Chapter Text
The door to the sheriff’s office slammed open as Sheriff Francis Davidson entered, dragging along a man dressed in blacks and greys and silvers, in contrast to the sheriff’s attire of whites, browns, and the one pop of colour coming from the blues of his jeans. The sheriff shoved the man into the cell, taking the key for it and locking it with a deep sigh, along with soft panting from the chase he was just on.
“You don’t know how long I’ve waited to see you locked up in here,” Francis stated, before raising his gaze to meet the outlaw’s smug, almost relaxed, face, illuminated by the soft moonlight coming from the window and the warm glow of the oil lamp across from the cell.
“Must feel real proud of yourself, Sheriff,” the man said with a cocky raised eyebrow. “Finally got your hands on the Grey Thunder. A real accomplishment.”
Francis rolled his eyes. “I feel relieved more than anythin’. You’ll be shipped off to prison in a week or so and then I’ll never have to hear about your antics or see your face on a wanted poster ever again.” The outlaw’s been terrorising people for at least a year, and only recently started hitting his town. People’s horses disappearing in the middle of the night, never to be seen again. Who knows what the hell he does with them afterwards.
“D’aww, you don’t mean that. I bet seein’ this pretty face of mine was always the highlight of your day,” he winked.
“I’ll let the prison officers know you’re delusional. Maybe you’ll be kept alone for the safety and sanity of everyone else,” Francis once again rolled his eyes, turning to his desk and wiping his brow of sweat before readjusting his hat. He was by no means out of shape, but boy, that outlaw gave him quite the workout. The outlaw leaned on the cell bars, tilting his head at the sheriff.
“Y’seem tired, Sheriff,” the criminal helpfully pointed out. Francis let out a deep sigh, glancing back at him. “Aren’t you observant. Thanks to you, I don’t get to rest in a comfortable bed tonight. Stuck with a rickety old wooden chair, starin’ at a criminal, with my wife alone at home,” he rolled his eyes.
The outlaw lightly raised his eyebrows, still keeping a smug smirk on his face. “Ooh, there’s a Missis Davidson, is there? Here I was thinkin’ I could possibly shoot my shot here,” he teased, his smirk growing.
Francis rolled his eyes once more, a light blush dusting the edges of his cheeks. “Wrong demographic, outlaw.” He’s not surprised this notorious outlaw would subscribe to some… less than common ideals. It was certainly not the most legal thing in their town, but Francis was taught better than to think less of men who prefer the company of others like them. Not his place to judge.
The outlaw tilted his head, resting it on his palm as he continued to lean on the cell bars, the black bandana loosely tied around his neck pushing up from his chest raising. “Funny, a buddy of mine south from here tells me a different story.”
Francis froze, glancing back at him. “...The hell are you talkin’ about?”
“Oh, nothin’. Was probably some other tall, muscled, brown haired, brown-eyed, big-cocked sheriff who agreed to fuck the brains out of a friend of mine a week or two ago while on the trail here. Could just be a coincidence, you think?” He narrowed his eyes at him, smiling wider.
Francis turned back to him, glaring, stomping right up to the cell bars, inches away from the outlaw’s face. “You watch your goddamn words.” Of all the people to hear about his one case of infidelity, it had to be the dick he just threw into a jail cell. Should’ve asked the guy he fucked for a background check. Would that have been too far? Who cares? It would’ve avoided him this drama.
The outlaw cocked an eyebrow, still with his smug smile. “Or what? You’ll throw me in jail?”
“I’ll beat your ass is what I’ll do,” Francis growled. Francis is decently intimidating, especially when angry, but the smug look on the outlaw’s face told him that this man isn’t easily intimidated.
“Oh, you’re gonna pound me, huh?” The outlaw lowly chuckled. “Maybe I’d like that. Ol’ Johnny on the trail said he had a nice time. Said you liked to go rough. I’m a big boy, I’d be able to take it~” He winked.
Francis glared, growling again. “It was a one-time thing. I’d been travellin’ on the road for days, needed some sort of stress relief. An ass couldn’t be too different from what I was used to.”
“Oh yeah? And which hole did you prefer, ‘ey, cowboy?” The outlaw cocked an eyebrow with a smug smirk.
“Doesn’t matter,” Francis huffed. “Anythin’ rubbin’ against a dick would feel good.” In reality, that man’s ass was a hundred times better than anytime he’s had with his wife. The friction, the tightness, and as much as he hates to admit it, the taste…
“Right, right. Clearly also applies to the fabric of your jeans, huh?” He gestured down at the sheriff’s crotch, where a bulge beneath the jeans was slowly growing. He smirked. “Willin’ to try it again, old boy?”
Francis looked down, blood flooding his cheeks, before he huffed, turning away and walking back to his desk, opening a drawer, taking out a bottle of whiskey and a glass. “Like I told you, one time thing. Don’t confuse yourself, I love my wife.”
“She love you, though?”
That one phrase caused Francis to pause. Well, sure his wife likes him. She’s just… prickly sometimes. Not like he can’t handle it. He’s a man. “That’s none of your business,” he said, setting down the glass and uncorking the bottle.
“Not an answer, big guy,” the outlaw smirked at him, still resting his chin on his palm.
Francis turned back and glared. “We wouldn’t’ve gotten married if we didn’t love each other.”
“Arranged marriages exist.”
“I know that, dickhead, but we weren’t arranged to be wed. In fact, she left an arranged marriage to be with me. Tell me that isn’t love.”
“Well of course. Anyone would be stupid not to marry you, man or woman. I mean, look at those muscles, the height, that ass, and that mountain growin’ in your pants is clearly indicative of a huge cock,” he said, gesturing to said huge cock.
Francis blushed, huffing, setting down the bottle and crossing his arms. “She’s not with me just ‘cause I’m apparently so attractive. It’s for love. That little moment on the trail was just… a moment of stupidity. I was thinkin’ with my dick and not thinkin’ about how I’ll have even better sex in a week or two. Even if, admittedly, I’d have to wait through all the beratin’ and slappin’ to get it,” he sighed, rolling his eyes a little.
The outlaw cocked an eyebrow, his smirk twitching. “She hits you and you call it love?”
Francis rolled his eyes, picking up the bottle again and pouring himself a glass. “I’m a man. I can handle it. Not like she bruises me every time. Doesn’t seem like you’d know anythin’ about this, anyway.” He admits he’d rather not deal with… all of the negative parts that come with being married to his wife, but what kind of man would he be if he didn’t deal with it? They’re married. They’re in love. Everyone always said marriage wasn’t easy.
“Sheriff, I’ve already told you you’re my type. Look me in the eyes and tell me gettin’ socked in the eye by a man like you wouldn’t hurt,” he stared at the sheriff, deadpan.
Francis rolled his eyes once more. “Good thing I’m not married to a man like me, then. Can we drop this, now?” He doesn’t need to be berated by some gay criminal for how he should live his straight loving marriage.
The outlaw shook his head with a snort. “Fine, Sheriff. Fine.”
Francis let out a deep sigh as they fell into silence, downing the glass of whiskey. Today has been much more stressful than it needed to be. And now he’s got one more problem to deal with. He glanced down at the bulge in his pants, now at full size, and he put his hand over it, giving a light squeeze. He could just rub one out in the next room, just deal with it, but he doesn’t want to hear all the comments and teasing from Grey Thunder in the cell right there. This doesn’t exactly seem like the kind he can just ignore, either. Damn him, thinking about how much he liked that hookup. Damn that man for having such a good ass. He poured himself another glass.
“Need some help with that, Sheriff?” He outlaw offered, tilting his head with a smug smirk once again.
Francis startled, nearly spilling some of the whiskey, caught off-guard by the question. He glared at him. “You guess the answer.”
The outlaw shrugged. “Just an offer. Go ahead and deal with it if you need to. Could do with a good rub-down myself…~” He said, beginning to unzip his black jeans. Francis simply stared, his cheeks flushing, making no move to stop the man or any attempt to look away.
The outlaw’s currently mostly-flaccid penis flopped out from the opening. Certainly not unimpressive by any means… The outlaw possibly has Francis outmatched in thickness, but Francis certainly wins in the length department. No matter whose penis is “superior”, Francis just couldn’t take his eyes off of it, especially once the outlaw took it in his hand and began giving it excruciatingly slow tugs and drags.
“Go on, Sheriff. Whip it out for me,” the outlaw stated, calmly. Francis’ eyes shot up to meet the outlaw’s, his blush deepening. The outlaw’s expression wasn’t any different, still a smug smile, relaxed eyes, calm posture and body language. This just seems like another Tuesday to him. The casualness and the near-demand turned Francis on even further, and he didn’t know why.
The sheriff slowly unzipped his jeans and pushed his underwear down slightly, letting his fully erect cock free, it bobbing a little as the fabric finally snapped back to his skin as it slipped off of the head of his cock. And it certainly wasn’t a bad cock, either. Fairly thick, nearly nine inches in length. It’s clear why Johnny enjoyed his night with the sheriff so much.
“Not bad, Sheriff. Not bad at all,” he commented, his smirk growing as he bit his tongue in his mouth. Francis rolled his eyes, blushing even more, beginning to slowly stroke his cock.
“Could do without your comments. Mind your own business,” he said. And yet, his own eyes were glued to this outlaw’s cock, as it very slowly grew in size. Francis wasn’t sure why he desperately wanted to see it up close, why he immediately wanted to see it in all its glory. He’s seen other men’s penises before, travelling with other men meant he’d inevitably catch a glance of their manhood while they bathe in a river. And sure, maybe his gaze has lingered at them a little, but the cock on this man, only a few feet in front of him… It was almost enchanting.
“Oh, yeah? Might wanna follow your own advice, Sheriff,” he smirked, glancing down at his own slowly-growing member. Francis’ cheeks burned and he huffed, opting to look at his own cock as he stroked it. The outlaw was right. No man should be staring at another man’s cock like that. Well, not a man like him. A man like this outlaw, maybe. What was he doing, giving this man a free show? He knows his penis is impressive. He should’ve charged admission.
“I could help you with that, y’know,” the outlaw offered, casually. “Just somethin’ quick. No strings attached.”
Francis whipped his head over to stare at him, his cheeks flushing once again. He considered it. It would be so easy. It would no doubt feel good… He also hates to admit that Johnny gave him a much better blowjob than his wife ever did. He guesses men just know what men like. Still, does he want to make that mistake again? One time is already one time too many.
“What– No. No, not happenin’,” he said, firmly. He stooped this low and even further once. He won’t do it again.
The outlaw casually shrugged. “Suit yourself. Thought just about anyone would’ve agreed to a nice hot tongue around their hog but eh, sure, be weird. Have fun with that left hand of yours,” he said, still casually lazily stroking his own cock.
Francis glared a little, just staring at the man across from him. Why did he ever think he’d agree to that? Ridiculous.
…Then again, it would be so easy. Even if it’s bad or sloppy, it would still feel so good. The feel of releasing down a warm throat rather than just out on the floor and in his hand…
Francis let out a deep sigh, grabbing the key and stomping right on over to the cell, his cock bobbing as he walked. “You’re goin’ to help me with this and then goin’ right back in here, alright? Am I clear?”
The outlaw smirked, as the lock clicked, the door to the cell swinging open. “Crystal. Lean back on that desk for me.”
The request was so casual, and yet, Francis felt immediately compelled to comply. Whatever. He’s getting his rocks off. He doesn’t need to think about the implications right now.
He backed up to the desk, practically sitting on the very edge of it, resting his hands at his sides. The outlaw smirked, getting on his knees, tugging the sheriff’s pants down to his ankles, slipping them off with his boots to get him more comfortable. Good thing the socks stayed on, now he’s certainly still straight. “I promise you, Sheriff, you’re not gonna regret this,” he remarked, planting kisses on the inside of the lawman’s thick, hairy thighs. Francis rolled his eyes. “Skip the romance and get to the sucking.”
The outlaw cocked an eyebrow, smirking once more. “Bossy, are we?” He said, and just as Francis was going to respond, the outlaw dragged his tongue along the underside of his cock, causing his breath to hitch, letting out a very soft moan. The outlaw smirked against his cock, continuing to run his tongue along the sides, always just barely missing the head, as he used one hand to slowly stroke the base of the cock, using his other to jerk his own.
“Fuck, Grey–” he breathed out. The outlaw let out a soft breathy chuckle, smirking up at the sheriff. “Hearin’ you moan my name does all sorts of things to me, Sheriff,” he said, continuing to work Francis’ cock. “Sh– Shut up,” he said, gripping the table behind himself. He hated how good this outlaw was making him feel but just couldn’t bring himself to stop him.
The outlaw breathed out another laugh, continuing to tease the sheriff’s cock, licking all across the shaft and the balls beneath it. Francis was panting, letting out very soft noises while the criminal on his knees pleasured him, before nearly whimpering as the outlaw wrapped his lips around the head of his cock, beginning to suckle on it and circle it with his tongue. Francis bit down on his bottom lip to try and muffle any other sounds of pleasure threatening to escape.
Francis glanced around in an attempt to focus on anything else besides the intense pleasure caused by the outlaw’s mouth, before he noticed the glass of whiskey he poured earlier. He grabbed it, downing it with a deep sigh. The outlaw glanced up and cocked an eyebrow, taking his lips off of the cock with a smirk. “Mind sparin’ a glass for lil’ ol’ me, Sheriff?”
Francis lightly glared in return, trying his best to slow his breathing to seem as cool and calm as possible. “Suck me off well enough and you might just deserve it.” The outlaw rolled his eyes, getting back to work.
The outlaw massaged Francis’ balls as he continued to work the head of his cock, and he continued to take slow, shaky breaths from the pleasure. He already felt like he was about to burst, but how embarrassing would that be? Francis already felt himself losing his composure despite his desperate attempts to seem unaffected only moments earlier.
“Come on, stop beatin’ around the b– bush–” His words suddenly transformed into a moan as the outlaw suddenly took the sheriff’s entire length in his mouth, his nose now pressed against his trimmed but still prominent pubic hair. His tongue worked the underside of the cock as he kept it in his mouth, milking some moans from the sheriff, before he pulled off of his cock with a pop from the head, smirking. “Well weren’t those some fun sounds from ol’ Sheriff Francis himself?” He said, continuing to slowly jerk both his and the sheriff’s cocks.
Francis blushed, rolling his eyes, his cock now twitching, a line of precum slowly dripping from the tip. “Shut up and get back to work.” He has to stay in control here. Getting a blowjob from a man he hates is already embarrassing enough, he needs to keep what little dignity he had left.
The outlaw rolled his eyes, still smirking. “Long as you sit back, relax, and leave all the pleasure-makin’ to me. Don’t shut up, though. Those sounds are good encouragement~” He winked. Francis went to respond again, before the outlaw licked up the underside of the cock again, rubbing his tongue on the tip to drink up as much precum as he could, before throating the cock entirely, causing the sheriff to make an embarrassing voice crack that transformed into a moan. His cheeks flushed, about to tell off the outlaw, but couldn’t as the pleasure from him finally truly working his cock overwhelmed him, a moan or a curse escaping his mouth with every tiny movement of the outlaw’s tongue.
Francis brought a hand up to his mouth to bite a knuckle to try and muffle the noises once more, but whimpers continued to escape, and the look of pure pleasure on his face was a true indicator of enjoyment in any case. He used his other hand to place on the outlaw’s head, his fingers weaving through the soft dark hair, streaks of dark grey cutting through the sea of black, shining in the moonlight. A contrast to his neutral brown hair and eyes. Now that he thinks about it, he didn’t quite pay attention to the colour of the outlaw’s eyes, and they’ve been closed this whole time… Maybe that’s for the best. The eye contact feels too personal.
He pushed down as the outlaw engulfed the cock in his mouth again, the sheriff hissing through his teeth from the sensation, relaxing the grip on his head when he ran his tongue and lips across his cock as he pulled back from it, repeating the process over and over, gently and slowly fucking the outlaw’s throat as he received the best blowjob he’s ever had. The incredible amount of suction, the precision and skill of his tongue, the lack of a gag reflex… If Francis weren’t a dedicated Christian, this blowjob would almost make him believe in a new god.
The outlaw’s hands were as busy as his mouth was, gently playing with and massaging and tugging on the sheriff’s balls, rubbing and pressing against his taint which Francis considered dangerously close to his asshole but not making any move to stop him, stroking up and down both their cocks when he wasn’t deepthroating the sheriff’s, it certainly seemed like this outlaw was doing everything he could to bring Francis to the best rapidly-approaching orgasm of his life.
When the outlaw wasn’t using his free hand to pleasure the sheriff’s cock, he rubbed his strong hand across the sheriff’s stomach, tracing his happy trail with his thumb as he reached up to rub slow, wide circles around the sheriff’s fuzzy chest, just barely missing his nipples each time. Francis never considered his nipples to be quite sensitive, but any touch to the erect nubs on his chest would feel like heaven in his current state, he thinks.
The outlaw’s hands moved to instead gently rub and massage all around the sheriff’s meaty thighs. The tops of them, the sides, even around his knees and calves, when the outlaw suddenly oddly shifted, grabbing the muscles just above the back of his knees. Francis was confused at the odd spot to grab, but too lost in his pleasure to truly care or question it.
That is, until the outlaw pushed up to cause his legs to dangle in the air as he laid back flat on the desk. Francis made a noise of surprise, his hat falling off his head onto the surface of the desk next to him, confusedly trying to look around his cock and his legs to see the outlaw’s face, who was currently placing kisses down his cock and down his taint. “Wh– What are you–” His words were cut off by a gasp, as the outlaw’s tongue pressed against his asshole, right between his muscled, soft, fuzzy cheeks.
The outlaw’s tongue dragged across the entire hole a few times as Francis panted and whimpered from the new sensations, before the outlaw began to use the tip of his tongue to circle the rim, massaging the previously completely unused hole loose.
“G– Grey– Oh my God–” Francis moaned, throwing his head back and squeezing his eyes shut, slapping his hands over his mouth and jaw. He couldn’t believe what was happening. He’s never felt so good in his life. How has he gone his entire life without experiencing this? The outlaw smirked against his hole, continuing to tease the outer rim of it as he pulled one of the cheeks aside with his hand, before moving to the centre and plunging into it, his tongue now massaging the inside walls of his asshole, sending shocks of pleasure through the sheriff’s body. He took his hand away from the cheek, using it to continue stroking the sheriff’s cock, using his other hand to jerk his own.
Francis bit his bottom lip hard and hissed through his teeth, arching his back, feeling infinitely more turned on from the stimulation of both his cock and his ass. In fact, it might even be too much. There were many thoughts going through his mind. Arousal from the… everything happening right now. Shame at enjoying this, especially enjoying something an outlaw is doing to him, no less. Confliction at feeling so… feminine, like a woman receiving cunnilingus at the full mercy of the man pleasuring her, and yet still not feeling out of place whatsoever. Overwhelmed and on the edge from all of the pleasure. He wasn’t sure what thought was the most prevalent at the moment, but many were telling him that they had to stop right then, whether because they’ve simply gone too far and needed to stop or because Francis was about to burst.
“Oh God– Shit– Wait– Grey, wait– Stop–” He begged. The outlaw cocked an eyebrow and complied with a smirk, stopping the assault on ass and cock just as Francis was nearing the peak, standing up fully and looming over him, the tip of his now fully-erect cock resting against his asshole. And fuck… Now that Francis sees it in all its true glory, it’s very clear that he is 100% both thicker and longer than Francis. Not by much, but still. Fuck. Francis was equally embarrassed, ashamed, and turned on. Why did this outlaw have to be such a grower?
“You agreed to leave the pleasure-makin’ to me, Sheriff~” He said, in a low voice that sent shivers down Francis’ spine.
“We agreed on a blowjob, not– whatever the fuck that was!” He growled at him, still panting.
“Don’t seem like a problem to me, I’m still usin’ my tongue, aren’t I? Those noises you were makin’ didn’t exactly sound like protests, either. Not to mention lil’ Francie down there drippin’ up a storm…~” He lowly chuckled, tapping a finger on the tip of his cock, making Francis hiss through his teeth as the outlaw slowly raised his finger to stretch the long line of precum oozing from it. Francis rubbed his face with his hands with a deep sigh, lots of conflicting thoughts running through his might. He was so turned on, so aroused, so horny, feeling like he could burst at any moment, and yet so ashamed, so stressed, so embarrassed, feeling so… vulnerable at the position he’s found himself in.
“Hey,” the outlaw started, softly. Francis removed his hands to look at his face, meeting his beautiful, bright, cold grey eyes, nearly twinkling in the warm light of the lamp. They weren’t the worst eyes to look at. Not at all.
“We don’t have to keep goin’ if you don’t want to. Sorry for, uh… crossin’ your boundaries ‘n all that. Could just… finish you off by suckin’ your dick like planned, or you can go and deal with it yourself– I dunno, whatever you want. Just thought you’d enjoy somethin’ new. I can guarantee all the new things you’d try would feel fuckin’ fantastic, but– We don’t have to try ‘em if you don’t want to. Say the word and it stops here, Sheriff,” he said, softly. Genuinely. He had an expression of sincerity, of genuine care. Francis wasn’t sure he’d ever seen a face quite like it. It… made him feel safe.
Francis stared at his face for a long while, his cock twitching intermittently, feeling the outlaw’s cock throb against his bare ass. Francis softly panted, the silence in the room and the sound of his breaths suddenly seeming so loud, the lack of noise threatening to cause his ears to ring. After a few long moments of consideration, neither of their erections even slightly letting up, he sighed. “...Fuck it. We’re already this far in,” he mumbled out. He wants this. For better or for worse, he really wants this. What does he have to lose? Besides his anal virginity, at least.
The outlaw raised his eyebrows in genuine surprise, before it transformed back into a face of suave smugness. “I’ve promised it before and I will promise it again; You will not regret this, Sheriff.”
“Yeah, yeah,” Francis rolled his eyes, waving him off.
The outlaw snickered. “Oil?”
Francis blushed at just the implication of needing oil for what they’re about to do. “Second drawer to my right,” he provided, sheepishly.
The outlaw cocked an eyebrow with a smirk, walking around the desk to open the drawer and retrieve the bottle of oil. “You just keep this around all the time, huh?”
“Don’t blame me for havin’ needs, horndog,” he huffed.
The outlaw snickered, unscrewing the cap of the bottle and applying some of the oil to his fingers. “No one likes a hypocrite, Sheriff.”
Francis rolled his eyes, as the outlaw leaned over him on the desk, beginning to spread Francis’ cheeks apart with his fingers covered in the cold oil. Francis instinctively tensed up.
“Relax. It’ll feel a lot better and a lot less painful if you’re not tense. Trust me,” he said, starting off by simply rubbing his fingertip around the rim of his hole. Francis took a deep breath and nodded, before glancing up, his cheeks flushing. The outlaw’s cock was right above his face. The outlaw’s long, thick, throbbing, twitching, dripping cock was right above his face. Above his mouth. Above his tongue.
Francis has never sucked a cock before. He could be horrible at it. He could hate the taste of it. He could hate the texture of it. He could hate the smell of it. He could make his jaw sore from it. He could puke from it. There are so many things that could go wrong from Francis trying to suck the biggest cock he’s ever seen in his life. And yet, in this current moment, there’s nothing he’d rather be doing.
Francis slightly raised his head, closing his eyes, his mouth open, his tongue connecting with the bottom of the thick member, just beginning to lick the bottom of it in slow, messy, sloppy drags, coating it with his saliva. He let out a soft moan, his eyebrows turned up in pleasure, his dick twitching out another line of precum. Every worry in his mind washed away. He could taste this cock all day. He could feel this cock all day. He could smell this cock all day. He was truly in heaven.
The outlaw slightly jumped in surprise, looking down, before giving a chuckle. “This is what we’re doin’ first, huh? Alright, fine by me,” he said. He began moving his hips back and forth, grinding against the sheriff’s face, rubbing his cock against his wet tongue. Francis let out a moan in reply, trying to get as much of his tongue onto this man’s cock as possible.
His hands snaked down his body, grabbing hold of his own cock and gripping it, giving a few short tugs. He needed this. He felt like he was constantly on the edge, he needed some sort of stimulation to himself. The outlaw grabbed the sheriff’s wrists and pinned them to his sides, smirking. “Ah ah ah. That’s not how we’re doin’ this, Sheriff. You get to touch yourself when I say you can. Got me?”
Francis let out a whimper in reply, but simply nodded against the outlaw’s cock, trying to lick against it even harder to compensate for the straining tightness coming from his own member. After a while of more licking, the outlaw pulled his cock back until just the tip was touching the sheriff’s lip. “Now I’m gonna teach you how a real man sucks cock. Feel we’ve had enough foreplay by now,” he smirked.
Francis’ eyes widened. That is going in his mouth? The longest, thickest, overall biggest cock he’s ever seen in his life was about to go down his throat. A feeling of dread pooled in his stomach, and yet, he wanted this. He desperately needed this. This was certainly not how he thought today would go. This was certainly not where he thought his life would take him. And yet, right now, he doesn’t feel an ounce of regret. Here he is. Sheriff Francis Davidson. Laying on his back, with a bare ass and a slobbered-up hole. About to be throat-fucked by the notorious Grey Thunder, whom he already just spent at least ten minutes drooling on his cock.
The sheriff was undeniably embarrassed by this entire situation. And yet most of the dread he feels is him thinking about when it will inevitably end. So for now, he’ll enjoy himself. At least he’ll try to. Maybe he’ll hate sucking this massive beautiful magnificent cock currently pressed against his lips and that will be enough clarity for him to snap out of all of this and call it all off. But even Francis can recognize his own wishful thinking.
“Deep breaths, Sheriff. Don’t try to be a hero, either. Whatever you can take is whatever you can take. Last thing I want is to hurt that pretty face and ruin that beautiful voice of yours,” he said with a wink, causing Francis to blush. He wasn’t sure if the compliments were genuine or simple teasing, but either way, it spawned butterflies in his stomach.
Francis took a deep breath and nodded a little, closing his eyes as the outlaw began to slowly slip his massive cock down his throat. “Keep breathin’, Sheriff. I’ve gotcha. You’re doin’ great,” he commented, softly, and Francis softly moaned in reply. He really wished this outlaw would stop making him feel so safe. He’s so used to feeling threatened around criminals, this one man is fucking up his whole system.
The outlaw very slowly, very gently thrusted into Francis’ mouth, each time going just a little deeper, rubbing against the sheriff’s tongue to allow him to taste more and more of his length with each thrust. Francis nearly reached halfway down the outlaw’s cock, before he gagged. The outlaw raised his eyebrows and immediately pulled out as Francis began to cough, sitting up as he held his throat.
“Shit– You alright, Sheriff?” The outlaw questioned, rubbing his back a little to support him in his coughing.
“Y– Yeah– I’m– I’m fine. Just… too much, I guess,” he said, grabbing the bottle of whiskey and taking a sip right from it, just to soothe his throat somewhat. Water would be better, but the only possible water around besides spit is one fluid from either of them that he’s absolutely not willing to try. Oh god, do gay guys like that sort of thing? Gross. Ew. He regrets thinking about it. He’ll stick to whiskey. He’ll get water later. Not… Ugh.
“You sure? You seem a lil’ lost in thought, there.”
“What? Oh, yeah, I’m fine.”
“Good.” The outlaw smirked. “Don’t need you pukin’ all over both of us. Up for more, then? You were obviously havin’ a pretty good time~” He teased. Francis blushed and glared at him, before lying back on the desk without a word. The outlaw snickered, slipping his cock back into the sheriff’s mouth. He continued to slowly fuck Francis’ throat, getting back into a good rhythm, before the sheriff gagged once again. Instead of recoiling, he instead let out a moan, slightly arching his back in a squirm as his own cock gently shot out another line of precum. The outlaw’s eyes widened.
“Oh my god, you’re into this, aren’t you?” He laughed as Francis blushed harder, making noises of protest. “No need to be embarrassed, Sheriff. Discovery is a natural part of life!” He said, his penis still actively throbbing inside the sheriff’s mouth. “Let’s keep goin’ and see where our findin’s take us, hm?” He smirked down at him, beginning to pull out of his mouth, and just as Francis was about to respond and protest, he thrust back in, harder than before. Francis’ face flushed as he gagged once again, his eyes rolling back in his head from pleasure as the outlaw began truly fucking his throat, the sheriff making choking noises every time the cock slipped as far into his mouth as it could go. The sheriff moaned, his own cock now nearly pouring out precum as his body squirmed.
His body was on fire as the most obscene noises rumbled out of his throat, the vibrations further pleasuring the man currently ramming it. In his absolutely horned-up mind, there is nowhere else the sheriff would rather be. He’s not in his office. He’s not lying on his desk. He’s not married. He’s not wearing a ring. He’s not wearing clothes. It’s just him and his outlaw in their own world. He didn’t know why he called him his outlaw, but he didn’t want to think about that right now. He’s too busy being ravished.
The outlaw continued to roughly fuck the sheriff’s throat with soft grunts here and there, leaning over Francis and coating his own fingers in more oil, beginning to probe and rub around the sheriff’s asshole. Francis let out more soft moans at the sensation, automatically lifting his legs once more. The outlaw smirked, continuing to massage the rim of it to try and get it to open up as much as possible, before slowly plunging his pinky finger into the sheriff. Francis loudly moaned, squirming even more, the pleasure overwhelming him and washing over his entire body.
“Oh, you like this, Sheriff? Yeah? You like bein’ stretched open like a cheap whore?” Francis moaned as he continued to gag on the outlaw’s cock. He couldn’t believe how good he felt. He almost thought he was dreaming. But the slight pain and ache from a foreign object entering his previously completely unused hole was proof that this was all very real. The pain was certainly violently overshadowed by the pleasure, though.
The outlaw continued to run his finger along the sheriff’s insides, before he added his ring finger into the mix as well, causing more moans and squirming from Francis, especially when he ran his long, thick fingers over his prostate. There was certainly nothing small about this outlaw. Francis can’t decide if that will soon be a blessing or a curse for himself and his insides.
Before long, four fingers were inside of him, stretching him completely, teasing his prostate with every rub along his inside walls. “Look at you, all stretched out”, commented the outlaw, smirking. “You ready to take this cock, Sheriff? Yeah?” The outlaw commented. Francis moaned against his cock, before it was pulled out, absolutely dripping from the copious amounts of the sheriff’s saliva on it, leaving Francis panting and drooling.
“Don’t worry, maybe you’ll be able to take it all in your mouth next time, Sheriff,” the outlaw said, smirking down at him. Francis glared at him a bit. “There won’t be a nice time, outlaw. Don’t even know how you talked me into this in the first place.” The outlaw rolled his eyes, smirking. “Sure. Okay. we’ll see about that.” Francis felt his cheeks flush.
Francis watched the outlaw walk around the desk and line up his cock with his hole, his cheeks burning and his cock twitching. He rubbed his cock against his entrance, teasing him, threatening to enter but always just barely missing, causing the sheriff to softly whimper. He tried to muffle his noises, playing it off as him wiping the drool from his lip and chin.
The outlaw smirked, grabbing the sheriff’s hat on the table and placing it on his head. “Not really my usual style, but I like it,” he commented, beginning to pour more oil across his cock, before setting it down and rubbing it all around it, applying a little more to Francis’ ass as well. “Ready to get your brains fucked out by Grey Thunder, Sheriff?” He cocked an eyebrow with a smirk, continuing to tease and grind against the sheriff’s ass.
Francis’ blush deepened, and he rolled his eyes, despite his whole body feeling raw and sensitive and so excited for what was to come. “Shut up and just– Get it over with,” he growled out with a little glare. He has to stay in control here. He’s already given this criminal too much power, letting him see him so vulnerable, letting him talk him into doing all this.
The outlaw smirked, before using his hand to properly line his cock up with the sheriff’s hole. “Be sure to relax, Sheriff. You’ll hurt yourself otherwise,” the outlaw suggested. Francis felt the urge to roll his eyes at the fondness and sincerity in the outlaw’s voice, but in fear of his ass being more sore than he knows it’s going to be, he simply nodded in reply. The outlaw smirked once more, beginning to push into him.
Francis gasped when the tip entered him, beginning to slightly arch his back and pant as the outlaw’s massive cock pushed deeper inside of him, his meaty thighs gripped by the outlaw’s strong hands. “Oh god– Shit– Fuck–” He softly moaned. The outlaw let out a deep breath as he bottomed out against Francis’ ass, feeling his near-excruciatingly tight asshole gently clench around his huge member. “All in,” he said, panting a little, revelling in the sight of the panting, blushing sheriff in front of him. “Ready for the fun part, Sheriff?” He questioned with a smirk, and Francis could only let out a soft moan in reply. Taking this as an acceptable answer, the outlaw began slowly pulling out of him, before pushing back in, just as slow.
Francis moaned at the sensation, feeling the outlaw repeatedly invade and escape his asshole, feeling each thrust press against his prostate. All he could do was lay there and whimper, forced to bask in his own very submissive and feminine-sounding noises with a look of pure bliss and pleasure on his face. He reached up to completely cover his face with both his hands in a desperate attempt to hide himself and muffle the noises being fucked out of him. No one should see him like this, no one should hear him like this, not even the man pleasuring his asshole with his massive member.
His wrists were suddenly grabbed, gently pinned above his head, and his warm brown eyes were once again locked with the outlaw’s cold grey ones. “Don’t do that,” he started, softly. “I like seein’ you like this. I like seein’ and hearin’ how good I’m makin’ you feel,” he said with a level of audible sincerity and fondness that Francis would never admit made his heart skip a beat. He swallowed, simply giving a shaky nod. The outlaw softly smiled in reply, before it morphed back into his signature smirk. “Keep your hands there. We’re gonna pick up speed, ‘kay, Sheriff?” The outlaw asked, cocking an eyebrow, and Francis gave another gentle nod. As soon as he received confirmation, the outlaw immediately gripped the sheriff’s hips, beginning to thrust a little quicker.
Francis immediately loudly moaned, arching his back, clenching his fists, obediently keeping them pressed above his head. His cock was practically leaking a pool of precum across his belly as the outlaw’s cock reached in and out of his asshole, practically feeling it reach deep into his stomach. He had to take a look down at his abdomen to make sure it wasn’t poking through, although he’d never admit to the slight twinge of disappointment he felt at it not quite being big enough to do so.
The outlaw slowly picked up speed, the increased rate of the thrusts causing high-pitched whimpers to escape from Francis’ mouth. The outlaw loomed over him as he got into a steady rhythm, his hands planted on either side of the sheriff, fucking him in even, steady thrusts, panting over the sheriff’s loose, sweaty body. “G– Grey–” Francis grunted out, panting. “Come on– H– Harder– Please–” He begged, locking his eyes with him. The outlaw’s eyes widened, before he smirked again with a soft low chuckle. “That’s more like it,” he said, before thrusting into him with full force.
Francis nearly screamed, his whimper was so loud. Each thrust, each pound against his prostate, each subtle movement, any tiny thing the outlaw did to him wrung a new noise out of him, whether a moan, a gasp, a shudder, a squeak, no matter what it was, it was music to the outlaw’s ears, Francis could tell. The outlaw simply smiled at the submissive display the sheriff was showing. Francis had never felt so embarrassed, so ashamed, so unmanly, and yet… He’s never felt so free. He knows he’s going to regret this in the morning. He knows he’s going to regret this as soon as he finishes. He’s desperate to cum, as any horny man would be, but he never wants this to end. If it ends, he goes back to his old life. He’s back in his office. Back on his desk. Still married, still wearing his ring, still half-clothed. He’d have to face reality again. He doesn’t want that.
He locked eyes with his outlaw once again as he violently rammed his ass. His face full of genuine adoration, genuine care, genuine happiness at seeing his sheriff so pleasured. “His” outlaw. “His” sheriff. Those terms feel so wrong and yet so right. Francis truly wouldn’t mind being called this man’s sheriff. Part of him hopes he wouldn’t mind being called his outlaw. Francis didn’t know what he was thinking. He’s thinking with his cock and his ass and the pleasure coming from them. And yet everything was compelling him to stay, to continue, to reach out, to live in this moment right here as if it will end soon. And it will end soon. It all will.
The time with his outlaw is limited.
…
Fuck it.
Francis grabbed the outlaw by his shirt collar, smashing his face against his in a passionate kiss. The outlaw’s eyes widened, before he moaned against his mouth, leaning forward into the kiss, making out with his sheriff as he was once again laying flat on the desk. It was sloppy, and messy, and wet, filled with so much lust, so much passion, as if the floodgates of their built-up love came crashing right open. Their tongues intertwined, invading each other’s mouths in a chaotic uncoordinated dance, fighting to feel as much of the other as possible, as the outlaw pounded the sheriff as hard as he physically could, feeling his balls slap against Francis’ hairy ass over and over, grinding up against him with every single thrust, pressing his dick right up against his sheriff’s prostate.
The outlaw soon pulled away from the kiss as they wrapped their arms around each other in a tight embrace, tracing kisses down his sheriff’s cheek, to his chin, to his neck, where he started sucking and gently nipping at the soft skin. Francis moaned, tilting his chin up to expose more of his neck as his outlaw placed lovebites along it. Both of them had a hand tangled in the other’s hair, each gripping it tight, the outlaw holding his lover tight as he ravished him, the sheriff finding comfort in the criminal’s beautiful hair through the pleasurable assault on his ass.
They continued to fuck, the outlaw pounding all the right spots as he panted over the sheriff’s shoulder and neck while he held him, the sheriff doing the same as his now very loose asshole was repeatedly stuffed and filled, them sharing pants and moans and grunts and whimpers. “G– Gettin’ close, Sheriff,” The outlaw said, ramming his lover even harder. “Y– You ready to get filled up?” He was clearly struggling to keep up his bravado and confident act while pounding the sheriff so hard.
“Oh God– Yes– Please– Grey– Please–” He begged, practically clawing the outlaw’s back, definitely would have left marks if the outlaw wasn’t still clothed. Francis simply couldn’t keep his excitement contained. He wanted this. He needed this. He was about to burst. The outlaw was about to burst inside of him. He was so ready. So ready to feel his seed inside of him, so ready to be filled up, so ready to feel the warmth of it.
The outlaw roughly pounded him a few more times, before loudly cursing and throwing his head back, releasing his hot load into Francis’ asshole, grinding right up against his ass, his cock violently throbbing and spasming right up against the sheriff’s prostate as the warm semen flooded out of it. Francis loudly moaned, arching his back, shooting the hardest and biggest orgasm he’s ever felt in his life. It ran a shock through his entire body, his cum practically spraying out of his cock, reaching right up to his chin as it shot across his entire chest and abdomen.
He laid there sweaty, panting, trembling as the outlaw kept his cock buried in his sheriff’s ass, before the outlaw leaned down to continue making out with him, much less sloppy and clumsy. The outlaw seemed just as shaken up, showing similar signs of exhaustion and coming down from overstimulation, cum dripping out from the small crack between his massive, slowly-deflating penis and the sheriff’s now very loose and relaxed hole. Goddamn, even the outlaw’s loads were big. How long was he pent up for that much cum to shoot out? Or are his loads always that big? Why is he concerned about the size of another man’s load flowing inside of him? It shouldn’t be there at all. But it is, and it’s so big, and it feels so much better than Francis would like to admit.
After a few long moments, the outlaw very slowly pulled his cock out of the sheriff’s asshole, causing him to let out a high whimper from the sensitivity, before the mass cum inside of it began to slowly leak out.
The outlaw began kissing down the sheriff’s chest, much to his confusion, before he began lapping up all the cum shot onto the sheriff’s body, collecting it all on his tongue. Francis blushed, before hissing through his teeth and whimpering as the outlaw cleaned off his very sensitive cock, licking it all over, leaving no trace of cum whatsoever, ensuring he did a thorough job before moving down to his asshole, beginning to dig his tongue into it. Francis moaned and threw his head back as the outlaw once again pleasured his asshole, running his tongue along every part he could reach inside of him, collecting all of the cum in his mouth.
He then stood back up, leaning back in to kiss Francis, him moaning as their tongues intertwined, sharing the mixture of their cum between them as Francis tasted his own cum, the outlaw’s cum, the taste of his asshole, the taste of his cock… It felt so filthy, yet like most other things today, it turned him on.
They both soon retracted their tongues and pulled away, swallowing the remaining liquid in their mouths. Francis gave a light grimace. “Well, we both definitely need a better diet.”
The outlaw gave a chuckle. “Speak for yourself, I’m always up for a good fruit salad,” he smirked. “Have I earned that glass of whiskey now?~”
Francis rolled his eyes, grabbing the bottle and handing it to him. “Knock yourself out.”
The outlaw snickered, filling the glass set off to the side and filling it, before downing it with a breath. Francis simply stared, now sat on his desk, his bare ass already sore against the wood. He’s never felt so relaxed. So exhausted yet so fulfilled. But he also felt so… ashamed. He just did that. He let a man do that to him. He let an outlaw man do that to him. And he liked it. He really liked it. What would his wife think? What would everyone else think? He didn’t know having something up his ass would feel so good. He didn’t even know he could get off without touching himself. He didn’t know a man’s cock could be so big, he didn’t know a man could be so skilled with his tongue, he didn’t know a man could be so attractive, he didn’t know a man could have such mesmerising eyes, such soft and beautiful hair, such perfect physique…
“You okay?” The outlaw asked, with a smirk and cocked an eyebrow. That snapped Francis out of his distracted trance.
“Huh– What?”
“You were starin’. Not that I can blame ya, but– Well, this was clearly new to you. First time’s always special, but always the worst,” he shrugged. “‘Sides, you’ve clearly got somethin’ on your mind right now, too.”
Francis rolled his eyes a bit. “Well, I have a few things on my mind right now,” he said, cocking an eyebrow. “One of which bein’ that any good outlaw would’ve been out the door by now.”
The outlaw looked a little surprised, before smirking once again. “Well, any good sheriff woulda been scramblin’ to lock me back up by now.”
Francis lightly shrugged, him glancing away with his hunched posture on the desk. “I’ve already succeeded at bein’ a bad husband. Might as well be a bad sheriff, too,” he said with a deep breath. “Just… Try to stay away from stealin’ horses for now? Please? Don’t wanna have to deal with you again.”
The outlaw stared at him for a moment, genuinely surprised, before he gave a small smirk. “...I think you’d make a pretty amazin’ husband, Sheriff. Just not to her,” he said, lightly shrugging, taking the whiskey bottle and stepping right back into the cell, closing the door himself. “I think I’ll stick around a lil’ while. Just ‘till it gets borin’,” he said with a shrug. “Who’d be here to keep you company if I were gone, right?”
It was Francis’ turn to stare at him in surprise. After all of that, he’s… staying. He could’ve just… gotten his rocks off, made the sheriff question everything he knows and book ass out of there, and yet… he’s staying. Francis let out a deep sigh. “You’re one weirdass outlaw.”
“Aw, thanks, Francie. You’re lucky you have such a nice ass, most wouldn’t get away with callin’ me somethin’ like that~” The outlaw winked. Francis rolled his eyes as his cock twitched. Down, boy, we just dealt with you.
Francis stood up from the desk with a wince, looking to the outlaw. “...C’mon. We’ve got a spare bath and a comfier bed in the other room. Usually for emergencies or if an officer has to stay overnight, but… You deserve that much for bein’ so… well-behaved, I guess,” he said with a light shrug. The outlaw’s eyebrows raised, before he smirked again, opening the cell door. “A good boy, am I? I’d love to see how you react to bein’ called that next time~” he said, seductively, winking at Francis.
“Like I said, there won’t be a next time. Keep your head out of the clouds,” the sheriff said with an eye roll. The outlaw scoffed. “Sure. You’ll get railed so hard you cum untouched only once in your life and never go back to it when a man offerin’ it is right in front of you for days. Likely story,” he teased, reeling his hand back to smack one of Francis’ buttcheeks, making him yelp and glare at him. “C’mon, let’s get to that bath, Sheriff,” he said with a wink to him, and Francis deeply sighed, beginning to limp into the next room as the outlaw followed close behind him, the fly of his jeans still unzipped as his now half-sized flaccid penis freely flopped around with each step.
Today was a pain in the ass. But Francis didn’t yet know that it was the best pain in the ass of his life.