An Escort Taught Me How to Sell Myself to Strangers Online

I met Amber at a party in LA, and when the "so what do you do?"part came up, she was not at all shy about informing me that she was an independent escort. She was in from San Francisco and had had a one-off client out here this afternoon, and would be heading back up the coast in the AM. Oh-ho? A fellow freelancer? I had so many questions. Where to begin?

Amber and I chatted a bit that night, but as it was our first interaction, I didn't feel comfortable enough to delve deep into the nitty-gritty. The next day, however, after looking at my bank statements, I wondered what sort of effort it would take to become a (straight, male) escort myself. We'd found each other on Facebook already, so I started asking her some questions. And then some more specific questions. And that's how I found myself getting a makeover with the intention of becoming an appealing and profitable prostitute.

It wouldn't just be a matter of me getting new clothes—Amber planned to give me a crash course on the best sites to use to set up my new persona and how to create a professional ad that would draw real business. I agreed to cede all authority in light of her years of experience and essentially let her mold me from clay.

(By the way, this was all to satisfy my curiosity. I have no intention of breaking the law, so if any police officers are reading this please don't come knocking on my door.)

My new sex work sensei came to my apartment the next week and we got to work on my look. Amber explained I'd want to dress in a neutral fashion so as to appeal to the broadest possible spectrum of potential clients. This meant I'd be ditching my look (I call it "Preppiest Bike Messenger") for something a bit smarter.

She prescribed a crisp white dress shirt, subtly checkered blazer, and simple dark denim. We cycled through a few pairs of dressiness-adjacent shoes before settling on some brown Chelsea boots. I put on the outfit and stared at the mirror in horror, as my gaze was met by a drab Jeff Foxworthy–looking dude ready to host another round of Are You Smarter Than a Fifth Grader? Amber walked into the room and could instantly sense my discomfort.

"I know you don't think it looks good, but it does. You're shooting for Orange County cougars or housewives looking to cheat on their husbands," she said, adjusting my collar. "They're going to want clean-cut. If they specify that they want someone a little more hip, you can dress for that. This is just going to be your look for the ad."

OK. Her word was law. We then took a trip to my barber to make sure I'd be presentable if clothes weren't a factor. Fortunately, Amber approved of me getting my usual high fade as it was now mainstream enough to be acceptable for even the more conservative blue-bloods seeking my services. I also needed a shave, but she suggested I take a second after picture after a day or so of stubble had grown back, as "every woman likes a five o'clock shadow on her man, no matter her dispositions otherwise."

When I returned to my apartment, I was eager to get cracking on the ad blitz that would ensnare my sex-deprived quarry. I immediately fired up Craigslist, but Amber stopped me in my tracks. "That's where the trashy clients shop. It's not worth your time, nor will you earn enough money there for it to be worth the trauma."

The modern, independent escort has to post paid ads to quite a few sites, many of which started out as Craigslist alternatives but have morphed into digital red light districts. Posting ads is a never-ending game of musical chairs for sex workers, as government agencies—who are clearly aware of the nature of these forums—can and do swoop in at any moment to shut them down, as was the case with the San Francisco–centric MyRedBook earlier this year.

The sites Amber recommended for a fledgling LA escort like myself were Cityvibe, Humaniplex, and the elder statesman of the group, Backpage. Let me be blunt here: These sites are hideous. Geocities hideous. They're utilitarian digital lean-tos clearly not meant to withstand the test of time. And that makes perfect sense. If Uncle Sam is likely to come bulldoze your house at any moment, there's no sense in investing time and money in painting and gardening when you only need four walls and a roof to stay alive.

As I wasn't planning on taking this game the whole way across the finish line, and placing each of these ads cost real American dollars, we figured it would be fine to just post one ad on Backpage to get the best response sampling. I also changed my name to "Chase" in the advertisement, since that seemed like a suitably sleezy name. (Apologies to any Chases out there; I'm sure you're all great guys.) I shaved and put on my official gigolo duds and we took some pictures where the only usable shot of me made it seem like I was either snapping my fingers like a Rat Pack–era crooner or talking to Johns (Janes?) about "a-spicy meat-a-ball."

"Normally, you could get some free glamour shots taken if you put your existing pics up on Model Mayhem," Amber explained. "They wouldn't be the best or anything, and it would probably be some creepy guy jerking off the whole time he shot you, but hey, free photography."

Crafting the meat of the ad took a bit more brainstorming. The women escorts seemed to be using a garish, 1990s AOL message template for their ad titles with unnecessary underscores, letter-case changes, and symbols littered throughout in aid of—I suppose—grabbing the reader's attention. The men were more succinct, and just laid out their main traits and/or what they offered: "Hung jock giving erotic massages," "Straight hung black dude," or, simply, "Irish-Italian." I couldn't compete with the Adonis-like figures who were my fellow flesh merchants, so we decided to play up my charm. Yes, I had become the prostitute equivalent of "I've got this friend you should go out with. He has a great personality."

Amber went through a short list of things to see what I would hypothetically be OK or not OK with as she typed up my profile. Upon completing the short paragraph, we looked at the payment options and decided I could use a nice prominent feature in the Backpage sidebar for a week. I opted out of the service that would bump my ad to the top of the page once a day for a week. If I wanted to really rake it in, this would be the most important purchase I could make, according to Amber. On these ad-bumping services alone, spread across maybe four or five sites, she calculated her monthly expenditures were around $700. She was quick to point out that the ROI was well worth that cost.

A click of the mouse and $9.80 debited from my card, I was now officially a male escort. Only thing left to do was kick back and let the requests pour in.

Guys. Lots of guys. "Women only, please," was right there, politely, in the text of the ad, but there were still plenty of scamps who tested the waters, one of whom wanted to know if I'd be down to maybe just get my dick sucked by a guy, "in the dark." Sorry fellas.

Amber had told me to expect this, so I rode out the storm. After a little waiting and staring at my inbox: paydirt. it looked like the tide was turning. A 31-year-old woman who said she dates younger guys messaged me. And get this: She said she likes to financially invest in them because that power dynamic was the crux of her fetish. Um, OK. Yes. You want to put all your money in "Chase"? Go right ahead! I'm only 27, but I've slept with women older than 31 before without getting paid for it. This sugar mama sounded too good to be true.

And alas, she was too good to be true. My response to her email was met with silence. Perhaps it was for the better. Who knows how tempting it would have been to go through with a transaction if she'd actually written back.

On that note, I was getting pretty discouraged, and Amber needed to get back to work. Sensing I was losing hope, she told me this looked like a pretty normal pattern. Depending how long I stared at my inbox and wait, I would most likely start getting a reasonable ratio of flakes to actual clients. I was already seeing detailed, if somewhat arcane messages.

There was an unwieldy shorthand to discussing "activities" in this world. The MyRedBook archives have a compendium of terminology ranging from the obvious BJ (blowjob), to the hilariously specific BBBJTCWS (bareback blowjob to completion with swallow). I wasn't sure I would ever have a hot little Nancy Botwin bon vivant requesting LK (light kissing) with FOV (finger outside vagina).

Sensing she had sent me down a dark path, Amber warned me about the dangers of discussing "activities" with potential customers. "A sure sign of a cop is when they keep going on about, 'Would you do this or that with me?' and I just reply, 'I'm looking forward to spending time with you, honey!' Make sure you're always discussing time. Never any acts. That's where you get caught up. If they keep pressing about what I'd do with them, I tell 'em, 'Listen, dude. You sound shady. Take care.'"

The odd message keeps popping up, and I'm still ignoring them lest the allure of the payout get the better of me. I can market myself as a prostitute, but do I really want to find out if I could make it as a prostitute? I'm not sure, but I still have my photos and what I'm told is a solid and highly reusable ad template. After all, these student loans aren't going away without a little help.

Follow Justin Caffier on Twitter.