Confessional Diaries

Just a gay guy who is a simp for the Winchester Brothers. This is a place for all of us to goon out over these hot men. Also this blog is Wincest centered & has explicit content. (18+ only)

[theconfessionaldiaries]

About Me & This Blog:

- This is an 18+ only blog.

- I’m semi new to the fandom. I’ve been watching the show for years.

- This account is pretty much a Wincest smut account. Or if I’m not talking about Wincest, I’m just glazing Sam and Dean lol. My blog is/can be very explicit.

- I love Sam Winchester, that man is hot as fuck to me. I love bottom!sam and top!dean the most.

- Idiots will be blocked. Live and let live.

- Feel free to send in an Ask.

[sisterwifesam]

i am tired of hearing about how sam is crazy without dean. we got three sam-less versions of dean who go completely off the rails, and no one ever talks about it.

endverse dean (who lost sam to lucifer), purgatory dean (left without sam), mark of cain dean (broken up with sam). all three of them become feral and take pleasure in killing and torturing in cold blood.

what the lack of brotherwife pussy does to a man.

[theconfessionaldiaries]

Jeeezz looking at these photos even I have pity on poor Dean… The man looks so lost. So angry.

Sam you better hurry up and give your straight big brother some of your boy pussy before things get even worse.

[codependency-is-real]

Personally I view wincest dynamic through the lens of strict, traditional gender roles. Dean is a masculine archetype and Sam as feminine.

Their emotional, domestic and physical mechanisms mimic a traditional, heterosexual marriage. Dean is a husband/father and Sam is a wife/mother. And I convinced that their sexual dynamic is the same.

Sam is the empath, often the one who connects with victims, especially women and children. He advocates for mercy, understanding for the “monsters.” He is the forgiver. No matter how brutal Dean gets, Sam almost always folds, offering reconciliation. This mirrors a trope of the long-suffering, forgiving wife. He provides domestic stability when possible.

Sam's concern with health, appearance, and cleanliness is a form of self-maintenance associated with femininity.

Sam does not weaponize his size. He deliberately disavows this physical advantage. He makes himself smaller and harmless. He chooses not to compete with Dean in physical terms.

Sam becomes more submissive over time because the system punishes rebellion and rewards compliance.

Dean loves the dynamic. He mocks Sam's lifestyle and beliefs, all tropes he codes as weak/domestic/feminine. This mockery reinforces the hierarchy.

Dean is the breadwinner and protector (gets the money, drives the car, etc.). He dictates when they talk and when they act. Sam's attempts at emotional communication are often shut down with a joke, a command, or anger.

The cycle of explosive fights (Dean's anger, Sam's flinching), followed by silent reconciliation and a return to "normal," mirrors the pattern of an abusive domestic partnership. The profound love is real, but so is the fear and control.

John unconsciously raised them to fulfill complementary, spousal roles. Dean was molded to be John's successor. Sam was shaped to be the wife and the mother of the family – Mary.

[theconfessionaldiaries]

All very accurate.

[theconfessionaldiaries]

I rarely see anyone ever mention how there’s like no doubt Dean would be extremely homophobic towards Sam when they have sex. Just straight up degrading nasty foul slurs.

Like a bully almost.

Dean does it because he finds himself in a position of authority and feels his manhood and Sam’s lack there of (also because of Sam’s attraction to men) makes his little brother less than a man.

[theconfessionaldiaries]

Question

What does Dean call Sam during sex, “Good Girl” or “Good boy”?

I feel like Dean would say both, now which saying depends on whatever slipped outta his mouth in the moment. If the brothers started their sexual relationship in the early seasons, then I would say Dean calls him “Good Boy.”

But honestly, as the show goes on and we get into the later Seasons as the brother’s dynamic slowly changes and their more permanent roles start to settle. I think Dean would call Sam his “Good girl.”

I feel like Dean has always feminized Sam in his mind to a degree, but once we reach those later seasons Sam basically becomes and is Dean’s submissive “girlfriend”. I don’t think the older brother even really acknowledges Sam’s gender.

That’s why Dean, despite being a heterosexual man, can still have sex with Sam. Sam is just Sam to Dean.

[theconfessionaldiaries]

Oooohhh.

I remember when these photos came out from that Men’s Health shoot.

These pics are so sexy, imagine this gorgeous man working out in front of you, putting on a show; flexing his muscles. Looking exactly like he does in the picture above and then when you can’t take it anymore you just pull down those workout sweats to find a hard 8 and a half inch veiny cock that’s drooling sticky precum. His balls looking full and heavy.

Like you just know that piece of meat feels weighty on the tongue.

Yummmy.

[inbredflies]

ꪆৎ ˚

dean prone boning sam with his huge bicep wrapped around his neck. his entire weight is resting on sam’s body, and his erection is driving into that tight hole with his pelvis rhythmically slapping against sam’s plush ass.

and it’s just too good on sam’s end, the constant thrusts of dean’s cock jabbing at his prostate and him being suffocated by dean’s muscular arm has his brain turning into mush and his own cock leaking on the mattress. there is not a single coherent word that is slipping past his mouth besides the little mewls and high-pitched moans.

sam can’t squirm away either; with the very little strength that he has, he takes every deep stroke dean is giving him. and he doesn’t realize that he’s starting to drool on his bicep till dean lifts his head with his other hand, where he sees a string of saliva connected from his mouth to dean’s arm. the room may have spun on a tilted axis, but his brother was the only pull sam needed. dropping his chin into the meat of dean’s bicep, sam clamped down. and dean just stares down at the messy, slobber-soaked display, chuckling as he tightens his hold. it wasn't a malicious bite, but a dull gnawing.

"look at that," dean crooned, his voice dripping with syrupy condescension as he lazily scratched behind sam’s ear. "my little puppy got himself a chew toy."

[theconfessionaldiaries]

Very hot

[theconfessionaldiaries]

hell yea we need more gay guys in this fandom! your takes are very in-character in my opinion :) keep on posting

-\ @angelgracebait

I like to think they’re in character too haha. Thank you. Yeah the brother’s dynamic is an easy one for me to understand. It’s as hot as it is special to be honest.

[theconfessionaldiaries]

I just wanted to say that I love your takes! You understand their dynamic perfectly :D

Thank you ;)

[theconfessionaldiaries]

I feel like there’s been times in the bunker where Dean takes a shower, then gets out completely wet/not drying off; he goes up to Sam (who’s probably sitting at the table doing some research) and then shakes his hips from left to right causing his half hard dick to swing side to side. The thick piece of meat making a smacking sound against Dean’s upper thigh with the swivel of his hips.

And Dean just laughs at an annoyed Sam, he loves taunting his younger sibling. Telling his brother that “This is what a real mans cock looks like Sammy! Look at it!”

That’s probably also Deans’ funny/creative way to tell his brother to get down on those knees and service him. He knows damn well poor gay cock lover Sammy (of all people) isn’t gonna be able to resist a big shaft in his mouth.

[codependency-is-real]

dean walks like it’s heavy ♡

[theconfessionaldiaries]

He really does though 😂. Just big, thick, and heavy. Ready to be pumped.

[sisterwifesam]

i'm your man, mitski

[theconfessionaldiaries]

I’ve read a lot of smutty/fanfic within different fandoms and none and I mean none of them, can get me off like reading Wincest smut or looking at Sam and Dean NSFW art.

The best part about the Supernatural fandom when it comes to fanfic is there is something for everyone. Everyone can and will eventually find their kink.

If you like Top!Dean & Bottom!Sam you’ll find it. If you like it vice-versa, you’ll find that too.

It’s just crazy for me to recognize that for years now, some of the best orgasms I’ve had are the ones Sam and Dean have given me from me reading fanfic 😩. And I know damn well I’m not alone on that front. That’s another good thing about the Supernatural fandom, we can all be horny and desperate over those big dick brother fuckers together lol.

Though of course I can’t stop shipping Wincest even after all this time, Sam and Dean have my gay ass by my cock and balls super tight and won’t let me go anywhere…. And I don’t want to either…. I like reading about that fucked up older brother just dogging out his younger sibling, using Sammy’s asshole like his personal pocket pussy. Treating Sam like he’s his girlfriend.

The masculine and feminine dynamic, it’s just all so hot and it’s extremely evident on the show as I’ve mentioned before and I wouldn’t have it any other way.

[theconfessionaldiaries]

Relationship Dynamics (Sam & Dean)

I wanted to expand on a previous post I made,

One of the reasons why I feel like Sam feels very safe with Dean and why they’re relationship works so well (outside of the basic reasons of course) is because Dean is your stereotypical masculine male. While Sam is very much a feminine coded male (in later seasons more so than early).

With that being said, in my fan headcanon, I do feel like the main reason why Sam is so attracted to Dean is because his older brother makes him feel like a girl that’s safe and protected.

And whether Sam would admit that out loud or not is another story, but he NEEDS that safety net.

Realistically Sam needs a dominant partner and I don’t even mean BDSM. Sam needs a “partner” or more specifically a man who is somewhat pompous, cocky, knows how to fight, can fix a car, and has an attitude problem with a possessive quality. Basically what Sam finds attractive when looking at another guy is that typical “straight male behavior.”

So Dean being a heterosexual man works perfectly in Sam’s favor. The older man doesn’t consider sex with Sam as even remotely gay and doesn’t even view his little brother as an actual male. In fact, I feel like if you were a stranger meeting the brothers for the first time and were to assume Dean was gay because of the siblings relationship dynamics, Dean might even be a bit angry that you assumed he was gay.

Dean gives the “I don’t mess with the faggot shit” type of attitude.

With all that being said, I think Sam loves the way Dean is and acts; his masculinity and his heterosexuality. And I believe Dean loves how submissive and feminine leaning his brother can be. Almost to the point where Dean (if it wasn’t for Sam’s cock) would 100 percent believe Sam is and acts like a girl.

In their relationship, Dean feels like he’s the guy with the hot cheerleader girlfriend on his arm and Sam feels like he’s the girl who’s dating the hot cocky asshole jock college football player.

It works so well when you look at the brother’s overall dynamic on the show and how they interact with each other in relatively normal circumstances (outside of their trauma of course).

[blood-covered-lover]

Dean Winchester is straight because he sees Sam as a woman and it wouldn’t even cross his mind as gay if he fucked him

[theconfessionaldiaries]

On a day to day basis, do you guys think Dean thinks of Sam as his “girlfriend” and not his boyfriend?

I personally think he does because in my own fan headcanon, Dean doesn’t really see himself as gay or bisexual. He see’s himself as a straight man who just so happens to be attracted to Sam aka another man aka his own damn brother lol.

Like if you were to ask Dean if he were gay since he was having sex with Sammy, he’d probably tell you “Sammy’s not a real man.” Or say “Sam’s practically a girl, not the same!”

Dean Winchester, ironically enough, is as straight as they come. I also think Dean gets off on treating Sam like “less than a man” when they’re together. I think Dean likes that Sam makes him feel like a “man’s man” because canonically Sam lets Dean take control often.

I simply believe Dean views his tall ass little brother as chick who happens to have a lengthy dick for the most part.

[theconfessionaldiaries]

I wanna see a season 14 Sam Winchester with a gaping asshole; him crying out as the thick 8 inch pink dildo destroys his manpussy.