I Had Sex With a Stranger from Craigslist and He Didn't Try to Kill Me!

I always wondered what sort of people replied to the sex personal adverts on Craigslist. It turns out, they are people like me.
Publish date:
September 7, 2012
casual sex, craigslist, Sex,

My guilty pleasure has always been browsing the personals ads on Craigslist. If you're bored enough you can browse through hundreds of ads for jobs, flats, furniture and of course, dating, missed connections and "intimate encounters."

It's here that I've found such gems as the man who wanted his balls kicked, the man looking for a woman to pretend to be a kitten, period fetishists, virginity-hunters, old men looking for granddaughters, men who buy used underwear, piss and scat fiends and a dozen Christian Grey wannabes.

There's also a lot of ads from regular guys looking for sex, but I tend to skip over them. They're boring. But then one night I was perusing the personals and came across a profile of a guy that I was CONVINCED was a friend of mine. The age, the location, the writing style, the very unusual ethnic mix, the shirtless photos, the cock pics (having never seen him naked, I took a guess at this) -- it all added up. "I don't mind how late it is --if this ad is still up, then I'm still looking," the advert said.

I used an old anonymous email account [glad to see you're taking Emily's advice. Also, PSA time, be safe kids! --Rebecca] to reply to his ad: "a photo of your face, gets mine."

A few moments later, I received an email with two attachments. I think you know how this goes. It wasn't my friend, but Jason* was cute. Very cute. I can't explain why I did it, but I sent him a link to my online dating profile, which surprisingly, didn't put him off, and we arranged to meet the next day.

I must have changed my mind back and forth about a hundred times in the following 24 hours. Anyone who knows me will know that I am rubbish with men -- I'm shy, socially awkward and have this amazing ability to accidentally talk myself out of sex at the last minute (I told one guy I had AIDS, as a misplaced attempt at a joke. Even when I told him I was lying, he said he didn't want to take the risk).

I'm the queen of pillow barriers down the middle of the bed and awkward, fully clothed sleepovers. There was also my overwhelming fear that I wouldn't fancy him, he wouldn't fancy me, the sex would be crap (thus a waste of a number) and that he'd axe murder me -- pretty much in that order.

He managed to waylay my fears that he was the next Bateman-in-waiting by sending me a photocopy of his ID, emailing me from his work email account and taking a photo of himself holding a piece of paper with my mobile number written on it (to prove his pictures were recent). It was at this point that I noticed he'd lied about his age -- he was 27, not 24.

We arranged to meet at a station next to my house. We'd go for one drink then head back to my flat. My housemates knew what I had planned and I'd forwarded on all his details to trusted friends. I figured that by this point that I had taken way more precautions than any drunk girl at a bar.

Oddly enough, I put in a lot more effort getting ready for my sex date than I ever have for any real-life guy. I curled my hair and wore a long red dress with a split down the side. We recognised each other immediately, thank God, and Jason seemed more nervous than I was. He was cute, well-dressed -- if I'd seen him in a bar I would have immediately fancied him.

He asked me what my reasons were for replying to his ad, and I told him exactly what I just told you. I asked him the same question and he explained that he really didn't understand the rules of dating: If you met someone and liked them, why couldn't you have sex with them right away? Why did having sex with someone you fancied have anything to do with your moral character? He said he didn't understand why it was immoral to have sex on the third date, but not the fourth.

Jason also struggled with the rules regarding contact -- what was the logic behind waiting a set time to reply? Why couldn't you text four times in a row if you'd thought of four things to say?

Craigslist ads were honest transactions. Everyone knew what they were getting. I quizzed Jason on his relationship history. He'd been on and off Craigslist since he was 20 and met quite a few people, but not as many as I was probably assuming. The first person he'd met was a 33-year-old businesswoman who'd taken him to a nice restaurant. He'd dated a girl he met on there for a year. Of course, he also had some bad experiences on there: like the woman with the Peter Pan fetish and the one who showed up drunk, angry and abusive.

We went back to mine, took some drinks in my room and lay on the bed listening to music. After about two hours I came to the conclusion that I'd really done it this time: I'd managed to friend-zone myself with a guy who posts cock pictures on the Internet.

But then he kissed me. The sex was amazing. It was so good that I felt guilty -- like I'd hired a male escort, or was somehow taking advantage of him by getting him delivered to my door. I'm not sure if he felt like he had to put in the extra effort because he was providing a service, but my God, it was good.

Afterward, we sat on opposite sides of the bed, awkwardly. I think I even patted his arm. I told him I wasn't sure what the etiquette was -- did he want to hang out for a bit, or did he have more house calls to make? He laughed and said that he could stay around if I wanted.

We had sex again (and again -- WOW) and he said he'd like to stay, so I offered him a spare toothbrush (I buy packs for guests ever since my sister informed me she'd been using the "communal toothbrush" that she'd found in the bathroom). At this point he freaked out a bit -- taking the toothbrush would be "too domestic." Brushing his teeth in my sink would have felt like he was "making himself at home too much."

I got ready for bed and got under the covers. He got on top of them, until I pointed out he'd just touched my vagina, so I was OK with him sharing my bed. We lay awkwardly under the covers, not sure if we were allowed to touch. I'm sure his hands were twitching to construct a pillow barricade.

In the end, we ended up spooning and I woke up several times during the night completely draped over him. The weird thing being that I can't usually stand to be touched, and refuse to hug or spoon even longterm boyfriends.

The next day Jason sent me four text messages saying he'd had a good time and he'd like to do it again. I looked for his ads later that night to show my friend and he'd taken them all down.

Would I meet someone off Craigslist again? No. To be honest, even Jason warned me not to do it -- he said it was too dangerous, you'd never know who you'd meet.

Would I meet Jason again? Yes. In fact, when do you think I should make another sex date with Jason?