When this hit 20,000 words, I decided to split it up into multiple chapters. I'm guessing it'll ultimately be 25,000 to 30,000, and I'll be arbitrarily split into 4 or 5 chapters, I expect. I tried to choose chapter breaks that made sense, sorry if they don't.

I am on massive levels of hormones that are screwing with me head and making me want to write *alllll the angst*. There is a lot of angst, and less smut than ya'll usually get from me (but there's some). I personally love angst, so I hope ya'll do to, and that you enjoy. :)

It is important for the reader to understand what "sub drop" is to better understand the level of angst going on in Dean's head in parts of this story. "Sub drop" is when, after an intense sexual encounter (it doesn't have to be sub/dom) causes the body to generate endorphins, those endorphins dissipate and by contrast the person feels depressed. This isn't necessarily that big a deal - though it can be - it varies by individual. For someone who has depression issues anyway, the endorphin crash of sub drop can be a really serious problem.

Trigger Warnings/Content Notes (not all in Chapter 1):

-Description of incest/twincest

-John Winchester's A+ Parenting

-No seriously he's a douche bag even though he's dead

-Homophobic language

-Accounts of past physical abuse

-Accounts of past emotional abuse

-Accounts of past prostitution

-Discussion/reminiscence of underage sexual encounters

-Implied/vaguely remembered accounts of sexual encounters between a teenager and an adult

-Dean's massive self-esteem issues

-Sub drop

FYI everyone, I haven't been super careful in constructing a timeline for this story, but here's roughly how I envision things (some of this info is new to this story):

Fourteen years before 20XA: Cas and Dean enter their freshman year at Lawrence HS together and become friends. Both are 14, as is Jimmy. Sam is 10 (Dean is 4 ½ years older).

Ten years before 20XA: Dean, Jimmy and Cas graduate. Dean stays in Lawrence. Jimmy moves west to start school at Berkeley. For a year, Cas goes to KU, but then he follows Jimmy to California.

Six years before 20XA: Sam graduates high school. He leaves for Stanford. Dean stays in Lawrence.

Three years before 20XA: John Winchester dies when Dean is 26 years old. Dean moves to San Jose.

Two years before 20XA: Sam graduates pre-law, starts law school.

July, 20XA: Dean and Cas start dating

November, 20XA: Cas invites Jimmy to join them (the events of "I Guess You're Just What I Needed")

Late March, 20XB: Dean says "I love you." (the events of "No More Than He Deserves")

Early April, 20XB: This story takes place.

A shrill alarm next to Dean's ear woke him instantly. Grumbling under his breath, Dean rolled over and shoved a pillow over his head, but the noise didn't stop.

"Cas, get up," he mumbled sleepily.

Through the thick fabric, the painful edge was taken off the noise, but it was still impossible to ignore. Sluggish thoughts began to register the situation in the bedroom. No one was touching his body. While he, Jimmy and Cas fit comfortably in the bed, it was unheard of for their not to be some kind of physical contact between them as they lay there. Jimmy tended to sprawl, and Cas liked to keep a hand on Dean at all times, and both tended to brush Dean since he slept in the middle. Fumbling between the sheets with sleep-numbed fingers, Dean found no tell-tale signs of warmth. That the twins would leave before Dean woke up was normal. Though Dean was a light sleeper, they were expert at sneaking out without bothering him. According to them, every morning Dean woke up, muttered good bye to them, and then passed out. Invariably, by the time Dean woke up again, he'd forgotten the exchange, and spent several seconds panicking that the twins' alarm hadn't gone off and they'd been late. He'd never been so comfortable anywhere, had never slept so well. At some point, without even realizing it, he'd given over feeling the need to be vigilant around Cas and Jimmy.

Flailing in the direction of the night stand, Dean brought his hand down on his cell phone, grabbed it, and squinted at the screen through sleep-bleary eyes. He swiped a finger over the display to shut the noise off, and the room went starkly quiet by contrast. The time read 7:02 AM, only an hour after the twins would have woken, 30 minutes since they left. There was no reason for Dean's alarm to be on, or his cell phone to be by the bed at all, unless Cas or Jimmy had put it there. A stab of heat colored his cheeks, rubbed phantom pleasure inside his ass, began to thicken his erection. Throwing aside the blankets, he half ran, half stumbled to the bathroom so take care of business before he grew uncomfortably aroused.

The apartment showed little signs of Dean's having moved in two weeks earlier. There were three toothbrushes in the cup instead of two. A third corner of the large bathtub held bottles of shampoo and aftershave. Originally, one drawer of the chest was given over entirely to Dean's belongings, but that organization had last roughly four days, until the first time the three of them had down laundry. Dean had folded everything in one pile, planning to separate it later. Instead, Jimmy had stuffed the clothing into whatever available space he could find. Just that soon, Dean's things became as mixed in with the twins' boxers and shirts and pants as the twin's belongings had been jumbled together before Dean moved in.

The formerly bare walls of the bedroom now held a single large frame, matted for six small pictures: Sam and Dean the day Sam graduated from high school, John depressingly yet gloriously nowhere in sight; teenage Cas and Dean hefting the enormous trophy that the Lawrence High Cornstalkers won when they beat the Dodge City Ramblers at the Kansas State Championship game; a slightly out of focus picture of Jimmy and Cas using two straws to drink from the same neon pink slushy; a photo of the Impala parked outside of Dean's first apartment in San Jose; a posed picture of the eight members the Novak family looking staid, demure and proper in suits and dresses, only Jimmy daring to wear a smile, sent to Dean as a Christmas card ages ago; and an old photo, yellowed at the edges, of the entire Winchester family, Mary, John, a chubby-cheeked youthful Dean and an infant Sam clearly on the verge of screaming his head off. When he lived alone, Dean kept the pictures hung in the back of his closet so no one would see his sentimentality. When Dean pulled it from the box of things the twins had carried from the Impala, he'd resolutely gone to the kitchen, grabbed a hammer and a nail, picked a spot near the window and hung the frame, all the while staring defiance that dared Jimmy and Cas to say one word. Neither had, though Jimmy had smirked like he was on the verge of laughing the whole time, and Cas had quirked his head to one side in confusion at the three pictures of himself. The next day Dean had entered the bedroom to find Cas covering the shot of his family with one hand, staring at the look on Dean's face in the football shot, frowning pensively as if seeing something in it he'd never seen before. When Cas had realized that Dean was watching him, Cas had turned abruptly away and left the room, but not before Dean caught a glimpse of stunning blue eyes awash with tears and warmth.

If Dean were any kind of man, he'd have gone after Cas and made sure he was okay. Instead, he'd heard the whisper of John Winchester reminding him that men didn't talk about shit like that. Instead, he'd stared at the pictures and wondered if he should take them down. Instead, he'd hurriedly joined Cas in the kitchen, and the two of them put dinner together while discussing inane things Cas' students had written in their most recent paper. Instead, that night in bed – not a scene, they usually only scened every week or two, and they hadn't since that fucking amazing night two weeks ago – Dean had made sure that Cas and Jimmy both had one hell of a good time with his mouth and his ass. It was the least he could do, after everything they did for him. He'd had fun too, but it was about them, had to be about them. Cas had given him the strangest look afterwards, one Dean still hadn't been able to figure out the meaning of, though it had troubled him ever since.

Steely determination kept Dean's eyes from more than glancing over at the table beside the bedroom door. It was Thursday, and early, and the chances that the twins would be home before 2 or 3 that afternoon were virtually nonexistent. If they'd set him an alarm for 7, they wanted him up at 7, but knowing them they expected him to take care of himself before beginning. To the accompanying drip of a brewing pot of coffee, Dean scrambled some eggs, toasted bread, and tossed some slices of pre-cooked bacon in the microwave. Sitting at the kitchenette in his boxers, he ate the meal and flicked through reviews on Rotten Tomatoes, wishing he had the money to take Cas and Jimmy out on a date night, take them out to dinner somewhere that had real table clothes and candles and dim lighting that was meant to be atmospheric, not to hide the stains on the carpeting. Fuck, if he could afford to take them all to damn McDonalds and get a Redbox rental, that'd be better than the reality. Pathetic.

Dean heaved a sigh, rose and took his dishes to the sink. The twins had left their breakfast dishes for him to wash, at his insistence that if he was living rent free the chores were the least he could do, Dean wondered, not for the first time, what he was doing there. Every week it became more flagrantly obvious that Cas and Jimmy were in love with each other, in the "love that dare not speak its name" way as well as in the "he's my brother" way. It was only a matter of time before they realized that they didn't need Dean and his major malfunctions cluttering up what the two of them had. When that happened, Dean would be shit out of luck, and it would hurt worse the longer he waited.

Fuck, but he was glad they were doing a scene today. The physical high from the last one had lasted a few hours, the emotional high had lasted a few weeks, but it was finally wearing off. In its wake, he felt like Dean Winchester again. He hated feeling like Dean Winchester.

Dean hated Dean Winchester.

The thought was a punch to the gut, knotting up his insides, destroying the light buzz of anticipation. Disgruntled, Dean walked into the living room, stepped out of his boxers, balled them up and tossed them under the table. The placement sent Cas and Jimmy the message that Dean was green light, a-ok and ready to go. The first was a total lie, he had no means to communicate the nuances of the truth, but the second was absolutely true. He was ready to be whatever they needed him to be so that they could get off. He was ready to be whatever they wanted, for as long as they wanted. Increasingly, it felt like there was a countdown running on how long before they neither needed or wanted him at all anymore.

How the fuck could Jimmy and Cas both love Dean Winchester?

Atop the table was a bottle of lube and an unfamiliar butt plug, dull matte black, several inches long, narrow at the top, bulbous in the center, narrow just before the base, entirely unremarkable looking. A faint line traced around the top of it, as if a seam had been left when it was cast, and though it looked rubbery, it was surprisingly firm and heavy. Between the three men, they owned four butt plugs nearly identical to this one. There was no reason to buy another. A wooden dowel, about waist high on him and a couple inches thick, leaned against the side of the table.

The note for the day had been written by Jimmy.

You're in for one hell of a ride. Go lie on the bed and get comfortable. We thought you might need something to hold on to.

Frowning, Dean took the plug, the lube and the rod to bed, wondering what they had in mind.

The familiar steps of prepping himself were calming, helped to clear his mind of the damning realization of minutes before. Self-hatred wasn't something he could deal with, not now, not ever. Once he began, there were no thoughts, there was only the cold slickness of lube in his hand, only the liquid dripping down his fingers as he coated them. He thrust the fingers into himself smoothly, smeared the lube within his body. There was no pleasure to be had in fingering himself, not when he was forcing his conscious thoughts away so complete. There was only the need to prepare, only the need to be ready for Cas and Jimmy. With therapeutic detachment, Dean rolled the plug in the lube in his hand and thrust it into himself indifferently. He grabbed a tissue from a box on Cas' nightstand, cleaned his hands, threw the tissue away, and settled back on the bed.

The rod was the mystery. Something to hold on to. He grasped it in one hand, considered the thick hardness of it in his grip. It was grounding, soothing, in the same way he felt centered when Cas grasped his shoulder or Jimmy let Dean hold his hand during a scene. It was easily long enough for Dean to hold in both hands, and he lay it across his belly, feeling the wood abrading slightly on the soft skin of his stomach. Taking it in both hands, he balanced it across body. Get comfortable, the note had said. The position, while interesting, was definitely not comfortable. A few other potential positions crossed his mind, but none that met the requirement that he be lying on the bed. He shifted his hips, felt the plug move in a way that finally gave a hint of pleasure, felt a chill of gusting air over the curve at his lower back. With a flash of inspiration, he slipped the dowel under his hips, right above his ass, and lay back down. It nestled comfortably there, digging in to his back just enough for him to be aware of it without it being a bother. Smiling that he'd found a solution – hoping it was one the twins would like – Dean settled on to the bed, wrapped both hands around the thick wood, wiggled his ass to give himself one last jolt of pleasure, and went still, arms at his side, shoulders rolled back, legs spread wide, cock resting mostly limp.

Breath in, breath out.

The ceiling was white, the only thing he could see without turning his head. The air was cool, ventilation stirring a breeze that brushed tantalizingly through the hair on his unshaved arms and legs, through the manicured shock of brown hair at the base of his cock. The comforter was plush, soft and easing against his skin. The wood in his hands was slightly rough, and he longed to rub his thumb over it, to feel the friction between his calloused skin and the unpolished pine grain. The plug teased at him, barely present enough to give him the hint erotic distraction, causing him to feel pleasantly stretched. His cock, half-hard with interest while he prepared, went flaccid. He would be waiting alone for hours. They'd never know if he moved, never know if obeyed. That didn't matter. He'd know if he did as instructed.

I have to be good for them.

Breath in, breath out.

Otherwise, what use am I?

Breath in, breath out.

It's just a matter of time before they realize that all they need is each other.

Breath in, breath out.

Pathetic.

Breath in, breath out.

His grip on the rod tightened, and the thoughts faded. He had chosen this. He had chosen them. They had chosen him, for some reason.

Reverberating pressure blossomed between Dean's legs, spreading him, vibrating through him, the toy turning on and shivering him with pleasure. More than that, it was moving, it was expanding, it was opening him, it was…he gasped, back arching involuntarily, as it pressed against his prostate. It was all he could do not to cry out, not to writhe against the mattress. He was hard instantly, unsure if he was looking at the white paint or if his vision had blanked. His hands convulsed around the rod as he collapsed back against the bed, gasping, struggling to accommodate the unbelievable feeling. The vibration toned down, but the constant touch against the sensitive nerves within him did not, and he bit his lips against constant whimpers. Part of him screamed for the vibration to resume, it felt so wonderful it filled the entire world with nothing but pulsing pleasure. Another part of him prayed it wouldn't. There was no way he could hold still with that feeling trembling through his body, no way he could withstand the need to touch himself, no way he could keep quiet.

Each panting breath he rasped in was ragged over his throat, his chest heaving. The whisper of buzzing touch created barely enough friction for him to be aware of it massaging through his channel. The constant stimulation to his prostate was like a light flashed before his eyes constantly, impossible to ignore, impossible to tune out. It was all consuming, wonderful, inexplicable.

As always, Jimmy and Cas looked after him. They knew that if Dean had nothing to distract him, he'd lose his damn mind. They knew he needed more than just a plug to occupy him for so long. They took care of him. He should trust them – would trust them. The vibration amped up once more and tears of bliss pooled in the corners of Dean's eyes. Silently, his lips mouthed, "so good, so good, so good" but he held the words back. Even though they'd never know if Dean disobeyed his orders, Dean would know. He'd follow his instructions. He wouldn't move. He wouldn't make a noise. He'd be ready and waiting for them when they got back.

It was easy to say that the first hour.

Dean never knew when the vibrator would turn on, turn off, increase in intensity, fade to nothing. He never knew when the butt plug would close in on itself – how the fuck was it doing that? – or when it would unfold and make him quiver with unsatisfied bliss. Long minutes would pass with nothing but his view of the ceiling, the loud sound of his own breathing in his ears, and the constant, urgent demands of his aching cock. There was no peace in those minutes, only tense anticipation that knotted his muscles. At any moment, the twins might activate the device again. His muscles rapidly grew fatigued as Dean kept his limbs and abs rigid against the certainty that when the plug turned on again it would be all he could do not to move, not to thrash, not to break and reach between his legs and thrust the toy in and out of his body, stroke his hardness. Inevitably, no matter how long he stayed tense, it was not until he began to relax that the pressure returned. The vibration was spectacular. His hands gripped the rod until his fingertips hurt with the strain and he silently cried, mouth agape, cock leaking against his belly, awash in the ecstasy he didn't dare respond to.

So it went, on and on, as Dean strained to breath in and out.

At least he was no longer thinking about anything other than how damn awesome this butt plug was and how essential it was for him to behave.

The toy had been inert for at least ten minutes, he thought, when it began to vibrate gently. The feeling was so faint that he hardly noticed, was sustained so long that he grew accustomed to the buzz of pleasure, so much so that he was barely aware of it.

The frequency increased abruptly, sparkles bursting before his eyes. The toy wasn't as arousing when it was folded up, but even so the constant massaging of the toy gave excellent friction, good but never enough. Time stretched out again with no change in the toy's modulation, and once more the feeling grew so much a part of the background noise that he nearly forgot the toy was on.

The reverberation kicked up another notch. Lights like fireflies scattered before Dean's vision. His cock throbbed, his pulse sped as if it were racing against the vibrations, trying to catch up with them. It felt like time passed by seconds, each one endless, covering him in the bliss his lovers were granting him from afar. It seemed impossible that Dean could acclimate to the intensity of the feeling coursing through his channel, through his body, through his thoughts and behind his eyes and down to his finger tips and through his cock. Time proved him wrong, though. The time passed and his muscles began to relax, the vibration imitative of a soothing massage despite the way it was driving him completely crazy with want. Blood pulsed in his ears, and the pre-come and sweat that cooled from his skin kept him from sweltering.

The strength of the vibration amped up again.

There was no ignoring it. There was no getting used to it. Dean could hear it buzzing like a swarm of bees circling him, feel it rattling through his teeth. His vision of the ceiling fuzzed out and the pulsations coursing through Dean's body made his muscles feel jellified and uncontrollable. His toes curled against the bedding, his legs twitched and spasmed, his head shook back and forth. Unremitting bliss threatened to drown him. He wanted to scream with pleasure. He wanted to come, fuck did he want to come, out of nowhere his orgasm threatened to suffocate him, his cock swelled and pulsing with heated blood and the semen being forced from the tip. Dean clamped down hard on the wooden dowel, strained against it with all his might, but the relief it offered was limited, his arms too rattled to hold on tightly, his grip weakened after so long. Frantically gasping for air, Dean held himself on the edge of his orgasm and prayed, fucking silently begged that the twins' unerring sense of his limits was on point, that they realized how far they were pushing him.

The plug unfolded, brushed that all-consuming resonance against his prostate, held it there, coursing unspeakable oscillation through the most sensitive nerves in his entire body. Dean's hips gave an emphatic, uncontrollable thrust into the air, and his tenuous hold on equilibrium shattered. To the accompaniment of desperate sobs of sheer elation, his orgasm swept over him, his cock spewed hot semen across his belly. All his muscles knotted and then released and he melted against the bed, cock straining, pleasure resonating through him, endless bliss. Semen oozed thickly towards his crotch, catching in the thickening triangle of hair feathering down his lower abdomen. The stimulation continued, endless instants of shivering rapture. His hips rutted at the air and contradictory thoughts begged for the feeling to continue, begged for it to just fucking end already.

His orders remained, a tenuous thread that screamed that he had to be silent, had to clutch the wooden rod. The importance of these directives was lost on him, nothing but white blankness and intense pleasure in his mind, but the need to follow them remained. He clamped his teeth against frantic groans as secondary and tertiary spurts of come weakly erupted from his burning cock to fall amidst his pubic hair. His body continuing to pulse a fourth, a fifth, a sixth time, even though there was nothing more to release. On and on the orgasm was prolonged, wracking his body to the point of nausea, to the point of pain, until the injunctions restraining him shattered, and words cracked free.

"Stop, stop, please stop, stop…make it stop…please…"

In answer to his pleas, the vibration cut off as if it had never been, the touch against his prostate shifted away, and the toy went dead. Ragged sobs scoured dryly over his aching throat as he rolled to his side, curled in on himself, banged his forehead against his knees and cried as he'd never cried in his life, clutching at his hair with limp fingers. The lingering heat of pleasure ebbed throughout his body, but it faded rapidly, overwhelmed by a fucking ocean of guilt and shame.

In the eight months he and Cas had been doing scenes together, he'd never failed so completely.

There was no getting past that single point.

This was the one thing that Dean had left that made him feel like he could get through each day, and he had failed utterly, spectacularly, even enthusiastically.

The silence in his blissed-out mind was smug as it mocked him. There was no need for John Winchester's taunting voice to point out Dean's inadequacies. There was no point in tearing him down further. The evidence was too clear to be ignored. It was smeared all over his belly, drying in his pubic hair.

Dean could get up, clean himself off, calm himself down, re-position himself, pretend like it had never happened. There were no cameras in the room. For all that Cas and Jimmy got off on knowing Dean was waiting, were surely closeted somewhere on campus right then enjoying what they imagined they were doing to him, unless Dean told them they need never know that he'd just creamed himself untouched over a fucking vibrator.

Cas' office was so small that it was crowded with two people in it. Office hours were open, but the no one came mid-semester, leaving Castiel and Jimmy the privacy they needed. Frantic hands pawed intimately at clothed bodies, frantic mouths came together, lips made rough and firm by urgency, tongues flicking against each other, separating, linked briefly by a thin streamer of saliva. Fingers rubbed at nipples, drawing whimpers so deep they bordered on growls. With a snarl, Cas forced their bodies apart, pushed Jimmy against his desk, attacked the button and zipper on Jimmy's pants, pressed palms against the erection clothed with in. A low moan escaped Jimmy.

"Cas…"

Normally, the fantasies brought pleasure, left Dean aching and waiting, but now he just hurt. The prospect of them learning the truth was agonizing. The vision played on, heedless of his control, his desire for it to stop and leave him to his unhappiness in peace.

Abruptly, both men stopped moving, gasping with the effort of self-restraint. "What about Dean?" asked Cas, voice low and throaty yet pained.

"Yeah," said Jimmy with disappointment. Despite his tone, his hips rutted gently against Cas' hands, still cupped against the bulge in Jimmy's pants. "He's waiting for us at home."

"It's going to be hours."

There was a long pause. The two men stared at each other, gorgeous blue eyes met, chests matched in rapid breaths.

"I don't want to wait, Cas," confessed Jimmy.

"Neither do I," Cas' cheeks colored, breaking their gaze, kneading more urgently against Jimmy's hard cock.

"What Dean doesn't know won't hurt him…"

With a shudder, Dean suppressed the thoughts. The twins never had anal when Dean was around, which he'd long assumed meant they had it when he wasn't. If he couldn't be a good submissive, obedient, well-behaved, eager and awaiting their pleasure, they would have no use for him. Regardless of how much both men enjoyed telling him what to do, Jimmy could, and occasionally did, enjoy the sub role as much as Dean did.

Dean was rapidly becoming irrelevant.

Dean could clean himself up, reposition himself, and act like nothing had happened.

It wouldn't change the truth. He knew he'd failed, utterly, and in failing he'd sealed his face. Cas always knew when something was troubling Dean. He'd find out.

A faint hum suffused his body, the toy turning on tauntingly, shutting off again moments later. The shiver of it in his senses continued long after the butt plug stilled. Unable to force himself to lay back down, Dean huddled in on himself, nearly fetal, accepting what little pleasure he could derive from the recurring teasing. Soon enough, it would all be over. Soon enough, they'd come home and they'd see him.

The thought was nauseatingly painful.

The unpleasant vibration through his spent body was the least he deserved for being Dean Winchester. A dull throb of pain etched dark lines through his mind, pounding behind his bleary, gritty eyes. A burst of intense vibration tingled through him, caused his spent cock to twitch, but there was no chance he could get it up again, not so soon, not with his prevailing depression. When Cas and Jimmy came home, he'd make sure they punished him like deserved. He could wait until then.

The fatigue of spending himself always left Dean blanked out, and usually that was a good thing, pleasant and warm, familiar and loving. Now, it was the opposite, a reminder of his utter inadequacy, and he wallowed in it, letting his thoughts drift.

Dean hated Dean Winchester. What a fucking useless jack off he was.

The butt plug I reference doesn't actually exist (I don't think...) but I figured we have the technology - I was heavily inspired by an actual toy I found on www dot extremerestraints dot com. If you want to see it, go to that URL and add this: /butt-plugs_1/remote-control-ass-anchor_ .

I kinda want to get the next chunk up tonight, but it might not happen, I'm pretty tired.