Supernatural Smut Oneshots

I Won't Let You Die A Virgin/Destiel

What this is based on is Season 5: Episode 3 (I'm pretty sure) Which had a lot of potential for some Destiel shit

Context: Cas and Dean are looking for Raphael and Cas is pretty sure he's gonna die when they find him so Dean takes him to a strip club because he doesn't want Cas to die a virgin, but that fails when Cas says something to the Woman he's going to have sex with that upsets her and gets him kicked out of the club.

"This is hopeless!" Dean says, exasperated.

"Dean I don't see why this is so important to you. It's okay if I don't have sex with the pretty woman," Castiel says. Truth is, he wasn't all that interested in her.

They had gone back to their current motel and were sitting at a small two-seater table across from each other. "Well if you're so sure we're both gonna die we should enjoy our last night," Dean says. "And that means getting drunk and getting off." He takes a swig of his beer and pours Cas a shot of whiskey. Cas reluctantly downs it and makes a face like he just sucked a lemon, even for an angel that shit burns.

"Well I understand the drunkness, but I don't see the value in your so called "getting off" as I believe I've never done that before," Cas says.

Dean raises his eyebrows. "You haven't even jerked it? Seriously?"

"I'm not sure what you mean by that," Cas says.

"Come on, cranked the hog, flicked the bean, tickled the pickle. You've been on earth a while, surely you've gotten horny," Dean says, leaning back in his chair.

"I still don't think I know what you mean, but I do know what horny is. Is that when I wake up with a hard and enlarged penis? Or when I see some people's bodies and get all hot and sweaty?" Cas asks.

"Yeah and it's not a 'hard and enlarged penis'. That sounds gross. It's a boner or a hard-on." Dean says. "I mean have you ever rubbed it to make it go away? Has anything other than piss come out of it?" Dean explains.

"I haven't ever rubbed it, but I have woken up with a white substance in my boxer briefs after dreaming of something explicit," Cas says, his cheeks flushing red.

"Okay yeah," Dean says. "Well it doesn't matter. We're not going to be able to find someone who can manage having sex with a confused angel by morning."

"Well you're here," Cas says. "Couldn't you manage?" Dean starts to choke on his beer. "Are you okay?" Castiel asks with his concerned head tilt.

"Uh yeah I'm- I'm okay," Dean takes a few deep breaths. "What do you mean Cas?"

"Well you want me to lose my virginity so bad, why don't you just take it?" he says far too casually.

"Cas I don't- I mean- I- no I mean- are you sure?" Dean struggles.

"Why wouldn't I be?" Cas says.

"Well we're friends Cas. You don't want to fuck that up," Dean says awkwardly.

"If we're dying tomorrow than what is there to "fuck up"?" Cas says.

"I guess you're right," Dean says.

"So what do I do?" Cas says.

"Just- let's go stand by the bed," Dean says walking over to the motel queen. Cas follows. "Come here." Cas stands closer to Dean. Dean pulls him closer by his biceps and kisses him eagerly. It takes Cas a second to figure it out but he starts kissing back. He puts his hands on Dean's back, pulling him closer as they continue to make out. Dean pulls back for air.

"Well I like that," Cas says. Dean chuckles.

"Yeah me too Cas. Take your shirt and pants off and lay on the bed." Dean says and does the same. Cas complies instantly as he has no concept of insecurity and trusts Dean completely. Dean straddles Cas's hips, both just in their boxers. "Just tell me to stop if anything makes you uncomfortable okay?" Dean says, seriously and sweetly.