I had been making a living on my back for about four months when I decided to move out of the three bedroom apartment I shared with five friends. I had moved out of my mother’s house the day before my eighteenth birthday, but failed to think through the inevitable difficulties that would arise from cramming so many people into a relatively small space. What had started out as an idyllic non-stop slumber party had devolved into an overcrowded dump with a revolving lineup of dirty travelers carpeting the floor. My home was not a place I could decompress after a tiring call, and that was not a good thing.

As luck would have it, Natasha, one of my roommates’ friends was looking for a new roommate of her own. At eighteen I did not yet feel ready to live alone with only my pet rabbit for company, so I invited her over to share a box of wine with me and figure out if we would be compatible as more than casual acquaintances. We were! Perhaps it was the box of wine, or perhaps we did have some genuine affinity, but we were pretty sure we were BFFs for life by the time we passed out on my kitchen floor.

Natasha not only knew of my career, she was also very enthusiastic about it… which made her an especially attractive candidate for roommate-hood. At first, I just figured she was glad to live with someone who could always pay the rent on time. Unfortunately I had no idea how enthusiastically Natasha would really accept my job.

Within a month, she had decided that she too wanted to join me in the world’s oldest profession.

It may sound harsh, but Natasha wasn’t pretty, presenting me with with a quandary. As a friend, I couldn’t tell her that she wasn’t physically suited to the sex industry… yet, at the same time, it would be cruel of me to be too encouraging. I’d only watch her crumble under the occasionally harsh criticism that men on Craigslist level at women who are not up to their specifications.

For a month, I managed to put Natasha off the idea of becoming a sex worker with noncommittal responses to her questions and mildly embroidered horror stories of needy, unpleasant, or simply annoying clients. I made a show of bemoaning every job I booked, and ostentatiously popped handfuls of ibuprofen when I came home to cure my over-emphasized and often fictional stress headaches.

Unfortunately even my best efforts did very little. If anything, Natasha became gradually more set on joining the ranks of whores.

…Fortunately, I had a last-ditch plan to fix this problem. I would bring Natasha along on a call and show her what she was getting herself into.

I had recently read Rent Girl by Michelle Tea. It is a wonderful book that everyone should read, whether or not they need to gently deter their less conventionally attractive friends from becoming sex workers. Towards the end of the book, Michelle and her girlfriend come up with a not-so-brilliant get rich quick scheme: since men love lesbian porn, they’ll really love a live action demonstration! Who better to provide this demonstration than Michelle and her girlfriend?

Their plan fails. It turns out that most men (and, I would imagine people in general) are quite uncomfortable watching a couple have sex right in front of them. Even though Natasha had also read Rent Girl I was certain that I could convince her that we could succeed where Michelle failed, and that our two-girl show would be a success. If we managed to actually book an appointment, I hoped that it would be enough of a disaster to put Natasha off the whole idea of entering the sex industry.

Despite the fact that this venture was doomed from the get-go, Natasha didn’t seem to see it that way. We recruited her boyfriend to take some softcore cuddling pictures of us in underwear, and I drafted our advertisement. I was pretty sure that the aesthetic differences between the two of us would be enough to nip the whole undertaking in the bud.

To my great surprise, we got our first response the next day and managed to pin down an appointment for that evening.

After packing up condoms, a vibrator, and a strap-on dildo, Natasha and I set off for our first appointment. On the way, I gave her a quick primer on sex work:

1) Fake orgasms are, for lack of a better term, prettier than real orgasms. Fake it at all costs.

2) The job is about performance, the show is more important than the experience and the show must go on.

3) Be clear about boundaries, do not be afraid to tell the client if he steps out of line.

I’m pretty sure I was as nervous as she was, if not more so. While I’d slept with plenty of women in my spare time, I had never done a two-girl show before and the fact that I wasn’t even somewhat attracted to Natasha made the prospect all the more daunting. There were a lot of things that could go wrong and I was… worried.

The guy lived on a tree-lined side street in a nice part of Chicago. He lived in a penthouse that took up the whole third floor. The first thing I noticed when we walked in was that it was obvious he didn’t live alone. There were little lady touches everywhere: the ballet flats by the door, the Audrey Hepburn print on the wall, and the general Anthroplogie catalogue feel of the whole apartment. He had a female roommate at the very least but it seemed more likely she was a live-in girlfriend. I was aware that a number of the men I saw were married or otherwise attached, but it had never been so obvious. I’d never actually gone so far as to essentially intrude on another woman’s home. It was awkward.

Our client handed us each an envelope, and led us to the bedroom. Natasha and I got onto the bed and started kissing. We had no chemistry and I hoped it didn’t show. We undressed each other awkwardly, I retrieved the vibrator and a condom from my bag, got behind Natasha and started using the vibrator on her. My reserves of dirty talk were already failing me, and the client hadn’t even pulled his dick out. I decided that oral was probably the way to go. Everyone likes watching girls go down on each other, right?

Maybe it was the lack of chemistry between Natasha and me, but I had never really noticed how ridiculous sex can be until I was performing it in front of this total stranger. There are weird positions, weird noises, and weird fluids; when you pause to think about it, sex isn’t terribly sexy. Crawling around from behind Natasha to get between her legs made me feel like an awkward, anxiety-ridden virgin and I’m sure that’s exactly what I looked like.

But what was I supposed to say?

“Sorry, this isn’t traumatizing or anything, it’s just too awkward for me. Here is your money back, sir.”

I started to go down on Natasha and immediately suppressed a gag. There was no warning, no bad smell, and no strange discharge, but as soon as I applied my tongue to her vag, it was clear that something was very, very wrong. Perhaps it was Natasha’s aversion to soap, or perhaps she had some kind of infection, but her unique flavor was like nothing I had ever encountered in any of my female sex partners. It wasn’t exactly fishy, but it was definitely in the same taste family. It was terrible. I really can’t emphasize enough how unpleasant it is to bury your face in a putrid vulva. I’m pretty sure that only H.P. Lovecraft could describe it properly.

Lucky for me, Natasha was building her undoubtedly fake orgasm much too quickly, and I didn’t have to keep up appearances for very long. It was clear that the time for the strap-on had come.

Trying to look sexy while buckling on a dildo harness is not easy at the best of times. Trying to look sexy while buckling on a dildo harness in front of a man who has just witnessed the worst sexual experience of your entire life, still has not pulled his dick out, and is starting to look very uncomfortable is practically impossible. I was at the point of praying to Ishtar that the guy would say something, but he seemed transfixed by what was probably the most fascinating trainwreck he would ever see in his whole life.

Once again, I didn’t have much choice but to go ahead. This time, however, I decided that I would make the spectacle as lurid as possible without causing any emotional scars.

I put a condom on the strap-on and ordered Natasha to get on all fours. As I started fucking her, I also let out a stream of abuse, hoping that the man sitting in the folding chair beside the bed would be turned off enough to ask us to stop. I called her a slut, I called her a whore, and I called her my bitch. I referred to the strap-on as ‘my cock’ and asked her if she liked it. None of this seemed to have any effect on our client.

Finally, as I smacked Natasha’s ass and asked if she liked being choked, the client spoke up, “Hey,” he said, “I’m sorry ladies, but this is weird. I feel like a creep. I thought this would be different.”

His voice was music to my ears. Natasha and I disengaged ourselves, got dressed, and got out of the apartment in record time. I’m sure that the experience was as awkward for her as it was for me because we never spoke of it again. Over the next few years she brought it up every so often when she wanted to impress someone, but she never went further than simply saying something along the lines of, “Yeah, Cate and I totally had sex.”

Despite the failure of her first foray into the sex industry, Natasha proceeded to try her hand at first prostitution, and then stripping. She failed at both of them, but at that point it wasn’t my problem any more since she wasn’t asking me for assistance with either venture. We had both learned our lesson: for each of us, at least, sex work was best left as an individual pursuit.
Cathryn Berarovich is a bit of a renaissance sex worker; she’s currently employed as a stripper (and writer) but has held numerous interesting jobs in the industry. Each week, she shares her stories in Harlotry.
(Still from Pretty Women by Touchstone Pictures)