Author's Note: This story is the mixture of two crazy minds my friend imcrazyfordean (Jo with the great imagination) and me (Asya the crazy one and writer), well it's her idea after all and I'm glad that we're sharing this story and that I had the pleasure to write it. Thank you in advance for taking the time to read this story. Enjoy!

Well as we mentioned this is Dean/OC starting season1 and continuing, we hope you'll like it. And we also added pics for Josie's car and top, find them on my profile :D

Imcrazyfordean (Jo) and Asya55 (Asya) ;)

Enjoy the story!!!

From Josie's diaries,

My name is Josephine Walden-Josie for short, I'm 24 years old and I'm a hunter. Well my parents were too, that's how I was introduced to that way of living in the first place. My father was a great hunter and my mom was a nurse, that's how they met. She treated him and knew about his life as a hunter and fell in love with him and got married but they quit the hunting scene when I came into order to keep me save but they kept helping their fellow hunters in research and stuff. They were awesome, yes were, my mom and my dad died when I was ten, no not in a supernatural way but in a way that made me cope easily with their death, they died in a car accident and the next day I was alone, but not for long. I went to live with my parents' best friend, Bobby Singer. Uncle Bobby is the best, he treated me like his own daughter and he taught me everything about hunting, he can take the whole credit for me being a great hunter.

And with me being in Uncle Bobby's house I met a lot of people, I mean he was and still helped the other hunters and every one who hunts practically knows Bobby Singer. But the greatest gift from god ever was me meeting the Winchesters, John Winchester and his two sons Dean the oldest and Sam the youngest. And we immediately became friends, no we became family; I'm older than Sam by two years and younger than Dean by two years but that wasn't a problem at all. First I got close to Sam, Sam is the sweetest person anyone can ever meet and he's like my baby brother literally, from the first time I saw him I knew he'll always be like my baby brother and we used to spend a lot of time together.

But it was a whole different story with Dean, I mean at first we weren't so connected, he was jealous of me and Sam's bond but got use to it. Dean and I became close too I mean I love cars, classic rock and skipping homework so we became buddies. He felt what I felt towards Sam-to me it was my own greatest disappointment-his other sibling, his younger sister the one he feels he needs to protect and take care of. Well I wasn't feeling that way towards Dean, I hate to say that but I had a huge crush on him…well I kinda still do, but I never told him, Dean was and still a total playboy plus I think he never had any feelings for me.

Well I stayed with Uncle Bobby till I turned 18 then he let me go hunt by myself with one condition, to call him every day twice a day or as he put it "I'll go hunt your ass myself dragging you home." And I know Bobby, when he says it he means it.

The worst day ever was the day Uncle Bobby and Uncle John had a huge fight and Uncle Bobby kicked Uncle John out, I was 14 or 15 at the time. I kept in contact with John and the boys and I used to help John with hunts and research, Sammy used to call me all the time but I didn't see the boys for almost 3 years or even more.

So, that's all about me for now, but my story with the Winchesters wasn't over, hell it's just the start.



Few years ago, in New Orleans, Josie who was 18 now and stared to hunt on her own.

"Hello," Josie answered her phone.

"Hey Josie, its Dean!"

"Damn boy! It's been ages."

"Ya, well I kinda missed you." Dean said.

"You're such a liar cause if you really missed me you would have at least called, but you didn't." Josie smirked.

"You know dad, he works my ass off all the freakin time." Dean whined making Josie laugh.

"Ya, I know John," she told him, "but let me ask, why am I honored with this phone call?"

"What? I'm offended. Can't a guy call and ask how you've been doing?"

"No, not in your case Dean, I bet a million dollars that you're calling for some kinda favor, I'm I right?" Josie asked, joking.

"Well, you know me well Josie. And I'm so embarrassed but I know you're staying in New Orleans now and I need your help, so when can I meet you and where?"

Dean and Josie sat a date to meet at the local bar near by her flat the same day at 7pm. Dean arrived first and then Josie walked in the bar roaming till her eyes found him sitting at the bar.

Josie came up behind Dean, he couldn't see her. "You've got such a nice ass mister, can I squeeze it?" she whispered in his ear making him chock on his beer.

He turned around to see who it was and found out it was Josie.

"Damn girl! You got so bold," Dean told her smiling Josie. "And look at you, you look hot."

Remembering Josie with her boyish style and her short hair Dean would never thought that the girl who used to share her Metallica t-shirts could get that hot.

Josie was so much different from the last time he saw her, she had now had long wavy shoulder length dirty blond hair, she got taller too she was 5.5, her body totally changed she was well curved and looking like a real woman now. And she replaced her tomboy style as she used to wear exactly what Sam and Dean wore. She was wearing skinny blue jeans and a very attractive white knot-front bra top, high heels and full make.

"They're real by the way!" Josie told Dean.


"My boobs that you're staring at they're real," she said, "Well the only fake thing on me is my copycat Victoria secrets' thong."

Dean for the first time looked at Josie in the eyes, amazed. "What?" he exclaimed.

"Oh, I forgot," she leaned into whisper in his ear, "I'm not wearing one." She pulled away, seeing the shocked look on Dean's face she giggled. "Hell Dean, I was joking."

"Yah, sure, I know." Dean said swallowing hard. She laughed.

Josie took a seat next to Dean and ordered a beer.

"Well, why are you here in New Orleans?" she asked sipping her beer.

"I'm on a case, isn't that obvious?" Dean smirked.

"No it's not, since when does John let you do jobs alone?"

"Since I'm old enough, I'm 20 smartass."

"Ohhhh, I'm scared Mr. I'm 20." She mocked and chuckled. "So, what about your case?"

"It's a hunted house case." Dean answered.

"I know, which one?"

"What do you mean? Are there many hunted houses?" Dean wondered.

"Are you kidding, this town has as many hunted houses as STDs in a ten dollar whore."

Dean chocked again on his beer. "You and your metaphors, you'll get me killed." Josie just chuckled.

"It's that house in the woods…" Dean started but Josie cut him off.

"Yah, the wizard's house, Yuk I hate that house," she said. "Well I've got most of the info I spent a month in this town collecting them, I cleaned like ten houses so far but that house is kinda creepy."

"So you're helping?" he asked.

"Sure, and we're goin tonight."

Later that night after Josie and Dean finished the job.

"Shit! That was one evil bastard." Josie said getting in her 1967 Shelby GT.

"I still can't believe Bobby gave you this car!" Dean said getting into the passenger's seat.

"Dean," she looked at him, "I can't believe you're talking about the car after such a crazy hunt. But to comfort you, Bobby gave it to me on my 16th birthday. And you've got such an awesome car, what the hell?"

"Dad was being an ass, he didn't allow me to drive it here and I had to take the bus, can you imagine?" Dean whined.

"His car, his rules," Josie smirked," but now we're gonna go celebrate our successful hunt."

"At the bar?" Dean asked.

"Nope, at my flat," she answered, "You, me and six pack and maybe some shots."

"I'm in."

Josie and Dean arrived at her studio flat.

"So what do you wanna do?" Josie asked, "Watch a movie? Eat? Get drunk?"

"Well all," Dean smiled wickedly, "What about some poker, strip poker?"

Josie didn't say anything she just took off her top. "Well if you want me naked all you had to do was ask." She smirked. Dean's jaw literally hit the ground.

"Josie, wow, I mean you're naked, you're crazy!" he exclaimed.

"I know," she simply said, "well Dean, I saw the way you were looking at me earlier and I'm sure you want this as much as I want it so what are you gonna do?" she got closer to Dean, his eyes were locked on her body licking his lips.

He got closer to her and his hand reached her body pulling her against him and their lips were locked in an eager kiss. Pulling back both of them were panting. Josie reached the hem of Dean's shirt and helped him to take it off.

"Josie, I hope you're not drunk!"

"No, I'm not Dean. I want this, I want you, NOW!" she said and pushed him on the bed. She took her jeans off.

"Oh, CRAP!" Dean exclaimed.

"Yah, I wasn't joking about the panties," she straddled his lap, "I don't wear any." She leaned down and they start to make out.

They switched the position and Dean was on the top now, he started to kiss Josie's jaws drifting lower to her neck, kissing and nibbling, she moaned as Dean got to her sensitive spot, kissing the crock of her neck.

"Dean," she groaned.

Dean stopped kissing her, took off his pants and leaned down to whisper in her ear. "I'll make you scream my name way harder Josie." He promised looking her in the eyes before leaning down to continue what they started.

Few hours later; Dean and Josie were cuddling on the bed.

"Josie!" Dean called.


"Why didn't you tell me that you were a virgin?" he asked.

Josie turned on her other side to face him. "Does that make a difference?"

"Well, kinda." He hesitated.

"Look Dean, I'm a big girl and I wanted to be with you, I wanted you to be my first." She paused, thinking. "I…um… I …"

"What?" Dean questioned seeing her like that, she wanted to tell him something but she couldn't.

She sighed. "Never mind," Josie huffed. "Did you call John I mean did you tell him about the hunt?" she asked changing the subject.

"No, he doesn't know that I called you, actually he asked me not to call you and to do the job myself." Dean grinned.

"So," she smiled. "Do you wanna spend the rest of the week here with me? Or call your dad and tell him you finished the job?"

"Well," Dean grinned wickedly. "Do you really need an answer for that?" he said starting kissing her body.

Josie giggled. "Not any more!" she replied.

End of flashback.


Back to Josie's diaries:

Well, I don't even know why I thought of that but I kinda do every single time I think of Dean and remember the good times we spent together but I also remember what happened next.

After we spent a whole week-mostly in my room-John called Dean and yelled at him, I don't know how but John knew that Dean finished the job already, or maybe he just guessed, I mean it's a simple job after all. So John asked Dean to 'get your ass back cause I need you on a new job in Ohio', and of course Dean didn't want to get his ass kicked and left.



Josie walked in her flat finding Dean packing his stuff.

"Hey!" she greeted kissing him lightly on the lips. "What's goin on? Are you leaving?"

"Yes," Dean huffed. "Dad just called and asked me to help on a job in Ohio so I gotta go; he already knows I've finished the hunt."

"That's so not good," she said disappointed and sat on her bed. "I've already planned for the next week or at least few more days."

"Sorry Josie, but you know dad. I really had a great time." He smiled and sat next to her, leaning to press a kiss to her lips and she deepened the kiss.

"Me to," she said pulling back. "So, I guess now it's time to say 'I'll see you later' right?"

"Right," Dean smiled. "Bye Josie."

"Bye Dean."

Dean walked out of the room leaving Josie there by herself.

End of flashback.


Back to Josie's diaries,

Well, that wasn't all for Dean, but I'm trying to remember the good stuff and for my relationship with Dean, it's rare cause he's a huge pain in my ass. I'm angry now, lets skip the Dean talk and talk about my sweetie pie aka, Sammy.

Sam Winchester, what a nice person he is, I mean I met a lot of people that I liked, loved but not a lot of respect, and Sam is one of those people that you respect and love, it's hard not to. But one certain thing about Sam, he hated his life. The hunting, travelling all the time and his life, he was the loner, shy, cute kid and seeing him making a great decision like leaving John and Dean and go to school was HUGE.

I knew about that when he called me one day and told me even before telling his father and brother.



"Hey Josie!"

"Hey Sammy, sweetie how you going?" Josie answered.

"I'm fine, in fact I'm great," Sam said. "And I got great news too."

"What! You're not a virgin any more?"

"Ha, ha so funny Josie," Josie chuckled imagining Sam's red cheeks. "I've decided to go to Stanford Law School."

"Oh my God! That's great Sammy," Josie was silent for a moment. "I can't believe it, my baby is all grown up now, I'm so happy for you Sam."

"I know Josie, but you gotta stop treating me like a baby, I mean you're only two years older."

"Shut up boy! I'll always be you big sister and you're always gonna be my baby no matter what, even with grand kids around you." Josie said. "So? Did you tell John and that brother of yours?"

"Nope, I'm so worried about that!" Sam said in a worry tone.

"If you need me with you…."

"No Josie, I'll do it and tell them," Sam huffed. "But wish me luck."

"Sammy, I always wish you the best of luck and don't worry I'll pray for you harder sweetie."

Two days later Sam called Josie again, but this time he was angry and frustrated.

"Hello," Josie answered her phone sleepily, it was 2am and she was asleep.

"Hey Josie, its Sam. Sorry for calling you now but I really need you." Sam said.

"God! What happened?" She snapped. "Is every thing ok?"

"No, my dad and Dean hated the idea of college and when I insisted, dad made me chose between them or school," Sam paused. "And I chose school, then dad told me that I should get used to being alone cause once I leave I can't come back."

"Crap, your dad can be an ass sometimes," Josie yelled. "Where are you now Sam? I'll come pick you up and I'll drive you myself to Stanford tomorrow."

End of flashback.


Josie's diaries,

And I did, I went to pick Sam up and took him to school and when John knew about that he was so mad at me, but I couldn't care less. Sam had a dream and I helped him to fulfill it I didn't do any thing wrong and neither did Sam. Sometimes I wish I was like Sam, to have a dream and to fight the world for it, but unfortunately I don't, well, still looking.

I saw Sam a few times after that but not Dean or John. And I used to go visit Sam in college, I even met his girlfriend Jessica and she's a sweetheart, the one for Sam.

But for about 7 months Sam didn't call me, I thought he was busy with school, but sadly I was wrong. And I knew that when I accidently met him and Dean when I was working a case in Iowa, but that's a whole different story.

End of the diaries.

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