Mixtapes for Hookers


On Escorting: Me, Three Months Ago
April 17, 2009, 10:33 am
Filed under: personal | Tags: , , ,

I had meant to send something to Susannah Breslin when she was doing the Letters From Working Girls series, but either I was too late sending it (probably) or she didn’t want to end the series with a letter from someone who wasn’t actually a girl (possibly) or maybe she just didn’t like it.  In any case, I just found it when I was cleaning out e-mails so I figured I’d post it here.


My roommate was the one who got me hooking. “You sleep with a lot of old guys all the time,” she said. “You might as well get paid for it.”

It was true. Fresh out of college and on my own, I was going through an especially sinful phase; I’d been going to gay bars since before I was legal but only recently had I actually started getting drunk. Insecure about my body, I tended to go for guys twice my age, and by the time I was twenty-three I was fucking more or less everybody that looked at me, regardless of whether I was into him or not. I remember one guy with severe cokedick, who kicked me out midway through a blowjob because he said he’d been up for forty-three hours and just wanted to be left alone. And I also remember going home with him again less than a week later. For a drink or two, if that, I’d kiss guys and listen to them sulk about their age and we’d trade blowjobs and sometimes fuck. Sometimes I’d even do things I didn’t like, just because I didn’t know how to say no, while at the same time I could barely afford food, I only worked fifteen hours a week at a crappy retail job, and credit card companies were starting to call my house all day long.

So I put an ad on Craigslist and started escorting. I got my first client off in about ten minutes, because I didn’t fully realize that sober and sexually-frustrated sixty-year olds don’t have the stamina of drunk fortysomethings used to getting head regularly. But I got $150 for ten minutes! That paid all my utilities for two months and I was totally giddy.

My second client lived on the South Shore; it was only about an hour from my house but I got lost and it took three. At the time I didn’t have a cell phone, but when I showed up he was very accommodating and gave me $220 for a short and fairly unsexy BJ. And $220 was still several times more than I was earning at my other job, even if you factored in travel time and all the coordinating.

But this guy was the one that really got me set up; he had a huge, dusty house on the beach that looked like it was frozen in a porno circa 1982 (including, oddly, cameras everywhere, which I didn’t notice and he didn’t mention until a later visit.) And apparently all he did was hire rentboys all day, because he told me which websites to list myself on, which ones were free and which ones charged, and which ones were known for their quality guys. He had hired me because he didn’t know any escorts that fit my description (though he did seem to know every escort in New England.) He said he liked me because I was average; tall, but not too skinny; hairy, but not bearish; and I clearly wasn’t a muscly himbo or a junkie hustler. I was normal, he said. Normal!

So I listed myself on a few websites and made some money. Three hours a month would pay my rent; even after I got promoted to full-time at my day job I’d still have to work forty to make that much.

I met some nice guys. My third encounter was with an estate lawyer who sued asshole investors preying on the elderly. The guy was going through a messy divorce and he had what is still to this day the largest penis I have ever seen; his firm paid for the session–which was more than double what I had asked–and we both understood that this was okay.

I also met some assholes. One guy came over in the middle of winter, tanned and talking up the two vacations he had just taken in Hawaii. That would have been annoying enough, since at the time I was using my oven for heat, but before we met he had also told me a sob story about how broke he was and how he hoped it would be okay if I only got $90 instead of the $150 I had asked for. (Best of all, the next week he’d start calling and IMing me asking if he could meet again, but if it could be a real date–you know, a free one–because he really liked me.)

I met guys who wanted a real massage and thought I’d know how to give them one. I met someone who wanted to give me a medical exam. I regularly met a mafioso who liked me to kneel in front of him and blow him; forcing my head down on his dick with one hand, he’d use the other to call his wife every time. I had a weirdly profound moment of clarity when one black client I was fucking repeatedly yelled that he wanted my big white cock.

I liked it; hooking was a pain in the ass, but I liked it. When I started I didn’t have a cell phone, or a car, or internet access at my house, which is a stupid way to be a Craigslist hooker. But I made it work. I missed shows and made excuses and stayed home a lot for guys who never showed up and didn’t apologize about it. I had to instruct successful businessmen and lawyers twice my age that the words “It’s okay, I’m clean” are not a suitable replacement for condoms. And I had to come up with all sorts of lies to borrow my parents’ car.

But it was fun. Consensual fucking is fun, or at least more fun than retail, at least ninety-five percent of the time, and I like getting off on other guys’ fantasies. I met some interesting people, learned some interesting things, and for the only time in my life I got paid a respectable amount doing work that I was good at and felt good about doing. And I set my own hours.

But I gave it up a while ago; I found a boyfriend and he wasn’t totally comfortable with it, but also the rigamarole of scheduling sessions got to be too annoying. I keep thinking about going back–I’ve hit it pretty hard financially again and haven’t paid any bills in months–but I’m also three years older now and thirty pounds heavier than I was then, so I haven’t decided if I’m ready for a letdown if business is slower than it used to be…


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