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Carry On My Wayward Son	By : Danyealle Category: Supernatural > Slash - Male/Male > Dean/Sam Views: 6695 -:- Recommendations : 2 -:- Currently Reading : 1
Disclaimer: I don’t own Supernatural, people with a lot more talent than I do have that honor. Nor do I make any kind of money off this story. I’m just playin’ with the boys. I promise to put ‘em back when I’m finished with them.

Chapter List
- 12
- 13
- 14
Chapter 13

Living easy

Loving free

Season ticket for a one way ride

Asking nothing

Leave me be

Taken everything in my stride

Don't need reason

Don't need rhyme

Ain't nothin' I would rather do

Going down

By the time

My friends are gonna be there too, eh

I'm on a highway to hell

-Highway to Hell

-AC/DC

(Tags: mutual masturbation, toys)

To say Dean was ecstatic about what he had just heard was the understatement of the century. Hell, despite it being completely out of character for him, he wanted to get up and do a happy dance but didn't. Nevertheless, he couldn't keep the excitement of getting Sammy to agree to what he wanted from growing. Along with that, a certain part of his anatomy was instantly hard. It had happened so fast that he was sure that he should be light headed from the speed his blood had surged southwards. Then, that part of his brain that dealt with such things, began to heartily lobby for something, anything, to go on right away. After all, he had been in a state of extreme sexual frustration since this whole thing began so, maybe, whatever would happen would alleviate some of that. The issue with that, though, was getting Sammy to agree. Hell, he was still fairly distraught by the whole situation and Dean was sure more fallout was coming his way over agreeing. But, dammit, he wanted this!
Shifting around, he tried to conceal the not so little problem in his shorts from the camera, no easy feat, and looked at the screen. Sammy was still just sitting there on the edge of the bed with his head down. From the look of the way his shoulders were moving, he was breathing fairly heavily. That was enough to tell him that his little brother was over thinking once more and second guessing what he had just done. No, that wasn't something that he could allow to go on. If he did that meant the situation was going to get worse than what it already was. Oh no, that wasn't going to happen! Things were bad enough as it was, he didn't want to see how bad worse got!
Propping himself up on his elbow, Dean looked, intently, at the screen then said, “Sammy...” to get his brother's attention. When the younger Winchester sibling looked at him, blushing, panting and generally looking panic stricken, the older one said, “Dude, calm down! Just don't go making yourself insane over this!”
Licking his lips, Sam shook his head then replied, voice uneven, “The impact of what I just agreed to is hitting me so it's hard not to panic, Dean!” Oh yes, on his end, there was panic! The ramifications of what he had agreed to give a shot was overwhelming him to the point that it was hard to breathe. The sheer wrongness of it was engulfing him like a tidal wave, making his stomach clench tightly and a sour feeling fill it. But he would admit, to himself anyway, that there was relief and excitement involved as well. He just wasn't going to say that out loud to Dean. On the flip side, though, those things also seemed to be fueling the guilt higher. Ugh... paradox! He didn't need this right now.
Nodding, at least understanding where his brother was coming from, Dean cleared his throat then said, “Gotcha, dude.” If it was anyone else, he would just tell them not to think about it but with Sam, he knew it wouldn't work. Hell, geek boy over thought everything. It was probably a physical impossibility for him not to over think. Seriously, his big brain needed to give him a break once in a while and let him just go with the flow. But, since that, obviously, wasn't going to happen tonight, it was time to work with it. Shifting, ensuring that his erection was still out of sight, he sighed then said, “Alright, dude, let's find something to talk about alright? Maybe that'll distract you.”
“I doubt it, Dean,” Sam snorted, looking at the screen. “Considering there is no hiding your 'enthusiasm' for this no matter how much you shift around, I can only imagine what the conversation will be about.”
Alright, it was now Dean's turn to look sheepish, giving a slightly uncomfortable grin. He guessed he didn't do as good a job at hiding it as he thought. But, with that a thought hit him and his grin grew. Teasingly, he said, “Well, you can't be that uncomfortable with it if you're looking, bitch!”
“Jerk,” Sam replied automatically, then looked away, flushing just a little, giving a sour look. “It's kinda' hard to miss, Dean!”
Since his brother had obviously seen what he had been trying to hide from him, Dean reached down and adjusted his erection into a more comfortable position then shifted slightly. “Can't help it, Sam. You should know that. Pulling the bitchface isn't going to do any good either.”
Keeping his eyes averted from the screen, Sam just nodded, swallowing thickly. Though uncomfortable with the whole thing, he couldn't help that his cock too was starting to stir at the possibilities of what could come from him agreeing. Though it appalled him, he couldn't help it. There was something thrilling about the whole thing in a way things that were taboo seemed to be, well, some of them.
Keeping an intent eye on his brother, Dean couldn't help but grin at the fact that Sam couldn't seem to look at him and the fact that there seemed to be a tent growing in his little brother's shorts. That was a good sign if there ever was one! Now to just shift the topic enough that direction to work with it. He wasn't sure what they could do over the computer to get some satisfaction but, maybe, they could do a mutual show together? That would work and relieve some stress.
Thinking it over, he thought he had a way to work with it. Clearing his throat, he said, “Sammy, tell me, dude, how different is sex with a guy than a girl?” Wasn't the best way to go about things with an opening line but it might get the ball rolling. Quickly, he added, “You're the one that's done this before, not me. That's the reason I'm asking.”
Brow furrowed, Sam looked up at the screen to see if Dean was pulling one of his not funny jokes on him. But, from the look on his brother's face, he seemed to be serious about the question. Though the topic was slightly uncomfortable, he shrugged then said, “Not much different. If you've tried anal with a girl before then it's about the same. Just the stimulation has to be done differently is all. If you tend to go with what you like when it comes to what you find arousing, you'll do fine.”
Nodding, absorbing that and filing it away, Dean replied, offhandedly, “Yeah, done anal before. So, everything with that is basically the same? I mean, girls and guys are build differently so are there some things you have to do differently?” Sure, he knew anatomy and all that it was just the fact that he hadn't gone down this road before and wanted to be certain he knew the best he could before he jumped in. Preparation is always the key to being good at what you do.
Scooting up on the bed, Sam leaned against the wall that it was up against, feet flat on the bed, knees bend then, loosely, clasped his hands around his bent legs, looking at the screen. Clearing his throat, he said, “It's pretty much the same thing, Dean. Yeah, the anatomy is different but the act is not much different. The only thing is that most try to hit the prostate when doing it because of the sensations that it causes. But it's not hard to do as it has more to do with just finding the right angle is all. With that, it depends on the person.”
That Dean filed away for future usage. He hadn't ever let anyone go there with him even though a couple girls had wanted to try. But he had heard, especially after finding that chatroom, the intense sensations that it caused. Nodding, he replied, tone thoughtful, “Since I haven't done that before, how can you tell? Do you know what it feels like, I mean when you're looking for it?”
Giving a wry grin, Sam chuckled softly, “When you hit it on your partner, you'll know, trust me! They actually call it the male g-spot to give you an indication of the reaction. The sensations of it being massaged is unlike anything else in the world and the reaction you get is a dead giveaway. As for what you're looking for... it's just a small bump in the anal canal, about the size of a chestnut, nothing more than that. It's about two inches in for most.”
Dean was taking some serious mental notes on this part. He was a master at finding the female g-spot and giving chicks the ride of their life. If a man's reaction to this part was about the same he was going to become a master of that as well! Glancing back at his little brother, he shot a bit of an evil grin then asked, smoothly, “I take it you've experienced this, Sammy?”
Grinning in an embarrassed way, Sam nodded but said nothing.
Chuckling once more, Dean shook his head. It was obvious his little brother had with the way he had fucked his own ass with his finger that one time on cam. But that raised another question, one he felt he had to know since Dean Winchester didn't bottom for anyone; male or female! Yeah, he had let girls ride him but he was always the one in charge when they did that, directing what they were doing. He wasn't about to bottom this time either. “Another question, Sammy; you top or bottom?” The answer to that question was going to determine how smooth this went for him and give an indication of how much work he had to do.
Clearing his throat in an uncomfortable, and slightly embarrassed way, Sam replied, looking away as he did, “Mostly, I bottom. I tend to gravitate towards the more dominant types so that lends to that.”
Okay, that couldn't have gone better if Dean had manipulated it before hand! It was absolutely perfect! All but rubbing his hands together in glee, Dean nodded but didn't comment on that, just saying, “Yeah, more of a top myself when it comes to things. Of course, that's been all women up to this point but I imagine it'll be the same thing with this.”
For Sam, that sent a lightning bolt of lust straight southwards to his cock. It was wrong, he knew that, but he couldn’t help it. Scrubbing a hand over his face, he groaned softly as all those fantasies and dreams he had been having seemed to surge back to him in one huge wave. Within seconds, he was fully hard and throbbing. Wiggling around on the bed, he crossed his legs, hoping like hell that Dean hadn't seen it.
As a hunter, Dean always prided himself on being the best there was. His observational skills were above and beyond most others he knew, especially beyond mere 'straights' that wandered around with their head up their ass for the most part, not seeing what was in front of them when it came to the strange and unusual. That was something that one couldn't just 'turn off' when he was on downtime, no matter how hard you tried. It was always there, whether he wanted it or not. With that in play, he couldn't help notice the boner from hell that Sam was sporting at this point. It didn't help his own in the least. In fact, it was beginning to hurt at this juncture of the night. Relief was needed or he was sure he was going to be in agony shortly. Problem was how the hell to go about this! Scrubbing a hand over his face, he tried to think. As the blood had left the upper head for the lower one, his thought process was muddled. This was a situation that involved tact and dancing easily, something he wasn't good at to start with so it was fairly certain that he wasn't going to be good at it at this point. Shit!
Sitting there, staring at the screen, more specifically what he could see of his little brother's crotch, he tried to come up with something but the only thing that came to mind was just do what he did best; go for it and be blunt. Shit, that's what Sam was used to with him so he didn't think that he would expect some kind of great courtship or wooing, he knew him too well for something like that and it wasn't something he did anyway with anyone. He figured, though it was a risk, that he should just go for it and deal with the fallout as it came. That was probably going to be what worked best for him. It would also give him an idea of what he had to work with when it came to getting there besides the obvious discomfort his brother felt. That was better than what he was dealing with right now, the not knowing what to go with or where he stood . Deciding that was the best course of action there was, he gave an internal nod then went for it.
Shifting around, he sat on the edge of the bed, legs spread, elbows on his knees. In that particular position, there was no way that one couldn't see his obvious erection tented out the front of his boxers. Looking at the screen, he grinned that grin that women seemed to love when he was chasing tail, the one that he had the most success with, then said, smoothly to stamp on whatever nervousness was there, “Shit, Sammy, this talk has got me hot as hell!” Stopping there he waited for his little brother's reaction to it.
Looking at the screen, Sam's attention was immediately drawn to the huge tent in Dean's boxers making him quickly face away and his own cock give a slow throb. Swallowing thickly, a riot of images ran through his head of what he wanted Dean to do with him, making him squirm on the bed. As a way of an answer, all Sam did was nod, not trusting himself to say a damned word.
Alright, Dean would admit that was a good reaction. As least Sam didn't tell him to go to hell or stop it. That meant he should be pushing forward a little. Attempting to decide how to proceed, he quickly came up with what he thought was the best plan for it. Trying not to grin, he coughed in a nervous way then said, “Look, Sammy, I got to see a couple of your shows, right? How about this... I put one on for you. You can watch or join in if you want. Work for you?”
Almost panic stricken, Sam glanced at the screen then stammered out, flushing bright red, “No, really, Dean, you don't have to do that, dude! It's fine!”
Seeing his brother, after what he had observed him doing online, stammering and acting like some innocent boy that was embarrassed by sex made Dean want to burst out laughing. But he didn't. No, doing something like that would just aggravate the situation. Keeping a calm, neutral tone, he shook his head then told him, “No, dude, it's alright! I want to! Just sit back and enjoy the show.” Before Sam could even form a protest to it, trying to wiggle or back out, Dean shimmied out of his boxers then leaned back on the bed, propping himself on his elbow so that he could see the screen then wrapped his hand around his cock and began to stroke it. Groaning, eyes sliding partially shut, he began to pant almost immediately, the sensations of his hand working on his cock making his skin prickle and a red flush spread across is body. Making sure to keep an eye on the screen, he gritted his teeth and moaned. As turned on as he was, this normally wouldn't take long but he wanted to stretch it out to entice Sammy into joining him.
Now, Sam was no fool. He had known his brother long enough to be able to pick up on a manipulation when he saw one. And he was seeing one right now. This was his brother's backhanded way of enticing him into joining. But, though he knew he shouldn't fall for it, he was. There was something about sitting there and watching Dean stroke himself that was more arousing than most things he had seen in his life. Sure, over the years he had seen his brother naked, many times. But this... this was far different. This was something that was, well, wrong! He knew that! No one had to tell him so. But he couldn't help himself, his eyes were glued to the screen, watching Dean stroke himself and was more aroused by it than almost anything he had seen in the past. Shit, it was making his already hard cock throb even more! Swallowing thickly, his eyes followed the movement of Dean's hand as he jerked off, resisting the urge to reach down and do the same thing as his body was demanding. He just didn't think he would be able to do that in front of his brother, knowing he was watching was all. But damned if it wasn't hot to watch!
Though groaning and wiggling around from the sensations his hand was creating, Dean didn't allow himself to get lost in that, ensuring that he kept an eye on the screen and Sam. From the look on his brother's face and the fact that Sammy was staring intently at what he was doing, he was certain that it would work. His baby brother was just going to need a nudge in that direction was all. And he thought that he might know what would work.
Shifting around slightly, he propped his feet up on the edge of the bed then spread his legs wide, giving Sam the best view he could. Lifting himself up more, bracing one palm on the bed, he began to fist his cock faster. Panting, he stared at the camera then, lowering his voice to that deep, husky growl so many females seemed to like, asked, “Tell me, Sammy, you been dreaming and thinking of me fucking you with this? Feeling my cock deep in your ass? Was that what was driving you nuts?” Alright, he would admit that the erotic dirty talk wasn't his strong point but as blunt as he was about things he thought it might work. Before giving his brother a chance to answer, he panted out, “If it's what you want, I'll do it for you, all you like. Just tell me and you can have it!”
Unable to stop himself, Sam groaned loudly and muttered a soft 'yes' though he hadn't meant to say it out loud. His cock was leaking pre-cum into his boxers at a steady rate by this point. As much as he had thought about this since Dean's admission to him, the fact was watching it was far better than anything he could have imagined! Reaching down, he palmed his cock through the thin cotton, shifting his aching flesh to a more comfortable position. Though he wanted to take it out and get some relief, he didn't.
Keeping an eye on the screen, Dean couldn't help but grin at the soft admission from his brother. That was good! It wouldn't take much more nudging to get him going the right direction from here. He could, and would, be doing that! Throwing his head back and groaning, Dean hissed through clenched teeth as the sensations in his cock grew more intense and liquid lightning seemed to be dancing down his spine. Already his balls were throbbing, telling him his completion wasn't going to be too far off no matter how hard he tried to keep it at bay. Taking his hand away, he panted heavily then looked at the cam, saying, “Sammy, I want to see you do this too! Come on, dude, put a show on for just me and use a toy so we can cum together.”
That was a bad idea Sam's brain screamed, telling him that it was a road to hell if there ever was one. But as aroused as the younger Winchester was he was doing a good job of ignoring it. All he seemed to be able to think about was the fact that he was so hard it ached and his balls were feeling heavy, the kind of thing that happened when he was to the point he needed relief of some kind. Then another part of his mind, something traitorous and he was sure the section that had been chucking up the unwelcome fantasies and dreams pointed out that he had done this on cam to where Dean had seen it already. Why not do it again? But, really, he was trying to ignore it. It was one thing, he reasoned, to do it on cam when he didn't know Dean was watching and another to do it when he did. He wasn't sure that he could knowing his brother was.
Still panting heavily, whole body seeming to throb, Dean stared at the computer screen, waiting. He could tell by the look on his brother's face that he was thinking about it but hadn't decided yet. That meant that he had to do something to push him over the precipice and get him to agree. Though not an easy thing to do with all the blood from the brain above the shoulders being south of the border, he quickly sifted through what Sam had said to him already. The bit his brother had said earlier about liking dominant men seemed to click into place. Thinking it was worth a shot, he figured he would give it a try. Giving a loud groan, he hissed, “Get undressed and play with yourself, Sammy! I want to see you fuck that ass of yours with a toy like some talked about! Give me a show, little brother, so we can cum together.” Though he wasn't barking orders like he did in serious situations that demanded he be listened to, there was enough force in his lust thickened voice that he thought it might work. Well, he hoped it would anyway! If not, he would have to try something else.
Shivering slightly at the tone Dean used, Sam licked his lips in a nervous way. Oh, he wanted to he just wasn't sure if he should. But, honestly, since he was needing relief at this point, he was seriously considering it. Finally, he stammered out, “Look, Dean, I'm not sure about this, alright?”
By now, Dean's whole body was throbbing, demanding release of some kind. So, really, he didn't want to have to spend time doing a long convincing thing with Sam. Groaning, he rolled his eyes then hissed, “Come on, Sam! You know you want to, dude! Show me how you want me to fuck you so we can both get some relief here. They said you use toys once in a while for a show so I know you have them. Use one for me! I want to see you fuck that ass of your with it how you want me to do it when we get back together.”
Blushing slightly at the reference of some of the shows he had put on, Sam wiggled around in an uncomfortable way but, really, as turned on as he was, he decided it was time to throw in the towel and just go for it. Honestly, doing a private show for his brother was arousing in a twisted kind of way that he liked. Since he had agreed to go for it he might as well put his money where his mouth was. Nodding slightly, he stammered out softly, “Alright, give me a minute.” Scooting to the edge of the bed, he wiggled out of his boxers then tossed them aside onto the floor. Groaning softly, he stroked his aching flesh a couple times, feeling it throb thickly under his palm. Pulling open the drawer on the bedside table, he pulled out the average sized vibrator he favored and a tube of lube he kept there.
Though he was going to do this, his face was flaming slightly. It was one thing to do this kind of thing in front of strangers who he didn't know but another to do it for someone he knew better than anyone else in the world. It was unnerving yet exciting at the same time. But, for once, he was just going to go for it and not second guess or think it through anymore than he already was.
Sliding back to the position he had been in, he slouched down slightly, spreading his legs far apart. Popping the top on the lube, he squirted some on his fingers then slipped them down between his legs and began to stroke around the opening. Since he had done this enough, it didn't take long for him to relax to where he could slide a finger inside. Slowly fucking himself with it, he groaned, eyes sliding shut, leaning his head back against the wall he was propped against. Quickly, he added a second, scissoring them to loosen himself up enough to allow the toy entrance without pain. It wasn't long before he slipped a third inside him, repeating the process.
Sitting there, Dean was all but holding his breath, eyes glued to the screen, enthralled by what his brother was doing. Though he had seen chicks do this before, both live and on video, it was entirely different to watch Sammy do it. And it was one of the most fucking arousing things he had ever seen in his life. Though his cock was throbbing, demanding attention of some kind, he didn't touch it. As turned on as he was, he would come in a matter of seconds if he did that, not something he wanted. No, he wanted to wait for Sammy. But, DAMN, that was among the hardest things he had ever done in his life!
Once he felt he had himself loosened up enough, Sam picked up the vibrator, turned it on then, ever so slowly, eased the thing deep into his ass. Once it was all the way inside, he began to fuck himself with it deeply at the speed he adored making sure to graze it over the small lump of his prostate with each stroke. After finding the rhythm he wanted, he wrapped his other hand around his cock and began to stroke that. For the first time since starting, he opened his eyes and looked at his brother on the computer screen. Licking his lips, he moaned his name and just stared at his rock hard cock, seeing, even on the cam, it twitch slightly, the head of it shiny with pre-cum.
Dean was mesmerized by what he was seeing his brother do. This was a fucking HUGE turn on! Once the vibrator slid into Sammy's ass and he was fucking himself with it, Dean could take no more. Reaching down, he started stroking his cock some more, using all the self control he had to stave off his end. He wanted to do it as close to when Sam did as he could get. Hissing, he manged to get out, “Oh hell yeah, Sammy! Fuck yourself! Just think that's me doing it to you! Cause, dude, I am so going to fuck you nice and hard when we finally see each other!”
Groaning, Sam arched up slightly, thrusting the vibrator in faster, hand moving on his cock. “Yes, Dean!” He groaned, imagining that it was his brother deep in his ass rather than the toy. Some of the vivid images that played through his mind as he did that was enough to send him over the edge. Positioning the vibrator right on the prostate, the buzzing triggered his orgasm. Throwing his head back, he groaned out Dean's name as he came, spraying his cum all over his stomach and chest.
That was all it took for Dean as well. Hearing Sam call out his name as he came, Dean groaned loudly then let his own happen, the deep pulsing in his nuts throbbing madly as he came, shooting his spend all over himself before collapsing back on the bed, panting.

About three AM, Dean woke up, thirsty. Taking a glance at the computer screen, he could see the still naked Sam sprawled on his bed, covers hanging off his body enough that his crotch was exposed, his limp dick resting against one thick thigh. Grinning, the older Winchester shook his head then tossed the covers off of his body and stood. The cool air of the room hit his naked flesh, making him shiver. After a stretch and groan, he padded off to the bathroom to get a drink of water.
Coming back, he sat on the edge of the bed and sipped at the cool liquid, staring at the computer screen, eyes locked on the sleeping Sammy. Tonight had been mind blowing and he wanted more. But, beyond that, he wanted it for real, not just a show over the computer. In fact, he wanted it so bad he could taste it! It was his thinking that, maybe, it was time to start pressing for a meeting. No, not a permanent thing. With all that was going on that probably wasn't wise but he wanted to fuck Sam enough that he was willing to chance a quick get together for a weekend or something.
Downing the last of the water, he set the plastic cup aside then crawled back under the still body warmed covers and curled up. Turning on his side so he could watch the computer screen, he decided the following day he would start dancing in that direction and see where it would take him. Sure, the fact that neither should be thinking of this slipped across his mind but he ignored it like he always did anymore, focusing on what he wanted instead.
With a deep sigh, he shut his eyes and starting thinking of all the ways to start coaxing his brother into what he wanted until he dozed off.

'Gets out the Hypnotoad' Please review, you know you wanna!
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Carry On My Wayward Son