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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?

We did all the right things to start:

  • Plenty of lube
  • Taking things slowly
  • Pushing a laundry chest against the bedroom door in case someone walked in halfway through

And still the experience was a bit ‘meh.’

He trembled with adorable nerves as he slathered about half a bottle of lube on his dick. I lay face-down on the bed and breathed like I was doing yoga, in a misplaced attempt to avoid getting tense. Forgetting, obviously, that I am such a stressy person that any kind of meditative breathing is more likely to make me panic than prevent me from it.

And then he fucked me.

“Is that OK?”

“Up a bit.”

“Like this?”

“No, like… hmm. Angle it up a bit?”


“Yeah. Maybe ten degrees more?”

I hadn’t yet learned that the easiest way to get it in with anal is to let the person receiving push back, but we squashed it in eventually, and after a few strokes, a couple of gasps, and a comment about how tight it was, he came.

That is probably the least sexy sex scene I’ve ever written, and I think the reason highlights what I actually find sexy about any fuck I genuinely love. The filthy posts which really do it for me are less about the act (‘first time anal’ being, as it is, a very popular topic) and way more about the effect it has on who I’m with.

What makes anal sex hot?

When I have anal sex now, the thing that differentiates it from a cuntfuck is that it’s a bit dirty and taboo. That it’s non-standard. It’s… although I hate the word… ‘special.’ It might be special because it fits a specific mood, or because we haven’t done it for a while, or because me begging him to put it in my ass makes him diamond-hard in seconds. Whatever the reason, though, it’s about the atmosphere.

Perhaps that’s why ‘first time’ searches are so popular – there’s a perceived atmosphere to the ‘first time’ you do anything that in itself can be super-hot. The combination of nerves, excitement and curiosity turns a particular sex act into a treat.

Sadly that first time, with my first boyfriend, the atmosphere was one of vague curiosity and casual entitlement. He wanted to fuck me in the ass simply because he wanted a fuck. Any fuck would do. His dick was hard anyway and he just wanted to come. So anal wasn’t special, it was just a means to an end.

Contrast that with the guy who grabs my hair, pushes his dick up against me, and tells me he really really wants to fuck me in the ass… the one who gets harder pushing a butt plug in because he knows that next up it’s his dick… the bloke who makes a muffled grunt of horny delight when I push myself back onto his lubed-up cock… it’s quite a difference.

I don’t want to say that anal sex is hotter if the guy who’s fucking me is ‘grateful’ – gratitude isn’t the right word, because it implies I’m doing it as a favour. But when I try and work out what made that first time rubbish and subsequent times brilliant, enthusiasm is definitely a key factor. Anal is a bit tricky for me – especially if you’ve got a thick cock. I need to be calm, I need to concentrate, and I usually need to get into exactly the right position. I need to feel like what I’m doing is out of the ordinary – both in the way I do it and the way you react. If we start getting ready for a hard ass fuck, I can tell from the minute you start slathering lube on your dick whether it’s something I can take or leave. From the width of your smile or the noises you make, or the speed with which you flip me over and bite my neck.

So it’s not ‘gratitude’, as such, but maybe ‘special.’ Or ‘different.’ Or ‘out of the ordinary.’ Maybe that’s why ‘first time’ searches are so popular – it’s the uniqueness of a particular act that they’re trying to tap into. Whether it’s the first time, the fifth time, or the hundredth time, some fucks are hotter if we see them as a treat.


  • Valery North says:

    Love this! The discussions of “specialness”, and “first-timeness” of an activity, really resonate with me. I love all things anal play, and I’m sure the reason is just what you describe (whether I’m giving or receiving). And I have definitely experienced (at least in online play) the un-hotness of one’s partner just being horny and “any hole will do”.

    Sorry I can’t add much more, but basically “yes”.

  • rare deeds says:

    I like so much how you’ve managed to retrieve something really horny from something that “wasn’t particularly sexy.”

    The thing about the push back in anal is, I think, not just that it makes it easier, but also how much it disrupts the usual “moves” of fucking – which is already into that space of the “special”.

    I think the “out of the ordinary” is so important – how we avoid the routine – but the connection with the “first timeness” is, I guess, in that moment when it becomes extra-ordinary, an *event*, something that doesn’t just fall into a series of repetitions.

    For me, when I’m receiving, the thing about anal is the feelings of being overwhelmed, the excess of feelings, which I can’t control – which I don’t want every time, but which are definitely “special” when they happen. When I’m giving, the feelings at the very moment of penetration, with the push back, are exquisite – I don’t want anything to distract from the intensity of those feelings – so I want to take time leading up, looking, touching, heightening in every way the intensity of the moment.

  • RB says:

    I struggle a bit with anal (I think due to its infrequency in happening – I just haven’t got used to it despite being very keen on the idea) but if I was to meet that person doing the google search I’d definitely tell them to take it by degrees. I think one mistake people can make sometimes is to assume you have to dive straight in without preparing yourself in increments first – fingers, etc – it’s a lot of pressure to live up to to just decide to do it having not explored a little beforehand. And god help people who watch anal scenes in porn and think it’s that easy. Oof.

    (Only properly successful anal fucking experience I’ve had so far was with a guy who was in an open relationship with another man. He knew his way around the area!)

  • I have the exact same problem of “breathe to relax” *sphincter locks the door*. My guy’s on the bigger side, and I do want to work my way up there, but I’ve been letting him play with toys back there for a while to a) stretch out a bit and b) get used to the idea of someone else doing stuff back there. I’m getting more relaxed definitely, considering the first and only time I tried to have him fuck me it was impossible and painful.
    Like the first time of anything sex-related, it will probably suck. I can see it being hot once everyone knows what they’re doing though.

  • Some people like anal and some hate like anything. I am not into Anal but once in a while it’s OK.
    The only aspect is The Angle. If the angle is right then it’s awesome. Even if you get a right angle, it’s very difficult to maintain that angle.

    How to maintain right angle comes with lots of practice.

  • Cheryl says:

    Intent is the difference between ‘hot’ and ‘meh’. My partners get so excited when I push back and now I think I understand why. It isn’t a favor but something I want to do …crave and without saying a word my body’s actions tell them.

  • Alice says:

    I was kinda scared to try anal with my partner. I’d done it before with other guys and had good experiences but there was still an irrational fear of it hurting.

    So one time he’s fucking my cunt and he inserts a finger into my arse and controls the fucking with it whilst he’s whispering deliciously filthy things into my ear. I was beyond horny, totally out of control and he made me so curious about anal. We stopped fucking, changed position, he started to slip his cock into my arse and I pushed all the way back. There was a long, drawn out moan from both of us and we fucked like it was our last day on Earth.

    Anal is definitely a thing for us now!

  • Lacrymology says:

    I am not a squeamish one, I’ll give head when menstruating no problem, and though PiV can be a bit annoying because of it getting dry and sticky easier than normal, a bit of extra lube does the trick. But yeah, the first time you find out about the chunks it can be pretty… icky?

  • John Rosenberg says:

    Love anal sex, don’t know why, but i prefer to have anal sex 1 time a week than regular sex 4 times a week

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