A/N: This story will be set alternately in flashbacks and present-day, which is at the beginning of Supernatural Season 2 and the end of Gossip Girl Season 2. None of the stuff in relation to Serena happened on GG and the Devil's Gate didn't get opened on SPN so the Winchesters can stop hunting whenever they want to. We're going with the GG timeline, so Serena left in 2000 and comes back in 2008. Serena is Bobby Singer's daughter, and Jo Harvelle's best friend; she's been away at school since she was 10, coming home periodically. The Winchester boys didn't meet Bobby until Sam was 15 and Dean was 19. That was right after Serena left for school. They've never met her before and now Serena is 18, Sam is 23, Dean is 27. Jo Harvelle is only 19 (need her to be close to Serena's age. This one-shot will be Serena/Sam, and suggestive of Jo/Dean. This is a songfic to Tim McGraw's "My Little Girl." It's an AU/Crossover story and the first in my Apple Pie-Universe. Enjoy!

My Little Girl

Gotta hold on easy as I let you go

Gonna tell you how much I love you

Though you think you already know

I remember I thought you looked like an angel wrapped in pink so soft and warm

You've had me wrapped around your finger since the day you were born

Bobby's POV, 2000

It was the day my baby was leavin' for New York City. Had to send her away, it was already too dangerous with all the demons and monsters that were creepin' around tryin' to get rid of us hunters. It was all I could do not to change my mind. But I knew my sister Lily was lookin' forward to havin' Serena stay with her and little Eric while she went to school. Lily was being pretty generous too, payin' for private school. All she said to me when I told her that was to remember it was my money too anytime I wanted it. But I left that life behind when I married Althea [don't know the name of Bobby's wife on the show]. I chose her over the money and the society trappings. Then I got the biggest blessing of a man's life – a baby girl. When Althea died it was hard tryin' to figure out a baby all on my own. Been nine years since then and now that Serena is ten she needs safety and proper schoolin'. So I'm sending her away. Believe you me, she don't wanna go either.

Serena's POV, 2000

"Daddy I don't want to go away! I got you, Jo, Ellen and all my animals here. Why would I wanna go live with Eric and Aunt Lily? I'll have to go to some hoity-toity snob school! Don't make me leave you!" I said, tears streaming down my cheeks. All I'd ever known was life with my Daddy and sleepovers at the Roadhouse, with Ellen homeschooling me and Jo together. He sighed and had a strained look in his eyes like he wanted so bad to give in to me. I know now he was just doing it for my own good. He was like Ellen was with Jo; he wanted to protect me from hunting no matter what. At the time though, it was the end of the world.

"Baby, you know I'm gonna miss you more than anything. But this will help you more than keeping you here with me would. You will visit me for holidays. Aunt Lily said she has no problem sending you back for that. Let her help you get used to things up there, it's a lot different that it is here. I'll see you again soon, and you can write letters to Jo. She'd love that a lot." Daddy tried to smile, but he couldn't quite manage it. I ran over to him and threw my arms around his waist, holding him tightly. "Alright, I'll go to New York. But I'm really gonna miss you Daddy." He ran a hand over my long, blond hair and said quietly, "I'll miss you too Angel."

You're beautiful baby from the outside in

Chase your dreams but always know the road that'll lead you home again

Go on, take on this whole world

But to me you know you'll always be, my little girl

Bobby's POV, 2003

It was our nightly phone call, and she was bubbling over with everything she'd done that day just like usual. All that energy reminded me so much of her Mother, brings a smile to my face just remembering how much alike they are. "Daddy, Daddy guess what I did today?" Serena said excitedly, barely stopping for a breath before she started speaking again.

"I beat Blair Waldorf in the school's spelling competition today. Boy was she so mad! She thinks she's the best at everything and she's so mean to people! I'm glad I showed her up, I can't wait to tell Jo all about it. Aunt Lily said I can get a puppy! We're going tomorrow to one of her friend's apartments to pick one. Her dog just had a bunch and they're Golden Retrievers! So, hunt anything interesting today Daddy?" She stopped and changed over so quickly, I just started laughing. She was confused but you could tell she was glad I was laughing for her. "What's so funny Daddy?" Serena wanted to know, curious about my outburst. I collected myself.

"Nothing darling, I'm just real happy to talk to you. Nothing real interesting today, just did a routine exorcism. So, you're getting' a puppy? What are you gonna name it?" I said with a note of laughter still hangin' in my voice. She started chattering again and I just kicked back in my Lazy-Boy chair, settling in for a nice long conversation with my baby. I was happy to know that she was happy. Also, I was glad that she hadn't been here the first time John brought his boys over. A whole lot of trouble had followed and it had been very dangerous. But my baby was safe and John always called ahead. So I could keep protecting her from hunting and the monsters that lurked in the shadows of my world.

When you were in trouble that crooked little smile could melt my heart of stone

Now look at you, I've turned around and you've almost grown

Sometimes when you're asleep I whisper "I Love You" in the moonlight at your door

As I walk away, I hear you say, "Daddy Love You More"

Serena's POV, Christmas 2005

I had been sent home early by Aunt Lilly because of the trouble at school. But it really hadn't been my fault. I mean it was Chuck, Nate and Blair's idea to moor the Headmistress' houseboat in the school swimming pool and have a party [idea borrowed from Dawson's Creek ]. I was just along for the ride; girls just wanna have fun after all! I will never forget the look on Daddy's face when he opened the front door (shotgun in hand as always) and saw me standing there, smiling my most innocent smile a week ago. I wasn't supposed to be home until December 23. I could tell he didn't know whether to laugh or cry when he saw me standing there, especially after I told him what happened. I was lucky to just be suspended and not expelled and I knew it. Not that I actually cared. I never even wanted to leave in the first place anyhow, so why would I care about being expelled? All that would mean is coming home finally and not waiting another two and a half years to graduate. The only thing I wanted to bring home with me anyways was Lucifer, my Golden Retriever. He was named that for a reason but I loved him none-the-less.

When I put my head on the pillow that night I heard Daddy's footsteps in the hallway outside my door. I knew what he was gonna say before he said it. We'd done this since I could remember and it always left me with a warm glow inside, and I missed his voice when I was away at school. "I love you baby." Whispered my Daddy, always acting tough, but I knew better when night rolled around and it was just me n' him. As he walked away I said, "Daddy love you more." I truly believe those words still to this day. I will always love my Daddy with my whole heart and nothing less.

He is the reason I will leave and go back to New York and apologize to the headmistress of Constance Billiard Preparatory School and stay on my best behavior. I will graduate and I'll do it well because my Daddy wants the best for me. Then I will come home again finally and waitress with Jo at The Roadhouse. One day soon I will be back where I belong and having that thought to comfort me lulls me asleep.

You're beautiful baby from the outside in

Chase your dreams but always know the road that'll lead you home again

Go on, take on this whole world

But to me you know you'll always be, my little girl

Serena's POV, May 21, 2008

Finally, I thought to myself. Finally I can leave and go home where I belong. I had stayed like I promised I would and now it was time to be me again and leave Serena Singer, socialite behind. I packed only t-shirts, jeans, sundresses, my mother's jewelry, and the letters I'd gotten from Jo over the years. I only had three suitcases to represent the last eight years of my life. Lucifer came up behind me, barking happily. I snapped out of my reverie and laughed. I had Luce too and he wasn't going to let me leave him behind. The only people I was really going to miss were Aunt Lilly and my cousin Eric. They had been my family for such a long time that they were hard to leave behind. But I didn't belong with them in New York City. I belonged at home with Daddy, Jo and Ellen.

Aunt Lilly had bought me a VW Bug convertible, red she told me, to match the fire in my soul. I just laughed and hugged her tightly. It looked like I was driving home; as Jo would say, time for a Road Trip! It was a really great chance to see the country's sights (biggest ball of yarn in the U.S., duh!) before settling down at home again. Daddy already knew that it was going to be another month before I was home. But I was going to take a week of that time and using it to stay with Jo at the Roadhouse. I'd promised her we'd spend a lot of time together this summer, and I really wanted to see her. It had been such a really long time since we'd seen each other. We'd been writing at least once a week for eight years, but we hadn't got to hang out since last summer. I couldn't wait to see her and Ellen again. I knew that there had just been some sort of apocalypse that they'd help to avert just recently.

Daddy thought he could protect me from anything supernatural by sending me away. He didn't ever find out that Jo told me everything that was happening. I had been told all about Dean and Sam Winchester. I could tell Jo had a crush on Dean from the way she talked about him in her letters. Now I could finally interrogate him as to his intentions for my best friend. I could run barefoot in the Sun, go to the swimming hole behind my house every day, rescue stray animals, and make dinner for me and Daddy every night. As Serena Lynn Singer, I could be free to be myself again. It was time to follow the road that would lead me home again.

Serena's POV, June 12, 2008

I stared up at the Roadhouse in anticipation, wondering if I would even recognize Jo anymore when I saw her again. She had grown up so much in her letters over the past year. Would she even want to hang out with me anymore? I wasn't a hunter like her, and I was still a baby experience-wise when it came to the supernatural world. Taking a deep breath I steadied myself and walked through the front door. It was just as dusty and full of hunters as I remembered from my childhood. The jukebox in the corner was playing R.E.O. Speedwagon, so I knew Jo was somewhere close by. Then Ellen spotted me standing there uncertainly and chased any fear I had from my mind. I didn't even notice the two boys at a corner table looking at me curiously as I pushed my aviator sunglasses up on my head.

"Serena Lynn Singer! As I live and breathe, you look more and more like your mother every time I see you. Bobby told us you were comin' home, that you'd finally graduated. We missed you so much around here girl!" Ellen walked over to me and threw her arms around me in a fierce bear hug as I laughed happily, a smile taking over my face.

"Teacher Ellen, you're lookin' as pretty as always. Where's your other hellion of a student?" I had no sooner teasingly asked Ellen, then Jo came running into the bar looking flustered. "Momma, we're almost out of tequila and you know how it gets in here on Friday nights. You want me or Ash to run up to the store and buy some?" Jo looked up and as soon as she saw me standing there she squealed. We launched ourselves at each other, dancing around laughing happily. We pulled away with matching mischievous twinkles in our eyes. Ellen backed away laughing. "Warning time isn't it girls? These hunters gotta know what they're up against." She went back behind the bar to watch us do our thing, all the hunters turning to stare curiously at her words. We looked at each other one last time and then we began our secret dance [better than a dumb handshake by far], a sort of cross between the tango, the Macarena and the YMCA. We looked ridiculous of course. Then we did our chant.

"Angel sisters, we were born of wicked blood. See us coming you better run. Fear we will strike in your hearts, because where we are the fire starts!" On the last word I bumped hips with Jo, the grabbed her and dipped her like in the movies. The whole bar started cheering and catcalling. We just looked at each other and burst out laughing. As we walked to the bar, arms slung around each other, I let out a loud and piercing wolf-whistle. Lucifer came bounding into the bar from where he'd been waiting outside, leaping up on the chair next to Ellen behind the bar. She just laughed again and went back to serving a dark-haired woman hunter a shot of whiskey.

Jo and I sat next to each other, hugging excitedly one more time. She decided to start the conversation first. "I can't believe you're finally home Seraphina! Maybe Bobby will finally teach you how to shoot that shotgun of his. Then we can go around together. If he doesn't, I will! That's a promise! I missed you so much this year." Jo managed to say all this in one breath. We both talk really fast and say a lot when we open our mouths. I answered, "Jolie I missed you too. Even after Blair stopped being a bitch, it was never as good as being with you. Bitch or not she was still a snob and she never understood why I'd come back to Nebraska. Especially after I got into Brown, Harvard, NYU, and Yale she was confused, but I know you get it."

Smiling I shouted over to Ellen, "Hey Teach, could you send over that bottle of vodka Bobby gave you for me? Love you forever if you give me alcohol Ellen!" She just shook her head with an amused look on her face. But then she yelled over, "Yeah Serena, I'll give you the vodka. But you and Jo better behave. I remember what happened last time. Jo's hair was blue for six months and Mrs. Everett wouldn't look me in the eyes for almost twice that long." With that I gave her my most innocent look as she pushed the bottle down the bar toward us. "Aunt El that wasn't our fault; we're angels, you know that." I smirked to Jo when Ellen turned away again. Then I noticed out of the corner of my eye the two boys in the corner. They were getting up from their table and heading this way. One had short blondish-brown hair and piercing green eyes. The other was really tall and had shaggy, longish brown hair and beautiful brown eyes. Both of them were trying not to crack up at the behavior of me and Jo.

Jo leaned over and whispered, "Those are the Winchester boys Serrie. You know, the ones I told you about. The one with short hair is Dean and the serious one is Sam. I'll introduce you to 'em." No sooner had Jo leaned away again, then they had reached us. Dean had a cocky smirk on his face and he looked me up and down with laughing eyes. Sam gave Dean a glaring look and Dean answered it with a look that said "what do you expect from me?" Then they both turned to Jo expectantly. "Who's your smokin' hot friend Joanna?" Dean asked teasingly. Jo blushed hotly and I laughed. She shoved me and I almost fell off the bar stool, but Sam caught me and helped me back up. I gave him a dazzling smile and he grinned back sweetly.

"Not that it's any of your business Dean-o," she answered bitingly, "but this is Serena Singer. She just got back from New York where she went to high school. Finally staying home though, 'cause she graduated." Dean and Sam exchanged shocked and confused looks. "Her last name is Singer? Is she related to Bobby at all? We didn't know he had family." I began opening the vodka and pouring me and Jo some shots. "Yeah, Bobby Singer's my Daddy. I haven't met you guys 'cause I've been away at school since I was ten, living with my Aunt Lilly. And Daddy tries not to mention me 'cause he didn't want the supernatural world to use me to get to him. It's why I've been gone. Jolie here and me have been best friends since we first started walking." With that being said, I downed a shot, fanning myself as the liquid burned a path down my throat. Jo downed hers next, slapping the top of the bar as it went down.

"Alright Jolie," I said turning back to face her, "we gonna get smashed tonight? And the bigger question is if these two are man enough to play the game with us." I gave a smirk equal to one of Dean's as I issued the challenge. No way was he gonna let that one go. Not from what I knew of his type. "We're man enough for anything you can throw at us!" Dean boasted, smirking suggestively at Jo. "One question though before we start. Why do you call each other Jolie and Seraphina?" Sam asked with a confused look on his face.

Jo looked at me and we both started cracking up. When we calmed down enough to speak I explained. "I call her Jolie because it means 'pretty' in French. She's the pretty sister and I'm the 'angel' which is what Seraphina means. It's just a running joke between the two of us." I downed another shot. "So Sammy boy, Dean thinks he has what it takes. How about you? Do you have what it takes?" I asked with a flirting tone in my voice. Sam took a couple steps forward and lifted my chin up so my eyes would meet his. I shivered at the intensity in his look. "I definitely have what it takes."

The Following Morning

I slowly came into consciousness, groaning at the sharp pain in my head. I looked over onto the floor at Lucifer. He must have found his way to me sometime in the night. I patted him on his golden head affectionately smiling and then grimacing at the pain. Slowly I flipped over onto my other side and my mouth dropped open in horror. Not only was I naked underneath the bed-sheet, but I was apparently not alone. Sam was still asleep and he looked so peaceful that I didn't have the heart to be the one to bring him into hangover-land. Instead I tried desperately to remember how this had happened. I could remember up until the second bottle of vodka was gone and then things started to get fuzzy. I remembered making out, and apparently at some point we'd gone to my room. Oh-My-God! Daddy was gonna kill me and Sam both if Ellen told him about this!

Officially freaking out, I started to sit up, propping myself on the headboard. My tank-top, jeans and panties were strewn all over the floor; so were Sam's t-shirt and jeans. He began stirring next to me. Opening his eyes, he grimaced at the light coming through the curtains at the window. Then he looked over and saw me sitting up, already awake. He lifted his hand, brushing a strand of hair off my face gently. "So I'm assuming from our nudity that we didn't just sleep last night." He said softly, drawing me closer to him. At his words I began to blush and answered, "I'm supposing not, although I don't remember much past our little make-out session in the bar." I covered my eyes in embarrassment and he let out that deep chuckle of his, causing both of us to wince at the noise.

"Well, a new day has dawned. I suppose we better go save Jo 'n Dean. If Ellen wakes up and finds them in bed together no one will ever find his body." I got up from the bed and slowly dressed. When I turned around with my hands on my hips, Sam had also gotten dressed. He was just looking at me with that soft smile of his, a look of slight awe in his eyes. I shook myself out of observational mode and grabbed his arm, gently pulling him towards the door, making a shushing motion with my finger. We crept down the hall into Jo's room. I had to stifle a laugh when I saw them sprawled on the bed, both snoring lightly. I motioned Sam next to me in front of the foot of the bed. Then I pounced on Jo and she sat up like a gunshot had gone off. I laughed at her startled expression, and cracked up fully when Dean jolted awake next to her.

"Come on you two, if Ellen comes in here and sees you we'll be diggin' Dean-o's grave before noontime. Let's go have breakfast instead." They both looked at each other in fear. Me and Sam turned away as they got dressed. Then we all went to the kitchen downstairs and had some hangover food for breakfast (eggs, bacon and grits). Then went outside to tan and catch up with each other while the boys fixed the radiator on Dean's car [I know nothing about cars]. We spent the rest of the week together. The four of us hung out during the day and at night it was me and Sam in one room, and Jo in another with Dean.

By the end of that week when it was time for me to go the few miles up the road to Bobby's house, I had fallen completely in love with Sam. It wasn't just the sex either. He was one of the smartest people I'd ever met in my life. I mean, he did graduate from Stanford pre-law. I could talk about anything with him and he would listen to what I had to say. We laughed together a lot. I overheard Dean telling Jo once when Sam went to the bathroom, that it was the happiest he'd ever seen his brother. I could see my future in his eyes and I liked it. Dean and Sam had pretty much already decided before stopping at Ellen's that they were done hunting. They'd caught the yellow-eyed demon and that was all they'd really wanted to do anyways. Now they could settle down and have families of their own. I wanted to have that with Sam more than anything I'd ever wanted in my life.

I got up on the morning of June 19th, 2008 and dressed as quietly as possible in a yellow mini-dress and flip-flops. All of this was running through my head while I pulled my hair into a high ponytail on top of my head. I was so lost in my thoughts that I didn't realize Sam was behind me until he wrapped his arms around my waist and kissed the back of my neck. I smiled lightly and turned around, kissing him gently on the lips.

"You know I'm just gonna be up the road a ways? Tonight if you come pick me up, I can introduce you to my Daddy as my boyfriend. Then he'll pull out the shot-gun and give you the talk." I taunted teasingly. Sam let go of me and turned so he was in front of me; then I squealed as he flipped me over his shoulder and walked down the stairs with me. Jo and Dean were already waiting for us and they laughed as he put me down on my feet again. I lightly punched him on the shoulder and he just laughed at me.

I walked forward and hugged Jo as hard as I could manage. "I'll see you later on Jolie. Love you so much and it's so good to be home with you." She threw her arms around me and we just stood there for a minute happy to be together again. Then she stepped back and I grabbed onto Dean. "Dean-o you better treat Jolie right. I'll be back later and you will be sorry if she's unhappy." He gulped and looked a little scared and then he laughed. "As if Sam would let you do anything to me." He taunted me, smirking happily. "Oh no man, I am NOT getting involved in this." Dean looked stricken and slightly terrified as me and Sam left him standing there with a very smug Jo.

I brightened up with a new idea as me and Sam neared my car with Lucifer wagging his tail between us. I turned to him. "How about you just come over with me now? Then you can keep Daddy occupied while I unpack. We can hang out for awhile and I won't have to leave you here with Dean and Jo." Sam looked slightly uneasy as we got into the car and looked at me, saying "Alright, but you have to protect me from the shot-gun." I squealed and clapped my hands together. Then we drove away, finally going back home.

Someday, some boy will come and ask me for your hand

But I won't say yes to him until I know, he's the half

That makes you whole, he has a poet's soul, and the heart of a man's man

I know he'll say that he's in love

But between you and me

He won't be good enough

Bobby's POV, Christmas Eve 2008

I think my heart has officially stopped. I knew that things were serious between them, but I never for the life of me imagined that my baby would marry John Winchester's boy. He just asked me for my permission and what else could I say other than 'yes'? I already know what she'll say. The same thing I said to him. We talked about this when she first brought him home and I know that she has been in love with him since they first met. Sam Winchester has made her so happy it makes me think of how me and her mother started off; which means they'll be together forever. So, here I am at my kitchen table with them in the living room, laughing with Jo, Dean and Ellen.

He has written her poetry and she hasn't stopped smiling at all since she came home. That boy definitely has the soul of one of them poets you read in school. But he ain't a sissy at all. I just took him and Dean hunting and the both brought down a deer each. Plus, though he's retired he knows how to hunt evil. He can keep her safe. She'll never know the pain my life has been made up of since her Momma died. Still it's hard to let her go. I know I have to. Especially because of what she said to me yesterday; turns out that in six months I'm gonna be a Grandpa. First time I've cried since the day she was born. She's plannin' on tellin' him the news later on tonight. In just a few minutes I'm gonna go in with the rest of the family and enjoy a peaceful holiday, hopefully the first of many. But for now I need just a few moments, to look back on my life with my beautiful little girl and the happiness she's given me. Soon I'll let her go, but for tonight she's still my baby. I wouldn't have it any other way.

You're beautiful baby from the outside in

Chase your dreams but always know the road that'll lead you home again

Go on, take on this whole world

But to me you know you'll always be, my little girl.

The End

A/N: Just had this idea and I couldn't let it go. It just flowed out of me like a thunderstorm. Let me know if you think I should do more one-shots in the Apple-Pie Universe. I have ideas for a Jo/Dean one-shot, a solely Sam/Serena one-shot of them and their child. Or, I could do one of when Serena's at school in New York. Just review and let me know what you want to hear more about. In this story the Roadhouse and Bobby's place were close for convenience and in Nebraska cause I couldn't remember where they were on the show. And that whole situation with Jo's Dad and John Winchester never happened. Hope you liked this story!