5 Tips for an Unforgettable One Night Stand
By: Ms. Part Time Wino
Tags: Sexuality, Dating Advice, Dating, Advice, Sex Advice

I’m a serial monogamist.

I had five serious boyfriends before I turned 20, cohabitated with four different romantic partners, been engaged twice, and got married once (and then divorced, but that’s a different story).

In fact, I would say that 98% of my adult years were spent in serious relationships.

But the tiny percentage of time I was single? Those few weeks or months in between ending love and finding it again?

Well, when I was single — boy, was I single.

I had perfected the art of flirting (or at least the art of swiping right). And I used that newfound sense of freedom to explore the world and all the beautiful penises that came with it. But to me, everything was just casual sex. After breaking up with a guy or getting my heart broken by one, the last thing I wanted was a new relationship.

So, having one night stands became my new hobby.

And while those phases of carefree fucking would only last short periods of time, they opened my eyes to a world of sex I had never seen before.

The truth is, one night stands can be great. Therapeutic. Even life-changing. And while I’m happily settled down in a long-term relationship (surprised?), I’ve learned a lot from my single days. And I want to share what I’ve learned with all of you.

1. Your partner doesn’t have to tick every box

Looking for love and looking for a one night stand are two different ballgames. Just because someone isn’t boyfriend or girlfriend material doesn’t mean they can’t be a great lover.

For example, my future husband should want kids. I want him to be nurturing when I’m sad, supportive when I’m lost, and communicative when things get rough. He also should be respectful, caring, and of course, funny.

But when I’m casually dating, those specific rules no longer apply. Of course, there will be some overlap (even the guys I fuck should be respectful and caring), but I’m not fussed about if they want kids, don’t want kids, or already have kids.

Letting your mind and body explore other types of people you wouldn’t normally chase after is a good thing. And who knows, you just might discover that your original checklist of characteristics isn’t as important as you thought.

2. Don’t be ashamed of what makes you horny

We all need to be liked. Okay, maybe not “liked,” but at least not outcasted and ridiculed.

And sometimes, that makes us wary of sharing our deepest, darkest secrets. Because we fear that it will be something so perverse and absurd that our partners will run out of the room screaming and tweeting about how disgusting we are.

You’d be surprised to know how many men have shared their unconventional kinks with me on a first date. There was the guy who couldn’t orgasm without me licking his nipples, the man who wanted to be choked, or the guy who liked to spit into my asshole.

*shrugs*

We hadn’t had sex before, so the only way for me to know what they liked was to tell me. And while every person should feel comfortable sharing those desires with everyone they sleep with, it’s just so much easier with a one night stand.

3. Understand that not everyone will want more

If you expect your one night stand to turn into a relationship, chances are, you’re going to be disappointed.

Sure, some one night stands can lead to serious relationships (heck, I’m in one right now), but that’s more uncommon than not. In most cases, a one night stand is just that. One night of sex. Nothing more, nothing less.

That’s why it’s important to set realistic expectations about what will come from your one night stand.

If you’re too wrapped up in making things more serious, you’ll miss out on all the wonderful things casual sex can bring. Like freedom, exploration, and really, really good orgasms.

4. Experiment, experiment, experiment

During my first few one night stands, I was extremely submissive. That wasn’t my kink — I was simply too worried about what the other person wanted over my own pleasure.

But as I got older? I used these one night stands as a chance to experiment with my different sexual personalities. If I wanted to be more dominant, I was. If I wanted to test out a new dirty phrase, I would say it. If I wanted to give a gaggy, slobbery blow job like you see in porn — honey, you better believe I gagged and slobbered with every ounce of my being.

While some people only feel comfortable experimenting with people they’ve been with for a long time, I believe there’s a lot of freedom in sleeping with someone you might not see again.

5. Accept your behaviors and beliefs

While I’m a big fan of having one night stands, I understand that not everyone feels the same way. My family, friends, and random people on the internet will all inevitably have strong opinions about my sexual behaviors and beliefs.

So, if you only remember one thing from this article — it’s this:

Don’t judge yourself for having a one night stand.

It’s nobody’s business what you do with your body except for yours. Give yourself permission to have sex with strangers (safely) and allow yourself to explore your sexuality.

Life is short — but our sex lives are even shorter.