BY DIANA HEMINGWAY

Identifying the moment that I first became a sex worker is sort of like pinpointing the anniversary of a casual relationship that later became serious. Do I count the first time I opened up my apartment to sex work? Or the first time I actually took a fee and saw a client?

If we go from that last starting point, I began my career as a sex worker a little more than 13 months ago. Here’s what I’ve learned in my first year on the job—and what you can learn from my mistakes.

1) Sex work means different things to different people.

Sex work is a variety of different business lines within an industry. It’s not necessarily just prostitution, and it’s not necessarily illegal. I consider in-person sex work to include services like exotic dancing, erotic massage, escorting, brothel work, fetish companionship, and outdoor prostitution.

Independent sex work has essentially made me a small-business proprietor.

These differ from other forms of sex work, where the consumer does not meet the provider in person. Porn, exotic and erotic photography, phone sex, and live-sex webcams are a few examples of non-IRL sex work. It’s a mistake to consider all sex work to be the same, or to take one person’s perspective of sex work as authoritative.

I started out as a transsexual dominatrix thinking I would not even offer a “sexual” experience. I was just going to make a little extra money from activities I’d already enjoyed as a member of the kink community. Since then, I’ve entered other areas of the sex-work industry, including full-time escorting, cam performance, phone sex, modeling, and porn. I have a diverse industry presence now, with different social media profiles and branding for various business lines, advertising for in-person services, and an official website. I really adore the personal connection with in-person clients, so that’s where I focus most of my time and energy. Independent sex work has essentially made me a small-business proprietor.

2) Sometimes I have to check my privilege.

I can simply walk into an upscale hotel to see a client without being accosted by hotel security.

Although we are generally considered a marginalized group, I have come to understand and acknowledge that even as a sex worker, I benefit from race and class privilege. For example, my whiteness and middle-class cultural affinity afford me a measure of access. I can simply walk into an upscale hotel to see a client without being accosted by hotel security. Many of my associates who are people of color are profiled and told to leave before they can even get to the elevator.To a lesser extent, I also benefit from gender privilege. Because I was socialized as male for most of my life, only in the last several years, after I transitioned, have I experienced the constant barrage of misogyny that cisgender women experience their whole lives. In my last career, I remember quite clearly sitting at the managers’ meeting, the only woman at the table, being silenced and ignored while trying to focus some attention and resources on women’s issues. I had never experienced that as a man.

Another area of privilege has to do with working conditions. A mid-range escort like me, who makes a couple hundred an hour working indoors in moderately safe locations, has advantages and opportunities that an outdoor (street) worker does not. Since I’m not highly visible to my neighbors, I am not subject to the same risk of law-enforcement action, assault, verbal abuse, or violence that my outdoor associates experience. I’m learning to check my own privilege within my industry, and not oppress, stigmatize, or further marginalize other providers who work in different niches under different conditions than I do.

3) When you’re a sex worker, the Internet is your frenemy.

The Internet is a powerful tool for my sex work business. Not only does it make my work possible by connecting me with a vast pool of potential clients, it also makes my work safer. I’m linked to an online global community of sex workers who share information on everything from legal issues to how to screen out dangerous clients. Some forums, such as Twitter, are quite public, while others are only accessible to those of us in the biz. For many of us, the online sex worker community is the only support system we have.

It’s a constant struggle to shut the f**k up. I can’t say hi to my mom on Facebook without exposing her to risk.

But the Internet is a double-edged sword. When it’s not used with great care, it can also be dangerous. Every little statement I make that can and will be used against me—whether in the court of public opinion or in a court of law—is recorded forever. For instance, because sex work is illegal, I can’t have an explicit email conversation when booking a client. This communication is necessary so that we both know what is expected during our time together and what that will cost. And if I’m not careful, the Internet can expose me and my loved ones to scrutiny and violence. I can’t even say hi to my mom on Facebook without exposing her to risk.

For me, it’s a constant struggle to STFU on the Internet, even when I really, really want to say certain things. Things like “Happy birthday, Mom,” “police violence sucks,” or “Yes, I’d love to have sex with you for $500 at your hotel in 45 minutes.”

4) Your non-sex work relationships will suffer.

“Free for lunch? Or do I at least get a discount?”

Getting paid for being a companion makes it hard for me not to think of my personal friends and lovers as potential clients. Every time someone in my circle wants to play, I immediately start thinking, “I’m not gonna get paid for this.” It doesn’t even matter that I might want it just as much as they do. After a year of doing sex work, that’s just where my brain goes: “I’m losing $1,000 because I’m making love to my boyfriend all night long for free.”

The reverse is true as well. My play partners and lovers have apologized in advance for asking me for a “freebie,” knowing what I do for a living. A friend who wanted to meet up recently sent me the message “Free for lunch? Or do I at least get a discount?” It’s an odd kind of discomfort that continues to this day. Even when I’ve hooked up with other providers, my thoughts have wandered into the territory of “this is an exchange of services.”

The line between when I’m on or off the job can be tough not to cross. So far, the best I’ve come up with is to intentionally tell folks which side of the line they’re on (and keep them there). With other providers, the distinction between personal and business relationships is more difficult to maintain, especially if we are intimate with each other outside of work, or if we work together in double sessions with clients. The struggle to figure that all out is worth another article in itself.

5) Great sex is still great sex, even with a client.

You might think that because my clients pay for my companionship, I might not enjoy sex with them as much as I would with a romantic partner. But I have met many wonderful, exciting, interesting, passionate people through my work. We’ve made the walls shake and broken the mirrors. We’ve kept an entire hotel awake.

Maybe their personality was so repugnant that I couldn’t get hard with a full bottle of Viagra.

We’ve unraveled the mysteries of the universe in just an hour or two. I’ve felt genuine connection and even love for many of the people that have come in and out of my life this way.

6) That said, bad sex is still bad sex.

Maybe the client’s idea of kissing was swallowing my face. Maybe their personality was so repugnant that I couldn’t get hard with a full bottle of Viagra. But at least I didn’t invest hours of dating, movies, dinner, discussions, and trips to awful tourist traps to get that bad sex. I went home happy anyway.

7) Escorting has been the ultimate self-esteem boost.

I have always been pretty confident in my sexuality, but I’d never really seen myself as sexy. I’m a middle-age trans woman who barely passes (and sometimes doesn’t pass) the “is that a woman?” gender-recognition check. Having clients show me the value of my sexiness in quantifiable terms has helped me wipe the dust off the mirror, and realize that I’m one helluva sexy beast. I’ll always know that now, even once I retire.

8) Sex workers have little or no safety net.

Because we are sex workers, we often lack support systems, legal recourse, or even sympathy. I was once raped by a client who wanted something that I wasn’t willing to provide. Although I’d heard countless tales of assaults, arrests, poverty, disowning, mistreatment, hunger, and murder from other sex workers, I wasn’t prepared to be blamed, chastised, and called names by my non–sex worker friends. They blamed me for being raped. I was called a jackass for even talking about it. I was told I was trying to get myself killed. I lost several friends when I told them about it. Only a couple people did right by me.

So far I’ve managed to avoid situations that could lead to being arrested. I’m careful with my advertisements, website, and client conversations to not incriminate myself with “sex-for-money” language. When I was raped, I knew that I could not call the police without potentially getting myself arrested.

I was called a jackass for even talking about

my rape.

The bottom line is, when shit goes south, don’t expect your non–sex worker friends or law enforcement to rally around you. When bad things happen, we stand alone.

9) Sometimes sex work is a whole lot more than a last resort.

I used to work in public health doing cutting-edge program development and coordination as an HIV-prevention counselor for high-risk populations. I was devastated when a perfect storm of funding cuts, organizational leadership change, transphobic employment discrimination, and my own mental health issues forced me out of that career and into full-time survival sex work.

One short year of good sex work has turned my mind and emotions around on that. This has been the best career move I’ve ever made. I’m not just surviving, I’m thriving! I’ve met some of the most amazing people through my work, from other providers to journalists to community advocates to clients. I love my work, my clients, my fans, and my sex-work associates. Sex work was the best choice for me, at I time when I had few other viable options, and I’m glad I chose wisely. It provides me with a modest but decent income doing enjoyable work. It empowers me to set my own value, rather than let some middle-management tyrant dictate my worth. It affords me the freedom to care for my mental and physical needs on my own terms. Sex work as an industry holds many great opportunities for future growth and upward mobility, even for an aging escort like me.

Sex work might not be the best choice for everyone. There is plenty of bad that goes with the good. It’s hard being my own boss and running a business, handling difficult clients, dealing with the effects of stigma and marginalization, avoiding the pitfalls of criminalization, and mitigating how my profession impacts the people I care about. It can be very lonely, even when I’m crazy-busy. But for me and countless others, becoming a sex worker has been worth every damned sexy bit of it.