Chapter Text
The red light blinks back at him from the front of his camera as the dual monitors light up. One with a live chat, a viewer count, and a tip total, and the other showing his mostly naked body. It’s what the viewers will see so Dean can make sure he gets the most bang for his buck.
Immediately, the viewer count shoots up to seventy-eight, his regulars popping on without a second’s hesitation. They know his schedule, and he lets the sly smile slide across his face at the sight.
“An eager bunch tonight,” he says, not bothering to keep quiet since Sammy’s staying with a buddy tonight. The chat lights up, pinging with silent messages, and Dean catches a few before he slides back on his bed.
My wife is gone for another 20. Gotta make this quick.
You always make it worth it 💦
Fuck that ass with that monster cock 🍆
🔥🔥🔥🔥
Dean doesn’t bother reading the rest. They scroll by faster than he cares to track, so he leans back on one elbow, legs bent, knees spread wide as he presses his other palm into his semi through the soft, black satin panties that make the tip jar go wild.
His head falls back, mouth dropping open as he lets out a soft moan. He knows how he looks, and the ping-ping-ping sound of cash dropping into his tip jar only confirms what he already knows.
It takes seconds for his cock to fill, hardening under the perfect friction as he rolls his hips and turns sultry eyes on the camera. “Any bets?” he asks, the same as always, one eyebrow raised as he traces one finger around the outline of the thick, leaking tip.
The chat pings, CrowDaddy writing 20 says you don’t last two minutes with the plug.
“Put your money where your mouth is,” Dean purrs, then adds with a soft chuckle, “Or where you want it to be.” He shoots the camera a wink as the tip jar pings with the money, and Dean rolls his balls between his fingers as the CJNova writes take the thick black one all the way, come untouched, and I’ll give you 100.
“Uh-uh,” Dean says with a tsk , “this is a pay to watch, not pay to play.”
CJNova: even if I make it worth your while?
Dean thinks about it for a moment. “Tell you what,” he says, sitting up with both palms flat on his inner thighs, tickling the soft skin with his calloused hands. “Whoever’s top tipper by the time I get my fingers up my ass gets to choose the toy and how I get off.”
CJNova: Deal.
CrowDaddy: I’ll fill your pockets while you fill your ass 🍆💦
CajunBear69: Gonna spend my whole paycheck to get you to put on the spreader.
That’s actually not a bad idea; Dean kind of loves being split wide, legs aching, unable to close them. It’s harder when he’s the only one in the room, but he’s done it before.
Dean fiddles with the monitor for a minute, setting up the top-tipper function so he can see the winner when the time comes. Then, with a quick glance at himself, he slides back into the center of the bed and starts pressing a finger to his puckered hole through the thin satin.
He clenches around the strange feeling, but lifts his hips and massages harder, knowing they love when he does this. Something about the way the tips shoot up and the comments go wild, beyond the money and the physical pleasure, sends a thrill through him. He likes that he’s pleasing them—makes doing the work that much more enjoyable.
Dean draws it out, letting his moans grow and fall, his hips rolling until the tips start to wane. Then, he slides off the panties, letting his dick spring free and making sure the wet spot is visible on the screen. His cock is hard enough to pound nails, dripping thick pre-come, and he slides his palm through it, smearing it up and down his shaft as he brings one leg higher, planting his heel on the mattress and letting his knees fall wide enough for his hip to ache.
“Fuck, I want a mouth on me,” Dean groans, head falling back to expose his neck as he twists his fist around the leaking tip. “Any takers?” He arches a brow in what Charlie calls his bratty look and eyes the camera, knowing the chat is full of all the takers.
“‘m sure you’d all treat me real nice, wouldn’t you?” he says, letting his voice melt into a subtle southern drawl he knows CajunDaddy69 loves.
Sure enough, CajunDaddy69 pops into the top tipper spot seconds later.
“Or maybe not so nice?” he adds, grabbing the lube from where he tossed it up by the headboard. He maneuvers himself onto his knees, ass facing the camera, bent at the hips, and spreads his asscheeks. “Hold me down and fuck me, huh? Press my face into the mattress and make me scream? Ruin my ass for a week, making me cry for it to stop—for it to never stop. Fuck…” Dean bites his bottom lip as heat burns through him, pumping through his veins as he gets a lubed up finger on his puckered hole.
Like this, he has to bury his face in the blankets, holding his ass open with one hand as the other plays with his rim. He does his best to turn his face toward the mic, but it’s hard when all he wants to do is close his eyes and sink into the pleasant burn of pressing a finger in to the third knuckle before he’s ready.
His hole clenches, fighting his shifting finger as he presses in before pulling out again. He shuffles his knees wider until his cock brushes the mattress, the thick head staining his sheets with pre-come as he works a second finger past his rim.
Lube slicks the inside of his thighs, dripping down his balls in a way he knows his audience loves, no matter how much more laundry he’ll have to do before his Saturday night session.
Ah, well, that’s four days away.
All thoughts of laundry flee his mind when his fingers brush that spot up inside him, and he lets out a soft moan as he hooks his fingers, going for it again and again before adding a third digit.
His hips roll, pleasure spiking in his chest as a fine sheen of sweat coats his skin. Fuck, he’s not going to last long.
Dean pulls his fingers from his ass with a wet squelch before twisting to look at the screen. “Time’s up, boys,” he says, glancing at the top tipper before a sly smile spreads across his face. He’d never admit it out loud, but he’s got a favorite customer. Always respectful, doesn’t ask too much, and tips like money’s going out of style. “ CJNova, what’ll it be tonight?”
CJNova: I changed my mind. Cock ring and the glass dildo. Fuck yourself deep and slow. Set a timer for ten minutes, and if you make it to the ten minute mark without begging to come, you can take the cock ring off and use your hands. If not, come untouched with the cock in your ass.
Damn, he put a lot of thought into that. Dean swallows hard, his arousal swelling like a tide, pressing against his tingling skin, aching in his bones as he gives a wink and his patented Winchester grin. “You got it.”
Dean doesn’t waste any time, sliding off the bed and out of the frame to grab his box of toys. The box hides in the back of his closet, made of dark cherry wood and lined with velvet. It is deep, with removable tiers containing dildos, plugs, blindfolds, gags, clamps, and other crap he uses on his livestreams. He grabs a simple chrome cock ring and the long, thick, glass dildo before snapping the box shut.
“Where do you want me, sir?” Dean asks, crawling onto the sheets with his eyes half-lidded and locked on the camera. The tips jump at that, and Dean takes a moment to pin CJNova’s messages before they scroll away from him.
CJNova: On your knees, facing the camera, legs spread wide enough to watch you ride that cock.
Dean does as he’s told, feeling a thrill move through him as he spreads his legs and shifts around until he’s in the center of the monitor. It takes less than a second to slide the cock ring down his aching erection. It fits snug at the base, restricting the blood flow in an almost uncomfortable way, but he slides a finger through the pre-come beading at the head, sucking in a deep breath as pleasure bubbles inside him.
After a moment of fumbling fingers and hitching breaths, Dean grabs the dildo and positions the tip at his stretched opening. The unforgiving glass splits him wide open as he bears down, the dry burn almost too much, and he takes half a second to pour some more lube into one hand and slick the dildo with it before continuing to lower himself down.
“Uh,” he grunts, mouth wide, eyelashes fluttering as he tips his head back to expose his neck. He clenches around the dildo, the glass far more solid than he’s used to, and cold against his inner walls. He shivers, stretched wide enough that he’s sure he’ll be feeling it in the morning. “Fuck, so good.”
Inch by inch, Dean slides all the way down, his thighs burning under the strain and his wrist cramping from holding the base steady. But the feeling of being stuffed full is so worth it, and Dean has to close his eyes and suck in a few deep breaths before he can remember what he’s supposed to be doing.
Deep and slow, no begging to come, ten minutes.
Dean pulls out his phone and sets the timer, making sure to flash it at the camera to CJNova can see how good he is at following directions.
He tosses his phone aside and gets down to business, straining his thighs as he pushes up, then drops back down with his full weight. The tip of the dildo punches his prostate on the first go, the curved tip setting him up for the same pressure over and over, so he does it again.
“Fuck,” he breathes as liquid fire burns through his veins, lighting him up as pleasure builds low in his groin. His dripping erection bobs with every up and down, cock ring flashing in the camera lights he has set up around the room.
“Uh-uh-uh,” he grunts, up and down, up and down, over and over and over, the pleasure ratcheting higher with his racing heartbeat. Something about this—losing himself to it all and just letting go—has his head spinning with want. More, more, more, he craves this high, it makes him feel wanted, worth something.
“Come on, come on, come on,” he whimpers, gritting his teeth as pleasure rockets through him, stopping before he can shoot his load. His dick is an angry shade of deep red, a thick vein pulsing with every beat of his heart, but he doesn’t dare touch himself—not yet. Not until CJNova says so.
By the time the timer rings, he thinks he’s going to die.
“Fuck,” he sobs, so desperate to come that tears leak from the corners of his eyes, and he grinds down on the dildo like it’ll do anything more than make the problem worse. “Time,” he pants, jerking forward to see the chat.
CJNova: cock ring off. You can touch yourself.
Dean just about tears his dick off when he pulls the cock ring free, but he can’t bring himself to care as he finally gets what he wants. He drops back onto the dildo, not bothering to lift himself back up as he uses his hand to grind it against his prostate over and over in an unending rhythm. His other hand clamps onto his weeping erection, flying over himself with the kind of urgency he hasn’t felt since he was a preteen who’d just discovered porno.
The pleasure claws up his chest, into his lungs and throat, back down his spine before winding tight. A rubber band stretched too far, it snaps, letting loose a tsunami of pleasure. Wave after wave crashes over Dean as he lets out a loud, “Fuck!”
Come spurts from him in a thick stream, coating his chest and neck, dripping hot over his sweat-slick skin as he shakes and shivers. Every breath burns his lungs as the pleasure eventually ebbs, his grinding slowing to a stop as he holds his spent cock in a loose grip.
After a moment, he finds the strength to peel open his eyes and look at the screen. He looks entirely debauched, eyes heavy-lidded, shiny with sweat and his hair a mess where he hadn’t realized he ran his fingers through it. Come coats his skin in thick, white spurts, and he takes a moment to run his finger through some of it, bringing it to his lips to suck clean.
A few last minute tips drop into the tip jar, and Dean gives the camera a sated smile before glancing at the chat one last time.
Right there, pinned at the top, is CJNova’s message, and something inside Dean’s chest heaves when he reads it.
Good boy.