1 - 20 of 32 Works in Dean Winchester Cries During Sex

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  1. Tags
    Summary

    Sam is too young, but Dean's eyes on him make his insides flutter. Even though Dean seems to hate himself for it.

    Language:
    English
    Words:
    1,494
    Chapters:
    2/2
    Comments:
    18
    Kudos:
    362
    Bookmarks:
    29
    Hits:
    10707
  2. Tags
    Summary

    Benny's taken aback when Dean announces, mid-fuck, that even being double penetrated isn't enough to sate his size kink. Fortunately, Cas has an idea of something bigger they can use that maybe, just maybe, will be enough to give Dean what he needs...

    Kinktober Day 3: fisting or medical play or orgasm denial

    Series
    Language:
    English
    Words:
    2,948
    Chapters:
    1/1
    Collections:
    1
    Comments:
    19
    Kudos:
    76
    Bookmarks:
    7
    Hits:
    1256
  3. Tags
    Summary

    Used to be all he needed was his Sammy, safe, him with the keys to Baby in his leather and a gun in his hand.

    OR

    Dean ruminates on how much he loves Cas... as Cas makes love to his ass.

    Series
    Language:
    English
    Words:
    306
    Chapters:
    1/1
    Comments:
    3
    Kudos:
    77
    Bookmarks:
    9
    Hits:
    1043
  4. Tags
    Summary

    I started writing this with the intention of creating some gratuitous sex involving body shots and sexy innuendo, but it ended up being...a lot sappier than I intended. It also took me such a long time to get them to the actual sexy times. Sometimes it's all about the build-up! The Tension! The Feels!

    Enjoy!

    Language:
    English
    Words:
    4,973
    Chapters:
    1/1
    Comments:
    5
    Kudos:
    132
    Bookmarks:
    15
    Hits:
    1080
  5. Tags
    Summary

    Jack wants Dean to give him "The Talk" like he promised, and Dean can't find a way to wiggle out of it. Luckily, Cas is there to shoulder the awkwardness with him. But Jack wants to learn about love, and not just sex. And what happens when Cas accidentally lets something slip?

    Language:
    English
    Words:
    14,685
    Chapters:
    1/1
    Comments:
    40
    Kudos:
    400
    Bookmarks:
    58
    Hits:
    3369
  6. Tags
    Summary

    Dean had come to apologise. To thank Cas. But pieces of Cas' broken heart were now on show, stabbing right through his beautiful face, slicing through Jimmy's muscles and skin. Dean could see it all now, pouring out through the jagged cuts; fear, shame, all the hurt—the lion's share of it of which Dean himself had caused. Cas was now wearing his pain on full display all over his body, like a shiny fucking outfit of the day.

     

    Dean had never hated himself more. Even after torturing an endless stream of once-human souls in hell.

     

    Cas let the pistol drop to the floor.

     

    "Then what, Dean?" he choked, "why are you here?" His wet eyes searched Dean's with such wretched frustration, Dean couldn't take it a second longer. Had to make it go away, end the pain. Ironically, Dean realised, he did want to make everything stop for Cas—for both of them—even if only for a little while. Just not by means of a bullet.

     

    How the hell do you make the whole world just stop?

    Language:
    English
    Words:
    7,316
    Chapters:
    1/1
    Comments:
    40
    Kudos:
    133
    Bookmarks:
    29
    Hits:
    2120
  7. Tags
    Summary

    Dean and Cas both have to face the consequences of their one-night stand.

    Or,

    The one where neither Dean nor Cas can seem to stop, for better or for worse.

    Series
    Language:
    English
    Words:
    43,766
    Chapters:
    7/7
    Comments:
    374
    Kudos:
    621
    Bookmarks:
    80
    Hits:
    9504
  8. Tags
    Summary

    Dean hasn't been doing well since being possessed by Michael. His temper flares at the slightest provocation and after almost lashing out at Jack, Cas is splitting his time between Jody's and the bunker when Jack moves to Sioux Falls in order to try and keep the peace in the bunker.

    During yet another fight with Cas, Dean breaks down and admits he needs help. Sam and Cas are worried, and vow to help him.

    While Dean considers retirement, they plan a family camping trip to try to enjoy the world they saved. Dean is dealt a blow when he realises his feelings towards Cas are more than friendly and then receives the bombshell that Cas has been in love with him for a long time. It's a lot to cope with and Dean struggles to work out what he really wants from life and from Cas.

    *Canon divergent. Jack killed Michael without using up his soul. Mary didn't die and Chuck didn't show up.

    Language:
    English
    Words:
    42,269
    Chapters:
    10/10
    Comments:
    28
    Kudos:
    158
    Bookmarks:
    38
    Hits:
    2025
  9. 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:
    31
    Kudos:
    262
    Bookmarks:
    39
    Hits:
    3932
  10. Tags
    Summary

    Dean tries extra hard to stop the next memory from barrelling through his mind like a runaway freight train--he really does.

     

    Cas stood--bold as balls in front of me with that impossibly blue stare--like pure fucking sex, my eyes practically screamin' at a vision of goddamn glorious nakedness; so many miles of tan skin and those mouth-watering, razor-sharp hip bones, sculpted literally by God himself… He lunges forward and grips me tightly by both wrists, roughly shoving my hands up above my head. The fucker then smirks, slamming me into the tiled wall, like blind fury on a really fucking horny day, his slippery-when-wet body crashing into mine and hot tongue pushing with surety into my waiting, wanting mouth as his thick, steel-hard cock presses into mine…

     

    Dean's dick twitches with much more than just interest at the scenario his memory is providing of his recurring shower-sex dream. But stoically he tries his damnedest to ignore it--breathing in and out, deeply--because Dean Winchester has standards and point-blank refuses to live in a fucking Fifty Shades novel.

    Dean's dick has other ideas.

    OR

    The one where Dean gets a little (definitely not blue) ballsy.

    Series
    Language:
    English
    Words:
    6,755
    Chapters:
    1/1
    Comments:
    28
    Kudos:
    120
    Bookmarks:
    13
    Hits:
    1769
  11. Tags
    Summary

    With love like faith, Dean gives worship at the shrine that is Castiel...

    Language:
    English
    Words:
    378
    Chapters:
    1/1
    Comments:
    8
    Kudos:
    53
    Bookmarks:
    6
    Hits:
    791
  12. Tags
    Summary

    Cas takes Dean away from the edge.

    Language:
    English
    Words:
    1,072
    Chapters:
    1/1
    Kudos:
    27
    Bookmarks:
    6
    Hits:
    676
  13. Tags
    Summary

    Dean is a little who turns to his brother to be his Daddy. After the worst night of Deano's life Dean turns to the one person he knows he can trust to be his Daddy. Will Sam be able to be the Daddy Deano needs?

    Series
    Language:
    English
    Words:
    34,864
    Chapters:
    9/?
    Comments:
    60
    Kudos:
    266
    Bookmarks:
    32
    Hits:
    12315
  14. Tags
    Summary

    Castiel and Dean were both like green bananas when they first started this. Dean topping, always giving. Back then, Cas had never had sex before, and Dean was more than happy to take the lead to teach him. But really, Castiel was the one teaching him. Sex didn't have to resemble the porn Dean had been consuming for decades, and Dean's real self emerged more and more as Cas helped him un-learn. Dean thought they’d peaked then, the perfect yellow fruit... but now, they’d somehow surpassed that. They made sweet banana bread together. Better than he ever thought he’d get. Better than he knew he deserved.

    Language:
    English
    Words:
    3,288
    Chapters:
    1/1
    Comments:
    12
    Kudos:
    169
    Bookmarks:
    21
    Hits:
    1739
  15. Tags
    Summary

    Cas wants to try masturbating. Maybe from a safe distance - like the other end of a cellphone call - Dean can talk Cas through it.
    (Take two: both in the same place this time.)

    Language:
    English
    Words:
    11,079
    Chapters:
    1/1
    Collections:
    1
    Comments:
    62
    Kudos:
    1174
    Bookmarks:
    190
    Hits:
    13798
  16. Tags
    Summary

    Castiel is inexperienced. Dean seeks to rectify this, one step at a time.

    "Their safe place, their haven, their little place carved out of heaven brought down to earth. He smiled softly and pressed a kiss just below Cas’ ear as they lay chest to chest, breaths heaving, flesh flushed hot and damp with sweat. Damn the heavens above. Heaven was a place under the sun."

    Language:
    English
    Words:
    17,505
    Chapters:
    1/1
    Comments:
    19
    Kudos:
    182
    Bookmarks:
    33
    Hits:
    4173
  17. Tags
    Summary

    "For Sam, it was a slow acclimation. Watching his big brother disappear under the creams and powders, soft fabrics in soft colors he would otherwise never wear.
    When Castiel turns Dean around to face the mirror, though, the shock of finding himself obscured visibly passes through his body."

    (In which Castiel pampers Sam and it gives him the idea to pamper Dean all the way into a dress and make-up.)

    Series
    Language:
    English
    Words:
    9,587
    Chapters:
    2/2
    Comments:
    42
    Kudos:
    140
    Bookmarks:
    20
    Hits:
    4092
  18. Tags
    Summary

    AU where Sam dies destroying Asmodeus, Dean can't handle it, and Cas is left to pick up the pieces.
    Inspired by 'You don't Know what it's Like', by Katelyn Tarver

    Language:
    English
    Words:
    1,104
    Chapters:
    1/1
    Comments:
    4
    Kudos:
    46
    Bookmarks:
    4
    Hits:
    976
  19. Tags
    Summary

    In that crucial split second, Cas moves out of the way.

    Series
    Language:
    English
    Words:
    11,309
    Chapters:
    3/3
    Collections:
    1
    Comments:
    93
    Kudos:
    402
    Bookmarks:
    57
    Hits:
    5685
  20. Tags
    Summary

    Dean thinks he's been hit by a sex curse that keeps him painfully hard until Sam gets inside him, but Sam knows the truth. He's been using telekinesis to get Dean in the mood, so he can fuck his big brother whenever he wants.

    A.k.a. the one where dark!Sam manipulates his brother into a blowjob and Dean isn't allowed to refuse.

    Series
    Language:
    English
    Words:
    5,776
    Chapters:
    1/1
    Comments:
    40
    Kudos:
    426
    Bookmarks:
    44
    Hits:
    16908

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