Harlotry: My Friend Wanted To Try Being A Prostitute With Me… It Was Awkward

The guy lived on a tree-lined side street in a nice part of Chicago. He lived in a penthouse that took up the whole third floor. The first thing I noticed when we walked in was that it was obvious he didn’t live alone. There were little lady touches everywhere: the ballet flats by the door, the Audrey Hepburn print on the wall, and the general Anthroplogie catalogue feel of the whole apartment. He had a female roommate at the very least but it seemed more likely she was a live-in girlfriend. I was aware that a number of the men I saw were married or otherwise attached, but it had never been so obvious. I’d never actually gone so far as to essentially intrude on another woman’s home. It was awkward.

Our client handed us each an envelope, and led us to the bedroom. Natasha and I got onto the bed and started kissing. We had no chemistry and I hoped it didn’t show. We undressed each other awkwardly, I retrieved the vibrator and a condom from my bag, got behind Natasha and started using the vibrator on her. My reserves of dirty talk were already failing me, and the client hadn’t even pulled his dick out. I decided that oral was probably the way to go. Everyone likes watching girls go down on each other, right?

Maybe it was the lack of chemistry between Natasha and me, but I had never really noticed how ridiculous sex can be until I was performing it in front of this total stranger. There are weird positions, weird noises, and weird fluids; when you pause to think about it, sex isn’t terribly sexy. Crawling around from behind Natasha to get between her legs made me feel like an awkward, anxiety-ridden virgin and I’m sure that’s exactly what I looked like.

But what was I supposed to say?

“Sorry, this isn’t traumatizing or anything, it’s just too awkward for me. Here is your money back, sir.”

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    • Amy

      Hi Cathryn, slightly off topic, but do you have any other book recommendations about being a call-girl/prostitute?

      • Cate

        Well, Belle de Jour’s books are excellent (The Intimate Adventures of a London Call Girl, and Belle De Jour: Diary of an Unlikely Call Girl are the ones I’ve read, but there are others) and Indecent: How I Make it and Fake It as a Girl for Hire is wonderful, although it isn’t about prostitution so much as general sex work. I also am a big fan of Whores and Other Feminists which is a collection of essays by sex workers including, but not limited to, whores. I don’t consider myself a feminist so I was initially kind of scared off by the title, but there are some gems in there.
        Also, Charlotte Shane’s blog Nightmare Brunette is full of some of the most beautiful things I’ve ever read. It isn’t a book, but I think it should be. Charlotte’s experience with sex work is a lot different, and probably more interesting, than mine.

    • Emma

      And now I need a bleach shower.

    • Meagan S

      OMG- that sounded like a horrible experience. Very interesting article. Thanks!

    • len132

      Yeah, I’m not pretty enough to be a prostitute. At least I know that, I guess?

    • Dami

      Wow….it amazes me how ‘cool’ whoring oneself has become nowadays, thanks in part to fabulous propaganda over the last 15+ years. It’s working!!! ;D (just ignore the data on the increase in rape, abuse, teen prostitutes, misogyny in the media and sex trafficking because they’re probably not correlated).
      But really, it’s sad that so many women and men rationalize this trade, which by the way is NOT the oldest in the world(think construction/labor, healer, cook, midwife, hunter, gatherer… etc…then maybe whore). <That again, is more rationalization. It's sad that women think they're liberated when they sell themselves. It's just been sold as so (for many many years, we're having another resurgence). But it's simply not true, but myself nor anyone can convince these women otherwise until one day they feel cheapened and worn out, empty by the whole experience, have some epiphany and become healers, therapists, activists for women, writers or some other trade to help other people overcome yada yada……
      Just breaks my heart the whole lie of it. And all the young women growing up in today's times angsting over the hell of choices they have to make armed with such idiocy, body loathing, degradation and debasing information out there. Those are who I really worry about, the girls growing up today. :( But people in this industry promoting it, I really don't think they care about those growing up today, the younger generations, except to help induct them into it.
      And yea, I'm an effing feminist(as in I believe in women's lib, don't believe in misogyny or whorification of women, nor objectification of women or sex, or hell even men for that matter). But that's just me. I do believe in intimacy, healthy passionate sex(between any configuration of humans of consent, love, respect, comfort within our own bodies and respect for others, the pursuit of joy and safety in this world etc……None of which I think is found through sex for sale.

      I do though however, wish you some better path and think you ought not to encourage other women to do this. Some part of your soul has had to shut down to fuck and suck strange men repeatedly I imagine…that or your a sex addict or you were abused or neglected…. Otherwise there just doesn't seem to be a sane reason to do this. (besides money which is just simply sick).


      • Dami

        Oh yeah…I forgot to mention, I’m of a different generation than the younger ones today so I was raised on a different value system(actually a value system period) that is practically non-existent today. Think 70′s/80′s kid.
        The people growing up in the last 15+ years have been inundated with such good, or bad, depending how you look at it-commercializing propaganda about everything, esp women, esp sex- that many people without some other positive influence literally, don’t know anything else but what modern society is telling them: that compromising or whoring oneself or even another to profit in any manner, whether it be sexual or professional….that selling out is absolutely Ok. And that as a result is teaching several new generations how to compromise themselves/others and spin sharp rational to justify it. This in turn, opens the gateway to other more insidious elements that don’t always turn out so good (think child porn and sex trafficking) because the gate is simply too far open…..

        And that’s just downright sad. :(

        Hopefully we as a society, can bounce around a little and recover ourselves a bit…as I don’t think swinging from one political or social extreme to another is healthy or good for anyone really.


      • Cate

        I know I shouldn’t feed the trolls, concern or otherwise, but I’m going to respond to this anyway.

        There is NO correlation between the increasing acceptance of the sex industry and increased rape, trafficking, and molestation statistics. Studies that claim otherwise have been disproved again and again. In addition to this, your claim that decriminalizing prostitution will contribute to sex trafficking and child pornography is laughable. If anything, decriminalization will help victims of trafficking by removing the possibility of their arrest if they go to the police for help. In addition to this, decriminalization will eventually help to remove the stigma associated with prostitution and create a much better quality of life for the women (and men!) in the industry.

        While I agree with you that sex work is not intrinsically liberating, it’s also no more degrading than any other job, and frankly I felt more degraded working as a bartender than I ever did as any kind of sex worker.

        You claim to be a feminist, but this entire comment ignores the personal agency of myself and women like me who choose sex work and often find it quite fulfilling. So sex work is not something that you could feel comfortable doing, that’s fine. There are a lot of jobs that I wouldn’t feel comfortable doing, but that doesn’t make those jobs inherently degrading. If someone enjoys being say, a garbage collector, who am I to tell them that they are wrong for choosing something that I think would be disgusting and awful?

        For your information I’m neither a sex addict, nor a victim of any kind of abuse and neglect, and judging from my experience I am hardly an exception. To be honest, most of the sex workers I’ve met have had perfectly happy childhoods and perfectly healthy relationships with sex. The claim that only a damaged woman would choose the sex industry is a symptom of the misogyny in the media that you claim to so revile. Naturally, a large part of my attraction to the sex industry has to do with the high earning potential, but I don’t see how that’s sick. I enjoy living alone, having nice things, and being able to rely on the contents of my savings account in case of disaster. All those things require an income higher than most people my age can realistically make in a non-sex industry job. This is not to say that sex work is a good choice for anyone who wants nice things, but for me it is.

        P.S. As someone who is neither a sex worker, nor an ally of sex workers, you should probably re-think your use of the word ‘whore’. It’s similar to other reclaimed pejoratives in that it’s still very rude to aim them at members of the group they are meant to insult.

      • Jen

        Wow. What an amazing response to a terrible (torturously long) troll comment.

        I wish I was savvy enough to post that gif of Citizen Kane doing the slow clap, because I’d put it right here.

        Beautifully done.

      • Cate

        Thanks Jen! I feel like I should still reply thoughtfully to concern trolls like this woman (I’m assuming it’s a woman at least) because a lot of people really do hold her views on the sex industry. These kinds of inaccurate and puritanical beliefs have to be dispelled before the stigma attached to sex work can be destroyed.

    • Shara

      Just a quick question here Cate, I’m wondering why you don’t consider yourself a feminist?

      • Cate

        I think that feminism, while it definitely has some good points, is far too exclusionary. The problems with the way people are treated in this society are by no means limited to women, and I think that at this point in time we require a much broader perspective than feminism can give us on its own.

      • Tania

        I think the problem with that isn’t the definition of feminism – that’s just equality between the sexes, and true feminists (as in, those who are solely after the definition – equality) aim to fix the inequities aimed at men as much as those aimed at women.

        The problem is what society has decided to pretend feminism is, thanks mostly to conservative pundits and those with female superiority complexes. (Like, does anyone seriously believe that if women ruled, there’d be no wars? There’d be a lot more poisonings over nice dinners, is what there would be.)

      • Cate

        Tania, I do agree with you on that, and I think that feminism definitely started from a really good place. If we’re really getting down to what I would define myself as on a personal level, sure I’m a feminist. However, there is such an overwhelming number of feminists who ignore the fact that women aren’t the only ones who experience gender-related difficulties in this society and so many people who have encountered THOSE feminists and had their view of feminism shaped by them that I prefer to just say, ‘I’m not a feminist, I just believe in equality’. I feel like ‘I’m a feminist, but feminism means something different to me than it does to a lot of people, here is my long-winded explanation of the kind of feminist I am’ is a lot less productive.

    • MeliMachiavelli

      Nice job Cate!

      Sorry — but I lul’d.

    • Megan

      What an awkward experience. lol But in all seriousness, I LOVE reading your posts weekly.

      • Miss Truth Hurts

        The whore that wrote this sh*t is disgusting!

    • auric

      Interesting “adventure”. There have to be literally dozens of stories about other uncomfortable scenarios that you have encountered – would make for a great book! Think “50 laid of Cate” or something ….

      Although I might be the most unpopular man contributing to this topic, I often wonder if some of the comments from people against sex work come from a desperate appeal to provisionally “level the playing field” (so-to-speak). Let’s face it … you see a lot more men bedding sex workers than the reverse. Women competing for the attention of men don’t want to have to compete against sex workers. They see women like you, I suspect, as “cheaters-of-the-game”, who make it that much more difficult to find a man and keep his interest (although I think that is a bit of a simplication). I know that, given the choice, when it comes to sex, I find it much easier to get what I am looking for by simply paying for it than the alternative (pursuing some woman that might not be interested in it after hours-to-months of pursuit). It is like the choice between going out fishing on your own or chartering a fishing guide that guarantees you will catch some fish. Sometimes it’s so much easier to simply choose the latter.