with regulars I met through that venue, and those developed into something more like the sugar roles than the traditional escort-client hourly agreement. The difference is that we still respect each other’s boundaries, personal lives, and occupations with no expectations of exclusivity. For me, that’s what has worked best.