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hippiegoth97 · 4 months

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You're a Winner: A Gator Tillman x Reader One-Shot 18+ Minors DNI

A/N: Hey, everybody! Just wanted to pop in and say 'surprise'! I've been watching the Fargo series lately and Gator Tillman has captured my attention. I also want to shout out two people who indirectly influenced me into writing this. First, is @morning-rituals for planting the seeds of the particular dynamic I've written here. And second, is my fic bestie @xxbutdaddyilovehimxx, for encouraging me to branch outside of Stranger Things with my writing. I'm also from Minnesota and spent a lot of years in Fargo as well. So, I figured it would be fun to make a story that goes back to my roots, in a way. (I will say my one gripe with the show is the accents are WAY over-exaggerated, but it is what it is.) Anyway, enjoy this totally unannounced story! -hippie ❤️

Description: You're a sex worker who's been employed by Roy Tillman to service his son, Gator. You've been seeing the young man for many years now, and it seems this long-term arrangement has brought on deeper feelings for one another...

Warnings: swearing, smut, sex work, smoking, one use of f-slur and r-slur, oral sex, praise/degradation, mommy kink, spitting, slapping, distension, choking, overstimulation, age gap, protected sex, mentions of erectile dysfunction, mentions of abuse/violence, light angst, a little bit of fluff

You're a Winner

He's late, you think as you look at the clock in your trailer. It's nine-thirty on a Saturday night, and Gator Tillman is tardy for his weekly appointment. You cross your arms as you sit on your sofa, staring at the door to will the man's presence on your weather-beaten steps. You've got yourself all dolled-up and everything, wearing your best red and black lingerie set and matching sheer robe. You've got the bedroom all set up for the little brat. Fresh sheets, lit candles, condoms at the ready. The only thing that's missing is your client.

This little arrangement of yours has been going on for almost a decade. From the moment Gator turned eighteen, his father Roy insisted on enlisting you to 'make him into a man'. In his own words, the sheriff said 'I'm worried he's gonna turn into a fag. The kid has never brought a girl home. Not even under the pretense of studyin'.' Shit, you'd never seen a grown man so concerned with his own son's sex life before. But given your chosen profession, and what a handsome young man Gator was, you agreed. For a hefty fee, of course. A kid like that was bound to come with a laundry list of hang-ups and deep-seated issues.

Nine years later, and Gator has essentially become your only client. You don't really need much more than what Roy gives you, and you're not the spring chicken you used to be. Forty ain't ancient, but it ain't all that youthful, either. But you're content in your work. You have your independence in self-employment, your cozy trailer, your cat, and any hobbies and small pleasures that suit your fancy. What else could you possibly want?

You suppose the only thing you want in this moment, is for the shitbird to darken your doorstep. This arrangement isn't something you begrudge, and it's not just because of the money. You enjoy your time with Gator, he's always very eager to see you. You've grown rather close over the years. You let him sit with you and talk about his day before you initiate anything. He seems to appreciate the companionship, you don't imagine he gets much love and attention at home. It's quite sad, honestly. But he never complains, not really. He just says how he feels about stuff, and you offer up some advice to lighten his mood.

A more crude reason as to why you like Gator so much, though, is because he's hung like a fuckin' horse. And once he built up a little stamina, hot damn, that boy can go round after round. You get just as much pleasure from these little meetings as he does, never left unsatisfied at the end of the night. An even more filthy revelation that comes from your trysts, is something rather scandalous. Something Roy Tillman would surely never approve of in a million years. Something that could probably tarnish the family name if it ever got out, hence a very strict 'verbal NDA' that consisted of a gun pointed to your head. The sheriff's not-so-precious little boy...has a mommy kink.

This kink was discovered by complete accident. You'd been seeing Gator for a couple of months already, having very fulfilling —if not rather vanilla— sex. You let the young man use you as he liked, after showing him the basic moves. He was so adorably inexperienced when he was first brought to you, his big brown eyes begging you for help as the only touch he knew was from his own hand. But after you showed him the ropes, he took them and ran. Gator is honestly the best you've ever had, and it's only gotten better with time.

But everything changed on one fateful night. Gator was particularly sad, and he wanted to spend most of his session just laying in bed and having you hold him. His head was resting against your breasts, and you were stroking his hair and letting him cry it out. You cooed kind words to him, and waited to see if he'd be up for anything else. You didn't mind foregoing the mind-blowing sex, though. He was looking to you for comfort. You'd eventually said something to him that dried the tears up, and he lifted his head to look deep into your eyes. And he said 'thank you, mama' in the sweetest voice you'd ever heard.

He'd never called you that before, and it took both of you by surprise. His eyes went wide, cheeks burning bright red. He tried to apologize, or clarify himself, anything to keep you from thinking he was some kind of freak. But hearing him say it...it stirred something inside you that you didn't even know was there. You liked it, and you wanted him to say it again. After a dissecting discussion about where his 'slip' came from, it was decided. Your entire dynamic would change drastically, as would your lives.

"Sorry I'm late, mama. Had a few extra heads to bust today." Gator says casually, strolling right through your door and tracking in snow on his work boots. He sees you sitting with your arms crossed, giving him a very stern look. His eyes drift along your body for a moment, drawn in by the sexy lace covering the most beautiful parts of you.

"I oughtta bust yours for makin' me wait." You snip, nudging your head as a signal for him to kneel before you for forgiveness.

"I know." He sighs, getting on his camo-clad knees and crawling over to you. You spread your legs, letting him apologize in the way you've agreed upon for many years now. "I'm real sorry, mama." Gator drawls, gingerly lifting your ankle in his hand. He leans his head down to kiss your stockinged foot. His warm lips slowly work their way upwards along your shin, to your knee, stopping at your thigh. "Lemme make it up to you." He says softly, eyes meeting yours again.

"Take your gear off first. You're trackin' snow everywhere." You gently command.

"Yes, mama." Gator does as you ask, sitting on the floor and untying his boots. He sets them neatly to the side, and takes off his holster, coat, and vest. He returns to his spot between your legs once he's stripped away the part of him that exists outside of your home. He allows his mind to slip into the place you've built just for him. Where there's no senseless violence, no one to tell him how stupid or useless he is, no self-loathing or insecurity. When he's here, he gets to feel good. You make him feel good. You administer his earned punishments with love, and with that love comes the strength he needs to carry on in the big bad world outside. You make him feel like a winner.

"Good boy, Gator. Doesn't that feel better?" You ask, noticing his demeanor has changed. It always does once you get things going. That douchey 'I am the law' attitude melts away like snow in spring, and he blossoms into a sweet, submissive little flower before you. Ripe for the picking.

"Yes. Much better." He smiles and nods, raising his hands to rest on your thighs. "Can I touch you now? Please, mama?" He pleads, growing rather desperate to taste you on his tongue. He's been thinking about you all day. Your sweet, succulent pussy is like nothing on this earth. Not even the most cavity-inducing flavors of his vape juice can compare.

"You may." You reply simply, shrugging your shoulders. Gator caresses your flesh, his hands still cold from the Lehigh winter air. But he quickly warms up as he continues to stroke you. He goes for the hem of your panties, looping his fingers around the fabric. You lift your hips up to help him as he slides them down. He takes his time, dragging the lace down to your feet before removing them altogether. You scoot yourself closer to the edge of the couch, spreading your legs open wide.

"Fuck, been thinkin' about this all day." Gator groans at the sight of your slick folds glistening in the dim lighting. Even though he's seen your cunt over four hundred times, it still drives him wild to see it every Saturday night. He craves it, dreams about it. All other women have been ruined for him at this point. It's not like you're actually dating or something, you're just his paid whore. But any attempts he's made to take a gal out on the town and make a move, they all fall flat. Those girls may be younger, and prettier than you, with bigger, perkier tits than yours. Nevertheless, he can't even pretend to enjoy their company. Because they're not you.

"Yeah? Did you miss mama's pussy, baby?" You ask, biting your lip at the spellbound look on his face. Even after all these years, he's still so taken by you. It makes you wonder, if this means far more to him than what your job description calls for.

"So, so much..." He nods and whimpers with need, licking his lips as he leans in closer between your legs. Your very center calls to him, the ambrosial scent emanating from it making his mouth water. Gator gently lifts your legs to sling them over his shoulders. The increasing body heat inside his sweatshirt radiates through to your flesh.

You patiently wait for him to take his first lick, admiring the way his breath stutters, and his pupils dilating with lust. His eyes drift closed as he goes in for the kill, planting his soft lips to your clit. "Mmm." You give an encouraging hum, letting your body fully relax against the sofa. You're gonna enjoy this. His tongue drags up and down along your slit lazily, gathering your wetness and spreading it all around. He's barely started, but it already feels amazing.

Gator takes his time, letting out little moans with every drop of your arousal landing on his tongue. "Tastes so good, mama." He pants.

"Only the best for my sweet boy." You coo to him, stroking your hand along his slicked hair. He melts between your thighs even further, licking and sucking on all your favorite places. "You're doing such a good job, Gator. You've got a fuckin' perfect mouth." You praise, unable to resist rolling your hips to meet his movements. You cradle the back of his head to keep him in place, the stubble from his semi-buzzed cut tickling your flesh.

Pleasure builds within your belly, a roaring fire growing higher and hotter by the second. Gator's mouth continues to work on you, your satisfied moans encouraging him to keep it up. Your pelvis grinds into his face over and over, his hands supporting the small of your back to assist you. He loves it when you fuck his face, making it so you're the only thing he can see, smell, or taste. His cock is straining inside his pants, aching to get out and have some attention of its own. He wants so badly to take it out and stroke it in his own hand, or even dry-hump the couch to get some kind of friction. But he knows better. He only gets to feel good when you say so.

"Gettin' close, honey. Don't stop." You moan as you near the edge. Gator's pace quickens just a little, and he adds more pressure with his tongue. "Fuck, just like that." You gasp, nails digging into the back of his head.

"Mmm." He grunts at the sting, his cock twitching and leaking a few drops of precum into his boxers. He can't wait to taste your release on his tongue, his mind swirling with the memory of how gorgeous your face looks when you cum. Anticipation grows in you both, making the air in the room grow thinner. Gator's mouth goes into overdrive, pulling out every move you've ever shown him to try to make you lose it. Helpless moans flee your lips at his ravenous tactics, your free hand gripping the edge of the couch for dear life. "Please, mama. Please cum on my face." Gator begs, his words somewhat muffled between your thighs. But his whiney tone comes through all the same, and it's more than enough to bring your orgasm crashing down on you.

"Fuck!" You cry out, thighs trembling as pleasure courses through you mercilessly. Your legs clamp closed, trapping Gator's head against your pussy. He doesn't seem to mind, far too focused on drinking up every last drop of you. Your pelvis rolls unsteadily into him while you ride this out, your lungs on fire from breathing so hard.

"Mmm." Gator hums into your folds, swiping his tongue along your slit to clean up the beautiful mess you've made. All you can do is sit half-slumped against the couch until he stops, completely consumed in a thick cloud of euphoria. He pulls away after what feels like a welcome eternity, meeting your glazed-over eyes. A satisfied smile plays on his shiny lips, and his hands carefully lower your boneless legs from his shoulders. "Am I forgiven, mama?" He asks, sitting patiently on his knees for your approval.

"Yes, baby. I forgive you." You return his smile, lifting your legs up on the couch to lie down for a moment. You're gonna need some time to recover after that. "Uff-da! You really rocked my world this time, Gator." You say as you stretch your body out a little, a few joints clicking beneath your skin causing you to groan. Shit,I'm gettin' too old for this. You reach behind your head for your pack of cigarettes on the end table, bringing it to your chest to open it and take out a smoke along with your lighter.

"You're not too tired to fuck me, right?" Gator asks, pulling out his vape from his pants pocket. He's about to bring it to his lips, when you smack his hand.

"Don't do that in here. I hate that fruity fuckin' cotton candy bullshit." You chide him, and he slips the device back into his pocket.

"Sorry. Can I have a smoke, then?" He asks sheepishly, cheeks burning in shame.

"You betcha. Here." You hold the pack open for him to take a cig, lighting it for him before doing so with your own. "And to answer your first question, no, I'm not too tired. I just need a minute. And then we'll have some more fun. Okay, baby?" You end nicely, realizing you've come off a bit grumpy with him. Of course, you're meant to be stern and 'in charge' within this dynamic. But you don't want to be mean if it's not intended to derive pleasure. Gator doesn't need another bully.

"Okay." His smile returns, and he gets up to sit on the edge of the couch to be closer to you. He takes a long drag of his cig, his nose scrunching momentarily at the bitter taste. He used to smoke all the time, multiple packs a day to wear away at the stress that comes with being the sheriff's son. But once vaping became a thing, he jumped at the chance to taste something other than harsh tobacco. He figured he'd smell a little better, too. It's safe to say Roy wasn't too pleased, saying it 'made him look like more of a pussy than he already is'. So, the habit is maintained out of spite as well as inescapable nicotine addiction.

"Whatcha thinkin' about?" You ask, noticing he's looking rather stressed. Something seems to have pulled him out of the comforting sub-space he usually resides in with you.

"Nothin'. Just been a long day." He forces a smile, brushing the negative thoughts away. He doesn't want to entertain them right now. Or burden you with them.

"If you say so. But you know you can always talk to me, honey. I may be a whore, but that doesn't mean I don't care about you." You say kindly, placing a hand on his thigh as you continue to smoke. He nods to affirm your statement, taking another drag. "Did you want a drink or somethin'?" You offer.

"Nah, I'm alright. Maybe later." He replies, leaning over to stub out his smoke in the ashtray. "Can I kiss you?" He asks politely.

"Someone's impatient today." You chuckle, exhaling a cloud of smoke and putting your own butt out next to his. "C'mere." You beckon him closer with your finger, giving him permission to shower you with affection. You love the way Gator kisses you, so eager and attentive. His lips are so damn soft, despite spending hours outdoors in the chapped air every day. And his wandering hands know where and when to touch you at all the right moments. His palms tenderly worship your flesh wherever they may land, never failing to make you melt in his touch.

Gator climbs over you, his knees on either side of your own. He takes a moment to admire your face, the flush of your cheeks, your skin glistening with a light sheen of sweat. "You're so fuckin' beautiful." He says softly, lowering his lips to press against yours. It doesn't take long for his tongue to find its way into your mouth, tangling hungrily with your own. Your hands reach up to cup his face, keeping him close so he won't pull away. He tastes like green apples and tobacco, a flavor combination you never thought you'd enjoy so much. His own hands run along your sides, setting your skin on fire. He travels upwards, settling on your clothed tits. He gently massages them, swallowing the moans he draws from you.

"Gator..." You breathe against his lips, wrapping your legs around his waist to pull him down closer. His sizeable bulge meets your bare cunt, and he grinds into you out of impulse.

"Shit— Sorry, mama." He quickly apologizes, realizing he didn't get permission to do that.

"S'okay. Just don't do it again." You pant out a reply as you feverishly devour his mouth with your own. He nods, closing his eyes to settle into the rhythm again. You keep kissing until your lips start to go numb, pulling apart with shuddering breaths. "Let's take this to bed, baby." You coo to him.

Without another word, Gator lifts you off the couch and into his arms. He supports your ass in his hands, and your arms wrap around his broad shoulders to hang on tight. He carries you down the narrow hallway to your bedroom. You're surprised to find none of the candles have managed to set the trailer on fire, having forgotten you'd left them burning unattended for so long. Gator carefully lays you down on the bed, standing upright to start taking off his clothes. He knows the drill. Once you're in here, everything comes off. You remove your robe and bra, tossing them off to the side. You also do away with your stockings and the garter belt holding them up, leaving your body on full display for him.

You watch on intently as Gator's sweater is shucked from his torso, revealing his thick chest hair and toned muscles. He definitely works out a lot, you're sure he has to in order to 'bust heads' every day. He doesn't look like a body builder or anything like that, but his physique is still quite impressive. So firm and tight, bulging in all the right places. Next goes the pants, some truly ugly camouflage things with way too many pockets. But what lies underneath is 100% Certified All-American Beef. His thighs are thick enough to crush a watermelon, not that you've tested that assumption. A massive tent has formed in his black boxers, a damp mess of precum seeping into the fabric. He slips the thin material down from his hips, allowing his enormous cock to slap against his stomach.

"Fuckin'-A." You mutter under your breath. You'll never get over how huge he is, no matter how many times you see his dick. Eleven heavenly inches that reach every single nook and cranny of your cunt. He's got a nice curve and some decent girth to him, too. You know you're gonna be feeling it tomorrow, and the next day, maybe even the day after that. That's what you're counting on. "Stand next to the bed, baby." You order.

"Yes, mama." Gator assumes the position, and you get off the bed to go to him. You set a cushion on the floor, kneeling on it before taking his cock in your hand. "Fuck." Gator gasps at you finally touching him.

"Oh, you naughty boy. Look what a mess you're making already." You tut, drawing his eyes to look at his tip. It's engorged and red, a sticky blob of pre-release in the slit. "I'd better clean you up." You smirk, bringing your tongue to his head to lick the fluid away.

"S-sorry...didn't mean to— fuck." He's cut off from his apology when you take as much of him as you can fit inside your mouth. He's a little more than halfway in before he reaches your throat, and you use your hand to stroke the rest. Gator groans at your hot, wet mouth encapsulating him. He wants so badly to push you down further, or buck his hips into you. But he won't. He can't. If he does, you'll throw him out in the snow. Besides, he knows how well you take care of him. He'll get everything he wants, as long as he behaves. And you certainly make that easy to do. "Feels so good, mama." Gator moans, his fists balling at his sides to resist any disobedient urges.

You draw off of his cock for a moment. "Yeah? You gonna be a good boy and stay still for me?" You ask, flicking your dominating eyes up at him.

"Yes. Yes, I'll be so good for you. Please don't stop." He whines, the sound sending a flare between your legs. There's something about having such a masculine man begging you to touch him that makes you feel powerful. It's intoxicating.

"I hope so. I'd hate to have to punish you, honey." You reply, taking him back in your mouth. You bob your head up and down along his length, your hand gently pulling and twisting the excess. Your tongue swirls around him as you suck, stealing the most pathetic little groans and swears from his lungs. You keep going just like this for a good while, the slurping sounds of your mouth on him filling the room along with his moans.

Gator's eyes are glued to the sight of his cock disappearing inside your head. You're a master at blowjobs, although he doesn't have much to compare it to. As it's been said before, he's tried with other women. But he just can't quite...get there. Sometimes he can't even get fully hard, which is kind of embarrassing for him. The girls never make him feel bad about it, assuming it's their fault. And it isn't exactly untrue. They just can't satisfy him the way you can. It does worry him sometimes, that he may never be able to move on from you.

"You're in your head again, Gator." You pull away, giving him a questioning look. "What's wrong?" You ask, still pumping him in your hand.

"I'm sorry." He sighs, rolling his eyes at himself. He's ruining this. The one thing he looks forward to all fucking week. "Can we talk about it after?" He asks. You're about to protest, but he insists you keep going. "I promise, I'll focus. Please?" He pleads, eyes watering in frustration. Don't fuckin' cry, idiot, he mentally scolds himself. He sniffs harshly, thinking about anything else.

"You sure?" You ask again, needing to know he's completely on board for you to continue. You search his eyes for the truth, to figure out what's bothering him so much. It's unfortunate you don't have the ability to read minds.

"I'm sure. I want you, I need you." Gator replies enthusiastically, forgetting all about his troubles again. All it takes is you actually giving a shit to pull him back into the warm blanket of safety you've crafted for him.

"Okay. Just let me know if you change your mind." You resume giving him head, speeding up a little to lead him even further away from his unpleasant thoughts.

"God— fuck." He grunts, already getting close. He was pretty far along until you stopped, and your increased pace has helped catch him up significantly. You bring your free hand to his balls, firmly massaging them to push him further. His nails dig into his own thighs as he gets closer and closer. "'M almost there, mama. Can I cum?" He asks with need. His stomach is threatening to tense up any second now. Gator's eyes watch and wait for you to give him some signal of permission, heart pounding in his chest as he holds himself right on the edge. "Please, please, please..." He mutters repeatedly, wanting so badly to let go. After what feels like forever, you nod to give him the go-ahead. "Oh, god...gonna cum— fuck, fuck, fuck!" He murmurs in a pitched tone, toes curling as his high courses through him. His brows furrow, and his mouth falls open to let out a load groan. His hips stutter slightly, and you feel his sticky load spilling inside your mouth. You swallow most of it, saving a little bit in your cheek once he calms down. You pull yourself away, and gently lead him to sit on the bed.

"Look at me, baby." You say softly, though he's still in a daze. You grab hold of his chin, lifting his face to make him pay attention. He gasps quietly in surprise, eyes widening. He's still coming down from his orgasm, his mind feeling fuzzy. "Open." You order. Gator does as you ask, his pretty lips parting in obedience. While still holding his chin, you straddle his lap. Your hand moves to cup his cheek, and you gaze deep into his fucked-out eyes as you spit the cum you'd saved into his mouth. He moans at the taste of his own release on his tongue, swallowing it hastily. "Good boy." You praise in a seductive tone, reaching between your bodies to grasp his softening cock.

"Shit." Gator hisses, feeling a little overstimulated. You start stroking him, trying to get him hard again. "Mama, please...too much." He whines, needing you to let him breathe.

"Shhh. You're a big boy, you can take it." You coo, squeezing his dick a little to make his eyes roll back into his head. He groans, beginning to grow in your hand as the pain turns into intense pleasure. "See? Doesn't that feel good?" You ask darkly.

"Y-yeah." Gator nods, pulling you in for a starving kiss. He needs to touch you, to do something to occupy his hands or he might just go insane. He grabs your ass, leading you to grind your clit against the base of his cock. You whimper at the friction, ignoring his slight breaking of your rules. It just feels so good, you don't want him to stop. His lips travel all sorts of places as you keep riling each other up for round two. He kisses your neck, your tits, your shoulders, nipping and sucking your skin. He leaves reckless hickeys in his wake. Everything he's doing is making you wetter by the second. You need him now, you can't wait any more.

"You wanna be inside me now, baby?" You ask, rubbing circles on his throbbing tip with your thumb. He's at a loss for words, only able to nod as his mouth continues to attack your skin. "You have to let me get a condom, Gator." You giggle at his lack of control.

"Sorry." He immediately stops everything he's been doing, his hands falling to his sides.

"It's okay. But I'm not always gonna be so forgiving." You warn as you climb off of his lap. You go for the bedside table, taking one of the condoms from the bowl sitting on top of it.

"I know." Gator responds quietly. You come back over to him a moment later, already holding the opened condom in your hand. You gently place the ballooned end on his tip, rolling the latex down his ample length. "Fuck." He mutters, still very sensitive.

"Is this position okay?" You ask, hoping he says 'yes'.

"Yeah." He answers. You straddle his lap again, one hand on his shoulder while the other takes hold of his cock. You drag him slowly along your folds, slick sounds emitting from between your legs.

"You hear that, honey? Listento how wet you've made me." You say through a moan.

"Mama...please, fuck me. I want your pussy so bad." Gator begs, almost on the verge of tears. His thighs keep twitching, and he can't stop making the most pathetic noises as you tease him.

"You promise to be a good boy? To follow the rules?" You ask, needing to hear him say it.

"I promise, just— please!" He pleads, his voice breaking as he can't take much more of this torture.

"Alright. Just calm down, baby. Breathe." You speak gently, holding him still against your entrance. His eyes meet yours again, and he does as you tell him. He slows down his breathing, forcing himself to relax. His chest rises and falls slowly, his heart ceasing to race. "There ya go." You give him a small kiss as a reward before moving things along. You carefully lead yourself downwards onto his dick, the air knocked out of your lungs as you do so.

"Jesus..." Gator's head falls back at the sensation of your tight pussy taking him all in. You keep going until he's fully sheathed inside you, his tip pressing firmly against your cervix. Your walls clench around him, low moans escaping you both.

"Mmm, that's my big boy." You chuckle in satisfaction. You feel so wonderfully full inside, you swear his cock is in your stomach. You take hold of Gator's hand, bringing it to your lower belly. You press his palm into your flesh, wanting him to feel the bulge his cock has formed inside you. "You feel that, baby?" You ask, drawing his eyes to yours. He'd been squeezing them shut before at the sensation of your cunt swallowing him up.

"Yeah." He barely exhales the word, his dick twitching at this discovery. He gently feels around the subtle protrusion on your stomach, curiosity getting the best of him.

"You like that? Knowing you fill me up so well?" You keep up the questions, smirking at the look of wonder on Gator's handsome face. He nods in reply, pressing two fingers on the bulge to see if anything happens. A quiet moan comes out of you in response, as the area he pushed has managed to stimulate your g-spot from the outside. In all your years of whoring, you've never felt anything like it. "Do that again." You order, and he does. The sensation returns, making your thighs clench. "Holy shit, Gator. I don't know why, but that feels so fuckin' good." You chuckle breathlessly, unable to believe you're just now finding this out.

"Should I keep doing it?" Gator asks, very excited that he's managed to surprise you after all the time you've spent together.

"You can near the end, baby." His face falls when you tell him to wait, his hand taking its usual place on your hip. You grab hold of his chin again, much rougher this time. "Don't be a brat." You warn, bringing your lips closer to his. "I know you're excited, honey. But you have to wait. You can do that for me, can't you?" Your tone toes the line between sweet and teasing, with a dash of danger to tell him you mean business.

"Yes, mama. I can wait." Gator answers agreeably, though he hopes you'll actually start riding him soon.

"Good boy." You coo, giving him a tender kiss. You let go of his face, placing your hands on his shoulders for leverage. You slowly lift yourself up, carefully sinking back down again. You repeat this action a few times, easing yourself into a steady pace on Gator's cock. It's best to ease into it given his ample size, you'd hate to end up hurting yourself.

"Need more...Y/N, please..." Gator whines, his hands gripping your hips so tight.

*SMACK*

You give him a hard slap across the face for using your real name. "Don't call me that." You cease your lazy bounces, wrapping your hand around the thickness of his throat. You give him a rough squeeze, cutting off his oxygen. Your eyes burn into his, and a subtle redness is spreading on his left cheek. "What's my name, baby?" You ask, expecting him to address you properly.

"Mama." He chokes the word out, growing even more aroused at you doling out his punishment. The sting on his face and the clog around his throat are going straight to his cock.

"That's right." You nod, returning your hand to his shoulder. "Now, no more funny business. You sit still, and do as I tell you. Got it?"

"Yes, mama." Gator answers, dying to feel you bouncing on him again. He's so hard it hurts, you didn't give him any time to collect himself earlier. And now, every twist or clench you make could set him off like a motherfucking pipe bomb.

You don't say anything else, going back to warming yourself up. You take hold of Gator's hands, bringing them up to massage your breasts as you move. It'll give him something to do, surely he's grown extremely impatient at this point. He gladly accepts the task, rolling your nipples between his fingers as he squeezes your tits with his over-sized palms. "Good boy, that's it, play with mama's titties." You praise, picking up speed a little. Breathy moans fill the air as you move, his dick squishing into your sweetspot every time you land on him. You've still got a long ways to go, and you have no problems taking the scenic route, so to speak.

The same can't be said for Gator, however. He's a complete mess beneath you already. His thighs are quaking, his hips threatening to pitch up off the bed. Thoughtless noises and swears fall out of his plump lips, his brows drawn together in a downward scrunch. It's taking everything in him and more to focus on juggling your boobs in his hands. Your cunt glides up and down his shaft with pointed precision, letting him feel every ridge and divot inside you through the condom.

"You're doin' so well for me, honey. Takin' this pussy so good. How's it feel, baby?" You ask, going even faster in his lap. Your thighs and joints are telling you to do otherwise, they're starting to burn and stiffen from the work they've done already.

"Feels s-so good— fuck. I love your pussy, mama, 's so hot and tight." Gator groans, trying so hard to keep from thrusting his pelvis. He wants so badly to flip you over and fuck you senseless, to slam his aching cock into you over and over until you're crying. Sometimes you let him do that if he's really good, and he's praying to the Lord Almighty that this will be one of those times.

"You wanna help me out, baby? I'm runnin' outta steam here." You huff, feeling the need to switch positions now. You thought you could soldier on keep this up, but apparently not.

"Yes, please." He replies excitedly, grabbing hold of your hips again. You still yourself, moving your legs from their straddling position to instead spread forward onto the mattress. You sigh in relief at the new angle taking the pressure off your knees.

"Go ahead, honey. Knock yourself out." You give Gator a warm smile, waiting for him to take the lead. He starts off nice and gentle, not wanting to give you too much too quickly. "Mmm, just like that. Pace yourself, baby." You speak softly, encouraging him. His hips lightly smack into you as he moves, his firm grip holding you safely in place. He speeds up a bit, stealing your breath away as his tip pierces deep within your cunt. "Fuck." You gasp, your orgasm building steadily.

"Can I go faster, mama? I wanna make you feel good." Gator asks sweetly, gazing at you with adoring eyes.

"Yes, please do." You reply, hoping he holds nothing back. In your efforts to tease him, you've been driving yourself crazy. You're unbelievably turned on, desperate to get the pleasure you crave. Gator snaps his hips upwards, setting a far more punishing pace now. "Fuck, baby..." You whimper, tightening your grip on his shoulders. Your head falls forward to nuzzle into his neck as you hang on. Your body jiggles at the force of his thrusts, loud moans and slaps of sweat-soaked skin filling the room.

"Mama..." Gator forces the word out, barely able to think as he pounds your perfect pussy. You lift your head up to see what he needs, his lust-blown eyes finding your own. "Hit me." He murmurs, wanting to feel the stinging slap of your hand across his flesh.

*SMACK*

Your palm cracks against his cheek, ripping a vulgar sound from his lungs. You find it a bit odd that he enjoys being slapped so much. You've heard all about the beatings he's recieved at the hand of his father. But you suppose this is his way of reclaiming the pain, by turning it into pleasure instead. You've never questioned it verbally, you'd hate for him to feel judged by you. You're his safe-haven, his salvation. You're here to give him what he wants, what he needs. Because no one else will.

"Again." He huffs, needing more. He continues to fuck you mercilessly, bringing you both nearer to the edge.

*SMACK*

"Fuck." He groans at the stinging warmth spreading along his skin. "More." He says, his eyes beginning to water.

*SMACK*

As much as it confounds you, it would be dishonest to say you don't gain anything from inflicting pain on the young man beneath you. As the self-proclaimed 'best hooker in Lehigh', you take pride in what you do. The way Gator's skin flushes to an angry red after every blow, and the noises he makes in response excites you beyond compare.

"Had enough, honey? I'd hate to leave a bruise." You ask, though the words come out a bit messy as he's kept up his jackhammering this whole time.

"Choke me. I'm gettin' close." Gator begs, taking your caution to heart. He'd hate to have to explain another 'bar brawl' to his father if he lets you go ham again.

"So am I, baby. You're fuckin' me so good with this massive cock of yours." You give him what he desires, wrapping your hand around his neck. You squeeze the sides of his throat, making his head feel light. His mouth falls open, struggling for breath. His fingers dig deep onto your hips, and he manages to fuck into you even harder and faster than before. "Oh god, Gator, you're gonna make me cum..." You moan as your high rapidly approaches. Your insides are beginning to flutter, your toes preparing to curl any moment now. You loosen your grip on his throat to let him breathe again. You grab hold of his right hand, quickly bringing it to the bulge his dick makes within your belly with every stroke. "P-press down, honey. Make me cum, make mama feel good." You frantically order him, helping him find the spot.

"Cum on my cock, mama. I wanna feel you." Gator groans, about to tip over the edge himself. His eyes fall to the area you've shown him, watching as the lump appears and disappears rapidly. He pushes down on the pudgy flesh, making you squeal.

"Yes! Just like that, don't stop!" You cry, so unbelievably close. The sensation grows and wanes with every pump of his dick inside your cunt, building and building as he continues to press your stomach with his fingers. You can feel the knot inside you about to snap, squeezing Gator's throat one last time to make him lose control alongside you.

"Mama, f-uck..." He chokes as he reaches his peak, his entire body trembling with pleasure. His hips buck wildly against you, his eyes rolling back into his skull. He doesn't stop pushing the bulge in your belly, and his aimless thrusting sends you head-on into your own orgasm.

"Gonna cum, I— oh, fuck!" You almost scream as blinding white heat consumes you. Your walls clamp down around his cock, and you cum harder than you ever have before. A hot, wet mess spills between your thighs, running down Gator's legs towards the carpet. You collapse into his arms, unable to keep yourself upright. Ungodly noises roll out of your mouth, landing haphazardly in the humid air of the room.

Gator's arms wrap around your middle as you both come down from your highs, your hearts pounding in sync after yet another mind-blowing Saturday night. Once you catch your breath, you carefully remove yourself from his softening length and he ties off the condom before throwing it away. He leaves the room for a minute, coming back with a damp cloth to clean you up with and a tall glass of water. He retrieves these things for you every time as part of the terms you'd established in this 'relationship' of yours.

Once he wipes you clean, he helps you get under the covers. He puts his boxers back on, and joins you. You sip at your water, setting the glass on the night table when you're satisfied for the time being. "So, spill. What's on your mind, baby?" You ask, breaking the long, comfortable silence you'd been sharing.

"I...I dunno. It feels a bit retarded now." Gator sighs, shrugging.

"I'm sure it isn't. C'mon, talk to me. You promised." You speak softly, running your fingers along his bare bicep to coax him into talking.

He turns his head to look at you, finding nothing but kind eyes and an even kinder smile waiting for him. "Alright. Just...don't laugh. Or take it too seriously, or whatever." He rambles. You give him a silent nod, waiting to hear him spill his guts. "I was just thinkin' about our time together. I really like ya, and what we have. I know it's just sex, and it's your job. But it means a lot to me, and...I've been findin' it hard to...perform with other women." He says, watching your expression with every word. He's waiting for you to laugh at him, or tell him he's crazy, or...he isn't really sure at this point.

"Uh..." You trail off, unsure what to say. You certainly weren'texpecting to hear anything like this today. You'd assumed Gator was just going to tell you about what a dick his father is again. That's what he usually talks about. He's never even brought up 'other women' before, probably thinking it would be rude.

"Well?" He asks, needing some kind of response from you. Every second that passes with you just blankly staring at him makes him want to run and hide.

"Sorry. I'm just surprised, I guess." You start. "So, what are you sayin', exactly? You 'like' me? In what way?" You ask, needing some clarification here. Because from the sounds of it, he wants far more from you than just raunchy sex once a week.

"I mean...shit. I dunno. I think maybe I...love you?" He says it like it's a question. Perhaps it is. After all, Gator knows next to nothing about love. He's been raised on hatred and violence. How the hell could he know love, even if it bit him on the ass?

"Oh, Gator. Honey..." You tut, about to try to tell him he can't possibly love you. You're his prostitute, for fuck's sake.

"I know it sounds crazy, okay?!" He cuts you off, almost shouting. You flinch at his volume, and he sighs again. He softens his voice, he doesn't want to scare you, or make you think he'd hurt you. He would never do that. "Look, I just— I've tried goin' out with other girls, tried to form a real relationship, and it never feels right. Not like it does with you. I don't expect you to think of me that way, I get it. I'm just a job. That's fine." He says, knowing full well you couldn't possibly feel the same way. He's just a dumb brat that his father pays you to fuck. How can you possibly form any sense of affection for him in this kind of arrangement?

"But you make me happier than I ever thought I could be. You're the one thing I got goin' for me. I look forward to seein' ya every week. You're the most beautiful, kind, amazing person I've ever met. You make me feel good, you make me feel loved. You make me feel like a winner." He speaks emphatically, meaning every goddamn word. He feels like a madman even saying these things out loud. But they're the truth, and he could stand a good helping of that for once in his life.

"I care about you too, Gator. I enjoy our time together, and you're such a sweet young man. I know ya like to act all tough and shit, but you're capable of so much more than that. I'm just not sure 'love' is the right word here." You talk to him as gently as you can. You don't want to hurt his feelings. You yourself harbor strong feelings towards him, it didn't take long for them to develop. But you've always shoved it down, pretended this is all about sex. Hearing him say how he feels for you, though, it's dredged it all back up again. No one has ever made you feel as appreciated and beautiful as he has. The way he's always so happy to be around you, it makes you happy too.

"Then what is?" He asks in annoyance. "We've known each other for a long time, Y/N. You could've given up on me a long time ago, everybody else has. I know Roy's money must've added up by now, enough so you won't have to worry about anythin' ever again. Years ago." He doesn't even care that he's used your real name again. You have to hear this, every last word. Because when he really puts his mind to it, the money and the sex can't be the only reasons you keep seeing him.

"I-I suppose you're right. I've definitely never serviced anyone for years on end." You chuckle, drawing a small laugh from him as well. "And I agree that there is...something here. But, it's not like you can bring me home for dinner or somethin'."

"Oh, I would never do that." Gator scoffs, making you raise an eyebrow. "I couldn't put ya through a Tillman family meal like that. Fuck no!" He laughs again, and so do you.

"Alright, alright. Fair enough. And look, I ain't lookin' to be wedded off or nothin'. But I wouldn't say no to retiring, and lettin' you take me on a real date." You say excitedly, biting your lip. It's so funny, you feel like a schoolgirl again. You have a real chance to actually spend time with Gator in a personal capacity. Something that you never realized you wanted so much, until now.

"That's fine by me, mama. I'll take you anywhere ya want." Gator grins, completely over the moon that you want this as much as he does. Where this exploration will take you both, neither of you knows. But you're willing to try.

The end.

A/N: I hope you all enjoyed this story! It's definitely a one-off but I'm glad I challenged myself to try something new! -hippie ❤️

#writers on tumblr #fanfiction #smut #gator tillman #fargo season 5 #midwestern smut #uff da #all cops are bastards #even the hot ones #dommy mommy #mommy kink

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