From Monogamy To Open Marriage: Was There Casual Sex Before The Internet? 

We sift through prospects — sometimes we post new ads on the sites I mentioned.

From Monogamy To Open Marriage is a weekly column devoted to the discussion of pursuing sex and love outside marriage. 


These are a few of my go-to sites:

Swing Life Style

Adult Friend Finder

Craigslist

Ashley Madison

Fetlife

How on earth did people arrange for all the different variations of casual sex before the age of the internet?

When we decide to find others to join us, I always have to make a conscious effort to shake the kid-in-a-candy-store mentality. I already know that every fantasy I could possibly conjure up is at my fingertips and it’s just a few keystrokes and clicks away. Two or three days of screening e-mails and going back and forth via messaging and we can find what I’m looking for. If we’re looking for instant gratification, we can find “close enough” in a matter of hours. For a couple, it’s fairly easy, but for a single woman, looking for sex on the internet has a choose your own adventure book in her hands, only she gets to write the story.
 

When I was newly divorced and I discovered the casual encounters section of Craigslist, I went a little overboard. First, I answered ads and learned that the men who post them seldom get a reply. When they do, and it’s not a spambot or solicitor, they’re over the moon. When they actually meet a real live woman, they literally regard the “date” as though it’s a fantasy come true. Through e-mail and messaging I could steer the situation in my favor a bit.

Eventually, I started posting my own ads. I started with brief and general details:

Single woman seeks fun with hung guy. Daytime tomorrow. Safe play only.

It never made sense to me that a woman who occasionally indulges in casual sex is perceived as desperate, insecure, or less desirable. I have yet to experience a greater feeling of independence and self awareness then when I harness the power of my sexuality and my freedom to choose to do exactly what I want.

After writing my ad, I’d click post, and sit back and watch the e-mails pour in. Sometimes there were more than 30 in an hour. I’d sift through the ones with photos and phone numbers. I’d find three that seemed ideal and I’d work on them. Those who responded immediately were at the top of the list. Those who used complete sentences and showed a tiny bit of personality and intelligence ranked higher than those who simply appeared to be physically attractive in their photos.

It was easy to steer the date in any direction I wanted. Since most men who answer ads like mine are primed and eager, it was easy to find someone who was agreeable to my specific requests and desires. I could be as vague (just fuck me) or as detailed (give me a full body massage and scrub my body in the shower, then dry me off, etc. etc.)

Soon after my first few “dates,” I was posting ads that were much more specific.

Single woman seeks:

Mutual oral only

A massage and a quickie

A rough thorough fuck

A fun evening of drinks, dinner, and who knows what else

If one prospect didn’t seem too interested in what I proposed, I could move on to the next and the next.

It was like a casting call for my own secret fantasy.

Once I selected who would play my leading man, setting the scene and selecting wardrobe were next on my list. It never made sense to me that a woman who occasionally indulges in casual sex is perceived as desperate, insecure, or less desirable. I have yet to experience a greater feeling of independence and self awareness then when I harness the power of my sexuality and my freedom to choose to do exactly what I want.

Finding casual sex with a partner is a different type of “project." We decide on a date and time frame and discuss what we want to do. We sift through prospects — sometimes we post new ads on the sites I mentioned. Sometimes we go through responses to previous ads. Sometimes we invite people we’ve enjoyed before.

We have our own preferences and hang ups: He doesn’t like when someone mulls over fine details of what they’re “allowed” to do. This may seem conscientious, but to him, it’s a sign that a person can’t go with the flow and won’t read us well. I don’t like too many dick pics. Send me one, or two if you need to display different angles. Sending your dick’s extensive portfolio implies that you are too eager and possibly unable to realize that this is our fantasy, too.

We both hate when someone repeatedly boasts that they’re going to be the best experience we’ve ever had…  What? You don’t even know us.

Twenty years ago, people had to invest valuable time and effort in getting ready and socializing and flirting in order to find a casual encounter. And there was no guarantee for success after that time and effort was spent, and the chance of finding someone to fulfill a specific fantasy on a whim was probably tiny. I don’t even understand how people did this before the internet existed. I’m glad for the conveniences at the tips of our fingers and taps of our phones. I’m almost afraid to imagine the ease with which these connections will happen 20 years from now.
 
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