you're joking, right? (he's not)
minors, dni! - 18+ only
pairing: roman roy x assistant! reader
summary: you spend a weekend away on a business trip with your boss, roman roy, who asks you for an unusual request -- and you pray these are one of those jokes he doesn't actually follow through with. a/n: i swear this started with an innocent "roman gets pussydrunk" prompt i came up with but it spiraled into something completely different - enjoy! cw: smut (fingering, oral, face sitting - reader recieving), dubcon, explicit language (thanks roman), f! reader, roman is your boss wc: 1.7k | masterlist | ao3 ────୨ৎ──── “Did you not hear me the first time?”
Roman sits with a smug smile, arms folded up behind his head and feet on his desk. You shift nervously on your feet, taking sudden interest in the patterned carpet on the floor. “Roman, it’s late and I’m not in the mood for jokes. Please, just tell me what it is you actually want so I can go to bed.” Working for Roman Roy has its perks, but you often find yourself victim to his ridiculous antics. But this? This has to be the worst one by far.
He huffs out a chuckle before sitting up, putting his elbows on the table. “Are you slow? You really want me to repeat myself again? Just, fuckin’-, look here.” He rises and walks over to you, standing closer than you’d like. “I said, I am going to lie down—” He pauses, gesturing dramatically towards the bed next to him. “And I want you to pull down those little panties of yours—” He taps your hip where your underwear sits. You recoil from his touch. “—so you can sit on my face.”
You can’t convince yourself that he is joking by this point. You glance up at him. His eyes are dark with mischief, neck slightly tense. He leans back from you, throwing his arms out. “C’mon, don’t be a fuckin’ prude. And I’m not joking. Just pull off your little shorts and sit on my face, that’s all,” he all but whines, as if he were a petulant, spoiled child. You sigh at that, folding your arms. “Roman. Stop playing with me. Now, unless you have something you actually need, I’m going to go.” You turn to leave, but Roman grabs your wrist with a quickness, tightening his grip. He spins you around to face him, putting you much closer to him than you were before. “No, no, no. You’re not fuckin’ going anywhere. Whatever you think you’re gonna do, you’re not, so cut it out.” At that, he pulls you in for a hurried kiss. You’re unsure you can really call it a kiss, though, he all but bites your mouth, tugging your bottom lip with his incisors and causing them to bleed a bit.
You pull away quickly, face flushing with embarrassment. “Roman! What are you— Why?” Suddenly, you’ve never felt more alone in your life. You left your phone in your room, keycard on the desk. You have nowhere to run. At this realization, tears begin to prickle at your eyes. “I don’t want to, please don’t make me…” You trail off, words breaking off into a small sob. Concerningly, Roman seems unmoved by your unnatural display of overt emotion. He hushes you, bringing up his other hand to wipe away a tear that had rolled down your cheek. “Oh, don’t cry like that. Just take off your shorts.”
You really begin to cry now, genuine fear striking through you. You shake your head rapidly as one last plea to let you go. “No, no, please, Roman?” Losing his patience, Roman grabs you by the waist and pushes you on the bed underneath him. His hands roam all over your body, teeth coming up to graze your earlobe. “Don’t you make me ask again,” he grunts into your ear, hands having found the edge of your waistband. With quick movements, he yanks down your pajama shorts and panties, having exposed your slit, unwillingly slick with your arousal. “Shit, you’re actually wet? You’re a sick slut, y’know that? Getting off on me having my way with you…” You let out a sob of fear and pleasure as he drags a gentle finger through your folds.
You slide up to move away from him, but a firm hand on your stomach keeps you in your place. “Please don’t, Roman…” you try again, weakly, falling victim to the attention his thumb is giving your clit. You let out a quiet moan. “No, shut the fuck up and take it. Besides, why are you asking me to stop when you’re clearly enjoying it?” He drags his hand up your shirt for your tits, beginning to fiddle with one of your hardening nipples. You reluctantly arch into his touch, biting your kiss bitten lip to hold in a groan. At that, he teases your entrance with the tips of his middle and ring fingers, tracing the outside and barely dipping in. You throw your head back with pleasure. “Please, Roman?” you whine out quietly, a voice almost foreign to you. Roman stifles a laugh, so as to not humiliate you further. How kind. “Holy fuck, no way you’re actually begging me, now. Don’t be scared, just let me in.”
He shoves his digits in your cunt, causing you to cry out. His fingers reach that soft, spongy spot of your walls, causing you to flutter around his fingers and keen loudly for him. “Fuck,” you groan to yourself, eyes rolling back into your head. Roman angles his head to look at you, movements slowing down slightly. “You don’t need to beg me, sweetheart. I’m going to give you exactly what you need,” he says smugly. At that, he pistons in and out of your pussy. “You take my fingers like a fucking slut, I can feel the way your cunt mouths at my fingers,” he mumbles to himself, locked in to the way you’re being stuffed full of him. You babble mindlessly, getting closer and closer to release. He twists his fingers in a particular way and he makes you cum, loudly and pathetically. Your hips buck with reckless abandon, and your bones feel like they’ll dissolve under the extreme pressure at your core. When you’ve come down from your high you lie still against the bed, tired and breathless.
Roman pulls his fingers out of you, eyeing the way your arousal coats his fingers. He brings them up to his mouth for a taste. “Wow,” he states breathlessly, having fingered you rather aggressively. “You’re a shitty liar if you said you didn’t want that.” You remain quiet, still shocked by his initial aggressive demeanor towards you. You lean up on your elbows to look at him, dazed. “Okay, Roman, you’ve had your fun. Can I go to bed now?” He kisses his teeth, shaking his head. “No, I don’t think so. Besides, I haven’t actually had my fun until you sit on my face.” You offer a shy smile at that, hoping it will deter him from continuing to be pushy. “I don’t want to suffocate you. I mean, what if you can’t breathe?”
He sinks down on the bed so his face hovers above your pussy. His hands slide up, holding you open for him. He gazes at your glistening cunt, arousal stewing deep inside of him. “Then I’ll have to worry about that when, or If, that becomes a problem.” Suddenly, he hooks his arms around your thighs and rolls over so you’re on top of him. Even though you’re more or less the same size, you thought he wouldn't have had that much strength. He moans underneath you, sending shocks of vibrations through your clit and up your spine. You shudder with arousal, causing your thighs to shake.
“God, your pussy is so perfect f’me. Just like I imagined.” He eats you out wildly, tongue gliding through your folds and circling around your bundle of nerves at the top. You bring your hands up to hide your face out of embarrassment as you rock your hips gently against his mouth. “Hey-hey, keep your hands down, I want to see you cum.” His eyes fix darkly on you, “Be a good little assistant for your boss and take your hands down.” He sucks obscenely at your clit, causing your back to arch deeply and make you hold onto the headboard for support.
His hands slide up your hips, digging his fingertips into your flesh. “Roman, Oh God, Roman, please make me cum! Please?” you beg, still grinding on his tongue. He groans again, sending another flash of ecstasy through you. He pushes you up to get room to speak, “Fuck, be a good girl and cum for me.” Sitting you back down, his tongue flicks out again over your clit, aggressively shoving you over the edge. You shatter above him, waves of bliss coursing through your body. Your hips rock uncontrollably, unknowingly causing your arousal to spread across Roman’s face. He drinks up your orgasm, lapping at your hole as you ride out your orgasm. When you finish, you flop over unceremoniously next to him, legs going limp. Roman sits up on his elbows as he tries to catch his breath.
You roll over to look at him and you see how your orgasm soaks his face and absolutely ruined his dress shirt. Your face blushes deeply as you scramble for an apology. “Roman, I’m so sorry about the shirt, I really didn’t mean to—”
He waves in your direction, silencing you. “Eh, it’s fine. I’ll just take the dry cleaning costs out of your next paycheck,” he says with a hint of bland humor in his voice. You pout at that, knowing that the few things he actually jokes about is your compensation. He throws a cunning look in your direction, filled with promise which makes you feel uneasy. “I guess that means you’ll have to make it up to me next time.”
--
The following week, you’re back at your desk at the New York office, typing away and organizing documents. Hearing a knock at your door, you stand up and round your desk to investigate. Upon opening the door, your vision is taken up by a huge bouquet of roses, about two or three dozen you think. The delivery man, struggling to hold the heavy vase, sets it down with a huff in front of you. After confirming your identity with him, he walks away trying to catch his breath.
You lean down, noticing a small white card buried in the petals of the flowers. Opening it, reading the tiny letters printed in the card makes you feel light headed. Round two in Stockholm next week? — RR













