Feature image via Shutterstock.

The first time I had post-break-up sex, it was awful and hilarious. I’d been browsing Craigslist’s w4w casual encounters section — always a good start! — and ended up emailing someone who said she was looking for someone to pamper. She wanted to eat someone out and offered the possibility of some kinky play together. I was into it. My breakup was hard, but I was finally, truly over the relationship and ready to have sex again. Lots and lots of kinky sex.

I invited her over, and we started to chat and get to know each other. Easy stuff. I’d mentioned in my email that I was not looking for a relationship. I wanted something quick, fun and, most importantly, with no strings attached. So after about 25 minutes or so, when I felt sure she wouldn’t chop me to pieces, we brought the conversation to my bedroom because we weren’t here to be friends; we were here to fuck.

We watched some porn together, got a little handsy and finally went for it. I’m embarrassed to say I don’t remember this girl’s name, but I do remember how cocky she was. Before we even got started, she mentioned how girls said that she was the best head they’d ever had, how she’d gotten girls to come 15 times in an hour, all of it. So when she tied my wrists together and started talking dirty, I was hype. Imagine being naked on a bed and there’s a hot butch top standing above you you saying things like, “I’m gonna tear this pussy up!” “Daddy’s gonna eat your ass so good!” “You’re naughty!” I was so ready before we really even started fucking.

And then she started to eat me out. And it was… okay. After all her talk, I was expecting something amazing — but maybe she was just getting into it. I wiggled around a little to try to help her find my clit, I gave a few verbal cues — “higher, lower, right there” — but it just didn’t get better. Instead, it got worse. She started to use her teeth. On my clit. I’m not here to yuck anyone’s yum, but teeth do not belong on my clit. So I lay on the bed, legs spread and shackled, arms tied above my head, and felt miserable. I couldn’t wait until she finished.

After about 15 minutes of this, I faked an orgasm. I know, I know… terrible. But I had to get up. She tried to keep going and I said something along the lines of, “I’m too sensitive, not right now.” She stopped, untied me and we spooned for a little. I packed us a bowl that we smoked on my porch and sent her on her way.

Why didn’t I just say something!? Why didn’t we have a conversation before we started? Why didn’t I tell her, explicitly, “no teeth”? There’s no real reason. Here’s what I think though: Being a sub who is in a relationship is easy, or at least easier than being a sub who is single. When I was in a relationship, my partner and I knew what we wanted in bed because we’d talked about it. I loved and trusted them, and because there was that foundation of trust, conversations about sex and kink were easier.

But as a single sub, I wasn’t going into one night stands with a solid foundation of trust and love. In this case, we’d never met in real life before. We’d sent a few emails, a few texts, and she came over. I didn’t want anything serious, and at that time for me, talking about wants and needs during sex felt too serious. I wanted sex as commitment free as possible; I was in love with the idea of a quickie with someone that I might never see again, and talking about it first seemed like a step in the wrong direction.

Falling in love with that idea is where I got in trouble. The idea of quick, non-committal sex with strangers sounds amazing, but there’s intimacy involved in sex, even if just for a night — or an hour — that requires communication, trust and respect. I had to learn how to be vulnerable with people I might never see again if I wanted to figure out how to have fulfilling casual sex as a single sub. I had to be comfortable enough to say, “I like this, but not that” to someone I’d just met, because if I couldn’t, I might get my clit bit again.

A few things helped me get better at communication as a single sub. One, I finally had an amazing one night stand, and it was with a top who wouldn’t touch me until I filled out an entire worksheet on BDSM. She also had me look up things that I was confused about, and talked to me about them before we slept together. What’s the most interesting is that all of this happened over about two days. We didn’t have some long drawn-out courting process, and we weren’t trying to build a relationship — it was just us making sure that we were having a good time together in the time we got to spend together.

I also started to use the worksheet in this You Need Help post. I have a blank one and one that I filled out and scanned, both saved on my computer. If I’m meeting someone new, I send them both sheets. That way, they immediately know what I do and do like, and I can find out what they like. It makes the conversation so much smoother because most of the awkward work is done.

Part of being a single sub is topping yourself sometimes. Which means that I have rules that I have to follow about who and how I’m fucking. I can’t fuck someone unless we are able to have a full, sober, adult conversation about what we want in bed. Even if they’re the hottest person in the world and I’m in the middle of Morocco and there’s a 100 percent chance I’ll never see them again. If we don’t talk, we don’t fuck. I’ve found resources to make those conversations easier. These worksheets have helped to guide conversations so that while they still might make me a little uneasy, they’re never more awkward than they have to be.

My rules work. They’ve allowed me to be more selective about who I sleep with — if she isn’t willing to take 20 minutes to fill out a worksheet about sex, then she doesn’t get to have sex with me. Talking about sex has gotten easier. It’s still awkward, and I definitely still laugh and blush, but it is easier. I feel better during sex. I feel better after sex. Being a sexually satisfied single sub is not only fun to say, but also hard work. But it’s also vitally important work. And when you do the work, the sex can be oh so good.

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!