1 - 20 of 69 Works in Dean Winchester's First Time With a Man

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  1. Tags
    Summary

    *clap*clap*clap*clap*

    Dean's perpetually single and lonely in a crappy apartment in his hometown, with no end in sight to the physical and emotional issues that prevent him from moving forward or fully participating in a life and world that's passing him by. His new roommate's turning out to be a bro. A bro who has a shit-ton of loud gay sex in the bedroom across their hall, but life seems to be progressing and Dean discovers he doesn't have to be alone as he'd thought.

    Complete, posting every day or so, all due to be posted by Christmas.

    Language:
    English
    Words:
    22,130
    Chapters:
    4/14
    Comments:
    15
    Kudos:
    48
    Bookmarks:
    10
    Hits:
    655
  2. Tags
    Summary

    Thoroughly fed up with Dean’s inability to open up emotionally, Cas walks away only to find comfort in another man’s embrace.

    Or,

    The one where Dean realizes his mistakes, but will there be enough time?

    Language:
    English
    Words:
    8,303
    Chapters:
    1/?
    Comments:
    44
    Kudos:
    53
    Bookmarks:
    7
    Hits:
    632
  3. Tags
    Summary

    Hearts are such Fragile things. Castiel has never felt his heart break before. When his feelings come to light after a face-off with another angel, the rejection that pours of Dean is like he has never felt before. Castiel doesn't know if his shattered heart will survive this pain. He doesn't know if things will ever be the same again.

    There is one scene involving another M/F. No more than that. Very Angsty! Destiel!

    Language:
    English
    Words:
    39,925
    Chapters:
    13/?
    Comments:
    47
    Kudos:
    79
    Bookmarks:
    13
    Hits:
    1353
  4. Tags
    Summary

    Castiel Novak is a respectable, if not a little boring professor at his university. He lives a comfortable, financially stable life with his cat in his modestly-sized apartment. It would appear he has everything he needs, including an over-eager friend and colleague, but when fate tempts him with a seemingly familiar new student by the name of Dean Winchester, Castiel's comfortable life threatens to get turned on its head and things start to get a little juicy.

    Language:
    English
    Words:
    86,470
    Chapters:
    21/?
    Comments:
    510
    Kudos:
    367
    Bookmarks:
    101
    Hits:
    9189
  5. Tags
    Summary

    When Castiel and Dean decide to become an official hunting couple, they are required to go through a semi-public mating ritual where one of them is to become the omega and the other the alpha. All is good and well, until John Winchester walks in right when his eldest son is being screwed into oblivion on the floor. Chaos and orgasms ensue.

    Language:
    English
    Words:
    5,471
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    195
    Bookmarks:
    25
    Hits:
    2316
  6. Tags
    Summary

    Hitting a low in his search for God, Castiel asks for Dean’s help. They prepare a trap for the Archangel Raphael, to get answers about where God has gone. Even if they succeed, it may be the death of Cas; Raphael is at odds with him in the brewing civil war in Heaven. As their bond of friendship grows stronger during the mission, pressures Dean and Cas face lead them to reach out for more.

    Language:
    English
    Words:
    33,012
    Chapters:
    1/1
    Collections:
    1
    Comments:
    19
    Kudos:
    79
    Bookmarks:
    30
    Hits:
    1692
  7. 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:
    56
    Bookmarks:
    1
    Hits:
    1372
  8. Tags
    Summary

    “I’m going to kiss you now.”

    Cas pauses, giving Dean a chance to back out, but Dean just licks his lips and waits.

    Cas’s mouth is up against Dean’s for a couple seconds before Dean responds, and then it’s Cas that’s being kissed senseless, because kissing is definitely not something Dean does tentatively. Dean reaches up to cup Cas’s jaw in his hand, tilting his head for a better angle, mouth plush, tasting like whiskey.

    Cas tries to remember what it was like the first time he kissed a man. All-encompassing, the world jerking off its axis, the feel of stubble under his fingers intense in a way it never really is with women, as much as he loves them.

    Language:
    English
    Words:
    78
    Chapters:
    13/80
    Comments:
    29
    Kudos:
    40
    Bookmarks:
    4
    Hits:
    1357
  9. Tags
    Summary

    Dean has been procrastinating on his suicide for a long time.

    It's been years now, he thinks. Like yet another apocalypse that's been happening silently in the background of all the others the Winchester brothers keep surviving. But this one, this special apocalypse is his own, personal, intimate one.

    Mary died a year ago, already. At forty-one, Dean's body has been broken so many times he can't hunt anymore. His relationship with Sam is slowly dying out and Cas only visits once every few weeks.

    He's alone.

    So he tries to blow his head off. He misses, of course, like the failure he is.

    But Cas comes back into his life when he's the most needed. He tends to his wounds and tries to help Dean exhume what's been buried for decades: himself.

    What if Dean actually likes talking about his feelings? What if he doesn't want to lie anymore? What if he's not straight? What if he's not who he thought he was?

    What if there's still hope?

    Language:
    English
    Words:
    62,504
    Chapters:
    30/30
    Comments:
    273
    Kudos:
    357
    Bookmarks:
    73
    Hits:
    4616
  10. Tags
    Summary

    Pressured by his brother Gabriel to get back out there, Castiel creates a dating profile. He meets a handsome, intelligent guy named Patrick and sets up a date with him - a date that goes so badly that he contemplates jumping out a window. Enter Dean, an even better looking stranger that happens to have the same idea.

    Or, the one where Cass is too oblivious to notice the hot guy he hooked up with at the bar is the same one he's been arguing with online.

    Language:
    English
    Words:
    22,506
    Chapters:
    10/10
    Comments:
    136
    Kudos:
    272
    Bookmarks:
    33
    Hits:
    2990
  11. Tags
    Summary

    Cas likes to hide behind the camera, but Dean has always seen him. He doesn't mind if the guy takes his picture but he sure wishes he could do it without so much distance between them.

    Series
    Language:
    English
    Words:
    12,271
    Chapters:
    1/1
    Comments:
    10
    Kudos:
    85
    Bookmarks:
    11
    Hits:
    1346
  12. Tags
    Summary

    Castiel is a member of the Bratva who holds a lot of power inside and out of prison. Dean is a former Army medic whose big mouth got him into deep trouble with the Aryan brotherhood just weeks into his sentence. He needs protection, or his measly two years in lockup could end as a death sentence.

    Series
    Language:
    English
    Words:
    30,177
    Chapters:
    5/5
    Collections:
    1
    Comments:
    248
    Kudos:
    634
    Bookmarks:
    108
    Hits:
    5675
  13. Tags
    Summary

    Dean Winchester loves women, and women love him. Except there's a rumor going around at the office that he's dating Castiel Novak. Which, according to Kali, is ridiculous because Dean is way out of Castiel's league. His ego wounded, Dean vows Castiel will soon be eating in the palm of his hand. It doesn't go exactly as planned.

    Bonus: You get to choose between two endings!

    Language:
    English
    Words:
    9,112
    Chapters:
    3/3
    Comments:
    2
    Kudos:
    70
    Bookmarks:
    10
    Hits:
    1253
  14. Tags
    Summary

    One insignificant decision completely alters the trajectory of a soldier's life.

    Dean is a battle-hardened British soldier on a reconnaissance mission in the forests surrounding Bucharest at the beginning of the Crimean War. A moment of kindness leads to his imprisonment, he captures the attention of the hedonistic prince, Castiel.

    Language:
    English
    Words:
    89,965
    Chapters:
    21/28
    Comments:
    196
    Kudos:
    261
    Bookmarks:
    45
    Hits:
    5684
  15. Tags
    Summary

    Dean and Cas had been dancing around their feelings for weeks. OK, years . . . but they’d been openly, actively flirting for weeks. Now that Jack had gotten rid of Michael once and for all, they all felt like they had a new lease on life, and none of them wanted to waste it. For once, Dean and Cas had the bunker all to themselves, and they finally (FINALLY) took advantage of it. Let there be sex!

    Language:
    English
    Words:
    4,142
    Chapters:
    1/1
    Comments:
    6
    Kudos:
    97
    Bookmarks:
    9
    Hits:
    1523
  16. Tags
    Summary

    When Dean Winchester’s fiancé announced that she was pregnant by another man and walked out, Dean swore off relationships. He couldn’t even bring himself to have casual sex, (which had once been his favorite pastime), with the notable exception of a single eye-opening night. Three years later, Dean’s brother Sam has had enough. A sibling argument leads to Dean signing up for a popular dating site, ‘A Profound Bond.’ When Dean’s first match opens their chat conversation with an outdated query, Dean has to decide if he can move past the other man’s awkward 1990s introduction, and finally take another chance on love.

    Language:
    English
    Words:
    15,372
    Chapters:
    3/3
    Comments:
    62
    Kudos:
    333
    Bookmarks:
    56
    Hits:
    3052
  17. Tags
    Summary

    It had taken Dean too long to realize that he had feelings for Cas and after the Croatoan virus overtook their world and Cas became human, he had only gotten even more irresistible.
    After a shocking truth reveals itself for Dean, he decides to do something about it, with the help from some of Cas's closest girlfriends.

    Language:
    English
    Words:
    3,266
    Chapters:
    1/1
    Collections:
    3
    Comments:
    2
    Kudos:
    35
    Bookmarks:
    2
    Hits:
    964
  18. Tags
    Summary

    Dean Winchester has a crush. A great, big, secret, gay crush. Okay, more like a great, big, secret, bisexual crush, if we’re being technical. Either way though, the relevant word here is secret, because Dean lives in Kansas, which isn’t exactly known for its thriving LGBT community. In fact, he’s pretty sure most of his neighbors don’t actually know what LGBT stands for and he’d be willing to bet that if asked, at least a solid 10% would think it’s a sandwich.

    So yeah, nobody knows that Dean’s spent the past six months crushing on Cas Novak, the sexy junior in his Spanish II class, and it’s damn well going to stay that way.

    “Hola, Señor Winchester,” murmurs a gravelly voice in Dean’s ear, straight out his dirtiest fantasies and close enough to raise the hairs on the back of his neck, as Dean suppresses a shiver. The smirk on the mouth housing that goddamn sinful voice tells him that while he may have resisted the full-body shudder, his red cheeks did not go unnoticed by the boy sliding fluidly into the desk directly behind him.

    “Hey, Cas.”

    Nobody knows about Dean’s crush except for Cas, that is. Cas definitely knows.

    Language:
    English
    Words:
    7,775
    Chapters:
    1/1
    Comments:
    28
    Kudos:
    263
    Bookmarks:
    34
    Hits:
    1998
  19. Tags
    Summary

    It started out like any typical sleepover they have had since middle school. Little did Dean know how different this one would turn out.

    Series
    Language:
    English
    Words:
    2,737
    Chapters:
    2/2
    Comments:
    2
    Kudos:
    47
    Bookmarks:
    4
    Hits:
    2440
  20. Tags
    Summary

    “Cas is coming home. I just thought you should know.”
    It’s those words from his best friend, Cas’ brother Michael, that unleash memories and feelings Dean Winchester hasn’t confronted in years. The way they parted thirteen years ago was terrible, there’s no other way to phrase it. Dean knows Cas has every right to be angry at him, yet the cold attitude still hurts. The fact that the adorable, pudgy nerd he once knew has turned into this smoking hot man doesn’t make it any better. And as if his own sexuality crisis isn’t enough, Dean’s daughter Grace seems to have found a new friend in none other than the man that makes Dean question his entire life as he knows it.

    Dean’s PoV of Angel Cookies.

    Series
    Language:
    English
    Words:
    32,013
    Chapters:
    8/?
    Comments:
    324
    Kudos:
    494
    Bookmarks:
    76
    Hits:
    8969

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