Title:   Halloween Crack!Fic - The Pirate and the Maid; Dean/Sam; NC-17

Author:  softbluebuddy

Genre:   Pure and Total Crack

Characters:   Dean/Sam

Rating:   NC-17

Word Count: 1261

Warning: Costumes and Cross-Dressing and sex of the Wincest variety

Credit for manip goes tostawberynvanila .   Sorry, I couldn't find a manip of Dean in a French Maid's costume.  You'll have to use your imagination for that.

Summary: Dean and Sam find themselves working a case on Halloween night. To be able to investigate unnoticed, they have gone to a costume shop and rented the last two costumes available. This is how their evening went.

 

The Pirate and the Maid

An exasperated Dean looked at his brother and said, “Tell me again why we are dressed like this.”

“Hello. Halloween, remember?” replied Sam.

“Hey smartass, I remember that it’s Halloween, but we don’t celebrate Halloween.”

“Do I look like I’m celebrating, Dean?”

“Well, no, not really.”

“Come on, you know we just need to blend in enough while we get that information we need to finish off this case.”

“But Sam, why do I have to be the French Maid?” asked Dean. He didn’t actually whine, but it was clear that he wasn’t overjoyed about having just shaved his legs and gotten dressed in a French Maid costume, complete with high heeled shoes, makeup and a blond wig.

“Because I’m almost six foot five, dude. You are tall, but I’d look ridiculous in a French Maid costume.”

“But why did we have to get a French Maid costume at all?”

“Ahoy matey, that was all they had left,” Sam laughed shaking his head and remembering them at the costume shop. “T' maid and t' pirate.”

Hours later, they had wrapped up the case and were back at their motel room, still wearing their costumes.

"Your French Maid outfit be lovely with your blond hair and high heeled shoes." Sam told Dean.

After an evening of listening to Sam talk like a pirate, Dean finally looked at his brother and with a funny look on his face said, “Sam, how is it that you are so good at talking like a pirate anyway?”

“Seriously? You think that I’m convincin'? Right on. Cool. Just lucky I guess. Haven’t you ever heard o' International Talk Like A Pirate Day?”

“What? There’s a whole day for people to walk around talking like a pirate? No, I’ve never heard of that. Is that some goofy holiday where they close the banks and everything?”

Laughing at Dean who clearly had no idea what ITLAP Day was, told him, “T' banks don’t close. It’s just a goofy day. It was big at Stanford. We’d walk around talkin' like pirates.”

“Right … So now I understand what a higher education is. And all this time I thought you were studying there.”

"Come on, lass just because we worked our asses off studyin' doesn't mean we couldn't have fun too you know."

~0~0~0~ Fifteen Minutes Later~0~0~0~

“I can’t believe that I’m letting you do this,” Dean told Sam.

“Argh, matey … ye not be letting me do it … I’m a pirate and I take what I want.”

“Sam, come on. Seriously, dude … I’m dressed as a French Maid and you have me bent over the couch. How fucked up is this?”

“Argh, you forgot t' mention it be t' Great Pirate Samuel that has t' French Maid bent over, I think that be even more fucked up, t' quote you.”

“All right then, Great Pirate Samuel … you gonna talk all night or you gonna fuck me?”

The Great Pirate Samuel had the beautiful French Maid Deana bent over the couch, panties torn off moments before and his cock lined up behind the already prepped and puckered hole.

The French Maid Deana was still wearing high heeled shoes, the blond wig and the makeup, but no panties and the skirt of the maid costume was shoved up around the waist.

The Pirate slipped the tip of his cock in to the maid’s ass as he said, “Argh, I think I've a mind t' be fuckin' you.”

Deana was whimpering and begging for more while bent over in those shoes, nasty ass wanting to be filled so badly

The pirate slapped the maid’s ass, and then slid his cock all the way home.

In general, Dean and Sam took turns topping, but when Dean bottomed for is brother, Sammy just fucking loved it. He loved hearing the little whimpering noises from his brother, and tonight was no exception, but somehow it was oh so much hotter with Dean’s freshly shaved legs, high heeled shoes, and the French Maid costume on with make up and a blond wig. 

Unfucking believable thought Sam. Dean was right, this was fucked up, but goddammit it felt good fucking into his brother while he was dressed like a girl.

He truly was Samuel the Pirate and he truly was pounding into the French Maid from the rear. But he suddenly decided that wasn’t nearly enough tonight. Sam pulled out of Deana and spun the maid around, balancing on the top edge of the couch and then slid back inside the heat of the maid’s tight hole.

“Fuck Sam…”

“Gotta see you Dean, never seen you like this, like a lass … so fucking hot.”

Dean grabbed onto his brother’s shoulders, wrapped his smooth legs around the pirate’s back.

“God, Sam … so nasty … I can’t believe I’m getting fucked by a pirate…”

"Oh, believe it you comely wench. And it feels so good too. I can hardly wait till I be fillin' you full o' me seed."

“Jesus fucking Christ Sam, how can you stay in character while you are sliding your fat cock in and out of my ass with my legs wrapped around you?”

"Not t' worry me lovely. Hang onto me shoulders and I'll reach on down here and give t' little maid a tug or two."

Dean immediately tightened his grip on the Pirate’s broad shoulders since Sam had let go of one of his hips to jack Dean’s cock in his huge hand.

Dean watched Sam intently feeling every thrust of his brother’s hips and every tug of his hand. It was amazing. He also noticed how smooth and sexy his legs looked wrapped around his brother. He’d never shaved his legs before, but Sam had loved the feel of his shaved legs. He wasn’t sure he’d ever shave them again, even for a case, but catching a glimpse of himself in the mirror, dressed like a girl in a French Maid outfit while his brother the Pirate was fucking him silly, well, he decided that was pretty awesome for a change.

The best part for Sam was probably because Dean always called Sam a girl. So in this instance Sam had gotten to turn the tables on his big brother.

Truth be told, Dean thought he looked pretty good as a girl and was actually glad that he was the one that got to dress up like that, although he wouldn’t mind seeing Sam in this outfit, if the situation ever arose. Too bad they had only rented the costume and had to return it.

Dean kept hanging on to Sam’s shoulders so he wouldn’t fall backwards over the couch as his brother kept a steady pace with his hips and his hand.

Sam timed everything just right so that he and Dean came together, come filling Dean’s ass and all over his stomach and the French Maid costume.

“Oops,” said Dean laughing out loud, “I guess we’re gonna have to buy this now.”

Sam laughed to, “Damn. And here I was hopin' we’d keep that outfit and t' wig before you dumped a load o' your spunk on it. I couldn’t have planned it better meself.”

Then Sam leaned down and gave his brother a slow wet kiss. “You be so hot dressed like a lass. I had no fuckin' idea.”

“Yeah? Well you are one hell of a pirate. Why don’t we just keep both of the costumes?” asked Dean with a sly grin at his brother, the pirate.

“Why don’t we indeed?” Sam agreed.

 




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