"It's Valentine's Day... Let me put it in your arse!"

You can't spell Valentine's Day without ANAL.

“Awww, come on Alice. It’s Valentine’s Day. The most romantic day of the year. The day for couples to show how much they care for each other… Let me put it in your arse!”

These were the delightfully romantic words uttered to me several years ago by my then boyfriend Ryan. And I immediately know what you’re thinking. How did I catch myself such a charmer?

Short answer: Our relationship had started as something of a ‘Christmas fling’ that had, somehow and despite the odds, survived until February. It was a largely causal affair but, I was assured, definitely more than ‘just’ casual sex as we also went on dates which, by definition, meant we were dating. At least, so I was told.

I’m being a little unkind. Ryan was a lovely, decent guy and, without wishing to sound too shallow, was incredibly good in bed. I’d always struggled when asked by friends what I saw in him to not answer too graphically. Because if I was being honest the two primary reasons could be summed up as:

Remarkable stamina.

A thing he could do with his fingers that I could neither explain nor mimic, but that - and I’m not exaggerating - worked every time.

It’s also worth me clarifying here that the above quote, while genuinely uttered by him, was said partially in jest. By which I mean he absolutely meant it, but simultaneously knew he was delivering a ridiculous argument.

I’m planning on keeping this post relatively brief so I’ll not launch into my entire philosophy when it comes to anal sex here. Suffice to say it’s not my favourite thing in the world but, equally, once every blue moon, it can be worth exploring just in case the veil can be pulled back and suddenly the mysteries of the universe are revealed.

So, Ryan delivers this remarkable line and gazes upon me with the largest and most sympathetic eyes seen on anything but the most adorable of puppies. He’d also, earlier in the evening, bought a far more expensive dinner than I think either of us were expecting.

I was all set to decline. For the appalling approach as much as intending to pass on the marginal discomfort while still feeling full of food. But damnit there was something so infuriatingly attractive about him when he looked mock-sad. And the meal had been delicious. And he could do that magic thing with his finger which could probably make even arse shenanigans fun for all involved.

“Fine,” I said, masking a sigh.

He sad eyes immediately disappeared and I swear he immediately made moves to remove his trousers. But I hadn’t quite finished…

“But since, as you so elegantly state, it’s a day for couples to show how much we care for each other, I feel you ought to share the discomfort.”

He looked both perplexed and aroused, which makes for an interesting combination. He also hadn’t faltered in removing his trousers.

“So. You can put it up my bum. But first, I get to slip something in yours.”

He froze. I could almost literally see his mind firing as he tried to decide whether or not to immediately pull his trousers back up.

But he was rarely one to go back on a decision. And, ultimately, he realised that he was getting exactly what he wanted, just with some bonus gritted teeth.

And so, stood with his trousers around his ankles, the very definition of dignity, he looked me square in the eye and in his mostly manly voice declared;

“Umm… yeah, okay.”

For the sake of brevity I’ll skip the foreplay. With sex as both the bedrock (pun intended) and largely soul purpose of the relationship, we’d been having a lot of it and were well acquainted with the minutia of what we most enjoyed and what was most effective. What we may have lacked in traversing the epic voyage of discovery, we more than made up for in glorious efficiency. It was also somewhat longer than so-called ‘standard practice’ as, by practical necessity of what was to follow, it also incorporated an incredibly thorough shower…

Additional moisture aside, it took no time at all using fingers (his) and tongue (mine) to get each other worked into a sufficient frenzy to consider moving things toward the rear.

I had no intention of being needless cruel, so liberally applied lubricant to the tips of my fingers and, while one hand was heavily engaged in stroking his cock, and whilst he was distracted by my tongue seemingly wrestling and pinning his to the base of his mouth like an oral thumb war, I reached around behind him and began to caress and tease his arsehole with my fingertips.

I must confess I grinned when I first heard him grunt and bite gently on my lip as a single finger tentatively eased its way inside.

With a gentle pace I began to slide the very end of my index finger in and out of his arsehole. Though I felt it tense under my touch, his renewed vigour in kissing suggested he certainly wasn’t finding the sensation unpleasant.

Reasonably content that he wasn’t going to scream blue murder as things progressed, I pulled my lips from his and slid down to my knees to renew my work with my tongue. I could sense his frown as he was seemingly questioning why things had slipped back to earlier foreplay.

He shouldn’t have doubted me.

As I took his cock into my mouth, ticking the underside of the head with horizontal strokes of my tongue as was his favourite, I kept my hand behind him, still teasing his areshole with soft circular motions. The precum I could taste seeping from the tip confirmed all was still well.

Which meant it was time to make a move.

In one motion - or as near one motion as a relatively uncoordinated me can manage - I slid my head forward over his cock, taking him deep in my mouth with my tongue wriggling and gyrating along the underside of the shaft. Simultaneously I ease on the teasing and slip my finger fully into his arse.

“FUCK!”

I don’t wait to see that was a declaration of enjoyment or discomfort as I’m confident I know the answer and have no intention of losing the momentum. I maintain the pressure and essentially assault him from both ends - my lips clamped tightly around his cock sliding from base to tip, while my finger slides in and out of his arse at the same pace and rhythm.

“FUCKING HELL” he declares again, as he almost immediately cums in my mouth. Shot after shot after shot - my finger again matching the spurts in motion and intensity.

He collapsed back on the bed, breathing heavily. Fortunately I saw this coming or he might have fully impaled himself on my finger.

I swallow his load and writhe up beside him, feeling exceptionally pleased with myself. I go to give him a kiss but can see he’s trying to pull a frowny face, despite his mouth being still locked in the almost rictus grin of post orgasm.

“Your arse was supposed to make me cum!” he said, grumpily through his breathless smile.

“It’s still Valentines Day for a while yet…” I grinned back.

Ryan was valiantly attempting to look disappointed despite being barely able to hide his broad grin and still gasping in the aftermath of what had been, even if I say so myself, something of a momentous orgasm.

For what it’s worth, my grin was easily as wide. Not only was I basking in the warm success of having generated such enormous satisfaction using mouth and a solitary finger alone, but more crucially my plan had gone without a hitch. Now, if he still wanted to ‘put it in my arse’ - the whole intended point of the endeavour - then he would need time to sufficiently recharge first.

And that meant at least twenty glorious minutes of him using his tongue and glorious fingers on me.

Devious? Yes. But given he would soon be inserting his cock into a part of my anatomy chiefly designed for things to move in the other direction, I felt it was forgivable.

“Better keep me entertained while you recharge so I don’t get bored and wander off…” I said, aiming for subtle and coy but missing entirely.

“Sneaky bitch” was his only response, a resigned look crossing his face as he laid me back on the bed, lifted my knees, and spent a little time finding a comfy position with his head firmly between my legs.

His oral skills were a moderately good six out of ten. Perfectly serviceable and able to get the job done, but very much not of the variety that make for a particularly entertaining anecdote. I’d often joke his tongue was wider than it was long, but what it lacked in delicacy it made up for in efficiency. Where his real skills lay were his, frankly, magic fingers. I don’t know what exactly it was he did with them as I could never contort myself into a position to see (Not that I imagine that particular angle is a good look on me), but whatever *it* was it was both effective and addictive.

And worked *every* time.

Subjecting myself to very nearly half an hour of this was more than enough to compensate for the discomfort I knew I was inevitably to follow. Which is to say that as I writhed on the bed, rolling almost 360 degrees, switching between grasps of the sheets and grasping the back of his head almost as though trying to pull him inside me, I really didn’t much care.

The bastard teased for the majority of the duration, always pausing or holding back if he felt I was getting close. He did it to annoy me, and to make a point.

He succeeded in both regards.

“Do I make you cum, then stick it in, then make you cum again? Or stick it in, make you cum and then see what happens next?” he asked, looking almost as smug as I’d been earlier.

“What do you think, Fuckwit?”

We were an endearing couple.

He dutifully performed his finger trick and didn’t stop until my legs were shaking. I genuinely think he wasn’t even intended to stop then, but to try to maintain the moment until he’d managed to get up my arse.

Watching him attempt to lube up one handed had me in such fits of laughter, it very nearly put me off my orgasm. It was akin to watching a great ape trying to be delicate with a tourist’s camera that has dropped into its enclosure, but instead inadvertently smashing the thing.

So I sat upright and lubed his cock for him instead. And It’s a good job penises don’t need to breathe, because I’d have drowned it.

We kissed as I stroked him back up to full erection, before spinning around and positioning myself on all fours. He took up position knelt on the bed behind me, his cock quite literally dripping with lubrication.

“Good luck!” he said, in an unbearably cheerful tone.

“Fuck off!” I replied, in an equally cheerful voice.

He reached forward and parted my arse cheeks so delicately and daintily that I burst out laughing. He asked me what was so funny and I told him that he wasn’t disarming a bomb and that it would be in his best interest to get on with it. Also to have his magic fingers ready.

He rubbed the tip of his cock against my arsehole for what felt like *hours*. I understand he was being gentle and careful and that fact is absolutely appreciated. But when you’re on all fours waiting for something to actually *happen* behind you, time very much slows down. Anticipation is a lengthy and cruel affair.

After several days had passed, he finally slipped inside.

“That okay?” he asked, hiding the delight from his voice.

“Mmm-Hmm” I replied, avoiding having to open my mouth. I’d be lying if I didn’t admit my teeth were gritted.

What followed was a truly unknowable length of time wherein his movement back and forth was almost entirely imperceptible. However, crucially, whilst it would be inaccurate to describe the process as ‘comfortable’, it certainly was in no way actively painful.

Several generations later, once it had been fully established that everything was fine, he picked up the pace. What it lacked in the aggressive rhythm of the best doggystyle sex, it made up for in sheer intensity.

Which is to say that he grabbed a firm hold of hips, and fucked my arse.

He sounded as though he was having a wonderful time. Every-so-often he’d ask me if I was enjoying it and, once I’d stopped gritting my teeth and unclenched my jaw I answered.

“Enjoying is the wrong word, but it’s fine.”

I know. I really aced the sexy talk.

My lacklustre answer however galvanised him into action. With his right hand he released my hip and reached around to the front.

Have you ever read a mystery novel and had that single moment of blissful revelation where you spot the vital clue and all of the pieces fully fall into place? Because that’s all I can liken the sensation to when he combined fucking my arse with his magic fingers.

It still wasn’t *comfortable*, but it did make *sense*.

My immediate and obvious enjoyment was all the encouragement he seemingly needed and, with his fingers deep inside me, he fucked my arse with the same pace and hungry intensity he’d fuck me normally.

With the renewed vigour it didn’t take long for my elbows to collapse, plunging my upper half down into the bed.

The sudden change in angle was apparently all it needed. Mere moments later he declared he was going to cum.

My head whipped around like lightning as I told him in no uncertain terms that if he came *in* my arse I’d slam a miscellaneous hard object down squarely on his testicles every night after he fell asleep.

He pulled out seemingly *just* in time, and shot several loads directly on to my bare arse. Normally I feel somewhat short changed if I don’t get to participate directly in the final act of completion - under normal circumstances I’d have spun around and finished with hand or mouth - but on this occasion I felt that, frankly, I’d already done enough.

But Ryan didn’t seen to mind. He was apparently too busy enjoying the image of his cum dripping from my posterior. He told me I had a really cute bum, and gave it a little smack supposedly out of appreciation, but mostly just splashing cum across the sheets.

I told him that earned him one night of heavy object on the testicles. He seemed reasonable sure I was joking.

-

After the cleanup he asked me if I’d enjoyed my ‘anal experience’. My reply is, to this day, one of the most spectacularly unsexy phrases I’ve ever uttered and will be noted as something of a milestone moment in my own personal history. If you found any of the above even mildly erotic (though i’ve no reason to believe you have) and wish to retain any sense of that feeling, i’d highly recommend to stop here and not read the final line. You have been warned!

“Put it this way,” I said. “I’ve had considerable worse shits.”