"Being kept is fun!"

Despite the failure of my first attempt at being a kept woman, I decided against cancelling my date with Dennis, a sixty-five year old testicular cancer survivor. The fact that he had sent me a picture of himself dressed as Hunter S. Thompson suggested he might be an interesting person, and the fact that he’d survived testicular cancer could bode well for me. I didn’t know much about the disease, but I was pretty sure most people didn’t survive it with both balls intact. One or even no balls probably meant a lower sex drive and I dared to hope the whole relationship could be conducted by way of shopping trips, theater performances, and fancy dinners.

Dennis had mentioned a financial arrangement in his email, but insisted on hashing out the particulars in person. After the debacle with Tony the Tattoo Artist, I was wary of such an arrangement and worried that he’d bank on some sense of delicacy preventing me from bringing the matter up. I had already ignored the dictates of good manners and asked directly about money once; I hoped I wouldn’t have to do so again.

I met Dennis at a nearby restaurant. It was a place I’d been many times before, but always with friends. The food was terrible, but there was something about the old-timey freak show posters on the walls and the servers who engaged everyone in too-lengthy conversations that made me love the place. It was strange to be there while the sun was up, even stranger to be meeting a client there. We exchanged pleasantries over the menu, and as we waited for our food, Dennis mentioned that he had been a sugar daddy before.

I immediately felt reassured; if he’d already had experience as a sugar daddy I probably wouldn’t have to deal with any awkward misunderstandings or navigate the social minefield of a discussion about money.

After showing me several pictures of his previous sugar babies, Dennis outlined the financial agreement he had used with all of them. He would pay me $50 per hour for any outings we might go on. If there was any sex, there would be a bonus of $150 for oral, $200 for intercourse. I would have preferred an allowance–and the prices for sex were much lower than my hourly rates as a prostitute–but it seemed likely that I could make as much, if not more, while expending significantly less effort. And possibly acquire some nice possessions in the bargain.

I waltzed home humming ‘Sugar Daddy’ from Hedwig and the Angry Inch. I was sure I had things made.

My first paid outing with Dennis was set for the coming Wednesday. Overjoyed to discover that I smoked, he insisted I try smoking cigars and arranged to meet me at a specialty smoking shop. I really had no interest in cigars (and I was somewhat nervous about whether the two of us could keep a conversation running) but if this was what it took to get my shopping trips and fancy restaurants, so be it.

For as long as I can remember I have looked to books for support in trying times. I grew up in a house where bookshelves lined the walls so densely that there was very little room left for pictures; as a result I see books not only as the literal object, but something that represents a certain safety and security. Even when I am fairly certain I won’t have an opportunity to read, I bring whatever I’m currently reading with me on any trip that might take a turn for the worse. This time my security blanket was Women by Charles Bukowski.

When Dennis finished buying the cigars and asked about my book, I was elated. Here was something I could talk about for hours! I wouldn’t have to answer questions about myself or my life (my two least favorite topics), I wouldn’t have to explain the absolute lack of meaning attached to my tattoos, and I wouldn’t have to hear Dennis talk to me about whatever old men think young women find interesting.

As I described that Women was about Charles Bukowski’s literary alter ego, Henry Chinaski, being old and ugly, picking up pretty young women with nice legs, holding on to them through pure talent and obstinacy, losing them, and learning from them… Dennis’ eyes lit up.

“So he’s a lot like me!” he exclaimed

I had no idea what to say to this. Had he missed the parts about talent? As I tried to formulate a response, I puffed on my cigar, inhaled, choked, and tried to conceal my disgust. I didn’t want to say that the only things that Dennis seemed to have in common with Bukowski were age, pitted skin, and a large nose, but I didn’t want to bolster his ego too much by telling him that Women was pretty much his life story.

“Well, I mean kind of?” I said, “But not really. It’s a lot different, you should read the book, you’ll see what I mean.”

“I’ll have to do that! I’ll pick it up on my way home,” said Dennis, “This Bukowski sounds like my kind of guy.”

Dennis did indeed pick up a copy of Women on his way home. He texted me excitedly a few days later to inform me that he’d finished it, was starting Ham On Rye, and couldn’t wait to talk to me about them. I had created a weird, eager monster. I’d expected him to read Women and either see and accept the differences between Henry Chinaski and himself, or decide that Charles Bukowski and his alter-ego were useless drunks with whom he wanted nothing to do.

Unfortunately when I saw him next, it was obvious that neither of these were the outcome: Dennis had obviously decided Charles Bukowski was his spirit animal.

I figured it was only a matter of time before Dennis developed an alcohol problem or bought a typewriter in order to be more like his new idol. Rather than doing either, though, Dennis decided that the thing to do was bring me to the apartment he and his friend kept (as a secret hideout from their wives) to prove exactly how much he was now like Bukowski: with some uniquely awful oral sex followed by a trip to a filthy hole-in-the-wall Dominican restaurant and a speech about how after great sex “one must eat meat in order to replenish one’s energy.” I refrained from telling him that a salad would be fine in this case and, once again, considered whether sugar-babying about was worth the annoyance.

I soon discovered that if there had been any hope for nice restaurants, shopping trips, and theater performances, all possibilities were dashed the minute I introduced Dennis to Women. His criteria for making decisions had suddenly become ‘What Would Bukowski Do?’ There was very little sex, but endless conversations about how many characteristics Dennis shared with his new favorite writer and countless exclamations about how some restaurant he was taking me to was exactly like something Bukowski would patronize.

It was obvious why Dennis would feel such an affinity for this writer. Here was a perfect justification for his late-life crisis, a license to be a dirty old man, even one who drank too much, yet it could still be “cool.”

After watching my mother survive breast cancer twice, I knew very well how devastating disease can be and how triumphant recovery is. I assume that a battle with testicular cancer is just as epic, if not more; not only is life on the line, but men are so very, very fond of their balls. And, although he never said it outright, it was clear that Dennis felt old. It wasn’t just his lusts that made him seek out younger women; he wanted me and all the girls before me to make him feel young again. He sought out common interests with something that can only be described as desperation, and when he encountered a total lack of common ground, he tried his damndest to create some. If he hadn’t been so irritating it would almost have been touching.

After my experiences first with Tony the Tattoo Artist and now Dennis, it was obvious that I was too headstrong to be a sugar baby. My experience may have been very limited, but it was obvious to me that the men drawn to a sugar daddy lifestyle are not simply seeking a sweet young thing to tote around like some kind of fancy accessory… they want validation just as much, if not more. I’ve never been very good at sustained bouts of flattery, and this was too much to maintain for long. Every time Dennis brought up how “well preserved” he felt he was, I had to practically restrain myself from telling him that he was no such thing. Instead, I cooed that he really was quite well preserved and if I didn’t know better I would think he was merely in his forties. Every time he brought up the similarities he felt he shared with Bukowski, particularly his fondness for much younger women, I bit back the temptation to point out that Bukowski didn’t have to pay his younger women.

Despite all this, I allowed Dennis to squire me about the city for three months. What with the few regular clients I kept seeing and the income from my outings with Dennis, I no longer had to worry about finding new business, yet I could maintain my standard of living. By the end of the three months, however, I was not only fed up with Dennis himself, but entering a relationship.

My boyfriend hadn’t asked me to quit prostitution–he had even told me that he understood the difference between work and infidelity–but I was fairly certain that it would become a problem down the line, and there were so many other things I could do.

I have never been very good at endings, and the financial nature of the arrangement made things much more delicate. I decided that the best course of action would be to simply stop contacting Dennis, respond to his attempts at contact with only the most cursory replies, and let things die of their own accord. After two weeks, he finally asked me to meet him for lunch at the same restaurant where we had initially made our arrangement. We both knew it was the end. I told him I had found a real boyfriend and that our relationship needed to end and he told me he had suspected as much. He asked me if I had any friends I could recommend for the position of his new sugar baby, and when I told him I didn’t he seemed downcast. He wished me well, and as I stood up to go he imparted one piece of advice, “don’t get married and don’t get pregnant.”

I couldn’t help but laugh at his grave delivery, but so far I’ve followed his advice.

Cathryn Berarovich is a bit of a renaissance sex worker; she’s currently employed as a stripper (and writer) but has held numerous interesting jobs in the industry. Each week, she shares her stories in Harlotry.