Finding a sugar daddy

I have a lover -- or perhaps an ex-lover, since we haven't done it in almost a year now and although she keeps saying we'll get back together some day it hasn't happened yet -- who works in the sex industry. It's been years since she's had a job outside the sex industry, and she doesn't plan on moving on anytime soon. She's 30, can pass for 22. At least she tells customers she's 22.

She was a stripper for a long time, did some lap dancing and now works at a massage parlor. After years as a stripper, in which she never made much money -- about as much as she would have made working 30 hours a week in a coffee bar, which is what most people her age are doing -- she's now pulling down hundreds of dollars a week jacking guys off. That's what she says she's doing.

For the first time in years, she has plenty of money. She finally went out and got herself some new clothes; after years of dressing in thrift store chic, she now shops at designer boutiques. It's nice to see her with some new duds, not because I disliked her old look, but because she had never managed, in years of thrift store shopping, to buy herself a decent warm coat. For years we walked around town with her shivering, and now that she's more comfortable, I'm relieved.

We went last week to dinner and a show, her Xmas present to me. Along the way, she ducked into a boutique on Fillmore Street, the nice part. It was empty when we went in, but as she was trying on something, a couple of other women came in; from their conversation, it was clear their names were Christy and Brandy. They had those loose California mall-rat accents, but it was clear they had plenty of bucks. After that we went into a makeup store; it was crammed with rich bitches from Pacific Heights.

"You know," I said when we were finally on our way to the car, "I'm glad you have some money now to spend on stuff, but isn't it kind of strange to be hanging with all these ex-sorority girls? It's not exactly the crowd you're used to."

"Yes, I know, it's hilarious," she said.

"Tell me," I went on, "has having enough money to buy what you want changed your relationship to things? Does it feel different?"

"Yeah, now when I go into a store, instead of saying to myself, 'Oh God, I can't even think of buying that $300 blouse,' now I can actually go, 'Hmm, maybe, if it fits.'"

The conversation didn't go much farther than that. I guess I wanted to have a conversation with her about materialism, but I didn't know how I could without it sounding like I was judging her somehow. And in fact, I have no room to talk, since I make plenty of bucks in the high-tech industry-- much more, for example, than I ever could have made in one of my former careers as a high school teacher -- and I don't exactly lead an ascetic life myself. Maybe I was just wondering how I would deal with suddenly making a lot more money than I was used to.

Something else she said disturbed me a little, though. She told me, without a hint of irony, that what she really wanted to do was to find a rich guy who wanted a mistress and would spend plenty on her, getting her lots of expensive clothes, taking her on trips, and if possible, getting her a nice apartment. She expected to find such a rich dude among her customers at the massage parlor, where it costs $250 for a hand job (I have personal experience that she gives great hand jobs. I suppose if you were pricing such things, $250 might be a reasonable price. It's out of my price range, but then again, maybe for somebody who frequently pays for sex, it's okay. Who knows?) Since it's located in an affluent suburb, she figures some of the customers have some serious money.

In fact, that week she identified her first prospective sugar daddy. A customer came in whose job is to "open" outlets around the world for a famous designer. He wore expensive clothes and basically said he was in the market for a new mistress -- I don't know if he used the words "I'm in the market" but he had said that his "current mistress" had moved to Hawaii and he never got to see her anymore. And he asked my friend a lot of personal questions like whether or not she smoked. "I answered, 'Oh, just a cigar from time to time.' And he seemed very taken with that answer. I don't think he would have asked me that stuff if he hadn't been treating it as sort of, you know, a job interview."