vANALtines Day. I’ll do your arse then you can do mine… (28f) [FM]

“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:

1. Remarkable stamina.
2. 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.

–

But this was supposed to be a short, quick post. So I’ll pick up on that in another follow up post later in the day!

Source: reddit.com/r/gonewildstories/comments/ljcxwr/vanaltines_day_ill_do_your_arse_then_you_can_do