you had been teasing dean all day. just the little things like when you would drop something and bend over right in front of him in your jeans, the curve of your ass and the fabric tightening around your thighs. the blood rushed straight to his dick right then and there.

or when you were changing before a hunt and slipped your lounging shirt off in a way that made dean have to stop and stare. his arms snaked around your waist from behind, “baby come on, let’s make sammy wait up just a minute?” he whispered into your ear. but you felt a little cheeky, and shook your head no, which was unusual for the two of you. “not right now, we have a job to do.” dean looked at you in a way that was almost like you refused to play with a puppy.

and just about an hour ago when you took a trip to the bar, you leaned over the counter and flirted your way to a free drink with the bartender. giggling and tucking your hair behind your ear, eyes never leaving the man’s face. dean watched, he was usually okay with it because you both agreed free is free but today he just wasn’t having it. you got your drink and finished it up dean pulled you out of the bar without warning.

and that’s what got you here…

legs spread, dean’s hands holding them open, his grip tight on your thighs. his mouth sucking at your clit and tongue sliding between your folds as you cried out his name. he’s been doing this for too long and he hasn’t allowed you to cum once. “dean! please- pleaseplease! fuck!” he tilted his head to look up at you, his mouth and chin glistening with your slick. “mhm, you wanna cum baby? yeah?” he cooed, and you nodded. your chest heaving up and down, trying to catch your breath. “that’s too bad isn’t it. y’ been teasing me all day, pretending you didn’t know what you were doin.”

his head tilted back down as he licked a stripe up your pussy, gently sucking on your clit. “you didn’t want this?” he rasped out. you just whimpered in reply, you were so sensitive and ready to release at almost any touch. “speak up baby, tell me you didn’t want this.” but you both knew that you love this, you wanted this. “that’s what i thought. dirty fuckin’ girl.”

dean’s mouth continued to work at your pussy til you couldn’t take it anymore, were squirming and tears fell from your eyes. “dean fuck— please! please.. i’ll be good!” you said loudly. very glad dean decided to do this while sam was out. dean smiled against you, “okay baby. let go, you deserve it.” and at those very simple words you released. your juices soaking his face, the lewd noises of him licking you up filled the room. your legs shook and your body spasmed as you came down from your high.

“we’re not done.” he said roughly into your ear. he grabbed your jaw and his hands were rough against your soft skin, he pulled you into a kiss and you could taste yourself on his tongue. “can’t tease me all day and think i won’t be cumming too.” he mumbled as he gripped your thighs and pulled you close to his hips. you looked up at him with your fucked out expression, “you can take it right honey?” and you just lazily nodded in reply.

he was only in his boxers but not for much longer, he pulled them down in a swift motion just enough for his cock to spring out. it slapped against his torso, you looked and it was throbbing and slick with his pre. you could already feel the heat pool in your tummy once again.

he gave himself a few strokes before sliding himself into you inch by inch. you gasped at the feeling, your brows furrowed and you let out a low moan as he bottomed out.

his movements were slow in the beginning, small thrusts that drove you crazy, you were still sensitive from the previous round and he just wanted to torture you. “feel s’ good around my cock. n you look so pretty fucked out, pretty slut.” you moaned at the nickname and once he started speeding up the pace. he held your thighs, your legs up on his shoulders, and his hips snapping against your skin.

his hand moved down to rub at your sensitive clit, his finger circling around it. “dean! fuck!” you moaned out. the sensation of your already used pussy and him continuing to overstimulate you made you feel almost dizzy. your vision was white around the corner of your eyes, you could barely see dean in front of you. but you could feel him, and there was nothing better than this feeling.

dean’s pace got sloppier and faster, he could feel himself getting closer and so could you. “can y’ give me one more baby? i know you can.” you nodded in reply. dean hit your sweet spot and you gasped, creaming around his cock. your vision went white and your eyes rolled into the back of your head, the overwhelming feeling washing over you.

he slowly pulled out of you as you came down from your high, his hand moving around his own cock and he came on your tummy. dean flopped down beside you, both of you attempting to catch your breath and collect yourselves.

“y’ all good baby?” he grabbed your waist, pulling you in closer. “mhm.. m’ just worn out.” you giggled, and he smiled. “let’s get you cleaned up.”

an: day one completed! i live pst btw if this is late for any of u! please lmk what you think ^_^ and stay tuned for day 2 luvvies.

@ackl3z @vodkanoredbull @anibeaar @wwvvii @impalaaa-67 @miretlerans @czsgonemad @surr4denec4 @zjasminelouvre3 @stariou @turkawkas @hot-and-confused @deans-1angel @spnbbunnyy @c1eepypas1a @abigolemess @anqelzi @otherluckywitnesses @a-gay-alien @yellowdinosour

day one: orgasm control . dean winchester

day two: coming untouched / dry humping . sam winchester

day three: threesome . dean winchester + castiel novak

day four: phone sex . sam winchester

day five: dacryphilia . sam winchester

day six: humiliation . dean winchester

day seven: blood play . ruby 2.0

day eight: puppy play . sam winchester

day nine: exhibitionism . dean winchester

day ten: punishment . cordell walker

day eleven: somnophilia . soldier boy

day twelve: infidelity. sam winchester

day thirteen: dom/sub dynamics . dean winchester

day fourteen: choking / gagging . soldier boy

day fifteen: semi public . castiel novak

day sixteen: fire play . ruby 2.0

day seventeen: messy sex . clay miller (friday the 13th 2008)

day eighteen: size difference . sam winchester

day nineteen: cream pie . soldier boy

day twenty: mirror sex . castiel novak

day twenty-one: omorashi . sam winchester (is this too freaked out)

day twenty-two: sensory deprivation . casitel novak

day twenty-three: praise kink . sam winchester

day twenty-four: free use . dean winchester

day twenty-five: double penetration . demonblood!sam + ruby 2.0

day twenty-six: lingerie . cordell walker

day twenty-seven: hair pulling . dean winchester

day twenty-eight: multiple orgasms . sam winchester

day twenty-nine: sugar baby . cordell walker

day thirty: breeding . soldier boy

day thirty-one: surprise!

you sat on your bed with your best friend, becky, giggling and laughing as she just hung up on her ex after pulling some dumb prank you guys saw on social media. he was just confused the whole time, “god he was never my favorite ex,” she said as she had finally caught her breath. “i can see why.” you replied, wiping tears from your face.

“okay your turn. who are you gonna call?” she asked curiously. “the guy from the bar was pretty cute.” you shook your head as you scrolled through your contacts, “sam.” you flipped your phone to show her the contact.

you and sam dated for about a year, and you haven’t even spoken to him in one either. becky’s eyes widened, “are you sure— i mean isn’t that kind of hard to take in, on both sides?” you nodded. “but, it’s fine. it’s just a dumb prank, we didn’t end off that horribly.” becky just shrugged, like whatever you say girl. your fingers hovered over the call button before finally pressing down.

ring, ring, ri— he picked up. only after two full rings of your phone. your heart was racing, becky was trying to cover her laughter already forming.

“hey sam..” you said softly, a smile playing on your lips. “.. hey? is everything okay?” sam replied. he sounded confused.

“i was just calling to say goodnight.”

“what the fuck?” he let out a single stunned laugh.

“that’s it. i’m sure you’re busy studying though, so just goodnight.”

he snorts, “okayy.. goodnight. are you sure you aren’t drunk?”

you clicked the mute button quickly, you and becky bursted into laughter. “he’s taking it better than i expected.” you said in between giggles, “okay okay shh. keep going.” becky encouraged. unmute.

“no no, i’m not drunk! im just saying goodnight, i can’t say goodnight?” she says with confused tone.

“we haven’t spoken in a year and all of a sudden you wanna say goodnight?” you could hear him shutting his laptop, meaning his focus was all on you now. “what are we doing here? y’ miss me?”

your eyes widened, you could feel your heart practically beating out of your chest. because i mean— your feelings weren’t the prank. you definitely missed him. but should you admit that with becky right here? i mean she was the one who encouraged you to not contact him after your breakup.

“something along the lines of that..” you said innocently. you brought the phone closer up to you, pulling your knees to your chest. “do you miss me?” you had to know. becky looked at you with a raised brow.

“yeah.” he says too quick. his voice was lower, he was serious. “…my roommate is gonna be gone tomorrow night.”

“…okay?” you said puzzled.

“so, are you trying to come over to talk?”

you spoke in a breathy tone, a little too flirty almost. “i only wanted to hear your voice.” his voice was like honey to you. so smooth and comforting, but sometimes left that burning feeling.

he groans softly, more exasperated with himself than her. “you’re horrible.”

silence stretches between the two of you. but he breaks that with “are you gonna take up my offer? seeing me tomorrow, my dorm?”

you glance at becky, her eyes narrowed. “maybe.” you replied, chewing on your bottom lip.”

“goodnight y/n.” and then he hung up.

you were then met with a slap on the arm from becky, “he’s right, you’re horrible! if you do see him tomorrow i don’t want you calling me and crying.” becky ran a hand through your hair, “well you can call. but don’t say i didn’t tell you that this is gonna be bad.”

you couldn’t say anything. because you were honestly excited to see him again, like a little high school girl with a crush. you just smiled at her. “it’ll be fine.”