HARLOTRY: HOW I (INITIALLY) FAILED AT BEING A SUGAR BABY

Sugar Baby No Na Easy Thing.....

For me, the worst part of prostitution was always setting up appointments with new clients. I had a few regulars, but by the time I decided to quit the economy was in a tailspin. Their business was no longer frequent enough to sustain my standard of living. It may have been the tableau reflected in the mirror ceiling that made me decide to quit, but it was the monotony of arranging appointments that made me stick to that decision. I didn’t repost my ad after I decided to quit whoring, but I went on a few calls with regulars anyway. After all, I had to eat.

Right about this time, it struck me that I had been very, very reckless with my money: I had enough to live on for about a month, but I should have had more. I had assumed I’d have the luxury of time during to decide which direction I wanted to go in but when I took a good look at my finances… I realized I had no such thing.

I considered looking for a straight job, but as I thought of all my friends who languished in cafes and behind cash registers it was obvious that I was destined for better things. Once again, I went to my friend Leslie  for advice. Leslie had recently embarked on what she hoped would be a flourishing career as a sugar baby, that grey area between actual dating and prostitution catered to notoriously by sites like Seeking Arrangement. The entire sugar daddy arrangement sounded wonderful to me; it provided the convenience of a regular client with (hopefully) greater financial rewards. So far, Leslie hadn’t had the best luck as a sugar baby, but I assumed that this had more to do with her reluctance to give so much as a single blow job, than any flaws in the actual system itself.

I found  seeking arrangement and sites like it to be quite intimidating. My fellow prospective sugar babies all seemed to be skinny, light skin girls. They were all exactly what I was not. I decided that since I’d already had such luck with prostitution sites, it wouldn’t hurt to post an ad on there. I wasn’t expecting much of a response, but I was pleasantly surprised when I received quite a few. With all the emails pouring in, I was pretty sure that at least one or two of them would be what I was looking for. I was well on my way to becoming a kept woman “of pleasure”.

The men who replied were far more diverse than those who replied to my advertisements for prostitution. There was a professor who wanted a girl to take on foreign trips, something that reeked of axe-murdering to me. There were a lot of men who simply wanted a prostitute, men who clearly didn’t understand the concept of a sugar daddy/sugar baby relationship–and a lot of obvious picture collectors. I narrowed down the candidates to a tattoo artist named Tony and a sixty-five-year-old testicular cancer survivor named Dennis who attached a picture of himself dressed as a Rapper.

I decided I should go on my first date with Tony the tattoo artist. Because he was only in his thirties, I assumed his finances probably weren’t equal to the older man’s, making him a great candidate for a practice run. We exchanged numbers and made a date for dinner at some restaurant of his choosing. I never got to the restaurant. About half an hour before our date, as I was walking to get a taxi, he cancelled and, in doing so, made it abundantly clear that he didn’t realize this was more of an interview than an actual date.

But Tony was neither old, nor completely unfortunate looking, so when he texted me the next day–apologizing profusely and offering to take me anywhere I wanted–I gave him another chance. No, he wasn’t really my type at all. And no, he didn’t seem to understand that ‘sugar daddy’ wasn’t just some outdated term for ‘boyfriend’ from the 1920s.

But if I could get some free dinners and possibly tattoos before I even put out, I couldn’t really count it as a loss. After all, wasn’t that what most people call ‘dating’ anyway?

Because I love grilled chicken, I chose a grill restaurant near my house. I assumed that on a Saturday night the place would be packed and the chatter of the restaurant would mask any awkward silences if it turned out we had nothing in common. Or, that there would be enough other people around and I could spend the rest of the dinner making witty, sparkling observations about our fellow patrons. Unfortunately I was wrong. We were literally the only people in the restaurant besides the staff.

The date got off to a very bad start. When I ordered a full chicken, Tony wasn`t comfortable about it, since they were far more authentic and urbane. I was fairly certain that calling him stingy would ruin my chances of ever being his sugar baby, but I have no doubt that irritation was written plainly on my face.

Suddenly the first flaw in the whole charade was obvious: being a sugar baby was almost exactly like being a whore, but with none of the simple transactional interactions and all of the pretense. Instead of pretending I cared about anything but the money for an hour or so, a sugar baby relationship would involve pretending that I didn’t care about money at all for as much time as I was to spend with my sugar daddy.

After his little rant against all but the chicken, I managed to steer the conversation onto his work. This, also, was a mistake. Because Tony was a tattoo artist, he had taken it upon himself to judge all other tattoos. Naturally my self-inflicted jailhouse-style work did not pass muster. When I informed him that I had done them myself he reacted the same way a surgeon might, had I told him I’d removed my own appendix. His expression went first to confusion, then outright anger, as if I had insulted him personally.

Why didn’t you just go to a shop?” He asked

“Because I was underage and I thought I knew best. Do you think you could cover them for me?”

Tony seemed skeptical about his ability to cover my tattoos, but stated that he could try. I should come into his shop, he said. When he mentioned the name, I was suddenly much more optimistic about his sugar daddy potential: he worked at one of the most overpriced, over-advertised tattoo shops in the city. At a place like that, it wasn’t out of the question for a thirty something to be making the money required to (at least partially) support a young lady, especially one whose only truly expensive habit was the accumulation of footwear.

The rest of the date went well, considering the fact that Tony was a self-involved oaf who liked nothing more than talking about himself and had a tendency to harshly criticize anyone who disagreed with him. I had assumed that the men seeking sugar babies would be much more insufferable than the men who hired prostitutes, but I wasn’t sure if I was prepared for this. I bit my tongue throughout the meal and gained a new sympathy for trophy wives.

Despite my irritation, I wanted to see the whole experience through. I had committed to this sugar baby thing and I would stick with it. If I could just keep my mouth shut and ignored the fact that I was sitting at a table with one of the more awful people I’d ever met, there might be a lot of money in it for me.

The only real problem was that Tony hadn’t brought that money up even once. When I asked him what he was looking for he said that he really wanted to get his tattoo art off the ground, maybe get featured in some magazines, possibly even create his own brand the way Ed Hardy had done. When I tried to make a hilarious and pointed joke about how he’d have enough money for three or four sugar babies if he got that far, he just looked at me blankly.

As we waited for the check, I puzzled over how to delicately ask about finances. I knew it would be rude to simply ask what he had in mind in terms of an allowance, but there didn’t seem to be much of a way around it. By the time we walked out, I had decided on what I needed to do.

Even though I only lived a few blocks away, Tony insisted on giving me a ride home. He had gotten a parking ticket during our meal and wasn’t in the best mood, but it was now or never. As he pulled up to my apartment building, he abruptly declared that he would like to see me again. I was surprised; was he just oblivious to my annoyance, or was I just that good at concealing it?

But I was glad that he had been so blunt. This gave me the opportunity I needed.

“I’d like to see you again too,” I lied, “but what were you looking for from this arrangement? I mean what kind of allowance were you thinking of providing?”

“What?” said Tony, “Allowance?”

“Yes,” I said, “I posted an advertisement for a sugar daddy. That means an allowance, or at least some kind of compensation. Shoes or jewelry could also work, but I think an allowance is probably simpler.”

If the car’s motor hadn’t been running, you could have heard a pin drop.

“Why do you think I posted in Adult Services instead of Dating?” I asked.

Tony finally found his tongue, but at that point it was too late.

As he launched into a rant about how he didn’t need to pay for sex, I cut him off: “Look, we have nothing in common. Why would I date you in my spare time? You’re a perfectly nice guy, but I’m not looking for a regular girlfriend-boyfriend relationship. I said that in my ad. I don’t know why you replied if you didn’t read it. If you aren’t interested in being a sugar daddy, I don’t see why we would see each other again. There are a lot of girls out there, and I’m sure you have something in common with some of them. If you don’t want this kind of arrangement you should say so now. I’ll apologize for making this awkward and we can forget all about it.”

Tony still seemed shocked. I don’t know if it was my bluntness that appalled him, or if he really hadn’t read my ad very closely, but he was certainly very upset. He told me that he had no idea I was seeking a sugar daddy, but that it was absolutely not what he was looking for. I said goodbye and got out of the car. I managed to walk very majestically to the door, but as soon as it was closed behind me, I bolted up the stairs, into my apartment, and straight to my bedroom to cuddle with my cat.

If this was what being a sugar baby was, I wasn’t cut for it. And I had another date the next afternoon.

I am a bit of a renaissance sex worker; I am currently employed as a stripper (and writer) but have held numerous interesting jobs in the industry.

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