dean taking your virginity, and he’s walking you through the entire thing btw. oh how i need this.
warnings: romance, love confession, foreplay f!receiving, fingering, oral f!receiving, gentle sex, unprotected piv, inexperienced virgin!reader
if someone had told you a few years ago, you’d be sure it was a lie, a trick. dean winchester, being in love with you? yeah, right. nice joke.
only it isn’t a joke. it never was.
and you didn’t believe that until he took your hands, looked deeply into your eyes with a serious expression, even when you were still cackling, and reassured you.
“y/n, i’m being serious. i… i love you.”
your laughter slowed to a stop, and your entire world shifted.
dean winchester, your ride or die. the same dean you were introduced to by your dads, hunting buddies, as a small child. the same dean you shot a rifle with for the first time. the same dean you snuck out to get drunk at a playground in the middle of the night freshman year with. your very best friend. the boy you fell in love with, he loves you back. he’s in love with you back.
dean’s hands were sweaty at this point, despite usually running cold. he looked like a deer caught in headlights. his eyes were scanning yours, looking for any hint of rejection. all he could think about was what you would say. he was terrified.
your lips curved up into a smile as a blush spread across your cheeks. you held onto his hands tighter.
“i never thought you’d…” your voice trailed off, and you shook your head, laughing in disbelief. dean swallowed a lump in his throat, still unsure of what you were thinking. his heart was nearly pounding out of his chest.
you let out a small, amused scoff and grabbed his face gently, moving closer and connecting your lips with his.
dean immediately relaxed, his hands finding your hip and back as he leaned in closer. he pulled away gently, smiling from ear to ear as he admired your features.
“so… you fell for me like every girl does or—”
“shut up.” you cut him off with a breath of words and another kiss. though you were secretly amused at him mocking you. it was true, you did always complain about him being a chick magnet.
he smiled against your lips, resting his forehead against yours.
“just in case you didn’t guess, i love you too, dean.” you whispered as your smile grew sheepish. he chuckled in return, his hands running up and down your back.
“god, i could get used to this…” dean mumbled as he just relished in your touch, in touching you. he was loving every damn second of it.
he wanted to feel you, all of you. in the most loving, innocent way possible too. for once, it wasn’t just gonna be a casual hookup or a one night stand. it wasn’t just lust, it was love.
and you, you’d never been so comfortable being in someone’s arms. his hands on your back and hip were like heaven. you wanted to be as close to him as you possibly could.
you wanted his skin on yours, everywhere.
the two of you sat there, your hearts thumping in your chests, your breaths heavy at just the thought of it. you both knew what you wanted. and you could feel that the other wanted it just as much.
your hands slid around to the back of his neck, and you swung your leg over his lap, resting to straddle him.
he looked up at you in awe. his hands running up and down your sides. his bright green eyes reaching deep into yours.
he opened his mouth to say something, but just couldn’t find the words. he was silently asking you a question, and you knew exactly what it was.
you nodded and your fingers found the collar of his brown leather jacket. you slid it off over his shoulders, letting it fall, painting a contrast against your white comforter with little flowers all over it.
you tugged at the bottom of his worn-down black t-shirt, silently asking for permission to take it off. he nodded eagerly, lifting his arms for you. you tossed it off to the side, not bothering to see that it landed at the foot of your open closet. it stuck out like a sore thumb next to the rows of mostly white and pastel colored dresses.
you lifted your own arms, letting him lift your comfy light pink dress off and discard it to the floor.
he was mesmerized by you. the way your white lace panties hugs your curves, your thick thighs, your soft tummy, and the way your matching bra perfectly held your tits. and all of this, you were giving to him. to say he felt undeserving was an understatement. he didn’t deserve any of this. any of you.
but, god, you’re right here. and you love him back.
his hands felt up and down your back, stomach, and thighs with such a loving caress. your fingers danced along his bare chest and abdomen. his breath hitches at your touch. he’s never felt so vulnerable, so seen,
but that still didn’t distract him from the nervous look in your eyes, the way you avoided his gaze, and you seemed to shy away when he got too close to anywhere too private.
“hey, hey…” he tilted his head to meet your eyes, his hand gently taking your chin.
“you okay?” he asked in a tone so soft, full of concern and focus.
you hesitated, taking a deep breath, trying to get away from looking him in the eyes again.
he understood what you meant right away, and his expression relaxed. he knew you’d had a few boyfriends here and there, some kisses. whenever you broke up with someone, you always told him it was because it just wasn’t working out. but dean knew it was because you weren’t ready for anything more with them, and they were all too dumb to want you without the sex.
“i know, baby. i know.” he nodded. “we don’t have to do anything you aren’t ready for. you hear me? not a damn thing. you call the shots.”
“no, i—i wanna have sex with you.” you rushed out, chuckling a little at how eagerly you had just said that. he smiled cheekily. any other time he would’ve made some stupid remark, but he knew how nervous you were. and he wanted you to be as comfortable as possible.
you took a breath, relaxing your body. “i wanna have sex with you.” you said in a calmer voice. he chuckled and blushed a little. “okay, sweetheart.”
he gave you a soft kiss on the cheek and held you close to him, turning the two of you so he could be on top. he rested your head against your pillows, making sure you were comfortable.
“just relax. i’m gonna take care of you.” he whispered into your ear. you nodded and your breath hitched as he moved to your neck, lightly kissing and sucking, surely leaving marks. his hand ran over your waistline, brushing against your underwear. you tensed up a little.
he pulled his hand and head back. “yeah?”
you took a breath, meeting his eyes. “um… what are you gonna do next?”
he smiled softly, bringing his hand up to caress your cheek. “i’ll walk you through it, okay?”
you nodded in response, putting your full trust in him.
he shifted to lay next to you on his side, his hand hovering over your upper thigh.
“is it okay if i touch you underneath your underwear, sweetheart?”
you nodded, your eyes never leaving his hand.
“has anyone else ever touched you there?”
“have you ever touched yourself there?”
your eyes widened a little at his question and you hesitated for a moment.
“nothing to be embarrassed about, you know i’ve done it too.” he chuckled lightly. that eased your nerves a little as you smiled and nudged him.
“you know your body better than i do. so, you tell me if i’m going too slow, too fast, if it’s not feeling good. anything like that. it’s just you and me. okay?”
you blushed at his words. that was already a turn-on itself.
“okay, i’m ready.” you nodded, resting your head on his shoulder and gripping his free hand from where it was resting on your shoulder.
he planted a kiss on your temple and slowly slipped his fingers under your panties. you shifted a little, sucking in a breath as his finger ran up your slit.
“fuck, you’re soaked, y/n/n.” he nearly groaned out his words. you felt so good already.
you let out a small gasp as his fingers found your clit. he started rubbing in slow circles around your sensitive bud. he watched in awe as your head fell back against his arm. your mouth dropped open and you rolled your hips slightly. instinctively, his motions started to speed up.
you gave his hand a squeeze. “s-slower,” you managed, and he nodded, not even realizing he had sped up until you told him. “sorry, sweetheart.” he chuckled lightly, still watching you closely. “s’okay… feels so good… god, dean…” you moaned softly, and his heart fluttered. he could tell you were already getting close, and he pulled his hand away.
you let out a whine as his hand slipped back out from your panties. “deeeean!” you pouted. he laughed a little and licked his fingers. he gave you a menacing grin as he shifted down the bed.
your eyes widened and you propped yourself up on your elbows. “dean, you don’t have to—”
“i want to. you taste too good.” he said firmly. “unless you aren’t comfortable with it. but i really want to.” he said, holding back from pleading with you. he didn’t want to make you feel pressured in the slightest.
you nodded and lifted your hips. he smiled and tugged your panties down. “atta girl… you wanna take that bra off for me?”
you happily sat up, unclasping your bra and tossing it to the floor. dean was nearly foaming at the mouth at this point. he threw your panties to the floor too.
he took a moment to admire your bare chest, the way your tits sat perfectly, fitting the rest of your body so well. your nipples we’re hardened too. and he looked up at you before silently asking for permission. you nodded, biting your bottom lip, and he wasted no time, his hands cupping your tits and thumbs flicking over your nipples.
he laid you back down, hovering over you as he stuck his tongue out, swirling around one of your nipples as he pinched lightly at the other. you arched your back slightly, your core only getting wetter by the second.
his hand traveled down your tummy, and he once again gently rubbed at your clit. your body twitched at the contact, and he pulled away from your tit with a pop. a string of saliva followed him as he licked and kissed down your soft skin.
it wasn’t long before his head was in between your thighs. he still rubbed at your clit, but slowed down enough for you to be in the right state of mind.
“y/n/n, i gotta ask you some more questions now, alright?” and you hummed in response, still relishing in the pleasure of his touch. your eyes were closed and your head was turned to the side.
“y/n.” he said in a firmer tone. “look at me, or i’ll have to stop. i know you don’t want that.”
he smirked a little as your head perked up, and you propped yourself up on your elbows.
“good girl. now, tell me… have you ever fingered yourself?”
you were once again embarrassed by the questions, but you knew they wouldn’t leave this room.
it’s just you and me. dean’s words rung in your head.
“i have… a few times before. but, um… not a lot.”
he nodded. “okay. that’s okay, sweetheart. i’m gonna go one by one, and if it’s too much, you just tell me to stop, alright?”
you hesitated a little before nodding.
“y/n/n…” he squinted a little, noticing your hesitation.
you met his eyes and shook your head a little. “it’s okay, it’s okay… i’m ready.”
“i want you to.” you said firmly, your tone much less hesitant.
dean smirked a little before nodding. he caressed the insides of your thighs before spreading your legs open wider.
“okay, baby… i’m gonna use my fingers and my tongue. think you can handle that?”
your stomach turned at his words. you hadn’t ever been so aroused, it was such a new and exciting feeling. and you wanted to give it all to him.
you nodded and laid back on the bed, closing your eyes as you felt his finger at your entrance.
“words, sweetheart.” his voice was low and firm, almost like a growl.
“yes,” you breathed out immediately. “i can handle it, just please…”
dean smirked in amusement at how desperate you sounded. again, he thought it’d be best to save the dirty talk for another time. this time was about focusing on you, learning what you liked and what you didn’t, for the both of you.
he slid one finger in slowly, watching how you grimaced slightly. “tell me how it feels.” he said in a firm but gentle voice. you eyebrows furrowed as he went in and out slowly.
you gave it a minute, adjusting to the new feeling. you jolted a little as he brushed against your g-spot, unaware of that feeling. “y/n/n.” he said, gaining your focus.
“oh, god… do that again.” you panted slightly. he found that spot again, making you gasp. “fuck, that’s it…” you moaned softly. it felt uncomfortable at first, but you were very much into it now.
dean kept his slow pace, feeling your juices coat his finger as his tongue found your clit, moving in slow circles as he kept his eyes on you.
you shifted your hips closer to him, surprising him a little with how eager you were. he sped up his movements a little, adding in a second finger.
your panting got heavier and you whined as he stretched you out, his fingers curling to that spot you loved. one of your hands went to his hair and you took his free hand with the other, holding onto him tightly.
“dean…” you moaned his name as you slightly rolled your hips against him. he groaned at hearing you say his name like that, and you shivered at the vibration.
he could feel you getting more eager by the second as your body was building up to your first proper orgasm. you were a breathy mess and squirming to get closer to him.
dean took his hand, still intertwined with yours, and used it to hold you in place, pressing firmly on your lower abdomen. you whined a little at not being able to move around as easily, but you quickly snapped out of that when he slipped in a third finger.
you let out a whimper as his fingers moved in and out of you at a faster pace, and his tongue was now going wild on your clit. you couldn’t get enough of him.
his name left your lips over and over. your voice sounded so desperate as you got close to your climax.
“dean, dean, fuck, m’so close, oh god, dean,” you rushed out, repeating words over and over like your mouth was on autopilot. you gripped his hand and the sheets tighter as your mouth dropped open.
you let out a loud moan as your orgasm shot through you. your entire body tensed underneath of touch and he slowed his movements, riding you through the high.
you were almost certain you’d see stars if you opened your eyes. once you did, you were only met with dean’s beautiful, sparkling eyes. he was hovering over you, lightly rubbing your clit before pulling his hand away.
he brought his hand up, sucking his middle and ring fingers clean of your juices, and you shivered at his stare. his eyes were fully locked on yours. but it wasn’t seductive, it was warm. his lips curved into a smile once his fingers were out of his mouth, and he held up his index finger.
“you wanna…?” he quirked an eyebrow, holding his finger to you. you looked between him and his wet finger before nodding. you stuck your tongue out and he let you take his hand, your tongue swirling around his finger and tasting your juices for the first time.
he let out a small gasp as you sucked on his finger. your lips were so pretty, he couldn’t take it. and your tongue felt like heaven on his skin.
after your lips left his finger with a small pop, he took a moment to admire you. he took in your features, knowing that he had the privilege to be here with you at this time.
he brushed a stray hair from your face and placed his hand on your cheek. he smiled wide, having such a look of awe in his eyes.
“i really love you.” he whispered softly. you smiled with him. it was all he needed to say, because you knew he was just so lost in every damn part of you.
“you’re so perfect.” he leaned down and placed a soft kiss on your lips, the two of you sighing into it. you rested your forehead against his.
“i really love you.” you said back, your eyes scanning his loving gaze.
he blushed and placed a quick kiss on your cheek. he then moved from his place above you, standing up from the bed.
“hey, hey, woah,” you grabbed his hand. “and where do you think you’re going?”
he looked a little confused, raising an eyebrow. “i was just gonna grab a towel… to clean you up, y’know… and i, uh, thought we could cuddle and watch a m—”
“who said we were done?” you cut him off with a playful tone.
his eyebrows shot up and a small smile played on his lips. “sweetheart… are you sure it wasn’t too much already for your first, y’know, pre-sex stuff?”
you chuckled and yanked him back toward you. he stumbled and caught himself by putting his hand on the mattress. your faces were close together and you smirked a little as you looked between his eyes and lips.
“i wanna go all the way. today.”
his eyes widened a little and he caressed your arms.
“are you sure? like, really sure?” he hesitated a little.
“i’m really sure.” you smiled genuinely and placed a hand on his cheek. you tilted your head to the side and ran your free hand down his bare chest, to his lower abdomen, til you hit the belt on his jeans, your eyes following your fingers.
you looked back up at him and saw how his breath had quickened.
“dean?” you questioned quietly. he hummed in response, still focused on your hand on his belt.
“do you wanna do this?” you asked hesitantly. his eyes shot up to yours. despite still looking nervous, he nodded eagerly. “i do. i really do.” he breathed out.
your lips curved into a soft smile and you gave him a small kiss again. he blushed and stood up straight, his fingers fiddling with the belt on his jeans.
you put your hands over his, sitting up on the bed in front of where he was standing.
“can i…?” you questioned, gently pulling his hands away. he nodded and dropped his hands to his sides, watching as you undid his belt and slid down his jeans and boxers.
he sprung free from his restraints and your eyes widened. you swallowed hard, your gaze stuck on his length. this wasn’t gonna be an easy first time, you were sure of that.
he pulled his clothes down the rest of the way, kicking them to the side.
his eyes stayed on yours, but you couldn’t pull your own eyes away from his cock.
“y/n/n?” he asked quietly, his hands finding your face. “we really don’t have to, if you aren’t ready.” he nodded, a small smile on his lips to reassure.
your eyes went up to his. “no, no, dean… i want this.” you reassured him too, placing your hand over his on your cheek. you placed a kiss on his palm and scooted back on the bed, pulling him with you. he crawled over you as your head rested on the pillows.
he was hovering over you, taking a look over your body again as his hand ran gently up and down your side.
“i don’t have any condoms.” he sighed, running a hand through his hair.
“i’m on the pill, for hormones and whatnot. but… you’re gonna pull out anyway. never can be too safe.” you chuckled and he laughed with you, resting his forehead against yours.
the air grew thick around you, and the two of you tensed up in each other’s arms.
“it’s okay to be nervous,” he said softly. “i’m nervous too.”
“i know,” you smiled shyly, nodding. “but i trust you, and i wouldn’t want it to be anyone else.”
he smiled at that, leaning in to give you a soft, slow, heartfelt kiss. he took his time with you, making sure you could really feel it.
“i love you.” he breathed out against your lips. he loved saying it.
“and i love you.” you whispered back. “i’m ready when you are.” you let out a shaky exhale and spread your legs open wider for him.
he got in a comfort position and stroked his length a few times while placing small kisses on your cheek.
he led the tip of his cock along your folds, coating it in your slick, the two of your breaths picking up as he did so.
dean placed his free hand on your side, squeezing you gently as he focused solely on your face. the tip of his cock was poking at your slightly stretched entrance, and you were dripping wet.
“baby… i’m not gonna lie to you, it’s gonna hurt. just tell me if you need me to stop or slow down or anything, okay?” he ran his thumb over your skin in a soothingly manner.
“i will.” you nodded, already holding your breath.
“breathe for me.” he took a deep breath with you before slowly pushing in. your mouth dropped open and you let out a gasp as he got maybe 2 or 3 inches in.
“stop, stop, stop.” you blurted out. he went completely still, his hands rubbing your sides, hoping it would provide some comfort.
you winced and took some more breaths, slowly adjusting to it. dean grimaced at the sight of you in pain. just as he was about to ask if you wanted him to pull out, you came back to.
“okay, you can keep going… slow, please.”
“sweetheart, are you sure?”
you nodded eagerly, holding onto his shoulders to ground yourself. he nodded in understanding and started to move slowly again, pushing himself further into you.
you squeezed your eyes shut, whimpering and wincing as tears prickled at the edges of your eyes.
“you’re doing so good, y/n/n. keep breathing, baby.” he stayed close to your ear, whispering sweet nothings to you. he was more than halfway in now.
you let out a cry and he stilled again. “shhh, hey, i’m right here. talk to me.” he was growing concerned, and he wanted to stop if it was hurting you too much.
you shook your head, taking another breath.
“keep going.” you groaned after a short minute. dean went in deeper, and it felt like pressure was released. you let out a breath, your head falling back to the pillow.
dean kept himself buried deep inside you as you fully adjusted to him. he waited for your command on his next move.
your grip on his shoulders was still tight, but a lot of your tension had let go.
“okay, m’ready. you can move now.”
he nodded and slowly pulled out about halfway, before pushing back in. he watched your facial expressions to be sure you were still okay.
after a couple of slow thrusts, the pleasure started outweighing the pain. it was still a little uncomfortable physically, but it was all worth it. having this moment with dean, being able to make love to him, was a gift.
once dean knew you were okay, he picked up the pace slightly, groaning softly as his cock twitched inside of you.
“god… you feel so good. you’re so perfect. shit.” he cursed under his breath, whimpering lightly at the feeling of your cunt clenching around his cock.
you held him closer, panting and letting small moans slip every so often. your arms were draped over his shoulders, and your breaths were mixing with each thrust.
“dean,” you breathed out, you back arching into him. you wanted more now that it felt better. it hurt in a damn good way.
he chuckled breathlessly and grabbed a pillow that you hadn’t been using for your head.
“y’know that spot that i hit earlier? with my fingers?”
your pussy throbbed at the thought of it, and you held back another whine. you nodded instead, biting your tongue.
your eyebrows furrowed and you whined as he pulled out of you, already feeling empty without him.
but you still did as he said, lifting your hips with your shaky legs. dean slid the pillow underneath, letting you rest on top of it.
“okay, so what is this gonna—?” you were immediately cut off by your own loud moan as he slammed back into you, hitting your g-spot so perfectly.
“fuck, dean!” you growled loudly. he stayed still for a moment, smiling in amusement at your reaction.
“feels good, huh?” he asked with that cocky little smirk of his, only now he was on the verge of busting out with laughter at how desperate you now looked.
“jesus christ, do it again, please.” you mumbled as you gripped the pillow behind your head. he got a firmer hold on your hips and thrusted in and out of you again.
you wanted to cry at how good it felt when he bottomed out. you squirmed to get closer to him. he couldn’t help but let a laugh slip, but that quickly faltered when you rolled your hips so deliciously against his. fuck, he was so gone.
he started to thrust in and out of you again at a steady pace, letting you adjust to the newfound pleasure before he went faster or harder. he wanted to hear that from you if you wanted it.
your free hand found his on your hip, and your fingers intertwined. he leaned forward and brought your hand up with his, pushing it into the mattress next to your head.
the two of you were face to face again, and you slid your other hand around the back of his neck, pulling him in for a kiss. it was messy and sloppy and the two of you laughed about it when you accidentally hit your teeth against his.
but that’s what made it so perfect.
“harder, dee…” you breathed out. you started kissing and sucking at his neck, feeling him shudder at your touch.
he grunted as he slammed into your pussy harder, feeling your walls clench around him again. to him, being inside of you was like fitting two puzzle pieces together that took forever to find. except… way better.
you had that knot again in your tummy, feeling it build with each thrust. dean noticed you squirming more, and quickly took note. he slid his hand between the two of you, finding your clit once again with ease.
he rubbed in circles at the sensitive bud as he fucked your cunt, feeling your wetness cover his cock.
you thrusted your hips up to meet his, setting a faster pace for the two of you. you could feel your second orgasm building, and you knew it was gonna feel like heaven.
“mmph, dean… you feel so good, fuck… my god…” you moaned as you scratched at his back, overwhelmed with the pleasure building up between you two.
“c’mon, sweetheart. cum on my cock… wanna feel you pulse around me…” he breathed these words out into your ear. “cum for me, y/n…” he said shakily, feeling himself get close too.
your orgasm shook your body, and the white-hot liquid pooled around dean’s cock, coating him in your delicious juices.
“fuck, that’s it, baby. you did so good…” he groaned as he felt your cunt throbbing. he helped ride you through your high, eventually pulling his hand away and gripping your hip again instead.
“y/n/n, i’m close, baby. where do you want it?” his voice was getting a little more high-pitched, and you could tell he was so close to that sweet release.
“in my mouth,” you rushed out. “wanna taste you.”
he let a moan slip at your words, his thrusts getting more sloppy.
“yeah? you wanna, or you need to?”
“need to, baby.” you breathed out, your body still shaking below him.
dean shuddered at your words again and he pulled out, the two of you groaning at the loss of being connected. once his legs were on either side of yours, you slid yourself further down the bed as he he moved up on his knees.
he was hovering over your chest, jerking himself off with his hand and cock covered in your slick. you rested your hands on his thighs, rubbing soothing circles with your thumbs as you egged him on.
“bet you’re gonna taste like heaven. m’right here, dee. cum in my mouth. i need to taste you.” he let out a breathy moan as you dropped your mouth open. your tongue was out, waiting to be covered in his load.
he groaned and threw his head back as his white-hot cum shot out into your mouth. he brought his head back to see your mouth all wide open, taking every bit until he was done. and when he was, you swallowed all of it. licking your lips and scooping up every last drop with your thumb.
his breaths came out in heavy pants and he moved from his place on top of you, flopping down next to you on the bed.
the two of you lay there, absolutely out of breath and spent, before you notice dean giggling to himself.
“what?” you turned and looked up at him, amused by his cute little giggles.
he shifted closer to you and wrapped his arm around your shoulder, pulling the blanket up over the two of you.
“i just had the best sex ever with a virgin who happens to be my best friend who loves me back. and she’s not going anywhere after this.” he looked at you feigning a serious expression.
you chuckled lightly and shook your head, leaning into his chest.
“you’re right about that. she’s not going anywhere.”
this was kinda a lot longer than i meant for it to be LOL, but i hope you guys enjoyed <3
reminder that requests are open, and you can check the “in the works” section of my MASTERLIST to see what’s up next. thank you for the support!!!
