dean winchester x angel!reader — first time.
warnings! mdni! smut. male masturbation. reader catching dean. female masturbation. mentions of oral (both m and f receiving). fingering. praising. first time. dean talking you through it. pet names. unprotected p in v (wrap it before you tap it). graphic language. dean has a breeding kink. grammar mistakes.
word count! 3.5k
you were just… so sweet.
so painfully sweet and innocent. and dean didn’t want to take that away from you. he wanted you to be that innocent angel, curious of everything as long as you could. without being scarred by an ordinary mortal like him. the fact you happened to love him out of all people still baffled him. but he wasn’t complaining since he was absolutely and utterly in love with you.
but then again, you were driving him crazy to the point where the ache in his pants was getting worse and worse, day by day, where now his hand wasn’t enough to satisfy him. at this point, he got cramps in his fingers and couldn’t squeeze them in a fist properly.
he needed you. badly.
and you were so oblivious to the effect you had on him. every time you brushed against his body. or when you were in his bed, curiously watching scooby-doo as you demanded he put it on since he told you it was his favourite show when he was a kid—and you wanted to know all his favourite things. or when you’d explore your boundaries, testing out some physical contact by randomly taking his hand in yours, tucking your head under his arm as you stood next to each other, cuddling together as you went to sleep or kissing.
christ, you were so adorable. he loved you so much.
and you were so good at stirring his cock to life, unaware of what was happening.
which was pretty much the reason for his current predicament. dean was making something in the kitchen, and as the curious little angel that you were, you came closer and snuck under his arm, so now you were placed between the stove and his body.
he inhaled sharply, his eyes widening as your plush ass rubbed against his crotch. it was enough for a red light to light in his brain, and his thoughts beginning to go haywire.
too close. too close. step back. step back, he kept repeating to himself.
but how could he possibly step away from you when you looked so gorgeous, just innocently trying to learn something new from your boyfriend? dear god, was he going to hell. again.
he looked down since you were shorter than him, which was a mistake. his eyes widened, and his mouth watered as he was met with the valley of your perky breasts, a deep cutout in your shirt doing only so little to help his fantasies.
not only that, but he did start wandering where you even get clothes LIKE THAT.
fuck, who was picking your clothes? stupid question, as if he wasn’t the one to do so.
the truth was that dean spoiled you immensely. now, instead of buying the newest copy of ‘busty asian beauties’, he was picking out some magazines for you to read. you’d look at all the pretty pictures—that’s what you’d call them, and point at clothes you liked. and dean would get them for you when you stopped by some shops. how did he know your breast cup size, though?
well, he was experienced like that. and he loved looking down at your boobs when you were sleeping in his arms.
anyway.
to complete the overall outfit, you were wearing those low-cut jeans that nicely accented your plump ass that he loved swatting as you went past him. and the way your white panties were sticking out just made him imagine his fingers slipping under the fabric and making it dampen as he—
he took a sharp breath. again.
dean took a step back after all, only to discreetly palm his crotch as he hummed some kind of response to the question you just asked him. however, he couldn’t think straight. so, making up some lame excuse, he kissed you on your temple and quickly went to his bedroom, sitting down on his bed and resting his back against the pillow, already propped up.
he rubbed the bulge in his pants, groaning at the feeling of his cock straining against the fabric. he couldn’t take it anymore. he fumbled with his belt and pulled his pants and boxers down, freeing his dick. his massive length sprung free, hard as a rock, already leaking beads of precum. he spat on his hand, not bothering to take the lotion out of his night drawer and started stroking himself.
he started off slowly, imagining that it was your delicate hand, your small fingers grabbing his dick for the first time, barely able to wrap around his girth. he imagined you gasping in surprise as you would start moving your hand up and down, letting him guide you through it, so you’d do your best to pleasure him. and you would—he knew it. you were such a good little angel for him.
dean groaned and squeezed harder, picking up the pace of his hand, his pants and moans getting more audible, but he didn’t care about it at the moment. now, he was imagining you taking him in your mouth. at first, you’d be too eager—you’d gag around him and quickly pull back with that sheepish smile of yours when you did something wrong. holy fuck. he’d reassure you, and then you’d try again, slowly, taking the tip first, gently suckling with your pretty plump lips he loved to kiss. then, you’d go lower and lower, your cheeks hollowing as you—
the door to his room slammed open, and his heart stopped. he widened his eyes and turned his head, seeing… you out of all the people.
fuck him (not that he would mind).
you entered the room with that godforsaken curious expression, closing the door behind you. then, you stood by the side of his bed, your head tilted to the side as you looked at him, blinking slowly, as if you didn’t notice his fat, messy cock, tightly gripped in his hand, with skin slightly reddened from the intense strokes.
“are you okay?” you asked softly, and dean wished that something could just kill him right now, his face as red as it could possibly get.
“yeah. why are you asking?” he chuckled nervously, quickly tucking himself back in his pants, even though it was painful at this point. god, he needed to cum so badly.
“i don’t know. you disappeared. and then you were panting and calling my name, and i thought something was happening and that you needed my help,” you just couldn’t be more innocent than that. “i was scared something was wrong,” you admitted shyly, fiddling with your fingers.
and gosh, he’d take your face in his hands if it wasn’t for one of them being covered in precum.
“hey, don’t worry, birdie. i’m okay. just needed—“ he sighed, straightening his back and trying to muffle a grunt. “some relief.”
“from what?” yeah, of course, you’d ask. your curiosity was picked up again.
“it’s nothing that you should stress your little feathery head with,” he smiled, adjusting himself, trying his best not to moan.
and you took a moment to look at him. you tilted your head as your eyes raked over his body, his twitching hand and the massive tent in his pants. you blinked a few times as that familiar feeling you didn’t know started pooling in your lower abdomen. ogling his groin, you rubbed your thighs together, and dean noticed that instantly.
so angels do get horny.
he swallowed thickly, his mouth practically going dry as he saw your face contorting in frustration as you swayed from one leg to the other, trying to get some friction between your legs.
that’s when dean decided that he wouldn’t leave you hanging like that.
“what are you doing, birdie?” he asked, licking his lips.
“i don’t know. i have this weird feeling in my belly,” you scoffed with a small pout. “like i’m excited or something.”
“that’s cause you are. you’re aroused, baby,” he hummed, reaching his left hand out to you. he hooked his fingers under the hem of your jeans, pulling you closer so you were now standing between his legs. he rubbed your hip and smiled softly. “do you know how babies are made?” a stupid question, but, he needed to know that you were aware.
“dean, i know what sex is. i just didn’t think angels could feel that. apparently they can, and i feel like that only around you,” you huffed in frustration while dean couldn’t be more ecstatic than that. you were horny only around him.
“well, have you ever done it?” he asked, almost breathlessly. it felt like the best day of his life.
“no. i didn’t have to,” this matter-of-fact tone only made the older winchester chuckle in amusement.
“birdie, it’s not something you have to do. it’s something you do to feel good. to have some fun with the person you love. it’s not some obligatory task, y’know?” he explained, squeezing your hip.
“like the pizza man?” you tilted your head to the side, and dean sighed. damn, cas, for showing it to you.
“exactly. like the pizza man,” a small smile on his lips as he leaned forward and placed a kiss on your stomach. “but my question is, do you want to feel good, birdie? do you want to do this with me?” maybe, after all, he’d take some of your innocence. but just a little…
you nodded your head, the ache between your legs only intensifying. dean smiled and stroked your cheek with his knuckles.
“good girl,” and then, he pulled you in for the kiss that couldn’t scream hunger any louder.
he was kissing you with a fervour that you happily returned, your fingers tugging on his short hair, making him gasp in your mouth. he’s tongue quickly dominated yours, tasting the familiar cavern of your mouth.
dean grabbed you by the nape of your neck, pulling you on top of him so you were straddling him. he grunted into the kiss, grinding his hips up into you. the massive bulge in his pants rubbed against your clothed heat, making you gasp so sweetly into his lips.
“fuck, i need you so much, birdie. can i have you?” he practically whimpered, looking into your eyes with so much desperation and pent-up feelings.
you smiled and nodded, placing a small kiss on the tip of his nose.
“of course, deano,” and it was enough to make him feel like he was on top of the world.
quickly, he spun you around, your back on the plush blanket as he made his way between your legs. his breath hitched as he fumbled with your jeans, slowly sliding them down. his eyes fell wide open, and he felt as if his heart stopped when he saw that your white panties were practically transparent from how soaked they were.
“you’re this excited, birdie?” he asked with a small chuckle, throwing your pants on the floor. he lay down on his stomach, right between your legs, looking at your dampened underwear as if it was the most beautiful sight in the whole world. “you’re so wet. for me,” he sighed, almost in disbelief.
meanwhile, you felt shy. you trusted dean, but it was something totally new, and you didn’t know what to expect. angels weren’t supposed to feel like that… at all. but then again, you fell in love with a human, so might as well go to hell with it.
dean started blowing on the dampened spot, his warm breath making you squirm, your thighs trembling. you tried to lift them up, bent your knees, but he stopped you, throwing your legs over his shoulders, scooting closer to your needy pussy.
“i didn’t know you were sensitive like that,” he chuckled and pressed a small kiss against your clothed core. you gasped softly, mindlessly moving your hips as if to grind against his face.
you were flustered and didn’t know what to do. which dean noticed and took it as his personal mission to make it feel good for you. he looked up at your reddened face with a soft smile, rubbing circles with his fingers on the soft skin of your thighs.
“i’ll make it so good for you, birdie. i promise,” he panted, and then, he practically ripped your white panties open. not that he was planning on getting rough with you—he just didn’t want to pull away from his new favourite place.
as soon as your pussy was bare to his eyes, he almost gasped in amazement. your pinky folds were covered in arousal, glistening deliciously as if to invite him to bury his face there. he brushed against them with his fingers, and then, slowly parted them open. he inhaled sharply through his nose as he placed his fingers on your clit, already feeling how swollen it was under his digits. he started rubbing it in soft circles, making you gasp and arch into his touch. jesus christ, it was like all his dreams came true in this moment.
“you have such a pretty little pussy, birdie. and you’re already so eager for me,” he muttered breathlessly, grinding his hips against the mattress as he was touching you.
his other hand moved to your entrance, his fingers probing it open, and then, he slowly slid one finger inside. you widened your eyes and inhaled sharply, sitting up and looking at what he was doing.
“shh, shh. it’ll feel good, baby. i promise. watch and learn so you can help yourself if i’m not around, okay?” he cooed, looking up to meet your eyes.
after receiving a nod of confirmation, dean continued. slowly, he started moving his finger inside of you, feeling your soft walls clamp around it greedily. fuck, he wanted to sink his cock inside you as soon as possible to feel you flutter around him, memorize his shape as it twitched eagerly inside of you, ready to spill his thick cum deep inside your womb, marking you as his. but first, he needed to prepare you for it.
then, he added the second finger, moving them in and out but also trying to stretch your tight hole for his dick. it could barely take in two of his fingers, so he was only imagining how tight you’d feel wrapped around his cock—which made it twitch painfully in his pants.
you were making such beautiful sounds—every shy groan, gasp or a whimper, sending him into oblivion as you watched him fingering you like a good little student.
however, as soon as he felt your walls begin to flutter around his digits, he slowly withdrew them, making you whine quietly at the sudden emptiness. he smiled and looked at you while his thumb was pressed against your swollen bud. “i know you want more, baby. but now it’s time for something better, and i want you to finish with me. but i’ll kiss that pretty pussy later and make you feel good again,” he promised, placing a soft kiss on your forehead as his thumb stroked your clit. you gasped and nodded, biting your lower lip as you looked up at him.
“i need you, dean,” you whined so pathetically that he felt he’d cum in his pants right at that exact moment.
he nodded his head, taking his clothes off at the same time, eager to sink deeply into your warmth. as soon as he pulled his boxers down, his cock sprung free, hitting his stomach. you widened your eyes curiously, tilting your head to the side as you watched it throb, precum leaking down from the tip. subconsciously, you licked your lips, your cunt only getting wetter. dean smirked cockily, getting between your legs once again.
“like what y’see, birdie?” he chuckled, stroking himself a few times, spreading the precum on his length.
then, he rubbed the tip of his fat cock against your dripping slit, coating it in your juices. finally, he nudged the head of his erection in your entrance, slowly pushing in, filling your desperate cunt. you gasped loudly, your eyes widening as you felt his cock stretching you out. with a whine, you leaned back on the pillow, your eyes rolling to the back of your head as you let out a few needy whimpers.
dean grunted, feeling your walls flutter around him, trying to accommodate his size.
“you’re so fucking tight, birdie,” he panted, slowly pushing forward, trying to sink in fully, just waiting for the moment his tip would brush against your cervix. one hand was firmly holding your hip meanwhile the other moved to your chest, giving your breast a firm squeeze as he rolled your nipple between his thumb and forefinger, feeling it harden in his touch.
soon, he was fully sheathed in you, the tip of his dick pressed against your cervix, your walls stretching on his girth, already memorizing each throbbing vein. he looked down at you with a soft smile, stroking your hair as he moved some of it out of your already sweaty forehead.
“how are you doing, birdie? feels good?” he asked. he wanted to make sure that it was 100% pleasurable to you, and he’d stop as soon as he noticed even a slight narrowing of your brows.
you nodded, biting down on your lower lip. “yhym. y-yeah. feels good,” you sighed, slowly relaxing after the intrusion.
dean smiled and kissed you lovingly on your lips, beginning to move as soon as he felt that you weren’t so tense anymore. you gasped softly when he pulled out, the head of his cock still nestled in your pussy, and then moved back in. you wrapped your arms around his shoulders, your nails digging into his back, leaving dark crescent marks on his skin. he hissed and groaned in pleasure, picking up the pace.
“you drive me crazy, birdie. feels so good. so wet. i should’ve put my cock in you a long time ago,” he moaned, his hips beginning to slam against yours, the loud sounds of skin slapping against skin echoing through the walls along with the sound of your pussy eagerly slurping him in.
soon, he was pounding in and out of you, your lovemaking echoing obscurely to the point it was heard outside of the room, and you just imagined the look of exasperation on sam’s face as he pondered over getting some earplugs. but it quickly disappeared from your mind, your focus landing back on dean and his cock, basically splitting you open.
he threw your legs over his shoulders, wrapping his arms around your thighs as this new position allowed him to go even deeper. you were holding onto the headboard, moans leaving your mouth nonstop, and as he hit that sweet spot inside of you, you almost screamed, clenching around him.
“you’re gonna cum? huh, birdie? cum for me,” he panted, thrusting into you even harder.
you yelped pathetically, feeling a knot forming in your lower belly, your body tensing up as it was preparing to fall over the edge.
“yeah, that’s it. cum for me, angel. you’re so pretty. fuck, i love you so much,” he panted, freeing your legs and just holding your thighs as he made you wrap them around his waist. then, he leaned forward, crashing his lips on yours in a desperate kiss.
and that was enough to send you over the edge. you clenched around him and then relaxed as your juices started gushing out on his length. he helped you come down from your high. however, his movements faltered as he was close too. he shortly followed after you, stilling in your cunt as he spilled thick ropes of his pearly seed inside your warm womb.
he drew out your climax and finally slumped down, resting on top of you. he cradled you in his arms, his head resting between your breasts as his soft cock was still nestled inside of you, your mixed juices dripping out, creating a mess.
“god, you were amazing,” he said, kissing the side of your breast. however, you quickly slapped his arm, making him hiss and raise his head at you, a small pout on his lips. “ow, what was that for?”
“don’t say his name now!” you huffed, your cheeks red as if you were caught doing something inappropriate. dean chuckled and lifted himself up, peppering your face with kisses.
“okay, okay. i won’t,” he murmured, nuzzling his face in the crook of your neck, just basking in the afterglow of your intense lovemaking.
after a while, he pulled out of you, watching his cum drip out of you. he smiled proudly and scooped some up with his thumb, pushing it back inside.
“just so nothing goes to waste,” he hummed. “we’re definitely going to do it more often from now on,” he grinned at you, studying your face. “you’ll be full of my seed every day.”
and once again, you had that curious expression on.
“can we do it now?”
dean was flabbergasted with how quickly you had recovered. but then again, you were an angel, and his dick was already hardening.
who was he to deny his little angel?
a/n: i didn’t expect it to be so long lmfao😭lmk what you think<3
༄♡ tags: @beausling @deanswidow @titsout4nicholas @a1ecmcdowell @figthoughts @aileenunfiltered @fitxgrld @angelicp0etry @hrtsoldierboy @deansbite @10ava01
