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Summary: John Gilbert owes money to the notorious Damon Salvatore and Klaus Mikaelson. What happens when the only thing he has that is of any value is Elena? AU/AH

Rated: M (for later chapters)

Disclaimer: I do not own any of the characters, only the plot is mine.


"Rise and shine, sleepyhead!" A voice sing-songed beside Elena's right ear. With a moan of protest she buried her head under the covers. "Elena..." Damon sighed attempting to pull the covers away from her.

"She's sleeping." Elena whispered, holding onto the covers.

"Right that's it, no more nice Damon." He murmured before he whipped the covers off the bed.

"Fine, I'm up." Elena groaned.

So am I, Damon thought as he took in the sight of her long legs and her round bottom which was only encased by a pair of red lacy boy shorts. He thanked the heavens that she hadn't realised that his shirt had ridden up on her and just enjoyed the glimpses of her body that he was seeing. She slowly got up, stretching her arms to the sky as she let out a mewl of pleasure.

"Mmm. Damon?" She sing-songed, swinging her legs against the side of the bed and looking the picture of innocence.

"Yes?" He questioned, suspiciously.

"My tummy's all rumbly." She pouted, rubbing her stomach.

"What do you want me to do about that?" Damon smirked.

"Breakfast, please!" Elena squealed. Damon chuckled at he enthusiasm before grabbing her and tossing her over his shoulder.

"Damon," She groaned, "why do you have to be such a caveman?"

"Shh, you love it." He refuted, giving her ass a light tap.

"I'm so getting you back for that."

"Go ahead, kitten, you can slap my ass any time." He punctuated his statement with a wiggle of his hips, eliciting a giggle from the brunette. Damon slowly lowered her to the kitchen counter, halting her when she tried to move.

"Ah, ah, ah. You're helping me cook breakfast."

"I'm a terrible cook," She groaned, "seriously, I burn stuff in the microwave!"

"Okay, I have to admit, that's bad. But, seeing as I am so terribly amazing, I think I can turn you into a pro." He winked. He watched as she contemplated his offer and slowly placed his hands on the counter beside her thighs, his thumbs rubbing tiny circles on her skin. He smirked as goose bumps rose on the flesh that he touched.

"Fine," She huffed, "but if this is a complete disaster, you only have yourself to blame." She warned, wagging her finger at him.

"Okay, I will heed your warning, Miss Gilbert." He chuckled, as he moved towards the fridge. "We'll start with something simple. French toast. Now, do you know what this is?"

"Damon, seriously!"

"Answer the question, Elena."

"It's an egg." She stated, with annoyance.

"Well done!" Damon exclaimed with fake enthusiasm, mussing her hair. "Now," he said handing her a bowl and whisk, "crack the egg into the bowl and whisk it."

Elena quickly did what he said but was intercepted by his hand on hers.

"Did I do it wrong?" She frowned.

"No, no. You just don't want to over whisk them." He explained. "I'll do the messy part for you." Elena watched as Damon dipped the bread into the whisked eggs before putting them into the pan. He slowly moved towards her, picking her up from the counter and setting her on her feet.

"Why couldn't you just ask me to get off of the counter?" She huffed.

"Because then I wouldn't have gotten to hold you in my arms. Now, come on, you have to flip these bad boys."

Elena was able to flip the French toast with only minimal help from Damon.

"I am good." She moaned, ravenously eating her breakfast.

"Fine, just take all the credit." Damon scolded, good naturedly. "We'll leave in about an hour. You can just add your clothes and whatever else you need to my suitcase."

"Okay. How long will we be gone for?"

"A few days, give or take." Damon smiled. "Now go get ready."


An hour later, Damon and Elena were on the road, their suitcase safely tucked into the boot of the blue Camero. Elena had subtly tried to hide some of the racy underwear Caroline had bought her amongst the clothes she had packed. What she didn't know however, was that Damon had also slid some of the raciest items in there too, thanks to Caroline's clues as to where Elena had hidden them.

Elena laughed loudly as she listened to Damon singing along to Taylor Swift. He couldn't help but stare at her. She looked beautiful in her white skinny jeans and sea green, flowing top. Her legs looked delectable in her thight jeans and his desire was only heightened by the silver high heels she wore which lengthened her legs to an almost impossible extent.

"Seriously, how do you know all of the words?" Elena managed to ask, through her hysterical laughter.

"I am a man of many talents, many of which I can show you in the bedroom." He flirted, wiggling his eyebrows at her.

"Cocky, much?" She scoffed.

Damon smirked, looking down at his crotch. "Very much."

"Are going to be this annoying the entire trip?"

"Ouch. That was low. I'll have you know many people would pay for my company." Damon teased.

"Yea, maybe as a gigolo." She muttered quietly, however Damon heard every word.

"You know, I wouldn't make you pay, my sweet cherry blossom." He smirked at her quick intake of breath.

"H-How did you know?" She murmured, her gaze turning to the floor.

"You have this aura around you, you're pure and innocent." He watched as a blush coloured her cheeks. "It's nothing to be embarrassed about. In fact, I think it's pretty great to wait for someone you feel comfortable with. I fumbled away my virginity in the back seat of a car with a girl I didn't have any feelings for." He said as he grabbed her hand, rubbing his thumb along the back of her hand.

"Thank you."

"For what?"

"You just have this uncanny ability of making me feel better, so, thank you." She smiled, leaning across the car to place a light kiss on his cheek.

"You're welcome." He whispered, awestruck by what she had just done. He watched as she tried to hold back a yawn and failed miserably. "Go ahead, sleep. You need the rest." Damon smiled as she closed her eyes, her hand still interlocked with his.


"Wakey, wakey, Sleeping Beauty." Damon whispered, shaking Elena slightly until she moaned sleepily. "If you don't wake up now, I'll have to try the whole princess technique and kiss you." He smirked as her lips quirked slightly. She was playing him, he thought, too bad he was the best at this game. He leaned in slowly, his breath fanning across her lips, and watched as they parted slightly. He allowed his lips to brush a mere centimetre past her lips, before he placed a loud, wet kiss on her cheek.

"Ugh, Damon, you're disgusting!" Elena yelped, using the bottom of her top to wipe his saliva from her face.

"Come on, we have to get a hotel room." He persuaded, opening her door further. He was waiting for her to climb out when she suddenly reached out for him.

"What?" He questioned.

"Carry me." She pleaded, smiling at him.

"Seriously?" He asked mockingly and watched as her head moved up and down rapidly. "Come on, then." He huffed, turning around so she could climb on his back. Elena wrapped her arms around his neck and her legs around his waist, snuggling against his back. Damon closed the doors to his precious Camero, grabbed his suitcase from the boot, and locked the doors. He was slowly walking along the car park when he felt a soft kiss being placed behind his ear. He smiled. A true genuine smile.

Damon smirked at the stares he got as he carried Elena across the lobby of the hotel. He managed to catch a few of their whispers and according to an old couple near the magazine stand, 'They were the picture of young love'.

"Hi, can we get a room for the next few days?" He asked the young man behind the desk. Damon watched as the boy's bored expression quickly changed to one of lust and awe as he took in the sight of Elena.

"Yea, a room. Erm, we don't actually have any rooms with single beds left so I guess you and your sister will have to share a double room." The boy, Tommy, uttered completely ignoring Damon, his eyes transfixed on Elena.

"A room with a double bed will be just fine. And just, FYI she's not my sister. Believe me, we would have committed a very incestuous relationship if she was." He smirked, leaning forward. "Can you make it a king's size bed, she's an animal between the sheets when she gets going."

"Damon!" Elena shrieked, hiding her face in embarrassment.

"Thank you." Damon smirked as Tommy handed him the key with a disgruntled glare.

"Why did you say that to him?" Elena asked through gritted teeth when they were alone in the elevator.

"He was about to get his flirt on with you. You deserve better than some pimply faced boy." He grunted.

"Were you jealous?" Elena teased, a beaming smile on her face.

"Of him? Please." He scoffed.

"I don't know, I thought he was cute."

"Cute?" Damon exclaimed but was cut of by Elena's tinkling laugh. "Oh ha, ha. Very funny, Elena." He huffed slightly, "Fine, I was jealous."

"I knew it!" She smiled as Damon made his way to their hotel room. He slid the card key into the slot and walked into the room, allowing her to slide from his back. He spun around to face her grasping her hands tightly in his. Elena looked up at his pensive expression.

"Damon? Is something wrong?" She tilted her head, studying him.

"Go on a date with me tomorrow night."

"Really?" She asked, a small smile on her face.

"Really."

"Okay!" She smiled, kissing his cheek.

Damon and Elena both got ready for bed, their long day of travelling had exhausted the both of them. They were both lying in bed in the same position as the night before, Damon on his back with Elena lying on his chest when she let out a low groan.

"I'm such a slut!"

"What?" He asked, incredulously.

"We haven't even been on a date yet and I'm already sleeping with you."


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