My Sex Work Bucket List: Caty

by Caty Simon on April 8, 2013 · 22 comments

in My Sex Work Bucket List

I'm at least as badass as she is, right? Right? (Image from the movie "China Blue" (1984))

I’m at least as badass as she is, right? Right? (Still from “China Blue” (1984))

In one sense, I’m an old pro of a ho, as I’ve been escorting for a decade. But in another, I’m actually an  innocent, because besides a few shoots for various feminist porn venues in my early twenties, escorting’s the only kind of sex work I’ve ever done.  So, now, at the ripe old age of 31—which is an eternity in whore years—I’ve accumulated quite the sex work bucket list. Here are some of the highlights.

1) Hire another sex worker as a client.

I’ve always been curious about what this work looks like from the other side. And I envy my clients even as I pamper them: What would it be like to be the sole focus of sexual attention in a coupling, to be the ultimate pillow queen and not have to feel guilty for it because you’ve paid for the right? I bet I’d be the worst client ever, though—unable to maintain the illusion necessary to enjoy myself because I’m too aware of the emotional labor necessary to create it, no doubt trying to be too chummy with my escort on the basis of our shared experience when all he/she wants is to finish the hour and be done with me. Or, based on that understanding, I’d be so overly, nervously apologetic that my escort would pray to God for me to shut up. Still, even knowing all the ways I could royally fuck up the experience doesn’t detract from the potency of the fantasy.  I’d love the ability to say, “Let’s do something else, I’m bored of this now” in the middle of a sex act and have that be my natural right.

I’ve yet to fulfill this fantasy because it always seems like a waste to spend hundreds of dollars on sex when they could be spent on drugs. Also, who would I even hire? The movement makes it feel like I know every sex worker out there. It’d be incestuous as all hell.

2) Attempt street work.

This one shames me a bit to admit because it sounds so much like a desire to go slumming. But I only have the highest, awestruck respect for my street working friends, and what I really want from this is to prove to myself that I’m capable of doing the most primal, back-to-the-basics form of sex work. I also want the reassuring knowledge that if I’m stripped to zero resources, I can make money just by sauntering into a ho stroll. And the idea of doing sex work in jeans and a tank top is so tantalizing to me I might start drooling. My prospects are dim, though. I’m reminded of the one time I tried to work sans ad in Las Vegas, approaching a man at the slot machines. He politely declined, gesturing at his wife who was about ten feet away. You could tell he was embarrassed for me.

3) Do an overnight.

I’m a solidly middle-class escort in a solidly middle-class market in the boonies, where there isn’t enough demand for a high-class/courtesan market to exist. Most of my clients would never think of splurging for an overnight. I’m mostly glad of this—I can be the Whore Madonna of my clients’ dreams for an hour or two, but I don’t think I could put up with the majority of them for twelve while remaining perfectly nurturing  and simultaneously sexy. Even my favorite regulars have never gotten anything beyond a few hours at the incall followed by dinner.  And I’ve heard and read such gruesome horror stories about overnight appointments—Jeanette Angell’s account of being kept awake all night by a stingy client determined to get all the, ahem,  bang for his buck who then also expected her to empty his kitty litter box in the morning comes to mind. Yet my coworker B does regular overnights with some of her longtime clients. They take her to local strip clubs and give her money to tip the dancers, spend most of their time in the bedroom sleeping, then take her to Denny’s for breakfast when she wakes up. Honestly, that kind of sounds like fun. She has this amazing ability to turn half-hour clients into regular overnighters. Surely I could do the same?  At root, this is another one of those Just To See If I Can impulses. Also, I want to stuff a client’s money into a Mardi Gras girl’s garters.

4) Make porn that doesn’t embarrass me the way the porn I made in my early twenties does.

When I was young I had quite the artiste‘s pretensions. I was going to make porn as political art,  exploding the stigma around a diagnosis of mental illness by confronting the viewer with a mad woman’s sexuality. This mostly involved masturbating furiously and smearing lipstick on my thighs to simulate menstrual blood while a long suffering Barbara DeGenevieve looked on. A couple of friends and I were even pretentious enough to film a scene where we were punished by an angry schoolmistress for not finishing our Roland Barthes reading assignment. And I still feel like I owe Courtney Trouble an apology for the sheer awfulness of the porn a friend and I did for in 2002.

Anyway, I also want my naked body to be immortalized now that I’m not slowly dying of iron starvation as I was in my vegan early twenties. Back then, I was also still wedded to the idea that miserable=profound, as evidenced by the expression on my face in most of my solo shoots. “God’s got your dog! Your puppy dog, he’s going to kill it!” exclaimed Jason Ragosta, when forced to shoot yet more footage of me naked and frowning.

The list kind of blurs together after that with the enthusiasm of my ideas. I’ve got various half formed visions: Apprenticing as a domme.  Sex working abroad from Thailand to New Zealand like a modern day Dolores French. Doing a double call with a guy coworker to see if het sex simulated for a client’s benefit is any different from dyke sex under those circumstances (Why would it be? Yet, I still wonder). Stripping in some dream universe where I wouldn’t immediately fall ass over lucite as soon as I attempted a floor show. Some of my ideas are implausible, designed to console myself about the fact that though I have long term experience, I found my small comfort zone early on in sex work and have stuck to it.  I’m not the adventuress I sometimes imagine myself to be. Still, there are other items on my bucket list that I can imagine myself checking off blithely tomorrow. I’ve checked off plenty over the years, from women clients to watersports. What it all boils down to is something that I revel in, something that keeps me from burnout in the long haul: my continuing fascination with the industry and the people in it.

{ 22 comments… read them below or add one }

Elle April 11, 2013 at 1:09 am

Okay, now I want to hear about all of these AFTER you do them. And I need to write my own.


Caty Simon April 11, 2013 at 6:29 pm

But maybe we should have a feature about trying something on one’s bucket list–I wonder how one would catchily phrase that.


Caty Simon April 11, 2013 at 6:27 pm

I totally want a proliferation of My Sex Work Bucket List submissions–Charlotte is responsible for the best thing since sliced bread.


Charlotte Shane April 15, 2013 at 9:42 am

You are too kind! I love this feature too, and hope we get a billion submissions for it. This one was fantastic, Caty. I feel like you stoked up some love and enthusiasm for the work that has been all too dormant as of late. (And this was so hilarious: “Also, who would I even hire? The movement makes it feel like I know every sex worker out there.”)

I soooo want to hire someone now, and write about it for the site.


Caty Simon April 15, 2013 at 11:56 am

Thanks, Charlotte! Yeah, I think this whole idea of yours is very good for reigniting enthusiasm for our work in general. Now I’m thinking of suggesting an overnight to one of my regulars tomorrow when I see him for our monthly call. We also need to figure out how to frame a feature in which people write about checking off items on their bucket list, b/c there seems to be some interest in that—and I’d love to write about what happens on my maiden voyage in overnight calls. Also I TOTALLY want you to write about hiring someone.


Kitty Stryker April 11, 2013 at 7:31 pm

1. Yes, paying another sex worker for sex is as fun and as awkward as you wrote. I personally had the same experience- so many of my friends were sex workers, so how could I experience this desire in a pure fashion? I went to Amsterdam and cruised the windows, which worked out well. The advantage to the windows, in a way, is that you have to flirt with eye contact- if the girl didn’t meet my eyes, I figured she wasn’t interested in women. If she looked at me and a man near me, I figured she was more interested in couples. But if she looked at me, met my eyes, and smiled… then I thought maybe it was worth going up to chat. I was terrified, excited, wanted her to enjoy herself, yet wanted to honor that I wasn’t purchasing her pleasure, just (hopefully) her consent. It was complicated. I’m glad to have done it, and would do it again- as a queer femme, having space just for my pleasure and mine alone was pretty strange and new. The insight it gave me into what it’s like for my clients to come to me was *intense* and really gave me a lot of compassion.

2. I also want to do this sometime, but actually wonder if as a fat sex worker I would be putting myself even more at risk. I get enough violence against my body as it is. :/

3. I’d love to do an overnight, this is definitely on my bucket list too. I can imagine being capable of exhausting a client or just being firm about my own need for sleep. Again, I’d worry about the vulnerability though. I don’t know if I’d sleep at all.

4. I feel glad I’ve gotten to do a fair amount of pornographic work that I’ve been proud of. My Little Pony live sex shows are probably tops on that list.


Caty Simon April 13, 2013 at 8:11 am

Whoa, I definitely want to hear more about 1, some time. In fact, I bet we’d be happy to post an essay about 1.


Robin D April 11, 2013 at 9:36 pm

I deleted a conversation on my facebook that was getting increasingly embarrassing but will repeat the original comment here:

Caty Simon, this is making me want to tell you some stories. Like, stuffing a girl’s garter with some dude’s money is indeed a shit-ton of fun. Not an “overnight” though.


Amanda April 12, 2013 at 8:21 am

Done 1, 2, 3 but never 4.


Caty Simon April 13, 2013 at 8:12 am

Um, details?!


Amanda April 13, 2013 at 11:05 am

1) A male who plays both sides of the fence. It was fun but no serious chemistry. I’d recommend him in a second though.

2) Paris, two nights. It was like flying without a net. Both good and bad. I’d do it again, and smarter too.

3) Regular escort work. It’s run the gamut from if-I-move-an-inch-I-get-molested to we-both-slept-like-rocks. Usually they fall asleep at some point and I stay awake all night. Overnights are serious sleep deprivation for me. I’ve never had a man last all night banging me though. Not clients, that is.


Caty Simon April 13, 2013 at 11:32 am

By both sides of the fence do you mean he’s both a worker and a client? What made you decide on Paris for trying street work? What mistakes do you think you made and how would you do it smarter next time? Ugggh, yeah, that’s one of the nightmarish visions that’s kept me from trying an overnight so far–the idea that I’ll keep getting woken up by the lecherous client.


Amanda April 14, 2013 at 9:48 am

1) Sorry. He has both male and female clients, though he markets to gay men. I don’t know what his personal preference is, I never asked (seemed rude to do that).

2) Long story. As for choosing Paris…it’s not the US. The US is a dangerous country, even if you’re just a woman walking down a street at night, much less if you’re a sex worker.

3) I’ve finally figured out to take a sleeping pill once it’s bedtime (make sure they don’t know this). I’m out like a light and at least this way I know I will get some amount of sleep. I’d much rather give THEM a sleeping pill but that’s wrong. I’m used to sleeping by myself and can’t sleep with someone else in bed with me, regardless of how nice (or not) they are.

Olivia April 12, 2013 at 11:43 pm

I’m kind of surprised that you haven’t done any overnights. I’ve only been escorting since last summer and I’ve done a few. They are pretty taxing, because I’m a super introverted person and it’s hard for me to hang out and talk with someone for that long, but the money makes it worth it! All of the overnights I’ve done have involved maybe an hour of sex and the rest of the time was spent going out for dinner, talking, and sleeping. I have a regular client with whom I’ve done three overnights so far, and he even sleeps in the other bed (hotel room)!


Caty Simon April 13, 2013 at 8:12 am

Like I said, there’s barely any market for them around here. Also, I’ve avoided them like the plague till recently.


Caty Simon April 13, 2013 at 8:13 am

Do you make it clear during these overnights that it won’t be 12 hours of sex, or does the client just recognize that implicitly?


Olivia April 13, 2013 at 11:12 am

I guess the clients just know, so far anyway. No one has expected more than two rounds of sex. Maybe I’ve just been lucky though!


Charlotte Shane April 15, 2013 at 9:54 am

Hope it’s not rude to jump in here re: overnights but I second Amanda’s experiences above, and Olivia’s too, though I’ve also had a decent amount of third category, both-of-us-slept-like-crap dates. I think some guys are really nervous about their snoring, or disturbing me, or the bed is too small and we can feel each other’s every movement…. It’s been very rare for me (thank god) to have the over-sexually active clients with no respect for my normal human need for sleep, but it has happened. Once I got fed up and simply snapped “I’m actually really tired” and he seemed appropriately chagrined. I also see many, many longer date girls specify on their sites that they need at least 6, 7, or 8 hours of sleep. I bet it’s one of those situations where the guys who need to be told don’t bother reading that anyway, but I guess they at least have a disclaimer to refer to if the guy is really being a pest.

I thought about taking a sleeping pill, too, because I’ve slept well with a client in the bed maybe once or twice out of dozens of times. (Now I want to go count through my records—80 would be my best estimate.) But I hate how I feel when waking up from any type of sleepy-making drug. I’ve resigned myself to every overnight being a night of little to no sleep, and try not to do more than one a week, and to cushion it with a day afterwards that’s not too demanding.

And I’ve only known two clients who arranged separate sleeping spaces for me. One hired girls ALL THE TIME and I think he’d heard that his snoring kept them from sleeping regularly enough that he didn’t want to hear it anymore. The other was trying to impress me, I think. It sort of worked? There is nothing better than getting paid for an overnight while having your own private space for sleep and just alone, quiet time. But so far, in my experience, it’s very rare. Usually they want to snuggle and keep their eye on you because they’re so infatuated that god forbid you have a moment apart. (When they talk to you through the bathroom door….ARGH. DON’T YOU REALIZE I AM GOING IN HERE FOR SOME FUCKING PRIVACY?!?!?)

I’m an introvert too, so back to back overnights (like extended dates with the same person) usually make me crawl the walls pretty quickly, even if the guy is not that demanding.


Catherine April 25, 2013 at 11:14 pm

Loved this! I am so psyched to have you on T&S!


Caty Simon April 26, 2013 at 2:26 pm

That’s a huge compliment coming from you–thanks!


xxXVicXxx July 6, 2013 at 5:04 pm

Ah,geez,I thought it was just me that didn’t do overnights.I never understand my justification for saying no.As someone who saw(I’m on a hiatus)a mostly elderly client base most of them would suggest overnights.I would always say “no,I have to let my dogs out”.Looking back on the money offered,what the hell is wrong with me?I just could never get over the creeping unease of not being in my own bed.When I go back to work I’m going to say yes!Go me!


Caty Simon April 15, 2013 at 11:56 am

Now I’m having naughty fantasies about slipping benzos into my clients’ drinks…But yeah, that’d be wrong.


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