So, I wanted to write this mostly because of Caitlyn Jenner. I also wrote this for my transgender friends :)
Samantha Winchester looked down at her fingers as she was lectured by her father. It wasn't necessarily something she had done. They were preparing for another year of school shopping. Usually when Samantha's - "It's Sam, dad" - clothing became worn out, she would just take some of Dean's old clothes. She was small, and it worked.
Lately, though, John had been obsessed with her acting her gender. He had already mentioned going shopping for some clothes more suited for a 'young lady' several times. Sam knew it was only a matter of time before he would actually follow through on what seemed to be a threat to her.
"Okay, Samantha," John started. He refused to call his daughter anything other than her birth name. No Sam nickname nonsense. "There will be no novelty t-shirts or flannel shirts, understand?"
"Yes, sir," Sam said quietly.
"I will not let my daughter go walking around looking like she hasn't showered in a month," John said.
"But, dad, I wear the same clothes you and Dean do," Sam argued.
"Dean and I are men, and you are a young lady," John said. "When you grow up, you can pick what you wear, but since you are twelve, you will wear the clothes that I buy for you."
"You sure this is a good idea?" Dean asked from the sidelines. He always tried to prevent a war in the Winchester household. "I mean, we don't have a lot of dough, and Sam can always wear my clothes." Dean would use the nickname 'Sam'. He was the only one.
"Samantha will wear clothes suitable for her gender," John said. "Let's go."
Sam hated shopping.
She hated it more than she hated her body, and that was saying something. Luckily, she didn't have to go through the torture that was shopping very often, as Dean was right, they didn't have a lot of money.
Sam would gaze longingly at the boys section of the store, wishing that she could get one of their t-shirts, or even just their jeans. Girl jeans always hugged the wrong places for her.
"What about this?" John asked, holding up some denim skirt that Sam hoped he would never see again.
"No thanks," Sam said.
"You have to pick something," John said. "We're not leaving here until you have a decent outfit for school tomorrow, and you only have an hour before I head out of here. Whether or not you like what you're wearing is not my decision."
In the end, Sam hated the outfit she was forced to pick.
It was that god awful denim skirt with a pink t-shirt that said something about boys on it.
Sam was so thankful when she grew out of it that next summer.
John didn't buy her any more.
When Sam was thirteen she woke up with a horrible pain in her stomach. Flipping out of the bed in order to get help, she saw a pool of blood in the spot of the bed that she had previously been occupying.
"Dean!" Sam called out. Dean was her only life-line when it came to problems like this. Especially embarrassing ones. By the blood on her pants, she knew this would be an embarrassing one.
Dean jumped out of the shower he had just been, wrapping a towel around his waist, and running out to the bed where Sam had been sleeping. He saw the blood, and instantly groaned.
"I was hoping you would be a later bloomer," Dean said. "You know, so we could avoid this."
"What is this?" Sam asked.
"You're, uh...you're a woman..." Dean trailed off. A shade of pink hit his cheeks. "Get changed, we gotta go to the store."
Sam went to the bathroom and showered in order to clean the mess off of herself. She then dressed into her jeans - her father had finally relented and bought her boy jeans - and a t-shirt that belonged to Dean.
The store had to be the most embarrassing part of the situation.
Dean had gone inside with her and immediately guided her to the feminine hygiene section. Apparently Dean knew where they were because he had gotten condoms over by there before, according to Dean, anyway.
"Excuse me," Dean said to a salesgirl to get her attention. "My younger sister just, uh...got her visitor for the first time. What do you think she needs?"
"Oh, I'll take care of her, dear," the girl said. "You can go a couple isles down to the video game isle."
Dean did so gratefully.
"Okay, sweetheart, what you're going to need is either pads or tampons," the girl started. "Since it's your first time, I'd go with the pads, but you can get both and experiment with how you feel and what you're comfortable with when the time comes."
After the salesgirl helped Sam pick out her items, Dean came back. Once he was back, he paid for the items and made his way home.
Sam stayed in bed for the majority of that first week.
When Sam was in high school, she was bullied. At every school she went to, she was a part of the guys for a while. Of course, that's until she started agreeing with them that the girls were in fact attractive. They suddenly shunned her for being a dyke.
The first thing Sam did when she got out of there, was change her name to Sam and go to school.
Sam met a great girl, who helped him with having a double mastectomy. She also helped him find information about testosterone supplements, and directed him to some groups that had people like him.
It was the first time Sam had ever felt completely confident with his own body.
Dean had always been there for him, sure. But that was as a big brother trying to keep the peace in his family. Dean steered their father away from the skirts and dresses. He also kept Sam away from anything too boyish, which meant that he wasn't allowed to cut off his long curly brown hair until he was fifteen and had rebelled.
"Dean?" Sam asked when he suddenly saw his brother - who he thought was an intruder - in his apartment.
"Sammy?" Dean asked. Sam knew that his eyes were not wide with anything but shock. He knew that his older brother was scared that he had lost his baby sister.
Suddenly, Dean grinned in a way that Sam did not expect.
"What took you so long, little bro?"