Chapter Text
When you agreed to tag along with Dean today you didn’t really expect to be doing this on the ride. To be fair, you should have considered the possibility knowing Dean but it honestly didn’t cross your mind.
It started when you placed your hand on Dean’s thigh during a long stretch of open road. There was nothing to do but listen to music and look out the window so your hand just naturally gravitated to your boyfriend’s leg.
You mindlessly started trailing your fingers up and down his thigh, not thinking much of the action until you hear a groan from the driver’s side. Looking over at Dean you noticed his tight grip around the steering wheel. You shoot him a confused look, wondering about his sudden intense focus for the road in front of him. You were a few seconds away from asking him what was wrong when you catch the outline of his half hard bulge underneath his zipper.
The unexpected sight gives you an idea, Dean’s covered cock making your mouth water. You look up at the road making sure that it was free of any other cars as it was a few minutes ago before giving Dean’s leg a quick squeeze. He jumps at the sensation, his cheeks blushing just a little now that he knows that you’re aware of his problem.
“So,” You start, reaching over the small space between you to slide down his zipper over his heated muscle. “I want to try something.”
“Oh God,” He says in reply, his voice trembling a little when your hand slinks under the waistband of his underwear wrapped around his velvety dick.
The car revs up as your hand starts to move up and down, jacking him off as best as you can. You pull him free from the confines of his boxer briefs and give him a few pumps to watch him grow fully hard in front of your eyes. You settle your body against the bench seat of the car to get your head in Dean’s uncovered lap. You get as comfortable as you can in the cramped space, running your tongue over the leaking tip of the older Winchester’s thick dick.
Dean groans above you and you take that as a sign to open your mouth and take almost half of him down your throat. You suckle at your boyfriend’s cock as he drives, your tongue tracing the veins on the underside of dick as the car speeds up around you. You bob your head just a few times, not yet getting a steady rhythm, before the Impala screeches to a halt.
Dean’s strong hands suddenly pulls you off of him, basically lifting you upright and towards his mouth to kiss you harshly. He’s growling against your lips as his hands grab at your hips, thighs, and anything else he can touch in your twisted position.
You pull away from his claiming kisses, breathing deeply to fill your lungs with air, as you take a second to recognize your surroundings. Dean’s stopped the car off the side of the road, tall trees encircling the Impala and keeping you hidden from any prying eyes.
“Fuck, Y/N,” He says when you finally gets his hands under your shirt. His fingers trail up your skin, stopping when he gets your bra covered tits and gives them a squeeze. “You almost made me crash Baby.”
You smile at his admission, closing the gap between your mouths to kiss Dean again. You suck his plump bottom lip in between your teeth and bite down hard enough to get Dean to groan. You take this time to wrap your hand around his abandoned dick and jerk him off slowly as you
devour his mouth.
“Can’t have that now,” You smile against his mouth, your thumb swiping at the head of his cock, “You can’t fuck me if we crash.”
Dean grunts as his hips bucked up into your hand. “Fuck. Get up up here.”
You scramble up until you’re kneeling on the bench seat of the impala, desperately tugging at your belt to get rid your clothes. Dean’s preoccupied with pulling down his own pants, his jeans going as far as his knees. His breathing picks up as he takes his own dick into his hands, one fist slowly pumping as you manage to get your pants past your thighs, knees, and off of your left leg.
“Get over here sweetheart.” Dean reaches for you and you shuffle over to him naturally.
The car rocks a little as you move toward the half clothed Winchester. You hold onto to the black dashboard of the Impala as you swing your left leg over Dean’s bare lap, grabbing onto the steering wheel to help you lower yourself onto his skin.
You’re facing the windshield, looking at the trees when Dean’s cock makes contact with your wet pussy. You moan as the tip of his dick rubs against your clit, your hips twitching so that his thick length slides between your full lips.
“So wet.” Dean whimpers. His hands find their way to your hips, helping you rock back and forth slowly on his cock. The sensation of his dick bumping your clit is causing you to shake slightly in his lap, the small amount of pleasure driving you crazy. You want more.
“Dean.” You whine, your fingernails digging into the dashboard as you try to keep your hips in check. “I need you to fuck me.”
“Hell yeah,” He breathes. He taps at your right hip once. “Y/N, lift up.”
You do what you’re being asked, lifting yourself up to your knees so that you’re hovering above Dean’s lap. You feel Dean reach under you to grab a hold of himself and shortly after you feel the head of his dick poke at your opening.
You slowly start to sit yourself down on Dean’s length, his thick cock widening your wet pussy as he enters you. Dean moans loudly, his voice bouncing around the car as your heat envelopes his member. You slink further and further down his dick until you’re flush against his lap again, relishing in the way his girth stretches you out.
“You cock makes me feel so full,” You say to Dean, rocking your hips to test out the feeling.
Dean’s hands start to wander over your back, his fingers lightly trailing over your spine and reaching over to cover your tits. His thumb rubs over where your nipple is covered by your shirt before he moves back to cradle your hips.
“You can move whenever you want to, baby.” He whispers to you, gripping your hips to let you know that he’s ready.
You take a few seconds to adjust to Dean before you use the steering wheel to lift yourself up and slide off of his cock. The moan slips out of your mouth before you even notice, the delicious stretch of Dean sliding back in invoking another moan out of you.
Your hips start slow, Dean letting you do all the work as you fuck yourself on him. Your pace starts to speed up, pleasure beginning to bloom in your stomach. You roll your hips over and over onto Dean’s lap, circling them when only the head of Dean’s cock is in you.
Dean’s moans spur you on even further, your hips starting to bounce in a progressively fast rhythm. Your thighs start to burn as you glide your cunt up and down Dean’s muscle. Behind you Dean starts to chant, a steady stream of curses leaving his mouth before he tightens his hold on you and raises his own hips to meet yours.
Your bodies connect with a hard slap, his dick driving up deep inside of you and short circuiting your brain. You hold yourself up on the steering wheel, stilling your hips as Dean surges up and fucks you.
Right now the only thing on your mind was how good Dean’s dick feels thrusting up into you, his thick length slipping into and out of your wet cunt as your knees dig into your leather bench seat of the impala. The car rocks under both of your motions, the impala bouncing along with the rhythm of Dean’s hips.
“You feel fucking fantastic, Y/N.” Dean growls, his rough hands digging tight into your hips. You buck back into his seated lap, grinding down when you feel the head of his dick press against your sweet spot.
Stars start to dance behind your eyelids as you roll your hips in a slow tantalizing circle. Dean’s fingertips dig into your skin as you grind against him, your own fingers tightening their grip on the dashboard and steering wheel. You use your knees to lift your hips up, slowly riding Dean’s length and fucking yourself at a slow and deliberate pace.
You moan as you hold onto the car, whimpering Dean’s name as he fucks upward every other time you lift off his cock. You can’t see his face since you’re facing the windshield but you catch a glimpse of his chiseled face through the rear view mirror.
HIs green eyes are glued to the space where you’re connected, his full lips partly open as moans tumble out of his mouth. He’s sweating, the car hot with all of your breaths and body heat mingling together, and his hair and t-shirt are all disheveled as you writhe against them. Dean looks fucking gorgeous as he fucks you in his favorite place.
You start to speed up your pace, your hips fucking on their own accord now that the familiar pleasure is bubbling up in the pit of your stomach.
“Fuck Dean,” You cry as you feel your legs start to tremble. “I’m about to come.”
Dean’s hands slide off of your hips to wrap around your waist, bringing in your body to lean against his chest. He starts to pound into you now that he has you close, his thick length widening and stretching out your wet pussy in fast and hard strokes. You gasp at the speed, gripping at his arms as your orgasam starts to rise.
“Come for me baby,” Dean grunts in your ear, his voice strained as his hips work up into you. “Come on Y/N.”
His dick pumps up three more times before the tingling in your gut really blooms and your orgasm runs through your body. Dean slows his rocking as your cunt squeezes around his thick member. You shake against his arms as your body goes through the pleasure shocks. Dean’s holding you tight as your orgasm passes through, planting kisses on the side of your neck as you catch your breath.
Once air starts to fill your lungs again, you raise your hips up and down remembering that Dean hasn’t come yet. He’s breathing hard against your ear, his arms lax as he watches you work. You glance out of the windshield, grateful that Dean parked in this deserted wooded area. You lift yourself up on your knees, bracing yourself on Baby’s steering wheel as you fuck yourself on Dean. Dean’s grip tightens on your skin again and you know he’s close to coming. You ride him until he does, moaning when his spunk spills inside of you.
“Fuck,” Dean whispers once he caught his breath. His hands are rubbing over your bare thighs. The motion helps you calm down from your high.
“That,” you say chuckling a little as the feeling comes back to your legs. “was awesome.”
Dean laughs along with you even as you tenderly rise off of him, his softening dick slipping out of your wetness. You move over to the passenger side, your bare but touching the warm leather as you sit properly. You reach down and pull up your panties and jeans that were hanging around your right ankle, covering yourself up.
Dean’s doing the same over on the driver’s side of the car tucking himself back into his boxer briefs. “And you said you don’t want to ride with me.”
You button up your jeans and roll down the window to let in some fresh air. You lean over once some of the hot air leaves the cab and kiss Dean on his lips. It’s a hot short kiss, Dean’s tongue licking at your bottom lip when you pull away.
“You can definitely sign me up for all future drives.”