Authors Note:

Oh my god, I am so sorry for how long I have taken to update this story and I apologize deeply. I didn't have the energy to write a chapter and I didn't want to give you an even worse chapter than I normally give you.

Haha.

Anyways I had a very close friend help with this chapter and will be helping me with further chapters. Hopefully when I'm too tired and lazy he kicks my ass and tells me to start writing for you guys.

I also updated my other story, Speechless. It's a TSLOTAT

Well, lets stop rambling and you'll stop reading this, though I doubt anybody reads Authors Notes... I know I don't... Oops.

I do not own any of these characters or The Vampire Diaries since they belong to Julie Plec and Kevin Williamson. I only own the story idea.


Elena's POV

My head throbbed and my limbs were unresponsive, reluctant to move. My throat felt like sand paper or maybe even a dry desert and I felt my eyes ache under my eyelids.

Multiple groans disturbed my thoughts of why the fuck did I drink last night. I open my eyes albeit reluctantly and I immediately will my hand to whip over my eyes to shield the harsh morning light, but I couldn't move my hand.

I pulled again on what was supposed to be my right arm and I realized my entire arm was tingly and I felt something weighing on my uncomfortable limb. I breathe in and I immediately smell a familiar scent of musk.

I let out a content sigh and opened my eyes gingerly still getting used to brightness that was surrounding the room. I'm met with high cheekbones, a masculine jawline, raven hair that falls and curtains a forehead, closed eyes, and delectable lips that were so close to mine.

After a few seconds and I process whats happening I jump back with a yelp and land with a thud effectively yanking my arm from the heavy restraint.

"God, Elena. Stop screaming. I have a pounding headache." Caroline wines from underneath the coffee table.

I let out a huff and roll my eyes. I look over to where I fell off from and it was the couch that Damon was currently waking up from. I realize that I must have had my arms wrapped around him; which was making me to flush, and causing my right arm to be pinned under his heavy weight.

I see Damon's eyes flutter open and smirk when he catches a glimpse of me on the floor. "Morning, sunshine." Damon greets without a care in the world and surprisingly which seems without a massive hangover.

I curse him for looking so damn good in the early morning after just waking up and I myself look like a ball was smashed into my face... repeatedly.

"Ugh. Don't even mention sunlight. Will somebody close the god damn curtains?" Tyler mumbles harshly and cradles his head back in place on Caroline's neck. I wonder if they got together last night.

"There aren't any curtains, but if you'd like you can go ahead and by some." I say sarcastically not knowing if I can make it out of this hangover alive with everybody complaining.

Oh God, I'm being influenced by Damon. Everybody who is awake looks at me weirdly and even Matt who had two couch pillows over his head stares at me like I've grown to heads.

I rolled my eyes again, though that was a bad idea because my eye sockets literally hurt. I go to get up and place a hand on the couch for support, but I regret once I feel like the Earth was weighing down on my head and I had lost fifty percent of my brain cells.

I sit on the couch with Damon and rub my temples trying to bring back any kind of cells that might not have died yet. I hear Damon chuckle beside me and I don't even have the energy to throw a nasty glare at him, but I did have a scowl on my face, which Damon noticed and chuckled louder.

"Would you stop laughing at my misfortune. Why aren't you experiencing a jackhammer in your head drilling away?" I ask and Damon shrugs before saying he was used to it.

Of course I should have guessed he would spend his nights alone going to a bar and drinking. I mean... We did see each other again at a club. "Well I've got an idea. Why don't you, the one who isn't suffering from a headaches and nausea, go do something productive. Like getting aspirin from the bathroom." I reply to him.

I count to five and wait for the moment he says something stupid and sarcastic and do nothing of what I just said. Instead I'm sort of pleasantly surprised. "Forgot I was your peasant." He says and walks out of my sight and into the bathroom.

I was sort of pleasantly surprised because he still had said something stupidly sarcastic. A few minutes later Damon had the bottle of aspirin and six glasses of water.

When I saw the beautiful H2O and lovely aspirin I swear the heavens opened up and the angels started to sing and dance around Damon.

The six of us eagerly took what was in Damon's hands and drank as if our lives depended on it and I'm not referring to yesterday. Damon disappears into the kitchen and I'm to exhausted to check what he was doing.

I lay down after being in a sitting position on the couch for far too long and before I even knew it, I was drifting off to sleep again.

Flashback (15 years ago)

The sun was beating on the crowd of 5 year olds to 9 year olds that were on the huge field. There was constantly a shrill of laughter and screaming piercing the energetic air.

It was field day and there were many competitive games to participate in, but the excited children were far more interested in the game of Tug of War, including a blue eyed boy and a chocolate haired little girl.

A round of Tug of War ended and the two oblivious children who didn't know each other came in to play on different teams. Six children were placed on both sides and unfortunately the chocolate haired girl was placed on the end.

A whistle urged them to start tugging hoping to win. The tension was thick and the grunts of the small children filled the air. In a matter of minutes one team lost causing them to all fall over one another.

A loud wail emanated from the little girl who was hurt in the process of falling so rapidly. Teachers and chaperones ran to the girl as fast as their legs could carry them, but the young boy with blue eyes was already there.

"Where are you hurt?" He said. She pointed to her small ankle and her lips wobbled. A few other kids had started to laugh and make fun and the tears were about to bring another onslaught.

The boy glared at the others and turned back to look at her. "It looks like its just bruised. You'll be fine after going to the nurse." He said and she nodded thankfully. Teachers finally surrounded and lifted the little girl in their arms to bring her to the nurse.

As they started to walk away the girl said, "Wait! I wanted to say thank you." She pointed to the boy and he faced her.

"Thanks..." She drags out not knowing his name. "Damon. I'm Damon." He said. "I'm Elena." She smiled shyly and gave a small wave.

"Your welcome, Elena. I'll see you sometime."

"Yeah. Bye."

"Bye."

After that day Damon and Elena were inseparable.

End of Flashback

A sweet aroma hit my nostrils and I'm relieved to say my hangover was diminishing. I stretch my limbs and look around to see nobody in the living room. I could hear chatter and laughter coming from the kitchen, so I decided to inspect.

Everyone was surrounding the Island as they talked and I glanced around to see Damon cooking. Finally, Caroline notices me and her bubbly voice booms.

"'Lena, you're awake." All the boys and girls turn to look at me and so does Damon. He smirks at me before turning around again and focusing on what was on the stove. "Hey, how long was I asleep?" I ask.

"Not long, but enough to drool dreaming about me." Damon sighs wistfully with a smirk plastered on his face. I scoff and the others chuckle along except for Matt.

I walk over to Damon and slap his arm playfully before asking why he was cooking.

"Because a good breakfast after a killer hangover is just what you need, so you won't go all bitchy on me." I do not go bitchy, I thought, "and because we can't have you being a bitch when we talk about the puckering of two lips." He whispers the last part and I'm the only one to have heard it.

I scowl at him and narrow me eyes. Truthfully I was dreading the conversation I promised Damon. I don't even know why I kissed him. The sounds of plates being put on a table brought me back to reality and saw that breakfast was ready.

"Come on, Spacey. Back to the real world." Damon whispers as he passes buy and puts even more plates on the table and I can't help but think how domestic Damon looked setting up breakfast.

I find myself laughing and I sit down with the others. Small chat is passed around the table and I'm glad to have had the way too many drinks last night.

Flashback (Last night)

"Oh my god, remember that time when your shirt slid off your shoulders in front of the teacher!" Caroline exclaims laughing drunkenly. My cheeks turn a bright red and I take a swig of my drink.

"How'd that happen, Elena." Tyler asks suggestively and then Caroline nods in enthusiasm. I get comfortable on the couch where Damon was also sitting and got ready to tell the story. All common sense flew out the window after the four tequila shots and three beers.

"Well, I wore this really pretty shirt. It had a zipper in the front from top to bottom. The most humiliating high school experience by the way, so I decided to unzip my shirt a little." I said as I scooted next to Damon and demonstrated by undoing the buttons on his shirt.

"Nothing to revealing. I mean it was hot in the classroom. Anyways I stood up after an hour of sitting down and turned in my paper. The only problem was that I hadn't realized my zipper was undone completely and as I was walking towards Mr. Williams' desk, our history teacher, with my shirt pooled around my waist." I proceed to undo the rest of the buttons on Damon's shirt and I look up at him with a small smile.

He smirks back at me and I push the shirt of his shoulders and leave it around his waist. I can't help the smirk that adorns my face, so I just continue smirking. "Leaving me in a bra in front of my teacher. Next think I knew he was handing me back my paper with an 'A' and a smiley face."

"To be honest it wasn't that bad since Mr. Williams was smoking hot." I say becoming hot over the thought of and a shirtless Damon next to me.

I hear Caroline snorting and trying to stop laughing and Bonnie is giggling beside her. I close my eyes and drink some more, making my thoughts become hazy. "I doubt you deserved that 'A'. You were never good at History." Damon whispers in my ear causing my eyes to open.

I lean forward next to his ear and say, "Oh I deserved it. These puppies never fail to surprise." Damon looks to me and lowers his eyes. They stop to stare at my breast and his eyes darken.

"Eyes up, Salvatore." I say naughtily. He grins and drinks his bourbon chuckling to himself. "Let's cheer to something." I say to him. He nods.

"Cheers to zippers."

"Cheers to breast."

End of Flashback

After breakfast everybody went back home and Jeremy locked himself in his room and that left Damon and I to...talk.

Damon's POV

I was anticipating this conversation. After Elena and her little hand compared to mine stripped me of my shirt and challenged me seductively, I couldn't wait to hear what she had to say.

Surely it would be to my amusement to see her flush and fidget with her hands and tuck her hair behind her ear when she's nervous. Or when she would bite her lip when she was unsure of something or look down at the floor when she was embarrassed and even when she would look anywhere but at you when she was guilty or trying to hide tears.

It was funny how things you would do years ago would still be with you. Elena hasn't changed at all except for her being stronger and I don't mean physically, but mentally and emotionally.

Elena interrupted my reverie when she sat down next to me after shutting the front door. I hear her sigh and see her tuck a silky strand of hair behind her ear and I smirked to myself. She turns to me and I turn to face her.

"Look, about yesterday-" she begins but I talk over her effectively cutting her off mid sentence. "You know what? You don't even have to tell me. I understand I'm very attractive." I say cockily and she says no.

"What? You don't see me as attractive?" I say mocking hurt. "Yes. No. I mean. You're changing the subject and I want to tell you why I kissed you." She says, so I look at her expectantly.

"I had no choice. I couldn't kiss Matt and you know exactly why." She said and I nod because Ido know. That kid was super clingy.

"And Tyler was out of the question. Tyler and Caroline totally have a thing for each other and I no way shape or form was I going to kiss my brother." She says with a cringe and I laugh at the thought of Jeremy and Elena kissing.

"And kissing you wouldn't have been the end of the world. I mean I've kissed you before. No big deal." She explains and I find myself reminiscing.

Flashback (9 years ago)

A low beat of music filled the silence in the cozy room. That was until a sigh was emanated and a text book was closed. "Tell me what's wrong?" I said and Elena looked up at me puzzled.

"Why do you assume somethings wrong?" She says and focuses her attention back on the textbook she had opened.

"Because I know you like the back of my hand and because you're biting your lip and playing with your hair. I very well know you do these things when you're nervous and/or unsure. C'mon, tell me what's got you upset." I tell her and she sighs loudly before sitting up from her lounging position.

"I'm pretty, right?" She asks looking down. I look at her gauging her expression. I try to suppress a laugh at the hilarity of her question. I put on a straight face and reply with, "No."

Her head lifts up quickly showing her surprised face. A let the information sink in before I see the tears welling in her eyes.

"I was kidding Lennie. Take a joke. You're not pretty because your beautiful." I tell her seriously and she furiously pushes me off the bed landing with a thud. "God! That hurt. If complementing a girl lands me on the floor than maybe I shouldn't at all." I groan and I see Elena peep at me from the bed.

"Oh, sorry. Did I bruise your ego?" She snarls and I push myself up and back onto the bed. "No, but I'm pretty sure I have a bruised ass though." I say bitterly.

"You deserved it buttface." She exclaims throwing her hands in the air in frustration. "Whatever. You're changing the subject. Yes, you're pretty." I say.

"I thought I was beautiful."

"Seriously, 'Lena?"

"Take a joke, Damon." She smiles at me and I smile back before giving her a pointed look. "Fine, I'll tell you. Are you ready?" She asks.

"I'm ready." I say nodding my head. "Are you ready?" I groan at her. "I'm ready." I repeat.

"Are you-"

"Yes! I'm ready."

"I'm sorry. I'm nervous." She says and I regret loosing my temper. "You can tell me anything." I reassure her and she nods.

"Boys are going to date me, but what if we kiss for the first time and I'm really bad at it? I mean I've never kissed a boy before, so yeah." She rambles nervously.

"Are you trying to tell me you have a boyfriend?" I ask her and she shakes her head quickly. "No. No. I'm just worried about my first time kissing." She says and I see her shoulders sag as if finally speaking those words lifted the Earths weight off her slim shoulders.

"There's an easy solution." I say confidently. "What?" She asks. "You practice kissing." I said. "Who's going to ki-" I cut her off the second time today.

"Me." I interject shrugging. It was no big deal. We're friends and we trust each other. "I don't know, Damon. I don't want it to be awkward between us." I hear her say. "It's not going to be and I won't let it be. There's no harm done in kissing." I say.

The look on her face screamed hesitant, but she finally agreed. "Okay, but this isn't to be spoken about to anyone." She says and juts her hand out in a way I knew what it meant.

Our hands meet slapping against each other two times before we fist bump up and down and fist bump again. Then we finish it off by doing a high five up high and down low.

It was our secret handshake and we would always do it when we were going to keep a secret or doing something that would surely land us in trouble.

"My lips are sealed. Your lips are sealed. Not until we actually kiss though." I smirk at her and she rolls her eyes. "Don't make me push you off the bed again." She warns me with a smile. "No need to get defensive." I tease.

"You're unbelievable and too sarcastic." She says mocking a slightly annoyed look when I knew she wanted to burst out laughing. "You love it." I say scooting closer to her and lean in.

"I guess I do." She whispers and tilts her head. I look down at her lips. Her pink, plum lips. Stop it. This is Elena Gilbert: your best friend. A simple peck on the lips and done. Nothing else because she's Elena.

Finally, when our lips graze, I knew. I knew that it wasn't going to be a peck. I mean, I've had my fair share of kisses before. I was fourteen, but she was eleven. I erased my thoughts and let my lips apply more pressure.

I lifted my hand and cupped her face trying not to let myself slip away from reality. I could feel the warmth of her lips enveloping me and her scent coming in waves. All I felt was confusion. Something bubbling up in the pit of my stomach and I've never felt it before until now.

Just as fast as the kiss started it ended. Our lips slowly detached and I looked at her before softly saying, "That was good." I dropped my hand and cleared my throat. "It was good?" She asks pleasantly surprised.

"Great even." I say and she jumps up on the bed making me laugh at her joy. "I lost my lipginity." She shouts with enthusiasm. "You're what?" I ask confused as she happy dances on the bed. "My lipginity. Lip virginity." She explains grinning down at me.

"Where did you hear that from?" I ask. "From some girls." She said still bouncing. "Well never say it again." I say to her looking up. "Lipginity, lipginity, lipginity! She shouts happily.

"Now you've done it, Gilbert." I say and yank her foot right from underneath her causing her to fall in a fit of giggles.

End of Flashback

That was a couple months before our tragic fight that separated us. Back then I wanted to kiss her again. Tell her it was the best kiss ever, but my huge ego; which I still have to this day, was telling me not to.

I look back to Elena and force a smile. "No big deal." I lie. It was a huge deal, but again ego. "Um... good. We have that sorted and dealt with." She says and the door opens abruptly revealing a giddy Jenna who hadn't seen them yet.

When she turned around she yelped and placed her hand over her heart. "Gosh I thought you would be out doing teenage things." Jenna says trying to control her breathing. I smirk and I stand up walking over to her. I take her hand and settle my lips on it.

"Jenna, always a pleasure." I say and she looks at me curiously. "I know you. You're Damon. Childhood best friend and all." She says giving Elena a look and I see her shrug. "The one and only." I grin.

"Mmmmh. Well I'll talk to you later Elena. Nice seeing you again, Damon." Jenna says and leaves the room and treading up the stairs. "I should go." I say and she nods and opens the door. I walk out and only giving her a nod.

"Heads up. Don't drink more than three beers. You get easily drunk." I holler at her as I walk. "Asshat." I hear her mutter under her breath. "I heard that." I shout to her.

"Goodbye, Damon." She says as I get in my car. "Goodbye, Elena." I say and I see her grow smaller and smaller as I drive away.

Elena's POV

I close the door leaning against the cold hardwood. I let my eyes shut just taking it all in. Damon and I were good. We had the awkward kiss conversation out of the way and I knew that Wednesday I would get to see Damon again.

A loud cough startled me and I opened my eyes to see Jenna giving me that 'you-need-to-explain-yourself-right-now' look and Jeremy coming down the stairs. "Look, if it's 'bout Damon, all I have to say is that he's my friend. Just a friend." I sigh.

"Last time I checked you guys were best friends ten years ago." She says and I roll my eyes. "Nine years ago." I correct her and walk to sit on the couch. "Not the point. As your guardian I-" She starts explaining putting her parenting pants on.

"Jenna, there's nothing going on. We're friends again and I'm happy. Isn't that all that matters?" I ask desperately. "Don't believe her. I heard that teenagers always pull this stunt off. Saying they're happy only to guilt trip you." Jeremy says smiling evilly and I shoot him an annoyed look.

"Wow. Never thought I'd see the day you talk so intelligently. Too bad it's all a load of crap." I say throwing a couch pillow at him. "Language, Elena." Jenna chastised and I see Jeremy sticking his tongue out behind Jenna's back at me. "Child." I mutter.

"Elena, I get it. I do. I'm glad that you're happy, but I just want you to know what you're doing. I don't want you to get a hurt a second time." Jenna says sadly. I take her hand and mine and giver her a small smile.

"I can't promise I won't get hurt, but I know that I've given myself a second chance to be happy with the only person who ever made me happy. Damon is my friend and I'd be a fool to give up on something that I enjoy especially after mom and dad died." I say and Jenna doesn't say anything, but hug me tightly and I see Jeremy leave, but now without saying a silent sorry.

I mouthed 'it's okay' and smiled at him as he left. Jenna and I let go of each other and wipe our tears. "No more crying. I have to tell you about my date." Jenna gushes excited.

"Yeah. How did that go? I'm guessing you slept over." I say as we walk to the kitchen and Jenna grabs two spoons and an ice cream carton from the freezer.

"Yup. It was awfully late by the time our date officially ended. To sum it up, I slept over leaving me to my dreams about how I really like this guy." Jenna says. "I'm happy for you." I say and we fall into a comfortable silence that is until Jenna laughs.

"I would've never thought I would be eating Rocky Road Ice Cream when I'm so happy. I usually eat these when in crying over my last boyfriend." I hear Jenna say and I laugh along with her and spending the afternoon eating ice cream and talking about our feelings.

Damon's POV

Getting home and taking off my jacket, I sit down down with a glass of bourbon. Taking my first sip, I hear a knock and stand up to get the door, instead Alaric came barging in.

"You should really lock your door." He says walking over to the cart of various alcohol and pouring a drink in a tumbler. "I'm a vampire, Ric." I roll my eyes and sit back down. "And I'm a vampire hunter." He retorts sitting across from me.

"A vampire hunter who's my friend and wouldn't try to kill me." I say to him. "Maybe I would, dick." Ric grumbles, but I could tell he was happy about something.

"So, what's got you barging into my apartment and stealing my alcohol?" I ask taking another drink. "I got you this for your birthday. Technically it's mine." He says pointing to his drink.

"Still haven't told me why you're here."

"Remember my date with Jenna?"

"How could I forget? You kept blabbing about it in my ear."

"It's not like you didn't do the same. You kept gushing about that date with Elena."

"Who are we talking about here? You. Not me. How'd your date go?"

"Perfect. We talked. Ate dinner and we got so sidetracked that we didn't see how late it was. She slept over... and there's going to be a second date."

"Did you have sex with her?"

"No! It's our first date. I'm not a man slut like you."

"I was just asking. Her hair was a little ruffled when she got home."

"It's not like I own a brush, Damon. Why were you at her house?" Ric questions. A look of realization etched his face. "Oh. I get it. You slept over with Elena." Ric says.

"Correction. I slept over with Elena and her friends." I said standing up and refilling my glass. "Right, because that makes all the difference." He says. "It does. We hung out, played silly teenage games, and got drunk." I say nonchalantly.

"You like her." I hear Ric say and I scoff. "Of course. She's my friend. Only a really close friend." I say. "Whatever you say." Ric teases. "And you all me a dick." I mumble annoyed.

Elena's POV

"Elena, do you want something to eat? Jeremy and I are getting takeout." Jenna asks with a purse on her shoulder. "No thanks. I'm not that hungry." I tell her.

"Okay well you have my cellphone number if anything goes wrong." Jenna says and I chuckle. "Yes ma'am." I say and she rolls her eyes before leaving with Jeremy through the front door.

I was alone sitting on the couch across from the Tv that was showing a ridiculous reality show. Then it hits me. I'm alone. Elena Gilbert is home alone. I could do anything. I dashed to the stereo and turned on an upbeat of music.

I danced in the living room while pouring myself some wine with my abilities. I zoom across the room just because I can. I move the couch and the coffee table out of the way with my strength and cartwheel in the empty space I had created.

Jumping on the couch I was disappointed that it wasn't as bouncy as I excepted. Quickly and idea came to my head and I transported to a room. I ended up in Jeremy's bedroom bouncing up and down on his bed.

His sheets gathered around my feet and I was careful not to spill any of the wine that belonged to Jenna. I couldn't stop my laughter and it kept coming full force. That is until I heard a car parking in the driveway.

I hurriedly tried to make Jeremy's bed look as decent as it can and super sped down stairs dumping my wine in the sink. Where would I put the glass? Thinking quickly I throw it in the trash, panicking.

Turning off the music in a millisecond and pushing the couch and table back in place, I sit on the couch casually as Jenna and Jeremy come in with bags of Chinese food. I had done all of that in ten seconds flat.

"Hey guys, I'm just going go upstairs. I'm pretty tired." I tell them. "Are you okay?" Jenna asks suspiciously. "I'm fine." I reassure her. "Okay then. Goodnight." Jenna says. I say goodnight back to both of them and tread upstairs.

Taking a shower and brushing my teeth, I get ready for bed. Cuddling myself in the duvets I fall fast asleep. The last thing I hear is from Jenna saying, "Why are one of my wine glasses in the trash?"


A/N:

Heads up guys. The real conflict to this story is coming in a couple of chapters, so just wait for it. I had fun writing the flashbacks in the story and I hope you enjoy them. Again, I'm sorry for the long wait.