Guest blog: The first time I truly loved anal play

Image by the brilliant Stuart F Taylor

Do you remember the first time you ever did anal play? I vividly recall the sensations – both physical and emotional – and the combination of nerves and excitement and taboo. Today’s guest blogger, Shar, is here to share her first anal play experience and explain why she went from ambivalent to enthusiastic…

First time anal play

A few weeks ago I would never have imagined that I’d be writing about my anal experience, as I was always the first person to say “girl, bye” when it came to anal play. But after one of my friends mentioned an alright experience with a finger being popped up her arse it got me thinking…

I’d say my sex life is great – well, more than great but let’s not blow my own trumpet. My fiancé is thankfully very good at doing as he’s told. Not that I’m a bossy bitch but he trusts me, and so far he’s been up for anything. He’d never mentioned anal sex to me, and we hadn’t been there yet (at least, not intentionally: we’ve all had the ‘slip out and almost enter your arse incident’, right? OUCH). But that’s as close as he’d ever been to my rear end.

Over the past few weeks I’d thought about it more and more until I came to the conclusion that I might like it, if done properly.

I bloody love exploring my sexual limits, so I’d looked into the subject on tushie play a lot. I read blogs, coming across heaven and horror stories – some made me flinch with tears in my eyes and others made me hot.

One bit of advice I came across was to start small: I had all the kit already from an advent calendar from a sex toy company. At least 10 of the items behind the doors were for anal pleasure! I was pretty pissed at the time, because as previously mentioned I used to think anything going up my arse was a definite ‘no.’ But after a few days of light conversation with my fiancé, I had a few too many one night and suggested we use one of these toys, seeing as I paid good money for them.

And like fools we got straight to it.

I have no idea why it was so weird at first… started small, was already pretty naturally lubed in the region near to my butt hole. I just did not enjoy it! So got it out of there and carried on with my beloved regular-ish sex.

I was ready to say that anything in my arse was not for me but at least we tried, right?

Oh how wrong I was!

At least a week went by until it was mentioned again in a sexting conversation.

“How about I use my tongue next time?”

I was like babe you can put your tongue where you like as long as you don’t actually enter my arse hole!

His reply was “I’ll just do when you’re not expecting it.” I said “You can try…” This “I’ll do what I want” approach doesn’t work for everyone, but not gonna lie: it worked really well for me.

Orgasms that start from somewhere else…

Cut to the other night: we were having sex and I could feel I was nearly at the point of no return when he removed his tongue from my throat and put something in his mouth. I didn’t really register what it was or what he was doing – I was just so into it.

Then he lifted me onto his lap and put one of my legs over his shoulder, removed this thing from his mouth, reached round and underneath me… Suddenly I heard a dull vibration and thought – wait, WTF is that? Before I could ask what it was he pressed it up against my arse hole as he plunged his cock in the front.

Now to the point of why I’m writing this anal play essay…

He then shoved that vibrating thing up my butt hole and I loved it. I FUCKING LOVED it.

I’m not one for screaming and moaning a lot during sex but this time I couldn’t help but moan while exhaling breath.

The next part took me a while to get straight in my head.

I’m very good at listening to my body: I can tell when I’m likely to climax just by judging our rhythm. And not at one point did I think I was definitely there considering the distraction of having a bloody butt plug inside me. So it came as a surprise when all of a sudden I felt this immense wave of emotion come over me! I felt tears building in my eyes, then that pre ogasmic tingle you get that usually builds from your core and then it consumes all your worries and fears all at once. So strong it can sometimes make me forget my name!

But this time instead of building from my core it was building from my vibrating arse… literally.

Then came one of the most delicious orgasms I’ve ever had, my whole body was quivering! I couldn’t see straight, think straight and just slumped my head over my partner’s shoulder in a paralytic state and wept happy tears.

So that was that! My first enjoyable anal play experience! High five’s all round! And that experience is going in my top five of all time too…


Note from GOTN: if you’re planning on embarking on anal play for the first time, I second Shar’s recommendation that you start small! Buy a small butt plug or use just one finger to begin with. There are some recommendations on the sex toys page here. I’d also suggest using lots and lots of lube (like any of these by System Jo who sponsor my site!), and making sure you’re communicating and checking in with your partner at every step of the way. Shar’s fiancé’s ‘I’ll do it when you’re not expecting it’ is super-hot for people like me who enjoy being told what to do, but not every relationship has that kind of dynamic: consent is key, always. 

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