Chapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Sam Winchester Has a Vagina, Vaginal Fingering, Squirting and Vaginal Ejaculation, Quickies
Series: Part 1 of Sam Winchester's Boypussy
There's no better way to relieve stress after a hunt than fingerblasting your baby brother!
Slippery When Wet (2277 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Masturbation, Brother/Brother Incest, Hand Jobs, Shower Sex, Anal Sex, Sam Winchester Has a Vagina, Top Dean Winchester/Bottom Sam Winchester, Bathing/Washing
Series: Part 2 of Sam Winchester's Boypussy
Motel showers are cramped, but that has never stopped Sam and Dean.
Starfucker (1333 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Episode: s02e18 Hollywood Babylon (Supernatural), Brother/Brother Incest, Trailer Sex, Clothed Sex, thigh riding, Sam Winchester Has a Vagina, Implied/Referenced Dean Winchester/Tara Benchley
Series: Part 3 of Sam Winchester's Boypussy
Sam Winchester has never fucked a (not even marginally) famous person before.
Lover's Lane (1453 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Cunnilingus, Sam Winchester Has a Vagina, Sex in/on the Impala (Supernatural), Dean Winchester's Self Care is Taking Care of Sam Winchester
Series: Part 4 of Sam Winchester's Boypussy
Dean takes care of his baby inside of Baby.
Easy Peasy, Mac and Cheesy (3710 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester, Original Male Character(s)
Additional Tags: Pre-Canon, Teenagers, Brother/Brother Incest, Bullying, Homophobic Language, Dean Winchester/Sam Winchester First Kiss, Weecest, Sam Winchester Has a Vagina
Series: Part 5 of Sam Winchester's Boypussy, Part 1 of Weecest
Sam can only think of one way to say thanks to his brother.
You're My Present This Year (2950 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Episode: s03e08 A Very Supernatural Christmas (Supernatural TV 2005), Angst and Porn, Christmas Smut, Drunk Sex, Riding, Sam Winchester Has a Vagina, Vaginal Sex
Series: Part 6 of Sam Winchester's Boypussy
Sam nearly forgets to give Dean his last Christmas present.
Mortality (100 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Drabble, Post-Canon, Aging
Dean observes Sam.
Friction (200 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Double Drabble, Stanford Era (Supernatural), Mutual Pining, Masturbation, Sam Winchester Has a Vagina
Series: Part 7 of Sam Winchester's Boypussy
Sam and Dean might be separated by miles, but their minds always come back to each other.
Sweet Love Sugar (100 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Fluff, Ice Cream, Drabble
Dean Winchester is a sweet-talker.
I'm In Love With My Car (600 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Episode: s05e08 Changing Channels (Supernatural), Sam Winchester as the Impala, Sex with a Car, Brother/Brother Incest, Crack Treated Seriously
Dean gets a few ideas while Sam is trapped inside Baby.
Breed & Breakfast (2704 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Bed & Breakfast, Breeding Kink, Gentle Sex, Vaginal Sex, Sam Winchester Has a Vagina, sam has an mpreg dream and dean wants to hear about it
Series: Part 8 of Sam Winchester's Boypussy
Sam and Dean aren't eager to get out of bed.
Ridiculous (2016 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester, Jessica Moore/Sam Winchester
Characters: Dean Winchester, Sam Winchester, Jessica Moore (Supernatural)
Additional Tags: Sibling Incest, Gender Identity, Vignettes, Trans Sam Winchester
Sam has never felt like the other girls.
Bone Call (11316 words) by wincestdotcomChapters: 2/2
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Stanford Era (Supernatural), Phone Sex, Mutual Masturbation, (but neither of them know that it's mutual), Mutual Pining, sam's having a very bad time but dean's here to fix it, Dean Winchester/Sam Winchester First Time Having Sex, Anal Sex, Dean Winchester in Denial About Sexuality, Angst and Porn, Blow Jobs, Come Swallowing, Aromantic Asexual Sam Winchester
Sam's psych class is getting into his head and he can't tell what's real and what's been impressed upon him. Thankfully, Dean can help.
Humidity (832 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Mature
Warnings: Underage Sex
Relationships: Dean Winchester/Sam Winchester
Characters: Sam Winchester
Additional Tags: Pre-Stanford Era (Supernatural), Female Sam Winchester, Body Image, Introspection, Implied/Referenced Sex, Sibling Incest, Codependency
Series: Part 1 of Girlchesters
All she sees are gangly limbs when she looks in the mirror.
Trauma Bonding (1277 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Rape/Non-Con, Underage Sex
Relationships: Dean Winchester/Sam Winchester, John Winchester/Sam Winchester
Characters: Dean Winchester, John Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Underage Sam Winchester, John Winchester Finds Out About Dean Winchester/Sam Winchester, John Winchester Being an Asshole, Underage Rape/Non-con, Codependency, Familial Abuse
John isn't happy to find out about Sam and Dean.
Day 1: Curiosity (100 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Underage Sex
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Pre-Canon, Voyeurism, Mutual Masturbation, Weecest, Sam Winchester Has a Vagina, Drabble, Kinktober 2024
Series: Part 11 of Sam Winchester's Boypussy, Part 2 of Weecest, Part 1 of Kinktober 2024
Sam likes to watch Dean. (Prompt: Voyeurism)
Day 1.5: Subtlety (473 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Voyeurism, Masturbation, Hand Jobs, Dean Winchester Has a Vagina, Kinktober 2024
Series: Part 4 of Dean Winchester's Boypussy, Part 2 of Kinktober 2024
Sam is struggling to focus on a case. (Prompt: Voyeurism)
Under the Mistletoe (1848 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Episode: s03e08 A Very Supernatural Christmas (Supernatural TV 2005), temporary tattoos, Cunnilingus, Dean Winchester Has a Vagina, Hair-pulling, Post-Coital Cuddling, Praise Kink, Christmas Smut
Series: Part 13 of Dean Winchester's Boypussy
Dean Winchester is the king of regifting.
Stars Shining Bright Above You (626 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: Rape/Non-Con, Underage Sex
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Pre-Stanford Era (Supernatural), Teen Sam Winchester, Sam Winchester Has a Vagina, Mutual Pining, Non-Graphic Rape/Non-Con
Series: Part 36 of Sam Winchester's Boypussy
Sam Winchester has a strange night.
Playing Doctor (700 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Pre-Stanford Era (Supernatural), Medical Examination, Unresolved Sexual Tension, Weecest, Mutual Pining
Series: Part 6 of Weecest
Sam needs a second opinion about his pain.
Seeing Stars (100 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, New Year's Eve, Riding, Vaginal Sex, Sam Winchester Has a Vagina, Drabble
Series: Part 37 of Sam Winchester's Boypussy
Just a quick one before the fireworks display.
The Being Unknown (150 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Mature
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Dean Winchester/Sam Winchester Mutual Pining, Trauma, Drabble and a Half
Sam’s desire was visible from space.
Oral Fixation (100 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Implied/Referenced Sex, Established Dean Winchester/Sam Winchester, Drabble
Dean Winchester loves his baby brother's mouth.
Acquired Taste (3485 words) by wincestdotcomChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Dean Winchester, Sam Winchester
Additional Tags: Brother/Brother Incest, Dean Winchester Has a Vagina, Menstruation Kink, Cunnilingus, Established Dean Winchester/Sam Winchester, Prompt Fill, Hair-pulling
Series: Part 14 of Dean Winchester's Boypussy
When Dean struggles to cope with his period, Sam decides to test the legitimacy of a fact he learned in college.
A Pretty Girl is Like... (1074 words) by bloodbrothersChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Sam Winchester, Dean Winchester
Additional Tags: Brother/Brother Incest, Skirts, Anal Sex, femboy Sam Winchester, Cowgirl Position, Riding, Sam Winchester Has a Vagina, Feminization, Established Dean Winchester/Sam Winchester, Praise Kink, Hand Jobs
Series: Part 38 of Sam Winchester's Boypussy
Sam finds a skirt at the thrift store and discovers a deeply-hidden part of himself.
In Any Universe (883 words) by bloodbrothersChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Explicit
Warnings: No Archive Warnings Apply
Relationships: HunterCorp Dean Winchester/HunterCorp Sam Winchester, Dean Winchester/Sam Winchester
Characters: HunterCorp Dean Winchester, HunterCorp Sam Winchester
Additional Tags: Brother/Brother Incest, Established Relationship, Sex Tapes, Voyeurism, Anal Sex
While playing the roles of Sam and Dean, Sam and Dean end up finding a video that they were never supposed to see but might just end up deepening their connection with their alternate universe counterparts.
Bathtime (1829 words) by bloodbrothersChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Mature
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Sam Winchester, Dean Winchester
Additional Tags: Brother/Brother Incest, Pet Play, Submissive Dean Winchester/Dominant Sam Winchester, Praise Kink, Bathing/Washing, BDSM, Men of Letters Bunker (Supernatural), Domestic Fluff, Cuddling & Snuggling, Established Dean Winchester/Sam Winchester, Non-Sexual Kink, Gentle Dom Sam Winchester
When Dean refuses to get out of bed and take care of himself, Sam resorts to the unconventional.
Bleeder (442 words) by bloodbrothersChapters: 1/1
Fandom: Supernatural (TV 2005)
Rating: Mature
Warnings: No Archive Warnings Apply
Relationships: Dean Winchester/Sam Winchester
Characters: Sam Winchester, Dean Winchester
Additional Tags: Episode: s06e05 Live Free or Twihard (Supernatural), Vampire Dean Winchester, Soulless Sam Winchester, Brother/Brother Incest, Familiars, Dark Dean Winchester/Sam Winchester, Blood Drinking
A night in the new lives of Sam and Dean Winchester.
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