Supernatural Stories and Imagines

Dean 13/ Bobby's Daughter Part I

Prompt: Imagine flirting with Dean Winchester before he finds out you're Bobby's daughter.

A/N: I know Bobby never had children, but let's imagine for now. I've got a cool idea, for the most part, to go with this prompt. As always, feel free to request any ideas you would like me to write! I've had quite a few Dean ones recently and even more coming up soon. Thanks for sticking with me.
Also, I just can't write a story without a backstory, I just need it desperately haha, so enjoy this midnight mess. And uhh, this one gets a little steamier than the others, just a heads up. Also this one is getting multiple parts!

It took you long enough to convince your dad to so much as let you hunt by yourself.

You heard the story of your mom once, and only once. Your dad hated discussing what happened to her. It broke his heart, losing the love of his life. Bobby often declared he didn't know what he would do without you, that you being born was a blessing and miracle tied into one burst of joy in this miserable man's life. That was quite a bit to live up to. Fortunately, you weren't stuck with him all of the time. Once he stopped homeschooling you, you were able to have real interactions and get to know the real world.

Every once and a while, a friend of your father would drop his sons off at the doorsteps to watch for endless amounts of time. Sure, the boys were a couple of years younger, but at least they never said you had cooties. They were excited to be with Uncle Bobby, though they weren't related. It occasionally made you doubt your place in his heart, wondering if he wished you had been born a son instead. However, it was nice to not be made fun of not having a mom and having a drunkard for a father. You saw the brothers young and at one point, hadn't seen them since. It wasn't uncommon for traveling hunters to occasionally leave their children for a weekend or two, so you didn't easily remember all of their names.

Growing up a female was tricky in small-town Iowa, even more so as a hunter. Your father spent some time away hunting when things began to go awry in nearby towns. You started public middle school around age eleven, but your father feared you were simply too young to spend nights by yourself, and you didn't exactly have a bunch of friends to spend the nights at. That ended up causing extra frustration and stress on his plate before you suggested an idea you watched on television: private school.

In a way, Bobby was a better father after you went away. You became more outgoing, learned what it meant to be a lady, and more importantly, how to use that to your advantage. You were encouraged to learn other languages, try extracurriculars. So you did, studying Spanish and French for the rest of your education. You joined the photography club, acted in theatre, and played soccer. You went home on holiday breaks, summer being your favorite as it meant spending more time with your dad. He did his best to be home as often as possible. You got excited to fix cars if it meant spending time with him. Despite his protests, you felt encouraged to hunt, so he gave you pointers. It was years before around age sixteen, he finally allowed your first solo hunt. It was thrilling and unsurprisingly, it went great. He preferred playing board games and watching television with you, making him overall pretty chill.

The one thing he was not a cool dad came to your dating life. You tried getting a boyfriend young and Bobby insisted on meeting him before your first dance. Let's just say the two of you didn't leave together by the end of the night. He was more lenient toward regular, mediocre guys. His one rule was the most adamant: don't date hunters. Fortunately enough for you, most hunters were around your dad's age, so, very much not your type.

That could lead to some very lonely tonights as you became an adult, leading to one night stands in apartments. Of course, you skipped past the whole college scene. Far too expensive and not something you seemed interested in, anyway. Despite your father's protests, you decided to spend time traveling rather than staying with him. You had gotten used to your independence and was somehow nearing thirty way too quickly. You considered yourself content in life. You were a darn good hunter, a woman that could hold her alcohol, and a successful freelance photographer. You weren't sure where your dad's income came from and you decided it best not to ask, sticking to making an honest living while hunting as often as possible.