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There's Something About Dean by The Huntress
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Author's Notes:
1) Thanks to Supernaturalgrl, Chrissy6299 and SammysSlave for the assist. They rule! All remaining mistakes mine and if you find any, Dean can come and paddle my ass. As per usual, I will not enjoy it, I swear.
2) It's rare for me to do sequels, but this one would not let me go.

 

Sam slept well that night, and when he cracked his eyes open he met Dean's already wide-awake ones. "Morning." He leaned in for a kiss.

"Mmm, now that's a nice way to wake up." Dean met Sam's lips, nipping on the lower one as he pulled away. He smiled, took care of his morning ablutions and motioned Sam into the bathroom when he was done.

Sam stretched, went in and washed up. He came out to see their things packed up, save for a change of clothes for him. "We leaving already, Dean?"

"I'm up, you're up, IHOP awaits and the cable isn't working."

"Okay, but you're buying." Sam got dressed and picked up his duffel.

"Don't I always?" Dean followed him out, his brain already spinning ideas as to how he was going to get revenge on Sam.

++++++++

Their next stop was in Bardstown, Kentucky, checking out a series of grave robberies. That was a bust, for them at least, because the robberies were being committed by a group of frat boys as an initiation. But the town was nice, the locals friendly, and the motel was clean, so they decided to stay for a couple of days. After supper in the diner, they returned to the room.

Dean called dibs on the shower and finished quickly, and then Sam took his turn.

When Sam came out, Dean was standing there smirking, and alarms and whistles went off in his head, but because it was Dean, he ignored them. Before he could say anything, he was flipped onto the bed, his arms pushed over his head and handcuffed to the headboard. He opened his mouth to question what Dean was doing, but he was gagged and blindfolded quickly.

"You like to play games, Sam?"

Sam muttered something through the gag.

"You're not shaking your head."

Another unintelligible mutter.

"Perverse Pirate and Virginal Captive - guess which one of us is which?"

A growl through the gag and Sam began to thrash about, trying to kick Dean.

"Whoa! Calm down, Sammy." Dean removed the gag. "You don't like games?"

"I like games just fine, Dean," Sam snapped, "but don't you think you should have asked me first? And asked me if I have a safe word?"

Dean felt his face growing hot and mentally kicked himself. "Yeah, I should have, I'm sorry, and what is it?"

"First, take the blindfold off."

"And what if I don't?" Dean challenged.

"I don't like not being able to see, Dean," Sam whispered. "Please take it off."

Dean felt Sam's body tense up beneath his and immediately complied. "If you want to stop, Sammy...."

"No, I just have to be able to see you." Sam gave him a small smile, "And it's...." He flushed pink. "Perry Mason."

"Perry Mason?" Dean began to giggle.

"I swear, Dean, if you don't stop laughing...."

"I'm sorry." Dean composed himself.

Sam nodded. "Now, where were we...oh yeah...pirate and...virginal...captive." He narrowed his eyes in anger and began to struggle. "Why have you kidnapped me, you heathen, and what are you going to do with me?"

Dean was impressed that Sam got into the game so quickly. "You're my prisoner, boy, and you're going to do what I say." He cupped Sam's chin in his fingers. "Now, young one, tell me your name." When Sam didn't answer, Dean grabbed his hair and forced his head up. "Do not make me repeat myself!"

"It's Sam."

Dean grinned at him lasciviously. "You're a virgin, aren't you?" He licked his upper lip and raked his eyes up and down Sam's body.

"That I am not!" Sam was indignant. "Many a wench have enjoyed me and I them!"

"Many a wench, hmm?" Dean smirked.

"Whatever it is you want, you should know that my father is wealthy and will pay any ransom you demand."

"What makes you think I want a ransom?" Dean grabbed his ass and squeezed it. "Have any men enjoyed this fine ass of yours?"

"Men?" Sam's eyes grew wide.

Dean sucked on a finger, reached forward and teased Sam's hole.

"NO!" Sam tried to pull away, but there was nowhere for him to go. "Do not touch me with your filth!"

"Filth is it?" Dean laughed and slid his finger deep inside.

"I will not allow you to sodomize me, you...you pig!" Sam spat at him. "You are vile and perverse!"

"You will not allow?" Dean pulled his finger out, returning with two. "I do not believe you have a choice in the matter." He upped it to three and fucked Sam like that for a while, watching Sam's cock swell. "And your mouth spouts no, yet your cock screams yes." He tugged on his own swollen cock. "I will have you, innocent one."

"You will not put that...that monster inside of me!"

Dean had to bite the inside of his cheek to stop the giggle at Sam's choice of words. "Then I shall not." Dean slid from Sam's body, rifled his duffel and went into the bathroom.

"Dean, what are you....?"

"Shut up, young Samuel, or I shall spank your bottom raw!" Dean yelled from the bathroom. He came out holding a blue dildo that was a little bigger than his own cock and laid it on the bed. "Since you refuse to allow me to take your virginity, I shall take it with this." He picked up the tube of lube and knelt between Sam's legs, motioning him to bend his knees. "By the time I am done, you will beg for me." He squeezed lube onto his fingers and slicked the dildo.

"NEVER!"

"We shall see." Dean teased the hole with the tip, one hand on Sam's ass, spreading him a bit. Taking a deep breath, Dean leaned forward, teasing the hole with his tongue - Sam's body jumped off the bed. "Did you enjoy that?"

"Yes," Sam squeaked.

"Good." Dean inched the dildo in, stopping every inch to jostle it a bit, listening to Sam's whimpered gasps. "Is it too much, young Samuel?"

"N-n-no, tis not." Sam's breathing had increased and he was starting to sweat.

It took every ounce of willpower Dean had to not shove the dildo up Sam's ass; he had to draw this out.

"Please...." Sam moaned, bearing down, wanting more.

"Do you wish my bare flesh within you, young virgin?" When he didn't get an answer, Dean smacked his ass so hard he left a handprint; Sam just moaned. "You will answer me or I shall stop this and leave you bereft." To emphasize he meant it, Dean removed the dildo. "Is it pleasure you want, young Samuel?"

Sam had forgotten, for a moment, that they were playing a game. "It's Sam, and I swear, if you don't fuck me right the hell now...."

"Tsk, tsk, young noble, you have the foulest of mouths." Dean moved up Sam's body, propping Sam into a sitting position, holding his cock in his hand, level with Sam's mouth. "Take it within your sweet lips."

Sam got back into character. "I'll not give you that satisfaction, you...you scalawag!" He pursed his lips and shook his head vehemently.

Dean rubbed the tip of his cock over Sam's lips, the precome glistening over them. "Your lips are wet with my spunk; taste of it with your tongue." Dean met Sam's eyes. "Go on, my virgin, I will not force it into your mouth." He brushed the hair from Sam's sweaty brow. "I am many things, but a liar I am not." To give his trust, Dean shifted back. "Do it."

Sam closed his eyes and ran the tip of his tongue along his upper lip, followed by the lower, a soft sigh escaping his lips.

"Do you wish more, virtuous child? A further taste perhaps?" Dean was jerking himself slowly, getting precome on his thumb, bringing it to his own mouth and sucking on it.

"Please, my liege, allow me to slide my lips around your cock, to learn to pleasure you." Sam flashed the puppy-dog eyes. "I beg of you."

"Liege?" Dean smiled. "Then I am no longer a vile and perverse scalawag?"

"Whatever gets me laid," Sam muttered.

Dean smacked his ass again. "What was that?"

"I will do anything you ask of me, I swear it."

"Perhaps I do not want you now," Dean teased, moving further back.

"No, do not discard me!" Sam whimpered. "I want to do this."

"Be forewarned, pure one, once I have taken you, there is no turning back." Dean palmed his face. "You will be mine forever."

"I understand." Sam moved his head forward. "But you must teach me, as I am unschooled in the ways of such things."

"If that is what you want." Dean brought the tip of his cock to Sam's mouth again. "Open."

Sam did as he was told and sucked on the head. "More."

"Yes...." Dean began the slow slide in, wanting to drag this out, but Sam was very talented with his tongue.

As he sucked on Dean, he teased with his tongue, and his hot breath was upon Dean's cock at the same time. With one quick motion Sam lunged forward and managed to get him all the way in, working on his cock, sucking hard, pulling back, his teeth grazing the length.

"HOLYJESUS!"

Sam pulled back, smacking his lips together. "I am doing well?"

"Oh fuck yeah," Dean moaned.

"I don't think pirates talked like that," Sam snickered a bit.

"This one does." Dean pushed his cock into Sam's mouth, held it there for a moment, and when Sam began to suck harder, he pulled back and teased some more, holding it just out of Sam's reach. "Perhaps you are enjoying yourself too much."

"No, I am not procuring any enjoyment from this." Sam gave Dean his best puppy-eyes. "I give you my word."

"Well then, if you are not receiving gratification, I will have to withhold this pleasure from you."

"I meant to say...I...."

Dean grabbed Sam by the hair and pulled his mouth all the way down his cock. "You're my whore, and don't you forget it." He held his cock deep within Sam's throat, undulated his hips, and then he paused, hearing a sound behind him. They had salted the doors and windows, nothing could have gotten in, and he slowly turned his head.

Castiel was standing there, eyes wide as saucers. "I...I...I will call ahead next time." And then he was gone.

Sam burst out laughing. "We just scarred him for life."

Dean tried to stop his giggles, "Shut up, young Samuel," and failed. "Gimme a sec, Sam."

Sam managed to calm himself. "Are you going to take my purity now, my captor?"

A nod from Dean, who managed to stop his laughter. "You wish me to do this?"

"Yes, yes, I wish for you to take this from me, to mark me as your property." Sam slid his long legs up Dean's chest, over his shoulders. "Take that which will forever belong to you."

Dean picked up the lube and anointed his cock. "If I do this, young swain, there is no turning back. Are you fully prepared to be mine, heart and soul?"

"Yes, oh yes, I will be yours." Sam arched his hips forward. "Take my chastity, defile and corrupt me...anything."

"So be it." Sam was already loose and Dean slid in easily, pausing when he was buried within the warmth that was Sam's ass. "Does my bare flesh feel good within you, my whore?"

"I am no man's whore!"

"You are my whore, young Samuel," Dean slid out, slapping his cock against Sam's ass, "and you will say it, lest I leave you to pine for release until you shed tears." He glared at Sam, waiting.

"No." Sam met the glare with defiance. "I shall allow you my body and my soul, but not my dignity."

"I will give in to you now, my whore, but only because your attitude impresses me." Dean returned with a hard thrust, grasping Sam's thighs so hard he left finger marks, followed by a slow slide out and more teasing.

Sam's whole body arched, but Dean's hands moved to his hips, preventing movement. "Tell me how much you want my cock fucking you until you scream. Beg me to fuck you, to fill your ass with my hot come." He knew he hit that sweet spot within Sam when Sam shrieked. "You are so beautiful like this. Did you know that?" He pounded harder, watching his cock moving in and out.

Sam was beyond any form of coherent speech; he was reduced to grunts and soft moaning.

"Fucking whore...my fucking and sucking slut. You just love my hard cock pounding inside your tight ass." Dean was close and knew Sam was too. "Tell me and maybe I'll take your dick in my fist and let you come."

"Yes, Dean, Dean please...need you...need...want...please...."

"Only for you, young Samuel, never anyone else again." Dean wrapped his hand around Sam's cock and jerked him hard. "Come, baby...I wanna watch you."

Sam came, fountains of come shooting in the air, and Dean tumbled after him.

"Oh fuck...holy shit, Sam, I never...it was never that hot with anyone." Dean panted and gasped for air.

"I...gotta...agree...." Sam managed to get out, his legs sliding from Dean's shoulders.

Dean pulled out slowly, retrieved a cloth and cleaned them, giving Sam the softest and most loving kiss.

"Dean?" Sam gave him a wan smile. "Are you going to uncuff me?"

"I don't know, Sammy." Dean sat beside him, taking Sam's chin in his fingers. "Who owns who? Who's the fucktoy?"

"I think..." Sam started, "...I think we own each other, and we both enjoyed being a fucktoy."

Dean kissed him again, nodded, and got him out of the cuffs, placing a kiss to each of Sam's wrists. "I didn't hurt you, did I?"

"No." Sam slid his arms over Dean's shoulder and pushed him onto his pack, returning the kiss with fervor. "It was fun."

"Fun?" Dean raised an eyebrow.

"Okay," Sam conceded, "just so your ego doesn't take a bruising, it was the most amazing time I have ever had. You are...talented, very talented."

"I know." Dean grinned. "And can I assume you've played games before?"

"Not role-playing." Sam rolled to his side so he was lying in Dean's arms. "Dean, tell me about the guy in Tulsa." He tilted his face up, a bit concerned. "What did he do to you?"

"He didn't do anything Sam, except let me fuck him silly. But...he mentioned that I was the second best sex he'd ever had, and I was curious, so I asked him to elaborate." Dean put his fingers over Sam's mouth so he could finish. "He then told me about the best sex he'd had. It seems there was a guy he knew in college, who performed a cleansing on a supposedly haunted frat house...."

"Oh shit," Sam muttered.

"Yes, Sam, oh shit. Told me the guy was, and I quote, 'inventive, knowledgeable, and quite kinky too.' And before he was done," Dean smirked, "I discovered that the guy he was talking about was named Sam Winchester, who, up until that point, I thought liked women, didn't sleep around and was totally vanilla."

Sam half-laughed. "I'm a Winchester. We don't fit any molds, you should know that."

"I was enlightened..." Dean nodded, "...with a 2x4 upside my head."

"Dean?" Sam snuggled closer. "Can we play prison guard/fresh meat next time?"

Dean blinked at him. "Where'd that come from?"

"I read it in a book," Sam said shyly.

"Okay," Dean replied, "but only if I can be the fresh meat."

"What about Castiel?" Sam asked. "He's going to be asking questions, I just know it."

"We'll give him porn," Dean suggested. "He's always wanting to know about being human; we'll tell him it's a requirement."

Sam absentmindedly drew patterns on Dean's chest wth his fingertips. "It sounds like fun."

"And can I assume," Dean inhaled sharply at the nail flicking his nipple, "that the big and bad guard will give me step-by-step instructions?"

"The big, bad prison guard has lots of ideas," Sam yawned, "but the virginal captive is tired and needs to sleep."

"Then sleep, young Samuel," Dean crooned. "I will watch over thee."

"Waffles for breakfast?" Sam murmured, almost asleep already.

"Anything you like."

"Love you, Dean."

Dean kissed the top of his head. "Love you too, Sammy-baby."

FIN

 

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