boy, you've been a naughty girl.
One thing this fandom definitely knows how to do right is kink, and one kink that there's plenty of-or not nearly enough of, depending whom you ask-is crossdressing. I figured this was an excellent kinktheme for my first rec list, because, well, why not? (It's worth noting that all of these fics are Sam/Dean, and that in the majority of them, Sam is underage. Age noted in the included warnings.)
Too Sexy For My Skirt by checkthemargins [ NC-17 | 12.4k | underage (Sam is 16) ]
summary: Dean has a request. Sam isn't as opposed to the idea as he thought he might be. Christmas turns out really, really good in the Old Hector Motel room.
This fic so totally captures what it feels like to be sixteen and in love, breathless. The slow build to the actual crossdressing is perfect, because it is filled with the boys just not being able to get enough of each other. And once they get there, well, it may be one of the most scorching things ever written.
Oh My Next Girl (She'll Be Nothing Like My Ex Girl) by oddishly [ NC-17 | 13.5k | underage (Sam is 16) ]
summary: It's amazing what you can get away with when people think you're a girl and your brother is your boyfriend.
The world the author creates here is so damn believable. Not that it's an AU, but there may be some robbing of banks and picking of pockets involved, not to mention boys (yes, boys) who dress up as girls to get away with things. Or boys who dress as boys to get away with things. There's shaving, there's exhibitionism, there's panties, and at one point, Sam makes it clear that he believes fucking in the car on the side of the road is too vanilla. Just, ahem.
Also written by oddishly, and definitely crossdressing-noteworthy, is Everything With Wings Is Restless [ NC-17 | 16.5k | mild D/s ], a magician!AU in which Dean's the lovely sidekick in the slinky red dress.
untitled commentfic fill by strive2bhappy [ NC-17 | 5.5k ]
Do not let the lack of a title and summary dissuade you, because this fic is stunning. The characterization of both of the brothers is spot on, and they're completely that, brothers. The different layers of love that the author managed to lay out are phenomenal, not to mention the hot, and the tenderness is just perfect.
Weekend At Bendy's II by valiant [ NC-17 | 11k | Dean/Sam/Lisa, underage (Sam is 16), genderplay, faux-lesbianism, impreg kink ]
Now I know you've read the prequel, Easy Access [ NC-17 | 3.1k | underage, genderplay, impreg kink ], but what's different about this fic is just how far it goes. It's a first time (threesome) fic unlike any other.
On The Road Again by akintay [ R | 3k ]
summary: After Stanford, Sam is plagued by nightmares and guilt and his feelings for Dean.
Be sure to first read this untitled Stanford-era ficlet [ R | 2k ], which is the beginning of the verse. These two fics just hit all of the right places. It's pitch-perfect Stanford era, with the longing that only true absence can create, and then back-on-the-road-together neediness resulting in a first-time all over again. It's panty kink, but not in your face, subtle, and second to the everything the boys are to each other.
Pretty In Pink by beckaandzac [ NC-17 | 3.2k | underage (Sam is 15) ]
summary: When Dean arrives to pick Sam up from a party, he doesn't expect to find his brother drunk and in a tutu.
That's right, a tutu-who would've thought it could be so hot, and who would've thought Sam would be so comfortable in one? Sam's voice in this is excellent, and the view we get of the care Dean takes with him is just as great.
Pretty Please by chemm80 [ NC-17 | 1.9k | underage (Sam is 16) ]
From this year's spnspringfling, so I know you've read it, but come on, read it again! To quote myself, EVERY SINGLE THING IN THIS IS PEEEERFECT. Young Sam and Dean, hiding in a dressing room, with Dean teasing the hell out of Sam with a pair of pretty panties? Yes, perfect.
Nylon by kat_lair [ R | 0.1k ]
Super short and not at all sweet. This one hits it right on the head.
Bearing Gifts by kid_viciously [ NC-17 | 3.6k ]
summary: Sam takes a chance on a little "out there" gift…
If you can forgive the overly abundant ellipses and lack of commas, then you're in for a wonderful surprise. Crossdressing done oh so right, with both boys daring to show their vulnerability.
Law Of The Talon by lexicale [ R | 2.2k | "SPN meets 'The Outsiders'" AU, androgyne!Sam, underage (ages unstated) ]
summary: Ever since R.J. left, Dean's been in charge of their neighborhood. That means that when there's a problem, he's got to deal with it -- the only issue? His hotass little brother is purposefully trying to distract him.
The only fic in this list that doesn't necessarily include outright crossdressing. Instead, this fic deals with a Sam that genders himself neutrally. And while it is an AU, it is just so them. There's also an amazing sequel, Figure Of The Anasyromenos [ NC-17 | 1.4k ], in which Sam "continues to be a hotass" at Dean. Wonderful hotassness, indeed.
All Their Favorite Rags Are Worn by orbiting_saturn [ NC-17 | 4.5k | underage (Sam is 15) ]
summary: The truth is, Dean wants someone to see him, even if that someone is his fifteen year old brother who will probably go into paroxysms over his tough-ass brother in a pair of pretty pink panties.
One of the many fics to take ahold of 2014!Dean's acknowledgement of Rhonda Hurley, but this one really runs with it in such an excellent way. And did you know that there's an equally scorching sequel, You Are What You Want To Be [ NC-17 | 1.5k ], and that there's podfic by the super talented afattribble?
And if you're still in the mood for more, check out this post at sd_recs. Of course, I'd love to know if you've got any others to rec, so please do share!
Too Sexy For My Skirt by checkthemargins [ NC-17 | 12.4k | underage (Sam is 16) ]
summary: Dean has a request. Sam isn't as opposed to the idea as he thought he might be. Christmas turns out really, really good in the Old Hector Motel room.
This fic so totally captures what it feels like to be sixteen and in love, breathless. The slow build to the actual crossdressing is perfect, because it is filled with the boys just not being able to get enough of each other. And once they get there, well, it may be one of the most scorching things ever written.
Oh My Next Girl (She'll Be Nothing Like My Ex Girl) by oddishly [ NC-17 | 13.5k | underage (Sam is 16) ]
summary: It's amazing what you can get away with when people think you're a girl and your brother is your boyfriend.
The world the author creates here is so damn believable. Not that it's an AU, but there may be some robbing of banks and picking of pockets involved, not to mention boys (yes, boys) who dress up as girls to get away with things. Or boys who dress as boys to get away with things. There's shaving, there's exhibitionism, there's panties, and at one point, Sam makes it clear that he believes fucking in the car on the side of the road is too vanilla. Just, ahem.
Also written by oddishly, and definitely crossdressing-noteworthy, is Everything With Wings Is Restless [ NC-17 | 16.5k | mild D/s ], a magician!AU in which Dean's the lovely sidekick in the slinky red dress.
untitled commentfic fill by strive2bhappy [ NC-17 | 5.5k ]
Do not let the lack of a title and summary dissuade you, because this fic is stunning. The characterization of both of the brothers is spot on, and they're completely that, brothers. The different layers of love that the author managed to lay out are phenomenal, not to mention the hot, and the tenderness is just perfect.
Weekend At Bendy's II by valiant [ NC-17 | 11k | Dean/Sam/Lisa, underage (Sam is 16), genderplay, faux-lesbianism, impreg kink ]
Now I know you've read the prequel, Easy Access [ NC-17 | 3.1k | underage, genderplay, impreg kink ], but what's different about this fic is just how far it goes. It's a first time (threesome) fic unlike any other.
On The Road Again by akintay [ R | 3k ]
summary: After Stanford, Sam is plagued by nightmares and guilt and his feelings for Dean.
Be sure to first read this untitled Stanford-era ficlet [ R | 2k ], which is the beginning of the verse. These two fics just hit all of the right places. It's pitch-perfect Stanford era, with the longing that only true absence can create, and then back-on-the-road-together neediness resulting in a first-time all over again. It's panty kink, but not in your face, subtle, and second to the everything the boys are to each other.
Pretty In Pink by beckaandzac [ NC-17 | 3.2k | underage (Sam is 15) ]
summary: When Dean arrives to pick Sam up from a party, he doesn't expect to find his brother drunk and in a tutu.
That's right, a tutu-who would've thought it could be so hot, and who would've thought Sam would be so comfortable in one? Sam's voice in this is excellent, and the view we get of the care Dean takes with him is just as great.
Pretty Please by chemm80 [ NC-17 | 1.9k | underage (Sam is 16) ]
From this year's spnspringfling, so I know you've read it, but come on, read it again! To quote myself, EVERY SINGLE THING IN THIS IS PEEEERFECT. Young Sam and Dean, hiding in a dressing room, with Dean teasing the hell out of Sam with a pair of pretty panties? Yes, perfect.
Nylon by kat_lair [ R | 0.1k ]
Super short and not at all sweet. This one hits it right on the head.
Bearing Gifts by kid_viciously [ NC-17 | 3.6k ]
summary: Sam takes a chance on a little "out there" gift…
If you can forgive the overly abundant ellipses and lack of commas, then you're in for a wonderful surprise. Crossdressing done oh so right, with both boys daring to show their vulnerability.
Law Of The Talon by lexicale [ R | 2.2k | "SPN meets 'The Outsiders'" AU, androgyne!Sam, underage (ages unstated) ]
summary: Ever since R.J. left, Dean's been in charge of their neighborhood. That means that when there's a problem, he's got to deal with it -- the only issue? His hotass little brother is purposefully trying to distract him.
The only fic in this list that doesn't necessarily include outright crossdressing. Instead, this fic deals with a Sam that genders himself neutrally. And while it is an AU, it is just so them. There's also an amazing sequel, Figure Of The Anasyromenos [ NC-17 | 1.4k ], in which Sam "continues to be a hotass" at Dean. Wonderful hotassness, indeed.
All Their Favorite Rags Are Worn by orbiting_saturn [ NC-17 | 4.5k | underage (Sam is 15) ]
summary: The truth is, Dean wants someone to see him, even if that someone is his fifteen year old brother who will probably go into paroxysms over his tough-ass brother in a pair of pretty pink panties.
One of the many fics to take ahold of 2014!Dean's acknowledgement of Rhonda Hurley, but this one really runs with it in such an excellent way. And did you know that there's an equally scorching sequel, You Are What You Want To Be [ NC-17 | 1.5k ], and that there's podfic by the super talented afattribble?
And if you're still in the mood for more, check out this post at sd_recs. Of course, I'd love to know if you've got any others to rec, so please do share!