1 - 20 of 145 Works in Castiel/Dean Winchester First Time Having Sex

Pages Navigation

Listing Works

  1. Tags
    Summary

    Cas uses mind control to turn Dean into his needy come addict and cock slut, constantly begging for it and totally dependent on him.

    OR

    Dean's having trouble with his dick. Cas "helps" him out.

    Language:
    English
    Words:
    16,807
    Chapters:
    5/?
    Collections:
    3
    Comments:
    171
    Kudos:
    381
    Bookmarks:
    53
    Hits:
    13350
  2. Tags
    Summary

    Dean and Castiel love each other but nothing has ever been easy between them.
    Collection of OS : sometimes bitter and sweetness, other times with laughters and tears or sadness and comfort.
    But above all, with moments of happiness, because they deserve it more than any other.

    Language:
    English
    Words:
    1,578
    Chapters:
    3/?
    Kudos:
    6
    Bookmarks:
    1
    Hits:
    161
  3. Tags
    Summary

    Amara injured Castiel's grace and he's dying. He thinks the Winchesters won't care. Just how far will Dean go to prove him wrong?

    “My grace has settled.” His voice sounds bitter to his own ears.
    Dean winces, and he can practically feel the man draw away. From the way the veil drops over his open, inviting gaze to how his eyes now flit everywhere but to Castiel’s.
    “You only did this to keep me alive Dean.”
    “How do we know it even worked?” demands Dean, “You don’t even know for sure? Let’s just finish what we started.”
    Almost amused, Castiel grins, “Well, seeing as I’ve had my grace for millions of years, I believe my opinion will do.”
    “No! It – you – Jesus!” Dean hooks his ankles over Castiel and turns them so fast they almost tumble off the bed. Castiel realises what Dean wants… what he’s trying to do.
    He wants this to continue as much as Castiel does. But he’s too scared to ask. Castiel can see the shame swirling in his eyes, filtering back into his brain like poison. Dean will destroy himself over this whether or not it happens.
    He brings his lips to Dean’s once more shifting his hips so that the tips of their erections graze each other. “Let’s finish this Dean.”

    Language:
    English
    Words:
    33,705
    Chapters:
    12/?
    Comments:
    39
    Kudos:
    135
    Bookmarks:
    36
    Hits:
    2835
  4. Tags
    Summary

    After a hunt that ruins Castiel's pants, he goes to Dean's room to try and see if he has a pair that'll fit. That is one motive. The other motive, however, is that he is rather impatient that he and Dean have gotten nowhere with their relationship. He thinks it's time to change that.

    Language:
    English
    Words:
    2,456
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    63
    Bookmarks:
    3
    Hits:
    759
  5. Tags
    Summary

    "Nope, not really." Sam finished folding up a shirt and slipped it into his bag. "You know what today is, right?"

    "No?" Dean shook his head and grabbed his phone. December 24th. "Huh, I didn't realize we'd been here this long. Christmas Eve. Hopefully, the roads aren't too packed."

    Sam shook his head. "It's not the roads I'm worried about. It's the shops and maybe even the mall."

    "Why are you worried about those places?"

    "Well, considering I haven't had a chance to go Christmas shopping. How about you?" Sam zipped up his bag and did a second check around the hotel room. "I already took your bag out to the car. Anything you want to save that can be saved, throw in the bag on my bed. Otherwise, we'll hit a dumpster on the way to the mall." Sam crossed the room to the motel door and headed outside.

    Dean stood in silence for a moment as Sam closed the door behind him. Shopping, on Christmas Eve?

    Series
    Language:
    English
    Words:
    7,473
    Chapters:
    1/1
    Collections:
    1
    Comments:
    11
    Kudos:
    121
    Bookmarks:
    14
    Hits:
    1422
  6. Tags
    Summary

    The rest of the group burst into laughter, as Charlie shrugged, defeated. "Fine. Have I ever mentioned you suck as a best friend?" Cas laughed, as he had, in fact, heard it multiple times. "Oh! Before you all go!" Charlie put the lid on the Castles of Burgundy and hopped up from her seat. "It's that time!"

    Where the group had been laughing, it turned quickly into good-hearted ribbing and complaining. Charlie pulled out a small gift bag and handed it out to everyone. "Secret Santa!"

    Cas rolled his eyes as Charlie came to stand in front of him, gently shaking the bag. He reached in and pulled out a slip of paper, waiting until Charlie moved to the next person. He flipped it open, and butterflies fluttered in his stomach.

    Dean.

    Series
    Language:
    English
    Words:
    7,813
    Chapters:
    1/1
    Collections:
    1
    Comments:
    18
    Kudos:
    188
    Bookmarks:
    14
    Hits:
    2453
  7. Tags
    Summary

    Every transit of Venus, angels go into heat.

    Dean helps Castiel through it the only way he knows how - with love.

    Language:
    English
    Words:
    8,810
    Chapters:
    11/11
    Comments:
    32
    Kudos:
    186
    Bookmarks:
    12
    Hits:
    3491
  8. Tags
    Summary

    Before all this end of the world fuckery, and not that long after the Angel of Thursday soared in on awesome black wings, Dean had been so goddamn grateful at realising he had his first real friend, that his lusting over dark hair and the bluest of all baby-blues had just been an inconvenient itch, one he'd simply decided not to scratch. So, a mostly closeted but wholly bisexual Dean ignored the whole damn thing like a seasoned Winner.

    But that shit just wouldn't go away.

    Dean knew he had to stop it. Needed to pull all the weapons he owned on its ass, take it down to the boneyard, battered and bound, then kill it dead fucking dead. Bury the corpse, salt and goddamn burn it and leave the charcoal-grey ashes to disintegrate into the dirt and the nothingness. Leaving only a burned-out hole; the one that now lived in his chest.

    Why? Because Dean didn't know what to do with such emotion—and he sure as sin didn't deserve a return on it.

    Language:
    English
    Words:
    7,300
    Chapters:
    1/1
    Comments:
    31
    Kudos:
    92
    Bookmarks:
    16
    Hits:
    1331
  9. Tags
    Summary

    "Fine." Cas slid his right pointer finger into the trap and almost instantly felt the trap snap around their fingers.

    "That's not right." Dean looked up at Cas. "What did you do?"

    Cas attempted to pull his finger out of the trap. "I didn't do anything."

    "Remember, push in, then we can slide out." Dean tried to push their fingers together. "What the hell?"

    "I thought you said this was a child's toy? What is this, Dean?" Cas tilted his head.

    Dean turned bright red. "Sonofabitch." He jumped up from the bed and ran down to Sam's room, dragging Cas behind him, and banged on the door. "SAMMY! OPEN UP!"

    Series
    Language:
    English
    Words:
    5,749
    Chapters:
    1/1
    Collections:
    1
    Comments:
    12
    Kudos:
    187
    Bookmarks:
    13
    Hits:
    2426
  10. Tags
    Summary

    It started off simple. An ad on Craig's List:

    Looking for a Roommate, 700/mo, Utilities included.

    My brother has apparently grown a pair and is moving in with his fiancée. This leaves me with an empty room in a spacious apartment downtown. I can afford the rent on my own, but I'd rather not.

    Your 700/month includes your room, utilities, a parking spot if you need it (apartment comes with two, and I'm using one), free use of the public areas in the apartment, and a -I like to think- pretty chill roommate.

    I only require a couple of things. Must clean up after yourself, must be LGBT+ Friendly, must be cool with guests (we'll respect privacy).

    Check out the included pictures, and if you're interested, send me a message!

    Series
    Language:
    English
    Words:
    9,031
    Chapters:
    1/1
    Collections:
    1
    Comments:
    12
    Kudos:
    220
    Bookmarks:
    18
    Hits:
    2869
  11. Tags
    Summary

    Without his wings to guide his descent after he was banished by the intruder in the Bunker, Castiel crashes into the ground, leaving his body nearly as broken and bruised as his heart. Only his promise to Dean to protect Sam compels Castiel to stand up again. After days of dragging himself back to the Bunker, Castiel discovers that Sam is all right and Dean is alive! What should be a joyous reunion is marred by Castiel’s self-doubts. If the Winchesters don’t need him, and Heaven doesn’t want him, where does Castiel belong?

    [Canon divergent from the end of 11x23 Alpha and Omega]

    Language:
    English
    Words:
    29,622
    Chapters:
    8/8
    Collections:
    2
    Comments:
    96
    Kudos:
    253
    Bookmarks:
    56
    Hits:
    2546
  12. Tags
    Summary

    Following the events of 15x03, The Rupture, Dean is regretful, Cas is heartbroken, and Sam is furious at his brother for treating Cas so badly. However, upon hearing Dean's reason for acting as he did, Sam vows to reunite his brother with Cas, whatever it takes.

    Language:
    English
    Words:
    8,378
    Chapters:
    1/1
    Collections:
    1
    Comments:
    28
    Kudos:
    190
    Bookmarks:
    18
    Hits:
    2390
  13. Tags
    Summary

    "So get this... We've got couples missing at a couples retreat the next state over."

    "Which lovely lady you going with?" Dean uncrossed his arms and smacked Cas' hand away from the tablet so he could scroll through the article.

    "Can't find one. Charlie's still not back. Jody's taking Donna on a hunt."

    Cas looked up. "Well, there was a lesbian couple that went missing. You can choose a male partner."

    "I was hoping you'd say that, Cas." Sam shot a look at Dean before smiling at Cas. "Will you do me the honor of being my fake husband for a case?"

    "Excuse me?" Dean shot a look at Sam.

    "Well, I'm not asking you, Dean." Sam shook his head. "That's... Yeah, no."

    Dean crossed his arms over his chest again. "Why are you and Cas going? Cas is my best friend. He and I can pull it off better than you two can."

    Series
    Language:
    English
    Words:
    8,491
    Chapters:
    1/1
    Collections:
    1
    Comments:
    12
    Kudos:
    244
    Bookmarks:
    22
    Hits:
    3064
  14. Tags
    Summary

    It's been three years since Dean's had any kind of vacation. Until now. Sam and Eileen gift him a cruise as a thank you for all the things he's done for Sam, for them, for the whole family.

    A week away at sea seems like an ideal vacation. Still, when your name is Dean Winchester, and nothing in your life has ever gone your way, it looks like a disaster waiting to happen. Can a new friend help him turn his luck around and help him navigate the rough waters?

    Series
    Language:
    English
    Words:
    36,947
    Chapters:
    20/20
    Collections:
    1
    Comments:
    144
    Kudos:
    262
    Bookmarks:
    62
    Hits:
    2293
  15. Tags
    Summary

    "You think I want to keep her here against her wishes?" Bobby shook his head vehemently. "She'd be one hell of a creature if she were one, but she should go back to the human world. There's a problem that you didn't think of."

    "What's that?" Dean spat.

    "Dean," Sam softly interjected. "The angels may not want or need Claire anymore because she can no longer be an angelic host, but she is still tied to a source of grace." They all looked at the Fallen.

    "I can protect myself!" Claire spoke up. "What do you think I had to do when Castiel couldn't come to me thanks to the stupid rules you all have in place!?"

    "Can you protect yourself from three or four or five angels?" Bobby stared at her. "I'll give you one or two, you're a spitfire. But they want him. They're not going to take it light and risk losing a couple when they need all hands on board."

    "So what? You want to keep her here?" Dean asked.

    Series
    Language:
    English
    Words:
    6,325
    Chapters:
    1/1
    Collections:
    1
    Comments:
    7
    Kudos:
    69
    Bookmarks:
    1
    Hits:
    882
  16. Tags
    Summary

    If Dean didn’t look away now, he’d be popping a boner like a fourteen-year-old finding his first skin mag under Dad’s bed.

    He resumed his saunter back to the table just as the Hot Dudes peeled themselves apart.

    "Cas..." Dean grunted, setting the drinks down and immediately sinking both his whiskeys as Cas joined them. “Who're these fellas?"

    OR

    The one where Destiel meet Sterek...

    Language:
    English
    Words:
    6,082
    Chapters:
    1/1
    Collections:
    1
    Comments:
    29
    Kudos:
    162
    Bookmarks:
    20
    Hits:
    2196
  17. Tags
    Summary

    “I’m still not going to talk about it, Sam.” Dean’s back was to the door, and his head was resting in his palms. “I’m not in the mood.”

    “Would caffeine help, Dean?”

    Cas’ voice caused Dean to whip around and look at the door. “Uh. Yeah, it’s um...” Dean ran his fingers through his hair. “It’s appreciated, Cas.”

    “I’m glad to hear it, Dean.” Cas set the coffees and the bag of pastries down on the table before carefully pulling one out of drinks out of the tray. He crossed the room and sat down on the bed next to Dean, handing him the cup. “Sam told me that you were suffering from some head issues.”

    “Son of a bitch.” Dean let out a half-hearted chuckle before taking a sip of his coffee. “Of course he’d say that.

    Language:
    English
    Words:
    2,450
    Chapters:
    1/1
    Collections:
    1
    Comments:
    14
    Kudos:
    142
    Bookmarks:
    14
    Hits:
    1984
  18. Tags
    Summary

    "Nobody told you. Nobody explained. You're just shoved out kicking and screaming into this human life, without any idea why any of it feels the way it feels, or why this confusion, which feels like it's … a hair's breadth from terror or pain. You know, just when you think you do understand, it'll turn out you're wrong. You didn't understand anything at all."

    After taking out the Rit Zien, Cas finds he has no where to go and asks Dean if he can spend the night with him in his motel room.

    Language:
    English
    Words:
    7,058
    Chapters:
    1/1
    Collections:
    1
    Comments:
    18
    Kudos:
    118
    Bookmarks:
    6
    Hits:
    1383
  19. Tags
    Summary

    Cas nodded and followed after Dean as they made their way to the elevator. They took the ride up in silence, Dean trying his damnedest to not stare and admire Cas. He knew that Cas humored him for the evening, listening to him rant about issues in Modena. But the looks he received in return, the smiles, the genuine interest. If there was any interest returned, Dean was screwed.

    The elevator dinged and the doors opened, letting them off onto their floor. They walked the few feet to their shared room, with the single bed and the probably not-as-comfortable couch. Cas unlocked the door and opened it, and Dean followed inside, turning to close it and lock it.

    As Dean turned back around, Cas was already sitting on the couch, taking off his shoes. He walked closer and looked at the bed before looking at Cas. "So, I was thinking."

    Cas looked up. "About?"

    "We're adults, right? It's a king-size bed. There's room for both of us on there. There's no need for you to sleep on the couch. It's not like you were kicked there for doing something wrong. You haven't done anything wrong."

    Series
    Language:
    English
    Words:
    7,080
    Chapters:
    1/1
    Collections:
    1
    Comments:
    24
    Kudos:
    210
    Bookmarks:
    16
    Hits:
    2003
  20. Tags
    Summary

    Dean wants to show Cas a movie, and Cas is excited to see it. At dinner though, Sam makes suggestive comments that confuse them both. Dean almost changes his mind about watching the movie in his room, alone, with Cas, after Sam makes him feel awkward about it. That night Dean has an... odd dream... that gets him thinking. He hopes Cas doesn't know about it, I mean, how could he?

    Language:
    English
    Words:
    11,119
    Chapters:
    10/10
    Comments:
    3
    Kudos:
    60
    Bookmarks:
    1
    Hits:
    1528

Filters

Filter results:
Submit

Include

?
Include Ratings
Include Warnings
Include Categories
Include Fandoms
Include Characters
Include Relationships
Include Additional Tags

Exclude

?
Exclude Ratings
Exclude Warnings
Exclude Categories
Exclude Fandoms
Exclude Characters
Exclude Relationships
Exclude Additional Tags

More Options

Crossovers
Completion Status
Word Count
Date Updated
Submit

Pages Navigation