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Pretty In Plaid
dark Jensen
Title:  Pretty In Plaid
Characters:  Dean/Security Guard, Sam. 
Genre: slash
Rating:  NC-17
Word count: 3500 approx.
Warnings/kinks:  Dubcon, case related cross-dressing, restraints, dirty talk, mild humiliation. 

A/N: This was my first foray into the kink meme world.  It was written some time ago but I've just recently claimed, cleaned and had it beta'd.  Thank you to Kasman!  When picturing the OMC for this a certain individual kept coming to mind.  I used his name as inspiration. 

Summary:  Sam and Dean investigate an underground sex club.  A security guard takes an interest in Dean..

Original prompt:  Dean in a skirt, for whatever reason, legs spread, fondled and fingered by someone other than Sam or John. Resistant and embarassed but so turned on that he can help but spread his legs wider and moan helplessly. Sam can be watching or not present at all.  


Liev watched the figures on the security screen and gave a cursory glance to the guest list.  Dascen paid him good money to make sure these underground events ran smoothly.  He wasn't about to lose out on a well-paying gig because of two loose canons. 

Whoever they were, they'd made sure to dress the part.  The tall one was shirtless beneath a dark chocolate leather vest and matching pants and never ventured far from the shorter one in the plaid skirt and white knee socks.  Had they even once stopped to fuck each other or stick their dicks in any of the various willing or unwilling orifices, he may not have taken notice of them at all. 

The fact that they didn't seem interested in enjoying any of the festivities, legal or otherwise, was a huge red flag.  The place was a smorgasbord for nearly every imaginable sexual kink one could think of.  The location was top secret; the entertainment hand selected, and the guest list very much invite only.  He was pretty sure these two weren’t on it. 
"Separate them," Liev said to one of his men.  "Bring tall, dark and possessive to a holding room.  I'll take care of the skirt."   
Aiden smiled knowingly, but said nothing.  "You got it, boss." 
He did a site check of all security camera locations and observed the doors long enough to figure out how his two uninvited guests got in.  Dascen's personal security was not nearly as diligent as his own. Liev replaced them with two of his men and ordered a check of the perimeter and all possible entry points.
Liev found the skirt by himself, poking around in an area that was a little less secure and a whole lot more secluded.  The young man was much more attractive than his tiny security screen had led him to believe.  He waited until the kid ventured deeper into a corner of the warehouse and away from the more populated festivities. 
Liev took him by surprise, which was likely the only reason he'd gotten the cuffs on him at all.  Fucker was strong, but Liev had the element of surprise, three extra inches of height and about twenty additional pounds of muscle.  He had just enough time to force the young man's arms up over his head and loop the chain over a broken piece of pipe before pretty boy knew what hit him.
Liev cut the curse off with a gasp as he reached under the skirt and wrapped his hand around a fully hard, silk covered dick. 
"Whoa," pretty boy tried to slow things down and explain.  "You've got the wrong...ungh!"
Obscene lips fell open as Liev jacked him nice and slow, hand as comfortable as if it were wrapped around the stick shift of his jeep. 
"Don't think so," Liev breathed.  "I know you're not supposed to be here." 
Palming his way down between the young man's legs he cupped uncomfortably restrained balls.
"Look...I...I can explain...I..." the kid made a breathless attempt. 
"Don't bother," Liev said as he hooked a knee and lifted it.  He toed a nearby crate and pulled it close, elevating the kid's foot, forcing the leg open at the knee and holding it in place. "I don't really care." 
Liev stroked the underside of silky balls with his fingertips, drawing forth a quiet noise from the back of the kid's throat. 
"Here to...to help..." the young man stuttered. 
"Oh, you're being very helpful," Liev said with a chuckle, finger slipping beneath an edge of panty and allowing one nut to slip free.  Liev tugged, twisted and rolled it between his fingers.
"Fuck...oh, fuck."
Liev smiled as the kid panted, lashes fluttering. 
"Nice outfit, by the way," Liev taunted.
Narrow green eyes flashed a delicious warning he'd be foolish not to take seriously... under other circumstances.  
"Those white knee socks?" Liev felt obligated to inform the young man, "totally to blame for why you're cuffed to a wall with my hand up your skirt." 
It was true. A kink he didn't know he had until now.

He pulled the elastic aside and took hold of the full sac, sliding his hand in and out between the kid’s legs, scraping the tender skin over his calloused palm.
A soft, reluctant moan escaped his captive, hips canting ever so slightly. 

"That's it, sweetheart," Liev encouraged, "just enjoy it." 

"Fu...uck you," The vehemence behind the statement was lost in a breathless stutter. 

Liev pulled his hand back and gave tight balls a slap.  His captive cried out, hips jerking.  He slapped them again.  Panting, the young man squirmed but managed to hold his tongue.

Smirking, Liev took proprietary hold of the hard cock once again, the tip of which was still trapped within the confines of silk panties.  He swirled his thumb over the flared head, the fabric slick and clingy with precome.  

"Damn, boy," Liev praised, voice husky, "I've fingered pussy that wasn't that wet." 

He ripped the panties roughly to one side, kid's jaw tightening as his dick bobbed free.  Liev fingered the slit with slow, smug deliberation, enjoying the twitch of muscle from clenched teeth and the rolling flutter of lashes as the young man fought his body's instinctive response. 

He fucking loved a challenge.  It made the surrender so much sweeter. 

Liev held the emerald gaze as he brought the come covered finger to his mouth.

“Jesus,” he said, “taste as sweet as you fucking look, kid."

"Look," voice a breathless tremble, "you have no idea what's about to happen. I...I can help." 

He gave the kid credit for another try but dismissed the comment.  He had the place on lockdown.  No one else was getting in or out until the party was over. 

Liev looked down at the boy's dick tenting the skirt and raised a suggestive brow.  He knew exactly what was about to happen.  He reached under and took firm hold right at the base, shifting his stance a little. 

"You wanna help, sweetheart?" he asked rhetorically, "fuck my hand like a good little bitch." 

Something subtle shifted deep within the glacial gaze as hips stuttered and the young man fought the urge to thrust.  Liev knew the look.  It was one of his favorites. The kid's mouth opened in a harsh pant as he rolled his wrist, slender hips jutting forward once, twice. 

"Be a good boy and I'll let you come when I'm done with you," Liev promised arrogantly.

A faint, desperate whimper lodged in the young man's throat as his hips twitched - a small, shallow thrust into Liev's tight fist.   

"There you go," he encouraged, teasing a moan from pouty lips as he pumped the silky smooth shaft with practiced ease. 


A ragged plea, one that likely cost dearly, but Liev recognized the latent desire simmering beneath.  The kid wanted it, he just didn't know it. 

"Too late for that, darlin," Liev informed him as he softened his grip, let it become more of a caress. 

The hand holding the boy's knee open  slipped beneath the skirt to fondle his sac as Liev jacked him. A tense line of beautiful muscle, his captive pulled against the cuffs, hips rolling forward of their own accord with a hot, helpless keen as his balls were squeezed and his dick found glorious friction against the palm of Liev's hand. 

"Fuck, yeah,” Liev breathed. 

The kid was dripping a steady stream of precome that slicked up his hand, a smooth glide that forced Liev to release him long before he wanted to.  He wanted the skirt hot and begging for it, not blowing his load before they got started.  He let go, watching as the kid lost his rhythm, thrusting into open air with a bitten off whine as he met Liev's amused gaze. 

"Don't even know how much you want it do you, pretty boy." 
The skirt turned his head, long lashes sweeping low in a modest attempt to distance himself.  Beneath the plaid, Liev’s fingers were invasive and proprietary as he fondled his way to the young man’s entrance and probed the tight ring of muscle. 
The kid came to sudden life, thrashing and bucking, renewing his struggle for freedom.

“No…” as soft as it was lost the word trembled with uncertainty, shimmered with heat.

Liev braced an arm across his chest, pinning him to the wall, cocked hip trapping the open leg in place as he stabbed the tight ring of muscle and fucked his finger into blessedly tight heat. With a broken cry, the young man stilled, breathing hard. 

"That's it," Liev soothed, "nice and easy, sweetheart. Take it like a good boy." 

An inarticulate noise slipped through slightly parted lips as Liev pushed deeper.  He eased off the young man's chest and pushed the knee wide again, wiggling his buried finger experimentally.  Pouty lips parted, going slack as dark, kohl-laced, lashes framed a rolling gaze of conflicted, but undeniable, arousal.

Smirking, Liev swirled his tongue over a rose-colored nipple as he thrust gently into tight heat.  A small, barely there movement.  He held in check the urge to stab and roughly fuck the little hole, sensing his captive would continue to fight against him, no matter how subtle.  While there was pleasure to be had in that, Liev prided himself on reading people, figuring out how they liked to be touched.  His gut told him he could break this one with more careful handling.

He ran his free hand along the back of the elevated thigh, slipping under the skirt to palm the firm globe of the kid's ass, squeezing and fondling the muscle with circular caresses. Tiny, baby thrusts of his finger wrung hitching breaths from the open mouth as the tip of Liev's tongue grazed a rock hard nub. 

"Come on, baby," Liev coaxed, "let go. I know you want it." 

He could feel the fluttery tremble of strain and arousal around his finger as the kid hovered at the edge of surrender. 

A long, slow lazy thrust drew forth an unrestrained moan.

"That's right," Liev whispered, establishing a rhythm of shallow, shallow, deep penetration that had the kid trembling, hips hitching uncontrollably. "Had you pegged for a finger whore as soon as I saw you."

Stroking upward from that tight ass, flipping the back of the skirt up as he went, Liev smoothed his way to the center of the broad back.

"Gonna give you exactly what you need," he purred knowingly, "fuck that tight little hole until you beg me to let you come."
Liev flicked at the hard nipple again with the tip of his tongue, mouth hovering. He felt the staccato beat of the kid's heart beneath his splayed hand and dispelled any lingering illusion of choice with a firmly spoken order that chased a shiver down the delicate curve of spine. 

"Put your nipple in my mouth." 

Hand at his back as a guide only, the kid did as he was told, arching into Liev's mouth with a pained whimper that wasn't nearly so hot as the way his hips jerked and his hole twitched around Liev's finger when his tit was suckled. 

"Yeah, baby," Liev praised around the nub, tonguing it, finger hitching in and out, "just needed someone to tell you what to do, didn't you, sweetheart."

Liev sealed his mouth around pebbled flesh, working the nipple, laving and grazing, flicking and stabbing with his tongue. He teased the kid with the tip of his finger, barely there thrusts just beyond the ring of muscle that had his captive tilting his hips and wounded, animal-like whimpers falling from his lips. 

The cell phone in Liev's pocket vibrated.  He ignored it.  It stopped for a span of seconds and started in again.  The distraction broke through the cloudy haze of forced arousal, green eyes momentarily clearing, muscles tensing. 

Cursing, Liev withdrew his finger in one swift movement, stuck two fingers into his mouth to slick them with spit and without preamble or additional prepping shoved them deep into the kid's ass and crooked his finger.  The scream that tore free echoed through the hollow, empty space as the young man threw his head back, thrashing against the wall and biting his lush lower lip to keep any other noises from escaping. 

Retrieving his cell phone with his free hand, Liev flipped it open as it started to vibrate again. 

"Yeah," Liev's voice a curt, a breathless growl. 

"Sorry to, uh, interrupt boss, but I'm not sure how much longer we're gonna be able to hold the other one.

"What the fuck does that mean?"

Aiden cleared his throat.  "It means he's a fucking handful. He knocked Cutty out, broke Galen's nose and is currently pacing the room like a caged panther.  Wants to know where his brother is, and I quote, ‘Right the fuck now.’"

Brother, huh?

Liev eyed the beautiful stranger. The kid was a prime piece of ass. He wasn’t about to be rushed.  Using the pad of his finger he stroked the young man's insides, felt him shudder and buck, a small helpless keen making Liev's balls tingle. 

"Handle it," Liev ordered brusquely, "I don't want Dascen getting wind of this." 

He could tell by Aiden's sigh that it was going to be easier said than done. "I may have to tase him."

"Do whatever you’ve got to do, but keep it quiet." Liev ordered, flipping the phone shut without waiting for a response.     

"Now," he said smugly, gliding his fingers in and out of tight, clingy heat, "where were we?"

Liev tucked his hand into the small of the young man's back and pulled him in snug, lips hovering perilously close to that pouty mouth.

"Wanted to do this the second I laid eyes on you," he whispered.

The words weren't even fully out of his mouth and Liev was piston pumping his fingers into that sweet hole with fast, rough strokes, swallowing the cry of surprise and the pleasure-pained mewls that followed.

Liev pressed him into the wall as he surged against the initial intrusion.  Whimpering into his mouth the young man finally let go, tension bleeding from the lithe frame as he rocked forward with a fluid thrust.  Liev pulled back to watch the wrecked reaction as the skirt opened his leg and just took it, pouty lips bruised and parted, stomach muscles contracting, hips rolling quick and hard. 

"Fuck, yeah," Liev breathed, "such a hot little whore." 

His captive responded with a deep, guttural moan.

Liev tugged on his tit, felt the jolt in the kid's hips as they spasmed.  He played with the tender nub, kneading and tugging until the young man's panting grew erratic and there was a faint flutter of muscles around his finger. 

He went from fast and furious to full stop so fast that the kid couldn't control the whine that broke free. Tossing his head back and forth, hips still working he looked at Liev with a vulnerable mixture of dazed confusion as he caught his breath. 


This was a game to him. A perk to working a gig like this.  Liev enjoyed it.  He got off on it. The power, the control, working someone to the point of completion, making them beg and then leaving them unsatisfied...those were his kinks, what did it for him. It was rare that he had the desire to complete the cycle and actually stick his dick in someone.  It was there now.  The urge to just flip the bitch over and claim him was so strong that Liev had to put his head down and just breathe through it. 

He didn't have time for that, nor was it professional.  He was still on the clock after all. 

The kid was writhing on his fingers, small circular movements and whimpers that were driving him crazy. 

"Please..."  Emerald green eyes desperate and begging, unable to voice anything more, the whispered plea carried an entirely different meaning than when previously spoken. 

Liev scissored his fingers and savored the helpless gasp.

Fuck.  There was no way he was going to make his scheduled round of the grounds.  

Liev dropped to his knees, free hand pushing and holding the inside of the elevated thigh open in a bruising grip.  Hard cock straining against the course material of the skirt, the kid was probably expecting him to suck him off. 

Liev prided himself on being a little more unpredictable. 

Slipping beneath tented plaid, Liev mouthed at the kid’s balls, licking and bouncing them off his tongue before sucking them into his mouth.  He gave a small shake of his head, like a dog with a bone, tugging on the tight sac as he pumped into that sweet hole with short, sharp strokes.  The body above him shuddered with a sobbing groan of surrender as he cried out his release, balls pulsing in Liev's mouth.

He took the softening cock into his mouth, humming around the appendage, the tip of his tongue probing at the sensitive slit.  Thigh muscle trembled beneath his hand, faint and fine as he suckled spent flesh, drawing forth gentle thrusts and an almost delicate moan.

Fuck, he could play with the kid all night.

Liev thought about cuffing him to a more secure location to come back to later, but he knew all bets would be off once he was free of the pipe.  He'd been lucky to pin him down this time.  He'd have to give Aiden a call and transfer him to the holding room with his brother.  He couldn't let them go until the party was over and the paying customers had scattered.  As it was, Dascen was going to be pissed when he realized their current location had been compromised.   

Liev released the young man with a sigh, tongue swirling and tasting as he gleaned each honey-sweet drop of come from his genitals. While he'd love to stay and milk another orgasm from the kid, he had to get back to his rounds. He withdrew his fingers slowly, garnering a plaintive whimper from above. On impulse he pulled his personal card from a breast pocket and slid it into the hem of a white knee sock. 

If the kid ever wanted to pick up where they'd left off, he'd know how to find him.  Stranger things had happened.  It wouldn't be the first time someone had tracked him down for more after one of these encounters.  Liev ran a hand over his face and through his hair, slicking away stray drops of come, oblivious to the flickering lights as he tugged panties back into place and smoothed down the plaid skirt.  They flickered again as he stood but it was an old building with hijacked electricity so he really didn’t think too much of it. 

The kid's eyes flew open as Liev thumbed his lower lip.  He jerked away from the touch with a half-hearted glare.  Liev chuckled.  He looked like an angry kitten.  Granted, a wild, potentially dangerous kitten that could do some damage if he weren't temporarily declawed, but a kitten nonetheless. 

When the lights flickered yet a gain, a static energy filled air and had him on sudden alert.

"Fuck," his captive cursed quietly.

A loud murmur and then screams were heard from the main room. Liev took a step towards the sound. 

"It's too late.  You can't stop it," he informed Liev cryptically. 

"Stop what?" Liev demanded. 

"It's tied to Dascen.  It'll happen again." 

Liev reversed his direction at the inherent threat and took a step back towards the kid just as his cell phone vibrated in his pocket. 

"Dean!" someone called in the melee of panicked voices.

Liev remembered what the kid was sputtering when he'd first cornered him.  "You said you were here to help." 

"It's too late for that now.  It'll have to run its course."    

Unable to ignore the commotion in the main rooms and the non-stop vibration of his phone, Liev took a couple more steps, sparing a final glance over his shoulder for his captive.  Bare chested, hands cuffed over his head the young man followed him with an intense gaze. Lips swollen, legs parted with one perched on the crate, he looked ready and willing to be used all over again. Liev could still see his hand print on the inside of the fair skinned thigh.  An image that would keep him company for several nights to come. 

"What's your name, kid?"

Resignation quickly followed hesitation, voice rough and business like. 


Liev spared him a parting nod, knowing the kid would be long gone before he could return.  He disappeared into the flickering darkness, retrieving his cell phone in the process. 

He'd barely made it into the fray when a familiar figure in brown leather cut him off.  Where tall, dark and pissed off got a shot gun, he never knew, but when the young man caught a glimpse of his security insignia, the barrel took aim at his chest, dead center. 

Liev raised both hands in surrender, cell phone held high.  No words were exchanged.  He simply cocked his head in the direction he'd come from.  The kid was too anxious to get to his brother to bother with a stand off.

They ran in opposite directions.

They would meet again.  


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This was amazing. I have a flist member rec this to me and I'm so very grateful. Wow. My head is still reeling.

Thank you so much! Glad you enjoyed it :) It is always an honor to be recced!

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