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It shouldn't be a big deal. In fact, it's not a big deal, he decides. It's just a skirt. A pleated, black, plain, soft skirt.
It's not a big deal.
Jess made him buy it after going back to look at it for the fourth time. She had smiled in that charming, bright-eyed way that made Sam fall in love with her more. You should try it on, she had said. It'd look good on you. Sam had scoffed, but turned a little pink at the thought. He had never worn a skirt before, or a dress, or anything that reminded him of femininity. Growing up, he had turned away in disgust from femininity, as did his father and brother, but there's a part of him, deep deep down, that's intrigued by it. Maybe even a hint of longing for it.
He's wearing one of Dean's old band tees that had gotten into his duffle somehow when he had left for Stanford, and it doesn't really go with the skirt, but it kinda does at the same time. He considers tucking it in the skirt, so he does. His legs are hairy, and he's not wearing any shoes, just some old once-white socks with a hole in the heel. But he feels… beautiful. He shakes his head at the thought, trying to make it disappear. He considers himself in the mirror. He smooths over his chest, down his body. He plays with the end of the skirt, which stops a few inches above his knees. He turns, twisting his neck so he can keep an eye on the damned skirt. Why does a piece of clothing feel so… powerful? Why does any of it matter? It matters to you, a small voice inside of him says. He sighs.
Sam takes off the skirt and goes back into his gym shorts, tucks the skirt deep into his closet. He doesn't think about it for a long time.
It burns alongside Jess and the rest of his belongings.
Back on the road with Dean, back into hunting, back to the same fucking life he has been running from. He had always meant to go back to California, but it grew more and more into a fantasy. Then Dad died, then Sam did. Dean sold his soul for Sam. Then Dean died. And now Sam is alone, alive when he shouldn't be.
He drinks straight from the bottle. He's squatting in an abandoned church, unable to afford a night in a motel. Hustling pool by himself is harder without Dean there, and all of his money goes to alcohol nowadays, and pills. Anything to take the edge off.
He looks down at his fingers, at the chipped nail polish. Another thing he's always wanted to try but was always afraid to. He nibbles on his fingernail absentmindedly. He wonders what Dean would say about his nails. If he would approve of the color-- black-- or if he would think the whole thing is for pansies and girls. He forces the thought away, as he does with all thoughts about Dean now. He takes another swig from the bottle.
He guesses it doesn't matter what Dean would think. He's fucking dead anyways.
Dean comes back from Hell. There's angels and Devils and Heaven and Hell and the apocalypse. Sam loses his soul, then gets it back, bloody and mangled. He hallucinates Lucifer. He gets nightmares worse than ever. There's Leviathan and Purgatory and vampires and trials to close the gates of Hell. It never stops. It never ends. One shitty thing after the other.
Sam is in his room in the bunker, and thinks back to the fucking skirt that Jess made him buy. Thinks about the eyeliner he bought earlier that day. It was an urge, a whim, that made him grab it and set it down on the drugstore counter, cheeks pink. The cashier said nothing, of course. But Sam hid it in his jacket from Dean and didn't let him see the receipt. He didn't need to hear what Dean would say. He's not even sure why he bought it. He holds it in his hands now, twirling it around. It looks just like a pencil, so why is there so much feeling behind it? Why does it feel like a dirty secret, like something exhilarating?
He looks to make sure his bedroom door is locked. Check. Then he pops the lid off of the eyeliner and leans in close to the mirror on his wall. With shaking hands, he lines his top eyelid with it. Then the other eye. He looks at himself in the mirror. The eyeliner makes his hazels pop, and there's something grungy to the look. He… likes it. He really likes it.
Suddenly he feels like crying. He blinks quickly to get rid of the burning in his eyes. Why is this so hard? Dean never seems to have a problem or daily crisis with how he looks. Dean is the most self-assured person he knows.
Why can't he be more like Dean?
It's Sam's birthday. A day, in the past, that either meant nothing or meant the end of the world. Never something he looked forward to. Never something worth celebrating.
However, this year is different. There's no death, no apocalypse, no soul-shattering revelation. Things have been… quiet. Good, almost, ever since they defeated Chuck. And Sam feels almost comfortable in his own skin. Which is an entirely new feeling, but not an unwelcome one.
His nails are a dark purple, and he's got smudged eyeliner on, and he's in his usual jeans and flannel combo. Dean was surprisingly cool with these little changes, claiming he'll always be his little brother no matter what; which didn't make Sam almost cry, nope. He still liked to experiment with other items of femininity, but he's more comfortable with it now. It didn't make him less of a man. What a strange new world.
Dean baked him a cake and he blew out the candles and wore the ridiculous headband Jack bought him. Cas gave him some new teas and some local honey. They all curled up in the Dean Cave and watched a movie that Sam got to pick out. All in all, a pretty damn good birthday.
Sam has never been more happy.