Requested by raelle23. Here we have Dress Up part 2 - Cas gets cute!

If you read the first part and still need warnings, you may want to check Naomi didn't scrub your brain clean. However, I'll do them anyway.

Incest, cross dressing, double penetration, group/threesome etc, full and flagrant disregard for the purity of an angel... Oh, and unprotected sex, which I actually don't condone in reality because condoms are good but for the sake of fanfiction lets play pretend.

There's some just plain ol' Wincest to start with, the good stuffs further down because it took me a while to get back into writing these characters - I write so much Young Dracula I almost wrote 'Vlad' multiple times.

-SPN-

"Dean, what the hell are we doing?"

"You heard Cas. Our fallen angel wants a dress."

Sam, who still struggled with the whole 'touched by an angel' thing since Cas' last visit, when Sam had been the one to bottom for the angel - not him and Dean together, they were on a hunt, he needed to be able to walk - and he realised they had literally defiled a vessel of heaven, shook his head.

"I'm thinking blue, bring out those eyes."

Dean had no such concern, though he was careful not to mention gender in the dress store they were in. It wasn't a conservative state, but two guys talking about buying a third a dress? Kinda weird, they were trying not to raise too many eyebrows. They still had to go makeup shopping yet - Dean was running low, and Cas may not suit their current collection.

"Whatever you think Dean, let's just get a move on. I'm hungry, and it is usually you who says that."

"Can't rush these things Sammy!"

Rolling his eyes, Sam perused the store quickly, hoping he would spot something suitable, they would buy it and find somewhere that sold a half decent salad, or at least a sandwich not coated in grease. His eyes landed on one, midnight blue and probably just above knee-length for Cas, with thin straps and - when he headed over to it - soft to the touch.

"Dean?"

Sam held it up, and Dean's eyes went dark as soon as he saw it.

"Perfect. Now for the matching underwear. Do you think Cas would prefer a thong or briefs?"

Sam closed his eyes, counted to ten and reminded himself Dean didn't put out when he punched him in the face.

"If you ask that any louder God himself will hear you!"

Dean was unapologetic, garnering several amused and confused glances from other shoppers. Sam didn't know if Cas even wore underwear - he undressed with angel mojo. And there was no criteria list for cross-dressing a heavenly host. All the same, he felt his cheeks heat a little when Dean held up a pair of snug lace briefs in powder blue, picturing Cas' pale thighs with those riding along the top.

"Bingo."

Food forgotten, Sam barely waited for Dean to swagger to the counter and buy the damned things before they were in the car, swinging the Impala into the motel car park at probably dangerous speed. That cheeky smirk across Dean's face told Sam he knew damn well what was going on in his head, which meant he was on board. A good thing really, because Sam had them both naked and lubed fingers buried inside Dean in under five minutes.

"Damn Sammy, this really brings out your fun side."

Their mouths mashed together roughly as Sam fucked into Dean's willing body, grunting and sweating like animals and Sam loved it. Loved Dean's thick cock rubbing and leaking against his abs, loved the half-lidded lustful stares beneath long eyelashes as Dean lost himself in the feeling. Hurried and rough, explosive and hot, Sam shuddered through his climax as Dean spilled, sticky and copious with a deep, erotic groan.

"Sammy?"

Muscles lax as he lay on his stomach, ignoring that his stomach was covered in Dean's come which would ruin the bedspread, Sam lifted his head and glanced through sweaty bangs.

"Yeah?"

"We still gotta go makeup shopping."

He could only groan weakly, leaning over to nip at the muscular shoulder that was in range and feeling the familiar heat in his stomach when Dean smirked.

A quick shower that ranged the full spectrum from arctic to hellfire in ten minutes later, the two were out hunting for a twenty-four hour diner, Sam now ravenously hungry after their... activities that delayed eating. The diner they found did nothing healthier than some overly dry scrambled eggs, so Sam relented and got a 'real meal', thick cut potato wedges, cheeseburger and the tallest coffee they made twice. He smirked to himself when Dean sat himself down a little delicately before devouring two bacon cheeseburgers - and stole half of Sam's side dish.

"I am stuffed. We gotta come back here again tomorrow when I don't look pregnant."

Dean paid, Sam added the tip and their bill had the waitresses phone number on. It was impossible to tell who for as she smiled at them both in a sickly sweet, flirtatious manner, but they weren't all that interested anyway. Dean smiled and pocketed it to be polite, then complained when they left they couldn't go back without it being awkward.

"If you stop complaining, I'll buy you a pie from that bakery when we drive to Sioux Falls tomorrow night. Now come on, that ghost won't gank itself and you've distracted me enough."

Fairly sure Dean only heard "pie", they slid neatly into the front seat of the Impala, stopped off at a late-night store for salt, beer and 'road snacks', Dean tossed a bottle of lube into the basket which made the teenage boy server blush so hard Sam thought he might die, they were on their way.

The ghost was an easy hunt, because they had already twigged the body was cremated and tore the abandoned house apart for remains. Watching the bloodied towel from beneath the floorboards go up in flames, Sam grinned.

"Right. Back to the motel, get my four hours, go buy Cas some mascara, get gas and then we can get going to the pie... I mean job."

They tossed the ruined topsheet off, crawled beneath the surprisingly cosy blankets together and slept like the dead. Sam was always the big spoon, regardless of who fucked who, because Sam's longer legs meant Dean's knees pressed uncomfortably into the back of his thighs if Dean spooned him. Dreams of Cas and a lingerie store meant Sam was achingly hard when he woke, rutting for friction against Dean's lower back before he was even conscious.

"No way are you topping again after last night. Man that was great. Roll over Sammy boy!"

Dean straddled his thighs when he had Sam lay on his front, drizzling the tingly-lube that drove him wild along his crack, teasing and just a little too cold for sleep warm skin. Sam wriggled and squirmed, feeling Dean's cock nudge between his cheeks and cursing that he always needed stretching and loosening when they did this, because his narrower hips made him tight and Dean's girth was almost too much anyway.

"Don't worry little bro, I'm gonna fuck you good."

Whining needily, Sam felt rough, calloused fingers rub the lube in, tingling along the sensitive nerves there until Sam could hardly breathe. Finally there were fingers inside him, working him open with practiced ease and the edge of tenderness Dean's touch always had like this, no matter how feral the fuck Dean would always do this part right, keep it up until Sam was sobbing, begging to be fucked.

"Ready for me Sammy?"

"Do it Dean. Fuck me, please!"

A little cliche, Sam had to bite the pillow to muffle his screaming when Dean finally penetrated him properly, lest he wake the entire motel and alert them to the fact his brother was about to fuck him, and oh wasn't that brilliant. Morning breath meant they couldn't kiss yet, but Dean peppered kisses along his shoulders, rolling his hips slow and deep to make sure he was ready to take it properly.

The slow, burning ache was amazing, the drag along his prostate with each push-pull thrust enough to make him see stars. Dean's stocky hips came flush to his ass each time, sliding home deep with each thrust until Sam was thrashing, cursing his lack of leverage to push back and whining, begging for more.

Never one to disappoint, Dean delivered brilliantly as he sped up, their lazy morning fuck a race to the finish line now, the tantalising friction between rough sheets and Sam's own stomach pushing his cock to spurt, a warm puddle spreading beneath him and the clamping of his muscles dragging Dean along with him as heat flooded his insides.

Ragged panting was the only sound for several minutes, then Sam's mild gasp of discomfort as Dean slipped free. Dean seemed to have a second wind already, slapping a broad hand on Sam's ass and laughing aloud when Sam reached behind to swat at him.

"Rise and shine Sammy! Pie!"

Cursing Dean to every deity his post-coital brain could come up with, Sam staggered to his feet and crawled under the shower, which had him alert in no time when it turned freezing cold and even Dean shrieked in surprise.

They found a different diner with a great breakfast menu, and Sam could happily have eaten a dozen of his cheese and spinach omelettes but settled for two, watching Dean scarf down pancakes and bacon. They ordered extra coffee to go, then it was back to their side quest - corrupting Castiel.

"You don't use blue eyeshadow for blue eyes!"

"It'll match the dress."

Ignoring the fact they were having possibly the campest conversation they had ever had - including the merits of strawberry vs blueberry scented moisturiser - Sam wasn't sure where Dean had learnt the next phrase he came out with.

"You don't display sapphires on a blue cushion!"

He couldn't help laughing, just a little, at the dumbstruck expression on Dean's face at the words that had come out of his own mouth. They eventually agreed on a 'smokey eyes' pallette, and Sam got the honour of picking out a lipgloss and mascara that he thought would suit Cas, while Dean 'treated himself' to some new things - they were ditching the cards they had on them that night, he was making the most of it.

Plus, Sam would undoubtedly benefit from whatever Dean purchased.

Rather than lip gloss, he found a moisturizing, fruity flavoured (according to the packaging) tint-lip balm, remembering Cas' chapped lips because the angel didn't need to drink. Pretty Cas should have a softer mouth to kiss and fuck. The angels lashes were already jet black like his scruff, and the soft little hairs that circled his nipples, so Sam went for something that was supposed to add 'volume and length' rather than a heavy black tint they didn't need.

When had he become such a makeup expert again?

The middle aged woman who rang up their purchases (Sam saw Dean had found protein bars in the diet section of this department store - they looked plain and nondescript next to the array of glittery, pretty things) seemed very surprised at the two stereotypical macho men dropped a basket full of beauty products on the counter, but they both smiled a little vacantly until she was done.

"I always forget how funny that is, like two good looking guys like us couldn't have girlfriends."

"I don't know man, she probably heard your sapphire comment."

"Shut up. I think it was the 'anal glide' that really did it."

"Or the baby lotion."

"Possibly the fact I bought three different glosses just for me."

Unable to maintain the fake-serious faces and busting into full out belly-laughter then, they sat chortling in the Impala seat for several minutes before composing themselves. A little. Sam tossed Dean a protein bar, unwrapping one for himself and taking a bite. Used to the plain, boring or chemical-chocolate taste, the sweet taste and slightly fruity scent confused him.

"What is this?"

"I don't know, they do all sorts of flavoured these days. I think this is banoffee pie."

Uncouth as ever, Dean grinned with his mouth full, displaying sticky oats all over his teeth. Sometimes, Sam wondered how he ever thought Dean attractive. Then he caught sight of the bags they hadn't loaded into the trunk yet, and his heart rate picked up just thinking about its contents.

He made good on the promise to buy Dean a pie, and the two had an intense, drawn out night where Dean tested out the multiple new products he had, keeping his gun nearby to "masculinise the whole experience" just in case Sam suddenly decided he was less of a man for it.

They dropped in on Jody Mills, enjoying a rare home cooked meal, beheaded half a dozen vampires together at just after dawn, then went back and crashed in their motel, too exhausted to do more than wash off vamp-juice before they hit the sack. It was nearly nightfall when they emerged from the bedcovers, ravenous as they microwaved leftover chicken and potatoes from Jody in tupperware.

"Chicken not shaped like a burger or nugget. Now that is novelty."

"You realise how weird our lives are that that even makes sense?"

Dean burped into the back of his hand, grinned and popped open a beer. Sam followed suit, feeling the beginnings of a pleasant buzz after the second.

"Now?"

Sam knew Dean had been just as interested in this as he was, waiting for them to have finished 'shopping' and have a night off but they both really wanted Cas back in their sex life. Not because they had tired of each other, it was anything but that - Sam got to enjoy Dean's kink for dressing up, but Dean had yet to really be on the other end of it since they agreed it didn't suit Sam. Plus, Cas was hot, they both agreed that so why not enjoy it?

"Let's get all his stuff out, so it's good to go."

Having gotten a room with two beds for a change - it was all the motel had available - they laid Cas' 'outfit' out on the spare bed. Sam dropped the baby lotion and lubricant into the bedside drawer - they didn't need it yet - and changed into clean jeans and shirt, no underwear. Dean did the same, then rolled his eyes when Sam indicated he should do the praying.

He couldn't deny, there was something that went straight to his cock about Dean praying to an angel so they could perform all sorts of dark and dirty depravities to him, near him, with him. The soft sound of wingbeats later, Castiel was in their room, the usual half smile they got instead of total vacancy ever since they had gotten intimate with the angel across his face.

"Hello Dean. Sam."

"Cas! We got you a gift."

"But Dean, I'm an angel. I require no material mmmph."

Sometimes the only way to shut Cas up was to kiss him, and Dean took that job on quite happily, teasing with his tongue until they knew Cas was more on their wavelength than before.

"Look."

Cas, eyes a little glazed now, turned to the bed, pupils dilating as he took in the ensemble waiting for him.

"So, Cas" Sam could see the effort it cost him to tear eyes away from the untouched clothing "wanna play dress up?"

He hadn't considered it until now, when Cas 'popped' out of his clothes and they heard him land in the bathroom, 'his' things disappearing with him, but he wasn't sure Cas would know what to do with the make-up. He didn't even have a normal face in heaven. He beckoned Dean closer, whispering into his ear.

"Don't laugh if he doesn't get the make-up quite right, he's new at this remember?"

Dean nodded shortly in understanding, then claimed Sam's mouth in a blistering kiss as the reality of what was coming began to hit them both, stripping out of their shirts as blood began to heat.

"Don't get carried away, tonight is about Cas."

They heard a mumbled curse and rattling plastic, and Sam could just picture a perturbed angel dropping the cap of his tube of balm or knocking eyeshadow all over the floor. Arousal began to ratchet up several notches as silence fell, and his heart hammered in anticipation when the door finally opened.

"Damn Cas, you look... wow."

Far from clumsy, his face was perfectly done. The habitual stubble waa gone, but he hadn't been gone long enough to shave so he guessed the angel could just pop it off. A touch of black eyeshadow was shimmering across his cheeks, highlighting his cheekbones and the gorgeous mix of silver, grey and black blended over his eyelids was amazing. A line of kohl beneath made his 'sapphires' pop even more, the hint of colour from his lip balm turning a chapped half smile into a soft, inviting pout. Mascara, lightly applied just right, meant that his eyelashes brushed the peaks of his cheekbones with each slow, calculated blink.

And the dress. Oh, the dress. Even without the usual breasts or hips that were often required to fill out such a garment properly, that slice of night sky was made for Castiel. It swished lightly just above his knees, the dusting of black hair over his shins not even registering. The colour highlighted his eyes even more, and Sam decided he would go to hell for defiling an angel happily, because it looked like that.

Sam was pretty sure he had forgotten how to breathe at some point, and when he managed to look at Dean, the exact same expression was mirrored on his brothers face.

"Did I do it correctly? I only watched three dozen instructional videos for this strange glittery substance, there were thousands more but I did not want to miss your call."

Blimey, Cas had studied how to put on eyeshadow. That was above and beyond, showed just how much the angel had been invested in this moment.

"You... Damnit Cas, I don't have words. Get over here!"

They pushed Cas to lie between them on the bed, taking turns to kiss the painted lips and caress the smooth fabric. He made appreciative little sounds, squirming happily between them. Sam leaned over for the bottle of lotion, both he and Dean backing up. Cas looked most perturbed, until they manoeuvred him to lie a little more like a starfish, Sam drizzling lotion along one arm and leg his side, then handing it over to Dean.

"We don't always go for moisturiser, but you look so hot this is a special occasion."

The lotion was chosen because it had the 'powdery cotton' scent - to most, it meant babies. To a hunter, it meant a first aid kit that didn't involve using their own clothes for bandages. Cas lay there while they worked it into his skin, massaging and kneading, tracing swirls in the slightly dampened hair across his legs before working his dress up, Sam desperate to see the briefs that had haunted his dreams since they bought them.

He wasn't disappointed. Stretched thin over the tip of his hard cock, a damp patch darkening the fabric and they cupped the curve of his ass so well Sam wanted to burn that image into his retinas for at least a year, just to savour it.

Skin soft and smooth here along his inner thighs, Cas wriggled at the ticklish sensations where their fingers traced up and down, still new to sex itself but a quick learner, pushing down to try and get their hands higher up. Years of working as a twosome, a team, meant Sam and Dean had no trouble co-ordinating their efforts as they taunted the angel.

"Is this torture-ah" Cas gasped, and it was a beautiful sound as a hand finally wrapped around his leaking erection "customary?"

"Not torture Cas. Foreplay. Sometimes, you just gotta take your time."

Sam palmed his cock while Dean kissed him, and Cas was wide eyed, sweating a little already and the strap on his left shoulder had slid down already. Coupled with his dress hiked up around his hips, the slightly smeared colour across his lips and the growing dampness of his briefs, he looked thoroughly debauched and they weren't even started yet.

"You want the back or the front?"

It was a painfully difficult choice, but Sam mused they could always do this again and trade places.

"Back. Your mouth was made for oral Dean."

He got a hint of a smirk, but didn't stop to enjoy it too much as he reached for the lubricant, feeling Cas quiver between them as they hoisted him up between their kneeling positions, sliding the briefs down just enough to access his sensitive areas better, but not so much Sam couldn't still feel them.

"It might feel strange, but we promise"

"You're gonna feel so good when we're done."

Cas hadn't bottomed yet, they had wanted to save it for this, give him the full experience. Snapping the lid open and trying to warm the slick oily substance between his fingers, Sam waited for a sign Cas had even heard them.

"My vessel is sturdier than yours, I am not concerned."

Figuring that was Cas-talk for "I trust you", Sam gently probed between his cheeks, loving the needy whine Cas made when he rubbed lube into his tight muscles, relaxing it slowly. He kept eye contact with Dean until they shared a nod, and Dean dropped down to seal his mouth around Cas' cock, timing it perfectly with Sam slipping a finger inside. The entire motel room rattled a little when Cas groaned, reaching to fist Dean's hair and grip Sam's arm for purchase when they hit him with dual sensations.

The soft fabric of the dress kept rubbing tantalisingly across Sam's bare chest, and he was surprised he hadn't torn a hole in his trousers for how hard he had been since they started, but tonight was about Cas. He could wait. Maybe.

Cas clenched around his finger, reminding Sam he had slowed down too much and hurried to rectify it, spreading lube around and feeling the tight muscles start to relax. Adding a little more lube, he pushed back in with two and sought the hidden treasure. The angle was difficult, but when his knuckles brushed against the right spot he heard Dean gag as Cas' hips jerked suddenly.

"Found it."

"What, my lungs?"

Dean's lips were swollen, reddened and wet with his saliva, making the visual of his gasping for air that much more intense as he recovered from the surprise intrusion to his throat. Instead of resuming his oral ministrations, Dean picked up the bottle from the bed, adding some to his own and sliding two fingers in alongside Sam's.

Cas whined at the sudden stretch, but Dean simply nipped at an exposed collarbone before reminding him with a husky whisper, that it was going to be a lot more to take Sam and Dean together. He saw the faint glow reflected in Dean's eyes as Cas took the challenge, and Sam felt the muscles around him loosen more than they had been.

"Did you do that Cas?"

"I'm growing impatient. And you both still have clothing on. This is not conducive."

They wriggled and grunted and Cas huffed before 'popping' their clothes off completely, trying to angle for position. Sam's legs were too long for him to kneel behind Cas without making it a very difficult angle, so he was relegated to flat on his back as Cas essentially mounted him, finally knowing the feeling of being inside an angel.

His body was a little colder than Sam or Dean, not by much but noticeable against human-furnace Dean. Cas rocked himself a few times, testing the depth and feeling before he pressed his body along Sam's, rubbing fabric against skin and staring deep into Sam's eyes for a second. Dean held up the discarded briefs with a smirk, then eyed where Sam was buried inside Cas.

"Is that my cue?"

"Yes."

The stretch must have been harrowing, but Cas took it like a champ as he felt Dean slide home next to him. Cas squeezed, moulded until he fit them like a glove and whined, long and low in his throat before spilling across Sam's stomach. They hadn't even moved yet.

"I ejaculated prematurely. I apologise."

"Don't worry about it Cas, we are very good."

Unsure what they should do just yet, Sam waited for Cas to soften, come down off the edge, thighs shaking with the suppressed desire to thrust and fuck up into Cas with abandon.

"What are you two waiting for? I am perfectly capable of multiple climaxes. Move!"

Supposing they had their orders, Sam nodded up at Dean, sliding out as Dean pushed in, thrusting back up as Dean pulled out. It was a little awkward to begin with as they found their rhythm, but eventually Cas grew bored with the waiting and started rolling his hips, taking them both to the hilt over and over again.

The dress was still around the top of his thighs, his cock still jutting out beneath the fabric as it rose and fell with him, stretching out the sinfully long torso as he leant back against Dean and fucked himself on the twin impalement, lengthened lashes brushing his cheeks with every blink as Cas lost the fight to keep his eyes open under the onslaught.

For someone who was new at this, Cas certainly knew how to put on a show that could make the devil himself blush. They had been holding out for far too long now, and even with "tonight is for Cas" in his mind, Sam felt the heat of climax tear through his body, feeling Dean follow as they both pumped into Cas, seeing stars and making unholy sounds.

He could feel Cas still firm against his stomach when he clawed his way back to reality, noticed the way he was shaking all over as Sam and Dean started to soften inside him.

"P-p-put your fingers back in me."

He didn't even blink when they both pulled out, making eager, greedy sounds when they both pushed two fingers back inside his leaking hole. From this angle, Sam could reach his prostate easily, Dean's fingers undoubtedly adding pressure until Cas whimpered desperately. Dean's other hand slid under the dress, and Sam watched rapturously at every pump of his hand, sliding beneath the fabric, up and down and back again.

Cas let out the most sinfully erotic sound yet, bucking into Dean's hand and squeezing hard around their fingers, sticky and sliding easily inside him from their own come. A dark stain saturated the fabric, fluid running down and dripping over Sam's hips and thighs as the angel finally broke, then dropped heavily onto Sam's body.

Extracting their fingers didn't even make him twitch, and though angels didn't sleep Sam wasn't sure that was true when Cas stayed still, eyes closed.

"I may have stained the fabric."

The words were barely a whisper, usual gravelly voice even lower and Sam's cock gave a hearty twitch at that, a heroic effort given how spent he felt.

"Don't worry, we can get stains out of anything."

Cas eventually pushed himself upright, and Sam could see where the dress clung to his groin, perfect outline of his sticky, sated self. Dean helped the angel stand on only slightly shaky legs. There was glitter on Sam's torso from the makeup Cas still had on. And the motel owners probably thought they were making porn from all the sounds, and the fact he thought the bedsheets were unsalvagable now. At least they had a spare tonight.

Despite the fact they were so fucked out Sam thought another round might kill them, he felt heat begin to build as Dean led Cas to the bathroom, winking over at Sam.

"Next time, we can both dress up, and Sam can be in the middle."

-SPN-

Actually had more fun with this than I expected! Thanks for the prompt!