~A/N Originally this was going to be a quick one-shot/drabble but I wrote a lot and started to get more ideas that can tie into it so I'm making it a multi-chapter fic. I have never written an actual "story" (basically only drabbles & one-shots) so bare with me. It won't be super long but I really had fun writing about Blair and her daughter and I most definitely want to write more. If you have any prompts or requests, you can find me on twitter or tumblr, my username is leightedwester. Thank you so much to the people that review, favorite, and follow, it truly means so much. xoxo ~M


Madeline Eleanor Bass, a four year old with as much sass and style as her mother.

The only thing on her mind recently is when she'll be able to have a girl's day. She has been non-stop asking Blair when they could have a day with just the two of them, nails, hair, and pampering.

Maddy, who's the only Bass girl, had been practically begging Blair to visit her Aunt Serena and baby cousins Sophia and Isabella.

Serena recently moved to LA after her split with Dan. After the birth of their twin girls, they dealt with constant fighting and disagreements which caused it all to crash down in flames. Serena, who was still mourning over their split, thought it would be good to move away from the city for a while. She was hoping that she could clear her mind and spend all of her time on the beach with her 14 month old daughters.

Since Serena had moved out to LA, Blair had decided it would be a fun idea to take a trip there with Maddy. Considering that's all Maddy has been asking for. All though, Los Angeles was out of her comfort zone, she wanted to make her best friend and daughter happy.

The two Bass girls woke up for their flight at six. It was a five hour flight and Blair knew her daughter would have a hard time sitting still. After their trip to Hawaii last fall, Blair knew she needed to pack things to keep Maddy busy. All though their trip to Hawaii consisted on her, Chuck, and their three bored and tired children - a trip with just Maddy wouldn't be as hectic.

She packed snacks, games, toys, and her own iPad Mini. She knew she would never get bored with her iPad, not to mention the television they had on the plane as well and the fact that Maddy might wind up falling asleep.

She quietly entered her daughter's room to wake her, only to find her already awake and attempting to clothe herself in the outfit Blair had out and ready for her.

"Good morning my love," she smiled, "Mommy!" She ran to her and Blair picked her up.

"You look lovely darling." "Thank you, I dressed myself!"

She leaped out if Blair's arms and on to her bed. She twirled around showing her mother her bright yellow Little Marc Jacobs polka dotted dress, with the zipper in the front.

Blair smiled, "It looks lovely my dear, just one thing, you have it in backwards. Most of the time the zipper goes in the back." She giggled helping her daughter fix her dress.

"Oh man! I thought I got it right this time." Her pout was priceless, as Chuck would say, identical to Blair's.

"Almost right," Blair said with a smile, "Hold up those arms," Maddy threw her arms up as Blair pulled the dress over her head and turned it around.

"Ah, much better. Isn't that much more comfortable?" She kissed her head, "Alrighty, let's wash our faces, brush our teeth, and fix our hair up. Daddy, Henry, and Liam are going to drive us to the jet."

Maddy smiled big, jumping off her bed and running to her own personal bathroom. Blair hears her daughter yelling, "Mommy can you do my hair first? Pretty please!"

"Of course darling." She followed her into the bathroom. Maddy was already standing on her pink step stool, holding her brush and yellow headband out to her mother.

"I want my hair to look just like yours Mommy, headband and all."

Blair couldn't help but smile at her little girl. "Sure my little mini-me."

She kissed her daughter's head and brushed her hair, her chocolate curls flowing down her back. She was beautiful, and so exotic looking. Her piercing blue eyes stared, watching her mother's every move; she wanted to be just like her.

Chuck and Blair wondered where she got her beautiful blue eyes, and then it clicked. She inherited them from Bart. All though it wasn't exactly what they were expecting, they never saw eyes anymore beautiful.

She placed her bright yellow headband on her head - matching her dress. "I love it mommy, my hair looks exactly like yours!"

Maddy washed her face and brushed her teeth. She then followed her mother into her bathroom to get ready, continuing to tell her about all of the things she wants to do this week. Chuck was still fast asleep in their bed, most likely exhausted from the night before.

"Shh, we can't wake up Daddy just yet, he'll be up soon to go for the ride with us later."

Maddy nodded at her mother with a grin, and put her finger over her mouth.

They entered Blair's bathroom, closing the door behind them so they wouldn't wake up Chuck.

Maddy jumped up on the counter next to her mother, watching her every move as she took out her bag of makeup. She applied her moisturizer and anti-aging skin creams first, then her face makeup, which Chuck would say is not needed. She continued on adding her light colored eye shadow and mascara.

"Mommy?" The tiny brunette asked curiously, watching her mother.

"Yes baby?" She answered putting her mascara on.

"When am I allowed to wear makeup?" She looked up at Blair with her crystal blue eyes, hoping they will help her into convincing her mother to let her wear just a little bit of makeup.

Blair stopped putting on her mascara to look at her, "You don't need any makeup my darling your beautiful just the way you are." She answered and continued putting her mascara on.

The little girl sat there pondering, "I wish I could wear makeup so my eyelashes are big like yours. And lip gloss too!"

She grabbed Blair's lip gloss out of her makeup bag, "Pretty please Mama? It's pink, my favorite color!"

She started to slowly open the lip gloss with a smirk and Blair rolled her eyes, "How could I ever say no to you?"

She smiled, "Sure. Only lip gloss though, mascara might hurt your eyes. Come closer and I'll put it on for you."

Maddy smiled big as Blair applied the strawberry pink lip gloss. "Ta-da! Look at that pretty face." She says squeezing her cheek, "Wait till daddy sees you. I don't think he'll recognize you."

Chuck slowly walked into the bathroom rubbing his eyes, "Wait until I see what?"

Maddy hopped off the counter and ran into her father's arms, "Daddy! Look at me, look at me! Mommy let me wear lip gloss!" She made a kissy face to show her father.

"Oh boy, is that my four year old daughter or a teenager?" He peppered kisses all over her face as she giggled uncontrollably.

"Daddy! You're gonna wipe off my makeup!"

"Fine, fine."

He placed her back on the counter next to Blair, and slowly made his way to his wife. He wrapped his arms around her hips, "And how's my lovely wife on this early morning?"

He kissed her cheek, "Exhausted, but overly excited to spend the week with my little girl." She winked at Maddy who was beaming.

"Oh how I'll miss my girls." Chuck said, giving them both another kiss.

"I better go wake the boys, this will be something to watch." He laughed.

"I want to wake up Henry!" The petite brunette leaped off the counter and ran out of the bathroom.

Chuck sighed and turned back to his wife, spinning her around to face him, he kissed her.

"I'm going to ache for you while you're gone."

Blair sighed, "So will I, it's only 7 days we can do it."

She kissed him again wrapping her arms around his neck.

"I'm gonna miss my daily dosage of this."

"Mmm, so will I. You have the whole week to yourself though, you and our boys."

Chuck grinned, "Of course me and my Bass boys. We will all miss you, especially Henry."

Blair frowned, "I'm gonna miss them. They're my little mama's boys."

"Don't worry we'll have fun, as for you too."

He kissed her again, "Mmm, not as much fun as I would have with you," she kissed him again and his hands made their way down to her ass as she let out a soft moan.

That's when they heard Maddy running back in, "Henry won't wake up.. Ew!" She covered her eyes.

Chuck pulled away from his wife, "You better not kiss boys, do you hear me Madeline?" He said with a laugh, picking her up, "Only me," He gave her a big kiss on the cheek.

Blair rolled her eyes with a smirk.

Maddy had Chuck right where she wanted him, wrapped around her finger. The manipulative four-year old could get away with murder in his eyes. When she needed to be disciplined it was always Blair who put her foot down. Chuck would pull the classic, 'she doesn't understand' or 'she didn't mean it' when she wasn't cooperating.

"I won't Daddy, kissing is yucky!" She put her hands on his cheeks.

"That's my girl. Now let's go wake up your brothers."

"Chuck, don't wake up the baby. I'll get him up as we're leaving, he's probably way over tired. He wouldn't fall asleep last night."

He gave her a smile, "Alright."

He continued out of the room with his little girl in his arms, "Let's go wake up your sleepyhead of a brother."

She giggled, "I'm gonna jump on him!"

"No, no you'll hurt him, why don't we just tickle him instead?" Chuck added with a mischievous smirk.

"That's a good idea!" She leaped out of his arms and continued into Henry's room. "Hennybear, it's time to wake up!" "In a minute," he yawned and turned his head to the other side of his pillow.

Henry loved his sleep. He can sleep as late as 10am if Blair let him, not so typical for a six year old.

Maddy crawled on her brother's bed, "Stop being so lazy," She pulled his dark blue comforter off of him, "Now I'll have to tickle you to wake up!"

She started tickling him and Henry now sat up on his own laughing, "Fine, fine I'm up," Maddy jumped up and down on his bed, "Yay! Are you gonna miss me?" She gave him a big smile. "Yes. I'm going to miss mommy more though." Chuck added, "Oh come on Henry, that's your baby sister." Maddy added quickly, "I am not a baby. Liam is the baby, not me." She stated placing her hands on her hips and head in the air. Chuck and Henry laughed, "You know I'm just teasing sweat heart," Henry was still laughing, "I'm going to miss you Maddy," he hugged her. Maddy hugged him back as Chuck added, "Now that's more like it."

Finally everything was packed; Blair and Maddy were both done getting ready. Their hair was the same and Blair decided she would wear a yellow dress just like her daughter.

Blair made her way to her two-year-old son's room, who was still fast asleep as she expected. She rubbed his cheek, "Oh how I'm gonna miss this face."

Chuck called out from downstairs, "The limo is here."

She picked him up and kissed his head and walked down the stairs slowly, meeting her husband at the bottom.

"He's out like a light," She smiled, and Chuck gave him a kiss.

"Not for long, I have a feeling he'll be up soon,"

"Me too," he rubbed his sleeping son's cheek, "Alright are you ready? Arthur put all the bags in the limo, Maddy and Henry are already in,"

They started walking out of the house and to the limo,

"I wish you were all coming with us."

"Me too, my love."

She slowly entered the limo with the baby still sleeping in her arms. He started to move around a lot and eventually opened his eyes.

Chuck stepped in and they were on their way to the Bass jet.

Along the way Maddy looked out the window, pondering about their trip and eventually Henry had fallen back asleep in his father's embrace. Blair thought she hasn't seen anything cuter.

"Oh mama, I'm so excited. It's going to be a week with all girls!"

Chuck added, "Aren't you going to miss your daddy?" He pretended to cry,

"Of course I will Daddy. I wish you could come with Mommy and I."

Liam lifted his head up from his mother's chest, "Good morning my little sleepy head"

She kissed his head once again.

"Are you still tired?"

She held him close and rocked him back and forth in her arms.

"Mommy," The two year old whined, "Shh," She rubbed his head and he struggled but sat up on her lap, blinking his eyes in exhaustion.

Liam was over tired and cranky, "Dada, dada!" He reached for his father who placed him on his other knee next to a sleeping Henry.

Blair frowned at the loss of holding her baby in her arms before she was leaving for a week.

Finally they arrived at the Bass Jet, they all got out of the limo. Chuck was still holding a sleeping Henry in one arm and an awake, but sleepy, Liam in his other arm.

Maddy stood there patiently with her miniature Louis Vuitton carry on in her hands.

"One of my babies sleeping and the other one is cranky right before I leave, what is this?" She said with a giggle.

She gave Henry a big kiss, "Sleep tight my angel, I'll miss you dearly."

She then kissed her two year old who was still sleepy and blinking, "And my other little angel," she kissed him and took him out of Chuck's arms, giving him a big kiss.

"You can't be cranky just before mommy leaves my darling. I love you." She squeezed him close.

"I love you Mama," Liam added.

"I love you more."

Chuck took Liam back from Blair and placed him and Henry back into the limo and in their car seats.

Chuck came out of the limo and opened his arms to his daughter, "Come here my little princess," Maddy ran into her father's arms,

"I'll miss you. Don't have too much fun without me, alright?"

He gave her a big smile and a million kisses all over her face.

"I'll miss you too Daddy, next time you are coming with us!"

Blair wiped a stray tear at the sight in front of her, Chuck was the most amazing father.

"Ok, next time I will come with you, deal." He kissed her cheek again placing her down. "Now why don't you go give your brothers a proper goodbye."

She trotted off into the limo and Chuck approached his wife.

He wrapped his arms around her waist as she wrapped her arms around his neck.

"I'll miss you so much." He kissed her passionately, leaving Blair breathless.

"I'll miss you more. I'll call you as soon as we land." She kissed him again, "I love you so much."

"I love you too. Have a wonderful trip, say hello to my lovely sister and nieces."

"I sure will." She smiled, leaving his embrace.

Maddy hopped out of the limo and to her mother's side.

"Maddy girl are you ready?"

She picked up her carry on, "Yep!"

"Well then let's go, say goodbye to daddy!"

They both blew him kisses, "See ya daddy! I love you!" Maddy added, grabbing her mother's hand as they walked off the Bass Jet.

"I love you more!" Chuck called out after them.

Finally after getting their bags on the flight and getting situated they were in their seats and ready to take off.

Maddy was looking out the window, you could see the excitement on her face. Blair shed another tear watching her daughter's excitement. She has been so emotional lately and she didn't know why – she didn't think much of it though. She always gets emotional at things like this.

"Are you ready to finally see Aunt Serena and the girls?"

Maddy turned away from the window, "I am so excited!"

She kicked her feet over and over.

Blair smiled big at her, "I'm so glad. We're going to have so much fun. Also me and Aunt Serena have big surprises planned too,"

Her crystal blue eyes widened, "Oh boy! Thank you Mama for taking me to visit, I love you!" She jumped on her lap and gave her a big hug and held her tight, more tears sliding down her face.

"I love you too baby, we're going to have the best girl's week ever."

She gave her a big kiss, she loved seeing her daughter happy.