• Vampire Diaries Fanfiction Self Insert
• Vampire Diaries Fanfiction Oc

The relationship between the cured vampire Damon Salvatore and the vampire Isobel Flemming was a sexual relationship. Damon turned Isobel into a vampire, and Isobel then came back to Mystic Falls, and threatened the girl he was in love with, who also happened to be her daughter, Elena Gilbert. “I wasn’t aware we were playing strip poker, sweetheart,” Klaus comments with unreadable eyes, his pronunciation of sweetheart only making her wetter. Still, when she levels him with a stare, he begrudgingly complies. First, he shucks off the black coat and tosses it behind him. Read The song you get dared to do a strip tease to from the story The Vampire Diaries Imagines and Preferences by courtgrande (Santa baby) with 708 reads.

A/N: My second Delena one shot! I hope you guys enjoy it. I may add a second chapter, with a lemon in it! This is Rated M for adult language.

Thank you to everybody who read and reviewed Don't Be Shy!

Disclaimer: I do not own The Vampire Diaries or any of the characters!

** 'If you obey all the rules, you miss all the fun.' **

Elena sat on her bed, staring out of her bedroom window. She felt like she should be crying, but the tears just wouldn't come. The supposed love of her life had just broken up with her, and she hadn't even shed a tear.

She'd be lying if she said she wasn't a little upset. They hadn't ended on a good note, and she felt guilty for hurting him the way she had. She didn't blame him for breaking up with her, she knew she deserved it. She was also glad in a way though. Stefan had changed her... a lot. At first she loved her new personality, she loved the commitment she was able to put into the relationship. But she had begun to miss being a fun teenager. She missed drinking on the weekends, playing dares and gossiping with Caroline, having movie nights with Matt and having slumber parties with Bonnie. She didn't really get to do these things when she was dating Stefan, because there never seemed time.

Of course there was the other reason for their breakup. She couldn't tell Stefan what he wanted to hear. How could she deny his accusation when it was obviously true?

'Need some company?' he asked, appearing out of nowhere

She gasped at Damon's sudden appearance. He had a smirk on his face, but she could see the pity in his eyes

'I'm fine, Damon. Does it look like I'm sobbing and screaming Stefan's name dramatically because my heart is broken into a million pieces. No.'

'I figured you'd be a little more upset than this,' he said, raising an eyebrow

'I just want to forget about it all. Starting now, I'm going back to the way I was before I met your brother,' she said, starting to feel irritated about everything

'Ah. The wild Elena Gilbert I've heard so much about,' Damon chuckled, sitting next to her

'I really did used to be a lot more fun,' she sighed

'Hey,' Damon said, pulling her chin up so that she was looking straight into his sparkling blue eyes. 'You are fun. That little timeout we had in Georgia was the most fun I've ever had.'

Her heart did a little flutter at what he had said. The fact his face was so close to hers didn't make it any easier either

'If you met me before I met Stefan and before my parents died, then you'd understand why everyone thinks I'm so different,' She said, staring at the floor

'Well, how about you show me how fun you used to be. I mean, I'm interested, and this is an opportunity for you to forget about everything for the night,' he offered

She knew there was no way she couldn't take him up on his offer. A night of fun was exactly what she wanted, and the fact Damon was joining her for it made it a whole lot better. She felt like she could be herself around him.

'We'll get out the alcohol, and we'll play truth or dare and you can gossip to me all you want. We'll do whatever you wish,' he said, a smirk on his face

'Sure,' Elena said, a smile on her face. She was grateful that he was here; she needed his company right now

Damon flashed downstairs at Vampire speed, and was back in less than a minute, carrying all of the alcohol that there was in the house

'Damn, you Gilbert's like to drink,' Damon muttered, placing the large amount of bottles onto her bed

'Says the man who has at least fifty bottles of Bourbon stashed away at home,' Elena giggled and Damon just shrugged

'Totally different.'

'Sure.'

He handed Elena a glass of Bourbon, unsurprisingly.

They drank and drank for two hours, and spoke about nothing and everything. Only when Elena started to feel a little drunk, did things get interesting

'Let's play Truth or Dare,' she giggled

'Look, Elena. You don't have to convince me to play Truth or Dare with you to get me naked,' he said, in a mockingly serious tone. Elena laughed and rolled her eyes

'There will be no nudity tonight, Mister,' She teased

'How about tomorrow night then?' he asked and winked at her

'Nuh-Uh,' She said in a sing-song voice. He pouted playfully, and smacked her butt when she stood up to grab another bottle of bourbon

'Hands to yourself, Salvatore,' Elena giggled, sitting back down with the Bourbon

'No promises,' he chuckled, taking the glass of Bourbon she handed him

'Let's get started. Truth or Dare?' She challenged

'Hmmm. Truth,' he decided, a smirk on his face. She scrunched her nose, concentrating.

'Got it!' Elena shouted. 'Is it true that you've been in love with someone besides Katherine?'

Damon sighed and nodded. He didn't like lying to Elena. He only did it if her life was in jeopardy.

'With who?' Elena asked, too curious for her own good

'Jealous?' Damon asked, smirking a lot

'Maybe. Now tell me who,' Elena muttered impatiently

Damon leaned forward until Elena could feel his hot breath on the shell of her ear

'I think you already know the answer.'

Elena shuddered at his words. She wasn't sure at first, but his annoyingly cryptic answer confirmed it. He was in love with her.

Damon spoke before she could question him. 'Elena. Truth or Dare?'

'Dare,' she giggled

'Flash me.'

'Seriously? That's your dare?' Elena doubled over in laughter. She knew it'd be something perverted, but not some middle school dare

'Yep,' he confirmed, a huge grin on his face

Elena rolled her eyes and lifted up her tank top. She had no bra on underneath

Damon's eyes nearly flew out of their sockets. He didn't think Elena had it in her. He thought she'd slap him and call him a pervert or something else that would highly amuse him. But instead of amusing him, she'd managed to make him incredibly aroused.

Damon's hands had a mind of their own. He slowly moved them towards Elena's breasts

Suddenly, she yanked her tank top down and slapped Damon's hands and smirked. 'Hands. To. Yourself.'

'Tease,' Damon muttered and Elena laughed

'Truth or Dare?' She asked him

'Dare, I guess.'

She smirked and told him what he had to do.

Elena watched him knock on her neighbour's door from her bedroom window. He asked the man if he had any ice cubes. When the guy returned, he handed Damon several ice-cubes, which Damon proceeded to shove down his pants

Damon sped into her room at Vampire speed, and started shaking all the ice out

'Cold, cold, cold!'

Once he'd finished complaining and getting rid of the ice, he sat back on the bed

'I will get you back for that,' he muttered, taking a sip of his whiskey

'Whatever,' Elena giggled

'Truth or Dare, Gilbert?' Damon asked, his smirk returning

'Truth,' She decided, drinking from the huge Vodka bottle Damon had brought upstairs with him

'Tell me the naughtiest thing you've ever done,' he chuckled darkly

'There are a few things for me to choose from,' She admitted, trying to decide which the worst was

'Probably the time when I played strip poker with the varsity football team,' She told him, cringing at the memory

'Just you and the whole team?' Damon asked, biting back his laughter

'Yes,' She sighed, staring at her sheets

'Tell me what happened,' Damon demanded

'Well, the team had just finished a game, and this was when I was a cheerleader. I walked into the locker room with a deck of cards and asked them if they wanted to play with me,' Elena explained. Damon was surprised at how... un-innocent Elena used to be

'They all said yes, of course. Once you were naked, you were out of the game. In the end it was just me and one other guy playing. The loser had to give one of the other guys a blow job and the winner got to choose who would be receiving it...'

'You lost, didn't you?' Damon guessed and chuckled. Elena nodded, a blush on her face

'Who did the winner choose?'

'Himself, of course. Typical guy,' Elena said, rolling her eyes

'Who was the guy?' Damon asked, incredibly curious

Elena was reluctant to tell him. It wasn't exactly one of her proudest moments.

'Tyler,' she mumbled under her breath. Of course Damon heard though, with his vampire hearing

Damon howled with laughter. He was stunned, yes, but that didn't make it any less funny

'I can't believe you've given Lockwood a blow job, but not me!' he chuckled

'I can't believe I've even seen Tyler's cock,' Elena muttered

'Wait! Isn't Matt a Jock?' Damon asked, his laughter starting again. Elena nodded, even more ashamed

'So you gave your ex-boyfriend's best friend a blow job, while he watched,' Damon summarised

'You know, I was beginning to not feel guilty about this, until you started talking,' Elena snapped, irritated by his humour

'Hey, it's not my fault you were such a wild child!' Damon defended himself, laughing slightly

'Yeah, whatever. Truth or Dare?' Elena muttered

'Dare.'

'Tomorrow night, you and I are going to the Grill, and you have to hit on at least three guys,' Elena dared him, with a wicked grin on her face

'Only if it's a date... after I hit on the guys,' Damon said

'Deal.'

'Great.'

Suddenly, Elena realised what she'd agreed to. She was so eager for Damon to do this dare, she didn't even think about what he'd actually said!

However, the more she thought about it, she realised it was harmless. One little date... no big deal. Right?

She shook her thoughts away. Tonight was supposed to be fun, so she'd worry about it tomorrow and just enjoy her stress-free night with Damon

Damon on the other hand, was thrilled. It'd been a few months now since he'd realised he was in love with Elena. And it seemed like with every passing day he just wanted her more!

'You know, Caroline told me once that you seduced your teacher to get a good grade, before you met Stefan,' Damon chuckled

'My mom and dad told me I couldn't go out with this really hot guy that had asked me out, unless I got at least a B on my paper. I was determined to go... so I flirted a little,' Elena admitted

'Seriously, you've managed to convince an entire football team to play strip poker with you and you managed to seduce your teacher. I need to see these skills of yours,' Damon said huskily

'You might get lucky tomorrow,' She said and winked at him

'I hope so,' Damon smirked

They carried on playing, and Damon learnt a lot more about Elena. He learnt that she wanted to be a writer, she'd had no other boyfriends besides Stefan and Matt, her favourite colour was red, she'd snuck a boy into her room once before, she'd played strip poker four times, she'd never smoked or touched drugs and he'd even got her to admit that she had dreamed about him.

'Will you tell me why you and Stefan broke up?' Damon asked, swirling his scotch around in its glass

'He... wanted me to tell him something,' She stated

'Could you possibly be less vague?' he demanded. Elena bit her lip, not sure if she should tell him.

She knew that one day she'd have to confess her secret to him anyway, but she wasn't sure if tonight was the right time.

She took a deep breath, and stared straight into those beautiful pools of blue that were Damon's eyes. It's now or never, she thought

'He asked me to tell him that I didn't have feelings for you and that we were just friends... and that's all that I would want us to be,' I whispered, toying with my glass

'And?' Damon inquired, getting more anxious by the second

'I told him that I couldn't lie to him,' Elena sighed. Damon stared at her, unsure of what to say. He was stunned, ecstatic and guilty and he didn't know which of those emotions to show. He chose the latter.

'I'm sorry... that I made you feel that way... and that it ruined your relationship,' Damon said sincerely. Much to his surprise, she laughed

'You didn't make me feel that way; it's not your fault. You can't help being perfect for me,' Elena chuckled humourlessly

'I know that you and Stefan just broke up, but I want you to know that I love you. I have for a while now... and I think I always will,' he admitted to her

'I do know that. I just... need time to think everything through,' She murmured and Damon nodded

They decided to call it a night. Elena was getting tired, and there was a lot of awkwardness in the air

'I'll pick you up at seven tomorrow for our little date,' Damon chuckled and she smiled up at him

'Okay. Goodnight, Damon.'

Damon leaned down, and placed a gentle, loving kiss on her forehead. They stared at each other, the sexual tension hovering around them

All too soon, Damon was gone. Leaving Elena in the same position he'd found her in. Staring out of her bedroom window. Only this time, she was thinking about how hard she truly had fallen for Damon Salvatore.

A/N: Okay, so if I get a positive response from this, then I'm going to do a second chapter. It will be about Damon and Elena's date at the Grill! I'm eager to write about Damon hitting on three guys :') I also feel like a lemon is needed!

Thank you for reading!

- Mia.

10 P.M. That Night; Mystic Falls, Virginia

'There goes your shirt, Elena. You better start winning, or pretty soon, you'll be naked.' Damon said with a smile. Apparently Elena wasn't too good at strip poker, though of course, Damon knew that from the start.

'Hey, I wouldn't be talking if I were you!' While Elena was sitting there in her bra and underwear, Damon had his pants on.

One round later, Elena had lost once again. As soon as she'd realized something had to come off, she just looked at Damon.

'You win.'

'Oh do I? From what I see, you still aren't naked. Those are the rules of the game, Elena.' Damon said, with his usual smile.

'I have a better idea.' Elena said, creeping closer to Damon.

'Oh yeah? And what's that?' Their faces were now inches from each others.

'This.' She said, in a whisper as she leaned in for a kiss. Then they made their way to the bedroom, but not before Damon reminded her to take her bra off. He did win strip poker after all.

The Next Morning; Mystic Falls, Virginia

Elena woke the next morning in Damon's bed, the covers wrapped around her body, concealing her nakedness. Last night was amazing. She realized Damon wasn't next to her. Then she saw a note on his pillow:

'Feeding.

Back soon after you wake up.

xoxo -D'

Vampire Diaries Fanfiction Self Insert

That explains it, Elena thought. Well she might as well get herself some food. As she looked around for her clothes, she realized most of her clothes were downstairs. Only her bra and underwear in the room. Oh well, she thought, it's a short walk downstairs. Slipping on one of Damon's shirts on over her bra and underwear, she walked downstairs to the table they had been playing poker at. There was her shirt, and her pants right beside it. Taking off Damon's shirt, she grabbed her own from the table. Before she put her shirt on, she heard a noise from behind her. Looking back, she saw...

Vampire Diaries Fanfiction Oc

'Stefan.' She took a step back, startled.

'Oh, um, Elena. I, uh, I wasn't staring. I...' He looked down, cheeks turning red. Then Elena realized she still wasn't wearing clothes.

'Oh my God. I need to get some clothes on.' Then she put her shirt on, with her pants following. 'You can look over here again now.' Taking a small glance over first, just to make sure, Stefan turned back around, and looked at Elena.

'Sorry, I didn't know you stayed the night.' Stefan said.

'No, really it's okay. I mean, it's not like you knew I would be walking down the stairs half-naked.' She tried to smile, but it came out as more of an insincere smirk. 'Maybe I should go...'

'No. You don't have to. Of course, you can if you want to, but I won't kick you out or anything.'

'Yeah, I'll just go. Tell Damon I said goodbye.' She said, grabbing her shoes.

'Okay. Goodbye Elena.' She took a few steps toward the door, then turned around, facing Stefan.

'Shit.' She muttered. 'My car is at home. Damon drove me here.'

'I could drive you home. If you'd like, that is.' Stefan said.

'I'd love that. Thank you.' She responded, smiling.