Author's Note: I don't own Supernatural. This fic takes place in the second season of the series.
Charlotte Winchester is an OC that I came up with on Tumblr, where I originally shared this fic. I wrote this to try and get back into writing fics. I may write more fics expanding on her character.

"How'd you get into this life, kid? I know that you didn't wake up one morning and decide that you wanted to kill monsters for a living. No one in this life ever does." Ellen took a sip from her glass, having heard nothing about any of the Winchester siblings from John.

Charlotte laughed nervously and took a drink, "It's never been a choice. It's the only life that I've ever had. I was born and raised by John since I was a baby after my mother's death." She supposed that her mother must have been a smart woman having taken the time to list John's info in case anything happened to her. It made Charlotte wonder if her mother was a hunter or knew about John's hunter life. Both were unfortunately questions she could never get answers to.

"At that point, he had already been hunting for Yellow-Eyes for a few years. Hell, it was so normal to me that he had to take me out of school when I was 8 years old because I would talk about it. Apparently schools take children speaking about real monsters as a sign that there are issues in the home environment." She shrugged. There had been plenty of issues in her home life. Her father was absent hunting monsters most of the time leaving her two older brothers to have to watch her. It had caused a drift between her and Dean for years, since he often had to act as the parental figure.

Ellen shook her head, "I never thought of John as the type to homeschool a kid." The woman had never seen the father side of John though, only the hunter.

Charlotte laughed, "Oh, he wasn't. Sam would tutor me when he'd get out of school because he's always been the book smart one." It was during that time when she was left unattended during the days that the bored child had begun snooping into her father's articles and seeing what he was hunting. Between the articles and lore books left lying around, Charlotte had thought that she was ready to be a pro-hunter back then.

Charlotte looked down into her glass, "I was a naive fool back then. I would snoop through my dad's stuff that related his cases while I was alone. I thought that I was ready. That all I needed was to know some lore. Hell on top of that, I used to actually think that I had the same mom as Dean and Sam. Like, oh, one day I'll help dad kill the demon that killed my mom." She laughed sadly. With everything going on, there were days that she missed the old days of childhood naivety. "Sam and Dean never did directly tell me the truth about us having different moms. Dean was too busy looking out for me and wanting to protect me from all the monsters that we knew were real. And Sam was my best friend. I used to tell him everything. Especially after Dean graduated and started hunting with dad more. It was just the two of us hanging out for years." Oh how things changed. Sam and John would clash, leaving Dean to be the one trying to convince Charlotte that everything was alright.

Ellen began refilling up both glasses, "So, when John finally decide it was time to tell you the truth about everythin'?"

"The young woman glanced up from her newly filled glass, "Did the John you met seem like the type to just explain everything?" She took a sip, "He never did. I overheard Sam and Dean talking about it when I was about thirteen maybe…" She shrugged, "Anyways, Dean was drunk and he was telling Sam how he thought it was time for dad to come clean about my mother's identity to me." Despite the years that had passed since the event, the pain was evident in her voice. She brushed her hair out of her face, "I probably shouldn't have told you that though, since I never did tell my brothers how I learned the truth. I'd appreciate you not telling them. All it would do is cause pain."

The retired hunter nodded, "Secrets and pain are the only constant in the hunter life, kid. Seems like you're used to it though." She sighed, "I won't bring it up. If either of them ask than there's no promise."

Charlotte smiled at the answer, "Well, thank you."

Ellen finished off her glass before restarting the conversation, "I thought ya said Dean was the one to convince ya things were alright. Didn't he notice that something was off? I mean, sorry, but it's obviously still a rough topic." Besides, Ellen had seen how protective both brothers were of her when they left her with Ellen to speak with Ash. Dean especially was the one who seemed to want her out of the whole Yellow-Eyes hunt.

Charlotte shrugged, "He noticed later that something was wrong. Hell, even dad noticed that something was different. He made me drink Holy Water." She sighed, "I just didn't wanna hurt Dean and I was mad at everyone, y'know? He wasn't the one who should've had to tell me, but all of them was lying to me. It was just kinda like what else is a lie." She smiled and attempted to lighten the mood, "Besides, that would have also meant admitting to Dean that I snuck out of my room after he had told me to stay in there for the night."

Charlotte picked up her glass, "After all that happened, I had decided that I had to prove that I was a Winchester like they were. Dad had taught me about hunting, but I was never allowed to go out with him or my brothers. One of the perks of being the baby in the family I guess. Anyways, with my ego from reading a crap-ton of lore, I decided that I was ready at fourteen for a solo-hunt." She shook her head, ""I was a fool." She paused when she noticed the blonde daughter of Ellen take a seat at the bar next to her mother.

"So, you're the kid of a hunter too?" Jo asked, having seen her with the boys.

The brunette Winchester nodded, "Yup."

The blonde turned to face Charlotte, "What were ya telling her 'bout?" It wasn't often that she got to hear about how other hunter's children did.

Charlotte took another drink, "Just how foolish I was when I attempted my first hunt. I snuck out of the motel to go after somethin' on my own."

Jo seemed interested now. "You were able to sneak out? How'd ya do it?" She had tried to sneak out to help her parents many times back in those days, but had never succeeded to actually get to see anything. She began filling a glass, a sign that she planned to stay in this conversation.

Charlotte grinned, "Well, dad and Sam had gotten into one of their many arguments. Anyways, after they'd argue, dad would pretty well just send us all to bed and go to bed too." She paused, recalling how that fight had been particularly vicious. It had worn everyone out and just added to her desire to prove herself able to help with cases. It wasn't easy seeing her dad so exhausted. "In my attempt to be useful, I snuck out of the motel after everyone else was asleep. I was actually able to track it down. It just didn't work out like I had hoped."

Ellen, wanting her daughter to know why it was good that she was never able to get past her parents, asked, "Didn't work out?"

"I had to get my ass saved by Dean, who had somehow found out that I had snuck out. It was embarrassing as Hell. That was the real deal type of walk of shame. I can still recall every word that Dean had told me on the way back." Charlotte took a drink. It hadn't been easy realizing how worried he was that she could've died. "Basically, I got scolded for being a reckless fool and asked what I thought I was gonna accomplish by doing this. I didn't answer him and he proceed to tell me that I could've died and that I better never do anything like that again." She smiled sadly, "And that's about it as far as my first hunt goes."

Jo frowned, realizing that her parents had good intentions. "What'd your dad do? Your dad's John, right?"

Charlotte nodded, "Yeah. He didn't do anything actually. Dean never told him. He just told him that he had killed the monster after running across it while going to pick some things up from the store." She supposed that's when she began opening up to Dean again.

Ellen offered a smile, "So, did Sam get a kick out of your first hunt story?"

Charlotte shook her head, "I never told him. He wasn't too into the whole hunting scene, so I figured it would've annoyed him." His desire to leave the hunting life is what had caused her to lose contact with him after he went to college. When he had said that he wanted to leave it all behind, he truly meant all reminders.

Ellen sighed, "Well that's a shame." She could tell that it didn't work out for him or else he wouldn't be here with them. The woman stood up and began walking away, "I'll leave you two young ladies to chat. I should go check on the boys."

Jo looked at Charlotte intently after her mother was gone. "So, how are ya a hunter with them now? Sam wanted to leave the life and Dean told ya not to get involved."

Charlotte sighed, "Well, I got involved in hunting after Sam left for college. Dean pretty much decided that I needed a distraction and began to accept that I planned to stay in this life. He began teaching me hunting tips and let me tag along with him sometimes. Of course, I was made to still focus on schoolwork, but it was an improvement." Her decision to stay was inspired by Sam's departure. She had seen the hurt it caused her dad and Dean and she refused to cause them the same hurt. She also couldn't leave Dean to be the only one to care for their father after everything he had done for her. "After I graduated I began getting more involved with cases." She sighed, "Dad later went missing while on a hunting trip, so I went with Dean to get Sam to help us find him. He's been traveling with the two of us ever since." The brunette looked at the other curiously with a smile, "So, what's your story? I've told ya mine."

Jo shrugged and rolled her eyes, "Nothin' too eventful. I've been taught how to shoot and where to stab by my dad. I was never able to go out on any hunts. Dad passed away and mom retired, so I never got the chance to as I got older."

Charlotte glanced over, "I'm sorry for your lost. The hunting lifestyle really isn't all that great though, so you aren't missing much. Just a whole lotta pain." She gave a small smile, "It sounds like they're finished. So, I should probably stop telling you how great the hunter life is. I feel like your mom would shoot me if I talked you into becoming a hunter." She listened as the footsteps got closer, "If you want, I'll give you my cell number. We can keep each other informed."

Jo smiled, "Why not? I'd love to continue hearing of the glorious life. Maybe I'll even meet you out on a hunt someday."

Charlotte stood preparing to greet her brothers, "Who knows with this lifestyle?"