The pitfalls of paying for it

The other day, I wrote a bit about the trajectory of most of the relationships I had during my CPOS days, when I was routinely paying for sex. Today, I don’t pay for sex. (As with all things, the truth is a bit more complicated – the nature of dating, even of poly/swinger/postmodern dating, especially if you’re a dom-ish kind of guy, is that you do end up paying for virtually everything, and I’ve been known to pay a companion to accompany me to a sex club, even subsequent to the days of my paying for sex routinely, but, well, I don’t pay for sex.)

But here’s one of the things about paying for sex: it brings into question anything you might otherwise imagine about an interaction, sexual or otherwise. Is she here because she likes you or because you’re paying? Is her orgasm real or performed? Is she really into you, or not? Now I’m not a rube, and I’ve been around the block. And, I’ve been with a lot of women who clearly weren’t having fun. But what of those whom I genuinely believed to be enjoying themselves? Were they? Were some of them? All of them? None of them?

I think I know the answer. I’ve even stayed friendly with a few of them in the years since I stopped, and these now are women who have no real incentive to lie to me, so I tend to take them at their word.

But one reader wrote me after a recent post, and gave me her own tale of participating in a SeekingArrangement threesome. First, she wrote, “My friend is on that site and I had a threesome with her and her sugar daddy a while back.”

I asked her to tell me about it.

“Are you sure? It wasn’t so sexy (in my opinion). I felt more like a performer.”

“Totally sure,” I responded.

She replied, at length:

We went over together to his hotel, I was wearing this really slutty leopard print dress (I like to dress the part). He was chubby, mid 40s, Jewish dad. Tshirt and gym shorts, the worst. We sat on the bed and talked and drank wine. The whole time I was thinking, there’s no charade here, why doesn’t he make a move?

And then he started rubbing my back and telling me how pretty I was. Since I had NO interest in kissing him (I don’t like to kiss usually), I started rubbing his cock through his shorts. We fooled around for a little bit, he was graceless.

He stood up, pulled me to the edge of the bed and started licking my pussy. I made little moaning sounds for a nice effect. He stopped and told my friend to play with herself. But in like an annoying way “oh E you look lonely, do you want to play with one of the toys I bought you?” Very passive.

Then he fucked me for a little, then he fucked her and finished. He got up to go to the bathroom and put [the money] in my bag. At that point I was ready to be done.

But then we fooled around a little more, and he tried to fuck me without a condom. And then he fucked her while I was behind him. Then I went home.

I’m not sexually attracted to this friend, I found him almost distasteful, and I didn’t feel comfortable to be as enthusiastic as I like to be. But I made a nice amount of cash for very little effort.

“Bummer,” I replied. “That sounds awful. What do you think his experience was?””It wasn’t awful,” she wrote. “He had a fantastic time.”

I asked a couple of follow-up questions. I won’t go into the details, but suffice it to say, her friend saw him one more time, she never did. The guy offered some excuses and went his way.

A couple of words, before I reply in earnest: I like this woman. She and I have e-mailed a bit, and she’s extraordinarily hot, sexy, and mysterious. If my life were to give me the opportunity to fuck her, I’d be delighted, though, for a variety of reasons, I think that actually unlikely.


Once in a while, I’ve been with someone who was interacting with me like this. (After all, I am a mid-40s Jewish dad, and I’m sure there were times when I didn’t exert the effort to change out of my shorts.) And I’ve found it horrible. When this happened, I would generally go through the motions myself, and count the minutes until I’d be alone, free to stop my own acting. Did this guy really have “a fantastic time”?

Far more often – because I was lucky? Hot? Talented? Deluded? Some combination? – the interactions felt genuine, like I was with someone who was, sure, working, but working at a job she enjoyed, was lucky to have, etc. This is the thing: I think that prostitution, in whatever guise, is a job. Many of us have jobs we love. Many have jobs we hate. Most have jobs with parts we love, and parts we hate. I genuinely didn’t want to be with a woman who wasn’t genuinely excited to be fucking, or sucking, or hanging out with, me. That was, in fact, a crucial aspect of what I was buying. And, as I’ve written, deciding to “buy” that is itself a somewhat… problematic… approach to meeting that need. Because no matter how much she did want to be fucking me, sucking me, the fact was, at the end of the evening, she walked away with a heavier purse, and I, with a lighter wallet.

So were they all thinking what my friend, above, was thinking? About themselves, their experiences? About mine?

All my instincts tell me that I’m actually fairly good at reading people – even those whom I’m paying to suck my cock, or to fuck. That I can tell when someone is having fun, and when they’re acting. Has a woman ever fooled me with a performed orgasm? I’m sure the answer is yes. But with performed affection, interest, empathy? I think that’s a lot less likely. Not impossible, but less likely.

And yet, and still, I was paying, so I can never know….

One comment

  1. I will pre-empt these comments to say that I am not in the most positive frame of mind today. So maybe some of the things I am about to say should be taken with a tiny grain of salt.

    I have never paid for sex nor been paid to give sex to anyone. Not in the sense that money actually changed hands. I would argue that many women get paid for sex quite regularly. The payment isn’t cash or via a credit card but comes in other forms, affection, power, a child they want, a marraige, not having to work, not having to do all the household chores, not feeling guilty about the new dress they just bought, the list goes on and on. Most of the men paying women in this way are convinced that these women feel genuine affection for them and probably most of the women have convinced themselves that they feel this affection as well. Maybe on some level there is affection but humans are complex creatures and rarely do we do anything for purely altruistic reasons.

    As far as convincing a man that her enthusiasm is genuine that is an art that many women learn and start practicing from birth. They practise on their daddies, their uncles, their grandfathers etc. They learn early on that their enthusiaism brings more pretties and other emotional rewards. Why would this ingrained behaviour change in adulthood?

    In summing up the cynic in me feels that women are often more skilled at convincing men they are enjoying things than men realise. Men often allow themselves to be convinced because facing the alternative, (admitting they are doing a bad job) is too hard.

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