AN: Thank you for the reviews, they mean so much! I hope you enjoy this chapter!

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.

Elena woke up with a soft moan of pleasure, stretching and rolling onto her side. Her hand reached across the bed, searching for the warm body she had fallen asleep on the night before, but it was met with the cold fabric of the sheets. Her eyes drifted open, taking in the sight of the empty bed, before he gaze landed on a folded piece of paper on the pillow. She pushed herself up against the headboard and reached for the note with her name inscribed on it. Elena's face held a grin as she read through the note from Damon.

'Good morning, beautiful. You're probably wondering where I am but don't worry, I'm just organising the plans for our hot date tonight. I will pick you up at six and I wouldn't mind if you wore that lacy underwear I found in the suitcase. I have to give you credit, you hid it well! Don't fret about what to wear, you will look gorgeous in anything and if you decide to wear nothing at all, I'm sure I can relocate our date to the hotel room ;)

See you at six, Damon x

Elena jumped out of bed when she realised she had slept until 2:30. She decided she would take her time to get ready so she looked perfect.

Two hours later, Elena's skin was almost withered after her long and relaxing bath. She slowly blow dried her hair before tying it up into a sleek ponytail. All she needed now was an outfit which would blow Damon's mind, she smirked, realising she had the perfect one.

At exactly six o'clock, Damon knocked on the hotel room door, his heart thundering in his chest. He quickly looked at his outfit. He was dressed in an impeccable black suit with a crisp white shirt underneath, a few buttons at the top of his shirt left unbuttoned, showing off a sliver of the tanned skin of his chest. His black dress pants were tight against his legs, showcasing his muscular thighs. He was dressed in head to toe designer gear right down to his very shiny, black shoes. His hair was sufficiently mussed so it looked sexy but not messy and unkempt. His head shot up as he heard the door being pulled open and his heart froze when he took in the sight of the goddess in front of him. Elena was dressed in a deep pink dress which wrapped tightly around each one of her deadly curves. A sequined belt was draped around her waist, pulling it in and pushing up her breasts. Her feet were encased in six inch black heels which just screamed fuck me. The heels lengthened and showed off her toned and tanned legs which seemed to go on forever. A few silver bangles rested around her right wrist and she held a black clutch in her left. Her hair was sleeked back, showing off her glowing face. She wore little make up, only a dash of lip gloss but she still looked beautiful and even the diamond earrings hanging from her ears couldn't outshine her beauty.

"Y-You look stunning, if it wasn't already obvious." He murmured, sweeping down to take her hand in his and brush a kiss along her knuckles before pulling her hand under his arm so it rested on his bicep. "Shall we?"

"We shall." Elena breathed, still in shock at how gorgeous he looked. "You look good too, you know."

"I know." He smirked as he led her into the elevator.

"Always so cocky." Elena laughed, shaking her head.

"Well, you wouldn't have me any other way... Would you?" His comment had started off confidently but soon turned vulnerable when he realised that he didn't know how she felt about him.

Elena sensed his vulnerability and was quick to reassure him, "I like you now, just the way you are." She whispered, leaning her head forward to press a kiss to his cheek. Her movement was stopped when he turned his head to look at her, their lips a mere inch apart. They both looked into each other's eyes, searching for any trace of rejection, before they closed their eyes and leaned in until their lips connected. Damon had never experienced a kiss like it; it was soft, slow and tender yet, he felt no need to deepen it. Their lips moved in sync, as if the act had already been attuned to perfection. They broke apart slowly and reluctantly, their noses brushing together as they parted.

"Wow." Elena breathed, her eyes flicking up to meet the ocean blue of her date's.

"I think that was the best way to start off the date." He smirked, placing another soft kiss on her lips. They broke apart as the elevator dinged, signalling their departure.

Damon intertwined his fingers with Elena's pulling her from the lift. They walked out of the hotel, both gazing at each other with love struck expressions.

"Where are you taking me for this hot date, then?" Elena questioned, a silly grin on her face that had been present since the elevator ride.

"That's for me to know and you to dot, dot, dot..." Damon replied, stealing a quick kiss from her lips. He couldn't help it, now that he was allowed to kiss her he found that he just couldn't stop. "We're nearly there anyway."

Elena tore her gaze from Damon, realising that they had walked down the street and into the local park. She gasped when she saw small lights in the distance. Upon futher inspection, she discovered hundreds of fairy lights were surrounding a blanket on the ground that was covered with various foods and drinks.

"You did all this for me?" She whispered looking up at his twinkling eyes with awe.

"Of course." He whispered, pulling her towards the blanket. He watched as she kicked off her heels curling into his side as he prepared their meals.

"It's so beautiful here." Elena whispered, not wanting to disturb the peaceful atmosphere that surrounded them. "Why is there no one else here?" She questioned, looking up at the twinkling stars that were covering the night sky, it was so romantic.

"I rented out the park." Damon explained nonchalantly, handing her a plate.

"The whole park?" Elena exclaimed to which Damon simply nodded. Elena looked down at the plate he had handed her which was covered with various little nibbles including chicken goujons, a small salad, pasta with a creamy sauce and some baby potatoes.

Damon watched as Elena ate greedily and moaned with pleasure. Her moans were doing sever things to his insides and he had to shift his pants to try and hide his arousal.

"You like?" Damon chuckled and watched as Elena nodded her head vigorously.

"Mmmm. This is so good! Did you make it?"

"Of course, it was part of our deal remember. I have to cook your meals to be able to enjoy your glorious company." He teased. "The hotel allowed me to use their kitchen so I was able to prepare all of the various foods myself."

The couple finished their meal in a comfortable silence, basking in each other's company.

"Ready for dessert?" Damon questioned, reaching behind him to pull out a bowl of chocolate covered strawberries and a bottle of champagne.

"You are amazing." Elena whispered as Damon fed her a strawberry. She couldn't help but moan as the sweet chocolate flavour covered her tongue and the juice of the strawberry swirled around her mouth.

Damon grabbed two glasses and proceeded to pop the cork from the champagne, enjoying the giggles that erupted from Elena's mouth as a splash landed on the skin of her bare leg. Her laughter soon vanished when Damon leaned towards her leg, allowing his tongue to lap up the fallen champagne. He slowly stroked her thigh, rubbing the dampness from her skin but producing an altogether new dampness on her lacy thong. He looked at her lust filled eyes and quickly removed his hand. Damon soon filled two glasses with the bubbly champagne and handed one to Elena.

"Here's to a great first date." He purred, clinking his flute with hers.

"First date, huh? So there's going to be more?" Elena teased, moving her head towards Damon's.

"Definitely." Damon murmured, crashing his lips onto hers. This kiss was not like their first. It was carnal and full of lust, need and passion. He groaned as he felt her tongue slide along the seam of his lips. Damon granted her access immediately, meeting her tongue with his own. Their tongues danced together as Elena moved on top of Damon. Her thighs rested alongside his hips as one of his hands rested on her bare thigh, the other on her neck, holding her head to his own so he could continue to plunder her mouth with his tongue. Elena was so caught up in the kiss that she didn't realise that she had started to grind down on Damon's erection until he groaned, breaking their kiss, and began moving out from underneath her.

"What are you doing?" Elena breathed, grasping onto the lapels of his jacket.

"I think we need to take a pause before this goes too far." He explained.

"What if I want it to go further?" Elena whispered, looking up at him through her vast expanse of eyelashes.

"Elena-"

"Damon, don't. I'm positive, I want you to be my first." She whispered giving him a chaste peck to his lips.

"Are you sure? Elena, you have to be sure." He explained, cupping her cheeks softly.

"I'm sure, Damon."

"Then, let's head back to the hotel, a bed would be a more appropriate location." Damon smiled as he pulled them up from the ground. The couple quickly tidied up their date into the picnic basket nearby and made their way back to the hotel, each nervously anticipating what would happen when they got to their room. The elevator ride was silent and as the couple made their way to the door, their nerves were evident.

"You ready?" Damon questioned as he slid the card key into their door.

"More than ready." Elena smiled, kissing him with passion. She pushed him through the door, kicking it closed with her foot.

I know, I'm awful to leave it there but the next chapter is most deserving of the M rating! Review, please! Amy x