Late Night Encounters
Summary: After studying with Sam runs late you run into John while leaving. Barely any plot, just smut
Warnings: Smut, Older John
I'll make up for John with a bunch more Dean stuff soon I promise.
~~~
"I'm so sorry I didn't realize the time!" Sam said as he helped you pack up your bag with books, the clock clicking over to 1am.
"No it's okay, I really think we made some great progress." You smiled back. Studying with Sam was far easier than by yourself, you were grateful for the company.
"Are you really okay driving back? It's not too late?" He said as he handed you your final book.
"Seriously Sammy it's fine, thank you for having me over!"
You slipped out of his room, quietly padding along the hall and down the stairs towards the front door, careful not to wake his older brother. You'd only met Dean a few times, and knew he worked long shifts to help support Sam at college while their father worked away.
You creaked through the living room, the cold air hitting your skin. You hadn't planned on staying this long, dressing for the summers day in a tank top and shorts, the chill was biting at you.
"And who", the lamp flicked on, a tall man stood in the corner of the room, a beer bottle in hand, "might you be?"
You stopped, your heart catching in surprise. "I- I'm sorry I'm just leaving."
"That didn't answer my question. Come over here." He stepped forward and you took him in, realizing he was the man from the photographs Sam had shown you of his parents. You walked towards him, suddenly feeling small in the presence of such an intimidating figure. He looked down at you, "What are you doing here?"
"I'm sorry, sir, time got the better off us I wasn't supposed to stay this late."
"Which of my boys are you fucking?"
You took in a small gasp. "Neither, sir, it's history- me and Sam are in the same class we just study together."
He took another drag from his beer, looking you up and down, not hiding his stare at your chest. Your lack of bra was coming back to bite you as you felt your nipples hardening in the cold air. You shifted your arms, trying to subtly cover your body from embarrassment. "A perky young thing like you deserves a decent fucking-"
"Sir I should get going." You had to admit he was hot, and his voice was starting to turn you on.
"-tell me, do my boys give it to you?"
"Sir we're not- I promise it's just studying."
He stepped in front of you, reaching out to push your arms away from your body, once again exposing your thinly covered breasts to the air. "Have you ever had even a half decent fucking?"
You looked up at him, meeting his steely gaze, "Half."
He chuckled, taking another swallow from his bottle, "You're funny. How old are you?"
"Old enough, sir."
"Sir's a good start, manners are important..." he reached out, pushing one of your shirt straps off your shoulder, your shirt slipping slightly down. He smiled down at you, tracing his finger down your collarbone. "You want this?"
You held his gaze, lowering your voice to a whisper, "Yes."
"You understand this won't be like making love to your childhood sweetheart? I'm going to fuck you and leave you, you get that?"
"Yes sir."
"Good girl, on your knees."
You sunk down quick, the hard wood slamming against your knees- you knew it would cause bruises.
"You know how to follow orders, I like that." He said, undoing his belt. "You ever suck a dick before, darlin'?"
"A few." You lied. You'd only ever sucked your on an off again boyfriend's in senior year of high school.
"Open your mouth."
You opened, waiting for his cock. He pulled it out from his pants, pumping it in his fist as he looked down at you. He put his hand hand under your chin, tilting your face up to look at him, and brushed his thumb lightly against your bottom lip.
With a lopsided smile, he roughly shoved himself into your mouth, your eyes growing wide as he filled you up. He barely gave you a second to get used to his length before he began lightly thrusting his hips into you, his tip hitting the back of your throat. He groaned and you looked back up at him, watching as he threw his head back, exhaling deeply.
"Gooood girl," he combed his hand through your hair, pushing you lower, "that's it, you're a natural."
You reached up to his cock, placing your hand on it's base, barely able to hold his girth.
"Nah-ah babygirl", he knocked your hand away, "you have to learn to take it all in your mouth. Hands behind your back."
You pulled your hands behind you, pushing your wrists together as though tied, and focused yourself on taking him deeper. He groaned again as he held your head down, enjoying the feeling of your lips wrapped around him and thrusted his hips hard, getting into a rough rhythm.
You looked up at him, eyes wide, and he swallowed hard, pulling his cock back slightly. "Stick your tongue out."
You opened your mouth wider, doing as he said, and he pressed his tip against your tongue, allowing you to taste him.
"You're good at this darlin'", he let his dick glide over your tongue, "usin' your mouth like such a good girl."
You felt your arousal growing, desperate to be touched.
"You like sucking my cock?" His hand cupped your cheek, an eyebrow raised. You nodded, locking eyes with him. "You want to feel good?" You nodded again.
He pushed his boot clad foot between your knees and you clasped your hands together tight behind your back. "You're gonna have to work for it- grind on me."
You lowered yourself down into him, slowly grinding against his boot. You felt vulnerable here, in the Winchesters' cold living room. Suddenly you remembered Sam upstairs- he thought you were on your way home what if he came down now- but as your clit rubbed against him you didn't care.
You let a small moan escape your lips, pulling yourself away from his dick as you focused on your own pleasure. You let the feeling wash over you, and he watched as you became undone on your knees below him, loving every second.
He licked his lips, drinking you in, his mind spinning from the beer and the image of you before him. He watched as another moan escaped your lips, your eyes closed.
"Stand up." You barely heard him in your needy state, but looking up at his serious face made you pause. "Stand up now, like a good girl, and let me see how wet that pussy is."
You stood up shakily, and he pulled you towards him, letting you feel the heat of his body radiating off him. His hand fumbled down into your shorts, fingers tracing over your panties. You let out a moan, your head leaning against his chest as he circled your clit, desperate for him to actually touch your skin. One of his fingers hooked around the corner of the fabric, pushing it to one side, and he dipped a finger into you, your wetness dripping over him.
"Jesus you're wet-" he laughed lightly, a surprised look on his face, "A cock in your mouth get you that turned on?"
You replied with another moan as you felt a second finger enter you, thrusting unevenly as your knees buckled. His other hand roughly grabbed your hip, keeping you steady, as he found his rhythm.
"You want more darlin'? You want me inside of you?"
You nodded, looking up at him, a whimper escaping your lips. He pulled his fingers out, and put them up to his own mouth, sucking on them one at a time. "You taste like cherry pie darlin." He said with a wink.
He found your shorts again, pulling them down to your ankles and you stepped out of them. Lifting your arms up he pulled up your tank top and stepped back, looking at you in all your naked glory. You felt vulnerable again, wearing nothing in front of this fully dressed man, but he gave you another smile that caused your thighs to squeeze together.
He pushed you roughly against the wall, pushing his pants down lower on his hips and pumping his cock in his hand. Your leg found purchase wrapped around him as he lined himself up with your entrance, giving himself a few gentle glides through your folds with his tip.
He pushed into you achingly slowly, letting his cock stretch you out, and you leaned against him again, desperately trying to hold yourself up. You let out a wining gasp at the feeling, wanting to feel him deeper.
He pulled out and began thrusting, hard and fast, barely giving you a second you catch your breath. His hand found your exposed breast, flicking at your nipple and causing your pussy to tighten around him.
You began to let out a loud moan, his hand moving fast to clasp tightly over your mouth. "You've got to be quiet darlin'. Can't be waking up the whole house now can we?"
He continued to thrust, his own head rolling back in enjoyment, hand still covering your mouth. You'd never felt this good before, his large cock almost splitting you in two.
You stayed like that for long enough to feel your knee buckling beneath you, desperately trying to keep yourself standing. He pulled himself out of his daze and looked down at you, hungry for more. "I'm gonna take my hand off your mouth, and you're gonna stay quiet for me, you understand?"
You nodded ferociously.
"Good girl."
He moved his hands down to your ass, lifting you up in a quick motion as both your legs wrapped around your hips. He pushed you back hard against the wall as he lowered you back down onto his cock, savagely plowing into you. At this new angle, you felt your orgasm rising quickly, biting your lip to keep yourself quiet.
He pressed his lips to your ear, speaking with hot breath into your skin. "You like that darlin'?"
You nodded, a small moan escaping you lips.
"When you cum you gotta keep quiet, you can do that for me?"
You nodded again.
He sped up his thrusting, driving into you hard. "Good girl. Go on then, cum for me."
You let the waves of orgasm wash over you, your head rolling back, nails digging into the back of his neck to keep your noises at bay. Your hips bucked into him, hungry for him to stay inside you.
Your orgasm barely over, he lowered you back to the ground and pulled his cock out, causing you to desperately whine.
"On your knees."
You did as he said, your buckling knees barely giving you a choice. He looked down at you as he pulled your hair out of your face, his large cock just inches from your mouth. You stuck out your tongue, wanting more.
"God you're good." He gave you a wink as he pressed his tip to your tongue, and you could taste your own wetness on his cock. He wrapped his fist around himself tightly, jacking himself off into your mouth. "You gonna take all of this darlin?"
You nodded, pushing your mouth around him.
"Good girl."
He let out a grunt as he came, and you swallowed it down, desperate to please.
He stepped back, giving himself a second to become composed, and looked back at you naked, kneeling before him.
"You're something else-" he laughed as he stuffed his cock back in his pants, grabbing his beer bottle from the side.
You stood up shakily, having to steady yourself for a second before slipping your shorts back on and tugging your shirt over your head.
He stepped back up to you, a hand reaching out to your breast and cupping it, pinching your still hard nipple between his fingers before stepping back again, eyeing you over.
"You best get going darlin'- it's getting late." He gave you a wink before retreating out the room, leaving you stood in the cold night air.












