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KINKTOBER ‘25, DAY 28: TWO AT ONCE. JEALOUS SEX.
PAIRING: tim drake x female! reader x conner kent
SUMMARY: tim drake and conner kent aren’t your boyfriend boyfriends, they’re situational and that includes the sex too… but when they notice you flirting with another guy at a wayne gala? they aren’t shy about their jealousy… and you experience it first hand when both of them stuff you.
CONTENT WARNING: 18+ CONTENT, double penetration, dirty talk, vaginal sex, anal sex, threesome, rough sex, big dick! conner kent, big dick! tim drake, unprotected sex, first time anal, jealous sex, competitive sex, ass slapping (a little), tummy bulge, they’re so in love with you—
AUTHOR'S NOTE: day twenty eight! like I’m so fucking sorry but this is straight up filth, I knew I wanted to do double penetration, and they’re just both so hot, how could I not? anyway, hope u enjoy!
tim and conner are competitive people. you knew this too well.
they’re also your “not-so-boyfriend” boyfriends, tim calls it situational boyfriends, conner calls it half-time boyfriends. they’re not your boyfriends all the time, other times they were definitely your boyfriends— dick jokes that they’re only your boyfriends when they need to be, which is more true than they could even think… but the problem with having two competitive, not-so-boyfriends boyfriends? they get jealous… and horny.
and jealous and horny don’t mix well.
you weren’t even supposed to be at the wayne gala.
you weren’t a fancy socialite or business person trying to sell people things. you weren’t even really dating tim (who was the one invited by dick and damian), though you’d fallen asleep in his bed more times than you can count on two hands and whenever you needed him, he was there in a moment.
but you went anyway, because tim dragged you along, which inadvertently meant conner was coming too— who wasn’t too happy to be leaving metropolis, but would put up with it because it was you two. conner was given a suit by clark (color coordinated by lois because god forbid clark cannot color coordinate to save his damn life) and tim used bruce’s credit card.
and how you ended up leaving the gala with two jealous doberman in human form, holding each one of your arms as you three got back to metropolis through conner’s flying abilities… that’s how you found yourself in this position; on your back, dress was ripped on the floor, both conner and tim were naked and stroking their cock as each one of their hands held one of your legs open for them.
then seeing you get hit on one of those stupid gentlemen swingers in gotham? they didn’t expect each other to get so jealous.
you weren’t even their girlfriend, why are they getting so mad about him? he’s not as hot as they are, he definitely doesn’t make you feel good like they can (and they’ve done before) and he’s definitely ogling at you for far too much for both of their likings. and that’s how you ended up leaving the party early, leaving that god forsaken gala through the front doors and ignoring people as they questioned why two men, fat grins on their faces hiding their jealousy, were pushing each other with you in their arms out the door.
so that’s how you ended up in this position.
“f-fuck…” you mutter as your legs shake. you don’t even get a second before they get on the bed with you, tim going over to the pillows and pressing against the headboard as he grabs you and puts you on his lap, conner getting behind you as conner straddles tim’s legs.
tim kisses your jaw, his right hand squeezing your breast as his left hand grabs his cock, murmuring a few shushes as conner lines up with your hole. “have you ever had two in one go, baby?” tim questions you, his blue eyes shooting into yours.
you shudder as four hands touch you so well. you shake your head, looking over your shoulder at conner as he kisses the top of your spine. “n-no, tim… ‘never had two dicks in me…”
“good.” conner gruffs against your hair, his tip pressing against your hole as tim’s dick presses against your cunt. “cause tonight, that’s what you’re getting…” he says, grabbing your jaw with his right hand and kissing you.
you moan against his lips, your shaky moans leave your lips as you feel both of their tips against each one of your holes. “j-just be gentle… please?”
tim smiles at your words, kissing your cheek. “of course baby, ain’t no way we’re going to hurt this pussy of ours…”
with no words needed, conner goes first since it hurts more to get a dick up your ass instead of your pussy.
his tip is bulbous against your hole but it stretches you so fucking good. you moan out as you feel your hole gets stretched beyond any point. conner’s hands spread your cheeks, watching in awe as each inch disappears, your muscles clamping around him like a vice.
he grunts, squeezing both cheeks in hand. “c’mon baby… don’t give me a hard time.” he gruffs, bullying open your hole as your moans fill the room. it’s a different pain from vaginal— a sharp yet delicious sensation that you tried to relax for him, but you can’t help it. “there you go…” he coos once your hole lightens up around him. “good fuckin’ hole f’me, making me so proud.”
tim grins at your response, stroking his cock with a methodical pace as he waits for conner to be fully seated in your ass. “you done, man? this pussy’s wet as shit on this side.” he says, putting his left hand right under your clit, feeling just how wet you truly are.
conner groans at the final inch, his balls resting against your cheeks as he adjusts his knees, fixing his posture. “her hole took it well, go ahead, tim.”
nodding, tim adjusts his hips and slowly pushes his cock into your folds. your pussy takes it easier than your hole, considering it’s less tight than your behind, but it feels so good. you feel so fucking full by the both of them, conner’s cock warms up inside you as tim’s cock slowly pushes into you.
“there you go…” conner mutters, moving his right hand to wrap around your waist, his hand sprawling on the top of your abdomen, feeling tim fill you. “this pussy doesn’t want anyone else… no one else can make you feel this good, can they, love?”
you shake your head, gasping with each shove of his cock. “s-shut up, con… fuckkkkkk.” you moan out as tim’s cock eventually hits your cervix, his balls brushing against your puffy cunt as now, both cocks sit heavy into you.
tim grins, kissing your swollen lips as they both let you adjust to two dicks in you, squeezing your right thigh. “oh c’mon sweetheart, don’t be like that.”
“you- you two are so- so fucking jealous…” you grit out, jaw clenched as your walls on both ends slowly ease up. you’re getting used to them, you’ve had both of them inside you but not like this— not at the same time. they’ve shared your pussy but not your pussy and your hole at the same time.
conner shrugs, thumb stroking the bulge in your abdomen as his left hand remains on your ass. “if the shoe fits, baby, you’re the one flirting with that guy… like he had a chance.”
tim nods in response. “conner’s right, sweetheart, you’re the one who flirted with him, looking at him like you wanted to fuck him.” he adds, feeling conner adjust behind you, his cock getting needy to move.
you roll your eyes. “i-i already said i’m sorry, for fucks sake… y-you guys aren’t even my boyfriends so why do you even c-care?” you question, knowing damn well the attitude ain't going to do you any favors, but you like it when they’re rough with you; but the broken words aren’t on purpose, it just feels that good.
“don’t give us attitude, sweetheart.” tim reads it immediately, purposely adjusting his hips just for that, which makes you groan out loud.
conner nods, lifting his hand to slap your ass— it’s not hard whatsoever, just a gentle tap, like a warning tap. “tim’s right, no need for the smart mouth. and for that boyfriends comment? it shouldn’t matter, baby, tim dragged us with him and we remained with each other, not flirting with other men ten feet away from one another.”
the jealousy shouldn’t be so hot, but it just is. the husky voice of tim and the deep voice of conner just feels too good vibrating against your skin.
you can’t respond, but it’s not like they were going to force that out of you… instead, they began to move their hips.
tim began his movements first, conner held you up so easily as tim began to lift his hips, thrusting upwards into your tight cunt. your moan is sharp-- unexpected as you feel pleasure hit your body instantly with tim’s cock. your pussy flutters around him. “tim!”
he grins, both hands remaining on your thighs as conner holds your hips. “now you don’t got that bitchy ass attitude." he remarks, not relenting on his hips as the wet slaps of skin echo throughout the bedroom. “taking my cock like the good girl you are…”
then, conner begins to move, and you are seeing stars at this point.
conner’s cock burns your walls as each thrust in your hole forces the muscle to open up and expand with each thrust, his cock bullying your hole as they held you in place, both cocks moving at different speeds and angles, but they’re both doing what they’ve intended to do, which is make you feel good.
the kryptonian behind you grunts out a few curses as he thrusts in and out, balls slapping against your clit as the robin below you keeps up the quickened pace rather than the behind’s deepening pace. they both feel too damn good that your body doesn’t know how to feel besides beg for release almost instantly.
“you feel that?” conner questions as each thrust hits you like a freight train. “you feel us fucking you, like it’s what you deserve… tell me baby.” he begins, grabbing your jaw and forcing you to look at him over your shoulder. “who’s the guy you were flirting with?”
your eyes look at him, you can barely keep focus with the amount of pleasure both cocks are doing to you and you can barely think about anything from the last five minutes, let alone an hour previous.
tim grins at the response you give conner, which is literally a fucked out response. “i don’t think she knows, man… think that mind is too fucked for her to even think.”
conner’s smile turns wolfish at tim’s words, stroking your jawline. “is he right, baby? is that pretty little head too fucked out to think of anyone else besides us?”
and at that, you respond. you nod, pussy fluttering as you find yourself closer and closer to the edge, so quickly and so pathetically— but you couldn’t care, you hadn’t cared the moment conner lined up behind you and tim in front of you. “y-yes, con… t-too fucked out… t-too good…. ah! oh fuck!” you let out as tim drills into a particularly good spot.
“she’s going to cum.” tim says, bringing his hand up to your puffy clit. “should we let her cum, conner?”
you try to nod, try to beg them to let you finish, but conner’s hand literally locks you there.
he pretends to think for a second before responding. he may be jealous, absolutely, he may be horny and pissed… but he wants to see just how fucked out they can make you… and that includes see how many orgasms you can handle. “i don’t know, tim, you think you can make her cum?”
that makes tim’s eyebrow raise, and his hips don’t falter at conner’s challenge, meanwhile your face was red, your moans hoarse as these two men argued below you.
“uhhh, i definitely can, not so sure if you can, considering you’re slow as shit.” tim responds, legs flexing as each thrust hits deeper and deeper.
and conner? he doesn’t respond, but with the way he moves you a little, bringing his right hand onto the back of your neck and his left hand on your hip and the sudden change of pace in his movements? that’s all tim needs to see to pick up his pace. you scream as conner’s cock goes faster, hitting the deepest parts in you, it feels damn good as his cock drags in and out.
you can’t tell who makes you cum, but you just know it as your eyes roll back, a scream of both of their names and an arch of your back off of conner’s shoulder is all you need to cum.
each cock remains to go faster as your orgasm tears through you, each finger losing sensation, legs clenched hard and needily around tim’s leg, locked in by conner’s legs as you fall over the edge. head thrown back, sweat dripping down your face.
and they didn’t give you a chance to think before they fall over the edge as well.
tim does first, like always for the regular human. for one whimper of your name, his cock hits your g-spot, and in an instant, you feel a gush of warm semen enter your folds. it’s fulfilling and its sticking to the inside of your walls as he grinds against you, semen pumping deep within your folds.
then, conner cums. a deep marking of his hand on the back of your neck and one groan, he’s cumming as well, this time in your hole. being half kryptonian, he’s much more forceful as his cum has a lot more pressure in it. it knocks the wind out of you as it enters your asshole. you can feel it, your nails digging deep into tim’s chest as you squeeze your eyes shut, his thumb stroking your neck as he cums deep.
both holes are filled with both of the superheroes’ semen, both panting as they catch their breaths. your eyes finally roll back to where they’re supposed to be, tim leans up to kiss your swollen lips and conner kisses your neck.
“t-turns out you can take double dicks…” tim remarks against your lips as he’s slow to pull out, but eventually, he does, with conner doing it first. both of them are out of their respective spots.
you nod as conner gently moves your body onto the bed and onto your back, careful to not hurt your backside. “f-fuck… tell me to never make you two jealous again… fuck.” you murmur under your breath. “n-need a damn shower.”
conner smiles, but you know that smile, it ain’t over for you. “who says you’re finished baby… you’ve got a lot more and last time i checked, tim…” he looks down at tim, who’s leaning on his forearms. “whoever goes flaccid first loses…”
tim smiles once again, and you just internally groan as his words fill the room. “oh you’re so going down.” he says as they both go to one of your legs, spreading you open all over again.
maybe making them jealous was the right thing to do…
main masterlist | kinktober masterlist
they’re just so fucking delicious, I want to eat them both— this is probably one of the nastiest ones I’ve done just because it’s double penetration and I’ve never written a three some like this (the only other one is my dick x wally x reader one) so hope u enjoyed! next one coming soon!
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MURDOCK-SLVT 2025!
