Summary: Reader and Dean have a bet on who can pick up the most people at the bar and things get competitive.
Characters: Dean x Reader
Word Count: 2172
Warning: Language, fluff, implied smut
A/N: Flirt war! Just let your imagination run wild at the end of this I guess, I fear my smut gets repetitive :/ Been nursing a pulled wisdom tooth for the last couple of days so apologies if it’s well… crappy. I’m not 100% but writing makes the pain lessen somewhat :)
Tag list originally from @spnfanficpond I deleted a bunch that didn’t seem to be working, and now some of these aren’t working either? I don’t understand Tumblr tags at all. Feel free to lemme know if you’d like to be added/removed.
“The next time Sam says ‘ooh it’s a simple ghost haunting, you guys can handle it’, remind me to hit him in the face with a brick,” You groan throwing yourself onto one of the motel beds.
“Noted,” Dean grunts as he copies you. You’re both covered head to toe in black goopy ectoplasm and cut up to hell. It wasn’t as simple as Sam thought but…well you had both handled it.
“Aw man, now it’s all over the sheets,” you grimace as you sit up and see a perfect black outline from where you’ve been laid, “Perfect.”
“Well, I’m getting a shower,” Dean announces getting to his feet, “Then we’re hitting the bar.”
“Ugh does it have to be we?” you scoff, “Do I really have to sit and watch you hit on skanks all night?”
It was about 2:00 a.m you awoke to a strange feeling on you forehead. You opened your eyes, dazed and sleepy, to find Taylor lying next to you playing with your hair. You gasped loudly as Taylor quickly, but gently, covered your mouth to muffle the noise.
“Don’t worry, Y/N. I know you’re surprised. I would be scared myself. But I’m only here to bring you pleasure,” he said softly as he uncovered your quivering lips.
You were wide-eyed and still confused as to why the hell your boyfriend Taylor Caniff snuck into you at 2:00 in the morning which in all honestly was really turning you on.
Taylor began to rub your left thigh as he gently licked and kissed your neck. You could feel your pussy begin to ooze with moisture. “Mmmmm,” you moaned as you instinctively grabbed the back of Taylor’s neck and pulled him closer. All you could think was that this must be a dream, but it felt too good to be a dream.
Taylor began moving down your neck down to your breasts.
“Does that feel good,” he asked awaiting approval. “Your body drives me wild.”
“Oh my God, yes,” You breathlessly replied.
His wet kisses felt cool from the breeze that was flowing through your room. You could feel Taylor’s erection through his jeans. His erection was throbbing with heat, you could feel it. It was about 8 inches and wasn’t too thick or too thin, it was perfect.
You exclaimed, “You’re perfect!”
“Thanks, I guess. Good genes maybe,” Taylor jokingly answered as he continued to pleasure you.
Taylor lifted your night gown and began sucking and nibbling your nipples, by now you were moaning and writhing, already wanting, almost needing, him inside you.
“I’ve never done this before,” you quivered.
“I know,” said Taylor. “Your first time needs to be with someone who knows what they’re doing, someone who you’ll remember. Don’t worry, I’ll take care of everything, just lay back and relax.”
You trusted him with your heart at that moment. You were scared and excited at the same time. You would’ve never thought a guy you loved would crawl through your window late at night and take you so confidently and passionately.
Your night gown was now on the floor; You could see the wet spot where your juices had leaked upon the smooth silk.
Taylor’s cock was hovering over your opening like a hawk ready to take its prey. He licked his way down your stomach and was even closer to your pussy than before.
He took off his shirt and his boxers, now he was also fully naked. You were in awe over his body. He wasn’t overly muscular, just muscular enough to make you squirm for him. And those biceps, oh those biceps, how wonderful they looked all bulged and flexed as he hunched over you holding his weight while he nibbled his way down to your clit.
You gasped as Taylor began to make gentle circles with his tongue around your clitoris. You couldn’t take it anymore; you were so wet you were oozing through the sheets. You saw that the tip of Taylor’s cock was also oozing with pre-cum.
“Take me now,” you shouted, “I want your cock to fill me up!!”
Taylor looked up from his work and replied, “All in good time, my love.”
He continued his way down from your clit to your moist lips. He opened them up with his glistening tongue. You felt his hot breath as he glided over your pussy.
“OOOhhhh, yes, YES…,” you stammered as his tongue tickled your labia.
Taylor opened up your legs and positioned himself sturdily between them, his bulging cock throbbing with heat and passion as it awaited entrance to your temple.
Your eyes met one another as you silently gave Taylor permission to enter you.
Taylor slowly entered you, to avoid causing you pain from the breaking of your hymen.
“Uhhhhh, ahhhhh…,” you cooed.
The head of his cock was at you wall and he ever so slowly proceeded to stretch your pussy so that he could fit his whole member inside you.
You gasped with pain as your hymen broke, you could both feel the small rush of blood that followed. The blood was more of a turn on than an inconvenience. It brought out the wild side in you that you had been hiding for so long. You suddenly wrapped your legs around him, pulling him in close. His cock was now fully enveloped in your flesh and you fucking loved it.
“I bet you didn’t expect that, did you, big boy?” you whispered in his ear, sending shivers down his back.
Taylor excitedly looked up and said, "No, but you sure know how to be fucked.”
Taylor began thrusting, slow at first to allow your vagina to accommodate his cock, but soon you both arrived at a medium pace, which you both liked. You both began to breathe heavily, it was so hot. Taylor nibbled and kissed your neck and earlobe. You were tingling with pleasure.
“I think I’m close, Taylor,” you whispered. “Take me all the way!”
You could feel the muscles of your vagina begin to contract; you squeezed your legs tighter around him and grabbed his shoulders. Your eyes opened wide and you took in short breaths, you then let out a moan that you’d been waiting to make your entire life.
“AHHHHH, FUCK TAYLOR!” you yelled, as you muffled your cries of passion to avoid waking your parents.
Taylor KNEW you were cumming for real, he felt the walls of your pussy close around his throbbing cock. He was moments away from pure pleasure himself.
“If that’s the way…you…want it,” Taylor replied in between shallow breaths.
Taylor sequenced his face and closed his eyes; he began to let out sighs and moans of ecstasy as he spilled himself in your tightness.
“I fucking love you so much Y/N!” He cried.
Suddenly, he withdrew. He was still climaxing. Taylor began to stroke himself and emptied the rest of his load all over your stomach.
“You like that, I bet you do! Lick it up; smear it on your pussy. Ugh…yeah…,” continued Taylor as you panted wildly underneath him.
Some of his juice even shot on the wall beside your headboard. You loved the feeling of his warm semen on your torso; you touched it and rubbed it in.
After stroking out every last drop of cum, Taylor collapsed on the bed beside you , both of you still breathing heavily and savoring your orgasms.Taylor’s cum was everywhere, on the sheets, the wall, not to mention on yourself.
You looked at each other and smiled. Soon, you were cuddling in the summer moonlight and cool breeze from the open window, reminiscing about the ecstasy that you both had just shared.
“I love you Taylor…,“ you whispered, still panting lightly.
“I love you more, Y/N.” replied Taylor, as he kissed your cheek
(A/N: (Y/B/F/N)= your best friends name)
"This can’t be happening.” you thought to yourself. You have imagined this moment a thousand times, wished for it on countless dark nights. That he takes you in his arms and lifts you up, kissing you passionately like it’s your last night together. It is your last night together…
It was first grade math class. You were sitting at your desk minding my own business when this boy sat down next to you.
“Hi, my name is Matthew” he said to you.
“Im Y/N” You told him. You smiled at each other. From that moment on you two have been best friends.
Now its 12th grade, you and Matthew are sitting together at lunch with all your other friends. your all laughing and smiling. Its your senior year. The principal just announced the date for Prom. All the girls are eyeing the guy that they want to go with. Unfortunately, its guys choice this year. That means the guy asks the girl. Your best friend (Y/B/F/N) leans across the table and whispers;
“Y/N, you should hint Matthew to take you to prom.” You glared at her, and whispered
“Matthew doesn’t like me like that. We're just friends."
"Sure your still in love with him though!” She teased
You kicked her leg. "Ow!” she winced. Everyone looked at her confused. “She kicked the table” You told everyone. Matthew laughed. The bell rang and it was time to head back to class.
“So who are you asking to prom?” You asked him.
He looked at you. His brown eyes made you want to melt. You were pleading for him to ask you. “Please, just please make my dreams come true.” you thought to yourself. Of course you’d never say that out loud.
“I don’t think I’m going to go to prom. I don’t have anyone to ask so what’s the point.” he said.
As he said that your heart felt like it was just shot with a machine gun.
“I’ll be right back” you told him.
You ran to the girls bathroom, locking yourself in a stall and started crying. You wanted to go to prom with Matthew so bad. You didn’t like anyone else like that. Nobody. Heck you didn’t like Matthew. You love him. Matthew has been the love of your life since the second grade. In first grade you were just getting to know each other but then BAM! You were in love. After a few minutes of crying your heart out you left the bathroom. You walked to your locker and (Y/B/F/N) was standing there.
“Y/N?, are you ok?“ she asked you.
"Then why does it look like you’ve been crying a waterfall?” she asked
"Because Matthew is not going to Prom.” You told her
“Aw, I’m sorry Y/N.” she said and hugged you.
She walked up to Matthew who was at his locker and slapped him across the face.
“What the fuck!” he said. You and (Y/B/F/N) walked into the class room and sat down at your desks. Luckily you sat next to (Y/B/F/N) during Science.
You and (Y/B/F/N) worked on your paper all through class. After class you went straight to your locker. Just your luck Matthew was there.
“Hey, are you ok? you seemed pretty upset when I told you I didn’t want to go prom with anyone.” You looked at him.
“I’m fine Matthew. Thanks for your concern.” You gave him a fake smile trying not to make eye contact.
“Well, who are you going with?“ he asked.
"The guy I want to go with isn’t going.”
"Oh who is he?, anyone I know?” he asked.
You stared at him dumb founded. You thought to yourself, you must be the most stupid person in the history of stupid people. Can’t you see I love you? You sigh.
“You don’t know him.” I said
“Really!? Then why did (Y/B/F/N) slap me?” He asked confused
“I don’t know ask her yourself.”
“Are you sure your ok?”
"Yes Matthew. I’m fine.”
The final bell rang indicating that we were dismissed from school for the day. You pushed past Matthew and rushed out the school door. Matthew walked over to (Y/B/F/N) locker.
“Hey, why did you slap me earlier?“ he asked her
"I slapped you because your the most stupidest pig head on the face of the planet.” She walked off. Matthew ran after her.
“Wait just one second.” He grabbed her arm spinning her to face him.
“What are you talking about?” he asked her.
“You hurt someone today, and you were too stupid to notice.” she walked off.
“Who are you talking about?” he asked.
She stops turning on her heels “Don’t you see!? Can’t you tell who you hurt!? Should I have to say her name?”
“Are you talking about Y/N?” he asked with disbelief.
She shook her head and walked away.
It was 3 days before prom. You decided you were going to go with your friends to prom instead of having a date. So you and your girlfriends all went to After Five (a store that sells prom dresses) Everyone picked out a bunch of dresses and you all went off to the dressing rooms. You all sat in the middle of the room and debated on every ones dress. When you came out of the dressing room in you beautiful, royal blue dress, all your friends stared with amazement.
“Y/N you HAVE, to get that dress!” (Y/B/F/N) squealed. You all laughed. You all walked towards the mens suits store, after paying for your dresses. When you all saw Matthew’s friends all giving Matthew comments on his suit he was trying on. You looked at your friends.
“He said he wasn’t going to prom.” You whispered at them
“I guess he is” (Y/B/FN) said.
“But whose he going with?” asked your other friend.
“The shirt doesn’t match the shoes.” your other friend said. You all stared at her.
“What the hell does that have to do with anything?” You all asked her. She blushed embarrassed, when you all noticed they were walking out with a bag.
"Shit here he comes! walk!” You whispered just loud enough for your friends to hear.
You all started walking down to Victorias Secret. The boys followed you girls in. You walked over to the strap less bra section. You were looking though the black bras when Matt sneaked up behind you.
“Hey, why are you getting this?“ he asked grabbing the bra from you with a small smirk on his face.
"Its for my boobs dumb ass. Give it back!” you glared.
He laughed handing it to you.
“I see you went shopping.” he said pointing to your dress bag.
You didnt respond, you ignored him and continued looking for your size.
“Why are you in here? This is a girls store, theres no boys department here."
Emphasizing the word boy. You finally found your size and cashed out.
“I’m here because I’m looking to buy perfume for my date.” he said.
Your heart sank. Date. Now you was sure he didn’t like you more than a friend. You noticed him glancing at his friends. They nodded. Each of them grabbed one of you friends and left.
“What the fuck is going on!” (Y/B/F/N) said to Cameron, since he was the one dragging her out of the store.
“Shh Matts trying to ask Y/N to prom” he said.
“Hes what!?” she squealed.
“Shut up ok I want to know how this goes too.”
Everyone stared through the display window into the store.
Matthew took your hand rubbing his fingers over it. You couldn’t help but smile at his touch. He looked up at you and smiled. You took his other hand and put your fingers between his. You felt your face getting hot. You were blushing. So was he. His face was as red as an apple.
“Y/N?“ he asked.
“Ugh will you um” he stammered taking one of his hands and rubbed the back of his neck nervously.
He bit his lip.
“Will I what?” you asked.
He swallowed hard
“Will you ugh go to Prom with me?” he asked.
He looked down biting his lip. You smiled ear to ear. You lifted his head so he was looking at you.
“I’d love to go to Prom with you.“
You hugged him. He pulled out two tickets with the words Prom on them in big bold letters. You heard screaming and cheering out in the hall. (Y/B/F/N) ran in and hugged you as tight as she could.
You tossed and turned all night in bed but you couldn’t sleep. No matter what you did. Finally morning came, you shoved the blankets off of you and ran for the bathroom. You stripped out of my t shirt and pink panties and turned on the shower till it was hot enough for you to handle. You took a razor from the shelf of bathroom supplies. It took you a while but you finished shaving all the parts of your body you needed to shave. you opened the shower curtain and stepped out. You walked back into your room and saw a long black box on your bedside table. Inside was a beautiful pair of chandelier earrings. There was a note attached to the box. “Hope you have fun at Prom tonight, Daddy will try and get home from work so I can see you in your dress.” - Love Daddy. You smiled and kissed the note.
An hour before Prom:
You were so excited this was finally it the moment where you get to put on your dress. You loved how it hugged your curves and showed off your breasts. You knew Matthew would love you in it. You put on my shoes and slipped on your black lace panties. You went into the bathroom to dolour makeup and touch up your sexy voluminous curly hair. You took a deep breath before looking over at the clock. You didn't realize how much time had gone by. Matthew was going to be here in less than ten minutes. You walk back to your room as you heard your mothers footsteps coming up the stairs. Probably to give you the parental speech about drinking and safe sex. Something embarrassing like that. She gave you a hug with tears in her eyes. “You’re growing up so fast.” She said. You and your mom were hugging in your room for what seemed like hours, when the doorbell rang. You both screamed in excitement. She fixed your hair giving you one last hug before making her way downstairs to greet Matthew who was standing next to your dad smiling. “I always knew this day would come.” Your dad told Matthew. You took your first step down the staircase, your parents were smiling at you while Matthew nervously stood there hold a clear box with the corsage inside. He was dressed in a classic black tuxedo with a nice skinny royal blue tie to match your dress. He looked up at you, with a flushed face and his signature bright smile. You continued walking down the stair case not taking your eyes off Matthew.
“You look beautiful.” complimented Matthew.
You blushed a deep red colour turning away.
“I um.. got you…” He stammered. He slipped the corsage on your wrist.
“Not as beautiful as you.” he said smiling.
You took the flower and pinned it to his jacket. You were so proud of yourself, you pinned it on him without hurting him. Your dad took out his camera. “Alright time for pictures.” he said. You took hold of Matthew’s arm as your dad took a bunch of pictures of you two. You gave your mom a look after your dad had taken over 50 pictures of you and Matthew signalling your mom to take the camera away from your dad. You and Matthew headed out to the limo which was waiting in your driveway. He helped you in and there inside the limo all your friends were screaming, laughing, smiling, and complementing each other.
After a couple of hours of party on the dance floor Matthew grabbed your hand and led you out to the hotel elevator where he pushed you against the wall and kissed you roughly. This sexually tension had been building up between you two all night.
You gravitated towards each other kissing deeply. You both came up for air and started removing each other clothes, in between deep kisses, your clothes were literally thrown all over the hotel room.
You kissed each other on your way to the bedroom, falling on my bed in a tight embrace. “I want this,” you whispered, reading the concern written all over Matthew’s flushed face.
He entered you slowly, wanting to savour the feeling you both desired since you laid eyes on each other twelve years prior. It felt like he had been penetrated by your soul, this was beyond sex. “You’re so tight,” he said against your neck. Wet could not even cover what you were, you felt like your entire purpose on earth was to receive him. He started a rhythm, pounding you as he placed butterfly kisses down your neck and on your breasts, with his hands stroking your every inch. You ran your hands down the length of his biceps, loving the feeling of his weight and arms on either side of your body. Your fingers fluttered over his chest, loving his erect nipples. You felt your pussy pulsing around his cock, embracing it, releasing it, embracing it, then releasing it. You look down at where your bodies meet and admired the sight of his cock entering you with such gentle fierceness. You raise your eyes to him to find him staring at you, he mouthed your name in wonder. You traced his lips with your fingers and said his name back; it was like you both were trying to ensure that it was not another fantasy but the real thing. Matthew felt so good, you could feel you were getting close. And then you felt his cock grow bigger as his breath started to flutter and you gripped him tighter with your pussy. His breath grew short and he started sounding like he was fighting a losing battle against his own body. He threw his head back and pounded into you, hard.
“Y/N! Y/N!” Matthew shouted as his flow splashed into you. You began screaming his name out with ecstasy as you came.
You both lay panting on the bed, both coming down from your highs.
Already many thoughts were running through your mind. You pushed the thoughts aside and moved closer to Matt. He hugged you closer as you felt him slip out of your drenched pussy. He sighed. “Y/N, I have a confession.” He laughed, panting. You turn to face him nodding your head giving him the go to proceed. “I’ve always loved you Y/N.” Matthew admitted. “I’ve always loved you too Matthew.” you say before pressing your lips against his.