Mar 19, 2021 • 12M

Five times I was legit terrible at sex

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The Overthinker's Guide To Sex is a sex and relationships newsletter written by freelance journalist Franki Cookney. This is the audio version.
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Crowdfunder update!

Friends, I am so excited and grateful for all the support this podcast has had so far! We're nearly at £3k which is just amazing. It means the world to me that so many of you are on board with what I’m trying to do, with this podcast series particularly, but also around sex and relationships generally. Every time I get a notification that someone’s donated I go and have a look to see who it is - literally every time! So I know who you all are and my heart is bursting. Thank you for being part of this community.

Every little bit you’ve sent my way spurs me on to keep doing what I’m doing and I’m so grateful to be in this sexy, talky thinky gang with you!

We’re now in the last week of fundraising and there is still a bit of a way to go to hit the target (by the way, if I don’t make it to £5k all the donations get refunded) but I know we can do it. There are around 1200 subscribers here in our little Overthinkers crew, of which about half tune in on the reg. So just think, if every single person who opens this newsletter today donated, we’d have that final £2k done and dusted! 

And believe me, if I’m able to get this series funded and made, I will be throwing the mother of all launch parties! I’d love to see some of you there! <3


I have spent the last five or six weeks talking about bad sex as though it’s something that only ever happens to us. But if we really think bad sex is only ever down to our partner, it’s time to take a long hard look in the mirror. When I talk about bad sex being a universal experience, I really do mean that we are just as likely to have been a crap shag as we are to have been the recipient of one. 

God knows I’ve been bad at sex. And if it comes as a surprise to hear me admit it, it really shouldn’t. I warned you from my very first newsletter! Just because I write about sex doesn't mean I'm good in bed, I told you. I was speaking in the abstract back then, of course. But I think it’s time to get into specifics. So, because I am apparently intent on making sure no one ever wants to sleep with me again, I’m going to share five occasions on which I truly and irrevocably sucked at sex.

My first time

I almost didn’t include this because it seems so obvious. Of course my first time was rubbish. But then I realised that “first times” stories for women are often based around what their partner did or didn’t do and I thought that actually it was quite interesting to examine what my own role was. First of all, it’s important to say that what I’m counting as “my first time” was really just my first time doing penis-in-vagina sex. I would have no hesitation in saying that the intense kissing and dry humping I’d done before was an awful lot hotter and more pleasurable to me than this “first shag” and one of the reasons for that is the way those activities allowed desire and arousal to build up. This “first time” by contrast was very much a race to the finish line. Not that I came, obviously (my first time doing that was on my own and I’m happy to say that was very good sex indeed!) but I was so desperate to get this activity ticked off, to have finally done it that I paid very little attention to pleasure - his OR my own. I actually have a distinct memory of lying there thinking “Where do I put my legs?” such was my level of detachment from the sensual side of it. Now, I’m not suggesting my attitude was wrong. It was, after all, very much the product of a complete lack of understanding about sexual connection and conflicting beliefs about how exactly my pleasure was supposed to work in partnered sex. I can own my own experience of it. But when I look back now, it occurs to me that it probably wasn’t a great experience for my partner either. He, like me, probably came away from it with a sense of teenage bravado and swagger. He got his end away. But did he have a “good” time? Honestly? I doubt it.

5am walk of shame

It was someone’s birthday and we were out in a club. We ran into some friends of friends and one man in that group started chatting me up. We were drunk and in high spirits and clearly feeling opportunistic but for all that he was actually very sweet. “You’re so pretty,” he told me. When I look back on the photos from that time my response is “yes, that is absolutely correct” but at the time I was unconvinced. He was just laying on the charm to get in my knickers, I thought. And while I wasn’t resistant to the idea, I somehow felt I had to stay aloof from it, to not “fall for” his moves. If I was going to sleep with him it had to be a rational choice on my part and not because I was… I dunno, enjoying dancing and flirting and being the object of someone’s affections. Pretending I was indifferent felt, somehow, like a way of retaining control over the situation. 

That sounds utterly bonkers to me now. But at the time I was battling with the dilemma of feeling like I needed to be up for sex, but without actually being too up for it. I touched on this when I wrote about why I’m so obsessed with sex. It was completely normal to want sex. But you weren’t supposed to actually want it.

Anyway, we went back to his where he continued to be nothing but fun and nice and, I think, genuinely enthusiastic about me. And I… behaved like a dick. I rebuffed his attempts to engage in genuine conversation in favour of “getting down to it” and then proceeded to engage in performative, detached sex before putting all my clothes back on and leaving at around 5am.

“You’re welcome to stay over and have breakfast later,” he said, sincerely and somewhat perplexed. “Oh no it’s fine, the first tube will be along shortly!” I replied breezily, inwardly applauding myself for being such a Cool Girl. So chill, so rational. No strings here, baby!

To this day I regret the way I behaved. The “walk of shame” here had nothing to do with the sex we’d had and everything to do with my own fucked up attitudes around it. What led me to believe I needed to be like that? Needless to say, I have a few hunches. But you’ll have to wait for the podcast to find out. In the meantime, consider this a formal apology to that guy and anyone else who’s ever been on the receiving end of such nonsense.

I got my comeuppance though. The first tube did not in fact arrive for another hour and I was forced to sit shivering with fatigue and my creeping hangover on the tube platform.

A drunken haze

Long story short it was my first ever date with a woman and I was so nervous that I got atrociously drunk and then went back to hers where I can only assume I was an irreconcilably terrible lay. So I guess I just wanted to quickly acknowledge the role that booze can play in bad sex.

I also then ghosted her. FUCK, I am the actual worst. Please just cancel me now.

The squeeze

I fancied this girl a lot. Like, a LOT. I hadn’t dated many women when I met her and she was sensationally beautiful and interesting and we both liked wine and falafel and honestly I was about ready to plan our wedding. Which is probably why I was so intensely intimidated when it came to sleeping with her. When she asked me “How do you like to be touched?” my response was basically “Um, I mean, like, whatever, what you’re doing is fine… or… I dunno, what do YOU wanna do?”

(I also now know that this is a more complicated question than it seems. Because there are a huge range of ways I “like to be touched” in the context of sex but if we’re talking about ways to make me come, the answer is more concise. This is the kind of thing a sex menu can help with.)

What she wanted to do, it turned out, was have me wrap my arms and legs around her during sex and squeeze her really hard. The sensation drove her wild, she said. Which was enough for me to throw myself into the task with a vim unmatched by my actual physicality. 

Afterwards my entire body would ache, sometimes for days. And I still wasn’t getting mine! After a few months of this, I inevitably realised I couldn’t keep it up. But instead of communicating that, I simply broke up with her. Great job, Franki.

I have no idea if she would look back on those dates as “good sex”. I think what this shows, more than anything, is that through an inability or reticence to articulate what you want and need, as well as a lack of boundaries you can also inflict bad sex on yourself

Faked orgasms

This is actually an amalgamation of a few different occasions on which I faked orgasms but I’m writing it up as if it was one event because the reasons behind the faking remain the same. I’ve written about faking orgasms before and from my point of view it’s usually down to two things, an inability to relax enough to “let go” with my partner and the sense of not wanting to burden someone with the task of making me come (which, after all, might take a while, especially if I’m feeling anxious about it).

I don’t really blame myself for doing this when I was younger but as I’ve got older, more knowledgeable, more experienced, I am baffled to discover that the temptation to fake it is still there, sometimes. With one partner, it just felt like too much effort to have to explain what I needed them to do to help me reach orgasm. “I can’t be arsed with this,” I thought, and faked it.

Another time, I was just not very turned on. I don’t know if this is because I didn’t fancy them as much as I’d thought or because we simply hadn’t spent enough time getting in the mood but orgasm was miles away. Rather than risk making them feel bad, or seem “difficult” to please (“Can you actually just go back and spend like ten minutes playing with my nipples, thanks?”), I faked it. 

Why am I like this? Once again, I have some ideas. I’m not including this as a self-admonishment so much as an observation that even when we are fully, wholly committed to having good sex and being good at sex, those internalised beliefs and what we thought were long-forgotten hangups can still have an impact. This is why it’s so important to me to really dig into the concept of bad sex, to really dismantle the narratives around it, and figure out what actually needs to happen in order for us to say goodbye to bad sex.

What do you think? Hit reply on this email or comment below on the post to share your views.

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A couple more things to (over)think about…

  • I loved this video by Lolo Cynthia talking about what we’re actually looking for when we have sex 

  • This New Yorker piece about whether multiple person marriage will ever be a thing is interesting

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The Overthinker’s Guide To Sex is written by freelance journalist Franki Cookney.
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