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eggcompany · 2 months

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Momma's got a HUGE cock

Dean was in town to see Sam, however he could never say no to hot college girls. Or older girls who wore cardigans and was a professor of theology.

Castiel Novak, mtf, 39, takes home Dean Winchester, ftm , 27, and makes him cry.

“Hey, can I get another?” Dean asked and looked around at the chicks sat at the bar. A red head to one side of the bar caught his eyes. A real Jolene, ivory skin and emerald eyes. He checked her out, trying to get her to look at him but she was chatting with someone else. He let his eyes look around again, a dude might be fun while he’s in town…

However, behind the red head, sat at a small table…

She was… wow. Dean walked away from the bar when the cool bottle touched his hand.

She had her long raven black hair clipped up in the back, head leaning on her hand, glossy blue nails tapping against her forehead, and was reading over a stack of papers. A drink forgotten at the end of the table, ice nearly melted in it.

Dean made his way over to her, god she was pretty, strong jaw, strawberry lips, long eyelashes, and the bluest eyes he’d ever seen. God and she was… broad shoulders, strong lookin hands, and, fuck, tits that looked straight up carved by heaven that fit so perfectly in her blue blouse under her crème cardigan. God, how could someone look so hot wearing a cardigan and slacks?

He leaned up against her table, causing her to look spooked and look up.

“Oh sorry, is, are you-”

“Hey calm down. Just wanted to say hi” Dean said with a smile, the lady blushed, putting her papers back down. She looked away, and waited nervously.

Dean took it as an invitation to sit down across from her leaning his chest on the table and look at the papers.

“Whatcha workin on, pretty lady?” He asked, sitting back and taking a sip of his beer. She rolled her eyes and shook her head a bit.

“I’m a teacher. I’m reading essays.” She said and took a sip from her drink. It had been a while since she’d been out to drink, usually opting for wine coolers at home. She’d seen most of the college aged guys in town and well… this seemed to be one of those college frat boys, all big muscles and smooth talk. He had cute pouty lips and pretty dirty blonde hair and eyes that seemed to go on for miles behind them. Quite… handsome. Alluring. Kinda like a magnet.

“Man… a teacher? Must be pretty smart. Wanna teach me a few things?” Dean flirted and the woman huffed a laugh. God she was pretty. And fuck he wanted her bad . At least for some kissing in the impala.

“I’m sure I could. But what’s your thing? Huh? Mister smooth talker?” She asked and gave him an appraising look and swirled her drink around her glass. Surely he knew her or something, a study guide or ‘extra credit’ in exchange for some sloppy sex. Though she just couldn’t put her finger on who he was…

“My thing? Hm… beer, my car, very very attractive women in bars who teach and wear sensible shoes.” Dean said with a smile, flicking his eyes down to the table where he’d seen her feet crossed, clad in a pair of plain tan and white sneakers.

She smiled down at herself, she was never one to dress up and go to bars, she prefers wearing her comfortable day clothes. Her regular tan slacks, a plain blue blouse, and she usually had a cardigan pulled over her shoulders. She looked back at him, he was wearing.. A lot to be honest. A tight black t-shirt with a red flannel over it and a leather jacket over it all. The jacket was a bit big on him but it suited him.

Then he leaned back, flipping his jacket open to show the small trans flag sewn on the inside of it, he scratched his jaw like he wasn’t showing.

The woman hummed and looked at it before looking back up at him. Of course. A kid looking for someone who understood.

“Your name then?” She asked, taking another sip of her drink. She never had much luck at bars. Never had much luck with… anyone. Except he was like a magnet, like she was being pulled to him. She wanted to touch his hand where it laid on the table and wanted to sit close to him and… maybe give him a kiss.

“Dean Winchester at your service miss…?” Dean said and waited for her answer. Her answer to anything.

“Castiel. Novak. Theology Professor.” She answered and he smiled, huffing an impressed noise.

“Wow, a real educated lady” Dean flirted and chewed on his bottom lip. She was the whole package.

“Mhm, ya know I have that same exact jacket, back at my place.” Castiel said hoping Dean would catch what she was pitching.

Fuck , She is more than the whole package.

“Oh really? Back at your place?” Dean asked, his face giving away how excited and happy he felt. Eyes wide as he swallowed thickly. He really hoped she meant she fucked trans guys or that she was… of the same persuasion. God either, neither, both, all, god, anything yes.

“About a four minute walk.” She answered, hands going to gather the papers and slip them into her vintage looking blue and brown messenger bag. She never usually feels like this, this weird compulsive need to take someone home.

“Yes ma’am” Dean said and slipped off the stool and threw some dollars on the counter when the bartender came to close his tab. He turned and she was standing, almost as tall as him. She was holding her bag in front of her. Demisexual and the new pride flag pinned proud on the front.

That’s fine. She could do whatever she wanted with him. Hell, she could take him home and make him sleep in her bathtub and he’d be happier than a clam. He just felt this… want. She was so pretty and hot and she probably had a bed and probably had a chair or couch and that sounds a lot more comfy than sleeping in the impala.

She was wanting, he just didn’t know or care what for.

“Do you still want to come home with me?” She asked, pulling him from his buzzed spiral of warm bed, boobs, bed, boobs, bath tub, boobs .

“Gladly” Dean said cheerily and followed behind her. And oh man , she had a nice ass, thick thighs too. He was busy staring at the way her hips moved when she walked to notice her calling his name.

“Oh yeah yeah? Hm?” He asked and looked back up to her smirking face. He didn’t care that he got caught staring. Especially when it caused Castiel to roll her eyes and smile at him.

“I asked if you go to Stanford or not.” She repeated, amused at the way Dean had caught up to her only to turn around and start walking backwards in front of her.

“Oh no, my uh my little brother does. I came up to see him. I'm not really the school type.” Dean said, throwing air quotations around ‘ school’ . He was never good at school, always had better things to do, other places to be. Though if all teachers were like Professor Novak it might be worth going back.

“Hm then what do you do? You’re what? 26?” Castiel questioned, should she really bring this guy home if he’s… bad? Sketchy at least.

“27, thank you very much. I um… I travel around a lot. Doin’ odd jobs and stuff. Well actually me and my dad do that but he said he had to go do something but then he didn’t come back so I came to ask Sammy if he knew anything. Uh Sammy’s my brother, he lives around here somewhere.” Dean said and looked around at the houses, turning back around to walk beside the woman.

“Oh, does your family live up here? There’s a couple of my students that live with their extended family while up here or in a summer home.” Castiel asked, it was easy to talk to Dean, easy to know she’s not overstepping a line.

“Nah… our mom actually uh she passed when Sam was six months. I was four. House fire actually. After that we just kinda… started surfing the road, never stopping or nothing. Sam was always good at school though so he got here all by himself. He’s a… he’s a really smart kid.” Dean praised, he couldn’t even start to explain how proud he was for Sam. How he wished he could have made a better life for himself too but… just roll with the punches.

“Dean… you’re a very sweet young man. Cute even.” She said and cupped his jaw in her hand. He breathed heavily for a second. Why was he so comfortable around her so.. open and in love already. Fuck, he was falling faster than a fridge tied to an anchor.

“You’re just… really pretty. And and I dunno. I dunno why I feel like… like I know you.” Dean panted out, eyes flashing from hers down to her lips and back over and over again. Her hand felt so.. Solid and warm and grounding against his cheek.

“I feel the same which… is so odd. I never connect with people like this. I always feel a bit like… like looking in through the window.” Castiel said, stepping closer a bit, just a breath away from the man who felt like his chest was getting squeezed when he realized they were still on the sidewalk.

“Can I come in?” Dean asked, tearing his eyes away from her to the front door. He wanted to get away from any eyes that peeped, any cars that passed.

“I… I think so. Yeah” She said and pulled away from him, hand sliding down his neck, shoulder, arm, to catch his hand and pull him along.

------

“No I, I kept my name. It’s after the angel of Thursday. It’s always meant a lot to me. My brother actually named me, my first two brothers were named after archangels, Gabriel and Michael. Then Balthazar was born and then me and my brother Gabriel named me because I was born on Thursday. I have… a lot of siblings. Gabriel named most of them.” Castiel explained as she handed Dean a cup of sweet sugared tea and sat down with her own honey stirred cup of earl grey.

He was sitting on the couch, boots kicked off at the door next to her sneakers, legs criss-crossed, jacket and flannel shucked off to the coat rack while Castiel’s cardigan was folded over the back of a barstool.

“Sounds kinda nice. My ma named me. Deanna. Doesn’t fit at all, everyone always just called me Dee, or Danny, Sammy called me Danny cause he had the worst time talking he messed up every word he ever said till he was like seven. I was thinking about Danny or Daniel but… Dean just stuck. Plus Dean Winchester has a nice ring to it, don't you think.” Dean said, sipping the nice dark tea that was perfectly sweet. It was nice to just talk about this crap. Plus Castiel was so… god her whole house smelled like her and it smelled fucking good like honey and laundry detergent and printer ink.

Plus the way she shook her head and smiled was… it made his heart do a weird flip flop.

“It does. I can’t picture you as a Deanna. I much prefer Dean.” She said and moved a bit closer to him, turning so she was facing him, curling up so her socked toes nearly touched his warm jean covered leg.

“Hm… you smell good.” Dean said and leaned forward a bit so his head rested on the back of the couch, lolled back a bit.

“Mmh~ Mister Winchester are you trying to get in my panties?” Castiel said teasingly as she leaned forward so her face rested a few inches from Dean’s. His breath was hot and stank of beer as it washed over her face and he felt the same only her breath smelled like everclear and mints.

“Yeah. Yeah I am. Please?” Dean asked, confidence fading for a moment only to soften the rejection if it happened. He doubted himself was this not what she had wanted? Did she just wanna chat? Was this pushing the line?

She took in a shaky breath and she couldn’t hold back, he was so willing and she hadn’t done it in so long, she’d not felt the need or want to do it for so long.

“God you’re cute it’s not even fair, come here” Castiel says and pulls him over to straddle her lap, her hand coming up to pull his head to hers, lips meeting. Dean was quick to moan and get his hands to her sides, pulling at her blouse. She had her hands on the sides of his head, keeping him from pulling away as their tongues met. He let her explore his mouth, easily giving up dominance of the kiss. He groaned and pulled at the buttons of her shirt, begging for it to be off.

She pulled back, staring at him, her lipstick smeared over his lips and to the side a bit. They were both a bit out of breath, her hands relaxing and dropping to his shoulders.

It felt good to… well feel good. She felt happy. And horny. It was great.

“Even deal, shirt or shirt” She said and pulled at the shoulders of his tight t-shirt. He smiled.

“Yes ma'am” He said happily and pulled the shirt off by the neck, throwing it over to the corner. Baring his muscular torso and strong arms, his thin red surgery scars framing his pecs, healed half-hazardly, puffed up in some places and thinner and fainter in others.

Castiel stared at him as he knelt over her, jeans low on his hips. He was… hot, tan, and… fuckable. He smiled and leaned down to kiss her again, short closed mouth kisses, with his thumb holding her chin.

“Your turn, Miss Novak” He said and sat back, fingers playing with the bottom of her blouse. She swallowed and nodded, giving him permission to start undoing the buttons. And soon she was bared down to her plain white bra.

“If I had known I was going to have company I would have worn something a bit more flattering.” She said and looked away from him. She had this bra since she got her boobs… and she’d washed it maybe 5 times in a year. She had other nice bras, lacey ones and push up ones and ones that made her look thinner and less broad.

“I think you look hot, really hot. Can I touch em?” Dean asked as he practically drooled over the perfect soft looking pale breasts that were cupped in front of him. God those were… the best. And he said as much.

“Those are the best” He said, which caused her to cover her face and laugh, embarrassment flooding through her.

“Yeah… the… the clasp is kinda busted in the back so I can- oh!” She tried to explain and reach back but Dean had already popped the two good clasps and wiggled the last one free. She was surprised but well… Dean probably had experienced bra issues in the past.

Dean’s hands found their way to cup and grab at the soft squish of her breast, groaning into the kiss he pulled her into. Fuck, she was warm and welcoming and undoing his belt but his hands stopped her from unzipping his jeans. He looked down at her… so pretty. So feminine, so pretty, so gentle, so… everything.

“I uh… I don’t got um… I haven’t… I’m still…” He struggled but Castiel cupped his face and gave him a sweet look, an understanding look.

“It’s okay. I haven’t had surgery down there either, at least not that kind of surgery. Do you wanna stop?” She said and let her thumb rub over his cheekbone, warm and comforting. Dean breathed and calmed down and shook his head, hands traveling from her chest down over her soft stomach down to her slacks, looking at her as he unbuttoned them and pulled the zipper down.

“I don’t wanna stop, I wanna keep going.” Dean said seriously and leaned down to kiss her deeply, tongues rolling together, as her hands came to his hips and slipped under his jeans, over his briefs, to press at him.

He pulled back and huffed, panting as her fingers pressed against his wet cunt, his briefs soaked through nearly. He let out a whimper, shoving his head into her shoulder, panting.

“Do you.. You can touch me. Please touch me, I’m so hard” Dean whimpered and rubbed against her hand.

She was so happy. He was… god so perfect, willing and wet and perfect. She pulled her hand back, pulling his jeans down but they wouldn’t get over his thighs.

“Up, take them off, all of it off, I wanna get my hands on your cock” Castiel said, letting her voice relax and drop a bit. Dean shuttered standing up for a moment to yank at his pants and underwear until it was on a pile on the floor. He climbed back into her lap, not embarrassed of how wet he was or that his cock wasn’t very big. He took testosterone when he could, when he could swindle it, John never helped him get it so he was all on his own. So his… his cock was bigger but not really… just enough to be able to get between his fingers and rub.

Castiel let her hands wander over his smooth back, feeling the muscles flex and relax before traveling down and giving his ass a grab. Dean jumped a bit but smiled and got his hands back on her soft chest, he wanted to bend down and give them each a kiss.

“Cas…” He breathed out, feeling a bit overwhelmed but… too horny to care. He leaned down and kissed her again but cried out when her fingers slid over him, finger tips pushing at his slick hole. He grabbed around her shoulders, whispering in her ear, too embarrassed to actually say it.

“You can put it in, if you wanna” He whimpered and Castiel shook her head and turned her head and kissed his forehead.

“Dean?” She asked, hand cupping him, feeling how burning hot and wet he was.

“Yeah, Cas?” He replied, which made her happy because well… no one ever called her ‘Cas’. And he was just… so cute.

“I’m gonna make you cum until you cry. Do you know why?” Castiel said, pressing her palm into Dean’s hard cock. Dean moaned out a little bit and breathed quickly, his stomach clenching up at the thought of Castiel… ruining him. He felt a little light headed, especially with her hand pressing right up against his cock and her fingers over his whole cunt and and- fuck

“Wh-Why?” He forced out grinding against her hand. She crooked her fingers up to just nearly be inside of him, inciting a gasp from him. She pulled him back by the hair on the back of his head, making him look at her, he was gasping.

“Because you’re so cute” She said and pulled him down for a kiss and shoved two of her fingers into his dripping hole. Dean moaned, grinding as much as he could against her fingers that seemed to immediately find a sweet spot inside him. She licked into his mouth, sucking his bottom lip into her mouth for a moment before kissing down his neck.

“Ah- I don’t like that. Just, kiss me up here” Dean said and pulled her face back up to his, he didn’t like getting necked. Never did, didn’t know why. Castiel kissed him and moved to nibble at his ear, her lipstick tracing a line from his lips over.

“Good boy” She whispered and started working her fingers in and out of him, forcing loud moans and groans from his throat.

-----

“Fuck! Fu-uh-uh-uck, please, oh god, feels so fuggin good! Please” Dean cried out as tears streamed down his face. His arms were wrapped around Castiel’s neck, hands grabbing onto her shoulders, she was squeezing his cock a bit tight and it was driving him crazy .

Dean cried out and covered his mouth, mumbling something.

“Say it baby, what’re you gonna say” Castiel egged him on, she loved the way he cried and all the noises he made and god hearing him was the best . She wanted to squeeze every noise out of him.

He leaned back, stomach tense and jumpy, he was breathing so heavily, his chest heaving, he’d never felt like this before. He looked at her, god she was so pretty why the fuck was he so loose lipped and and god her hands -

“Oh fuck momma, I’m so close” Dean whimpered, clenching down on her three fingers. He looked at her as her eyes got big and her mouth opened in surprise, her hand stopped moving on him. He immediately tried to back track, most women he was with didn’t like that. He liked it but most women thought it was… weird.

“I’m sorry I-” He said and tried to raise himself up off her fingers but she had him by the hair, pulling him down so they were nearly nose to nose. She pulled her fingers out of him and had his cock between her fingers.

“Say it again.” She nearly growled, feeling her cock throb in her panties. She didn;t think she had any kinks but that was… jeez Dean was her kink.

“I’m so close momma, fuck, rub my dick please, please touch it” Dean whimpered desperately, she was really squeezing him and fuck he was so close he was getting a headache.

“God, yeah, you like mumma’s fingers in you?” Castiel asked and kept her fingers stead on him even as he twitched and jerked. She felt like her skin was alight with fire, everywhere they touched it felt like they were burning, their chests, stomachs, everywhere they touched felt like they could never pull away.

“Yeah, love your fingers in my cunny momma, please! Please! I feel so empty but I’m so c-close” Dean begged he just wanted to cum, he was so close. Castiel pulled her hands away, grabbing at his body as she surged up to kiss him.

“God Dean, I haven’t felt… like this in so long. Can I fuck you?” Castiel asked, huffed against his cheek as he kissed down her jaw. It was like a rushed fever had washed over them, an overwhelming need.

“Yes please please fuck me fill me up.” Dean begged and Castiel was standing, hands hauling him up with her.

“Holy shit, you’re so fucking perfect, so strong, fuck me momma, fuck me” Dean cried as he was carried through the house, loving the view of Castiel’s boobs where they pressed up against his sternum. He shoved his forehead against the top of her head, taking in the sweet scent of her hair.

She got through to her bedroom, kicking the door shut behind her, and dropped him on the bed. He shoved himself up to be in the center of the bed. She was quick to shove her slacks off and to crawl over him. She straddled him looking down at his red cunt and throbbing cock. He reached up to play with her tits, roll her nipples between his fingers and squish them together.

“What’re you gonna fuck me with? What’re you gonna shove in my cunny?” Dean asked, setting what he wanted his junk to be called. She smiled and leaned down to kiss him, guiding his legs apart so she was knelt between them, not letting each other get very far.

“I’m gonna fuck you… I’m gonna put my… I don’t wanna say it. I wanna put it in but I don't want to say… those words.” She said, self conscious about saying cock or dick or anything else. She didn’t wanna think about that.

“Okay, just stuff me momma, I’m… I’m dying for it” Dean said and looked down to where her panties were bulging out in the front. She was so pretty, her thighs looked strong and he liked the way she had a happy trail which he traced down, it was soft and short.

She knelt up and covered the trail and her bulge, looking away, face turning even more red.

“If I knew I would have company I would have shaved… I haven’t um… I’m not very smooth down there.” She explained and he huffed and shook his head. He usually kept himself trimmed with his electric trimmer just because he liked it. He reached down and moved her hands.

“I think it’s cute. I think this is cute too…” Dean said with his bottom lip caught in his teeth as he traced down her bulge. She leaned down and kissed him again smiling against each other, so comfortable.

“Am I still a pretty lady with this?” She said and when she leaned back she pulled her panties down so her cock could slip out from behind the thick cotton fabric. Dean looked at it with hungry eyes and a wolfish grin.

“Prettiest lady I’ve ever seen…” He said and let one of his hands wrap around it and give it a few strokes… goodness he could barely get his hard around it and it was… at least eight inches long.

“That’s… that’s big. Uh you have any lube?” He asked, nervousness creeping into his voice as he took in how… heavy and long and thick her cock was… hell his toy was probably half as big.

“Yeah I do. But there is something else I wanna do…” Cas said, letting her hips roll up into his hand a few times before nipping at his neck and pulling away. Dean looked at her eyes and then at the big thing in his hand, that would not fit in his mouth but but she was so… he would choke on it if she asked.

“I could- I’d you wanna- I mean-” Dean started but she was quick to press a kiss to quiet him.

“Can I blow you, Dean?” She asked, hand going down to lightly dance over his inner thighs, sticky with drying slick, shaking with desperation. He was nodding, eyes squeezed shut, trying not to cry out.

“Fuck… yeah. Yeah you can gimme head” Dean finally struggled out after cracking his eyes open to see Castiel perfectly content petting around his inner thighs and just above where he wished she would touch. She smiled and kissed his lips before making her way down to his dripping cunt and hard cock.

----

“Fuck fuck fuckfuckfuckfuckfuckfuck, ‘m gonna cum. Fuck, Cas, Cassy, I’m gonna cum” Dean cried out as Cas kept on just barely grazing her teeth over his cock, keeping her fingers rubbing at all the good spots inside him.

She pulled back, sucking harshly as she did, cock leaving her lips with a pop. She looked up at him and stilled her fingers, she had a devilish smile on her lips and shook her head. She blew out a cold breath onto him, causing him to shiver and whimper.

“No! No no no I can go again. I can’t can fuck like four times no problem please please lemme cum” Dean begged, he was at his limit, he felt like he was burning alive, tears rolling down the sides of his face, throat nearly sore from yelling out.

“Oh I dunno… you’re cocks pretty hard, might just wanna play with it all night” Castiel taunted, nail coming to run up the bottom of it and flick the tip of it. Dean cried out, hips bucking up and hands finally leaving the sheets and grabbing at Castiel’s hands.

“Please momma lemme cum and I’ll take you so good, all the way, I’ll be so good if you lemme cum.” Dean tried to convince and his voice cracked and… well Castiel couldn’t turn him down when he looked so… pathetically attractive like a wet cat.

“Then I guess it’s fine” Castiel said in a fake put out kinda way and pinched the nub between her fingers and started jerking him quickly and harshly. Dean cried out, quivering against the bed. He was screaming out legs going to wrap around Cas’s waist, crushing her tightly.

“Cas! Fuck! Fuck! Please! God Fuh! Momma, god, yes, yes, yes yesyesyes” Dean begged and grabbed onto the sheets so tight it felt like he could rip through them. He took in one big breath and let out a high pitched moan, feeling like his brain turned off as wave after wave of pleasure twisted him all up and untied all at once. He relaxed down to feeling like jelly against the bed, catching his breath.

Cas shushed him, gently running her hands over his belly, up and down his sides, on the outsides of his legs. She was staring down at where he was dripping, her white blanket turning dark with how much he’d cum, how wet he’d gotten. She ran her fingers through it, up and down over his folds.

“It’s okay, you’re okay, what a good boy. Such a good boy. Look at that... Came all over mumma’s fingers. Look at that…” She said and brought her dripping hand up to her mouth, his rich lovely scent encompassing all her senses. God he tasted good. God she was hard, her heart was in knots too though. She moaned around her fingers, groaning at how he tasted, smelled, how he everything.

“That’s not fair…” Dean groaned as he finally came down, watching her lick his slick off her hand. Castiel smiled and dropped her hand to give her cock a few tight strokes, staring down at him, all tan muscles and wet cunt.

“I don’t care. Can I put this in now?” Cas said and scooted up to slap her cock against his folds. She smiled at him, tongue poked between her teeth. Dean closed his eyes, he just came but… it was like his mind was made of putty and she had her hands in it.

“Oh momma… yeah. Yeah fuck me deep. Put it in my cunt.” He whimpered and pulled her down for a kiss, her breast squishing against his chest.

Castiel guided her cock into him, panting against his neck. Dean whimpered and held her around her shoulders, he tried to relax but god… it kinda hurt. He really wasn’t used to things that big being… crammed into him.

“Cas… cas… It’s too big I can’t, it’s gonna hurt me” Dean said sorrowfully and looked heartbroken when Cas pulled out a bit and got on her hands over him, He didn’t wanna look at her… he hated being looked at like this when he was getting fucked.

“I don’t think this is a good position, I’m not fond of… well humping like an animal.” She said and that caused them both to crack up as she pulled out and they sat across from each other, each a little amused with the situation.

“Ya know I’ve never met a gal like you before.” Dean said, leaning his head against his shoulder, looking at her as she sat down across legged, cock still hard between her legs. She looked at him with a look that was… it made him feel sparkling.

“I’ve never met a man like you either.” She said and then a thought popped into her head. Dean was about to say something but she cut him off, crawling toward him to kiss him and smile.

“I know the perfect thing, move over.” She said and laid down, unclipping her hair and throwing the clip to the side, waist length hair falling down around her like a dark halo. Dean watched and man… she was pretty. He was lucky as hell, huh?

“Okay now you get like you’re gonna fuck me and and lemme pull my legs up.” Cas said excitedly as she pulled her knees to her chest. Dean got between them and looked at her funny, what was she doing?

“Okay see, now just… lean forward, I’m flexible, don't worry…” She said and pulled him down over her so he was pinning her down. She smiled and moved her hands between them, guiding her cock back up to his cunt. Dean looked down at her, this was… it was like he was fucking her position wise. But also… it wouldn’t offer a lot of penetration.

“Man… I knew you could teach me” He said and smiled as he leaned down to kiss her, she held her cock up for him to lower down on it. Castiel huffed as he lowered down onto her, he was so warm and wet and tight.

“That’s good Dean… Now fuck me.” Castiel said and it only took Dean a few tried to get the hang of it, he had to kinda rock back and forth and not really thrust but fuck it was good. He never felt so good and Castiel made such pretty sounds, eyes closed and lips in a perfect O.

----

“Do you wanna get a shower with me?” Cas asked as they came down, laying next to each other covered in sweat and cum. Cas had reassured him that she had a vasectomy and that she was clean, he’d said fuck it to a condom. Dean had rode her until she’d cum, filling him, and then had gotten too strained and rode her regularly, until he’d cum again, her fingers on his cock.

Dean was just barely awake, struggling to not doze off on the soft cozy comfort of her bed. It had been so long since he’d had the comfort of a warm bed, and a cuddle, and a shower without having to look for roaches or used condoms.

“God yes, last time I showered I had to wear boots because of the fungus.” Dean said and sat up, a twinge in his back but a dull perfect ache inside himself. Castiel chuckled and looked over at him, hand coming up to trace shapes in his lower back.

“Sounds gross, lucky for you I’m a clean freak so.. No fungus.” She said and sat up, holding the blanket over her chest. Her nipples ached a bit from Dean’s toying with them so much, well toying and sucking and biting and damn she had class to teach tomorrow she’d need to put bandaids over them. Dean groaned when he stood up, slick and jizz sliding down his legs, Cas stared cause fuck that’s…

“Are you gonna eat me, Miss Novak? Naughty naughty, I thought you were a sweet gal.” He said teasingly, pulling his ass apart to both show where he was dripping and to spread himself just enough for another rush of cum to slip out of him. Cas was nearly hard again when she saw that.

“Now, now, that’s asking for trouble” She said and looked back at Dean’s smiling face. God he was cute. He turned back to her, shameless of his form.

“Come on, I don’t like being sticky, makes me sad.” He said, looking down face pulling into a sad expression. Cas stood up, pulled him into a kiss, a soft gentle kiss.

“It’s okay, I’m not fond of being naked or sticky.” She said and pulled him to the bathroom right outside the bedroom, she was quick to pull him behind the glass door and turn the hot water on.

“It’s so late, I have a class at nine tomorrow.” Castiel complained as she stood under the water, letting it hit her in the face and soak through her hair. Dean hugged her from behind, resting his head against her shoulder.

“Sorry, I can leave now if you want” Dean offered, stepping away from her, he’d leave if she wanted, it wasn’t very far to the impala. Castiel turned around and pulled him under the water as she stepped back out of it.

“Aw but how sad to sleep alone when I have a big strong man to hold me.” She said which caused Dean to smile and kiss her. They kissed a bit more before the woman got a bottle of body wash and a bath sponge.

“Oou… frilly. I feel so pampered.” Dean said jokily as she started scrubbing him down, smiling at him. She let her hands wash him, a weird feeling of… content enjoyment as he basked in the warm water. She got a little lost in the movement of it, that was until she was on her knees in front of him and felt his hand on her shoulder.

“Cas, get up.” He said, not looking at her, just looking kinda sour to the side. She rose up, looking at her with her head cocked to the side, confused.

“What’s wrong?” She asked but Dean was pulling her into a hug. She hugged him back but he wouldn’t let go, He just held onto her, water hitting his back. She rubbed his back and felt him sniffle once before pulling away. She held his face in her hands and she kissed all over his face, cheek, forehead, nose, chin, everywhere.

“So emotional, do you need mummy to kiss it better?” She asked, only sorta kidding. Dean cracked a smile and nodded and they kissed again, Cas loving the way Dean was. Just everything about him.

“Why’re you so hot and so sweet? Why’re you just… lovin on me?” Dean asked and kept his forehead leaning on her shoulder.

“Cause I like you” She said and held him. She did like him. He was cute and funny and kind and she just felt pulled to him. He huffed a laugh and pulled back to look at her, all soaked from the shower and gleaming with post orgasm glow.

“Yeah I like you too” He agreed and made her smile as his hands traveled back up to her boobs.

“You like me or you like my tits, cause they were expensive” She said and he laughed and bent down to kiss and lick them for just a moment before kissing her.

“Boobs are definitely a plus. Uh… is it weird if I ask you on a date?” Dean asked and looked at her for a minute as she turned the water off, she was rinsed it was enough. She could shower in the morning.

“Do my boobs get to come too?” She joked and he nodded, smiling widely, eyes scrunching up.

“They can definitely come too, also can I borrow some pants?” He asked and soon they were snuggled in bed, dirty blanket tossed to the floor and new one pulled from the closet. Dean was out like a light, enjoying the company and comfort.

---

It was easy to find work. Cas let him stay, promising he’d be good. They slept together and Cas learned that he could cook an amazing breakfast and a mean burger but also loved milkshakes and smoothies. Dean learned that Cas had… quite a sex toy collection. Dildos, vibrators, beads, rings, all sorts of stuff that made Dean’s little blue dildo seem like a household decoration.

She had also given him enough confidence to talk to Sam. He had turned away and left when he’d seen his brother one too many times, just not having the guts to say something.

So one Thursday when he knew Sam would be walking through the parking lot he was waiting. Well not waiting. Cas didn’t have a class for another two hours so they had gotten lunch and Dean was napping off his carbs while Cas was reading papers in the front seat of the impala. It was a beautiful day so the windows were down and Dean only had Cas’s soft cardigan thrown over him.

“Hey De- Professor Novak? Why’re you in my brother’s car? I didn’t know-” Sam said as he spotted the impala and came up to see his brother. He hadn’t talked to Dean since he left for college. He loved Dean, never really saw him as a sister anyway. However he was incredibly surprised when he saw the theology prof in Dean’s car. Especially when he didn’t know Dean even knew the professor.

“Dean, sweety, wake up. Sorry we just had lunch.” Cas said and reached over to stroke through Dean’s hair which was usually a major no go. Sam gawked at them when he saw that. He looked at Dean who yawned and sat up.

“You’re boning. Jesus! Dean, I haven’t seen you in like a year and you come and smash one of the professors!? You dickbag!” Sam said and stepped away from the car and turned back to it, hands on his hips.

“Technically she smashes me but whatever. I need to talk to you but uh… I’m gonna be in town for a while.” Dean said and leaned over the front seat, shit eating grin pasted on his face as Cas smacked his arm and shook her head at his nasty talk.

“Smashing the theology professor. You’re a dog, you know that?” Sam said and climbed into the driver’s seat leaning over to give Dean a half hug. It was still nice to see him.

#egg_company #fanfic #smut tag #dean x castiel #castiel supernatural #castiel #destiel fic #destiel #destiel smut #dean winchester #trans castiel #trans dean winchester #f/m #smut fanfiction #supernatural smut

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boywifesammy · 9 months

Text

imagine repressed & closeted transfem dean who never figures it out. imagine the sheer amount of guilt, fear, self-hatred and disgust he’d feel at what he is. big, clunky, dangerous. he takes comfort in his power, but it makes him feel sick. when he looks into the mirror and sees his hard edges, his body feels like it’s trying to rip open from the inside, yet he has no idea why.

dean plays his father’s wife until he dies. he takes care of sam and raises him as if he’s his own son. he’s a housewife in everything but reality. he desperately wants family, desperately wants to nurture, but his body isn’t built for that.

he’s taught by john and the world that he has to be strong. he has to be a man. he can never show emotion, because it’ll only be a weakness, and weakness is deadly. dean can never have a family because his body is wrong and he can never love like a woman because he cannot be weak.

so dean holds tight to those little moments of female connection with sam and his father like a dirty secret. he lays in bed at night and pretends he doesn’t think about being softer and lovelier. he stares at himself in motel mirrors until it makes him sick. he builds muscle and crops his hair short because this thing inside of him terrifies the hell out of him and he has to do anything to keep it at bay.

women comment on his looks a lot. when he’s young, they call him pretty, beautiful, gorgeous. they compliment his soft green eyes and plush lips and spattering of freckles. secretly, dean loves it. it makes that thing inside of him flare up in joy, which is why he knows that this is dangerous, and not something to be indulged. he stays up at night obsessing. shaves every morning and runs his fingers over his soft cheeks, flutters his long eye lashes, tries to find the soft edges of his cheekbones.

this thing is slowly eating away at him. the closer he gets to it the more volatile he feels. he jerks off under the blankets with a hand over his mouth to stifle the gasping, whimpery sounds he makes. the sound of his own voice scares him. his throat chokes up when a guy hits on him and john gives him a glare. one time he puts a finger up his ass and comes so hard that he sees stars, not because of the stimulation, but just from the idea of being wet and slick and pliant between his legs.

dean loves women and it makes him feel sick to the very core. he wishes that he loved women in a normal way. instead, he sees their curvy bodies and an awful, disgusting mixture of greed-lust-jealousy rocks through him. it’s all a strange, roundabout way of wrecking himself, because it’s extremely easy to play the role they want him to play, but god if it doesn’t hurt like hell.

dean loves fucking women. he’s desperate in bed but he’s always sure to be gentle with his thrusts. it makes him feel less disgusting. he likes shoving his face into a chick’s pussy, eating her out until she’s dripping, or nuzzling into the crook of her neck as he fucks her wet cunt. he likes listening to their gasping whines and moans. the feeling of it all makes his teeth clench with guilt; her cunt on his dick, his strong thighs, the way she keeps moaning his name. but it’s so easy to pretend in moments like these.

dean puts his face into her hair, and smells her citrus shampoo as she wails out cries. he doesn’t imagine being her, but he focuses on her noises, on the softness of her body and the wetness of her pussy. he always cums silently, his entire body quivering and shaking, because he’s too scared of the noise that’d come out of his mouth if he opened it.

when rhonda hurley makes him wear her panties, he nearly throws up on her carpet from how hard his heart is beating. they’re silky on his dick. rhonda calls him pretty, beautiful, she strokes at his flaccid penis through the panties and kisses messy lines up his belly. dean is hard and shivering by the end of her teasing, leaking through the panties and flushed from head to toe.

rhonda is both the best fuck that dean ever has and his worst fears coming to life. she calls him good girl as he fucks her. it ends embarrassingly early. when dean cums, it’s with a gasping cry of her name and a girly little keen that haunts his nightmares. he doesn’t remember ever cumming so hard in his life. he shook with aftershocks for minutes after, dazed and disgusted with himself.

rhonda gives dean her number. he never calls her back. after dean leaves that town, he burns the panties and stops shaving his stubble so short. memories of rhonda make him angry. he sinks into hunting and drinks until he’s cross-eyed. dean takes solace in the horror of violence. he bathes himself in that disgust and he feels right at home in the middle of it.

sometimes, dean can’t sleep at night from how sick he feels. he tries to figure out why, but he can’t place the reason. it eats him up inside. makes him feel like a monster. he thinks that he may just be a disgusting freak of a man.

as dean gets older the comments about him getting pretty melt away. he knows he’s objectively extremely attractive, in a male model sort of way, but it doesn’t match up with the images in his head.

the thoughts get more and more humiliating as time goes on. he’s not a twink anymore and he can’t be fantasizing about being fem, but he can’t stop it. he stays up at night itching in his own skin, brutally aware that he’d look hideous and disgusting in anything girly. his body is too big and bulky. he’s a freak for being into that sort of thing.

dean eventually admits to himself that he might be a little gay. he keeps it on the dl, visits gay bars when they hit more liberal cities, and doesn’t ever repeat the same place. he likes being dressed up and bent over. he chalks it all up to a crossdressing fetish, and while that’s humiliating and sickening, it’s easier than having to deal with whatever it is that’s going on with him.

dean aches inside perpetually because he is flawed. he wants to hold his child in his arms and wear dresses and flirt shamelessly with men. he knows he’s a freak for it but he’s accepted that he’s going to perpetually live with this pain.

he gets older and older and the dysphoria gets so fucking bad that he can’t even look in the mirror anymore, but it doesn’t matter at this point. he’s completely disconnected himself from his body. he’s a sick, perverted freak in the body of a man and none of it feels right. he uses his body like a tool, a weapon, and he purposefully keeps it masculine and well-toned to push back any illusions that he’s anything but a man.

and sometimes, he’ll go to gay bars and let himself get railed to incoherence. he’ll drive three towns over while sam’s asleep and put on his makeup in an alleyway nearby. he always looks for men bigger than him. men who’ll call him pretty and beautiful and treat his ass like a cunt.

and if he’s lucky, maybe they’ll let some other words slip. maybe they’ll call him babygirl or darling or play with his pecs like tits as they pound him deep. and sometimes, if he’s really lucky, he’ll get to wear something pink and lacy. sheer panties. a bralet. stockings or a necklace.

he always cums in the first few minutes on those nights. he doesn’t mind being fucked until the other guy finishes, as long as he keeps calling him a good girl for taking it.

dean always throws up in the club bathroom afterwards. he spends hours wiping off all the makeup from his face and sleeps in the impala for the night. he gives himself another wipe the morning after and tells sam that he was out with a one night stand. it technically isn’t a lie.

one time, sam makes a joke about dean being a woman. he pushes. he calls him a pretty lady, and dean is horrified when his eyes wet a bit at it. he can’t take it. he starts the fight, but sam wins it. he pins dean down and starts to yell at him. then he sees that dean is crying. he isn’t making any noise or shaking, but his cheeks are wet.

don’t, is all he says. it hurts like hell to get out. sam seems confused, but he doesn’t question it. he doesn’t make the joke again. dean forgets about the whole thing and pretends he doesn’t feel the weird looks sam sends him sometimes.

dean dies like that, alone and angry, in a body that’s all hard edges and grief and hatred.

he’s the same in heaven. he can’t imagine being any other way. he doesn’t even know what he wants, what would make him happy. most days, he’s happy with driving his impala aimlessly, drinking while watching sunsets and tuning into the world around him. thinking, and thinking, and thinking. about rhonda hurley and her satin panties and his father and the soft, warm thing buried inside of him.

dean doesn’t know why he feels sick inside when he looks at himself, but he’s too broken to ever figure it out. the only thing that he knows is that he doesn’t feel guilt the same in heaven. that means that when he has those strange dreams of warm kisses, strong arms around his tiny waist, and the warm, beating heat of his child’s heart against his own pillowed chest, he can spend some time in bed in the morning trying to recollect the memories without hating himself for it.

#oc #supernatural #spn meta #transfem dean winchester #mtf dean winchester #sam winchester #character analysis #trans headcanon #me ramblibg incoherently again about tbe nuance and intricacy of trans winchesters #this ended up WAYYY longer than i intended #but god my heart HURTS just thinking about her #transfem dean is so uniquely devastating she tears me up inside #i use he/him prns for her here because it works better with context #and she never actually comes to terms with her gender #but god i love her to bits she’s my little girlie

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