ok so I had to look up what that was but apparently if you take a cowboys hat you have to ride the cowboy?? idek I fell in love with that idea and that’s how this happened 🫶🏼 ive missed you guys a lot so I’m just happy to be back
————
Cassidy chugs down the rest of his whiskey, setting the glass back on the wooden bar counter with a thud. He licks the amber liquid off of his lips and flashes you a grin. “Be right back, darlin’.”
You raise an eyebrow but say nothing, waiting until he’s just out of sight before reaching for the cowboy hat he’d taken off an hour earlier. You always wanted to try it on, but the man was practically attached to it and you never had the chance. Until now.
You set the vodka cran you’ve been drinking down on the counter and slowly place it on top of your head. “Call me Cassidy,” you mock his accent, “Cole Cassidy.”
“Now, now, I don’t think I sound like that, do I?”
You almost go white when you hear his voice over your shoulder, but you recover quickly. “No, my voice is a bit deeper.”
“Yeah?” He sits back on his bar stool next to you and orders another whiskey. “Ever heard of the cowboy rule, y/n?”
“The cowboy rule?”
He smiles knowingly at the bartender who sets a glass of whiskey down. “Do you know the cowboy rule?”
The bartender glances at the hat on your head, then at Cole, and flashes you a smirk. “Ah, don’t drag me into this.” He returns to cleaning glasses behind the counter.
You look anywhere but at Cole, choosing instead to look at the wooden support beams around the room. You can feel his whiskey eyes boring into the cowboy hat that rests on your head, but you make no move to look at him until he starts speaking again.
“So the cowboy rule,” he starts, “proclaims that if a woman takes a cowboys hat, she’s gotta ride the cowboy.”
Your face burns at his words and in your shock, you whip your head back to stare at him. “I—what?”
He’s grinning at you, his ears tinged pink. “You heard me, pumpkin.”
You clench your thighs slightly, and you can’t tell if the sudden heat in your stomach is from his words or the alcohol, or maybe a combination of both. He’s handsome, sure, and from the stories you’ve overheard, he knows what he’s doing.
“So if I do ride you,” you start, suppressing giggles at the surprise on his face, “do I get to keep the hat on?”
“I guess there’s only one way to find out.”
You knock back the rest of your drink and wave the bartender back over to pay for your tab. Cassidy grabs your hand and practically drags you out of the bar.
“Slow down, cowboy, we’re not even home yet.”
“Who said anythin’ about goin’ home?” He clicks the unlock button on his keys just as you approach his old red pickup truck.
He opens the back driver side door and gestures for you to get in.
You raise an eyebrow at him. “In the parking lot?”
“Is that a problem?”
You shake your head and slide back in the seat, reaching up to grab him by his collar and tug him on top of you. He hooks his boot on the door handle and shuts it behind you guys before moving to straddle your waist.
You try to think of something snarky to say but Cassidy shuts you up by pressing his lips to yours. The taste of nicotine and whiskey floods your senses, a slightly sweet tinge to his tongue.
He sucks on your tongue and presses a knee between your legs. You can’t help but thrust your hips up and grind against his thigh, the friction making you whine.
You reach up to grab something to ground yourself, your fingers finding his hair and tangling with the chocolate strands. You give it a tug and he moans into your mouth, pulling away to smirk at you.
“I knew you liked it rough,” he teases.
You roll your eyes at him, “you don’t know the half of it.” You lock your legs around his hips and flip yourself over so that you’re on top of him. “That’s much better.”
You have your legs on either side of his, his bulge rubbing right up against your core. You’re practically gushing, so wet it leaves a dark spot on his jeans. He reaches his hands up your shirt, squeezing your tits through your bra.
“Lord,” he groans, “I’d give you every hat I have if I could see you like this everyday.”
You lean and press a kiss to his lips, “easy cowboy,” you move your lips down to his jaw, “don’t make promises you can’t keep.”
He shivers under your touch, swallowing hard when you move your lips from his jaw to his neck and suck a dark mark into the skin. His calloused fingers dig into your hips, “e-easy now, no teasin’.”
You bounce on his hips slightly, his hard cock grinding on your throbbing clit through your pants. He grunts at the friction and you bite your lip to keep from whining.
His hands travel from your hips and up to your shoulders, lifting up your cowboy hat momentarily to tug your shirt over your head. He places the hat on again and cups your face, before he tugs you down to kiss him again. One of his hands wraps around your back to unclasp your bra. If you weren’t so needy, you’d be impressed.
“So pretty,” he hums, moving his mouth down to kiss the tops of your boobs. He’s gentle, applying just enough pressure for you to feel it.
“D-don’t tease,” you whine.
He pulls back. “Why don’t you use that pretty little mouth for something more useful than complaining?”
He rubs the tips of his index and middle fingers on your lips, slowly pushing them into your mouth. On instinct, you wrap your lips around them and start to suck on them.
“That’s a good girl,” he pets your head before returning to your chest. “Keep at it.”
He slowly kisses down your left side, kissing in a square pattern on the outside of your nipple. His mouth is hot and wet and has you squirming for more. Cass moans when you dig your hips a little too hard into his.
Finally, his hot mouth closes around your nipple and you moan around his fingers. He’s an expert, knowing exactly how much pressure to apply and when to use his teeth and when to go soft. You whine against his fingers, arching your back and thrusting your hips into his.
The friction does little to help the throbbing in your core and only succeeds in making Cass go harder. Finally, you can’t take it anymore.
You let his fingers fall from your mouth and pulls way from him. Cass looks at you with an eyebrow raised, “did I say you could stop?”
You place a hand on his chest and shove him back on the bench so that he’s laying down. “I’ve had about enough of you being in charge,” you grab the hem of his shirt and tug it over his head. “It’s my turn, cowboy.”
You never would have guessed that Cass has a submissive side. Yet, he laid down on his back and let you use him all the same.
You run your hands over his smooth chest, admiring the scars and the way his metal arm seems to meld into his skin perfectly. You plant light kisses across the border of metal and flesh, and Cass sucks in a breath.
Your hands run lower, following his treasure trail to the top button of his jeans. You pop it open easily, making quick work of the zipper and propping yourself up on your knees to tug his pants off. You’re greeted with his hard cock straining against his red boxers, and you drool at the sight of it.
“So worked up for me,” you sigh, running your finger across the outline of his dick.
Cass pants at your touch, especially when you start to trail your fingers across the waistband of his shorts. You slip a finger in and run it across the skin on the inside. You hook another finger inside and finally tug his boxers off.
His cock springs out, hard and veiny, the head red and dripping with pre cum. You grip the base snugly, giggling at the way Cass sighs and throws his head back.
You lick the tip, the salty sweet taste of his precum flooding your mouth. He bucks his hips forwards, trying to force more of his cock into your mouth.
“Not yet, cowboy. You cum inside me or not at all.”
Cass groans at your words, the sheer thought of stuffing you full of his cum and fucking it back into you is almost enough to make him cum. You tug down your bottoms almost too eagerly, your sopping panties practically dripping onto his lap.
You slip your panties off and move so that your entrance is above the head of his cock. “Ready, cowboy?”
“After you, cowgirl.”
You slowly sink onto the head of his cock, your pussy so wet it slides in easily. He’s big enough that the stretch is almost painful, your walls squeezing around him. The two of you moan in tandem as you pause just after his head, trying to adjust.
Cass grabs your hips, fingers digging into your soft flesh. You slide down a few more inches, eyes rolling back in your head at the friction. He bottoms out a few seconds later, your cunt flesh against his balls. Both of you are breathless, Cole’s hands slightly shaking in anticipation.
You move back up his length slowly before going back down, the feeling of his cock stretching your walls almost overwhelming. Your movements are slow at first, hesitant, but as it starts to feel good, you get more confident.
You start to bounce on his cock, your thighs slapping against his with every thrust. Cass helps guide you up and down his cock, desperate for more friction. His hat bounces on your head with every impact, your hair falling in your face.
“S-shit,” he hisses, using his hands to slam you against him, “look so damn fine in my hat.”
You mimic the way he tips his hat, interrupted when he lifts his hips to slam into yours. You can feel your orgasm approaching quickly, heat building in your stomach. Cass continues to lift his hips to meet your movements, moving one of his hands down to your dripping cunt to rub your clit.
The friction is enough to send you over the edge, your orgasm rolling through you. Your muscles give in and you collapse onto his chest, your head hanging over his shoulder. Your walls clench around his cock, and Cassidy makes no move to slow down.
He thrusts into you harder, trying to chase his own finish. “My little cowgirl,” he grunts, “cummin’ all over my cock. Such a naughty little slut.”
You whimper into his neck, feeling another orgasm starting to build up.
“Want me to cum inside you baby?” He coos, “want me to stuff you full of my cum?”
“Y-yes!” You whine, wrapping your arms around him to keep yourself grounded. “Breed me, p-please Cass!”
Your words send him into overdrive, a primal growl ripping through him. He’s thrusting into you impossibly fast now, his balls slamming against your ass with every thrust.
You squeal his name, your own voice sounding far away as you succumb to the pleasure. Cole’s thrusts get sloppier, and then he gives one final, hard thrust before spilling his cum deep inside of you. The warm cum filling you up is enough to bring about your own orgasm, intense shockwaves of pleasure washing through you.
Your vision and hearing black out for a second as you cum, your muscles going rigid and then relaxing. Cassidy holds you to his chest, petting your back and mumbling in your ear while you cum.
When you come to, you’re breathless and laying on top of Cass, his cock still buried inside of you.
Finally, a kofi sketch I can post! Okay, I admit, I indulged a little because @pancake-expert donated for me to draw my favorite subject, Gabe with long hair!
