Shortly after my ex abandoned me and my two young children I started doing sex work. I luckily had very few bad experiences, quickly found four regular clients, and was able to stop advertising and made enough money to keep us in an apartment in a safe neighborhood.
A few months in, I met an amazing man. After meeting several times I made the amateur mistake of moving him from customer to boyfriend. Things went well for a bit but he progressively got less generous. (This is common, I've since heard.) Six months after we met he bought me a car and considered any financial obligations to me "complete." We had a discussion about how I was going to get a "regular" job and be in a monogamous relationship with him. The only problem was, no regular job was enough to support my family. I struggled and hinted that I needed some help, but he encouraged me to persist. Instead I reached out to a former client and he happily started paying me for regular visits again. The extra cushion kept us afloat and since I thought of it as work, I convinced myself I wasn't technically cheating.
You probably already know where this is going: My boyfriend found out, was crazy jealous, and insisted I "dump" the other guy. And I was so dumb and in love that I did... until my older kid needed braces and my younger kid needed glasses and my bills were out of control since we live on the poverty line. (Did I mention my boyfriend was making six figures?) After months of going back and forth, he dumped me for good and took back his car. Now I'm ready to start dating again but I'm not sure how to approach it. I work retail, but still see my one client for whom I provide a specialized niche service usually about once a week. I don't consider myself a sex worker anymore really, but the couple hundred extra dollars a week is intrinsic to my family's survival so I will not give it up. Do I have an obligation to disclose this work to future suitors? I feel like if I do I will never find a man who wants to be in a relationship with me. For what it's worth, the service does not involve PIV sex, and is more "scene" acting.
Worried Over Recreational Kinks
You aren't obligated to disclose your side hustle to a casual partner—and anyone you start dating is a casual partner until the moment you decide he's not.
Setting aside your family's financial security and your responsibility to factor that consideration into your disclosure decision, WORK, the fact that you aren't engaging in PIV sex with your only client gets you off a very significant hook. Because the single best pro-discloser-of-sex-work-to-new-romantic-partners argument is informed consent, e.g. a new romantic partner—someone you've made a commitment to, somehow who might reasonably assume* you're exclusive—has a right to know about sexual contacts you have outside the relationship, whether you're being compensated for them or not, because they arguably present a health risk to your new partner. But if you aren't having PIV sex with your only client—if you aren't having the kind of sex that presents the greatest risk of transmitting a sexual infection—you're under less obligation to disclose. And if you're not having oral sex either, WORK, if all you're doing is roleplay with some incidental physical contact, your moral obligation to disclose all but vanishes.
Actually, let me back up. The best arguments disclosing the fact that you do sex work are 1. you aren't doing anything wrong and 2. you shouldn't have to hide and/or shoulder the stress of hiding. But in reality... the stigma and the legal risks are so great that disclosing your side hustle to a new or newish partner presents too great a risk. As you've already experienced, WORK, even a romantic partner who seems comfortable with sex work at first can reveal himself to be possessive and controlling asshole who isn't okay with sex work—and your ex was a client before he became your (controlling, stingy) boyfriend! Even more worrisome, WORK, are the okay-with-it-at-first boyfriends who reveal themselves to be vindictive assholes after the relationship ends for unrelated reasons. If an angry ex were to out you to your employer, your family, the authorities, the father of your children, or all of the above, WORK, you could lose your job, your home, and custody of your kids. The potential negative consequences of disclosure—however remote they may seem during the honeymoon stage of a new relationship—argues against disclosure even if you were doing PIV with your one and only client.
You have good reason to hold this information back until you're sure you can trust a guy, WORK: Your family's financial security and the ability to provide for your children. Your kids come first. And if you meet a good, decent, and understanding guy and, say, two years later you decided to disclose, WORK, he should be able to wrap his good, decent, and understanding head around the reasons you didn't disclose earlier. And if he can't, WORK, then he isn't the good, decent, and understanding guy you thought he was.
* Not always a reasonable assumption. People shouldn't assume their partners are exclusive until they've had a conversation about, you know, exclusivity. But exclusivity is the default-if-not-always-reasonable assumption in most heterosexual relationships—I'm not talking hookups here—and if we know that someone's default/reasonable assumption is likely inaccurate, we're kindasorta morally obligated to set them straight. Allowing someone to labor (or fuck you) under a false-but-reasonable assumption is a shitty thing to do. So if you're married but on dating apps and don't wear a wedding ring, for example, you do need to disclose that fact.