I met “R” last week at a mid-scale bar not far from my apartment. I got there early, already a drink down, as I was, needless to say, horribly nervous. I sat down and immediately ordered another to sip while I waited.
I hadn’t eaten since breakfast that day, and unfortunately the alcohol went straight to my head. By the time R showed up I was reasonably tipsy, but at least much more relaxed and laidback as a result. The first thing I noticed was how much older he looked than in the picture he sent me. Not strikingly older, but the hair was a bit greyer; the hairline farther-receding. He, on the other hand, immediately complimented me, saying that I looked much more striking than in the pictures I had sent him (which, I should add, were all fully clothed). He sat down next to me and we got to talking.
Since I was relatively imbibed, I only recall snippets of what we talked about: my studies; his ex-wife; movies; music; his real age; where we grew up. I remembering fumbling for my bag when I excused myself to go to the bathroom, which I did, twice - a little embarrassing. I remember him awkwardly touching my back a few times, as well as awkwardly kissing me goodbye.
Also, quite unexpectedly to me, he decided to bring up our “arrangement” while we were sitting there, in public, at the bar. While I suppose it appeared unusual enough for a 60-year-old man to be having a casual drink with a 20-something woman on a Monday night, I thought he’d use a bit more discretion in discussing our financial arrangement and the terms of it. Either way, he laid it out: once a week, with a solid figure per month for us to be “intimate,” as he put it. I agreed immediately, mostly so the moment would pass and we could get on with normal conversation. It was more than I was anticipating, and I was happy enough. Either way, it certainly was more than I was currently making at my other job, and I needed the money.
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I got back to my apartment and e-mailed him right away. He e-mailed back and we set up a time to meet later in the week, at his place. So all I’ve had to do the last few days, besides school and work, of course, was wait and anticipate our first time together. I was feeling more confident about it a few days ago, but now, as the day approaches, I’m getting nervous again. Well, we will see!
It was late, and I have a habit of browsing Craigslist for fun. I collect random screenshots, things I find amusing, and usually the best and most hilarious are from the Casual Encounters and “Adult Services” section. Well, suffice to say, I often tend to get sucked in myself. I’ve certainly used CL for it’s more noble purposes - buying things, selling things, posting a cute “missed connection” here or there - but I’ve also delved into the seedier realms of the website, hooked up via it a few times; I even dated a guy I met for casual sex via Craigslist for nearly a year.
This is a side of me that very, very few people are aware of, and if they were, most would be relatively surprised: I’m a graduate student at a reputable private university on the East Coast, work a few jobs, pay my own way, and am relatively reserved and soft-spoken - not at all the type one might consider an avid Craigslist user. But, perhaps that’s part of the thrill of it for me, the deviousness of searching for sex online and the sexual openness and prowess I can express in an entirely anonymous environment.
Anyway, one night a few weeks ago I was browsing through the jobs section, found myself tempted by the “adult services” section, and went ahead and clicked through. I’d certainly been tempted before; last year I’d hesitantly applied to an escort service, a few local porn films, private modeling, etc., but nothing ever went anywhere. This particular night, I went through the listings rather flippantly - I’ve gotten pretty good at spotting the fake/”too good to be true” shit that’s out there - when one in particular caught my eye:
“Meet me.”
“Once a week.”
“Monthly allowance.”
Tempting; it was very tempting. And the post was (by Craigslist standards) well-written, mature, and thoughtful. “I could do that,” I thought. And so I responded, and that’s where this story begins.
