What to wear on a date with your crush and his wife

A few weeks ago, I went on a date. Dinner at a lovely restaurant, a playful argument over who was paying, and a walk through a London’s beautiful streets in the cooling air. It was brilliant. There was some flirting, some teasing, and – on my part anyway – some blushing. They’re both wonderful, clever, attractive-as-fuck people: one of them I want to be like when I’m older, and one of them who I want to fuck right now.

The fucking isn’t on the table – for sensible reasons that my cunt doesn’t totally agree with but my rational brain does – but I have an undeniable crush on them. They know, and their partner knows… and while I could write this piece in gender neutral terms, I know I’ll end up giving it away even if you had assumed that it was a hetero couple from the title. There is a brilliant, kind, funny guy that I am attracted to, while also having huge admiration and respect – and a bit of a writing-crush – on his wife.

In some ways, I wish that this story could be a sexy one: one where I wore a butt plug to dinner and got bent over the table and fucked in the ass with it. It isn’t though, though it was brilliant. It was also a date. The word “date” had actually been used, which – as I’ve been on barely a handful – didn’t exactly help my nervousness. As much as a tiny bit of me hoped something would happen, I knew it was going to be a meal with two people I really like and count as friends.

But even if nothing was going to happen… I knew I wasn’t going to get fucked, but I wanted to tempt him. Both of them, in fact. I wanted them to look at me and think about fucking me, to have to remember the reasons why it wouldn’t be a good idea. This meant I had to choose my outfit carefully – and I don’t know about you, but I don’t actually know the etiquette for when you want to make a man who you’d like to call Daddy think about spanking you.

Like any millennial, I took to Google to seek answers. A couple of my friends knew who I was meeting, but while they were all supportive they didn’t have any advice about what I should wear. Apparently, google didn’t either.

The internet search for ‘what to wear on a date with your crush and his wife’ yields zero helpful results. Even when you refine your search, specifying you want all of those words, or try being a bit kinder and going for options like ‘clothes for date with an older guy’. What I did find, though, was an article that made me ever-so-slightly very, very angry.

The article was a list, a list of the things you shouldn’t wear on a date. The list includes thigh boots, clothing that is too tight or too loose, and has slogans or distracting prints. All black clothes, tight skirts, yoga leggings, perfume, sports bras, and noisy jewellery are apparently also forbidden. Not wearing dirty clothes is fair – though possibly unnecessary – advice, and I am always an advocate of wearing shoes you can walk in. I personally don’t understand what “ugly underwear” is, and definitely wouldn’t be showing it to anyone who would care whether I was in worn cotton knickers or green silk panties.

The one that really annoyed me, though, was sweaters. I all but live in sweaters and am of the opinion that I look utterly adorable and kissable in them.

In case it’s not clear, I don’t do well with people telling me what I can’t do. In fact, when someone tells me that I can’t do something – whether that’s studying physics or liking girls or having more than one partner – I have an additional urge to do the thing. My desire to say fuck you to societal conventions will probably get me into trouble at some point, but it also leads to some wonderful adventures.

It took me a while to calm down and stop trying to work out how to combine every piece of this advice into an outfit that does the exact opposite. Ultimately, though, no one had any advice on how I should dress to go to dinner with this attractive, dominant man and his gorgeous, sexy wife. The article had given me an idea, though. In telling me everything I shouldn’t wear, the internet had reminded me of one of the most subversive, rebellious things you can do: love yourself.

So, what do you wear for dinner with your crush and his wife? Well, if you’re me, you eventually decide that the most important thing is feeling good about yourself. The boots that make me feel confident and powerful, my favourite skirt, a sex-positive shirt from an independent clothing store. No tights, because it was a warm day and the warms of the sun felt good on my bare legs.

I felt really good, because I felt like me.

I had a feeling that she wouldn’t be wearing knickers, but mine were very much in place between my legs as I waited for them. Part of me wondered if I could tweet I’m wearing knickers because I don’t want to leave a puddle of arousal on the chair in this restaurant, but sometimes you have to be honest and tweet about how you feel you might be about to throw up from nerves. As I leant against a tree and checked my phone for the hundredth time in a minute, I caught sight of my reflection in the restaurant’s window.

In dressing like myself, I realised that I’d done something else. The white t-shirt and short, dark skirt made me look, out of the corner of my eye, a wee bit school-girl-esque. The barely-legal, naughty school girl look plays very much into my kinks, which he knew. I couldn’t quite believe that I’d managed to put together a look that looked totally natural but also might, if you knew about my fantasies, give a little bit of innocent-young-girl-begging-to-be-corrupted vibe.

The thing I can’t decide, even now, is this: if he had texted me to tell me what I should wear for dinner, would I have followed his instructions, hoping that I would get a satisfied nod of approval and a whispered good girl as he hugged me? Or would I have worn something else in a deliberate act of disobedience, in the hope that he’d notice and growl in my ear that I am a bad, bad girl and he’s going to punish me later.

All that is hypothetical, of course. As hypothetical as the butt sex with the anal plug I had in my bag under the table but was too nervous to have inside me.


Ode to sexting
You can't tell lies with a cock in your mouth

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