Title: What Might Have Been
Author's: Shilohx & DSM
Pairings: Jensen/Jared
Rating: NC17
Warning: Slash, Dean/Sam role playing, come thru penis plug, rimming, cock rings, mentions of past blood play, dirty bad wrong sex, and dirty talk.
Disclaimer: We don't own Supernatural, Jensen or Jared. We just spend a lot of time obsessing over them!
Summary: Five years after Supernatural ended, Jensen and Jared meet by chance in an airport. They discover that the passion between them is still alive. Is this a chance to discover what might have been or will they touch briefly and say goodbye.

A/N This fic was written as a special request for a close friend. XXX Shi

'For all sad words of tongue and pen, the saddest are these, what might have been.' John G. Whittier

What Might Have Been

Jensen watched the flight board change as all flights were canceled due to snow and fog. He groaned at the thought of spending the night at the Denver International Airport. Now he'd have to call Matt and give him the bad news. Then see if he could make arrangements for a hotel for the night.

Jared cursed under his breathe as the flights were canceled and he faced what he knew would be an unpleasant conversation with Gen. He hated the thought of making arrangements for an impromptu overnight stay.

Jensen and Jared were both hearing the same story. There were a couple of large conventions in town and the hotels and motels were booked. There was a bed and breakfast that seemed to have vacancies but it was supposed to be haunted. Jensen and Jared were several hundreds yards away from each other as they received this news but they both smiled and arranged to take the airport shuttle to the haunted bed and breakfast.

Jensen was arranging his luggage in he overhead compartment of the shuttle when someone bumped against him.

"I'm sorry, man." Jared turned to face the guy he had jostled while shoving his bag into the luggage bin. Green blue gold eyes met jade green and locked on as Jared's mouth opened in an oh of surprise. "Jen?"

Jensen was in shock. What the hell was Jared doing on his shuttle? "Jay, what are you doing here?" Jensen's tone was a little harsher than he had intended but what the hell, Dude!

"My flight was canceled same as you." Jared answered reasonably as they finished getting their luggage stored.

There were only two seats left in the shuttle so Jensen and Jared sat down side by side. Their shoulder's touched and both men felt a jolt of arousal. Jared couldn't stand the silence. "So, how's Matt? I saw his movie where he played the devoted husband who couldn't save his drug addicted wife. He was awesome! You guys have been together quite a while now."

"Matt's great. He's going to star in one of those Nicolas Spark's book based films. The fan girls will definitely be squeeing over it. He's got half a dozen, mostly nude, love scenes in it. We've uh, been together over four years now. How's Gen, Jerry and Kaylee?"

"Jer is already a little jock and he's only in kindergarten! Kaylee is a doll! She just turned four. She is my little angel." Jared smiled happily as he talked about his kids.

The conversation ran to talk of Supernatural where they had met and been lovers in what seemed another life time. They still kept in touch with several members of the cast and crew who had become an important part of their lives during those years. They joked about Jeffrey Dean Morgan being in a movie called Dead & Breakfast that they had watched during the first season.

When they arrived, Jensen made sure he let his hand casually brush Jared's hip. Jared gasped at the unexpected contact and got hard in his jeans. Jensen smiled at the reaction and thought to himself payback is a bitch.

Jensen and Jared waited patiently in line to check in hoping that no one would recognize them and start a fuss. They took in the hard wood floors, antique furnishings and family portraits. When they reached the desk, the lady informed them the only room left was in the attic. It had it's own bath and king size bed. Jensen said they would take it before Jay could register a complaint or comment.

"What is your name?" The fortyish red head asked him.

"I'm Dean Winchester and this is my younger brother, Sammy." Jensen answered with his trademark charming grin.

Jared's eyes widened and he licked his lips nervously but he did't refute Jensen's statement.

"Is there a bathroom on this floor?" Jensen inquired.

"Yes just go right down the hall. It's the third door on the left." the lady answered returning his smile.

"I'll meet you in our room, Sammy." Jen said with a wicked grin.

The look in Jensen's jewel toned eyes made Jared's heart rate speed up and his palms get sweaty. He simply nodded at Jen not trusting his voice and headed for the stairs.

Jensen ducked into the kitchen on his way down the hall and searched in a few drawers til he found what he was looking for. He chuckled darkly, concealed the item and headed up the stairs to join 'Sam'.

When Jensen got in the room, Jared was putting his things in the left hand bed side table. Jen smiled and went to the right side table to store a few items he might need later including the one from the kitchen. This all felt so familiar and comfortable like nothing had ever changed between them. When they finished unpacking Jensen set up his ipod and 'Highway to Hell' filled the air in the room.

Jared turned, a smile on his face and Jensen was right there. Jen reached his right hand up and around Jared's neck and pulled him in for a kiss. He tilted his head just right and sucked on Jay's lips a moment before biting down making Jared gasp sharply. Jen took advantage of his parted lips and plunged his tongue inside. He licked in deep feeling him out and rediscovering Jay's taste. Jared moaned and arched his hips against Jen's. God, he had missed this and fuck he's harder than he's been in years. Sex with Jen had always been the ultimate pleasure. He still fantasized about it when he jerked off in the shower.

Jensen pulled back from the kiss. His liquid emerald eyes laser locked on Jay's shimmering blue green gold and pure sexual heat sparked between them. They had both dreamed of being together like this again. Each of them had pretended with their partners that they were fucking each other. Now, here they were face to face with their fantasy and it was perfect.

Jensen captured Jared's lips again as he reached under Jay's shirt to touch the toned flesh beneath. Jay tugged on Jen's sweater resenting anything being a barrier between him and honey toned freckled flesh. "Too many clothes." He panted as he lifted his head and tugged at the sweater.

"Let's strip and move this party to the bed." Jen suggested with a wicked grin already unzipping his jeans.

Jared pulled off his clothes and tossed them carelessly in the corner. He crawled up the bed and laid in the middle propped up on his elbows. His hungry eyes were locked on Jen as he watched him undress. Jensen stood at the end of the bed looking down at Jared spread out before him looking like the garden of eden. Guess that makes me the serpent Jen thought and smiled wolfishly. Jared was almost mesmerized by watching Jensen stroke his huge cock as he stood on display at the edge of the bed. He's a fucking work of art Jared thought and felt himself grow impossibly harder. He'd never in his life wanted anything as bad as he wanted Jen at this moment.

"Fuck me, Dean. Open me up with your huge cock and make me beg to come." Jay knew Jensen wouldn't be able to resist that.

"You always were a big cock whore, Sammy. I've got some toys in my party pack to make this more um stimulating." Jen grinned darkly and walked to his side of the bed. He got out some items, did something Jay couldn't see, then turned back to the bed. "Put this on, Baby."

Jay took the leather cock ring and snapped it on. His heart was pounding with anticipation as he saw Jen hold up the come thru penis plug. Jen snapped on his own cock ring then crawled up the bed with the plug that he had dipped in ginger oil and lube. "Oh, Sammy, have I got a treat for you."

Jen kept his eyes locked on Jay's as he swirled his tongue over the head of his cock and moaned softly. He lowered his head teasing the hot spot under the crown twisting his hand on Jared's rock hard shaft. Jay was glad he had on the cock ring cause fuck he was already on the edge of shooting his load into the perfect wet heat of Jensen's mouth. Jensen worked him a bit longer before pulling off so he could insert the come thru penis plug. He worked it in with the lube and waited for Jared to respond to the feeling of the ginger oil.

"Jesus fucking christ, Jen! It unhh... God … burns but fuck... is good..." Jay felt like he was losing his mind as the pulsing heat radiated from the plug in his throbbing prick. It felt fucking amazing. Jen had learned some new tricks. Damn, he loved Jensen's party bag!

Jen moved up and kissed Jay like his life depended on it. Their tongues tangled and they each sucked on the others tongue as their hands rediscovered all the dips and curves of each other's flesh. Their cocks rubbed against each other and they groaned into each other's mouths swallowing the sounds of their arousal. When the need to breath became overwhelming, they pulled apart. Jensen's eyes were totally black now with lust. They were both panting and Jen moved back, grasped both their cocks together and started to jerk them almost violently.

"Fuck, Jen, the burn. Oh God!" Jay's head was thrown back, neck arched beautifully, body bucking and writhing under Jensen.

"How bad do you want this, Jay?" Jensen growled as he continued pumping their throbbing cocks.

"What?" Jared looked at Jen confused.

Jen let go of their dicks and slid off the bed. He reached in the bed side table and pulled out the Filet knife he had borrowed from the kitchen. He climbed back on the bed and straddled Jay's thighs. Jay's eyes locked on the dangerous sliver sheen of the knife's blade.

"Remember, Jay? How I used the blade to trace the dips and ridges of your delectable abs. Then I would lick up the blood and you would kiss me like you wanted to devour me?" Jen's voice was velvet over steel.

Jared licked his lip and his eyes left the knife to stare into Jen's looking deep inside him. He knew if he refused the knife, play time was over. He wanted the knife but how the hell could he explain the marks when he got home? Jen moved a little causing friction against Jared's leaking prick and banishing all coherent thought from Jay's mind. He had to have this, consequences be damned!

"Do it, Dean. Cut me!"

"That's my boy." Jen smiled approvingly. "Close your eyes, Sammy."

Jensen reached over and put the knife on the table. He had never intended to use it. He just needed to know that Jared would have let him. He leaned down and traced Jay's abs with his tongue. Jared gasped and arched up wondering where the sting of the blade was. Why Jen was using his tongue instead. Jensen took his time licking, nipping and tasting Jay's skin.

"Put a pillow under your hips." Jensen commanded and Jay quickly complied.

Jensen popped the top on the strawberry flavored lube and coated his index finger. He knew Jared was going to be tight. It had been years. He teased at the pink bud of Jay's opening loving the noises Jared was making. He pushed the tip of his finger in the tight heat and Jay immediately pressed down on his finger.

"Such an eager cock slut, Sammy. You haven't let anyone else fuck you since your bachelor party, have you?" Jen purred as he slipped a second finger in opening Jay up more.

"Only ever let you fuck me, Dean." Jay moaned pushing down harder on Jensen's fingers wanting more.

Fuck, Jen thought, he deserves a reward for that. He dipped his head and pressed his tongue into Jared remembering how much he loved that.

Jared's whole body bowed at the exquisite feel of Jen's tongue in his ass. It was one of the things he dreamed about on a regular basis and would wake with a raging hard on at the memory. His cock was weeping out of the penis plug and dripping down his stomach. Jensen continued to tongue fuck him and Jay thought he would lose his mind at the sheer bliss of it.

Jensen pulled away and looked at Jay taking in his weeping cock, flushed face, heaving chest and eyes blown black with desire. Damn, he's gorgeous like this. He had wanted to torture Jay a bit longer but he needed to get inside him right the fuck now!

He got in position, leaned in and kissed Jay tenderly totally opposite of what Jared was expecting. The loving soft kiss totally disarmed Jay and he let go of the last of his defenses. Jensen felt it happen and pushed inside the velvet crush of Jay's ass.

"Oh, fuck, Dean!" Jay cried out at the too full feeling and arched against Jen.

"It's okay, Sammy. I got ya, Baby." Jensen pushed steadily til he was all the way in then he paused to let Jay adjust to the huge cock in his tight ass. He kissed, licked and nipped Jay's long throat to distract him.

"Move, Dean. Please." Jared's voice was hoarse and shredded with emotion.

Jensen pulled out and thrust back in hard making sure to nail Jay's sweet spot. He was rewarded with a high pitched keening and Jay moving his legs up against his chest so Jen could go deeper. Jensen knew exactly how Jay liked to be fucked and he started to drill into him hard and fast nailing his prostate with each deep thrust.

Jared's body was like a live wire beneath him shivering, shuddering, thrusting up and against him. Jensen was glad he had the cock ring on or it would have all been over far too soon. He continued to pump into Jay loving the feel of him clenched all around him like a vise so damn hot and tight. He braced himself on one arm and reached between them to stroke Jared's red swollen prick. Jared was mumbling incoherently and overwhelmed by all the sensations Jensen was causing to pulse through his body.

"Dean, need to come. Please..."

"Come for me, Baby." Jen purred as he unsnapped the cock ring and aimed Jay's dick towards his face. Jay watched as his release pumped out of the penis plug and into Jensen's mouth. Fuck that's hot he thought as his body convulsed around Jen's cock. Jensen's rhythm faltered for a moment. He released Jay's softening dick and reached for his own cock ring to release it. He came instantly filling Jared's tight ass with his warm spent. He could feel some of Jay's come dripping down his chin.

"Lick me clean, Sammy."

Jay leaned up and licked all the come off Jen's face. Then, he kissed Jensen sucking the taste of himself off of his tongue. They drew apart to breath and Jared started up at Jensen's gorgeous face. "Dean, you are awesome."

"Yeah, I know, Sammy." Jen answered in is best cocky Dean voice. "Time to hit the shower."

"I think I'm just gonna rest." Jared was totally boneless and ready to sleep.

"You've been having straight sex too long. We're not done. You aren't gonna just roll over and go to sleep on me." Jensen reached down and slapped Jay's cock twice. "Time for round two in the shower, Baby." He was pleased that Jared's dick was already getting hard again.

"I can't fucking believe you slapped my cock." Jay stared at Jen and shook his head. He noticed his dick was standing at attention and hadn't minded the smack at all. Damn, how did Jensen always do this to him.

"Come on, Bitch. Let's get your fucked out ass into the shower."

Jen adjusted the water temp and turned to pull Jay up tight against him kissing him deeply. "Tell me you love my cock, Sammy." Jen licked and kissed down Jay's neck stopping to pay attention to the pulse point that he knows makes Jared crazy.

"Love your huge cock, Dean. I want you to fuck me again. I need it, Dean. Please, fuck me." Jared's voice is thick with need and hoarse with lust.

Jensen spun Jared around and Jay braced himself against the tile wall of the shower. Jared stuck out his ass out in invitation and spread his legs wide.

Cock in hand, Jen presses the head into Jay's tight hole. He grabbed onto Jared's narrow hips and eased slowly farther in.

Jared whimpered and pressed back against Jensen loving the feel of Jen inside him.

Jen kept pushing steadily and then he's all the way in. Jared's eyes were screwed shut, his mouth open and breathing hard.

Jensen pulled out slow and then thrust back it quick and deep. Jared cried out, his voice breaking as he pushed back to meet Jensen's thrust. Jen changed the angle and rocked his hips forward nailing Jay's sweet spot dead on.

Jared 's eyes shot open and he keened, fingers clawing at the tile. Jensen set a merciless rhythm hitting that same spot over and over. He drilled into the exquisite heat of Jay's ass with abandon chasing his orgasm.

Jared became frantic, muscles clenching and hips bucking as he mewled and shuddered. Jen reached around and started to jerk Jay's cock in time with his thrusts. Jen's cock was crushed in the velvet heat of Jared's ass as Jared came with a shout against the tile wall. Jen can't hold out any longer and let go filling Jay with his come. Jensen's entire body convulsed with the force of his orgasm and he leaned unsteadily against Jared's back while he recovered.

When they finished their shower, Jensen led Jared to the couch in their room and asked him to sit down. Jared did as he was told wondering what Jen had in mind. Jen straddled Jay's thighs and sat on his lap. His hands grazed down Jared's chest making his nipples erect and leaving a trail of heat in his wake. "You've been very good tonight, Jay. You deserve a reward." Jensen leaned in and licked deeply into Jay's mouth capturing his tongue and sucking hard on it. "I'm going to let you finger me open and fuck me."

Jared's dick twitched and his heart pounded in his chest. He would never have asked for this. He knew how rare it was for Jen to offer this and it was truly a gift. "God, Jen want that so bad. Thank you."

Jensen smiled and Jared thought again how damn beautiful he was as Jen handed him the lube. Jen moved off his lap and got on his hands and knees on the couch. He slid his fingers along the crack of Jensen's ass and then pushed two inside the tight entrance. Jensen squirmed and hissed at the feeling. Jared pushed them in and out, trying to make room for his eager cock. He scissored and crooked his fingers until he could squeeze his tongue between them and lick deeply inside Jen. Jensen made a needy kitteny sound that went straight to Jay's throbbing cock. Jay fucked him with his tongue reaching deep inside vibrating and humming against Jen's velvety muscular walls. Jen keened and pressed back against him.

"Fuck me, Sammy!" Jen ground out his voice ragged and harsh with lust.

Jared lined up against Jensen's opening and pushed in hard and deep. Jen started to make this keening sound, still twisting his body like Jared's cock is driving him crazy. Jared grabbed Jen's slim hips in a bruising grip as he thrust deeper. Jen felt the burn of the thick shaft stretching him. There was some pain but it felt amazing too, and he pushed himself back, taking Jay's cock even deeper. Jared watched Jen fuck himself on his dick and moaned loudly. It was mesmerizing and beautiful watching his cock disappear into Jensen's hot ass and Jared was transfixed. Jensen's hands clawed into the couch and he arched his back. Jared rammed deep inside, loving the heat and tightness squeezing his cock like a vise. He shifted his angle a little, in order to get a better hold, and managed to slam right up against Jensen's prostate. Jen keened and his eyes were dark and liquid with desire. Jared thrust faster and harder, reaching a hand around and pumping at Jensen's dick. Exquisite sounds started pouring out of Jensen soft, desperate growls and groans. Jen pushed back onto Jared's cock then thrust forward into his fist. His head snapped back, as he gasped for air. He felt the liquid heat building in his spine. He cried out Jared's name as he came hard all over Jay's hand and dripped onto the couch cushion beneath him.

Jared kept pumping hard and deep and soon his orgasm ripped through him whiting out his vision and scrambling his brain. He slammed his body, full-force into Jensen, as he shot his seed deep inside him. Jared leaned forward against Jen's back, gasping for air, breathing hard against the hot, wet skin. When they recovered enough to move they took another shower.

As they were leaving the bathroom, Jen turned toward Jay, "Now that we've both been proper fucked. It's time for a well earned sleep."

"Amen to that, Brother." Jay said and smiled contentedly.

Jen snuggled up to Jay's broad back and spooned him as he had when they belonged to each other. It still felt perfect and right. They locked together like two pieces of a puzzle. He kissed the back of Jay's neck like he had done hundreds of times before in the wee hours of the morning. "Good night, Bitch."

"Good night, Jerk." Jay was smiling as he fell asleep in Jen's warm embrace.

A jangling sound jarred Jensen out of sleep and he growled as he reached for the phone. "Yeah."

"The airport called. The shuttle will be here to pick you up in an hour." It was the red head who had checked them in yesterday.

"Okay." Jen hung up the phone and turned over to find Jay staring at him. He relayed the phone conversation.

"One more time, Jen. Please." Jared's green blue gold eyes seared him.

"Open your mouth and suck my fingers. That's the only lube I'm going to use." He knew Jared would be feeling him for a week after this.

Jared took Jen's fingers in his mouth and sucked them hard. When they were dripping wet he released them, laid back and spread his legs wide pulling them up against his chest.

Jen ran his fingers along the crease of Jared's ass, he found the opening, and gently eased one inside. Jared pressed down onto it, taking it in deeper, not waiting for Jen. "More. Harder. Please."

Jensen moaned, added another finger, twisting and pushing them inside the tight heat, even as Jay thrusts his hips down again and again onto them.

"Now, Fuck me now!"

Jen shoved his rock hard dick into Jared's ass not stopping until he was buried to the hilt inside. He grabbed onto Jay's dick running his fingers up the shaft in a slight twisting motion, and then back down again. He rocked his sinuous hips and did a small twist with each powerful thrust. Jared gasped his hips thrusting forward into Jen's fist.

Jen locked his other hand around Jay's hip, pulling him back then holding him still. He thrust a couple of times even harder into Jay's tight, hard ass. Jared grunted panting and sweating. Jensen kept twisting and stroking his fingers up and down Jay's shaft making him whimper, that was it for Jen. He drilled even harder into Jay for a moment rocking his body with each thrust. Jay came with a shout clenching down on Jensen's cock like a velvet vise. Jen thrust a couple more times before surrendering to his own orgasm. They collapsed together on the bed holding tight, knowing their moment was ending and they would be going back to the real world where they led separate lives.

They said their final goodbyes at the terminal. Each of them knowing this might well be the last time they would ever see each other. They was so much in each of their hearts that neither one could or would say. They boarded their flights and waited for take off. Jay got out his wallet and reached into a well hidden back compartment. He kept his three favorite pictures of he and Jen there. He stared at the photos with hungry eyes as he relived every moment of the time they had spent together.

Jen settled into his seat with a heavy heart. He fired up his ipod and chose Little Texas 'What Might Have Been'. He closed his eyes as the words went straight to his broken heart and a single tear rolled down his freckled cheek.

What Might Have Been song lyrics

(Porter Howell/Dwayne O'Brien/Brady Seals)

Sure I think about you now and then
But it's been a long long time
I've got a good life now I've moved on
So when you cross my mind

I try not to think about
What might have been
'Cause that was then
And we have taken different roads
We can't go back again
There's no use giving in
And there's no way to know
What might have been

We could sit and talk about this all night long
And wonder why we didn't last
Yes they might be the best days
We will ever know
But we'll have to leave them in the past

So try not to think about
What might have been
'Cause that was then
And we have taken different roads
We can't go back again
There's no use giving in
And there's no way to know
What might have been

That same old look in your eyes
It's a beautiful night
I'm so tempted to stay
But too much time has gone by
We should just say goodbye
And turn and walk away

And try not to think about
What might have been
'Cause that was then
And we have taken different roads
We can't go back again
There's no use giving in
And there's no way to know
What might have been

No we'll never know
What might have been