While it may seem surprising given that I was a prostitute for almost a year, I’ve never knowingly deflowered anyone (professionally or privately). Despite the fact that I’ve never harvested a single virginity, I’ve provided innumerable first experiences. Sex workers don’t just provide human contact to lonely people and outlets for desires, a large part of our job is teaching. Of course, good teachers are also willing to learn along with their students.

Even after three months as a prostitute, the nervousness that came before each call hadn’t quite worn off. Every time I went to see a new client, my legs would magically turn themselves into Jell-O and I would obsess over all the potential disasters. I was never afraid of being chopped up and left in a dumpster, but I am an immensely awkward person, and I was horrified by the probability that I could be exposed as the ungainly little girl I was.

Luckily, most people who patronize prostitutes are—in my experience—just as graceless as I am. When you have two awkward people, one of whom is trying to pass herself off as a fantasy, the potential for social pitfalls is enormous. I also hadn’t yet learned that while clients were absolutely seeking sex, they were primarily seeking intimacy. It hadn’t occurred to me that a somewhat awkward, extremely human woman could make someone feel more at ease than an ethereal creature exuding poise and grace.

When I made the appointment, I had no idea that “Jeff” had never hired a prostitute before. I knew that he lived in a hip neighborhood and that he didn’t attempt to haggle the price. He described himself in his email, something that prospective clients often do. I suspect that the descriptions come from some desire to arouse genuine lust or at least interest, but the practice of volunteering idealized physical descriptions always confused me. No matter what they actually looked like, these men almost always claimed to be six feet tall, 200 lbs, and dark haired with blue eyes. Every so often they would also give aspirational penis measurements (seven or nine inches, never higher or lower) but that was more unusual than one would think.

…Unlike most of my prospective clients however, Jeff gave a description of himself that seemed truthful. The honesty of his email and the unquestioning acceptance of my rates was enough to make me suspect that there could be a higher than usual awkwardness potential.

Jeff lived in one of the ugly new condos that had been going up around Logan Square for a few years and recently started creeping into my perfectly nice ghetto. As soon as I saw his building, all fears of awkwardness vanished. I was fully prepared to hate and scorn him (giving me the upper hand).

When I got to Jeff’s apartment, though, it became very clear that hating this man would be completely unfair: he was an average-looking aging-hipster type, maybe in his mid-thirties. He had red hair, glasses, and a somewhat wispy beard.

The first word out of his mouth was “Wow,” rapidly followed by, “You are beautiful.” I was immediately concerned.

I have never really known how to accept compliments beyond the first ‘thank you’, and clients are often given to a kind of verbal diarrhea. It begins with, ‘you’re beautiful’ and then the adulation pours out until they are saying things that defy all reason and telling you that you’re the most beautiful girl they have ever seen, something that cannot be true. Jeff seemed as if he might be at an elevated risk for word vomit, but instead of disgorging a stream of escalating praise, he quickly apologized, confessed he had never done this before, offered me a beer (which I politely refused), and informed that he’d had a few beers of his own to relax.

As I followed him into the bedroom I noticed five Guinness bottles on Jeff’s coffee table and, although he didn’t seem visibly drunk, I became somewhat anxious about how well this call was going to go. After some fairly awful making out (by the end of which we were both stripped down to only underwear) it was clear that my suspicions were legitimate: there were no boners to be had in the room.

I was faced with a conundrum. Either I could 1) break my number one rule of disease protection and try to get him hard enough to put on a condom with an unprotected blowjob or 2) I could just give it up. Jeff seemed to have finally noticed that something was wrong too and began apologizing profusely. This didn’t help matters and I decided that, unless there were any obvious indicators of disease, I should just go for the blowjob.

Somewhat against my better judgment I proceeded with the strangest, most unpleasant blowjob I have ever given. I’m not entirely sure ‘blowjob’ is the correct word for an act of fellatio in which the receiving partner remains completely flaccid, but unless ‘sucking a miniature elephant’s trunk’ is a real euphemism, ‘blowjob’ is the word I have to use. After the first five minutes, it was obvious to me that the mixture of nervousness and alcohol running through Jeff’s bloodstream were conspiring to make my efforts completely futile. It took about ten minutes for Jeff to come to the same conclusion.

He sat up on the bed, “I’m sorry,” he said, “I think I drank too much, it isn’t your fault, you’re wonderful, but this isn’t going to happen.”

I had no idea what to do. I had only encountered erectile dysfunction once before: with an almost-boyfriend and after so much whiskey that we were both too drunk to fuck. There were no real expectations and certainly no money changing hands. We laughed about it and lulled each other to sleep with a slurred rendition of the Dead Kennedys song.

Now, however, laughing and impersonating Jello Biafra didn’t seem like a good solution.

I wasn’t about to insist that we keep trying and I didn’t know how to handle the situation gracefully, so I ended up mumbling “it’s okay” and trying not to seem too relieved that he’d given up. Or too concerned that he’d ask for a refund.

As we put our clothes back on, I wondered how exactly I was going to leave. I was buttoning my skirt when Jeff turned to me and asked if I could stay, at least for the remaining half hour of the appointment. I asked what he wanted to do, and was surprised when he told me he just wanted to talk.

Jeff and I sat on his balcony and talked for almost another hour. He asked me why someone so seemingly well-adjusted would choose to be an escort and I explained how the “damaged whore” is just a terrible stereotype. We talked about whether we thought Obama would really win, and if he did, whether he’d really keep all his shining promises of hope and change. I was suddenly able to see this man as a human being rather than a penis-controlled ATM and it came as a shock. Jeff may have come to me seeking sex, but when that didn’t work out he didn’t just settle for conversation, he chose it.

Until that night I had looked at my job as a fairly frivolous way to make money. Sure, I knew I helped lonely people, and yes, part of helping those people was talking or even just listening to them, but I had no idea how important it really was.

Jeff never hired me again. I don’t know if he decided whoremongering wasn’t his cup of tea or if he simply found it too humiliating. Still, even though I never saw him again, Jeff made me a better sex worker: while I taught him that we aren’t all stupid, cruel, or damaged, he unwittingly taught me that the men who hired me weren’t either.

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)