Chapter One

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Being transgender has never been nor will it ever probably be easy. Trying to comprehend what you're feeling. Attempting to make sense of the chaos that is in your head.

The only thing Cassandra Winchester had going for her is that she was Dean Winchester's little sister. Dean was on the football team in high school and let it be known that he acts the same off field as he does on it when it comes to his family. Everyone knew who he was, and everyone knew not to fuck with his little sister. He never treated Casandra like a little sister though. Cassie was always included in the vigorous training that John put Dean through. Something about the family business, upholding the 'family' part of it. John was a hard ass. But it was tough love. He treated his kids like they were his most prized possessions. Which to him, they were. Cassie came home one day from school only to see John and Dean training again in the back yard.
"Hey guys," she sat on the back porch steps, a book in her lap.
"Hey Cassie," Dean punched the pads their father was holding up for him, "how was school today?" Another punch.
"Boring, mostly. We just got to Benvolio's big scene in Romeo and Juliet today." She flipped through the book on her lap.
"No track tonight?" He asked. Cassie didn't want to admit that she was feeling so uncomfortable with herself that she was skipping. She usually works through it and just goes but today was different. More painful for her.
"No, they, uh, cancelled it. Something with the coaches.." She trailed off.
"Is that the book right there?" John asked.
"What?" Her face scrunched up in confusion.
"Is that 'Romeo and Juliet' right there?" They paused their training.
"No, this is 'Scars'. I really like it so far." She found her page and began reading, only to be interrupted.
"What's it about?" Dean looked alarmed as he glanced at the front cover.
"A girl named Kendra. She's an artist and was raped from a young age till she was 12. She's gay and self-harms to keep herself from remembering who hurt her. She doesn't have a good relationship with her parents really. But she's got Sandy, so it's okay. It's really interesting. I really like it." She looked up after talking and she saw the looks on her families faces. "What? I like books like this." She shrugged her shoulders.
"We'll talk about that later." Dean laughed and went back to training. Cassie got up and went inside so she could read in peace.

A little while after Dean came inside and asked if Cassie wanted to come on a run with him.
"Are you sure? I don't want to slow you down." Cassie set down her book to give Dean her full attention. Pushing her glasses up the bridge of her nose.
"Cassie, I've watched you run in track. You're one of the fastest kids out there. If anything, I'd have to keep up with you." Dean went around the island in the kitchen and grabbed a bottle of water from the fridge.
"Oh. Um, then uh, yeah. Let me go change." Cassie bounded up the stairs and to her room. She grabbed a sports bra, athletic shirt, and shorts and stood in front of her mirror. Looking at herself in the mirror she felt unsettled. It felt like something wasn't right. She changed into the sports bra and shorts, looking at herself again. She hoped that this run would help her feel better.
There was a knock on the door. She quickly threw her shirt on and opened it. It was Dean, landing at her feet.
"Why were you leaning against my door?" She laughed looking down.
"I was, um, waiting and I just kinda, uh," Cassie laughed harder, "shut up." He got on his knees and tackled her to the ground. A wrestling match ensued, Dean ultimately winning in the end.

They ran roughly four miles around town and then stopped at the ice cream shop before going home.
"So, are you going to tell me why you skipped practice today?" Cassie choked on her ice cream.
"How'd you, um, find out?" she could feel her face getting redder by the second.
"Cassandra. I'm not stupid. And I have friends with younger siblings you know. They asked me to ask you why you weren't there. So? Why'd you skip? You've never skipped before." He didn't sound upset or anything. Just genuinely curious.
"I'm not...I'm not really up to talk about it right now." She piled a giant spoonful of caramel ice cream into her mouth, causing a laughing fit from Dean.
"You eat like a guy." He gasped between chuckles.
They ran home and showered. They ended up crashing that night on the couch while watching Shameless. John walked in and saw them there, but didn't bother to wake them. He put a blanket across them and went to his own room.

--

The next morning Cassandra woke up late because she never plugged her phone in.
"Shit, Dean? Dean, wake up!" She tugged at Deans sleeve.
"Cassie? What's wrong?" he groggily sat up and rubbed his eyes.
"We fell asleep, never plugged in my phone, no alarm, dad's gone, gunna be late.." she trailed off into small whispers as she hurried around to get ready.
"Whoa, okay. Slow down, alright? I'll take you, just go get ready?" Dean got up and went to the kitchen while Cassie went to go shower.

30 minutes later Cassie bounded down the stairs still in a panicked state trying to get her shoes on.
"Why're you so dressed up?" Dean put a piece of toast into her open mouth and set a mug of coffee on the island in front of her face.
"Track meet," she said around the toast, "you ready?" she slammed her foot down to force her shoe on and transferred the coffee to a to-go cup. She stole a drink from Dean's mug finishing it off for him.
She clicked her tongue, "ew, sugar. This early Dean? Really?" She went to stand by the door to hurry the process of him getting ready up.
"Don't judge me. Do you train for six hours everyday? No? Okay then. Go start the car I'll be out in five." He threw the keys out to her and went to his room.

She was sitting in the impala when she remembered what Dean had told her yesterday. How she eats like a guy. He tells her that a lot now that she thinks about it.
'you eat like a guy'
'you train like a guy'
'you play like a guy'
She decided she'd have to dwell on this later. Right now she has to get to school so she can take her chem test.

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