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Dean + Losing the people he loves | requested by @isitsowrong ⇴ Song: Hate To See Your Heart Break by Paramore

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Dean Winchester | 15x13 Destiny’s Child 

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Walk away.

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DEAN WINCHESTER — DEAD IN THE WATER

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Keep grinding. No matter how much it hurts, no matter how hard it gets, you gotta keep grinding. And that’s how we’re gonna win. And we’re gonna win. We’re gonna save Cas, we’re gonna ice the Devil, and we’re gonna shank the Darkness. And anyone that gets in our way. Well, God help ‘em.

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Headcanons: Masturbation

I had all this written up and queued it and tumblr ate it! If it posts twice I am apologizing in advance. 

So @sleep-silent-angel asked for this AGES ago. (Edit: In the year-of- Satan 2016.) I’ve finally delivered (even though I ought to be ashamed of myself). 

Sam:

Sammy, Sammy, Sammy. I feel like he tried to be very circumspect about it in the beginning. I mean, he grew up with Dean, who probably left girly magazines laying around pretty frequently. It was probably desperate and sweaty- in the shower if Dad was gone; in bed under the covers if Dean and Dad were both gone. He was probably incredibly prideful too: not proud of himself, but prideful. He wouldn’t use the same magazine or rented porn that Dean used; he wasn’t about to jack off to the same girls as his brother.

In the beginning Sam’s fantasies were probably about fucking the girl he grew up next to, of having his own car and gently undressing her and then doing it in the backseat. He probably daydreamed about saving some girl, of telling her the truth about him and his family, and then riding off into a sex-filled sunset.

Jess was probably his first time masturbating over the phone. Maybe she was on a class trip somewhere and he was at home and she calls from her hotel room. She tells him it’s really fancy; that there’s even a phone in the bathroom and her roommate is asleep and she misses him.

I love imagining Jess with a dirty mouth. I love imagining her telling Sam that she misses his beautiful cock, misses it in her mouth and hand and pussy. That she feels so empty, that she is imaging his mouth on her nipple and his hand on her clit and his dick in her cunt.

I love imaging Sam saying basically nothing but yes, oh god yes, and pumping his fist up and down his dick hard enough to leave finger prints.

And then, when Jess comes home, I like to imagine Sam getting her in bed and whispering to her that he had to change the sheets before she got home; that he missed her so much that he was left covered in spunk and sweat and lube.

Both Winchesters are probably like most people in that they go through porn phases. Sam, I imagine, rotates through standard porn- professionals, man/woman blowjob/fuck/cunnilingus type stuff. I also like to imagine he’s the one that watches BDSM porn; that he gets off on the idea of gently tying knot after knot until some beautiful, smooth female is left helpless and open and trusting in his bed. I bet in his softer moments, when it’s dark and his bed is empty and he just wants to feel something he just imagines Jess, or Madison, or some faceless, nameless girl that isn’t as embroiled in grief and nostalgia. Anyway, he probably just imagines being able to reach out and touch someone, to wrap himself around a girl all soft with sleep, to wake her with lips and kisses and cock, and then to fall asleep tangled in limbs and sheets.

But purely for my own enjoyment… can’t you just imagine walking in and seeing Sam? Can’t you just picture him sitting in bed, his laptop open in front of him, his beautiful long cock gripped tightly in his hands- fuck fuck fuck those long, calloused fingers wrapped around his dick, sliding up and down, the head peeking out and disappearing in quick jerks. Imagine Sam seeing you watching; imagine him locking eyes and staring at you with those kaleidoscope eyes, maybe raising one eyebrow and daring you to join him.

Hnnnng.

Dean:

Oh, Dean. Our Busty Asian Beauties connoisseur, our fan of all things female. Dean probably started masturbating later than he’d like most people to think- I mean, not super late, not late at all, just probably not at the age of about nine like he likes people to think.

His original fantasies were quite likely very cowboy-style. Dean rolls into town and steals the heart and favors of the homecoming queen. Dean saves the beautiful damsel from a ghost, says something along the line of it’s what I do, miss, you’re safe now and then bangs her in the back of the Impala.

Grown-up Dean doesn’t get off on the damsel in distress anymore. He doesn’t want to feel responsible for anything else; he’s already dealing with the whole damn world. Adult Dean likes to imagine a commitment-free girlfriend type person: someone he can spend a weekend with if he’s in the state; someone he can occasionally call when he wants to hear a friendly voice. Basically, by the time Dean is thirty all he wants is a familiar set of curves, a bed he’s woken up in more than once, someone understanding and lonely and who kind of wants the same thing. That’s the only fantasy that Dean can see himself actually getting.

But when it comes to porn, well. Dean’s of the mindset that he’ll try anything once, and so he’s seen just about everything. He likes homemade porn a lot, he likes how it isn’t all staged and all for the man’s pleasure. He gets off on hearing girls come; porn starlets who are known for not faking orgasms are the ones he follows with acolyte-like devotion.

In a weird twist, porn is one of the only things that Dean frequently talks about with Sam. Here’s an example:

The boys are in the Impala driving along some stretch of highway without a lot of traffic. Trees and fences flash by.

“I’ve really gotten into lesbian porn recently.”

Sam will look at his brother with his mouth slightly open and eyebrows up. “I don’t want to know that Dean! This is something we shoudn’t talk about.”

Dean’ll continue like Sam didn’t even speak. “I love how into it they get; and a lot of the videos are long. I mean, some of these chicks can eat pussy longer than I can. I admire that. Plus, boobs.”

Most likely Sam would just roll his eyes and go back to staring out the car window.

I think- I know- Dean is very into mutual masturbation. Let’s try this out for size:

Dean has a lady friend he drops in on from time to time. She’s fun and pretty adventurous in bed. He goes to see her one weekend and Dean’s watching her undress and he breathes, “No, wait, leave your bra on,” and she does, and she looks at him with dark dilated eyes, waiting to see what Dean says next.

He catches onto the game and has her slowly shimmy out of her underpants, take down her hair, unclip her bra. He has her rub on her nightly lotion, watching with his dick pressed hard against his jeans zipper. Then, god, he has her sit in the little wingback chair in the corner.

“Put your left leg over the arm of the chair.”

She hesitates, blushes.

”C’mon, sweetheart. You know you’re so pretty there; soft and pink and feminine.”

She slings her leg over the chair arm.

“Now the other one.”

More hesitation.

“I’ll do your favorite thing later, and the whole time you can think about how much I love that bit of you.”

She bites her bottom lip and does as he asks; she’s now leaned back in the chair, her weight resting on her tailbone, her legs wide and pussy exposed.

Dean pops the button and unzips his jeans, he has to. If he doesn’t his pants might just give him some kind of condition from cut off blood circulation.

“Touch yourself. Pretend I’m not here and you’re thinking of whatever hot thing turns you on.”

She slid her first two fingers down to slowly circle around the top of her pussy. “I think about you sometimes,” she whispered, and Dean groaned.

“Touch your tits,” he asked, eyes wide and fixed on her.

She rolled a nipple between the fingers of her other hand; her mouth opened slightly as her breathing sped up.

Dean realized his hand was his cock, which was so hard it had passed right over pleasure and into pain territory.

She closed her eyes.

“Keep ‘em open baby, I want to see you come; Jesus honey you’re so pretty, I just want to come over there and touch that pretty skin and your wet pussy and your swollen clit; god I can see it from here. Yeah, just like that sweetheart, make yourself come for me, I want to watch you-“

She hummed a little in her throat and squeezed her eyes shut as the pleasure contracted her belly muscles and made her pussy clench.

“Oh, shit baby,” was the last thing Dean said before he was shooting little spurts of hot come all over his hand and lap.

 PS. I bet back in the day Dean would go out of his way to seduce himself. I could see him putting on music- granted, it would be rock, but still- and getting fun tingly lube and just enjoying himself.

Little Sexy Ask Fics

Wow I wrote this in 2016 and just found it again. So much and yet so little has changed. 

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From a new interview in The Telegraph with author Dennis Lehane.

These days Lehane is a screenwriting veteran, and recently adapted one of his short stories into the underrated film The DROP. He made extensive changes to his screenplay when he learnt that Tom Hardy and James Gandolfini were playing the leads. 

“I cut a lot of Tom’s dialogue. He didn’t need to be given speeches. I knew he could do it all with his eyes. 

I’m pretty sure I’ve never seen anybody think to that degree on screen.”

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Bailing out of social interaction like

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— glass animals

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spn | 8.07

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Dean | SPN 8.03