Supernatural Short Stories

The Chauffeur

Jensen x Reader AU

The sleek black Rolls Royce pulled to a stop in front of the Manor house as you carefully made your way down the steps. Your Dad held your arm, acting as if he was guiding you down the steps. Instead, he was whispering all sorts of warnings in your ear. Warning you to act demure and polite. To not make him look bad in front of everyone else.

"Why don't you come along then?" You shot back. Grinding his teeth together, he grabbed your shoulder, forcing you to face him.

"You know I can't," his words were low, mean. "But this means everything to us. You need to make a good match, girl."

You wanted to scream back at him. To remind him that it was his fault your family was this way. That you didn't care about the money, you just wanted a normal life. But you stayed quiet, knowing it was the smartest thing to do.

"I know you're a good girl," your Dad continued, loosening his grip as the chauffeur climbed out of the front seat, opening the door for you. "But you're too headstrong. You know that you'll be ruined just as much as me if today doesn't go well."

He pushed you towards the car, and you didn't miss the narrowing of eyes by Jensen, the chauffeur. Trying hard not to let your father see you cry, you slid into the seat, letting Jensen shut the door.

The car was already running, and Jensen smoothly pulled away from the curb and down the long drive. The gates parted, and you were free from the house that had become more of a prison cell than anything else.

"Straight on then?" Jensen asked, his eyes intent through the rearview mirror as you hastily whipped away a tear.

You shook your head, knowing that while your Father would be furious, you needed time to collect yourself before you made your way to what was nothing more than an auction. Sure, it was written off as a tea for upper-class daughters, but you knew the main reason. There were plenty of wealthy men there, looking forward to finding some pathetic woman who would help their stature rise. Which is exactly what your Father expected.

"Our normal then?" Jensen offered you a smile, and you shook your head once more, barely able to speak. Sure, Jensen was your chauffeur, but he had quickly become a friend, and then more.

Speeding the car up, Jensen swerved around another vehicle, turning down the next street. A couple of turns later, he stopped in front of another gate, quickly entering a key code. Driving through, he parked in a dark garage, empty of anything but the two of you in your Father's car.

"Thanks, Jensen," you whispered, watching him closely as he came around the side, sliding into the backseat with you. "How do I tell my dad I don't want anything to do with those pompous idiots? All I want is...,"

Your words were quickly muffled by Jensen's plump lips against your own. Turning in the backseat, you let him pull you onto his lap. Your dressed bunched awkwardly around your thighs, the silky material refusing to give. The heels you hated wearing dug into the leather of the seats Jensen's hand wrapped around your neck, holding you still so his lips could plunder yours.

"Jay," you whispered against him, pulling away slightly.

"Y/N, you know you don't have to go through with this," Jensen pleaded with you, his hands dropping to your waist, bunching in the silk of your dress. "Just say the word. You and I...we'll run. To the U.S., or wherever. I don't care."

You wanted to, more than you cared to admit. But you couldn't do that. Not when it would leave your younger sister and brother suffering.

A tear slipped down your cheek, and he quickly brushed it away. "I hate seeing you like this. Let me know what I can do to help. Please."

"Just help me forget," you sighed. "At least for a little bit. Show me what's it like to be loved for me. Not because of who my Dad is."

"You sure?" Jensen asked. "Because...,"

"Please," you pleaded. "At least I can give this to someone I decide. Please, Jensen, show me what it's like."

Breathing heavily, Jensen laid you down on the spacious backseat, his bottom lip between his teeth as he stared down at you. "Y/N, as much as I want this, I don't want you rushing into things. You know what could happen if...,"

You took matters into your own hands, reaching down and pulling his dress shirt up and over his head. The overhead light was the only thing illuminating the entire car and building, and you could barely see his forest shaded eyes before he was pulling your dress up and over your head. Carefully hanging it over the driver's seat, he turned back to see you laying there, wearing your plain white bra and panties. "Beautiful," he mumbled, his thumb brushing against the tender skin of your hip.

You were nervous, never having done this before, but Jensen was gentle, brushing his fingers lightly across your skin, his lips following suit. Up your stomach to your cotton clad breasts, pulling the cups down until he could press kisses to the underside of your breasts.

His other hand slid under your knee, pushing until you lifted it up, your foot barely on the seat. Running his fingers up your inner thigh, he cupped you through your panties, driving a moan from your lips.

"I've been wanting to do this for so long," he mumbled against your skin, running his tongue along your nipple. "Sure, there's been the touching when your Dad's not looking, but I've wanted more. Even though I always knew it would be out of my reach."

"Jensen, please," you insisted, reaching for and threading your fingers through his hair. "I've dreamt of this happening."

He smiled up at you then, raising an eyebrow. "Really?"

You nodded. "I've always known it's you that I've wanted to be my first, and I've dreamed about it more than once."

"I wish it could be more than just in the backseat," he apologized as he slid farther down the seat, almost crouching in the corner so his head was level with your hips.

"I don't care Jay." you closed your eyes and threw your head back when his fingers slid under your panties, pulling them down before tossing them somewhere on the floor. His fingers traced your folds, barely brushing against your bundle of nerves, and you clenched around nothing, needing more.

"As much as I want to take this slow, you'll be missed if you don't show up soon," Jensen groaned, barely pushing against your entrance. Pressing in, he watched as your mouth shaped into an O, your hips arching off the leather seat. Jensen pressed your hips down, gently curling his finger deep inside you before sliding back out. In and out he slid the finger, driving you wild. Hovering over you, he added another finger, stretching you while his lips found yours.

Suddenly you were empty, as his hands fumbled down below. Then he was back, the tip of him pressing against your entrance, sliding in.

Reaching up, you grasped his shoulders, gasping as he pushed through in one motion. You felt a slight twinge but it was gone as he fully sheathed himself inside you. "Okay?" He asked, his eyes searching your face.

"Perfect," You answered.

Jensen set the pace, and you let him take control, reveling in the feelings he sent rocking through your system. The windows started to fog up, your perfectly coiffed hair unraveling around your head. But you didn't care. All that mattered was the feel of Jensen on top of you, inside you. And you knew, that no matter what happened this evening, no one could take this moment away from you.