Timeline Season 5
The Impala is breaking the speed limit by 27 miles per hour, the road flying by, the dark trees on either side of the two-lane highway seemingly a blur.
“I really don’t think you should be dr–,” Sam starts.
“Shut up, Sam,” Dean growls, cutting Sam off.
Dean’s already sweating. Cas can see the slight tremble wracking Dean’s body. He can’t see Sam’s face, but by the tone of Sam’s voice, Cas knows Sam’s worried.
“We’ll be there soon,” Dean says through clenched teeth. “Me ‘n Cas will go to the room. Go and get yourself a room at the other end of the motel. I’ll text you when everything’s okay.”
“Okay,” Sam says, though Cas knows Sam doesn’t like the plan. Or the fact that Dean’s driving in his condition.
Castiel knows this could easily turn into a disaster. He’s glad Sam wasn’t anywhere near the patch of flowers they walked into. If he had the full power of his grace available to him, Cas could fix them both, but he doesn’t.
It feels horrible. And Cas can’t even imagine what it must be like for Dean, who doesn’t have any grace at all. It feels as if there are bugs crawling all over his skin, and his physical body is craving sex badly enough that he’s been painfully hard since just a few seconds after they walked through the flowers.
“Do you guys need–,” Sam starts again.
“Shut up, Sam,” Dean barks.
This time Sam stays quiet. Cas knows Dean’s freaking out. He knows why Dean’s freaking out. He knows Dean inside and out, saw everything when he raised him from Perdition and made a new physical body for him.
Castiel knew Dean had sexual experience with men before Hell, and he’d even liked it, though it wasn’t all that often he did it. But Cas also knows that Dean hasn’t been with a man since Hell. Dean would never admit to all the things Alastair did to him in Hell, and Cas wishes he could erase it from Dean’s memory.
He’s offered to do that very thing, but Dean said no, and Cas respected his wishes. Cas knows it’s still hard for Dean to deal with, and he knows Dean would be out there enjoying sex with both men and women if it weren’t for what Alastair did to him.
The tires of the Impala squeal as Dean makes a fast turn into the parking lot of the motel they’re staying in. Sam gets out of the car before Dean’s even got the key out of the ignition. Dean’s panting, and after he pulls the key out, he sits there just shivering and breathing.
“You’ve never been with a guy, have you,” Dean says.
He knows Dean’s not really asking, but he answers anyway. “No.”
“Fuck,” Dean breathes, scrubbing his face with his left hand, the right hand tightly clutching the keys.
Cas wants to say something, to do something to make this all better. He can’t fix it, and there’s a physical ache in his chest because of it.
“Okay, c’mon,” Dean says, opening the door and getting out. “I feel like shit, and I know you gotta be feeling pretty bad yourself, so let’s do this,” he says, then slams the door and heads toward the motel room door.
Castiel follows him, slamming the car door as he goes. He’s got enough grace left to perform a quick check of the motel rooms close to theirs, and he’s grateful they’re unoccupied. By the time Cas gets into the room, Dean’s pulling off his own clothing.
Cas’ hands are shaking as he closes the door. He can already feel himself sweating, and his clothes are sticking to his body in uncomfortable places. His dick is throbbing, and he’s trying hard to concentrate on keeping calm. He doesn’t want to attack Dean even if his body seems to want nothing but that.
Dean kicks his shoes into the corner of the room, his back turned to Cas. “I’m gonna let you top, er, I mean, I’m gonna let you fuck me because you’ve never done this before,” Dean says.
Cas can hear the tremor in Dean’s voice, and it makes that ache in his chest even worse. “I’ve never had sexual relations, but that doesn’t mean I have no knowledge of sex at all, Dean,” Cas says.
Dean huffs. “I know you’re not stupid, Cas,” he says as he kicks his pants and underwear off in the same direction his shoes went before. “It’s just different when it’s actually happening to you, and I already am having trouble controlling myself, and I don’t wanna hurt you,” Dean blurts, his shoulders tense.
Cas doesn’t say that he’s worried he’ll hurt Dean himself. He doesn’t say he’d rather be in pain than cause Dean pain. He doesn’t say he knows why Dean’s so scared, that he knows it’s not just because he thinks he’ll hurt Cas, but that it’s also because he’s worried he’ll like hurting Cas. He doesn’t say he knows how much Hell changed and damaged Dean. He doesn’t say that Dean’s soul is so beautiful and wonderful that it’s slowly ridding itself of that damage it received in Hell.
“I trust you,” Cas says instead, because he really does trust Dean. With all his flaws and the dark and distorted places on his soul, he’s still a good man who tries his best even with forty years of Hell inside him.
Dean snorts. “You shouldn’t,” he mumbles.
Cas is about to say something else, but Dean stalks over to the bed, climbs onto it, and settles in the center on his hands and knees. The sight is enough to make Cas moan loudly, and his cock throbs so painfully that he grabs his crotch, pushing and rubbing even though he knows it won’t make it stop hurting.
“Do you have lubrication?” Cas asks, and now he can hear his own voice trembling.
Dean’s shoulders slump. “Outside pocket of my duffel,” he says softly.
Cas tears his clothes off, the tie choking him in his haste. He quickly locates the small tube in Dean’s duffel, then walks up to the end of the bed. Dean’s dick is hard and leaking, and his body is shaking hard instead of just trembling like it was before.
“It’s gonna be okay, Cas,” Dean says.
Cas climbs onto the bed behind Dean, his love for Dean strong, because even though Dean’s terrified and in the middle of the effects of the pollen himself, he’s thinking of Cas, making it easier for Cas.
“Relax,” Cas says, reaching out and running his hand over Dean’s back.
Dean flinches and gasps, then gets himself under control again, though he’s still shaking. “Just fuck me,” he says gruffly.
Cas can feel the effects of the pollen clouding his brain and the small amount of grace he has left. The urge to force his way into Dean and fuck him until Dean’s a screaming mess is damn near overwhelming. He panting and sweat is rolling down his forehead into his eyes. He wipes it away with the back of his hand, then fumbles with the tube in his hands.
He squirts too much of it on his fingers, some of it dripping onto the bed, and then dribbles a bit at the top of Dean’s crack.
“Fuck! Cold!” Dean complains, but he keeps still except for the shaking.
Cas closes the top on the tube and sets is next to him on the bed. He blinks the sweat out of his eyes as he pushes his index finger into Dean.
“Ah!” Dean yelps, lunging forward, Cas’ finger pulling back out of him.
Cas whines, his thighs shaking and his dick so full and red that he swears it’s going to explode if he doesn’t fuck Dean right the fuck now.
“Sorry,” Dean says, getting back into position. “I just, that, I didn’t expect you to just shove your finger in there. Sorry.”
Cas holds his breath, grabbing Dean’s left hip with his hand so Dean can’t get away, then shoving his finger back inside Dean. Dean yelps again, trying to get away, but Cas holds onto him. He pushes in as far as his finger will go, pulls back, then shoves his middle finger in alongside his index finger.
“Fuck! Cas, gimme a sec!” Dean says.
Castiel feels bad that he’s being so forceful, but he needs this so much that he’s getting scared. There’s a feeling of doom running through his body. He doesn’t know if Dean feels the same thing, but he needs to fuck something. Anything. He can’t be fucked himself. That won’t work. He has to fuck.
Cas shakes his head, trying to get a hold of himself. He’s fingerfucking Dean, and Dean seems to be relaxing into it a bit more now, but he knows he’s already hurt Dean.
“I’m sorry,” Cas mumbles, gentling his left hand on Dean’s hip, rubbing Dean’s skin with his thumb in apology.
Dean makes a noise like he’s trying to hold something in, and if Cas wasn’t so affected by this pollen, he’d know how to help.
“Just fuck me,” Dean says again, more force behind his words this time.
Cas pulls his fingers out, then slicks up his cock. His fingers are shaking badly enough that he has a hard time aiming his cock, but he gets it to Dean’s hole, then starts pushing in.
Dean’s panting so hard it sounds like he’s gulping in air, nearly grunting with the effort to keep still and let this happen. And once the head of Castiel’s cock pops inside, Dean lunges forward again, yelling and babbling as he loses his balance and falls face-first into the pillows, his legs and arms all over the place.
Cas knows something has changed in Dean. He can tell by the way he’s no longer attempting to control himself, by the way he’s whimpering and jerking on the bed.
“I didn’t mean to!” Dean blurts. “I won’t get out of position again, sir! Please don’t! Don’t do the, don’t, fuck, don’t make me, please!” he says, a sound like a sob coming from deep inside him.
Cas melts. Even though he’s in pain, so hard he’s scared he’ll explode, he can’t leave Dean like this. He recognizes the words. He knows Dean’s stuck in a flashback, doesn’t even remember it’s Cas behind him and not Alastair.
“I won’t do it again! Don’t make me hurt him! I’ll stay in position, just don’t make me hurt him!” Dean begs, pulling himself back to his knees again, but so shaken by everything that he’s having a hard time doing it.
Cas nearly cries. He knows what Dean’s asking for. Alastair was very good at his job. Dean was expected to hold still for anything Alastair did. He could say anything he wanted, scream as much as he wanted, but he had to stay in position or Alastair would come up with horrific things to make Dean do.
Alastair knew Dean inside and out, almost as well as Cas knows Dean now. He knew that for someone like Dean, you could hurt them by never even touching them. Sure, he hurt Dean plenty. But when it came to punishment for things like not staying in position, forcing Dean to do things to souls Alastair manipulated to look and act like the ones Dean loved topside was the real torture.
Cas wipes his hand clean on the blanket below him, then grabs Dean’s legs, manhandling him onto his back with Cas between his legs. Dean’s got tear tracks down his cheeks, his eyes are watery, and eyes are wide, but he’s looking at something over Castiel’s left shoulder that isn’t really there. Something he saw in Hell.
“Look at me, Dean Winchester,” Cas says in a voice as different from Alastair’s tone and inflection as he can. No teasing tone. No haughtiness. Still forceful enough to get Dean’s attention, but with no anger.
Dean whimpers, more tears leaking from his eyes and running into his hair. “I’m sorry,” he whispers, panting so hard that Cas worries Dean will make himself pass out.
“Dean,” Cas says, a little softer this time. Nothing is soft in Hell. Nothing is kind. Cas needs to pull him out of it with something different. Something real and right now and here. “It’s Cas. I’m not going to hurt you. Look at me. I’m not going to do anything else until you come back to me,” he says as he rests his hands on Dean’s upper thighs, gently running his fingers over Dean’s skin.
“Don’t make me do that,” Dean whispers, his eyes roving about for a moment longer, then finally focusing on Cas.
“I’m not going to make you hurt anybody,” Cas says, softening his words even more now that Dean’s eyes are focused on him. “Calm down and match your breathing to mine,” he says, noticing that Dean’s body has relaxed some.
Dean finally comes out of the flashback the rest of the way. Cas can tell immediately when he does because his eyes clear, his breathing slows, and the bowstring-tight posture relaxes.
“Fuck, Cas, I’m sorry,” Dean says, wiping at his face with his hands. “Sorry, I, fuck, that was fucking ridiculous,” he says with a tone of voice that says he feels really stupid.
Cas knows Dean well enough that he doesn’t try to say everything’s okay. Because everything’s not okay, and Dean doesn’t fall for bullshit like that. Instead he leans down and kisses Dean gently, his lips caressing Dean’s more than anything else.
Dean’s body tenses again at first, but then he relaxes into it, his eyes falling closed and his hands sliding up Cas’ sides and over his back to pull him closer.
Castiel has never kissed anyone before, but he immediately likes it. It’s intimate in a way that nothing else he’s done so far has been. When he feels Dean’s body relax into his, he feels triumphant. He still has the urge to fuck Dean mercilessly for hours, but the man under him is worth denying himself, worth controlling himself with every last part of his being.
Cas pulls out of the kiss, looking down at Dean with as much affection as he can project. He knows he’s not good at social cues. Dean’s told him that plenty of times. But he must be getting it somewhat right because Dean looks surprised. Pleasantly surprised.
“Keep looking at me,” Cas says. “This is me, and I won’t hurt you. Just stay with me,” he says as he reaches down and gently pushes his index finger inside Dean, projecting his movements so Dean isn’t surprised.
Dean doesn’t flinch this time, and when Cas pushes his middle finger in with his index finger, this time Dean works at relaxing, his eyes fixed on Cas’.
“Sorry,” Dean says again, his eyes welling up some.
“You have nothing to be sorry about,” Cas says firmly, using his left hand to smooth over the skin of Dean’s leg, his stomach.
Dean lets out a noise somewhere between a laugh, a snort, and a sob. “I really gotta fuck or my dick’s gonna explode,” he says.
Cas smiles, then adds a third finger inside Dean’s hole. “If that were possible, mine would’ve already exploded,” he says.
Dean laughs, and it’s a wonderful sound. “Well, then fuck me!” he says with a grin, wriggling his hips and wagging his dick back and forth with the movement.
Cas chuckles as he pulls his fingers out. He lines up his cock and slowly pushes in, keeping eye contact with Dean. Dean grimaces, but he doesn’t loose eye contact with Cas.
Dean takes a shuddering breath, whimpering as Cas bottoms out. “I haven’t been with a guy since Hell,” he says.
“I know,” Cas says as he leans over, getting as much skin-on-skin contact as he can, knowing it will ground Dean and help keep the memories and flashbacks at bay as much as possible.
“I couldn’t,” Dean whispers.
“I know,” Cas says softly, then kisses Dean again, just briefly so that he can reestablish eye contact, starting to fuck Dean at a slow, lazy pace.
“Oh, fuck, you’re fucking me,” Dean breathes with a smile. “Sam owes me twenty dollars.”
Cas tilts his head. “Why?”
“He said I wouldn’t be able to get you to lose your virginity with a girl, much less a dude,” Dean says.
Cas nods. “Then we should use the money to buy more lubrication,” he says.
Dean laughs. “It sounds like you think you’ll be doing this again,” he says, his body already writhing on the bed, his hips pushing up to meet Cas’ thrusts.
Cas fucks him a little faster, enjoying the way Dean’s legs wrap around his waist to pull him in harder. “I knew you wanted to have sex with me, and I was hoping it would’ve been under better circumstances, but I was giving you time to see that you could survive, to see that you could be the man I already know you are.”
Dean’s breath catches, and his eyes well up again, but he breathes out a laugh, pulling himself out of the darker places in his head. “I was getting around to it,” he says.
“I know,” Cas says fondly, kissing Dean again.
“But I really gotta come soon or that exploding thing is definitely gonna happen,” Dean says.
Cas laughs, pushing himself up to get better leverage to fuck Dean harder. Dean unwraps his legs from around Cas’ waits and lets them fall to the bed, spread wide, and it sends a flare of arousal through Cas that Dean’s this comfortable with him. He knows it’s not going to be an easy ride, and flashbacks will continue to be a threat for a long time, but they can do this.
“C’mon, Cas. Faster. Fuck me,” Dean groans, pushing up into Cas’ hips.
Cas does as he’s told, fucking Dean harder and faster. He reaches down and starts jerking Dean off with his right hand while he holds himself up with his left hand.
“You sure you’ve never done this before?” Dean asks, arching his back and groaning.
“I have knowledge but lack experience. I plan on receiving a lot of experience very soon with you,” Cas says with a grin.
Dean moans. “Oh, yeah, lots of that,” he says, grabbing onto the sheets as his body tenses, this time in pleasure instead of fear.
“Dean!” Cas says in surprise as his orgasm hits him unexpectedly. Having never experienced one himself, he didn’t realize it would come that fast, hit so hard, feel that awesome.
Dean gazes up at him, and it looks like he’s drinking in everything Cas is experiencing. “So fucking hot,” Dean breathes.
Cas slows as his orgasm fades away, forgetting for a moment that Dean hasn’t come, and when he remembers, he starts jerking him off again, fucking him again. He recalls the little things that Dean likes, so he adds a twist at the tip of Dean’s dick as he jerks him. Dean moans loudly when he does that.
“That was your first orgasm,” Dean says, as if he just wants to say it out loud.
“Yes,” Cas says, “you gave me my first orgasm.”
“Oh, fuck. Fuck! Cas!” Dean yells, his body tensing, back arching so much that Dean’s head is holding his weight as he comes all over his stomach, body trembling and his eyes squeezing shut.
Cas watches it all. He’s never seen it this way before. He’s never been the one to make Dean come. He’s awed by it. He wants to do it many, many more times.
Dean flops back down, panting and smiling as his eyes open and he looks up at Cas. He chuckles. “How many times do we have to fuck? I still feel like I gotta fuck,” he says, glancing down at his dick, which is still red and full.
Cas smiles, realizing his own dick is still fully hard inside Dean. “Let’s find out,” he says.