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FIC: Walk a Mile, NC-17, 1/2

angstyboys by soul_flowers
Title: Walk a Mile, 1/2
Author: CloudyJenn
Fandom: Supernatural
Pairings: Dean/Castiel, implied Sam/Gabriel
Rating: NC-17
Word Count: 13, 400+
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.
Warnings: genderswap, smut
Summary: Gabriel's deal is worth saving Bobby's life. Still, being stuck as a woman for three weeks is not Dean's idea of a good time.
Author's Notes: I wrote much of this on twitter ages ago and then it was lost to the twitlonger ban. So I pulled it together, finished it up and here it is! I'm planning several one-shots set in the time between the end and the epilogue as well as telling Sam's side of the story.



"Oh for god's sake."

Dean doesn't want to wake up. He knows it's going to be bad. If it had been for anything less than saving Bobby's life, Dean would never have agreed to the deal.

"Sam?"

"It…could be worse."

That cautious tone does nothing to reassure Dean. It's the one Sam uses when he's afraid Dean's going to flip his lid.

It's a band-aid. Just rip it off.

Dean opens his eyes to see his baby brother staring at himself in the mirror. Staring and cupping a fucking massive pair of tits in both hands. Words fail Dean. His eyes travel down from Sam's long shiny hair past the boobs on down to the rounded hips barely holding up Sam's sleep pants.

"The fuck? That's what he chose? Oh god." Dean immediately sticks his hand up his own t-shirt. "What the hell? Mine are fucking tiny!"

Sam winces. "That's why you're upset? You know he only gave me these so he could leer at me."

"Still," Dean grumbles.

"You're just mad because you want to play with them." At Dean's silence, Sam glares at him in the mirror. "No, you cannot play with my breasts, you freak."

Dean sits up and yelps as a pile of hair flops down over his shoulders. He leaps from the bed, but the hair follows him. It trails all the way to his waist, thick and dark blond.

Sam snickers.

"So he gave you hair instead of boobs."

"What the hell, seriously, what the hell!" Dean tugs at the hair and while he has to admit the locks are soft, they're also knotted, clearly in need of a long brushing. Anger boils in Dean's blood.

"He did this on purpose!"

A rant bubbles in Dean's chest, but the full implications of this transformation hits him square in the face.

"Oh wait!"

Dean stumbles into the bathroom and jerks down his pants. For a split second, it's just too weird for Dean to conjure any rational thought. Fear shivers up his spine.

And then he's dipping his hand between his legs, trailing fingers over surprisingly sensitive flesh. A frisson of pleasure sneaks up the same path the fear had taken. Dean presses his back against the closed door and grins.

Well…the deal had been sealed with blood. Gabriel can't break it. Dean will get his dick back.

In the meantime, he might as well see how the other half lives.

"Dean, are you touching yourself in there?"

"Yep."

*************************

"What happened?" Castiel asks in dismay.

Sam burrows deeper into his coat and glares out at Castiel. "Your hideous brother turned us into women in exchange for saving Bobby's life."

"I…don't understand."

"No one understands him!"

"Why are you doing that?" Castiel asks, nodding at the way Sam has captured his hands under his arms.

"Because I don't have a bra! And they…bounce," he grumbles. "I had no idea how annoying it was. It's supposed to be hot. It's not hot. It's making me sore."

Castiel honestly has no idea what to say to this outburst. He's slowly learning the sexual appeal of human bodies. Both males and females have so much to offer, but Castiel's never been attracted to a particular set of breasts. He thinks the appeal has to do with soft texture, but he's not certain.

"Okay, I can't take it. All my shirts are too fucking huge."

Dean pauses in the bathroom doorway. But he looks entirely different. His facial features have softened into something distinctly feminine and his hair now pours down his back all the way past his waist. In place of the thick angular body Castiel once reconstructed, there is a slender form with wide curving hips and shapely legs.

He's not wearing a shirt. Without really understanding why, Castiel drops his gaze to Dean's chest to the slightly rounded breasts facing him. His breath catches in his lungs and the impulse to feel the breasts against his hands is so strong, his palms actually itch with the desire.

"Dude, Cas! Warn a guy," Dean snaps, clutching his shirt to his chest, hiding the breasts from Castiel's eyes. Disappointment flares strongly in his Grace along with a good dose of surprise. He's grown accustomed to the strange fantasies of pressing his hands against Dean's shoulders, the strong desire to cup his hips and taste the skin beneath his jaw.

He did not realize these urges would translate to a female body.

"You pervert," Dean gripes.

Castiel fears he may be correct.

*******************

At first Dean doesn't blame him. It's not like Dean hasn't stared at his fair share of tits, but seriously. Sam is the one with the perfectly sculpted breasts. Not that Dean's looking too closely because it's still Sam. But Sam's not Castiel's brother, so why he's staring openly at Dean's mini-boobs is beyond him.

But whatever. Dean can't blame a man for looking. What he can blame him for is making that hot shivery feeling grow between his legs. Alright, fine, there may have been a few times when Dean was jerking off and Castiel popped into his mind. But that's no reason for warm heat to flash through his body just because Castiel's eyes are on his borrowed tits.

"Stop it!" He finally snaps.

"I'm sorry?"

"Quit leering at me," Dean growls, though it's a lot less impressive in his high girly voice. He shoves the hair out of his eyes. "You're creeping me out."

"Like he doesn't stare at you all the time," Sam complains from the corner. Dean glares at him. Sam's been a real bitch since this started. He must have transformed directly into his period.

"What are you talking about?"

"I don't stare."

Sam snorts. "You look at his ass all the time, man."

"You look at my ass?"

Castiel disappears with his usual flapping noise and that can't possibly be disappointment settling in Dean's stomach.

"You jerk," he says.

"Don't snap at me just because you get off on Cas' stupid staring."

"Dude." Dean grips Sam's shoulder. "Midol."

"Fuck you."

***********************

"Alright, that's it. I can't take it anymore."

Dean's attention breaks away from his episode of Dr. Sexy, M.D.. Which is a relief because he'd begun mentally putting himself in Nurse Piccolo's place, imagining how it'd feel to be pushed up against the elevator door with his legs wrapped around Dr. Sexy's waist. Because with his slimmer body, it'd be so very easy for a strong man to hold him up and thrust, especially a man with angelic strength…

"Yes, what?" Dean blurts. "What's wrong?"

"These fucking things are driving me crazy," Sam rants, cupping his breasts with both hands and shaking them in apparent frustration. From an actual woman, Dean might find the sight enticing. From Sam, it's mildly disturbing.

"What you gonna do? Chop 'em off?"

"Oh if only." Sam tugs on the jacket that's now gigantic on his body. It doesn't hide his obviously feminine form, but it'll probably save him the inevitable leering and whistles were he to walk down the street with those puppies unleashed. "No, we're going to buy bras."

Embarrassment curls in Dean's chest. His life can't possibly be this screwed up. Having breasts is one thing. Going out in public and pretending to be an actual woman is quite another.

"Speak for yourself, Knockers, I don't need a bra."

"I know you think that, but when was the last time you let a woman walk by who obviously wasn't wearing a bra without leering at her?" Sam challenges and he's got a point. It doesn't matter how big or small the tits are. If Dean can see nipples through a shirt, he's looking. Strange Dr. Sexy ponderings aside, Dean's not prepared to be fantasy material for random dudes on the street.

"Fuck," he says, but he drags himself of the bed. "What do I do with this hair?"

"You probably could chop it off," Sam suggests.

"You think Gabriel won't instantly put it back?"

"Okay, yeah. Um…we'll stop at a Wal-mart first for hair stuff."

"We're not going to Wal-mart for the bras?"

Sam makes a face. "Hell no. We're hitting Victoria's Secret."

*******************

If Dean weren't so utterly humiliated, this might be pretty hot. The chick running the bra section of the local Victoria's Secret is a cute blond and she's got her arms fully around Dean, pulling one of those tape measures tight around his chest. Sam watches with barely concealed glee from one side, but Dean thinks he won't be laughing so hard when it's his turn.

"So many women wear the wrong size bra," Cute Blond comments with a sweet platonic smile. "We'll get you fixed up with something comfortable."

"Right."

She's so close he can smell her flowery perfume and almost feel the swell of her own nicely sized tits against his chest. While she pulls back to check the tape, humming slightly under her breath, Dean wanders away into a girl-on-girl fantasy. Not unlike ones Dean has had before, only this time it's much more personal. And not quite as pleasing. Not because it wouldn't be hot with the right woman, but because Dean has no idea how women feel during sex. Would he enjoy penetration? If not, would he enjoy doing the penetration without the benefit of his penis or would he most enjoy just rubbing against the chick? Oral sex is a good option, but how does receiving compare to a blowjob?

Clearly he needs more experience having sex as a woman.

His mind flashes to his elevator fantasy, his legs hooked over Dr. Sexy's hips and staring up into his heated blue eyes…wait, no Dr. Sexy has brown eyes. Well, whatever, the point is Dean should try getting laid as a chick.

"Alright, I'd say you're a 34A," the woman says.

"Wow," Sam comments. "You're tiny."

"Shut up," Dean grunts.

The blond gives them a strange look. Presumably because a woman in her thirties would at least have a hint of what size bra she wore. Dean shoots Sam a glare.

"Your turn, Princess."

Dean doesn't have time to mock Sam for being declared a 36DD because that's the moment that Castiel appears at his side with a small puff of air. The blond yelps when she turns and sees the strange man staring at her with abject confusion. In the changing room area.

"What are you doing?" Cas asks.

Damage control time. Unfortunately, Sam's tongue loosens before Dean. "It's okay," he reassures the woman. "Cas is Deana's boyfriend."

Oh, he will pay for that.

*****************

"What the hell?"

Dean loves sexy bras. Especially ones that only cover about half the actual breast and push the rest up into his face. Over the years, he's become something of an expert at removing those same bras in record time. Sometimes with his teeth. But it's something altogether different when you're faced with dozens of choices of bras that you yourself will eventually wear.

"What's wrong?" Castiel asks.

Of course, he's hovering at Dean's side. It's just Dean's luck that Castiel managed to pick up the 'Quit being weird' vibe and went along with Sam's obnoxious cover story. So now the staff thinks that Castiel is the rumpled suit-wearing boyfriend of the chick in ill-fitting clothes with a giant messy ponytail. God, they probably think Dean's wearing Castiel's clothes.

They really need to get some regular girl clothes after this.

"There's like a billion choices," Dean complains.

Castiel considers the rack of bras with a thoughtful expression that amuses Dean. Like Castiel has any fucking clue how to choose a bra.

"This one," he says, lifting his choice from the rack and handing it to Dean.

Dean raises an eyebrow. It's a slinky scrap of barely there glossy black material. Like clearly a 'getting lucky' bra, the kind girls wear for the five minutes before sex when they're doing those little strip teases.

"Seriously? This one."

"Yes," Castiel says with a nod. "It's pretty."

"Riiiight."

But he doesn't put it back. He grabs another few might actually cover him and stalks away to the dressing room where he can hear Sam cursing quietly. His mood lifts once more. No matter how weird this is for Dean, at least he knows Sam is in the next stall over trying to shove massive boobs down against his underwires.

Castiel follows Dean, but to his credit, he doesn't try to follow Dean into the actual changing booth.

The first one Dean tries is the sexy bra. The little touch of lace at the top worries him, but that concern fades away in favor of trying to get the damn thing on. Unhooking these things is way easier. His first attempt to put the bra on cup first is a complete failure. Dean ends up turning in three circles trying to see the hooks before he finally gets the idea to hook the bra first and then swivel it around his body. Once the cups slip over the breasts, he's relieved to discover the lace is padded so it won't scratch. He adjusts himself several times and then looks in the mirror.

Huh. Well. That's not so bad. In fact, Dean has to admit, he looks pretty hot. The bra pushes his small breasts enough that they swell upwards. Not quite making cleavage, but creating a sexy little valley he instantly imagines someone pressing their face against. Dean turns to one side to admire that angle. Still not the kind of breasts that would have caught his attention, but better than he thought they'd look.

So that's his excuse for his next behavior. All he's thinking is 'hey, I wanna show off!'. Not, 'hey, I'm about to flash myself to the nearest man.'

"Look at this," Dean says as he opens the door.

Castiel's eyes pretty much fall out of his head.

Dean's not entirely stupid. He's seen the odd side glances and felt the lingering touches Castiel's been giving him. He's not come close to dealing with the implications or the way it makes him feel warm in odd places, but he knows it's happening. Until that moment, Castiel's attraction hasn't been overt, so Dean could easily ignore it.

But then he's not been prancing around half-naked, shaking his dick at Castiel either. That's probably the equivalent of what he's doing right now.

"Yes, well, that is to say," Castiel stammers, then falls silent.

Dean's panic very nearly ruins the moment, but just as he's about to slam the dressing room door in Castiel reddened face, Dean looks straight into Castiel's eyes and sees the outright lust simmering in his gaze. Castiel's standing very close to Dean, his eyes are roaming over Dean's body and instead of embarrassment, Dean feels…excited. And powerful. Like he could drive Castiel completely insane just by walking past him and maybe he always could. But having these body parts, by easing the panic created by frightening confusion, Dean can better concentrate on the underlying desire.

"You like it?" Dean murmurs, almost startling himself by how deep his voice sounds.

"Yes," Castiel says, his own voice unrecognizably gruff.

The desire abruptly grows, a dip in his belly and Dean sways closer to Castiel. He has no idea what he's thinking when he says, "You should feel it," but when Castiel instantly reaches up to cup one breast with a slender hand, a peculiar kind of wet heat blossoms between his legs.

"Hey, guys, I was…holy shit," Sam yelps.

And once again, Castiel disappears in a whirl of feathers.

"Goddamn it, Sam," Dean grunts.

"Well, excuse me, but we're in public," he nearly shouts, apparently scandalized beyond measure. "What the hell is going on with you two?"

That's exactly what Dean wants to know.

****************

In the end, Dean chooses both an average tan-colored bra and the scrappy black thing Castiel liked. He doesn't ask Sam what he chooses, but he does tease him when Sam makes them stop at the bathroom right after they leave the store so he can change into his new purchase. His overwhelming relief once the boobs are strapped down amuses Dean for the next half hour or so.

Right up until the moment Gabriel appears.

They're standing in front of a Old Navy, arguing about how much money to spend on temporary clothes when from behind them, they hear a low whistle.

"Looking good there, Winchester." When they both whirl around, Gabriel tips his head to one side and stares openly at Sam's new body. "And by Winchester, I mean you Samantha. No offense, Deana, but you're not really my type."

"Well, thank God for that," Dean growls. "How long are you going to keep us like this?"

"Long enough to teach you never to agree to a deal without specifics," Gabriel says.

"You wouldn't tell us specifics!" Sam accuses, his face still beet-red from Gabriel's comments.

"What can I say? I'm a fickle bastard," Gabriel says. "But since you're hot and I'm in a good mood, how about we say two more weeks?"

"Two weeks?"

"No way!"

"Ladies, ladies." Gabriel holds out both hands, palms up. "Let's be honest with each other. Neither of you have the best track record when it comes to respecting women. I won't name names, but you deserve far worse than you're getting."

"Look who's talking," Dean says. "You don't respect anyone!"

"True, but then, I don't have to play by human rules. And I don't discriminate based on gender, class, race, sexuality or level of intelligence." He winks at Dean. "Or lack thereof. I only torment those who need it."

"You fucking-"

"Dean!" Sam snaps. "Shut up before he adds more time."

"Too late. Three weeks it is," Gabriel says happily. "Now, the first order of business." He steps closer into Sam's personal space. "Understanding how women feel you objectify them." Dean's stomach turns. The look Gabriel gives Sam is heated and possessive. The fantasies currently running through his twisted brain are clearly pornographic.

"God, stop it!" Sam says. "Dean's the one who leers at women!"

"True," Gabriel says, abruptly dropping his lascivious expression. "But Dean's clearly beyond help in that area. No, his lesson is a different one altogether."

"Oh god," Dean mutters. He's too afraid to ask Gabriel's meaning, but Sam has no such fears.

"What are going to do to him?"

"Oh nothing," Gabriel assures him. "I already have an unknowing accomplice in Dean's training."

"I…don't like the sound of that."

"You don't have to." His smile is evil. "Just wear that black bra and everything will take care of itself."

********************

Dean gets hit on for the first time at lunch.

After Gabriel thankfully disappears, Dean and Sam decide their long sentence required a purchase of clothes. Especially for Sam, who'd shrunk a good six inches and could barely hold his pants on his hips. The staff in Old Navy give them the same confused looks they'd gotten at Victoria's Secret, but no one bothers them as they pick out shirts and jeans. Dean's fashion sense is restricted to solid colored shirts and button down plaids, so the vast array of choices overwhelms him. In the end, he goes for comfort over style and chooses simple cotton tees, plain blue jeans and a few tank tops since the weather is warm.

Once they're both dressed in new outfits, Sam in a pair of khaki pants and a button down that hugs his new curves, another problem becomes apparent. So it's back to Victoria's Secret for underwear that doesn't bunch up under their new pants.

Dean waits until Sam is occupied with a saleswoman to add a pair of lacy black panties that happens to match his black bra to his pile. Not that he's going to be showing them off to anyone or anything.

"I'm done," Sam announces as they emerge from the store once more. "I've shopped more today than I have in the last year. I'm starving."

"Me too. I need some meat," Dean says because red meat is men food, but the comment only earns him a snicker from Sam. "Shut up."

"You do seem to be more interested in meat than I realized," Sam says.

"Shut up! I didn't see you saying no to Gabriel."

"You also didn't see me letting Gabriel feel me up in a changing room either," Sam points out.

There's no arguing with that and besides thinking about it just makes Dean's stomach feeling funny, so he only glares and keeps walking. His new underwear slides against his skin under his pants. Fucking weird girly material. It clings to his ass, but doesn't actually cover anything along the side, so his bare hip and leg is rubbing against the inside of his blue jeans. The salesgirl assured him this was the most comfortable style, but when you go from boxer briefs to what's basically a thong, it's hard to agree.

"Are you okay?"

"This underwear."

"Well, if you'd bought the regular kind…"

"I thought I could trust the underwear lady!"

"You were flirting with the underwear lady. I have no sympathy for you."

They're still bickering when they get into the car and all the way to a diner Dean had noticed that morning. In fact, the only reason they stop is because Dean catches a glimpse of himself in the window's reflection.

He looks one hundred percent female now. With his strappy tank top and hip hugger jeans, long dark blond hair spilling out of its ponytail, Dean looks like one of those bubbly athletic girls who play beach volleyball and go surfing. Beside him, Sam is the perfect image of a preppy chick with her long perfectly styled hair and casual, but stylish clothing.

"Oh my god," Sam murmurs, obviously caught by the same image.

"I don't know how, but we have to find a way to make Gabriel pay for this."

"Yes."

That feeling is only enhanced when Dean's waiting in line to place his order and a tall guy with a douchy smile and bleached blond hair sidles up to his side.

"Hey," the guy says. "What's up?"

Dean just glares at him.

The guy does not get the message.

"I'm Alex. What's your name?"

Before he can answer, Dean hears a familiar flapping noise and all he can think This is not going to be good.

"Her name is Deana and she is my girlfriend," Castiel says.

Yeah. Not good at all.

"Hey, man, I'm sorry. I didn't know."

"Now you do, so please leave."

Dean never knew how annoying it was to have someone talking for you. Not that he wants the idiot to hang around, but Castiel could have given Dean the chance to tell Alex to fuck off. He certainly could have done it well enough himself.

"Calm down, Cas," Dean says, but damn if he doesn't sound like a frustrated girlfriend.

"Yeah, dude, calm down," Alex says.

It's amazing how fast Dean can turn from annoyed to defensive. Maybe that's why women confuse him so much. It's like they want independence, but they'll still say shit like what comes out of Dean's mouth.

"He doesn't have any problem kicking your ass."

Alex scowls at them both, but he leaves without making a scene. Which relieves Dean. It's not until that moment that he realizes he doesn't know if his new body is at the same level of athletic ability. Dean could beat a guy into unconsciousness, but judging by his slender muscles, he doubts that's still true. The realization has him unconsciously moving closer to Castiel's side.

"You're not my fucking boyfriend," he grunts.

"I know, but I could sense your disgust. I thought hearing a warning from what he perceives as the larger threat would be more effective."

Dean makes a face. He ought to be able to protect himself without worrying that some jerk won't take him seriously.

But since that's dangerously close to what Gabriel had been saying, Dean shoves off the thought and turns to see Castiel leering at him again.

"What?"

"You have new clothes."

"You don't have some kind of x-ray vision, do you?" Dean asks suspiciously.

"I've never tried to see if I do," Castiel says.

"Well, don't try now!" Dean says, crossing his arms over his breasts. Castiel can't answer because it's finally Dean's turn to order his food and when he orders an extra cheeseburger for Castiel without thought, neither of them comment on it.

Castiel manages to stay with Dean and Sam all through lunch. There's one point where Castiel makes a soft pleased moan in the back of his throat over the taste of his burger and Dean wishes he had the power to fly away. Because he immediately imagines that same moan vibrating against his inner thigh and Cas is either spying on Dean's thoughts or maybe angels can smell pheromones because right after Dean thinks it, Cas gives him a thoughtful and very interested look.

So yeah, wings would have been nice.

But since it's not possible, Dean decides the only course of action is to finally satisfy his curiosity so he won't keep having crazy fantasies. Which is the reason he ends up at a sex store that afternoon. Castiel's disappeared back to Heaven on mysterious errands and once Sam realizes what Dean's going to do, he's makes Dean drop him at the motel so he can get his own room. That kid really needs to loosen up. Dean's not pleased about losing his dick and staying a woman for three weeks, but he'd be crazy not to take advantage of this situation. It's free fondling! No strings attached. And how could Sam not be curious about how sex feels in his new body? He has no imagination.

Unfortunately, imagination doesn't help Dean in the slightest when faced with dozens of different sex-toys. Nor does it help the freaked out panic. The idea to explore his female body was much easier to swallow when he wasn't looking at piles of massive realistic looking dildos. When he's got one, Dean's no slouch in the penis department, but some of these things are fucking ridiculous. How could any real guy compete with this stuff if that's what a girl needs?

"Do you need some help?"

Dean snaps out of his thoughts and smooths out his stricken expression. He doubts this salesgirl would understand if he told her the dildo display was making him feel like less of a man. It's not like he's never seen a dildo before, but he very rarely ever handles them himself. What's the point of toys when he's got his dick to use? He hadn't realized how large and complicated they could be.

"That one has attachments," he says stupidly, pointing to a sparkling blue dildo with more parts than a Swiss Army Knife.

"Oh yes, it's one of our best sellers," she says. "But you seem like you want something more simplistic?"

He considers making up a story, but quite frankly, he's already tired of pretending to be something he's not.

"I've never used one of these things and actually, come to think of it, I'm technically a virgin, so I guess I need one with training wheels."

The salesgirl can't quite hide her flash of surprise, which does wonders for Dean's ego. Because clearly someone would have nailed a girl as hot as him before now.

"Oh, well, in that case. Are you interested in a dildo or do you just want clitoral stimulation?"

Dean makes a face. Clitoral stimulation sounds way less sexy than it is.

"Both, I guess? Sure, yeah, I'll take it all."

"Okay, well, I'd recommend this," she says, reaching for a small package hanging near the top of the display. "The Magic Fingers. Basically, it's like a vibrating finger puppet."

"Kinky," Dean says.

"A bit, yes," she says with a smile. "I love this one. It works wonders."

"Oh really?" Now normally, this would be where Dean raised an eyebrow and pursued this topic until he had a clear image in his head. The salesgirl isn't gorgeous, but she ain't half-bad either. But in this body, he has no idea what to do. Is he allowed to flirt? Or does that scare girls? And what's more, does he really want to flirt or is that just his ingrained habit?

"Definitely," she says, apparently missing his struggle. "It's my go-to toy when I don't have a lot of time. It's great for sextoy beginners."

"Uh, right."

Dean takes it and sticks it under his arm.

"As for a dildo, I'd suggest something like this," she says, unhooking a large package from at knee level. "It's fairly simple, but it has a vibrating option in case you like that. And it's not too intimidating."

Speak for yourself, Dean thinks. The thick green dildo's five inches look terrifying to him. Presumably, it will fit, but Dean just has no idea what sensations to expect.

Still, if he's going to do it, he needs to just do it.

"Right. Awesome."

Ten minutes later, Dean officially ready for his night.

***************

You can do this, Dean tells himself. It's just pussy. He's touched plenty of them. Just because this one is attached to his body doesn't change the fact that Dean knows what he's doing.

So why he's so nervous, Dean's not sure. He tries to ignore the feeling as he puts batteries in the toys and makes sure the room door is safely locked. Then he sheds his clothes. Dean doesn't masturbate fully naked unless he's in the shower, but girls probably need more space. Plus, he wants to see the free show. Once he's naked, Dean sits on the bed opposite a dresser with a mirror. Releasing his tits from the tiny bra actually feels pretty amazing. The cool air released by the chugging AC hardens his nipples. Dean considers them. They're on the small side and lighter in color than he's used to. In his male form, Dean's never much pleasure from them. But that one fleeting moment of Castiel's warm hand pressed against his nipple felt amazing, even through the bra.

Dean curls his hands around either breast and squeezes lightly. They really are nice little tits. His first judgment of them hadn't been fair.

He's concentrating so hard on his male perspective on how it feels to hold the breasts that he's not at all prepared for the sensations that rocket through his body when he flicks a thumb over one nipple.

"Holy shit," he breathes.

The pleasure settles unexpectedly between his legs. When Dean rubs his thumb in the same motion, the pressure only grows. So he doesn't stop and in fact presses harder and harder until he can barely breathe. It's only when he first feels the wet sensation that Dean stops. He can't help it. This part freaks him out. With a partner, it's great. Dean loves knowing she's turned on by him, but he can't help thinking it feels wrong, however much his current biology disagrees.

He stands from the bed and walks around it to retrieve the Magic Finger. If he thinks about it too much, he'll quit. Best just do it quickly and get his experience points. Sitting again at the head of the bed, Dean fluffs up his pillow and leans back. The image he sees in the mirror is pretty fucking hot, but oddly enough, Dean's not very affected by it. Yes, he's a sexy curvy thing leaning back on her elbows, her tits heaving and legs spread wide like a whore but…it's still him. He can't get past that fact.

Dean sticks the toy on the end of his index finger and turns it on. There are four settings. With a shrug, Dean goes for the highest setting and immediately presses slips it against his clit.

His head smacks against the headboard and Dean's actually embarrassed by the high-pitched moan he releases. The pleasure explodes, insistent and unlike anything Dean expected. Because it couldn't possibly feel as good as shoving his dick into a hot wet space, right? Sure, girls really like the sex, but it couldn't feel as good for them, not when clits are so much smaller than cocks.

God, he was so wrong. Wrong, wrong, wrong. His free hand grasps uselessly at the bedspread as Dean rubs the Magic Finger in a circle and holy fuck, he's soaking now. If he'd been worried about coming up with a good fantasy, that worry is thoroughly erased. The sensations are too unexpected and unfamiliar to require anything more than pressing harder, harder, harder. His hips move of their own accord, thrusting up against his hand and a low burning grows deeper in his body. A longing ache for more, but there's no time to try for anything else before Dean's pushed hard over the edge. The pleasure peaks into a hard climax, both like and unlike what he's always known. The sensation of release feels very much the same, but it diffuses faster across his body and once the initial pleasure fades, Dean immediately wants more. He's not tired and spent. His skin is raw and he feels edgy.

"What the fuck," he pants, flopping back and staring at the ceiling. "Goddamn."

More. He wants more. The longing from earlier tugs at him again and Dean fumbles for the dildo. Again, he doesn't waste a moment. The plastic is cold against his overly hot flesh, but Dean soldiers on, spreading his legs as wide as they'll go and pressing the tip against his clit. An odd shivery uncomfortable feeling drags a hiss from between his teeth. It takes another few shallow thrusts before Dean understands that he's feeling a little sensitive.

Whatever. That's not going to stop him. Pushing himself up on his hands again, Dean watches his reflection position the dildo and with a deep breath, he pushes hard.

"Goddamn," he grunts again.

The first sensation is not pleasurable. Dean shifts his hips and tries again. Doing this is a lot harder from this angle. He leans back a bit more and yelps when the dildo abruptly slides inside. Fuck, it's tight and initially painful. The natural lube eases the way, but Dean's still doing this for the first time and he has to pause for deep breaths more than once before he feels comfortable building a rhythm of thrusts. The sensation is beyond strange. Once, he spent the night with a particularly adventurous girl who insisted on using her strap-on. All Dean can remember from the experience is the utterly alien sensation of being filled. That and the weird intense orgasm he'd had. He's having the same feeling now. The pleasure hovers at the edge of his consciousness, but it's held back by how weird it all feels.

To distract himself, Dean lays against the pillow and pinches at one nipple again, sighing with relief when bright now familiar pleasure sparks.

Unfortunately, it makes him think of Castiel. His muscles clench around the dildo at the massive wave of pleasure crashes over him and for a moment, Dean resists.

But only a moment. Because it feels so fucking good. His mind runs wild. God, if it were Castiel's dick inside him instead of the dildo, then Castiel could lick and bite at his nipples and the pleasure would be three times as potent. As if from a distance, Dean hears himself moaning and cursing the frightening climax rushing towards him. It's something altogether different that first. He's trembling with the power of it, his control totally gone as he shuts his eyes and imagines Castiel's heated gaze, hears that incredible rough tone whispers encouragements as he works them both towards orgasm.

"Cas, oh fuck, Cas, Cas," Dean chants.

There's a flutter of wings, a short silent intake of breath and when Dean opens his eyes, Castiel is staring down at him with dark intent.

Dean comes so hard, he afraid he might pass out and all the time, he's still calling Cas' name.

Part Two

Comments

( 5 comments — Leave a comment )
cider_jelly
Apr. 9th, 2012 11:38 am (UTC)
Im always kind of cautious to avoid the sex change gen, however Jen your writing is always so brilliant~ this is definitely the first sex change fandom that I dared and finished readining, very funny , get some bra, Sam, and stop touching yourself, you perv Dean~~ :D
neotoma
Apr. 14th, 2012 12:05 am (UTC)
"You pervert," Dean gripes.

Castiel fears he may be correct.


LOL. Poor, poor Cas! He has no idea what he's doing or why.

Dean ends up turning in three circles trying to see the hooks before he finally gets the idea to hook the bra first and then swivel it around his body.

So Dean is wearing the wrong size anyway? Oh well, that's what he gets for going to VS.

"Look who's talking," Dean says. "You don't respect anyone!"

"True, but then, I don't have to play by human rules. And I don't discriminate based on gender, class, race, sexuality or level of intelligence." He winks at Dean. "Or lack thereof. I only torment those who need it."


Oddly enough, we never hear of Gabriel attacking a woman during his Trickster days. In fact the only woman (-shaped person) he interacts with who isn't a figment of his imagination and phenomenal cosmic powers is Kali, who can pretty much hold her own against him.

And how could Sam not be curious about how sex feels in his new body? He has no imagination.

...o rly? Sam is just more discreet than Dean, I bet.

but it couldn't feel as good for them, not when clits are so much smaller than cocks.

This is where Dean's poor education bites him on the ass, right? :D
kurosachia
Aug. 9th, 2012 03:18 am (UTC)
So, this is awesome. I'm an avid reader of your fics, and I always thought you stayed away from smut because you didn't like to do it or weren't able to. BUT THE LATTER IS SO OBVIOUSLY INCORRECT. GOOD. JOB.
joseluis118
Mar. 18th, 2013 03:13 am (UTC)
OMFGGGGG! This is amazinggggg!!!! I can't wait to read part two! Who knew I would like genderswap. At first I was like "mehhh...I don't think this is my kinda thing," but then I was like, fuck that. 'Cause let's be honest, I'd read your freaking grocery/to-do lists if I ran out of fics to read from you. Lol. Funny thing is...I'm definitely not kidding.
camelfeathers
Oct. 13th, 2014 02:48 am (UTC)
Oh goodness. I didn't expect how emotional I would feel about this. The idea of Cas and Dean having their own child, albeit a scary nephilim baby, is just awesome.
( 5 comments — Leave a comment )

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