• Don't go overboard in your introduction. Pick three really hot fantasies that you want to realize, and phrase them concisely, in a sentence or two each. In a private consultation with Cleo, she'll work with you to flesh them out.
• Don't show up, unannounced, without a girl. Be honest if you don't have a lover to bring to class. Cleo won't take kindly to students who expect her to bottom for them, but in a guided play session, Cleo can partner you with an experienced submissive, usually a very cute girl wanting to learn SM herself (which is how I met Cleo). She can also connect you to places where you might meet a new kinky girlfriend.
• Don't try to take charge of the class. The standard geek response, when threatened, is to start telling other people how to do their jobs. If you try to prove your dominance, you'll get eighty-sixed fast. Sure, you might feel like an actual dork with a whip in your hand for the first time. Don't freak out — that's why you hired Cleo. Just think of her work like any other kind of troubleshooting offered by a consultant with over 20 years of experience — only she has really keen taste in leather.

She had a client she wanted me to meet. It was about a year into our working relationship and I had graduated to taking clients on my own. But this day she needed a guest star, and asked me to bring a suit over to her place with me. She received clients in a two-room commercial space in SoMa, an office and a dungeon.

While we got dressed, she ran down the details of her client's fantasy scenario: We were his bosses, and we were going to "catch him" jacking off to photos on his laptop. Not porn, even: screenshots of female Fox News and MSNBC anchors with their mouths half-open. So while I'm glad my mentor taught me how to use a whip, and how to tie someone up, and how to discreetly take off my heels once a guy was blindfolded, I couldn't have done this scene without borrowing lines from her, straight out of a sexual harassment training she'd attended at her former day job.

In real life, he told us, he was in San Francisco for a conference. She rented a dungeon walking distance to the Moscone Center for a reason.

(Photo courtesy of Natasha Strange, the Kitten with a Whip)

Name: Anne Marie, the Educated Escort

Rate: $12,000/day, 2-day minimum

Launch: 1999

Notable media appearance: Slate, January 2000: "She played me a message left on her voicemail from a self-described Silicon Valley geek about to retire, who wanted to know what her annual fee is."

Anne Marie's bio puts her geek pedigree like this: "She also continued her education studying technology and working with some of the pioneers in the computer industry. In fact, one certain technological event landed her on the front of the New York Times and forced her to dodge reporters until this day." Not at all press shy, to get the word out, she gave interviews to Slate and Salon, the kinds of online publications her potential clients might actually be reading. Now retired, she still moderates the High Dollar Hottie web forum. See one of her earliest saved posts there, from 2002, where she responded to those who can't afford her.

Name: Jet Set Lara

Rate: £6,000/day

Launch: 2003 (archive of her first escort site)

Notable media appearance: GQ, January 2006: "Some men seduce by manipulation, while others are more organic, it just flows", she explains as we drift into a blur of champagne."

Lara courted blogger chic from the beginning. Her advertising angle was to get her hotel reviews linked to by Gridskipper and HotelChatter. She was also the first paid companion that you could actually hire that Jason Kottke blogged. Lara's blog is still live, but reports from colleagues say she's now more interested in being hired for writing. Typical!

Name: Brazil

Rate: $5,000/overnight

Launch: 2002

Notable Press Appearance: Numerous in 2004, after $61,000 in assets were seized from her safe deposit box, later claimed as a gift from Ask.com co-founder David Warthen.

Brazil was one of the first high-dollar hotties to go down for the content of her message board postings, bragging about her ability to pay off student loan debt with her escorting income. She left the business, got hitched to Warthen, and now reportedly owns a boutique in the Bay Area. Her legend still haunts the next generation of Internet call girls — a cautionary tale (report your income) with a Valley-twisted Cinderella ending.

Name: Samantha Waters, "The Dot.Com Call Girl"

Rate: Unknown

Launch: Unknown

So Why Is She Here: Waters was "a dynamo sales representative for a Silicon Valley tech firm" who worked as a call girl on the side. Her book is a memoir of those days. I'm not sure which will happen first — I'll either meet a former client of hers soon, or discover that I already know her.