What do most sex workers, from cam girls to escorts, have in common? Their regulars! Whether they’re consistently annoying, consistently charming, or consistently forgettable, they’re certainly an enduring feature of our lives. So we got a stripper, a pro domme, and two escorts into an endless e-mail chain together to see what they came up with on the topic. The round table that follows is an edited version of that conversation. (Read the second part of this round table here.)
Who was your most memorable regular?
Josephine: My favorite was a squirrely little white guy named Sheldon. There are two words that describe him: horny and nerdy. Sheldon was about 5’4″, rail thin, and shamelessly sported a suede fedora (not the douchebag kind, the Indiana Jones kind). He’d breeze into the club about once every two weeks unannounced, skip buying a drink, and grab me for dances. While I danced he’d rattle off [the plot of] the latest fantasy or science fiction book he’d read. I gave him a copy of Do Androids Dream of Electric Sheep? for his birthday and within a few days he e-mailed a proper book report. Sheldon was some sort of layman but he always wanted to be a writer. The most endearing thing he ever was did was write a short fantasy story —about me. I can’t remember what it was about except that I was a mermaid princess and he ad’hered to a go’ofy fantas’y dialect that used lots of apos’trophes and acc’ents.
Leigh Alanna: For a couple of years, I’ve had a standing weekly appointment with an older regular. And I do mean regular—every week, Sunday night, eight o’clock. Even the staff in the deli nearby know me, and have a coffee waiting for me at 7:45. Still, we’ve always sent each other a confirmation e-mail sometime in the couple of days before. One Sunday morning, instead of waking up to a friendly “Hey, same bat-time, same bat-network?”, I got an e-mail from his daughter telling me that her father had had a fall and while he was fine, he was going to be in the hospital for a couple of days and wouldn’t be able to make our appointment. I thanked her for letting me know, and sent appropriate good wishes, but entirely lacked the stones to ask her (or later, him) who she thought she was e-mailing. Did she know she was writing to her dad’s dominatrix? Or was I some bright young mentee?
Ephemeral: Probably the nightclub guy. He was in finance, mid-forties, a young face that didn’t match a rapidly aging hairline. He loved to take me out to all the “sexy spots” (his words) in the Meatpacking District and LES. We would go out “late”—10 PM. Which was great because I don’t know anyone who gets there before 1 AM. He drank way too much, and hated drinking alone. He was too tall for how bad his dancing was. Afterwards, he’d take me home to fuck while 80’s rock blasted from a sound system: “ITS SUCH A RUSH, YOU KNOW?” The moment of giving a blowjob while the Eagles played and him saying this line is the only time I’ve ever felt ashamed of myself as a sex worker. He had no idea what he was doing with his life, but the Ivy League degree, and two story Manhattan apartment would suggest that he didn’t need to stop and re-evaluate. Just keep drinking, just keep trying to dance, keep buying hot girls to dance with him. He was constantly perplexed as to why I couldn’t stay the night for the same rate, because “we’re having so much fun!” I’ll never forget anything that infuriating.
Caty: My weirdest regulars were the ones I inherited when I first started working, from the group of women who trained me–the same dysfunctional frequent callers we all saw. You know, guys like the gambling addict who was the only one we all trusted to pay with a check, a guy who had what looked like elephantitis of the balls, who’d go through every outcall in total, eerie silence.
There was the pretentious ex-military officer whose dick was literally as big as a baby’s arm holding an apple. He’d boast, “Oooh, the girls are all afraid of it at first, but then they’re bouncing up and down on it like there’s no tomorrow!” My rule with him was that as soon as I said stop, he had to pull out no matter what. One time, I told him to get off me and he just kept keening, “Oh, baby, I’m almost there, I’m so close…” So in a display of hysterical strength, I flipped him off of me and he sailed over the bed ass over teakettle, landing headfirst into a lamp. After that I had his perfect obedience.
Then there’s Rick, the most entitled, whiny Jew boy I ever did meet—and having grown up in the Russian Jewish community, I know from whiny Jew boys. There’s nothing atypical or particularly memorable about him except for the fact that he’s everything that annoys me about clients taken to the nth degree. When I first started to see him he used to complain to the other escorts about me, because I wouldn’t massage his pasty white anus—”she has a shitty attitude!” I always wanted to point out that I might have a shitty attitude, but he had a shitty ass. Nowadays whenever I see him he always goes on at length about how FAT one of our mutual escort friends has gotten and how DISGUSTING it is. I always want to turn his face to the mirror to look at his washed out, chubby, bald self head on, but so far I’ve resisted the temptation. Rick is a pharmacist, but that’s never allowed me any drug-related advantages. He’s always wondering why he can’t get a date while complaining vociferously and at misogynistic length about every woman he meets over dating sites. He’s also the one client I ever worried might DIE while in session with me—he came in to see me once right after getting stung by a bee in the parking lot of my incall, and his allergies were so severe I thought I’d have to out him in order to call an ambulance for him for a few minutes till he gathered himself enough to drive himself to the ER. Death by allergies—so stereotypically whiny Jew boy, if you’ll pardon my self-hating anti-Semitism.
What do you value your regulars for the most?
Josephine: The best regulars, in my experience, have never been huge spenders. But they have are always consistent, predictable, reliable and trustworthy. My favorite regular doesn’t even spend $100 on me. But he does come in almost every day like clock work. The co-workers and the staff love him. He’s generous and funny and really laid back. He knows me like a significant other would know me, it’s amazing. I think long term regulars are the sort of people that, if you had met in the civilian world, you would still be friends with. You’ll have similar personalities and interests. I guess what I value the most with my best regulars is the general experience; I’ve never felt like I’m hustling them. I can just be myself and get paid for it.
Leigh: My regulars aren’t especially less annoying or troublesome than new or more sporadic clients. But what makes them ultimately easier to deal with and worth the extra administrative overhead of dealing with them (more time answering texts and doing “friendly” emotional labor outside of sessions, bending rules about advance booking, or going a little over on time) is that the ways in which they’re going to be annoying are predictable. I know that Joe is always going to be ten minutes late, and that Charlie will whine about wanting to meet my imaginary girlfriend and session in my apartment, and that Pete is going to insist that I help him pick out his accessories for the day. So I can go to each appointment prepared to minimize any negative impact on my day they might have. Because of that, regulars whom I’ve known a long time are a lot less taxing even than new clients who are objectively “better.” Of course, the other big advantage is that regulars make it much easier to plan your finances. The clients I would class as regulars tend to fall into a very predictable pattern of booking, whether it’s once a week, or every other month, and so it takes some of the uncertainty and stress of doing freelance sex work out of the equation.
Ephemeral: In short…the money, and where that money gets me. I’m going to be completely blunt here: if they didn’t hand me large sums of cash I would not be having regular interactions with these people. While I’m sure they are complex, significant, and maybe even interesting creatures to others, clients to me are only what is in the envelope and how frequently they are handing it to me. The allure of regulars, despite all the potential drawbacks, is that they allow some level of dependability in what would otherwise be an insanely unpredictable stream of income. Short on rent? Need to buy a last minute plane ticket? Want to take next month off? Just send out a cute candid photo to the regs. With enough regulars (or one single regular who books frequently enough to qualify for “sugardaddy status”) you have something of a cushion: they essentially cover your average monthly expenses without costing you any investment into advertising or time spent screening. With a secure enough cushion you can invest your new surplus of time and money into self care, education, building an additional brand/persona, etc…you depend much less on the unknown of advertising venues and the stranger clients they bring and can learn the patterns of your repeat clientele. (Not to mention you lessen the risk of LE exposure!) The money of regulars offers a certain ease of mind and flexibility that at best makes escorting much easier, and in the worst case scenarios, saves your ass.
Caty: For me, the value of regulars comes from the absence of the unknown, specifically in terms of the danger of arrest or violence. When I was arrested in a sting as a baby hooker it was partially because I’d declined to go see my taxing but predictable developmentally disabled client in his close-smelling room in favor of going to another call with a new client which was closer by.
I know that one can never truly know what another person is capable of, and that even a regular can turn on you, but in my experience, I’ve never found that to be the case. After 12 years of escorting, I’m an expert judge of character. When I choose to see someone multiple times, it’s because I’m pretty sure that no matter how obnoxious they are, they pose no threat to me. If I only have enough energy or time in a day to do the one appointment, I’ll choose a regular even over someone who’s likely to pay me more, just for that invaluable peace of mind. And then, of course, there’s the less crucial but just as reassuring peace of mind gained knowing a client will actually SHOW UP and PAY ONE’S FEE. In an industry in which there are no consequences to the client in behaving unprofessionally—oh, how many times I’ve wished I could bill people for missed appointments like a therapist’s office—sometimes I feel like the most frustrating part of the job is how many times I’ve been stood up, proverbially all dressed up with nowhere to go. Of course, occasionally this has tripped me up—I notice that I keep seeing this really awful kid who asks me for short time appointments and has been known to short change me just because I know that even though he’s a miserly pain in the ass with no manners, he’ll be there and he’ll pay me, even if inadequately.
We’ve all heard horror stories about dating clients, but what about clients as friends? With long time regulars we genuinely like, how do we best negotiate that boundary?
Josephine: I’ve never had to negotiate that boundary, thankfully. When you have a really good regular, it won’t feel like he’s exploiting your time and energy. Maybe I’m lucky, but I guess most of my regulars “get it.” My advice for someone in that situation is: if it starts to feel like the boundaries of your relationship are blurring, then you need to reevaluate how valuable that regular actually is. Don’t beat yourself up if you give the guy a few freebies, or go beyond the call of duty to satisfy him. He probably has earned it! But if starts to feel like he expects that of you…maybe he’s not so great.
Leigh: I’ve never found emotional honesty to be a particularly rewarding experience with my clients, even the ones whose company or kinks I enjoy, or whom I think of as good, ethical people, and so I’ve never had a client who I really think of as a friend in any meaningful way. So managing “friendship” with my clients always comes down to giving as good a facsimile of genuine friendship in the interest of maintaining the revenue stream while avoiding setting up unrealistic expectations in terms of how available I’ll ever be outside of session. Whenever possible, I try to do this with soft refusals. As in, I try not to say, “No, I’m never having a museum day with you for free,” but instead [I] just can’t ever manage to make the scheduling work, or [I] conveniently forget to reply to that portion of the message. For me, at least, this minimizes how much clients feel able to push my boundaries in terms of emotional availability in that, there’s nothing being communicated to them that they can actually argue with. A lot of times, they won’t even necessarily notice a boundary has been set.
As to why emotional honesty has not been especially rewarding for me: My persona with my regulars leans heavily on [the] illusion that I’m really emotionally genuine. I pretend to be a lot pickier and low-volume than I actually am, basically. I always call it the “luckiest girl in the world” brand. And so part of the problem is that there’s no space for clients to recognize that something unique or out of the ordinary is being shared with them if I do break character and speak authentically (which, for me at least, is the root necessary circumstance of friendship, much more than sharing activities or passions). A few times, mostly earlier on, I’d feel like I was potentially able to connect my actual self rather than my work self to a client, and, pretty consistently, when I followed through, I’d notice that a) the clients in question, even the ones I thought of as both good and interesting, personable people, actually weren’t listening particularly actively, and if they did notice, they were actually put off or nonplussed. Possibly I just haven’t met the “right” clients. But actually, and this is something I was discussing recently I think a lot of it comes from the fact that, when I think of a client that I trust, whose company I enjoy, who I feel genuine, caring affection towards, [the way ] Josephine [describes], those are clients who really solidly get the transactional relationship and its boundaries. [The aforementioned] really good, well-behaved, once-a-week-same-time-like-clockwork regular has been seeing me for going on two years, and has never even mentioned the fact that the name he calls me isn’t my real name. Part of what makes especially good regulars for whom I could have friendly feelings is their understanding of boundaries and their total lack of interest in crossing them. Which means that the friendship I have for them is, if not strictly speaking one-sided, split by an unbridgeable gap, because there’s no way to communicate this to them without wrecking it.
Ephemeral: If I have a regular I truly like, I consider myself lucky to be having an easier time that evening. I’ll use the mindset I go into when I’m with him to meditate my way through less enjoyable dates. That’s the only tactical value in “friendship” with clients, in my opinion. I’ve tried other ways…I honestly fell hard for one man, but I won’t bore you with the same old stories.
This is what I do: As a sex worker, I have “personas”—not just a different name (and age, and weight…) but each has a unique backstory, hometown, favorite cuisine and color, studies a different major, prefers a different style of clothing, everything. Everything is manufactured. I’ve spent hours reading psychology textbooks and watching bad romance films to build quite a well-reinforced, shiny wall around who I really am that reflects a “perfect girl” to the eyes of any client trying to examine me. I do this because negotiating myself, my boundaries—any more than I already do—is too much. Parsing out the details of who you really are to a client who is becoming more than just the envelope he carries, opening up, becoming vulnerable—I can’t do that, and quite frankly I can’t even suggest advising any other sex worker that it may sometimes be a good idea.With this method, every single client can have the illusion of friendship romance, even—with minimal “wear and tear” on my mental and emotional resources. I’ll say from a marketing perspective, it works insanely well. I consider the sensations of candor, passion, and openness to be part of the service I provide to all clients. It’s a big part of my business model that I convince all clients that what we experience together is not just another appointment. Instead it is a very real and very potent, enthralling, visceral interaction that we share with equal enthusiasm. I know, it’s fucking ludicrous. So I suppose, I negotiate that boundary by manufacturing a new boundary far outside of myself, and letting them all think they’re the lucky, rare one allowed to cross it.
Caty: I actually posed this question to the group because I’ve been grappling with this issue lately. I used to be like Leigh and Dominique—it used to be all emotional labor of the surface acting sort with me. Sure, I could feel distantly fond of clients, but they were clients, with whom I had a commercial relationship, not friends with whom I had a personal relationship, and never the twain would meet. I’d been burned early on with a regular I had as a newbie, a swaggering, funny, leather-jacketed man in his 60s who reminded me of my partner, a man who claimed to have done some sex work of his own as a gigolo for a tiny market of rich women. (I never knew whether to believe him about these yarns or not, but they sure were entertaining.) He always went on about how we truly understood each other—all that bullshit client blather meant to foster pseudo-intimacy—but he was informal and friendly with me, and sometimes we’d go over time just talking and trading stories. Once, I called him when my partner and I were both desperately dopesick, asking if we could do a session that day so I could get well. I’d been open with him before about my habit, and he was an ex-drug dealer himself and had always been accepting and sympathetic about it. I was vulnerable and honest with him on the phone about why I needed to do the appointment that day, even though I felt humiliated breaking an unspoken law of escorting: “Let them come to you.” Anyway, he swore, “scout’s honor,” that he’d do an appointment with me the next day (well, thanks for 24 hours worth of more agony, asshole), but of course he never showed up. Years later, he contacted me again, and now he’s once again a regular of mine, but now I know better than to ever open up to him in any real way again, even though he still keeps the patter going about “you and I, we have a special thing going…”
But this last year, I’ve found myself growing closer and closer to one particular regular. I have no romantic feelings about him, but I admire his integrity, I genuinely enjoy spending time with him, and he makes me feel supported and appreciated. Unlike my richer clients, he always tips generously, even paying cancellation fees unasked. He’s also the first client I’ve felt comfortable enough with to ask for bridge loans to be paid back partially by discounted sessions. And the way he wants to be close to me isn’t intrusive—he understands that I have a partner, and he understands that our sexual relationship is just my job. He just seems to enjoy talking to me and e-mailing with me, which I’ve started doing without feeling like it’s more work, which is how I feel about extended e-mail correspondence with other clients. He’ll take me out to eat and pay me generously just for that when he can, as well. I feel like I can depend on him, both emotionally and financially. Maybe this says something about my tendency to isolate myself, that I’ve grown so friendly with a client because honestly, I have more regular contact with him than I do with many of my friends. I’ve probably told him more about myself than I’ve told many of my friends.
Maybe I’ve gotten myself into this difficulty because my work persona is just a hairsbreadth away from the “real me,” anyhow—I’ve no head for acting or lying, and I find I do best in sessions if I just relax and “be myself”—focusing on the nurturing and heterosexy aspects of that “self,” anyhow. So when someone shows what I gauge as genuine interest in that self, I can’t tell myself that he doesn’t actually know me.
Maybe these are the stereotypical daddy issues that mainstream media ascribes to sex workers, rearing their ugly heads? Or maybe I’m just a lower middle class escort who mostly does hour long sessions who’s just going about having a sugar daddy wrong. I often feel like I’m breaking yet another implicit rule of ho-dom because of the fact that I truly do count him as a friend, without that prerequisite of distance that’s necessary in all my other client interactions.
Read the second part of this round table here.