A/N: what's that? And update?! I am so so sorry that this took so long! In the past couple months I've visited 3 cities, 3 states, and 2 countries, it was a crazy and amazing experience, and then my boyfriend proposed, so I was still getting over the shock and excitement of that. Now that my life is returning to normalcy I promise I will be doing regular updates! and it's extra long to help make up for lost time

Also… This chapter is definitely rated M


Elena's POV

Damon and I come tumbling though my apartment door, all lips and flailing limbs.

After he kicks the front door shut with his foot, he quickly pulls my shirt over my head, not wasting any time. He lifts me up and presses my back against the wall and presses wet opened mouthed kisses on the parts of my breasts that are not covered by my bra

"Bedroom" I gasp out

Without a word, he carries me over to my room and gently lays me down on my bed before crawling on top of me

"You're so beautiful Elena" he runs his finger across my cheek before leaning down to kiss me tenderly

Our kiss quickly starts to heat up again, not wanting to waste any time I reach down for the hem of his shirt and pull it up over his head

God this man…

I run my hands down his shoulders to his chiseled chest

He reaches behind me and undoes the clasp to my bra, freeing my breasts from their confinements

"So perfect" he groans before leaning down to pull one of my nipples into his mouth

I let out a whimper, an honest to god pathetic whimper, because it's all I can muster right now

"Damon" I moan, begging him to give me more, I grind my lower body searching for some sort of much needed friction, I moan when I come in contact with his thigh that's resting between my legs

When his attention shifts to my other nipple, I start shamelessly grinding on his thigh, needing some relief

Sensing my distress he reaches down with his free hand, undoes the button of my pants and dips a delicious finger inside

"Oh god" I let out as his finger makes contact with my clit

"That's it baby, scream for me" his voice is so sultry that I swear I almost cum right then and there

He pulls my pants down further for better access and dips his finger into my core

"Yes" I moan

"Right there?" he curls his finger and hits the magic spot

"mhmm" is all I manage

"You're so beautiful like this, cum for me 'Lena"

So I did.

Slowly I start falling back down for my high

"You ok?" he smirks

"Never been better" I giggle

"You're entirely over dressed" I comment when I notice he still has his jeans on

"Am I now?" he leans down and presses another kiss to my lips "why don't you do something about it" he challenges

"It would be my pleasure" I lean over to pull his pants down his body

I take a deep breath and pull his boxers down; I never thought this moment would actually happen.

After he's completely naked he lean over to me and kisses me

"Are you sure about this?" he asks, looking me directly in the eyes

"Absolutely" I say with complete confidence

"Ok" he smiles and positions himself at my entrance

He reaches up to push some stray hairs away from my forehead, leans down to kiss me and slowly pushes inside me

Inch by delicious inch,

When he's finally all the way in I'm amazed by how well we fit together, he's not too small, and not too big, he's perfect.

I move my hips a little, letting him know it's ok to start moving

"Oh god, Damon" I moan as he slowly starts moving in and out of me

"So, beautiful" he pants between labored breaths

His hand trails down my leg to me knee, lifting it to hook over his hip

I groan at the delicious change of position

"Faster" I beg

He starts to pick up his speed, and it's unlike anything I've ever felt before

Damon's movements start to become jerky and uneven, I know he won't be able to last much longer

As if he can read my thoughts he reaches down between our bodies to rub his thumb across my little nub, and just like that I spiral into bliss all over again, only this time I take him along with me

Our bodies collapse together, neither of us moving, for fear of popping this amazing bubble we've created

"Oh man" he lets out a heavy sigh

"What?" I begin to panic that maybe he's starting to regret what we just did

"No, no nothing bad" he eases my worry "It's just that, that was… amazing" he smiles and rolls over to face me

"Yeah, it was" I smile back at him

"What do you say we get some rest, you wore me out Gilbert" he laughs, and pulls me into his embrace

"Sure" nuzzle in to him

I start to drift to sleep with a smile on my face, everything is going to be ok, maybe for once things are going to go the way I want them to, I mean sure it's not the ideal situation, he did just sleep with one of my best friends but we'll cross that bridge when it comes, I'm sure Katherine will be happy for me, she's known how long I've wanted this.


Damon's POV

I wake up to the sound of a lawn mower somewhere outside; slowly I realize I'm not in my own bed

I smile as last night's events start to reply in my mind, man if I had known what I was missing out on all along I wouldn't have fought my attraction towards her for so long

And on top of all that, she told me she loved me.

Now I'm well aware of that fact that I didn't say it back, not because I was too scared, but because I didn't want to rush things

I know I like her, a lot actually, but I'm not sure exactly what love is, and I'm not going to reciprocate those words until I'm absolutely positive that I know I mean it.

I reach over to her night stand for my phone

One text message from last night

From: Katherine

We need to talk, call me.

Oh geeze, what we had was a one night thing, and I was positive that a girl like Katherine understood that, I didn't think I was going to have to deal with left over emotions from that mistake of a night…

Ignoring her text I place my phone back on the night stand, grab my pants from the floor and head to the kitchen

I pull out all the ingredients to make my famous pancakes, and search the fridge for blueberries, since those are Elena's favorite

I put the bacon in the pan and get to work

"Mmm something smells good" she says as she wraps her arms around my middle from behind

"You better be talking about me and not the bacon" I tease

"Maybe it's little bit of both" she smirks

"Let's eat shall we" I lean in to kiss her before grabbing our plates and heading to the table

"So, what should we tell people" she asks after taking a bite of food "Or should we not say anything?"

"Uh, well… I mean" I pause to collect my thoughts "I mean I guess we can tell them whatever you want to tell them"

That didn't exactly come out right, I notice her try to hide her disappointment

"Shit, Elena… That's not what I meant, look; I like you a lot and I'm not very good at this, all I meant is that I want to explore what this is between you and I without everyone else's input" I smile "that being said, I know Caroline is your best friend, and I'm not going to ask you to lie to her, if you feel like you need to tell her then that's up to you"

"I'll think about it" she smiles

"Ok" I reach across the table and grab her hand

"Shit" I say out loud

"What…"

"Random question that I probably should have asked you last night… Are you on birth control?"

"Um, yeah" she looks down trying to hide her blush

"Don't get embarrassed" I rub her hand

"I know, it's silly; it's just still weird hearing us talk about these things, I mean we went from friends to a relationship, in like ten hours" her eyes widen "I mean not a relationship… a you know.. I mean… that's not…" she continues to scrounge up the words she's searching for

"I think relationship is the word you're looking for" I say easing her panic

"Really?" the relief in her voice in palpable

"I mean yeah, why not… it might seem like we're moving fast, and yeah… in some ways we are; but then in others it seems like it's been four years in the making, we're both just finally in the right place at the right time" I smile, shocking myself by the truthfulness of what I've just confessed

"I agree, it feels right" she smiles

"Let's celebrate" I suggest

"I think we already did… last night" she smirks at me

"Elena Gilbert… you little minx" I laugh "as much as I enjoyed last night and as much as I look forward to repeating it again sometime soon, I was thinking more along the lines of dinner, let me take you out on a date"

"A date, like a real one?" she asks skeptically

"Flowers, dinner, a movie, hey even dancing if you want, but yes a real date"

"Ok" she answers simply

A shrill phone rings from inside her bedroom, interrupting our conversation

"I have to grab that, it might be work. I'll be right back though ok"

She just nods

"Hello" I answer

"Damon…"

"Ugh, seriously Katherine… what do you want"

"I need to talk to you"

"Look I've known you for what like 4 years… and I could probably count all the times you've called or text me on one hand, so what the hell is so important"

"Not over the phone, can you just meet me later, like around 5 o'clock?"

The only thing that is telling me to agree is the shakiness in her voice; normally Katherine's voice is purely laced with cockiness

"Fine, where?"

"The Coffee Shop on 9th Street"

"Ok" I agree

"Ok see you then"

I shut my phone and place in pack on the nightstand

I take a few deep breathes and try to push this nagging feeling in the pit of my stomach away before returning to Elena

"Hey" she smiles warmly at me "Everything ok?"

"Yup, just the office like I thought" I kiss the top of her head, not knowing why I lied to her

"I have to run actually, they need me to come in for a couple hours to approve some proofs" why did I lie again "but I'll be back here at 6 o'clock sharp, to pick you up for our date, so be ready for the night of your life Ms. Gilbert" I smirk

"I will, Mr. Salvatore" she walks me to the door a gives me on last goodbye kiss


After leaving Elena's house I went straight back to my place, knowing that I didn't really need to go to work

I need to approve some proofs… what the hell was I thinking, I never lie to her, and what is with this gnawing feeling in my stomach…

I just had one on the best night of my life; I should be over the moon right now, but instead all I feel is this cloud of impending doom hanging over me.

After taking a quick nap, I hop in the shower and get dressed for our date, knowing I won't have time to come back here after I meet with Katherine

I walk into the coffee shop I spot her in a booth near the back

I don't order anything because I don't plan on staying any longer then I have to

"Hey" I greet her as slide into the booth

"Hey" she sounds broken… there's not a trace of her usual self-confidence

"What's up" I ask

She just sighs, as if she's trying to figure out where to begin…

"Are you ok? Did something happen?"

Not a word

"Helloooo" I wave my hand, trying to bring her back from la la land

Nothing.

"Did someone hurt you?"

She just shakes her head

I start to lose my patience

"Well what's going on Katherine, you call me and demand a meeting and then now you're not saying a word and …"

"I'm Pregnant" she keeps her eyes downcast on the table

"I'm sorry you're what…"

"Pregnant" she repeats coldly, finally lifting her head up to face me

I don't say anything

"Damon…"

"You're not suggesting it's mine are you" I laugh bitterly

"Yes Damon, I am"

"Well then you're even more insane then I thought" I shake my head

"I'm not insane, you're the only person I've been with in the last month, and I'm 5 days late"

"These things happen all the time, maybe you're just stressed out or something" I shrug

"Yeah that's what I was hoping for too, so I went to the doctor just to make sure, and they did a blood test…I'm pregnant Damon"

"Stop..."

"The timing is right, from the night we slept together"

"I Said stop it" I cringe at her choice of words; the timing is not right at all, it's all wrong.

"Look this is the last thing I want to be happening; with the last person I want it to happen with, but it is happening, there's nothing we can do about it now"

"How the fuck did this happen?" I ask

"Well I mean we weren't exactly careful, we didn't use a condom"

Damn it, what is wrong with me lately, first forgetting with Katherine, then Elena…

"Aren't you on some kind of pill or something?"I bark out, annoyed with my own lack of responsibility

"No" she shakes her head "I had some kind birth control of shot, turns out it expired right before we got together"

"This can't be happening" I shake my head, hoping that it will wake me up from this nightmare

"Well it is, and I can't do this alone Damon" she look so defeated, it breaks my heart

"I know, I know; god… I just… I need to wrap my head around all this"

"I have a doctor's appointment tomorrow, they're going to tell me the due date, you're welcome to come if you'd like, it might help if you see everything firsthand" she suggests

"Uh, yeah I'll be there, what time should I pick you up?" I ash

"11 o'clock?"

"Ok" I nod

"See you tomorrow Damon" she grabs her bag and heads for the door, not bothering to wait for a response

I glance at my watch and notice its 5:45

"Shit… Elena" I mumble to myself

Knowing there's no way I'll be able to focus enough to take her on a date tonight I quickly write her a text

To: Elena

I'm so sorry but something's come up,

I'm gonna have to reschedule our date

I'll fill you in soon.

I know that sending her a text is the cheap easy way out and by no needs up to the standards that she deserves but if I were to call her now she would immediately sense that something was wrong as soon as she heard my voice

How did this happen… why is the universe determined to take away my happiness…

Ok, I'll admit… I'm not exactly the nicest guy on the planet, I'm even a little mean sometimes, and hey, maybe I had this coming… but Elena; Elena doesn't deserve this. She doesn't deserve to be hurt by my failures and mistakes, and that exactly what's going to happen.

Not wanting to see her disappointed response I power off my cell phone, start the engine to my car and head in the direction of the nearest dive bar.


Elena's POV

"Wait! You and Damon?!" I pull the phone away from my ear as Caroline continues to scream "I mean it's about damn time Elena, we all knew this was bound to happen, we've just been waiting for you guys to come to your senses"

"I know, I'm really glad we were both finally honest with each other, I'm really happy Care" I smile

"Good, no one deserves it more than you 'Lena" she says sincerely "Oh my god, you know what this means!"

"What?" I laugh

"If you guys get married, we'll finally really be sisters!"

"I think it's a little soon for that, we're just going on our first date tonight" I laugh "that's actually why I called you, I wanted your opinion on whether I should wear the brown or black heels with my green dress"

"Brown definitely. So where is he taking you"

"I don't know, I guess he's going to surprise me, god I still can't believe this is happening Care, it all still feels like a surreal dream"

"You better call me later, I want all the details! Or you know in the morning, if you're too busy to call tonight " she squeals

My phone chimes in my ear

"Oh text message, maybe it's from him" I giggle, it's ridiculous how happy I am

My smile fades after I read his text

"'Lena, are you still there"

"Oh uh, yeah"

"Was it from him?"

"Yeah it was" all my enthusiasm suddenly gone

"Well, what did he say, was it something dirty? Ohhh a dirty picture maybe? Wait, ew; gross that's my future brother… forget I ever said that. Did say where he's taking you? Oh come on, don't make me pry it out of you" she sighs

"Uh no; change of plans… he's not coming"


End A/N: Haaaaard chapter to write, I've gone over it and over it, hopefully you guys like the end result, please leave a comment letting me know what you think,. I know a lot of you are going to be disappointed, cause a few begged me to not let this happen, unfortunately that's what the whole story is based around, but I promise it won't always be a sad story, just stick with me .