Lessons in commercial sex

Dear female reader who is starting off on SeekingArrangement (henceforth in this post, “SA”):

I learned a few lessons in my time as a CPOS, and I thought you might benefit from them.*

1. Everyone lies. This is true in life, of course. But it’s especially true at the juncture of sex and money. We are so ambivalent about so much that takes place at that juncture, we rarely are honest with ourselves, let alone with those whom we’re fucking or with whom we’re exchanging money. And least of all, with those with whom we’re doing both. Much of the lying that takes place on SA isn’t exactly lying – the teller of the lie doesn’t necessarily know her or himself to be lying, and s/he may be lying to her/himself as much as to you. Men tend to overstate, in this way, our desire to have just one, long-term, relationship; we underestimate the power of our desire for variety, for newness. Women, similarly, tend to indulge men in the fantasy that we are the only man with whom she is “doing this.” And much of the lying is more in the category of “performing”: I never told anyone my real name, and I rarely told anyone my real profession. While some among us are pathological risk-takers, who get off on the possibility of discovery, those of us who aren’t, who don’t, perform an alternate reality. And also? Performance allows us to alter ourselves in directions we might prefer: I often understated the number of women I’d met previously through the site. This was as much for my own benefit as for my audience’s.

Men and women both lie about what they have to offer – height, weight, age, wealth, income. There is an absolutely shocking – and entirely statistically improbable – quantity of women who are 29 years old on the web site.

2. The arc of value is radically different for men than for women in commercial sexual relationships. For women, the beginning of a relationship is risky, scary. Will he be violent? Will he pay? Will he be disgusting? Degrading? Cruel? As the relationship proceeds, as a woman gets to know a man, she feels safer, more comfortable, and the relationship becomes more valuable to her. For men, it’s the opposite. The beginning of the relationship is the most exciting, most satisfying part: as I’ve written elsewhere on this blog, it rarely is the case that sex with anyone is better than the sex we imagine with that person before it happens. Getting is better than having. The grass is always greener. Whatever. As a relationship with a woman progresses, that incredibly exciting discovery diminishes, and familiarity – that foe of passion – sets in. SO… men tend to shed women just as women are getting comfortable. This is a source of great frustration to women.

3. There are unsavory women and men who take advantage of these different “arcs of value.” Women often demand money up front, simply to meet. Some do so without ever intending to have sex. It’s possible to make a pretty penny doing just these “compensated first dates.” Men, on the other hand, often refuse to pay a penny, even going so far as to promise allowances, collect sex, and then disappear. Or simply go on a string of uncompensated first dates, collecting the titillating experience of meeting, talking with, sharing a meal or drinks with, an attractive young woman (who may well have dolled herself up, made herself look extra sexy), for nothing more than the cost of a few drinks.

[A note on this: women often said to me, “My time is valuable,” unaware of the irony of what they were saying in the context of the conceit of the website, and of just how much this made them seem like the whores they were so desperate not to be. Had a woman said to me, “I know it’s valuable to you to have a drink, or meal, with me. I’d like to be compensated for the value I’m delivering you,” I would have responded far better.]

4. Discussions of money are almost impossible to have well. Most women on the site want to think of money in units of “dollars per month.” Most men? In units of “dollars per hour,” or “dollars per date.” Almost every woman I ever paid for sex was desperate – desperate – not to think of herself as a whore, prostitute, hooker, escort, or sex worker. The “dollars per hour” or “dollars per date” way of thinking called that particular question in a way that generally made women uncomfortable (“It just seems so cheap.”). Men learn this, that the desired conversation is about an allowance, that women value obscuring the transactional aspect of things. Unfortunately, because of what I wrote above in 2 and 3, and 1, this then leads to much lying, some intentional, some not: men say they’ll pay an allowance of X, but lose interest after the first, or second, or third consummated date. I had one friend on the site who made the mistake of letting a guy see her three times before he was due to pay her first “allowance.” Which he never did.

5. Everyone is ambivalent. Very few people on either side of commercial sexual transactions are unambivalently happy to be participating in those transactions. Men, for the most part, don’t like paying for sex (unless the fact of paying is itself a turn-on for us, in which case we probably have some other shame making the whole thing complicated). Women, for the most part, don’t like having to have sex for money (although, interestingly, many do like being paid for sex – a dichotomy worth exploring, but not in this post). So here we are, all of us, locked in a dance of some combination of shame, sadness, and secrecy. Which makes us all ambivalent. Which, more than anything, leads to people being stood up, often at the last moment. If I had a nickel for every time a relative of a first date got sick, I’d have a lot of nickels. And then there are those who didn’t even call. People are late, chaotic, unreliable. And far more so in this realm than in any other realm of their lives. In my own case, because on some level I was battling myself every time I acted out sexually, I was prone to last-minute cancellations when my conscience was, momentarily, ascendant. I can only assume there was a similar process going on in the minds of the women who canceled with me at the last moment.

But it doesn’t just lead to people being stood up: it leads to a sort of heightening of all emotions. People are more prone to take offense, to feel insulted, aggrieved, slighted, and therefore, there’s a fairly high rate of implosion of relationships very early on, when the logistics and finances are still being worked out.

As a result of these, and other, lessons, here are just a few recommendations:

1. Be honest with yourself: to the extent you are, you’ll be much more comfortable, and happy. What you’re doing is sex work. You’re accepting money for sex. If you’re ok with this, you’ll have a much easier time on logistics.

2. Don’t idealize too much: while there surely are great guys out there, guys who’ll give you a handsome allowance and keep you on retainer for months, or years, those guys are few and far between, and it’s not where the market is on the site. If you’re gonna find that prince, you’ll likely have to kiss a fair number of frogs.

3. Don’t believe anything anyone says: I don’t mean that people are lying. I mean that people rarely know their own truths in this area. You’ll do best if you’re a skeptical consumer of everything anyone says to you.

4. Know what you want to get, and be crystal clear about that: women on the site get swamped with attention. There’s absolutely no reason not to be explicit about exactly what your ideal arrangement would look like. And then, be ruthless in your selection process. You shouldn’t meet anyone who hasn’t already agreed to your financial terms in principle. (Be prepared to do that on the phone; no one likes to agree to an illicit relationship explicitly in e-mail.)

5. Don’t meet with anyone too quickly; have an extended e-mail exchange with anyone before meeting them. As I wrote, for us men, that first meeting is itself valuable. One way to handle that is to collect money for that first date (but that may well rule out many serious men who object, rightly, to paying for the privilege of an interview). Another is to use e-mail to screen. By the third or fourth e-mail, people tend to communicate about themselves very effectively, and fairly comprehensively.

I think that’s it for now. Any other questions?


* Throughout this post, I write in generalizations – about men, about women. These are self-conscious generalizations, drawn from my experience. They’re not universal, and there certainly are exceptions. But I’ve been around the block enough to know that what I say here is, if not universal, at least extremely widespread.


  1. Have you heard about this new book Lost Girls by Robert Kolker? Its about a series of murders of women who were Craigslist sex workers. Many reviews say that the book explores sex work and how its been changed by the internet. I haven’t read it (yet) & real crime stuff doesn’t interest me, but sex work and the internet does.

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