Dean sat in the shadowy corner of the bar watching an older gentleman in another equally shady corner of the bar. He was pretty sure that he was being watched in return but the purple nurples he was interspersing with his beers seemed to have gone to his eye sight.
Dean grabbed a lanky teenager who was too young and new it to be in the bar and pushed him into a chair, 'sit here and don't move until I get back,' Dean ordered, he was on his sixth beer and had had twice as many nurples and had yet to visit the john. He blinked and the older gentleman seemed to vanish, he looked around the bar, from his vantage point he could see both the entrance to the bar and the doors to the bathroom.
'But-' the redheaded kid, who had been making his own way to the bathroom, squirmed as he protested but Dean just glared at him.
'And don't touch anything,' he demanded as he headed to the back of the bar, to unload his bladder.
'Mr. Winchester.' A gentle British voice announced from behind him as he washed his hands. Dean spun around as he tried to wrestle his gun from where it was tucked into his pants. Taking in the older gentleman who was now leaning against the closed bathroom door, Dean's cock unexpectedly twitched.
He glared at the offending appendage, never before had he ever shown any signs of interest in the same sex, until now. Though why it was this man Dean had no idea. He was easily as old as John would have been give or take a few years though he did have a full head of thick, salt and pepper, mostly peppered, hair and intense hazel eyes.
Suddenly Dean had been backed against the far wall of the men's room in this small roadside bar by this man, and as he was pressed against the wall he realised that while his assailant was about the same height as himself, he also came to notice that as he was pressed against the wall by this older, attractive man he was incredibly turned on even if his cock was slow to fill, that somehow made it better.
'It would seem, Mr. Winchester, that you are interested in more than just watching me.' The older man, who had a silver cross dangling in his ear, commented as he pressed his thigh between Dean's.
Dean groaned even as he corrected the man, 'it's Dean, Mr. Winchester...' he began as he rubbed himself against the thigh that was pressed against his crotch.
'Is your father,' the man finished for him as he attacked Dean's neck.
Dean chuckled and began to reply but it quickly turned into a moan as his Adam's apple was suckled.
The man cupped Dean's ass then and squeezed then the warmth that was pressed against Dean was gone and Dean groaned in disappointment.
'Get your stuff that the gawky redhead is about to piss on and meet me out front.' He commanded before he, with great reluctance, pulled himself away from Dean and headed out in to the bar.
'Wait,' he paused at the door, 'I don't even know your name,' Dean winced at how, wimpy and girlie it sounded. The older man simply chuckled,
'Tonight you can call me Ripper,' he replied before he left.
Dean took a few moments to compose himself by washing his hands again and splashing cool water on his face. He pulled open the door and smiled when he noticed that Ripper was downing a shot of something at the bar, apparently Ripper needed to bolster his courage for the night.
'Beat it kid,' Dean snapped as he stuffed a twenty into the kid's hand as he bounced in the seat Dean had all but tied him to. The kid bolted for the washroom.
Dean grabbed the bag that was under the table, apparently the spirit that haunted this particular bar only appeared on Mondays, Wednesdays and every third Friday and as it was a Thursday well, probably going into a second Friday Dean hadn't been expecting to see much.
Sam had insisted they at least check out before promptly being taken down by the flu. Some hunter he was.
He checked his bag to make sure nothing had been tampered with or stolen he glanced back to the bar to find that Ripper had left. He pushed his way through the crowd to the door. As he pushed it open he wondered briefly why he was going with this man. Then he caught sight of Ripper and he stopped wondering. There was something about the man and as he leaned casually against a support beam with a cigarette Dean had a sudden understanding that this man was offering him what he needed.
'I have a room across the way,' Ripper said not moving from his spot. "Across the way" was across the street and about a block down from the bar. Dean paled slightly.
'What room?' he asked.
'11, why?' Ripper asked in concern.
Dean visibly relaxed, 'because my brother is suffering from the flu in room 23,' he replied. The motel, Cloud Nine, was a three building complex with the main building being the front desk and a gym with an indoor pool. Two larger buildings, the rooms, flanked either side. They were two story buildings that each had 12 rooms. 11 was as far from 23 as you could get.
'Shouldn't you be..?'
'What playing nurse maid?' Dean asked, slightly offended. 'He's a big boy he can take care of himself, besides he prefers to suffer alone.' Dean replied with a roll of his eyes.
'Odd,' Ripper replied as he unlocked the door.
'Yeah well that's my brother,' Dean replied with a shrug.
'So Dean, tell me, why were you at Haven tonight?' Ripper asked pulling some more liquor from the well stocked mini fridge.
'My brother and I were on a cross country road trip, brotherly bonding and all that, and he got sick and I didn't want to get infected so I headed to the bar since it was closer and more lively then the one here.' Dean replied a little uneasily.
Ripper gently took the bag from Dean and tossed into a corner, 'You don't have to lie to me Dean, I already know what you and Sam do.' He said as he gently cupped Dean's cheek.
Ripper's thigh found its way back between Dean's thighs and Dean moaned as it was pushed into his rapidly hardening erection.
Dean's leather jacket thumped to the floor as both men toed off their shoes. Ripper guided Dean to the bed which he collapsed onto, and as Ripper held himself on his arms over Dean, he was suddenly overwhelmed with emotion and he did the only thing he could to quell them. Ripper firmly attached his lips to Dean's, who eagerly returned the attention.
They broke the kiss only to pull off their shirts, when it resumed Ripper trailed kisses down Dean's throat to nibble on his collar bone, Dean yelped with Ripper pinched his nipple only to kiss it as he laved it with his tongue.
Dean's hands traveled to settle in Ripper's hair, it was thicker and softer then Dean had initially thought it to be.
Dean shuddered as Ripper travelled down his chest to his abdomen and as he tongued his belly button, Ripper unbuckled Dean's jeans.
Dean moaned as the cool hotel room air hit his heated flesh, he wasn't wearing boxers, or briefs. Or boxer briefs. Or anything.
Ripper drank in the site of all of Dean as he tossed the clothing to the floor. 'Beautiful,' he breathed as he lowered himself to cover Dean to once again devour the younger man's mouth.
Dean moaned as he thrust up into the cloth covered erection above him even as he fumbled with the belt buckle. 'Up,' Ripper nudged Dean further onto the bed and followed him but settle between Dean's thighs.
He kissed Dean's left knee before trailing down his thigh leaving red bites along the way.
Dean writhed in pleasure is body vibrating in anticipation. He cried out wordlessly as Ripper engulfed his cock suddenly.
If he could have Dean would have curled around Ripper as the older man sucked greedily at the younger man's cock. Dean's hands curled into the man's hair and he was so focused on the sensations on his cock that he hardly noticed as Ripper began to stroke the flesh beneath his balls then began to massage the muscles around his entrance.
Dean exploded, flooding Ripper's mouth as the older man pushed a well lubricated finger into his hole. Dean whimpered at the intrusion, it didn't hurt, not like what he was expecting it to, it burned and it was uncomfortable having something in a place that shouldn't have something in it. He squirmed as the finger inside him moved. He then surprised them both by pulling Ripper up so he could kiss the man, tasting himself.
Dean was a whimpering pile of need as Ripper buried three fingers in his ass. 'Turn over,' Ripper commanded softly and Dean hastily complied.
'Rip, please,' he pleaded unable to keep from dropping to his elbows so his ass stuck up in the air for Ripper to appreciate.
He caressed the smooth globes before him before he knelt behind the younger willing man and position the head of his neglected cock at Dean's entrance.
Ripper caressed the muscled back as Dean pushed back against the hardness invading him, they both groaned as Ripper's cockhead popped into Dean.
Ripper pushed into Dean gently but the younger man still whimpered at the unfamiliar sensation of being filled and the fact that Ripper's cock was significantly larger than the three fingers had been. Dean clutched at the pillows under him and pushed back, it hurt, not as much as he had expected but there was still pain and then Ripper was murmuring to him. Gentle nothings as the man stroked his sides, his back, his chest, his cock. Finally Dean began to rock his hips against Rippers,
'Move damn it,' he growled as he tried to thrust against the cock inside of him. Ripper's weight, not much more than his own, possibly even less than Dean's was enough to keep him still. Ripper kissed the back of Dean's neck before straightening up and gripping Dean's hips tightly.
Ripper pulled out of Dean slowly before pushing back in with just as much control. That lasted for a about thirty seconds when Dean half moaned half demanded, 'harder, you jack ass!'
Ripper smirked and without speeding up his thrusts, he pushed in harder, rocking them both forward with the force.
'Ah! Faster!' Dean begged, on hand clutching the sheets below him while the other steady, or tried to steady them, on the head board.
As Ripper's thrust got faster and harder his hand, what had been on Dean's waist pulling him onto his cock travelled under Dean to grasp his leaking cock and began to stroke it in time with his thrust, or he at least tried to.
Dean's pending orgasm, which he had up until now been ending off with Herculean effort, crashed down around him. He moaned out a butchered Rupert and spurted onto the sheets and over Ripper's hand and as Dean's muscles contracted around Ripper he spurted into the tight channel that was wrapped around him, letting the walls milk his orgasm from him.
They collapsed to the side so to not land in the cooling puddle and panted in silence for a few minutes.
Dean, who was curled up on his side whimpered at the loss of heat at his back when Ripper left him. A few moments later Ripper returned and sat on the bed. He gently wiped Dean's limp cock before letting him roll onto his stomach.
'I didn't hurt you did I?' he asked in concern when he noticed a pink tinge to the spunk he was cleaning off of Dean's ass.
'No, not really, I mean I won't be driving long distances tomorrow or sitting for long period's time but I'll live. Besides I hear bleeding is common if it's your first time.' He added as he burrowed into the pillow as Ripper caressed his back and butt.
'Why didn't you tell me?' he asked half angry half honoured that his beautiful young man had let him be the first.
Dean shrugged, 'It didn't seem important Rup,' he pushed the soiled duvet away and tugged Rupert onto the bed. 'We can talk about it after we sleep.'
Rupert Giles sighed as he settled next to Dean who had curled into him, twining their legs together. He pulled the blanket up to cover them.
He gently stroked the head that was on his chest and, soon enough, he too was joining the younger man in sleep.
Standing in the door way were too transparent men, one about Dean's age the other older, possibly about Giles' age.
The younger of the two men smiled up at his older counterpart and snuggled into the man and the pair, clad only in towels, disappeared.