Politics Magazine

What Does It Take to Be a Gigolo Or Kept Man?

Posted on the 08 November 2013 by Calvinthedog

A regular reader writes in to tell me what he feels are the essential elements of what a gigolo would need in order to be successful. I agree with most of what he says. Surely, gigolos are not common. However, I knew a man who did this in 1983. He would take women to Las Vegas for the weekend and was paid about $150-200 for the weekend. However, he said that many of his customers were overweight or homely, so this was a downside to the job. I also agree that a gigolo would be more of a companion than just a sexual serviceman. Certainly this type of work is not common. Of course there are no straight male streetwalkers (all male street prostitutes are selling homosexual sex to gay or bi men) and there are no gigolos advertising on Craig’s List.

I also agree that the best gigolo would be:

Intelligent and well-spoken (older women are much more interested in a man’s mind than a younger woman is, and they are much more educated and interested in intellectual subjects than young women are.)


Socially versatile or a social actor

Empathetic and understanding of the female mind and probably somewhat androgynous in this way.

Good dresser

I also agree that your average slacker, cad or user/manipulative type would probably make a poor gigolo for women. Women would catch on to his jerky ways very quickly. Women are deluged with these types as it is. Why pay good money for another one. Asshole males are a dime a dozen. A good gigolo really should be above that, something worth paying good money for – a man who is not a lazy, sleazy prick.

I really know very little about that sub-culture. What little I know indicates that it is a high-end type of business; you don’t have man-hoe streetwalkers or straight prostitutes doing much in the way of Craig’s List-type postings, so that, to me, means that it includes much more in the way of companionship, as opposed to just fucking women.

I would think that in order to be very successful in such a capacity, a guy would have to be reasonably well-spoken, charming, possess social versatility, have enough empathy to be able to read a woman properly and also have a decent sartorial sense (as well as wardrobe).

As far as “Alphas” go, I think it would have to depend upon one’s definition. To me, a true “lady’s man” is usually not a “man’s man”; in other words, he is not insecure enough to be concerned with dominating and intimidating other men. So, by that atavistic definition, I would say not.

However, by my own estimation (since I consider myself to be a lady’s man and not a man’s man), I would consider this to be the description of an Alpha from a more modern societal standpoint, for I consider it to be a sign of breeding and evolution to be able to understand and gain the trust and affection of women as opposed to merely dominate and subjugate them.

But what the fuck do I know? My girlfriend is an opera singer, an extremely emotionally complex and sensitive creature, yet I am able to understand, appreciate and nurture her where others have only been intimidated and frustrated by her; in that sense, I consider that my abilities make me a true, modern Alpha and I would equate those qualities to being necessary for a successful gigolo.

But as far as slackers, cads and users go, I don’t think that those types of men would be able to achieve any type of real professional success as a companion.

This man, a former straight male porn star (Yes, I have porn star friends) then relates his career as an occasional kept man:

I lived off of women for a time when I was younger. I had exhausted the modest inheritance from my mother’s death financing my musical career and, having had no examples growing up of a normal 9-to-5 existence, I was having a bit of a tough time learning how to live as a “mortal”.

One of the women I lived off of wasn’t rich, but she was a stripper in Houston who would soak rich guys and then take care of me. I lived in Sherman Oaks at the time in a house with my bandmates and she would pay my rent, buy me clothes, send me spending money and even finance my recordings; all I really had to do was let her fly me out about every month or so for a week, fuck her and let her show me off to her friends. That got old after not very long.

A bit later in my life, I had a bit of a thing with the divorced wife of a casino owner in Vegas while I was living there; I was about 30, she was 40 and quite nice looking, but an utterly reprehensible, elitist, paranoid Jewish-princess cunt, so I didn’t let that go on for very long. However, she did pay my rent a couple times, took me on a couple trips, etc.

There were a couple others in between, mostly divorced women, not super-rich, but former LA trophy wives whom I would meet at some of my shows that fancied being with a younger “bad-boy” and would invariably spend some money on me, usually in the form of helping with rent, some dinners, weekend trips, maybe pay for my weed or buy me some clothes, but nothing really in terms of an exchange; I think you’re familiar with the set-up. They’d usually get weird on me, though.

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