I Sleep With Strangers I Meet On Craigslist

Tell us a little about your early life and experimentation with sex.

I was raised very conservatively, but I was educated on anatomy and the nuts and bolts aspect of things. I was raised in a tradition leaning towards Fundamentalist Christianity, which advocates waiting until marriage for even the first kiss. Despite this, I started out being very curious about sex: I was pretty aware of my body, and thankfully had proper sex education. I masturbated regularly, and at age 16 I started out with webcam sex – basically mutual masturbation through a random chat site.

Did you have any contact with the opposite (or same) sex before graduating high school, even kissing?

Zero…not until this year (technically my 2nd year of college).

What was that experience?

My first was a guy with whom I’d had webcam sex. We traded numbers, and at some point it came up that I was a virgin. I don’t recall how I said that I was ready to lose my virginity, but he did ask if I would be willing to lose it to him. I said ‘Yes’ and he was shocked. It turned out he lived not quite an hour away, so he came to my town. I had already decided prior that I wanted my first time to be with a stranger. I didn’t believe in saving it for a special someone – be that a significant other or your future spouse – as I think relationships have enough other issues to deal with before finding out you’re sexually incompatible. I also didn’t want to compound the emotions of a first encounter with having feelings for that individual. I was already comfortable with this guy, and I made sure we would meet on my own turf (where I could easily take control if things went sour). We met in a parking lot and used his backseat.

How was the sex, and where did things go with the guy from there?

I enjoyed the sex: it wasn’t particularly awkward from my point of view. We’d already discussed via cam stuff that I was comfortable with and wanted to try. He made sure I was relaxed and told me that I could stop at any time if I felt uncomfortable. We made out for a bit and then got down to business. He went down on me and made me cum first. I took my turn on him, and I was pleasantly surprised that the process met my expectations (LOL). He started eating me out again, and then went inside me. After managing a few different positions in a cramped backseat, I finished him off orally (yummy). Afterwards I was actually really happy (I’ll blame the hormones). It wasn’t a huge burden rolling off my shoulders or anything like I’d heard, as I wasn’t hung up on the idea of “losing it.” We met up once more later on, but the roundtrip drive was a lot for him as I’m unable to travel at all or host.

Following that second encounter, how did you whet your developing appetite for sex?

HA! Right before my first time with this guy, I had actually posted an ad on Craigslist to lose my virginity. The idea is super creepy, I’m not going to lie, but the response was overwhelming. I later had two partners from that pool of responses.

How were those encounters, and where did you have them?

Both were blowjobs – one of which happened in the middle of a parking lot in broad daylight! The second guy was someone I’d texted with for a long time, but we could only coordinate schedules recently. He was a virgin, and said that our hookup was his first sexual experience of any kind.

How did you settle on Craigslist for finding guys – as opposed to, say, online dating?

I didn’t think OKCupid needed a worse name than it already had. Craigslist Casual Encounters is dedicated to just that: no-strings-attached sex. Not saying a “forever love” is bad, but it’s not what I’m looking for. For me, love and sex definitely do not represent the same thing. They could coexist in one relationship, but they don’t have to.

Why do you reject the love aspect of a relationship outright?

I’m not ready for it. It’s a beautiful thing with the right person – it’s just not something I’m looking for right now, as I don’t have the time to invest in love. Sex, on the other hand, is something I consider a basic physiological need, much like eating.

Do you feel truly safe when you meet up with strangers – both in terms of your physical security, and the other person’s sexual history?

Let’s take physical security first. For the majority of my encounters, I’ve arranged to meet and fuck in a public place. This usually meant it was dark, but my town is relatively out of the way, and few of the guys I’ve hooked up with are very familiar with it. This is my turf: I know how to get around here. I’m also not afraid to do anything in self-defense (just saying). Now, there were two guys who I just gave my address to and had them show up. Super risky I know, but it went well both times. I don’t think I’d do that again however.

I barebacked the first guy. He told me his sexual history and I was pretty comfortable, otherwise I wouldn’t have agreed to have my first time with him. My better judgment has since won out, and from then on I’ve insisted on condoms. I am in healthcare and I’m very much aware of the various issues involved. So do I feel truly safe? No. I’m always on the alert. I do trust my partners to a certain degree: that’s why I agreed to meet them in the first place. I expect that with repeat encounters, trust can be built up, but I’m always on the lookout.

Thanks for giving us your candid perspective Kate. What would you recommend for those seeking NSA sex?

Make sure you’re actually looking for NSA sex. That sounds like a “duh”, but from a female’s perspective, make sure that you know what you really want and expect. Stay safe, and have fun. Lastly, don’t get hung up on any one individual – that’s the whole point of it.