boyfriend’s best friend simon
(18+ smut, fem!reader, infidelity but your boyfriends a cunt if that makes you feel better)
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you don’t know how this happened. you don’t know when this happened. all you know is that it is happening, and you really don’t want it to stop.
simon’s everything that your boyfriend isn’t. has everything that he lacks. communication, understanding, selflessness; commonsense, emotional intelligence, a big cock,
the list goes on, frankly.
but here you are, your bedroom sweltering around you, swimming beneath distorted waves in your vision. convection currents radiating from your conjoined bodies.
simon’s hands were large and calloused on the soft fat of your hips, fingers toying with the taut lines of stretch marks passing onto the thick of your upper thighs. his hands gripped and pulled and moved you against him, slamming you up and down, grinding you against him.
he was leaned up against the headboard of your bed, head cocked back with dark, hungry eyes glued to your body and a coy smirk plastered across his face. the way he looked at you, gazed you, admired you as if you were some kind of prize, had your stomach in knots.
maybe you were a prize. after all, he was balls-deep in his best friend’s girl, and he didn’t have a care in the world. didn’t have a care in the world that his cock had chubbed instantly when she opened the door to let him in an hour ago.
you panted above him, thighs burning, shins pressed into the warm sheets of your bed. you were hesitant to be on top, to perch your body weight across his pelvis. your boyfriend never assured you it’d be okay, just agreed with you and fucked you flat on the mattress. simon was different.
“what? think i can’t handle myself a girl like you, eh?” simon had uttered, looking you up and down. a prize. he was also knuckle-deep in your pussy by this stage, two fingers scissoring you open. “oh, sweet girl, you have no idea.”
and now you were here. straddling simon riley, the formidable ghost that you’d seen only occasionally with your boyfriend. a recluse of a man, a mountain of a man. was always kind, always respectful.
an army dog, a government mutt. always so obedient, and so polite. well-trained and well-mannered. clearly, until he had a pretty bird like you stretched across his lap. a prize.
“yeah, ride this fuckin’ cock, baby,” simon grunted, helping you fuck yourself down onto his cock. his thick, fat cock— a cock that hit you so deep, stretched you so wide, that the joke of ‘is that a gun in your pocket, or are you just happy to see me?’ had died on your tongue because, holy fuck,
he could use it. he knew what he was doing. you should have guessed it with the way he spat on your cunt ten minutes into you letting him into your flat; the way he licked the glob of spit from your wet folds and fucked it into you, tongue warm and searching. you also should have guessed when he rubbed at your clit with his thumb while stretching you open on his fingers; the way he moved them at just the right pace to make you come twice in a row. now:
“s’all yours, baby. s’all yours,” he uttered, pushing his hips upwards to meet your downwards movements.
your tits bounced with each of his thrusts, the mattress creaking beneath you. the sheets were bunching, the heat in the room thick and molten. liquid, drowning you.
you gasped, air in your lungs. you were not drowning, just fucking delirious with the way his cockhead knocked up towards the plug of your cervix.
panting, you clutched at his shoulders. broad and muscular. you could feel the difference in texture where skin ended and scar began. a few times, your fingers wandered upwards, and you drew the tips through his hair. once cropped, now grown out. scruffy, rugged,
handsome. sweat beaded on his forehead, turning the lighter strands dark, sticking to his skin. between the filth he spewed from his mouth, you could hear him grunting and moaning. you wished he’d moan louder. maybe once he stopped talking it’d be different. but you weren’t sure how soon that would be.
“fuckin’— look at the fuckin’ state of you. such a pretty girl. such a pretty— fuckin’— girl,” simon groaned, thrusting up into you. the force made you hiccup around a long moan. simon smiled, triumphant. “look like a dream takin’ all o’ my cock, sweetheart. perfect little pussy letting me stretch her open, huh?”
“simon,” you moaned, and that wasn’t the first time you’d said his name tonight. but he acted as though it was.
a dog with a bone, simon flashed a wicked grin, canines showing, and redoubled his efforts in pushing his cock in and out of you, rutting against your body.
“yeah, baby, i’m here. your simon’s righttttt here,” he said, grinning, as he took one of his large hands and placed it over the mound of your belly, pressing gently and squeezing you there. he couldn’t actually feel his cock inside you, but the added sensation knocked an airy moan from your chest, your eyes rolling. simon hummed, pleased as he fucked you. “‘m reaching so far, aren’t i? so deep. bet your lad couldn’t reach up here, could he?”
you whimpered, and you wanted to whimper a ‘noooo’ but it died in transit. instead, you whimpered, like a wounded dog, as his cock hit that perfect spot inside you. it made you want to scream.
you continued to bounce against him, his thighs pressed close to yours. he fondled you, squeezed your hips while you both worked each other towards release.
“simon,” you pleaded, breathless. “oh, fuck—”
simon wanted so badly to beam with pride. but he resisted, cocking his head and watching the way your greedy cunt sucked his cock in with wet squelches at each upward thrust.
“you feeling good, sweet girl?” he asked, tone warm and honey-sweet. well-trained. then, “this cock making you feel good? he followed with an obvious lilt. mutt.
you replied with a yes, that trailed off into a high-pitched moan when simon’s thumb found your swollen clit, rubbing against it and beginning to draw small, tight circles.
“thaaat’s it, baby. sing for me.”
“siiimon,” you mewled, body tiring but stomach growing tight. bubbling hot, molten like the atmosphere of your bedroom. the knot in the base pulling tighter and tighter with each nudge of his cock against your g-spot.
your cunt was soaked around him, dripping out onto his pelvis and onto your bedsheets. making a mess.
tight, velveteen walls clutched at his cock as your climax built. gripping tight, holding him against you, keeping him with you. wet and warm and the closest to heaven a non-religious man like simon’ll ever come close to.
“beautiful,” he suddenly whispered, eyes on your face now. “beautiful girl.”
well-trained. damn, your boyfriend wasn’t even close to being this well-trained. he was more used to chewing you up like a toy, and heading off to do god knows what once he’d finished. once he’d satisfied himself.
you weren’t a toy for simon. just a prize. much different than a toy, for your information.
a toy is something you play with. a prize is something treasure. savour. and with the way simon revelled at the silky feel of your pussy against his bare cock, he intended to savour you forever.
“you wanna come?” he asked softly, but you knew the soft tone wasn’t going to last. not with the way his eyes glinted, his soft abs flexed, and his mouth curved at the corners. “can feel this pussy startin’ to make a fuss. so desperate for it, isn’t she?”
personifying your pussy. a new one, but one you weren’t entirely afraid of.
so you answered. “yes. simon, please—“
simon quickened his pace, thrusting deeper. your flesh rippled, thighs and stomach and tits moving with the sheer force of his movements. he grunted and panted, eyes drooping, fingers tight in your hips, chasing his own high too. he still had a hard-working finger drawing sharp shapes across your puffy clit.
“go on then. come all over my cock, sweet girl. show me what i’ve been missing out on.”
the tension in your body grew and grew, sweat accumulating across your skin. shiny, dewy, completely ethereal, you hurtled towards release with wind in your sails. sweating, hot, on the brink of overstimulation, you let your mind go fuzzy. you had a heartbeat in your clit. you could feel the stickiness of your inner-thighs. you could hear simon,
“come for me, baby.”
the coil snapped as if on cue. maybe you were the well-trained dog in need of a new collar.
your release rocked you off balance, and you slumped forward, ready for simon to catch you. he did, of course, leaning you against his chest as your body shook, twitched, jerked with the force of your orgasm. it travelled through you like electric shocks. an electrical current that fizzled out after a few long seconds, and left you boneless against simon’s chest.
he was close behind you, his balls drawing tight, tip leaking inside you, flared head now ruddy and red.
he moaned. “god, baby. feel so good around me.” a speechless moment, filled only with pants and— moans. simon moaned loudly, eyes snapping shut as his orgasm quivered inside him. bees trapped in a glass jar.
“just needed a proper cock to split you open,” he said suddenly, voice deep and rich. “pretty girl like you needs a big cock to keep her happy.”
rutting, in and out. desperate mutt. canines flashing, grip tightening, moans increasing. military stamina you hoped wouldn’t last all night. a working dog, too, this man. god, what a man. not perfect (you wouldn’t want him to be), but pretty fuckin’ close right about now.
“simon,” you whined, desperate.
he groaned deeply. “oh yeah, fuck, that’s it, baby. say my name— yeah, say my name when i come inside you.”
“simon…”
“that’s it, baby. that’s it. fuck, m’so close. m’so close, baby, keep going.”
“simon, please—!”
“mhm, thaaat’s it, fuck,” simon moaned, then shoved his cock as far in as it’d go (making you gasp and choke on a loud moan) and then came inside you.
you felt the heat. more heat, more liquid fire. molten. lava. you were drowning again.
he filled you, cum painting your insides as he moaned out your name, whining as his head flopped backwards, his large hands keeping you firmly in place.
then, everything stilled. your heartbeat clanged loudly in your ears, heavy in your rib cage. your puffy clit beat in tandem with it, and your hole fluttered around his cock, now still and plugging his release inside you.
for the briefest moment, as you lay against simon’s chest in the warm, sex-laden air of your bedroom, you thought of your boyfriend. the man you should’ve been doing all of this with.
but the thought was merely a linger. it flitted away, brushed aside by simon’s lips, that came to rest against your tacky forehead. he peppered a few kisses there, rubbing your hips, arse and back soothingly as you fizzled down.
“pretty girl…” simon whispered softly, hugging you to him. “my pretty girl.”
his prize.
he always thought his mate was a bit of a prick, anyway.
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"I've been waiting for ages for somebody to unmask them."
This moment tends to elicit negative reactions in a first read through, and I've got some opinions about why where Kabru is coming from here actually makes a lot of logical sense. So I thought I'd elaborate on that.
I think people hear this and go, "He thinks they must be hiding something because they gave money to someone? What a cynic." Or "he dislikes them because they did charity?? What's wrong with this guy!". And obviously, a lot, a lot is wrong with him. But I think this makes more sense than it seems at first glance! What people evaluating this judgement miss is why Kabru is paying attention to Laios and co to begin with.
Kabru knows of the Touden siblings because (he's a little bit of a stalker-) he is keeping an eye on all the relevant parties in events developing on the island, in order to be able to guide them to his preferred outcome. This includes adventurers because they are the ones actually exploring the dungeon! He's well aware that something as minor as internal tensions between party members could be key to the historical events that are developing. (He would love the assassination of Archduke Franz Ferdinand.)
His desired outcome is that whatever the rewards are of breaking the dungeon's curse, whether that's kingship or the ancient elven secrets of dungeons, are claimed by:
A) a short lived person
B) Someone who will be a good, effective leader and/or use those secrets and the power they carry wisely, with foresight, and to establish a political bloc for short lived people.
The person he can best trust to do this is, of course, himself. But due to his PTSD regarding dungeons and monsters, he's not able to develop the necessary skills to conquer the dungeon. Once he realises this, he starts looking for someone else who he can support to that end.
But most of the adventurers don't have any intentions of conquering the dungeon, don't have the skills, or are unsuitable in other ways. In fact, it seems like some potentially suitable people are the Toudens. There are a lot of good rumours about them going around - they actually seem to have a very positive reputation! That's what Kabru means when he says "unmask".
So when Kabru is observing something like them giving money to an old comrade from their gold-peeling days, he doesn't consider it a problem because "they're giving money to this person who doesn't actually need it" or because they must have some dark secret if they act superficially nice. I think he actually understands this situation and what it implies about Laios (in particular) perfectly well.
Laios and Falin gave money to an old comrade who got injured and couldn't work. That person then healed up but kept taking their money. Then he used the money to start smuggling illicit goods to the island.
The key is that for Kabru, the problem here is the same as with the corpse retrievers - people using the dungeon's resources to fuel dangerous, selfish, or violent pursuits cause problems for the island, attract more criminals and people with motives other than breaking the curse, and increase the chances of the whole situation ending in tragedy.
Kabru is willing to work with the Shadow Lord of the island if it gets him to his goal - he isn't scrupulous - but the criminal element of the island increasing is something he sees as a major issue.
Also, when you're evaluating someone as a candidate for power, riches, secrets, potentially kingship - then being curious about how the money you give to people is going to be used is kind of a relevant trait!
Interpersonally, Kabru's actually very easygoing - I mean, Mickbell isn't exactly an upstanding guy, is he! But Kabru likes him and they get along well. These traits wouldn't be a problem at all in a friend, or a comrade, or someone Kabru was confident he could use. But he can't get a handle on Laios, and Laios is someone who has the potential to be a major player!
On Laios' end, this is the same as with the marriage seeker who joined their party. She kept asking for things and he gave them to her, because he tries to be nice to others. He even gives her money! It's the exact same thing.
That's fine, but it became a problem because he basically wasn't interested in her motives, didn't notice she was trying to manipulate him, and it also didn't occur to him that the other party members would notice or be affected. We can assume the situation with the gold peeler is the same. When Kabru says that "It's not that they're bad people, they just aren't interested in humans," he isn't wrong.
The extent to which this is true of Laios is linked to his autism imo, (because it isn't just disinterest - he genuinely isn't able to notice nonverbal cues that people are lying to him or have ulterior motives) but to a greater or lesser extent I think it's a very common trait. Most people aren't actually that interested in other people who aren't close to them. Kabru is the weird one here. It isn't an issue except as a leader - which is why we see an immediate comparison to the Island's Lord, because that's how Kabru is evaluating them.
And disinterest in/lack of ability with people to the extent Laios exhibits it, it does, actually, make him a worse leader... it's just that as we see in the story, people can help him out. The rest of the party tell him the marriage seeker is taking advantage of him so he tells her he can't give her special treatment anymore. They're pissed and it's a crisis point - he couldn't have recovered their trust without Marcille and Falin - but that's exactly the point. With Marcille and Falin, he was able to recover their trust.
And he has other good traits that make up for it, such as his intelligence, strategic knowledge, open-mindedness and sense of fairplay.
Kabru doesn't disqualify Laios as a candidate based on what he sees about him from afar, though - he still tries very hard to get close to him, obviously hoping that if he manages he can steer Laios to defeat the dungeon and make up for his lack of people-skills in the aftermath. (Which... he does eventually achieve that goal!) He completely fails until the events of the story, so... definitely I think "They just aren't interested in humans" could also partially be a stung reaction to Laios' complete disinterest in him.
Anyway, that's my read on what exactly Kabru's "issue" with Laios is. Obviously, once he does find out what Laios' true nature is like - about his love for monsters - he develops an entirely new set of fears about Laios' priorities. But since Laios kept that a secret until the start of the story, he has no idea of that yet.
Given all that, I think it's interesting that he says that he doesn't think that the Toudens are suitable to defeat the dungeon, and that he's hoping they'll turn out to be the thieves. As some of his few potential candidates, people who he thinks may play a big role in the island's future, you'd think he'd hope they would be good people!
I suppose it's better, in his eyes, because it means that he's involved in something "interesting". They haven't just had their stuff stolen by regular criminals (boring, puts them further away from his goal) - they've been caught up in the beginning stages of "a historic event". The desperate and dwindling group forgetting morals in their quest to retrieve their lost comrade probably appeals to his sense of melodrama. Because he also just... loves drama.
Despite it being "uglier than anything he was expecting", he still pursues Laios as the person he wants to conquer the dungeon pretty much as soon as it becomes clear that he won't be able to do it himself and they are out of time. That's because... well, to be fair, there aren't any other options. And he fits standard A: he's short-lived!
and Kabru still hopes he can fit standard B, too, and be persuaded to use the power he wins for good. No matter how many nightmares he has about Laios, or whether he thinks about killing him. He doubts him, but ultimately he puts his faith in him and seems happy after the manga's ending that he made the right decision.
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