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First time anal sex: how not to do it

Someone found my blog the other day by searching ‘first time anal.’ It’s quite common, this ‘first time’ thing, and it comes up a lot in search. ‘My first anal’ or ‘her first facefuck’, like someone’s researching an incredibly explicit series of picture books. Anyway, the search prompted me to think about first times, and it occurred to me that while there are a few first times in my book, I’ve not actually written about ‘my first anal fuck’ before. Mainly because… well… it wasn’t particularly sexy.

The first time I had anal sex was down to 50% curiosity (me) and 50% ‘you’re on your period so how about we…?’ (him). Please forgive him for this – we were both young and silly, and he was still getting over the slight horror that came from discovering that menstrual blood sometimes has chunks in. If I met a guy these days who assumed that buttsex was the only possible option while I was bleeding, I would kick him out on his arse, but back then it was not considered weird for him to ask, and I think he was bored of me practising blow jobs.

Besides, I was very keen on the idea. I was still in the kid-in-a-sweetshop phase of sex, wanting to try every new thing I’d heard of to see if it worked for me.

It didn’t.

Just writing that seems a bit strange, because now anal is one of my favourite things. So what went wrong?

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“I want you to hurt me because it makes you hard.”

This is one of those posts that goes into the sometimes dark places in my brain. As a result, it involves discussion of things like pain, BDSM, and roleplaying sex-as-punishment. Everything in the post is 100% consensual, but I’m just giving you a heads-up so if those things are likely to disturb you please don’t read on. 

We’re discussing the difference between corporal punishment and what I’m going to call ‘angry punishment.’ I explain to him that, in previous role-plays, I’ve struggled with the idea of rigid, ordered punishment. Counting spanks, measured chastisement, that kind of thing. The type of role-play where I am a naughty girl, and a guy in a position of authority is responsible for correcting me:

He orders me to bend over and touch my toes, stretching my thighs and arse taut for the cane or tawse. He makes me wait for what feels like an achingly long time, as my calves tingle and my cunt gets slick, and I wait for the first thwack.

At that moment what I’m hoping for isn’t one sharp stroke. I’m not anticipating a measured, precise stripe across my backside. But usually that’s what I get. One stripe – carefully applied – then the inevitable order:

“Count them.”

And I count. One, two, three, four… I count the strokes and I thank him for each one. This controlled, dominant guy, who will dish out exactly as much pain as I deserve and no more.

That’s nice – it is. But it’s not the best.

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How to have the best orgasm ever (if you are me)

There are any number of sex writers who’ll tell you how to achieve the ultimate, mind-blowing, amazing orgasm. Unfortunately, the way your body works may not be the same as the way mine works, so I can’t promise you stars and explosions and earth moving unless you happen to be formed in exactly the same way I am.

What I can do though is tell you that the other day I had the Best Orgasm I Have Ever Had, along with some lurid and sticky detail.

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Threesome director: Teach this stranger how to fuck me

“Two dudes.”

“Fuck’s sake – I know. You always want two dudes.”

“Yes but but but but. It’s more than that.”

“Honest?”

“Honest. The specific nature of this two-dudes fantasy makes it different to all the rest.”

“Really?”

Really. Let me tell you about my threesome director fantasy… 

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Good anal sex versus great anal sex

Anal sex is a topic I have done to death here before. If you’ve been reading for longer than a few weeks, you know that it’s one of my favourite things. The tightness of it, the promise of something deliciously taboo, the way he’ll whisper ‘good girl’ in my ear as I wriggle back onto his cock… unngh.

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