AN: Warning: I am not a trans woman. While I am transgender, I do not claim to have the experiences of a trans woman. I've had a headcanon that Sam Winchester was a trans woman for some time, and I wanted to bring about a bit of closure in this. If I in any way have offended someone reading this, I apologize, feel free to correct me.

It all started in November.

Actually, that's a lie. It all started, well, most of it, those two weeks in Flagstaff where the first thing she did (after finding somewhere to sleep) was go out and get a dress.

"It's for my sister," she said when the cashier looked at her strangely on her way to the fitting room. "We're, uh, twins."

It wasn't the nicest dress, but it was hers and she spent what time she could in it. She knew Dean and Dad were out looking for her, so she only put it on for a little while at a time.

"Samantha," she giggled into the mirror as she twirled the skirt around her legs.

Then there had been the case with the drag queens, one of whom was the witch they were chasing. Sam suggested one of them go undercover, and Dean slapped him on the back.

"Why don't you go ahead and do it if you're so keen. You'd make a beautiful lady, Sam." She knew Dean was joking, but she felt warm all the same. She nearly gasped when she finally saw herself all made up, looking like she'd always dreamed. Sure, her face was still a little too harsh, and her body was still big and square, but with the fake T&A, the mirror showed her a pretty good picture.

"You look lovely, darlin'" one of the queens said. "You done this before?" Sam shook her head. Sure, drag queens were exaggerations of women, but being in the getup was the closest she'd ever come to looking right.

Plus, she'd been rewarded with the massive pair of cherry pumps when she saved the drag queens. Dean nearly laughed his ass off, but Sam secretly kept those heels in her bag.

She would admit that she was a little disappointed when she was pulled out of Hell. Not that it hadn't been torture, but down there it had been just her and her soul, so she didn't have to think about what she'd rather have on the outside. The worst part about going back was that it meant being put back into that too-tall body with the too-deep voice.

But back to November.

She was in the bunker with her brother and Cas. She liked times like these, where there was nothing to do but laugh and she could see Cas smile. That was always nice. The angel had a little too much to drink, and he had always been a bit of an oversharer anyway.

"So that must be why you feel the need to pleasure yourself while looking at others fornicating."

"How the-"

"He has a point, Dean."

"Aw, c'mon man, you too?" Cas stopped laughing then looked between the two. Dean sensed he was missing something. "What?"

"Sam is a woman," Cas said matter-of-factly. Dean looked between them. Was Cas serious? He almost laughed until he saw tears forming in Sam's eyes.

"I gotta go," she said. She went to her room and shut the door, then broke down on the other side. Great. Now Dean, the last person in the world she wanted to know, knew. She looked over at her bag. Well, she'd be kicked out sooner or later, might as well pack.

Back in the main room, Dean turned back to Cas.

"What do you mean, 'Sam is a woman'?"

"Sam possesses a female soul that was unfortunately put in a male body. Sometimes souls are mixed up and put in the wrong place, like Sam's."

"So he's always been a chick?" Cas shrugged.

"At least as long as I've known her. Have you not noticed this unrest? She must hide it well."

"So this whole time he's, she's been my sister." Dean swallowed. "God, that must be hard. Especially with no mom…"

"I doubt your father would have been willing to address her as such." Dean stood up.

"Can you go keep Sammy company? I, uh, gotta clear my head."

"Of course."

Sam heard a knock on her door, then heard it open. Must be Cas. She looked up at him.

"Let me hear it. Is Dean kicking me out?" Cas furrowed his brow and sat on the floor next to her.

"I don't think so. He's gone out for a moment, but I assume he'll be back." He turned to face her. "He doesn't hate you, Sam. You're still his family, after all." Sam paused for a moment.

"Hey, Cas?"

"Yes?"

"Uh, how long have you known I was, well, me?"

"I could always see it. I'm sorry, by the way."

"For what?"

"When I pulled you from Hell. I wish I could have given you a better body, but it was enough hassle getting you out in one piece, which I managed to mess up anyway."

"It's not your fault," Sam looked at her shoe. "But uh, is there any way you could fix me now?" Cas shook his head.

"I have no such power, I'm afraid. One of my brothers, perhaps, but any angel that might have been able to is dead."

"Well, worth a shot I guess. Maybe there's a spell or something."

"Perhaps."

"Cas?"

"Hm?"

"Will you wait with me until Dean comes?"

"Of course."

A few hours later, there was a knock on the door.

"Sammy?" Dean's voice called from the other side.

"Thanks, Cas." Sam stood up to answer it and Cas flew away. She opened the door to see Dean standing there sheepishly with a plastic bag.

"Heya, Sammy. I got you some stuff. It's not much, but I though, you know," Dean was blabbering. Sam took the bag and looked inside. There was some makeup stuff, and…

"You got me plaid tights?"

"I hope they fit. Listen, I just wanna let you know that you're still my, uh, sister, and I just want you to be happy." Dean smirked. "Plus you'll need some makeup for that face."

"Shuddup," Sam said. She squeezed Dean tightly in a hug. "Thank you," she whispered into his ear. She was crying again, but for the right reasons.