Summary Your favorite boy is turned into your favorite girl. Time to test drive the new parts.
CWs Butch pillow princess!Dean x top!reader. Oral sex. Fingering. Feminization. Lots of teasing.
18+. 3.5k words
AN Girl!Dean I would die for you. Title is from Peaches' "Boys wanna be her".
Smutober prompt Gender swap
Smutober masterlist ⏐ Dean Winchester masterlist
You grab Dean by the hips, pull him back against you and bury your face in her pussy again.
She bucks, giving a loud, needy moan, hands fisting the blankets on the bed below her as you run your tongue along her wet, sweet cunt, then press in, tongue fuck her as you hold her in place. You’ve always loved the taste of Dean’s come, but you didn’t think her slick would be even better than her jizz.
Dean presses back, another cracked moan leaving her and you move one hand from her hip, bring it to her clit, pinch it hard and she gasps loudly, tries to pull away but you follow her, press your tongue into her again.
You grin against her, move your tongue faster, take her clit between your fingers again, slowly roll it. And Dean whimpers.
This was not how you saw this day doing, but you’re sure as shit not complaining. It was supposed to be just a normal hunt, a small coven of witches over in Missouri causing trouble. Pets going missing in the neighborhood, then some suspicious deaths. Easy peasy.
Except that the witches packed more punch than you thought. You have no idea what they were trying to achieve with a sex swapping spell. Maybe they were trying to do something completely different, but at the point the spell hit there was only one of them left, so maybe she just didn’t have the mojo to pull off what she wanted, or grabbed cat’s teeth instead of raven’s eyes or some shit.
When the dust settled - literally - you had raised your revolver and shot her right between the eyes. And when you turned, you looked at Dean. Except it was also very much not Dean.
She’s shorter, but still tall for a girl. Her hair was ruffled, giving it a pixie look. The freckles are still there, of course, her clothes too big but somehow still sitting just right. The necklace and the rings and the attitude still intact. You gasped, which Dean interpreted as shock, leading to her looking down at her body, seeing the change. But it wasn’t shock at all. Well, not entirely.
She’s rolling her hips now, fucking herself back against your face and to remind her who’s in charge, you pull your face back, drag your tongue out of her, then land a loud smack on her perfect peach ass.
“Are you gonna be good?” you say and Dean groans, but it’s full of desperation. God, she fell apart so much quicker than you expected she would. It’s perfection.
“Just, fuck, keep going,” she pants, her still deep voice sounding rough and needy. “I was close.”
You bring both hands to the backs of her delectable thighs, run your fingertips up them, making her squirm even more.
“I said,” you say, voice low and clear so she has to strain to hear it as you lean forward and let your lips graze over her ass. “Are you gonna be a good girl?”
Dean stills her movement and her sounds. She’s still nearly vibrating, but she’s containing it. At least for a second.
“Yes,” she says, breathing out through her nose. “Yes, I’m gonna be good.”
“Say it,” you cut in, your hands moving to the cheeks to her ass, squeezing the two perfect handfuls. “What are you gonna be?”
Dean presses back, just a little, more into the hold of your hands so you squeeze harder. It makes her arch her back in a way that makes you think she was born for exactly that.
“I’ll be a good girl,” she finally says. You bite your lip over your grin.
“Turn around, baby,” you say and Dean immediately does what you say.
She shuffles and you knee your way onto the bed, look down at her there below you.
She’s perfect, just as perfect as she was before, but differently so. Her chest is heaving, perky tits rising and falling, her amulet resting between them. She looks at you, green eyes staring defiantly, pouty lips swollen from her biting them while you were edging her. She’s got nice, full hips, thighs that you can really grab on to and the hair between her legs isn’t hiding your favorite dick in the world, but a beautiful pussy, currently flushed pink and dripping wet, courtesy of you.
You crawl over her, lay your equally naked body on top of hers and kiss her deeply, very aware of how she must be tasting herself. Dean whines into your mouth and you nip at her lip.
“Sweetheart,” she complains and you raise your head, look at her pretty face. “Can you just, please?” You grin at her.
“Just what?” you ask, voice dripping sweet like poisoned honey and Dean groans in that way she does, making you laugh.
“Just make me come,” she says, raising her head to kiss you but you pull back, just stay out of reach, making her drop back down with a groan. You raise one hand, bring it to your lips and lick over your middle and ring finger. Then you bring your hand down to between Dean’s legs, tickling her lips, just barely, softly.
“Like this?” you ask and Dean actually throws her head to the side as she tries to push her body down, gain more contact, but you don’t let her. Instead you press your tongue against her neck, lick along it, her taste salty.
“Please,” she whimpers as the tip of your tongue reaches her jaw. “Please just eat my fucking pussy.”
God, it’s like a symphony in your ears. You run your teeth over the bone of her jaw, then push yourself up.
“Okay, baby,” you say, slowly moving yourself lower. “But only ‘cause you asked so nicely.”
Dean mutters something that sounds like fuckin’ tease under her breath, but you don’t let that deter you. You stop at her tits, lick over one of her nipples before sucking it into your mouth. Dean makes a loud throaty noise over you. You’re pretty sure you could die from the bliss you’re feeling.
He was funny about it, at first. Shocked, of course, at suddenly being inside a body that for all intents and purposes was a completely different one. Then came the jokes about finally having a pair of boobs to fondle 24/7. You raised your eyebrows, and he gave that charming, apologetic shrug he always gives, but seeing the girl-version of him do it sent a violent shock of arousal right through you.
“Yours are better, of course,” he said and you slowly let your eyes roam down his body.
“I don’t know,” you replied, “that’s a pretty nice pair, baby.”
When you looked back up, there was a deep, red blush on his face.
Dean knew you’d been with women, as recently as just before the two of you started getting serious. He thinks it’s hot, of course, sometimes asks for details, but you’ve been keeping stumm about it, not wanting to pimp out your past hook-ups and relationships, but Dean kept wondering.
He won’t have to wonder anymore. Not after tonight.
You lick along her stomach, around her belly button. She’s basically humping the air at this point, and there is something so sweet, so perfect about it that you could almost cry. Your hands go over her hips to her waist, squeezing there. You catch yourself wondering if maybe Bobby will take long enough to reverse the spell for you to dust off the strap you have hidden deep in your duffle. Seeing Dean squirm and come at the end of your hot pink dick might be an experience to remember.
“Please, darlin’,” she pants above you and you grin to yourself. Later. Right now, your girl needs to come.
You move lower, leaving slow, hot kisses in your wake. You’re surprised your spit doesn’t sizzle where you leave it - Dean’s body is heated, her movements and sounds like she’s burning up. You’ll cool her down soon enough.
You reach her pussy, and lick a long stripe over it. Dean shivers, then clenches her thigh. You push yourself a little higher, nudge her legs.
“Get them up, baby,” you say, your breath fanning over her making her squirm some more. “Up against your chest.” Dean still has the wherewithal and attitude to scoff at that.
“Who do you think I am?” she complains, while raising her legs and bringing them closer to her body. “Mary Lou Retton?” You grin up at her, look into her eyes and then press against the backs of her thighs, pushing them closer to her chest. Dean hisses at the stretch.
“Always wanted to fold you in half,” you say with a shit-eating grin and before Dean can shoot anything back, you lower your head and dive in.
There’s some wetness on the inside of her thigh, transferred there by her relentless moving, and you lick along that, then over her pussy again. She shudders, just as beautifully as boy Dean does when you take him deep into your mouth for the first time. You stop at her clit, close your lips over her, gently suckle.
The moan that leaves Dean is high and feminine and it nearly makes your eyes roll to the back of your head. It’s like those whimpering noises he makes sometimes, the ones you know mean he’s really letting go, no pretense, no act. Just pure pleasure. It’s the greatest reward in the world. You briefly unlatch from her.
“Play with your nipples, baby,” you say and you’re not sure if she’s heard you until a second later her hands go to her tits, fingers more dainty than the ones you know running over the sweet milky valley of her chest, over the hardened pink nubs.
“Do it like you know I like it,” you say, still watching, and Dean does, not talking back this time, you notice. Takes her nipples between her thumb and the side of her index finger and twists a little, like she’s looking for a good radio station. You dive back in at the same moment.
She bucks under you, but your weight keeps her down. You suck on her, press your tongue against her at the same time, circling slowly.
“Oh God,” you hear Dean panting over you, and you don’t look, but her voice sounds shaky. “That feels so, so, oh wow…”
She doesn’t have to say what it feels like, cause you know. This is what Dean does to you, the way he makes you fall apart. It gives you a wild sense of pleasure to know that she’s feeling the same now. Not that you don’t love sucking her dick, but there is something so perfect about getting to make her feel exactly what he makes you feel.
“Ready for some fingers, baby?” you say, letting go of her again. “Believe me, it’s gonna feel amazing.”
And when you suggested the same thing earlier, when you and her were making out in the alleyway behind the bar, too fucking horny to stay around for drinks, too desperate to get to each other, and you whispered in her ear that you were gonna finger fuck her until she couldn’t remember her own name, she didn’t seem so eager. But she’s eager now.
“Yes,” she pants, words pressed out, “want you inside.”
A shudder goes through you that makes you sure you might come without being touched even for a second. Your heart blooms with love as you shift, bring your hand up.
You swirl her entrance but she’s already so open, so willing. You can see her clenching, like her pussy’s trying to grab you. You have half a mind to get your tongue in there again, feel the pulsing of her around your muscle, but you’re gonna need your mouth for something else. So slowly, you push two fingers into her - fuck starting with one. You want her to feel full.
You feel her tense for a second - it must be strange to have this completely new sensation to explore. You play with Dean’s ass sometimes, but it’s never been more than a pinkie. This is different, you know. So you lower your head again, kiss her clit as you start with lazy, soft strokes. Dean stutters a moan, then a long sigh leaves her puffy lips. You can’t see them right now, but you can imagine.
This is how you work her up, slow but sure, watch her react, watch her move. See what she pushes herself closer to. It’s like getting to learn about your lover all over again. You can’t imagine anything else ever making you this happy.
At some point, you begin focusing more precisely, your movement picking up. Dean gives a shaky moan, her shoulders pulling up just as you press up against her wall and suck on her clit at the same time. Bingo.
“Oh my God,” she groans. “Oh, that, oh my God.”
And yeah. You couldn’t agree more.
You go a little faster, a little harder. Don’t change your pattern but intensify it. Dean tosses her head from one side to the other, you see as you crane your neck to look at her without letting go. Her eyes are squeezed shut, her cheeks flushed. She’s so perfect.
You detach your mouth, nip her thigh with your teeth and she doesn’t even flinch, just moans deep in her throat.
“You’re so fucking beautiful,” you say, shocked at the emotion in your voice. “You’re my perfect girl. I love you so much.”
And Dean blinks her eyes open, and you can tell she’s completely out of it as you keep running your fingers into her. She turns her head to you, then lets go of her tits and reaches down.
You think she’s going to pet your cheek or brush some hair out of your face, but it’s not what she does. What she does instead, and what makes you feel like you’re gonna gush down your own naked thighs, gonna come right now, magically, somehow, is grab for the back of your head and press it back against her. Hard, desperate, her chest rising and falling and her legs raised like she’s been fucked like this a million times. She looks down at you with low lids and you moan at her neediness and start fucking her in earnest.
Dean’s head drops back when you clamp down on her again. Her tits are pushed up by her arms and you can’t see her face anymore, but you can hear her. Her sounds are animalistic, she’s nearly keening as you assault her g-spot from both sides.
It’s not long before she starts rolling her hips again and with her hold on your head still there, it’s like she’s face fucking you. You moan again, go faster. Your fingers going in and out of her pussy are drenched, make a sucking noise every time you push in.
Dean’s head shoots up again when you can tell she’s getting close.
“Mo– more,” she pants and for a moment, you’re too blissed out to understand what she wants, but then you do. Your girl wants to be filled, feel stuffed. You can do that.
A third finger joins the other two and you go harder, watch her keep her head up, skin flushed on her pretty face and on her chest, see her press her teeth together, take hissing breaths through them. Her stomach is clenching and small broken sounds leave her.
“Oh f–” she grunts, and then she comes.
Her whole body tenses, shoulders going up, stomach clenching, the most beautiful, twisted, pained, ugly expression on her face. If you could die from love, you would right now. Your lips pop off her and you slow your hand movement. Dean whines, your fingers drenched in her juices.
She slumps back with a grunt exactly the way she always does, completely emptied, a tad dramatic. Her legs go slack, one dropping on the mattress next to you, the other on your angled arm. Her breaths are deep and full bodied. You slowly pull your fingers from her. She sighs at that.
When you don’t move up her body, the way you would if you’d just blown her, she blinks, then looks down at you, a questioning look still on her exhausted low-lidded face.
“Babe?” she asks, voice a little cracked, making her sound so damn sexy. You let a grin heavy with meaning stretch over your face.
“Not done,” you say, and Dean’s eyes widen.
You make her come two more times, and then only stop because she insists, voice desperate, that she can’t take another one. You’d like to test that theory, but still you crawl up her body, drop down next to her on your side.
Dean’s eyes are closed and you just watch her for a second. You bring your hand up, run it over her cheek. She stirs at that, opens her eyes.
“I love you,” you say, voice quiet. Dean blinks, slowly, then brings her hand up, lays it over yours.
“I love you,” she replies. “That… that was nuts.” You raise your eyebrows with a smile.
“Unusual, that’s for sure,” you answer and she gives a half-hearted chuckle.
“But you liked it?” you ask. Dean clenches her jaw. She’s as handsome as a girl as she is pretty as a boy.
“What does it say about me that I did?” she asks quietly, and you can hear that telltale shaking in her voice, the one she gets when she’s holding back emotions. The intonation is the same but her voice is higher. But she’s all Dean. Stoic, too strong for her own good. As vulnerable as a kitten under it all.
“It doesn’t say anything,” you say, pressing your thumb against her cheek, which makes her smile a little. “It says I’m damn good at giving head, no matter what I’m working with.” Dean huffs, then rolls towards you.
“Well, I knew that,” she says and you grin, bring your face closer, run the tip of your nose over hers.
“I know you do,” you reply. “Still always nice to hear you scream my name.” Dean huffs, indignant, shakes her head.
“You know,” she says, “when Bobby turns me back into a dude, I am so getting payback for this.” You raise your eyebrows.
“You still got hands,” you point out, voice challenging, “a tongue. Not like you can’t do anything.” You press closer to her with a shit-eating grin. “Exhibit A: you being as fucked out as you are right now.” Dean shifts around, nose scrunching up, beautiful freckles dancing.
“I just…” she says, then stops, fidgets. You raise your head, laugh.
“Oh my God!” you say, voice loud. “Dean Winchester is a pillow princess, I can’t believe it!”
“Stop!” Dean says just as loudly, her hand going up and over your mouth. You try to get away from her, laughing, but she holds you close, keeps you quiet but soon she’s laughing too, pressing herself close to you, the soft smell of her and the happy face making your heart beat faster.
She lets go when both of you quiet down and the two of you just lie there, lazily dragging your fingers over each other’s bodies. You’re halfway to falling asleep when Dean’s phone buzzes.
She turns, reaches for it, then holds it over her face as she reads the message. She closes it, then turns to you.
“Bobby’s got the spell figured out,” she says and you hum.
“Too bad,” you say, throwing her a sideways look that tells her you’re joking, at least somewhat.
“Yeah,” she says, fidgeting with the phone, looking past you. You look at her, then purse your lips and reach for the phone.
“What–” she says but you shake your head, quiet her as you type out a message, send it.
“Telling Bobby we picked up a case,” you say as you snap the phone closed. Dean has her eyebrows raised when you look back at her.
“We didn’t pick up a case,” she says and you shrug.
“Sure, but he doesn’t have to know that.”
Dean narrows her eyes at you.
“What are you doing?” she asks. You push yourself up and she drops onto her back again as you hold yourself up over her.
“You know those black leather pants I have?” you ask and Dean raises her eyebrows.
“Y–yeah?” she answers.
“I’m thinking those, with the combat boots,” you reply. You see the twitch on Dean’s lips, something unsure but excited going through her.
“And, and then?” she asks, her usually so tough demeanor cracking to show you something beautiful and bright underneath.
“And then,” you say, “I’m taking my girl out on the town.”
