AN: Sooooo... I was just gonna do one chapter for Friday, but uh... Cas got a little impatient and needy and then stuff happened. I apologize for nothing. (lol it of course means I didn't do *any of the things* I'd originally planned for this chapter)
Side note, I really hope I can finish this and have it posted before Thursday evening. Otherwise it'll have to wait til next week (I'm out of town Friday-Monday). I *theoretically* should be able to do that, there's not much left, but if Cas and Dean keep going off the script it might take longer.
I think I've got something like: Friday Afternoon (possibly a short chapter); Friday Evening (*waggles eyebrows*), Saturday (sort of an epilogue?)
As always, tags have been updated to reflect this chapter.
Dean's not cruel enough to make Cas walk back to his dorm like that. He lends him some sweatpants (though the look he gives Cas when he's fully dressed in nothing but Dean's clothes... well, it's a close call but Dean might've been thinking about round two) and puts the butt plug in a discrete brown paper bag. Not that it doesn't feel like there's a neon sign floating above him flashing, "THIS BOY HAS A PURPLE BUTT PLUG IN HIS HANDS! JUDGE HIM!"
His walk back to his room as quickly as possible. The paranoia he's feeling is unjustified, of course, but he can't shake the feeling that everyone knows.
Oh god, he thinks. If this is how bad it is just carrying the damn thing to my room, how am I going to feel wearing it all day tomorrow?
When he gets back to his room, he tries not to look guilty. Luckily his roommate is out so he doesn't have to awkwardly avoid eye contact as he slips the bag into the drawer of his nightstand. Or try to hide the way he's half hard, has been since he left Dean's room.
There's a moment when he's safely tucked in his bed, cozy in his blankets and masked by darkness, that he's tempted. Tempted to stroke himself to full hardness and think about the plug on a few feet way. Allow himself to fantasize about what Dean has planned for tomorrow (because by now he knows the older boy well enough to know he won't stop there, oh no, he'll have so much more in mind).
But Cas also knows he can't come. So he could tease himself, work himself toward a finish line he's not allowed to cross, but for what? He'd be more worked up than he is now, and short of calling Dean and begging him to reconsider-
His brain kinda short circuits at that thought. Because he could ask Dean, couldn't he?
He scrambles for his phone and flips through the contacts. The frat brothers gave their pledges their numbers the first day, just in case they needed something. And the brothers have their numbers, just in case they* need something. Dean's name has been there since Sunday, waiting between Balthazar and Gabriel's numbers. It'd never occurred to him that he might need it, but now...
It's late, he reasons with himself. Dean's probably gone to sleep. Disturbing him to ask for permission to jerk off is hardly going to go over well.
Cas is wavering back and forth, finger hovering over the call button, when he hears the key in the door. He nearly jumps out of his skin. In a panic, he turns off the phone and shoves it under his pillow. The door opens, light sweeping across the room just as Cas has finished settling down to pretend to be asleep. Heart beating out of his chest, he's not entirely sure he's convincing. But mercifully his roommate doesn't notice (or at least says nothing if he does).
There's some puttering around for a couple minutes before his roommate also goes to bed. With only a little annoyance, Castiel acknowledges that the decision's been made for him. He tries not to sigh too loudly.
Of course he doesn't sleep well, either. It takes a while for him to actually drift off, and even then he's plagued by vivid dreams and the idea of calling Dean and asking pleading begging to get off. The thought has ingrained itself so deeply into his subconscious that as soon as he hears his roommate slip out for an early class, he's instantly awake.
Although he's reasonably confidant that Dean doesn't have class today (he might need to TA, but otherwise he's free), Cas doesn't want to interrupt. He opens up a new text message. Luckily (or unluckily), he's too groggy to put much thought into what he sends.
8.02 AM: Sir, may I come?
8.02 AM: Pls
The minutes drag out in silence and Cas starts to worry. What if this isn't Dean's number? What if it's one of the other frat brothers or its just some random number he'd typed in by mistake? Or maybe it is Dean's number but he doesn't know it's Cas? Cas hopes that Dean wouldn't be doing... whatever it is they're doing with other people. But maybe he is and maybe he's wondering who is sending him this message and-
8.11 AM: Cas, I told you - you gotta EARN getting to come
Cas lets out a sigh of relief that at least some of his concerns have been addressed. It's short-lived when he registers that he has not been given permission. He whines out loud and starts typing out a reply with angry frustration.
8.12 AM: PLEASE sir - I've been thinking about you all night
He pauses right after he hits send, an idea occurring to him.
8.12 AM: Is there anything I could do to earn coming?
No answer. He thinks maybe he pushed too far, that his punishment is that he won't even get a reply in addition to his lack of relief.
8.15 AM: You alone?
He can't type a reply fast enough.
8:16 AM: Yes sir my roommate is in class
8:17 AM: Gimme a minute
Castiel does his best to be patient, but he squirms in his bed and palms restlessly at his cock, straining against his boxers and soaking the front in precum and- Oh shit, Dean's boxers. He's still in Dean's clothes from yesterday. Fuck that's... that's unexpectedly hot.
8:19 AM: Get out the bag I gave you
Eagerly, he does as he's told. He didn't inspect it after Dean gave it to him yesterday, too embarrassed to do so in front of Dean and too paranoid to do so on the walk back or when he returned to his room. Now he carefully takes it out and empties the contents on his bed. The butt plug is still in its box, just as he'd expected, but there's also a container of lube. Which... okay, yeah, good thinking. He's not even sure he has that much left.
8:20 AM: Get undressed
8:20 AM: Call me when you're ready
He strips in record time then positions himself against his headboard with the pillows cushioning his back, opening up the box and making sure the lube is within reach. Cas takes a moment to calm himself down, steady his breathing, before actually hitting the Call button on his phone.
"Cas."
"Sir," he hisses out, because fuck Dean's voice is right in his ear and if he weren't already hard, he would be at that.
"So eager for me, couldn't even wait til tonight, could you?"
"No, sir, please-"
"You hard yet?"
"Yes, sir. Have been all night..."
"You didn't open the lube yet, did you?"
"No, you- I was waiting for you to tell me to. Tell me what to do with it." He reaches for it in anticipation.
There's a hiss on the other end of the phone and some movement. "Yeah, yeah I can do that for you, sweetheart. First I want you to stroke yourself a bit, just to ease some of the tension."
Cas does as he's told, working himself slowly. He wasn't kidding when he said he's been hard all night, but it'd been more of an ever present arousal that never fully left even in the few hours of sleep he managed. Now it takes no more than a few strokes to feel his erection aching for more than the teasing he's currently allowing himself.
A whimper escapes before he can bite it down, but Dean must hear it. "That good?"
"Not enough," he whines.
"Alright, baby, don't worry, I'm gonna take real good care of you. I want you to grab the lube, get your fingers nice and coated."
He lets go of his cock in favor of following the directions. He props the phone against his shoulder to free his other hand when he has issues opening it. This is heaven, honestly, having Dean whispering what to do. It's so much better than the half-formed fantasies he's been running through all night, because now he can do something about it. Not just imagine Dean helping him get off, but move towards that goal.
The lube's cold, but he doesn't take the time to warm it up between his fingers. No, that's an unnecessary distraction. So instead he coats his fingers generously and starts tracing gentle circles around his rim. He's too tense, too excited and needs to relax first.
"Talk to me, Cas."
"I'm-" He gasps as he tries to push in with one finger. It goes in at first, but the intrusion just causes his muscles to tighten up again. He pulls back out in frustration, whining. "I'm just... Haven't gotten... I..." The rest dissolves in a wordless plea.
"You need to calm down. Can you relax for me? Please, baby, want you to feel good. Keep circling your hole for me, nice and slow. You doing that?"
"Yes, sir."
"You keep doing that, and when you're ready, you push in. Just one finger for now, okay? That plug I got you is kinda big, don't want you to get hurt stretching out too fast."
"Yes, sir." His body has already loosened up just listening to Dean, so he tries his index finger again. He sighs when it meets no resistance, keening happily as he gently pumps in and out.
"Sounds like success so far. You ever done this before, Pretty Boy? You ever opened yourself up for a toy?"
"Yes." It's hard to concentrate on what he's doing while talking, but he doesn't want to disappoint Dean. He swallows and tries to collect his scattered thoughts. "I... I have a dildo that I use. Got it... A friend got it for me for my birthday when I was sixteen..."
Dean laughs. "Must've been a real good friend, takin' care of you like that."
The memory of his sixteenth birthday replays. Meg smiling deviously at him as she hands him the gift, wrapped in obnoxious pink paper with a big white bow. He'd blushed so much when he'd opened it but he'd been so pleased. He wasn't brave enough to buy one for himself, but Meg had a way of seeing through the front he put up and what he hid underneath. That's why they'd gotten along so well.
"Yes, sir. My best friend from high school." He's much more open now, so he hesitantly adds a second. The stretch doesn't quite burn, so he gets back to work pumping in and out, occasionally scissoring out.
When he next hears Dean, the gravel of his voice makes his movements stutter. "They show you how to use it or let you try it out on your own?"
A new image comes to mind, this time of Meg's bedroom. Her coy look as she'd pushed him onto the bed and opened him up just like he's doing now. Of her pegging him as he begged for more.
"Yes," he whines. "Yes, she did."
"She- she?" Dean splutters and then moans himself. "Jesus, Cas, you are best thing that's ever happened to my sex life, I swear to god."
Cas hums happily.
"How many fingers you working into that pretty hole of yours, Cas?"
"Two," he says, but then adds some lube and pushes in a third. "Three, sir."
"I bet you look so fucking beautiful, on your bed and working yourself open. Gonna look even better with that plug in you, keeping you stretched out all day for me."
He can't help but moan at that, because sure he'd thought maybe... But Dean's words are so suggestive, hinting at what else he has planned for him. On a whim, he pulls his phone from his ear and opens up the camera app. Takes a short video of himself, fingers at work and cock leaking precum onto his belly, and then sends it before he can change his mind.
Cas knows the exact second Dean gets the message, hearing the little notification bing, and even better he can tell when Dean's finished watching the video.
"Cas-" he gasps and then there's movement. And sure, it's muffled by the phone, but it sounds like-
"Sir, are you- Are you touching yourself?"
"Fuck yeah I am. You think I can watch my- watch you open yourself up for me and not jerk off?"
"Can I- Sir, I think I'm ready for the plug, may I-"
"Yes, fuck Cas, yes!"
His fingers leave him feeling empty, but that's not going to be a problem. Not if he's expected to have the plug in all day. Wear it until Dean's ready to use him. Hell, maybe he'll even draw this out, wait until tomorrow. Make sure Cas is full until then.
With those possibilities in mind, he squeezes lube onto the plug, coating its considerable girth. (And maybe he compares it to how Dean felt in his hands just a few days ago.) He shifts so he can get it between his legs and angle it just right. At the first push, only the tip breaches the puckered opening.
"Cas- Tell me... tell me what you're doing."
"I'm pushing it in, just a little." He lets out a shaky breath as he adjusts. It's firmer, less forgiving than his fingers were. Cas pushes a little more forcefully. "Maybe an inch now, sir. Should I-"
"Hold it there for now." Dean's breathing is labored and his words come out in a rush. Cas can almost see him, sprawled out on his bed, and working his hand needily over his cock. "Push it in another half inch, then pull it almost all the way out. Push it in a bit farther, pull it almost all the way out. Keep doing that, baby, work it in inch by inch."
"Sir," he whispers, afraid to ask but wanting, needing to see if Dean's really as debauched as he's picturing. "Can I... can I see you?"
"You wanna see me? See me jerking off while I picture all the things I'm gonna do to you later? While I'm listening to you get ready?" Cas can only manage a whimper in reply. "You be a good boy and keep working that toy into you, okay?"
"Ye- yes, sir, I... Yes."
He waits eagerly, phone warm against his ear. It's an awkward place to hold it, but the idea of turning the speaker on is too distressing. He likes having Dean's voice close, likes pretending he's leaning back into his arms instead of his pillows. Sure the stiffness in his neck almost ruins the illusion, but it's better than the alternative.
By the time his phone vibrates with the incoming message, he's gotten most of the plug in. Cas scrambles to open it - no small feat considering what he's doing and that he can barely navigate the phone with just his left hand. It's worth the trouble when the video starts playing.
Dean's on his bed, jerking himself fervently as his thumb reaches up to smear the precum down along the head. Unlike Cas, who's completely bare, Dean has most of his clothes on. Instead of undressing, he's simply shimmied a bit out of his pants, pulling them down just enough to get them and his underwear out of the way.
He expected a few seconds that he could play over and over, save to enjoy for later, but it keeps going. There's a low groan, something deep and guttural he'd barely heard when it happened a few minutes ago, and then Dean's coming onto his shirt. The first spurt nearly hits the phone, but the rest pools by his belly button.
So entranced by what he sees, Castiel doesn't notice that his last push sent the plug completely into him. He clenches around it and moans. "Sir, you look so good when you come... Wish I was there to clean you up, to lick it all up-"
"Next time, don't worry. You got that plug in yet, baby?"
"Yes-"
"You've been such a good boy for me this morning, you know that? I think you've earned being able to come."
"Thank you, sir-"
"But I've still got plans for you tonight. You gonna be able to come for me later if I want you to?"
"Yes, sir, I think so. For you, I could."
"Alright then, here's what you're gonna do. You're gonna jerk yourself off right now. While you're doing that, you're gonna tell me all the things you thought about last night that kept you up. Let me know exactly what got you so worked up you texted me this morning in the middle of breakfast. And then you're gonna clean yourself up and go to class. Can you do that for me?"
He nods, already moving his hand to his poor neglected dick, then remembers that Dean can't see him. "Yes, sir."
"Tell me what you thought about, Cas. Wanna know so I can do all those filthy things to you."
"I... I thought about how good it felt giving you head, how I- how I liked being on my knees for you. Thought about other ways I could... I could service you. Braced against your headboard, or- Or bent over your desk. Wished... wished I could jerk you off in one of your classes like you did for me..."
Dean keeps coaxing more out of him. All the dirty fantasies his imagination had run away with over the course of the last week. Cas starts to lose coherency towards the end. He pumps into his fist (thank god for the extra lube), uses his other hand to tease his balls and at the edges of the plug.
"So close, aren't you baby? Come for me, Cas. Wanna hear you."
Normally Cas would try to keep quiet - between growing up with family that was always around and his current roommate situation, he's nearly a master of the silent orgasm. But he's alone and Dean wants to hear, so he lets go and moans loudly as he comes all over himself. If he thought Dean almost hitting his phone was impressive, it's nothing to how a few drops of cum land on his chin.
In his post-orgasmic haze, he blanks out. His senses don't register anything other than the physical sense of relief that washes through his system. Eventually he hears Dean whispering, "You with me, Cas?"
"Yeah. I'm... I'm here."
"You sound pretty fucked out right now."
"Yes," he agrees. He might be able to answer, but higher brain function is beyond him.
"Wish I was there to enjoy it." Any part of him that thinks Dean sounds wistful is easily ignored.
"Me too." Later he'll have time to worry about if that sounds like a confession or not. For now, though, it slips out because it's the truth.
"Alright." Dean sounds hoarse but a quick cough covers it up. "Get yourself cleaned up. Don't be late to class on my account. And uh, take it easy today."
Cas lets out a shaky breath as he moves, the plug suddenly very much there. Taking it easy will definitely be a necessity. "Okay."
There's a lingering silence, as though Dean has more to say. Castiel waits patiently as he shifts a bit, learning the ways his body will be able to move without sending jolts of pleasure/pain through him. "I'll, uh... I guess I'll see you at free hour, then."
"Of course, Dean."
