Kaytlin Bailey first wrote to me several years ago; she had started hinting at her sex work experience in her comedy act and wanted my opinion about coming out more fully. I was honored that she had confided in me, pleased when she started to make it in comedy, and proud for her when she decided to fully own her experience. We went out together one of the nights I was in New York last summer, and I’m grateful she replied positively to my request for this guest column. Her story isn’t funny, but it is, I think, a triumph. Her one woman show will debut in New York City at The Tank Theater July 10th, 11th & 12th. You can follow her on Twitter at @kaytlinbailey.
People tell me I’m brave. I try to remind them that I might be stupid.
I will never sleep with anyone ever again who doesn’t know. Not after he threw me up against a wall, or held me down on the sidewalk until I apologized for the things I had “done to him” five, six, seven years before we met. I was never afraid of a client, but I was terrified of a man I loved very much, who I thought I knew very well.
I started working as an independent escort when I was 17. There were other things going on in my life: I was the president of my high school debate team; I maintained an impressive GPA; I had a nice, age-appropriate boyfriend to whom I had dutifully lost my virginity months before; my parents gave me a generous allowance; I didn’t drink or smoke pot. I had never been raped, but I was sure that if I ever was I would report it and that my rapist would be punished. I had never been hit by a man. All of that came much later. For the first few months I couldn’t even legally rent my own hotel room; I remember one incident where after-school detention cost me over $1,000.
There were, of course, consequences. Making $400 an hour before I had any bills to pay, and spending hours in bed with deeply-unhappy rich men, gave me a lot of weird ideas about money & intimacy. I maxed out my Roth IRA for a few years and paid for a few decadent dinners with my friends, but mostly I parked wherever I wanted to; every morning I parked directly in front of the “no parking” sign in front of my high school, and never cared about the tickets because I thought I had “fuck you” money. I continued to see clients until it wasn’t fun anymore; I had the luxury of doing that. I went to college, got a few degrees, then started working in politics. At first I loved it; then I burned out, started doing open mics, became a comic and moved to NYC, in that order. And that’s when I met the man I thought I was going to marry.
I had so easily dismissed the slut shaming language of my hometown, the colloquial idea that there was such a thing as “the marrying kind”, or that anyone interesting enough to fall in love with would want such a woman (the kind I imagined busying herself with making cupcakes and saying no to perverse invitations). I saw the Madonna/whore complex, and maybe I bought into it a little too much; if there were really only two types of women, I was going to be the free & wild kind. I rejected the pervasive and perverse myth that when a man and woman go to bed together the woman gets up having lost something, and the man gets up having won something. I thought it didn’t matter how many men I slept with, because I was still me. And so I told him, and even though I hadn’t seen a client in over 6 years it broke his heart. His whole body crumpled up, and he shook first with grief, then with rage. He wanted so badly to make sense of me, to reconcile his love for me with things he thought he knew about “whores”.
Sometimes he would press me to give him the narrative of a desperate woman using her body as a last resort, or a victim of some horrific crime, or a stupid girl who got tricked into turning tricks. He was enraged by the truth, and couldn’t accept that I had been curious and turned on by the idea. I was not ashamed of what I had done until I saw what it did to him. It drove him mad, and so I left him even though I believed that he loved me. I left him because I knew that if I didn’t, he would kill me. And after I left I believed for a really long time that he was right, that there was something fundamentally wrong with me.
After I left him I started telling my story; I wanted to see if people who didn’t love me as much as he did could get past what they thought they knew about being a whore. They could. I started by telling audiences, tentatively at first. As a stand up comic I can tell my story with quite a bit of winking distance with lines like “its hard to go from making $400 an hour without a high school diploma, to making $10 with three degrees.”
I know there are consequences to telling my story. I’m afraid that stupid people on the internet are right. I’m afraid that when the sum total of my life is calculated I will have taken more than I have given. I’m afraid of giving birth to children that hate me. I’m afraid to tell my parents; what if I tell my Dad and it drives him to suicide? What if I give my mom the ammunition she’s always wanted to prove I’m not just difficult, but crazy? I’m afraid that I will find myself old, living in poverty, and neglecting myself and my dependent (a smelly dog who, justifiably, resents me). But at the same time, I’ve always suspected that people without a complicated history aren’t taking full advantage of life’s exhilarating opportunities. Sometimes I think I’m wired weird; maybe I’m crazy, or a “bad investment.” Maybe I’ve put myself in a percentile of people who are undatable…unloveable? But that’s what New York City is for; it’s where all the unmarriageable go to mate with each other.
I’m not an activist or a role model. I know it’s complicated & I don’t pretend to have a prescription for making anything “better.” I’m not even sure that the human experience can be made to be “better”; it’s pretty messy for everyone, even “the marrying kind” of girls. People ask me if I’m worried I’ll be pigeonholed. Yes, but also no. Was Dave Attell pigeonholed a porn addict? Jim Norton a pervert? Amy Schumer a slut? Chelsea Handler an exhibitionist? Well, yes, they were, but it didn’t limit them. I don’t know the future, so I’m choosing to talk about my experience, and I hope my audience finds me.
Go girl.
Thank you Kaytlin. One more example of something real.
You are FAR from being “unmarriageable”. And, there ARE guys out here who don’t care how many men you’ve slept with – or what reason you slept with them.
Life is really too short to give two fucks about what other people think.
And … never give up on the “wild and free” part.
My mother worked as an escort, can’t say I hated her for it, it was something she chose to do.
And so far from what I gather from this post your witty, intelligent and ambitious the trouble is perhaps finding someone who hasn’t been filled with preconceived judao christian ideas (one way or another) regarding sex workers, this I think might be hard especially in the US, but not impossible.
Anyway good luck with the comedy and anything else you wish to pursue.
Judao / Christians DO NOT have a monopoly on aversion to sex work. This aversion is quite common in most other religions – and among many atheists.
Just wanted to get that on the record.
While as an atheist, I still do not get the idea of “aversion to sex work” and sex-workers at all, I do agree that this time religion does not seem to be at the core of the problem and at most fulfills its time-honored role of making things worse.
That said, the reaction of Kaytlin’s lover reminds me very much of that of an arrogant and superior fraudster that has gotten caught by a mark, and just cannot cope with his superiority turning out to be purely in his imagination. The end to that relationship may have been for the best, because if some abstract, non-critical fact about a lover is more important than your concrete, hands-on experience with them, then something is really badly messed up deep inside you.
“Judao / Christians DO NOT have a monopoly on aversion to sex work”
Perhaps, although in the current context we are talking about the US.
And even atheists can adopt Judao Christian values without adopting the rest of the religion.
I agree with Krulac, I think you were just unlucky to get involved with a man who really believes the Madona/Whore myth.
The biggest problem (but perhaps not the only one) I had as a child who had a mother who worked as an escort was the conflicted understanding I had of her chosen job, which I attribute to the barrage of disinformation that we are constantly assaulted with regarding the sex industry, as a child (and some would say still now) I was very bookish and read a great deal, however that seemed to only add to my confusion.
The end result of this particular issue is that I as an adult I am now very skeptical of information presented un critiqued, I tend not to accept things as said, unless its comes from someone who has consistently shown themselves to be an honest, intelligent and trusted source.
In which case I then listen very carefully.
I’m not an activist or a role model.
That is precisely the point. If a group is to be continually marginalized and stigmatized, members of that group must be denied access to the mainstream. All members of that group; because each new one is another nail in the coffin for the silly prejudice against sex workers.
A little melodramatic, I bet she carefully selected a man with a certain character, and would have felt disgusted if she found out he used to be a “hobbyist”, though there probably wouldn’t have as much conflict since she simply would have never thought about him again.
I’ve actually dated a hobbyist briefly. Our relationship ended for other reasons, we’re still good friends. It was refreshing to be with someone who had their own experiences in sex work & didn’t fetishize/minimize/violently react to mine.
What an honest and enlightening column. Bravo, Kaytlin, for telling your story, and Maggie, for allowing her to do so.
While I don’t claim to have a huge amount in common with you, Kaytlin, since in truth I probably don’t, there is so much you say about yourself and your experience with which I can identify, beginning with your lead paragraph.
The other thing I really identify with is the need to be absolutely honest about our backgrounds with those with whom we would become intimately involved. Not telling the whole story, and not expecting the same of our would-be SO, is a recipe for disaster. At best it blocks intimacy, creates false images and forces us to live existences of quiet desperation, and at worst it leads to things like your sidewalk drama and broken hearts, loves, and lives.
The dilemma of what to tell parents and other family members is a bit trickier, as you express, but given a public existence, as you have, I’m not sure they don’t already know or can guess. I still lean toward honesty, at least on a “need-to-know” basis. Our children, on the other hand, deserve nothing less than honesty, and respect. Denying those things to them leads to the kind of resentment you fear.
I also can identify with how you see yourself ending up (my worst self-image is to be old and living alone in a run-down apartment in St. Pete — or at least as St. Pete was — and eating tinned pet food). And I lovelovelove your quote: “. . . I’ve always suspected that people without a complicated history aren’t taking full advantage of life’s exhilarating opportunities.” YES!!!
It often does take courage to face our own past, but that pales in comparison to the courage it takes to face our future. I admire your doing so through the prism of your past, acknowledging who you are but not knowing who you are yet to be.
Thank you!
I agree entirely with your statement regarding honesty, possibly it can be included within a discussion about unwarranted social pariahs, covering skin colour, perceived race, ethnic groups, class or professions etc.
Kaytlin continues to be brave and strong, challenging others to do the same. (Yay, Kaytlin!)
Well written. Reminds me of the colour of life. Not much black and white. 🙂
Hi Kaytlin, it is not really that important whether you are stupid or brave, it matters what you do with the possibilities it gives you. Personally, I also found that with things I fail initially at, if I keep at them, I eventually get better at them than at the things that I managed to get right the first time (booooring….). So keep at it, and if full-disclosure about a job you did a long time ago is necessary to screen out the occasional closet-psycho, so be it.
Thanks, Kaytlin, for the heart felt column. And I hope you success with your shows in New York. I wished I were there to see you. There is no doubt I have always been weird, and maybe a bad investment myself, but I never doubted that I was lovable. And like you, I always looked for the path others feared to tread. When I finally go married in my 60‘s, I told my wife that I once had a whore for a girlfriend, well, a high class call girl, and maybe I was even a pimp-daddy because I would help her a bit with her business. My wife thought this was hilarious and likes to joke about that girl (who in her own mind) was a high class call girl. The world in full of all kinds of people and there is a great percentage who will love and adore you.
Thanks so much for telling your story and being honest about your experiences in sex work. Because of you and many others who are brave enough to be open about their (past) work, people’s ideas about prostitution and sex workers are changing. You’re paving the way for others :).
Be a shame if your human need to belong gets usurped by the agenda of others Kaytlin. Lotta people blowin a lotta smoke about how things outta be – “u go gurrll” – heh. I invite you to consider the long game kiddo. There may be regrets for experiences missed, but I bet even more for legacy not left after your passing. Remember that not every defining experience is necessarily one that we would recommend for all our fellow passengers on this lovely Blue Boat Home. Some say it takes more courage to admit that than to double down. In the meanwhile, fair seas and following winds for thee and thine fair lassie.
When real love goes to war with the delusions men construct to protect themselves from pain, well… it can be murder (figuratively, and sometimes literally, too). I wish I could engage in some fancy intellect-speak to distance myself from your ex-fiancee’s state-of-mind, but in all honesty, I cannot; when the love of my life confessed to me that she had indulged men for drug money my reaction was “Yeah. And?”. It sure wasn’t because I was “enlightened” – I just simply never had any romantic expectations for myself (that, and the fact that I suspected it early on; it’s not that difficult to recognize a bird that doesn’t cage well). And that is the crux of the matter – I thoroughly understand what he realized in that moment (even if I never reacted to it in the same way); that the person with whom his fate is now entwined with will never need him as much as he needs her. Yesterday, you were a normal “civilian”, bound (in theory and/or dogma, at least) by the same restrictions he was. Today, you’re someone else that are far beyond them. Deep down, he wasn’t enraged by your “wrongfulness” (no matter how much he tried to define it as such) – he was enraged by the fact that his own “value” was now an unknown and completely in someone else’s hands. And if it ever hit the “expendable” mark, he’d be the last to know (strange this, because it pretty much counts for everybody anyway). That’s why he needed you to conform to this or that stereotype – he probably did love you very much, but if he couldn’t get you back onto his level there was no escaping the inevitable. To a lot of men, it’s pure, stark yet empty logic that cannot be argued with, and that logic can knock men back (yours truly included) into the vulnerable, scared little boys that men all hope they had left behind at the schoolyard. If it sounds as if I’m using hyperbole here, then I apologize. It’s a pretty brutal awakening when your’e naive. Of course, to women this seems quite bizarre and incomprehensible, and rightly so, but at that stage you had about as much chance of mitigating it as spreading your arms and stopping a tsunami in it’s tracks. If you believe that he was going to kill you… then I believe you too. There is only one thing you could have done to prevent this – and that would have been to continue the lie and become the dutiful (or whatever) housewife (or whatever). I don’t have to imagine what that’s like… I see it on people’s faces everyday. I never married because I couldn’t stand the idea of someone I love doing that.
You’re pretty brave to do stand-up comedy. I love crowds, but not when they’re all staring at me (reminds me too much of hungry zombies). And New York sounds like the perfect place for another “unlovable”, “undateable” person like me, too.
What an incredibly insightful, sad, uplifting comment. I almost kinda feel like I better understand some men some of the time now, not something I’d really thought I needed much help with (I kid, but compared to most women, the little knowledge I’ve achieved on the subject of men can make me feel like I’m psychic.)
Thanks. It’s nice to know my rant made sense to someone, lol.
I can think of more than a few escorts whom I would gladly marry after their escort careers were over. Don’t let one man’s idiotic reaction to your past ruin your view of men. You’re a beautiful, intelligent and funny woman. I envy the lucky guy who gets to marry you.
[…] From her article: […]
[…] From her article: […]
I’ll confess that my first reaction was to that photo: beautiful, hot, cute. Do you know how few women can pull off all three with one photo?
The story you tell isn’t nearly so pretty. I don’t understand his reaction. I’ve been angry with a woman, I’ve been disappointed, but have never gotten violent like that. And if I had, it sure wouldn’t have been over that. I don’t understand his reaction. I’m sorry you had to experience that. Your decision to never again sleep with somebody who doesn’t know is probably a good one, though I suspect that reactions like his are rare. But, well, better to get it out of the way at the beginning?
I’m gonna go see if I can find you on YouTube, since I’m not likely to get to NYC anytime soon. Best of luck going forward.
Kaitlyn, the only advice this awld dawg could offer, is the only thing that matters; be true to yourself, love yourself for who you are, and know yourself.
The one thing I’m 100% sure of is that, regardless of the haters, and the wretched abuse that sex work is getting, we’re all just plain folks trying to rub along as best we can; wether we’re clients, workers, commediennes, Honest Courtesans, friends, partners or just strangers on the Internet Train.
If I were to find out that my beloved wife had been a Lady of the Night, to be quite honest I’d still love her, because real love is a warts-and-all thing, not something you cut into slices, and any truly strong person feels love in a way that sacrifices, never asks why, and goes to the wire not just when things are great, but when they are awful, too.
The best one can do is love that way, and hope to get it back. 💕
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[…] contar mi historia. Y se la conté a todos. A gente en el bar, en el avión, en citas. Escribí un artículo. Grabé podcasts. No podía dejar de hablar de eso. No pasó nada malo. La mafia agresiva que […]
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[…] This week on the podcast I sat down and spoke with former political campaign activist, former sex worker, and comedian Kaytlin Bailey. She was in Boston for the Women in Comedy Festival and to kick off the Cake Comedy Tour. We talked about having to stay in an AirBnB with the fear of bedbugs, putting together a comedy tour, being a political activist, and Kaytlin’s time as a teenage and adult prostitute. Find more about Kaytlin’s story with her father, her one woman show, and the sex worker industry. […]