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.