Chapter Seven: The Dirty Devils
Pairings - Sugar Daddy! Dean Winchester/ Journalist! Reader/ Sugar Daddy! Sam Winchester
Warnings - SMUT BABY, Finally!! And Some Slight Degradation 🤤
✨charity case✨ | Winchester Masterlist | Angels, Demons and Monsters
The air was tense and freezing. Why you would think a silk dress in cool weather was a good idea is beyond me. Your nipples were visible now and Dean was finding it harder and harder to handle where his gaze landed. But nonetheless you had decided to ride along with him.
You were watching out the window, pondering on the shadows in the trees, slipping past your view and awaiting Sam's car to fly past the site as well. Goosebumps spread throughout your body, as cold a palm pressed into the soft skin of your leg. "It's a bit cold with the windows down."
He pointed out and you were now more aware of the thin fabric laying on your body. You crossed your arms. Squeezing your thighs together in embarrassment. He tightened his hold on you harshly and you shivered. "Come closer." You scooted from the passengers seat to the middle, his grip never leaving you.
He spread your limbs apart and ran a testing finger along your folds, his eyebrows shot up just as quick as a smirk appeared on his lips. "I have a feeling you wanted this darling. Wearing no panties could get you in all sorts of trouble." You started to stutter something out but gave up half way, distracted by his unwavering movements. Your hips jerk forward after a teasing minute, hands clenched at your side. "I was wondering when you'd realize and deliver, I like my punishments, but you don't look like the type to do it right." You grinned cheekily.
His jaw tightened, "Just to let you know sweetheart, I can let a joke or two slide before you really piss me off, Sam on the other hand-" He let his finger dip in you, flicking over your clit to pronunciate his brothers name. "Doesn't stand for any games." You let a mewl escape and you watched his adams apple bob.
He moved to lift your dress in the slightest, exposing your wet cunt to the head lights that passed every so often. The car jolts, Dean frantically looking towards the road to correct his steering. "Fuck." He curses under his breath at the sight of you. You move his right hand and grind down on it. "Please."
A sinister expression pressed on his face and he clears his throat. "Huh? What was that sweetheart?" You turn your head to look at him in the eye, frustrated at his stubbornness, a small pathetic pout planted on your features. "Please De-" He shifted his hand to grip your jaw and pulled you closer. "It's Sir, understood?"
You had to bite your lip to keep from saying it. You didn't want to just yet, you wanted to tease him as much as he teased you. As if he read your mind his rough fingers wrapped around your jugular. "Understood?" You nodded as best as you could, "Yes Sir."
The two of you jumped at the honk from behind you and Dean reluctantly pulled over to the side of the road. As he reached a stop he hoisted you on his thigh, bouncing it once like a silent demand. You placed your grip just above where your core met his suit pants.
You rocked your hips slowly at first, taking your time to relish in how it felt to be watched while committing such a vulnerable act. You choked out a moan at the thought, and as a reaction, Dean's hands flew to your hips pulling you against him harshly. His hand slipped under your dress and lifted it up slowly.
He took his time to memorize your body. You had to take initiative and let the straps of the clothing fall down your arms just to speed the process along. He watched your body move, an expression on his face so unholy. A hand slapped the passenger window, making you jolt, Sam lent down moving his hair from his view. His gaze was on you sternly, you caught his eyes once but averted them quickly.
Your cheeks heated up as the lock to the car sounded and the door opened. A soft bang made you jump and not long after, fingers enveloped your jaw turning your focus to the right side of the vehicle.
"Why'd you start the fun with out me?" Dean straightened his body and bounced his leg. You swore the both of them heard the small whimper in the back of your throat and the older Winchester groaned. "My fault, but please" He paused emitting a low chuckle. "Take it out on her."
The younger Winchesters big hand ran down your throat and over your chest. "I wanna see her squirm." He cupped your left breast and lightly massaged it a moment. Deans hand were working too, creeping up your legs, your sides only to capture your wrists.
The fog in your brain kept getting thicker, and in the next moment Sam has the passenger door open, laid out on his stomach. Before you know it, or can fully comprehend what was going to happen your back was arched over one of Deans knees. Your breast would bounce every slight movement he made and your head was positioned right between his legs. You could feel his hard member resting against your right cheek.
The younger Winchesters facial hair ran along your inner thigh making you twitch. Though Deans callous fingers that dug into the flesh, just an inch or so below your ears, kept your view limited. The lack of air making your toes curl. Cool wind blew on your wet cunt lips, your first instinct was to squeeze your legs together but his palms were holding them firmly to the seat leather.
Two ice cold digits spread you open, and you gasped. Your gaze caught Deans and his pupils were blown out and lustful, his tongue ran over his bottom lip and his hips jerked upwards, you could feel the heat of his cock through the slack material. He unbuttoned them slowly pulling himself from his pants. The tip was red and swollen and as if you've done this multiple times you let your tongue roll out from behind your lips.
Sam gave a broad lick to your core and you presented another small whimper, as you left a slick trail on the underside of the older Winchesters cock. He threw his head back and released a shaky breath. Combing his hair out of his face.
The tongue that swirled around your clitoris was making you lose focus, Deans hand redirecting you back to work more than a few times. Three digits were eased into you, the stimulation on you're clit causing goosebumps to gather atop your skin. You arched a little farther, drawing Sams body in close. He wouldn't thrust his fingers or anything, your desperate attempts to grind down on them laughed at. Proved by the low chuckle that came from between your thighs.
Finally he pulsed his movements, you knew he could feel your walls twitch around him and your cheeks burned red at how little you were going to last. You squeezed your eyes closed and arched your back even more if it was possible. "You can not come yet." Sams dark, stern voice just made it harder. You were trying to hear anything other than Deans hot whimpers, but it seemed effortless as your thighs shook almost right after.
Sams left palm tightly held back your plump flesh, the other leg on his right shoulder. His fingers inside you, seemed to strive to reach greater depth and you let out a humiliating cry. Not seconds later there was something warm dripping down the side of your neck. Out of breath and now running his finger tips along your jaw, Dean rubbed his cock and the remaining cum along your lips. You opened your mouth to catch the taste and hollowed your cheeks around his tip.
Sam sat up with a disappointed expression, wiping his mouth with his thumb, then dragging it down his tongue. Your brows furrowed, you could see the large tent in his pants and you sat up quickly. "I suppose we'll try again next tim-" Before he could finish you were rubbing his thigh with curious eyes. His own hooded and his jaw tightened. He leaned farther back in the seat, he nodded to his lap. "What are you waiting for then, whore?" Your heart rate picked up speed again and your arms were shaking as you reached to unbutton his slacks.
He was so huge he had to help you pull himself out, you hesitated when it was on full display. Subconsciously biting your lip at the sight. A rough tug was made at the nape of your neck, from behind you. "Hurry up, I wanna hear you gag on it." Then a harsh push made you stumble your face into Sams lap. You laid your tongue out and licked a wide stroke from the base of his member to the tip. You watched through your side view the way his let his arms drape over the seat.
It was like he gave you thirty seconds of control, until he grabbed a fist full of your hair, he was gentle for another minute or so but then you were complying to Deans demand. Your gags loud and perhaps a bit obnoxious, tears running down the sides of your face and you could see Sam smile. You could tell he loved the sight of you, it was written all over his face.
You've never had an experience this rough before. You had to close your eyes to focus on your breathing. Though it became harder when Dean dipped his tongue between your pussy lips for a taste. He moaned loudly, "Damn, sweetheart." You made a sound to reply and Sams grip wove in tighter, it hurt but the pain seemed to heighten your pleasure. You relaxed your throat a little more, still feeling the small kitten lick Dean was spoiling you with. The younger Winchester hummed in approval of your obedience with his pace. Picking up speed not but a few moments later.
He threw his head back and grunted, "If you keep taking it like that, I'm not gonna last." His words made your body melt, you found out pretty fast. You did your best to hollow your cheeks and move your tongue just in the slightest. The rhythm stuttered, his hips skipping a beat. Both hand pushed your head onto him and before you could take a breath he shot his load down your throat you pulled off with a few coughs, trying to ground yourself back to reality. A string of saliva still connecting the two of you.
Both of the brothers didn't miss a moment to put your dress straps back on your shoulders and brush your hair from your eyes. Deans thumb swiped the corner of your mouth calmly, your gaze hazily looking toward him. You opened your mouth to collect it without thinking and the two of them groaned. The youngest Winchester brother ran his nose along your jaw and bit your neck lightly. "Dean will clean you up and give you your reward," He lazily opened the glove box and threw Dean a case of wipes. You saw there was a couple water bottles stashed in there and you reached for one as Sam stood outside the car to re-button his pants. When he pulled off onto the highway, you could feel Deans anger.
Though his touches were gentle and caring as he wiped at your core once, before getting another one and wiping away your sweat. He lightly tapped the bottom of the water bottle and spoke. "Drink." You did as you were told and after that you were back on your path home. It was quiet the whole time, his now warm palm resting on your thigh your own resting atop his. You were sitting in the middle this time, it just felt right to sit closer to him now. The silence was needed, so you were grateful for it. You pulled up to your apartment complex and sighed.
You cleared your throat as you lent down to the floor board to grab your purse. "Thank you I had-" He smashed his lips to yours and hummed, "Don't be so quick to leave with out the cash sweetheart." He playfully chastised, "It'd be a dumb move on your part." He then proceeded to place a stack of bills in your hands.
All you did was nod and thank him, letting him walk you to your door and wink at you good night. "I'll text you in the morning, see how you're doing."
The whole apartment was dark when you entered, looking to the key holder you find Carmens keys aren't hanging up. You shrug walking to take off your heels. Your phone pings loudly in your purse. 'Did you make it home alright?' It was Sam.
You now had a small inclination as of why Dean was angry, Sam left his brother to pick up the mess. You furrowed your eyebrows and sent a reply, 'Yes, tell your brother I’d love to do it again sometime.' You knew he might not deliver the message though maybe it'll piss him off enough to stay a little longer next time.
@valsworldofcreativity @hobby27 @kikirebelqueen @bun-dpdbny
Lmk if you wanna be tagged they’re always open ALSO now that they’ve semi fucked it’s never going to stop 😌
