Disclaimer: I do not own anything related to The Vampire Diaries, TV show or books. However I decided to have a little play around with the characters (I would definitely like to play with Damon).

After some careful consideration, I have decided to do these stories in show order. Although the one-shots themselves may seem unrelated, the diary entries are not. This is now chapter one as it will be literally setting the scene for the rest of the story right up until the point they become a couple in the show. One Good Man has been moved to chapter two as that is the appropriate position in the show timeline. There have also been some small amendments made to that chapter.

I must stress, there is a plot behind this, however almost every chapter will be smutty and if that is not your thing, this may not be the story for you, although the smut is essential to the plot. However, there is the option of stopping at the smut as the build up is as important as the smut itself.

This is only a short chapter but it is necessary.

At points in the future, Elena will refer back to this chapter.

This chapter will be very different from almost every other chapter (there might be and occasional chapter without smut, or very little smut if it is essential to the plot).

All will be explained after in the very important notes at the end.

Friday Night Insights

Dear Diary

Last night Stefan and Bonnie came to mine for dinner so Stefan could win her over (which he totally did :) ) and it was a great night until Caroline turned up uninvited with Stefan's brother Damon. He told me a little bit about him, Stefan and Katherine, but that's not what was strange. He seemed to...understand me. He was the only one who realized I was unhappy with cheer leading But that wasn't what was really weird. The strangest part was when I fell asleep.

E

The previous night's dream...

After the dinner party, Bonnie, Caroline and Damon left, leaving just Elena alone with Stefan. They headed up to Elena's room, and sat on her bed to do some history homework and talk about the earlier events of the evening.

"Tonight wasn't so bad. I had fun." Elena smiled shyly at Stefan.

"Hmm. That makes one of us." Stefan frowned.

"Come on." Elena sighed. "Your brother isn't as bad as you make him out to be..." she said, however Stefan stopped her from talking as he gently put his finger to Elena's lips before he touched her cheek and began to kiss her.

Stefan pushed Elena's text book on to the floor to get it out of the way so he could get closer to Elena's body as he deepened the kiss. Feeling confident, Elena pushed him on the bed and straddled his hips as Stefan threw her teddy bear off the bed, whilst they continued to kiss. Deciding to take their make-out session one step further, Elena sat up and removed her top so she was just wearing her white bra, as Stefan sensually slid his hands up her body. Stefan began to remove his shirt and lifted it over his head, however when his face emerged from underneath, it was no longer Stefan who was looking up at her, but a grinning Damon. Elena jumped away and began to scream, backing herself into the dresser.

In a flash, Damon finished removing the his shirt and was on his feet in front of Elena at superhuman speed, backing her up even further into the dresser. Damon put his finger to Elena's lips, mimicking Stefan's earlier action to quieten her.

"Shh." he said softly and reassuringly, as Elena's breathing suddenly began to return to normal in a way she couldn't explain.

"Why are you here?" Elena whispered. "Why am I dreaming about you?"

"Maybe it's your subconscious telling you what you really want." Damon replied. "Or maybe it's curious?" he added as Elena frowned.

"Why would I want you?" she asked. "I'm with Stefan."

"Remember the back to school party when Bonnie predicted your future?" Damon asked as Elena nodded. "What did she say?"

"She said she saw a man, a crow and fog." Elena looked at Damon with interest. "Why?"

"When was the last time you saw a crow?" Damon replied as Elena's frowned.

"At the boarding house." she said quietly.

"That was my crow." Damon told her. "Bonnie was talking about me."

"How do you know all of this?" Elena asked.

"It's only a dream Elena." Damon smiled. "Why do you think Bonnie saw me in your future and not Stefan?" he asked, tucking a stray hair behind Elena's ear, sending shivers down her spine.

"I...I don't know." she stammered.

"Because some time, in the not too distant future, you'll leave Stefan to be with me." he told her confidently. "It'll be just you and me forever." he smiled.

"Why should I believe what Bonnie said?" Elena asked as Damon inched slightly closer.

"Because she's a witch Elena." Damon replied. "So enough of the questions, aren't you at least a little bit curious to know what it will be like for us?"

"What do you mean?" Elena's voice hitched as she suddenly became hyper aware of their near nakedness.

"When we touch, when we kiss." Damon's voice suddenly became husky and seductive.

"Won't I be cheating on Stefan?" Elena asked innocently.

"Relax, it's just a dream Elena." Damon reassured her once more. "But if Bonnie is right, you're cheating on me with Stefan." he smirked. "You are dreaming about us, so I suspect you must be at least a little bit interested to find out, otherwise the dream is pointless." he said as he ran his hand down the side of Elena's face, causing her to lean into his touch, which she put down to curiosity.

"I guess..." Elena hesitated, before reaching out to touch Damon's face as he held his hand over hers and momentarily closed his eyes before turning his head slightly and kissing her wrist, causing Elena's breath to quicken.

"Calm down Elena." Damon said softly. "I won't bite." he promised. "I'll let you take the lead and I won't do anything you don't want me to do." he promised. "But remember, it is only a dream, nobody else will ever know, but it's your choice Elena." he whispered.

Deciding dream Damon was right and nobody would ever know, Elena hesitated for a second to allow herself to examine his fabulous body, her eyes momentarily drawn to his treasure trail, before placing her hands upon his chest and sliding them up to his neck, pulling him towards her. Damon wrapped his arms around her back, holding her in closer. Standing on her tiptoes, Elena placed a chaste kiss on Damon's lips, before pulling him back and looking at him in the eyes. It was the first time she'd allowed herself to truly look at him, and she had to admit he was probably the most gorgeous man she'd ever laid eyes upon. His icy blue eyes stared back at her with a look of adoration, fanned by dark eyelashes, set against a background of pale white skin with a shock of raven hair. He had a strong jaw and high cheekbones which most women would kill for. His overall look was one of a masculine beauty which oozed sexuality, yet at the same time gave off a strange dangerous, inhuman vibe, which she couldn't quite put her finger on.

Realizing Bonnie's words were indeed what must be triggering the dream and that nobody would know about what she was dreaming, Elena threw caution to the wind and pulled him back into a kiss, this time with more passion, not unlike the way she'd kissed Stefan earlier in the dream. What was different, was how Damon responded. Elena was used to teenage boys, not a man. Stefan's kisses were warm and tender, whereas Damon was all fire and passion. Initially their kiss began exploratory, however their tongues soon began to dance, knowing exactly what each other needed. Electricity began to ignite all over Elena's body like she'd never felt before, yet she felt an odd sense of peace, of finally being home overwhelmed her her, making her feel safe and secure in his arms.

Elena scraped her fingers through Damon's hair as he pulled her in tighter so their jean-clad hips were molded together, his erection pressed up against her, sending heat pooling to her stomach. Desire ran through Elena's body like she'd never felt before, a craving for Damon's body to be closer to her, touching her, inside of her, which was a desire she'd never truly experienced before.

Damon lifted Elena up and she wrapped her legs around his waist as he walked her back over to the bed and lay her down, dropping himself down and hovering above her, whilst they continued to kiss. Their hips ground together, creating more and more friction, causing the heat to pool in Elena's stomach like never before. Elena had been turned on in the past, most recently by kissing Stefan, she also suspected she'd had an orgasm once, although she wasn't entire sure, but she'd never in her short life felt like this. He was making her feel wanted and desired which was far more erotic than any previous experience with either Stefan or Matt.

Damon's kisses made their way down Elena's jaw and neck, where he licked up one side of it and scraped his teeth down it before purposely sucking on it, almost like a vampire. The words nearly made her laugh out loud considering what Matt had told her about Vicki's hallucination in relation to her animal attack.

Once Damon made it down past Elena's neck he looked up to her for permission to remove her bra, which she gave willingly, after all there were two potential scenarios. The first being that this was just a dream, so no reason to be shy in a dream. The second was that there was a minuscule chance that this could be something real and magical, meaning that at some point she'd leave Stefan for this man and they'd be together for the rest of their lives, so there was no point in being shy with the man who was going to see her naked forever.

After he'd expertly removed the offending item he circled his tongue around Elena's areola as he gently pinched the other nipple, causing them to both pebble, before he began to suck, nip and lick her breast, all the while his eyes never left hers. Elena had never know her breasts could be so sensitive, and his actions were causing her panties to dampen.

Damon switched breasts and continued his ministrations, as he began to stroke the side of her body with feather-lite touches, causing her to become even more aroused. Suddenly, much to Elena's disappointment, Damon stopped and made his way back up to hover above her once more. However her disappointment didn't last long, as he began kissing her with the same fiery passion as before, whilst at the same time grinding his hips against hers. His hand swept down her body before pulling up her thigh and wrapping her leg around his waist so she could feel the growing bulge of his erection in his jeans pressing against the exact spot she needed.

"God you're wet, I can tell." Damon mumbled between kisses. "You have no idea how hot and sexy that is." he added as Elena began to moan with pleasure.

Elena forgot to question how Damon knew how turned on she was through their jeans, especially when she realized that there was a distinct possibility that she was going to have an orgasm from dry humping alone, which she'd never imagined to be possible. Damon's hands continued to sensually roam her body as she did the same to him. One of her hands running through Damon's soft raven hair, whilst the other stroked his chest, feeling slight tufts around his nipples, before making her way to his back and down to cup his behind so she could pull his crotch in closer to her core.

"I want you inside of me." Elena begged as Damon stopped and closed his eyes.

"I can't." he frowned.

"Why not?" Elena asked, disappointed, her body desperate to find it's release, she couldn't believe Damon would work her up like this only to leave her hanging.

"Because I want it to be real Elena." Damon opened his eyes to look at her once more as he ran his fingers along her cheek. "I want our first time to be real, not in a dream and not here." he sighed, his voice full of disappointment as he rested his forehead against hers and a flash of a room with wood paneled walls and a huge bed, briefly flew through her mind.

"Mhmm, please?" Elena pouted, she had a desperate need for some type of relief.

"Don't worry." Damon told her as he stroked his hand down the side of her body. "I can help if you want me to."

"But you said..." Elena started, however Damon put his finger to her lips.

"It's not the only way." Damon said kissing her on the nose as his hand drew circles on her stomach.

"But Matt couldn't..." Elena started again.

"I'm not Matt." he smirked. "There are a few ways, I have my own favorite, but I don't think you're ready for that right now." he winked.

"Why not?" Elena asked. "What is it?" her voice was beginning to sound desperate as Damon bent down and took a nipple in his mouth and sucked it causing Elena to moan with pleasure, earning her another smirk from Damon.

Damon lifted his head and leaned over to Elena's ear. "Because I can be very wicked when I want to be, and you're not quite ready to go there yet. You are a little too...innocent right now." he whispered seductively, leaving Elena practically panting with need at his words.

"Wicked sounds good." Elena pleaded.

"And passionate, and very adventurous." Damon added with a glint in his eye. "And even a little dangerous at times." he said, his tone of voice reflecting his words.

"I can do that." Elena told him, nodding.

"One day very soon, it'll be right." Damon told her. "Just not right now, not tonight." he sighed sadly causing Elena to frown. "But for now, do you want me to make you come in a more...appropriate manner?" he asked, a note of uncertainty in his voice.

"Please." Elena begged, as Damon unbuttoned Elena's jeans and pulled them down, before sliding his hand down her panties, whilst his mouth molded with hers as he began to kiss her, drowning out her moans of pleasure.

Elena wasn't prepared for what came next. She'd had sex with Matt, he'd fumbled around, clearly having very little knowledge of a woman's anatomy and needs. Damon was a different type of beast, he knew exactly what a woman wanted and how to give it to her. With the exact amount of pressure required and the expertise of knowing the exact spot Elena needed him to touch, he began to gently circle his fingers around her nub, eliciting moans from her mouth into his as she began to arch her back. Damon must have realized she was close as he inserted one finger inside her whilst he continued to massage her clit.

"God you're so tight and wet." he groaned in a voice that sounded like he was getting almost as much pleasure from this as Elena was.

Heat was beginning to take over her core as Damon inserted another finger as he managed to alternate between massaging her nub and pumping his fingers inside her, working her up into a frenzy she'd never experienced before. Her body felt like it was on fire and electric currents were running through it, threatening to turn into full on electric shocks as Elena began to moan loudly.

"Come for me Elena." Damon instructed her in a voice that left her no room for argument as white hot spasms began to take over her core, causing her body to go rigid and her back arch.

"Oh my god...oh my god...Damon..." she cried out as the spasms seemed to be out of control and she was starting to feel overwhelmed with the sensations wreaking havoc throughout her body. "Fuck!" she screamed as Damon muffled her cries by kissing her whilst her body started to shudder before she began to recover from her high.

Soon Elena was panting, exhausted from Damon's ministrations as she watched him remove his fingers from inside her and suck them. "Mhmm, delicious." he smiled as of he was eating the tastiest piece of chocolate ever, causing Elena to frown with suspicion. "I was right." he smirked as he clearly noticed the expression on Elena's face. "You're not ready for my preferred method." he added with a grin as it suddenly occurred to Elena what his 'preferred method' might be, causing her to be shock, resulting in a chuckle from Damon.

Deciding to change the subject, Elena nervously ran her hand over the bulge in Damon's jeans. "Do you want me to..." she started to ask but Damon put his finger to her lips.

"It's just a dream Elena." he reminded her. "It's all about you're pleasure, not mine." he told her.

"But..." she started.

"No buts!" he insisted. "Although I do have a question." he said.

"Go on." Elena looked at him suspiciously.

"Was that the first time you came?" Damon asked with interest as Elena blushed and nodded.

"I thought I had before, but now I know that was my first time." she admitted.

"Glad I owned it." Damon grinned. "That means I will not only be the first, but I'll be the last to make you feel like the." he said, cupping her face.

"That's nice." Elena sighed leaning in to his touch, feeling a little tired from her very intense experience.

"Shh...close your eyes." Damon whispered as Elena did as she was told, whilst he placed a chaste kiss on her lips. After a moment however, everything was suddenly quiet. Elena opened her eyes only to find Damon was gone, the wind blowing through her open window and she was wearing her PJ's. However, her heart still racing from the orgasm she'd had in her dream. Getting up, Elena picked her glass up from her nightstand, opting to get some water to try and distract her from what had to be, up until that point, the most erotic moment of her life.

This chapter is different because Damon has entered Elena's mind and is prompting the dream, however Elena doesn't know that, which is why it is in her fantasy diary. Damon is allowing her to take the lead to some degree because it gives him more of a feel for how attracted to him Elena is. We have to take into consideration what Damon's mindset is at in the show at this point. His primary goals are to get Katherine out of the tomb and annoy Stefan. He hasn't had his humanity switch back on for long and he's a fairly horrible person. However, we know he was already falling for Elena and deep down knew she was the one, not Katherine.

This chapter was extremely difficult to write as I didn't want to portray this as sexual coercion, however at the same time, he's trying to get a feel for how much she wants him. This is why I've taken a few liberties with Damon's knowledge.

Another problem I had was trying to write Damon and Elena's characters at this point in the story. Elena is vulnerable and naive, and Damon, is a character that is nothing like the the person he becomes post 1x10. This meant I had to reign in the steaminess. Don't worry, it will be back, however this chapter is for plot purposes.

I wrote chapter this because I wanted to eventually try and add scenes from season two. It will still be tough and there won't be many due to the lack of Delena interaction in season two, but it allows me to use scenes that otherwise would have been out of bounds.

Thank you all for your kind reviews. They are always appreciated.

Please like, follow review. It helps motivate me to get the chapters out quicker.

Mandzipop.