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For the vast majority of his life — pretty much all of it, in fact — Lord Oyster thought he knew exactly what his future was going to look like. He was going to restore his family’s reputation and status, go and work out at sea, find a woman to marry and continue the family line with her. That future was never something he thought to question. It was just… his destiny. Fate. The done thing.
But then he met you and suddenly he found himself becoming more reluctant to find a suitable woman to wed. He spent his days at sea longing for your company and his days on land by your side happier than he’d ever been before. He started to see you in everyone and everything: the hue of your eyes became his favourite colour, he saw your smile in the faces of his shipmates, he heard your laughter in the aimless chatter of crowds in the market, he looked at the treasures and trinkets he stumbled across and found himself thinking of you before anyone else. ‘He’d like this one’, ‘he mentioned wanting something like this a while ago’, ‘oh he loves these, I’ll bring them back home for him’ — you occupied his every waking thought and he even started to see you in his dreams.
And for so long he tried to rationalise this attachment to himself as him simply caring for his best friend — forced himself to swallow down the bitter taste of disappointment every time he remembered that the two of you were just that. He put himself through arranged meeting after arranged meeting, going from eligible family to eligible family and finding plenty of suitable women that he got along with well enough, and continuing to reject the idea of marrying them because they weren’t you. Because he stopped being able to picture a future without you in it, stopped being able to stomach the idea of marrying anyone else but his dearest friend.
But eventually, thankfully, there came a time where it finally dawned on him that he was truly in love with you — after a particularly lovely dream wherein the two of you were wed — and the realisation hit him hard. Left him flushed and confused and spiralling for the rest of the morning until he was finally able to pull himself together enough to make the decision to tell you how he felt… and to formally ask to court you if you were as receptive as he hoped you would be.
So, a few more hours of fretting over his appearance and second guessing his decision about a thousand times over, Lord Oyster steeled his resolve and left his family home in search of your estate — praying to just about every deity he knows (and the witches too for good measure) that his training as a sailor gave him enough confidence to make it through this meeting without making an utter fool of himself.
~•~
Less than an hour later he found himself completely bare in the middle of your bed with two of your lube covered fingers slowly massaging and easing his asshole open. Your movements were slow and steady, about as gentle as the kisses you were peppering across the flushed sensitive skin of his chest, and you were whispering all sorts of lovely praise and reassurances that had him biting down on his lower lip to stop himself from whimpering.
‘It’s okay,’
‘Take all the time you need,’
‘I’ve got you, sweetheart,’
‘I’m right here,’
‘I’m not going anywhere,’
‘Let me take care of you, my love,’
With each word his body relaxed further and you were able to push your fingers deeper and deeper inside of him. Going carefully millimetre by millimetre until you were knuckle-deep and the cold lube you were using was starting to leak out and smear onto the tight ring of muscle with every small movement of your hand. Watching for any minor change in his expression as you started to slowly, experimentally, crook and scissor your fingers inside of him — skilfully searching for something that Lord Oyster couldn’t even begin to consider until your fingertips brushed against something inside of him and a loud, trembling moan burst forth from his bitten lips. It was something between a breathless gasp and a blasphemous cry, something he’s never heard from himself before, and you have an expression on your face as if you’re the cat that caught the canary — like you’d found exactly what you were looking for — and Lord Oyster’s dick ached in anticipation for what that might have meant for him.
He felt your lips moving against his collarbone but, mind too foggy to process what you were actually saying, he asked you to repeat yourself in such a shaky voice that you couldn’t help but press a wet kiss against the swell of his Adam’s Apple before pulling back to look him in the eye again as you repeated yourself more clearly.
‘I asked if you wanted to cum from my fingers,’ you crooked your digits into his prostate again for emphasis and delighted in the way his cheeks reddened in response, ‘or from my cock? Tonight’s about you so I’ll do whatever makes you feel the most comfortable. Don’t say what you think I want to hear, we can always keep the other stuff for next time,’
A quiet flustered sound came from the back of his throat and he looked anywhere but into your imploring eyes as he considered his answer — with the thought of either option being enough to have his cock dripping and his skin burning. But after several seconds of contemplative quiet your lover finally spoke up, his decision obviously made with a good degree of certainty despite the embarrassed tremble and cracking of his voice as he verbalised it to you.
‘Y-your cock,’ he swallowed thickly and you leaned down to peck his lips to reward him for trusting you so much.
‘You sure?’ He hummed and nodded and turned his head to the side which gave you a perfect view of the darkening blush coating his cheeks and neck. ‘Okay, sweetheart. Just let me know if it gets to be too much, yeah?’
He nodded again and whispered a quiet, if pitchy, ‘thank you’ that broke into a whispered moan when you pulled your fingers out and spread his legs further apart to accommodate you. And it was the most beautiful sound you’ve ever heard.
~•~
Once you finally bottomed out inside of Lord Oyster you were unable to stop yourself from moaning, so overwhelmed by the warmth and tightness and intimacy that you had to force yourself to cling to your lucidity and stay still for him. And your boyfriend wasn’t fairing much better either, doing well to adjust to the unfamiliar sensation of being so full but still obviously needing some more time and reassurance to grow comfortable enough for you to actually start moving — so that’s exactly what you gave him.
‘You’re doing so well,’
‘Shh, it’s okay,’
‘I’ve got you, babe,’
‘Breathe, sweetheart,’
‘Relax, I’ll take care of everything,’
Shifting from patient encouragement to semi-lewd compliments once you finally got his permission to start moving. Your voice was straining and pitching and cracking over the words as they left your mouth, the sentences broken up by gasps and grunts and moans, but despite that they remained just as effective as before — their effect much more plainly obvious to you as you saw his dick throb and drool and twitch in response to your praise.
‘So handsome,’
‘Fuck you feel so good,’
‘Like you were made for me,’
‘I love you so fucking much,’
‘Say my name, scream it,’
‘So — fuck me — so fucking tight,’
‘Y’look so good right now… wish I had a mirror in here so you could see it too,’
‘So so good,’
‘Louder,’
‘You’re — ah — taking me so well,’
‘Such a pretty cock too… fuck, you really are perfect…’
‘So hard — hah — you like it when I praise you? Cute,’
‘Don’t hide from me,’
‘Let me hear how good I’m making you feel right now,’
‘That’s it, good boy,’
Every brush of your swollen tip against his prostrate pushed him closer and closer to climax, and you found yourself getting so lost in him and how responsive he was to you that you slowly stopped being gentle with him: after an experimentally deep and sharp thrust coaxed the sluttiest moan from his lips, you were quick to adjust your pace to be faster and deeper and rougher — driven by an instinctual, almost primal, need to hear your name falling from his lips as you fuck all other thoughts out of his head; after the lightest grazing of your teeth against one of his nipples had him arching his back up into you, you adjusted your position on top of him so that you could reach his chest without straining your neck as much; after lazily tracing your fingertip along the prominent vein on the underside of his length had his dick twitching and his pale skin flushing a darker shade than before, you couldn’t stop yourself from encircling your fist around the base and jerking him off — delighting in how hot and heavy and wet he was in your hand and how vocal he became once you were finally giving his neglected cock some attention. You were enthralled with the way his pretty eyes glazed over and rolled back when you milked his prostate, enamoured with the way he began to chant and gasp and moan your name like a prayer or a hymn, endeared by the tears and drool wetting his blushing face and dripping down onto the pillow underneath his head, enchanted by how much more reactive and sensitive he becomes when he’s been fucked dumb, and thoroughly determined to leave him so completely and utterly cock-drunk by the end of the night that he’ll have forgotten the sound of his own name.
And based on how much of a mess he’d already become underneath you, how much his dick was twitching and leaking in your hand, you were already incredibly close to your goal. So close that you could feel his building orgasm as much as you could feel it on him — in the tightening of his ass around your cock, in the cracking and wetness of his voice, in the trembling of his legs where he locked them around your waist — so close that all he needed was one last push, one perfect touch, to send him tumbling over the blissful edge of climax.
So you experimented for a short while, your own pace faltering as you tried to find that spot on his body that would have him screaming your name until all the world knew he was yours. You brushed your lips along the column of his throat. You nipped at the skin just behind his earlobe. You grazed your teeth over his sensitive chest. You groped at his sides and thighs. You rubbed the pad of your thumb over his drooling slit. You bullied your cock into his prostate until he was sobbing. But he didn’t get that final push until you finally turned your attention to his balls, gently playing with those taut twin pearls for the briefest of moments until his whole body tensed and he was cumming — covering your hand, and his stomach and thighs, with his seed as he groaned and grunted and cried out your name over and over again. His voice getting pitchier and more hoarse as you roughly fucked him through his orgasm, desperately fighting off your own climax until he was so far gone that he was only able to incoherently babble and sob and gasp through his pleasure, so wholly fucked out and messy and beautiful underneath you that you couldn’t even hope fight back against your own release any longer. Barely able to hold out long enough to utter one final bit of praise before you came with a groan and collapsed, gasping, on top of him.
‘Y’did so good f’me. Love you s’much,’