AN ANGEL d.winchester
𝜗𝜚 WORD COUNT - 4.5K
DEAN WINCHESTER X FEM!READER
𝜗𝜚 SUMMARY - You're nervous to lose your virginity, Dean shows you everything that you've been missing out on.
𝜗𝜚 WARNINGS - smut, dom!dean, sub!reader, nervous/shy!reader, unprotected sex, creampie, p!v, teasing, loss of virginity, fingering, hickeys (r.recieving), size kink, praise kink, dean is experienced, reader is inexperienced, (1) thigh slap, big dick!dean, boob fondling, boob sucking, reader is smaller than dean, illusions to past masturbation, reader blushes, petnames, intended lower case, nothing i write is ever proofread 🩷
dean liked having you sat in his lap.
this wasn't the first time, your legs stretched around his waist while your hands scrunched idly at the black shirt he'd been wearing, your lips against his own. making out with you had to be possibly the best thing he'd ever done. it was like getting sent to heaven and back, between each breath he damned the gods that disallowed him to press his lips against yours for forever.
but you were new to all this.
he had to be gentle.
dean was the first real relationship you'd ever had. and if he was being honest, you were sort of the first real relationship he'd ever had too.
he used to hop from girl to girl, bed to bed and not think twice about it. you were the absolute opposite. you were the type of girl that didn't speak unless spoken to, you kept your head down and got through everything without so much as letting your imagination wander with what it would feel like to be with a man.
then you met him.
his hands were pinching at the fat of your thighs, he found it hard to keep his hands to himself when you were like this. between kisses, he could hear the shakiness in your breaths, it drove him unbelievably mad.
you felt almost sorry for dean, knowing it'd taken this long to get comfortable enough to even make out with the man. you knew his history and how he wouldn't go longer than a week without someone in his bed. now he'd went more than three months with you like this, aching for more.
and it wasn't like you didn't want more, believe me, you'd been aching just as horribly.
you were just... scared?
deans hands moved harshly against your skin, right hand coming down to gently slap your thigh before gripping it once again. the feeling prompted a low whimper to leave your lips.
dean almost groaned. he could get used to hearing noises like those.
when the man pulled away from your lips, heavy breaths still leaving his own, you swore you could have whimpered again just from the loss of contact.
he looked down at you, eyes all blown wide, lips slick and swollen, it was a sight he hoped was never erased from his memory. he wanted to remember this forever. "y'so needy." he had that cocky grin on his lips, cocking his head to the side as he viewed you as a whole, all his, right in his lap for the taking.
you felt your cheeks get hot at the sentence, eyes immediately darting anywhere other than his face. "don' be mean." was the mumble you let out, eyes adverting and voice lowering. you weren't able to talk to him, not when he got like this, all 'bigger' than you, it made you feel small, it made you feel wet.
"'m not, 'm not." he spoke with a low chuckle, one of his hands raising to meet your face, you felt the padding of his thumb wipe across your hot cheeks, he could tell you were nervous. then again, you were always so nervous. "i think it's cute."
again, your face got increasingly hotter but dean didn't leave you any room for words, dipping his head so his lips could meet your neck.
there was something so surreal about being like this, your hands gripping at his shirt, top lip clamped down on your bottom as he kissed against the skin of your neck.
again, this wasn't the first time he'd done something like this. makeouts and hickey-leaving was getting more and more natural in your relationship, common, even.
he'd come home from his hunts with sam and all he'd want was you either below or on top of him, his lips against anything they could reach.
you felt his lips part, sucking against your neck as one hand ran up your back, the other cupping the back of your hair. once he sucked, his tongue would smooth over the skin, pleasure to ease the pain. and he'd go again, gradually moving to different places on your neck. marking you.
your own lips were strewn shut, you were hoping and praying on every star that you didn't let a noise slip from you. you were too nervous, too embarrassed but the whole point of this was to feel good, wasn't it? so why did you feel so embarrassed to show him how good it felt?
your eyes fluttered shut, the feeling suddenly overwhelming.
you didn't register the move of your hips until his lips left your neck and his hands clamped down on your waist, low grunt leaving his mouth.
you stared at him with those big eyes and he swore he was gone. "y'can't do that, sweetheart." despite his words, his tone was gentle. "can't start something if you don't want to finish it."
he knew how inexperienced you were, he thought you wanted to hold off on losing your virginity which is why he'd never made such a move but by the way you were looking at him now, he swore you wanted nothing more than for him to take you.
and he'd gladly do so upon your command.
"i do..." you uttered. ".. want to." the words made your insides twinge, made your nose scrunch and your lips purse.
you were too nervous, shaking like a leaf on top of him. even so, with so much anxiety bottled into a human, dean made no movements of caution.
you sort of liked that dean wasn't as awkward or nervous as you were. dean was confident, that much was for sure. but being so confident also gave him this openness, seeping comfort into your veins as his large, warm hands trailed up and down your thighs.
"yeah?" his voice was breathy and his smile had left his features. he didn't need to be so teasing now, he knew you would simply burst of shyness. and he didn't want you in a position of uncertainty. "what d'you want?"
he wasn't trying to tease you, though he knew his fingers that began to dance against your skin were doing nothing to calm your nerves.
he just needed to hear you say it.
you planted your face into his chest with an incoherent mumble, cheeks alight as flames.
dean could have laughed at you but he didn't want you thinking you'd done something wrong. on the contrary, he found it downright adorable how shy you'd been getting. but you couldn't help it, this was such an unfamiliar feeling bubbling in your stomach.
"can't hear you, sweetheart." his head came down to sit atop yours, his voice a gentle whisper. "i need you to tell me what you want, okay?" his free hand tipped your chin upwards to look at him, those pretty green eyes held so much sincerity. "use your words f'me, baby."
words felt stuck in your throat, you couldn't seem to get them out. but dean didn't want to let this get away from him, he steadied your chin between his fingers.
"i want..." your voice was all breathy, all needy. it had dean reeling. "i want you to touch me."
and as the words passed your lips, you swear all the air was knocked from your lungs. listening to yourself talk had made your head feel fuzzy. before dean, you couldn't have even imagined such words leaving your lips.
dean was struggling to compose himself but nonetheless, he did. his lips quirked into this proud yet sly smirk as his fingers ran up and down your thighs. "where, angel? here?" he practically mocked, fingers against your knee.
at this point, dean had never seen an angel, he didn't believe in them. but he was sure that if angels did exist, you had to be one of them.
you could have corrected him verbally, told him to stop teasing or even scolded him for mocking you while you were all worked up like this. but instead, you chose to grasp his bigger hand in your own and trail it towards your core.
as your hand cupped his own, he could feel them shake, he almost cooed at you but he didn't want to make you more nervous than you already were.
but when his hand finally reached your clothed core, he couldn't help but let out a groan.
it didn't take longer than a second for dean to have you flipped over with your back against the mattress of the bed. a noise left your lips as he towered over you, that infamous smirk etched to his lips.
but a type of seriousness washed over him. "are you sure you want this?"
you knew he wasn't asking you to tease you or make you wait, he was being sincere and you couldn't have been more sincere back by bucking your hips with a low whine of the word, "yes." quickly followed by a "please."
"so needy." he mumbled back, lips moving to your neck while his fingers fumbled at the cotton material of your baby blue sleep shorts. he hooked his fingers around the waistband and tore it off skilfully.
he supposed his experience was paying off.
you didn't have any time to counter what he'd said, too focused on the feeling building in your stomach. much of it was worry, anxiety even but the majority of it was this foreign, amazing feeling.
"fuck." his ring clad fingers circled against your panties. you were suddenly hyper aware of how worked up you'd gotten while making out with him, a blush creeping in on your face as you turned away from him.
dean all but tutted, dragging your face back.
"don't get shy on me now, sweetheart. This wet for me, the least you can do is look at me." he had that empowering stare that told you he was in charge here, it had you shrinking further into the mattress.
but dean wasn't demanding, sure he was dominating but he didn't make you uncomfortable. truthfully, you'd been rather scared of getting this far with anybody but you were sure that if there was anybody you wanted it to be with, it was him.
his hands toyed at waistbands of your panties. "this okay?" his eyes were glued to your face, trying to watch every way your face contorted, making sure you were okay.
believe it or not, there was a lot one could tell from just looking at someone.
you nodded your head briskly, darkened and bitten lips parted slightly, covered in the slick left behind from your tongue. your cheeks had turned a darkened colour too, blush spreading across your face.
there was something so surreal about looking at you like this, knowing nobody else ever had. he pulled the panties down your legs, watching you steadily with his own lips parting open. his eyes moved from yours to trail down your body, landing on your sopping core. he couldn't help but breathe in a breath.
"you're so pretty, angel." he moved his hand upwards again, closed fingers gently toying with your clit, which earned a soft gasp from you. his lips quirked as he brought his hand away, using the other to slip off his ring. he took your wrist, holding it up gently. "take care of this for me, yeah?" you nodded as he slipped the ring onto your thumb, seeing as your other fingers wouldn't fit it. "good girl." he mumbled, pressing a kiss to your cheek.
he was suddenly hyper aware of the fact that you were a virgin.
now, dean wasn't necessarily put off by the fact that you were a virgin. dean couldn't have cared less what you were. but he needed to make sure he was gentle, more so than any other time.
because he was the first, the one you'd remember forever.
though, he intended to be your very last, too.
his fingers trailed across your pretty tank top, down to your hips and finally edging between your legs. he peppered kisses against your face and down across your jaw, finally landing on your neck, fingers pushing your legs apart with ease.
as shy as you were, you didn't hide from him, you allowed him to part your legs, his hand was against your inner thigh, softly soothing up and down against your skin.
but he had to make sure, before he touched you. "sure this is okay? not having second thoughts?"
of course dean wanted to but he only wanted to if you wanted to. but you nodded anyway, swallowing though your mouth was dry anyway. "'m just nervous." you admitted softly.
it was no secret to dean that you were a nervous creature already. he knew this was all new to you but he didn't want you to feel shy around him. "you don't need to be." he pressed a kiss against the supple of your cheek, hand moving further as you let out a shaky breath. "not with me." as the whisper left his mouth, his hand came up to touch your hot core.
the noise that left your mouth should have embarrassed you but right now, you couldn't think of anything other than the feeling of his hand right where you needed him.
he collected your wetness onto his fingers, spreading it up and down your folds, two fingers parting from the rest as he gently eased them into your hole.
heavy breaths suddenly left you, chest rising and falling while dean's face was practically hidden in your neck, peppering kisses, sucking and licking against the soft skin while his fingers settled inside of you.
he gave you hardly any time to adjust to the feeling, pulling them out and then thrusting them right back into you. "you're so warm, sweetheart." he mumbled in slight awe. suddenly, the image took over his mind, the image of him inside of you. he couldn't seem to wipe it away.
he knew that giving yourself to him even just like this was a lot for you, he didn't want to push you any further than he already had tonight.
however, the image still tainted his memory.
as the speed of his fingers increased, so did the volume of your noises.
a sticky, wet sound bounced from wall to wall, causing your cheeks to warm incredibly further. you flushed, your own hand coming up to cover your mouth, suddenly aware of how loud you'd been.
a coo left his lips, free hand coming to drag your wrist away from your mouth. "wanna hear every noise you can make, angel."
and his words alone made you whimper.
the palm of his hand bounced against your clit with every thrust of his hand, emitting these noises from you that you'd never been able to draw from yourself.
"y'sound so pretty, you know that, baby?" you made a noise to show you were listening, though all it told dean was that you felt good. "look so pretty too. so beautiful. all mine."
dean couldn't keep his hands to himself.
his free hand dragged against your skin, pushing at it as if trying to get closer to you in any way possible.
against his fingers formed a creamy ring. he looked down at his digits sliding in and out of you, wetness surrounding you both, keeping you together by a wet string.
he let his thoughts wander.
as evil as it was, he simply couldn't think of anything else, he imagined it was his dick sliding in and out of your hot, wet hole, the noises you'd make would be so much louder, you'd be so much fuller.
then he was suddenly aware of your experience once again.
you were tight, incredibly tight which only made him scissor his fingers. if you were going to take his dick, he needed to stretch you out first.
"dean!" you spluttered out as he scissored his fingers inside of you. "c-cant."
your hips bucked backwards, as if you were trying to tell yourself to stop, but it felt too good to stop.
and dean knew your body well, more than you knew it apparently for he only tutted, holding your wrist in his free hand. "you can take it baby, there you go." and he must have known what was happening because your insides were turning to mush.
you'd orgasmed by yourself before but this? this was true bliss.
he held your waist down to the mattress as your body squirmed, head falling back into the pillows as his name fell on your lips, moans and whines blissfully leaving your slick lips.
"good girl." he mumbled, pressing kisses anywhere his lips could reach. "you're so good, there you go. atta girl."
his words of praise fell on your lips, only making you squirm impossibly more. but nonetheless, he kept up his pace, fingers moving to help you ride out your high.
dean swore he'd never seen something so beautiful.
he watched in awe, staring at the way your face scrunched up, pretty lips parted and your eyes screwed closed, though he could only imagine you were seeing stars behind your lids, not that he was being cocky or anything.
the sight was pure bliss, angelic, even.
he swore he'd been to heaven and back, just watching your face contort.
and he'd watch it forever, if he could.
he was suddenly aware of how tight his jeans felt.
"i need to fuck you." he was mumbling with a slight neediness in his tone, kissing up and down your throat, his hand only coming to a halt when your own practically pushed it away, the overstimulation becoming too much. "can i?" a beat passed. "please?"
his face rose to meet yours and you stared at him, all blissed out. you swore that his fingers were the most skilled, pleasurable feeling you'd ever felt, much better than to how it felt when you'd done it by yourself. your lips were glossed over, heavy pants leaving your chest. huge eyes and flushed cheeks.
almost a whine of the phrase, "uh-huh." passed your lips.
and it was enough for him.
his lips crashed into your own, kissing you ever so softly, though there was passion hidden somewhere between your heavy breaths.
needy hands pawed at the end of his black shirt, his own hands reached down to cup yours, helping you tear it off of his body. his amulet dangled downwards, just below your face and he was suddenly very aware of the fact that your top was still on. he supposed he'd been too focused on making you feel good to realise.
his hands reached the end of your own top, helping you push it over your head.
no words left his lips but they parted, tongue passing over the bottom one as he stared.
your pink bra was so pretty on you he almost had to think to decide whether or not he wanted to keep it on. but he decided with the latter, hands unhooking your bra skillfully, as if he'd done it a thousand times before.
he hardly got to see your boobs, for his hands cupped them as soon as they were let out of the bra. he cursed out a grunt under his breath, one hand leaving your breast so his mouth could replace it.
against the mattress, your back arched, stomach against his own while you bit back the pretty whimpers which he yearned to hear. his mouth worked against you, rolling his tongue back and forth, practically flicking your nipple in his mouth making you unable to contain the sounds you so desperately tried to keep back.
"d―dean!" you spluttered, eyes fluttering shut. his own eyes looked up at you, watching your face contort once again.
he had to have you.
as his face left your chest, a string of spit connected your boobs to his lips.
he wiped it away, though nothing could wipe away that smut smirk he held. nonetheless, he helped himself to shimmying out of his jeans, taking his boxers off with it.
it wasn't until he took everything off that reality set in. you stared, eyes blown wide, he was, well... big. and it was sort of hard not to get nervous, even with the fact that his fingers had just been stuffed inside of you, you weren't so sure it was going to fit.
"you okay?" he leaned down, towering over you. he realised your eyes hadn't moved from his dick, pulling your chin up with his two fingers. "are you sure you want this?"
you nodded your head, thoughts a mere muddle of clouds. "i just... 'm nervous." you admitted, feeling your stomach fill with this fuzzy feeling that you only got when you talked to dean.
"you don't have to be nervous, sweetheart, not with me, okay?" the palm of his hand rested on your face. "do you want this?"
"yes." you answered without a beat.
"promise?" you could have melted right then and there. dean winchester was of many things but above all, he was gentle.
"promise." you mumbled, finding yourself relaxing just at the mere sound of his voice. his hand trailed up to find your own, fingers interlocking yours. his free hand moved down to his dick, pressing it in his hand.
you watched with curiosity yet also nervousness. you'd never seen this done in real life, so the shyness was creeping in as you watched him move his hand up and down his shaft, dragging it towards your wet hole. instantly, a sound left your lips, blush instantly creeping in as your eyes snapped up to him. he only smiled gently at you, finding your shyness rather adorable.
the head of his dick slowly pushed inside of you and that alone had you feeling awfully stretched. he wasn't just long, he was thick too meaning he stretched you out completely. "okay?" you nodded at the sound of his question, the feeling of his lips on your cheek moments after. "'s gonna hurt a little, alright?"
you nodded your head, eyes shutting closed as you braced yourself.
you weren't an idiot either, you knew first times were supposed to hurt but luckily for you, you had dean right there, holding one of your hands tight in his own, soft whispers and kisses against your skin.
what more could you really ask for.
he slowly eased himself inside of you, worried he was hurting you. then again, there wasn't really any other way to get inside without hurting you. he watched as your face contorted, a gentle whimper leaving your lips but he knew it wasn't one of pleasure, more of pain, actually.
he mumbled gentle apologies and left a trail of them in kisses from your neck to your cheeks.
finally, he was in completely and he couldn't help the string of curses that he mumbled under his breath.
dean stayed as still as he could. worry set in, he didn't want to hurt you, not when you'd been so nervous in the first place. he'd been with many girls but you were a tight fit around him, swallowing his dick whole. he couldn't help but almost coo at the way your hole clenched around him.
he felt your hips shift, and he knew you were ready. "can i―fuck, sweetheart, can i move?"
again, you nodded with a subtle whine that told him in other words, yes, he absolutely could move. and that was exactly what he did.
he slowly pulled his dick out from inside you then suddenly slammed his hips back in, his dick hitting the spot deep inside your walls. instantly, he was met with a mewl.
"shit." he uttered, wanting to draw as many sounds like that out of you as he could. his two hands now rested on yours tightening his grip as he placed them over your head so he could gain better access. "oh, fuck, sweetheart, you're so fucking pretty."
it seemed as though dean had the mouth similar to a sailor when put in a position like this.
but he couldn't help it, you were staring at him with those doe eyes, pretty noises falling from you. his hips moved with ease, slamming in and out of you, it didn't take him long to pick up the pace either.
your legs lifted to surround his waist, moans leaving the two of you as his hips slammed inside of you.
"shit, you're so good for me." he was a mumbling mess, he meant every word of what he said, though he wasn't too sure what was leaving his lips as of now. "oh, my sweet girl, thaaat's it."
he tipped his head forward, connecting his forehead to your own. your whimpers and whines were swallowed by a kiss, gentle yet so full of neediness, it was exactly what you wanted.
"feels..." you mumbled once your lips had parted, though you were sort of dazed, not all the way there. "feels so good."
"good girl, 's it, take it all." you felt his hand suddenly trail down, fingers soft against your clit while his dick still hot between your gummy walls. "'s okay, you're okay."
you shook your head, swallowing thickly as your hips bucked. "'s―'s too much!" you panted out, moans leaving you as if you couldn't keep them inside.
"you can take it, baby, know you can." but he could tell by the way your face twisted again, you were close.
and so was he.
"you gonna let go f'me? huh?"
at this point, your eyes had fluttered shut and you lips were parted as you nodded, brows strewn together. "gonna... 'm gonna cum, dean."
"that's my girl." he answered, pressing a kiss to your forehead. "cum all over my dick f'me, sweetheart."
you supposed you were more obedient than you thought.
dean watched as you squirmed and moaned, eyes screwed shut as you finally let go around him. he could feel your gummy walls squeezing him tighter, a ring of slick had formed at the base of his dick. the mere sight, his dick still stuffed inside your cunt and you, cumming all over him.
well, it was enough to have any man weak.
which was why he'd finished so quickly, too.
after all, he'd been holding on since you were sat on his lap.
and that one feeling, cumming in your wet, hot walls and watching you with that pretty, stricken and worn out face as you came on him too... he swore he had really been to heaven and back.
when you both rode out your highs, he laid himself on the bed next to you, watching as you reached your hand up, playing with his silver ring that sat on your thumb.
he swore he was staring at an angel.
main masterlist/dean's masterlist