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Once they were all sat on the couches comfortably, Elena started rubbing the palms of her hands over her knees anxiously.

Caroline and Bonnie were her best friends. They knew everything about each other since kindergarten. Every disappointment, every unrequited love, every crush, every secret, every little detail…they shared everything.

So why now that one of the most imporant girl-y talks was about to happen, Elena felt so nervous? The truth was that she rarely talked about this level of intimacy. It made her feel uncomfortable and out of place.

Oddly enough Damon was the only one she felt so at ease with regarding the subject. With him it all seemed to come down naturally.

In five days they would be alone and together in another city for two weeks. It was impossible to think that either of them could keep their hands for themselves, considering how they were always all over each other. It had to happen sooner or later, Elena was aware of it, and she was also aware of the fact that she couldn't picture anyone else but her Damon to finally make her take that step. She was 22 years old for god's sakes, it was about time, no?

"Elena?" Caroline called, making her snap out of her thoughts.

The blonde was giving her a knowing look full of curiosity. Hell, Caroline seemed more excited about the argument than she was.

Bonnie was sitting on the armchair in front of her, looking pretty curious as well as wary. Although Elena knew that they were both dying to know about the dirty little secrets that she was about to spill.

"Come on now, don't make us beg you. You know that you can talk to us about everything." Bonnie reassured.

Elena sighed deeply, kicking her shoes off and interwining her legs on the couch.

"I want to sleep with Damon." She finally admitted.

"Like…sleeping as in rolling between the sheets and having some hot monkey sex?" Caroline asked, her eyes sparkling and wide open.

Elena nodded shyly and Caroline started squealing and clapping her hands loudly while Bonnie rolled her eyes in amusement.

"Of course you want to! I'm actually surprised that you haven't jumped his bones already. Just go for it, it's as natual as drinking a glass of water. I promise." Caroline exclaimed.

She took a look at Bonnie's doubtful face and that immediatly reminded her of how judgy she tended to be.

"Have you really thought about this Elena? It's a big step, and you have to admit that Damon is kind of a player." She grimaced slightly.

"Oh don't be ridiculous, Bonnie! It's clear that she's in love with him and wants to be with him in that way too. Don't be such a buzzkiller. Let her have her own experiences." Caroline stated, crossing her arms.

Suddenly the blonde's head snapped around to look at Elena, giving her the look.

"Because you do are in love with him, right?" She asked for confirm.

Elena nodded, grinning happily.

"Yes. I love him."

Bonnie's features softened at her words, allowing a smile to creep across her face.

"I've always trusted your opinions. So if you really do love him and believe that he's the one, then what's stopping you? I mean he is hot." Bonnie chuckled.

They all chuckled a little and Elena felt the tension that she had been feeling for the whole time starting to fade.

She actually couldn't wait to hear all the things that they would advice her and tell her. For her – their – first time Elena wanted to appear and be extraordinary. She wanted to be the best he'd ever had, even though it did sound like a challenge considering Damon's experiences.

"So, did you two have oral sex?" She heard Caroline asking bluntly.

She blushed hard and shook her head. "Nope."

"Well I think that you should. It would help you to get intimate…but not actually going there, you know. It's a start."

"You're making it sound like it's obligatory or something, Care. A lot of people practice oral after having actual sex. Some don't at all." Bonnie shrugged.

Elena looked between the two as they went back and forth and she couldn't help but laugh.

"Calm down. I'll see about that, okay? Maybe I should just talk to Damon…"

"No!" Caroline exclaimed baffled. "You do not talk to your boyfriend directly about such things. 'Oh honey, do you want a blowjob by any chance? Now should I swallow or should I spit?' Hell no. If you want to do it, you just do. Talking to him about it is almost a turn off. He's your lover, Elena. Not your friend."

Maybe Caroline was right, but if she wasn't allowed to talk to Damon about their intimate relationship, then to who the hell should she? She couldn't always go to her friends asking for advices or opinions.

"I kinda agree with Caroline on that. These are things that you learn from experience, not from having a confidential talk with your boyfriend about it. You could make him feel uncomfortable if in the end you decide to not go there but he obviously wants it. I mean sure you can talk about sexual positions and stuff, but that's different." Bonnie said.

There was an awkward silence for a few moments until Elena spoke up.

"We're taking off to Chicago in five days, we're going to stay there two weeks and to be honest I kind of want it to happen there. So do you guys think I have time to do some shopping with my girlfriends?" She smirked.

Their faces immediatly lit up and Elena giggled a little.

"We're so not done with the sex talk, Elena Gilbert." Caroline said with a pointed look. "But oh my gosh absolutely. Why did you even have to ask? I'll just need to kill this stupid flue in a couple of days and I'm all yours. We're going to Victoria's Secrets, then a sexy shop that I know…"

"Sexy shop?" Elena snorted.

"Caroline is obsessed with it apparently." Bonnie rolled her eyes. "Anyway, I'm in too, of course."

"Yes, there are some great outfits to buy in there, trust me. Not to mention all sort of pleasurable toys." She wiggled her eyebrows.

"You're impossible." Elena said chuckling.

"You'll thank me for that, honey. I actually think that we should buy you a vibrator. The medium size perhaps? I bet that Damon is big, so you'll probably need to adjust first."

"Caroline! I'm not buying a vibrator. Especially not when I'm about to have sex…what's the point?"

"Let me ask you something Elena." She said crossing her arms. "Do you masturbate?"

She hesitated for a long moment but replied eventually as Caroline's glare was almost burning her.

"From time to time. So? I don't get the point of this." She shrugged uncomfortably.

"So what's the problem with using a vibrator? It's even better." Caroline pressed. "Look, it will only help you relax about the whole thing. It will make you feel more confident."

"I'll get some ice-cream. This is getting interesting." Bonnie said as she stood up.

"You think?" Elena asked coyly.

"Absolutely." Caroline nodded. "In my opinion, the best moment to do it is after a shower or a bath. Laying on your bed naked...starting playing with yourself…then you'll get so wet that you'll just crave the need of something inside of you. Besides you get to think about Damon while doing it, missy."

"Holy shit." Elena breathed, feeling turned on just by what Caroline said.

Maybe she was right and she should start exploring more of herself and feel more confident about her body before actually going there with Damon.

She pleasured herself sometimes, but she never quite pictured the act as erotic as Caroline made it sound.

"Oh, and I want you to do a waxing down there before you leave."

"Down…there?" Elena raised her eyebrows.

"Yup. And I don't mean only your groin, if you know what I mean." The blonde said smirking devilishly.

"I kinda got that when you said down there." Elena chuckled humorless.

"You look worried." Caroline said smiling. "I'm not gonna lie, it's pretty painful, but trust me it's oh-so worth it. It's a turn on for basically every man."
Elena tried to force a smile but shuddered lightly at the thought of having a waxing that would make her look like as bald as a newborn.

Just then Bonnie came back with their bowls of ice-cream and the girls started chatting about Chicago and how great it was that Damon was getting so comfortable to allow her to be part of his old life too.

Indeed she felt honored and happy that he was opening up to her so completely. She knew it was hard for him.

"I can't believe that's really Damon Salvatore. I mean he just…looked so different in high school. I would have never recognized him if Elena hadn't told me it was him." Bonnie admitted.

"I know right. Just the other day I was looking through the high school photo albums and it's like this is his good looking twin now." Caroline laughed.

"We were different too." Elena suddenly said harshly. "We were freaking bitches and I'm not proud of it. So let's just cut the crap please."

Both Caroline and Bonnie immediatly stopped laughing after hearing the sound of her voice and how serious she looked.

She didn't know why, but she had felt the sudden need to defend Damon proudly. She didn't like their tones and how lightly they were taking the fact that they were awful persons back then. Because they were.

"Okay. Sorry." Bonnie said quietly.

Elena's features remained hard as she stood up to take her stuff.

"Wait, where are you going? If we said something wrong then I'm sorry El." Caroline said apologetically.

They really looked honest about it and she softened up a little before speaking up. Perhaps she had just overreacted, but she couldn't help it, something inside of her had just called it.

"Don't worry about it." She said smiling a little. "Just give me a call if you feel better so we can go shopping and do…the other things." She chuckled lightly.

"I can't wait." Caroline grinned and they all said their goodbyes.

As she headed outside Elena called Damon. It was getting dark and maybe they could meet up at The Grill to eat something.

"Hello, Elena." He picked up at the first ring with his seductive tone.

She rolled her eyes a little and chuckled.

"Hello yourself."

"How did the girly afternoon go?" He asked.

"Fine." She quickly replied, blushing a little as she thought about what they had talked about. "You and Stefan? Is everything okay?"

"Yep. And apparently he lied to you, he didn't have to give me anything back…that chicken just wanted to talk to me about that Rebekah girl." He chuckled.

"Seriously?" She gasped. "I have no idea why he would lie to me about it, but Damon come on it's not cool that you aren't keeping this for yourself. He clearly feels uncomfortable with me knowing. It was supposed to be your brotherly secret or something." She scolded.

"I don't have secrets with you." He said, the seriousness in his voice making her gulp a little. "Now turn around."

She arched her eyebrows in confusion but did as he said. A few meters away from her there he was with his blue Camaro, waving at her with his devilish smirk.

She grinned at him and shook her head, ending the call as she approached him.

"Need a ride, beautiful?" He said cockily.

"Sorry, but I don't think that my boyfriend would approve. And he's extremely badass so I wouldn't try it again." She teased as she kept walking with a smirk on her face.

A few moments later the suddenly felt a pair of strong arms wrapping themselves around her from behind, lifting her from the ground.

She squealed loudly but as she felt the familiar masculine scent she immediatly relaxed in his arms.

"I guess that your badass boyfriend will just have to suck it up." He whispered huskily against her neck.

She turned around in his arms, giggling lightly as she wrapped her arms around his neck and looked into that ocean of blue.

"Oh yeah?" She cocked her head to the side a little.

"Yeah." He said kissing her desperately.

She gripped the back of his black hair and let him dominate the kiss. He seemed hungry for her just as much as she was for him.

He finally pulled back and looked into her chocolate eyes, a sweet smile across his face.

"Let's go." He said, leading her to the passenger's seat.

"Where to?" She asked once inside the car.

"Boarding House." He replied. "The Grill is still closed. Go figure."

"Strange." Elena said thoughtfully.

"Remind me to bring you to lots of restaurants and bars in Chicago. We'll make it up for the lack in here." He said.

"I can't wait." She said sincerely, taking his other hand in hers as they drove off.

Five days passed quickly between spending quality time with Damon and doing all the 'commissions' that Caroline and Bonnie gave her.

On Thursday they all went to the mall and first thing she knew, they had dragged her inside Victoria's Secret and made her buy at least ten different bunch of outfits. They had told her that she looked incredibly sexy in those and Bonnie specifically demaned her to wear the red lace corset during their first night. Elena had at first opted for something more natural and comfy, but she'd be damned if she didn't use all this exhausting shopping to seduce her man!

The worst part though was when Caroline brought her to their usual SPA just yesterday. You would guess that it was all about relax, but little did she know that Caroline had indeed booked a full body waxing for her.

She had almost cried like a baby when they went down there and still now it felt and looked incredibly weird...thankfully right after that she had her relaxing sauna and chocolate body scrub, making her skin as soft as silk.

She wanted to look, smell, and taste flawless for Damon when the time finally came. It was becoming an obsession.

Not to mention that Caroline's self-pleasuring suggestion had indeed worked awesomely…she definitely should listen to her more often about these things.

"Elena, wake up sleepy head." Damon shaked her softly.

She lazily opened her eyes and suddenly remembered that they were still in the cab that drove them from the airport.

It was rainy and cold outside and she had found herself feeling incredibly sleepy. Her head was resting on Damon's shoulder and she looked up at him, smiling sweetly.

She looked outside the window as Damon paid the driver and she gasped a little at the sight. He had told her that for the first week they would stay at his apartment. The building and the surroundings were beautiful and she immediatly understood that they were probably in a pretty cool neighbor of the city.

They got out of the cab and as Damon took both of their suitcases, she started feeling giddy and nervous. Her heart was beating faster than it should have and she wondered why it had hit her all of a sudden.

It was like she had just now realized that she was indeed in Chicago. With Damon. They made it. She got to share a part of his world.

As she predicted, the inside of the building was magnificent. It was large and renomated, the walls made of white marble and a red carpet all over the lobby. She had never been in such a fancy place and to be honest she was loving every minute of it.

"Mr. Salvatore." A middle-aged man immediatly cheered.

"Good evening, Rob." Damon replied politely.

"You can leave me your luggage here, sir. I will make sure to bring it upstairs for you."

"Thank you." Damon nodded. "I would like to introduce you to someone. This is my girlfriend, Elena." He then said, turning around to smile at her.

She was standing a little behind him and he couldn't help but grin at how cute and shy she looked.

"Girlfriend?" Rob repeated a little baffled. Of course…

He saw Damon giving him a look and he immediatly recomposed himself.

"You've made quite a catch, Mr. Salvatore." He said as he took her hand. "Enchanted to meet you, Miss."

"Likewise. And you can call me Elena." She said smiling.

"You two can go rest now. I will bring your luggage to Mr. Salvatore's apartment in a few minutes."

Damon wrapped his arm around the small of her back, leading her to the elevator. They headed inside and she saw him pressing the button for the tenth floor, which was also the last floor of the building.

"You didn't tell me that your apartment was on the last floor. Is it a penthouse?" She said surprised.

"Why? Does it matter?" He asked stepping closer, encircling her waist with his arms.

"Not that much, Mr. Salvatore, but you have quite the fancy lifestyle I can see." She teased.

"Had, baby. Had. Now I've become monogamous because of you." He chuckled into her hair.

She chuckled too and ruffled his hair a little, running a hand through its softness and staring into his sapphire blue eyes.

"I'm glad to be here with you Damon. I really am." She said seriously.

"I am too." He whispered, brushing his lips over hers in a soft caress.

The elevator's doors opened and Elena felt that giddy and nervous feeling all over again. She was about to see the place where Damon had spent the last six years of his life.

He was letting her in – in every way.

"Are you ready?" He smirked as he unlocked the front door.

As soon as it opened, she couldn't hold back the gasp and the wide eyes at the sight. This wasn't an apartment, this was a freaking luxury loft.

She kept looking around not quite believing that this was really someone's place and not a suite of some luxury 5 star hotel.

It was modern and huge, furnished and decorated in detail. It was stunning.

"Damon this is…wow." Elena said speechless. "This is the most beautiful house I've ever seen. Movies included." She chuckled.

"I thought that you might like it." He winked.

He headed to the living room/parlor and quickly started a fire, turning it on with some kind of remote.

"I want a tour of the house." She grinned excitedly.

"Can't it wait? Right now I just want to lay on my comfy couch with you." He groaned.

"Be that way, lazy ass." She crossed her arms. "I'm just going to do it by myself then."

He huffed quietly and stood up, reaching her in the middle of the room.

"I may be a lazy ass but you sure are a pain in the ass when you want to." He said narrowing his eyes.

"Oh please. You can't bring me in here and expect me to just sit around and wait for you to show me the amazingness that this house is." She hushed him quickly.

She had pretty much seen all of the parlor - which was covered in dark wooden floor, white walls, and lots of cool forniture. The sixty inch TV was what caught her eyes the most.

The other part of the parlor leaded to the kitchen and dining area which were well fitted and thought as well.

Elena was mesmerized. Sure the Boarding House was a wonderful maison too, but it was old style and Damon didn't even live there anymore. It was a given to say that his apartment in Mystic Falls couldn't even begin to compare with this one. How could he let something like this go?

"Want a cup of coffee or something?" He asked, pulling her out of her thoughts.

"Why not." She smiled, sitting on the stool next to the counter. "So how did you manage this? I mean this is…wow." She said out loud.

He chuckled a little, pouring them some coffee as he leaned on the counter in front of her.

"My friend Sage is an architet, she helped me with everything when I first moved in. Believe it or not, this apartment was nothing compared to what it is now." He shrugged.

Elena stayed quiet for a few moments, contemplating about what he just said. Did he really think this through? Leaving the city, his job, his home…she didn't want him to make one of the biggest mistakes of his life. She wanted nothing more than Damon by her side but she needed to be sure that he wanted this too.

"So let's show me the upstairs?" She asked excitedly after a few minutes, jumping off the stool.

"You want to get to the great stuff already, I get it." He smirked.

She gave him a coy look, waiting for him to show her. He walked over her and gently took her hand in his, caressing its palm soothingly.

They marched on the modern stairs which leaded to his master bedroom and the bathroom.

Needless to say that his room was quite the sight as well. Armed of a California king bed, a huge desk with his laptop and papers, and a soft dark-rouge almost brown moquette it made it look like a luxury room even in here. Maybe she was just overreacting over the beauty that this house was but she couldn't help but be surprised and mesmerized at how much Damon had accomplished. Just then she noticed the same fireplace that was downstairs too and her mind started leading to erotic dreams where she and Damon would spend hours making love on the floor by the fireplace.

She mindlessly sighed softly in awe, immediatly realizing how crystal clear she must have sounded. She blushed a light shade of pink and then shyly glanced at Damon, who just glanced back at her with a knowing smile on his face and a little wink.

"And this is the bathroom." He concluded, opening the black door that leaded to another big classy room.

Her eyes widened in disbelief when she spotted the jacuzzi at the bottom of the bathroom.

"My god, Damon!" She exclaimed. "You might as well have told me that this was more like a royal residence than 'your house in Chicago'."

He chuckled amused and approached her, ruffling her hair.

"What can I say?" He shrugged casually. "When I first came to Chicago I was eighteen and I happened to have a pretty great trust fund."

"Maria would smack you if she knew that you spent most of your money just to please your spoiled ego." Elena said smirking.

"Did you just call me spoiled?" He raised an eyebrow.

"Very much so."

"You are becoming one sneaky thing, young lady." He tsked her.

"And you like it?" She asked huskily.

"Very much so."

They smiled at each other until he picked her up bridal style and she locked her arms around his neck. When they were this close it was impossible for her not to lose herself in those sparkling ocean blue eyes.

She stared at him for a few seconds and then kissed him softly. He rubbed his noise against hers as he started kissing every inch of her face and she giggled lightly.

"Wanna take a relaxing bath?" He asked her sweetly.

There was no innuendo or subtle pressure behind his words and Elena couldn't help but smile at his sweetness. He had been so comprehensive and patient about the whole thing. She didn't know herself how they hadn't jumped each other's bones already to be honest.

"Wanna take it with me?" She offered hesitantly, her voice small.

His eyes widened a little for a few seconds and his mouth fell open, leaving him speechless. He hadn't seen this coming. He quickly recomposed and gave her a reassuring smile.

"Are you sure? I mean love me some naked Elena, but if you're not ready…" He started saying.

She giggled lightly and pushed his chest. "I may not be ready for that right now, but I'm definitely in the mood for some naked Damon too."

He grinned happily and pecked at her lips, putting her down right after.

He headed towards the jacuzzi and opened the water. As he moved to begin to take his shirt off, Elena reached him and caressed his chest lightly, her fingers lingering on his nipples a little bit longer.

"Allow me." She said as she began to undress him.

He looked at her in awe, savoring in the moment of his Elena undressing him until he would be completely naked.

When his shirt was laying on the floor she licked her lips as she looked at his bare muscled torso. His jeans started to feel a little too tight for his growing member and he decided that he had to touch her too.

He went to unbotton her silky shirt in one rapid move, hungry to feel her nude skin against his own. Her black lacy bra flied next to their shirts moments later and his eyes grew dark and lustful at the sight of her perfect round breasts. Her perky rose nipples were already hardened and he was craving to take them in his mouth.

His eyes though immediatly snapped over to look at her in the eyes, which held so much vulnerability at the moment.

He gently pushed his chest against her own, their skins milking.

"You are beautiful." He whispered in her ear, his hands slipping up to her breasts and squeezing them softly.

Her soft whimper made his jeans uncomfortably tight by now. He took a deep breath to control himself as his right hand went to unbutton her jeans.

He reached the hem, slowly unzipping it and sliding her jeans down her long legs. She was now only left in her tiny panties and he groaned loudly when she rubbed herself against him a little.

"Your turn now." She said as she reached for his zip.

He felt her hands trembling slightly as she tried to manage it open. He started kissing her neck, trying to soothe her and distract her as his hands joined hers to unzip his jeans.

"First thing first." He said huskily. "I need to touch you." He then pleaded softly.

She held his gaze intently for long moments, contemplating what to do next. She then just went for it and took off her panties, throwing them on the floor near their discarded clothes.

"This is it." She shrugged a little, her eyes filled with emotion and vulnerability. "I'm yours, Damon."

There she was; her olive smooth skin completely revelead in front of him. Her long chestnut hair was wildly cascading down her shoulders around her round breasts. His eyes darted to her bald pussy and his hard member throbbed painfully in need.

His lips twitched to hold his sheaky breathing and lust that he felt at the sight of Elena naked and innocent right in front of his eyes.

Damn, he hadn't felt this way in…never. Troughout the years he'd had tons of experience with women but somehow Elena managed to make him feel and act as a completely clumsy.

Her big brown doe eyes were shimmering with something he couldn't quite explain and he smiled at her, the most genuine smile he had ever smiled in his life. He cupped her face in his hands, his lips covering every inch of her skin, kissing from her chin to her closed eye-lids.

He didn't care if it wasn't the right moment or she wasn't ready to hear it – he had to tell her now. Every fiber of his being was screaming at him to do it.

She lazily opened her eyes only to find him staring right back at her with overwhelming emotion.

"Elena, I…" He was just about to spill the magic word when the sudden loud rang echoed through the house and made them both jump.

"Shit." He muttered, pissed that whoever it was rudely ruined the moment.

"Who is it?" Elena asked clearly baffled. She seemed upset just as much as he seemed to be.

"This is probably Rob with our luggage." He said as he zipped his jeans and quickly threw his shirt on, not bothering to button it.

He kissed Elena on the forehead and stroked her cheek softly.

"You go get in the tub, I'll come in a sec." He said winking.

Damon quickly hopped downstairs trying to mask his annoyance. How he fucking wished that it was Rob though when he opened the door and found a little surprise behind it...

His jaw clentched and his eyes turned piercing and cold. A look reserved only to people he would gladly slice to pieces.

"Katherine." He acknoweledged out loud.

"Missed me, lover?" She purred in delight.