.11 It's Never Like That - LaPilar - Supernatural [Archive of Our Own]
A bad dream while on a dragon hunt leads you to confess to Dean that your virginity is putting the team at risk, and you'd like him to fix that. He agrees, the gentleman he is.
My First - theinsandoutsofcastiel - Supernatural [Archive of Our Own]
reader (like 18 or 19)xdean where she’s known him her whole life & he’s her best friend & she’s in love with him and wants him to be her first so she asks him one night in the bunker?
Virgin - theinsandoutsofcastiel - Supernatural [Archive of Our Own]
a Dean fic where like the reader is a virgin, and Dean teases her about it but the reader gets mad and storms off only later to bring back a random guy she plans to hook up with, and Dean gets really mad/jealous?
The Price of Love - indigo_carter - Supernatural [Archive of Our Own]
he reader and dean have sex and the reader is a virgin so when dean enters her it really hurts and after she is really sore and he takes care of her and stays with her and they keep having sex
My boys - Iliketowrite_2 - Supernatural [Archive of Our Own]
You’ve dated the Winchester brothers for a while, but you’d never gotten to do anything dirty in the bedroom for a reason. You’re a virgin.
Ask Me - evansrogerskitten - Supernatural [Archive of Our Own]
You’re drunk with the Winchester boys and you want to play a drinking game. Oh, and you want to fuck them both too.
New Mexico - aly_m_cap - Supernatural [Archive of Our Own]
You never thought your Dreams would actually come true when it came to the oldest Winchester. You were pleasantly surprised with how things turned out when you and Dean left for a hunt in New Mexico.
Free To Be You and Me - thingyoudowiththatthing - Supernatural [Archive of Our Own]
Memory Trips And Scraps Of Paper - kittenofdoomage - Supernatural [Archive of Our Own]
Sweet Communion - rockhoochie - Supernatural [Archive of Our Own]
While Sam and Dean are out working a case, Y/N enjoys a little alone time. But when Dean returns to their motel room early, things take a sinful turn
Aesthetics of Hate - khalisey - Supernatural [Archive of Our Own]
Hate is a strong word but not nearly strong enough to describe how much you abhor your asshole of a step-brother.
'cause my body's sweet like sugar venom - darcychick - Supernatural [Archive of Our Own]
confounded by sex and why humans do it. Dean is more than willing to help her understand.
A First Time For Everything - LavenderNomad - Supernatural [Archive of Our Own]
virginity and gives you your first orgasm
No Touching - MimiWritesHerFandoms - Supernatural [Archive of Our Own]
Imagine playing a game with Dean where you watch porn together and whoever touches themselves first loses.
Regular Check-Ins - dianapowerslit - Supernatural [Archive of Our Own]
You and Dean have been friends since he saved your life, but is there more there? Is it mutual?
We Got Time - coveredbyroses - Supernatural [Archive of Our Own]
Dean takes the reader's virginity, she's moved to the bunker as well, Dean and her had always flirted a little every now and then, but he considers her too young, (he's 35, in s10, she's 19ish), and is afraid to hurt her, but she reassures him she's fine and admits how freaking much she thinks about him. :) She's suddenly got a dirty mouth on her even though she usually is a bit shy and Dean gets turned on and ends up wanting her too, so he takes her virginity."
Based on a few imagines from dirtysupernaturalimagines on tumblr. Chapter one is 'Imagine changing in front of Sam and Dean and they find your hunters tattoo on your pelvic bone' and the beginnings of 'Imagine a witch cursing you with a spell so that you're constantly horny so the boys help as much as they can'.
Not Without Me - spnsecret - Supernatural [Archive of Our Own]
Dean walks in on you taking care of yourself while he's away. He decides to watch and have a little fun.
Similar But Not The Same
She's Sams mate, Dean shouldn't be able to have this effect on her
Paid in Full - Dustybaby - Supernatural [Archive of Our Own]
Imagine being left alone with the Impala, Dean leaves the keys on the table so you can’t resist the urge of driving her but end up crashing her. (I couldn't wreck her.)
Apple Pie - AvaJune - Supernatural [Archive of Our Own]
You're not entirely sure when it started, this little obsession of yours. But it feels like it's been going for a long time, maybe as long as you've known them. The Winchester brothers are both unfairly attractive, but while Sam is definitely a man you enjoy seeing shirtless, it's Dean who holds your heart and soul in his hands. Whether you would be someone Dean would want is unknown, but frankly, irrelevant. The world is always ending, someone is always getting possessed, and there just never is time for much of anything except work when it comes to the Winchesters. In which the Reader is a sweet little cupcake, Dean is stubborn, and Sam is long-suffering.
Bring It On Home to Me - evansrogerskitten - Supernatural [Archive of Our Own]
Dean drowns his sorrows in whiskey as he faces what he said to you.
Walls - Chelsea072498 - Supernatural [Archive of Our Own]
Mary leaves the boys. Reader tries to help.
Dive - BecaAMM - Supernatural [Archive of Our Own]
You and Dean… You weren’t a real thing. Sometimes, when you were too drunk and needy, you slept together and pretended it didn’t happen in the morning and that was it; but when you fall pregnant and the only possible father is no other than Dean Winchester, you need to make a hard decision. How hard would it be to hide a pregnancy from the Winchesters while living with them?
Drawn - kittenofdoomage - Supernatural [Archive of Our Own]
The reader is an Omega, but after an incident ended up with her family hurt, she put herself into self-imposed isolation. She never expects that she’d find her Alpha in a supermarket whilst he’d buying medicine for his flu-ridden brother.
Curves And Edges - kittenofdoomage - Supernatural [Archive of Our Own]
Reader is plus sized, and never even imagined Dean would look at her that way. Boy was she ever wrong...
You And The Winchesters: Tales of Smut, Antics and Pie - WordsAreMusicForTheEyes - Supernatural [Archive of Our Own]
You And The Winchesters: Tales of Smut, Antics and Pie
Laundry Day - Mvampirefreak - Supernatural [Archive of Our Own]
Laundry day is the reader's day to relax and unwind and listen to her music. Today, however, Dean has a different activity ready for her.
Being Right Isn't Always a Good Thing
Sam and Dean aren't listening to you, and you become annoyed, especially when it puts Dean in danger.
Undress Me - Girl_WithTheDirtyMind - Supernatural [Archive of Our Own]
Dean spontaneously volunteers to take you shopping after the brothers find you upset in your room at the Bunker. You've had a crush on the rugged Hunter for a while now. . . Smutty smut ensues ;) I was feelin' it today, so here's a quick fic I wrote up :) Enjoy~ Dressing Room fic.
Professor Dean Winchester AU - DeansDirtyLittleSecret - Supernatural [Archive of Our Own]
Professor Dean Winchester AU
Does a Hoodie Count as Lingerie? - ninaloveshiddles - SPN [Archive of Our Own]
Dean has been in love with the reader for a long time, but the reader is a little too innocent and clueless to notice the looks he gives her. On a hunt, they have to share a bed for the night and she wears one of his old hoodies; only his hoodie. Dean finds out and smut ensues. Reader is sweet and inexperienced, but Dean knows how to take care of her.
Never Even Been Kissed - DeansDirtyLittleSecret - Supernatural [Archive of Our Own]
Reader lives with the boys and does research for them while they're on hunts. She's kind of quiet and when Dean finds out that she's never even been kissed he shows her how. He's super slow and gentle. Then it leads to them making love. (request on tumblr)
Demonic Control - MistyAnn_Winchester - Supernatural [Archive of Our Own]
Imagine being on a chase after Crowley with Dean and Sam, and every time you find a clue to where he is, he gives you an orgasm with his demon powers leaving you, Dean and Sam baffled and horny.