Disclaimer: I do not own The Vampire Diaries.

Please note that there is heavy language, dark themes, and sex scenes in the chapters to come.

1.

Elena Gilbert stepped out of the library at closing time, waving goodbye to the librarian as she did so. Her eyes swept the dark and empty parking lot, and she sighed as she realized that once again, her older brother Jeremy was late in picking her up. She pulled out her cell phone and called him, huffing when she got his voice mail, but decided to leave a message for him instead of just hanging up.

"Jer, not even kidding, this is the fifth time this month that you've been late picking me up! I know you're busy, but you are always telling me how unsafe it is on the streets! Leaving me alone in an empty parking lot is not showing good safety practices! Call me back soon, I love you."

She sat down on the curb with the cell clenched in her hands nervously looking around. She was so mad at her brother for forgetting her again, but she never forgot to say that she loved him. After the loss of their parents, both of them knew how fleeting time was.

As the minutes crept into the half hour, she started to get worried. Not for herself, but for her brother. For reasons unknown to her, after the death of their parents, and they moved in with their Aunt Jenna, her brother started running with a gang called the Machiavellians. She thought it was just a phase, borne out of grief, but now that he was in his fifth year in the gang, and the leader, she realized it was a permanent life choice, and one she wasn't proud of.

His being in charge of the gang was the sole reason for him not wanting her out on the streets alone at night, or anytime for that matter. He would never leave her waiting this long if something wasn't wrong.

She was starting to get chilly sitting on the curb, the fall Chicago night affecting her, causing her goose bumps. She opened her phone, preparing to call one of her friends, Bonnie Bennett or Caroline Forbes, when a motorcycle roared into the parking lot and came to a screeching stop in front of her.

Her jaw dropped as the man sitting astride the motorcycle pulled off his helmet to reveal a perfect, handsome face. He dangled the helmet on one of the handle bars and leaned forward predatorily. "Elena Gilbert?" He asked in a silky voice, seemingly ignoring her open jaw, but she could tell by his smirk that he had noticed, and was enjoying the attention.

"Do I know you?" She asked carefully, not giving away any answer to the question. With her brother being in his position, she knew better than to give her name out to any stranger on the street.

He chuckled, still straddling the running bike, the dark machine matching his own darkness perfectly. With his black jeans, shirt, leather jacket, and hair, the man seemed to be made out of shadows, blending in seamlessly with the darkness. She was struck by the raw sensuality in his gaze, and shivered a little when he answered her in a low tone. "You're careful. I like that. Never know who to trust around here." He winked at her, which she answered with an eye roll that seemed to delight him. "My name is Damon Salvatore, I'm an… ah… associate of your brother. He got caught up with something and asked me to come pick you up."

She narrowed her eyes at his explanation, taking 'associate' to mean he was a member of her brother's gang. "Are you a Machiavellian?" She asked cautiously, thinking as she stared up at him from her seat on the curb, that she should get up. Him being so much higher up than her put her at a psychological disadvantage that she didn't appreciate. He raised an eyebrow at her question, and then inclined his head slightly, leaving her to take that as a yes. "Prove it." She demanded, once again seeming to amuse him in some way.

Wordlessly he rolled up his right sleeve and leaned down so she could see what was on it. There, right at the crease of the elbow, where a doctor would normally draw blood, was tattooed the letter 'M' in old English script.

"Anyone could get a tattoo," she said, but she was warming up to him now that she saw the ink on his skin.

He leaned back up to sit fully on the bike, and his eyes darkened at her statement, as he stared down at her. "Anyone with that tattoo has earned it; no one else is fucking stupid enough to walk around with it if they haven't." He replied chillingly, causing her to shiver for the second time that night, this time having nothing to do with the cold. She wondered idly what one had to do to 'earn' the tattoo.

They stared down each other, her looking up, and him looking down, and until finally he sighed, saying, "Fuck this," and turning off the bike and swinging off of it.

Immediately she was off the curb and backing away from him warily eyeing him as one does an animal that might attack. She was suddenly aware of how much bigger he was then her, with him straddling the bike, he didn't seem as intimidating. He was now though, all six foot four of him approaching her.

He rolled his eyes and said, "Relax, I'm calling your brother." He pressed some numbers on his phone, held it to his ear, and then handed it to her when the person on the other end picked up.

"Jeremy?" She asked tentatively.

"Elena?" He replied sounding confused.

"Jeremy! Why didn't you pick me up?"

"Calm down," he snapped, and then seemed to get control of his temper. "I got caught up with something, but I sent Damon to pick you up. You're on his phone, but where are you guys? Still at the library? Don't tell me, you wouldn't get on the bike with him." When she said nothing, he chuckled. "Don't get me wrong, I'm glad that you're being careful, but believe me, you can trust Damon, I wouldn't send him to you if he wasn't trustworthy." She glanced at the man in question, and he waggled his eyebrows with a mischievous grin as if he knew what they were talking about. Her brother sighed heavily, bringing her attention back to the conversation. "Just get on the bike with him, tell him to drive carefully, he's carrying precious cargo. I'll see you home in twenty minutes."

With that, he hung up, leaving her shaking her head at his parting words. She handed Damon back his phone, relaying Jeremy's message to drive safe, which he took with a roll of his eyes. "Can we go?" She asked finally. "I'm freezing out here, and I have a paper to type up." He immediately straightened up, shrugging off his jacket and handing it to her, while simultaneously grabbing her messenger bag to put in the tiny trunk of his bike.

"What am I supposed to do with this?" She asked him holding the jacket by the tips of her fingers away from her body as if it was a disgusting animal.

"You put it on, if we crash, it's going to protect you from road rash. Glad you wore jeans and sneakers today. Sure you're not psychic?" He asked with a playful grin, as he straddled the bike once more, turning it on and revving the engine loudly, waiting for her to get on.

She reluctantly put the jacket on and swung clumsily onto the bike, sitting as far back in the seat as possible, to avoid touching him. She had never been on one before, not even with her brother; he said it was too dangerous. She wondered why he was taking the chance now.

"How often do you crash?" She asked nervously, raising her voice to be heard over the engine.

He turned to her with a roguish grin, calling out, "Not often. Well, not lately. Oh, and here, your brain bucket." He pulled his helmet off the handlebar and handed it to her. "Don't worry, I don't have cooties.

She took it from him, and thankfully yanked it on, strapping it on securely. "What about you?" She asked after raising the face guard.

He winked at her, and asked, "Worried? Don't be. I've never crashed." He laughed as he snapped down the face guard, and yanked her forward quickly, so she was forced to wrap her arms around his waist, and then he was off before she could blink.

She clung tightly to Damon as he sped through the city of Chicago, the buildings all turning into a blur around her as she looked out through the tinted helmet. In that moment, as they raced so fast that she couldn't see any landmarks, she had no idea where they were, and she felt lost, disoriented. But as she clung tighter to the hard body in front of her, she suddenly felt safe and secure, wrapped up in his jacket that smelled of smoke, and grease, and something unidentifiable. She briefly squeezed her arms around him, and then wondered if he recognized the gesture for what it was: A hug.

All too soon, they pulled up in front of the house she shared with Jeremy, an inconspicuous two-story, twenty minutes from the heart of the city, and thus the library. They had made the trip in ten minutes.

"Wow," she breathed as Damon cut off the engine and turned around on the bike to face her, still straddling it. She was struggling to catch her breath, dizzy from the fast and dangerous ride she'd just been on.

He chuckled at her reaction, surprising her as she thought he couldn't hear her through the helmet. "I know." He replied, and then jokingly added, "I told you I wouldn't crash."

She yanked off the helmet, and handed it to him, replying playfully, "No, you said you'd never crashed before. There's a first time for everything Damon."

"Never." He replied, his tone and eyes serious. "Not with you behind me. I've never driven so carefully in my entire life."

It was on the tip of her tongue to ask, 'That was careful?' But she found the words stuck in her throat as she stared deep into his eyes, which suddenly seemed so blue. She wondered why she hadn't noticed them earlier, instead focusing on his dark dress and features. She felt like a fool for overlooking them, they were suddenly the only things she could focus on.

He tossed the helmet onto the grass, and then for the second time that evening, yanked her forward, causing her hips to meet his and her legs to become entwined amongst his own. He caught her and balanced her out, as she was startled by the sudden movement.

"You feel it too, don't you?" He asked, and all she could do was nod dumbly, and then he was smirking and leaning forward. The man that she had known for barely an hour, and whom she knew for a fact was a member of a dangerous gang, was going to kiss her… and she was going to let him.

Right as she could feel his lips ghost over hers, so close that she could feel his breath as it quickened in anticipation, her brother burst out of the house. "What the fuck is going on out here?" He roared, pointing at the two of them together so intimately, and she blushed as she realized that in their position of straddling the bike, they probably looked quite scandalous.

Elena found herself being pushed once again, but this time it was backwards, causing her to fly off the bike, luckily into the grass, where all that was injured was her behind and her pride. "What the hell?" She spat out, for once losing her control of her manners. In a matter of seconds, Jeremy was at her side, helping her up, and checking to make sure she was okay. She glanced to see if Damon was worried, not that he would be as he was the one who rudely shoved her off his bike, but she wanted to see what his expression was.

But when she looked in his direction, he was already getting back on his bike, snapping on his helmet, and then he was gone.

Jeremy barely paid his 'associate' any mind; too busy being concerned over his baby sister, helping her into the house though she was perfectly fine.

"Are you okay?" He asked, setting her down on one of the kitchen chairs, and then grabbing a beer before sitting down across from her.

She had to grin at the sight he made. Mussed up hair, ripped jeans, grease stained shirt, tattooed arm, and beer in hand. He looked like exactly what he was; a hardened gangster, except for the little detail of the expression on his face. It was the look of complete and utter parental concern.

Ever since their Aunt Jenna had left them two years ago to study at Princeton for her doctorate, Jeremy had taken on the role of caretaker and protector, doing his best do protect his little sister from all dangers, from rival gangs to paper cuts.

"I'm fine Jer, really, just a bruised butt," she teased, earning herself a scowl from him as he took a swig from his beer.

He narrowed his gaze at her, and she suddenly felt like she was being x-rayed. "What were you doing with Damon on his bike?"

She suddenly found herself unable to meet his eyes. "I don't know…." She replied hesitantly, stunned to realize it was absolutely true.

Her brother nodded and then leaned forward, locking her eyes with his own. "Elena, you have to hear me out on this, and take me seriously for once, don't write it off as me just being an older brother." She nodded, and then he continued. "Damon is a bad guy, alright? He's my second, my best friend, and I love him like a brother, and there's nobody I would trust more to have my back in a fight then him. But you're my sister, and quite frankly I love you more, so I have to tell you not to be with Damon. I know he seems mysterious and troubled, and knowing you, you want to save him, but you can't. He doesn't want to be saved." Jeremy finished his speech by taking a long sip from the bottle in his hands.

She wiped away the tears that had inexplicably sprung to her eyes before her brother could see them. Hearing him talk about Damon in that way stung her. She felt that they had shared something on his bike, a moment, and to hear that it was probably a farce, made her want to break something.

She forced a smile at him and replied in a cheerful tone, "Of course Jer! I honestly don't want to get involved with Damon. Didn't you know that he's a gangster?" She dropped her voice to a playful whisper on the last words, teasing her older brother, causing him to laugh.

"Yes, I have heard that. You should be careful; those gangsters can be mighty dangerous." And they burst into laughter together.

Their playful moment was interrupted by the ringing of their doorbell. Jeremy didn't seem surprised, so she figured that he was expecting company. He finished off his beer, and tossed it into the sink. "Go to your room Elena." He said firmly, rising from the kitchen table, and turning her to the direction of the stairs.

She wasn't surprised by his command, knowing that it had to do with his gang. He refused to ever tell her anything about it, telling her it was to protect her. She didn't bother fighting it, merely whirling around to kiss him on the cheek, before skipping up the stairs to her room, sneakily pausing on the top step so she could see who was at the door.

She gasped as it was Damon who came into view. He had his arms wrapped around two girls, one of which seemed to be for Jeremy, because she wiggled from Damon's grasp and into Jeremy's arms. The other girl seemed to be perfectly content to stay wrapped up in Damon's embrace.

As if he could feel eyes on him, Damon looked around the room, until he spotted her hovering on the stairs. As their eyes connected, she gasped, whirling away from him and into her room.

The rest of the night was spent working on typing up the paper she had written by hand in the library that afternoon. She congratulated herself on having the foresight to pre-write the paper, as she knew if she had had to write the whole thing that night she would have been distracted by the chatter and giggling that drifted up from the floor below.

It wasn't until she was finished typing her paper, and was getting ready for bed that she realized she was still wearing Damon's leather jacket. It was well worn and bulky, and it was huge on her. But she realized, as she stared at herself in the mirror while wearing it, that she had never felt more beautiful.

A/N: Well, this is the first chapter of BoB. This is my second over all fic, but my first Vampire Diaries fic. The title is from a song by The Rolling Stones, with a cover done by Bette Midler. I feel that it could fit from everyone's perspective, from Elena, to Damon, even from Jeremy's point of view. Please don't be mad at Damon, remember, right now he doesn't want to be saved. This is a dark story, about gangs, fights, death, but it is still a love story, trust me on that.

Also, the reason why this story is located in Chicago is a matter I want to address now, because I know I will be questioned about it. I chose to place this story in Chicago because it involves gangs, and honestly? Gangs in Mystic Falls? So for the sake of this story, no one has ever lived in Mystic Falls. I chose Chicago specifically because of its ties with gangs in the 1920s. It seemed fitting.

So, if a guy were to give you his jacket, which would you prefer? A leather jacket or a letterman's jacket?