While You Were Sleeping – Part IV

'Cause I see you in the daytime, and I hear you at night
There's a pale imitation burnt in my eyes
I don't wanna be here, I don't know what to do
Sometimes I'd rather be dead
At least then I'm with you

…

2033 – Eleven Years Ago:

"Bailey!" Bonnie called up the stairs. "Hurry up you're going to be late for school." She waddled back into the kitchen, hand soothingly running over her full belly. She was due any day now, and it couldn't come soon enough.

Damon was already in there, dressed for work in jeans and a black button up with the sleeves rolled up as he cut up some fruit for Stefan. "Here you go, buddy." He sat down with him, ruffling his curly hair as the three-year-old eagerly went hands first into the bowl. He stopped Bonnie as she came around the kitchen table, kissing her belly as he did every day. "She still being stubborn?"

Bonnie let out a sigh. "Yeah, a trait I'm convinced she gets from you."

Damon chuckled, kissing her sweetly. "I'll talk to her." He headed up the stairs, knocking on his daughter's door before poking his head in. "Hey bella…you're still in you pj's? You don't want to be late for your first day." He sat on the edge of her bed.

Bailey huffed, a pout on her lips. "Why can't I go back to my old school?"

"We talked about this…now that you've come into your magic you need to learn how to control it. This school is going help you do that." He knew it was hard for her to switch schools, and make new friends after three years in public school, but ultimately this was the best thing for her.

Her blue eyes met his. "Am I being punished?"

His heart broke. "No…no Bailey, of course not." He pulled her into a hug, cradling her against him. "It's just that…you're special. You're like your mom, you have this gift, but if you don't learn how to control it someone might get hurt." He explained gently as he pulled back looking down at her and brushing the curls from her face.

"Like Ms. Merrick?" That was the moment Damon and Bonnie realized that she couldn't go to public school anymore. Bailey had accidently set a small fire with her magic and her teacher suffered some minor burns. For the most part they lived a fairly normal life, but this warranted a call from Caroline to compel it all away. The last thing they needed was to try and explain a spontaneous fire.

Damon nodded. "You'll like it at this new school, I promise. Plus, Uncle Ric's going be there, and Lizzie and Josie, and eventually mom will come back after the baby's born. And there are going to be lots of other kids that are special just like you." He bopped her nose making her giggle. "Now please go get ready. I'll drop you off myself." He added with a wink.

"Okay, daddy!" She got up and rushed off the bathroom, her bare feet slapping the hardwood floor.

Damon came back down the stairs with a victorious smile, and Bonnie stood at the bottom, with Stefan clinging to her leg and she closed her eyes in relief. "Thank you. She always listens to you."

He wrapped his arms around her. "She thought she was in trouble over the fire incident. I just told her this is a good thing. She'll be okay." He eyed her with concern. Her due date was last week, but despite their best efforts to induce labor, her water still hadn't broke. "Are you okay?"

"I'm tired; everything hurts. He just doesn't want to come out." Her hands cradled her belly as she looked down at it, and Damon's hands joined hers. He kicked hard against their touch. "He's strong though that's for sure."

"Just like his mom." Damon praised. "I know this pregnancy has been harder on you than the others. I'm sorry."

"I'll be okay. But this is the last one! You have your tribe." Bonnie joked poking him in his chest. Bailey came down the stairs ready to with her backpack on and both her parents graced her with a smile. "Hey baby…you got everything?" She nodded. "I'll come by the school around lunch time with Stefan, okay?" That made her daughter smile, and she leaned down to kiss the top of her head. "I love you, have a good day."

"Love you too, mommy." Bailey crouched down, and gave her little brother a hug and kiss. "Love you, Stefan."

"Wuv you, Baiwey." He said back with a dimpling smile.

Damon kissed Bonnie and shot her a little wink. "Call me if you need anything and I'll be right over. I don't want you pushing yourself too hard this close to the birth."

Bonnie smiled indulgently, knowing he was concerned. "Yes…I'll be fine. I've got my little man to help me out right, Stef?"

He nodded exaggeratedly, and squealed in delight when Damon hoisted him into his arms. "You be good for your momma for me, okay. Don't give her any trouble. Promise?" Stefan nodded again, taking his role very seriously. "Cool. Knuckles?" He made a fist and Stefan fist bumped him. "Love you, buddy."

When Damon and Bailey left, Bonnie turned to her youngest. "Okay, let's get you cleaned up. Then we can go to the park later; how does that sound?"

He bounced on his feet. "Will Kara be there?"

She smiled. He had a cute little crush on Kara Donovan, Matt's youngest daughter. "I'll call her mom and see if she's free."

.

Damon was buried in paperwork in the office of the Grill, sorting through the expenses when he got the call. The school's name coming up on the caller ID. "Hey Ric."

"Daddy?"

Damon froze. "Bailey? What's wrong?" Panic tore through him.

"Mommy never came by for lunch." Her voice wobbled. "And she's not answering her phone."

Damon was already out of his seat, grabbing his keys and jacket and heading out the back door. "Okay honey, I need you to do something for me." He told her calmly. "Stay with Uncle Ric, I'm going to swing by the house and check on mom. She's tired, maybe she took a nap." He tried to reassure the both of them. "I'm sure she's fine."

After saying goodbye, he hopped into the car and raced towards the house. When he rushed in the door, nothing seemed to be out of place. "Bonnie!" He took the stairs two at a time, and into their bedroom only to find it empty and bed made. He slapped his hand against the wall. He whipped out his phone to try and call her again, as he did the whole way home, when it rang in his hand. "Hello?" He paused listening to the woman on the other end. "Is she okay?" He let out a relieved sigh. "I'll be right there." He hung up, storming through the house and back to the car to call Ric.

When Damon arrived to the hospital, he barreled towards the emergency desk. "Bonnie Salvatore. My wife…she was admitted an hour ago. She's pregnant." He panted.

As the nurse went through her system, his son came running towards him from the arms of another nurse. "Daddy!" Damon felt him latch onto his leg, and held him close. "Mommy fell."

Damon scooped him up, hugging him close. "It's okay Stefan, she's going to be fine." He turned back to the nurse. "What happened?"

"Someone at the park called it in. She collapsed and shortly after went into labor. There were some minor complications, nothing serious for the mother or baby, but the doctor is in with her now monitoring her."

The elevator doors opened, and Caroline, Bailey, Lizzie, Josie and Ric headed directly towards him. "Thank you." He turned back, meeting them in the waiting area.

"Is she okay?" Caroline asked anxiously.

Damon nodded. "Nothing serious."

"When do we get to see her?" Bailey asked quietly.

"Soon, honey." He squeezed her shoulder reassuringly.

The minutes felt like hours. "Mr. Salvatore?" The doctor appeared in the double doors.

Caroline extended her arms. "Here, let me take him." Damon handed Stefan over to her, and he immediately cuddled into her. They had a very close relationship.

Damon walked over to the doctor. "How're they doing?" He asked nervously.

The doctor smiled, easing his worry. "They are both doing just fine. She's asking for you."

Damon glanced back and his family with a grateful smile, and headed towards the room. When he walked in, she was already holding their son, an illuminated smile on her face. "Hey baby…" he whispered breathlessly, coming around to stand beside them. He kissed her forehead as she beamed down at the little bundle in her arms. "Hey little guy." He brushed his thumb over his head. "I'm so glad you two are okay."

She grinned at him, her face still sweaty and her hair stuck to her forehead. "Sorry if we scared you. For someone that didn't want to come out weeks ago, he sure came quickly." Bailey took her time. Bonnie was in labor for forty-eight hours before finally giving birth and Stefan came within a few hours. She passed him carefully to Damon and watched as he fell in love with his son. He'd grown so much over the years; all the worries he originally had of whether or not he'd be a good father had been washed away the second he held Bailey in his arms the first time, and ever since, everything he ever did was for his family.

Shortly after, Ric knocked on the door, and they all came filtering in. Bailey and Stefan hopped onto the bed with Bonnie, and she wrapped her arms around them as they cuddled into her. Caroline walked over to Damon with tears in her eyes. "Congratulations…he's beautiful."

"Meet Leo Salvatore." He said glancing up to meet Bonnie's eyes.

Bailey sat up eagerly. "Can I hold him daddy, please?"

He nodded with a smile. "Come over here." He gestured to the lounge chair and placed him carefully in her arms once she was comfortable. "Keep his head supported, okay."

Ric and Caroline hugged Bonnie, watching Bailey gently rocking her sleeping brother. "I'm your big sister." She whispered down to him. "That means I'm always going to protect you."

It was such a special moment, that it brought a tear to everyone's eye.

…

2044 – Present Day:

Elena looked around the boarding house as Damon led her in. Everything was different. Gone were the old antique red sofas, and it was replaced by a u-shaped sectional. Above the fire place was a TV and pictures all along the mantle. She looked at each one as Damon headed to the kitchen to grab them each a drink, before rejoining her.

"You guys look happy." She whispered, looking at a picture of all five of them, taken a few years earlier. From the looks of it, it was in the backyard, sitting on a picnic blanket. Bonnie was cradled between Damon's legs, with their youngest, Leo in her lap and Damon's arms were wrapped around Stefan and Bailey, who flanked him on either side.

He handed her the glass of water. "We were. Elena, I'm sorry. I know this wasn't what you were expecting. Honestly, I wasn't expecting it either." He admitted dragging a hand over his face.

She shrugged helplessly. "How did it happen?"

With a grunting sigh, he sat down on the sofa, and she followed suit. "After I became human, I was miserable. Stefan was gone, I was struggling with the fact that I may never see you again, and Bonnie was the one that gave me the strength to get through it. She never gave up on me. We both lost people we loved, and we healed by leaning on each other. Somewhere along the way…something changed, and we couldn't fight it anymore."

Elena nodded as tears sprang to her eyes. "Then I'm glad you had each other." She was silent for a long moment, staring down at her hands. "You named your son Stefan." Glancing up she shot him a watery smile. "I'm sure he'd be very proud."

"I hope so." His voice still caught in his throat at the thought of his brother. Damon stood, going to the bookcase and pulled out a stack of journals. "Bonnie wrote to you a lot, pretty much until the end. So did I." he mumbled hoarsely. "We wanted you to know that we never gave up on trying to bring you back. And even though you weren't here…we still wanted you to be a part of our lives." She grabbed the books from him, opening one of them. "Take all the time you need." He left the room with a hesitant smile that didn't reach his eyes, and Elena cuddled further into the couch as she started with Damon's journal.

.

Dear Elena,

This is hell. I thought I could wait until the day that I could see you again, but with each passing day, I miss you more. And it's making me irrational. So, I've decided. I'm going to do what's best for everyone and desiccate, right here beside you. I love you…I'll see you soon.

Damon

.

Dear Elena,

I've made a mess of everything. Again. And what's worse…I hurt Bonnie. I thought by desiccating I was helping them, instead I made it worse…and she suffered the most. She could die. And that guilt will eat at me until I find a way to fix it. She deserves at least that for everything she's done for me.

.

Dear Elena,

I turned it off. And now the guilt is overwhelming. I'm doing everything I can just to hold it together. I can't do this without you.

.

Dear Elena,

Stefan's dead. I'm human…and I miss you. But Bonnie is relentless, and she's doing everything she can to bring you back to me. I'm not sure where I'd be without her, honestly. She won't give up on me…or you. I'm lucky to have her in my corner.

.

Dear Elena,

We're in New York. Sometimes I feel like I can see you walking towards me in the streets. A couple years ago, it would have made me sad…now I can look back on those days with a smile. Bonnie has been keeping my spirits up; she's a good friend. We miss you.

.

Dear Elena,

I think I'm going to be okay.

.

Dear Elena…

I'm sorry. I tried, but I can't deny it anymore. I love her. And it doesn't mean that I love you any less, it's just different with Bonnie. I don't know what I'd do without her…and I don't want to find out. Please forgive me…

.

Elena closed the journal, wiping the tears from her face. It was too much. With each entry, one theme was evident. Bonnie. She was deeply embedded in his life; it was no wonder they fell in love. But she couldn't blame either of them.

"You're my Aunt Elena, aren't you?" Elena's face snapped in the direction of the voice, and there was the girl she saw in the hall yesterday. Her hair was half up in ponytail, the rest falling passed her shoulders in perfectly natural ringlets. Her eyes were a shocking blue against her smooth skin. "I recognize you from the photos."

The brunette stood, smiling at her sympathetically. "Yeah…Bailey, right?" The girl nodded. "I'm sorry about your mom. I know what you're going through. I lost my parents when I was a little younger than you."

Bailey swallowed painfully. "Does it get better?"

Elena shook her head sadly. "No…it's always going to hurt. But you learn to deal with it."

Surprisingly, the young girl opened up to her, letting the mask she saw earlier slip away. "I'm trying to keep it together…for my brothers, and my dad." Her voice broke. "But I can't help feeling like this whole thing is my fault. This never would have happened if it wasn't for me."

Elena came around to comfort her, and Bailey without hesitation buried her face in her shoulder, sobbing quietly. "Hey…this isn't you fault." She pulled back, looking down at her. "You know, your mom was always very brave. She's saved my life more times than I can count; all of us. Because that's the thing about Bennett women…they will do anything for the people they love. And for Bonnie, that's you."

Damon was about the enter the room again when he saw his daughter cradled in Elena's arms, and he stopped, watching silently from the doorway.

Bailey wiped her eyes with her sleeve. "I just worry that I won't be able to live up to her, you know? I'm not as brave as she is."

Elena ran a hand down her hair affectionately. "I don't believe that. Caroline tells me you're quite the talented witch. Top of your class." She praised her softly. "I'm sure your mother's very proud of you. And if there's one thing I know about Bonnie…even when she's gone, she's still here watching out for you."

Bailey sucked in a breath, owning it and smiling gratefully. It was what she needed to hear. "Thank you."

Damon walked back into the room, meeting Elena's eyes and giving her a thankful nod. He was having a hard time offering words of encouragement to his children when he was so miserable himself. The last few days, he had been a shell of the man he used to be. He could barely get out of bed; his only nourishment had been the bottle of bourbon that sat on the nightstand. And Bailey, she had been the strong one through all of this. For being only nineteen, she slipped easily into a caregiving role – making dinner, looking after her brothers, picking out the dress Bonnie was buried in, because Damon couldn't. He couldn't do anything besides spiral. He'd lost his other half, and he cursed the world for taking her first.

.

Two Days Ago:

Bailey knocked twice before peaking her head in the room. "Dad…?" She called out, slipping in and shutting the door behind her. She didn't want Stefan or Leo to see him like this. He was a lump in the middle of the bed, his back to her, and buried under the comforter. "You should eat something." She urged gently. He grunted in response. Navigating through the broken lamp, chair and litter of clothes, she sat on the edge of the bed, pulling out an empty bottle that she accidently sat on. "Dad…please." Tears pooled in her eyes, though she tried hard to keep them at bay. "It's been a week; you can't just stay in here forever."

He released a wretched sigh. "I ca-I can't." He whispered brokenly, the grief sitting heavily in the center of his chest like an anvil. It was a time like this when he wished he was still a vampire. He'd never felt heartbreak like this before, and all he wanted was to turn it off.

"I know it's hard…I miss her too." She cried, resting her hand on his shoulder. "But you don't have to miss her alone. We need you, and you need us too. And we all need to say goodbye…" she broke to him gently. Caroline had planned the funeral for tomorrow, and she only could pray that her dad could pull it together long enough to get through it.

He scoffed ironically to himself. He'd done everything alone for majority of his life, until Bonnie. He hadn't been alone since, and he had grown to love that. They went from a team to a tribe. And now he needed to be there for them. Turning, to look at her over his shoulder he realized she was already moving to get up, taking his non response as an answer. Damon grabbed her arm, and pulled her back, wrapping his arms around her and kissing the crown of her head of curls. "I'm sorry, bella." He apologized in a hoarse whisper. "You're right. We need to stay together. We're all we got now…"

She looked up at him. "Where do you think she is?"

His throat tightened. He'd been wondering the same. He knew it wasn't a prison world, or the other side, but wherever she was, he hoped she was at peace. She deserved at least that. "Someplace beautiful."

There was a long stretch of silence as they both got lost in their thoughts. "Dad…?"

"Yeah?"

"I know you're tired, but…you really need to take a shower." And for the first time since his wife died, he laughed. Bailey joined him, their bodies shaking uncontrollably. "I mean, seriously, it's a next level stink that's coming from you right now." She chuckled harder when he pushed her out of his arms playfully.

"Hey, it's not that bad." He sniffed his shirt and made a face. "On second thought…" With a groan, he finally got out of bed, and padded around barefoot as he headed to the bathroom. "Hey…" Bailey turned back to him, stopping on her way to the door. "I love you...thank you."

"I love you too, dad."

.

2042 – Two Years Ago:

She loved the gardens here. It was probably Bailey's favorite place at the Salvatore School. More often than not, she found herself coming here to escape and lose herself in a book, or even just to feel the hum of the plants and the energy that came from them. She liked being alone. When everyone knew you were the offspring of the infamous Bonnie Bennett and Damon Salvatore, it was hard to find a moment to herself. Having been a talented witch herself, she was usually the first one they went to for help.

A shadow blocked the sun from the pages she was read, under her favorite oak tree, and she raised her blue eyes up to see who obstructed it. "Can I help you?" She tried not to snap at the young man looking down at her.

"I was hoping so." He smiled charmingly. "The Dean said I'd probably find you out here. I'm Cain." He held out a hand as she stood, brushing the grass from her school uniform.

Realization came over her. "Oh, you're the new guy. I'm Bailey." She shook his hand, feeling a chill run through her. "Vampire?"

He chuckled. "How'd you guess?"

She crossed her arms, cocking her hip out. "Well, if you were a witch I'd feel your power, and you don't smell like a wet dog so you're not a werewolf." He snickered to himself, dimpling his cheeks.

"Not a fan either I take it?"

"Not particularly. Anger issues and a lack of control…not the best combination." She looked him over subtly as she slipped her bag over her shoulder and tucked her book inside. "Come on, I'll show you around." He was cute…really cute. Tall, hazel eyes, dark hair and a confident swagger.

As they walked the grounds, he noticed a lot of eyes on her as she moved through the campus. "You're pretty famous around here, aren't you?"

Bailey scoffed ironically. "I guess you could say that. Kind of hard to fly under the radar when your name is on the door."

He smirked at her. "Can't imagine how you could. I mean…you're beautiful."

And he's charming. She thought begrudgingly, disappointed at the flush that rose to her cheeks at the attention. Bailey averted her eyes, barely hiding the little smile that pulled her lips. "Thanks…"

He shoved his hands in his pockets as they walked towards the main building. "So, you're a Bennett witch then, one of the legacies."

"Oh God, is that what they're calling me? Like I need any more unattainable standards to live up to." She grumbled under her breath. Bailey stopped walking, turning to face him. "Look, don't treat me any differently than you would anyone else here, okay. You don't have to suck up to me or boost my ego to get in good with my uncle or my parents. I'm not special." She explained irritably. Everyone around here always thought they had to treat her like royalty just to stay in her family's good graces, and as a result, she found it hard to trust people's true intentions. They all wanted something.

Cain canted his head, narrowing his gaze to read her. "I think you are. And not just because your parents are Bonnie and Damon Salvatore. I've been here less than a day and everyone I talk to sings your praises. Why do you think I had to meet you?" He shot her a crooked smile. "Listen, I don't care about getting in good with the Dean…how do I get in good with you?"

Her heart raced. No one had ever been so bold with her before. Dating had never been high on her priority list, she preferred to focus on practicing her magic. But this guy seemed different. "Well…you're off to a good start." She mumbled shyly, ducking her head, feeling nervous under his gaze. "Come on, I'll show you the training room." She nodded in the direction of the entrance, and he followed her with a grin.

Bonnie watched from the window of her office, phone to her ear as she spoke to her husband. "Uh oh."

"What is it?"

She chuckled to herself. "There it is…that look. Our daughter is totally crushing on our new student."

"What? No, it's too soon for that." There was mild panic in his voice on the other line.

"She's seventeen, Damon. She wasn't going to be our little girl forever. He's cute." She smiled to herself watching them walk off.

"Okay…so what do we know about him? Evil warlock, vengeful vampire, wicked werewolf."

Bonnie rolled her eyes as she sat back in her chair. "None of the above. His name's Cain Hightower." She flipped through his file. "Both of his parents died five years ago in a car accident, in and out of foster care, no history of violence with police, turned into a vampire a year ago and his uncle and mentor…" she flipped a page skimming it quickly. "Samuel, sponsored his admission. Squeaky clean."

"Hm." Damon grunted. "I still don't like him."

She laughed. "You don't even know him."

"I know enough. She deserves better than some vampire boyfriend." He huffed.

"You were a vampire when you met Elena." She pointed out.

"Yeah, and look at how that turned out. I just want what's best for her, Bon. The last thing I want is her going through that kind pain." She could hear the worry in his voice.

"I know. But she is our daughter, Damon…she's headstrong, and stubborn. The more we try to push her one way…"

He sighed heavily, and she could picture him running a hand over his face. "The more she'll push back, I know. Just…keep an eye on it? Please?"

"Of course. I have to go; my class is starting soon. I love you."

"I love you too, Bon."

.

Three Months Later:

Damon moved around the kitchen, making breakfast for everyone before they left for school while Bonnie got ready. He kept a close eye on Bailey, who's phone kept pinging with text messages. He watched her cheeks flush and a smile come to her face as she texted back. "What's got you so smiley?" He asked curiously, putting the plates in front of each of them. She was like him, grumpy until she'd had a coffee.

Stefan snorted loudly, as he scarfed down his food. "More like who." He mumbled, earning a slap to his shoulder from his older sister.

"Shut up, Stefan." She hissed back with a glare. "No one dad. Just a friend."

Leo giggled. "Yeah, a booooyfriend."

Her cheek reddened in embarrassment. "Judas'…both of you." She accused, pointing at her little brothers. She could feel her dad's eyes on her and turned back to him with her tail between her legs. "He's not my boyfriend; I mean it's not official or anything."

"So who is it?" he asked coolly, popping a piece of bacon in his mouth. "I'd like to meet him."

Letting out a long groan Bailey looked skyward. "Dad…please don't get all weird and stalkerish."

Damon held his arms out innocently. "What? I don't get weird and stalkerish."

All three of his kids tried desperately to hide their snickers. Bailey's lips twisted as she held back her laughter. "Yeah, you do. I get it, you just want to protect me, but not everything is out to get us. You don't have to interrogate everyone new that comes into our lives."

He came around the island, leaning against it. "Yes, I do. Because it's my job as your father to make sure you're safe."

She crossed her arms defiantly. "But I'm not a little girl anymore."

He smiled. "Well…you're always going to be my little girl, Bailey. I wish I could say we live in a world where there are no monsters to protect you from…but I've been around a long time, and your mom and I know all too well how dangerous it can really be." He stated seriously, capturing their attention. "So…indulge me, okay?" he shot her a half smile.

With little roll of her eyes, she caved. "Fine. His name is Cain Hightower. Aaand he's a vampire," she admitted, but quickly rambled on. "But he's really sweet, and funny and he really likes me, and I really like him." Damon's jaw clenched, and he let out a disapproving grunt, but he kept his comments to himself. When Bonnie first told him about this new student, he'd had his suspicions of the young vampire. And while his history appeared to be clean, Damon couldn't help being thinking there was more to him than they knew. Okay, yes…maybe he could be a bit stalkerish, but when it came to protecting his family, there was no limit to what he was willing to do. Bailey scoffed, drawing his attention back to her. "Seriously? Judgmental much? You used to be a vampire, dad."

"And for the first hundred and fifty years of being a vampire I did a lot of terrible things, Bailey." He argued back. He and Bonnie never kept the truth about their past from their children; in fact, they were brutally honest. "Look, maybe I'm wrong; maybe he's one of the good ones. But I'd like to meet him, and if he really likes you then he's going to have to come through me first, got it." He added with a playful narrow of his eyes. "Dinner, Saturday. At the Grill. I'll ask Javier to put your favorite on the special's menu."

Despite herself, she allowed a resigned sigh, a little smile pulling at her lips. "Okay…got it."

"Good. Now eat your breakfast, before it gets cold." He urged. Shortly after, Bonnie entered, dressed in a pencil skirt, blouse and black pumps, her long hair pulled into a high pony that bounced in tight curls. He let out a long whistle, his eyes raking over her hotly. "Mrs. Salvatore…" he drawled, tugging her wrist so she fell into his arms with a chuckle. "You look ravishing." He whispered, earning gagging noises from their children.

She laughed it off, leaning up to kiss her husband. "We have a big donor coming to the campus for a tour. Alaric asked me to play tour guide." She slipped out of his arms, grabbing a piece of toast from the plate on the table and putting it in her mouth as she poured herself a coffee.

They continued with their morning routine; eating their breakfast, and cleaning up before Leo, Stefan and Bailey piled into the car while Bonnie and stole a couple moments to themselves. "So…our daughter has a boyfriend now." Damon grumbled conversationally, rinsing the dishes.

"She finally told you, huh?" Bonnie laughed at the surprise on his face. "Yeah, I knew. She was worried how you'd take it." She stated, leaning against the counter watching him.

"Why didn't you tell me?"

She shrugged. "She wanted you to hear it from her. Your opinion matters to her, Damon…more than anyone else's. I think she was worried you'd shut it down." She sipped her coffee.

Wiping his hands to the towel, he sighed. "What if this guy isn't who he says he is, Bon? It wouldn't be the first time someone has deceived us hoping to gain something."

"Caroline and I vetted him ourselves. Everything checks out. Look, I know you're worried…" she started, resting a hand on his chest. "But Bailey is at an age now where she's going to start making choices we aren't going to like. And sometimes she's going to get hurt, no matter what we do to try and protect her. I mean…" she chuckled. "Do you remember what we were doing when I was her age?"

That did nothing to ease his worry. "Yeah…you were almost dying trying to kill Klaus; was that supposed to make me feel better about this, because it didn't." he grumbled, tight lipped.

Bonnie wrapped her arms around him. "She's strong, and smart. We have to trust her."

"Okay…but I don't have to like it." He pouted, to which Bonnie leaned up and kissed tenderly.

"I love you, have a good day." She patted his cheek.

"Love you too." He continued as she walked away. "And make sure he keeps his hands to himself if he knows what's good for him."

She shook her head with a smile as she walked down the hallway to the door. From the moment Bailey was born, she knew he'd be fiercely protective of her. She was his little girl, and no matter how old she was…she always would be.

…

"Soo…" Bailey started, closing her locker and leaning on it, facing Cain. "I told my dad about you this morning." She watching him hesitantly.

He grinned. "Finally. How'd he take it?" he brushed a curl that fell from her face.

"Not as bad as I thought. But he wants to meet you." The cool touch of his fingers sent a shiver down her back.

He lowered his head, trying to catch her eyes. "And that freaks you out, doesn't it? Look, you don't have anything to worry about. I can handle the third degree. I like you." He shrugged easily. "And if meeting your dad is what he needs for me to prove that, then so be it. Plus, I'm dying to see the inside of that house anyways." He smirked.

Her eyes widened. "Oh…um actually we're doing dinner at the Grill. You see, my dad has this rule…we're not allowed to invite vampires into the house." She saw him deflate slightly. "I'm sorry."

He forced a smile. "No, it's fine. I get it. Trust is big in your family." He leaned down, kissing her hand. "So I intend to earn it." He shot her a wink, before walking off to class.

Bailey felt the flutter of butterflies in her stomach, and let out a dreamy sigh as she leaned her back on her locker.

"Gross."

Her head shot a glare to her brother who shut his locker right beside her. "Ugh, how long have you been eavesdropping, you weirdo?"

"Trust me, I wish I didn't hear that. Why do you think he wants to see the house?" he questioned curiously.

She blinked, before shrugging. "I don't know. Maybe because it's like two hundred years old." She shot back defensively. "Cain likes history, and our house is basically a museum."

"Hm." Stefan mused to himself.

She rolled her eyes. "Don't do that, you know I hate it when you do that. What?" She demanded.

"Nothing. I'm sure you're right." He said slinging his back over his shoulder and heading to class.

Bailey watched her brother leave, left contemplating his non answer. Stefan was always so cryptic. He was quiet and stoic at times, but that also meant he was very observant, even for a twelve-year-old, so if he was questioning it…should she?

…

AN: Hey everyone! I think there will be one more chapter after this one. I appreciate all of your reviews and comments! We're going to have a few more flashbacks and some more present-day scenes before we wrap this story up. I really wanted to show the family dynamic the Bennett-Salvatore's have and what I thought their kids would be like. I hope I did it justice 😊 Thanks! - Vanessa