Sext appeal: message like an adult

I recently spent a happy 3 hours on a train. This is a rare and – in my life so far, completely singular – occurrence. Train travel normally stinks, but in this instance I was lucky enough to be travelling first class, and was doubly lucky to be having a blistering whatsapp conversation with my significant other.

Ah, how did people live before instantaneous private messaging? Focus on the private here, what goes on between the swain and myself is none o’ yo business. (Sorry about that, but it’s not like there aren’t some other excellent writers around here who are willing to get personal).

I used to consider myself something of a wordsmith – you can eye-roll, go ahead, I’m cool with it – and so sexting (an unwieldy portmanteau, but given the circumstances I’ll take it) was an opportunity to combine two of my favourite things: sesquipedalian loquaciousness and sex. It’s something I have put a lot of thought and effort in to over the course of my adult life. And, even after I realised that I wasn’t quite Henry Miller, in my continued attempt to take sex seriously I’ve tried to get better at sexting.

What follows are some personal thoughts. Having not sexted every man and woman on the planet (yet) I cannot say with certainty that these tips will suit in every case, but I have tried to stay away from cliches and stick with stuff I thought was hot. Think you can do better? Share your tips, stories and best – or worst – sext messages in the comments.

Before we start – this is guide for partners, or at least people who know one another. Blind sexting – via dating sites, apps and the occasional wrong number – is unknown, treacherous territory, and by the time you know it’s happening you’re already fighting with your autocorrect. So this guide isn’t really about initiating sexting, it’s about how to be flippin’ excellent once you get started.

They’re all texting the dude on the far right. He’s playing Flappy Bird.

Be honest

want 2 mess around? 😉

As a conversation starter it’s not exactly Oscar Wilde, but it has some useful features. While steamy text conversations often develop naturally, one party looking to fool around when the other is disinterested, tired or busy is a going to lead to mild disappointment at the least and potentially hurt feelings at worst. Simply asking if the other person is up for it – cheerfully, casually, cheekily – gives them a chance to say no with good grace and provides about as good a start to the whole process as you’ll get if they’re interested. Asking a question also has another benefit – whoever you ask can’t help but wonder if maybe they do want to mess around. Sometimes all an erotic encounter needs is that tiny little spark, a little driver of interest to awaken feelings that are always present but normally subdued. Do I feel like messing around? Not while I’m looking at this spreadsheet, no. But now I know it’s an option… actually I think I kind of do…

Know your reader

I used to hang out with a woman who loved the C word. Said it all the time, with real relish (she said it was something to do with attending Catholic school). She said it during sex as well, with equal relish, and so I said it back (in context, obviously, we weren’t just calling each other c*nts in the middle of coitus). But with her, although still taboo and a bit naughty, the word didn’t have its normal power to shock and unsettle. Using it at another time, with another woman, even during a heated situation, would have been a mood killer. While sexting is a great opportunity for fantasy and play, you should always be aware of the effect your words – your specific words – may have. You’re looking to excite, not shock, provoke, or disgust – even by accident. So c*nt is right out, unless you already know otherwise (as are words like moist and fluid, no one wants that). Everyone has preferred words for discussing intimate things. Find out what your partner’s are, and use those instead.

Don’t rush

The most difficult and important thing, in my opinion. A gentle escalation to a theoretical point of climax is super hot (…not when you put it like that, obviously). Escalation also drives itself. If you’ve just got started, telling your partner that you’re going to jam it in ’em is, firstly, premature enough to spoil things, and secondly a difficult level to increase beyond. Because there is no physical sensation, every message needs to contain something different to stop it getting repetitive. And that lack of physical sensation makes it hard to de-escalate. In real life if you want to slow down you can just go back to snogging. But if you’re sexting and you’ve already got to the serious business, real word porn, how do you take a backwards step? Better to tease away the time – you’ll get more enjoyment out of the whole thing, it’ll last longer and it might go somewhere genuinely new and interesting.

Be aware of the limits

One thing about continuous escalation is that it has to stop somewhere. Everyone has a limit, and if yours is pretty high – you’re totally into talking about weird butt stuff or whatever – your partner’s is probably lower. This means that the quicker you get to the hard stuff the greater the chance that escalating things will take you close to your limits – which can be intensely sexy – or beyond them – which totally isn’t.

In a way it’s similar to a nude photo – once you’ve seen all there is to see, the only way to top it is to grow ever more explicit.

You might confidently send someone a photo of your dick, but be a little uncomfortable if the return message demanded a picture of you inserting something somewhere intimate. Be aware that words can have a similar effect.

Don’t make it twee

Be sparing with your 😉 and your :p , your emoticons, puns and innuendo. Wry and knowing is good, and if you’ve got an absolutely killer one-liner prepped then by all means tickle some funnybones. But coming off as twee – or worse, immature – is a mood dampener. It makes you appear inexperienced, like you’re substituting broad humour because you don’t have a fucking clue what you’re meant to say next.

Be active

Being passive is draining. It’s less fun for you and more work for your partner, who has to take all the responsibility for where the conversation goes. It’ll also, if they’re a nice person, make them question whether you’re into it. If you aren’t into it, or you were and now you’re losing interest, then that’s cool. Just leave ’em wanting more and then tell them you’re stopping. Make an excuse. But putting all the onus on them is kind of like lying there in bed like a log. Someone horny enough is probably going to keep going, but it’s not very flattering.

Be inventive

A picture can be worth a thousand words, but most of them really aren’t. A single carefully deployed word can be worth a thousand clumsy pictures.

One of the things about taking it slow is that you have plenty of time to think about what you’re going to write, and plenty of time to be inventive. You don’t need colourful metaphors or to dig out the thesaurus, but sexting is fantasy at heart – you can do things you would find impractical or unlikely in real life.

When the only explicit image you could get on your phone was 3========D


Be bold

Pushing the envelope is part of what makes the experience sexy – you’re supposed to be naughty, that’s kinda the point. Go as far as you dare. This is also a good reason for being the active role – if you’re in some control over where things are going, you can keep some boundaries. You can go as far as you dare, and then no further.

Be kind

You gotta be kind.

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