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Hey ya’ll I low-key started this a year ago so I apologize if certain parts are choppy.

It was a Friday evening and you were walking around the house that you shared with Sam and Dean. You were wearing nothing but a long t-shirt and your shorts that were so short could pass for underwear. Sam was out that night so it was just you and Dean home alone. You were curious as to what he was up to so you went to check on him

As you walk into Deans room unexpectedly, he quickly closes his laptop with a slight jump and he looks flustered.

“Were you never taught how to knock?!” He asks surprised at your sudden appearance and at your lack of clothing.

“Woah sorry if I interrupted something I was just checking on you because you’ve been quiet,” You said with a smirk. He tried to smoothly push his laptop under his pillow but you noticed it and he knew that. Dean looked up at you with one of his signature smirks, but you could still see the blush in his face.

“No uh—you just startled me that’s all,” he smiled slightly.

“What are you up to anyways?”

“N-nothing I was just uh…Researching a case.”

“Sure you were,” you inquired teasingly with a slight smirk.

“What do you think I was doing?” He asked slightly offended but embarrassed at the same time.

“Nothing, nothing it’s just you were quick to close your laptop as soon as I came in and-“

“I wasn’t doing anything bad!”

“I didn’t say you were”

“G-good because I wasn’t,” he stuttered.

“Are you lying to me,” you were interrogating him now. Not because you cared if he was watching that sort of stuff but for the sheer hell of it. You loved watching him get all nervous and flustered. It went against his normal ‘strong guy who gives everyone hell’ persona. You saw through him.

“N-no I swear.”

“Dean.” You raised your eyebrows and stepped closer to the bed he was sitting on. He sat up ready for your next words. You stepped even closer, and before you could reach the him, he swung his legs over the bed, facing you. You stood with your legs pressed up against his closed knees.

“I-it’s embarrassing..” he looked up at you with his model green eyes, and his lips parted. His face was flushed and there was no hiding how flustered he was now

You looked down at him with a smirk on your face, thinking about what to say to him next. You brought your hand and raised it to his face. You carefully grabbed his cheek and caressed it softly.

“You don’t have to say it honey I know what you are hinting at,” You began to tease him with a soft smile on your face. “You have nothing to be embarrassed about for the record I don’t judge.”

“Really?” He asked surprised. You and him were close but never talked about this sort of thing. Truth is, he had been sweet on you for quite some time now and barging into his room with nothing but a T-shirt on and an authoritative tone didn’t make it any better.

“Pinky swear,” you held out your pinky at him and smiled. He reluctantly went to meet your pinky half way and intertwine them together. When they met, you felt the room suddenly get hotter and it seemed that he felt the same way, judging on his face

He was looking up at you with his mouth slightly agape, and his eyes sparkled as you kept your fingers interlocked. His blush was still there, and his face could not hide his fascination with you and you took note of that.

You slowly pushed his legs apart with your leg and stepped in between his legs. His heart began to beat rapidly as he looked up at the ceiling, suddenly finding it interesting. He was so nervous you could hear every breath he took and you looked down at his lap, not surprised to see the growing bulge in his pants. You could clearly see his print and you would be lying if you said it didn’t cause you to grow wet.

You grabbed his chin and directed his face to you so you could look him in the eye. He struggled to make eye contact.

“Dean look at me,” you instructed. He reluctantly complied, awkwardly smiling. “Hey there.”

“H-hi.”

“Is someone nervous?” You asked teasingly.

He did not respond. He was thinking of some sly reply in his head and kept opening and closing his lips as if he was going to say something but he couldn’t. Instead of using his words, he nodded timidly.

“That’s what I thought,” you said before leaning down closer to him. You hesitated for a second before climbing onto his lap. You studied his face for any objection before you asked him forwardly:

“Is this okay Dean?”

Your faces were inches apart now and you could see him continuously glancing at your lips. He looked at you adoringly and responded:

“Of course it’s okay.”

Instead of giving him what he wanted straight away, you lingered there for a moment to see what he would do. His face was hot and he could not take it anymore.

“Just kiss me already!” He whined.

You smirked a devilish smirk and chuckled slyly. You leaned in closer to him and glanced down at his pink plump lips. They looked delicious. Finally you grabbed his face and pressed your lips against his. The kiss was slow and passionate and you were reveling in the way he tasted, it was just as you imagined; whiskey and apple pie.

Soon, you began to kiss him more passionately, opening his mouth and exploring with your tongue. Instead of fighting for dominance, he enjoyed the way you had your way with him, maybe a little bit too much. You slightly bit his lip and he let out a soft moan.

You pull back and smirk at him before asking, “Did you enjoy that?” Dean’s face flushes with embarrassment as he recalls the noise he just made from your bite on his lip. He is quite too timid to give you an actual response, and mumbles something under his breath instead.

“Can you speak up please,” you ask him. He huffs and repeats what he said under his breath.

“Yes I liked the way bit my lip,” he says with a sassy tone.

“Was that a hint of annoyance I picked up in your tone? Hm?” You questioned him to rile him up while simultaneously running your hands through his hair. He pursed his lips together before responding:

“No ma’am.”

“Good, that’s what I like to hear.” You smiled at him and continued to attack him with kisses. You focused on his jaw and then the middle of his neck, trying to find his sweet spot. He was enjoying this just as much as you were given the soft moans he continued to let out.

While you were attacking his neck you suddenly struck gold; you had found his sweet spot. Dean let out the most high pitched, pornographic moan you had heard from him yet, which made you peel back for a second to look at him. He immediately resorted to covering his mouth out of embarrassment.

“Why are you covering your mouth baby?” You asked with a smirk as if you knew exactly why he covered his mouth.

Dean looked to his right side, avoiding eye-contact with you, and let out a frustrated sigh.

“I-I-I didn’t mean to sound like that, m’ just not used to just sitting like this—doing none of the work.” He confessed to you embarrassingly.

You smiled at him with delight recalling the noise he had made. The moan was unlike anything you had heard before in a guy, it was marvelous and inviting. You relished in the thought before speaking your mind.

“Dean that was the hottest thing that you have ever done thus far, and I hope from the bottom of my heart that it happens again.”

You stared into his eyes as you shared this with him. His face flushed as you told him this and he grew shy thinking about the moan he had let out. He wondered how a woman could be turned on by such a pathetic, high pitched squeal. The idea was so new to him.

He looked up at you and smiled timidly. “Y-You sure it wasn’t a turn off to you?” His eyes sparked as he questioned you.

Starting off soft with SFW

Definitely MELTS when he catches you sneaking glances at him during class. Like if the teacher is drilling on about some boring homework assignment, and you happen to look at him, he will literally crumble (in a good way). It brightens his mood because here he was listening to the teacher babble on and on, and then all of a sudden, his stomach flocks with butterflies all because of you.

Loves writing you little love notes and sticking them in your locker between classes. Like he’ll write them in his classes when he’s bored and thinking about you, and then drop them off at your locker and wait for you behind a corner to see your reaction

ABSOLUTELY LOVES HAVING HIS HAIR PLAYED WITH in an innocent way but also sometimes…😏 giving it a little tug does something to him but that’s something that belongs down below. Anyway, it’s one of his favorite ways of spending time with you. He loves to lay in your lap and feel your fingers softly combing through his hair talking to him about your day. Sometimes, most of the time, he ends up falling asleep because he’s so relaxed and comfortable with you

He’s more out going around you than he is with the other boys because he knows you wouldn’t do anything to make him feel different

He gives you book and poem recommendations 😇 this man loves some Whitman

If he’s having trouble sleeping, he calls you up and asks you to sneak into his dorm because again, you just calm him down. He feels tired around you a lot because he’s relaxed around you.

Low-key hates scary movies, so if you guys are watching one, he’s always cuddled up to you, and clinging onto you during every jumps-care or slight change in music.

Will let you do his makeup if you ask really nicely

Likes being called pet names or names of affection like “baby” and “sweetheart” sometimes you let a “honey” slip by too once or twice

Like’s having his face held when you kiss him. Whether you’re kissing him on the head, lips, or cheek, he loves when you softly grab his face.

Has a secret sketching talent, and draws you when you guys hangout. If the conversation has died out, instead of awkwardly sitting there, he pulls out his sketchbook and draws you. Sometimes he adds color to these sketches and gives it to you. He absolutely melts when he walks into your dorm and sees that you have hung up his most recent sketch, or even framed it.

Definitely a cuddle bug. So please hold THE FUCK out that bitch😍. He low-key loves to be the little spoon and feels safe when you have him wrapped around your arms. In fact when you guys get up in the morning after spending the night he’ll protest “five more minutes…” He’s just that comfortable around you and feels safe in your embrace.

Reads to you. Yes, just yes

NSFW

I foreshadowed a bit in the SFW up there with the hair pulling…yeah…Need I explain more?

I guess I will ^ if you guys are heavily making out and you happen to run your hands through his hair, his mind immediately goes blank and anticipates the eventual hair tug from you. When he receives said hair tug, he becomes a mess. He’ll moan into the kiss and his legs will turn into putty so if you’re standing up, his balance will fly out of the window

Was very shy the first time you guys…you know…But once he realized that it was a safe environment with you and that you wanted it to be a memorable experience, he came out of his shell and it was magical

Very inexperienced and was only with one other person before you (Neil) (I’m kidding, or am I?😉) So he has done it, but not as good as it was with you. You kind of had to show him how to touch you and what felt good where, but he got the hang of it eventually because he’s a fast learner

Speaking of fast learning, he wanted to learn how to eat you out so he could reciprocate the pleasure you brought to him. He had never done it before, so when he was in between your legs he was so nervous that he was going to do something that hurt you instead of make you feel good. You reassured him that he was doing a good job, and to just not focus on it too much. So he took your advice and when he did…Oh Lord the things he did with his tongue. For someone who had never done that before, it was like he knew the ins and outs of you and his mouth perfectly fit on you. He kissed and sucked on your clit passionately and would look up at you occasionally for validation with those big blue puppy dog eyes of his and you would give it to him alright 😉 you ran your fingers through his hair and he moaned into your pussy as he ate you out and was simultaneously grinding his hips into the bed—he was really enjoying himself.😛

Loves when you’re on top and taking the lead

Still gets very flustered when you straddle his lap as if you guys haven’t done that a million times before, it’s adorable

I’m pleased to inform you that this angel WHIMPERS. Like I’m talking full on high pitched, almost pornographic whines. His breathing gets all heavy and he tries to bite his lip to stifle the noises but that fails every-time

Was kind of embarrassed the first time he let out a noise like that because he thought you would view him as less “manly” That was not the case however, and you wasted no time explaining to him that you found it extremely attractive and encouraged him to not be shy😏

Kissing him on his neck immediately turns him on

Has a sweet spot right about the crook of his neck and when you kiss on it he lets out the loudest whines ever