Raelle23 - I'm glad you enjoyed it! I hadn't considered skirts much to be honest, but that was good inspiration so here it is!
Shannonisabanana - There is a third chapter! With both dressed up and Sam the poor victim... Well, there is now! *points down*
Sorry this took so long to write, but I'm shit like that!
-SPN-
"Whatcha doing Cas?"
Dean dropped heavily into his seat, muscles aching with the werewolf hunt from hell and leaned over to see what the angel was staring so intently at.
"Browsing. Would you say I am more of an apple or pear?"
The thing in question transpired to be a fashion magazine, and the article in particular Cas was reading was all about how to "dress for your shape". They had created a monster.
"Uh, neither. You've got no curve in your hips or waist. You got a freaking great ass, but no fat on your thighs. So you are neither. Why, what are you thinking?"
Cas indicated his goal, winning a smirk from Dean as they looked over at Sam.
"I'm gonna take a quick shower, then we can go shopping. I'll get dinner on the way back Sammy!"
The first was said only to Cas, the latter called out to Sam where he was across the room, polishing his pistol.
"Where are you going?"
"To get food. And Cas wants to check something out. An hour, two tops. Anything in particular you want for dinner?"
"Not dripping in grease, otherwise too hungry to care."
The hot shower did a miracle of sorts to his tired muscles, and Cas' idea had given him a second wind - as did the promise of bacon cheeseburgers. There was beer in the motel room, so they were good on that front. Though he remembered they were low on lube... ever since Cas and the dress happened, their menage-a-trois relationship had continued to blossom with a surging heat.
"Dean, what dress size is this vessel?"
A couple of nearby patrons gave Cas sideways looks, but his strange words combined with that half-vacant not-of-this-earth expression on his face meant most were content to just ignore the strange man in a trench coat. Grinning to himself - Cas was a hoot - Dean scanned the shelves for something to his tastes.
"You're about a ten. That dress was anyway. Maybe a twelve if it's tight."
Spying a display of A-lines, he knew he was on the right track and moved in that direction. Castiel, it turned out, wanted to go one further while they were out, eyeing up some stiletto heels. Jesus, Dean didn't know how the world would cope if Cas' gorgeous legs got any longer... Sam was bad enough for that. He could just about fit in the largest size available in that store - Jimmy Novak had fairly small feet it seemed.
"This is a frivolous purchase."
Cas contemplated the box on his lap, a couple of bags in the back of the Impala containing all the more pleasant treats of the evening.
"So is using lube on you when you can make it yourself. Sex is a frivolous thing to you. Basically, shut your pie hole and keep the motor running."
Brow creasing, Cas leant back and watched the Impala while Dean hit the convenience store for candy bars, protein bars, the weird Greek biscuits Cas liked and a couple of bottles of lube. There was a sale on the bags of road salt now winter was easing off, so he grabbed two of those - they came in handy for ghost-proofing whole rooms at once.
"Here ya go Cas!"
"I am an angel, I don't need to eat."
"I once saw you eat three hundred cheeseburgers. You like those."
A small smile fixed itself on Cas' face, and the little honey covered crunchy things disappeared one by one into the angels mouth between the convenience store, the diner and then finally the motel room.
Sam noticed when he kissed them in greeting - Dean first, then Cas. He licked his lips, tasting the sweet confectionary.
"You been treating our angel?"
"Oh, you have no idea Sammy boy. Soups on."
Sam handed him an opened beer, Dean handed back a cheeseburger with all the salad, sweet potato fries and some flavoured water thing.
"Wow. Almost healthy. What's the occasion?"
"Cas and me want you to have your strength back for tomorrow is all. We got a surprise but you're too beat up. Plus it's getting late and we've done the job but we're paid through til Friday. So eat up, sleep up and get ready."
The anticipation may well have almost killed all of them... ok, maybe he was being a tad overdramatic. A good nights sleep and breakfast Sam went out to get later, both Winchester brothers were feeling a whole lot better. Dean sent Sam to shower while he and Cas got 'ready', knowing there would be a near instantaneous reaction from him when he exited the bathroom.
"I think this garment may be too small."
Cas looked perturbed by the fabric that barely stretched across his ass, only just long enough to disguise his cock at the minute. Dean hadn't realised it was quite that short himself.
"Nah, it's meant to be like that. You bought a mini-skirt Cas. Come on, get the shoes on before Sam comes out!"
A new sort of bonding for the two had been that they now took turns doing the others make-up - sometimes with Sam watching, because he would get hard just watching the accentuating of features, the delicate dusting of colour and shimmer across usually textbook-masculine-strong faces.
Cas had even learnt not to jab Dean in the eye with the mascara wand. Checking his reflection in the black screen of his phone, Dean pouted at himself to check the sheen of his lip gloss.
"Yeah, I'd do me."
Testing himself in the stilettos, Cas was naturally graceful as an angel and the effect they had on his legs was literally mind-blowing. Dean felt the slim green skirt he had on tighten, aroused by the miles-long legs extending from the navy mini that currently barely hid a thing.
"I'd do you too, damn Cas. But today... today is all about torturing Sammy."
The shower shut off, and Cas still being Cas sat down, crossing his legs awkwardly which only served to make his barely-there skirt ride up higher, revealing the edges powder blue briefs that drove Sam crazy with their lace detail.
Dean could detect the sounds of Sam having to roughly towel dry his long hair, then comb it through to prevent it being a chaotic explosion as it dried. Sure enough, there was a couple of muffled swear words where he came across knots, because they didn't always have conditioner to hand on the road.
Eventually the door opened with a cloud of steam billowing out, Sam in nothing but a towel appearing like a beautiful apparition in its midst. There were stray water droplets rolling down his gorgeous bronze chest muscles, leading down the firm stomach to be halted by the impeding towel. Raking his eyes back up, Dean finds the damp hair drying at the ends already and settling around his broad shoulders.
"Wow. Cas was made for heels."
"Right? You gonna stand and stare or what little brother?"
He crossed the small room in two loping strides and dove in to kiss Dean, mapping the bare torso that led to the slim fitting skirt.
"I think we found your new hunting outfit."
"In your dreams Sammy. We would never get anything done."
His mouth tipped up in a smirk, then Sam turned to kiss Cas deeply too. The angel tipped his head back, letting Sam ravage his mouth repeatedly while Dean enjoyed the view. Inhumanly strong, Cas pinned Sam down on the bed beneath him and the tangle of impossibly long legs, gasping sounds and Cas' pert little ass peeking out from under his skirt had Dean wanting to abandon the 'plan' there and then.
"Damn, it's hard to believe you were so innocent a year ago Cas. I think Dean's a little lonely though, and today was his idea."
Cas twisted his head around, observing Dean with his big blue eyes and offering position.
"You are correct. He does look lonely."
"How do you want us Dean?"
Pulling Cas to stand up at the end of the bed, Dean manipulated Sam's endless limbs up onto his hands and knees, stripping the towel away to reveal the heavy erection jutting out from his body. The outline of Cas' cock was pressed tight against the fabric of his skirt, and when Sam spied the tempting little briefs beneath he made a needy whine.
"Don't give him what he wants too easy Cas. Make him work for it."
Sam whined again, nuzzling Cas' groin and releasing hot little mewls. Dean knelt up behind Sam, dumping lube into his hand and setting to work Sam open quick and hard. It would still hurt, still stretch just a little too much but when he was in this sort of mood, Sam loved it like that. Watching ravenously, he saw Sam had managed to roll the mini up over Castiel's full cock, straining against the fabric that was rapidly dampening with a mix of precum and saliva where Sam mouthed hungrily at it.
Dean had never really been in the middle like this himself, but knowing how it felt to have Cas thrust into his throat and have Sam fuck into his ass separately, he could only imagine how intense, how overwhelming it would be for Sam very soon.
Seeing Cas stare hungrily, Sam turned his head to see where Dean was lifting his skirt up, rolling the (comfortable, sue him) lace-front panties down to sit just behind his balls. That pushed them forward and gave Dean an added sensation around the sensitive area, and judging by the dilated pupils in both sets of eyes on him, it looked hot as fuck.
"C'mon guys, you're killing me here."
"Actually Sam, you are statistically more likely to die from sexual intercourse than unsatisfied..."
"Cas, shut up and give the man his treat."
Dean grinned as Cas fell silent, both Winchester brothers much used to the angel reeling off random facts that didn't improve the mood. Slicking his pulsing erection with lube, Dean paused to ensure Cas wasn't in Sam's mouth and at risk of being bitten, then pushed himself in in one slow, sure thrust. Sam keened, squeezing and pushing back on the intrusion to ensure Dean was flush to him, hips to bottom.
He pulled out, slid back in a few times, making sure Sam wasn't about to be jolted in surprise - just because Cas could heal any injury didn't mean they wanted to test it. When the muscles almost constricting his cock began to relax as they adjusted to the pressures, and Sam was making pretty little moans as his prostate was stimulated, he gave Cas the nod.
Sam mewled happily when the fabric finally came down, letting him take the thick erection into his mouth and he gagged a little in his haste to suck at Cas' cock. Dean smirked at Sam's easy submission, moving his hips again at last to take his own pleasure from the sublime body beneath him.
The angel fisted his hands in Sam's hair slowly, using his grip to control the motions of Sam on his cock and letting his head drop back as pleasure overcame him. Cas was naturally seductive despite his awkwardness, and the fact he never realised he did it was even hotter. Dean couldn't quite help himself, thrusting harder into Sam's tight ass as he watched Cas fuck into the hot mouth wrapped around him.
Sam became overwhelmed first, letting go of Cas to drop his head and howl out his release as the muscles around Dean contracted and spasmed tightly. Cas was too close to hold back, gripping himself and stroking three or four times before he came explosively, painting thick white stripes across Sam's shoulders and back with a deep, quiver-inducing orgasmic groan. Dean couldn't help himself, pulling out and adding to the canvas of lean, long muscles along Sam's back with his own come.
The quickest to recover, Cas righted his underwear and mini skirt, wobbling in his heels slightly as his body came down from the endorphin high. Sam was still gasping, trying to work his abused throat muscles properly but across the board, Dean knew all three of them were grinning. He reached down a hand, slapped across the taut curve of his little brothers ass and enjoyed the hypersensitive, pained moan.
"Don't worry Sammy, once you're feeling a little better me and Cas will trade places."
-SPN-
The biggest issue, I find, with writing these one shots is that they tend to happen when I'm really out of practice writing slash and so it always seems... sub-par.
Still, I'm gonna call Dress Up done!
(unless someone gives me another idea I simply have to write, but I feel like it's all been covered personally)